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It wasn't a shock, but I was surprised by the turn of events. I was in upper management for a small company for the past 18 years. We had grown our company, improving sales every year. I felt pretty secure where I was, but you never relax. So when the owner got a takeover offer from a bigger firm in our line of business, I wasn't shocked that he took it. The buyout made him a millionaire several times over. But what surprised me was in the takeover transition, my job was identified as a duplicate with one of the existing jobs in the bigger firm, so I wouldn't be retained. However, the impact was softened by their offer. They would pay me half my salary for two years, as long as I would be available to provide information and guidance to the person who would be blending my job with his role at the larger firm. It seemed like a considerate offer, I mean they could have just let me go. But later I realized it kept me from going to another competitor while they combined the two companies. At the time, for me, it seemed perfect. I had been thinking of trying something new, so this gave me the opportunity to refocus and rest while deciding what to do. Plus, I only needed to spend about 15 hours a week, online or on the phone, to give them guidance. I didn't even have to go to an office. I took the time to evaluate my life. I was only mid-40s, Emily and I had been married since we were 28, and we had decided against having children. With my new free time, I began to focus on things in my life that I had ignored. I began to landscape things around the house. I had always enjoyed working in the yard, but never had time. Now I did. Similarly, I began to help Emily, my wife, with meal prep. When I was younger, I enjoyed cooking so I started doing more of it, focusing on healthy meals. I made time each day to read, usually fiction, something I had loved growing up, but had abandoned when I started college. Other things were simply experiences I wanted to try now that the shackles of a daily job were gone. I tried growing a beard. The new look was okay, but I couldn't stand how it made me itch, so I shaved it after a month. I let my hair grow out, something I hadn't done since college. Not that it got real long, but I could make a short ponytail. That was okay. But the most important thing I decided to do with my free time, was to get in better shape. I had gradually added weight to my naturally thin frame, as my job kept me busy 50 to 60 hours a week. Lots of fast food, snacks and hardly any exercise made it easy to gain weight. I had ballooned all the way up to 200 pounds, a ridiculously heavy amount for me. I couldn't even fit in any of my jeans. So I started simple. I began to count calories and walk in our neighborhood. The combination produced instant results. I lost weight each week, until I reached what had been my 'usual' weight over the past 10 years of 180 pounds. My jeans fit. But I had the bug, and wanted to be slimmer. I had never thought about it before, but at barely 5'7", I should have weighed less, like I did in high school. By slightly reducing the amount of calories I ate every day, and varying my walking from 4 to 7 miles a day, I was able to keep losing weight. I not only was getting thinner, but I felt healthier too. I was determined to be 'thin', a designation anyone would make if they saw me. Something, I had never really been in my life. My wife, Emily, loved my new attitude. She had been concerned about me having a heart attack or developing diabetes from being too heavy. So, she encouraged my efforts. She often walked part of the neighborhood with me, and made allowances in our meals for my calorie goals. We'd been married 15 years and as we adjusted to me being home more, both felt this was like a preview of what retirement might be like. The only difference, was we wanted to travel and do more socially. I had the time now, but wanted to finish my weight loss first. Once I got below my old weight, my clothes didn't fit quite as well. But I was determined not to buy new ones, or very many new ones, until I had gotten to a target weight. Since I had no reason to leave home for work, it was easier to keep this goal. I just got used to putting more holes in my belts, cinching them tighter around my pants, and even wearing sweat pants around the house. I admit I looked like a baggy version of my old self. Emily hounded me about getting some new pants or shirts, but I refused. Not till I met the target. That kind of determination was one of the traits that made me successful in management. What was ironic, was the definition of the target. When I started, I had hoped just to get to my old weight. When I made that, I wanted to lose another 10 pounds. When I made that weight, the goal kept moving, another 5, maybe another 10. Just to be 'thin'. It was addictive to see the number on the scale be smaller every week. A sort of continuous reinforcement of my efforts. When I plateaued, staying the same weight for a week or two, I'd double my efforts to get back on a losing track. Emily was fine with me continuing to lose weight, although she did press me occasionally to set a firm number. I think she was worried I had become almost too focused on my weight. I was becoming thin enough, she said and didn't want to be married to an anorexic. So I did choose a firm target, 155 pounds. I told her once I hit that, I'd focus on maintenance. If I could stay at that weight for a month, then I would be stabilized and we could expand our social activity again. It had been about a week with me at 155, when Emily said we had a social event to go to. It was one of neighbors. An anniversary party - cookout, nothing fancy but she insisted we go. I had been reticent about it, still nervous about buying any new pants until I felt I was stable, weight wise. So when it was time to head over, I had put on my smallest jeans, a size 42 waist, cinched them up with a belt and tucked in my white tee shirt. I planned on wearing one of my size 18 shirts. I knew I still looked baggy, but with my shirt untucked, at least you wouldn't see how cinched up my belt was. Emily took one look and refused. "Dana, that won't do. You look like a one of those blow up lawn ornaments that had been partially deflated. We've got to find something else for you." "But Emily, these are my smallest pants. What else can I wear? Maybe you should go without me?" "No way buster. Tell you what, let me try something. Take off those pants." I did as she said, while she disappeared into our walk-in closet. She reappeared with a pair of dark wash jeans. She handed them to me. "Try these." I looked at them, and could see they weren't a pair of mine. Although they weren't wildly different, I could tell from the trim that they were hers. But I could see she was determined I try them, so I did. I had to admit, they fit me better, although still pretty lose, than mine. "These are yours, aren't they? I guess they're okay." Emily came closer, ran her hand around the waist, between me and the jeans. There was a couple of inches clearance, enough that I would have to cinch up a belt on these too. Not as much, as with my old pants, but still... "Yes, they are mine, but they're still too baggy. I can't believe that. These are a size 10, my normal size. I thought these would be tight on you. But, wait a minute, go ahead and take them off. I want you to try another pair." This time, Emily went to our spare bedroom to look in that closet, while I took off the first pair of jeans. Coming back in the room, Emily handed me another pair of jeans. These were a regular blue jean color, with lines radiating around the fly in front like whiskers on a cat, and a bit more embroidery detail on the back pockets. I already suspected she'd bring another pair of hers, so some sort of details were expected. I worked them up my legs, pulled them over my hips and onto my waist. I zipped up the fly and buttoned the front. They seem to fit perfectly, not too tight or loose. I looked over at Emily. "Those fit don't they? I was sure they'd be tight. Well, you bastard. Those are my smallest jeans. I bought them, as part of my 'new wardrobe' after my training. You remember, a few years back, all the neighborhood girls decided to do the charity half-marathon. We trained for a couple of months. I lost so much weight, I dropped a few dress sizes. I thought I'd be able to stay that small, so I bought a whole bunch of new clothes. So I could wear those size 6 jeans instead of my normal 10s. Of course, once I stopped running six miles a day, I went back to my normal weight and regular clothes. Now you waltz in here, and just slip right into them. Damn." If she hadn't been smiling, I would have thought she was mad. But she seemed genuinely pleased that the jeans fit me. I was apprehensive about them, not wanting to wear my wife's clothes. "I know they fit, but they're women's jeans. One look and everyone will know. I can't wear these." "Oh, don't be silly. The only way you can tell, is by the brand name on the front button and the pocket details. If you wear a dress shirt, untucked, those details will be hidden. Personally, I'm proud of your weight loss and these jeans really show that off. But I don't like them with your underwear. Those boxers are too big for such tight jeans, you can see them bunched up. Take off the jeans." I did as she asked while she went to her dresser. She fumbled around there for a few minutes, until she pulled out something. Holding it up, I could see it was a plain white pair of women's' underwear. She handed them to me. "Take off those boxers, and try these. I got them as part of my tiny wardrobe." "I can't wear women's underwear." "Why not? No one will see. Those are plain hip-hugger panties, not really different than guy's briefs except there is no fly. Try them." I relented, took off my boxers, and pulled on the panties. They did fit, perhaps a bit snug, but I could feel them stretch. So I put the jeans back on. Gone were the lumps caused by my bunched up underwear. "Much better, you look so trim in those. Let's put on a top and see how they look." I reached for my shirt, but she shook her head no. Back to the spare room closet, she got another shirt, also plaid and handed it to me. By now, I had given up arguing, so I put it on. I fumbled a little with the buttons, so she helped me out. A quick look and I could tell this shirt fit me, much, much better. The sleeves might have been a tad short, and the collar was small, but everything else was okay. The main color was rust with pale green and light pink as accents, not exactly manly but it wasn't bright pink. It was long enough to cover my jean pockets, so that was good. Inside I knew this was one of her blouses, which explained why I had trouble buttoning them since the buttons were on the opposite side. Emily seemed pleased. "Now that looks one hundred percent better. You can tell you lost weight, lots of it. The top and jeans fit you. It would look better without that undershirt, can you try without it?" "No, I need it. I look fine." Emily relented on this point and I got my socks and shoes. I felt a little awkward and self-conscious about wearing her things, but I had looked myself over pretty good in the mirror. About the only noticeable detail was that the jeans were a skinny style that fit close to the leg. I hadn't any jeans like that. I knew more men wore the style, but it felt odd for me. Still, I also felt pretty proud of my weight loss, so I overlooked that detail. We got ready to go, and I grabbed my wallet. But I soon found it wouldn't fit in the back pockets, as they were too narrow. Obviously women never put anything in their back pockets. "Emily, my wallet won't fit in the jeans." "No big deal, put it and your phone in the purse on the table. I'm going to drive, so just bring it along." I did as she suggested, and we headed to the party. Emily seemed excited, both to be going out and because the party was for a couple that had been married for quite a while. She also seemed to be proud to show off my weight loss. As we got out of the car, she handed me the car keys. "Put these in the purse. I don't want a bulge in my pockets." I unzipped it and put the keys inside, but when I tried to hand her the purse, she just smiled and continued walking to the front door. "No, you hang on to it. It goes with your outfit. Didn't you notice how it matches your blouse?" I glanced quickly at the purse. It did have similar colors as my shirt. I also looked around to see if anyone was near. I didn't want them hearing her call it a blouse. "Emily, I can't hold on to this all night. It will get in the way." "Then use the strap and put it over your neck. It's a cross-body bag, so it will hang by your side. Sort of like those old fanny packs you used to like." She laughed and continued on. I didn't know what else to do, so I looped it over my head and around my body. By the time we got inside, I had more or less forgot about it. The party was nice. I had a good time and got lots of compliments on my weight loss. I had also forgotten how much fun it was to socialize. Since leaving my job, I had been at home almost constantly. As I lost weight and stopped going out because of the poor-fitting clothes, I had become even more isolated. So talking with the guys and their wives was relaxing and entertaining. By the time, we left I was glad we came. Emily suggested I drive home, and as we rode along, she had a big grin on her face. "What's up? You look like you know a big secret, no one else knows." "Oh, I'm just pleased about the party. Everyone really was impressed with how healthy you were becoming. There were so many compliments." "Yea, that was nice. I had lots of people congratulate me on losing all that weight. They mentioned seeing me walk all the time." "Yes, the girls were very impressed. I mean, they realize how tough it can be to lose weight and you've done a great job. Plus, they loved your outfit. They couldn't believe you were wearing size 6 jeans and size 8 top. Not only that, but when I told them how well my size 4 panties fit they were amazed." This revelation changed my mood. Now I was upset. "You told them that? Why? I thought it was our secret. I didn't expect you to blab to everyone, or I wouldn't have agreed to wear this stuff." "Oh, settle down. What was I supposed to say? They could tell right away you were wearing girl's clothes. No woman alive, would have missed the button details of your blouse, and although your jean pockets were covered when you were standing around, whenever you bent over or reached for something, you could see the pretty details. Besides, sweetie you were carrying a purse. The other thing that stood out, really surprised me when I watched you at the party, was how naturally feminine you looked. Many of your hand movements, the way you stood and walked, and just your facial expressions were all girl. Several of my friends mentioned it too. Apparently they had seen hints before in your body positions, behavior, and motions, but in male clothing they just took it as you being more sensitive. Once they pointed it out, I saw it clearly. Personally, I love it. You just seem so much more attractive without the typical macho posturing so many guys do. I like having someone that is so in touch with their feminine tendencies. Now I'm sure the guys didn't notice. Men never see details like that. So don't worry. I mean the girls were also impressed that you could wear my 'thin sizes' and you were smart enough to not repeat my mistake and buy a whole new wardrobe that you might soon would grow out of. Waiting a month or two, to be sure how much weight you can reasonably keep off is a great idea. That reminds me, when we get home I want to measure you. You've been so focused on the weight, you never looked at your body measurements that really determine sizes." I was still irritated, but what could I do? I convinced myself that as long as the guys didn't see it would be okay. Back at the house, we went to the bedroom. Emily had me undress down to my underwear and got a cloth measuring tape and a note pad. She seemed really excited to see what I was now. "Stand up straight, I want to get these measurements right. As you go on, we can check these as well as your body weight to see how well you're maintaining your new size." Emily started with my inseam, then my calf, and thigh. These were more or less to see if I was changing over time. She quickly did my hips and then waist, smiling broadly as she wrote down the numbers. "Dana take off your tee shirt so I can measure your chest." "Do I have too? Can't you just measure over it like you did the underwear?" "That shirt is too baggy to measure over. What's the problem?" "I'm just a little embarrassed. Despite my overall weight loss, I'm still pretty flabby, especially my chest." "It will be fine. Just take it off for a minute." Reluctantly, I did as she asked. I blushed immediately, as I knew my upper body was flabby. That's one of the reasons I had kept trying to lose weight, as I just didn't like having fat around my chest, kind of a male boob look. When I had my shirt off, Emily looked, slightly puzzled. Then she positioned the tape. "Help me line it up. Keep it straight and right below your nipples, on your rib cage." I did as she asked. Then helped move the tape up, so it was centered across my nipples, and finally above them, going through my underarms. Emily finished by measuring around my neck for my collar size and down my arm for sleeve length. She seemed to be doing some scribbling with the numbers. When she was done, she shook her head, as if in disbelief. But instead of telling me my sizes, she put the pad down and went to her dresser, opening the same drawer she had gotten my panty from. Digging around, she found what she wanted and came back over to me. I saw immediately what was in her hand. "Oh, no. I'm not putting that on." "Hush, just put your arms though here. I want to see something, just to be sure." I was really embarrassed now. She had brought a bra over, a light blue one. She held it out, so I could slip my arms through the straps, and then she moved behind me to hook it together. Emily adjusted the straps, stepped in front of me, and told me to lean over. Pulling the cups forward, she adjusted them around my body. Finally stepping back, she shook her head again. "I can't believe it, even though I'm seeing it. Honey, your body measurements are unbelievable. You've got a real hourglass shape. Your hips were 35.5 and your waist was a tiny 25. You always had a round butt, sort of sticking out, but you're waist made it seem average, as you were bigger there. Now, you've got such a sharp change between hips and waist, it gives you a very feminine look. However, what floored me the most was your chest measurements. That's why I had to put that on you. You are a perfect 34B. I thought it couldn't be true, but look. You fill out the cups completely. When I ran, I lost so much body fat, I dropped from my normal 36C to a cup size smaller. That was one change I didn't like. Your measurements are like mine were then. Your band size, around your ribs is 34, across your breasts is 36 that translates to a B cup. No wonder you could wear my clothes." Emily reached up and put one hand around the bra cup. She lightly squeezed and fondled it, as if to be sure that I had filled it completely. I had. There was no doubt that her old bra fit me. I was blazing red by now. So humiliated that I could wear a bra. That I could fill out a bra. All the positives I felt about losing weight were gone in that moment. I kept thinking about the measurements, 36-25-36. They were so close to that old standard men used about a woman's ideal figure. I stepped over to see how I looked in the mirror. I cringed when I saw my reflection. I could see the indentation where my waist was above my hips, but what really caught my eye was up top. With the bra, my chest had turned into a pair of breasts. I turned slightly sideways. There was no mistaking my profile, I had boobs. Boobs snuggled into blue lace cups of a bra. I looked down at my chest and saw a hint of cleavage. My god. As I looked over my image, the hourglass shape she mentioned jumped out at me. I never had this shape before. It was so puzzling. Why had my waist gotten so small, but my hips and chest remained fatter? This was a nightmare. But Emily didn't seemed fazed, she was smiling. She saw my reaction. "Dana, it's okay. Really it is. You just need to change your workout regime. You've focused this whole time on your weight. That one number. But you need to pay attention to other things too. I'm sure if you do some weight lifting, put on some muscle, maybe run instead of walk, that you can adjust your body proportions. But until then, let's have fun with it. To be honest, I find it exciting that you look like this. Do me a favor, I want you to try on some more of my 'thin' clothes." I couldn't believe what she was saying. I mean, the part about changing my workout regime was worth a try. But not about her lack of dismay that I had breasts. "Honey, maybe it seems okay to you, but not me. I mean, it is so frustrating to me, that despite my attempts to lose weight, and my success at it, that I'm left with this flabby chest. I mean, I knew something was wrong. That's why I went to our family doctor. He did a couple of blood tests, said my hormone levels were fine, and that there were no abnormal findings. He just dismissed it as a cosmetic concern, not a health issue. Now you seem, to not only be okay with it, but almost happy about it. Don't you understand how I feel?" "Of course, I do Dana. As a woman, I felt those kind of self-image issues all my life. Growing up, I worried about being fat, too thin, not having any breasts, my breasts being too big, my nipples looking funny, my ass being flat not round, my nose being too big, and any number of other issues. Now, I realize that most, if not all, of those issues were never noticed by anyone else. Every girl growing up worried about her breasts being normal, whether she was an A-cup or a D-cup. So, the fact that you might have some fat on your chest isn't really life shattering. Dr. Palms is right, if your health is okay, that's what is really important. Plus, I'm convinced that you'll be able to shape yourself closer to what you want. Just don't obsess over it. What I want you to do, is to let go. This is a once in a lifetime chance, for you and me. In a few months you will look different and it will be over. So please consider this an opportunity to see life from the other side. Now how about we try on some of my other jeans and pants to see if they fit?" Emily had come to me, wrapped her arms around me as she talked. When she was finished, we kissed and she continued to tell me it would be fine. Finally, I relented. I saw her point that it would take time, and maybe until then, I should go with her desires. So, we went to the spare bedroom, where she had stored all her 'thin' clothes. I was surprised at how much was there. I knew she could be a clothes nut, but it looked like enough for two wardrobes. We spent the next hour or so trying on her 'thin' clothes. As we went along, I could sense that there was something else in this. In some way, if I wore these clothes over the next month or so, that might take the sting out of her failure to keep her weight at a level where these fit her. Inside, I knew that feeling. That's one of the main reasons, I wasn't buying any clothes till I found out what I should consider my stable, target weight. I had to admit, some of her clothes were difficult to put on. Not because they didn't fit, but because they were super feminine. She had several pairs of pants that zipped up the side or back. She had jeans with sparkly or embroidered details. Styles could be challenging too. Capris, very skinny jeans with stretch so they molded tightly to your shape, or low-rise jeans that went only half way up my hips. Colors were an issue too, including some that were not in the usual masculine palette. Overall there were only two or three that didn't give me a feminine look. We also tried on her tops too. She had more blouses like the one I wore tonight, but also styles that had scoop or v-necklines, were sleeveless, had ruffles, or lace, and spanned a whole range of colors. Trying these on was more challenging than the pants, as Emily insisted I keep the blue bra on. I could see immediately how my boobs changed the look of each top. It didn't help, that she would interject comments that a top needed a different bra style or color, or I needed a camisole as the fabric was too sheer. Emily also was relentless cheerful about it all. She loved how almost every one of the items looked on me. I could tell she was having a ball. Just about when I thought the worst was over, Emily emerged from the closet with another item for me. A dress. "Oh come on Emily. You can't expect me to try that, can you? When would I ever wear it?" "Relax, just let me see how you look. I've got lots of dresses, as well as some skirts. If you're going to do this for me, it would be a shame not to go all the way. I mean, who would know if you wore a cute dress for dinner at home? Now this was one of my favorites. It's a sweater dress that fits snug but not too tight. I always felt it highlight my curves just right, so I want to see how it does for you." I relented and after removing my pants and top, allowed her to slide it over my head and zip up the back. She turned me to face the wall mirror. I could see her smiling broadly, probably as pleased with how it fit me, as anything I had tried on so far. For me, it was the worst thing. She was right, the dress molded itself to me. So it emphasized my hips, narrow waist and visible bust. It stopped about mid-thigh and had a low scoop neckline that with the right bra, would show some nice cleavage. In fact, I actually remembered how sexy she looked in it. Now the shoe was on the other foot, and for the first time, since we started, I blushed. My embarrassment wasn't just from how I looked in her clothes. But because I also felt something different. Was it pride? Did I actually like how I looked in the dress? For a fleeting moment, I wanted to see how it would look with a pushup-type bra. These feelings were confusing. Earlier when I had on blouses, or pants that were feminine, I had been impressed with how nice they looked on me. I didn't want to admit that, but I knew it was true. So, I was really getting confused. Emily came to me, still smiling, and wrapped her arm around my waist. I could see she loved how the dress looked on me. While we stood there, she undid my ponytail, and using her fingertips, sort of arranged my hair. I felt like a doll she was playing with. But I just couldn't take my eyes off my figure, as I tried to decide how I got this way. Finally, I was done. I had to think all this over, before we did any more. "Emily, this is enough. I'm tired of trying on clothes and want to go to bed. We can talk about this more tomorrow." "Okay sweetie, I agree it's getting late. Thanks for doing this for me. I had fun and you got to admit, you looked pretty good in most of these clothes. I just wish we had a similar shoe size, I'd love to see you in this dress with a nice pair of heels. Also, maybe we should consider doing something with your hair. Something easy, but stylish. I'm sure there'd be a look that would be adaptable to what we need. Get undressed and we'll get ready for bed." I removed the dress and lingerie, while Emily put on her nightgown. As I went to go into the bathroom to get my pajamas, a baggy pair I had from when I was heavier, she handed me some folded garments. I took them, and held one up. It was a pair of loose Capri style pajama bottoms with a small flowery print in blue and green. The matching top was a pullover with short, cap sleeves, a rounded neckline, and ruffled hem. I groaned inwardly. "Try these. I think they're big enough for you. I'm getting tired of sleeping next to a pile of baggy clothes, with a cute guy inside." Despite her attempt at a humorous compliment, I wasn't happy about this. It was worse, when her PJ set fit me perfectly. Resigned, I crawled in bed. Luckily, I was so tired I fell asleep quickly. The next morning, Emily woke up first, made me a nice breakfast. She had left out a short robe that was part of my sleep set. So we sat eating, both in our coordinated pajama and robe outfits. I told her I needed to work for a few hours this morning, so I would be going into our downstairs office. I had some calls and emails to make. I told her, we'd sort out everything else later. She agreed, saying she had some stuff to do upstairs. After catching up on my work for about three hours, I was ready to go upstairs and change. Even though my PJ set was comfortable, I wanted to put on some of my old sweats to go for a walk. I needed a chance to clear my head. But as I was headed upstairs, Emily came out with a couple of large trash bags. She put one down, and showed me the other. "Dana, take this bag to the trash, its stuff that's not useable any more. This other bag, I'll drop off at the charity thrift store, as the things are good but we don't need any longer." I took the first bag and put it in the garage next to our large trash bin. Back inside, I went upstairs to change. But I saw right away, as I opened the chest of drawers where I had kept my sweats, what was in the bags Emily had filled. My old clothes. A quick look in my closet confirmed that. All of the old clothes, that were far too big for me, were gone. On my side of the closet were now, all the 'thin' clothes that had been Emily's. I guess they were mine now. The dresser had similarly been culled. All my tee shirts, workout clothes, and underwear were gone. My drawers now held panties, bras, and some sleep clothes. It also looked like some of her workout gear. I hadn't realized she was going to go this far. So, I went to the bathroom, where she was putting on her makeup, to talk. "Emily, I wasn't quite ready for you to clean out my things. I mean, I thought I'd only wear your stuff occasionally. Especially, like the underwear and things I wore to walk in. Where did you put my sweats?" "You're not digging those out. They are trash. Every time you went outside in them, I'd cringe. Besides being way too big for you now, they had holes or stains. I gave you some of my workout gear. It should fit you much better now and look good too. There are a couple of light jackets that go with leggings and tank tops, with built-in bras. They should be more comfortable too. As far as the other clothes, you may not stay at 155, but we know you're not getting back to 185 or 220 pounds. Nothing you have will fit you going forward. Your new wardrobe is fine and I see no reason to delay. In fact, I'm going to make a hair appointment for you with my stylist. She is wonderful and I'm sure she can recommend a nice, easy to take care of look. Something that'll go with either a dress or jeans, depending on how you comb and style it. Dana, just follow my lead, and everything will be fine. I know how sensitive you are about your new appearance. So, I'm going to help you starting working to shape your body the way you want. I didn't mention it before, but when the girls saw you last night, saw how much weight you'd lost and how great you looked, they wanted to revive our running group. If you ran with us, it would not only give you a good cardio workout, but should help shape your muscles. If we join a fitness club, then we can add some muscle for you and help make me firmer. There's a woman's only gym, near the grocery. Something like that would be low key, no pressure form guys, just what we'd need. I decided I need to get with the program, if I'm going to have such a sexy husband. So, just go with the flow, it will be fine." Her arguments didn't totally convince me, but I knew when she made her mind up, that it was impossible to change it. I reluctantly went to see what those workout clothes looked like. I found a matching jacket, tank top, and long legging, in black with blue trim. There were several other sets, including one for running with ridiculously short shorts, and what looked like a pair of tights with an attached skirt. I would have to talk with Emily about those. I also looked a little closer at the underwear that was now mine. I found two plain pair of panties, in beige and black that looked like the pair I wore last night. But most of the panties, were far more feminine. Some seemed so small I wasn't sure I could even wear them and still cover myself. The drawer with the bras was even worse. Almost all of them were very sexy looking, much more so than the blue one I had tried on. Maybe I'd buy some new men's underwear that fit. Just as I was trying to decide what to do, Emily came back in the room. "Dana, great news. I called Tiffany and she's actually got an opening this afternoon. So, I need you to take a shower, but don't bother washing your hair. Just shave, brush your teeth and get ready. I'll lay out something for you to wear. I can't wait to see you in a new hair style." I had little chance to argue or protest, Emily had already decided this was the best decision. So I did as she wanted, getting cleaned up and ready. When I came back into the bedroom, I could see some clothes laid out on the bed. On top of the pile was a small panty in a soft peach, basically two triangles connected by strings on the side. My heart skipped a beat, as it looked so cute and inside, deep inside, I was eager to try it on. It looked too small, but I gingerly began to work it up my legs. Just as I had it to my thighs, Emily came back in. Seeing me, she put her hand on my hip. "I loved those panties. They fit so well, even though they look small, but it's because they stretch. But since you've got more up front than I do, and there's not a lot of fabric, so why don't you line up your cock so it's pointing backwards?" I did as she suggested, sort of holding it back, while she pulled the panty over my hips. The head of my cock was nestled in the cotton crotch, leaving enough fabric in front to cover the rest. The way it stretched covered most of my ass, but part of each cheek was exposed. Emily seemed pleased with the way it fit. "Here's the matching bra for these panties. It is a soft cup, very comfortable. I'll help you with it this time." I let her put it on, and she was right the soft lace fabric and thin band was hardly noticeable. Again, I felt conflicted. It dismayed me a little that my boobs filled the cups completely, but I also loved how I looked in the bra. Plus it felt better to have them supported. The top was a tunic style with a cowl neck that came down to mid-thigh, with two side slits. It was a marbled green with a rear zipper. I expected it to be really loose as I put it over my head. But when it was zipped up, it molded to my frame, showing off my both my hourglass shape and my bust. Rather than jeans, Emily had picked a light peach pair of leggings. They were sheer, with a band of lace at the bottom of each leg. They again looked small, but when I pulled them on, they stretched enough to cover my panty. This was a much more feminine outfit than I would have chosen, but Emily said we needed to go, so I didn't argue. She also suggested that since my shoes would be too clunky for this outfit, I should just wear a pair of flip-flops. Of course, she handed me a small purse as we headed out the door, her driving again. I couldn't believe this was really happening. It had occurred so fast, I hadn't thought about going out in such a feminine outfit, let alone even had time to think about whether I really wanted the hair cut she seemed so eager for me to get. The salon was only about 10 miles so we got there fairly quickly. That was the easy part. Getting out of the car and walking into the building was hard. First, it looked really busy, with about ten stylists all working on customers, an area where nail techs were working, and a couple of customers in the lobby. Second, I was dressed like a woman. Emily said the tunic was like a sweater and the leggings like pants, but to me the outfit was closer to a dress and tights. Third, I was coming here to get a woman's hair style. To make a change in my appearance that I couldn't easily remove, like a piece of clothing, or that I wouldn't have to admit was not just for practical reasons. So I was scared. But deep inside, I was also excited. I sort of wanted to see how I might look. Plus, I was proud of how the tight tunic reflected my new body image. The conflicting emotions bounced around inside my head. The receptionist recognized Emily and they chatted briefly, while I stood there awkwardly looking at the ground and wanting to die. After a few minutes while they sorted things out, Emily's friend Tiffany brought her a book to look at it. She had flagged a few suggestions for us to consider. She had to finish another customer first, but by the time my other services were done she would be available. I looked sharply at Emily, who just smiled and whispered that she thought it would be best if I did it all at once. I was just about to find out what else she had planned, when another woman came up to the front desk. "Are you Dana? Hello, I'm Stacy. Come with me and I'll get you taken care of." "Dana, I'm going to run a few errands but will be back before we meet with Tiffany. Just do what the ladies have lined up." I felt abandoned now, and meekly followed Stacy. She led me past the nail techs, down a hall to a small room. She opened the door, suggesting I go in. "Go ahead and get undressed to your underwear. You can get on the table and cover yourself with the sheet until I get back to start." I felt like I was going to pass out, but I had to know what was planned. "So what is it you're doing for me?" "Emily had you scheduled for some waxing, I thought you knew. Just relax, if this is your first time. It's not as bad as you've heard." I nodded and went in, while she closed the door. My head was spinning. I wanted to be mad at Emily, but it was too late now. I quickly got out of the tunic and leggings, slipping under the sheet on the table. I left the bra on, not knowing what Stacy considered underwear. I hoped that maybe she was only going to wax my legs, but deep inside, I knew she wouldn't have had me take off my top if that was the case. Stacy came back in just a few minutes. She glanced over at me, lifting the sheet to look at my legs. My arms were folded across my chest on top of the sheet. Smiling she turned to move a cart next to the table. "If the rest of you has about the same density of hair as your forearms and legs, this will go real quickly. The best part is, the first time is always the worst. It will get easier and easier every time I wax you as the process affects the hair follicles. Just try to relax, I've done this a long time, so you're in good hands. I'll start with your arms, but slip off your bra first." I blushed at her reference to 'my' bra, but took it off and she put it with my other clothes. Then Stacy began the process on my forearms. I did not have a lot of hair, and what was there was fine and a light red. She made quick work of both arms, then moved to do my underarms. The pain was sharp, but was over quickly, leaving only a stinging feeling that lasted for a few minutes in each area. I was impressed with how efficiently and fast she worked. When my underarms were done, she folded down the sheet from my chest to just below my belly button. Because of how flabby my chest was, it was embarrassing but she made no mention of it. Again, I was lucky, only have a small clump of hair in the center of my chest, between each nipple and a thin line of hair running to my navel. Stacy chatted away with each step and when done with my chest, she moved the sheet back up and switched to waxing my legs. These took longer, and she alternated from left to right. As she worked up past my knees to my thighs, I was hopeful she was almost done. But she kept inching upward until the edge of my panty was exposed. At that point, she had me roll over so she could do the back of my legs. It seemed it took less time to do the back of my legs than the front and she was soon at the junction of my thighs and butt. Again I was hopeful about her being finished. "Dana, you are so lucky to have light, fine hair. It's taken me far less time to do your legs and body than we had planned, so I how about I do your bikini area as well? It won't cost you anymore and will make your overall appearance much nicer. Okay?" I didn't know what else to do but agree. When I did, she asked me to lift my hips, and she adroitly removed my panty. I felt so exposed, but she acted as if she saw guys, or maybe more accurately, girls' butts all the time. I only had short fuzz over the cheeks, but she removed it all, as well as a small patch at the base of my spine. Then she ask me to roll over so she could finish. My hesitation was obvious. "Don't worry honey, I do men and women all day. You'll find once you get over it the first time, you won't feel any anxiety the next time I wax you." If that was supposed to make me feel better, it failed. I just told myself, that this would be the only time I had this done. So I closed my eyes and rolled over. As with the other areas, Stacy made quick work, stopping only to ask me if I had a preference for my pubic hair. When I hesitated again, she suggested that a small triangle might look good for me, so I agreed just to finish. I was surprised that once she had my pubes shaped, she started on my cock and balls. This was definitely much more painful than any other areas, but it went quickly. Finally it was done. With the hair gone, Stacy lightly applied a lotion to the waxed areas of my chest, arms, and legs to help soothe them. She told me I could get dressed now. I quickly picked up my panty and pulled it up my legs. As I got it to my thighs, I tried to discretely position it as I had before. But she saw me. "Dana, here try this. I've done lots of fem guys and have learned a few tricks. Now that you're smooth, it should be easy. First, take your fingers and move your balls around. You should find an opening that they will go into. Once they are in your body, pull your penis back, so it is snug between your legs, pull your panties up, and you'll be nice flat, and smooth. It should be more comfortable too. It's called tucking. Here let me show you." She put her hand on mine, and helped me position my balls and then my cock. When I had my panty up, I had to agree it looked better. Inside I was conflicted. I should have been mad when she referred to me as a 'fem' guy, but I wasn't. Plus I should have resisted tucking my cock and balls like this, but I didn't. In fact, I sort of liked it. Because although it felt really odd to have everything tucked away like that, it wasn't painful and I love the smooth appearance I had in the front of my panty now. I then finished dressing. After seeing Emily do it all these years, I was able to get my bra hooked and on without any issues. I could immediately tell a difference on how nice the leggings felt on my now smooth legs. Also, without any chest hair, my boobs looked much better in my bra. That hidden thrill, that I wanted to look nice in these new clothes, returned. I then followed Stacy back out to the salon A quick look around, showed me that Emily had returned. Stacy told me to sit in one of the nail tech chairs, as I was to get my nails done next. Emily came over, just grinning. "Well how did you do? When I called to make your hair appointment, I checked to see if we could get other things done and it just worked out. I was afraid if I told you what all I wanted to do, you might not come. But trust me, once you see how nice you look in your new clothes, you'll be glad you got rid of that hair. The next steps are a pedicure and manicure. I don't think you need flashy polish, so the tech is going to do your toe nails in this nice, warm beige. It will just make you look more complete. We may use this, or do plain clear for your fingernails. Let's just see how you look." I was surprised at how much work the nail techs did, as part of the pedicure and then manicure. It was almost relaxing. Emily loved the look of the nude like polish on my toes, and went ahead with it on my fingernails. After having my whole body waxed, and then having my manhood tucked away in my panties, I had no fight left to protest having polish on all my nails. Plus, I liked now the polish looked on my nails too. After they had dried, Tiffany came to us. She was ready to do my hair. I sat down in her chair, and all three of us looked at possible hair styles. My hair barely reached the bottom of my neck, so it wasn't very long, and wasn't uniform in length all around, since my last haircut was a male style. Given those limitations, Tiffany suggested a cut that was tapered in the back, had a side part to give me bangs, and curled under to frame my face. She also suggested I get some blonde and red highlights. My naturally red hair was pretty uniform in color, and with highlights, my short hair style would have more impact. Emily loved it. I said it was perhaps too extreme, as I was thinking of when I stopped this fem stage, even with a shorter haircut, the highlights would still be there. But I was overruled. The process took about an hour to complete, finishing with Tiffany, showing me how to blow dry my hair to get just the right amount of curl. "Oh my goodness, Tiffany you made Dana look so much better. I love how those highlights look. Don't you honey? This is just what I was hoping for. The best thing is that it should be easy to do. Even in between shampoos, we can just use a curling iron, to help curl your hair. I just love how it frames your face. Tiffany, do you guys have a lipstick that would go with the nail polish color?" "Sure, do you want me to do a quick makeover? Let me do his eyes, lips and with a little blush you'll be amazed." I just sat there, as Tiffany quickly worked on my face. I had to admit when she was done, I looked so much more finished. And so much more feminine. My lips sort of glowed, my eyelashes were long and curved, and the metallic green eye shadow went so well with my tunic. Combined with my new hairstyle, I hardly looked like the man that had come in a few hours earlier. Emily was literally ecstatic. She admitted she hadn't envisioned me with makeup, until seeing my hair. But now, she was sold. Secretly, so was I. When we finally settled the bill, I left with three shades of lipstick, blush, foundation, face powder, a palate of eye shadows, eye liner, mascara, and brow powder. And an appointment in two weeks to have my nails done again. As we headed to the car, I was only half hoping we'd head home. "Darling you look so cute. I can't believe how much your look has changed. You're going to look so good in your clothes now. But we need to get a few more things, and I'm starving. How about we stop at the mall, get what we need and eat?" Emily didn't even wait for an answer. It was pretty clear after my transformation in the salon, that she was totally calling the shots. I felt like I was someone else. In fact, I should have felt embarrassed to be out like this, but when I looked at myself in the side mirror, it didn't even look like me. It was like I was inside some sort of costume. At the mall, Emily headed straight for a large shoe outlet store. Once inside, she got a saleslady to measure my size, and we began shopping. I was stunned at the choices she wanted for me. The first one seemed okay, a simple loafer with a low one inch heel. The next two weren't bad either, ballet flats, one in black with gold decorations across the toe, and the other in nude with scalloped edges. But after those choices, she went straight for heels. What to me seemed extremely high heels, although she just laughed and said I'd adjust to a four inch heel in no time. She picked out pumps, ankle strap sandals, gladiator sandals, sling-backs, more styles than I could imagine. I tried to argue that I didn't need so many shoes, that she was making the same mistake that she'd done with her 'thin' clothes. But she just shook her head no, telling me that my shoe size would stay the same, even if I gained some weight. She had one of my new outfits in mind with every pair. Plus a woman could never have enough shoes. Maybe if I didn't like how they looked on me, I might have argued more, but I just let her have her way. What that told me, was she might want me to continue this masquerade longer than we initially talked about. Emily finished by having me try on some thigh-high boots, with nearly 5 inch heels. She loved them. Again, I argued that it was early fall and that these were for winter. Why would I need them? She just smiled and laughed, telling me she knew best. The last straw was trying on some ladies running shoes. Very flashy colors, bright designs, that she insisted would match my work out clothes. I felt like I'd never get back to male clothing. As if to cement that point, she asked the saleslady if I could wear the gladiator sandals out. "Of course she can, I'll cut the tag. Are you doing more shopping?" "Well we'll probably grab a bite to eat, first. What do you think Dana, is it time?" Out of habitat, I glanced at my wrist. But my watch wasn't there, it was too big and bulky. Emily said it didn't go with my outfit. "I don't know, I don't have my watch. I miss it. I always wore a watch." This was intended more as a complaint against my current style of dress, but the saleslady didn't catch that meaning. "If you looking for a new watch, Zane's Jewelry is running a great sale. One of our clerks just bought a new watch today. If you buy an item at sale price, you get a free ear piercing and three earrings at half price. It be just right for you." Emily agreed and we wound up at the jewelry store, after a slow walk in my new heels. Again, my protests about taking this too far, for the time frame were ignored. I went in hoping to get her to limit our purchases to the watch and earrings, but after looking around my resistance melted. I had to admit, with my new hairstyle, the sparkle of the earrings really complimented the new look of my hair and face. It was nice too, to have a watch again, even if it was covered in shiny CZ jewels and was a third the size of my old one. Emily told me jewelry was something every girl needed, so getting a tennis bracelet, a ring to go with my wedding band, two necklaces, and a sexy ankle bracelet, all in shiny CZ jewels seemed normal. Of course, I wore some out as we left. I personally loved how the ankle bracelet flashed as we walked. We headed to get something to eat and I was beginning to get the hang of walking in heels. I slowly was adjusting to how they changed the center of gravity as you took each step. But what really got me was how they sounded. You couldn't walk quietly in them, especially on the tile floors at the mall. Every step rang out, a series of click-clacks as you made your way to your destination. It was like they were designed to draw attention, both in how they made you look but also in how you sounded. I saw several men look our way, and I tried to tell myself they were looking more at Emily, but who really knew. In any case, my heart raced when I saw them look over. Emily told me we had one last stop before dinner. She steered us into a small shop, featuring socks, tights, and a wide variety of hosiery. Normally, I would have been embarrassed standing next to Emily as she asked for pantyhose in my sizes. But I knew now, I looked the part, no one would question buying such items. This time I wasn't surprised at how many pairs she bought. I had just accepted that I would be wearing girls' things for the foreseeable future. We finally made it to a restaurant, a cozy little fern bar type place, with secluded booths. We sat in a booth, Emily facing the door and my back towards it. I had to pinch myself as I saw my reflection in the marbled mirrors around the sides of the booth. If I had glanced at this image before, I would have thought nothing more than there is an attractive woman. It stung somewhat to know that's how I would look to others. It also stung a bit, that I couldn't keep my eyes off my new look. I liked how the makeup hid my facial flaws and emphasized my positives, even if they were female positives. My hairstyle, did fit the shape of my face, and I liked how if I moved my head, my hair would still fall back in place when I was done. The glitter of the earrings in my newly pierced ears only complimented that look. So, I wanted to be angry with Emily, for pushing me this far, this fast. But inside it felt kind of thrilling to know I looked pretty. Emily also saw me checking myself out, so I figured she thought she'd made the right choice too. Looking at the menu, Emily suggested we limit ourselves to a small salad and sharing an entr?e. She was determined now to lose some weight, and wanted me to stabilize my weight at 155. But before we ordered, we decided to splurge and we each ordered a cocktail. She wanted to celebrate my new look. I found it hard not to feel good too. Just as the drinks arrived, a couple of women came to our table. I almost fell out of my chair, they were Tina and Andrea, a lesbian couple that lived in our neighborhood and had been at the anniversary party. "Emily! Hello, we didn't expect to see you here. Where's Dana, he...." Andrea stopped dead in her tracks, as she looked closer at me and then recognized that I was the cute redhead sitting across from Emily. Tina lightly hit her on the arm, as she saw who I was right away. "OMG, is that you Dana? I love your hair. It's so pretty and seems perfect for you. You look so put together. Tina, doesn't she look gorgeous?" "Very nice. I thought the other night that you looked good, but today even more so. I was very impressed with your weight loss, and seeing how you transformed your image, I must say you look stunning. But I am curious about what's happening." "Hello ladies. You getting a drink? You can join us if you want. We're just celebrating. Andrea, I agree Dana's hair is perfect. She went to the salon today and I confess we got a little out of hand. You know I told you last night, Dana was wearing some of my 'thin' clothes from when we ran the half-marathon. I liked how everything looked on her and we decided to play around with her look. I mean, we didn't want to repeat the mistake I made after losing my weight, and buy a new wardrobe in a small size, then gain some weight back. So we're in a stabilization period. It was partially driven by her new body proportions, but I also when I saw how cute she looked in a bra and panty, I wanted to take it further. So, we're going to experiment for a few months. So you like her new look?" The ladies nodded yes, and both looked at me. They seemed to be waiting for me to add something, or at least validate what Emily had said about what we were doing. When she explained it, it seemed so odd or over the top. I mean we'd already spent a lot of money just at the salon and the stores we visited. I could have easily bought a limited selection of men's clothes to wear while I 'stabilized'. The explanation just didn't seem solid. I glanced down at the table, trying to come up with something to say. The quick glance showed my polished nails, with my new sparkly bracelet and ring. Beyond that was my heels. I liked the images I saw and knew we were doing more than just bridging some size changes in clothes. "I'm glad you like it. I was pretty scared at the salon. I mean I was embracing such a new look. What had started out as a temporary solution to give me something to wear, began to go somewhere else. It was one thing to wear Emily's jeans and shirt. But as you see now, I've fully embraced a feminine identity. It seems more than the fact I can fill out a bra, or that I have hourglass measurements. It's like I'm connecting with a part of me, I've kept hidden. You must know what that is like, right? But I'm just not sure where it will lead us. For now, I'm just going to enjoy my new experiences, and try to learn as much as I can. So, do you want to join us in a drink? Emily, you want to move over so I can sit next to you and they can sit down?" I moved over next to Emily, our neighbors ordered some drinks, and we sat and talked. I enjoyed it all right from the beginning. It wasn't like talking with the guys at all. No sports, no overblown bragging, no complaints about work or politics, and no slut taking about women. We talked about last night, a little about shopping, some about the women wanting to renew the running group, and some give and take about our sudden shift in our relationship. I felt in some ways, Andrea was dying to hear more about us, particularly our private interactions, but she only hinted about it. I know lesbian couples don't have to be a female version of husband and wife, but Andrea was much more feminine, while Tina had short hair and generally wore pants and simple shirts. We had just finished our drinks, and were starting to look at dinner, when it hit me. It had been a long day, starting with coffee at home, tea at the salon, and now a cocktail. I had to pee and it was pressing. I felt panicked. Should I go to the ladies? Or stick to my side? I looked over at Emily and whispered my problem, trying to keep it low. She looked at me, as if I were dumb. Andrea had heard, so she interjected. "Do you have to go Dana? So do I, come on." I felt another flush of panic. Not only was I going into a women's restroom, but with one of my female neighbors. Was this a good idea? Even legal? Finally, I just followed her as she got out of the booth. We walked toward the room, holding our purses. Andrea had suggested I bring mine along, as I could touch up my lipstick. Andrea opened the door, and I meekly followed. A quick look around and I saw that luckily, no one else was inside. The other thing I noticed right away, was how nicely decorated it was. There was soft lighting throughout, with more focused lighting for each mirror. There was a couch, the sinks were in a long counter, with a lighted mirror in front of each, and there were only stalls. It was so different than a man's bathroom. I started to go in a stall, when Andrea opened her purse and held up a small box of wipes. "Here take one of this antiseptic wipes. I always wipe off the seat before I use them. I imagine, you're not in the habitat of seating to pee in a public setting, but I never liked the idea of sitting my naked butt where so many others had been." I took one and went in. The toilet was cleaner than most men's toilets I had used, but Andrea was right. I had only sat down in a public toilet, twice in my entire adult life. It was far easier to use the urinals. So I quickly wiped it down. I hung my purse on the hook on the door and began to pull down my leggings and panty. As I sat down, I used my hand to hold my cock back between my legs. I felt immediate relief, as I started to pee. But I noticed Andrea's legs outside of the stall. "Andrea did you not have to go?" "Oh no, not really. I just thought you'd feel better if I came along. Also, I wanted to ask some questions, you know privately. I mean I'll touch up my makeup once you're done, but still I wanted to talk." "Oh, okay." "So, your change seems really sudden. I mean, you've been losing weight for some time, but when I saw you walking you always wore men's clothes. Now you're out at the mall, totally fem. Is this something you've thinking of for a long time?" "Umm, no it just sort of happened when Emily had me try on her thin clothes." "Have you been a secret crossdresser for a long time, then?" "No, not at all. I never tried anything like that at all." "Then why so suddenly are you fully embracing a female appearance? I know Emily said her clothes fit you so well, and that it would be waste not to have you wear them, but switching genders so completely seems more than that. What's up?" I was quite surprised at how forward she was with her questions. No holds barred. But I guessed being gay, she was used to dealing with different situations, as well as personal inquiries. "To be honest, I'm not quite sure what all triggered it. I mean, I know I felt so unusual when she put a bra on me and it fit. It really fit. It wasn't like I didn't need one, I really had boobs. I had tried to fool myself by calling my chest flabby, but it was clear once she fitted it around my chest that I had a bust. Similarly, when I saw my figure, really saw my figure. I think you could see how curvy I am. I have an hourglass shape typical for a woman, not a man. Now maybe those things wouldn't be enough, but what got me was how I felt when I was trying on her things. Somehow, it felt I don't know, good or maybe natural would be a better descriptor. Then today, first at the salon and later shopping. With every step, or action, it felt better, real and true. I wasn't willing to admit it right away, but after my hair was done, and they did some makeup for me, I saw myself. Saw my inner self, for the first time in my life. I liked the way I looked. I know it seems clich?, but trying on shoes, picking out jewelry, and seeing how I looked in them, seemed perfect too. I know it's a radical change, and maybe I'll regret it later. But for now it seems like the right thing to do. Finally, and almost as importantly, was how Emily reacted. She seemed energized by my transformation. With every step, she became happier, more excited, and thrilled. We seemed to be forging a closeness we hadn't developed over our marriage before. It was like she was connecting to me in a more important way. So, that helped me feel again, like it was the right thing to do and natural. So, how do you see it? Does it look totally strange to you?" By now, I had finished peeing, put my clothes back together and came out of the stall. I went to the counter to wash my hands, while I looked at Andrea and waited for her response. She had moved to the sink next to me and was getting ready to touch up her makeup. It seemed like she was carefully considering her answer. I thought she was going to be very critical, since her lifestyle had often been challenged and perhaps she say me as role-playing too much. "Well it's much more organic than I had imagined. I thought you two were playing cross-dressing games. I have to admit seeing you in this top, you do have a woman's figure. Anyway, even if this is all real, all how you actually feel and it seems right. You need to understand how big a step you're taking. If we were any other couple in the neighborhood, seeing you in a dress, heels and with your hair and face done, you would immediately be classified as a crossdresser, pre- surgery sex change, or more. You would no longer be a normal, regular guy. You'd be in your own category. Plus it's a one-way street. Once you cross over to showing your feminine inner-self, no one will see you as a man, at least a masculine male. So think about it, for sure. I don't want to be all negative, you need to be who you are, for sure. But be real. It took a few years for the neighbors to accept a lesbian couple as okay. But you said something that intrigued me. You said you fill out a bra. You're telling me that you completely fill out a bra? Is it an A-cup? I can't get over that, you've got real boobs? And you've not been on hormones?" I blushed at her questions, as much as I worried about her warning. I had to be real though. "Yes I do fill out the cups. It's only a B-cup, but that's without any padding or liner. And no, I've never taken any hormones. I can't understand it either. But I am what I am." "Any chance, you can let me have a peek, you know girl to girl? Let's step back in the stall for privacy." I was more than surprised at her curiosity, but did as she asked. I turned around to let her unzip my tunic, pulling it forward, down my shoulder until my peach soft cup bra was visible. I turned back around. Her eyes lit up, widening as she saw me. She hesitantly reached out. I could tell she wanted to touch them. This was so strange. Was I cheating on Emily? Did it matter, since there was nothing sexual? Andrea stopped just short. I was getting real nervous now, with both of us in a stall that someone else would come in. I just wanted it over. "Yes, go ahead. But be quick, this is making me uneasy." She smiled, and quickly ran her fingertips over the cup. It was such a light touch, no grasping, squeezing, just floating over the fabric. She did take her time outlining my areola, causing my nipple to start to react. Then she reached down to help pull my top back up. "Turn around and I'll zip you up. Very nice, by the way. I like the size and shape, especially your nipples and areola. I expected them to be small like most men's. I appreciate you being so open. That tells me a lot. I always found women to be more open and truthful than men. So, you're certainly acting in a more natural way than if you were just role playing. But I have another personal question. What are you and Emily doing about sex? Still doing it like regular? Or are you shifting to a female-female coupling? You don't need to answer, but if you want some ideas, tips, whatever for better girl sex, let me know. I'll be glad to help." By now I was zipped up, and turned around. She hugged me and smiled. We left the stall, and touched up our makeup. I was reeling in emotions. I felt I had passed a big test, but she reminded me there was much more to decide about. Since the party, Emily and I hadn't really even included sex in our discussions, let alone have any. I had no idea what she would want to do. I had a hard time even imagining how we would have sex without my cock. Did we have to? The other comment that stuck with me was about by areola. I had never really noticed them before. I mean when I was heavier, they seemed proportionate to my size. Now I realized they were big for a guy. They were closer in size to a woman's. Added to my overall breast size, and how my hip-waist ratio was feminine, puzzled me. Why were all this physical factors leaning toward female? By the time, we got to the table, I had pushed these thoughts back in my head. I would need to talk with Emily later. We did have an enjoyable dinner. Lots of conversation, laughter, and a nice release of tensions. By the time we left, I felt closer to Andrea and Tina. I had never talked with them much before, I guess since they were 'different' or maybe because I was just another suburban man with little to offer them. Now I expected to see them more often going forward. At home, I wanted to talk with Emily, but she gave me little chance. As soon as I put away my new purchases, she wrapped me in a big hug from behind. Lightly nibbling on my neck, and running her hands over my body, she suggested I get undressed. The way she played with one of my nipples, it was clear why. She unzipped my tunic, to help me out. I was soon stripped down to my bra and panty. She had undressed to her panty as well. With a practiced hand, she quickly unhooked my bra, freeing my breasts. Grabbing me by the hand, she pulled me into bed. "Dana, I want to try something. While you were in the bathroom with Andrea, Tina and I talked about sex. She had some good points about how our relationship might be different with your feminine appearance. So I want to try some of her suggestions. Let's keep our panties on to start, and just follow my lead." Emily started by simply kissing. Slow, deep, and soft, with lots of tongue play. The sort of kisses we hadn't done in years. Paying a lot of attention to each other's lips, our tongues seeking out each other. I don't know if it was her goal, but this sort of real slow foreplay, was making me hornier. At one point, she moved to one of my breasts, repeating the type of kissing we had done, only focusing on my nipple, and then the curve where it raised off of my body. Breaking away, she offered hers to me. I repeated the slow, soft, nibbling on her breasts, hardening my nipples as well as hers. By now I was really stoked. My cock, still tucked in between my legs had gotten stiff in my panties, even though it had not been touched. Emily shifted focus to my butt, softly stroking it, rubbing across my cheek, with a light feathery touch. Pinching it just enough to cause it to tingle. Slipping a finger under the edge of my panty, so she could run it at the edge of my crack. It was an extended tease. I did her as well. It was a welcome relief to follow her lead, not having to be creative, but just replicate her moves. Finally she started shifting positions, moving her body away from me, but mingling our legs together. She wrapped her legs among mine, so our crotches were next to each other, the central focus of our connection. She slowly began to rub her pussy lips over my cock, pressing against me. I could tell she was excited as her panty was wet. Seeing her excitement made me even more excited. The pressure of her pussy on my crotch would have been painful normally, but with my balls tucked inside me they were safe from excess pressure. All I could feel was the stimulation of my cock, its shaft and head by her swollen pussy. As we rubbed our sexes together, she lightly played with my legs. Her touch and soft kisses on my silky smooth legs, sending shivers up them. Of course I reciprocated. Gradually she began to increase both the pressure and speed of which she was grinding against me. I could sense she was getting really excited, as was I. Finally were rubbing against each other very intently, my cock being as stimulated as if it were actually inside her. I was leaking and so was she. As we both reached climaxes, we pressed our legs tightly against each other's' bodies, holding as tight was we could as the orgasms washed over us. My cock filled my panty with cum. I could tell she was having multiple climaxes, and I felt in some way that I was too. With this sexual release, we again shifted positions, so we were face to face. We kissed again, soft and slow, like we had started. I looked her in the eyes, trying to let her know how special she was. I had never come this way before, and it had to be among the best sex we had ever had. Even though I hadn't penetrated her, I felt like we had connected in a special way. If this was an example of 'girl' sex, then I was all for it. But as we cooled down, my thoughts returned to the warning Andrea had given me. About once I went down this road, I couldn't go back. I needed to talk with Emily about this. But first we needed to clean up. "Wow that was special. I'd never considered a position like that or having sex without you being inside me. Tina told me about it, calling it scissoring. Apparently it is common with lesbians. I'd ask you if you liked it, but I can see your panties are soaked, so I assume so. How about we get up, take a quick shower together, and then snuggle back in bed?" I nodded my agreement and went to shower. It felt odd striping off my soaked panty. Emily also insisted I use a shower cap, to protect my new hairdo. We quickly washed up, she soaping my body, while I did hers. In the past if we did this, I'd get hard again, but I stayed soft. I was so spent there was nothing left. We dried off, and then both put on short, sheer nightgowns with tiny thong panties. As we crawled back in bed, I tried to imagine how I had gotten here. It seemed like a long journey, but I realized we had really plunged in so quickly over the past few days. That prompted me to talk with Emily. "Honey, I have to admit this is a whole other level of eroticism. I feel totally different and so sexual, but in a new way. But this is a big step, a really big step. While we were in the bathroom at the restaurant, Andrea asked me about our changes and made it clear that not everyone would see our situation as we see it. That if most couples in our neighborhood saw me like I was dressed today, in women's clothes with makeup and my hair done, they would see me in a totally non- masculine way. But perhaps not a feminine way. To her our gender fluidity seemed real and natural, but warned me that once I started down this path, this path of feminine identity, then I likely could never go back to just being a man, one of the guys, in the neighborhood. I think she's right. If I saw one of my male friends in a dress and heels with his hair styled and his face with makeup, that image would stay with me. Even if it was only a one-time thing. Seeing him dress femininely for a month or two, then I would only view him that way. Our explanation that it was driven by the availability of your clothes that fit my new size seems flimsy. Especially now that we've added so many new things, like shoes and jewelry. Not to mention my hair and body preparations. We've gone beyond just being frugal and practical. I think what is even more critical, is how my body conforms to the image of a woman. Do you think any of our neighbors who saw me, say in that red sweater dress with the low cut top, would consider me a guy any longer? With the dress molded to my hips, waist and bust, legs covered in black hose, walking in the matching red pumps, and my pushup bra showing deep cleavage, nobody would imagine me as a guy ever again. Even if I wore baggy jeans and an old flannel shirt, they would imagine my body under that. I know guys would be fantasizing about thong panties and bare boobs underneath it all. Over the next month if I constantly wore your 'thin' clothes, it would mean I'd always be in something tight, form fitting, reveling, or all three. Combine that with my cute new hair style, with my face highlighted by lipstick, eye shadow, and mascara, it would force everyone to admit that I had a woman's shape. No man could flaunt the type of cleavage I have unless they weigh 300 pounds, not 155. So I think we need to consider if this is really how we want to live the rest of our lives here?" I could see the impact of my words on her. She looked at me, as if she knew I was right, but wasn't sure what to answer. I could also see her looking at my body. A quick glance revealed what I had been worried about. Snuggled in the soft sheer lace cups of my nightgown, my breasts were prominent. The areolas and nipples of a girl not a boy, and the deep cleavage that would always be there. I knew if I looked further, I'd see the tiny panty showing my shaped pubes, hinting at a woman's sex, as even now my cock and balls were tucked away. A position that had rapidly become second nature for me to put them in while I wore this attire. Finally, she took my hands in hers and looked at me intently. "Dana, you are so right. This is a big step for us. It may be like the Andrea said and one we can't take back. I realize that and I'm glad you're thinking about it too. So let's assume we go back to our regular ways. We go out and buy you some male clothes that fit, get you hair cut short, take out your earrings so your holes will heal up, and remove all your polish and makeup. All that is pretty easily done but where does that leave you and us as a couple? Your bodies shape isn't likely to change back dramatically. You'll still have breasts, a small waist, and hips. If we run a lot, we might trim them some, but it will be hard to get rid of your breasts without surgery. I don't know about surgery, you've never been one to take such a radical step, even when you had a more life threatening situation. But maybe now. But you will still have your larger than normal nipples and areola. Since I don't understand how your waist got so trim, while your hips didn't, I don't know what we do about that. Perhaps working with weights would add some muscle mass, but how would that reshape you significantly? My point is, that you're likely to never have a typical male body again. I can't imagine you wearing tight tee shirts, or going to the pool or beach. Would you feel comfortable in a male swimsuit like you are now? So if we opt to continue to portray you as all male, then we will still face limitations. But for the most part, outwardly you'd still be considered a man, by our casual acquaintances and neighbors. I guess you'd be okay with going back to being a man, wouldn't you? Or would you? I know I'm biased, but I've watched you closely over the past 24 hours and I've seen an interest, a spark that wasn't there before. I saw how at first you were mortified by the fact you could wear a bra, in fact, needed to wear one. But as you got over that shock, I saw you beginning to adjust to that idea, accept it, and finally embrace it. You can't tell me that when you slipped on some of my dresses, or fitted your bra back on after being waxed, or slipped into this nightgown, you weren't proud of your breasts. I would be willing to bet, you've even imagined wearing sexier bras or tops to show them off. I think that's true for your long legs and curvy body too. It wasn't my imagination when I saw how your eyes lit up after Tiffany did your hair and makeup. Or when Tina complimented you. And although you've not told me, I think something happened in the bathroom between your and Andrea. Again, I could see a mix of joy and pride on your face as you returned to the table. So the question remains, is this choice the right one for us? Now? And likely forever? I think I know the answers, but it's more your decision than mine. I imagine you need some time to think. To do some soul searching about who you are and how you want to live your life. I get that. Let's sleep on it and we can talk more tomorrow. That's one think I've already noticed about you. You're much more willing to share your feelings now than before. I hope that stays whether you're in panties or boxers." She pulled me close and we kissed, touching foreheads. I knew we couldn't decide tonight, so I went along with her suggestion. Besides it began to hit me, how really tired I was. It had been a long day. As we laid there, snuggled against each other, her breasts pressing into my back, and one of my breasts cupped by her hand, I began to drift off to sleep. It felt like this had been going on for weeks or months, but in reality only slightly more than a day had passed. I was awakened the next morning by soft kisses on my cheek. I opened my eyes and saw Emily smiling at me. She told me she was going to get up, make us some coffee with cut up fruit to start our day. She wanted me to slip into something. We'd stay here most of the day, as there wasn't a rush to get anything done. She slipped out of her nightgown, pulled on panties and a bra before getting into some jeans and a loose top. As she went to the kitchen, I went to the bathroom, to pee and check out my appearance. It struck me right away that I sat down, almost instinctively, to pee, peeling the panty down my thighs while holding my penis tight against me so I could keep it in a tucked positon. When had I developed this trick? I finished and stood up to brush my teeth, checking out my reflection in the mirror over the sink. The first thing I noticed, was my hair still looked nice. It had held its shape overnight, despite me sleeping on it. That reminded me how Tiffany said it was a low maintenance hair style. The sides still curled under toward my face and my bangs were straight. The second thing I noticed was how pale and blank my faced looked. I had removed my makeup in the shower last night as well as shaved. I felt my cheeks, and they were still smooth. But my eyes, cheeks, and lips now looked empty somehow. I reached over to where my makeup sat on the counter. I knew this was not something a man would do, and likely many women wouldn't. I mean we weren't even going anywhere. But as soon as I covered my lips with color, I began to feel better. A quick application of eye shadow, mascara, and a little blush and I felt my face looked good again. Although I had mostly seen Emily do it, putting on the cosmetics went smoothly. Something about the makeup made it fit with my hair. I could smell the coffee, so I needed to slip into something. I quickly removed my nightie, pulling off my panty last. I was standing by my dresser and reached for a replacement. I picked up one that was a rich mocha, being a lace tanga style. As I pulled it on, and it settled around my hips, I noticed that my balls stayed inside of me and my cock remained up against me. It was as if they knew this new positioning for them was right. Looking over my shoulder in the mirror, I could see the lace of the back of the panty covering only about a third of each cheek. It was more than a thong, but not a lot. Somehow I liked this look, as it seemed to highlight my round butt. I had also picked this panty, because I knew I wanted to wear the matching bra. I opened that drawer, searching for it until I found it. I slipped it up my arms, reached back and hooked it tight. As Emily had shown me, I leaned forward, pulling the cups out a little so my breasts would settle into the bra. Straightening up, I immediately liked how my breasts looked. This bra had thick pads in the bottom of each cup, and used widely spaced straps. It was all trimmed in lace, so the resulting uplifted breasts with a deep V between them were as highlighted as my ass cheeks had been. I checked out my profile in the mirror for a minute or so, before moving on. I knew I should just do like Emily and slip into some jeans and a top, but something was pushing me toward another choice. So I went to the drawer where she had put my new hose, found the package I wanted. Soon my legs were encased in a warm chocolate color hose, sheer to the waist. I loved how the hose made them look and new just what else to wear. I went to the closet and put on one of Emily's thin dresses. It was a tight fitting knit, color- block design with brown, tan, and very light taupe. It was quite short, coming only to my upper thighs, which made sense since I was slightly taller than her. It also had a low cut top that my uplift breasts filled out nicely. I finished out the outfit with a pair of brown, ankle strap heels. I heard Emily call out that breakfast was ready, just as I finished a quick look in the mirror. Walking toward her, I thought about last night. And this morning. How do I reconcile my worries about my outer male persona with my suddenly intense need to appear ultra-feminine? Not many women now-a-days would be dressed in hose, heels, and a dress to just hang around the house. But as soon as I started to get ready, that's all I wanted. Was I just protesting Emily's plans for me to be dressed in her old thin clothes, as a front? To be sure, she thought I was still a man, despite my obvious desires to wear her clothes? All I knew was I felt great looking like this. Entering the kitchen, I saw Emily look up and smile. She had already put some fruit and coffee at my place on the table. "Dana, you look fabulous. I love that outfit. I think it looks better on you than it ever did on me. The way it just shows off your bust, waist, and hips not to mention those killer legs, is amazing. I like your face too. But you seem overdressed a bit. Did you think we were going somewhere?" I blushed. I knew I couldn't readily explain why I had dressed this way. "Um, no I guess not." "So, why such a pretty look?" My face flushed a deeper red, so red it felt like a flame. "Well, when I looked in the mirror, I was surprised at now my hair had kept its' new style. I hadn't expected that. I mean, it was only slightly messed up from all we did yesterday plus sleeping on it. I knew I could easily brush it back in place. But when I looked closer, my face seemed so pale. It seemed empty now, after I had seen how makeup gave it depth and color. So, I just put on a little, does it look okay? I felt like I did a good job, except maybe too much eye shadow." "No, your face and eyes look nice. Good job for your first time. But just because you put on makeup didn't mean you had to go all out. You knew that right? Jeans would have been fine." I found myself trying to give a logical explanation that I didn't have. I just did the best I could. "Yes, I saw you put on your jeans and to be honest I was going to do the same. But when I started to select my panty, I saw this lovely lace pair. You know the one. The tanga in mocha. I just had to see what it looked like on me. So, I picked it and I did like the way it felt and looked. Of course, I knew it had a matching bra. And I put it on. Again, you know it, right. As soon, as I saw how it changed my appearance, gave me such a lovely bust, I don't know I just lost my control. I loved the look and knew you had bought hose and heels to complement the color block dress in browns that would make such a lovely outfit. I felt drawn to put them all on, to see what the outfit looked like on me. Again, to be honest, I knew I was overdressed, but I loved how it made me look. Something about the outfit connected with my feelings, so I kept it on. Sorry, I went so far." Emily smiled once more. She held her hand out and pulled me down so I could start eating. The whole time, she kept looking at me. We talked, but mostly pleasantries, or her asking questions about my dressing, makeup, etc. We agreed that there wasn't a need to go anywhere right away, at least out of the neighborhood, so I mentioned I might do a little work later. By the time we finished our breakfast, I felt guilty about how feminine I had dressed and was ready to upstairs and just switch to jeans and a loose top. Something much more casual and closer to my male sensibilities. I had just put our dishes in the dishwasher, when she offered a suggestion. "Dana, I wonder if you'd help me out. I need to do some bills, and update some of our records, but I also promised Jan Stanton that I'd verify some information for the houses on our street, so the homeowners' association could finish their directory. You know Jan, she's the VP on the board. It's pretty simple stuff, about a page of questions. I lack ten homes, so it shouldn't take long." "Okay, you have their phone numbers right? I'd just need to call and see if I can catch them at home." "Not really, Jan wanted me to visit them in person. It's part of their commitment to personal attention to the residents of the neighborhood. I thought since you were already dressed so nicely, you could just walk over and see who's at home." "You mean see them in person? But that would be a lot more exposure. I'm not sure I'm ready to take that step yet. You know we talked about it last night." "Honey, be honest. I know you expressed reservations last night but then, the first chance you get, you go all in. It's not just that you choose a dress to wear, but it's how you accessorized it. I mean you picked the sexiest bra in your dresser to wear. You admitted that seeing yourself, now, without makeup you felt unfinished. I know that feeling. For most of my life, I had to apply makeup, almost the first thing I did after getting up, to feel normal. Now you've expressed the same feelings. So if you want to dress this way, to use makeup, and take advantage of my thin clothes, then you can't expect to hide inside all the time. Were you planning on changing completely for dinner? I don't have anything to cook, so we'd be eating out. What were you going to do with your new hair? Your polished nails? I don't think your view of your face is going to change that quickly, that you'd go out without makeup. I think you made your choice already, so this will give you an opportunity to slide into your life for the next few months. I mean, in our neighborhood at this time of day, it will be almost exclusively women at home. So you won't have to talk to the guys if that's your worry. Why don't you just go touch up your makeup, put on some jewelry, and I'll get the paperwork together for you?" She smiled and started toward our office. I began to panic. The idea of going out like this, was terrifying, but somehow insanely tempting. I knew I looked pretty, perhaps a little overdressed for this time of day, but everything was so coordinated. I hesitated a second and then went to do as Emily suggested. I brushed my teeth again, reapplied my lipstick, and added a little more mascara. The whole time I was checking out my look. I decided to add a necklace, a long strand that had a sparkly solitaire jewel that nestled in the upper part of my cleavage, a couple of bracelets, and the ring that went with my wedding band. I put some makeup in a purse, and went to our office. I still felt very nervous, and just hoped that maybe few people would be home. Emily gave me the forms, a list of houses, and a clipboard. It really was an easy task, under normal conditions. But as soon as I went out the front door, and headed toward my first house, I could feel my heart racing. It felt so exciting to walk along the street, my heels clicking, the breeze almost caressing my legs through the sheer hose, and out of the corner of my eye, seeing my bosom slightly bounce with each step. It was empty more or less, but I did see one neighbor working in his yard, an older man who had always been pleasant but not particularly friendly. He glanced over at me as I walked past. I was sure he didn't recognize me, but he smiled broadly and waved. I gave him a little wiggle of my fingers as a reply, a definitely feminine response. I knew all he really saw were my legs in their short skirt and my exposed cleavage. He had no idea that I was the man who live three houses down on the left. Finally I reached the first house. I took a second to be sure I looked okay. I pulled down on my hem, smoothing the dress over my butt. I lightly straightened my bangs with my fingertips, licked my lips and then knocked on the door. I was holding the clipboard in front of me, shielding my low cut top. It seemed like an eternity, but it opened. Standing there was a woman, a few years younger than me. I had seen her before, and knew she had three younger children, who'd be in school, and was married to rather large man, who could stand to lose a few pounds. She was petite, with a cute friendly face. We had met once or twice at neighborhood functions, but never interacted much. I wasn't sure if she knew who I was or not, so I just plunged in. "Good morning. Hope I'm not interrupting anything, but I just wanted a few minutes of your time. The HOA is updating their directory and needs a little information from you. I promise it won't take long. I assume you are Pam Woodley?" I could hear my voice cracking from nerves. I knew I had a soft voice with a tone that someone had joking referred to before as melodious. It certainly wasn't a typical male voice. So I felt, it would fit okay with my current appearance. As I spoke, the woman smiled and did a quick once over. I immediately felt more self-conscious, as she was dressed in what I expected would be the one of the outfits of the day, dark leggings and a loose top, very casual. Nothing as dressy as what I had on. "Yes I'm Pam and you did catch me at a good time, you want to come in, Miss?" Inwardly I breathed a sigh of relief, but realized I had forgot to introduce myself. "Dana. Dana Culberson. I live about a block up the street. I'd like to come in, if that's okay." "Of course. I wasn't sure I recognized you at first. I mean, I thought it was you Dana. You seem to walk up the street almost every day. There aren't many redheads in the area, but you're dressed differently aren't you? Plus you seem to have lost a lot of weight." I felt a blush on my cheeks. You think I'd be used to it by now, but somehow this was much more intimate, personal. I guess because we were in her house. "I have lost a lot of weight. That's part of the reason, I'm dressed differently too. It's a complicated story, but to make it quick, I had lost so much weight none of my clothes fit, but I was leery of getting new sizes, as I wasn't sure what I would stabilize at. My wife, Emily had gone through a similar thing a few years ago after training for a run event. Long story short, her old 'thin' clothes fit me, so she suggested I give them a try. Somehow my weight loss was rather spectacularly uneven and her things fit better and more appropriately than I could have imagined." At that point, I glanced down at my bust, clearly showing her that some areas hadn't lost weight at all. I think she understood my implications. "So, we opted to sort of adopt a new look for me while I waited it out. I hope it's not too distracting?" "No, no not at all. You're very attractive, in fact, I hope you don't mind me saying this, but you certainly don't look like a man at all now. I can see why you choose this option. That dress just looks so good on you. Plus your hair is gorgeous. I always thought you had nice hair, but it looks so good in that style and compliments your face spectacularly. Tell you what, why don't we go in the kitchen. I'll make us a cup of tea and we can fill in your form for the HOA." She reached down to take my hand and led me into her kitchen. I didn't know how to feel. Pam was so complementary of my appearance, but it was of course a direct rebuke of my masculinity. I sat down, as she poured some tea. I realized pretty quickly that she must be lonely, being alone in the house all day with her children at school and her husband at work. She chatted almost nonstop. But we quickly filled in the form and talked a bit more. Finally, I told her I better leave her to her work, as I needed to talk with a couple more residents today. She smiled and led me back to her front door. "Look, Dana, some of the ladies have a book club that meets about once a week. We talk about the book selection, drink a little wine, and just socialize. If you want to try it, we meet next Thursday at 2 PM here at my house. I'd love for you to come. Bring your wife Emily, even. I'd like the chance to know you two better." I thanked her and told her I'd think about it and headed up the street. The next couple of houses, were very easy. The women and I just stood at the door and filled in the form. Neither one seemed surprised, or seemed to know me, so I guess that made it easier. I was able to find three more ladies at home, but the other homes were empty, so I headed back to my house. It was getting to be near lunch, so I was figuring Emily would be looking for me. As I walked along, I had become quite comfortable being outside. Everything had been fairly painless. But then I heard a car approach from behind me. I could hear it slow down, a little at first, but then very noticeable. So much that it was just creeping along, behind me, not going fast enough to pass me. My first thought, was oh no, a bunch of kids had seen me, figured out I was a guy and were going to give me grief. I held the clipboard tightly to my chest, my arms crossed with my purse tucked into the crook of my elbow. It seemed to be the only protection I had. I just tried to walk as briskly as I could, knowing I was several blocks from home. Finally the car began to pull up alongside me, a long hood passing me by. The big hood of one of those old muscle cars, like an Impala. My heart sank inside me. I glanced over at the driver who was now beside me. "Dana! Dana is that you? Dana, it is isn't it." A beaming face was looking up at me. Ham Huddle's face. Really it was Hamilton, but everyone called him Ham. He was part of a group of guys that I had known through work. A rowdy group that had gotten together to play golf, share some drinks, maybe play poker, and watch sports at the club. A small local golf club with an intimate bar like a pub. Ham, me, Todd, and Brick, everyone used his last name, Brick, rather than his first name James, had gotten together regularly for several years. When work scaled back, I sort of lost touch with them. I mean, in most ways, we weren't similar. They were all into big muscles cars, and loved sports way more than me, like golf. I never played unless it was them, and of course I was the worst one. Same with drinking, they went at it like fish, while I rarely had more than three beers. The one thing I did like was watching replays of the morning soccer matches from Europe. We all go to the pub, and waste several hours. I guess the main reason I did it was because all three guys were important customers for my old firm. Once I dropped out of the regular work, I sort of dropped out of this group. Seeing Ham was probably the worst thing that could have happened during my extended stroll in heels and skirts. "Hmm, hello Ham. I didn't expect to see you around here." "Yeah I went by to get a part for my car from a guy who lives near here. I was just headed out of the subdivision when I spotted a ginger walking up the road. I thought right away about you, as I knew you lived near here. But when I got close enough to see some details, I didn't think it was you. Anything but you. But it is. Wow, you look good. So good. Seeing your ass wiggle in that tight dress, I just had to slow down to enjoy the view, you know what I mean. And those legs, man-o-man, they go on forever. You know that they lead right to the Promised Land. I just can't get over that this hot chick is you? Better yet, you aren't short changing anything up front either. Wow. Just Wow. I don't know what's up with your new look, but you're sure nailing it. Hey, I was on my way to join the guys at the club, why don't you come along? There's a replay of the Man Union game. I'm sure they loved to see you. It's been awhile, ever since you got canned, we haven't hung out. Seeing your new look, I kind of understand why. But hey, if it works, do it. We can have a few drinks, cheer on the team, and catch up. What'd you say?" I was stunned. Both by how he referred to me and how it didn't seem to matter why I looked like this. It was as if I was so hot, he didn't care. But the idea of going with him to the club and then joining the other guys was in no way, anything I wanted a part of. So I decided to just beg out of it. "Well I know it's been awhile, but I don't think I can join you today. I mean Emily is expecting me back home soon and we've got stuff to take care of. Maybe some other time?" "Oh come on Dana! You never let your wife keep you away before. You're not telling me you need her permission to go out with the boys, are you?" "No, it's not that, it's just like she's expecting me to come back." "Well, how about I call and see if it's okay?" Before I could answer, he whipped out his smart phone, searched his contacts and hit my home phone number. I could hear it ringing as he had it on speaker. I just hoped Emily was gone or would understand. Finally she picked up. "Hello?" "Hey Emily, its Ham. I was checking on Dana." "Hi Hamilton, how you been? I'm sorry but Dana's not home at the moment. Can I take a message?" "Yeah, I know that. I ran into him on the street. I invited him to go with me to the club, like old times. You know, hanging out with the guys. But he said, you were expecting him home. So I wanted to check to see if it was okay. Can Dana come out to play?" He laughed at the last part and I sort of heard a giggle from Emily. I was petrified, hoping she'd tell him no, so I spoke up. "Emily, it's okay, if you need me there, I'm only a few blocks away. I'll understand." I hoped I had enough pleading in my voice that she'd catch my hidden message that going with Ham was my worst nightmare. "Well, I still have some paperwork to do here Dana. Did you visit all the houses on the list?" "Yes, yes I did." "Great, well then go have fun with the guys. Tell you what, I'll just drop by the club to pick you up for dinner. That way you won't have to bring her home Ham. You can play till then." My heart was now in my feet, my pantyhose-covered, high-heel wearing feet. Ham was delighted though. "Great Emily. I'll take good care of her and we'll see you later." He turned off his cell phone, put parking brake on and the car in neutral, and quickly hopped out, opening the driver door. The Impala had one of those old-fashioned bench seats in front. "Just slide in honey, and we can go." I had noticed once Emily referred to me as 'her', Ham had switched to feminine pronouns for me too. The way he suggested I enter the car, is how guys had their girls enter when they were dating in the old day in these cars. It put the girl in the middle of the seat. I turned and sat down, trying to keep the hem of my dress down. Lifting up my heels, I sort of scooted my butt across the smooth upholstery. Because it had a floor mounted shifter, I stopped and carefully moved one leg around to the passenger side, and was ready to move over all the way, when Ham got in. He reached over with his big right hand, and put a tight grip on my thigh, not far from my crotch. The skirt had of course moved upward, as I scooted over the seat, so that I was showing a whole lot of leg. I was just glad the pantyhose were sheer to the waist so no darker panty showed. "That's far enough Dana. No reason to slide all the way over. I like shifting more when I've got a cute thing straddling my shifter." He reached up with his left hand and turned my face toward his. I was really blushing now, as I felt so vulnerable and humiliated. He just had a big shit-eating grin on his face. "Honey, I don't why you made this change, but I like it. You were never much of a man before, I mean you couldn't reach any of the greens with a driver at any hole on the course. You never worked on cars. You couldn't hold your liquor. Plus your voice was so sing song, you sounded like one of those Disney princesses. But now, you look great, especially the way you dress. I love a woman in heels and short skirts, especially if they wear hose. So just relax, if you're going to embrace your inner woman that's fine with me. You certainly seem to have all the parts for your new role." With that he slid his right hand up my leg, and ran it over my crotch. Of course it was smooth and flat as I was tightly tucked. As he let go of my face, he moved his left hand down, under my breast and cupped it, giving it a little shake. His smile got even wider, and keeping the car in neutral, he revved the engine, as he released me. "Dana I swear, you feel as good and natural as you look. Let's go introduce your new look to the rest of the boys." Ham put the car in gear, his hand positioned on the shift lever crudely placed between my legs, and we lurched forward. I felt trapped and so disrespected. I had never been in such a situation before. I knew he had fully embraced my new look, but for likely the wrong reasons. It also stung me at how quickly and in his mind justified, as to why I would want to be female. I was clearly a failure as a man, so why wouldn't I be a girl? As we sped down the roads, he seemed to take great pleasure as he shifted in and out of second and forth gears, as both meant he pulled the lever back tightly between my legs. He had kept me next to him, whispering once when we made a sharp turn that put me against his shoulder, that it was okay if I wanted to feel his muscles. By the time we made it to the club, I was totally shook up, both by the physical beating in the front seat, and his mental assault on my confidence. Of course, he offered to help me up off the seat, pulling me forward toward him, in one quick motion. I fell into him, my breasts pressing against his chest and my lips grazing his cheek, as I wobbled in my heels. I felt so exposed, as I knew my dress was up near my waist. But Ham used one arm to hold me tight while he put a hand on my ass, tugging down my hem. Finally I was able to extricate myself from his clutches. I glanced around, but luckily on one else was there to see my humiliation. When we turned to go to the club bar, Ham grabbed my hand. "Let me lead you there sweetie. It's been so long since you've joined us, you might not know the way." I tugged my hand, trying to pull it away, but he kept it tight in his grasp. "Don't worry Dana, my wife knows girls throw themselves at me all the time. She's never worried about my little flings, as long as we do everything outside her house." Ham roared at this 'joke' and we made our way up a short flight of stairs. At the entrance, he finally released my hand. We were just outside the bar entrance, where the rest rooms were located. "Dana I got to take a leak. Why don't you go powder your nose in the ladies, and I'll meet you back here. Then we can see if the others are here yet." I quickly retreated into the bathroom, safe from his advances. I wasn't nervous, since I had been in the restaurant restroom, but I did suddenly really need to pee. I quickly found a stall, hung my purse on the hook, and worked my panties and hose down my legs. I felt an immediate release as I began to pee. My mind was whirling though. What was I going to do for the next few hours with this gang? I could already tell that once Ham had a few drinks in him, he would be all hands. I had seen it before with one of the real flirty cocktail waitresses. Brick and Todd weren't much better, and who's to say they'd even accept me like this? I could easily see them calling me a freak, sissy or worse. Once I was done, I put my clothes back together, being sure to smooth out my hose so there were no wrinkles or bagging. I left the stall and checked out my face in the mirror. I was so glad we came here first, my hair was a mess and I need to touch up all my makeup. As I got to work, I was inwardly thankful that Emily had put all this in my purse. It took a while for me to finish, but finally I exited the restroom. Of course, Ham was standing there, as I was sure he would be. To be honest, he probably got in and out so quick I doubted he even washed his hands. He grinned though when I came out. "There you are darling. I thought you were hiding in there it took so long. But I guess you just can't whip it out and whiz anymore can you? I saw the guys are in the bar and they've got us our regular table. Man this is going to be fun, probably better than before." I pivoted to head to the bar, and Ham stepped next to me. Wrapping his arm around his waist, he pulled me close, as if he was going to escort me in. In the restroom, I had thought about similar moves he might make, so I tried out a response "Come on Ham, you don't need to hold me like that. I can find my way. Besides, you don't want to limit your choices by making us look like a couple. You never know what pretty girls might be inside." At first he seemed put off, then he laughed. Loosening his grip on me we entered side by side. I scanned the room and spotted our old table. Todd and Brick were already there, eyes on the screen adjacent to the table. A quick look around confirmed there were only a few other customers. A group that looked like they were having a post golf round of drinks, a couple and two single guys. More or less a normal crowd for this early at the Pub. The first thing I noticed was how loud my heels were. The rhythmic sound caught the attention of my former friends and they turned toward us. I smiled, trying to act as if everything was normal. I immediately saw the reaction on Brick's face. His eyes widened, and mouth dropped open. I could see him checking me out, but I wasn't sure if that was good or bad. Todd was more stoic, although he did smile. Finally they motioned us over. Ham had his hand on my lower back, as if he were guiding me in. Deciding to try to take charge of the situation, I spoke up. "Hello guys, it's been a while. You look good. Everything been okay?" After Ham's mention of my voice, I indeed heard the sing-song quality in my question. I knew my voice was feminine, but now the rest of me was too. I tried to remain calm, but inside my heart was racing. They quickly glanced at each other and then back at me. Todd made no pretense of the fact he was staring at my bust. Brick was just grinning like an idiot. Finally, he just blurted out a reply. "We're okay, but how about you? I don't know if I'd recognized you if you weren't with Ham. I got admit though, you do look good Dana." "Isn't she a knockout guys? When I first saw her, I couldn't believe how hot she looked. I mean I was driving toward her and saw a killer ass and dynamite legs walking down the street in a tight dress. When I got next to her, I about drove off the road. I couldn't believe it was Dana, our old pal Dana. Hey sweetie, turn around so the guys can see what I mean about your ass." Ham's crude explanation shifted things rapidly to a place I didn't want to go. I had hoped, to sort of gloss over my appearance. Hoping perhaps that the guys would be polite enough not to mention it or keep comments to a minimum, sort of respect my privacy. But not Ham. I should have known better. He repeated his call for me to turn around. I felt like a piece of meat, but I knew him well enough that at some point I'd just have to do it to shut him up. So I turned around, so I faced Ham, with my backside toward Brick and Todd. I finished my turn and let them look. "See? Didn't I tell you it was killer?" My face flushed, and just as I was about to turn back around, Ham reached down. He grabbed the two sides of my dress and pulled it up, over my butt and up to my waist where he held it. My ass was now exposed to Brick and Todd, covered only by the sheer to the waist pantyhose and my tiny lace panty. I squirmed trying to break Ham's grip and lightly hit him on the chest with one of my hands. "Ham stop! Pull my dress back down now!" "Check it out guys, grab a cheek. I want to be sure it's as real as the rest of her. I already confirmed her tits were real and I'm pretty sure she's got a pussy now. How's it feel?" Before I could do anything, I felt two hands, one on each check, grab my butt. Lightly at first, then they squeezed or stroked it. I wiggled again, trying to move it out of their grip. That just caused them to hold me harder and pushed me more into Ham, my breasts once again pushed into his chest. He just grinned. "Feels like a girl's butt to me, soft, squishy and hot. I love those little panties too, don't you Todd?" "Yeah, she passes the Charmin test, soft and squeezable." All three guys laughed, prompting me to wiggle and squirm more trying to break free. I even hit Ham again in the chest, this time harder. "Okay let her go guys, I think we'd proven she's all girl." I felt the hands release my cheeks and I tried to pull back from Ham. He did release my skirt, but swooped his hands down so he was cupping my cheeks, kneading them like bread dough. This unexpected move prompted me to squeal which brought another round of laughs from the guys. Ham then lifted me up, so my breasts were in his face, and I was no longer standing. I squirmed harder now, my legs kicking in the air as I tried to push back from him. All that did was bring more laughter. He looked down at my cleavage and then over my shoulder at his pals. "I definitely like this version of Dana more than the old one. This one's not only a treat for the eyes, but I bet she's more fun too. How about we get a few drinks and start our party? "Ham put me down now! This isn't acceptable!" "Okay, okay, I was just playing with you sweetie. You can hardly blame us, if we want to get to know the new Dana better, can you? I mean if you wanted to change to being a woman and dress so sexy, you had to expect men to react like this. We'll be good we promise." With that he put me on the ground and pulled down the hem of my dress. I wobbled a second in my heels as I was so mad at how they treated me. I guess I should be glad there didn't act worse, I mean they were treating me like a woman, more or less. Even if I wasn't sure I truly wanted to be seen as a girl, it beat the alternatives. Now I just needed to get through the next couple of hours and then I'd be done with them. I thought maybe it would help if I sat at the table, rather than stand there. So I looked again, and I suddenly realized something. We'd always used this table because of how close it was to the TV, but it wasn't a dining table. It was a bar table, higher than a dining table, with bar stools to sit on. That meant, I would be perched on a stool, my legs front and center. But there was little choice, as I wasn't going to stand here the whole time in these heels. So up I went. I tried to smooth out my dress as I sat down and slide against the backrest, but it did little good. When I put on this dress at home, I realized it was short, but when I was standing it was long enough to be okay. It was a different story when I sat down. It crept up my body, so that it only came down to the top my thighs in front, and just beyond the curve of my ass in back. I'd have to live with it. I crossed my legs to help minimize any up skirt views, but that of course put more emphasis on my legs. I had just settled in, when the cocktail waitress came to take our drink orders. The guys all ordered a shot of whisky and a beer, pretty standard start for them. After jotting down their orders, the woman turned to me. She was dressed in a typical pub-type uniform, short leather skirt and white blousy top showing a hint of cleavage, black tights and heels of a reasonable height to work in. I considered getting a beer, what I normally ordered but wasn't sure. The waitress smiled at me, ready to take my order. "What will you have Miss? Same as the guys?" "Oh no, nothing that strong. How about a glass of the house white wine? Is it a Chardonnay?" "It is, then one glass of wine for you. Ham said he was paying for your drinks by the way. He tends to pay for most of his girls." Then as if she wanted to limit who might hear her, she leaned closer, next to my ear and whispered. "Oh, since you're new here, the manager wanted me to give you a few rules. Mostly, next time don't wear something so revealing. We get some families or couples here most days, so we ask working girls to keep it a little more covered up. And if you want to play little show-off games like you just did, you'll have to do it somewhere else, okay? It's not that you aren't welcome here we just want it to be more subtle, okay? I'm sure the guys enjoyed you flashing your butt like that but other customers might be offended." Then she cut her eyes over toward the bar as if checking to see if they were watching. "I don't want to be judgmental, but I had to pass the message along sweetie. If it's any consolation, you are certainly the prettiest escort we've had here in quite some time." I nodded my head as she left. As the content of her message sank in, I realized what she was saying. They thought I was a hooker. From the outside, I could see why it might look that way. My face burned. It was bad enough to be treated like a plaything by Ham and the guys, but having others see me as whore put a whole new twist on it. When she came back with the drinks, I desperately wanted to say something, but knew it would likely fall on deaf ears. In some way even, it would be better if they thought Ham was paying for me to be so sexy and available. I mean he was standing right next to me, with his big hand resting on my leg above my knee. I had moved it off once already, only for him to put it back. So I just smiled and whispered thanks to her as she gave me my wine. The guys all slugged down their shots and began drinking beer. Luckily the game was on by now, and it was a good one. They rapidly focused their attention on it, rather than me. The waitress returned several times to bring them more drinks. I was nursing my wine, as I didn't want to get drunk. After their third drink, Ham noticed I was still on my first. "Come on Dana, you've got to keep up. Let me get you another glass. I told you I'd take care of you. I don't' want you to not have a good time." The waitress was standing there, but I still had a half a glass and was in no way interested in more. So, I decided to try playing my girl card and see if I could manipulate Ham. I uncrossed my legs, spreading them apart. I put my hand on Ham's waist to maneuver him in between them. Once he was in position, I lightly trapped him there by moving my legs together. Leaning forward at the waist, I put my uplifted boobs right in front of him. I then took my free hand, and lightly stroked the side of his cheek. Giving him as pouty a look as I could I whispered to him. "Ham, I'm fine. I want to be able to remember this all, okay? It isn't every day, I get to spend time with such a nice hunk of a man. Don't worry you're keeping me more than satisfied." I moved back in my seat, smiling. I had hoped he'd take the compliment and I could see him react with his big old grin. But then he leaned toward me, his whiskey breath about knocking me over. Before I could react, he put his lips on mine kissing them deeply. His tongue darted in, thrashing around in my mouth so quickly I was totally surprised. I finally broke it off, and he moved back telling the waitress, to just bring me another glass anyway. He winked at me, and turned back toward the game, but not before running his hand down along my stockinged leg, from the thigh down to my shin. His moves sent shivers up my body. I was also blushing as I realized how massively I had failed at my distraction. I may look like a woman, but I had few of their persuasive tricks and moves. I saw Brick elbow him, he obviously saw my moves and Ham kiss me. I guess he thought I was flirting with Ham. The waitress returned with the drinks, and after she gave the guys their beers she put the wine next to me on the table. She stood looking at the bar, again as if she wanted to be sure no one saw her. "Just another hint honey. Ham gets awful frisky when he drinks this much. I don't know what all he's paid for, but if he offers to take you to the restroom beware. Management's caught him more than once, with some pretty thing kneeling between his legs in the men's room. They tend to come down hard on the girls, since he's a steady customer, they just give him a verbal warning. On the good side, he's apparently quite a mouthful. Just saying, be careful. Try using the staff restroom, up the hall to the left. It's a single stall and the entry door can be locked. Enjoy." I was petrified now. Just the thought of doing something like that, with any man, let alone Ham was enough to make me gag. But damn it, as soon as she mentioned the restroom, it made me realize I need to pee. I had a notoriously small bladder. Even less than a glass of wine, apparently would fill it up. Plus I realized I need to fix my lipstick. There was a smudge on Ham's lips, so I knew mine would be a mess. The last thing I wanted was to have Emily find me with mine smeared and half of it on some guy's mouth. So I made a plan. I drained the rest of my first glass of wine to give me some courage. I then dug through my purse for a tissue. I had to clean Ham up. I wiggled off the stool, going slow until my feet were stable on the ground. The guys were standing up, as they had been the whole time, watching the action. I lightly tapped Ham on the shoulder. He turned first, followed by Brick and Todd. He did have a little lipstick on him. Smiling I moved the tissue toward him. "Ham, let me wipe that off. You got a little of my lipstick on you and I don't think passion pink is your color." They guys, including Ham laughed. He let me wipe it off. I could tell he liked my attention. But I needed to let him know I was going, as I didn't want him looking for me. Once he was clean, I smiled again, placing my forearm on his chest, my fingers near his cheek. "I need to go fix my lips, as I want them to look good, you know? I'll be right back guys. Keep an eye on the game for me." They sort of mumbled a response, as I turned and began walking away, carrying my purse in one hand and the tissue in the other. With each step, I realized how much I needed to pee. And how much harder it is to walk in heels, when you're a little tipsy. I had decided to take advantage of the staff restroom, since it locked. Finally I got to there, tossing the tissue, I reached back and flipped a lever on the door, figuring it was the lock. Then without any hesitation, I went into the stall, both pulling my dress up and my hose and panty down as quickly as I could. I began to pee almost before I was fully seated on the toilet. The relief washing over me, as I let it go. But then a sudden bang rang out. It sounded like the door had swung open and hit the wall. Then there was a heavy handed second slam and a loud click. I was shocked. I guess I hadn't really locked the door. But what I heard next almost made me puke. "Dana, you little flirt. I knew you'd be my kind of girl. You hiding in that stall?" Before I could react to the sound of Ham's voice, he began to push open the door on my stall. There was just enough clearance to get it all the way open, only if I moved my legs. I didn't want to do that for sure. "Hold it Ham. Don't come in, I'm peeing for gosh sakes. Give me some privacy." "Don't worry honey, I've seen girls go before. Besides that means you're sitting down which should be just about right, let me in." Given the disparity in strength, there was no way I could hold the door shut against him. I shifted my legs slightly wider apart, as the stall door swung open. Ham stepped him, and with a quick move shut it behind him. He was grinning like he had won the lottery. I felt totally exposed, as my panty and hose were at my knees, the dress was up at my waist. I had just squirted out the last drop of pee and was wiping off my cock head. Luckily it was still up against me. But I felt so vulnerable, being focused most on pulling my panties back up to cover my privates. So I lifted up slightly, and quickly pulled my panties up to my waist. At the same time, I hit the flush button. I wanted to signal Ham I was done and ready to leave. "Let's go Ham. We're missing the game." "Don't worry it's only soccer. Nothing happens most of the time. Besides, I know why you're here. Annie the barmaid told me, she let you know where to go if you wanted to get a little more personal, if you know what I mean. That's why I knew to look here. I figured you'd be like this. You were dressed too sexy, and were way too flirty to not want to try some Ham. You want to snake it out yourself, or do you want me to serve it up to you?" "Quit it Ham, I'm still partly undressed and sitting on a toilet. This isn't what I wanted at all." I tried to push back on him and I could tell he was surprised. Guys like Ham were used to getting their way with girls, and if he'd been paying for them, none of them ever said no. But he kind of looked sheepishly down at me. "Okay, I'll step out and let you get dressed. There's a couch out here if that would be better..." He kind of left that last statement hanging and left. I quickly stood up, pulling my hose up to my waist and taking some time to smooth the nylon up my legs. I grabbed my purse and reluctantly stepped out of the stall. Ham was standing next to a small loveseat with fluffy pillow for seats. "Here is this better? It should be soft enough to kneel on." I felt cornered. He was between me and the door, with the sofa next to him. I was trying to think of whatever might get me out of this. Finally, I decided to try a little pleading, begging, and guilt mixed in with a few lies. "Hamilton, you know I can't do that kind of thing. I mean, it may not mean anything to you, but I am still married to Emily. This would be cheating on her. I can't. Besides, I'm not ready to take that leap. How about I give you a little taste? I've seen you drooling over my boobs. I can let you kiss and suck them, I guess." "Well, I don't know. I was hoping for more." I saw him start to weaken and went for it. I pulled down the front of my dress, just enough so I could reach into my low-cut bra and lift out my boobs. Even out of the bra they jutted forward, the cool air causing the nipples to harden. Ham saw them, and grinned. Then leaning forward he began to kiss, lick, and roughly suck on them. Reminded me of seeing a young calf find its mother's udder for the first time. Only a calf wouldn't bite down on the nipple that hard. I could tell Ham liked it, as he was sort of moaning. Then he stepped back a bit, and unzipped his pants. He reached in and was starting to pull out his cock. I looked at him. "Now don't over react, just take it in your hands and play with it a little. That's not cheating. I just got to have some relief somehow and soon." I felt trapped again. He had his junk in one hand and reached up with the other to grab one of my hands. Soon, I was holding him. It was hot, sweaty, and a more than a handful. He was rapidly getting totally erect. I just shook my head and went ahead. Using both hands I began to stroke him. He leaned back against the door. I felt so slutty, my boobs out of my dress, while I whacked off a guy who had been one of my friends. But it only took a few strokes and I could feel him tremble, as if he were right at the edge of coming. I went a bit faster, rubbing his cockhead a little more, but he stayed right there at the edge. I decided to up my game, spitting in one hand to give me some lube to work with and taking his ball sac into my other hand. I was trying all the tricks that worked for me, but he stayed right at the edge. It was probably due to his drinking. I was ready for this to be over and so was he. I felt like if something didn't happen quickly, he'd start to soften. He finally opened his eyes and looked down at me as I worked on him. "Dana, just take the head into your mouth, just a little please? I'm close, so close. If you kiss it some, run your tongue over it that'll do it for sure. Please?" I didn't even want to think about that. I considered running a finger up his ass to trigger him, but that wasn't sure fire, then I'd have his stank butt smell on my finger for nothing. I tried changing pace again, lightly massaging his balls as when I returned to a faster speed. But no go. "Come on sweetie, just the head is all I need. I'll come for sure if you suck it. Like a lollipop. It won't be bad." I couldn't believe I was saying this, but I was so over this. "If I do, you've got to let me know when you're about to come, understand?" "Sure, sure I get it. I tell you when I'm coming. I promise." "Promise?" "I swear I'll tell you as soon as I can. Promise for sure." I looked down again at the purplish cock head. As far as I could tell there was nothing special about his cock. It was normal size, maybe a little thick, but circumcised like most cocks. There was starting to be a drop of pre-cum in his slit. I figured he was close. I knew for me, feeling the soft warm lips of a woman's mouth at this point would push me over the edge. But could I do it? Why should I? Finally, I just closed my eyes, opened my mouth, and slid it over his cockhead. The response was immediate. He moaned, softly, showing satisfaction with my touch. Inwardly, I groaned as the taste was tart, musky, and unappealing. But I had done it. I put my lips just behind the rim of his glans, sealing them against the shaft of his cock. I lightly began to suck his cock head, with my tongue teasing the tip. I wasn't ready to go wild, as I was trying to minimize my touching him. But there was more reactions from Ham. He got noticeably stiffer. I could feel his balls twitch in my hand. It seemed like more pre-cum was leaking too. So, I decided to ramp up my efforts. I sucked a bit harder for a few seconds, then moved back to release his cock from my mouth. It was openly twitching in the air, so I began running my lips around the rim of his cockhead and tracing patterns with my tongue over it. Again, I could sense a greater urgency on his part, both from how his cock was acting and the moans he was making. He also placed his hands on the sides of my head, sort of steadying himself. Seeing he was getting closer, I reasoned one more push would send him over the edge, but I wanted him to remember to tell me. "Getting close aren't you Ham? Just be sure to tell me when you start to come. Don't forget." "Oh my gosh, I won't, I promise. You're so good at this, baby. I never imagined you'd be so talented with those lips, even though they always looked like a girl's." I took his last comment as a compliment, in a way. But I went ahead and took his cockhead fully into my mouth again. I forcefully sucked on it, sort of a slurp, slurp, slurp rhythmic pattern, where I sucked hard then soft then hard again. My tongue was playing along the rim and then his slit, alternating between them. Again, I could feel him getting close, very close to coming. I was just about to pull back from his cock, when I felt him tighten his grip on my head. "Get ready baby, I'm close. Keep sucking, keep it up, I'm oh so close. Come on, girl, you can do it. Ahhhhh, oh god, I'm coming, here it is. Get ready to swallow honey." I could tell he was ready. But Ham was holding me tight. He wouldn't let me take my mouth off his cock. This was my worst nightmare. No way did I want his jism in my mouth. I tried pulling back harder, but he just thrust his pelvis toward me, keeping his cockhead well into my mouth. I was just about to panic, when I felt the first ejaculation. I could feel it in his balls, as they tightened up in my hand. I could feel his cock's extended twitch as he shot it out. I could feel it as the semen landed on my tongue, warm, thick, salty, and tangy. The taste immediately filled my mouth and the scent moved into my nose, filling my consciousness with his orgasm. At that point, I was beyond being mad. It was just going to happen, too late to pull back. If I tried moving now, I wouldn't get far enough away. I'd get a few shots of cum in my face. That'd be worse than this. So I took it. He had shot another load, and I could feel it starting to pool up in my mouth. Then a third shot added more. I had briefly thought about just holding it in my mouth and spitting it out when he was done. But he didn't seem anywhere near being finished. Two more twitches followed in rapid succession, my mouth starting to get so full, I thought it might start leaking out down my chin. Again, I didn't want any cum stains on my dress. So I swallowed, then swallowed again. He was still shooting, weakly, so I started lightly sucking again, pulling any remaining come from his rapidly deflating cock. I twirled my tongue around his cockhead one more time, sort of wiping it off. Now when I started pulling back, Ham let me. He had released my head. I think he was so drained mentally as well as physically that he was in a daze. As his cock emerged from my mouth, I licked it to be sure nothing was going to drip. Then with my hands, I stuffed it back in his pants, as I leaned back. He had finally opened his eyes and was looking down at me. Slowly he zipped up his pants, sort of regaining consciousness. "Dana that was amazing. It was one of the best blowjobs, I've ever had. God, you knew what to do and when to do it. The way you sucked me dry, I mean no girl's done that before. You seemed to really want my cum. I loved it. I don't' know what you were so afraid of, I told you I'd let you know when I was coming. I wasn't going to let you miss your chance to get some of ole Ham's special sauce. If I had known you were such an expert cocksucker before, I would have let you do me a long time ago. I should have known you'd be good at this, as you always seemed a little swishy, before. Now I know why. Really, you don't know how much I appreciate this. My wife won't suck me, says it's not something proper women do. But I swear, a girl like you really knows how to please a man. I tell you that. I'll be happy to let you have some anytime you want. In fact, if you need something in return, you know, I wouldn't be opposed to that either. You never mentioned it, but if you're short on cash because you got fired, I'm sure we could work it out. It's not like I haven't paid girls to do it before, just never any this good. Well I guess we'd better get back. I'll go first and let you cleanup. I'll see you at the table sweetie in a few minutes. Thanks again, you're the best." Ham flipped a knob on the door, obviously the lock that I had missed, and left. I was still kneeling on the couch, my head reeling and overwhelmed by what I just did. Did I really do that? To Ham? The strong, taste and smell still filled me, so I knew it wasn't some sort of strange dream. I had just sucked one of my friends. He even called me a cocksucker, complimented me on how good I was at, and to add insult to injury suggested he'd be willing to pay me. So, I was now a cock sucking whore. Nice. I realized I needed to get going. I slowly stood up and even thought I didn't want to, went to the sink and looked in the mirror. The reflected image only confirmed my new status. My boobs were still outside of my bra and dress. Most of my lipstick was gone, what was left was smeared. My lips were now coated with a shiny, pearlescent slime. I started to run my tongue along my lower lip, but decided I had enough. I got a tissue and ran it under the faucet. I wiped away the last of Ham's release, and then began repairing my makeup and hair. I bent over to wiggle my boobs back where they belonged. I wanted to look like nothing had happened, so I took extra care. That was really difficult because it meant staring at my face. I was beating myself up inside, for being so weak, for not refusing and fighting him off, and for just being such a wimp. It made me think of how easily I had given into Emily and her silly reasoning about wearing these clothes in the first place. Now, I had transformed into a hooker in training. After I had everything right, including checking my hose and dress, it still took me a few minutes to get the courage to go back out to the table. I was pretty sure Ham would be bragging to his friends, so my lapse of willpower would now be a character defining moment. I tried to act confident, or nonchalant, like nothing had happened at all. I strode to the table, my heels clicking, my ass wiggling under the tight dress, and my boobs bouncing lightly in their bra. The first thing I saw was the sick grins from the guys. Ham had told them, everything I imagine. They stood in a cluster, separated from the table, in front of the screen. Like they wanted to be near but not with me, at least for now. But what I wanted most was a drink. I had to get his taste out of my mouth. I picked up my wine glass, and drained it. It removed some of the taste, but not all of it. Then from out of nowhere Annie, the barmaid came over. She put a shot glass of clear liquid and another glass of wine on my table. She was grinning widely and winked at me. "Well honey, congratulations. From the way Ham's describing it, you more or less invented the BJ. I know he's had more than a few here, and never reacted that way before. So you must do something really special. Also, I don't know about you, but for me, afterwards, I just want to get rid of the taste. So, try this. It's a shot of peach schnapps. That and some wine, should clear your palette. By the way, if you're interested I know several regulars, guys that come here nearly every day that would love to make your acquaintance, if you know what I mean. You could get a regular clientele going, if you want. Just leave me your number on a napkin, and I can set it up for you, no cost. I've found when guys like Ham get drained, they buy more and tip more, so it would be win-win for both of us. Also, I bet our manager Stewart, would easily overlook how you want to dress, if he was on that list too. Might be easier to give a freebie away now and then than invest in a new wardrobe. Just saying." Annie winked again, as she walked away. I was so disgusted by it all, I just was stunned. But I did try the shot and wine. She was at least right about that, there was only a mild trace of Ham now. I was sipping my wine and starting to really feel the buzz of the alcohol, when Brick broke from the guys and slid over next to me. He cleared his throat as if he was trying to get up the courage. He didn't really look at me, but just sort of glanced over as he pretended to still be watching the game. "Um, Dana. I just want to let you know, whatever you want to do with your life is cool with me, you know. I think people ought to be free to choose their own path, without being judged, right? So I totally support your new look. I mean why wouldn't I? You look killer. Also, everybody should be free to express their sexuality however they want. You know like you and Ham. So, if you want, I'd be open too, if you know what I mean." When he finished, he glanced over again, only this time, he was looking down at my boobs, staring more accurately. I couldn't believe what I had just heard. Apparently, he thought I was up for sucking all of them. He was nice enough to say that was okay. That whatever I wanted to do to express my new found gender, he'd be happy to help. I don't know what it was, maybe the insulting portrayal of the barmaid, the guilt I felt from Ham, Brick's implications, or just the booze. Whatever it was, it made me react in a way I would never have imagined. I took a slow sip of wine, then pursed my lips, lightly running the tip of my tongue around them. All the while staring intently at Brick. "Sure honey, I really appreciate that. To know you have my back is so nice. But if you want what Ham got, I need a little something, something. You know? I mean, Ham's been covering my bar tab, so I'd need something else from you. I don't have the cash flow now that I had before. So if you'd be willing to help out, I'm sure I could find a way to thank you, personally. Here, I'll give you a note." I reached in my purse and pulled out a pen. Taking a cocktail napkin, I jotted down my name, cell phone number, and '$100'. I'd never paid for sex, but thought that would be so high, he'd never take me up on it. Plus I was sure it would turn off the other guys as well. I put it on the table and showed it to him. But before he could say anything, I heard the door opened to the bar. A quick glance, showed that Emily had come to pick me up. I didn't want her to see the note, so I drained my wine, flipped over the note, and set the empty glass on it. She was grinning, obviously pleased with herself for setting me up with my old friends. I'm sure she saw this as a way to break me out of whatever resistance I might have to dressing as a woman. She had no idea how it had turned out. She walked toward us looking very sexy herself. She had skintight, pull-on jean leggings that she had tucked into black velvet, thigh-high boots. She was wearing, what looked to be a body-suit. A black sleeveless turtleneck, molded to her body, and showing that she wasn't wearing a bra. A long sweater duster in taupe, completed her outfit. Emily had curled her hair and done her makeup, she looked great. I was just glad to see her, as it meant my torment here with the guys was over. But they also noticed her arrival. They turned and we all met at the table where Brick and I were. The guys were all smiles. "Hello fellas, having fun? Hi honey, enjoying your play date with your buddies? Looks like you're all having a good time." "It's been great. I hadn't realized how much fun Dana added to our group. She's got to be a regular again. Don't you agree, Brick, Todd?" "You bet, we want here, whenever she can. In fact, Dana, when you were in the restroom, we talked about how long it's been since you joined us for golf. You've got to play a round with us. How about this weekend? We've got a tee time and I'm sure we could make it a foursome. What do you say?" "Why don't we get a round of drinks and talk about, I'll buy. What do you want Emily?" "Thanks Ham, that's so sweet of you to offer, but I'm starving. I just wanted to say hi, get Dana, and go to a nice restaurant. But I like your golf idea. What do you think Dana?" I felt trapped now. Not only did all the guys want me to do it, now Emily was joining in. But I thought I had a good excuse. Getting back together with these guys was not on my agenda. "Well I'd considered it, but I don't have any golf clothes that fit any longer. I think we even donated them. About all I have left are the shoes, and I don't think they're my style any longer?" To emphasize the point, I lifted my leg and rotated my ankle, showing off my heels. I thought I made my point, as everyone was silent for a moment. "I think we could find something for you to wear, from what we have available honey. I mean, it's not like you have a standard uniform you have to wear. I bet I can find some shorts, a skort or something similar you could wear with a stretchy top. All you really need is to be able to move and have something that moves with you." "If you come early, we can go to the pro shop here and get some shoes. They carry a nice variety. We'll even pay for them, won't we guys? I mean having you back as part of the group would be worth it." "Yeah, in so many ways. I really want you to be part of the group again." That last enthusiastic statement from Brick worried me. I should have expected Ham to offer to buy me shoes and I know Emily was just trying to help. In her eyes, getting me back together with the guys, and in my female attire, would only help me adjust to my feminine portrayal. As far as she could tell, my visit today turned out great, so why not? As I had many times lately, I felt cornered. I decided to agree and back out later. "Okay, let's make it a foursome. When is your tee time?" "It's at 10, so if how about I meet you at 9 at the pro shop? That'll you plenty of time to shoe shop and find something that fits your new look, okay?" I nodded yes, a sinking feeling inside. With that settled, Emily and I left. She was all bubbly as we walked to her car. Going on about how nice the guys were, how I surely missed hanging out with them, and it would be a good stress reliever. The last part was the least accurate statement. Not only had I had to deal with her insistence I transition, but I had begun to worry about the bills and our reduced income. I mean when the company offered me the 2-year deal, it seemed like a blessing. But now, I saw how it really limited me. I had only a day or so left on their contract, and despite repeated efforts to find similar jobs with their competitors, I had struck out. Turns out my two year absence from the workforce was what employers saw rather than my advisor role. It made them worry about how dedicated I'd be or whether I really wanted to work or not. Plus I was kind of out of touch with the current market. So, with our regular bills, worsened by Emily's shopping and salon spree for me, I saw deficits coming. I really didn't want to tap into our retirement savings, but we'd soon be running on empty. All this was only compounded by what happened between Ham and me. I just had to tell her, as it was eating at me inside. So, when we got in the car and she started driving to the restaurant, I decided to speak up, when she gave me the chance. "Dana, tell me about your happy hour. Were there any difficult adjustments because of the new you? Did they accept it okay?" "In a way, I guess they did. Ham did of course. Brick and Todd were more surprised, as Ham just told them he was bringing me, and said nothing about my appearance. But it felt so awkward, as they didn't treat me like the old Dana, but as what I look like, a woman." "How so? What was different?" "Well for starters, Ham was all hands from the start. Plus he not only starred at me unrelentingly, but made comments about me. How my tits were so hot, my ass was awesome and my legs went on and on. I felt like a piece of meat by the time we got to the Club. In the car, he made me enter from the driver side, and stopped me, so that I was spread-eagle by the shifter. Which of course, allowed him to play around between my legs so to speak. He also had no reservations about checking out whether my breasts were real or anything else. I mean, he ran his hand over my crotch once when he shifted. Later, he more or less told the guys that I must have had surgery to be a complete woman, as he felt nothing there. It made me cringe, both from him touching me and how easily he accepted the idea that I was better off as a woman. The others soon followed his lead. I talked to Brick for about ten minutes of which only about thirty seconds did he look anywhere but at my chest." "That's not too bad, I imagine it was just part of them getting used to your new appearance. I know the shifter trick is one that almost every women has run into at least once. Besides how can it hurt if they think you really are all woman? In some ways, it should help as they won't question your appearance." "I can tell you how it hurts. They assume that if I'm now a woman, then I must like men and what they have to offer." "Oh don't worry, I can't imagine they're like that at all. I mean they're your friends, they'd respect you more than anything. I bet it's just stupid old guy stuff, fooling around, making dumb comments. Every woman experiences that. It will be fine." "No, not really. Once Ham thought I was no longer a guy, then he put on the full court press. Plus it didn't help the way I was dressed. I think he assumed I was advertising or something. I mean, one of the first things he did when we got there, as he told the guys how he noticed my big ass shaking in my dress as I walked, was he flipped up my dress to show them. Not just for a second either, he held it up, almost to show me what he could do, as much as show the guys what I had. It was horrible. But that wasn't all. Because of my dress and his silly antics, the waitress came over to warn me about what they expected escorts to do when they were in the bar. Apparently, Ham's been bringing hookers there and so has a reputation. She saw me and just assumed I was a new one. It didn't help that he was paying for my drinks, rubbing on me, and calling me baby, sweetie, or sugar. I could see how they made that assumption. She even warned me about him taking hookers to the restroom for blowjobs." That brought a giggle to Emily, as she glanced over from her driving. To her it seemed more like some sort of initiation to being a girl. "Still that's not too bad. So they think you're so sexy that you're a pro. Ham finds you so hot, he acts silly and stupid. Get used to it Dana, you're a very attractive woman. It's part of the territory. As long as you draw the line, and stand your ground everything will be fine." "It may be too late for that now." "What do you mean, too late?" I was close to crying now, tears welling up in my eyes. I had to tell Emily what happened, but it was difficult. I was embarrassed, ashamed and afraid she'd never see me the same again. But it was too big to keep a secret. "Well after some wine, I had to go pee. So I went to the staff restroom, as the barmaid suggested. I thought she was offering me a tip to keep me safe. But it really was just where the bar preferred the hookers do their stuff, with guys like Ham. Of course, Ham followed me in there, caught me on the john and began to pressure me. He was so whinny about being horny, about me being so sexy, and that his wife wouldn't give him blowjobs. It was unrelenting. I felt so exposed, with my panties around my knees and him standing over me. Finally, I told him I couldn't do that. It wasn't me, plus I was married. Finally I told him, I'd do something to help, just to get him to leave the stall so I could get dressed. But he was still there when I came out, as pushy as ever. He corned me on a couch and wouldn't let me leave. So finally I made a deal with him. I'd let him play with my boobs, kiss and suck them whatever, and I'd jerk him off. Nothing more. So that's what I did. But it only got him so far. He was close but wouldn't come. That's when he really begged me to do him. That if I just licked his cockhead it would be all he needed. Finally, I got so sick of his bull, I just did it. I don't know why, but I did. Took his disgusting cock in my mouth and did it. It was horrible, but it was over. I just didn't know what else to do. I feel terrible." I stopped to see how Emily took it. She had gone totally silent, quietly driving along. She wouldn't even look at me. I felt like I wanted to die, I was sure my marriage was over. She had to hate me for what I'd done. Finally she spoke up, softly. "Well, that's a surprise. Tell me did you swallow his cum?" "Yes." "Did you gag on it, or feel sick?" "No, I mean I felt disgusted the whole time, but it was just something I had to do. He's promised me he'd tell me when he was coming. I had hoped to just have him shoot in my hand. But he wouldn't let me move my head, held it there until it was too late. I couldn't move without getting it in the face or all over me. So, yes I swallowed." "So, you felt it when he shot his load in your mouth?" "Yes, it was horrible, I could feel it land on my tongue and the taste was sickening." "But you didn't get sick?" "No, I guess I was too scared and just wanted it over." "Well that tells me a lot. I had a roommate in college. She loved to suck guys off. Something about being in control, and all. She always swallowed their cum. No problems. I asked her how she did it, how she handled it. She told me she was a natural. That the first time, she had no negative reactions, she just sucked the guy and when he came, despite being surprised she swallowed it down. It was her theory that some girls were born cocksuckers. Just naturals. Sounds like that's what you are. Was Ham happy, did he like it?" I was blushing furiously now, wiping away tears and trying to understand why she thought I was a natural at such a sick thing. Why she wanted to know if he liked it? "Yes, he did. Ham seemed so enamored by it, that of course he bragged to the other guys about how good I was. I think he was just so drunk and overwhelmed by me agreeing to do it, that he thought it was better than it was. That's all. It just made me feel so cheap. That's one reason I don't want to play golf with them. I just feel so odd around them now." By now, we had pulled into the restaurant parking lot. Emily parked toward the back, away from other cars, sort of private. She turned to me and lightly put her hand on my upper arm. She was smiling in an odd way, but with empathy. "Dana, it's not bad what you did. It's okay really. I mean you lick my pussy all the time, so oral is just something that people do. The way Ham pressured you, is awful to me, but unfortunately it happens all the time to women in our society. Even with the heightened awareness, sometimes a girl has no choice but to submit. At least he still values your friendship. I'm sure you can work out an arrangement so he realizes such acts aren't acceptable. I think him offering to buy you some golf shoes, probably reflects that knows he overstepped the boundary between friends. I'd suggest you give your old friends another try. I want you to know I don't feel you violated our marriage either. It sounds like you had no other choice. In fact I like how you were worried about what I would think, but still wanted to tell me. That shows me how much you do love me. And I love you too. I think this is just another step in us figuring out how our life is going to change with your new image. So, let's fix your eyes, go inside to eat, and we can talk about it some more." Emily leaned over and kissed me while she moved her hand to mine to hold and squeeze it. I was both surprised and pleased about how she took the news. The reality that such pressure from guys was something she acknowledged as almost an expected hazard did open my eyes. I guess since I hadn't been that kind of guy, I never imagined how common it might be for women. Inwardly, I cringed when she seemed to think that meeting them for golf was okay, but maybe she was right. Without all that booze, maybe Ham wouldn't have been so aggressive. I tried not to think about whether my sexy attire led him on, it shouldn't be a reason for a guy to cross any lines. Emily helped me fix my eye makeup from the tears, and by the time we entered the restaurant, I was feeling better. We got seated, ordered, and continued to talk. It seemed Emily was proud of my oral skills with Ham, telling me that it didn't surprised her in many ways, because I was so good with her. She also promised me a sexual surprised later when we got home. We had just finished our meal, and were having coffee when my phone rang. It was a number I didn't recognize, and was going to ignore it, but Emily suggested I answer. Maybe it was one of the guys or even a work follow-up. In fact, she answered it on speaker, so I could talk as she held the phone. "Hello?" "Hi Dana? This is Annie from the bar. I got your note. I'm so glad you decided to do this. I think it will work out great for both of us. I just wanted to check on a few details before I started talking to customers. First how do you want to do this? Do you prefer a few each day, all week, or maybe bunch them up on a few days? Unless you have a preference, I'd suggest doing Tuesday and Thursday. I work both days, they are generally slow days, except for the regulars who'd likely be your clients, and it will keep a lower profile for you if you're only here a couple of days a week. But I don't know your usual schedule. So I don't know if you can be one place for 3 to 4 hours. The only other thing would be meeting with Stewart. Are you going to be here anytime soon? I'd suggest you drop by, so he can meet you and the two of you can discuss how it might be something you'd both profit by. Okay?" I was shocked and embarrassed. Emily just looked at me puzzled, and curious at what this woman was talking about. I had forgotten all about the napkin I had shown Brick. I assumed it had gotten thrown away. But apparently Annie found it and took it as a sign I was agreeable to her proposal. I didn't know how to respond without first explaining it to Emily. So I opted to just delay. I needed to talk first. "Annie, what a surprise. Thanks for calling so soon. I hadn't thought about the details, I mean, how we might make it work. Tell you what, let me think about your questions and I'll call you back tomorrow. Is that okay? As far as meeting Stewart, I'm supposed to play golf with Ham and the fellows on Saturday. That would be the soonest I'd be there." "Sure, sure that's fine. I'll be up around 10 and don't have to be at work until four, so if you can call between then. Talk to you later Dana and thanks again for this. I sure could use some extra tips. Bye." As soon as I hung up, Emily looked at me with this puzzled expression. I was so embarrassed, I just turned a bright red and tried to stumble out an answer. It was so complicated, I wasn't sure I could really explain. "Emily, I know that sounded strange and I was shocked too, but let me explain. As I mentioned, the barmaid, Annie, assumed I was one of Ham's hooker girls. She had that image of me from the start. When I figured out what she thought, it shocked me, but it sort of stuck in my mind. After I returned from being with Ham, she had heard him bragging about how good I was. She told me that was new, and assumed I was really good at it. She then suggested she could arrange more hookups with other customers if I was interested. Apparently happy customers mean more tips for her. She thought of it as a partnership. Of course she wasn't the only one who heard Ham bragging about my skill. Just before you came in the bar, Brick had sidled over to me, making it clear that if I wanted to suck him too, that would be fine. By then I had several glasses of wine and a shot of schnapps, so maybe I wasn't thinking straight, but I decided what the hell. I figured it would be easy to stop this, if I told Brick that he'd have to pay to get one too. So I jotted down my phone number and a dollar amount that would be so high he'd never do it. I showed it to him, and said if he wanted it, this would be what it would take. Of course, he just stared as if I had punched him in the gut. But when you walked in I didn't want to have to explain it, so I just put the napkin under my drink. I thought it was thrown away, but I guess Annie found it and assumed it was for her. I'll just call her tomorrow and tell her I changed my mind. It's just so embarrassing to even be thought of as a hooker." As I explained what happened, Emily began to smile and then laugh. She thought the whole thing was funny. She liked that I was so good that Ham was bragging but understood totally about what happened afterward. "So how much did you write down, $300, $500, more?" "No, $100. I thought that was enough." "That's not too high. From what I heard from expos?s on television, that is a common price for a good escort. I mean if it was any cheaper you'd have to be a street whore. No wonder Annie thought you were serious. To be honest, I'd expect Brick to call you too. With your old job ending, maybe you should consider a new career." She laughed again. "Ha, ha, not funny. It's embarrassing to even talk about it. Besides, I can't believe there are enough guys willing to pay for sex for it to even be more than a joke." "Well I'm not sure about that, guys seem desperate for sex these days. But in any case, I find it sexy, to think about all those guys wanting you. I know I'm getting turned on just hearing about it. How about we go home, I've got something I want to try out." I agreed I was ready to go home. I wanted out of these clothes and the idea of sex with Emily was perhaps the only way to save such a horrible day. We paid the bill and hurried home. Once in the house, she told me to get undressed, she wanted me wearing only panties while I waited for her on the bed. I quickly complied and was soon waiting in anticipation. It wasn't lost on me that twice in a row Emily had specified I keep my panties on for sex. It was clear my penis was not going to be the focus of most of our sex going forward. She had gone in the bathroom after me, and soon emerged. She was carrying something in her hands. When she got next to the bed, she held it up for me to see. It was some kind of sex toy, a purple one, sort of like a dildo but with a couple of shafts. Now I was the puzzled one. She saw my reaction and laughed. "Don't you get it? This is a dildo for lesbians. It fits in me, without a clumsy harness, and lets me take you. The double shafts will please both of us, let me feel what it's like to be in control, and lets you get more in touch with your girly side. I'm going to put it in, and then we can play." I could see her lube up the shorter shaft, and slip it in her pussy easily. I was surprised at her desire to try something so wild, but after the boundaries I had crossed earlier today, I wanted to be sure Emily was okay with me. So I would do anything she wanted. Once she had it secure inside her, she looked at me, ginning. It was like she was proud of her new cock, a look I'm sure most guys have when they're about to do a woman. She stepped toward me, sort of waving it around. "How's it look baby? Making you hungry?" She laughed, and stepped closer. "Tell you what, why don't you show me what you did to Ham? I'd like to see why you're so special." "Oh come on Emily, don't do that." "Dana, just do it, I think it will help you get past it and understand it is just sex, nothing more, nothing less. Now show me how much you love me." Again, I could tell this was something Emily wouldn't back off from. So I decided, what the hell. It's not like I haven't done worse today. I dropped to my knees in front of her and lightly grasped 'her cock' at the base. I then took the head into my mouth. I mimicked what I did earlier, trying to show her how I had pleased Ham. She seemed delighted, but when I sat back, and stopped she was surprised. "Was that all you did for him? Didn't you take more of the shaft into your mouth?" When I shook my head no, it surprised her further. "Well if you got that much response just from licking his head, let's see what else you can do. Try taking as much shaft into your mouth as you can. Swallow me baby." Although it was still embarrassing, I did what she wanted. I closed my eyes and began to take it in. At first it seemed strange to slide something that big into my mouth, but after the first few inches, it just felt odd, nothing worse. I kept pushing my lips down over her purple shaft, sort of waiting to gag, but never did. Before I realized it I felt my nose tickled by her pubic hair. Opening my eyes, I confirmed I had indeed swallowed her whole shaft. It made me feel stuffed in an odd way, the head of the dildo in my throat, but not so much as to be uncomfortable. Mostly, I had to adjust my breathing through my nose, and how I swallowed any salvia I had. "Oh my word, you took it all! I can't believe how easy you did that. You didn't even gag once, did you? I was right, you do have a natural talent for that. I could never take more than a couple of inches without feeling like I was going to choke. Even my college roommate never went past about five inches. But I know this thing is seven inches plus. Very impressive. Now show me how you'd use that skill." Again, I saw no point in protesting, plus I couldn't talk at the moment. So I went up and down several times, experimented with using my tongue as I did, and even managed to flick my tongue on the outside of her labia when I had it all the way down. I could tell it was entering my throat, but no matter how many times I went down, how fast I moved, or how hard I pushed to take more, I never felt like I was going to gag. I could tell Emily was impressed. But I could also sense, my movement on the external shaft was moving the smaller one inside her. Finally she'd seen enough. She pulled the shaft out of me and began to put some lube on it, slowly stroking it like a man would his cock. "Back on the bed honey. On your knees, head down, ass up. I'm going to fuck your tight pussy now." The rough talk from Emily seemed so out of place, but I guess she was just getting into her role. I did as she asked, and she was soon behind me. Pulling my panties aside, she positioned the dildo at my ass, then began to push inside me. I could tell the lube was working, as I felt pressure but it was sliding in smoothly. The more she entered me the more animated Emily became. She not only began thrusting, but talking too. Lots of intimate chatter, telling me how tight I was, how I was turning her on, as well as more aggressive clich?s, like who's your daddy now, how she was such a stud, and whether I'd ever had such a hung lover. It seemed so weird, but exciting too. The more aggressive she began, the more I began to respond. She plunged all the way in, and lay on my back, reaching around so she could fondle my boobs, which hung down from my chest. Light love bites on my neck, blowing in my ear, and pinching my nipples, Emily looked to excite both of us. She even reached between my legs to stroke my cock, which had gotten hard despite being trapped backwards in my panty. Finally, I could feel her tremble and momentarily stop moving. She had come. After that brief interlude, she resumed fucking me, getting wilder and more physical. Emily set up a real rhythm and my ass was burning. The heat was getting my cock excited too. As she began to shake and reached another orgasm, I was there with her. With both exploded as our climax washed over us. She fell next to me in bed, her cock still buried inside me. Wrapping her arms around me, we cuddled for a while before rising and getting cleaned up. This was the second night in a row that I had been driven to a new type of orgasm by my wife. My life was now entirely different than before, with perhaps the only bad aspect being my mistake with Ham. Snuggling with Emily as we drifted off to sleep made it seem like a bad dream, I could learn to really like the rest of this. The next day felt really weird. Emily had a certain attitude toward me, different than normal. But I couldn't really classify what was different. Maybe it reflected how she was becoming dominant in bed. Maybe it reflected my compliant attitude toward appearing more feminine. Maybe it was how I had actually functioned as a female outside of her home. I know she bragged on me again about what a good job I had done gathering information from our neighbors. She also complimented me on my attire, even though I had selected a more modest blouse and jeans with flat shoes. I had done my makeup and hair. I was just about to call Annie and tell her of my change of heart, when I noticed I had a message on my phone rang. It was her. "Hello Dana, I just wanted to touch base, as I've had to go into work early today. I went ahead and spoke to some of the guys who might be interested in meeting you. Wow, bonanza. There were at least 16 who were interested. I'd bet they even want to be regulars if you're as good with them as you were with Ham. By the way, I told them it would be $150 each. I figured if you're better than average, then you deserve more. I wouldn't be surprised that you could get two bills even, once they sample your product, so to speak. I know you needed some time, so don't feel pressured. Tell you what, why don't you just think about it? If you want to do it come see me after your golf game on Saturday. That'd be soon enough." I was surprised in several ways. First about her upping the price and again about the level of interest. A quick mental calculation told me that many guys at that price would be $2400. I never suspected she'd be talking that kind of money. It ate at me actually, because if that was per week, and you looked at yearly total that would be like my old salary. More in fact. The annual number stayed in my head, because I had looked at my projections for next month's bills and my available income. It would be the first month we'd be short. I could handle it with savings, but hearing what guys would pay for such a minimal act really shocked me. But at that point, I put it aside as Emily had some work she needed help with. We spent most of the day, cleaning, going to the grocery, and just doing chores. It was relaxing in a good way, and I felt pretty good about myself as I seemed to be much more comfortable in my female things. It was far easier going out in jeans and flats, no one even seem to look my way. That night was also good, as Emily and I shared a long bath and we watched a movie in bed, snuggling kissing and playing with each other, although we refrained from actual sex. Friday we woke up, shared breakfast in our robes, and talked about what we might do. I really had no commitments, because yesterday had been my last day on payroll. For Emily, she didn't feel like shopping and the house was clean and organized. Maybe we could go to an art gallery? There was one an old friend of ours had some paintings on display. They usually had a Friday afternoon wine and cheese thingy too. That sounded like a possibility. But first she said, if I was going through with my golf outing we needed to see if had something to use. I agreed, although not enthusiastically. "I know you used to wear slacks and polo shirts, and maybe a sweater or light jacket later in the fall, but it's still pretty warm. Did you ever wear shorts?" "Occasionally, yes. I mean in the heat of the summer. I admit this time of year is a tough choice, but I guess I wore slacks usually." "Well, we don't have any of those type of pants that fit you now, only jeans. But I do have a couple pair of casual shorts. We could pair those with some tights, a fitted top, and a light jacket. How's that sound?" "Tights, I don't know about that." "These are a footless style that I used for yoga, not a dress tight. They're a suntan color that just make your legs look smooth and nice. Tell you what, let's try them and we'll see how it looks. Also, normally I'd recommend a sports bra, but you don't have one. So, we'll use that nice lace, longline bra with the sheer, full cups. It will provide a bit more support than those pushup bra styles you like." Reluctantly, I agreed to try out her ideas. The bra and hipster panty were fine, a plain white, but with lots of lace. I saw what she meant by a little more support, as the wider band at the bottom and full cups held my breasts firmly. The tights too, worked better than I had imagined. They were thicker than pantyhose with more stretch. The color was fine, being just a bit darker than my normal skin tone. I'd wear short socks with them. For the top, Emily suggested a tan, stretchy body suit that had long sleeves, a thong style bottom, and scoop neckline that wasn't low enough to show cleavage. It fit tightly on me and because it had a built in bottom, it would stay in place throughout any swings or movements. The top was pretty sheer though, revealing my lace bra easily. Emily said that shouldn't be a problem if I wore a nice jacket or sweater. The shorts were a forest green, with a size zip entry, and scalloped edges around the bottom of each leg. Because there was no front fly, it had a nice flat and smooth look in front. The legs were pretty short, but because I had tights on underneath, their length was okay. The final piece was a light jacket, in the same color as the shorts with matching scalloping on the cuffs and bottom of the jacket. The shorts and jacket were items she'd used for walking, so they were made of cotton with a bit of spandex for stretch. Although, it wasn't what I had imagined, I could see how the outfit would work for golf. As I was trying on the golf outfit, Emily noticed that I had already chipped a fingernail. It was almost time for her to get her nails redone, so she suggested we both go and get new colors Because I had embraced my new femininity full time, she also wanted me to get some extensions. Nothing very long, probably just a half inch or so. It would just give my hands a more womanly look. Emily also suggested I go with a richer color this time, perhaps a cinnamon red, maybe with some sparkle. I wanted to protest, more because of the cost, but I understood that Emily was really beginning to like how we could do things together, as girls, we never could before. So reluctantly, I agreed. Our plans were to go the salon in the early afternoon and then head over to the art gallery. The major question was what to wear. We discussed several option, while looking in our closet. We wanted something simple for the salon but something we could dress up for the gallery. Finally, Emily decided on having us wear similar outfits. The base of our outfits were pull-on, stretch Capri pants, hers in white, mine in black. She paired hers with a blue, silk sleeveless top, while I wore the same style in red. We'd wear these as is to go to the salon, but later for the gallery we'd add short cropped jackets that matched our pants. Emily wore white underwear and mine were black. Our shoes were high-heel sandals that would show off our new pedicures. The final touches were lots of accessory jewelry and small wristlet purses, white for her and black for me. I was amazed at how she created similar outfits but in different sizes. She admitted she found certain styles she always wanted to wear, so she had those no matter what size she was. Emily sort of blushed too, as she confessed that sometimes she felt like she had a shopping addiction. I could tell that was another reason that my wearing her 'thin' clothes made her feel good. In the back of my mind, I had always known she loved to shop. I mean we had a three bedroom house and until recently, my male clothes were no more than quarter of one of the walk-in closets. Now that I had her 'thin' clothes, they all held only female clothes. With our outfits planned, we started to get ready. Both of us needed to shave our legs and underarms, so we took showers. I also washed my hair, as I wanted Emily to help me blow dry it. The next hour we got ready. It felt both odd and intimate to sit down next to Emily, in our bra and panty, at the vanity, to do our makeup and hair. She gave me nice little tips, and corrected mistakes as I gingerly applied mine. She had suggested I go with a smoky eye shadow that would go well with my new cinnamon lips and nails. I really worked on my hair, as I wanted Tiffany to like it if she saw me. First blow drying, then a curling iron, and finally hair spray to hold it all in place. When we were finished, I felt good about how I looked even with the nude lipstick I wore just for the trip to the salon. We quickly got dressed. I liked how the outfits were comfortable, and agreed we looked simple but classy. I wore almost all my jewelry, and especially liked how my sparkly ankle bracelet caught the light as I moved. This time the trip to the salon did not make me anxious. I was even eager to see how the fingernail extensions would look. We spent over an hour at the salon, partly because we were so chatty, but also because Tiffany was so happy at how nice I looked. She complimented me on my hair and makeup and agreed that I needed longer nails. She lobbied for a full inch gel nails, and got her way. She was confident I'd adjust to them easily and quickly, as I seemed to be naturally feminine. That assessment both made me feel good and a bit uncomfortable. If I appeared that way to a casual acquaintance, how did those that knew me better see me? Did I always have a feminine persona that I kept under some sort of masculine false front? Certainly, my interactions with Ham agreed with that assessment. That thought disappeared as soon, as I saw how the rich red lipstick and nail polish changed my look. The longer nails made my fingers look so much more feminine, especially with my rings and bracelet as accessories. I felt like a million bucks as we drove to the gallery. Emily was sure our friend would be there and was excited to show her the new me. We got to the area a little early, so Emily suggested we go into some of the nearby shops. We spent the next hour looking at shoes, clothes, and accessories. In one small specialty shop, she found a glittery, cocktail dress in silver and a pencil skirt in black that she just loved. Emily said the dress would be perfect for me, and she needed a skirt. But I had to point out to her that she had already had a skirt almost identical to this one, and questioned when or where I would ever wear such a party dress. Not to be deterred, she told me she wanted to buy it for me, as a gift. I loved the sentiment, but inside I was worried because it was expensive. When I worked as a manager, I had lots of cash flow and Emily never had to worry about money. She loved to shop and buy me presents, even though it was lost on her that I was in reality paying for them all. Now that my income was gone, I saw this as a potential problem. Finally, I was able to convince her that we should hold off, just in case I couldn't keep my weight down. I told her once I was sure I was stable, we'd come back here for some real shopping. That satisfied her and we went on to the gallery. The next few hours were fun, interesting and surprising. We got a glass of wine and a small plate of snacks and explored the space. It was really a lot bigger than I had expected and quite crowded too, Emily's friend, Dee Ann, was eccentric, adventurous, and totally nonconformist. Her art reflected those spirits and I really enjoyed her paintings. After about a half hour, we ran into her. She looked like she always had, dressed in a bohemian style with lots of artistic flare, including a wide purple streak in her hair. She was excited and happy that Emily had come and gave her a big hug. She gave me a friendly if somewhat distant hello, which we figured out pretty quickly as Dee Ann asked where Dana was. She almost fell over when Emily told her I was Dana. She gave me a quick if intense once over, a big hug, and then kissed us both. She seemed as excited by my transformation as she was seeing Emily. She whispered in Emily's ear several times, which led to fits of giggling by both. As she left, Dee Ann made us promise to have dinner with her one night at her loft, as she had to know all the details. With a second glass of wine, we continued to look at paintings. Knowing her like we did, we saw a lot of Dee Ann's experiences in her work. For example, Dee Ann made no secret of the fact she like women as well as men. That flavor was evident in a large painting, ostensibly of naked arms, and legs intertwined. But, if you looked closely, in a certain way, you could see vaginas and penises, created by the overlapping limbs, sort of like a looking at a 3-D image. We had been standing there, examining the piece for some time, when we heard someone clear their throat. Looking to Emily's left we saw two young men, probably 15 years our juniors. Very handsome, dressed a little oddly, sort of a mix of hipster and cool jam. The taller one had a beard, while the other one, had a mustache. They were each holding two glasses of wine and smiling. "Hello, I'm Jansen and this is Leonard. We couldn't help but notice your interest in this painting. It's a favorite of ours too. We also saw your empty wine glasses, so we took the initiative to bring you a fresh glass. Would you like it?" Each of them held out a glass to us. It was clear this was a pickup move, although a very nice one. Emily seemed especially pleased by the attention of this two young studs. "Well thank you, that's very nice. I'm Emily and my friend is Dana. I do find the painting intriguing and for me so reflective of the artist. It seems like the more you look, the deeper it gets. She's like that too." "Oh, I totally agree. We met Dee Ann a few years ago, when we moved into the condo building. We've become very close friends and love her work. How do you two know her?" Emily explained our past with Dee Ann, and of course the talk led to more general conversations. It hadn't been lost on me that Emily introduced me as her friend. She was very animated with the boys, often touching their arm, or even bumping into them slightly. Emily was definitely flirting and to some degree I guess I was too. She seemed to be encouraging me to have a little fun with this. Having been on their side before, I could sense that Leonard had zeroed in on me, while Jansen had eyes for Emily. After about 30 minutes of conversation, it looked like it was winding down. Jansen shot a look at his friend, who nodded in return, as if it were some sort of prearranged signal. "Emily, Dana, we've loved this conversation, but unfortunately we need to head out to other obligations. I couldn't help but notice you're both wearing wedding bands, but we've not seen your husbands here tonight. Is this just a girls' night out, or something more adventurous? If the latter, Leonard and I would love an opportunity to see you again. You're both so attractive and intelligent, I hate to miss out on a chance to get to know you better. If you're interested, maybe I could call you later this week to see if we might get together?" "Jansen, that is so sweet of you. I mean, you're right this is sort of a girls' night out, but I don't see why we couldn't try for something a little more exciting. Do you Dana? I've really enjoyed talking with men who know so much about art and yet are down to earth. Tell me your cell number and I'll call you so you have mine." I was stunned by how forward Emily was. She sent Jansen her number and as they started to leave, she leaned over and gave him a kiss on the cheek. Of course, I felt obliged to do the same for Leonard. He was grinning ear to ear, and slipped his arm around my waist. Holding me close, he whispered that his heart had been racing from the first time he saw me and now it was flying. As he loosened his grip, he kissed my lips, lightly at first then more forcefully. I was so surprised at how forward he was, I meekly kissed him back, our tongues touching just at our lips. It was such a strange sensation, as we kissed, his surprisingly soft beard rubbing on my skin. They left on cloud nine and once they were out of the building I turned to get some explanation from my wife. Of course, she flipped the script on me. "Well, seems like someone has made more than a new friend. Were his lips as hot as they look?" "Oh hush, what was I to do? You practically invited them back to our house. I can't believe you gave that boy our number and kissed him. What are you up to?" "Relax Dana, I was just having some fun. It was obvious they were looking for some cute, sexy older women, at least older than they were. I found it complimentary that they thought of us as a couple of cute MILFs. Personally, I loved how they thought we were married women out on the town, leaving our husbands at home. I'm sure that made us seem more erotic. It was just some harmless play. I doubt they'll even call. Tell you what, I'll call Dee Ann later this week to see if she knows anything about these two hunks. Is that better?" "Not much, it just seems like you've changed. You're taking more risks, doing things you'd never considered before. It's like you're a new person." "Ha, that's so cute. Coming from someone who at her first cocktail party decided it would be nice to reward her old friend in a very personal way. Not to mention being so eager to stroll around our neighborhood in a very sexy dress and heels. If I didn't like how you've changed I might make the same points. Truth is I like the new you and maybe you'd like the new me, if you give it a chance." With that, she brought her lips to mine and we kissed. I was still a little annoyed at the game she'd played with those boys, way too young I thought. But inside it did make me feel good that such a handsome young man found me attractive too, even if it was just a BS line to get in my panties. We spent another half hour at her gallery, finally saying goodbye to Dee Ann with more hugs and kisses. As we headed back to our car, Emily suggested we stop for some coffee and maybe split a sandwich before we went home. I agreed as the wine had given me a buzz, which I expected Emily did too. We made it home that night shortly after 10. As compensation for her flirting with the boys, Emily wanted us to fuck the old way, after I gave her an orgasm or two with my 'magic mouth'. She lay back on the bed and I crawled between her legs. It didn't take her long to heat up, wiggling and moaning as my tongue worked on her clit. As has been her pattern lately, Emily was much more vocal, encouraging me and purring as her pleasure overwhelmed her. After her second orgasm, she pulled me up, took off my panty, and began to lightly stroke my cock. It felt good but surprisingly a little odd. It seemed like a long time since I had been excited outside of my lingerie. Emily continued to take charge, flipping me over, and mounting me. She worked up and down my cock, grinding her pussy against my body when I was all the way inside her. Not that she didn't take advantage of my breasts being in reach too. She leaned forward multiple times to kiss and suck them, lightly biting my nipples to keep them rock hard. It had seemed like we were fucking forever, but in reality it only took about 5 minutes for me to come. After our recent unusual couplings, intercourse in the normal manner seemed almost anticlimactic. Despite the friction caused by her pussy walls on my cock, my orgasm was disappointing. Perhaps because I came quickly or I had gotten used to being surprised by new approaches. In any case, we took a quick shower, put on our nightgowns, cuddled and talked before falling asleep. Again surprisingly, we both wanted to talk about our earlier incident with the two young men. Emily couldn't quite get over how enamored they seemed with us. For me, I had to confess that in retrospect, I too liked their attention. I also had to admit that I liked her being flirty with other men, even though it was a blow to my masculinity, it seemed to empower my feminine needs. Although I didn't tell her, I kept drifting back to Leonard's kiss. Even worse, I kept trying to imagine what his cock would be like. Little did I know, Emily was thinking the same about Jansen, and she confessed she was secretly jealous that I got a full kiss while she didn't. Eventually we both stopped whispering and fell asleep. This time, I woke up first. Somehow knowing I was going out again with the guys had my nerves building up. I made some coffee and sat thinking about all that I happened. My life had changed so fast in such a short period. It seemed like months ago I was wearing men's clothes. Now I not only dressed as a woman, but my thoughts seemed rooted there as well. I had begun to see myself as only feminine. I guessed it was partly due to constant reminders, like seeing my longer, polished nails as I held my coffee cup. Feeling my silky smooth legs, as I crossed them under my lace nightgown and fluffy robe. Smelling the traces of perfume, makeup, and hair spray that helped create my new image. But it was also, deeper thoughts, like how much more I enjoyed Emily using her new toy on me than I did our intercourse last night. Also, the electric jolt that the touch of man's lips on mine had sparked last night and somehow stayed with me. I not only thought about how I was now living my life differently, but I returned to worrying about our money situation. I hadn't mentioned any of my concerns to Emily and I could tell she would want to go on as she always had. Why wouldn't she? Plus, I knew that my new addiction to feminine things would pull me that way as well. Even though it had only been two visits, I had gotten to where I truly loved going to the salon. Just the pampering alone made it desirable, but also being able to create new looks was thrilling. Despite my throttling Emily's desire to buy more clothes last night, I could feel those urges creeping into my soul too. I kept going back to that darling cocktail dress she wanted me to try on. I wished now that I had. I'd love to have a new sexy dress, maybe to wear to impress a young suitor? But mostly my money worries were about day to day costs, and how quickly those would drain our retirement savings if my income was stagnant. Those thoughts of course, prompted me to think about Annie's proposal. I mean the money sounded great. Just what we'd need until I could get a regular job. But I really doubted that I could do such a thing. I mean I was still convinced that Ham's overreaction was driven more by alcohol and my surprising conversion than any sexual skill. So I didn't think I could duplicate that response in other guys. Plus, could I really do strangers, and several in a row? How could I manage to get them excited? Should I worry about diseases? How could I manage to overlook the illegal aspects of what I would be doing? What would Emily think about this? Would she be shocked or hurt? Should I even tell her? But most important, could I accept myself if I knew I made my living as a professional cocksucker? Would the money be worth knowing I was now a whore, to put it crudely? All I knew at this point, was that I didn't know anything. I had no idea what I would decide to tell Annie, so I just focused on the golf. I would get through that and then talk with her. As I wound down my inner conversation, Emily came into the kitchen, smiling brightly and looking gorgeous. She leaned over to lightly kiss me, before getting some coffee. "Moring honey. Ready for your outing with your friends? I love knowing you're getting back to doing things with them. I had felt guilty when I went out with my girlfriends, knowing you were stuck here. Now, I feel relaxed. What's the plan?" "I'm supposed to meet Hamilton at 9 at the pro shop to get some shoes. I know he offered to pay for them, but I don't feel comfortable with that, so I'll just a pick a pair and pay myself. I will probably let him pay the greens fee since he invited me. Then we tee off at 10, which should get us back at the Club around 1. They'll probably want to do lunch or at least a beer. That'll put me back here at 2 or 2:30. What about you? Anything going on?" She grinned again and looked down at the table. I could see she was fidgeting a bit. "Well after last night, I want to call Dee Ann to find out more about those two cute boys. I didn't mention it last night, but Jansen texted me twice. I also have two more this morning. Nothing of consequence in them, just the sort to show me how much they were attracted to us. I can tell he'll call soon and I want to know more about them before that. Plus I need to do a couple of follow ups for our HOA survey. Then, I also want to take a short run. I need to get in better shape. If I want to catch up to you, I'll need to get started. So having you come back in the early afternoon will be just right." I liked how she had stuff planned, but was caught off-guard by the texts. I told her that was exciting and she showed them to me on her phone. Emily was accurate in her description of them being rather bland, but it was more the hidden message of their attraction that made it so exciting. I decided not to hide my interest this time, telling her I couldn't wait to hear what Dee Ann thought. I wanted Emily to know I wasn't against further contact, especially since they seemed smitten with her. We chatted about them some more, and I could tell she was pleasantly surprised at how I now felt positive about them. Finally, I told her I needed to get ready. I grabbed a bagel and headed to our bedroom to get ready. Since I already knew what I was going to wear, I but on my bra, panty, and the yoga tights. Sitting at our vanity, I steadily fixed my hair and did my makeup. Emily had suggested I go with emerald green eye shadow, with a metallic sparkle. She also suggested I use more mascara, blush and powder than normal since I would be active. It would last longer if it started out a little thicker. So it took a bit longer to get ready, but soon I had the rest of my golf ensemble on. I decide to wear some ankle booties, with a nice stiletto heel and just carry some socks to use with my new golf spikes. I put the socks, some makeup, a hair brush, and a couple kinds of lotion in one of my purses. Although I had been upset when Emily made me carry my first one, it was becoming very clear how nice and convenient they really were. I also liked how you could use them to accessorize your outfit, a sort of crowning touch. I had already decided that was one thing we needed to shop for. I got done just in time to leave, telling Emily to enjoy herself and that I was looking forward to finding out more about our new friends. The drive to the club didn't take long, but I could feel my anxiety building the closer I got. I arrived about ten minutes late and as I pulled into the parking lot, I saw Ham's car. So I parked next to it, got my clubs out of the trunk and headed to the pro shop. It felt very odd, walking in heels carrying the bag. There was the usual bustle of weekend golfing, lots of guys, in pairs or foursomes, going to and from the course. I felt a little exposed, as I was one of only three or four women around. The Club, although technically open to everyone, tended to attract mostly single men, or husbands who would occasionally bring their family. Because of my unique attire, including my heels, I got more than a few stares, mostly appreciative. Finally I entered the shop and saw Ham chatting with a clerk. He grinned when he saw me. "Dana, I was worried you weren't going to show. The guys and I are pretty excited about getting you out on the course. I've told Donnie here, that you need some new spikes, so he's gotten out a few of their best sellers for women. Take a look." I smiled at them and as I got close, Ham gave me a big hug. It felt strange getting that kind of physical contact from someone who would never have done that to me before. Now, he seemed to expect it. It wasn't lost on me, that he pulled my boobs into his chest or that his left hand gave my ass cheek a quick squeeze as he let me go. But I just smiled and started looking at the shoes. I was surprised that many looked like sneakers and most had some colorful trim. I found two I liked and had Donnie bring me those in my size. I tried them both on and quickly decided on a leather pair that looked like saddle shoes. They were white and tan, but with pink accents including the inner lining and a feathery bow across the toe. Unlike my old shoes, they were light weight, with a thin soles, short spikes and low cut along the sides. You could tell they were women's shoes even at a distance. As we were headed to the course from there, I went ahead and put them both on, putting my heels in a side pocket of my golf bag. The only hitch was my wanting to pay for them, luckily they were under a $100 dollars so it wouldn't be too bad. Ham tried to pay, but I refused him at every turn, finally consenting to him paying for my round. He felt like a hero and I knew it was what I wanted all along. We headed to the course. As we walked, I could see more guys check me out and also noticed Ham sort of puffing up, like he was proud I was with him. I continued to be amazed at how quickly and completely he had categorized me as a woman. It was if our previous ten years of friendship never happened. We met up with Brick and Todd at the first tee. They had already gotten a cart and we were scheduled to tee off in a few minutes. I noticed both of them seemed excited but awkward too, as if this was something special. But once we started playing, it seemed like old times. I was still the worst golfer in the group, even though they insisted I be allowed to hit from the ladies tees which were much closer to the greens. The fact that I was now a woman, at least in their eyes, didn't keep them from needling me, although it was much more subdued and G- rated than in the past. The fact that I was still a poor golfer, didn't faze me much, as I was just happy that I could grip the clubs without damaging my new longer nails and that my outfit was fairly functional as well as attractive. I really liked how my new shoes went with everything. Overall I was having a good time, even with Ham's frequent hugs and the odd, sort of longing looks, I was getting from Brick and Todd. Maybe that was a reflection of how abruptly I had left the other evening. We had played through the first thirteen holes and were riding from the green toward the fourteenth tee, when Ham swung the cart down a side path. The path was an infrequently used maintenance access point, which went through a thick grove of evergreen shrubs and pines, very secluded. It had been a spot where, if one of us had to piss before we got back to the clubhouse, we could relieve ourselves. As he guided the cart into our normal stopping spot, I looked around trying to figure out who had to go. But when we stopped, no one got out, they just looked at me. Finally Ham spoke up. "Dana, I want to let you know how much we like having you back in our group. I hope you don't mind me saying this, but you're much more fun now than before. Not to mention cuter. Given that, we have a proposition for you. We all realize how hard it must have been to lose your job. It must have put a strain on your finances. So when Brick told us about your note and offer you made to him the other night, we decided it might be a way we could help." At that point, he took his wallet out, opened it, and began to lay down $100 bills. "Dana, I know you said you wanted to pay for your own spikes, but I won't have it. Here's two hundred for those, plus another two hundred so you can get a new golf outfit or two. We know you ladies want to look nice at all times, so I'm sure you can find more things to wear. Although, I'd vote for something like a golf dress or something similar to what you're wearing now, looks good. But we want you to make this a regular thing, if you find it works for you. Finally, here's three more hundred. That's to sweeten the pot so to speak. Brick said that you needed something on your end to make it worthwhile. I hope this fits the bill. If so, I'd suggest you and him go down the path a ways, while Todd and I stay here. When he's done, then we'll come down one at a time. I'll be last, although I can hardly wait after the last time. I even brought a blanket for you, so you wouldn't get your knees dirty. You know this is a safe spot, no one can see, and we'll be blocking any other carts. So, does sound like a plan that will work for you as well as us?" I sat there, stunned. I could feel my face getting warm, and knew I was blushing a little. The guys were staring at me, intently, as if waiting to hear the results of the big game. I could tell they were anxious about what Ham had proposed, hoping it would be accepted. I had put these kind of thoughts out of my head while we played. Earlier I had decided to tell Annie I declined her offer. But here I was faced with the reality. Stacked in a pile was $700 dollars, easily enough to cover our bills for a few weeks. The lure of the money was strong. But I wasn't sure if I could really deliver. I mean do all three guys, in a row, in the day, without them having any drinks? Could I even satisfy one of them? I was confused and uncertain. I knew Emily and I could use the money, but I was so afraid of disappointing them, not to mention how it would affect me emotionally. They sat there waiting, getting more nervous while I thought about it quietly. Finally I decided. "Ham, that is such a nice offer, you guys too. But I'm not sure this is what you expect. I think you're making our time at the bar to be better and more than it was Ham. I'm afraid it will be a disappointment, but given your eagerness and generosity, how about I try one of you and then we'll see if this is even a good idea at all?" "Okay, if you want. Sure. I'm positive it will be great, but yeah let's just start with Brick." The guys had looked at each other, happy but a little concerned it may not pay off all the way. But Ham gave Brick a thick blanket and he got out of the cart. I stepped out too, but hesitated. I had thought about these kind of moments when I heard the offer from Annie. I had decided that it would likely be best if I could excite a man even before we got to the meat, so to speak, of the action. I knew from personal experience that if I was already sexually excited or hard, it wouldn't take nearly as long as otherwise. So I decided to try that here. "You guys don't mind if I get a little more comfortable do you? I just don't want to take a chance on messing up my clothes." I unzipped my jacket and removed it, sliding it down my arms, before folding it and putting it on the front seat of the cart. That exposed my sheer top and my lace bra underneath. I heard a sharp intake of air from Todd, telling me that my idea was working. Next, I undid the side zip of my shorts, but pulled it only half way down. That made me have to wiggle it down over my hips, allowing me to do a little show as I pulled them down. I had to hold the shorts just right, as I bent over, to work my new shoes through the leg openings. Of course, this meant I was showing off my butt cheeks, as the thong bottom of my blouse was wedged tightly in my crack. After I put the shorts on top of the jacket, I went through a few adjustments, smoothing out my tights, pulling down my blouse, even repositioning my bra. The guys were eyeing me the whole time, a sort of golf strip act. Finally, I was ready. I took my purse, and reached out to take Brick's hand and we went down the golf path around a short curve until we were hidden from view. I could tell he was scared, as there was a tremble in his hands, but he was excited too, if I believed the bulge in his slacks. I put the blanket down and with his help, I knelt down. "Okay James, I'm ready. Are you?" He was so nervous, he just nodded. I think using his first name was a good idea, as it seemed to respond to it differently. I reached out and started to unzip his pants, but he was faster, unbuckling his belt, working the zipper, and then holding open the fly. I wasn't sure how this part would go, but it seemed he wanted me to take it out. So I did, reaching in, sliding my hand underneath his sack and cock, and using the other hand to coax it out. In the light of day, I could see he was average in size. He also was excited, very excited. Once his cock was out of his pants, it stiffened immediately, with a drop of cum, already forming. Seeing that my show had seemed to work, I decided to continue the strategy I had devised when I was considering whether I could do this. "Oh James what a cock! It looks so thick, and strong. And your balls are so big! I can barely hold them in my hand. Umm, you just look so delicious, I swear." As he had fumbled with his belt, I had squirted a small amount of lubricant in my hand. It was a lightly scented, warming sex lube that was edible. I had decided that jerking guys off, like I did Ham, before sucking them would be a good idea and had put it in my purse, before I had decided to tell Annie no. Now, I'd see if it would work. A few slow strokes up and down his rod seemed to be working. His cock twitched and more pre-cum leaked out. So I took the plunge, putting my lips around his cock head, closing them right behind it. I lightly sucked it, sort of following what I had done to Ham, while I pumped him. His reaction was quick, a slow groan escaping his lips and he bucked his hips slightly. I worked over his knob for a few minutes, running my tongue over it, sucking it harder, and playing along the rim. All that fired him up more. Then, making a big show of it, with my eyes focused intently into his, I took his head in my mouth again. However, this time I kept moving, down his shaft, slowly swallowing him. I could see him react, his eyes widening, as I went down further and further. I was moaning too, as if I were tasting a rare treat. Finally, I had him all the way in my mouth and throat. My nose was firmly in his pubes, making it look like I was even further in. I was moving my tongue back and forth, under him, sort of massaging the shaft, while I sucked on the whole thing. I could hear the slurps and moans, mixed in with his sounds. He still seemed in shock that I had taken all of him in my mouth. Having established I could take him, I began a slow pattern of sliding up and then back down his shaft. At the top, I focus on his cockhead, swirling my tongue over it. I even ran my tongue down the shaft and back up, it twitching the whole way. While I worked on his cock, I still held his balls in one hand. I could sense when he was getting more excited, as they would tense up. My pattern established, I began to increase the speed that I went up and down, as well as how hard I sucked his cock head. For me, Brick was surprisingly different than Ham. He tasted less tangy, but with a unique flavor. His juice had more consistency, already being thicker with a stronger odor than any of Ham's. Once I was past these differences, though, sucking his cock was more like Hams. Both were smooth, soft to the touch, but resilient. They both twitched and reacted to almost every move or touch of my mouth and tongue. It was sort of gratifying how easily their cock responded to me, and I immediately felt more control. So I already felt better knowing I could handle a different cock without negative impacts. In a very short period, I felt his balls get really tense, sort of pulling into his body. Anticipating his climax, I focused all my effort on his head and in a few seconds he started to come. Quick, but powerful squirts of come, signaled his orgasm. He filled my mouth about half full, and as he began to emerge from his orgasm, he opened his eyes that had closed when he came. I pulled his cock out to the very tip of my mouth, holding part of the head lightly in my lips. I then swallowed dramatically, twice, as if he had so much it was all I could do to take it in. Then I sucked his head lightly, running my tongue over his slit, as if I were milking his last drop, like it was a magic nectar. Finished, I gently began to put it back in his pants. At this point, now all I was worried about was whether it was good enough. I hesitantly looked at him again. He was smiling, a good sign. "Dana, I don't know what you were worried about. That was fantastic, easily the best I've gotten. Usually when I hear Ham brag about something I take it with a grain of salt. So I was prepared for much less. But this time he was right. I really loved it, and appreciate you doing this. You know I'm still single and although I date regularly, truth is most end without sex, or at least this kind. Personally, there's nothing better than oral and now no one better at it than you. So, I'd suggest you wait right here, and I'll tell Todd its' his turn." With that, he turned and started walking up the path, leaving me on my knees, his taste filling my mouth. I wasn't sure how I felt. I mean it seemed good that I was just as effective on Brick as I was on Ham. It seemed to go smoothly and I didn't feel like gagging or anything. The smell and taste were strong, with that unique semen component, but not like I couldn't handle it. The appreciative comments also made me feel nice. The flip side was it meant I was a good cocksucker, something I had never even entertained as a possible descriptor a week ago. But I little time to ponder that, I wanted to check my face before Todd came. It just took a little cleanup, but I reapplied my lipstick so it looked like new. As I finished, Todd came around the corner. He was walking slowly and seemed surprised I was kneeling. He approached me with a worried look on his face. "Umm hey Dana." "Hi Todd, come on down." "Err, Dana I just wanted to tell you that I always liked you. You were a nice guy, I mean no matter how much we picked on you, you just rolled with it. I liked that about you. But now, it seems different somehow. I guess one way is real obvious how. But this just seems almost like too much. I just wanted to tell you that if this is uncomfortable for you, if you feel pressured to do this, or it's not something that feels right, you don't have to follow through. I mean, you shouldn't feel like you have to do this or anything. I'd be fine if we just finished with our round." This caught me totally off guard. Todd seemed concerned that Ham had sprung this on me, leaving no other option but to do it. Either that or he was uncomfortable. "Todd, that is so sweet of you to ask. I always liked you too, and not just because you rarely teased me like the others. You just have a nice personality. But really I wouldn't have agreed to this if it was a problem. I know Ham seems to get his way and I admit the other night he was pushy and over the line. But not today. I could have easily said no. But I feel the same way, if you are uncomfortable with me, you know with our history and all, I understand too. I know this wouldn't be for every guy. I could see how I may not qualify as a female to some guys, and that's fine. So if you'd rather just go back, get your share of the money, it won't hurt my feelings or change how I like you. Okay? I'm fine whatever." "No, no, I'm good. I just didn't want to be that kind of guy, you know? But if you like it, I'd love the experience. Truthfully, I had a hard time sleeping after Ham told me his plan. I was so excited by the idea I couldn't think of anything else." "In that case, come here and let me see if I can live up to your dreams." He smiled at that, and got close to me. I could sense he was nervous, so I was more active. I undid his pants, and widened his fly. Todd always wore baggy pants, even before it was the style, and these were no different. They were easily two sizes too big in the waist, but they did give me easier access. I could see he wore boxers, so I just plunged in with both hands to try to find his cock and bring it out. Right away, he felt different than the other two. Way different. My right hand went into his boxers and started feeling around, I felt something but it seemed way too big, like I was trying to grab his leg. My left hand had gone lower, ideally to scoop up his ball sack so I could pull it all out together. I found one ball, but it seemed huge, easily filling my fingers. I was puzzled, so I moved my left hand up until I found the base of his cock. I widened my hand to put my fingers around it. I did, but they were so spread apart. He must be huge. I was still wrangling his shaft with my right hand and finally managed to pull it out of his boxers. When his cockhead and then shaft came out, I was speechless. Todd was huge. He must be nine inches, and he wasn't even hard. I put one hand back in to slowly pull out his sack. It was proportionally big too, spilling out of my hand. I just couldn't get over it, as it seemed godly. I could barely wrap my fingers around the shaft. With it fully out of his pants, it began to respond, with the shaft getting stiffer, but not much thicker. As it became rigid, you could see it getting slightly longer too. I just couldn't believe it. I looked up at Todd who had an odd expression on his face. "Todd, what is this? I don't think of ever seen anything like it." "I know, I'm sorry. I should have warned you, but it's difficult to talk about it. I've had to deal with it ever since I was a teen. I understand if you want to change your mind." "Why, it's the biggest cock I've ever seen, I think even including porn movies. Why did I not hear about this before? I'd think you'd have girls crawling all over you." "Not really. I mean I'm not a virgin, but I don't have a lot of experience. More than once, when I get to that point in a relationship and they see it, women have just told me no. It's too big. A few have let me fuck them, but only if I put just part of it inside. I've never had a woman take half of it, let alone all. Sometimes we'd try and it wouldn't be good for her, she try just her hands, but that wasn't any good either. It's just depressing. I mean, I know I only date smaller more petite women, as I couldn't get comfortable with one who was taller than me, but still, it just seems horrible." "Oh honey, it's not horrible at all. It's amazing is what it is. Here let me try and see what I can do." I was really eager to take Todd in my mouth. He was so different than the other guys, it was exciting. I did put some lube on my hands, using both to sort of pump and stroke him. As he got fully erect, his glans almost glowed, it was a deep purple red. I almost imagined he'd taste like grape. But I wrapped my lips around it, slowly beginning to suck on it. It did open my mouth, but luckily it was really more super in length than width. With the head all the way in my mouth, I sucked on it, and worked my tongue, with some difficulty, around his rim. I was finding out, that every cock had a slightly different taste and aroma. I smiled inwardly, because I could taste a hint of body wash type soap. It was clear, Todd was worried about how he would taste. As I sucked, kissed and licked his head, Todd began to react. Still he wasn't leaking pre-cum. I pumped him harder and alternated between having his cock head all the way in my mouth, and running my lips and tongue over the outside of his shaft. Finally I coaxed some pre-cum from him. With him getting more excited, I decided to go for it. I was going to swallow as much as I could. I started by licking all of him, sort of adding salvia to the lube. I then tried to raise up on my knees, so it would be more of a straight shot into me. I spread my lips wide, and slowly began to inch down his shaft, keeping my teeth off of it. Once I got past the head, he started to slide in easier. I felt a little odd, stuffed, you might say and I had to be careful in how I breathed. But I was taking him in, I got what looked to be a third of his shaft in and could feel his cockhead pressing into my throat. I took a few seconds to let my throat adjust to his size and pressure, then I pressed forward. My lips slid over him, my tongue ticking the underside of his shaft, while he went further and further into me. I had more than half down now. Todd was getting ecstatic. He was lightly holding my head, or running his fingers in my hair. He moaned more, with every half inch that disappeared. The whole time, I had to keep sucking, as I was slobbering all over this monster cock. At one point I stopped, as it felt a little uncomfortable. After resting a few seconds, I pushed more of him in. By now, I had about three quarters of his cock in my mouth and down my throat. He was going insane, babbling about how good it was, how I was an angel, a magician, and so sexy. At that point, I decided I had gone far enough, although a part of me wanted to see if I could handle all of him. So I slowly began to slide back up this beautiful cock. As it came out of my mouth, I used my hands to start masturbating him. I wanted Todd to always feel like he was being stimulated. I wanted to give him a new experience. When I finally reached his cockhead, I let it out of my mouth with a noticeable pop. Then like a starving kitten, I licked, licked, and licked it's gloriously purple knob. Todd was moaning loudly now, so I had to whisper to him to be a little less vocal. I also could taste more of his pre-cum, a sure sign he was getting closer. As I licked his cockhead, I had a sudden urge. An urge I didn't experience with James or Hamilton. I wanted to see if I could get one of his giant balls in my mouth. Dropping down from my raised position I fed one of them into my mouth. It was hairy, much hairier than the shaft, but it was also silky smooth. I knew how sensitive they could be, so I sucked with just a minimum of pressure, all the while almost violently pumping his shaft. When I finally released his nut from my mouth, lifted up again to resume working his cock, I was greeted with a huge gob of cum, oozing from his slit. I used the tip of my tongue to recover it. The taste was now sweet, like icing on a doughnut. My urge to suck his balls satisfied, I began to swallow him again. This time it went in so much easier and faster. I got almost to the point I was before, but started back up. I was intent now, on using my mouth to pump him, to pump him dry. I used the approach that had been so successful before. First set up a steady pace, up and down, at a speed I could handle. Once you feel his balls start to tense up, switch back to the most sensitive part, the glans. Suck that cock head till it pops, using you lips, tongue, and mouth. Of course during this all, Todd was not the only one moaning. I had begun to vocalize as soon as I tasted him, often just humming as his big cock was so far into my throat I could do no more. But as he approached climax, I returned to soft, moan similar to a cat purring. It was a sound of joy, satisfaction, and met desire. Those sounds reinforced what Todd was feeling and finally it happened. I felt his whole body go stiff. His hands tight on my head, nothing moving, nothing but his shaft twitching as he ejaculated. I had half-way expected this, but when he started to come, really come, he filled me up quickly. I had to swallow, twice, three times, and finally four. Each time my mouth seemed about to overflow. Perhaps it was also that his cock took so much room, but still it felt like I had swallowed a gallon of his juice. As his orgasm swept over him and left, Todd gradually regained consciousness. I also began to recover, holding just the tip of his glans on my lips, so as to keep any stray drops off my blouse. That allowed me to return to a normal breathing pattern. I felt like I had really worked for him, my jaw muscles were sore, my throat felt stretched and my lips were a little raw. What a wonderful organ. Opening his eyes, he seemed distant. But he reached down to lift me up. Although I knew Ham would be here next, I wanted to get up and stretch anyway, so I let him do it. As I rose up, he wrapped his arms around me and kissed me. Not a soft kiss, but a forceful one, his tongue exploring my mouth. He didn't seem to worry about it being coated with his own semen, but kept kissing me for more than a minute. Finally I broke off. He seemed so happy, just staring into my eyes. "What an angel you are. I can't thank you enough. That was the most realistic, complete orgasm of my life. I felt things and experiences I had only dreamt of before. No women had been so willing, so open to embrace my size. Thank you, oh thank you Dana." I looked at him, a sly grin on my face. "So, you liked it? I was worth it?" Todd only laughed and kissed me again. Then I think he realized that maybe he had crossed the boundary. I mean after all, he had paid for me to suck him off, not kiss and hug him. I was a former friend still married who had turned into an escort and shouldn't have to be so giving without compensation. But as he put his cock away, somehow stuffing it in those baggy pants, I had a sudden longing for it. I really wanted to see if I could take it all. But I knew that would be up to him. I just hoped he liked me enough to give me a second chance. As he walked back up the path, I told him to have Ham wait a second before he came down. I knew my mouth and likely part of my face was a mess. I took a few minutes to wipe off and reapply some makeup, so I looked like I did before. I knew Ham would not want to see me as used, I had to be fresh for him too. After the previous two men, I made quick work with Ham. I knew more about him, and he succumbed easily to my tricks. He still shot a fair amount of come and he seemed to really like my work. Since I knew how he thought of himself as a stud, I made sure to brag on him. I sort of whispered that he gave me more than the other two combined. When he finished, I once again cleaned up. He retrieved the blanket and we walked together to the cart. After showing off just a little more, I wiggled the shorts back up over my hips and zipped them in place. But I didn't put on the jacket, as I was quite warm from all my activity. I was feeling pretty good about everything. First, I proved it wasn't just the booze or the moment. I was pretty good at this. Second, I handled three guys, in a row, with no break. Plus I found, at least with Todd, that it could be pretty exciting for me too. But the real moment of Zen, was when Ham handed me the stack of hundred dollar bills. I held it briefly before slipping it in my purse. At that point, I realized I had made all that money in less than a half hour. The next few holes I played pretty good, even having the best score on seventeen, the first time I had ever beat all three of them. I wanted to think I was getting better, but I knew that being able to see my bra and my boobs through the sheer blouse, likely was a significant distraction. When we finished the last hole, Brick went to take the cart back, while we checked out. Ham was going to take his clubs to his car and I was able to get him to drop mine in the back seat of my car which was unlocked. They all wanted to meet for lunch, which was fine for me. I just had to run a quick errand first. I had switched out my spikes for my ankle boots. Before I went to see Annie, I went to the bathroom. I wanted to clean up a little, redo my makeup, brush my hair, use a little perfume, plus I needed to pee. Sitting there, holding my cock while I went, I just knew I wasn't like those guys any more. Somehow holding their cocks, felt like I was holding a man's organ. When I held mine, it gave me an entirely different vibe. I guess to me, it felt closer to a girl's clit than a penis. I was uncertain now about what I would tell Annie. Before the round of golf, it was clear. I couldn't really do what she wanted. But now, maybe? I mean that stack of hundreds felt really good, and even after doing all three guys, I felt like I could have handle a few more. Would that be enough? What if someone found out? I guess I'd have to tell Emily. Would she freak out? Maybe I needed a drink first. So, I checked my face one more time after I put my 'clit' back in its panties. Then I went out to find Annie. The bar at the pub was pretty slow and Annie was standing there talking to the bartender. She saw me approach, and came over to me, all smiles. "Hey girl, I like that look. Kind of risqu? but not." "Hi Annie, I put it together to play some golf. I hadn't really played in a while, so I had to make do. The guys seemed to like it though." "Which guys?" "Oh Ham and his buddies." "Sounds like fun. So did you think any more about my proposal? It's up to 30 guys by the way and I've not even talked to all of my potentials. Of course, not all would be weekly regulars, but I bet you could get a dozen or so. The others would be once a month more or less. You just have to make it through that first round, as almost everyone wanted to try it as soon as possible. We'd just have to pick a couple other days besides Tuesday and Thursday to work them in. Do you want to go for it?" I had still been on the fence when I came in the bar. I could see how the money would solve so many problems. But it would mean accepting that I was a sex worker and not a glamorous one like in the movies. It might seem okay now, but after a few weeks would it be repulsive? How would it affect how I feel about myself? I decided I did need a drink. Especially since I could still taste the guys. "Annie, this is a big decision. How about one of your shot and wine combos?" "Sure, why don't you go sit at that booth and then we can chat while you drink." I went to the booth she suggested, it was in the back and sort of private. She brought the drinks. I quickly did the shot, the peach schnapps clearing away some of the slick feeling in my mouth. I took a sip of wine, too. I had decided to be totally honest with Annie, well almost totally. "Annie this is a great proposal. It would solve so many financial issues for me right now. But I need to tell you something. I'm not an escort. I don't do this kind of stuff for a living. So much of my hesitation comes from not knowing if I could really do this on a regular basis. You know doing one or even a few guys, isn't the same as having a stable of men to service. I worry about the other ramifications of this choice, like how my partner would feel. Plus it has risks, both legal and disease-wise. But in other ways, it sounds so exciting. Plus, after this morning, I can't deny I seem to be good at it." "Wow, I didn't realize you weren't a pro. I just assumed since you were with Ham, did him like the others, only better, and the way you teased them with your body that you were comfortable with it. That it was your lifestyle. But what do you mean about this morning?" I chuckled and looked down at the table. Then took another sip of wine. "Well turns out, the guys wanted me to play more than a round of gold. They all wanted what Ham got the other night. I felt sort of trapped, plus I wanted to know if it was just a fluke with Ham. Well it wasn't a fluke and it was actually easier in some ways than I expected. But I still have worries about going pro, so to speak." "Okay, I understand and respect that. But if you've found that you do have a special skill, that's a very profitable skill, seems like a waste not to use it. Especially if you need money. I can remove a couple worries. First, we never have cops here, and we've got ways to isolate your actions from the money. I know all these guys, probably better than they realize. Their professionals, family men, and part of the inner social echelons of town. I wouldn't see any of them as having disease issues. In fact, I could probably get them to give me some sort of 'medical clearance' that they were clean, as a prerequisite. But I understand your other concerns. Tell you what, I'll modify my proposal. I'll line up enough men for Tuesday night that might represent a potential regular crowd. You can try it out, see how it goes, and then decide. Plus, you're not signing a contract or commitment. You can always say enough, at any time, and it will all go away. What do you think?" I took another drink of wine. I could feel a buzz starting to build, as I normally never drank this early in the day. A buzz that reminded me how I felt when Todd started shooting his stuff. "Okay, what the hell. I'll do it. I've never been afraid to try before and I agree it would be a waste if it's something that I can make work. Set me up for Tuesday." Annie was all smiles now, and reached over to squeeze my hand. She told me she'd call to let me know the details and was pretty sure I was making the right choice. But she did encourage me to tell my partner first. This isn't the sort of thing you want him to hear from someone else. I didn't tell her my partner was a woman, but I agreed. All we needed to do now, was talk with Stewart. So she went to see if he was available. Returning in a few minutes, she waved me over to the bar. "He's in his office, back there. Just go and knock, he'll let you in. Stewart's real private, but just listen and I'm sure he'll make this work for us. He's a good boss." I went down the hall and knocked on the door, entering when he said to. Stewart was sitting behind a regular desk, papers scattered over the top, with a laptop computer and phone to one side. He was average looking guy, blonde hair, short and parted down the middle. Short mustache not readily visible because of the blonde hair, brown eyes, and light skin. He was wearing a dress shirt, slacks, but no tie. He didn't smile, looking me over, before motioning me to sit in the small chair in front of his desk. I decided to try to break the ice. "Hello, I'm Dana, Annie told me." "Yes, I know. She's kept me informed of her proposal to you. I guess this means you've accepted, which is fine. My focus is on the bar and pub, keeping them profitable, and out of trouble. As long as you help with those goals, we'll get along okay. I trust Annie, she's been here a long time and is a top notch waitress. So, if she thinks you're okay, then you've got that going for you. But I've a few requirements I want you to understand. First, no exchange of money in the bar or pub. In fact, I'd suggest you let Annie handle cash, and cash only, for your services. You can collect from her at the end of your shift, that way you'll avoid disputes with customers. As a waitress, everyone expects her to handle money, so it looks fine all around. Second, no propositioning of customers on site. Again, let Annie line up your customers, she knows our clientele and can keep it all low key. Third, no discussion of what you're doing, who's seeing you, or any of your business activities, while you're here. Don't use language normal to your work. You're a service provider, not an escort, hooker, or anything else. You have customers, not johns, marks, or sheep. The less out there, the smaller the chances for problems. Fourth, no outrageous outfits or behaviors. The other night, you were dressed sexy, but classy. Nice dress, shoes, hose, looking more like a customer than an escort. Only you're behavior, flashing your rear was an issue. Avoid that from now on. Fifth, I know Annie is doing this mostly for tips and bigger tabs, but consider giving her something extra, amounts or percentages are between you two. She will be doing a lot for you to make it easier and safer. Appreciate her. That should be about it, any questions?" "No, not now. I see no problems with any of that. I like your approach to keep it low key and under the table. I have no more desire to see this spread or become highly visible than you do. Also, I'll talk to Annie, as I agree she'll be irreplaceable. But there is one thing, you didn't mention, that Annie brought up. I know your focus is the success of the bar, but shouldn't I let you verify the quality of my services?" He looked at me again. Then he got up from behind the desk, as if he were going to leave. Then he smiled, for the first time. "Very good. I wanted you to offer some compensation for how accessible I'm making this for you. I won't need it often, but when I do this is what I want. I'm going out for a minute, when I return I want you undressed. You can put your clothes in the bag under my desk, then you can crawl under there and wait for me. When I return, you can fulfill your obligations." "Undressed?" "Yes, I want you naked." "Well, I'll strip down to my panties, but no further." My heart was racing at his point, first from the odd request, but more so because I couldn't take the chance of being fully nude in front of anyone. My secret might be revealed. "Fine, in your panties." He left and although somewhat relieved, my heart was still pounding away. I didn't hesitate though. I found the bag, undressed and put my things in it. Crawling under the desk was more humiliating than it sounded. Waiting was worse, as I began to imagine all kinds of horrible things mostly that this was a setup and it would be the police that would return, taking me to jail, in my undressed state. It was dark and cramped. I had to rest on my knees, with my back bent over, which made my boobs hang down. Finally I heard the door open. I could only see his shoes and lower pant legs, but as he pulled out the chair and sat down I knew it was him. Stewart wasted little time, unbuckling his pants and taking out his dick. Moving his chair even closer, he had me pinned against the back of his desk, so it was pretty clear I should start. I used my routine, stroking him first and then taking only his cockhead in my mouth. It was so dark under his desk, so I hadn't realized he was uncircumcised until I felt him with my tongue. He had a very strong taste, not unpleasant but different. It was interesting to tease his cockhead out of its sheath. I then began to suck, lick, and pump him in the ways that had worked well earlier. I felt like I was getting him close when the phone rang, I stopped momentarily when he began to talk, but he reached down to wave me on. So I resumed my work. He talked like nothing unusual was happening, managing to hide his excitement in his voice, but not his cock. Somehow talking to someone while I did him, made it better. Finally he hung up the phone. But within a minute, I heard knock on the door, and he told them to enter. This time I didn't stop, I knew what he wanted. The visitor sat in the chair where I had been and began to talk. It was Annie and she was going over details of the pub plans for the rest of the day. I couldn't believe it but he sounded level, under control, and as if nothing were happening. But it was, about half way into the conversation, he began to come, filling my mouth. As he wound down, I continued to suck him, trying to drain the last bit from his cock. Finally, Annie left and it was just the two of us. He rolled the chair back, prompting me to release his cock which he put back in his pants. "You can come out now. Very nice." I slowly emerged and wasn't sure if he was talking about my blowjob or my semi-nude body. He reached out and fondled a breast, rolling the nipple between his thumb and forefinger. I just sat back on the edge of his desk facing him, holding the bag with my clothes. He looked me over some more, and put his other hand on my other breast, so he was feeling them both. "I think you will be very successful here. You follow directions well and stick to your task. Annie told me you were an expert cocksucker and you'll get no argument from me. You can get dressed now." At that point, he stopped feeling me, but he did watch me get dressed intently. When I was fully dressed, he waved me out of his office. I emerged and decided to try to find the boys, after I redid my makeup, in the employee restroom, for what seemed like the umpteen time today. They were well into their second drink. I joined them, ate a sandwich and had another glass of wine. I was feeling excited but nervous about accepting Annie's proposal, so I was lost in thought the first time he asked, only barely hearing it the second time. "Oh, sorry Hamilton, I didn't quite hear you." "I just asked if you were up for a round of golf next week. We enjoyed it so much we'd like to make it a regular thing, you know every week." "Every week, I'm not sure if I could make it that often. Especially on weekend mornings." "We could do it during the week. Would Friday work?" "Yes, Friday morning would be better James, but maybe it would be better once a month. I mean I had a good time, but still I'm not as in to golf as you guys." "How about if we make it $200 each? Could we do every week then?" I glanced quickly at Todd. I had thought they just meant golf. But they wanted to repeat it, all of it. My mind was going now. If I could handle it, this would be perfect. Start with $600 quick ones in the morning, and be ready for extra customers from Annie in the afternoon. I smiled at Todd and put my hand on his. "Well, since you asked so nicely Todd. Sure, I can do it then. So, it's a date then, Friday at 10 am, just our little foursome. I'll try to find some pretty little golf outfit for the occasion, something appropriate, for the whole event." Todd smiled broadly, although I could see the other two weren't quite as happy with his offer. But what the hell, they could all afford it and where else would they get such skill? I said goodbye and went to my car. I was starting to get nervous about telling Emily. When I got there, I could hear her in the shower. She must have just finished her run. I had tried to think about how to break the news to her, even rehearsing a few lines. But I just couldn't figure out how to tell her I was becoming a hooker. But first I needed a shower too. I stripped off my clothes, leaving them in the hamper. I didn't want to scare Emily but thought maybe we could share. "Honey, I'm home. You almost done, or could you use some company?" She stuck her head out from behind the glass door of our walk-in shower. Must have been a good day, as she was beaming. "Company sounds good, come on in." I put my towel next to hers, and entered the shower. She moved to hold me and we kissed, rubbing against each other. After a minute or so, she stepped back. I could tell she had just shampooed her hair, and was soaping up her body. So, I took the washcloth and started on her back. She was humming, always a good sign. When I finished her backside, with lots of attention on her butt, she turned around to face me. Spreading her arms wide, she allowed me to gently wash her breasts, stomach, and down between her legs. She giggled and whispered to wait till later. Emily rinsed off, including the conditioner from her hair and left to dry off. Assuming we were staying in because of her wet hair, I shampooed and conditioned mine as well. Then washed my body and face, removing all my makeup. I finished with a quick shave of my face. I had gotten where I hated to have even the tiniest stubble any more, even if it was so short as to not be noticeable. After I dried off and wrapped my hair in a towel, I grabbed a robe to join her on the bed. Emily was propped up on some pillows, smiling slyly and checking her phone. I crawled up next to her, prompting her to lean over to kiss me. I loved moments like this, but was nervous inside because of what I had agreed to do. I would have to find just the right time to talk about it with her. If we had a relaxing, stay-in evening, maybe I could tell her then. But for now, I sensed she wanted to tell me something. "Well how was your day? Did you get the HOA information? How was your run? You seem pleased." "I am pleased, but I didn't get everything done I wanted. I cut short my run, because I was limited on time, and it was harder than I remembered." She laughed as she said the last part, but was still smiling. "Just starting again, is the main thing. Maybe I can join you next time, although I may not be able to keep up. I haven't even jogged in a long time." "Okay, it's a deal. So, how was your golf game? Things work out better this time with the guys?" "I'll tell you more later on, but we did work it out to everyone's satisfaction. But I almost forgot, did you call Dee?" "I was going to, but surprisingly she called me first. Seems she is having an after party tonight at a club near the gallery. It's a celebration for how well her exhibit went. She invited us to come. Dee was so excited about the new you. We talked about it for a long time. She admitted she watched us a little at the gallery after we talked with her." "A party? Tonight? What did you tell her?" "I accepted of course. I figured it would be a perfect time. Plus, she gave the scoop on Jansen and Leonard. She thinks they are wonderful. Very interesting, intelligent, and friendly. Turns out they both work for a non-profit group helping the homeless, especially veterans. She said they had golden souls - ha, you know how she talks." "When is the party?" "It really doesn't start to around 10, so we have time to rest and get ready. I think it will be lots of fun. But, Dee had some other interesting news about the boys. Seems, soon after they moved into her building, she hooked up with them. Both. At the same time. She was very impressed. Says, they are wonderful lovers, very attentive, and bigger than average. Dee highly encouraged us to have a fling, again her words." "Sounds like her, she always seemed to work in sex with her new friends. Sort of a short cut to getting to know them. But I don't know about us having a fling." "I know, it seems more like her than us. But we can figure that out as we go, because after I talked to Dee, Jansen called. We talked for a while. He really does seem like a nice boy. Seems Dee called him, told him about the party, and suggested he invite us. So he did, meaning we have dates with them for the party. They're coming by to pick us up about 9:30." "Dates? Isn't this a little fast. Plus, I'm not sure I'm comfortable being in that kind of situation with a guy." "Come on Dana. It's just a date. I mean you seemed to have no problems kissing Leonard before. And before you protest, I saw you respond, it wasn't just one-sided. The way you closed your eyes, tilted your head back, and moved your lips on his, it was pretty clear you liked it. Besides, I know you're getting more intimate with men. Oh, by the way, Annie called again. Seems she lost your cell phone number, and Ham gave her our house phone. We had a nice talk." "You talked with Annie? Well, I..." "Yes we had a nice talk. She was surprised that your partner was a woman. She thought you were worried about your boyfriend finding out about her proposal. Seems you two agreed on a plan that will benefit both of you. I hadn't realized you were serious about that. When did you make that decision?" I was panicked now. This wasn't how I wanted to present it to her. I was hoping to work up to it. But not now. "To be honest, it wasn't until after I played golf with the guys. Turns out they had more than golf in mind. This time I didn't feel trapped, but there was pressure. But once I started everything went well, very well. And the stack of cash they gave me was sort of alluring. That's what I meant by an arrangement earlier. They want me to golf with them every week, for $600. I just couldn't pass on that. So once I made that decision, agreeing with Annie's proposal, at least to give it a try, seemed doable. Emily, I haven't told you this, but I'm no longer getting paid. We were going to be running out of cash soon, like next week. I had no job prospects. This seemed like the only solution. If not for the money, I wouldn't consider it. I was just trying to figure out how to tell you." Emily moved close again, reaching into my robe to fondle my breast, gently, sensitively, as only a woman who knows the feeling herself, could do. She also kissed me. A deep soulful kiss, her tongue playing in my mouth and inviting my tongue into hers. I noticed how soft her lips were, soft and inviting. After a minute or so, she broke her kiss, but stayed close to my face and whispered, as if she and I were in a crowded room and she was sharing a secret. "Dana. Don't you trust me? I trust you, so if this is what feels right, then I'm fine with it. I mean it seems clear that you have oral talents that can please men or women. Personally, I think it is part of your inner femininity expressing itself. From what you've told me, I can see financially it will be very beneficial too. So relax, I'm fine with you utilizing your natural talents. But I need you to realize, I want to express some of my inner needs. I mean being with you and having sex in a new way, has reawakened my sexual urges. I want to explore life in new ways, and bring you along too. So given what's happened today, I expect you to have a great time tonight on our date. Besides I have a surprise for you. Wait there." Emily got off the bed, and went to the closet. She emerged holding a pair of strappy heels and a cocktail dress, both in silver. The dress was the one she wanted me to have before. "See, I knew this dress was destined for you. I have several nice dresses to wear to a club, but you didn't. So I went back to the shop, got these and some accessories so you'll look hot tonight. Take off that robe and try it on for me." I took off my robe and stood up. I felt a little awkward as my cock had stiffen from Emily's touch, but she didn't seem to care. She removed the dress and help me pull it on over my head. The design was like a baby doll night gown. It had double spaghetti straps and a lightly elasticized top that clung to my body, just above my nipples. The rest just hung down, loosely but only reaching just below my crotch, which now left my cock expose. Because the fabric was a silky, metallic silver, it seemed to float and swirl around my body. Emily was smiling. "I knew it would look great on you. Most of your dresses are form fitting, tight against you to show off your body. This is different, because it seems barely attached to you. It will definitely catch the eyes of the boys. You could go braless, but I think your strapless bra would be perfect. It's a lovely soft rose color, with a touch of lace, and of course, is your favorite style, a pushup. It should show off your breasts wonderfully, even if it peeks out occasionally when you dance." I saw what she meant in the mirror, but it looked way too short. Because the fabric was so light, the slightest movement caused it to swirl, showing the curve of my butt or my crotch. "Emily isn't it too short? I mean, it really doesn't cover anything." "That's the point. A dress like this is meant to emphasize your body. With a dress this short, there are a couple of options. One, wear a body suit, so everything is still covered when you move. Two, wear a fancy, pretty pair of panties that hide most of you. Three, wear sheer hosiery that make what's underneath pretty and sexy. That's what you're going to wear. I bought an expensive pair of pantyhose. Sparkly silver metallic, very sheer with a minimal waist band, and no seams. Without seams, the fabric will mold tightly to every curve, crack, and cranny. It will be like your skin is silver. You'll be covered but exposed at the same time. It will look best without a panty underneath." "How can I do that? If you haven't noticed, I seem to have a rather unfeminine part that if the hose really molds to everything, would look very noticeable and out of place." Emily giggle and smirked, in part because as I talked my cock bobbed in front of me, under the hem of my dress. She then held up another smaller bag. "I know, I think I have the answer to that question. You see, when I talked to Dee Ann, she was very inquisitive about your transformation. First thing she wanted to know, was if you had gone all the way. When I told her your situation, we talked about what we were doing. She loved that you were trying to be as fem as possible. She asked about tucking, how to hide it, etc. Turns out, of course, she knows several trannies and they talk about their secrets. So she suggested I go to this shop, near the gallery that caterers to that crowd. That's where I found this." She pulled something out of the bag. It was a light flesh color, not very wide but long, like a rectangle. As she held it, I could see what it was. It looked all in the world, like a fake pussy, with both outer and inner labia. As she realized I recognized it she laughed. "Isn't it a hoot? It's just like a girl, except no vagina. It's designed so you can tuck you penis into a rubber sleeve that actually has a hole in the end to let you pee. Then you attach it using medical glue and there you go, no cock but now a pussy. She says her trans friends use it for special occasions. In the right light, it looks real and covers all your stuff. It will be perfect under your pantyhose. Plus it will stay put until you use the solvent to remove the glue, so it will never come loose while you're out and about. Let's try it, I can't wait to see how you look." "I don't know. Sounds uncomfortable, plus I don't know about having chemicals that near my junk." "Oh come on, it can't be much different than having a panty tightly hold your cock back, can it? Besides its medical grade, all around, including the chems. Let's try it, take off your dress and lay down on the bed." I reluctantly did as she asked. Emily positioned it where she thought it would go and it lined up pretty well with the top right next to my small triangle of pubic hair. Following the instructions the clerk gave her, she applied glue to the form, lined up and pressed down. That put some glue on me sort of showing where more glue was needed. Emily then applied more to the form and the area around my cock. While she waited for it to get tacky, she worked my cock into the rubber sleeve on the inside. It went in with a little problem, but she had it lined up with the hole. When she was ready to attach it, she had me push my balls inside while she pressed the form on me. I then held it for a few minutes, while she worked a spandex control brief up my legs. With everything lined up, she pulled the brief all the way. It fit tightly, holding my form against me while the glue set. I lay there another 15 minutes, before Emily would let me sit up. At that point, she wanted to let it really attach, so she suggested we roll our hair, and try to take a quick nap. It didn't take her long to put medium size rollers in my hair, rolled up just to my ears, so I would have tighter curls tonight. She then put a few in her hair, mostly to give her big loose waves. By now, even with the excitement of all that was planned, I was getting sleepy. So we shut the curtains, and crawled under the covers, next to each other. My mind was stilling tumbling over all that was happening, but somehow I fell asleep anyway. Next thing, Emily was gently kissing my cheek telling me it was time to get up. I looked at the clock, and we had managed a good 2 hour nap. I pulled on my robe, and followed her to the kitchen. She had made us a salad to eat, so we sat there, talking about the plans for the evening, while we ate. Refreshed and refueled, we went back to the bedroom. We had about an hour to get ready. The first thing, was to take off the control brief and see how I looked. The form was well attached, all the edges were smoothly glued to me. There was a definite difference in color, so it was noticeable. But once, I slipped on a sheer panty, the difference was minor, whereas the shape was still visible. With my 'pussy' firmly in place, Emily and I began to do our makeup and hair. She wanted to do my face, as she insisted I look my best. She applied my usual cosmetics, but used silver and gray eye shadows, false eyelashes, and a slightly darker blush. I had to admit when she finished, I felt I looked the best I had so far. I took out my hair rollers, brushed everything into place, and set it all with hair spray. Even though, it had been just a week, I was beginning to get comfortable with many of these tasks. Emily did her makeup in a similarly evening look. She had decided to put her hair in an up-do, with loose curls around her face. She worked on it and it looked so elegant. A few more touches and we were ready to get dressed. I watched her, as she got ready. She had decided to wear a long, halter dress in red that featured a very high slit in front. I wasn't surprised that she opted for no bra, as the dress was backless. But after pulling on a pair of black thigh-high stockings, she started putting on the dress. I looked at her questioningly. "Emily aren't you wearing panties?" "Not tonight. One of the things I love about this dress, is how you can maneuver the front slit for your advantage. If I sit just right, or cross my legs just so, or hold it in a certain way when I get out of a car, it gives you a brief glimpse of my pussy. I could wear a pretty panty, or small thong, but both would break up the smooth lines when I'm standing. Plus, if this is a much fun as I hope it is, I might just want to show off a little for Jansen. He's such a cute boy. I know it seems pretty risqu?, but I suggest you reserve judgement until you're dressed." Given her advice, I let it go. I put on my bra, the pushup pads giving me lots of lift. Emily handed me the package of stockings, telling me to be very careful putting them on. I took off my panty sat on the bed, and began to work them up my legs. The sheer silver of the nylon made my legs glow. As I worked it up, over my hips and around my waist, I saw what she meant by how the fabric really formed to your body. Without a seam or gusset, the nylon slid into the valley between my cheeks, between my thighs and the outer edge of my fake pussy, and even in between the false labia. You could see my whole body, shimmering in silver, except for the narrow, lace waist band. I was stunned. Anyone looking at me from the front would swear I had a full woman's body, with a complete pussy. I slipped the dress on over my head and put on my sandals. A few quick turns in front of the mirror, revealed how when the dress moved, it gave glimpses of my 'pussy', even more so than Emily's dress. I smiled and looked over at her. "Well, I guess we're going to give both the boys a show. I have to admit I love it. I feel so sexy and complete. When Ham had me trapped in the stall that first day, I was so panicked that he'd see my cock. With this little thing, I look like a real woman, no matter how much I show." Emily laughed and came to me. She lightly ran her hand over my crotch, using her fingers to outline the silvery, folds of my 'pussy'. She then took my hand and had me feel. "Oh my god, it even feels like a woman. I was worried about this date, now I can be more relaxed. No matter what happens, I'll be good." We smiled and air kissed, to avoid messing up our makeup. It was almost time for the boys to arrive, so we finished up. Emily had a black wristlet purse, just big enough for her ID, our house key, and some of her makeup. Mine was a bit larger, being a silver cross body bag, with a long, fine link chain. I put my ID, although it bore no resemblance to me at all anymore, some cash, a compact, mascara, and lipstick. I was checking myself in the mirror, one more time, when the doorbell rang. They were here. Emily looked at me, and smiled. "Dana, before we go, put that anal lube in your purse. I want to make sure we're ready for anything tonight." "Lube, really?" "Yes, silly, it's like when you were single, you never went out on the town without a condom in your wallet. But now, some lube is more appropriate. In the heat of the moment, it's better to be ready than not." As she said that, I saw her drop her diaphragm into her purse, a sly smile on her face. With that she turned and started toward the door. I watched her glide effortlessly, her ankle strap sandals made her legs look so long, as they flashed out of the slit in her dress. Her long dangling earrings bounced around her neck, her hair piled on top, making her look like a girl going to a prom. I could see how the dress molded to her ass, each cheek wiggling as she walked. It was pretty clear she had no panties, as not a line was visible. The back was cut so low, it almost touched the top of her ass. All I could think of was Jansen sliding his hand down inside there. I know if she were my date, and we were at all flirty, I'd be tempted. The whole scene seemed surreal. Watching my wife opening the door to our house, letting in two boys, well young men, who I'm sure had the same intentions every man has when he takes a woman out on the town: have fun, party, and get laid. I slowly walked toward the three of them. This seemed to be as big a threshold to cross as the one I had with Ham. Emily was clearly excited. She hugged both of them, Leonard first and then stayed with Jansen, her hand lightly around his waist. They were dressed in nice suits, no ties, but very stylish. Leonard was staring at me, a big smile forming on his face. As I joined them, he gave me a hug, intimate, but not too tight. Sort of a hello, you look gorgeous, can we fuck later, type of hug. I smiled at him, and let him keep his arm around me. We made small talk for a little bit. The guys complimenting us on how great we looked, what a nice house, and so on. Jansen sort of glanced around, and I sensed he was looking for something, a picture, memento, or some sign. Then it hit me, Emily had said our husbands were not with us at the gallery. Was he worried one of them would be here? I guess Emily had the same thought. "I really appreciate your offer to come pick us up, Jansen. I wouldn't have had nearly as much fun, if knew I had to drive home. My husband doesn't like me to drive when I go out. He knows I'm a terrible driver when I've had a drink or two." "Your husband? Is he here?" "Oh no. He's over at Dana's house. They were going to watch the game tonight. They're nice guys, stable, good providers, but not really into any nightlife. At their age, they're not into dancing, or late nights. They know that Dana and I have more fun on our own. I guess they trust us to come home again. Truthfully, we've found that younger men, more active men, more virile men, are better suited to such things. That's why we appreciated, you and Leonard offering to escort us to Dee Ann's party. We've been so excited all day. I just hope we can keep up with two. We're not as young as we used to be, but we love to dance and have fun." "Oh, it's all our pleasure. We've not met such interesting, intelligent, and beautiful women in a long time. I'm sure we'll have as much fun as we can. We'll do our best to make it a wonderful evening and get you home safely." "At some point, at least." Leonard had interjected the last bit, which prompted laughter from us all. I was so nervous at his point, as his hand had moved up and down my side from waist to thigh while we talked. I could tell he knew I wasn't wearing any panties either, the thin nylon of my hose being my only covering. I could also feel the top of my dress, slide down a little and I had to readjust a bit to keep my bra from showing. I could already tell that kind of adjustment, which would look so sexy to any man, would be needed all night. Finally, Jansen suggested we head out, as it would take a half hour or so to get to the club. We went out, Emily locked the front door and we got in their car. I had to chuckle to myself, as their car as a Prius. I knew these guys were just starting their professional careers, and would prefer something sensible to save money. Jansen helped Emily into the car, and I saw her carefully hold her dress as she sat down. She had done a good job, of letting him see a little, but not the prize. I was sure she'd be more revealing when he helped her out again. I slid in the backseat with Leonard following right behind. My dress was so short that it was basically around my waist in back, only the sheer pantyhose covering me. I could also see Leonard look down at me, which made sense, as my pushup bra created a tempting show. When we met at the gallery, I was dressed much more sedately. Now I was displaying all of my charms, much to his delight. The ride went quickly. The boys were good conversationalists. We talked about their jobs, more about Dee, and our lives, at least a good cover story of it. I was surprised at Emily, she painted quite a story about her and me. Apparently we had been friends for years, I was her maid of honor in her wedding. Neither of us have kids, but we were happily married. I thought she might dance around this, but she seemed to revel in giving details about our husbands, what kind of daily activities we liked, and for a return to truth, how we both were working on getting in shape. That might have been a bad move, as both boys liked to run too. They liked to hit the parks in the city, and suggested maybe we do some together. Although both expressed surprise that we were interested in losing some weight. In fact, I thought I heard Leonard mumble under his breath, that he thought I felt just right. One of things, I did notice was Leonard preferred to whisper when it was just the two of us talking, leaning in close to my ear when he spoke. The warm breath on my ear and neck sent chills through me, and I was sure I blushed when his beard tickled my cheek. Arriving at the nightclub, Jansen pulled up for valet parking. He put the car in gear and came around to help Emily out. He reached out and took both of her hands to help lift her to her feet. This time, I noticed she was very strategic in how she allowed the slit to open. I'm sure he saw what she wanted to show him. Leonard too got out and turned to help me. I knew there was no way to avoid it, as my dress was already pushed up. So when I put my legs on the pavement, and he helped me out, I flashed him as Emily had Jansen. But I went one step further, as I tugged down the hem of my dress as I stood up, down went my top so that the whole upper edge of my bra, with a hint of nipple under the lace was practically in his face. I wanted to die, but acted as if nothing had happened, as I casually rearranged everything. We made our way inside, the loud, beat of music vibrating through our bodies. The first thing we did, at the boys' insistence, is get drinks. Then we searched for Dee Ann. It wasn't hard to find her, as she was dancing amongst several friends. We said hello, congratulated her on her successful art exhibit, complimented each other's outfits, and said we'd talk later. At least that's what I assumed the conversation was. The music was so loud, I only heard bits and pieces, as our mouths moved. We worked our way around the dance floor, until Jansen got us a small table. Of course, Emily wanted to dance right away, so they headed out. I worked on my drink, as Leonard leaned in, as close as he could, to talk. Finally, he took my hand to get me on the dance floor. I was more than a little reluctant, if for no other reason than leaving our purses on the table unattended was new to me. But he kept us near the table, so we could see it as we danced. The first few songs were typical fast paced, but the third song shifted into a slower, softer style. Leonard immediately swept me up, so we could dance real close, so close that he actually pressed up against me, his arms holding me tight. At first I thought I was imagining it, but a quick glance confirmed that the large lump that occasionally bumped against my hip was indeed his cock. It seemed rather impressive, and I liked how he tried to move his body so it wasn't pressed into me. After another slow dance, I raised up on my tip toes so I could talk in his ear. I needed to take a break. We went back to the table and we ordered drinks for the table. After another dance, Jansen and Emily returned. That was the pattern for a while, dance, have a drink, dance again. My feet were killing me and I had to pee. Finally, I got Emily's attention away from Jansen and we headed to the restroom. Inside it was a mad house of women, talking, doing their makeup, and going to the restroom. Finally a stall opened and Emily pulled me into it. She sat down first, since all she had to do was pull up her dress to her waist. She went quickly, wiped and moved so I could take her place. It took me a minute or so to work my pantyhose down so I could go. It felt weird, in many ways, but mostly because I had gotten used to holding my cock backwards when I sat to pee ever since I assumed my feminine persona. Now I could just go, as the fake pussy held me right where I needed to be. I sat there and glanced up at Emily. I noticed she had opened her purse and gotten out something. Her diaphragm. She always put spermicide jelly on it when she put it back in the case, so it was just a matter of her working it into place in her pussy. She winked at me, as she left the stall. I soon joined her and we touched up our makeup and hair. I had to admit she looked so sexy. I knew Jansen had been all over her when they danced, and I could tell from the way her lipstick looked, that they had kissed. I wanted to feel jealousy, or anger, or something. But honestly, my life had changed so much, that maybe I was beginning to believe we were best friends, just out cuckolding our husbands together. That might explain when Leonard and I slow danced, how I always moved so his cock would be against me. I was dying to squeeze it, just once through his pants, but I resisted. I did, however, make sure that my dress was near my waist every time he took my hand to help me from the stool, legs spread ever so slightly, just enough that my silver nylon clad pussy could be seen. We had talked twice more with Dee. You could tell she was blasted but having the time of her life. It was clear she had two, very close admirers this evening who would be escorting her back to her place. Elizabeth and Martin. I imagined they would have a wild night. Finally, about two, Emily whispered to me. "Are you about ready to leave? I can't hold off Jansen much longer. He's been trying to get us to go with them to their condo." "Their condo? I'm not sure I'd trust him to drive anywhere. He's had at least six drinks." "Don't worry, we'll take an Uber. They only live about three blocks from here. Apparently, he does this a lot. Says he can pick up the car in the morning. He just tips the valet, and they give him the keys. We can be there with them in just a few minutes." It was clear that Emily wanted to go. She was probably as hot for Jansen as he was for her. I knew too, that if we went, I'd wind up sucking Leonard, or taking him up my ass, or both. Strangely after about my third drink, I couldn't think of much else. Even the idea that my wife would be fucking someone else, didn't deter me from wanting to give myself to him. "In that case, sure let's go. I think we owe the sweet boys something at least. I mean, what could would their stories be about the hot MILFs if they didn't get to fuck us." Her smile told me she totally agreed. I could see the reaction on Jansen's face, after she whispered in his ear. Followed by an immediate call on his phone. I assumed the Uber was on its way. We found Dee, said good bye and headed to the front door. It was only about five minutes till our ride showed up and another five to their place. The whole time, my legs were beginning to tremble. It had seemed fun when she suggested it, but now I wasn't so sure. Their condo building was an old restored brownstone, very nice. We went in the front and took the stairs since they were on the second floor. Jansen was leading the way, with Emily attached to his hip. He unlocked their door and we went in. I was surprisingly pleased, it both looked bigger than I imagined, and was better furnished. They had an eclectic mix of furniture and decorative items. I had expected a sort of college-chic, you know, empty wine bottles with candles in them, book shelves made from old boards and cinder blocks, and maybe a coffee table made from old crates. But everything looked new, very stylish, and well organized, although much of it was stock Ikea stuff. There was no trash, dirty dishes or anything out of place. Jansen went to their well-stocked bar and made us each a vodka Collins. The boys seemed pleased with their place, offering to show us around. Besides the open living room with bar, there was a small dining area off of the kitchen, which had granite counter tops and nice built-in appliances. They also had a small office, a spare bedroom, and half bath. I could see Emily was looking around. "Jansen, why don't you show me your bedroom. Is it back there down the hall?" She didn't wait for him to answer, but downed her drink, took him by the hand and started to go that way. He barely had time to mumble sure, finish his drink, and go along. At the back of the hall, he opened the door on the right, led her in, and shut the door behind him. I immediately began to panic. I looked at Leonard. "Is that the only bathroom? I need to go." "That's the guest bath, but if you want more privacy, each of our bedrooms have an attached bath. Mine's the left one. Here let me show you." He took my hand and we went to his room. When he opened the door and switched on the bed lamp, I saw the door to his bath and went on in. I didn't need to pee, but I did want some privacy. I knew what was expected, so I carefully removed my pantyhose. I had been surprised they had survived the wild night without a snag or run, and wanted to get them out of harm's way. I also removed my dress. He had a hanger on the hook on the door, so I hung up my dress, draping the hose over them. I reached in my purse, found the lube, and prepped myself. I also found the small thong that matched my bra. At the last moment, Emily had put that in my purse, just in case. I knew it concealed my fake pussy enough to get me by. I lightly touched up my lipstick and decided I would go out in my bra, thong, and heels. Opening the door was difficult, as I expected Leonard to be on the bed, probably nude. But he wasn't even in the room. I softly walked to his door, and peeked out. He was making a drink, I guess he wasn't going to assume anything. I thought for a second, is this what I want? Then decided. "There you are. I thought I'd lost you." He turned to look at me. I walked down the hall to him. Seeing how I was dressed he smiled. I took the drink from his hands, put it down and molded my body against his. I could feel his cock now. Smiling I looked up again, whispering like he did. "Leonard, I hate to be a bother, but it's really not a good time of the month for me. I hope you don't mind oral, or anal. I can do either, or both." I didn't wait for an answer, but raised up on my toes and kissed him, my tongue plunging in. I could really feel him throbbing, so I did what I had wanted to do all night, I lightly squeezed it. I let out a soft moan. I couldn't believe I did that. I sounded just like I was with one of the guys earlier today. But Leonard loved it. He took me by the hand to lead me back to his room. Inside, he began to remove his shirt, shoes, socks, and finally his pants. I had slipped off my heels. I knelt on the bed facing him, reached around and undid the clasp on my bra, letting it fall on the bed. I then reached out and helped pull down his briefs. His cock popped out, almost hitting me in the face. I instinctively grabbed it, wrapping my fingers around it at the base. I could tell he wasn't as big as Todd, but was longer than the others, and by far thicker. Plus his cockhead was twice the size of the shaft. I really liked that his pubes were cropped, really short. It helped emphasize his size. I looked up at him, a sly grin on my face. "May I? It looks delicious." He grinned and sort of waved me on. I didn't need a second invitation. I used my other hand to cup his balls, holding him firmly. I then slowly licked his glans, kissed it a couple of times, then slid my lips over him. It seemed so wide, but I loved how it felt when I closed my lips down on the shaft right behind it. I sucked it, gently at first but then more forcefully, I also lightly stroked him. I wasn't sure I was going to suck him until he came, but I did want him fully lubricated. But I did want this to be different than the others that I had done. I removed his cock from my mouth, took his hand and pulled him into the bed, having him lay on his back, propped up by pillows. I then repositioned myself, so I was between his legs, facing him. With him where I wanted him, I started what I hoped to be one of my signature moves. I took his cock holding it lightly right behind the head. I looked up at him, making eye contact. I smiled at him, and then began to take it in my mouth. I slowly started swallowing him, maintaining eye contact. Down I went, further and further. I had gotten to where I loved the feeling of when a cockhead started entering my throat. Something about what it meant, maybe my surrender to this man or just the full feeling it generated made me hot. Tonight, that feeling was magnified as his cockhead was so big. Still, I loved it. With his cock now in my throat I shifted slightly so it was easier to continue swallow him. Finally, my nose was buried in his short pubes, the sweat and musky odor from a night of dancing very strong. With his cock entirely in me, my lips and nose pressed into his body, I moved my face sort of side to side. Leonard was going wild. He held my head lightly and whispered how much he loved this. It was unbelievable, how he'd never had a woman so skilled. I loved how men showered you with compliments once you had all their dick in your mouth. They knew what I was giving them was special. But his kind words weren't all I heard. From the other room, I could hear Emily. She was making short, rapid oh sounds, starting slowly and building up. That was a familiar sound. She made it when I fucked her. Now someone else was giving her that feeling. I could tell from her voice, she was having a great time. That triggered an urge in me, I wanted to taste Leonard's cum. I began to move back up his cock, letting it slide out of my throat and mouth and then plunged back down. Although he was the fifth cock I had sucked that day, something was different about this time, very different. Somehow sucking a man for fun, his and mine, made it altogether different act. I worked on him, finally getting some pre-cum, a tease of his taste. Leonard was not surprisingly, very different. There was more spice to him, plus a sweetness that I'd not found before. I continued to suck on him, using techniques that I knew had worked earlier. Only this time, I didn't rush it. When I felt his balls tighten, I would change my focus, go slower, perhaps pull off of him to tease his glans with my tongue, and just do something different. By now he was actively moving around, being much more vocal, and reacting more. I hoped I was giving him the best head he'd ever had, and in some measure wanted to continue bringing him to the edge and then backing off, so he'd feel more. But I was getting selfish. I so wanted to taste him fully. To have him fill my mouth, or maybe my throat so I would know him like only a few others had. So, this time when I felt his balls tighten up, a pre-sign of his desire to come, I shifted to the techniques I knew would guarantee an orgasm. And they did. His whole body stiffened, he held me tighter, one hand on my head and the other on my shoulder. As he started to shoot, I plunged downward, my throat massaging his massive cock head. He filled my throat too. Two, three, finally four streams of cum. Once he was well into his ejaculations, I moved back up. I caught the last one on my tongue. Sweet, spicy, strongly tangy, I loved his taste. As he started to deflate, I continued to suck, pulling the last drops of cum from him. His orgasm had overwhelmed him, silencing him enough, that I could hear the oh, oh, oh, from the next room. That had to be Emily's second orgasm. I smiled. Not just because she was getting pleased, but because Leonard's cock was getting hard again. When he was all the way stiff, I let him out of my mouth, and looked at him. "Baby, I love sucking your cock. It's so thick and strong. It fills me up so completely. But I need more. Do you mind fucking me? I have to feel you inside me. Right now, I want this big cock in my ass, please." The expression on Leonard's face was priceless. Not only had he gotten a wonderful blowjob, he was getting begged to fuck my ass. For men, somehow, anal has become the most intimate, desirable but forbidden pleasure a woman could offer. For once, it wasn't him pleading for it, the girl was begging him. He raised up on his elbows. "Let me get ready and I'll gladly give you a fucking to remember. Move over, get on your knees, and put your head on that pillow. I'll be right there. While I did as he said, Leonard reached into his nightstand, got a condom, and put it on. Then he got between my legs, laying his cock in my crack. He leaned over my back and told me this would keep everything cleaner. Moving back, he took his cock in his hand, holding it right behind that huge head. With his other hand he took the rear string of my thong in his hand and spread one of my cheeks back, exposing my hole. He put his cock at the opening and began to push in. At first I resisted a little, but as he penetrated, his cock found my lube and it started to slide in easier. Not that it didn't create a hell of a sensation. When Emily had used her dildo on me, I felt it. It was a new sensation, something my ass had never experienced. Leonard's cock on the other hand, took this feeling to a new place. I felt my asshole stretching as it tried to accommodate his thick glans. It was an equal mix of pain and pleasure. At one point, I wasn't sure I could handle him, although I desperately wanted it. I wiggled my ass, I pushed back against him, trying to open my sphincter on my own. But it was his mass that split me open finally, I felt my muscles contract, as the head plunged all the way in. The shaft, which just minutes ago, would have felt immense, was now a relief. A sweet relief. I began to purr as he went further in and then began his rhythm. I knew what he was feeling. I knew how nice it was to get in a woman's pussy. To have your cock stimulated on all sides by her wetness. So I knew what Leonard was feeling. But I also knew what it was like to have a cock inside your own pussy. To feel this powerful force inside you, touching your soul and bringing you unbelievable pleasure. As he sawed away, in and out, of my ass, I felt corresponding waves of pleasure. My asshole was now numb to the pain, and I could only feel reams of pleasure. I closed my eyes, and began to shift from soft purring to a new sound. A sound that I had not made before. A sound that I had not known existed in me. As he pounded my ass, it just came out. Slowly at first, but then building in speed. Oh, oh, oh, oh. The whole time I had been with Leonard, first sucking him, and now getting fucked, my cock had reacted. It swelled up in its rubber sheath beneath my plastic labia. It got as big as the rubber would allow. The tightness when I sucked him, was simple pressure. But when Leonard started fucking me, my cock could feel his cock through the walls of my ass. It wasn't enough to make it come, but it made it hard. So hard, it almost hurt. But in a good way. I wasn't sure if I was leaking pre-cum or not, nor did I care. Honestly, I only focused on Leonard's lovely cock and all the pleasure he was giving my ass. I began to sense a change in his rhythm. He was speeding up, plunging in as deep as he could, and slamming my cheeks harder. He was pounding me so hard, I could feel his balls in their sack plopping against my inner thigh. Then it happened. Leonard plunged in and stopped. He grasped my waist firmly, his body stiff. Inside my bowels, I felt his cock twitch several times. I couldn't be sure, but I bet he'd orgasmed again. For me, it was like I had fallen off an emotional cliff. The mere act of his climax, triggered a mental climax for me. My cock was unable to come, but my mind could. I squeezed my sphincter tightly on his shaft, as he twitched. My fingers, which had drifted to one of my nipples, pulled and twisted it, sending jolts of more pleasure. Finally, Leonard collapsed on me. He lay still for a few moments, catching his breath. I loved feeling his weight on me, still pinned to the bed by his cock. But slowly he began to soften. Leonard slid to the side, pulling me into him. One hand began to fondle my breast. He softly kissed my neck, nuzzling me as he did. With his cock now flaccid, he withdrew it, making almost no physical presence as that beautiful cockhead left me. I was spent emotionally. I had been on such a roller coaster all day, that now I had no energy left. No desire to do anything but lay there. However, deep inside me I knew I had to get up. I looked over at the clock on his nightstand. It was 4:30. Emily and I needed to get home. We couldn't stay here overnight, having two studs bring us to our safe, suburban home in broad daylight, dressed as we were for a wild night of dancing and fucking. I heard nothing from Jansen's room. I figured they too, were recovering. So, I took his hand from my breast and lightly kissed it. I looked over my shoulder at him. "Sweetie, that was amazing. You are such a spectacular lover. I've never been so moved. I won't forget it. But I can't stay. I need to get home. My husband may be understanding, but I can't expect him to accept me staying away all night. Emily and I need to go." He whispered that he understood. He kissed my cheek and told me he'd see if they were getting ready, while I went to the bathroom. He got up, stripped off his come-filled condom, and dropped it in the trash can. He worked his pants up his legs, without underwear, just so he'd be covered. I got up, looked around to find my bra, and then went to his bath. Turning on the light was a shock. Much of my makeup was smeared, my hair was a mess. I sat down on the toilet, peeling my wet thong down my leg. I peed and wiped my ass and crack. I was pleased by fake pussy was still glued tight to me. Even though it was damp, I put my panty back on, hooked my bra, and slid the dress over my head. I took a few tissues and wiped up my face as much as I could. At least removing the smears. I lightly coated my lips with my cinnamon lipstick, satisfied that I would be good enough for the Uber driver. I left the bath, found my heels and joined the rest of them in the living room. I could tell Emily looked about like me. She'd touched up her makeup, but her fancy up-do, was now a simple ponytail. Jansen was holding her tight, still trying to convince her to stay. When she saw me, she smiled. I returned her smile with mine. Finally, the Uber showed up. The boys escorted us downstairs, telling us that they'd text later. In the car, we looked at each other and then lightly kissed. I think to the pleasure of our driver and the boys still standing on the sidewalk. Finally we snuggled for the thirty minute ride. Emily fell asleep. We got to our house, and in our bed right around 5:30. We were so tired, that we just undressed and crawled into bed as we were. The next thing I knew, I was rolling over. I was very thirsty, with a mild headache, and needed to pee. Looking around, I realized I was in my own bed. The clock said 12:07. I rubbed my eyes and looked over at Emily. She was still sound asleep. She looked so innocent, like she always did when she slept. But I realized she had fucked another man last night. She'd had another man's cock in her for the first time since we'd married. We weren't the same couple we'd been a week ago. Because I also had a man's cock in me too. I had moaned and made the same sounds as Emily had. We'd both been overwhelmed by wonderful cocks. So I felt like we were closer now than ever before. Her being with another man, was not a bad thing, but good. In any case, I needed to get up. I made my way softly to the bathroom. I started the shower, while I sat to pee. My cock was still in its sheath, put away, under my fake pussy. Again I liked how I could sit and pee like any other girl, no need to hold my cock. As I sat there, I felt a slight burning in my ass. I could feel it was sore from last night. A tingly, buzzing feeling, different from normal, but not bad. I thought about how good it felt when Leonard was in me. I finished peeing and looked around for the small instruction sheet that had come with the rubber form. A quick read told me, it was safe to wear the pussy for several days, but that it should be removed no more than 72 hours after being attached. With that settled, I looked in the mirror to begin cleaning up my face. I removed my false eyelashes, used makeup wipes to remove my eye makeup and pinned my hair up. A quick brush of my teeth and a drink of water helped, short-term. The two aspirin I took should help later. The shower felt great, warm jets of mild pressure massaging my skin. I soaped up all over, using a loofa to scrub myself. Moving my hand over my pussy, gave me chills. The soapy suds made me slippery and I could feel every fold and indentation of the form. That was a special feeling I had got from washing my penis. Anyway, I felt the grime wash away, and I quickly shaved my face once all the makeup was off. Getting out, I toweled off, applied some lotion, and brushed out my hair. I put on some deodorant and perfume. My face looked so pale and innocent without makeup. I could see light freckles sprinkled across my nose and cheeks. It was hard not to do my face, but I forced myself to just apply some light pink-tinted lip gloss. Before quietly going back into the bedroom to get dressed, I looked at my full image in the mirror. My breasts, areola, curvy body, and smooth hairless skin were all perfect for a female. But what really caught my eye, pleasingly, was my pussy. Even with the slight color difference of the rubber, I loved how I looked. Turning side to side to see how my labia looked from different angles, I saw how complete it made me. The way it gave me a nice gap between my legs, nothing hanging down, just a smooth curve back to my ass, seemed perfect. I smiled again. That look seem so right for me now. I crept softly by the bed, Emily's light breathing telling me she'd be asleep a while. I gathered some lingerie, went into the closet for clothes and shoes and back to the bath. I pulled up my panty, a sheer tanga style in soft pink that did nothing to hide my new pussy. The bra was a pushup style with lots of lace and padding. Emily was absolutely right. Given any choice it was my preferred style. I just loved how it made my breasts look bigger and sexier. I hadn't grabbed hose, as I didn't expect to go anywhere but to the mailbox for our paper. I pulled up my floral skirt, stretchy fitting tight around my ass and stopping at mid-thigh. My top was a light pink, ? sleeve with a deep ruffled neckline and lace trim. My heels were simple thong sandals. Pink straps and a high cork wedge. In the kitchen I started a pot of coffee. Heading out the front door, I realized that it was the middle of the day. Cars were going by, a few kids played in the front yard up the street, and our neighbor across the street waved to me as I got the paper. She seemed comfortable seeing me in my skirt and heels. I guess it was normal for me now. I waved back and smiled. Walking back, I felt my ass cheeks wiggling under my tight skirt. Going up the steps, I could see my breasts bounce slightly. Apparently so could the elder gentleman next door. I saw him peeking out his window. I'm sure he felt safe behind the curtain. I couldn't help it, but I accidentally dropped my paper, then bent over from the waist to pick it up. I almost thought my boobs would pop out, but although they bulged out the V of my top, they stayed in place. He'd like that I thought. Inside, I poured myself some coffee and started looking at the paper. As I skimmed it, I was drawn to ads for women's clothes, articles on fashion, household hints, and gossip about the latest move stars. I only glanced at the sports, stories I would have devoured before. Partly because I knew all the guys would be talking about them, and partly because I felt it was expected of me because I was a man. Now that pressure was off, I skipped them. I looked at my horoscope, read the advice column. What I spent most of my time reading was an article on the newest fashion trends and one about challenges women face in the work place. There was also a sales flyer from our biggest department store. They had a sale on cosmetics, women's accessories like purses and hosiery, and winter wear. I knew most of my things were more for late summer and fall. I certainly needed a heavier coat, a few scarves, and maybe a cute matching glove and hat set. It would probably be smart to buy some heavier tights too. I knew myself well enough by now, that I wouldn't stop wearing skirts and dresses just because it got cold. The other ad that caught my eye, was one from a sporting goods store. Seems they were running a clearance sale on golf supplies, including golf clothing for women. Just what I needed. When I finished the paper, I felt like cooking so I made up a batch of muffins and put them in the oven. They were just about done, when I heard feet shuffling. Looking up, Emily was finally awake. I could see she had showered, although she just had on a robe and slippers. She smiled at me, as I poured her a cup of coffee, but she really wouldn't look me in the eye. "Good morning honey, how do you feel? Any hangover effects?" "No, I'm okay that way. I think coffee and something to eat would do the trick." "How about you?" "I had a little headache earlier, but it's gone now. Amazingly, I feel all right. I mean, it's been a long time since we stayed up that late and we've never partied or done anything like that since we married." "Yeah, it was pretty wild. I'm sorry. I guess it was mistake to follow through like that. I hope you can forgive me. I guess I just lost control." I could see Emily was worried. It was a wild night, something a week or so ago, I would have bet a million dollars against. But it happened. "Emily, don't feel like that. It wasn't just you. I was right there with you. I mean, just because it was outside of our normal comfort zones, doesn't mean it was wrong. You can't tell me you didn't have a great time, both at the club and later with Jansen. I know for me, it was real eye opener about myself. The key is whether it changed how we feel about each other. I know I still love you. Did what happen last night change how you feel about me?" "No, oh lord no. I love you more than ever. I just feel I pulled us over the line. I fell for all the attention Jansen was giving me, you know? It was so flattering to have someone new tell you how pretty and sexy you are. I know you still feel that way toward me, but it was just my ego." "Don't beat yourself up about it. I kind of felt the same way, probably more so, given my current state. Besides, it's over and done with. We can't take it back, not that I want to, it's just part of us now. I think the bigger issue, is what we do, if the boys continue to reach out to us." "I know. Jansen's already texted me today. I guess that's the younger generations' equivalent of sending flowers the next day." I laughed. Then leaned down to kiss her. "Emily, how about we just try to figure this out as we go along? I've already taken a huge leap off a cliff by agreeing to something that I'd never imagined I'd do. My self-image is morphing so fast, I can't keep up. I mean I gave five men blowjobs yesterday. Five. Plus I had anal sex with one. But I never felt more real in my life. When we married I felt complete. But now, it's like complete plus. If you aren't put off by how much I've changed, I certainly don't love you any less for garnering some attention from a young, hung stud. I mean how can I compete with that now?" I lifted up my skirt, showing off my 'pussy' through the sheer panties. That brought a laugh from Emily and perhaps an acceptance of how wild our life has changed and we still loved each other. At that point, the oven signaled the muffins were ready. I took them out, and we sat at the table, like two girlfriends, or maybe two lesbian lovers, talking about everything that happened last night. I really wanted to know about how great her sex was with Jansen. Emily definitely wanted the details about Leonard and me. By the time we finished our second muffin each, we felt much better and we're okay with our new direction. I had Emily help me remove my pussy form, so I could see how the solvent worked and whether I had any skin irritation from wearing it. Luckily, it seemed to be pretty tame, making my skin light pink, which disappeared in an hour. I didn't tell her, but taking it off and returning to having my penis exposed, was depressing. I had really enjoyed how it made me look and the realistic feel. But I knew I wanted to wear it on Tuesday, so I was prepared to go a few days without it. We spent the rest of the day relaxing, reading, and planning the next week. I showed Emily the sales ads in the paper and we planned a day of shopping on Monday, another girls' day out. Most of the afternoon, we were bombarded by texts from the boys. They were so intent on seeing us again, quizzing us about if we had a good time, and just silly romantic type chatter. We both laughed about how odd it was that these young boys seemed so taken with two older women. Maybe it was the allure of our experiences, or maybe it was just that we seemed to really enjoy sex with them. Emily and I talked about what we should do next and agreed we'd slow play it. Laughingly, we agreed that after a few days maybe their hormones would settle down and we could judge the true level of their interest. We ate a simple dinner, cuddled in bed and watched a movie. Being so close to each other, we wound up kissing and stroking each other. It seems it wasn't only the boys whose hormones were elevated, Emily kept pushing me for sex. She was stroking my cock through my panty and whispered whether I wanted to fuck her. It was a little embarrassing to admit, but I replied, I'd rather eat her and then rub together. I shouldn't have worried, she liked this idea even better. Emily came twice from my kisses and we both climaxed as we rubbed out crotches together. My explosive climax, filling my panty with come, revealed how much I had been inhibited by the rubber pussy over the weekend. Its first real shortcoming. The other thing that was revealed was how much our sex drives had been increased by these wild transitions. We'd had more sex this week, than we had in a couple of months previously. As we snuggled in bed, just before sleeping, we took turns texting the boys. It seemed the only way to satisfy them. Monday turned out to be super fun. We got up, dressed and headed out to shop. Rather than be very dressy, we both wore skinny jeans, short- sleeve tops, and pumps, with just a bra and panty. The idea was to be able to get undressed easily to try on outfits. We hit the golf stores, several large department stores, and a few specialty places Emily liked. We went to the golf outlets first. I wound up with three golf outfits. The first was a clingy, sleeveless dress with a matching sweater in reds, blues and whites. The second was a polo shirt, hoodie, and skort in purples and pinks. The last was a long-sleeve, V-neck top with a skin-tight pair of leggings in bright greens with yellow highlights. The dress and skort came only to mid-thigh, while the leggings basically revealed every curve. I figured the guys would like this show. The best part was I stayed under the $200 the boys had given me. In the department stores, we looked more than bought. We both tried on lots of clothes and shoes and looked at sexy lingerie. We did look at sports bras, but they were so functional, they didn't look sexy or fun. So I opted for more of the lace long-line bras, with of course, one being a pushup style. I coordinated their colors with the outfits and including matching, tiny, tiny thongs, as I planned to wear my pussy when I golfed. I did buy a couple of sweater dresses, a cute winter coat, and a new pair of thigh high boots, as well as tights to wear this winter. Emily loved how I was embracing my feminine role, especially how I was planning ahead for clothing, which suggested I was fully committed to my new identity. She also got some tights and a new coat. As we paid the bills in cash, I was further convinced I had done the right thing by agreeing to Annie's proposal. The specialty shops were the most fun. We tried on all sorts of outfits, with lots of attention from the salesladies. Because Emily was a frequent customer, they didn't even seem to mind too much that we only bought a few accessories, like a wide belt with a big buckle, a couple of cute, trendy necklaces, and two purses. I was beginning to see why Emily loved to shop. It was fun and really reinforced a positive image for yourself. As we entering the last store we planned on hitting, we both got texts from the boys. They seemed desperate to see us. Despite our reservations, we agreed to meet them for dinner in an hour. We picked a restaurant about half way between their urban condo and our suburban house. We told them this was all the time we could spare without raising suspicions with our husbands. We didn't realize it, but we wound up spending more than an hour at the last shop, so with travel time we arrived about 15 minutes late. We found the boys sitting at the bar, nervously awaiting us. But their concern turned quickly into smiles when they saw us. I was a little embarrassed, as Leonard came right up, hugged me and gave me a big kiss. He looked me over and told me he loved how I always looked sexy. I felt like a teenager, as he took me by the hand as we went to a booth for dinner. Emily and I each had a fancy cocktail, then we shared an appetizer with the boys, before our meal. I was starving, but I also was concerned about following Emily and gaining weight. So I opted for a simple salad. While we ate, the boys talked about the party last night, Dee Ann, and how much fun they had. The elephant in the room was our visit to their condo. It was like they didn't want to say the wrong thing, but I could tell they were dying to talk about it. Maybe it was because, I was becoming so more comfortable as a woman now, but I decided to address it. But first, I wanted to just feel it again. I reached over, under the table, and began to slide my hand up Leonard's left leg. I had noticed his bulge there when he hugged me. His cock was soft, but it didn't take but a couple of light squeezes and some rubbing to make it grow. When I touched it, he looked over at me, a sly smile on his face. "I don't know about you, but I really liked seeing your place. I loved how it was decorated. I never expected single men to have such nice taste. You were so welcoming and such good hosts. Especially in the bedroom. Emily, didn't you have a wonderful time too?" She looked at me with a sly smile and giggled softly. "Yes, it was far more than I expected and very, very enjoyable. Jansen was so welcoming and made sure I had such a good time. We really wanted to thank you two. It was a super finish to a fun evening." They didn't seem to know what to say, as they smiled and I think Jansen even blushed a bit. I could tell from Leonard's hard cock that he was thinking of how to do it again. "We'd love to have you back over again, if you want? Maybe you two could come over for dinner this week?" "That's so sweet, Leonard. But to be honest, I think this week is going to be far too busy. I've got a lot of things going on at home as well as some commitments with my husband for his business. Also, I think we should host you next. It's our turn and you've not seen the inside of our house. Emily, what about in two weeks, do you think we could have the guys over to your house? You know, when our husbands are going on the fishing trip. They'll be gone overnight." I turned back at Leonard and smiled, while I still stroked his cock. Emily smiled. I could tell she would like the idea of them spending the night with us. It would be much easier for us to send them home than try to do it ourselves. "That's a great idea. Jansen, do you think you'd be open? I mean, we'd love to spend some time, real quality time, with you and Leonard. Would you mind come over to my house for the evening?" He grinned, said yes, and leaned in to kiss her. I looked at Leonard and he followed suit, kissing me deeply, with his tongue inside my mouth. I just couldn't get over how different kissing a man was from a woman. His kisses were so much more forceful, and seemed to melt me inside. We broke our kiss and I looked over at Emily. "Well sounds like a date. We'll text you the exact time and date, so there's no confusion. But I'm afraid I have bad news. We need to get going, as Ron, my husband, was expecting me back soon. I promised him I'd be home by seven." The boys said that they'd get the check, and stood up to let us out of the booth. We both exchanged one more kiss before we walked out to the car. As we headed down the road, Emily looked at me. "I can't believe you did that. What a great idea. I wanted to be with them again, and this will make it so much easier. I love how you're using our fake husbands to set up our meetings just the way we need them." "Well to be honest, I was afraid if I didn't end it at the restaurant, I'd be tempted to go out to Leonard's car for more than a kiss. I don't know what it is, but his kisses just melt me. I love kissing you, but it's so different than his." "I know what you mean. I hadn't mentioned it, but after you began to dress, and express your feminine persona, our intimate time together felt different. You are softer, sweeter, and more connected to me somehow. Your kisses are great, but different than before. When I kiss Jansen, it just seems to have more force, power, or something. It touches me differently. " "Yes, yes I agree totally. Kissing a man is a million times different than kissing a woman. Both are great, but I can tell it will be difficult to not want both kinds of sex. Is that okay?" "Of course, it is honey. I started you on this journey. Helped you transition, so I have to be understanding. Plus, you've freed me too. I mean my sex with you now is so different than before. You're giving me sensations, emotions, and orgasms that come only from a woman. So why would I deny you the chance to have both kinds of experiences too? I think, if we continue to be honest with each other then everything will be fine. I still love you more than anything in the world." "Me too." We'd gotten to our house, so I reached over to kiss Emily. A soft, sensuous kiss that seemed more emotional than physical. She smiled at me, and we got out, taking all our purchases into the house. The rest of the evening we spent trying to relax. I selected what I was going to wear tomorrow for my first day on my new 'job'. I wanted something, sexy yet classy. I also got Emily to reapply my pussy form. I didn't tell her, but once it was fully attached, I felt normal again. She must have sensed something because she spent some time with me, working with cosmetics to make it blend better with my skin tone. Although we were both horny, we decided to avoid sex. I wanted that edge to help drive me tomorrow, and we were both a little sore from our adventure with the boys. I had hoped to sleep in on Tuesday, but it turned out I was too excited about my new adventure. So I followed my morning routine. After Emily joined me, we talked about our plans. She needed to meet with the Homeowners Association for lunch, wanted to do a short run, and then since I would be gone that night, was going to watch a movie on Netflix. I had to laugh at that, because she had been dying to watch the latest of those car chase, save the world flicks, but I found them boring. I offered to do some housecleaning to offset my absence that night. She happily agreed. So the rest of the day we went our ways, time passing agonizingly slow for me. Finally it was time to get ready. I was to be there at four to meet with Annie. I took a quick shower, shaved, and started to get ready. I was getting quite proficient at my hair and makeup so I soon had those done. I even used false lashes again, as I was getting too really like them. For my first day on the job outfit, I had gone with a combination of new things and some of Emily's thin clothes. The top was her black V-neck sweater, with ruffled cuffs and neckline. It fit snug but not too tight. I paired it with a warm caramel colored skirt, again tight but loose enough to allow me to move. The skirt was short, not quite to mid-thigh and I used my new wide black belt with a big silver buckle to emphasize my waist. My bra was a black pushup, panties were a beige thong, and my pantyhose were black sheer to the waist with large mesh black fishnet design woven in. For shoes, I chose light brown, thigh- high boots with 4 inch heels. Accessories were a new silver necklace, my jeweled watch and bracelet, and a new large caramel purse, big enough for my makeup, lube, tissues, and even an extra pair of hose. I felt I struck the perfect balance between sexy and refined. I wanted my customers to realize I was not a street hooker, but would still give them the best blowjobs that could get. I felt okay until the drive to the Club. My nerves were getting to me now, as I had all sorts of doubts starting to surface. I parked around back, in the employees' lot and made my way inside, looking for Annie. As usual she was in the bar. When she saw me, she did a double take and smiled. "Wow, nice outfit. I love those boots, super sexy. I bet the guys will love them too. Are you ready? I hope so, because a couple of your customers are already here." "Thanks. I just had to wear these, even if it isn't very cold. I hope I'm ready. To be honest I was good until I got here, now I'm a little nervous. Do I just wait at the bar to meet them?" "No, Stewart and I talked about it. If you are in the bar, then you'd have to make an exit with each customer, return alone or with him, and then leave with someone else. It would look way too much like a revolving door and might attract attention. He suggested we set you up, in the side room. We use it on holidays when we have extra traffic or when groups rent it for parties. Come on, let me show you." We walked from the bar, but instead of turning right into the Club dining room, or straight to the entrance foyer, we made a sharp left turn. A set of glass double doors, normally closed had one side open. Inside was a moderate sized room with round tables with chairs. But to the side was an area, they must have set up. It had a smaller, higher table, like the bar tables with four stools. They had a floor lamp on, as well as a fragrant candle in a glass holder. "We set it up so you could meet each customer here, have a drink or talk beforehand. Besides tips, the other way I'll make money is with drink orders. I've told the guys you expect them to buy you a drink or two on your 'date'. What I'd like to do is rather than bring you a drink with alcohol, I'll just give one plain. You'll drink a coke, but I'll charge them for a rum and coke. That will keep you from getting drunk and give me an extra $10 or so per customer. Just order things that I can leave alcohol out, like a cocktail, rather than wine or beer. But if you do want a real drink, when you order tell me you'd like a taste of wine or a taste of rum and coke. That'll be our code. So after drinks, when it was time for you to do them, you go back to a more private room." She led me back a little further, where a regular door led to a small room. Inside was a couch, an arm chair, and a small end table. The lighting was muted. I looked around. "Oh Annie, this is nice. I was worried about using the staff bathroom. This is a much better approach. Plus, I agree about working from the bar, it would look suspicious. But this is so out of the way, perfect. Thanks. That reminds me, I want to give you some kind of cut for all your work. I know the tips should be better, but you deserve more. Would you be okay with a percent bonus?" "Dana, thanks I appreciate the offer, but really between tips and your drink charges, I will do fine." "Well is there something else I can do to help repay you? I just feel like I'm getting so much." "Umm, there might be something. I hate to ask, and tell me if it's uncomfortable for you, but yes I do have a way you can help pay me back. Currently, I live with my boyfriend and two sons. He's a nice man, a good role model for my boys, and always pays his share and more of the bills. But he does have one preference that gets to me. He loves oral sex. He's always pestering me to give him a blowjob. I will, but I don't like it really. So if you would give him one, for me, maybe once a month that would be worth more than money to me." "LOL, okay, I can do that. But let's start him with one every two weeks. If he likes them so much, and this works out as well as I hope, I'll gladly give him a freebie. It's a deal." With the details worked out, it was time to start. I sat at the table, while Annie went back to the bar. When she returned she was carrying a drink tray and was accompanied by a man. He looked like a regular guy, nothing unusual or different. He did seem a bit nervous, but truthfully so was I. Annie put the drinks down and introduced us. His name was Hal. I smiled and went into full sales mode, being friendly but not to inquisitive. We started drinking, mine was a plain sprite, and he seemed to relax. After a few minutes, as soon as he finished his drink, I decided it was time. Now or never. "Well Hal, you seem like a nice guy and you're very attractive. I hope you'll like what I have for you. Why don't you follow me to a place a little more private and we can see." I stood up and reached my hand to his. He took it and followed me to the small room. Inside, I was all business, placing him on the couch and kneeling in front of him. He was eager, undoing his pants for me. I made a big show about his cock, complimenting it and stroking him as I held it. He was average in size but seemed pleased by my attention. I started him, as I had every guy after Ham. I had mentally laid out a process that I hoped would work with my clients. I started with just his cock head, then working up and down his shaft with tongue and lips, lightly sucking his balls, and then back to his cock head. The real heart of my blowjob, was the long, slow swallow of his entire cock, my eyes locked on his. Hal reacted as all the guys had. Once I had him excited, I worked a regular rhythm driving him to a climax. Of course, I worked in a few different moves. But inevitably, he came. Again, I made a show of swallowing his cum, licking all the drops of his cock, and sucking every bit down. From my limited experiences, I knew how men loved to see this. It was like confirmation that they were so hot that a woman had to have every drop of his precious cum. This had little to do with the current blowjob, but was aimed at luring him back for more. I wanted steady, repeat customers if possible. When he was done, I could tell he felt awkward, so I bragged on him again and as I got up to my feet, made sure to lean over and give him a good look at my boobs, basically right in his face. He got up, straightening himself, and after a few minutes of chatter, he left. I glanced down at my watch. The whole thing had taken only twenty minutes. I checked my image in the mirror over the table, fixed my lipstick and went back to the table. Right on schedule, Annie brought the next customer. As he sat down, she took our drink orders, and cleared the table. We chatted making small talk until the drinks came. We talked a little more. I could see almost every one would want to drain their drink as fast as possible. They weren't there to socialize with me, but to get blown. So I complied with their wishes. The second guy was much like the first, and it took just about the same amount of time. When he was done, I got ready for the next. I did five guys like that. I found that they each had something unique about their cock, how they tasted, or their climax. But overall my role was the same. I was pleased it wasn't too stressful on the muscles of my jaw and mouth. I had worried about getting tired. But I was fine. So far my first day on the job was going very well. Then Annie surprised me. She brought three guys back to the room. I looked at her as if she were crazy but she just smiled. I could tell they had already been drinking. "Dana, these are Jack, Ben, and Mathew. They're best friends and usually come to the Club for a few drinks a couple of times a week. They'd rather just wait here, have their drinks, and talk while they take turns with you. Since I set aside an hour and half for all three, I figured that would work. So what do you guys want to drink? Dana, how about a shot of vodka? I'll bring one for each guy." This was odd, but after I threw back my shot of vodka (tonic water). I took the first one back to the room. When he was done, we sat back at the table and in a few minutes Annie returned with another round of drinks. I wound up doing all three guys, and they each bought four drinks, as when I finished the last, Ben, we sat and talked. They loved this and were very complimentary of my efforts. We actually talked about other things as well. Even though they had all come, they seemed to like just talking with me until their whole time was up. Annie showed them out and then came back. "Dana, that's all the customers I had lined up for today. How you doing?" "Fine, really good. It went so much better than I had expected. No troubles getting any of them to come and they all seemed like really nice guys. Very friendly, polite even. I could see this working out." "So, you're not too tired?" "Oh no, I'm fine." "Well if you want, there are two clients at the bar who had expressed interest in your services but I hadn't lined them up for a day yet. I'll be honest I went ahead and set up both Thursday and Friday, assuming you'd be fine with this. If you feel like it, I can bring them back, one at a time and you can make more money tonight. You up for it?" "Hell yes. I mean, it's only 8 o'clock." So Annie brought me two more. Both were fine, although the second guy was kind of small. The smallest one I'd done. I spent extra time with him, sucking his balls more, running my tongue over his shaft, and sort of extending his excitement before I let him come. I didn't say anything about his size, assuming he might be sensitive about being small, but instead bragged more about his taste, his stamina and after it was over the amount of cum he gave me. I could see he felt better about it when it was done. He immediately asked if he could do this again. I told him I'd be glad to do him, as it was a treat for me too. He just needed to talk with Annie to get on the schedule. After he left, Annie came to me. I could tell she had something to ask me. "Dana, can I ask you a favor?" I nodded my head, so she continued. "My boyfriend, Brad, is at the bar and it would mean a lot to me, if.." "Sure, bring him back. Just bring me a taste of wine and two shots of peach schnapps." She laughed and left. He came on his own, and she followed with the drinks. He was a cute guy, seemed young, but attractive. He also was nervous, cutting his eyes at Annie when she gave me the drinks. I could sense he was nervous. Kind of like he was worried this was a trap or some kind of trick to see if he was faithful. So I decided to clear the air. "Brad, Annie tells me you love oral sex. I understand, most guys love a good blowjob. Unfortunately, not every woman enjoys doing them. So, that's where I enter the picture. Annie's been very good to me, making my life very easy and profitable. Plus she seems to be one hell of a girlfriend. So, if you're okay with me covering for her, taking care of your needs this way, so she doesn't have to, then this will work. If I agree to please you, then you have to agree to layoff pressuring her for one. Now this doesn't mean you can go elsewhere when you want. Other than me, you still need to be true to Annie like any good boyfriend would. Is that a deal? Good. Then why don't we go back to my office and I'll see what I can do for you." I took him back to the room. I wanted him to really enjoy this, so I spent extra time with him. I gave him as much attention as he could handle, but I stretched out his orgasm. By the time he finally came, I was certain he loved it and he did. He swore it was the best blowjob he'd ever have. If I was willing to give him this kind of sexual excitement, then he'd be more than satisfied. I sent him back to Annie at the bar. At his point, I finished my drinks, the alcohol giving me a nice buzz. I touched up my makeup, made sure my clothes and hair were neat and then went out to the main bar. I was a little surprised to see several of my clients still there, drinking or eating, including the three friends. I could see if they tipped well, then Annie would be fine. She saw me as I sat down at the bar. I just wanted to touch base before I left. "Well, Annie you're right. This worked out very well. I'm ready to go forward with this. So I'll be back on Thursday at 4. Was everything okay on your end?" "Definitely. I've already made about $500 more than a normal Tuesday, as it is usually very slow. Plus Brad was thrilled. You're a godsend. Open your purse, and I'll drop your cash envelope in when I bring you a glass of wine. By the way, I've got six guys who want to do this every week, including the triplets. They loved it. I see no problems setting up a regular customer base every week with some monthly regulars too. I think this will be a wonderful partnership. Stewart's pleased too. Your traffic here means more profit for the bar." She left and when she came back, discretely dropped the envelope in my purse. I took my time with the wine. I was trying to figure out how I felt about the whole thing. It had been much easier than I expected, although my knees and jaw were sore. Really as soon as started sucking the first cock, my nerves settled down and I actually enjoyed it. Emily was right. I am a natural cocksucker. I could tell the guys loved it too. Only one guy had what I might consider an unclean cock, but I had assumed that would be something I would encounter occasionally. Everyone said nice things and I found I was actually getting turned on. In fact, I couldn't wait to get home. I hoped Emily was horny, because I wanted her cock in me so bad. I finished my wine, gave Annie a hug and left. When I got home, I checked the envelope. It was bulging with cash, $1500 in hundred and fifty dollar bills. I felt a wave of relief. If this really settled down to a regular routine, I might be looking at $3500 to four grand in cash every week. My only worry would be how to report this kind of income to the IRS. But my cash flow worries would be over. But for now, I needed sex with my wife. I went inside and found Emily huddled in front of the TV, as her show was just ending. She looked at me anxiously. Inside, I was still worried she would look at me differently. But I needed her now. I started toward her. "Hello honey, I'm home from work. How was your evening? I hope you're in a good mood, because I sure am." I lifted her up and wrapped my arms around her. I was concerned she might not want to kiss me, because of all the cocks that had been in my mouth. I lightly kissed her neck and the rim of her ear. "How about we go to the bedroom? I need to brush my teeth, undress, and if possible, get a hard fuck from your big cock. Any chance of that?" Emily giggled and kissed my cheek, while running a hand up my dress to stroke my pantyhose covered ass. "Sure, I can tap this ass for you. How did it go? Any problems?" "No, it went really well, actually better than I could have hoped. Our problems going to be how to handle all this cash. But we can talk later. I'm so horny I can hardly stand it." Emily took the hint, grabbed my hand and literally pulled me to the bedroom. I went to brush my teeth, undressing in the bathroom. Because of my fake pussy, I stripped all the way down. When I went back into the bedroom, I was greeted by a lovely sight. Emily was sitting on the edge of the bed, her part of the dildo inside of her pussy, while she stroked my side, coating it with lube. It looked wonderful. I had noticed when she used this on me, she instinctively took charge, so I just waited. "Up on the bed honey, on your back with that throw pillow under your ass. I want to see your face as I give you my big cock." I did as she asked, spreading my legs and rotating my ass upward as she knelt on the bed. I felt her guide the cock to my asshole and start to push. I loved how she was being so aggressive. No foreplay, or horsing around. She was just going to fuck me. It began to slide in, my asshole spreading open for me. Immediately, I began to quiver. I had been building a sexual need all evening. Now that tension was being released. The deeper she went, the more I squirmed, moaned, and pulled her in. Emily reached down to fondle my breast, rolling my nipple between her fingers. As her cock embedded in me all the way, she began to rock back and forth. Leaning forward she kissed me, roughly, love biting my lips and plunging her tongue all the way in. She withdrew her cock about half way and then plunged back in. My ass was on fire, my cock had swollen up as much as the tight rubber sleeve of my pussy would allow. It was already leaking cum, as I began to experience waves of sexual pleasure. I was becoming so used to having my boy pussy fucked, that it felt natural. Subconsciously I noted how Emily fucked differently than Leonard, both good, but separate. I liked that, as I wanted her to be unique. I began to push back, as she worked her cock in me, moaning loudly when she pulled back. I whispered to her that I needed her to suck my titties, to bite my nipples. She did so, roughly handling them when she didn't use her mouth. The physical sensations were starting to peak for me, and for her. I could feel her increase her rhythm, going in and out faster, but also grinding harder when she had her cock all the way in me. This position also meant more of her body pressed against my rubber wrapped cock. I could feel pressure from inside my body when she moved her cock and from outside when she moved her torso. It was becoming too much, and I began to orgasm. I was screaming now, calling her name, telling her to take me, use me, and give it to me. I could feel her tensing up as well, our orgasms feeding off of each other. Finally I actually felt my cock shooting come and her body quiver and then go stiff, as we both hit our climax. After a few seconds, she collapsed on top of me, both of us breathing heavily from the exertion. I lightly kissed her face and neck, whispering how much I loved her, how great she was, and how I needed her touch. We lay there, in each other's arms, her cock still in me, for a few minutes as we recovered. Finally, Emily propped herself up on one elbow, looked at me, with a sly grin on her face. "God, did I need that. I sat here in the house all night thinking about you and all those guys. I was getting worried you didn't need me. But when you practically begged me to fuck you, almost as soon as you came in, that made it okay. I can't get over how much I like this new sex and how much I want it. Knowing you want it too is just fabulous. I love you Dana, I'm just so glad you're my husband." I looked up at her, my eyes only halfway open. I moved up to kiss her softly, dropping my head back down. Even though my ass burned, I loved feeling the hardness of her cock. It just meant such a more intimate connection to her. But I was also starting to realize I was starving. I hadn't had any food since lunch. "Honey, I could lay here all night, feeling you inside me, but not now. I am about to starve. How about we take a shower, and get something to eat? You had dinner yet? I can make something light for us." Emily agreed that she too was hungry, although she had eaten something light earlier. We got up, she pulling her cock from me and we took a shower together. I loved both soaping her body and having her clean mine. We kissed almost the whole time. After drying off, she wanted us in matching baby dolls, with robes, so we dressed and went to the kitchen. As I made us some sandwiches, she peppered me with questions. She wanted to know all about my adventure. I gave her the details, all the details. I was surprised when she pressed me for more graphic descriptions of the men and their cocks. She loved how Annie had christened the three friends, 'The Triplets'. Emily also was surprised at how easily she allowed her boyfriend to be serviced by me. But most of all, she was overwhelmed by the cash. When I took it out of my purse and laid it on the table, she couldn't believe it. In some ways hearing about money, even a lot of money, doesn't have any impact. But if you see it. See the bills. You get a whole another impression. She was full of smiles as she fan it open, to see all the 100 and 50 denominations. After a couple of hours of talking and sharing a piece of cake, we were both tired. I loved crawling in bed, her body molded to mine. We both fell asleep quickly and slept soundly. There was nothing to get up early for, so we stayed in bed until later in the morning. Finally, I got up, put on my robe to go make coffee. I got it going and then slipping on my thong wedge heels, I went outside to get the paper. Old Mr. Glass was next door, raking his grass, as I went to the mailbox. I knew he had to be looking. The nightgown and robe were both very short, just past my crotch. I felt mischievous again. So as I pulled the paper out of the slot, I let it fall to the ground. Then I bent over, from the waist. I knew the entire length of my smooth legs were exposed, as well as my bare ass. I bet if he looked real close, he'd see my pussy, although I doubt at that distance he could. After picking up the paper, I walked back, looking at it, as if I was unware he was there. I had noticed, since I embraced my feminine self, that I enjoyed such teasing. As I thought about it, it wasn't so much that I was feminine that I enjoyed it or even did it. But because women and their bodies were viewed as sexual objects that could be displayed, such moves now had value. Old Mr. Glass would have never looked at me before, but as a woman in a short robe and heels, suddenly I was much more attractive. In a way this desirability was a type of power. I sensed the same thing when I sucked a man's cock. For a brief period, he abdicated his power to me. Surrendered his strength to me, allowing me to take the most private and sensitive part of his body and manipulate it and through it, him. Similarly, when I was dressed to emphasize my sexual attributes I felt very strong. Maybe society didn't view me as strong, but inside I felt strong and powerful. That was another reason I liked being a woman. Despite my position at work, I never felt that way as a man. Emily finally joined me for breakfast. We spent the rest of the day, doing mundane things, no pressure. I went ahead and took off the fake pussy form, as I knew I'd want to wear it a lot over the next few days. Somehow, when I peeled it off, allowing my penis to be free, it seemed like I was being unfaithful. I was beginning to do more than really enjoy portraying a woman. Somehow my life over the past few days had become what I wanted to feel as normal. Taking off the prosthetic, just emphasized to me how I felt incomplete now. These were feelings I hadn't shared with Emily, and I wasn't sure I could, yet. So I kept them inside. But we did have fun the rest of the day. We actually went out to a movie and a restaurant for dinner. We talked, and laughed. Mostly, at the texts from the boys. They seemed to be constantly sending us notes, comments, and questions. I told her I was excited to be with them again, and she confessed she was too. I saw that look in her eye, like somehow her interest in Jansen was a threat to me. So, I told her I was just as excited about the idea of him pleasing her with his big cock. Emily looked at me as if I had lost my mind. I laughed and told her, it was fine. In fact, it was so natural that she'd want to have him. I leaned over and kissed her. I admitted mine wasn't as nice as his, and I was okay with it. She didn't have to miss out because we were married. I also admitted I liked our new styles of sex better than what we did before. She beamed at that, and agreed. I could see some relief in her face that her desires weren't causing us any marital problems. I did confess that I was getting worried about having sex with Leonard again. Before, I used the implication that I was on my monthly period to avoid vaginal sex. Now that excuse wouldn't work, even the dullest man knew periods didn't last several weeks. I mean, he seemed to like taking me anally, but every man wanted pussy too. Emily admitted that might be tricky, but she'd think of something. She wanted to know if I was horny, but seemed relieved when I asked if it would be okay, if we just cuddled and watched TV. I had been in a sexual whirlwind lately, between our new sexual styles, my new job, and our new boyfriends. Just being close to her would be fine. So we did that and got to sleep early. Most of the next day was again low-key. But because I had to go to the Club for work, I started getting ready early in the afternoon. First was a shower with a thorough shave of my face, underarms, and legs. Next was putting on my pussy prosthetic. I checked the holes in my ear piercings and was happy to see they were healing up enough that I could switch from the post earrings to new ones. I inserted longer, dangling styles, so when I went down on the men, they would flash and shine as I bobbed up and down. I styled my hair and did my makeup. I again used the false eyelashes, as I loved how hot they made my eyes look. This time for my outfit, I decided on a look that I could make more revealing once l was in my space at the Club. I picked a sexy white lace pushup bra and thong, and suntan thigh-high stockings that didn't need garters. I paired it with a sheer, totally see-through white body suit, a dark red mini skirt and matching short jacket. I would wear the jacket in, but remove it once I started servicing my clients. Ankle strap high heels in red, a red mini-purse, and my CZ-jewelry completed my look. Emily had decided to give in and meet Jansen for dinner. No sex, just dinner. I laughed as she seemed to be taking as much time getting ready as me. She was more demure in her outfit. As I was getting ready to leave, she wished me luck and asked again if it was okay for her to go out. I told her I trusted her and that I loved her more than ever. This time the ride to the Club wasn't as stressful and I entered the bar very relaxed. Again, there were only a few people there. I was pretty sure that three of the guys, nursing drinks, were my clients. Annie saw me and briefly came to chat. "Everything okay? I got the clients lined up and the room is ready. I went ahead and booked ten guys, as I figured you'd like to do as many as possible. Do you want to start with a real drink?" "No, I'm good. We'll use the same code as last time, as I'm sure I'll want one at the end. I take it those men are here for me?' It was pretty obvious as they all looked at me and Annie. I could see them checking me out, so I smiled really big. I was getting excited about the new guys I would meet. Somehow, this job was becoming addictive to me. I gave Annie a hug and went to get ready. The room looked the same and I went to the smaller side room. I wanted to do something about the setup. Taking one of the throw pillows from the couch, I placed it so that when I kneeled to suck them, my knees would be padded. I also moved the lamp, so I had a better view of their cocks. I didn't want to miss any details. I checked out my appearance in the mirror and went back out to my table. Annie brought the first guy a minute or so later. I had seen him in the bar earlier, but hadn't envisioned him as one of my customers. He was short and quite heavy, although he was dressed nicely. He smiled at me and introduced himself, white Annie took our orders. I could tell he was quite nervous. Although he wasn't appealing at all, there was something about him that made me want to be sure he enjoyed this. I asked if it would be alright if I removed my jacket and he said sure. I unbuttoned it and started letting it slide down my arms. But I turned, so my back was toward him, asking if he minded helping. He quickly moved to take it off. As I turned to take the jacket from him, he saw my exposed breasts in the lacy bra. I was pleased that he inhaled sharply and he was laser focused on them. When Annie brought our drinks, we chatted a little. I was trying to make him as comfortable as possible. When he had finished, I stood up, asking him if he was ready. He followed me into the room. From there, most everything was the same. As I had suspected, he wasn't overly endowed and it did take some work to get past his large stomach. But once I began sucking him, he was like every other guy. I sort of giggled to myself, as he began to leak pre-cum. His was so sweet, it was like sugar. Finally he climaxed, thrashing around on the couch. As I got him back together, and touched up my lipstick, he thanked me. It was more than he hoped for and was a good investment. Again, I sort of laughed to myself, as I had never heard it referred to it in that manner. He left and soon another guy followed Annie to my table. The evening went by quickly and smoothly. The guys were all nice, seemed to enjoy my efforts, and most complimented me. It seemed more routine this time than the first. I guess I was adjusting and it wasn't so new. But I was feeling the same kind of buzz in my crotch as the first time. I just hoped Emily would be as horny from her date with Jansen, as I was. I had one guy left and Annie came to see me before bringing him back. She looked a little sheepishly at me. "Dana, I have a request from your client. He has actually been here all night, and saw you enter earlier. He wanted to know if you would be nude for him. I told him that wasn't part of the deal, and was about to say he could back out. But he offered an extra $50. He wouldn't touch, but he said you looked so magnificent, that was his exact word, that he was dying to see more of you. What do you think?" It took me a second, but I quickly decided. "Well, I'd be willing to strip down to my thong panty, but no more. If that will do, bring him back and I'll give him a show as well as a blowjob." She laughed and left. To my surprise, she returned with a tall, distinguished looking older man, probably late 50s with a touch of gray in his hair. Nice suit, a gold ring, and Rolex watch suggested he was well to do. Annie took our drink orders and we just chatted until her return. After she left, I spoke up. "Annie said you wanted to see more of me, so let me get comfortable. Is it okay if I leave my heels and hose on?" He smiled and nodded yes. I began by unzipping my skirt and letting it drop. I unsnapped the bottom of my blouse and slowly worked it up and over my head. I took a second to readjust my thong, making sure it was molded tightly to my pussy and well between my cheeks. As he looked intently, I reached around and unhooked my bra. Taking it away, my breasts fell down into a more natural, relaxed position on my chest. I could see him smile a bit more and he really seemed to be examining me. "You look as impressive without clothes as you do with them. I like how proportioned your body is, nice ratios. I am a bit surprised at your breasts, especially how large your areola are. Normally that doesn't occur in most males even with heavy hormone treatment. How long have you been on hormones?" I almost choked when he asked that question. I just looked at him, sort of in shock. I didn't know what to say. "Oh, don't get the wrong idea. It's not like you're unconvincing in your feminine portrayal. In fact, you're very nicely done. But I'm a professional. A plastic surgeon and I can see the minor details in your face and now your body that indicted I was correct in my original assessment that you are a biological male. Your gender identity is female, obviously, and you seem quite suited to it. But that doesn't change some of your physical structures that occurred as a male. I hope I haven't offended you, I was just curious. So when did you start hormones?" "I, I never took them. I just sort of developed liked this as I lost a lot of weight. Truthfully, I never noticed how my body had changed as I lost weight, I was focused on how much I weighed. I was surprised as anyone when I really looked at my figure. I had never had the typical male body shape, but as I was heavy, I had a sort of block look. When I started to lose weight I was just driven to reach a number. But I never made a move to look more feminine. I mean, as a teen, I had some gynecomastia, but never this amount of development. I was totally surprised by this." "Fascinating. Utterly amazing. It is very hard to believe in fact. The weight loss might accentuate the difference between your torso and breasts, but the nipple and areola development, the narrow waist and wider hips would need at least some feminine hormone influence to be this significant. Is it possible you got them from some source that you didn't recognize as hormone based?" "Perhaps, but I don't take any pills regularly, even vitamins. I don't smoke marijuana, nor ingest foods that might have estrogen-simulators from plants. It just happened." "Fascinating. Totally fascinating. As equaling intriguing is how you came to be so comfortable in a feminine role. Your identity usually takes a lifetime to develop, but even watching you for a short period indicates you have some innately feminine qualities that would not have been easy to learn or even practice. So do you intend to complete your transition with sexual reassignment surgery or stay like you are?" I blushed now. It was obvious my pussy prosthetic didn't fool him. But I also blushed because I was somewhat afraid to answer. It was hard to admit. "Truthfully, I haven't decided. Although every day I get more comfortable wearing the prosthetic, so I appear real, than going as I am naturally. I could see myself as becoming a full female. It's just that I have others in my life to consider which makes the decision harder." "I totally understand. Look I hope you're not offended, and I will still pay your fee, but I think I'll pass on your offer of service. I would much prefer we develop some other kind of relationship. I've helped lots of transsexual individuals reach their desired goals and would like to counsel you too. I'd like a chance to do a better examination, in my office of course, that would include physical measurements, blood work, and a more precise evaluation of your mental state. I find your case is quite unique and I think it would be good for both of us. Eventually I could give you the female genitalia that suit you, as well as some other minor tweaks to maximize your female appearance. I could even do breast enhancement if you desire. Even without a physical manipulation I can see your breasts have quite a bit of potential for enlargement, and still maintain a natural look. You're a B-cup most likely, but you have the ability to fill out a full C- or even D-cup after surgery." I was stunned now. Not only had he guessed my true sex, but now he was critiquing my body. I was lost and just responded automatically. "I didn't realize my breasts looked bad. I guess I was surprised at their presence at all. I do appreciate your offer, I mean it does sound helpful." "Oh, dear don't take my suggestion that way. Your breasts are lovely. I'm merely speaking from a balance standpoint. Sometimes as a plastic surgeon, when I see someone's body I look for the ways I could tweak or improve it. That is entirely up to you. But I do wish you'd come by. I won't charge you anything for any of my introductory advice, or examinations, and could provide you with the way to make your life complete. I'll leave my card. And again, you're magnificent in appearance, and after this brief discussion, a very interesting and likeable individual." He put a card on the table, stood up and left. I felt overwhelmed and didn't know quite what to do. I went to the table and picked up his card. It had his name, Dr. Clarence Clark, with his address, and a list of accreditations, and a website. I was standing there looking at it, when Annie came back in. She walked a few feet and then stopped as she saw me. "Oh, I'm sorry Dana, I thought since your client left, you'd be done. I take it he was satisfied by your appearance, he seemed to be pleased when he left. I'll go and let you get dressed. Do you want a drink?" I looked at her and smiled. I could see her looking at me and for some reason, it made me feel good. I had always been self-conscious about my appearance. But now, I enjoyed showing off my body. I turned so she could get a good look and noticed her glance at my breasts. "Yes, can I have my usual? I'll take it at the bar. But first, what do you know about that last client?" I reached down to get my blouse and began to put it on, slowly, working it carefully over my head. I had decide to skip the bra, since I would soon be heading home. As I got dressed, Annie watched me, in the way women watch other women do things, not sexual, but observatory. "He's a nice guy. Comes here for a drink or two, a few times a week. I think he plays golf, with a couple of the other doctors. He's a surgeon, I know that. He did a breast enhancement for one of the waitresses here. She loved it and his work. I also know he's done a few charity type things, like fix a cleft palate for a young boy whose mom was on assistance. I've lined up escorts for him before, not often, but enough that I thought he might like you. Although, he never wanted them nude before. Why, he didn't do anything creepy or out of line did he?" "Oh no. He was a perfect gentleman. He just intrigued me that's all. Well I'll be out in minute for my drinks." I had worked the skirt up my legs by now and was starting to gather my stuff to go. Annie went back to the bar. I checked my makeup and hair, slipped on my jacket buttoning it so my breasts wouldn't be visible to the casual observer. Putting my bra and the business card in my purse, I joined Annie at the bar. I had just sat down, done my shot of schnapps and was working on my wine, when a young man approached. I had seen him when I came in, as there were only a few people in the bar. He was the only one who hadn't been one of my customers. He smiled, stepped right next to the bar with his hand on it, moving close and facing me. I could see him checking me out, scanning my body, especially my legs, since the lace band at the top of my stockings were showing. "Hello, what a nice surprise. There's usually never anyone this beautiful here. I'm Blakely. Can I buy you another shot? Vodka or Tequila?" "Hello Blakely, that's a nice offer, but I'm fine." "Oh come on, the nights young, live a little. I'll just order you one, Miss?" "Dana. You're sweet but it's neither of those, its peach schnapps." "Woah, that's different. What led you to do that drink?" I had to laugh to myself. This young Romeo was trying his best to be cool. But he didn't even look like he was old enough to drink. Had to be barely 21. I mean it was complimentary that he thought I was attractive enough to hit on, despite the wide gap in our ages. Sort of like the boys, but even younger. But I knew he was just trying to score, and he was right. There were no other females here, beside Annie that were remotely attractive or single. I couldn't help it, and decided to play with him. I made a show of unbuttoning my jacket, letting it fall open. He noticed my bare breasts immediately. I put my hand on his thigh, right below the developing lump where his cock was reacting. Then I leaned in close to him, so I could whisper in his ear. "Oh schnapps is the perfect drink after you've given someone a blowjob. Cuts through the aftertaste of his cum, so you're fresh and ready for more." I moved my hand up his thigh, gripping his cock through his pants leg. I lightly massaged it, making it grow even more. I could see the shock on his face. He obviously never had this kind of open sexual response to any of his moves before. I could sense he realized he was in over his head. Giving him one last stroke, I moved my hand away and leaned back, smiling broadly. "But I'm about ready to go home, so I won't need another one. Thanks so much for your offer Blakely, you're a cute guy. Maybe some other time, okay? It would be fun to get a little more personal." He finally smiled, realizing his effort was not going to work tonight, but he was even more energized both by my flashing him and by my touch. "Well if you give me your number, I'd love to see if we could find some time better suited to get together." "Let's not. I think it would be better if we just run into each other again. I enjoy sex much more if it's spontaneous, don't you?" At this point, Annie came by. She seemed amused, as she had watched his moves and my reactions. "You need anything before you go, Dana? How about you Blake? Another drink on your daddy's tab?" I could see him blush now. He shook his head and left. As soon as he turned away, Annie put an envelope in my purse. "I see you met Blakely. He likes to come here, because his dad lets' him run a tab. He's at college, but comes home, now and again. Cute kid, but not very experienced." I laughed and nodded my head to agree. "I'm going now, I'll see you tomorrow after my golf game. I may come by the bar first thing to drop off a change of clothes. Is that okay?" "Sure, they open the restaurant at 7 am on weekends, including Fridays, as some golfers grab breakfast first. So you can get in to your side room. I'll be here at 10 for my shift. Night honey." I waved bye and left. I winked at Blakely, slowly buttoning my jacket as I passed him. By now I was starving. So, I called Emily, told her I was picking up Chinese, and did she want any? She told me was still full from dinner, so I swung by to get it before going home. But my thoughts kept going back to Dr. Clark. That and wondering how Emily's date went. Emily was waiting for me at our kitchen table when I got there. She had poured two glasses of wine, put out a plate and chopsticks for me. She must have just gotten back, as she was still wearing the skinny jeans and semi-sheer loose top she had worn on her date, although her pumps were by the door. I was going to change, but decided against it since she had everything ready. I did remove my jacket and heels, before sitting at the table. She noticed my braless look right away. "Well I bet that look was well received. I thought you were wearing a bra under that blouse?" "Oh, I did. It's just that my last client wanted to see more of me, and offered an extra fifty if I would be nude for him. I agreed to strip down to my panty, but when I was getting dressed to come back, I just left off my bra." "Any other unusual stuff at work?" "Not really. Most of the guys were okay, normal looking. Just regular guys, there was one short stocky guy, but he was nice and an older man, the one who wanted to see more of me, gave me something to think about. But we can talk about that later. Tell me all about your date with Jansen." She laughed, and it looked like, blushed a little. "He's so cute. He pestered me with questions all night. I swear, if I had known these two were going to be like this, I might not have agreed to go out with them. He is sweet and I have to admit in some ways having a cute young thing being so attentive to me is an ego builder. But what I find most fascinating, is his interest in my 'husband'. Jansen asked as much about him, as he did me. I think the idea that he is doing some other guy's wife is a big turn on for him. Sort of a validation of his sexual prowess." "So where did you guys go eat?" "We went to Conner's. I had a big steak and a few drinks. It was nice." "Anything happen afterwards?" I could see her blush again, and she looked down at the table. "Well, we did make out in his car in the parking lot. Guys that age just have so much pent up desire, it's like being next to a stick of dynamite." "Did anything happened with that stick?" She looked up and smirked, her cheeks still a little rosy. "I may have played around with it a little, you know to keep him interested in us." "Nothing more? No sex?" "I wouldn't call it sex. I did take his cock into my mouth. But only briefly, I started to gag almost as soon as it hit my tongue. I took it out, and started to try again, only he stopped me. He said I didn't need to do it if I didn't like it. That was nice, but I could tell he was really disappointed. After that he brought me home. It was like an old fashioned date. He walked me to the front door, and gave me a good night kiss. I whispered to him to make it quick, as my husband was home. I could tell that fueled the fire." "You shouldn't be toying with him like that. I know I'm still worried about our planned night with them. I just hope it will be okay." "Well, good news. I have it all figured out. When I was trying to please Jansen, it hit me. We've been treating this like they were our boyfriends. That's the wrong approach. First they're starting to get attached, wanting more from us, and pushing for more of our time. Second, we only wanted them for sex, so we need to focus back on that. There's no reason it should be just Jansen with me, and Leonard with you. We need to switch partners. It would break the boyfriend- girlfriend dynamic that is building. It would allow me to give Leonard some pussy, taking the pressure off of you. It would allow you to use your natural oral talents to please Jansen, giving him the release I can't. So what I propose we do on Saturday is turn it into a sex party. We'll all be in our big bed, same room. We'll change partners. We'll show them our whole relationship with them is about sex. Plus, we have to use our imaginary husbands to our full advantage. We tell them we can't have emotional contacts with them. It's only sex, because we are married. You can tell them, that they can't have your pussy because you've promised your husband that is off-limits to your lovers and only he can have it. That way, it will solve your intimacy issue and still allow Leonard to have intercourse. I think if they believe we are cuckolding our husbands with them, they will be even more turned on. The idea that we are available for sex with them, with no strings or commitments should be what a couple of young men like that have dreamed about. What do you think?" I smiled at her and squeezed her hand. "I should have known you'd figure it all out. It's perfect in so many ways. But it will be challenge. I have to confess, it may be difficult to watch you with another man. I know you're doing him, and even heard you that first night. But to see it, well that will take some control for me. Plus, having you watch me suck a man is another hurdle for me. I mean, it's obvious that I'm firmly in the cocksucker camp, but still I will have to get over that too. I mean, will you still think of me as a man?" "Honey, I have to confess something. I think of you as a girl now. All the time. I mean, you dress, act, and look totally female. We've developed a closeness that we never had has husband and wife. I like having you as my girlfriend and lover. Personally, I can't wait to see you go down on Jansen. Both to see his reaction and watch your special skill. So don't think that I will change my impression and love for you with this. I think once you see a man fuck me, you'll be even more at ease with your femininity. But enough about them, tell me more about this one guy at work. What did he give you to think about?" I looked at Emily, trying to read her. I know she just said she thought of me as a woman already, but how would she feel if I truly became one? Would she love me the same, if I had a vagina and labia rather than a penis and testicles? Is she thinking of my femininity as a role-play adventure? Plus, what did I really think? Could I do it or was this just an infatuation? "Well turns out he was a plastic surgeon. He was the one that wanted to see me nude. Apparently, he'd seen me earlier tonight, in the bar. So when it was his turn he wanted to see more of me, but not for the reason you might be thinking. Turns out, he made me. He saw some of my features, structural I guess, that meant I was male. He did compliment me on my appearance. I think he was amazed at how I looked, without being on female hormones. So he made a few observations and suggestions." "I can't believe he identified you as a man. You are so convincing, I just imagine anyone seeing who you really are. What kind of things did he mention?" "Well he talked about my breasts. He said there were nice, as they are, but I had potential to be bigger if I wanted." "Bigger? Did he say how big?" I could see a sort of twinkle in Emily's eyes. We were both about the same up top, but maybe the idea of me being busty was appealing. "Oh he said I could probably go to a C- or even D-cup and still look real natural. But he would want to do a hands on examine first." "Wow, Ds would give you a whole other look, so much more sexual. Anything else?" "He mentioned a few tweaks, minor things he saw that he could address to make me more feminine. But didn't give many details. However, the one thing he did notice that we discussed was my prosthetic. He saw right through it and could tell I was still a man. He said he did those kind of surgeries too." "You mean make you a woman? Completely? Remake your privates?" "Yes, although he said he'd have to confirm everything with an exam. But he thought I was a good candidate, as I had so many feminine features already." I was looking at Emily intently. Looking for a sign, good or bad about this idea. I was afraid to say much more, since it was a life changing decision. If she wasn't prepared to go that far, I didn't want her to know how much it appealed to me. I mean, I wasn't sure the appeal of having a vagina was sincere for me either. I could just be getting swept up in the moment. She looked down at the table, a telltale sign she was nervous and entering unchartered territory. "Did you like that idea? You've really seem to enjoy and embrace being a woman. You've even seemed to adjust to having sex that way. Have you thought about it?" I hesitated. I didn't know how to respond. But Emily sensed my uncomfortable feeling. "I'll be honest. I've wondered if you wanted to be a complete woman. Maybe I misread you, but it seems you enjoy wearing the prosthetic more than being without it. You have a certain glow or attitude with it on. I could certainly see you having your own real vagina and being happy with it. Did I read you right?" I knew I had to answer. I couldn't keep it hidden any longer. "Yes, I have thought about it. You're right about me feeling better, maybe more complete is a better term when I wear the prosthetic. But sex reassignment surgery is such a major decision, a one-way choice that it is difficult to tell if what I feel is real. Even after the surgery, there would be a need for lifelong hormones, not to mention legal and society issues. Dr. Clark, he gave me his card, did offer to do a free examination and a consultation session. Maybe we should go to that, and find out more." Now I was the one starring at my hands on the table. I was afraid to look up at my wife. Afraid that my interest in being her wife, physically, rather than her husband was too much. "I think that would be an excellent idea. I mean, you should see what your options are and I would love to hear about what tweaks he might have in mind. I would love for you to consider getting your lips done. Big, plump and full. I think it would so enhance your appearance. Especially if you decided you wanted to be all woman too. Do you think you get choices on how that would look too? I have no idea whether they can make you look just one way, or give you options. I know I wish my labia were bigger, sometimes I just feel so small down there. But first things first, figure out when you might go. Then we'll be able to make a better decision." I looked up at Emily, again feeling so lucky to have a wonderful partner like her. I felt like my life was going in a new direction, an exciting direction and was glad she wanted to go there with me. After I ate, we both agreed we were tired and started getting ready for bed. My earlier desire for sex had been lost during our intense discussion of my future. I washed my face to remove my makeup and picked out my outfit for golf tomorrow. We crawled in bed, spooning until we fell asleep. It felt great to have her cradle my breast in her soft hand, her body molded to mine, like a security blanket. I had set an alarm for the next day and awoke to the music. I quickly did my bathroom duties, including shaving my face. I had decided to do my full makeup, as I would be working after golfing with my friends. I also curled my hair and sprayed it as it would be outside. I assumed I would need more touchups after my game, so I packed my beauty supplies in a small tote to take to the Club. I had decided to wear the golf dress, with lace ruffle socks, sheer thong and matching pushup bra, both in light blue. I also gathered my work outfit, heels, and matched it with a small purse. After I put my clubs, supplies, and clothes in my car, I had some coffee and a breakfast bar for some energy. I was planning out my day, thinking about my each step. But I kept coming back to Todd. Even though he was so big, I had developed an urge for him. Something about the way he filled me to the max, made me love sucking him. I still couldn't believe he had trouble getting dates, given his cock size. He was all I could think about on the drive there. I parked again in the employee lot, carried my clothes and supplies to my little area off of the bar. Once everything was stored away, I went back to get my clubs and put on my spikes. I got to the first tee, just as the guys were pulling up with the cart. They all greeted me, eyeing my outfit. I put my clubs in the back of the cart, bending over as I did. I knew that would flash my ass. The dress had a short-leg panty, made of matching fabric, to wear for modesty, as the hem was very short. Of course, I had opted not to use it, as I wanted them to get glimpses of my thong, whenever I swung my club, bent over to pick up or put down my ball, or generally move at all. Although they were all very friendly, I could sense a sexual tension, as I was sure they couldn't wait to get to our hidden spot. My assessment about their eagerness was correct, as none of them were playing very well. I was actually quite close in score with all of them, which in the old days would have been unheard of. Now they weren't concerned about it and only teased me a little about my game. It felt odd, as I rarely felt like I was a part of their group. Now it was more like they accepted me, in a special way of course. We finally got to the cart path before the fourteen hole. Ham maneuvered the cart into place just like before, and turned to look at me. I could tell they were all anxious, but weren't sure how to start it. This is where I took over. "Todd will you help me with my dress? I think it would be best if I took if off before we get started. I just hate getting stains on my new clothes." I turned so my back was toward him and he slowly unzipped it. I could feel his hands shake as I he pulled on the zipper and smiled to myself, as I realized despite this being the second time, they were nervous. I stood up, and wiggled the dress down so I could step out of it. I stood there, in only my sheer bra and panty as they checked me out. I adjusted my bra first and then tugged my thong a little, both for show more than anything. I pulled the thong up, so it looked like it was painted on my pussy, both the labia majora and minora clearly visible. If they had any doubts about me being a girl, they were gone now. "So who wants to go first? You bring the blanket Ham?" "Yes. We drew straws in the locker room, so it's going to be me first, then Brick, and Todd last. Is that okay?" "Perfect. Let's go, I feel real hungry this morning." I winked at them, as I took Ham's hand. We went down to the most secluded spot, put down the blanket and I knelt in front of him. Ham was excited and it didn't take long to bring him off. I was getting pretty good at controlling men's orgasms, extending them if I wanted, or speeding them up. Either way they were happy, especially as I always sucked and licked every last drop of their cum, like it was ambrosia. I sent Ham back up and he was replaced by James. Again, I made him come quickly. Although I had sucked quite a few guys now, when I saw each cock, unique in its appearance, I remembered what that guy liked or didn't. So even though it went by fast, their blowjob was still among the best of their life. When Todd came back down, it was a different feeling. I was getting excited and knew I would want to stretch out our time together. I unzipped his pants and took out his killer cock. Just holding it was a thrill, as it totally filled my hands. I looked up at him as I held his cockhead inches from my mouth. "Umm, Todd, I've been wanting this all day. I love tasting your cock, it's so special. I hope you don't mind if I take my time." I started on him and as soon as I put my lips around that big cockhead, I felt a shudder in my cock and balls. It was like a mini-orgasm. I began to use all of my techniques, bringing him close to coming several times, before backing away. Any time I swallowed all of him, taking his cockhead way down my throat and having his shaft fill me all the way back to my lips, I felt that mini-shudder. I loved it. Finally, after a good fifteen minutes, I began to drive him to his orgasm. He exploded like a bomb, putting so much come in my throat and mouth, I thought I might drown. Finally as I used my tongue to wipe off his cock head, I looked up at him. He had already complimented me multiple times. "Oh Todd, that was great. I hope you liked it, as I have to confess, I enjoy doing you more than any of the other guys." He smiled and helped me off my knees, then picked up the blanket. I could see he was checking out my pussy as I did so. "Dana, do you mind if I ask you a personal question?" "Sure it's okay to ask." "Well I guess I didn't think you'd really gone all the way, but I think it's pretty clear you did. What caused you to make such a radical change? Weren't you scared?" I smiled and laughed softly. I reached out and stroked the side of his face. "Todd, it was just something inside of me. I didn't feel complete, or even authentic. I made my way as a man, because I had no other choices at the time. But when the opportunity came, it was right. I love being a woman. So it was an easy choice. But yes, I was scared. I still worry. I know it seems odd, but having you guys accept me this way, really helps. So are you okay with me like this?" "Not to mince words, but hell yes. You're probably the best woman I've ever met. I mean beyond your personality and looks, no girl has ever embraced my cock like you. Even though you do it for money, you still stand out. I just wish I could find someone like you, who wasn't in a relationship." "Tell you what, let me check around. I might have someone who would be right for you. Now let's see who can finish the last holes the best." Todd smiled and took my hand. Back at the cart, he held my dress for me, so I could step into it. I put my hands on his shoulders and as he held it open, I stepped in. I just happened to lean forward as I did, so my boobs, pushed up by my bra, rubbed across his face. His blush told me all I needed to know. After he zipped me up, they gave me an envelope with their payments. We went on to finish the round. Of course, I finished last. Before we had always bet on the games, which meant I routinely owed them drinks. They pestered me to join them for lunch, but I knew I needed to work. So since it went so well today, I decided to pay off. "Look guys, I can't join you for lunch, but I know I finished last. How about next week, I give you a 50% discount? Is that a deal?" They all agreed, gave me hugs, and left to go to the locker room. I made my way toward the bar side area. As I went, I thought about Todd's question and my response. I answered him honestly, and knew what I needed to do now. But what I wanted to do was find out more about Dr. Clark. Maybe Annie's friend Denise, the barmaid who had surgery by him, would be here. In any case, I started to get ready to work. I touched up my makeup, which was more difficult than it sounds. I wanted to look sexy, but I realized that during the day I couldn't go overboard. I focused on my eyes and lips, trying to hit a nice middle ground. I had already taken off my dress, so I worked a pair of sheer pantyhose, a lovely taupe color that went well with my outfit, up my legs. I had a simple shift dress that conformed to my shape, going down to just above my knees. The top had a rounded neckline that showed just a hint of cleavage normally, but when I was on my knees in front of a client would give a much better show. The pattern was an abstract gray, dark beige, and black, simple but suitable for daywear. I paired with black suede pumps, again not too dramatic. After I was all set, I headed into the bar. I was pleased, Annie was talking with Denise, the barmaid I was seeking. As I approached, Denise left to wait on a new customer. Annie saw me and smiled. "Long time no see strange. Weren't we just here a minute ago? But I do like how prompt you are, perfect employee. None of your clients are here yet, so it will be a few minutes before you can start. We've got a total of six, with a possible seventh." "Good, I'm glad we've got a minute. Do you think I can ask Denise about her surgery? I'd like to talk with someone who's been one of Dr. Clark's patients." "I think it would be okay. It wasn't like she hid anything about her boob job. That's kind of her MO, she likes to tell things about herself." "Oh really, not a private person?" "Well at least not to other women. She's told me about her craving for dark chocolate, how she likes to go commando when she's off the clock, what kind of guys she likes, and even description of her latest date and their sex." "LOL. That's a hoot. So many women won't share anything. I guess you know her type then?" "Oh, she's a definite size-queen. She can't hold back if she finds a guy with a big cock, even if they treat her badly. She'd do anything if the guy has a sausage in his pants." "But how about her? Is she a good person? I might have someone you'd be a good match for her, but I want it to be the right kind of connection." "Well, I've always liked her. She's a good co-worker, honest, and funny. I know she shares an apartment with a couple of girlfriends, is smart with her money, and gets along with most people. She dates, but not a lot. I think she's a sweet person who just hasn't found the right guy." "Okay, thanks. I think I'll go see her. It looks like she's coming back to place an order." Denise was at the order station, pouring a couple of soft drinks and giving the cooks her orders. I came up her, and asked if we could talk after she took her customers the drinks. She nodded yes, went to the table and returned. I could see she was sort of puzzled by what I wanted. "Hi, I've got a minute now. It's usually slow here at first. You're Annie's friend aren't you? I know she's working with someone new here. What can I do for you?" "Hello, I'm Dana. Annie told me a little about you and I was hoping you'd be able to tell me something about Dr. Clark. I'm considering getting some work done by him, and she said you were a patient of his." "Yes, I was. He did a great job for me. I guess she told you I had a breast enhancement. It was everything and more than I expected. I went to him, wanting to be really big, but he told me he'd only go so far. That I would be happier if I had a size proportional to my body and that looked realistic. He was so right. I pushed for something like a DD, but I wound up with a full C cup. I love them. I'm big enough now, but can still wear a wide range of clothes. Plus my boobs don't look like two swollen balloons on my chest. The best part was he helped me arrange financial payments that didn't break me. So if you're considering him, I'd fully recommend him. Are you thinking of getting a boob job?" "Yes, and maybe more. I haven't fully decided. But I like your recommendation. That's the kind of advice I'd want my doctor to give me. I want to look better, but not like a freak, you now? Thanks for sharing, I appreciate it. But I have another question. Are you up for a blind date? I know a guy, real nice person, has a good job, and is sweet, kind and caring. I think you and him, might hit it off. I'd like to suggest he talk to you if you're interested. Plus, he has that special feature that Annie told me you like. He's more than nice in that department, if you know what I mean." "Oh, really? If he's so nice and equipped, why does he need a blind date? That kind of man usually has more than he can handle." "To be honest, I was surprised too. But he doesn't see what he has as a positive, but more a liability. He's not the tallest guy and it seems the petite girls he dated before weren't thrilled by his size. He's not really had a great sexual experience. But I can assure you, he's loaded. He comes here quite often, you've probably seen him. In fact, I expect him to have lunch today. His name is Todd Jost. I could get Annie to show you him when he's here. If you're interested, I'll hook you two up. I think it might be good for both of you." Denise smiled at me and said sure. I told her I'd talk with her later. Annie signaled me that one of my dates had gotten here. I told her to show Denise who Todd was and then left for my 'station'. I was beginning to think of this as any other job. It was becoming routine and I didn't get too anxious when I was with a client. I only had to get over that initial awkwardness, when I went to get their cock out of their pants. After that, I was in control. The next couple of hours went smoothly. A couple of the guys were really nervous, but settled down once I got going. Most of them came quickly, with only two taking extra effort on my part to get them to climax. I was getting much more comfortable with the range of cocks I was handling. The great majority were in a narrow size range, only a few were uncircumcised, and all of them seemed very satisfied when I finished with them. About the only negative, was having to redo my makeup in between customers. But I was adjusting to that as well, I would just need to pick up another tube of my signature cinnamon color lipstick. When I was done, seven guys, I joined Annie at the bar for a quick drink. I wanted to see if Denise had said anything. She did get a look at Todd and thought he was cute, even if he was probably slightly shorter than she was. Denise came by and told me, she'd seen him in here before, even waited on him a few times, and never realized he was packing, so to speak. She was very agreeable to meeting him. I told her to let me see what he said. I warned her, that he wasn't highly confident and might be reluctant. But I would do my best. So, after my shot of schnapps and wine, I headed out to my car. The ride home was smooth, with my thoughts bouncing between helping Todd, our upcoming sexual escapades with the boys, and whether I was ready to meet with Dr. Clark. I knew I felt ready to take the plunge and have surgery. The more I had thought about bigger boobs, the more excited I got. I already loved showing them off, and if they were bigger, firmer, with more cleavage, I'd be unstoppable - LOL. But other surgeries would mean so much more. I knew I loved the look of my pussy prosthetic. But could I part with my cock and balls to get my own real one? There was no turning back from that. I knew I felt best when I looked all girl, but would that joy fade and be replaced by resentment at having sacrificed my cock? I knew I had only been immersed in femininity for a very, very, short period. I had doubts that my desire for my own labia and vagina were just a product of my infatuation with my new image. Would I still feel I made the right choice in a year, five years or more? I had spent all my life as a man. I thought I wanted to spend the rest as a woman, but was that real? I would need more time and advice from people like Emily, Dr. Clark, and maybe others like our lesbian neighbor, Andrea, or Dee Ann. Beyond the physical and emotional change, I knew I would face a gauntlet of legal hurdles to become female in the eyes of society and the government. I pulled in the driveway and put these thoughts aside. I had to focus on what was next. Inside, I took out my pay envelope. With the money from the guys, and even with a short shift I made well over $1500 today. The total for the week was now more than $4500. God, it seemed like so much for so little effort. I knew I loved sucking cock. Each one was like a present. I had gotten to where I was eager to find out how they looked, what they tasted like, and how much cum they would give me. The time I was at the Club flew by, and I was always done with my customers before I knew it. Making this much money for having so much fun seemed sinful. But I'd take it. I just needed to setup a cover story, like a consulting firm, to account for my income. But first, I wanted to find Emily and see what our plans were. Inside I looked and then called her name. She responded from the bedroom. As I walked in, I could see a couple of shopping bags on the bed. Good thing was now I wasn't worried about her spending, I was covering it easily. But I was curious about what she had gotten. I could see by the smile on her face, whatever it was made her happy. "Hello honey, I see you've been shopping again. What'd you get this time?" She moved to me and gave me a quick kiss, standing by me as we looked at the bags on the bed. "I had another wild hare idea, and was able to find what I was looking for. I think you'll love it too. Go ahead and see what's in the bag on the left, that one's yours." I went to bed and opened the bag. Inside was a lovely, rich burgundy and black piece of lingerie. As I held it up, I could see it was corset. A pushup, strapless style, with four garters. There was also a matching G-string panty. I turned to look at Emily. She had come over and opened the other bag, to reveal the same style corset in her size. Smiling she looked at me. "I wanted us to have something super sexy to wear for the boys. Something that says sex is the only thing on our minds. We'll wear these, some sexy black stockings, red heels, and nothing else. I know the plan is to go out for dinner. When we go, we will wear those cute wrap-around coats we bought for rainy weather. They come down just far enough to cover our stockings, but it will be easy to flash the guys when we want to. I want them super horny from the minute they pick us up for dinner, and all through the night. If we both don't come at least five times, then I'll be disappointed. We're going to set the tone for the rest of our relationship with Jansen and Leonard, that sex is our focus with them." Emily was beaming. She was so pumped up about this. This attitude seem logical now, but it was such a departure from our lives just a few weeks ago. It was hard to imagine that this sex kitten was my wife. That she was planning on a night of wild sex that weeks ago would have been only an unbelievable fantasy. But that was who Emily was now. I could only imagine what the boys would think. To have two married, middle-aged, but still sexy and attractive, women plan an evening of wild sex for them, would have had to be among their most desired fantasies too. I looked closer at the corset. I knew it would look sexy on and only hoped it wouldn't be too constricting. I already knew from just a few weeks of assuming a feminine identity, that women will often endure pain just to appear more beautiful and sexy. I had to admit, I would love seeing a woman in something like this when I was a man. I also had to admit, the idea of wearing it to excite the boys, was thrilling for me too. I knew deep inside that I wanted to be as sexy as possible. I looked over at Emily. "Well let's try them on. I can't wait to see how we look. I just hope the boys can keep from coming in their pants when we show them how we're dressed." We both laughed at that, as we stripped down to try on the corsets. It took a bit of work to get them on. We had to loosen the laces, then wiggle the corset up over your hips to settle around your waist, and then take turns tightening each other's' laces until the garment was snug, or very snug to your body. It turned out my fears were well grounded. The tight control of the corset as it pressed against my ribs and waist was painful. But I loved how it held my breasts up and enhanced my hourglass silhouette. I would gladly endure a little discomfort to look even sexier. It ended right above my pelvis, so my ass and pussy were visible. But the pretty G-string gave me enough coverage in front, but would allow an eager dick to get to my asshole. It took some effort to attach the stockings, especially making sure the back seam was straight, and put on our shoes, but it did make a very appealing image. Standing next to Emily, we looked like a couple of burlesque dancers getting ready for a show. Emily got our coats, and we tried them on over our lingerie. It worked perfectly, covering us so that our stocking tops weren't visible when we walked, but when we sat down flashing both the lace top and the stretched out garter. Of course, undoing a few buttons, showed off the whole ensemble. I loved it. I may be new to being a woman, but I was enjoying feeling like a real sexual being. As a man, I knew women who embraced their sexuality and desirability were unparalleled. I couldn't wait to give the boys, as well as my wife and I, a night to remember. Emily suggested we wear the corsets for a few hours so we would be more accustomed to them. I agreed, and we spent the rest of the evening with our bodies tightly held by them. She also pointed out how she had modified our house to reflect our cover story. She had photo-shopped another man into pictures with her, including a wedding photo, and put them on display in the house. Any image of me as a man, was gone. She had even picked up a couple of items from the thrift store to re- establish some sort of male presence in our bedroom, including a robe to hang on the back of the bathroom door, some slippers, and a couple pairs of pants and dress shirts to leave casually strewn on top of the laundry basket or over the back of a chair. It reminded me just how far I had gone toward being a woman that she had to buy things just to make it look like a real man lived here. After a light dinner, and a little more preparation of the house, we finally took off our corsets. I had to admit, the release from being tightly held was nice. Emily did wonder if we could actually wear them all night, to which I responded, only if we were being fucked all night. If the boys wore out, I was going for a nice baby-doll look. She laughed and told me she didn't know which option to hope for more. Since there was no rush, we both slept in, trying to bank as much rest as possible in anticipation of a wild night on Saturday. For most of the day, we just went about getting things ready. We made a last minute shopping run to get a big bouquet of flowers for the bedroom, two bottles of champagne, and an assortment of colorful condoms to fill a bowl at our bedside. I could tell Emily was getting really excited, and truthfully, so was I. We went over details in the house, that were far too minute for the boys to ever notice, but then again, we wanted it to be perfect. That extended to preparing ourselves as well. We both washed our hair, so we'd have nice perfect hair styles. We took a long bath, to allow us to shave every part of our body so we'd be silky smooth no matter where they touched us. I checked to be sure my pussy prosthetic was firmly attached. We did minor touchups on our nail polish, filling in a couple of color chips and then applying a full top coat, so they all would shine like lights. When it was time to start getting ready, we took extra care with our makeup. Emily helped me with mine, her expert touch insuring the small details, like eye liner over my false lashes, and even outlining my lips so my lip stain wouldn't creep outside of my lips. As we started to dress, we laced up each other's corsets, help put on each other's stockings, and shoes. The tight fit of the corset seemed more worth it now and we both asked the other to pull a bit more on the laces then we did yesterday. I could already feel Leonard's big hands grasping my tiny waist as he filled me with his cock. I'm sure Emily felt the same. Finally, it was time. We were totally ready and when Jansen texted us that he was pulling up the street, we both couldn't help grinning. Tying the sash tightly around our coats, we grabbed our purses and went to meet the boys in the driveway. We had suggested a nice romantic restaurant nearby that served simple American fare. They were so attentive and talkative. We walked in and found a nice booth in the back. Emily and I had decided to eat light, both because of our corsets and general lack of hunger for anything other than sex. As we stood by the booth, Jansen continued to be the perfect gentleman. "Ladies, do you need help with your coats? Let me take yours Emily and I'll hang it up." We turned toward each other and grinned. Then facing the boys, so that no one else, more or less, could see, we undid the sash and held our coats open. They practically fell over. "Umm, I think we'd be better off keeping them on through dinner, don't you think sweetie? I mean we wanted to be ready for you two as soon as we got back to the house, but I don't think we could start here." We buttoned our coats and slid into the booth, the boys following us in. To say the dinner was an afterthought would be an understatement. Everyone had the same idea and we all ordered light meals which we ate quickly. Emily was now as chatty as the boys, allowing me to just enjoy the moment. After they settled the bill we headed back to our house. Of course, we had pre-arranged that we'd remove our coats for the trip home. The boys were never more excited. We each gave our coat to them to carry as we walked to our front door. Again, as we had planned, we turned to face them. Emily wanted to lay out the ground rules for the evening. I stood there, the early fall temperatures causing my nipples to hardened, and goose bumps to form on my bare ass cheeks. I almost hoped old Mr. Glass was watching us. "Jansen, Leonard, we want to make a few things clear before we go inside. I know we've been on a few dates already, but I think you may have the wrong idea about our needs. We aren't looking for a true boyfriend. We don't need it to be Jansen - Emily and Leonard - Dana, all the time. So tonight we are going to share, each other. We are also going to stay in the same room and same bed, for all our fun. There's no reason we can't all enjoy each other. As we told you, we sent our husbands away for the weekend. They do know we have some young studs who are going to pleasure us, but they also know they'll get rewarded when they come home. We know they'll be horny and willing, because we locked them in their metal chastity cages before they went on their outdoor adventure. We don't want you to think we don't love them, that's another reason we want to move away from a pure one-on-one relationship. Now I have no restrictions, but Dana promised her husband that she'd not let you have her pussy, that's reserved for him. But her mouth and ass are fair game. So, no offense, but what we need from you wonderful young men, is your sexual expertise, not a boyfriend replacement of our husbands. So do you have any problems with these conditions or are you ready to come inside?" Rather than a verbal answer, Jansen leaned over to me and kissed me lightly, while running his hand up the back of my leg and over my cheek. Emily liked his response and did likewise to Leonard. Grabbing our new partners' hand, we pulled them into the house. I was feeling totally electric and free. I had never been more excited in my life, both because of the sexual adventure that awaited us and the bond that had formed between Emily and I as we prepared for this evening. As husband and wife, we had shared a lot and gotten really close. But as girlfriends, doing our makeup, hair, helping with the intimate details of our lingerie, and doing it all together in anticipation of having a wild night of sex, created a unique bond that built on our love for each other. Now we were going to expand that love. The first thing we did, is open a bottle of champagne. We toasted to each other, as we kissed and made our way to the bedroom. The bed was ready, silk sheets laid back, and sex accessories on the tables. I slowly began to strip Jansen, while Emily did Leonard. I was determined to suck him, to show Emily my special skills, and reward him for his patience with her. I also couldn't wait to see Leonard stuff his fat cock into her juicy pussy. I knew both of them would enjoy it. So, when I had Jansen nude, I made him sit on the foot of the bed, and I took my position, kneeling on the floor between his legs. I slowly began to lick, suck, and kiss his rock hard cock. Emily meanwhile had laid back on the bed, her legs spread wide open, as Leonard worked his thick cock into her. Her moans of pleasure soon blended with Jansen's, as they both approached climax. I worked up and down on his shaft, easily swallowing him whole, despite his girth and length. I could tell he was impressed and pleased as he began leaking pre-come almost from the start. He started to orgasm a few steps ahead of Emily, but as they hit their peaks, both were screaming in ecstasy. I milked his cock, easily draining him. He had my head in his hands and leaned forward to tell me that was magnificent, the best he'd ever had. I didn't let up, but licked and sucked his wonderful dick until it was rock hard again. I wanted to take him in my ass, it had been twitching the whole time I sucked him. But first, I thought I should revitalize Leonard, as Emily had wanted him to take her in the ass at the same time I got mine. So, I moved over to where he lay beside her. I took his juice covered cock in my mouth and began to tend to it. This time Emily patted my head and watched as I coaxed life back into his fat dick. When he was ready, Emily and I put condoms on our lover's cocks and moved to the end of the bed. We put our asses up, and heads down, while the boys took their positions behind us. As they began to spread open our cheeks with their cocks, Emily and I slowly kissed, which further fueled the boys. Being together on the bed created such unique opportunities. As the boys fucked us, they fell into a synchronized rhythm, pounding in and out of our asses on the same wavelength. Emily and I were both very verbal, crying out, moaning, and praising these young studs. Having come once already, they had even more stamina and it took quite a while before they both orgasmed again, having giving my wife and I our orgasm too. As we lay there, recovering, we took off their rubbers, cleaned their cocks to let them rest. But I couldn't pass up the opportunity to move between Emily's legs. I used my special oral skills to please her one more time, letting the boys watch this lesbian encounter. This meant, of course, that I tasted Leonard's cum in my wife, a first for me. But I already knew I liked his taste so this was good as well. As expected, this sight brought their young dicks back to life. We spent the majority of the night in this kind of wild cycle. By the time we finally fell asleep about five in the morning, we had all experienced many peaks of sexual pleasure. I had been fucked in the ass by each boy. I had also sucked them off twice although their second rounds didn't produce much cum. I gave Emily two orgasms as well as just cleaning her pussy to prepare her for her next encounter. She'd shared her pussy twice with each boy, and her ass once each. She had even used her dildo on me, as a sort of entertainment for Jansen and Leonard. I was constantly amazed at the boys' stamina, although their ejaculations became increasingly smaller through the night. But still, they were amazing, even for young men in their prime. When we finally fell asleep, my ass and mouth were sore, plus I was mentally fatigued, but extremely pleased. We slept for about six hours, before I got up to get breakfast for everyone. I slipped into our spare bath to take a shower, quickly shave my face, reapply my makeup, and put on a simple baby-doll nightgown. With the coffee made, I woke up our partners and my wife. I undid her corset and sent her to the shower with them to get cleaned up. They joined me at our table, the boys in their boxers and Emily in a nightgown, still tired but oh so happy. We chatted softly, as we ate a light breakfast. Finally, they finished dressing and we walked him to the door, kissing each of them before they left. Emily and I then retired to our spare bed, so we could get more rest in clean sheets. It was another eight hours before we would emerge again. This time it was Emily who woke first. She began kissing me softly, until I too woke up. We exchanged brief soft, almost non-sexual kisses. We also talked about our evening, how special it was and what we liked about it the most. By now, we were both hungry again, and got up to get dressed to spend a relaxing day at home. But first, I went to the bath to remove my pussy prosthetic. I had worn it for days and it needed cleaning, and my skin needed a break from the glue and rubber. I did look a little chaffed, but I knew with proper care, it would be fine. What felt strange was seeing my cock. I had gotten to where it was totally gone from my mind. I had felt so complete while wearing the prosthetic that now, seeing it hanging there made me feel incomplete. Also, after being so intimate with Jansen and Leonard's fat dicks, seeing mine made it clear that I was not the same kind of man as they were. That summation was supported by how much better I felt once I had on a nice dress and heels. Even if I weren't going anywhere, I now felt incomplete unless I was properly attired. Emily and I shared more intimate thoughts about our night. I could see her now in a whole different light after watching her with the boys. It had been a total turn on to see her reactions to being fucked by those young studs. I also learned much about myself, as I knew more and more that being feminine was not just a phase, but it was touching me in ways I had never imagined as a man. A longing was developing, a desire to have a cock in my pussy. My own, wet vag to offer to a man. I felt so much more complete and genuine now. I found that my relationship with Emily felt stronger too, as we could both relate the same to situations, sexual or not. We finished our day by cuddling in front of the television watching a nice romantic comedy. We needed a bit of down time after our wild night. The next few weeks, we set up a more or less regular schedule. I worked two nights and one day a week. My clientele had settled in to a select few. About fifty percent of them visited me weekly and another thirty percent had a monthly appointment. The rest were single fill-ins, or infrequent customers. I didn't quite keep the workload of the first week, but it was plenty of action. I was easily bringing in three thousand dollars give or take a few hundred. I had started depositing in my bank, using automated deposits mostly. I had also figured out a way to account for my cash inflow. I checked with a couple of contacts and found that I could purchase vending machines and even subcontract the maintenance of them. I would get any profit minus expenses and handling fee. But for me, it was more that I needed a business that took in cash to help explain why I was always depositing cash to my bank. I made it even better by getting my pay from Annie in a range of bills and not just big bills. So I was feeling pretty good. But the best part was I had an appointment to see Dr. Clark. It was time to see what was possible. The day of my appointment, I got ready and dressed conservatively. Emily wanted to go too, but I thought for my first visit, I should go alone. At his office, I had to fill out several forms and gave them my insurance card, even though I wasn't sure they would cover any of this. Dr. Clark had waved the fee for this visit. Once I went to an exam room, the nurse asked me more detailed questions about my medical history. She also briefly inquired about the type of plastic surgery I was interested in getting. Once I had answered her questions, she gave me a short gown that tied in the front and told me to get undressed down to my panties. When she left, she said Dr. Clark would be in shortly. After removing my clothes and putting on the gown, I waited nervously. I wasn't sure what to tell him, but I was anxious about what his exam would show. He knocked and then entered, followed by the nurse with her tablet. I could sense he wasn't going to mention how we met. "Good morning, Dana. It's good to see you again. I'm glad you took me up on my offer to see me about your situation. You've met my nurse, Miranda. I have her here to be sure I fully understand my patients desires, and we get it all recorded properly. So, have you considered what procedures you're interested in today?" "Hello Dr. Clark. Thanks for seeing me. I have thought a lot about what you said and do want to know more about my condition. I have also thought about how to fully address my needs. Emotionally, I think I'm ready for this. I've thought about it for a long time. But it is daunting to finally consider it. As far as procedures, I'm interested in the breast augmentation you mentioned, as well as what the tweaks to my appearance were that you thought might be beneficial. I'm also very interested in hearing more details about the process of sexual reassignment." I glanced at the nurse as I said the last sentence, not sure if she knew what all I might need. But she showed no emotion, just entered information on the tablet. Now that I expressed my desires, out loud, I felt both relieved and very anxious. The conflicts were the kind of emotions that ran inside me all the time since I began this gender adventure. Dr. Clark smiled and took my hand. It was as if he know the turmoil inside me. "For the breast enhancement and the sexual surgery, I'll need to exam you first, but the tweaks, as you called them I can show you as we talk about them. As I told you earlier, your face is structurally very neutral with only a slight masculinization. We can make it more feminine, by addressing a couple of things. First we can make your nose more feminine looking, by slightly modifying the tip and changing it from a straight slope to a slightly concave one. Although minor, this change will help offset some bone structures that are surgically much more difficult to change. Second, but adding a small pad to each cheek, we can give you the appearance of higher cheekbones of a woman. Third, we can enlarge your lips, particularly your upper lip, again using small silicone pads to give them the puffy appearance of a female. The only other modification would be to reduce some of your facial wrinkles, probably with fillers, which is a procedure I routinely do for many woman of your age. All of this are minor surgical procedures, and can be done with other work or scheduled individually. For your breast modifications, I need to see more. Please slide your gown off your shoulders." I did as he asked, untying the gown and pulling it down to reveal my chest. I knew he'd seen me before, but that seemed like ages ago and in another world. I looked nervously at Miranda and she smiled at me, a sort of accepting look to make me feel better. Dr. Clark moved closer and began to softly feel each breast, lifting them up to feel their mass and then probing a bit deeper in the tissue of my ribcage under each one. Once he was done, he moved back slightly and looked at me. "So what type of enhancement are you interested in? Do you have a size in mind?" I blushed a little at his question. It was difficult to admit to something that only a few weeks ago would have been outrageous, but I took a deep breath and answered him. "I'd like to go up to at least a C-cup and if possible a D. But I don't want them to look like balloons stuck on my chest. I want it to look natural and be able to create cleavage with the right bra. I spoke with one of your previous clients and she raved about how you helped her find the right size for her. Do you think you can you make me that big?" "Yes, I think so. You have sufficient space under your breast tissue for a larger insert. I can also keep it natural looking, although I can't really tell until the actual surgery. What I would like you to do, is before surgery use our breast prosthetics to gauge how the size changes your appearance. We have a range of sizes for the forms, so you can a pair that would translate to a C and a pair for a D. I also want you to understand the implications of a larger breast, as they will be heavier than you currently are. Wearing the forms for a few weeks will give you more of a real idea. I do think you'll look much better with a larger breast, balancing out your body shape. Miranda will help you with the forms and you'll just need to buy a couple of bras to use them. Now for your sexual reassignment surgery, I need to examine you more closely. Please slip off your brief, lay back on the exam table, and put your feet in the stirrups so I can get a look." Now for the real challenge. I did as he asked, really blushing now. The nurse had been entering data in the tablet, but at this point she stopped to help me remove my panty and get situated on the table. I felt so exposed with my feet in the metal cups. She made it even worse by spreading the stirrups apart further, widening the space between my legs so he could get in between them. I was sitting with my butt on the very edge of the table, which meant my penis and testicles were hanging down unsupported. Dr. Clark moved his stool between my legs and with his gloved hands softly manipulated my genitals. I hadn't really thought about how he would exam me and this was far more invasive than I had imagined. He continued to handle me as he spoke. "Everything seems fine and healthy, so that shouldn't be an issue. The surgery itself is rather involved and I'll give you some material to read and links to look at online. But the basic surgery involves removing your testicles and penis and creating a cavity in the body. We use the skin from your scrotum and penal shaft to line your new vagina and labia. I use your glans to create a clitoris as the glans is heavily patterned with nerve endings that should give you the sensations any woman would have from her clitoris. Now I will have a little leeway on how I sculpt your new vulva, and I have used silicone pads to create more pronounced labia or you can go smaller and less visible. If you have a preference, we can talk about it before surgery, perhaps look at a few photos and decide how to proceed. Of course, I cannot guarantee an exact look, as I'll have to be flexible in surgery. After we create your new genitals, then you'll have a few months of recovery, with much of that involving the use of stretchers to make sure your vaginal cavity remains open and flexible. But I think if it is something you truly want, then it will be worth doing. Again, this is the most life changing surgery I do, so we want to be sure it is best for you. I'm pretty sure you're a good candidate but I still want you to talk to a couple of my colleagues. They work with Trans people regularly and can give me the kind of evaluation I'll need. When you get clearance from them, which I expect, then I'll put you on female hormones. I want you to have six months at least, and preferably a year, of hormone therapy before any sexual reassignment surgery. We can do the tweaks before then, but I suspect you'll respond very well to female hormones. I wouldn't be surprised if you gain quite a bit more size in your breasts. After we see how you respond, then we can adjust your breasts to your desired size and schedule your final surgery. The other step I'd highly recommend is permanent hair removal. Areas like your face, chest, and select areas around your genitals make the process more effective. Does this sound like something you want to pursue?" When he was describing the surgery, I got both a surge of excitement and anxiety. This was a non-reversible step. If I went ahead I would be fully renouncing my male life and assuming a fully feminine one. But I saw it now as something I really needed to feel complete. I told him I would want to go forward. He smiled and said he thought so, as I seemed the ideal candidate. With that, he moved back, told me he would see me later and left. Miranda helped me select a couple of breast forms to use. She also took photos of my nude body, from many angles. They would work up a couple of images for me to look at that showed how I would look with the different sized breasts, with the facial modifications, and even some choices on vulva construction. Finally I was allowed to get dressed and the receptionist made a couple of appointments for me with the psychologists who would interview me and a clinic where they would do my bloodwork for the hormone treatments. By the time I left, I was so excited. Driving home to tell Emily about my visit, I could hardly keep my eyes on the road. I kept thinking about now quickly everything had happened, but it still seemed like a long time. I began to realize that my quest to be thin, to lose weight so I could be as perfect as I could, was not about how finding the 'thin' man I thought I wanted to be. It was more about finding out who I really was. I knew now, that hiding inside me was a girl, a feminine creature that I had denied all my life. Instinctively, I knew she was there. It was obvious in how I acted, moved and even how I thought. Then there was my body image. When I was younger, I had ignored the real shape of my body and acted as if it wasn't as feminine looking as it really was. I compensated for my feminine body by projecting a masculine front and dressing so as to hide her away. Now that I had seen the girl inside me, had let her out and helped her mature into a beautiful, sexual woman, I knew she was the real me. A 'thin' man was not my true identity. I was really a woman, more in thought and behavior, than even in body. Now I was ready to embrace her fully, to breathe life completely into her, so that I might enjoy life as I truly wanted to do. I knew the process would be difficult, both emotionally and physically. I would face challenges from my old friends, my family, and going forward, to find a stable work path. I knew I loved cock-sucking, but it couldn't be but a short term solution for us. But I was sure, as a woman, I could find a new career that would satisfy me. But most of all, I knew that the woman inside me had a wonderful ally in Emily, who'd be there to help me blossom and make my new way in life. All along I had focused on shedding the extra weight that I thought was hiding who I wanted to be, but with her help I had found what I really needed. I couldn't wait to take that journey.