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I had to admit it was boring. I mean this was our fourth stint here and we'd visited most of the bars near us. At first it seemed like an adventure. Brad and I were assigned to work two weeks every month at the offsite location, part of a total revision of the manufacturing plant design and function. The company had even rented us an apartment rather than have us stay at hotels, because we were going to be here for at least a year, maybe longer. Our supervisor even hinted we might have to stay here all the time, once the project really got going. But for now, we were trying to find stuff to do. Luckily, we were both single, although he had a steady girl at home, and young enough that spending half of our lives on travel didn't mess up our regular lives. But still, we had to find something different. Brad had seen the bar once, and decided we should check it out. It seemed okay when we walked in. Not a sports bar, there were plenty of those, nor a snooty place either. A sort of relaxed, old style neighborhood bar. We were into our second beers, when he spotted her. Tall, blonde, long legs with a short skirt, not quite pretty, but her big boobs caught our attention. We both stared a while until he turned to me with a shit eating grin. "She's hot, right. I mean those legs alone make you hard." "Not too bad. Certainly worth a second look." "That's a guy. Look closer at the face. I swear that's a guy. Still, nice legs and her boobs are huge." "No way. Really? You think that is a man? What makes you say that?" "Well, mostly the face. The eyebrows are low, close to the eyes, the nose is too wide, and the jaw seems too strong. Second, there's a bump on her neck, small, but it's an Adam's apple for sure. Not many girls have those. But most of all, it's just the way she moves, feminine but a bit too masculine. Still nice to look at." "I guess I see what you mean about the face. And I've never seen a woman stand quite like that. But if you think that is man, why do you still look at her, him, or whatever?" "Why not? If she thinks she's a girl or even just wants to play like one, I'm fine with it. I mean, I bet the sex would be great." "I don't know about that. I can't get too excited about a guy, even if he's dressed like a girl. Sometimes Brad, you say the oddest things." "Well think about it. If she's dressed up like a girl, especially a sexy girl, she's looking for a reaction. I mean not every guy in a dress would look good, but some are. It's a fact. Second, if she's dressed sexy, sex is on her mind too. Finally, she'd know what a guy likes, really likes, because she is one. So, she'd not only look like guys want a girl to look, but act and do exactly what men want a woman to be. I'd bust a nut in her for sure." "Wow, you are the ultimate horn dog. You never fail to amaze me." "Yeah, okay. Let's go talk to her." At first, it was awkward. She even had a stripper name, Brandy. Up close, it was more obvious she was male. But she did have a sexy voice, sort of husky, very breathy, and low. Brad brought her a drink and we all chatted. I could tell he was taken with her. Then he bought another, and began to ask questions, personal questions. How, why, and when type questions. Brandy was very friendly and open, even flirty about it. After a couple of hours, I finally had to nudge Brad, I needed to go back and get some sleep. "Look we need to head home. If you want to sleep with her, do it now or another time. I've got to get some rest." He looked at me and smiled, and said okay. We said our goodbyes and left. In the car, I looked at him. "I wasn't sure if you were going to pick her up or what. Sure seemed interested a lot." "No way. Sure she was hot and a bet she'd suck dick all night, but no telling how many she's had. Too big a risk. If I took a disease back to Janet, it would be over. Plus who wants to spend the rest of your life with herpes." "But other than that, you'd do it?" "Of course, it would be perfect. Especially since we're stuck here half of our lives. You could just tell she spent all of her waking hours either thinking about sex, or making herself look pretty for it. And her two options, oral or anal, my two favorite choices." "God you are a dog." The rest of the week was hell at work. Long days, stress, and unforeseen complications. It wasn't a surprise when supervision told us to just stay here another week, before we could go home. Brad didn't like it, as I was sure he missed Janet, but at least he was getting compensation. As the senior engineer, he was getting paid at least twice what I was. I mean by the time I paid for eating out, and going to bars all the time, I wasn't making as much as if I stayed at home. So when Brad wanted to go back to Shooters, the bar where we met Brandy, I tried to beg off. Finally, he said he'd buy my drinks. When we walked in, I could tell he was happy. Brandy was there. He went right to her and started talking, even suggesting the three of us get a booth. The rest of the night, he chatted her up, but this time more questions about how she started dressing, who helped her, what all did she have to do to look so hot. I was really beginning to get weirded out by his interest. Then he topped it off. "So, do you think all guys could look like you? As sexy as you? Or is it only certain types?" "Oh honey, being pretty isn't for every man. It takes a lot to look this good. I mean, look in the mirror, there is no way, even the best makeup, prettiest wig, or cutest dress could make you look fem enough to pass. Sorry, it just won't work. Now you can feel good doing it, but never be convincing. But your friend here, Patrick, he'd be cute, very cute." "What, I don't think so. I mean, not that I'm ugly, but I just don't see it at all. My face alone wouldn't work." Brandy just giggled, cast a glance over at Brad and then back at me. "Oh don't be hurt sweetie, it's not a bad thing. But truthfully, your face would look nice with the right help. I mean, it's soft, your skin is smooth, beard is light, your eyes are big, and you've got full lips for a man. Even your eyelashes look long. I can just imagine them with mascara. I'd kill for your lashes. Plus, you're not tall, heavy or even very muscular. I bet Amber, my friend, would make you look like a million dollars." "Really, you think Patrick could look like a girl. A pretty girl?" "Definitely, plus, no disrespect honey, but you seems like the right personality too. Very polite, quiet, friendly, the kind of boy who prefers to get along rather than make waves. Just the way you sit, hold your hands, and even your walk has very feminine touches to it. Wouldn't take much practice until you would act as cute as you'd look. That's my biggest hurdle, my body movements and behavior are a bit too butch for my liking. But Patty here seems like a natural. Amber could do wonders in no time with him." "Wow, now that you mention it, I see what you mean. So is Amber a friend or what?" "Yes, she's sort of a local mentor, a mom to lots of the queens around here. She does hair and makeup at a salon and then helps men who want to look pretty on the side. I got my first makeup lessons from her and she styles all my wigs now. I see her every once in a while too. She likes to go out to Desires, the bar downtown. It's a bit too fancy for me. Why?" "Just wondering that's all. So Amber is a guy too?" "Oh no. She's a woman. She's even married with kids. Just that she likes to help boys look pretty, that's all. If you want I can give you her number. She's very nice, friendly too." "This is silly. I got to go pee, I'll be right back." I stood up and went to the john. Sometimes Brad did the craziest stuff. I was a little creeped out by his interest in this. It was even stranger that Amber thought I'd be able to look like a girl. When I came back, she'd left. We had another drink and talked more, but he quit talking about her or his sudden interest in the whole subject. The rest of the week we were able to get the job back on track, enough to go home for our regular two weeks. It was nice being in my own place, and not having to eat out all the time. But it was boring. At least on assignment, I had someone to talk to and share stuff. At home, it was just me. Well me and my neighbor, Claire and her cat. A nice old lady who took her cat for a walk. When I thought about it that way, it made me look kind of sad. Even still I wasn't quite prepared on Monday when my supervisor said he wanted Brad and me to stay offsite all the time. Seems management wanted someone there constantly, so the conversion would make more progress. He told me they would help with the reassignment. They weren't sure how long we would have to be there, but he suggested I put my stuff in storage, and get out of my apartment. The company would help me break the lease, at no cost to me. They'd even ship some of my stuff, a limited amount, to the apartment Brad and I rented. I hated the sound of this. I knew I couldn't protest, as I needed this job, so I was hoping maybe he'd refuse to go. I mean, surely Janet wouldn't like it. When I saw him later that day, he disappointed me. He had no problems with it, even seemed excited in some ways. He just told me, he'd go back on weekends now and then to see her, or she'd come visit. I guess it was partly because the conversion job was challenging, something better than our normal assignments. He liked the new work. So reluctantly I agreed. Breaking the lease was easier than I expected, and the company shipped out three large boxes for me. I told Brad I had to have some of my kitchen stuff, because I didn't want to eat out every night. The apartment they had for us was furnished, but only furniture and a bare minimum in the kitchen. Having stuff to cook with did help, as I wasn't eating out all the time. I was a little disappointed, because Brad told me he had no cooking skills and so all of the meals defaulted to me. He was appreciative though, telling me I cooked far better than Janet. Going out to bars, was still our preferred choice of recreation, though, despite it being costly to me. The next three weeks were still hectic at work, but we made enough progress that the project was on schedule again. Getting everything running smoother, allowed us to live a more normal life. Because we were going to be here every week, on top of the process, meant we didn't have to work long days and weekends like we did when we were only here half of the time. Our supervisors told us, we were doing great and the local management liked this approach better too, as the plant workers were more receptive to our help. But that meant, since we weren't always at work, that we had more free time. Free time to fill. For Brad, it meant more bars, drinking, etc. That was okay, except it was eating up all my money. Sometimes he'd go out on his own while I stayed at the apartment. But that was boring too, as we only had 12 basic cable channels. Plus he still wanted to talk with Brandy. I really think he was developing a thing for her. That all came to a head the first three day weekend we had while on assignment. The plant was letting most of the workforce take off Monday as a holiday, so there was little for us to do. Apparently that triggered an idea in Brad's mind. A crazy idea. Friday started as normal, we swung by a bar on the way home. Shooters. As I expected Brandy was there. We got a booth and she joined us. Brad bought everyone a beer, as I was already broke and we had two weeks to payday. After our first drink, Brad got a strange look on his face, glancing back between me and Brandy. "Honey, that friend of yours Amber. She still doing her thing, you know, helping guys look pretty?" "Sure of course Bradley. I talked with her earlier this week, as I need to take a wig to her tomorrow. Why do you ask?" "I was just wondering if she'd be willing to see what she could do with Patrick here. You know if she could give him a makeover?" "What? What gave you that crazy idea? That I would be remotely interested in doing something so strange. Brad you're off your rocker." "No, no, hear me out first. I just keep seeing an image in my mind, of how you might look. I think you'd be cute, that's all. Like Brandy here. I dunno why, but it's like the idea is haunting me, you know. So I thought since we have a long weekend, you might try it out. I know it's strange. But I'll make you a deal, make it worth your while. If you do it, I'll cover your bar tab for a month. If you look at yourself and think you don't look like a woman, then you don't have to do anything but try it once, I'll still pay for everything. The cost of you makeover plus all your drinks for the next month. What the heck, I'll pay for you to eat out too. But if you look okay, and would be willing to dress once in a while, I'd not only pay for your drinks but food too, groceries and whenever we ate out, for as long as we're here. The whole assignment period. I know you're strapped for cash. And it would be worth it to me, what do you say to that offer?" I had wanted to punch him, when he first suggested it. I mean, he was questioning so many things about me, my appearance, whether I was masculine, and even my sexual orientation. Worse, he was suggesting I would look good as a girl. I wasn't a physical guy like that, to start a fight, but he made me mad. But when he offered to pay, for drinks and maybe food, I did a double take. First because I was broke. I didn't even have money for anything to eat more than Ramen or rice and beans. If he covered my drinks and food, I'd actually be able to save some money. Put something in the bank, even pay off my car note. I'd be ahead for once, and it would make being offsite really worth it. So I didn't respond right away, held back a second. What worried me most was him. I'd seen the way he'd looked and talked about Brandy, girls like her. If I dressed like a woman, would he think about me that way? "Oh, I'm sure Amber could work magic with Patty. She's the best and he actually has a lot of potential. I could see him turning out really cute. Do you want me to text her and see if she can work Patty in tomorrow? I'd be glad to take him over there and you could pick him up when Amber's done." "God that'd be perfect. It would certainly spice up the weekend. Give us something different for a change. What do you say, buddy? I swear it will be fun. A good break from the boredom too. And profitable for you. How about it?" As soon as Brandy made her suggestion, I cringed inside. I didn't really like the idea but I was so broke. It began to sound like a bargain I could make. I started to really consider it, despite all my misgivings and the way I kept feeling it was a big mistake. But, getting back on track financially would be so nice. I mean no one besides Brad knew me here, so that wouldn't be an issue. And he hadn't really been out of line with Brandy. She was more like a female friend than a girlfriend. I mean, surely Brad wouldn't do something, try something with me? So I thought about it again, seriously this time. Even if I only did it once, I'd still have a month free of most expenses. Finally, I couldn't believe I was saying it. "Well okay, I'll try it. But don't call me Patty. That's my mom's name and it just sounds creepy." "Fine, we can let Amber pick out a good name for you. She christened me Brandy, and I love it. I'm sure once she makes you over, she'll have just the right moniker for you. Here I'll text her." Brad was all smiles now and patted me on the back. Brandy's fingers flew on her phone and she sent the text. Within a couple of minutes she got a response. The one she hoped for I guess, from her smile. "She said she'd do it. But you owe me big time. He has to be there at nine, so she can work him in among her regular customers. Normally I never get up that early on a weekend, but I'll take him there. Then he can call you when is finished. Tell me where you guys live, so I can find it." We spent the next 20 minutes talking about it. Brandy asked me more questions and seemed surprised that I had never dressed before or even wore something as simple as panties. She looked at the two of us, sort of like she was trying to figure out if we were really gay, but just hiding it. Then she shrugged, and told me to wear something comfortable in the morning because I'd be out of it almost as soon as I got there. Turns out, Amber's shop was located in the middle of a row of stores that sold everything I would need, shoes, dresses, and lingerie. When she outlined the obvious need for Brad to not only pay for my makeover, but for an outfit too, I was surprised. He didn't blink an eye. All he asked for is to be allowed to pay a deposit in cash and then when he picked me up, the rest on his card. To seal the deal, he gave me a hundred dollar bill. It was at that point I began to get nervous, realizing what I had committed to do. To calm me, Brad bought me two shots and another beer. Finally, we left with Brandy prepared to get me in the morning. I heard her car horn, outside our apartment right on time. I'd not slept well, and finally had gotten up, taken a shower, shaved and dressed in some old jeans and a tee shirt. I'd eaten some eggs and toast, as I wasn't sure if I'd get any lunch or not. When I got in the car, I was shocked. Brandy wasn't dressed, at least as a woman. When I saw his regular look, I couldn't believe it was him or that he could actually look like a woman. On the way over, he told me that I would love it. To just relax and go with it. He whispered that once I felt nylons on my smooth skin, I'd be hooked. The salon was a literally in the middle of a row of shops. I could see from the signs that Brandy wasn't lying when he said it was surrounded by everything I would need. As we got out, he carried his wig box and led the way. The place was real busy, even from the lobby I could see all the stylists' chairs were occupied and there were two more women waiting. The receptionist smiled, recognizing Brandy and called out for Amber. I wasn't sure what I expected her to look like but it wasn't this. Amber was petite, a pretty brunette, with long hair, with soft curls. Of course, her makeup was flawless, her nails, although short, were polished, and she wore tight jeans and scoop neckline top that gave glimpses of her small boobs. She had lots of jewelry, and looked really nice in a casual, put together way. But what struck me most was her smile. She seemed happy to be here and very welcoming. "Hello Brandy, bit early for you isn't it? Is this the friend you told me about? Hi, nice to meet you, I'm Amber. You ready for a change? Let me take a look at you, honey." Amber came right up to me, looking intently at my face, hair, taking hold of one hand and then lifting both arms to sort of look at my body. She was smiling the whole time, and talking too. She told Brandy to leave the box and it would be ready Monday as she promised. But before she left, Amber looked at me again, staring in my eyes. "Okay, you sure? I promise you I'll make you look wonderful. Brandy told me that your boyfriend is covering the whole works, makeover, clothes, shoes, everything. Is that right?" "Yes, well he's just my friend, not a boyfriend. But yeah, he gave me a hundred as a deposit and then he'll pay the rest on his credit card. Is that okay?" "Sure, sure honey. I would have trusted him for the whole thing, since I wouldn't release you without getting paid." Her laugh relaxed me a little, as my heart had been racing since we came in. I had hoped the process would be private and still wasn't sure how it all would work. "How are you going to do it? I mean will I have to go to these shops to get clothes? First or after? And are you going to make me over out here?" Amber sensed my nervousness and squeezed my upper arm. By then Brandy had left and I was on the verge of panic. "Well what I suggest is that I measure you, and then I can go buy what you need while your makeover is going on. Normally, I'd do it all myself, especially for a girl's first time. But because it is a work-in and not a previous appointment, I'm going to have to let some of the other women help. Don't worry, they're all pros and have done lots of guys before. The good news, is I had a cancellation at 1 so I can finish you early. Now, Brandy said your boyfriend, rather your friend, wanted the full treatment. So let me describe what we're going to do for you." The list seemed like a lot and I was surprised, but not, by what was included. A full body wax to start. Nails, including extensions. Makeup, and then hair style. She admitted she had expected to use a wig, but looking at me, she felt she could give me a feminine hair style with my own hair. If I wanted a wig later she'd help. I knew my hair was longer than a lot of guys, but I was still surprised she felt like she could make it work. Because she had other clients today, each step would be done by a different stylist, but Amber would do my hair. Once I was fully made up, I could get dressed in the outfit she'd buy. Then I'd be ready to go. It all seemed like it would take all day, but she assured me it would be quicker than that. "Last chance to change your mind, you set?" "Yes, let's do it." "Marvelous and relax, it will be fun, I promise. I know women do a lot to look pretty, but it's nice to be pampered, you'll see. Let's go meet Tanya. She'll wax you, as that's her specialty." The next few minutes were embarrassing. First stripping in front of two women, two strangers. Amber wanted to measure me for clothes, while Tanya got ready. Fortunately, this was all done in a private room. When Amber told me, I'd have to remove my boxers, as my 'friend' had requested a complete wax, I actually blushed. Mostly, because it made me worried about why Brad wanted me smooth, down there. Not that I was ashamed of my cock, but still I wasn't in the habit of being nude while others were clothed. Luckily, it behaved, neither getting erect or shrinking up. Amber measured me for a few essential areas, also checked out my frame closer. I told her my shoe size and what I normally wore in men's clothes. She seemed pleased, smiling the whole time, which peaked my interest. "Is everything okay, I mean can you work with my sizes?" "Oh honey, definitely. I hope you don't take it the wrong way, but you seemed almost designed for women's things. First you shoe size is small, I think I can get you in women's 8s. Then your body proportions are good too, very narrow waist, with hip and bust bigger, if only slightly. Your hips are a little narrow but that's offset by your round ass, very cute btw. Finally, you have just enough up top, some extra that I can work with to give you a woman's bust appearance. Overall you'll be an easy conversion. Best of all, your personal area, isn't overly big, which should give you a nice smooth line in panties. I think you and your friend will both be pleasantly surprised by how nice you'll look. Okay, I have all I need, Tanya do your best. When you're done, just get Denise to do his nails. He'll need some extensions, let her use her judgement on length but I'd prefer a rich red, maybe something like OPI's Candyland Kingdom or Big Red Apple would be good. Bye honey see you in a bit." When Amber left, I felt really awkward all of sudden. And why not. Laying down on a table, with just a towel to cover me, while a woman, who I just met, began the process of ripping away my body hair. It hurt, worse at first, but even when she was almost done, it hurt. Just pulling the strip of wax away, sent a sharp wave of pain from the area. I had almost become numb to it, or more accurately resigned to it, when she finished the back of my legs. Overall she had worked quickly, the process not taking as much time as I thought it should. All that was left, was my 'personal area' as Amber called it. I really wanted to beg out of it, but Tanya just asked me to get up on my knees, and spread my legs apart a little, as if she were asking me to sit down at lunch. Not slowing enough to let me protest. The first bit of hair she ripped from my ass crack was the worst pain yet. But she made her way down until she'd done all of my backside and even the back of my sack. She had me turn over at that point and finished off my cock and patch of pubic hair. I hadn't noticed it at first, but Tanya had been quiet most of the time while she worked. Until she started on that area. I guess it was awkward for both of us. I mean, it was the first time a woman had touched my cock, in any fashion, for over a year. Again, I was pleased my cock didn't overreact in either direction. With my body done, she told me Amber wanted her to shape my brows, just a little, so she touched those up last. When she was finished she applied a light coat of soothing, moisturizing lotion, softly rubbing it into my skin. That did make me feel better. When I sat up, I immediately looked at my brows and was pleased that they weren't too narrow or exaggerated. Just a bit thinner with a hint of an arch. Leaving the privacy of the room, wrapped only in a long, fluffy robe and slippers, did not make me feel good. I felt exposed, with my bare legs uncovered and no underwear. I wrapped the robe tightly around me Tanya took me out into the main area of the salon, where Denise had an open chair for me. Denise was the exact opposite of Tanya, talking the whole time. This process was much nicer. Getting a foot rub, soaking in a warm bath and having someone sand callouses off of your feet, was almost relaxing. She agreed with Amber on color choices and soon my toenails were a glossy red, very different. Doing my fingernails took much longer. She applied tips, extensions of a full inch to each nail, gluing them on and then layering some solution, a gel, she said, to each nail. Once that dried, she sanded it smooth and then began the polish processes. Clear first, then two coats of color and then a final clear to seal and protect. Hands under a device in between to speed it up. It seemed like so much, but the change was dramatic. My fingers now looked so long, slender and definitely feminine. I was worried once I saw how extensive the look was, and asked about how I could take them off. Denise, sort of chuckled, looked at me oddly. I just asked if I needed to remove them, how would I do it, but to make her feel better I said they did look great. She smiled when she said, regular nail polish remover could remove the color, but I'd have to soak the tips in acetone to remove them. But then she whispered, that once I got used to the length, that I'd fall in love with the look. She even wanted to book me for a polish change in two weeks. I just let her do it, as I figured, I would just call and cancel. When she was done, she asked Amber what stylist was supposed to do my face. She had just finished a hairstyle for a middle-aged woman, so rather than just answer, she headed my way. "Honey, I've been thinking about your hair style, and it needs a little something. So I'm going to start it before you get your face done. Follow me back to my chair." I moved from Denise's place to the just vacated chair. Amber wrapped me in a plastic gown and immediately began to work on my hair. She took a gooey looking mixture, with an odd smell, and using a small brush began to apply it to my hair. After doing a section, she'd wrap it in foil and move to another area. Half way through, her next customer came in and she just had her go get her hair washed by the shampoo girl, and then finished with me. I was beginning to get nervous at this point, about what exactly she was doing. It seemed like maybe a color change, but when I asked she just laughed and told me, I'd love it. Once she had applied all she wanted, Amber put a plastic bonnet on my head, covering all the hair. Then she took me to a dryer, one of those old- fashioned ones where you stick your head in a big plastic bubble and I sat under it. Of course, she gave me a magazine and told me it would be about 20 minutes. She left to work on her customer. I was officially nervous now. Reading the magazine, or more accurately leafing through it, I couldn't help but see how the long nails changed me. The movements alone seemed so strange, plus the flash of pretty color on my fingers was decidedly different. Every time I turned a page, I was confronted with my new longer nails making me realize how they changed my sense of touch. Also, what would my hair look like? I had assumed when I agreed to do this, I would have a wig like Brandy. Amber had been so nonchalant about doing my own hair, I hadn't thought about how I would look later. If it was too bad, I guess I'd just have to get it cut off before Tuesday. All I could think about, was I hadn't worn a crew cut since I was six. I was lost in worry, when I felt a tap on my leg. The shampoo girl wanted me to follow her, so she could wash out my hair. That turned out nice. I had never had someone shampoo and condition my hair before. It was so relaxing and I felt calmer when she wrapped my hair in a small turban towel. She'd been totally friendly. Amber had just finished her client. The ladies' hair was now in curlers and she had gone to the dryer where I had sat a while ago. I sat down in Amber's chair. She used her fingers to tease out my hair. I could see it in the mirror, but because it was wet, I didn't see a color difference. When I had started work, my hair was longer. I cut it and then slicked it back, to look more professional. But as I had gotten used to my work situation, I let it grow out again, stopped using gel, and just had a short ponytail in back. Enough to keep it out of my face. As I watched Amber play with my hair, I saw her part it on the side, combing some over and the rest toward the back. She seemed to know exactly what she wanted, and began clipping some hair, giving me a new shape. At that point, she had turned my chair so I couldn't see what she was actually doing. In reality, Amber didn't cut off much, or it seemed that way. When she put down her scissors, I thought she was done. But reached into a side tray of curlers, selecting a few. Then she rolled my hair, but mostly on one side and in the back. I couldn't move my head, but glanced up at her. "Don't worry honey, you won't have to do this every time to get your new look. I just find it helpful, when I give a girl a new style, if I put it in rollers. That will help the hair adjust to a new direction for it to lay. Also, it will give you a bit more volume, In the future, you can do it this way or with a curling iron. Much easier and quicker. Now I want you under the dryer for about 10 minutes, then you can start getting your makeup done. Beth will grab you when it's time." I sat down next to the lady Amber had worked on earlier. She glanced my way, looking up from her magazine. I was prepared for her to give me a nasty look, since she would be wondering what a man was doing here, but she just smiled. Reaching down, she picked up a magazine and offered it to me. I smiled back, mimed a thank you and started looking at it. When I did, I realized there was probably no reason for her to look at me oddly, I mean, my nails were long and polished. I was wearing a woman's' robe and slippers, my hair was in curlers, and my smooth, hairless legs gave me the look of any girl. This time I actually looked at the magazine, which featured latest clothes styles. When a woman, tapped me on the leg again, I smiled and stood up. She lightly touched my rollers. "Feels dry enough. I'm Beth. I'll be doing your makeover. Amber told me you wanted something easy to do, but still dramatic enough to take out on the town. So what I'm going to do is focus on your eyes and lips. Lucky for you, your skin looks pretty smooth, so you'll just need a little foundation. Since this is all new, I'll describe what I'm doing with each step. I think you'll be able to do it on your own. But the first thing is to give your eyes a little extra. Your lashes are okay, long even for a guy, but longer ones would have much more impact. Lots of women use false lashes, but they are so hard to put on for a newcomer. You can use lengthening mascara, but it takes a lot of effort and doesn't quite give you the length you need. I think lash extensions would be best. The good news is, the application process is about as easy as it can be. You just lay there, let me do my job and try not to fall asleep." Beth laughed a little at that point. She took me to a chair, reclined it a little and then began the process. I could feel her gently placing something on my eyelids, right at the juncture of my lashes. She talked while she did it, telling me this would give me a nice look all the time. I could use mascara with it, if I wanted, but even without it, I'd look good. The best part was it was all natural. The process was relaxing and it did take some effort to keep from falling asleep. After about 30 minutes, she told me I was done, and put me in an upright position. I opened my eyes and immediately noticed the longer lashes on top. Beth said she applied longer lashes about every other one, basically gluing extensions onto my real lashes. When I asked how long they'd last, she told me 4 to 6 weeks is normal. The extensions would fall out when my natural lash did, a normal process. She'd only done a light application, just enough to give me a pretty look. It was usual approach for a first-timer. But she winked and told me, most girls came back and got a fuller set once they saw how easy it made doing their eyes. At that point, she began to apply the rest of my makeup. With each step, she told me what she was putting on, how to do it, and why it was needed. I kind of knew what each product was, as my first girlfriend had used a lot of makeup and I had seen her get ready more than once. Still, to see it put on my face was a different experience. The process took about 45 minutes. Beth gave me the works including foundation, powder, blush, eye shadows in three shades, eyeliner, brow pencil and powder, lipstick, and lip liner. She had been working so I could see my face in her mirror. That way I could see exactly how she did each step. In total, it seemed like a lot, but each part was fairly simple. I was so focused on each step, that I didn't really comprehend the overall impact until she stepped back and told me to look at my face. I sat there, quiet for a second. The reflected image had hints of me in it, but an entirely different take on who I was. My eyes seemed enormous, pretty, with long lashes and soft colors. Very pretty. My lips were nothing short of luscious. So soft, alluring and I hated to say it, kissable. The foundation and blush made my skin look smooth and soft with high defined cheekbones. I knew the face was mine, but it was also clearly a woman's face. A soft blush rose up, as I realized how feminine I really looked. Of course, Beth was smiling, very proud of her work, as she stood next to me. At that moment, Amber appeared in the mirror, standing behind both of us. "Beautiful, isn't she Beth? Nice work, she looks natural but so pretty. I love her eyes. The way you accented the small arch in her brows, and her lashes are perfect. Did you use some extensions? Great choice. Don't you love your look honey? I'm sure your boyfriend will, once he sees the new you. Well let me finish your hairdo and then we can get you dressed." I was so enraptured by my new look, I didn't even bother to correct Amber's reference to Bradley. I moved over to her station, still glancing at my new face in the mirror. Amber quickly unrolled my hair, turning me away from the mirror to work. She brushed out the curl, sort of pulling it up over my head and then curled under on one side. I could tell the other side was shorter. She finished by combing the back of my hair, sort of repeating the curl under moves she used on the side. With everything combed out, she lightly coated it with hair spray to keep it in place. Then she rotated the chair back so I faced the mirror again. I had sort of expected this, to look different, but not this much. My hair now had wide streaks of blonde, way lighter than my normal dark blonde color. The side part changed the look of my hair, so the longer side fell across my forehead like bangs. Then it curled under at my chin. The other side was short, almost like a man's and tucked behind my ear. I didn't have side burns, but small wisps of hair were there instead. A short but definitely feminine hair style. I couldn't see how I could easily transition it back to a male look without a real close cut. Worse yet, I couldn't see how I could disagree if Bradley said I looked like a woman. Because I did. It was at that moment that the gravity of what I had done, what I had agreed to, hit me. Bradley had made me a simple proposition. Once would be enough, if I didn't look enough like a woman. But if I did look feminine then he would expect more. Now that I had passed that simple test, I wasn't sure how much Bradley would expect me to dress. For him. That was the other part. I had glossed over that implication. I had seen how attracted and turned on he had been with Brandy. Not being conceited, but what I saw in the mirror was much prettier than her. But then I realized part of what turned Bradley on, was her body. Her long legs, big ass, and bigger boobs. My face might look feminine, but I wasn't sure how my body would look. That was my only hope. Amber had watched me look at myself and waited. Finally, catching my eye in the reflection, she smiled. "I take it you like what you see? A very attractive woman. I think you'll love it even more, once we get you dressed. Come on, let's go try on something pretty." I stood up from the chair, and she took my hand, leading me to the lobby. I panicked a second, until, she opened the side door and we went into a private space. An office, with a desk, chair and a small couch. The far wall was all mirrors. Stacked up by the couch were several large shopping bags, quite a few in fact. I glanced back at Amber. "I hope you don't mind, but I called Bradley. Brandy gave me his cell number and I wanted to know what kind of outfit he wanted to buy for you. Well, we talked a few minutes and he asked if I thought you'd look nice. You know pretty and feminine. You were just getting your nails done at that point, but I could already tell you'd look darling. When I told him yes, he said to buy what I thought you might need for a long weekend. And more. So I went on a shopping spree for you. For today, he said he wanted something special, very feminine, as he was going to take you out for a nice dinner, drinks, and dancing. So, I'll help you get dressed in that, okay?" My heart was racing, not from excitement but fear. Looking at all the bags I knew she'd bought a lot. A lot of women's clothes. Bradly had told her to buy enough for a long weekend. That meant, I was already committed for more than one time. But maybe it wasn't too late. I still had to look good, have a girl's body. So I nodded yes. "Great, we'll start with some underwear. Panties. This pink bag has those. I picked out a complete ensemble, lingerie, hose, dress, and heels. Even accessories. This may be a little over the top, but he seems like such a nice man, I was sure you'd want to make him happy. I mean, not every boyfriend would spend this much on a girl. So here slip these on." Amber had reached into the bag and brought out a black panty, holding it up for me to see. It seemed complicated, not just a plain one. I mean in front there was a small triangle of satin with three or four straps connected to a much smaller strip in the back. At the top of the back was a large bow. Spreading it open, she held it for me to step into. As I did she worked it up my legs, under my robe to mid-thigh. "Do you know how to tuck? Most girls like you, sort of put their boy things away, it's easy if you've not done it before. Just take one hand, place it over your testicles and move them around until you find openings to push them inside your body. Once you've done that, push your penis back between your legs and then we can fit your panties. It sounds harder than it is." I was blushing now, but did as she directed. I knew my balls retreated in cold weather, but never really tried it on my own. Amber was right, a little bit of effort and they slipped through openings to disappear. I tucked my cock backwards and held everything in place with one hand. Seeing that, Amber helped me pull the panty around my hips and snug enough in the crotch that I could take my hand away. The fabric did hold me tightly. My front now was smooth and flat. While I looked at that, Amber was straightening the four strings that held the front to the back, and making sure the bow was in the right spot. She told me to take off the robe and look. When I slipped it off, I turned to see my reflection. It struck me that I looked like a package, with a bow on top. The straps were spread equally spaced over my ass, with the bow at the top of my crack. The narrow strip of fabric in back barely covered my crack, again making me feel like I was on display. I guess I was. By now, Amber had reached into another pink bag and held up some more lingerie. I recognized it as a garter belt. Matching the black satin panty, it too had several satin strings that went from front to back, with a sheer wide strip to match. She put it around my waist, hooking the main connection in back, and pulling another strap around to the side where a small hook went into a fabric loop. She then worked each garter strap under the straps of my panty. As she did, she glanced up at me. "Most times you'll wear pantyhose, easier to put on and wear, than garters and stockings. But every once in a while a girl likes to dress as sexy as possible, so you need to know how to wear these too. It's important that you wear your panties over your garters. That way, when the time is right, your boyfriend can take them off, while you still wear your gartered stockings, very sexy. Men love the way it looks in bed. I'll show you how to put on the hose in a second, but let's get your bra on first. You'll find that as much as panties are necessary, a girl's most important underwear is her bra. For girls like you, it means more of a choice too. Regular girls don't get to choose the size up top. They can be big to small and buy the appropriate size bra they need. But you actually get a choice. Now I hope you won't be mad, but I didn't go real big up top. I prefer to size a girl's bust so it looks proportional to the rest of her body. I think it looks more natural that way. Now Brandy, disregarded my advice and went big, real big, thinking it made her look more feminine. But I think, it just draws attention to her and makes it harder to pass. For you then, I went smaller. Not small and sassy, like me, but more realistic." Amber smiled when she said the last part, sort of shaking her boobs too. I had to smile too, even though I was petrified by all of this. While she had talked, Amber had removed three items from a bag, two boxes and a black satin bra. She opened one box and I could see a pair of beige pad like things, I assumed were my falsies. Holding them up, she resumed her explanation. "You'll find this little item to be so helpful. They're silicone, soft, life-like, and do give you a little more size. But their real purpose is to create some cleavage to enhance your illusion. Some real girls use them too, often in place of a regular bra. They have a sticky backing to hold them to your skin and are connected by this small hook." Amber disconnected the two pads and put them individually on my chest, one centered on each nipple. She then told me to press them against me, so they would stick. She explained that the adhesive would hold it on, unless I danced too much so my sweat would break the seal. But they could be used again and again, after a quick rinse off and drying before being stored in their box. While I held them in place, Amber hooked the bra around my chest, right below my hands. I noticed the bra didn't have straps. Seeing my reaction, Amber smiled. "I chose a strapless bra for you, because your dress leaves your shoulders uncovered. Don't worry it will be tight enough to hold everything in place. In case you're wondering, your bra size is a 34C. I'm a 28A and Brandy, bless her heart, is a 38DD. The number refers to the distance around your rib cage and the letter sort of describes the size of your boob. Now on my frame, a C cup would look huge, but for you, it's just right. I normally keep a few breast forms on hand, and was lucky enough to have just what you need. Take a look." With my bra hooked around my body, Amber opened the other box and took out two large silicone forms. They had realistic areola and nipple, in a darker brown but most of the form was light beige, close to my skin tone. She'd described them as small, but the forms looked huge to me. After showing them to me, she set them down and turned back to face me. "I think those should stay now, so you can remove your hands. Pull your bra up over them and I'll show you how it works." I did as I was told, realizing how tight the bra was around my chest. I also saw the small pads came nowhere close to filling my bra cups. If these were small, Brandy's must look like duffel bags. With my bra in place, Amber reached under it from above and pulled the two pads toward each other, snapping the clip in place when she did. After she pulled her hands back, I could see what she meant. The pads, stuck to my chest and pulled my loose flesh together, creating a shallow valley, a girl's cleavage. She then picked up my forms and slipped each one into the bra cups. I now had full, sexy breasts. Boobs like a real girl. It was hard to take my eyes off my reflected image. With my hair, makeup and smooth body, the fake breasts tucked into my bra completed my look. I knew now that Bradley would see me as a girl, a sexy woman, and not his old roommate. "Looks wonderful doesn't it? I think you'll love it even more in the dress. Now, you don't need to wear the stick-on pads unless your outfit needs cleavage. Usually your forms will give you all the bust you need. They can also be attached to your chest, I've included the medical adhesive you need for that too. Now let me show you how to put on stockings. The process will be about the same for pantyhose too, you just need to do both legs at the same time." Amber got the package of hose and opened it. Each stocking look long and so sheer. They were a light black with a darker black band around the top. Starting at the top, Amber gathered the silky material together, working her fingers inside the leg. She pulled fabric up into a bunch, working her way down the length of it until it was all gathered together, the reinforced toe stretched between her hands. Telling me to lift my leg and point my toe, she slipped it over my foot and stretching as she went pulled the stocking up my leg. What hit me immediately was how silky and soft it felt. It literally glided up my smooth, hairless leg. I quickly remembered what Brandy had said about this and she was right. It both gave me goosebumps and caused my tucked cock to twitch. With the stocking up around my thigh, Amber took one garter, opened the clip and showed me how to attach it to the stocking. She did the same in back. She then gave me the second stocking and watched as I repeated her efforts, only at a much slower speed. While I worked, she commented. "It's better to go slow than try to hurry this, with pantyhose as well as these stockings. Hosiery is very sheer and because of that it is very vulnerable to snags and runs. That is one reason to always keep your nails neat and filed. Also, the hose I bought you is especially sheer, a very expensive brand. Wolford is the recognized world's best hosiery. Normally, I wouldn't start a novice like you in such perfect hose, but Bradley said to spare no expense. And they do make your legs look like a million bucks. But for everyday wear, after this weekend you'll probably be best to go with a brand like Hanes, or Hue, solid pretty styles that will last longer and are less expensive." I was barely listening as I was trying to hook the stocking to the garter tab. With my long nails, this was harder than it had looked. I finally got both done, although I had to seriously twist my body to do the back clip. Finished I turned to see how I looked. When I saw my reflection now, it was truly that of a woman, a sexy woman. My legs looked long and sexy, even longer than Brandy's had. My hips and ass were decorated in the pretty panty, looking every bit like there was only a pussy beneath the small triangle of fabric in front. Up top, my bra jutted forward, the cups supporting what appeared to be full breasts with nice cleavage to boot. My face was pretty and now fit harmoniously with my body. Even my hair was sexy, short but styled in a flirty way. I could see I was now every bit a woman from top to bottom. Again, I was positive this was what Bradley would see, a pretty, sexy girl. His girl for the weekend. While I stood, staring again at my image, Amber continued. She had opened a box from one bag, a bag from a shoe store. She held up a pair of black sandals with a very high heel. I would later learn they were four and half inch heels, from a designer known for sexy shoes, and were a style called ankle strap heels. That would be logical for they were held onto my feet by only a very narrow twisted band, covered in small bows, that fit right behind my toes and a similar twisted band with a bigger bow at the back which encircled my ankle. Amber was pleased with herself, I could tell, both because she had gotten these on sale and they were a perfect match for my ensemble. After she fit them on my stockinged feet, I stood up, slowly and awkwardly. Since I never had worn heels before, let alone any this high with such a narrow heel, I wobbled just standing there. Amber took my hand and I slowly began to walk. After a couple of trips across the room, she let go of my hand and made me go solo. She supplied little hints as I haltingly made my way. Take short strides, land on the ball of my foot first, and imagine you're walking on a straight line out if front of you, so that you swing your feet inward with each step. After ten minutes of this, I was beginning to feel a little more comfortable in how to walk, but I could also feel some pain. I realized that women wore such shoes to look pretty but not to be comfortable. All that remained was the dress. Amber went to one of the dress bags that were hanging on a hook behind the door. She unzipped it and took out a slinky black dress. It sort of sparkled as it moved. Across the top there were several rows of small sequins with reflective fibers woven into the body of the dress. She unzipped and again held it for me to step in. This time I had to balance myself by placing a hand on her shoulder as I still felt wobbly in the heels. With both feet inside of the dress, she pulled it up body, until the top went over my bra. I put my arms in the sleeves and felt her zip up the back, and it tightened around me. Amber began to adjust the fit a little, pulling down the top so the top line of the dress fit at the edge of my bra, exposing most of my cleavage. All of my shoulders were exposed, as the top went around my chest and the sleeves were attached below my armpits. The sleeves themselves were sheer with sparkly cuffs, which matched the top. Looking down, I could see the dress extended about half way down my thighs, beyond my gartered stockings, but not by much. I slowly turned to see how it fit in back. There was another bow, a large one at the cinched in waist, coordinating with the bows on my shoes and subtly with the one on my panty. Amber was beaming. "Isn't it lovely? And you too? It turned out even prettier on you than I had hoped. Your boyfriend is going to love this. He seemed so happy when I told him how you were looking. I'm sure you'll get what you want, looking this gorgeous. Again, I normally wouldn't dress a girl in something like this for her first time but you were such a natural beauty. I made the right choice for sure. He promised me he'd take you out on the town to celebrate. Walk some more for me, while I get the matching purse. I'm going to put what you need in it from your old wallet." I did as she asked walking back and forth. I couldn't take my eyes off my image. I would have thought such an image was indeed among the prettiest girls I had ever seen, if it wasn't me. I could only imagine Bradley would see it the same as I did. It helped me to just focus on walking. Kept my mind off other things. I did see what Amber meant about walking toward an imaginary line. I could see the action in my hips as I walked, It gave me a decidedly wiggle to my ass with each step. Not that I wanted that per se, but using the image helped me keep steady. Finally she was done and handed me the purse. My purse. It was a small clutch, black and sparkly like my dress. I looked inside. There was a smaller clutch with my ID, credit cards, and other personal info. Plus three dollars. All the cash I had. That reminded me why I had agreed to this. Then I looked closer, one of the bills was the hundred I had given Amber. "Amber, did you put this in here by mistake? Bradley wanted me to use it as part of your payment." "No, mistake. When I talked to him and told him what I thought everything was going to cost, he told me fine. Also, to put the hundred in your purse, you'd need some mad money. I don't know what your relationship is to Brad and it's really none of my business, but if I were you, I'd hang onto him. Someone so sweet as to pay for all of this and give you some cash too is special. Plus if he's as cute as Brandy said, what a bonus. She told me she's been flirting with him since they met, but hasn't been able to move from the friend zone. Sounds like he's had eyes for you all along. By the way, just in case I dropped a small tube of my favorite lube in your purse. You may never need it, but it makes it much better if you do." Amber's description made me blush again but I just tried not to think about it. She then showed me how to tuck the clutch under my arm, next to my boob, or to lightly hold it in my hand. The bright red nails silhouetted against the purse. I was becoming, more and more comfortable in my new identity. Amber had me sit, cross my legs, and showed me a few ways to hold my arms and hands. With each step, she praised me. Told me it was just right, I had simply marvelous feminine instincts. Then she asked me to say something, a simple phrase. Afterwards, she repeated it, with an emphasis on how a woman would say it, and how she would sound. I tried again. Better, but she made me repeat it a half-dozen times until she was satisfied. To my ears, I was speaking much softer, slightly higher than my usual, with a sort of sing-song rhythm that went up at the end of each sentence. Once Amber felt I had the right tone, she and I had a simple conversation. At first it took me longer, as I had to think about each word, but soon it too was becoming easier if not quite natural. But Amber was thrilled. She promised I would pass so well as a woman, that the only looks I would draw would be from admiring men and jealous women. Finally, she called Bradley. She told him I was ready. For him. At that point my nerves really set in. He had told her, he'd be there in minutes, as he'd been waiting just up the street in a bar. We gathered my things, the shopping bags with one small bag containing my old clothes. My male clothes. I was half afraid she'd thrown them out. Bradley, hadn't been lying because his Corvette pulled up and parked right in front of her shop. I had stepped to the side, as Amber and the receptionist were talking to a client at the counter. He came in, smiling, and looking around. He glanced my way, only briefly then saw Amber. He stepped to the counter, as the receptionist took the lady back to the salon. "Where is she? I can't wait to see how she looks. I thought you said you were done." "I am Brad. And she is ready. Right there." Amber pointed to me. Bradley turned and looked at me, again. This time intently, his eyes searching, as if he were trying to find someone but not seeing them. Suddenly his eyes grew wide and he started smiling, beaming actually. He looked quickly back at Amber, as if in disbelief, before looking at me again. "Hello Bradley, don't you recognize me?" My question, soft, with a bit of a tremble, was all I could muster. He didn't answer at first but moved closer, real close. "No, no I don't recognize you. I thought I was meeting my old buddy Patrick. But he's gone. I don't think we've met before. I would have remembered such a strikingly beautiful woman. What's your name, honey?" "Brad meet Cashmere, she's been dying to see you." He smiled and we both looked toward Amber. She too was grinning broadly. It seems everyone was happy, but me. I was still too nervous. "Brandy told me you wanted me to name your new friend. I think Cashmere suits her perfectly. She looks smooth, sexy, pretty and expensive. Plus you'll find she is soft to the touch, silky too. What do you think?" "I couldn't agree more. Cashmere is perfect, she is more than pretty. She's gorgeous. She deserves a sexy name." When he answered Amber, Bradley put his hand on me, lightly touching my forearm and then moving it down to hold my hand. I don't think he'd ever touched me before except maybe to punch me in the shoulder or pat my back. My heart was beating so fast I was sure he could hear it. He lifted my hand up, holding it so my nails were showing. I was getting scared quickly, as it just seemed so wrong. I mean, even if I looked like a girl, I wasn't. He knew it too, but we were both acting like I was what I looked like. "How about you, do you like the name Cashmere?" "Well, it is unusual but it may take me some time to adjust to the sound of it. So if I don't respond to it, give me a moment, okay?" "I love your voice, its soft, sexy, and yet totally innocent. It will take me a while to adjust to that for sure. But I can't wait to go out tonight and celebrate. You look ready for a nice evening. We need to go back to our place so I can shower and get ready. Amber, are these the rest of her things?" Bradley was still holding my hand but had looked down toward where the huge pile of bags were on the floor. It struck me how much money he'd spent on me. I suddenly became embarrassed by asking him to pay for all of this. It seemed unfair somehow. "You know Bradley, I really don't need all of these. I didn't expect you to buy more than one outfit, right? Plus you're covering all my salon bill too. That's just too much money to ask from you. Amber, can you return these and have the stores credit it to his card?" "Well, I could if you're serious about..." "What kind of outfits, clothes did you buy for her Amber?" "Just what you said. There is a casual outfit, jean skirt, white blouse, and boots. A versatile floral sundress with heels. And a business casual outfit of matching blazer, skirt and heels. Plus lingerie, hose, and accessories. I already put all of her makeup, hair products, and an inexpensive curling iron in bags for her. I basically put together a weekend care package. Was that too much?" "It sounds like it. How much was it?" "Don't answer her, Amber. If the amount is what showed up when I looked at my card total when you called, then it's no problem. In fact, I may want you to take her shopping for more given how she looks. Cashmere, just hold the door open for me, and I'll put them in my car." "But Bradley, are you sure?" He didn't answer, but started grabbing bags, so I held the door open and then opened his trunk. The whole time I felt guilty, like I was getting everything and he nothing. But he was smiling and when everything was in the car he told me to get in. Then he went in, gave Amber a hug and thanked her again. As we drove off, I was still nervous but he was all smiles. The ride was awkward, neither one of us saying anything. We stopped at a light, and I kind of moved in the seat, and my dress rode up my thigh, exposing the top of my stocking. Bradley looked over, down at my legs and then at me, a smile on his face. "Are you wearing stockings? With garters?" My face blushed and I self-consciously pulled down my hem. "Yes, yes I am. Amber told me, uhh she told me they'd look nice in this dress." I flushed a little more, as I almost said she told me, men liked stockings, men like Brad. He grinned wider. "Let me see. Pull up your dress and show me." I didn't know what to do, so I gave him a glimpse. I pulled the hem up, past the black welt at the top of my stocking, to show him the black satin garter holding it tight, but not far enough for him to see my panty. He let out a soft whistle, a wolf whistle. "Nice, very nice. Amber did a great job. You look pretty, sexy, but nice." Once we got to the apartment, Bradley carried all my bags to my room. Once he had everything in, he told me he was going to shower and get dressed. Then we could go out. He suggested I put my new things away. I was so nervous about everything. I just started doing it. I started with the pink bags, as I knew they had my lingerie. The first bag had four bras and a nightgown, a soft peach colored baby doll with a thong panty. The next had a half dozen panties, and the last pink bag had three packages of pantyhose and another one of stockings. The rest of the bags had blouses, skirts, two dresses and what seemed like endless numbers of shoes, purses, makeup, and my hair stuff. I hadn't realized she really had bought this much. It looked like way more than I needed for a weekend. The last bag, a small one had my old male clothes. All of it was on my bed so I had to decide where to put it. I hung up the dresses, skirts and blouses in my closet and put the shoes and boots on the floor. With a little uncertainty, I put my male underwear, socks, and tee shirts in bags. That let me put my new lingerie in the dresser. I thought since it was just the weekend, it was sort of like going to a motel and transferring your clothes to their dresser from your suitcase. It was a little harder with my makeup. My bath had only a sink with no counter space and shallow shelves in the medicine chest mirror above it. The toilet was next to it, so I got one of my pillow cases, put it down on the toilet tank top, and then put most of my makeup there. It didn't look too bad, so with my stuff put away I went to the living room. Bradley had just finished showering and suggested we have a beer. I opened two and took him one. It was a little awkward, as he only had a towel wrapped around his waist. I guess I never realized how broad and muscular his chest was. In short order, he finished getting ready, joining me wearing a nice sport coat, dress shirt, and pants. It was a much nicer look than his normal jeans and polo shirt, when we went out. As we drank our beers, he outlined his plans for the evening. "I've lined up an Uber to take us to each place. That way, I can have a few drinks without any danger. We're starting at La Pierre, that nice restaurant at the top of the Barnard Building. After dinner, we'll go to Desires. Amber said it was a great place for drinks and dancing. Then home. How's that sound?" "Wow, I didn't know you liked to dance. We've not done that before." "Well, I've not had such a beautiful lady to take out. Besides we need to celebrate. We're finally doing something different and fun. No boredom tonight." As I looked down at the way I was dressed, I had to agree. It was more scary than boring. Our ride showed up in a few minutes and we were off on our adventure. I was still anxious about my appearance, but after a fancy cocktail at the restaurant I began to relax. I couldn't believe Bradley had gotten us in. It had a reputation that it took months to get a reservation. We had a wonderful table, next to a window and a stunning view of the city at night. The meal was outrageous, multiple courses, each better than the last, but not so big as to make you feel stuffed. Bradley had chosen a nice bottle of wine and when we finally finished, I had a pretty good buzz going. In the Uber, Bradley sat right next to me, his hand on my leg, lightly rubbing my stocking. It was such a different feeling. Desires was as exciting as Amber promised. The music was great, lots of people, dressed nicely and having fun. Again, Bradley wanted to celebrate and ordered a bottle of champagne. We watched and talked for a while and finally, he was able to drag me out on the dance floor. I had always loved dancing but still felt awkward as I had to change my style to something less frantic. Dancing in heels was a big adjustment. We'd danced to about three songs, faster paced, when the DJ put on a slow ballad, a love song. I thought that would signal a break, but instead, Bradley wrapped his arms around me and pulled me close. I had no choice but to slow dance the next two songs. He held me so close my head was basically laying on his chest. It was then I realized how really tall he was. Even in heels, my head didn't go above his shoulders. It felt so odd, to have his arms hug my waist so tight. I tried to avoid it, but his body was firmly pressed against mine. I just tried to ignore the lump, even though I pretty much knew what it was. When the second song ended, we went back to our table and he ordered more champagne. We were having so much fun. The next thing I knew I was rolling over. My head hurt a little and I felt worn out. I opened one eye and looked around. Thank god I was in my own bedroom, although it was a mess. Most of the covers were on the floor, clothes were strewn everywhere, and one side of the bed felt damp. I felt disoriented and it took me a minute to remember yesterday. Seeing my long polished fingernails brought all the details rushing back. My makeover, dressing and going out with Bradley. Regaining some semblance of sanity, I realized I had to pee. Really badly had to go. I swung my feet off the bed and stood up. That's when I noticed I still had my garter belt and stockings on, but no panty. I shuffled to my bathroom, and as if I had always done it, sat down to pee. I lightly held my cock to be sure I didn't spray anywhere, but it was so soft I let go halfway through. I was still trying to remember last night. I got as far as the club, but didn't have any recollection of leaving and getting home. I guess Bradley was smart to get a ride lined up, as he always drank more than me. I sat there, my head in my hands as I finished. My ass hurt, like I had to go, but not really. I guess what I needed now, was a shower, then some coffee, aspirin and maybe a scrambled egg. Something light but with protein. I had felt worse for sure, but knew it would likely be afternoon before I was totally okay. What I couldn't get over, was how I looked. My hands were women's hand, with long nails brightly polished red. I had glanced at the mirror on the way to pee. I was a sight. First, I still had makeup on, although my lipstick was gone and most of the rest was smeared. My hair was tousled around, but the basic hairdo was intact. A woman's hair style. And why I still had on hose and a garter belt was beyond me. I would have thought I'd taken it off when I removed my bra and especially my panties. Even after yesterday, that still sounded odd. These thoughts were processing in my addled head when I heard footsteps. Bradley suddenly appeared in the bathroom doorway. Naked, completely nude, his big cock and balls swinging between his legs. "Bradley! What are you doing? Put some clothes on for god's sake." "Oh, I'm sorry. I guess I figured after last night, why bother." "Last night? What do you mean?" "You don't remember? Last night, after we got home? Or more accurately, even on the ride home. Really? Oh wow." Suddenly, I felt sick, not to my stomach, but just a bad kind of feeling. I looked up at him, almost afraid to ask. I had my hand up, to cover his crotch. I wasn't sure I really wanted to know what happened. "I don't remember anything after the club. Really even leaving the club. Did something happen?" "Cashmere, I'm sorry. It's just the way you acted. How eager you were. I mean you couldn't keep your hands off me in the Uber and when we got inside. You just, I mean, you didn't seem out of it." "Oh god, what did I do?" "Well, it began on the ride home. When we got in the backseat, you slid right next to me. Put your head on my shoulder like you were going to fall asleep. But you didn't. You reached over and began to feel me, fondle my cock through my pants. When I looked down at you, you were smiling and kissed me. We kissed all the way home. By the time I tipped the driver and we got inside, I was rock hard. You didn't even miss a beat, you pulled me over toward the couch, unbuckled my pants, and pulled them down. You were so eager. Your hands were on me in a second, stroking softly. Then you pushed me back onto the couch and you fell to your knees, between my legs. Then you, well you. It was the best I've ever had. You were so good, it was mind blowing." "Oh no, I didn't. Not really. Tell me you're joking. Messing with me. I couldn't have. I'm not that kind of guy." "Well I'd be lying if I said I wish it hadn't happened. You were the best. You actually swallowed me, all of me. No girl has ever done that. Most can't even get a third of me in their mouth. But you swallowed me like I was nothing. Even when I busted a nut, you swallowed like it was the sweetest nectar you'd ever had. You may not be that kind of guy, but you were the perfect girl." I was about to cry. I couldn't believe what he was saying. I kept looking up at him, hoping he'd break into that silly grin of his and tell me I'd just passed out. But he kept a straight face, in fact, he had the sorriest look I'd ever seen him show. I almost didn't want to know, but asked anyway. "Was that it? I didn't do anything else did I? "Well, it wasn't just you. I mean, after I came, you licked my cockhead and stroked my shaft until I was hard again. Then you stood up, helped me up and kissed some more, while you stripped off you dress. Then you grabbed my cock and pulled me to your bedroom. There you got undressed. Or at least took off your shoes, bra and panties. By then I was on autopilot. I was so horny and you were so eager. You know how much I love anal. I guess you wanted to really please me. So you got on the bed and asked me to take you. You were on all fours, your head on your pillow and your ass up in the air. You even reached back to spread your cheeks, open for me. I couldn't resist. We both came that way. Twice. I guess you came, I mean, you were still soft but you were leaking the whole time. After the second time, we both collapsed and slept in your bed. I just got up a few minutes ago, right before you. I had to piss and needed some coffee, so I started a pot. You want some?" My head had been in my hands the whole time he told me what we'd done. That explain it. Why my ass hurt and why I had this strange taste in my mouth. And why, I had such strange dreams last night. But they weren't dreams, they were real. What got me was how, even knowing what we'd just done, Bradley was so even keel about it. He'd even asked if I wanted coffee like it was a regular morning. It took a second, but I knew I couldn't take it back. We'd done it. But I had to figure out where we went from here. I took my head out of hands and looked at him. "Yes, please. Could you put some cream and sugar in it for me? And bring it here? I need a shower. I look a mess and have to get cleaned up and dressed. And can you put on some pants too?" He smiled and said sure. I wiped off, flushed and stood up. Starting the shower so it would be warm, I slowly unhooked my garters, took off my stockings. I had to spin the garter belt around to unhook it. By then, Bradly returned, in pants, with my coffee. He handed it to me, still with that sort of hang-dog look. "Cashmere, I'm really sorry about last night. I would have never done anything if I really thought you'd be upset. But you were so eager, so happy, and so horny. It seemed all okay. You know that don't you? I wouldn't take advantage of any woman, ever." "It's not your fault Bradley. I guess I was too drunk. I can't think of another explanation. Let me get cleaned up and we can talk, okay?" His next move caught me off guard. He leaned and kissed my cheek, softly, then smiled as he left. The coffee tasted great and I took a few aspirin with it. By then the shower was hot. I knew I was still going to have to dress as a woman, and didn't want to redo my hair. So I put on a shower cap, one of those free ones you get at a hotel. The shower felt wonderful, I washed myself, using the scented body wash and a pink shower pouf that Amber gave me. I spent extra time cleaning the makeup off my face and then shaved it. When I got out, I also put scented body lotion on, as she emphasized that my freshly shaved skin needed it. Looking in the mirror, I thought even though my hair was okay, it could use some touch up. I plugged in the curling iron. While it got hot, I went to my dresser. I remembered Amber mentioning a causal denim skirt and white blouse outfit, so I was going to wear it. I picked out white bra and panties and a pair of black mist pantyhose. I slipped the panty, a lace fronted thong and reflexively tucked myself as I pulled it over my hips. The bra was lace too, sheer cups. It took me a minute to look around and find the bra from last night. Laying on the floor, my forms were still in it. I picked them up and put one in each cup. Immediately I felt more like a woman. I then opened the package of hose and carefully, very carefully worked them up my legs using the technique Amber had shown me. Once again, the feeling of the silky soft nylon on my bare legs was electric. A quick glance in the mirror confirmed I was already looking better. Returning to the bath, I used the curling iron to refresh the way my hair curled under around one side and the back. It was a bit awkward to use, working sort of backwards in the mirror. But I did okay. I finished with some holding hair spray. Now it was time to make my face. I had tried to really pay attention when Beth showed me how yesterday. Still, I was more than pleasantly surprised at how much I really remembered. Foundation, blush, and face powder was easy. Doing my eyes was much harder, but I managed to put on the eye liner without smudges. I used just two eye shadows, a darker brown and white for contrast. Then I filled in my brows with brown powder and used a light coat of mascara to finish. I had to admit, my lashes looked long and sexy. The bright red lipstick was the last step. By now, it had almost been an hour and I figured Bradley was going to get aggravated waiting this long. In the closet, I slipped on the white blouse. It was long sleeved, with a band collar, fairly sheer with a square hem. The denim skirt was light blue with a frayed look hem. Short, very short. When I pulled it up my legs and tucked in my blouse it barely came below my crotch. Amber had included a black belt, decorated with round silver badges, a sort of outlaw look. It set low on my hips making my skirt look even smaller. When I looked for a matching shoe, I saw the black, suede thigh-high boots. They too had silver badge type decorations, one at the ankle and one at the top. I had to sit down to put these on, and couldn't believe how high they went, ending about mid-thigh. The heel was ridiculous too and it immediately reminded me of how my feet felt yesterday in the heels. But I had to admit when I looked in my mirror, I was hot. It was a casual outfit but sexy, the long boots making all the difference. A quick check in back let me know to be sure not to bend over, as the skirt would ride high enough to show off my butt cheeks and thong under my hose. I was glad the pantyhose were sheer to the waist with no visible seam. The nylon seemed as if it were painted on me. So, even if I forgot, I would look sexy. I knew I needed a purse. The appropriate one was easy to find, a big black hobo style with the matching silver badge. Once I had that, I straightened up my room a little, putting my clothes from yesterday in the hamper and lightly washing off my 'cleavage-maker pads'. But I couldn't find my clutch. I began to panic. Maybe I had left it somewhere? "Bradley, Bradley, have you seen my purse? I can't find it. I might have left it last night. Do you remember seeing it here?" I came stomping out, well in my boots more like prancing out, of my room. I was frantic, because it had all my IDs, cards, and cash. Plus if I had to do anything dressed like this, I wasn't sure I could. But he was all smiles. "It's over there on the end table. You laid it there right as you came it, before you got distracted. Wow, I like your 'casual look'. God those boots are killer. That skirt is nice too." I had gone right to the end table, and bent over to pick up the clutch. I knew as soon as I did that Bradley was getting an eyeful. But what the heck, he'd seen my ass closer than that. I just went ahead and transferred the contents of the clutch to my new purse. As I did, I realized I would need to grab some makeup too, plus a real hair brush. But as I moved my things, I picked up two surprises. Something I didn't remember seeing before, two tampons. I guess Amber had put them in my clutch when she originally put my wallet items in it. But why? Suddenly, I knew why. "Are you ready to go? I'm starving and I thought we'd get a bite at the soup and sandwich shop at Broadway. It's close and good too." I turned back toward Bradley straightening up. I could see he was tired of waiting. I had taken a long time to get ready. He'd just thrown on a tee shirt and his tight jeans, ready to go in a minute. But I wasn't quite done. "Just a second, I need to grab some lipstick before we go. I'll be right back." I could see his frustration, but I had no choice. I hurried though, as quickly as I could in the heels. In the bathroom, I grabbed my hairbrush, lipstick, face powder and mascara and put them in my purse. I had only used one for a day, and already appreciated their value. Not only a nice accessory to your outfit, but you could take so much stuff with you, just in case. But now, I had a pressing need. I quickly pulled down the panty of my hose and my thong as I sat on the toilet. I felt a little drip out, slowly but there. I wiped with some paper, and yes it was what I thought it was. Amber must have had a good idea that Bradley and I would wind up in bed. Smart girl. I unwrapped the tampon, looking at it in a new way. I vaguely remembered looking at a box of then when I was a young teen at home. A quick look at the design confirmed my memory. I raised up a little off the toilet seat, reached back to pull one ass cheek to the side, and placed the cotton end of the tampon at my asshole. I pushed and it went in, easily. I blushed realizing my recent activity with Bradley must have loosened me up. With the applicator in as far as it would go, my fingers against my ass, I pushed the insert until my hand met my fingers holding the other part. I then slid both tubes over the string and it was done. I gently tugged the tampon in place, just to be sure it was at my opening. It was embarrassing to know I needed one, to keep from leaking the results of my lovemaking all over my panties. But still necessary. With that done, I pulled my thong into my crack and stretched my pantyhose back over my hips into place. I looked in the mirror, and everything looked fine. I joined Bradley back in the living room. "Sorry. I really am ready now." He was already standing at the door, with it open. I went through and as we walked downstairs he wrapped his arm around my waist. I don't know why, but somehow that made me feel better. I know I had crossed a line with him last night. A line I couldn't go back over. From now on, he would see me much differently than before. But just knowing, he still liked me enough to hold me, made it better. I guess I was worried he'd think I was just a slut or was actually gay and had never told him. I still found it difficult to admit I had not only submitted to him, but aggressively pursued him sexually. I was sure he'd never taken advantage of me, being that drunk, unless I had encouraged it. Well that was water under the bridge. He was nice enough to open the door to his Vette for me and I sat down, pivoted and swung my legs in. I could tell already that this skirt would require my constant attention or I'd be flashing every guy in town. We drove quickly to the diner, and I repeated my move, although he did extend his hand to help me up. That of course, allowed my skirt to slide up in front. But at least, he was used to that view now. He took me by the arm and escorted me inside. The food was good, simple but tasty. It was the last part I needed to clear out all the headache and cobwebs from last night. As I sipped the last bit of tea, I asked what he had planned now. He had pulled out his phone to check something, a normal habit. "Well, I thought maybe we'd go for a drive and then I need to stop by the plant. We have to sign a few papers." "The plant, with me like this?" "Don't worry. First of all, the only one there will be the entrance guard. He knows I'm coming. He won't recognize you, because you look nothing at all like Patrick. I expect all the workers to be gone, as management stopped everything for the holiday. We'll sign a few papers, fax them, and drop them in the mail slot then we're done." "What kind of papers? Why the rush?" "Just a few forms the home office needs. A clarification on a request of mine. No big deal. I just got a text from them yesterday, but forgot about it. But first, let's drive up the overlook to the pass. The weather's so nice, the view from up there will be amazing." He had reached over and squeezed my hand. Then he hit the gas and his Vette leapt forward. I had never been comfortable riding with him before, and usually we took my car. But now, somehow it felt right. I settled in and watched the scenery fly by as we headed up into the mountains. Every once in a while, Bradley would put his hand on my knee, then slide it up until it went under my skirt. I removed it every time, but he'd just smile and do it again in another ten minutes. I could tell he loved having me so close and available. I knew he'd love it even more, if I was wearing stockings again. Amber was a very smart girl. When we got to the summit, he pulled over so we could step out and look at the view. It was spectacular, and today it looked like you could see forever. I moved over to the rock guardrail and Bradley followed. As I stopped to look, he moved right behind me, enveloping me in his arms. The whole day had been like this, him being very close and touchy. I wasn't sure how to react. How I really felt about it, or what I should do. I knew we'd crossed a line last night, but we were still men. At least, I was still male. But it was like a switch had been thrown and in his eyes, I was a girl. All girl. Like now, he pulled me closer, tight against his body, and lightly kissed my cheek. Just a soft peck, the way lovers do. Part of me wanted to push him away, but another part was okay with it. Then he nuzzled my neck, kissing and lightly rubbing me. That prompted a reaction, because it tickled and gave me goosebumps. He also held me tighter. I was starting to get annoyed. There was another couple there, a middle aged one. Who just stood and looked. I felt like Bradley was purposely kissing and hugging me for them, to show off. When he moved from my neck and started nibbling my ear, causing more goosebumps. I reacted. "Bradley, behave. You're tickling me." "Oh you love it, you know you do." When he said that, he released his grip on my waist and moved his hands to the back of my thighs, then right up and under my skirt, squeezing my buns. I turned to look back at him, ready to scold him for being so forward in such a public place. But as I turned he leaned in and kissed me. Pressing his lips on mine firmly, he extended his tongue and I relented and let it in my mouth. Feeling overwhelmed, I kissed back. From the corner of my eye, I saw the older couple had noticed us. They looked at each other, smiled and went back to their car, holding hands. His kiss did feel good, soft, sensual, but strong. I'd never been kissed like that. I had always initiated kisses, but now he was taking the lead. My heart was starting to race, as he didn't seem to want to stop. Finally, he moved one hand from my cheek, upward to cup my breast, my form. He squeezed it like it was real. Then he broke off, a big grin on his face. "You know this would be better if these were real. I bet Amber or Brandy would know a good local plastic surgeon. You could get a nice pair, something that when I held them, or sucked on your nipple, you'd feel the pleasure." "Well get over that. I don't need anything like that. Nothing that permanent for sure." "Just saying, I'd be glad to help, if you want a nice pair. Be good for both of us." "You're incorrigible. Now stop." "Okay, we have to go anyway. We need to get to the plant." Bradley took my hand and pulled me toward the car. He was still a gentleman in many ways, as he opened the door for me. Going down the mountain I kept thinking about what he said. Why would he even think I'd consider getting breast implants? I was hoping he'd see this wasn't practical, and settle for a weekend to break the boredom. As soon as I got lost in my thoughts, his hand would gently rub my thigh, playing at the edge of my skirt. Honestly, I don't know how Janet handles him. Out of the mountains, Bradley made the turn toward our plant. I was starting to get nervous. It seemed too risky for me to go there, dressed like this. Maybe I could wait, while he went. "Bradley, are you sure this is a good idea? What if someone recognizes me? Why don't I wait by the diner down from the main entrance?" "You worry too much. First of all, I bet the only person we see is Mr. Hansen or one of the other security guards at the main gate. He rarely sees you and would never think this lovely lady is Patrick. Second, I need you to sign the forms too. But it will be quick, I don't think we'll be more than 15 minutes, unless the fax acts up. Relax." By now, he'd turned onto the road leading to the main entrance. I sort of slumped down in my seat, making sure my skirt was pulled down as far as possible. When he slowed up at the guard shack, I could see it was Mr. Hansen. Bradley stopped to talk and let him open the gate. He was holding his badge for the guard to see. "Hello Hansen, pretty slow today I bet. I just need to make a quick trip inside." "Hello, you're right. You're only the second one to come by today. Who's your passenger?" "Oh, that's a potential new hire. Cashmere May, she came in for a job interview and I thought I'd show her the place. We've been driving around looking at some of the local sites. Beautiful weather and all." I about choked when he told Mr. Hanssen that name. The guard leaned down to look closer inside the car. I smiled and wiggled my fingers at him, in a girly wave of hello, my polished nails reflecting the light to give little flashes. He straightened back up and looked back at Bradley. "New hire, huh? Well don't be too long and stop on the way out, so I can make sure you both leave. Have a good day." Bradley slowly pulled away from the gate, headed toward our building. Once we were out of earshot, I spoke up. "What was that about? Cashmere May?" "Well I figured he'd ask, since you didn't have a badge. Or did you want to show him the one for Patrick Myers?" He laughed as he parked in front of our building. We got out and made our way inside. The whole time, I was looking around, my heart racing. I followed him to his office. We had been given a small suite, two larger outer offices, with windows, fronted by a small reception area where our printer, fax and copy machine were located. He went to his office, opened his computer and printed out some forms. Once he had sent them all, he picked them from the printer, put them together, and laid them on the desk. The top form was a requisition for supplies, and a couple equipment items, routine. He signed on one line and I signed the next one. After we did the cover, he just folded back the pages to show the signature area for three more pages so we could both sign. Once he had them together, he turned on the fax to let it warm up. While it started to hum, he opened a file cabinet, rifled through it, until he found what he was looking for. He laid the form on the desk, and filled in a few lines. "Sign this for me. Sign it Cashmere May. It's a job interview form. I'll put it in the plant mail to HR. That way, if Mr. Hansen decides to check up on us, we'll be covered." "You sure? What if HR calls about it?" "Well, I just say it didn't work out. Ah good, the fax is ready." I reluctantly signed the papers and he asked if I would get his cap from his office. He'd forgotten it Friday when he left for the weekend. I heard the pages running through the machine and only had a short wait for them to finish after I got his hat. I was never as happy to leave the office as I was now. The ride out went uneventfully, my smile and a small wave to the guard as we slowed down was all it took to open the gate. As we headed out, Bradley was smiling. "Now that's over, let's go out for something to eat and a few drinks. How about Shooters? I bet Brandy would love to see how you turned out." Bradley was right. Brandy was thrilled at how I looked. When she saw me, she gave me a big hug and made me do a little twirl so she could check me out. We sat in a booth and I had to tell her everything. Well most everything. I was quiet about what had happened after dancing. Bradley was in such a good mood. We had hamburgers from the grill and a couple of beers while we chatted. I told him I wasn't eager to drink too much after last night. He smiled and agreed. So we mostly talked. Finally, it hit me. I had to pee. I leaned into Brandy and whispered. "Brandy what do you do if you have to go to the bathroom? Which one do you use?" "Oh, honey we look good enough to use the girl's. Come one, let's go. I need to touch up my face anyway." I followed her lead and inside I headed straight to a stall. As I sat to pee, I remember my tampon. It had been in most of the day, so I reached back, found the string, and pulled it out. I wiped off, got my panty and hose back in order and went out to wash my hands. I thought I should check my makeup too. Standing there next to Brandy, as we worked on our makeup, I suddenly felt like I needed to confess and get her opinion. "Brandy, have you ever needed, I mean used, some feminine protection, after you've been..." "Oh my yes. Don't tell me. You and Brad! I knew he wanted you. Was it good? Oh my word, you lucky bitch. I've had the hots for him for months and you nail in your first day as a girl. Can't say that I blame him, you look so good. Of course, I always use a tampon. I put it in right after. I swear you'd think a man is leaving a gallon, the way it just sort of leaks out. I'm so happy for you, really." We talked a little more and she even hugged me, telling me that she loved having another girl to share such stuff with. When we got back to the booth, Bradley told her I'd need to do some more shopping and asked if she could help. I sort of downplayed it, making the comment that I already had more than I needed for a weekend. Bradley smiled. "Come on, you're not reneging on a deal are you? I told you I'd cover your food and drink for our entire stay if you looked like a girl. You're not going to try to argue you aren't pretty?" "Well, I mean, it's not like it's something I can do easily and I, it's just that I..." "Sorry sweetie. I think you lost that bet. Amber texted me after you left her salon and said she'd created a princess and I agree. You're cute and beautiful. I'd thought you might look good, but you exceeded my expectations. What really makes it, is how natural it seems for you. Your walk, body movements, even your voice all are so authentic. Plus, you have to admit, being a girl is a lot of fun, right?" Brandy laughed as she said it. Then told me she'd could meet me outside of Amber's salon at 1 tomorrow, so we could do some more shopping. I looked over at Bradley and he too was grinning. What really worried me now, was how I'd get changed back enough to go to work on Tuesday. But those thoughts were pushed aside. Brandy wanted to congratulate me and bought a round of shots for us. I did mine, but told them I wasn't doing any more, as my head couldn't take a repeat of last night. Bradley agreed, surprisingly, and suggested we go home early. Before we left, Brandy hugged me again and asked if I needed more fem protection. Then laughed. The ride to our apartment was kind of quiet. I needed to talk with Bradley. We just got in our place, when I stopped, turned to face him. I held both of his hands and looked him dead in the eyes. "Bradley, I know you won and all. I have to admit, I do pass as a girl. But this isn't really practical. I can't go to work, like this. If I take off my nails, remove my polish, eyelashes, and cut my hair back to look like a man, then I won't be pass as a woman. If I don't do all that, then I can't go to work. I was just hoping we could enjoy this weekend and then be done with it. I admit it's been fun, in a weird way, sort of exploring life from the other side. Today was super, sightseeing and all. We've been here months and not done this. Plus the first night will always be special. Let's leave it at that, okay?" He didn't answer right away and I took that as a good sign. He's pretty practical and had to see my points were logical. Finally he squeezed my hands, and surprised me by leaning in to kiss me softly on the lips. I wanted to turn away, as I knew I was another man after all, but I didn't want to anger him, while we were discussing how this would work. "Cashmere, I can see your argument, but let's not rush any decisions. I mean, we've got tonight and all of Monday. Let's enjoy our time together first. Honestly, I'm sort of surprised you've not wanted a follow up yet. You were so hungry for me last night. Want another taste?" Bradley had leaned into me as we talked and I could feel him, his cock pressed against my body. I had been dreading this moment all day. I knew after what we did last night, the aggressive way I apparently pursued him, that he would expect more. More from me. But whatever got into me last night, the liquor, the forbidden thrill of looking like a girl, the sexy lingerie, whatever, it was gone now. Just thinking about having sex again with him made me anxious and a bit sick to my stomach. Now the moment was here. "Bradley, I don't know. I mean, I can't deny what happened last night. But I'm not sure anything more is good idea. It was probably just the booze making me that way. Not how I really feel." "Oh come on. I saw it. In your eyes. The lust, desire and the satisfaction when we were done. You were in a dreamland. It may have taken a few drinks to let it out, but it was real, the real you. Give it another chance, this time when you can remember it all. I'm sure once you start, you'll love it, again." As he talked, he had unzipped his pants, and pulling one of my hands in through his fly, placed it on his cock. I could feel it, the heat, and the blood pumping even. I could tell he was getting excited and expected me to react. Maybe he was right. It was hard for me to imagine I would have done anything I wasn't really wanting to do, even if I was drunk. I had never been attracted to men, not seen them as sexual partners. But if I had been that eager last night, maybe it was something I had always repressed. There was only one way to find out. "Okay, let me see. I'll try it again." As I relented, he pulled his pants down leaving his rapidly hardening cock in my hands. With a gentle push down on my shoulders, I dropped to my knees as he settled back on the couch. I was now face to face with it. His cock, thick, long, and hard. His cockhead looked huge, a soft purple. A drop of pre-cum appearing in his slit, signaling his desire. Both of my hands were wrapped around it now, their pretty red fingernails looking very appropriate as I held him. That only emphasized how big he really was as even two hands didn't cover his whole shaft. I could smell him too, musky, tart with that unique odor, a male odor, a semen scented bouquet. Not appealing in any way. My heart was beating so fast, not from excitement but fear and hesitation. How had I been so eager last night? I felt like crying. But I knew it was too late. Bradley was expecting me to please him. I started toward him, moving my mouth closer. As I did I closed my eyes. Then I heard him. "No keep them open, your eyes. I loved how you looked at me, showed your joy to me, as you swallowed my cock." Trembling I did as he wanted, and then I felt it on my lips. Burning them with its sexual heat. I didn't know how to start, so I kissed it. Closed lips at first, then opened more, and finally a French kiss, my tongue tracing over his cockhead. I was struck by how soft and smooth it felt. The taste was strong at first but when I circled my lips around it, put his head entirely in my mouth to suck it, I adjusted quickly to it. I kept it like that for a minute or two, just the head in my mouth. It was as if I were afraid to take in more. It was also so hard to look at him as I did it. It was far more submissive than I expected, not sexy at all, but more an exchange of power. I could see his smile, a signal that he was approving of my actions. But I could also tell he wanted more. He finally placed one hand at the back of my head and applied some pressure, just a little. "Go on, swallow more. Show me how much you love it. I know you do. It's okay, it's natural for girls to love sucking a man's dick." I had hoped the taste, the action, the feel, or anything would have triggered the response I had shown last night, the desire for his cock. But nothing happened, except I was feeling sad, trapped, and of course full. His cock was stretching out my mouth. All I could think about and hope, was if I pushed on, that it would stimulate my desires. So I began to slide down his shaft, my tongue flattening out at the bottom of my mouth to let him pass. I kept waiting for some kind of gag reflex. The one time a girl had taken my cock in her mouth, she gagged after I put an inch or so into her. But I felt nothing like that. Just the strange feeling of being stretched out. And full. I was focusing on keeping my teeth away, letting the shaft glide on my lips without scraping his sensitive skin. I was sucking too, both to stimulate him and to swallow the spit that was forming in my mouth. His cockhead hit the top of my throat, ready to go forward. I glanced down, breaking eye contact momentarily, to see how much was in. It looked like I had more than half. I knew I'd have to slide him into my throat if I was to swallow him whole. I had last night, so I tried again now. Bradley had put both hands on my head, not pushing just holding. A sort of light reminder of his control and my submission. Slowly I pushed forward, pushing this big cockhead into my throat. And down it. Once the head passed the opening it slid in fairly easily. Apparently, I had no gag reflex to speak of, as I only quivered once, a small reverberation, but nothing that would stop his progress. I was so intent on keeping eye contact and swallowing all the saliva so I wouldn't choke, I was taken by surprise by it. My nose, ticked by his pubic hairs and his balls pressing into my chin. I had taken him all the way in. Maybe that meant I did like sucking cock? Bradley let out a deep moan and said softly, 'that's my girl'. I kept him there sucking as hard as I could. I could feel my throat muscles contract around his hard shaft every time I swallowed. I could hear his pleased response too. Finally, I figured I should let it slide in and out some. I had heard once, in a porn movie that a good blowjob was like a good fuck. The girl should let a man run his cock in and out of her mouth just like her pussy. So I slid up his shaft, all the way, until only his cock head remained in my mouth. With my tongue free, I licked his glans as much as I could. Then I pulled it all the way out. I was not looking at Bradley's face now, but staring at his cock. The feeling of having it out, reminded me of how much he stretched me when it was in. His cock was twitching now, as if trying to breathe. But gentle pressure, from his hands on the back of my head, told me I needed to swallow him again. So I did. This time, I went faster, until my nose again smelled his pubic musk. I began to bob my head, going part way up his shaft and then down again. Each time I traveled a slightly different length, teasing and pleasing him. I could tell it was working too. He was more vocal and he was leaking more too. More and more of what I swallowed had a stronger semen taste. He was getting more excited. I had removed my hands from his cock so I could take it all in. I used one to cradle his balls. They filled my palm, warm, hairy and sweaty. I was going faster now, up and down. Each trip bringing more reaction from Bradley. I had stopped looking at his face, as he had rolled it back. His eyes were shut and his mouth open. He gripped me tighter with his hands, and began to move his pelvis some as I sucked him. Then it began. I had just swallowed all of him, my stretched lips taut against his body. He held me tight, tighter than before. I also felt his balls tense up, the sack twitching, as they moved in my hand toward his body. I knew he was going to cum. I wanted to move up his shaft, so my throat wouldn't be so full. But he held me in place. I felt it, the first shot, both in his balls and cock, twitching. Then another, in rapid fashion. He was moaning loudly too, and saying stuff like oh god, yeah, suck it, yes, yes. With the explosion of cum, came an explosion of taste and smell. An overwhelming scent coming up my throat into my mouth and nose, filling my senses as much as his cock was filling my throat. I had to just take it, as he came and came. I swallowed furiously and was able to take all of it without choking. I had even stopped breathing to be sure. Finally he relaxed his hands and I quickly moved my mouth up so only his cockhead remained in my mouth. I had to breathe. Deep breathes, through my nose, completely saturated with semen smell His cock was still pulsing, leaking come. So I used the tip of my tongue to clean him, flicking across his opening. I didn't want a string of come linking my mouth to him when he pulled out. I must have touched the now highly sensitive tip too much, as he used his hands to pull my mouth off his cock. I looked up at him now and he returned my gaze. He was satiated, totally fulfilled, at ease, calm, now breathing slowly with a wide grin. I felt used. At no time did I get excited, horny, or even pleased at how I satisfied him. What had triggered me that first night? Still, I smiled at him, weakly. He rubbed my face with his hand, a soft touch. Then he sat up a little, glanced down at his cock which was still resting on my chin. "Go on, you can lick and suck it again. I want your ass pussy tonight too. I know you want as bad as me. You can't tell me you didn't love sucking my cock. You were so good, that eager mouth, that unbelievable throat. No girl has sucked me like that. I bet your panties are wet too. They were last night. We'll see when I take you to your bed to fuck you. But first get me hard again." The way Bradley talked, it was like, it didn't really matter what I felt or thought. If he saw me as excited then I was. I wasn't sure I wanted his dick up my ass again, but I rationalized I need to feel it all, tonight, to know for sure. Reluctantly I opened my mouth again, suddenly aware of how sore my jaws were from being pried open so wide for so long. I put his cock head in my mouth and sucked. My hand stroked his wet shaft, sliding up and down. Bradley didn't disappoint. In moments he was rock hard again. I knew this time, it would be a while before he came. Seeing I had prepared him, he stood up, extended his hand and easily pulled me to my feet. My legs were almost asleep having knelt for so long, but a step or two and I was alright. What surprised me, was how forward Bradley was. He put his hand between my legs, and felt my crotch. His smile broadened. "Yeah baby, you're soaking wet. I knew you love sucking dick. What a girl. Now, let's go upstairs and I'll fuck you so hard, you're squirting everywhere." Even after what I had just done, sucking him to climax and swallowing his cum, that was more embarrassing. How could I be wet there? I didn't feel excited, especially excited enough to even leak cum. But I just followed him, as he held my hand and pulled me into my room. When we got there, he turned to face me again. "Man I'm going to love fucking you in those boots. Turn around and let me tear an opening in those pantyhose so I can put it in." "No, wait, let me take them off. They're expensive and I don't want to waste them. I'll take them off, my thong too, then put my boots back on for you, okay Bradley?" "Well okay, honey but be quick." I don't know why I reacted like that. He paid for them after all. But the idea of ruining a pair of 50 dollar hose just seem like such a shame. So I sat down, unzipped my boots, and peeled off my hose and panties. As I did, I saw the wetness Bradley had felt, a small blob of white slimy liquid right where my tucked penis had been. I hurriedly put my boots back on, and stood up. He was sitting on the bed, stroking his cock, having watched me strip and get ready for him. I suddenly remember the lube Amber had given me. I had taken it from the clutch and put it in the bathroom. I glanced at Bradley, unzipped my denim skirt to let it fall too. Then smiled. "I'll be right back, I have to pee first." Not waiting for an answer I went to the bathroom. I grabbed the lube and sat on the toilet, because I did have to go. When I was done, I put the opening of the tube at my asshole and squirted it inside. When I had repeated that a few times, I put it down. Seeing myself in the mirror, I took the time to remove my blouse but left the bra on with my forms. Plus I cleaned and replied my lipstick. I walked back toward Bradley, anxious but willing to see how it was. "God you look so hot. I love your legs in those boots. Get up on the bed, up here, head down." I was getting nervous now, he looked so big and thick. But I guess I could handle him again, if I had already. I awkwardly got on the bed. I felt so submissive, putting my head down and exposing myself. Bradley wasted no time, putting his hands on my cheeks and spreading me open. Then I felt it. His cock, right at my opening. Again, no wasted time, he began to push. It was slow at first, but he hit the lube which helped. As he forced his way in, I felt like my asshole would rip, it was painful. But it was also such a different sensation, having something in me like that. My ass felt on fire as he plunged in further. Bradley, was loving it. He lightly spanked one cheek and told me I was his bitch. He leaned over my back and whispered in my ear. He told me that he knew I loved this and that I had shown him Saturday night that I belonged to him. By then, he had buried his cock all the way in me. "Come on, wiggle that ass. Show me how much you need me." As much as it hurt, the pain of him stretching me open, Bradley's comments were worse. But I wanted to know for sure, if I really did want this, deep inside me somewhere. So I did as he told me to. I pushed back against him and moved my ass, side to side, in the best wiggle I could. I felt my face flush. It was such a submissive act, so humiliating. But Bradley loved it. He pulled out a little, spanked me lightly again, and plunged in quickly. This time I felt his balls slap my ass. By now he had a firm grip on my waist, right above my hips. He was developing a regular rhythm, getting into fucking me, pull out, slam in, pull out, and slam in. I kept hoping that somehow, at some point, it would become pleasurable for me. I could tell it was for him. The pain had lessened, and I could feel him inside me, as he stretched my opening. But I mostly felt taken, owned, and just a piece of fuck meat. Maybe if I tried to get into it more, it would help. So I pushed back when he plunged into me, I wiggled some more, I moaned and told him he was so good, so hot, and that I needed it so bad. I even reached back to fondle my cock. It was still soft, but wet, leaking more pre-cum. Of course he loved it, and fucked me harder. I knew he had stamina in bed, or so he had told me before, but still I kept waiting for his climax, so this might end. As he plowed me, he alternated between griping my waist and moving one hand to squeeze my ass cheek. Then he plunged into me, as deep as he had, and pressed his body down on mind, stopping for a second. His hand found the clip on my bra and released it. Then his other hand slipped under my cup to find my nipple. Pulling and squeezing it, he played with me. "Now don't you wish you had real tits, big nipples, so you could enjoy this even more? I know you want them, every girl wants big tits. But don't worry honey, I'll take care of you, just like you're taking care of me. We'll get you some real soon." The way he had me pinned, and then whispered it in my ear, was so controlling. I felt like I had lost my free will. It was like the final extension of this crazy weekend. Then he lifted up, let go of my breast to grip my waist again, only tighter. I felt his speed increase as he became more excited. I looked back, under my body toward him, not sure what I'd see. Front and center was my cock, still small, still soft, but leaking a steady stream of cum. A puddle already formed on the bed. I was crushed. All of this had seemed so bad, horrible in a way, like I was being abused, my male identity raped by him. So how could I be coming like that? No wonder he thought I loved it, why wouldn't he if I squirted cum liked a teen girl gets wet? Then it happened. He tensed, plunged in all the way, and his whole body jerked, once, twice, and a third time. I couldn't really feel it but knew he was filling my ass with his cum, like he had the other night. Collapsing on me, first on my back, then pulling me so we lay side by side, Bradley wrapped my upper torso in his arms as he tried to recover. His breathing slowing, he kissed my neck and cheek, softly, lovingly. I wanted free, so I tried to move but he held me close, so I relaxed. "God you are so good. Cashmere you're such a good fuck, your pussy is super tight. It feels wonderful. I like how you fuck back too, you wiggle like it means everything to you. I'm so glad we decided to try this, do it this weekend. I could sense when you were really losing it, just like last night, you start talking dirty and telling me how much you want my cock. But don't worry, I'll give you all you need." I cringed hearing him, because the way it looked and sounded he couldn't think anything else. But all I wanted was to break free. I knew he was still in, so I tried to move away, lifting one arm. But he would have none of it. Holding me even tighter, he chuckled. "Hold still little girl. I'll give you another one. I always fuck my pussies twice. The second time will be even better. I get just as hard and last twice as long. That's how I know you're perfect for me, I can already feel it getting hard again. This time I want to go deeper, as far as I can. Lay on your back with your feet in the air. I'll give you my best." Bradley moved back, pulling his cock from me. It was hard again, amazingly. I moved into the position he wanted. On my back, my legs in their long boots, held up and pulled back toward my chest. My ass spread, my 'pussy' open for him. He moved on his knees between my legs and closer to me. Grabbing my boots, he put one leg over each shoulder and holding his cock put it at my opening. It slid in as easy as if I were made to take him. He pushed forward, going deeper, and deeper, and deeper. I could feel he was in more than before. Not quite believing it was possible. His face was grinning, he glanced down at my cock, still soft, but running like a faucet. He reached out to tweak my nipple again. Then he began to fuck me, seriously, as if he were on a mission. I lay back and took it, letting him have his way for a few minutes. Then I had to do something, I had to encourage him to come again, or I'd be here forever. I rotated my ass toward him, every time he pushed in me. I began to moan and thrash around, as if he were the best fuck ever. "Oh Bradley, give it to me, let me have it. Oh you're so good. What a cock! What a man! I want this so bad, fuck me, fuck me harder. Oh honey, please do me, more, more." My sex talk seemed to do the trick as he started going faster and faster. Fucked me harder and harder, moaning, thrusting as deep as he could. Finally he started to come again, shooting it in me on one upstroke. Then with a grin on his face, he pulled free of my ass, shooting cum on my cock. It was soft, small, and covered in its own juices. But he layered his cum over it, like a statement of ownership. A demonstration of who was the man and who was his cunt. Done, finally, he grabbed my boots at the ankles, and held them apart, spreading me open. He rocked back on his haunches looking at me. My ass was still gaping, still open from the presence of his cock in it for so long. While my cock, shriveled and now slimy with cum, looked nothing like his. He had softened, hanging down but still several times my length. He grinned. "There you go baby. I took care of you. Gave you the big fuck you needed, you craved. You were even better than last night. I hoped you'd be wilder if you weren't drunk and you were. Man, I wish I had my phone. I'd love a pic of you like this. Maybe next time. But I need a rest and a shower. Come on honey, let's go get cleaned up." Bradley got up from my bed, please with himself and headed to my bath. He started the shower and went to the toilet to piss. I heard him start as I was unzipping my boots. I felt so nasty. I knew his cum had been inside me, and I'd even swallowed it. But to see it on me, my skin and my cock, seemed like a stain. I slipped off my unhooked bra and carefully made my way to the bath. He was done pissing and put the seat down for me. It was a small thing, but he made it clear, I was now a girl. I felt embarrassed, but I sat down, while he watched, and peed. I was hoping some of his stuff would come out too, but not yet. So I flushed and followed him into the shower. He'd lathered up his hands and gave me the bar of soap. As he washed his face and upper torso, he told me to do his cock and balls. Like he was giving me a treat. They were nasty from fucking me but I did them, as well as his legs and ass. Of course, when he was rinsed off and done, he kissed my cheek. "I'm going to dry off. Since your bed is all wet and messed up, come sleep with me. I want you there, next to me." "Okay, but it will take me a while. I have to clean my face and shampoo my hair. I'm going to have to put it in rollers too. You sure you want me in your bed?" "Course, no problem. Janet sleeps in them all the time. I think they look cute." With him gone, I washed my hair and then conditioned it. I also shaved my face, after I used a facial cleanser. I did my body with the pouf and scented soap. By the time I got out, I could feel my ass, it hurt more than it did this morning. Also, it felt loose. I found my purse and got the tampon. It was another humiliating moment to put it in. A sort of emphasizing touch of my new feminine status. After that I used the rollers Amber had put in my beauty bag. I had seen my sisters do their hair when I was younger. Because mine was short, eight small ones were plenty. Covered with a pink hair net, I decided I should use my baby doll nightgown. When I went to Bradley's room, it was dark and he was already snoring. I crawled in, falling asleep despite his racket. The light touch of a hand, running over the curve of my ass woke me. It took me a second to realize where I was. As I moved, the hand squeezed my cheek and then moved to playfully tug on my thong as it came out of my crack. I felt a body move against mine and a soft kiss on my neck. Goosebumps. "Morning sexy. I hope you got a good night's sleep. You were wonderful last night. So hot, so eager to please. By the way, I got you something to start your day." I felt it against my ass, his hot cock, rock hard. Another kiss on my neck, then my cheek, close so he could whisper. His hand was cupping one of my breasts, through the nightgown, enough to make my nipple hard. "Why don't you go ahead and take care of it for me, sweetie? I'd love to feel your mouth on it again, perfect way to start my day and yours too, right?" Bradley had moved so he was reclining on his back against the padded headboard. He reached over to turn my upper body. I saw his cock, jutting upright, like a spear. I cringed. After last night, I wasn't eager to repeat more sex, especially this part. It seemed so humiliating to use my mouth for him. But I could tell he expected it, still with the delusion that I loved doing him. Something I had created, mostly of my own free will. So I sat up, moved to him, on my knees and started. I was becoming acclimated to him now, his taste, his needs, and desires. He was so horny, I was done in five minutes. He had cradled my head in his hands holding my curlers so I would swallow it all. He'd made comments as I bobbed up and down, like a cheerleader, or commentator, complimenting me on my cock hungry skills. As I licked the last bit of his cum, off his cockhead and let go of him. I sat up, worried he'd want to fuck me now. But he seemed satisfied. "What a perfect way to start the day. Good job, honey. But I'm hungry. We got any food left? Can you make me some coffee too?" "I think we've got eggs and toast, will that do? I normally would have gone to grocery by now, but missed it." "That's fine, you can go today. You'll do some laundry too, won't you? I need some clean underwear." That's was the kicker. Not only was I to be his cock slut, but his maid too? I wanted to say something, but honestly, I'd been doing both chores for a while. I mean I liked to cook, and did my own laundry, so why not his too? I just smiled and headed to the kitchen. I had the coffee brewing and started the rest. There were only three eggs and two pieces of bread, so I put them all on his plate. I wasn't really feeling hungry any way, the taste of his cum in my mouth made me just want some coffee. When he came to the table, he was just in shorts and a tee. "Looks good Cashmere. I put my dirty stuff in the hamper. Be sure to buy some dinner stuff, maybe steaks or pork chops. You do well with those. And get me a few six packs too, I'd be nice to have some beer at home. I figured I'd watch a few games today, so beer would be just right." "Okay, I will. I've made a list while you were in the bedroom. I'll buy enough for three or four meals, and your beer, if you want. I figure I can use that hundred you gave me." "No, that's for you. Mad money if you feel like getting a treat. Buy something special with it. You can charge the food and any new clothes you buy with Brandy on my card. I called last night and added your name to the authorized list. Just sign your name on the charges." "Oh, thanks, so Patrick?" "No honey, your new name, Cashmere May. If you're going to be dressed as a girl, use your girl name. And do me a favor, when you go shopping with Brandy, buy some cute little house slippers. You know the kind that girls wear, with a bow on top with heels. I'd love seeing you in them with your nightgown." I took my coffee and headed to my room. I guess it was nice of him to add me to his card, but it was more evidence that he wanted me to continue playing girl for him. I did make the deal, but I was getting worried about work and how to balance both. I glanced down at my long, red nails holding my cup. I'd gotten used to their length surprisingly easy, and liked how they made me look more feminine. But I couldn't wear them to work this way. Same with my hair. I had decided, I'd just have to trim both, use clippers to cut my hair short. I was sure Amber could fit me with a wig. Embarrassingly when I sat to pee in my bathroom, I could see where I leaked into my thong, again. I guess pleasuring Bradley did have some effect on me. Quickly brushing my teeth and shaving, then, I settled into what was already a morning routine for me, lingerie, makeup, hair, dress and heels. I went to my dresser and picked out my bra and panty. Yesterday's makeup was easy, so I did the same. I had to admit once my face was done, even with my hair still in curlers, I looked like a girl. I knew I was wearing my floral dress, it had multiple shades of red, pink, and peach, in swirls of large flower patterns. To match, I had picked out a bra and panty in a muted pink. I knew the dress was a sundress, with triangle cups and low cut in front. So I used the adhesive pads, to create cleavage, and my forms to fill my cups. Simple nude pantyhose was a perfect complement to my outfit. The dress slipped on over my head, with only a little trouble from the rollers. Because it was a sundress, with spaghetti straps, my bra straps showed when it was on. But the colors matched and they had pretty lace trim, so I figured it was okay. I'd seen other girls show that look. Doing my hair was a challenge. The curlers gave it body and volume, but I still had to comb it in place, holding it with lots of spray. Still when I looked at my image, I was pleased. If I had to go out as a woman, I wanted to be pretty and passable. The heels were floral sandals that matched the dress. I transferred my necessaries to a cross body hobo bag, in the same pink as my lingerie. Somehow, being all color coordinated was important. The thing, I didn't like the most of all of this, is how long it took to get ready. Before, I'd already be at the grocery by now. Maybe if I did it enough, I would be quicker. As I headed out, I saw Bradley was in the living room, sprawled out on the couch watching pre-game shows. I also saw he'd left his dishes on the table, not cleaning up at all. Being careful not to mess up my dress, I tidied up the table and kitchen. Sticking my head in the living room, I asked if there was anything else he needed. He shook his head no, and smiled. "Love that outfit. It's so short and shows your long legs perfectly. Are those pantyhose? I thought so, well when you go shopping pick up some more stockings and garter belts. I love how sexy those are. You should really wear them whenever you can. Makes me hard as hell. I still can't believe you can make your boobs look so real and sexy. I can tell you like showing them off, just think what you could do if you had real ones? We've got to get yours done." With that, he turned back to his TV. I wish he'd give up on that breast enhancement. Made me cringe when he mentioned it. There was no way I could do that and make it every day at work. Let alone for the rest of my life. Driving the car in my heels was different. I was just glad I had a small economy car with an automatic. It wasn't as sexy as Bradley's Vette, but it was sensible. I had gotten a good deal on it, although the color, a light yellow wasn't my preference. Now, I guess it suited me better. At the store, it was fairly busy but I got a cart and started shopping without any problems. With my list, I just focused on it, and tried to look like I did this all the time. I was very nervous as I still felt so exposed in a dress. Plus none of the moms or other women had on hose or even heels. But the men seemed to appreciate my look, especially when I bent over to get something off a shelf. I was glad I had pantyhose rather than stockings. I had to reach a top shelf to get an item. The way I had to stretch, up on my toes, stockings would have shown for sure. I soon had most of my list done. But the hardest part was buying a couple of items, I knew I needed but didn't want to shop for. It took me a few minutes to get the courage to go down one aisle, set up for female customers, the feminine protection aisle. It had makeup, some hosiery, and all sorts of women only items. But I did it, selecting both a box of tampons and some panty liners. I also picked up some cotton balls, makeup removal wipes, and a bottle of nail polish. I looked at the makeup for a second. There were so many colors, styles, and brands. Before when I saw a woman in that aisle they would be there forever, it seemed. Now I knew why. Checking out went smoothly. Dressed as I was, there was no issue with my feminine items. The clerk had no problem with my signing on Bradley's card and the bagger insisted on helping me to my car. I'd been to that same grocery a dozen times, and they never offered. Today, the young man told me it was part of his job. He even refused the two dollars I offered as a tip. I guess this one of the benefits of being a pretty woman in a dress. At home, I hoped Bradley would help me carry in the bags, but his game had started and all he said is bring him a beer. I did, but only after putting everything away. Since it was a couple of hours before I was to meet Brandy, I gathered the laundry in a basket. That was the worst part of this apartment, you had to go to a central laundry to do your clothes. Luckily no one else was using the machines, so I could start different loads of sheets and towels, whites, and colors, each in their own washer. I figured if I worked it right I could get them dried and folded before I left. With the machines running, I went back to our apartment. I had left my hose and lingerie there. So I hand washed those in my sink and hung them up to dry. My mom and sisters had done that so much when I was young, I knew just what to do. By the time I finished my delicate items and got back to the laundry, my wash was done. I transferred them to dryers. Rather than go back up, I waited, taking the time to text Brandy to confirm our shopping date. She seemed pretty excited and asked what I wanted to buy. I told her, I'd need some lingerie, hose and maybe a dress or two. Her reply text, said she'd heard from Brad. He told her to be sure I bought more like five or six outfits. Plus accessories. Seems he loves how I've been matching my lingerie, dresses, heels and purses. I replied, we'd see. I mean, I have four outfits already. That would cover two weekends right there. If I bought another dress and a skirt outfit, I could easily cover a month. I figured he must have some crazy idea that I'd dress up during the week. Given all that it takes, I was going to draw the line there. Our deal was not specific about how much I had to dress. As I was texting, another girl came in. I'd seen her before around the apartments. She was pretty, but had never been very friendly. I guess I hadn't been her type. I was a little afraid she'd recognize me, so I kept my head down, looking at my phone. I felt awkward too, as she was dressed casually in Capris, a crop top, and flip flops. She had only a little makeup and her hair was put up in a loose bun. But she looked at me, with a smile. "You aren't using these washers are you? I need a couple." "No, go ahead. My things are in the dryers. I should be out of your way in a little while." "Your dress is cute. I love florals. You look too nice to be doing laundry. Usually when I get to laundry day, all that's left are my least favorite things. I look like a slob." "No, not really. You just look comfy, that's all. It's just that I had some errands to run and then I'm meeting a friend to do some shopping. I'd rather be dressed casual like you, but it made more sense to stay this way once I was dressed." "My name's Valerie by the way. I've not seen you around the place before. You just move in?" I was getting nervous now. I always worried when I had to talk for a while with someone. That I'd slip back into my male voice and speech. Or in her case, she'd recognize me. But I just smiled. "Yes, I'm new here. My name's Cashmere." "Well hello and welcome. There aren't many women here, mostly guys. It's nice to see another girl here. Do you have a roommate? I live alone, in one of the single apartments." Now I was really getting nervous. I was trying to think of what to say and how to phrase it. I knew when I took my clothes out of the dryer, she'd see men's and women's things. So I had to be careful. She looked at me, waiting for an answer. So I just told the truth, or what would look like the truth. "I do. I moved in with my boyfriend. My first weekend here. I have another place, with a girlfriend, but I guess I'll stay with him, at least on weekends." "God, I wish I could meet a nice guy. All the ones I run into, either want a one-night stand or just want to be 'friends with benefits'. You know what I mean?" "Yeah, I know. It's hard to find someone. I mean you're so pretty, I'd think you'd meet someone nice." "I guess, not lately, but there's always tomorrow." Luckily she turned to put her things in the washer. I went back to my phone, as Brandy sent me another text. In a few minutes, my dryers stopped, so I got up and began to sort and fold my things. It made me glad that I'd told her I had a boyfriend, as it seemed most of the things were either Bradley's or my male stuff. It clearly looked like I'd only been there a weekend. Valerie watched, sort of out of the corner of her eye. When I had my stuff in the basket and was ready to leave, she looked up. "Maybe I'll see you around. At least in here. I don't know why, but men seem incapable of doing their own laundry. I hope your boyfriend appreciates you for doing his." "Oh he does. Bradley pays for most of our things and is real sweet." As soon as I said his name, I realized it was a mistake. But I tried to act casual. "Besides, most of my stuff is hanging up in our bath drying." We both laughed at that, as she knew what I meant. Even though it seemed harmless, I wanted to get back to our place. But she didn't let go. "Is he the tall guy, dark hair, drives a sport car. Lives on third floor right?" Shit. "Yes that's him. You know him?" "No, but I thought he had a male roommate. I've seen him go out and come back with another guy." "He did. For a while, but Bradley said he had to move. So, when he suggested I could stay, I thought I would. Well got to run, see you later maybe." I walked out, mad at myself for reveling too much. I was worried she could tell I was the male roommate. Anyway back in our apartment, I put away our clothes, his in his closet and dresser. I was a little more torn about mine. For now, I put my male stuff in the bags on the closet floor. I was still unsure how my week would go, so I would need to play it by ear. But I was already late, so I said bye to Bradley and headed out to meet Brandy. Driving there, I was getting increasingly more nervous. The first day had been hard, but it was so scripted I had no choice but to go along. Now, it would be me, trying to find what women's things appealed to me. Actively selecting, trying on perhaps, and then buying items that would reinforce my current status. I was torn between wanting to end it all or continue doing what Bradley wanted, just to satisfy him. I had already appreciated being able to buy all that food at no cost to me. The rest of the weekend had been the same, I had spent nothing. But I had sacrificed my self-image as a man to get it. I found it hard to resist now, since I had already submitted multiple times to his desires. I got to the street and found a parking spot not far from Amber's salon, where we were to meet. I headed there and found her and Brandy chatting. I was glad, in a way that Brandy had dressed. It felt like today should be a girl's day. When I came in, they both turned and greeted me. "Hello girlfriend. Nice outfit, if I do say so myself. Come here, let me check you out a sec. Did you redo your hair? Looks good." Amber was very chatty and Brandy piped in to, they were both happy that so far everything was okay with my weekend. Brandy bragged about how sexy I looked last night and how taken Brad seemed to be with me. She told Amber, he had texted her insisting I buy at least six outfits. Plus a special request. I gave her an odd look. "Special request? What do you mean?" "Pretty clear, he loves you like these. He asked if Amber or I knew any good plastic surgeons. He was sure you'd be wanting a breast enhancement, probably the sooner the better. He even offered me a bribe a sort of finder's fee, if I was able to help." "Oh my word. He is crazy. This is a weekend lark, at most. I mean it has been such an eye opener, in so many ways. I have to admit I've passed, mostly, better than I expected, far better. But still, I'm a guy. I have to go to work tomorrow even, as a guy. So anything like he's talking about is more fantasy than real. In fact, I wanted to ask you, Amber if I could buy a nice wig, maybe later this week. As good a job, as you've done, I'm going to have to cut my hair just so I can go to work. If Bradley wants a girl on the weekend, I'll do that to keep the deal I made, but I can't be a full time one. That's why I don't understand his insistence on so many clothes. Does that make sense to you two?" "Cashmere, if men want to buy you nice things, you should just let them. I mean, we give them enough anyway, so if it makes them feel good, what's the harm. Besides, you can never have too many clothes, right Brandy." "Honey, I take whatever that man wanted to give me. Just keep him happy, most guys want to sponge off you. As far as any enhancements, I do know a good surgeon. I got an opinion from him, on what he could do for me. It was free and really fun. They take a photo, of you naked from the waist up. Then do a computer image kind of thing and can show you photos of what you'd look like with different size breasts. Truthfully, that's one reason I bought the bigger forms. Now I couldn't afford the operation myself, but again, if Brad was paying, sign me up." "I understand your points but still, I don't know. He has asked me to buy a few things, so we can get those and I guess if I buy an outfit and don't need it, I can return it, if I haven't worn it right?" "Sure, so you've nothing to lose. Brad did tell me he wanted your ears pierced. I can do it now if you want. Won't hurt or take long. I like guys with earrings, whether they dress or not. I've got simple posts too, nothing too feminine for work. Like the extra dresses, you can take them out if you don't like them and your ears will heal. But I'm sure you'll love them. Come on back." I was hesitant, as this was another step I hadn't expected to take. But it didn't take Amber long to pierce my ears and it didn't hurt. She suggested two in each ear, and since she'd been right about most of my conversion, I agreed. I had to admit, with my short hairstyle, they looked good. She told me in four weeks or so, I'd be able to switch to any kind of earring I wanted. While she had worked on me, Brandy had laid out our shopping plans. Bradley had told her that I needed a few more sedate dresses, not overly short or too low cut, but pretty. A couple more skirts would be nice too, with feminine blouses. Amber had some suggestions too. She thought I should have a couple more lipsticks and a variety of eye shadows. We looked at her selection and picked a few. Both of them kidded me when I told them Bradley had added me or at least Cashmere to his card. Amber had to work, so Brandy and I made the rounds of stores along the street. It was actually fun, trying on different outfits once I got over the initial anxiety of undressing in the change rooms. Having Brandy to bounce off ideas or opinions on an outfit made me feel better about each one. Somehow, it was easy to buy outfits that weren't so sensationally sexy. Having a flowing dress that went to my knees, or a scoop neckline that only revealed a hint of cleavage seemed more like something I could wear and not look like a hooker. In the back of my mind too, was Bradley's request I wear more stockings. Longer skirts would make that easier. I guess I had in mind that a typical weekend would probably be more like today. Going to a store, running errands and doing laundry or housework, then finishing by eating out or cooking him a nice dinner. So when we were finished I had four more dresses, three skirts, two blazers, and five blouses, with which I could make over ten outfits. Of course, Brandy insisted I get more shoes and despite some desire for flats or lower heels on my part, I wound up with a half dozen new heels, in both pumps and sandals, none with a heel lower than four inches. Included in that was a pair of slides with a cute lace bow on front. I knew it was just what Bradley asked for to wear with my nighties. Purses that could coordinate with multiple outfits added more flexibility to both my style and look. The final stop was the lingerie store. Here I didn't really try on anything, as I knew my sizes pretty well. But this was the place it was the hardest to keep from buying too much. Brandy loved it when she heard Bradley had requested more garter belts. So we started with those. She thought I should have both different colors and looks. So we got a couple that were only garter belts, something she called a waist cincher, and a pull-on open body shaper. The last two came in lovely colors with lace trim or panels. She even persuaded me to buy a garment that had a built in bra, sheer body panels and garters. Of course, we bought panties and bras to match many of my new items. I also gave in and bought a couple more nightgowns, one a sheer lace chemise and another baby doll with thong. The last selection included more stockings as well as a few more pantyhose, for practicality. When we were done and had taken everything to my car, I started to panic. I was worried I had gone too far, spending too much money. I decided to call Bradley. I actually cringed when I told him how much I had spent. But all he wanted to know was if I bought more stockings and did I have plenty of dresses? Once I told him I was good, he said that it was fine by him. He told me couldn't wait to see me, plus he thought we'd go out to eat once more, before our holiday was over. When I got home, he had changed into something more appropriate and actually helped me bring in my purchases. The hard part was fitting it all into my closet and dresser. The only way to make it work was to remove more of my male clothes. I'd have to figure something out, as I was left with only a couple of pant and shirt combos I could wear to work. Maybe I could buy some sort of standalone wardrobe for my male things, just big enough for five days' worth of clothes. I'd talk to Bradley about it at dinner. He had another new restaurant in mind. When I told him, I wanted to freshen up before we left, he asked if I could change my hose? I reluctantly agreed, since he was being so generous with his money. So I touched up my hair and added to my makeup to create a more dramatic evening look. I thought my dress was okay. But I did replace my pantyhose with a sexy lace garter belt and dark stockings. The dress was short, so I'd have to be careful. But I did a little twirl, and actually like the way you could see the stocking tops. A subtle but sexy look. My final touch, was to put a liner in my panty. I was pretty sure Bradley would do something to make me leak again, so I wanted to be prepared. As we were leaving to go eat, I saw my new friend, Valerie. She waved and said hello. I could see she thought Bradley was good looking, as she flashed me an okay sign as we walked away. He wanted to know who she was and was pleased when I told him how I had made a new friend. The dinner started out nice, real nice. It was a small Italian place, with candles on the tables, low lighting, and soft music. After sort of taking advantage of me today, Bradley was back to his charming self, full of compliments and engaging conversation. He asked for details about my day, what Amber and Brandy said, and even told me, he should take me shopping for some jewelry. He liked how my earrings flashed when I turned my head and admitted he'd overlooked that detail in my outfits. When he brought that up, I decided I needed to talk about how we would do this going forward. "Bradley I have to admit you've been so supportive and encouraging about this whole dress up thing. I was afraid it would be a humiliation where you were teasing me or putting me in awkward positons. I mean, there's some of that, just being intimate with you is something I never imagined and honestly, haven't quite come to terms with. But overall I guess I can handle it, if we do it this way. I figure we can limit it to weekends. But that means we have to dial it back at work, during the week. For example when we get home, I'm removing my nail polish and trimming my fingernails. Plus I have to use some trimmers to cut my hair into something more suitable for a man. I figured I could get a wig from Amber by next weekend. I'm sorry to limit this role play this way, but it is the only practical option." I waited for him to protest or even explode with an angry counter argument. I mean he'd just spent several hundred dollars on me. But he was calm, almost as if he didn't hear me. He was even smiling and took another bite of his linguini and drank some wine before he responded. "Cashmere, I understand your worries, I do. But I think you've overreacted. As well as underestimated me. I knew you'd face a problem like this, so I designed a workable solution. In reality it was the only solution to numerous problems that have been surfacing the last few weeks. You know how much management is putting on this project. They literally are counting on it to save most of the company. The profits at the main facility have narrowed so dramatically that without getting this site on line in record time, the company might fold. So to make sure we can achieve that I was able to get some concessions from them. Those will make all of this much easier. First, and this is hard to tell you, but I need better engineering work than you can give me. Your job should really be filled by a senior engineer, who has more experience and skills than you. If we had someone more qualified then we could almost double the pace, since he could deal with issues by himself while I did other work. Management already recognized that and we've talked about making a change. We've agreed that Tom Hartley would be assigned here. That would mean you would go back to the main site. Only they don't have a need for you there. So, you'd be let go. Sorry but it's true. But secondly, I was also able to convince management that one other aspect of our job that is killing us on schedules is all the paperwork and documentation that is needed. You know that we spend easily a third of our day doing those kind of tasks. That would only get worse if we added another senior engineer since the work pace would increase. So as part of the reorganization here at offsite, they agreed to let me hire an administrative assistant. That's where I got creative. So the final part was filling that slot. Remember yesterday, when we did that paperwork to fax to the main site? I had you co-sign several forms in the package? Well, I wasn't quite straight with you on what all was in the package. The top copy was a purchase requisition but the other forms were termination papers. Officially then, Friday was your last day. I know, it was deceiving and mean, to do it that way. But hear me out. They had told me to fire you before bringing Tommy here. So it had to be done and it has. You no longer work for us. Which means you'd have to leave the apartment and go, try to find a new job. That's where the creative part comes in. I also had you sign a form with your new name, Cashmere May. I told you it was just a visitor's log in case the guard checked up on us. But it was really an application form, for the admin assistant job. Home office now has a request to hire a well-qualified young lady for the positon. Someone familiar with the project, with engineering background who can understand the terminology, and who has already been recommended by the project lead, me. So tomorrow when you head to the plant, you're going to go to HR first. There you will have a brief, perfunctory interview with the head of the administrative support group, the lead secretary so to speak. She's going to make sure you're familiar with proper document prep, phone etiquette, dress codes, and all the rules and regulations of the job. I imagine she'll want you to take a few in-house classes and attend their weekly secretarial meetings, after you start. But once you two talk and she sees you can do it all, then you'll fill in an acceptance sheet, sign it, and be my new office girl. So all your worries about these clothes and your feminine look are solved. You can continue to live as a sexy and pretty girl, all the time. I even was able to get Janet to help. You know she works in computer tech at the main site. So Tuesday, once your termination is official, she'll make a small change in the social security listed on the termination file. So your new application, with your real social, won't trigger a conflict when they enter it into the system on Wednesday. Work setup will be easy too. Just move your things from the office to the entry space. That desk will be yours. You can handle the machines there, greet anyone coming to see me or Tommy, answer phones and fill in all the paperwork for us to sign. I'm sure you'll love it and do a great job. You may not have all the engineering ability the job needs but I'm sure you'll make more than a capable secretary. Plus be probably the prettiest one at the plant. I thought of everything. Including Tommy, he's dying to meet the new you. We figure, he can take the third bedroom in the apartment and fit right in. I've already told him how good you are, how you enjoy sex so much, so I bet he'd be open to it too. That's one reason Janet liked the idea. She knows I can't limit myself to her visits once every couple of months. I need some kind of sex in between. She didn't want me going to hookers or trying to find some local girl. So knowing I'm with someone sexually who's safe, clean, and not looking to take her place as my real romantic partner, is fine with her. It will be even easier if you do the same with Tommy, not such a one- on-one relationship with me. More like roommates with benefits. Something to resolve our boredom issues. Knowing how horny you are, how much you like sex, sucking cock and being fucked, having two men to take care of you will be like a dream come true. It always amazed me that you never had any dates with women since I've known you. I mean you've actually met more women this weekend than since I met you. So given your failures as a man on the love front, getting it all the time from me and Tommy should be a real bonus. Plus for me, Tommy has agreed to share all your costs, new clothes, makeovers, food, and drink, everything. He even likes the idea of you getting breasts. He told me, he'd gladly pay for those all himself. So for you and me, this is a perfect solution. At first when I made the proposition, I figured you'd say no. It would make you mad, I mean what man would do that just to save some money. I hoped you might even quit, so I wouldn't have to fire you. I mean you were a nice guy and all. I hated it that you couldn't cut it as an engineer. But then you agreed, caught me off guard. I did think it was just going to be for the weekend, a way to end your time here. But you were so eager, so hot that night, in bed, and so good at it. I changed my mind, started looking at other options. If you hadn't been so willing, so accepting of the role of a sex kitten roommate, then I would have never even imagined this. Now I see it as the perfect solution. I mean I really liked the challenge of this project but being away from Janet and my best friend Tommy made it hard. Now I have solved all those issue, avoided the boredom of an offsite appointment, and saved your job too. So I want to celebrate tonight. I was thinking we go up to the lookout point. I bet it's lovely at night. I can't wait to spread you open on the hood of my Vette and fuck you. How's that sound?" I was looking down at my plate. When we ordered, I thought about how I looked when I was trying on new dresses. I was a little pudgy around my waist. So for dinner I ordered the small ravioli and only ate two and just half of my breadstick. I was going to take the leftovers for lunch tomorrow. At the plant. Now I just played with them. Then picked up my glass and drank some more wine. Trying to keep it together and comprehend what all Brad had just told me. I couldn't even look at him. It was hard to hear I was a failure as an engineer. That I was so bad, I was going to be let go, and replaced by Tommy. He was a jerk and had always made fun of my two-year technical degree. That I would have no job, no place to stay, and nowhere really to go. It had taken me over six months to get a job at the plant. If they wouldn't keep me who would? Hearing how I was a failure at dating hurt too. Mostly because it was true. I had only three girlfriends in my life and only had sex with two of them. Both relationships ended quickly after the first and only time we had sex. It was clear I wasn't satisfying to women as a man. But to hear it put so bluntly hurt. It also was a punch to the gut to know Bradley thought I would enjoy remaining as a girl for sex. It was hard to hear Brad say he never expected me to go along with dressing up to save money. But when I did he played along, for sport it sounded like. Only I was such a slut, so eager to please him, that he changed his mind. So much so, that he manipulated everything to keep me here. Keep me as his 'roommate with benefits'. For him and that jerk Tommy. I could imagine having to please both of them sexually. Plus, be their maid too. I'm sure both would assume I'd love to clean, cook, and wash their laundry, as much as I'd liked fucking and sucking them. How could I have been so eager, so sexy that night? I had no recollection of that at all. That kind of feeling and desire, never came back, either. Unless leaking pre-cum into my panties counted. But how could I argue with the way Bradley put it? I'd already sucked him three times and been fucked more than that. I pushed the food around on my plate and took another sip of wine. Finally I looked up at Bradley. What I saw was the only option I had. I swallowed my pride. Given my choices, I had to be practical even if it wasn't what I really wanted. I mean, after a year I would have some money so I could make a choice then, whether to be Cashmere or Patrick. "Sounds hot Bradley. I appreciate you taking care of me like this, I mean I don't know what I would have done otherwise. With no job, no place to stay, and no prospects either. But it takes a long time to get up to the point right? How about letting me have some desert on the way? That way you won't get bored and you'll last longer when I'm on your hood. Oh by the way, Brandy texted me earlier. She got me a consultation visit with her doctor on Wednesday afternoon. You think I could have off from work to go see about getting my augmentation? If I did it soon, then you and Tommy could reap the benefits sooner too. Wouldn't that help keep away the boredom?" Bradly didn't answer, but put his hand on my leg, sliding it up until it reached the top of my stocking. Tugging on the garter, he leaned in to kiss my cheek. Smiling, he nodded his head. "Yeah I think we've solved our boredom problem for good."