I meet a girl, the most gorgeous, sexiest woman I've ever seen. It turns out that she's actually a shemale! We dated for months until she finally let me touch her crotch. I'm thoroughly amazed. I'm too nice a guy to be disgusted. She knew I would be shocked, because she knows how incredibly feminine she is. I've made out with her dozens of times. I've sucked her nipples. She has sucked my cock, and swallowed my semen. Now that I've got her willing, and since 95% of her is stunningly gorgeously female, I decide to pretend that she's not a man. I fuck her in the ass first. But she wants more. She makes me reach around and rub her big fat cock. I pretend it's my own. Before I know it, we're doing it missionary style, and her cock rubs against my belly. She flips me around, so that she's sitting on top of me. I caress her beautiful boobs, and her perfectly proportioned waist. I fondle the belly-button ring. She moves up and shoves her cock in my face! I'm so turned on by her body that I comply, thinking, my god, this is the first time I've ever had a cock in my mouth! She comes in my mouth, and I spit it out – not out of disgust, but out of surprise. All this time, of course, my penis has been untouched. It is desperate for some action. I am still captivated by her figure, and her breasts. And her semen all over my face. I slide her back down off my chest to my crotch, and fuck her again for a bit. My hand is on her cock. She asks me if I'm grossed out by her penis. I tell her, truthfully, that it sorta turns me on, even though I love her femininity above all else. She asks me if she can fuck me, and not understanding, I say yes. She turns me over roughly, and I clue in. I interrupt her, and she begins to pout, but I don't stop her – I reposition myself so I can see her behind me by looking in the closet mirror. I beg her to fuck me. All I can see is her titties bouncing up and down and the look of ecstasy on her face. It hurts at first, but it's such a turn-on that I get used to it, and start to enjoy it. A lot. I have her stop for a second and turn 90 degrees so I can see from a different angle. Now I can see her cock ramming me in the ass, and it feels even better. She reaches around and jerks me off half-heartedly, concentrating on her own pleasure. I come hard when I feel her pumping her semen inside me, savouring the thought that I am her bitch, even as her beautiful, slender, feminine fingers caress my dick. I feel so naughty about losing my virginity that it turns me on, but we're both so tired and spent that we can no longer continue. She cuddles up against me, her cock against my thigh, and we both fall asleep.
We talk about these confusing events in the morning. It turns out that she, as a young boy, had decided long ago that she would rather be a girl. She has tried very hard ever since her mid-teens to make herself as feminine as possible. I am amazed by the overwhelming magnitude of her success. She looks like a supermodel in a bikini, and in lingerie. She has the whole world fooled.
Still, I have misgivings about the situation. I make them clear. I don't want to be a homosexual. She promises me that she will have surgery correcting that last little problem as soon as she can afford it (she's been saving for years). But when she starts getting dressed, I become incredibly aroused. I snap the elastic on her panties as I admire her cute little girly ass. Before we know it, we're fucking again. I am very confused about my feelings about her penis. Part of me wishes very much that she had a pussy, like other girls; but part of me is very intrigued about how a boy can turn himself into a female sex goddess; and of course there's that last little part of me that's terribly excited about tasting cock and feeling it in my ass.
We stay together, and we have mind-blowing sex. What turns me on so much about her is her transfermation. I grill her about what she was like before she was a girl. She talks reluctantly about her unhappy boyhood, and the dificulties of asserting her femininity through puberty. It turns me on so much to think that this perfect piece of female ass that other guys ogle at and are envious of actually is a man. I try to imagine what it must feel like to wear the things she wears. I ask her, and she gushes about it. How liberating it is. How sexy it feels.
I ask her what would happen to me if I ever wore women's clothes. She says probably nothing. Anyway, she says, she likes me all butchy and manly, so she doesn't care for it. How manly can I be, I ask, if I'm sucking and fucking cock on a regular basis. She blushes, and says nothing.
I start to envy her her wardrobe. I think to myself, that could be me in those fishnet stockings, fuck-me boots, and little black dress. I start trying things on, just for fun. I try to include her, but she doesn't like playing dress-up with me. So it becomes my secret. I get my own panties and bikinis and lingerie. Eventually, she finds out. We slowly break up over it.
Now I realize how fucked I am. I realize that I'm still incredibly attracted to pussy, but that I really love the idea of Andrea. I love the thought that I can become just as feminine as her. Nothing turns me on more than that. I date some women, and steal their underwear every now and then. It never lasts long, because they either find out about my fetish, or I feel trapped when I can't make myself girly. So Andrea comes back into my life.
She is just as disappointed in my girlish habits as any normal woman, but she can't be disgusted, because she does it herself. I am still incredibly aroused by her, but she can't even use her decrepit dick anymore, because of all the hormones. I am not in love with her anymore, either, so we get along. I meet her sister, who guided her through her own effemination. Together, they teach me. This is how I learn that I can become ultra-feminine too, by taking on a female persona, and wearing nothing but female sexwear at all times.
It's difficult at first, but practice makes perfect. The first few weeks are all about discovery. I wear the skankiest clothes, and I do so in public. At first, I'm hideous, but with a lot of work, can look pretty feminine. I start hanging around in gay areas, because those are the only places where I can feel safe. I start meeting other men, and can't resist the taste of cock. I am now in Andrea's place.
A few years later, I am even more feminine. My tits are bursting out of my bra, and I can't get enough cock. But the best part is that my own penis is completely gone: I have a pussy! And it's all natural! I've transformed my body not with chemicals or surgery, but with sheer willpower! And I love my new body!