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Ever since I started working from home, Carla seemed upset. She still had to drive an hour to and from work, plus she wasn't that fond of her job. On the other hand, I could just roll out of bed, get some coffee and sit down with my laptop and be on the clock. Of course, working from home paid me less than before, but I really had no other options. My company downsized a whole branch, eliminated the location in our town, and just offered a lucky few the opportunity to remain with them as customer service reps. In other words, I spent all day either answering online questions or calls from customers, generally angry customers. But since I had designed some of the electronic components, I usually had good answers for their complaints so that by the end of the call, they were happy. What I liked was that I could choose what length a shift to work, and when, as long as I got in my weekly assigned hours. Since the company sold all over the country, they needed CS reps just about any time of day or night. The other part that I liked was I no longer had a required dress code for work. So, it was jeans or sweats and a tee-shirt most days. Plus I could finally let my hair grow out again. When I was a teenager and in college, I kept it long, down to my shoulders. But when I graduated and took a job, I cut it off. So now I had a chance to go back and I really liked it. Unfortunately, Carla didn't. She met me after I was working so had never seen me with long hair and wasn't particularly in favor of that look. In fact, almost every time she saw me with my hair down she'd make some negative comment. It bothered me, but I tried to ignore it, figuring it was partially related to her job situation. As I saw it, my long hair reflected my new work from home job in her eyes, because I didn't start letting it grow until I had my situation had changed. I reasoned she would become accustomed to it and the comments would stop. Until then, I just let her vent. So when we sat out on the porch for a drink before dinner and she started to comment I let her go on. "Phil, you need to get that hair off your face. I can hardly see your eyes or expressions to talk with you. I know you like it but it irritates me seeing it hanging there looking so sloppy. Although I have to admit, since you've started working from home you've stepped up in taking care of our house. It seems you see the need for it to be neat and clean, so I wish you'd do that for your hair." "Thanks for noticing all my hard work around here. You know it wasn't my idea to work from home, but I did realize I could do more housework and allow you to get back some of the free time you lose by commuting. As far as my hair, it's clean. I shampoo regularly and always comb it. What else I'm I suppose to do?" "Well if you're going to keep it long, you need to spend more time taking care of it. For starters, you should condition it every time you wash it and with the length it's getting to you should probably use some kind of styling product on it too. If it was my hair, I'd put some wave or curl in it to lift it off my face. You know, you could do the same too. I'd be glad to show you how, if you'd let me." "I don't know, I never did anything to it when I let it grow out before. Why now?" "Well you didn't have a girlfriend back then either. Now that you have a wife, whose opinion should be important to you, you might need to consider doing something to make it look better." "Tell you what; I was going to wash it tonight. Do you want to help me? You could show me how to condition it and maybe even use something to style it." "Sure, if you'll let me do what I want, I'd be glad to help. I can see you're adamant about keeping it long, so I might as well help you make it look presentable rather than just griping." So after dinner, when I went to wash my hair, Carla helped. She added conditioner and as we let it soak in, she explained how and why she used a few of her styling products. Her hair came down past her shoulders and she wore it with bangs and a wavy style that kept it to the sides of her face. After she washed the conditioner out of my hair, she looked intently at it, as if she were weighing options on what to do. Then she combed it out, giving me a side part rather than my usual center part. Next she applied some styling gel, took her hair drier and worked on it a few minutes. Once she had it mostly dry, she picked up a curling iron and started working on the bangs she had created with the side part as well as the longer strands near my face. I was a bit nervous about her using her hair dryer and the curling iron especially. But I figured I could endure it if she would be more receptive to me having longer hair. Finally she sat back, used her fingers to position some of the curly strands and lightly sprayed it with hair spray to keep everything in place. Looking it over, she smiled. "Now I can see your face. maybe that's what made me unhappy with your hair, now that it has a bit of style, I kind of like it. Before you looked disheveled but now, it looks neater and more appealing. Take a look, and tell me what you think." She moved away from the mirror so I could see my reflection. The change was striking, although it wasn't something I would have chosen. My hair did look shinier and wasn't just hanging off my head. She had put lift in it, so it gave an airy, fuller appearance and not plastered down. But she had also added loose curls to give it a decidedly feminine style and the spray kept everything in place. The way it was curled did move the hair off my face, but at what price? I would have said my hair was a girl's look now. It was kind of funny, because I always thought of myself as having a rough face, but with the way she styled my hair so it framed my face I could see a bit of a woman's look to it. I mean my nose wasn't big, my skin was smooth with only a light beard which was blonde, and my lips were full. Even my eyelashes were longer than most men. In total, with my curls I would have assumed I was looking a woman. I was torn now, because I wanted Carla to like my hair but was it worth this look? "See what I mean, it looks much nicer now, doesn't it? Not that you have to spend this much time on it every day, but if you just used the curling iron to help your bangs stay back off you face it would be a big improvement. In fact, I really like how you look, pretty sexy to me." Without even giving me a chance to respond, she leaned in for a kiss, which I reciprocated. She continued to kiss me aggressively and ran her hands over my chest. She started unbuttoning my shirt and pulling it off. With me shirtless, she grabbed me by the arm and took me to our bed, where she pushed me back on it while she pulled off my pants and underwear. This was totally new for us. Carla never initiated sex and was never aggressive when we did. With me totally nude, she knelt between my legs playing with my cock. Of course it responded and when she had it hard, she began to kiss and lick it. I lay back, thoroughly enjoying this surprise. I always thought she was good at oral sex, but she was generally reluctant to give me some. But tonight she was eager, taking in as much as she could, running her tongue over it, and even sucking my balls. Finally she brought me off, swallowing as I finished. But she wasn't done yet. Carla continued to play with me until I was hard again. This time she quickly stripped off her clothes and crawled on top of me. With her in the dominant position, she guided me into her pussy, which was very wet. She rode me to another explosive climax, coming with me as I came a second time. This was great, easily the best sex we had in the past year. After we came, she snuggled next to me and we relaxed, semi-napped, intertwined for a while before she spoke up. "Wow, I missed that. You looked so scraggly before that I had no interest in you. But seeing your hair tidied up, reminded me how cute you could be. I know it is a bit more work for you, but don't you think you could keep yourself a bit neater for me? I'm certain there would be decided benefits for you, and me, if you did." We kissed again as she lightly played with the curls around my face. It was hard to argue that I didn't like what had just happened. Maybe it would be worth taking some extra time with my hair. I mean, I couldn't even remember the last time she went down on me, let alone let me come in her mouth and swallow it. So what, if doing my hair made me look a little feminine, it's not like I had to go to work the next day or anything. I imagined if I pulled it back, it would look more or less the same anyway. So I let her know I would be willing to invest a little more work on my hair if it made her happy. But she would have to show me what she wanted done, unless she was going to do it every time. She said she really did enjoy doing my hair, but she could show me some simple things so she wouldn't always need to do it. The next few days were really a change. It seemed like she actually looked forward to seeing me and we spent a lot of time together. She showed me how to do my hair with the dryer and curling iron, what products she thought I needed, and a few different ways to put tight and loose curls in it. The part I liked best was we always followed it with sex. I mean, it had been years since we screwed that often in a week. So whatever misgivings I had about making my hair look nicer with a bit more style, even a feminine style, were easily dismissed. By the weekend, I was open to about anything she wanted to do. Her request that I trim back or shave more of body hair seemed reasonable, since I knew I hated to get hairs in my mouth when I went down on her, so I understood her complaint. Plus as she pointed out, I was not very hairy, most of it being in random patches and so light blonde that it didn't appear noticeable when it was gone. It was hard to argue with someone who's stroking your cock, keeping it hard, so she can shave it smooth and then when it is, goes down on you. By the time she was done, I had only a symbolic, small triangle of fuzz above my cock, being smooth everywhere else. The next couple of weeks, we did similar stuff. During the week, I'd do my own hair and on the weekends, she did it for me. She enjoyed trying new looks, including having it pulled back with barrettes, working up lots of curls, braiding it or even pinning it on top of my head in an sexy up-do style. She also surprised me by shaving herself smooth, something she had never done. I was more than willing to kneel and bring her off with my mouth and tongue, which would lead to fucking. But after the first time, she insisted I wear a pair of her panties, as I tended to drip pre-cum as I worked her over. I questioned wearing her things, but she just said it looked cuter and sexier than guy's dull briefs. Again, with my sex allotment gong sky high, it was just another small adjustment that was easy for me to make. That seemed to be a pattern for her, she asked me to try something and then reward me with sex if I did. Wearing lipstick, so we could kiss and feel our lips sliding against each other's, keeping her panties on all day on the weekend so she would be thinking about me looking sexy, or allowing her to use her perfume on me, all of these steps seemed small and insignificant in comparison to our expanded sexual activity. Plus she had totally stopped complaining about my long hair. Now she complimented me all the time, saying I looked cute, or my legs were sexy. Having me do my chores in a pair of her short shorts led to a wild afternoon of mutual oral sex or going to bed in one of her frilly baby dolls resulted in a long night of multiple orgasms. No, so far there was nothing she had suggested I do, that I didn't feel was worth any potential consequences. Her most common request was for me to get 'dolled up' as she called it, while I did my household cleaning. She told me repeatedly how much it meant to her that I took over that duty from her. So when she asked if I still planned on my monthly intensive house cleaning on Saturday, I told her yes. I liked to hit it hard on the first Saturday of each month, so it sparkled. That way the weekly chores would be lighter and it still looked nice. Hearing that I was sticking to my plan, she had a request. "Phil, I've really been thinking about setting your hair using old- fashioned rollers. That kind of set gives you much more body that lasts and lasts. So I would like to wash your hair on Friday, put it in rollers while it's wet, and then you can let it dry overnight. That's an approach I used a lot myself before we married. Having your hair in curlers that long really gives it curl and you have so many options for styling it. If you agree, I'd style it for you first thing on Saturday morning and you'd look cute all day doing your housework. I think you know how that would motivate me for that evening. What do you say want to let me try it?" This seemed like an escalation in the process, so I was a little hesitant. But so far everything Carla had suggested had been great. She had been able to solve issues that had been causing problems between us and in fact we were closer now than ever before. I know the sex was certainly better. So what the heck, I told her I could do it, if she wanted me to. "Oh Phil, I love this new side of you. I really appreciate your willingness to try things for me. It makes me horny just thinking about it. Why don't you go take a nice bath, shave everywhere real close, and then I'll come in and wash your hair for you. I want to give it a deep conditioning treatment before I roll it up." After I was smooth and clean, Carla came in to do my hair. It was luxurious to have someone wash your hair and massage your scalp. Totally relaxed, I got out and dried off. She insisted on applying lotion all over me, before I dressed in a silky soft nightgown and slippers. I sat at her vanity looking in the mirror at her, while she carefully applied the rollers. The first few felt a bit tight against my scalp, but I loved watching her spray a section of my hair with holding lotion, tightly wind it around the curler, and then clip it firmly so it would hold. It took longer than I expected as she did every bit of my hair using either medium or small size curlers. Once she had it all done up, she pulled a bonnet in stretchy pink fabric with ruffles over them to hold everything in place while I slept. The whole time she worked on my hair, I had a rock hard erection that my panties could barely hold back. I could tell she was excited as well. Not unexpectedly, after she finished, she slipped off her pants and panties, positioned me between her legs kneeling on the floor and had me lick and kiss her to orgasm. While I serviced her, she babbled about how hot it was to feel my rollers brushing against her thighs as I pleased her. The only disappointment for me was her insistence that I not orgasm, as she wanted me hot and horny while I worked tomorrow. She promised me more surprises and an evening to remember if I agreed. Of course at this point I went along with her. Sleeping was a bit fitful, both because of my unfulfilled sexual desires and the uncomfortable feel of the curlers tight against my head. It took a lot of tossing and turning to find the right position where I could fall asleep. I must have gotten some sleep, because Carla had to wake me the next day and it was already 10 o'clock. She gave me a cup of coffee and asked me to shave my face so I would be smooth for her. Finishing that and my daily preparations, I re-entered the bedroom where she was waiting for me. She had already dressed, wearing skin tight skinny jeans, a low cut top and flat sandals. Lying on the bed was a silky sheer pair of lace trimmed thong panties in a bright coral. It was not unusual for me to wear silky panties now, but there was also a matching camisole with lightly padded cups. It was obvious she wanted me to wear both. I questioningly looked at her, but she just smiled. "Phil I bought you a few new things I want you to wear for me while you clean. I've loved how sexy you look when I did your hair before. You looked hot in either panties or your nightgowns, so I want to extend that look for more daytime attire you can wear for me around the house. Since you agreed to let me give you a full woman's hair style using the curlers, I don't see any reason you can't let me finish the look. I have a whole matching outfit for you and I want to try out a bit more makeup than just your lipstick. I have the feeling that seeing you this way will pay big dividends for you later. So slip on your new undies and come sit down at the vanity so I can do your hair and face. I know you have a lot of housework to do and since I let you sleep in, we need to get you ready." "You never mentioned more makeup, is that really necessary? Plus if you want me to wear something sexy, can't I just keep my nightgown on? I really don't know about going further with this." "Phil don't be such a party pooper. You've loved everything we've done so far and if you agreed to let me do a complete women's hairstyle, it would be silly not to take it all the way. Besides I've already got your new clothes so just relax and enjoy it. I'm sure after tonight you'll agree it was all worth it." Carla emphasized that the discussion was over by picking up the camisole and helping me put it on over my head, negotiating the curlers took both of us. She commented that next time, a simple bra would be better and easier to put on. While she watched, I slid the thong up my legs, reflexively tucking my cock and balls as it settled in my crack. With the sheer fabric, the thong made my front look just like a girls. I looked at my reflection in the mirror over the vanity, and could see that the padding in the camisole although minimal did create a change in my profile. The slight increase in my bust stood out against my smooth stomach now encased in the sheer lacy fabric. Carla wasted no time and once I was sitting at the vanity, she began to apply the cosmetics. I had hoped it would be just a few things, but it was clear she intended to fully makeup my face. She was quite good at it, and it really didn't take that long for her to apply a foundation in medium beige that matched my skin tone. The feel on my face was like a lotion that didn't soak into the skin and the thin layer evened out all of my skin tone so that it looked smooth. With the base complete, she quickly added blush across my checks, eye shadow in two shades across my lids, put a little color in my brows to highlight them, followed by multiple layers of mascara, before she finished with both lipstick and a shiny gloss. Most of the cosmetics were noticeable only by feel or smell, but the mascara so emphasized my lashes that they were highlighted in my vision. It would take some practice to get used to that. I had adjusted to the feel and taste of lipstick, so I hoped I would not be bothered by the new items. I had to admit the cosmetics really altered my image. I didn't have a gorgeous woman's face, but it was more feminine than I had guessed it would be. Carla practically beamed when she was done. "I knew you would look cute. I love how your eyes look so much bigger and your lashes are so long. You're a natural for makeup. You really should wear it all the time, especially if you're going to style your hair. Next time, I'll start showing you how to apply everything. It will be so much fun, just like when I showed my sister Donna how to do her face, only yours looks much better." "Carla, I don't know about that. Once will probably be enough for all of this. I mean it's not like I'm going anywhere. Plus makeup is a girl's thing not really for men." "Oh don't be so old fashioned. Some say that long hair is just for girls too, but you've convinced me it is the right look for you. I'm positive that once you play around with makeup and try different looks, you'll find one that suits you. And if it takes going out to make it worth it for you to wear makeup, I can arrange that too. Anyway, let me take the rollers out, so I can style your new hair-do and then you can get to your chores." Carla began to remove the curlers, and I immediately noticed how much more curl my hair had with these compared to a curling iron. Each curl bounced back tight against my head when she unrolled the curler. When she had them all out, she used her fingers to loosely shape them, and they relaxed a little. She took a hair pick and lightly gave me a side part, and positioned my bangs. Once she had the curls where she wanted them, she applied hair spray to keep it all in place. Again, I could see she was happy with how it looked, as her face was beaming. "Phil that looks so good on you. I knew rollers were the best option for your hair. The good thing is, we can do lots of styles this way. If I brush it out or back comb it, we can create a range of styles, including sexy big hair looks, to loose curls that give the impression of a more casual style. I think the best approach will be for me to show you how to get these styles and then you can do it for yourself. Once you can do your own makeup and hair, you can look this pretty all the time. But now that you're ready, let's finish getting you dressed. This is a work day after all little girl." She went over to her closet and took out a couple of clothing items. The first one she handed me was a sheer camp shirt in a light green with large pockets in front and rolled up sleeves that came to the elbow. I slipped it on, and saw immediately that my camisole was visible through the sheer fabric. The patch pockets on the front lined up with my padded cups to create a bit more of a bust. Once I had the blouse on, she handed me the matching bottom. It was a skort design- looking like a skirt in front but shorts in back- that zipped up the side. The fabric wasn't sheer but it had the same color green as the blouse with a coral print design. I pulled it up to my waist and closed the zipper. The legs were very short, and it fit tightly across my ass. While I was putting on the clothes, Carla had gone to her closet and brought out a pair of sandals with a ? inch heel. They had a thong strap in front trimmed with coral beading to match the short design. Once she saw these on me, she said we had to do my nails as well, since she had a lovely shade of coral that would be just right. I was getting more and more nervous, as I now had a completely feminine look. But at this point, she wasn't taking no for an answer and soon I had shiny finger and toe nails in a soft pastel coral shade. She added a necklace and bracelet with the same coral beading as the sandals and a delicate gold anklet. Stepping back, she made me pose for her. She seemed thrilled with how I turned out. "Phil you are just darling. I thought you would look good, but it all seems so perfect. You are almost too pretty to do housework, but then again someone has to do the wifely chores. Be sure to use the rubber gloves when you scrub the bathroom or kitchen fixtures, as I don't want you to ruin your manicure. 'll let you get started, while I read the paper but I have one last little surprise." She went back to her closet and returned holding a small piece of clothing in a light coral. Handing it to me, I unfolded it and saw it was a little half apron. It was sheer with a ruffle and an embroidery vine in light green around the hem. I could see immediately that it matched the rest of my outfit, so I tied it around my waist. It wouldn't offer much protection for my clothes, but it did have a symbolic impact, making it clear that I was the house cleaner. Knowing that I had a lot to get done today, I began my work. The first chores were to start the laundry and clean the bathrooms. Fortunately, I kept on top of most of the house during the week, so there weren't any disastrous messes to handle. It was different though. Noticing the sparkle of my nails as I moved around, feeling the tight but still comfortable grasp of the skort across my hips, the way my seemingly long and smooth legs emerged from the ruffles of my apron extending to the pretty toes in the ornate sandals, and seeing the small mounds on my chest, all made me realize what a feminine presence I had. But what really sealed it, was when I saw my reflections in any mirror or shiny surface in the house. My hair was a gorgeous mass of curls, appearing soft and fragile, but held in place by the hair products. Matching that was my delicate looking face, a presentation I had never imagined possible for me. Carla had used just enough makeup to highlight it, giving me alluring eyes, prominent cheek bones, and making my lips so inviting. I almost blushed looking at it, because it was so obviously female that it seemed like I had surrendered my masculinity. To avoid these feelings, I tried to focus on my cleaning, but every time I passed a mirror, I had to stop and look. My fascination with my new look, was not lost on Carla. I saw her catch me more than once glancing at my reflection or studying the way the camisole gave me a bust line. That did make me blush, as I wasn't sure at all, I wanted her to know how appealing this look was to me. So again, I plunged into the house cleaning with renewed fervor. I decided the best way through this was to work and get to the end, where I would be sexually rewarded by Carla for my full foray into femininity. I had almost finished the list of chores and at first barely heard her on the phone. But as I took the last load out of the dryer, I distinctly heard her chatting with a friend, from the conversation, likely Diane, one of her best friends. Diane and I didn't exactly get along, but I put up with her because of Carla. Diane had a way of needling me that got under my skin. That and the fact that she was nearly six-feet tall, towering over me, made every encounter a test of my patience. Diane liked to reference our height difference whenever she could, giving me nicknames like, short-stuff, mini-man, and little one. Carla just laughed at her insults, insisting to me that Diane just like to kid around. She had taken a lot of abuse when she was growing up about being so tall for a girl. Now she liked to use it to her advantage. So, I had no interest in hearing them talk on the phone and went upstairs to continue my cleaning. I had just finished vacuuming upstairs and was carrying the vacuum downstairs to put it away, when I heard Carla say her name. I glanced over to where I heard her voice and almost stumbled down the stairs. Diane was walking in the front hall way, where Carla had just let her in our house. I tried to turn around to go back upstairs, when Diane saw me. I cringed as I knew I was going to get roasted for my appearance. "Hello Phil, Carla told me you were cleaning the house today. That's really nice of you, most husbands wouldn't be so helpful. But to be honest, I had to come over to see for myself, as I couldn't believe it. Now, I really can't. How can you be cleaning in such a cute outfit? I love how you accessorized everything and the way it matches. Plus your hair is just gorgeous. Carla told me she had been working with you to make it look better, but you look totally different. When I first saw your long hair, you looked like some bum, but now, all I can say is wow! The only suggestion I have for you, is if you are going to wear such cute short skirts that you might want to wear some hose. Your legs are a bit pale. Either a nice suntan shade, or even some colorful pastels would do wonders with your outfit. Also, now that you're wearing pretty shoes, if you tried some with a heel, maybe three or four inch, they would help you from being such a shortcake." She laughed as she finished and came over to me. I was literally blazing red from embarrassment. But Diane wouldn't let me off the hook, as she came to me to look at my outfit closer. Carla seemed to be enjoying this, as Diane continued to compliment my new look. I tried to move on, telling them that I had work to finish, but Carla said to take a break, make us some tea, and we could visit a little. I reluctantly agreed, put the vacuum away, and went to put some water on the stove. I was mad at Carla for exposing me like this and wanted to have it out with her, but didn't want to argue in front of her friend. I brewed the tea, preparing a tray with cups, sweetener, and some cookies. I felt so foolish for letting Carla talk me into going this far with my appearance modifications. I mean, it seemed worth it for the sex, but having been exposed to Diane, I really regretted being so compliant. I would have to change things once Diane left. I took out the tray and served both women before sitting down. At first, Diane made a couple more comments about me, but then our conversation became more routine covering our day to day events, some celebrity gossip, local news, and finally they switched to their upcoming charity event. I had to admit, it was enjoyable. We talked in a way that men don't, including being more open emotionally about what they said. I was surprised that they both were treating me like another woman. By the time they decided to go over the plans for the charity event, I stood up and cleared the table since we were done. They were both on the planning committee for the Downtown Historic Renovation Society. The group had chosen to have a Dine-n-Dance to raise money. There would be live music, drinks, games, and of course a dance floor in the middle. The group decided to set up small caf? type areas for eating and drinking and Diane and Carla had one of them. The women had chosen a French Caf? style, like what you might see in the French Quarter of New Orleans. They had everything else set up, except for finding enough helpers. To go with the caf? theme, the servers would be dressed like sexy waitresses. They would wear short skirts, dark hose, high-heels, and a white peasant-style, off the shoulder blouse. Complimented of course, by matching white aprons. "You can run the kitchen, where Dorothy and Ann will cook. I'll run the Bar area, with Jill and Tanya as bartenders. I will also direct diners to open tables, take payments, and welcome everyone. The only problem is we need more servers. I've got Tina, Janelle, and Lana, but for the number of tables we need at least one more. We can't wait too late either, as we've got to have time to have their costume fitted. Don't you know any cute ladies who'd help out? Come on Carla, think." "Don't you think I've racked my brain trying to figure out somebody, anybody? I asked every woman at work, some from my exercise class, even the lady who does my hair. But everyone has plans or isn't suited to wearing a revealing costume. Maybe we can go with a waiter or two. I could rope a man in to helping." Just as Carla said that, she and Diane looked at each other and laughed. It seemed so obvious now. Outrageous, but obvious. As their laughter faded, Diane looked at Carla, a serious tone to her face. "Do you think he'd do it? I know he seemed embarrassed as hell to have me see him this way. Can you convince him to parade around in front of the whole town in a pretty skirt and heels? I doubt anyone would suspect that you have him in panties at home, but would he be confident enough to test it out? Or are you more in control than even I know about?" She laughed softly, as she said the last part. Carla could see in her eyes that she was dying to know about how she was able to convince Phil to go as far as he had. I mean, just convincing him to let her curl and style his hair in such feminine hair-dos was remarkable, but now she had him wearing makeup, lingerie and cute little outfits. What was her secret? "Well, I think we can get him to do it. We just have to be smart about it. For instance, I know from the way he reacted when you teased him about his bare legs, that he is sensitive about his appearance. From the start, Phil seemed more concerned that he would look silly or ridiculous than he would look too feminine. It was almost like if he was going to do it, he wanted to do it well. So I think his biggest worry would be that he wouldn't really look like a woman. So if we can convince him he will not only be passable, but be very believable as a girl, then he'll go for it. What I want to try is to have you teach him the fine points of being a woman. You know body position, attitude, stride, and stance, all the behavioral and physical markers that signal a woman. Most men who dress, don't get it that the small details, like how you positon your arms, wrists, and hands when you are standing around, help define someone as feminine as much as whether they have long hair, big bosoms, or smooth, hairless legs. Luckily, we have a few weeks to work on him. If you handle his behavior and demeanor, I'll refine his appearance and clothing so he can pass without questions. Are you willing?" "Oh, you bet. I'll be glad to bring out the girl that's inside of Phil. But with me at my shop most of the time, I can only give him a few hours during the day. Will that be enough?" "Not really. That's why my plan is to have him come over to your place. I mean you live right above your shop, so if he's with you during the day, he can bounce between your home and the shop, when you don't have customers. Since he does his work online, he can work as well from your location as from our house. In exchange for your time and help, I'll have him clean for you. That way you can watch him move, walk, and see what he needs to focus on. Will that work for you?" "Having someone clean my house and shop for me? Oh yes that will work. I suggest if he does this, that we dress him in various skirts or dresses, so he gets the idea of how to move with them. Of course, he will be in heels the whole time as well. Do you have an idea of how you want him to look in his waitress outfit? For instance are you going with the small, young girl look he has now, or something bustier up top?" "He definitely needs to be large up top. Of the women who are helping, only Lana is big busted, so having another one should help. But I don't think Phil needs to practice wearing a range of outfits. We only have two options for the waitresses, one with a tight skirt and the other the flared and pleated look. Since he will be in one or the other, I want him to wear just those. But I do think it will be best if his skirts are short, very short. I think his legs are his most feminine feature, so I want his skirt to show them all off. Plus, he has a cute little butt, round, not too big, with a nice curve to it. If we put him in very sheer pantyhose, with only a thong underneath, and a tiny skirt, he could flash his booty too. The more we get the customers excited, the better we do at the till." "Well if you want his skirt that short, we need to get him fitted so we can hem it. How are you going to ask him? Or is it more like you're going to tell him?" Again Diane finished her question with a soft laugh. I could tell she was really curious about our dynamic at home. But I wanted to keep that secret, for now. "Let's see, what he thinks. I bet he'll go along with it, if we persuade him in the right way. Phil! Honey! Can you come in here for a minute? Diane and I have a question for you." When I heard her call for me, I was finishing the laundry, so I grabbed the dish towels which had just come from the dryer. As I entered the kitchen, I felt my face flush a little. Even though Diane had seen me earlier, I was still sensitive about how femininely I was dressed. It just felt uncomfortable. But I smiled at them, as I wasn't about to let her know that it bothered me for her to see me dressed like this. "What's up honey? You want more tea or something else to eat?" "No, we're fine. We just need to ask you something. You know we are working on the charity restoration project, right? Well we've got just about everything covered but we need a little more help. Would you be willing to volunteer?" "Sure, I guess. I do think it is a worthwhile effort. What do you need? I know you guys are running one of the food sites. Do you need me to help set up, or cook? I can bus tables if need be." "We do need help with the food, but what we're short of is wait staff. We have enough cooks, and set up is being handled by a caterer who is volunteering their equipment. We just need one more to take orders, serve food, and bus tables. We have three women already and just need one more. Can you handle it?" "I think I could. I was a waiter part time in college, so I know the routine. Is the menu complicated? How many tables would I have to cover?" "We can fill you in on those details later, but first we need to know for sure that you will agree to be one of our waitresses." "Just a minute, I'll be a waiter, right?" "No, we need a waitress. Our theme is a French Caf?, and our staff is all female. That is one of our selling points. But we both think you can do it. In fact, Diane is sure you'd be one of the cuter girls, if you let us help you get ready. Will you do it please? We've exhausted all our other options. Otherwise, I'd never ask for this kind of favor. Come on honey, do it for me. I'm positive we can make you look very attractive. I'll make it worth your while for sure, if you know what I mean. What do you say?" "Carla is right, you'd be perfect. I've already figured out the right costume, what I need to do to make you look your best, and how to help you be as cute as possible. Plus, I'll work with you so that your behaviors and movements are as feminine as your appearance. Don't let us down, please. I promise, I'll be nice to you from now on." I looked at them and shook my head. I was so surprised by their request. I mean, I was still embarrassed to be seen by Diane now, even after spending an hour or so dressed this way in her presence. I couldn't imagine doing this for a few hours, in front of hundreds of people. No matter, how well they helped dress me, I'd still feel vulnerable and embarrassed. "I don't know Carla. I don't think I can do this. I mean, I don't' think I can be convincing as a woman and I don't want to be in public as a guy in drag. I just couldn't handle that can of exposure. I'm already embarrassed standing here in my own house in front of Diane. How could I do this in front of more people? I'm more than willing to help you any other way, but I can't be a waitress." At that point, Diane stood up and came over to me. She stood beside me as we faced Carla, and wrapped her arm around me. She towered over me, being a good six inches taller, and more muscular too. Giving me a light hug, she leaned in to whisper in my ear. "Phil, you are such a sweet person. I know I've given you a hard time when I visit Carla, but inside I'm quite jealous of her having such a great partner. That's even more so now, that I've seen you dressed like you are today. She's indicated to me, what a tiger in bed you've become since she started helping you style your long hair, adding makeup, and little bits of lingerie. I can't imagine how much better your sex with her will be if you allow me to transform you for our charity event. I can promise you that I can make you look deliciously sexy and feminine. No one will doubt that you are a girl. Plus just because you are more feminine looking, doesn't imply anything about whether you are a man or not. Look around, there are plenty of guys who like to look nice. So don't be scared to try this. I swear if after being coached by me, that you don't feel that you past the mustard, then you won't have to help. Is that better?" I felt my face flush when she mentioned how better in bed our sex had become. I hadn't realized Carla had shared those kind of intimate details with Diane. But I knew it was true. Something had been sparked between us, when I allowed myself to be more feminine. I also knew I secretly wanted to see if I could be even more convincing as a woman, both to see if I could do it and to find out if Carla and I could reach better sexual highs. Taking just a second, I looked up, first at Diane and then over to my wife. "Okay, okay. I'll make you an offer. I agree to give it a try. But if I don't feel like I am convincing in this role playing, I can drop out without any consequences. If that is acceptable, then I'll try it." Carla smiled broadly, got up and came to me. She gave me a deep kiss and hugged me. I was surprised she was so forward in front of Diane, but I couldn't help but react. My cock twitched inside my panties, as I felt the delicious sensations of my lipstick coated lips being kissed by Carla's lipstick coated lips. They seem to float across each other. At that point, Carla pulled me back to the couch and Diane sat next to me. They began to tell me their plans for the event, how I fit in, the costume requirements, and how they expected me to learn to be more like a woman. I was surprised at Carla's insistence that I spend so much time with Diane. But I sensed how important this project was to her and I could see how being coached intently would help me move like a woman almost instinctively, if everything went well. I was even more surprised at how detailed they were about my appearance. As we talked it became clear that I was to have little to no say in how things were going to go. My role was to do as they directed and apply all my efforts to being the 'best girl I could be.' The first step in that process really surprised me. "I think we should go ahead and measure you, so Diane can get your uniform fitted. Since, we can choose what size we want your bust to be, we can adjust for that later. But now, we need your waist and hip measurements for sure. I'll go get the tape. Phil why don't you go ahead and strip down to your panties." I looked at Carla, surprised at her request. I understood I would be working with Diane to learn to play a feminine role, but I wasn't expecting to be so undressed in front of her. I knew my panty was quite small and sheer enough that I wasn't comfortable being measured in just it. "Do I need to take off my shorts? I mean they aren't that big and my underwear is a little skimpy. Can't we get my measurements like this?" I heard Diane laugh and turned to look at her. "It's okay Phil, I've seen lots of boy's thingies before. I expect by the time I'm done training you, we'll both be comfortable with you being in front of me with next to nothing on. Carla and I talked about this earlier, and she trusts both of us to be adults about it. So be a good girl and do like your pretty wife says." "Of course we need you in just your panties. Don't worry, like Diane said I trust you too. She is like my sister and I'm comfortable with whatever she needs to do with you. In fact, I'd appreciate it if you respect her like you do me, okay honey?" I could see I had little choice and reluctantly began to get undressed. I removed my blouse and had just slipped off my shorts when Carla returned with the measure. I had already started to blush, but my face really flamed up, when Diane took the tape and pulled it snug around my body. She first measured across my camisole, getting a few numbers. As she did, Carla and her chatted about how big I should be up top. Diane calmly told her that she could order breast forms in any size and felt I might be best suited if I went with a really large bust, at least a D- cup. I wanted to protest, but I was so embarrassed at that point that I remained silent. They continued to measure my body, getting both waist size and hip numbers. As Diane finished getting the size for my hips, with the tape snug around my butt, I felt her hand firmly run down the curve of my ass, caressing it as she moved to the juncture of my thigh and butt. Her move sent goosebumps up my body. With her hand still on me, Diane looked at Carla. "You never mentioned Phil had such a round profile to his bottom. It's not particularly big, but it has a nice shape. I think we should design his costume to take advantage of this sexy little feature. I mean he looks real cute in this thong. Maybe if he has a cute pair of sheer pantyhose we can shorten his skirt so his bubble butt will be obvious. I'll see what I can come up with." Her laugh as she finished made me cringe. I couldn't imagine a skirt so short that my ass would be on display, but by now I was overwhelmed by what was happening and couldn't protest her suggestion. Especially once Carla agreed that it was a good idea. I just hoped that once I had a skirt on, they would see it was too short for serving in public. With my measurements done, Carla told me I could get dressed again, and finish my housework. By the time I left the room, the women were deep in discussions about their next moves. By the time Diane left, I was really starting to have second thoughts, but Carla removed any doubts for me. She was super horny, and told me she loved seeing Diane play with my ass when she measured me. To reinforce that feeling, she pulled me right into the bedroom and sucked me off twice. Once while she knelt between my legs and the second time, while we did each other in a sixty-nine position. It seemed like every time I had second thoughts about the way our life was going, Carla would ratchet up our sexual life to persuade me. It worked again this time. Although I had agreed to this, the next few steps tested my resolve. I had been pretty good at keeping my feminized image hidden, but now I was being forced to take it more public. The first thing they both insisted I do, was to go to a salon for some beauty treatments. They cajoled me into accepting a full treatment. Because Carla had work duties, I went with Diane. As a way to soothe my fears, she was very upfront with the ladies at the salon about how I was helping them out. Everyone was surprisingly very supportive, with the owner and receptionist both telling me they thought I was very impressive for taking such measures. That positive feeling only lasted until the first strip of waxing cloth was ripped off my calf. Although I had shaved before, Carla insisted that I be waxed, because it would give me a longer lasting and smoother look that I couldn't get with shaving. So I bore down, handling the small doses of pain, while the young technician carefully removed the stubble from my legs, underarms, forearms, and torso. Just when I thought we were done, Diane whispered to her that my wife preferred me smooth all over, and suggested she finish me off with a Brazilian. I interjected that Carla had only talked about the areas we had already waxed, but Diane insisted my wife would love it if I surprised her. So, I caved once again. Although I had been embarrassed, by having to lie on the table in only my panties, taking them off to let her work on my privates was almost more than I could bear. My embarrassment was quickly replaced by pain, as waxing such sensitive areas was worse than what I had experienced before. At least Diane was nice enough to leave the room until I was completely smooth, front and back. I had hated it while it was being done, but afterwards, I knew the super smooth feeling on my ass, cock, and balls would be something that Carla would love. Once I was smooth, I got dressed for the rest of the treatments. The pedicure was enjoyable, as the soaking, scrubbing, and massaging felt very pampering. The manicure was nice too, although I was a little concerned about the gel tips the nail tech applied to lengthen my fingernails. When they had polished all my nails in a rich, rose gold color, I had to admit they gave me a very feminine look. Diane had promised to be nice, and she actually only said complimentary things, but it was hard to feel good about yourself as a man, when her compliments focused on how pretty my hands were, how dainty my feet looked with my polished nails, or her prediction that once I adjusted to my nail extensions, I wouldn't go back to my unkempt look. That unease was reinforced by the technician, who remarked that my fingers look so long, slim, and sexy with my longer nails that I would find lots of ways to show them off. With my nails done, the next step was to work on my face. The aesthetician commented that I was lucky to have a nice bone structure to my face, as well as finer facial hair. I would look better if I had my beard removed, but I wasn't the right type for laser treatment and electrolysis was expensive. She did suggest I use a special depilatory cr?me designed for women with facial hair. It was effective, immediately giving me a smoother look. It should last longer than shaving, since it removed the hair below the skin level, but was still gentle to the skin. The next steps included a mud mask, followed by a deep-pore cleansing, application of a tightening gel, and finishing with a soothing lotion. I was skeptical at first, but the treatments made my face even smoother with a softer look. The last bit of work she did was to shape my brows, giving me a little arch, just enough to open my eyes. I was nervous about her plucking my brows, but she told me in a few weeks it would grow back, if I decided I didn't like a neater look. Of course, Diane was pleased with everything, commenting several times that with the right makeup, I'd look very cute. The last step was one that worried me most. Carla and Diane had both been adamant about me getting some work done on my hair. They insisted I needed some highlights, as well as a professional trim to give me better overall shape to my hair. I was reluctant because I had been so pleased with how my hair looked longer that I didn't want to mess it up now. But the salon stylist showed me a couple of options, finally convincing me to let her do some minor cutting and selective highlights. I could live with the highlights, as they were designed to give more depth and variety to my hair color, but the cut she suggested wasn't one I was fond of. What she thought would look best, was to give me straight bangs, and then shape the rest of my hair so that if framed my face. The photo she showed in the design book, made it obvious that this was a very feminine cut, with the kind of bangs that men rarely wore as they came down straight to the top of my eyebrows. But Diane loved it, telling me that Carla would be ecstatic about me embracing this role for her. So despite my reservations, I let the stylist do as she wanted. When I left the shop, I felt very conspicuous as my hair, nails and smooth face made me much more feminine than when I arrived. At home that evening, Carla was indeed thrilled by my new look. She took some time to do my makeup and I was surprised how the little bit of brow work allowed her to make my eyes look more like a woman's. She had me try on a pair of stay-up stockings with a tiny panty and my nightgown. Of course this led to more playtime in bed, and she could hardly keep her hands off my silky smooth cock and balls. The feeling of her sucking each testicle into her mouth, running her tongue over it, and then engulfing my cock made the waxing almost worth it. I came three times that night, once in her mouth and twice in her pussy. I still couldn't believe the sexual change in her, but didn't complain. I was a little nervous about the next day, as it was the first one where I would go to Diane's to begin my training. But Carla told me just to follow her instructions and everything would be fine. We headed over to Diane's place early the next day, with Carla dropping me off on her way to work. She had me wear just a plain beige thong, jeans and tee shirt. I had no makeup, and my hair was pulled back in a loose ponytail. When I arrived, Diane was already inside the business portion of the building, but smiled when I entered. Because she had several customers in her shop, she only talked to me briefly. "Good morning, Philip. I can't wait to begin your conversion, but I have to do my work first. So what I want you to do, is go upstairs into my apartment. I've laid out some things on the bed for you to wear. There is also a few cosmetics on my vanity, all new items in a bag that I got for you. Do your best with them. The main thing I want to get done today, is to begin getting you used to wearing and walking in heels. I apologize about my place, its' a mess. But Carla said you love to do housework, so just make yourself at home and start cleaning up. I should be able to join you for lunch around noon. Thanks honey and enjoy yourself." I took her key and left to go upstairs. At that point, I was unsure what I had gotten into, and a little miffed at Carla for telling Diane that I loved housework. I didn't mind doing ours, but it's not like I really enjoyed it. Once I opened the door, I paused a moment. Diane hadn't lied about how messy her place was. It was like she intentionally left things undone. Walking around, I could see lots of work. In the kitchen, the sink was full of dirty dishes, counters were covered in crumbs and dried food stains, trash can was full and the floor was dirty. The living room wasn't much better, as it was dusty, with lots of stuff strewn everywhere. Sticking my head in the bath, showed it was the dirtiest room yet. It was hard for me to believe a woman would let her place get so bad. The bedroom was just full of clothes, most on the floor. The bed hadn't been made, with the cover just pulled up enough so I could see the items for me to wear. I was surprised by what Diane had chosen. There was only a pair of pantyhose, high-heel black sandals, and a full, white apron. I blushed a bit at the idea of cleaning her place, in such a semi-dressed state. But I decided to just plunge in. Carla had shown me how to pull on hose, so I worked the dark tan pair up my legs until the darker sewn-in brief was up to my waist. Given that I had worn a nude thong panty, It looked like I had nothing on underneath. I slipped on the heels, immediately feeling how they stretched my calf muscles and made me feel slightly tipsy and wobbly when I stood up. The apron was plain cotton, with ruffles at the hem and around the halter top. It came down to mid-thigh and had a wide sash to tie in back. My reflection in the mirror, made me looked dressed from the front, but my ass was exposed from the rear. Not worrying about that, I went to the vanity to sort through the bag of cosmetics Diane had gotten for me. The bag contained more makeup than I had anticipated. The basics were there, like foundation, concealer, powder, and blush, but she had more choices for other items than I expected. Diane had bought four colors of lipstick with several shades of gloss, a whole palate of eye shadows, two colors of mascara and eyeliner, and every utensil I might need. I hadn't really done my own makeup, but having watched Carla do my face several times, I sort of knew what to do first and how to apply it. I quickly decided to go light, with a coordinated lipstick and eye shadow, but skipping the gloss and eye liner. It was harder to do than it looked, so it took me a good 30 minutes to achieve even my rather plain look. With my face done, I undid my ponytail, combing it out, so my hair framed my face and I set it in place with some hair spray that Diane had left on the vanity. I stood up and looked at my image in the full-length mirror. I did look feminine, but not quite as sexy as I hoped for, as I lacked any bust. I couldn't quite understand why she didn't include a bra, as I know she had my sizes, but didn't go further into it, deciding to just get started cleaning her place. Now that I was dressed, I began to clean, starting in the bedroom. Looking at her bed, I decided to go ahead and change the sheets. Carla had trained me well on how to multi-task when doing housework, so while the sheets and some towels were in the washer, I went through the whole apartment gathering items that were out of place, like dirty dishes in the living room and old newspapers in the bedroom. With the clutter out of the way, I focused on the kitchen. Once I started, the morning went quickly. By noon, I had the laundry done, bed remade, kitchen clean and organized, and was just about ready to dust and vacuum the rest of the apartment. But I heard steps, and Diane entered her place. "How's it going so far? Let me take a look at you. Oh my, you look rather cute. I mean, you could have done more with your face, but it's neat and presentable. Turn around, let me see how your figure looks. Even without a full outfit, you have a certain feminine presence about you. I see you still have on your heels. How do they feel?" "Well it took a little while to get used to walking in them, and my calves and toes are starting to hurt, but I think I've got the feel for them now. I don't imagine I will ever get used to them, but I think I could handle a few hours okay." "Good start. We will likely have the caf? open for at least six hours, so I think if you wear heels for extended periods over the next few weeks, you'll be fine. But I do have another surprise for you." Diane held up a medium size postal box, express shipment, as if she were showing it off to me. "Guess what came this morning? Your new boobs! I intentionally didn't leave a bra out for you, because I wanted to wait until the forms came. Let's go into the bedroom and get you set up." She turned and headed there, with me following. It made sense now why she hadn't put out a bra. I have to admit, I was bit anxious to see the forms. But when she took the first one from the box, I gasped audibly. First it was so realistic looking. Second it also looked so big. Third I knew they would draw men's attention once I had them in a bra. But Diane wasn't content to just let me put them in a bra's cups. She had also ordered an adhesive designed to attach them to my chest. So after taking off my apron, she had me lie flat on the bed. Following the directions, she sprayed the glue on the back of the form, placed it on my chest to transfer some adhesive to me, and then resprayed the form to help seal it. She had me lay there, with my hands pressing the forms lightly against my chest. It was an odd feeling, my hands cupping the breasts, like I had done before to women, but now these were my breasts. After a few minutes, Diane told me to sit up. Doing so, was a reality check. I removed my hands, and the forms stayed put, but with a gravity induced pull on my skin. I could feel their weight, something I had never thought about when I saw large-breasted women. The forms were securely in place, although the edges could be seen, but they felt real to me. "Phil you look so good. I was right about you being perfect for a big bust. You should be able to wear these for extended periods, but even though they would hold without a bra. I think it would be best if you wore one anyway. You like your new boobies?" "I guess. They're heavier than I expected, and so big. Aren't they too big? They don't look real to me, more like a cartoon. Maybe we should exchange them for a smaller size." "Nonsense. They're perfect for your frame. Plus, I want you to draw men into our caf?, and with your curves, long legs, and a cute costume, you'll be just what we need. Now put on this bra, and your apron and help me make us a light lunch. I need to get back to the shop and you still have housecleaning to do." I took the lightweight garment from her. It was a plain beige, sheer lace style with full coverage cups. I did as she instructed, with her showing me the best way to put on a bra. Once the straps were adjusted, the weight of the forms was even more evident. The sheer fabric of the bra hid the edges of my forms, but allowed them to be seen, especially the areolae and nipples. With my apron on, I now had a very projecting bust line, not so much so, that I couldn't see my feet, but my new size was always in my peripheral vision. As we went to the kitchen, I felt my boobs bounce in the bra, a totally new sensation. I could tell it would take quite a while to get used to that. In the kitchen we made some sandwiches, and a pot of tea. As we ate, Diane asked me about my makeup application and gave me a few pointers to try next time. She also smiled constantly, I think she was enjoying my awkwardness in adjusting to my new breasts as well as talking about my new femininity. Before when we had talked, it had always been in the presence of Carla and I hadn't felt comfortable around her. This was still awkward but in a different way, mostly because I felt self- conscious about my appearance. Once we were done eating, I got up and placed the dishes in the dishwasher and wiped off the counter. I could feel her eyes on me the whole time, as she silently evaluated my progress. I felt real exposed as I stood at the counter, knowing my bare ass, covered only by the thin nylon pantyhose was on display. My concern was well founded, as she spoke up. "Philip, we need to do something about your look. Although your butt is cute enough, seeing you like this I can tell it's not a girl's ass. It's your tan lines. It's obvious you've never been in the sun in anything but long-leg shorts. What you need is a bikini tan line, something almost every girl has. Even if she wears a one-piece suit, the tan line is right at the edge of her butt. Your arms show the same masculine pattern. Your tan stops at your upper arm. Girls more often show strap marks, or at least a bra pattern. But it shouldn't be hard to fix this. I think I have a bikini you can use. With a few trips to the tanning salon, we can give you a look that will really accentuate your smooth body." "Diane, is that really necessary for a onetime thing? I mean I don't tan very easily, as my body is pretty pale. If I wore opaque hose wouldn't that cover up everything?" "Oh you men can be so silly. You're right that a thicker tight would hide your legs, but part of the beauty of pantyhose is that they really allow the viewer to see your body. With your sexy legs, a sheer hose makes you look much better. Plus, all the other girls will be wearing similar pantyhose, so I want you to match. Our goal should be to have you look like a real girl, not a drag queen. Unless you would prefer that all the customers know that you are a man dressing in girl's clothes? I thought you'd prefer to be just one of the waitresses, not the odd one out. Am I wrong?" My face flushed momentarily, both from the thought of how exposed I was now and how I would be dressed similarly in front of strangers in a few weeks. I rethought the idea of getting a tan, and realized quickly that I did want to pass as a woman. Like my smooth, hairless skin, a female tan line would eventually revert back to a manlier look over time. "I do want to pass, as much as possible. If I need to get rid of my short and t-shirt tan, why don't I just tan allover? Wouldn't that work?" Diane smiled at me and took a sip of tea. "Yes, it would work. But what fun would that be? Having cute bikini tan lines makes it unambiguous that you aren't a man at all. That's the goal for now. I promised Carla I would make you into the perfect girl, so that's what I'm going to do." Her response stunned me in its outrageous honesty. I had suspicions about why Carla had entrusted Diane with helping me portray a woman. Now her reasons were clear. Her brazen answer laid it out. If I didn't protest now, then I would be accepting her characterization of me as not really a man. That I was more suited to be a girl. I had noticed that term, girl. Diane seemed to like calling me a girl. I guess for her that meant that not only was I not a man, but I wasn't mature enough to be a woman. "I don't like that idea at all Diane, in fact that doesn't sound like Carla either. You all promised me I would only do what is necessary for this event." "Gotcha! Didn't I? I swear Philip you can be so easy to tease, it's almost not any fun. I'm just kidding about that. But I do think you'll be more convincing with a bikini tan line. Most girls, even if they go to a tanning booth, still have an outline because they wear one when they're