It All Started With

It all started when my wife decided to take some cosmetology classes to help with her photography. Because, while most of the women who came to her for boudoir pictures, were fairly competent with their own makeup there were always some whose choices made it almost impossible to get the desired results. Either way too much foundation and mascara, or shades of lipstick that were either too dark, or too light for a lingerie photo shoot. I mean, if you wanted pictures to excite your husband or your lover, you didn't put your makeup on with a shovel, or use colors that made you look like a cheap slut. So my wife took those classes to help those who needed professional assistance to look good on film.

However, while most of the other students had daughters or close friends they could practice on, we didn't have kids yet, and my wife was too busy with her studio to have the kinds of friends who'd let her experiment on them. So, naturally, she wanted to use me to do her homework assignments, because I was the only person she had available. And, she got real good grades on her initial techniques, because her teacher gave her extra points for difficulty, after seeing that her subject was a man, not a woman. But, we ran into a snag, when she got to the lessons that wouldn't completely wash off when she was done. Like eyebrow shaping, since there'd be no way to hide the fact that I'd let my wife pluck mine down to a thin line, or shaved them off all the way and drew them back in.

Her teacher helped her with that, since she was a real makeup artist, by creating some false eyebrows exactly like mine, that I could glue on until my real ones grew back in. And, my wife talked me into it, by playing the sex card, and promising me that not only would she finally try to suck my cock, she'd do it every class night until this part of the lesson was over. And, it was worth it, because she was actually eager to learn how to drive me up the wall, the way I did her when I ate her pussy. Except, the first time I came in her mouth, she quickly decided she didn't like the taste, or the feeling, and would pull away when I started getting close, and finish me off with her fingers. But the lesson, and of course the blowjobs, didn't end two weeks later like she'd said it would. Because they moved on to hair styles, and bushy eyebrows would completely ruin whatever effect she was trying to create with my wigs.

It was during this phase that my wife started teasing me about what a beautiful woman I'd have made, and asking if I'd flirt with a girl who looked like me when I went out. I did have to admit that she did wonders with my makeup, and that in a darkened room I might think someone like that was pretty. But, if we were in harsh light, no matter how closely I shaved, my 5 o'clock shadow showed through, and makeup heavy enough to cover it, made me look like a $5 hooker. That's when she made her next sexual bribe offer, that even though she really didn't like that part, she'd let me start cumming in her mouth, if I let her take me to an epilation salon, to completely get rid of my facial hair. Initially, I thought she'd offered more than it was worth, especially when she gagged the first couple of times. Because, I might have gone along with it anyway, since my face is very sensitive and shaving really irritates my skin. I hated it so much that I would have grown a beard if that hadn't irritated my face even more. So, this was a win win situation for me, because not only would I never have to shave again, I was also getting to cum in my wife's mouth three nights a week.

But, the first time she was able to let me do it without choking when I came, she raised the price to me, by expecting me to kiss her after she finished. She had a very logical reason for it too, that if she didn't think it was disgusting to kiss me after she came in my mouth when I ate her pussy, it shouldn't be disgusting to kiss her after I came in her mouth either. I mean, it's not like it was somebody else's sperm, although she did have to admit that when I had my makeup on, it almost felt like she was sharing my cum with another girl. That got her fantasizing about us having a threesome one day, because she'd love to have a girl eat her pussy after I fucked her, and she might even try licking the other girl herself. It didn't take long though, just two weeks of that fantasy, before she asked me to be that girl, because there wasn't much difference between kissing her after blowjobs and eating her pussy after I made love to her. And, in return, and so she could get used to the taste of pussy herself, she'd give me my blowjobs after I fucked her instead of before. Then she added another twist, by stuffing her panties in her cunt, after I licked her clean, then having me wear them at the start of my blowjob, so she'd really feel like she was licking our threesome girl.

Her beauty classes didn't stop though, once she'd learned all they could teach her about makeup, hairstyling and doing my nails. Yes, my nails, because who else did she have to practice on. Those came right after she talked me into getting my tongue pierced, by getting hers done too, and at the same time, getting my other ear done, because only wearing one earring spoiled the effects she was trying to create. Anyway, her classes didn't stop there, because her teacher offered to instruct her in costuming, since that would definitely help in her photography. And, it cost my wife her last virginity, meaning her tight little asshole, to get me to have all my body hair removed with the same laser they used on my face. It's not like it would be the first time I'd ever removed the hair from my arms and legs, because I used to shave my body when I was on the swim team in high school. So what if this was permanent and shaving wasn't, I'd enjoyed being hairless back then, and would have no problem being hairless for the rest of my life.

Anyone who knows anything about laser hair removal knows the main reason for multiple sessions isn't the size of the area. It's that hair grows in stages, and the laser only works on final stage dark hair, not on the fine middle stage hairs, or the almost invisible first stage hairs. So, while they were able to remove most of the easily visible hairs in two long and slightly painful sessions, I'd need to go back every two weeks until they were sure it was all gone. However, except for closeups, I was hairless enough to start modeling the gowns and dresses my wife wanted to work with next. There was an immediate problem though, and it was that without any tits, I was too androgynous for the look she was trying to achieve. And while padded bras helped with closed neck period costumes, they didn't work at all for anything with an open neckline. Like with my eyebrows, the solution came from her teacher, a professional grade latex chest panel, that with the proper blending makeup, provided realistic looking breasts even in the most revealing lingerie.

Of course, having me wear it, cost my wife nothing as far as sex was concerned, since it didn't require any changes to be made to my body. What did cost her though, was getting me to pose for a boudoir photo set and being allowed to upload the pictures to her web site. Her argument was that if she could make her followers believe I really was a girl, in that kind of setting, she'd know for sure that she could make the plainest woman look beautiful without cheating with PhotoShop like some photographers did. And her offer was to add another blowjob to our sexual activities, this one after the ass fucking, although I'd have to lick her asshole clean as well, which she didn't think I'd mind doing for her. The results exceeded her wildest expectations, and dealt a blow to my masculinity at the same time. Because those pictures got more likes than any set she'd posted before, as well as a ton of comments.

Those comments were the subject of her dirty talk, while she was sucking my cock that night, about how many men, and a couple of women too, had written things that made it clear they'd love to fuck me. And she had to admit that thinking about having a two girl, one guy threesome, where I was one of the girls, made her horny as hell. When she saw the look of horror on my face, she asked what was wrong with that idea, besides having me dress like a woman in front of a man? If we started having threesomes, she'd eventually want one with another guy instead of just with other girls. And, just like I'd want her to do certain things, like kiss the girl after I came in her mouth, or lick the girl's pussy and asshole after I fucked them, she'd want some things too. Like kissing her after she sucked the guy's cock, licking her clean after the guy fucked her, and maybe even licking her pussy while the guy was fucking her. She wouldn't demand that I suck the guy's cock myself, just because she ate some girl's pussy for me. But, she had to admit that she wouldn't mind if I wanted to do that, and would love to watch him cum in my mouth, if I did. Then she spent the rest of the night talking about that, and pretending that the sperm I squirted in her mouth, and the cock cream I licked out of her pussy and ass, were somebody else's, not my own.

Even though she hadn't left a comment on my wife's page, my wife's teacher was one of the women who said she'd love to fuck me, even more so than if I was a woman, because she already knew I was a man. And she asked my wife if her and I would be be interested in a threesome, although she did request that we let her take us to a fancy dinner first, and that I come dressed as a woman, so she could see my wife's masterpiece up close. Of course, my wife made honoring her teacher's request a condition of her accepting, because she also wanted to see how well her handiwork held up in a public setting. Well, and that we'd also start looking for a suitable guy for the other threesome, because she wanted that as much as I wanted this one. And I agreed to all her terms, because her teacher was really high on my list of women I'd love to fuck, especially that awesome ass of hers.

They set it up for a little over two weeks later, for the Friday after my last laser treatment, to make sure all my arm and leg hair would be completely gone. That, and if it was as fun for everyone as we hoped it would be, they both thought we might keep going all weekend. During that two weeks, since my wife felt we'd already talked about this fantasy enough and she'd just started talking about the new one, almost all of her dirty talk was to get me used to thinking about what she wanted then. It worked too, because the disgust I'd initially felt at the idea of tasting another man's sperm was first replaced by resignation, then slowly started to thrill me more and more. I mean, I was already licking my own cum out of her every time we made love, so licking someone else's out of her wasn't the real problem. The real problem was doing it in front of the guy who put it there, and what they'd think of me. I definitely didn't have to worry about what my wife thought, because she made it clear that what would thrill her the most was me acting like the woman she planned to dress me as, and doing everything she did. And she meant everything, including me sucking the guy's cock until he came in my mouth, and him fucking my virgin ass, before I sucked his cock again. One thing she kept promising me, during her dirty talk, was that the man we found for this, would feel the same way about me doing those things, as she did and would gladly treat me like a woman all night long.

The night before our big date, my wife took me shopping to buy the perfect dinner dress. What she really wanted to buy, was a slinky off the shoulder evening gown, with a slit up the side, but it wouldn't be a good idea, since the slightest arousal on my part would give the whole game away. Instead, we went with a semi sheer red blouse, and a short black pleated skirt, to show off my legs, along with some red sequined fuck me pumps and a matching clutch purse. Yes, I could walk in the high heels, because I'd worn them quite often during our photo shoots, and had learned how to run to the bathroom in them when we took breaks. Then she took me to Victoria's Secret, to get a darker red lace bra, for under the blouse, since that would be even sexier than having my fake nipples show, and my first g-string to show off my ass in case my skirt blew up. And finally, we got me my own set of lingerie, to wear when we got home, a white satin negligée that looked a little like a wedding dress, although I didn't realize the significance until much later.

When I got home from work on Friday, my wife immediately rushed me into the shower, and used her body wash instead of mine, so I'd also smell more like the woman I was going to dress like. Then she spent about two hours, doing my makeup, hair and nails, before dressing me in my new clothes and adding the earrings and necklace she'd bought to go with my outfit. When she was finished, and wanted me to see how I looked, I had to admit that she'd outdone herself, and I looked so sexy in those clothes that even I wanted to fuck me. Her proudest moment though, was when we entered the restaurant and most of the men turned their heads to stare at me as I walked past. She even had me smile sexily at two of them she wouldn't mind inviting to our bed for her threesome, and the smiles they gave back made me feel even sexier. I saved my sexiest smile for her teacher though, and the look she gave me in return would definitely have made me ruin the evening gown.

She had nothing but praise for everything my wife had done with me, from my makeup to the choice of outfit and accessories. And, she made her praise on the physical level too, by caressing the leg closest to her throughout the entire dinner. Since she'd come by taxi, she rode to our house with us, and asked my wife to drive so we could get to know each other a little better in the back seat. That meant her tongue down my throat, and her hand under my skirt, while she directed my attention to the breasts she admitted she'd paid a pretty penny to make as nice as they were. When we got to the house, my wife pried us apart, to go change me into my new negligée, and fix the mess her teacher's lips had made of my makeup. Then, when we returned to the living room her teacher spent a good 30 minutes inspecting me closer than she could have in the restaurant. Again, she had nothing but praise for how beautiful of a woman my wife had made me, until she got to the bulge in my panties. Then, as she started softly stroking it again, she said we needed to find a way to hide it or at least make the swelling go down, before kissing me deeply and saying she knew just how to take care of that. And with that, she pushed me down onto the sofa, and kneeling between my legs, began to lick my cock through my panties, the same way my wife did when I wore them to bed.

After a few minutes of that, she started sliding my panties off, while telling me I had really beautiful legs, then finally taking my aching cock into her hot wet mouth. She was an awesome cocksucker, and didn't just suck my cock, she made love to it, with her lips tongue and fingers, the way all men wish a woman would do. She didn't rush the blowjob either, because she obviously got almost as much pleasure out of sucking my cock, as I got out of her doing it. And when she finally let me cum, some 20 minutes later, I had no problem kissing her sperm filled mouth as long and deep as I kissed my wife's. Then, after my wife kissed me herself for a few minutes, she asked me if I'd like to return the favor, and lick her teacher too, before we moved to our bed for the real fun. But, when I went to start opening the buttons on her teacher's blouse, my wife said she wanted us to undress her together when we got to the bedroom. So, could I just raise her skirt and slide off her panties and lick her to one orgasm here on the sofa first, like she had me?

It was only when I raised her skirt, an area she'd deliberately kept me away from in the car, that my wife's last sentence, about licking her the way she had me, made sense. And it also explained why all her dirty talk lately had been about us having sex with another man. Because my wife's teacher wasn't a her, he was a pre -op transsexual, with a cock every bit as big as mine. When I went to pull back, my wife put her arms around me and told me she knew I really wanted to do this, because she'd read the stories I'd written and hidden on my phone. And, it was ok for me to have those fantasies, because she had some of her own, that she'd like us to make come true together. Like, as she'd already told me, bringing other girls to the house, so she could lick their cunt juice off my cock, and so she could lick my sperm out of their pussies and assholes.

But, she had to be honest and admit that her biggest fantasies didn't start until she began to use me to practice her makeup on. Because her teacher had told her that with a little work I'd make a very beautiful woman, and after he admitted that he was also a man, living as a woman, her fantasies were born. That's when she asked her teacher for advice on how to make both of our fantasies come true. The eyebrow plucking, the laser sessions, and the piercings were all for her side of the fantasies. And the kissing after blowjobs, sitting on my face after I came inside her, and all the other incentives she'd offered me, were ideas her teacher had given her, to make sure I wanted this. Now, the sooner I slid my lips over the head of his cock, the sooner I'd get to taste his delicious sperm when he came in my mouth. Then we could move to the bedroom, where they could teach me the rest of what I needed to know about being a woman, like how wonderful it felt to have his cock slowly fucking my asshole. Because he knew both of the men I'd smiled at in the restaurant, and knew that neither of them would mind that I was really a man, as long as I happily sucked their big cocks and let them fuck me like a woman. And she was planning to invite both of them to the house tomorrow, so they could fuck all three of us together.

Here's where my wife's two weeks of fantasy talk paid off, along with most men's curiosity about what thrill women and gay men got out of sucking cock. And the fact that the cock was attached to a woman's body, meaning they definitely wouldn't ridicule me for doing this, her or my wife. So, with a moan, I let my tongue slide over the material of her teacher's panties, and their answering moans told me that they both wanted this as much if not more than I did. Had either of them touched my head, to hurry things along, I might have stopped at that point. Instead, my wife made her desire plain in a different way, by sliding her teacher's panties down a little, so my next tongue swipe would be on flesh not nylon, and telling me she loved me, she kissed my cheek then pulled away to watch from a more comfortable distance. It was me that rushed things, by lifting his cock and lowering my lips over the head of it before I had too much time to think about what I was doing. Once it was in my mouth though, it felt so natural there, that even if my wife suddenly changed her mind, I was going to finish what I'd started. She wasn't going to change her mind though, that's for sure, because when she commented about how beautiful I looked with his cock in my mouth, I glanced over to see her with our HD video camera, filming my first blowjob. If anything could have stopped me, knowing she had proof of what I was doing should have. But, I just smiled at the camera, then smiled up at my wife's teacher, the way my wife did when she was sucking my cock. The only thing the camera really did, was push me to make it the slowest and sexiest blowjob I could, and to really act like the woman I was pretending to be.