Fiction: Losing In Style

It’s such a release to wear your clothes, to turn myself into a sexy, gorgeous girl, like you.  It makes me feel so unbearably sexy when I pretend to be a girl.  It feels so naughty.  I should definitely not be doing it.  But it’s so much fun!  I love the way silk and satin feel on my skin.  More than that, I love the way your clothes are themselves innately feminine.  I love the way my wearing them obliterates any pretense I ever had of being masculine.  

I long to wipe my manhood away, and reveal myself for the woman that I am.  I long to transform myself into a girl, and do everything that real girls do with complete impunity. 

It starts when I make fun of homosexuals.  I laugh at them and denigrate them.  But my girl, she takes offence.  She says that my making fun of them is proof that I’m not comfortable with my own sexuality, and that the fact that I laugh at gays only betrays the fact that I am secretly like them, or at the very least that I secretly want to be gay.  She goes on with this ad nauseum.  I joke with her that she’s a lesbian, and would love to have pussy.  When she objects, I call her a hypocrite for being afraid of her own homosexuality.  So we make a bet: she says she’ll see me take a cock in the ass and in the mouth voluntarily in no more than 90 days; I say she won’t, but I’ll have her eating carpet by that time.  If I win, I get to have a threesome with her and another girl of my choice; if she wins, she gets to have a threesome with me and another guy.  In either case, the more numerous gender must perform lewd homosexual acts for the entertainment of the lone member of the opposite sex.

90 days is a very short time to completely transform any man, and especially me.  I ask her how she expects to do it (we stipulated at the time of the bet that there would be no force allowed, nor any psychological shanghaiing such as hypnosis, nor any surreptitious feeding of hormones or mind control drugs; it would all have to be done through conscious actions; she would have to win me over with convincing arguments) and she tells me that all she has to do is plant a seed in my head, and I’ll begin my slow but inevitable transformation immediately.  She also mentions that I won’t even know what the seed is until it starts to eat away at my façade of manhood.

She tells me that the only way I can avoid becoming a flaming faggot in 90 days is by wearing her underwear.
I laugh at this blatant contradiction.  More likely I would begin my hopeless spiral into gayness only if I did as she said.  


"So then," she says triumphantly, "you admit that it’s possible that you’re going to become a total raging cocksucker."  


"Never," I reply.  


"Then why are you afraid of wearing panties and a bra?"


"That would be gay.  Besides, that’s just your trick to get me to fall into your trap.  I will not make myself the least bit feminine for any reason."

With that the seed is planted.  I try to imagine how wearing women’s underwear could possibly save me from becoming a fag, but I just don’t see it.  Confident in my manhood, I start to imagine the ways I could convince girlie to develop a taste for pussy.  Visions of girls making out together dance in my head.  

I am pretty confident at this point.  I am so confident that I laugh some more about the idea that my wearing women’s underwear could somehow undermine my manhood.  I figure that I could probably do it and come out unscathed.  Nothing can change what I am.

She starts to taunt me when we make love.  She tells me to imagine what it’s like for a girl when she gets to have a big fat dick slide inside her.  She tells me to picture what a girl tastes when she has a mouthful of cock.  Meanwhile, I proselytize about the wonders of femininity, about how incredibly sexy women are, and how she knows it.  I convince her that she looks at fashion magazines because she knows how pretty girls are, and she wants to taste one.  This gets me hotter than hell.  I love thinking about her fucking another girl.  Girls everywhere.  Nothing but girl.  Girrrrrl girl girl woman girl girl girl girlie girl.

Somehow, my appreciation of girls becomes tainted with the graphic detail my girlie gave when describing how it feels to have cock inside her.  I begin to imagine being a girl.  Not fucking or anything, just being.  Being sexy and girlish and curvy and effeminate.  I know what makes girls sexy, and I can feel it all over myself.  By day 30 I’m worried sick about losing the bet.  I can’t stop thinking about how sexy it must feel to be a girl.  Every time becomes more intense.  Soon I start fantasizing about actually wearing her panties.  The idea makes me incredibly horny.  I figure, it’s gotta be worth a shot.  Maybe she wasn’t kidding, and wearing her panties will save me from these nasty thoughts.

The moment I put them on, as my knees quiver and buckle while I collapse in a sexual heap of girl-mad femininity, I realize that it was a trick, that I had now lost all hope of ever winning the bet.  Worse, this realization filled me with unbridled ecstasy.  While I wore those panties and that bra, I rejoiced in the fantasy that they would turn me momentarily into a complete perfect female, and that I could start fucking and sucking dicks forthwith.  I pictured myself as a girl, with a big fat cock in my pussy, in my mouth, and luxuriating in every second of it.  I could feel the bra shaping my chest into a pair of full, perky tits; I felt the panties mould my butt into a cute little round girlie’s ass, and suck in my waist, and wither away my precious cock into a delicate, delicious cunt.  And when I came I turned livid with shame and put it all away never to be spoken of or thought about again.

That’s when I knew that she wasn’t kidding after all.  The experience of wearing her panties showed me just how close I am to becoming a flaming homosexual.  I could never even think of doing it again for as long as I live.

Just to be sure, I repeated the experience with all kinds of lingerie, swimwear, and anything else I could think of.  That ought to teach me.

By day 60, I could no longer pretend that I could win.  This is when I realized that my pride wasn’t worth giving up the intense pleasure of being feminine.  I couldn’t help but celebrate by buying my own lingerie and electrolyzing off all my unsightly body hair.  I still kept up appearances for girlie’s sake, because I wanted to surprise her.  I sucked my first dick on day 75.  I got fucked in the ass the very next day.

I manage to surprise girlie on day 89 by contriving to have her walk in on me sucking and fucking dick simultaneously while wearing my own babydoll and fishnet stockings.  From then on, we become like sisters, except we have a threesome with this gorgeous hunk of a guy to seal the bet.

Diary: Hollywood

I spent this evening in Hollywood, enthralled by the multitudes of gorgeous, sexy women.  Now I’m wearing the outfit I bought a few weeks ago: my vinyl mini-dress, matching lace garter belt and thong, and fishnet stockings.  I didn’t see anyone wearing anything like this, but I desperately need some femininity.

I did come across one of the most exquisitely beautiful women I’ve ever seen.  She was slightly oriental, young, and wearing a form-fitting backless red formal dress.  Her body was perfect, and she carried herself like a model.  The slit in her skirt only came up just above her knee, but it revealed a stunning pair of legs.  Exquisite.  I should hang around there more often.  There are many sleazy lingerie shops along Hollywood Boulevard that I might thoroughly enjoy.

I wish I could describe exactly what it is that femininity does to me.  I can’t even describe what it is.  The way women move, the way they carry themselves, has so much to it, and yet I can’t even put my finger on how it differs from men.  And why do I love it so much?  Maybe it’s a certain innate delicacy to their every gesture.  Their limp-wristed, butt-wiggling walk.  The way their feminine features, from their soft, smooth, hairless skin; their slender arms, shoulders, necks; their soft, rounded bottoms; the exquisitely slim curves of their waists; their round perfect breasts; all billowing out from them without their even knowing it. 

And here I am, wearing a fucking dress.

The appeal is so ridiculously strong.  I want to be even more feminine right now.  I want to make myself utterly female.  It’s not good enough that I’m wearing sexy lingerie and sex wear; no, I am fantasizing about wearing my corset bra.  I need that extra layer of womanhood.  I need something to accentuate my breasts, and taper down my soft, soft, slim, sexy waist.  I want to abandon myself to it.

There, that’s much better.

I love brassieres.  I love the way the part under the arms looks.  I love the way the straps (I’ve removed them from my corset bra because this outfit looks much better without them) accentuate the delicacy of female shoulders.  And of course, the titties.  

Considering how much I worship women, is it really any wonder that I can’t resist the urge to pretend to be one?  Given the chance to dress up like a girl, I can’t imagine how a normal man wouldn’t be overwhelmed with temptation.  I love how lingerie makes me feel so sexy.  I imagine myself as a girl.  I imagine myself recklessly, remorselessly, unhesitatingly abandoning my manhood.

The fantasy is this: I love a girl.  I want to be her.  I tell her as much when I make love to her.  Finally, I beg to wear her clothes.  I know she disapproves, but I beg her, and promise to do anything at all for her if only she lets me wear her panties.  And so she does, but I must serve her every whim.  She allows me the privilege of wearing her panties.  I become her slave bitch.  She insists that I forsake any pretense of manhood if I want to wear her clothes.  I have to get my own wardrobe, and dispose of all my male clothes.  I am no longer allowed to wear anything the least bit masculine.  Only lingerie, dresses and skirts, and high-heeled shoes.  I must completely abandon my manhood.  But I already want this, even though I’m afraid to go out in public that way.  Eventually my desires prove far stronger than my humility.  So she insists that I bring her men to replace me.  And I do.  And I get men of my own, too.  I become a complete transsexual.  And I love every second of it.

Fiction: Devotion

Heidi was my goddess.  I worshipped the ground she walked on.  I collected and catalogued every one of the 594,391 photos of her I could find.  I humbly deferred to her every whim.  She was sometimes difficult to please, but I did everything in my meager power to satisfy her in every way possible.

I stumbled upon her when she had a photo shoot in the desert hills in Southern California.  I knew instantly who she was, from all the swimsuit issues and lingerie catalogues and calendars and so on.  Somehow, I caught her eye, and she had me getting her water.  Her photographic entourage waited on her hand and foot, and I got caught up in it, too.

We became very close.  She was so vulnerable.  She wouldn’t let me touch her much at first.  She was afraid I would just fuck her and leave her, bragging about it to my friends for the rest of my life.  I assured her that wasn’t so.  Still, she resisted.  Who was I to argue?  If I had to be patient for this one, the woman of every man’s dreams, I would wait forever.

Nonetheless I struggled to get her to become intimate.  She always questioned my dedication, even after a few months.  I had only kissed her a few times, and gotten to rub lotion all over her body for some photo shoots.  I had seen her naked many, many times, as she was perfectly comfortable changing in front of me.  I even got to gather her discarded bikinis whenever she needed to change into a different one for the next series of shots.  

She got to trust me quite a bit.  We started spending some intimate time together.  She made me do all sorts of things to prove to her that I truly did love her.  But she never fully bought into them.  They usually involved me making a fool of myself publicly.  Every time, I acquiesced without hesitation.  If I could convince her without a doubt that I worship her, she would surely relent.  When I thought of my ultimate goal of winning her heart, it was easy to agree to do anything.

At first, I simply waited on her.  I got her absolutely anything she wanted.  But that was easy.  She then made me kneel and bow my head when I brought things to her, and I did.  Happily.  I so desperately wanted to be worthy of her!  She had me singing love ballads to her at the top of my lungs on the spur of a moment.  She only had to look at me a certain way, and I would stand on my head for her amusement.  The more she got me to humiliate myself, the more readily I would do it, just to prove my deep, passionate lasting affection for her.  

She must have thought I would have been horribly humiliated about wearing her bikini at one of her beach shoots, with hundreds of bystanders gawking at her.  It was one of the biggest crowds I had ever seen.  Usually, they keep these shoots private, because it makes everyone involved more comfortable, and more open.  This time the photographer wanted to capture the crowded beach as a counterpoint to his shockingly beautiful subject.  Even in a sea of people, she would stand out.  And so, feeling shy about the mob around her, she asked me, very publicly, if I would try on her swimsuits first, not only so she could see what they looked like on others, but to deflect some of the spotlight from her so she could concentrate on looking beautiful.  

I had some difficulty putting them on at first, but she had some of her aides help me.  By the end of the shoot, I had no trouble putting on a brassiere.  It felt funny at first, wearing her sexy bikinis.  I always thought of women’s underwear as being innately sexy.  She said I blushed when she told me how cute I looked.  I liked the snugness of the panties on my crotch, and the delicate way they caressed my butt and my hips.  I knew I looked ridiculous, and that the entire crowd was laughing at me, but I didn’t care.  I was pleasing Heidi Klum!  I was the focus of her attention, after the photographer.  I was publicly humiliated, just for her, and I didn’t care.  I even made several of the local papers, and some worldwide news wires.  The world would henceforth forever question my virility, but I honestly did not care.  It was a worthwhile sacrifice for my Heidi.


Still, she questioned my commitment.  She was convinced that I would want to get back into my clothes the instant the shoot was over, so I could reclaim some of my dignity.  I proved her wrong.  I dared to beg her to allow me to continue wearing her bikini if it pleased her, and pledged my continued subservience, not in spite of, but because of her grace in allowing me to wear her sexiest clothes.  She frowned and thought about it for a while, then commanded me to wear my regular clothes.

Unfortunately, my readiness to humiliate myself at her every whim enticed a suspicion in her that I was only trying to get her to relent.  She began openly flirting with other men to test my resolve in the face of jealousy.  I steadfastly stayed by her side.  She rewarded me by continuing to allow me into her most intimate circles.  She had me bring her men, whom she would fuck right before my eyes; but when she kicked them out of her bed, she snuggled up to me and slept.  She told only me what was on her mind.  But she still didn't believe that I loved her enough.  She made it quite clear that if I objected to her sleeping with other men who she barely knew, it was proof that I only wanted her for sex.


It was one thing when she made me wear her bikinis in public.  It was quite another when I wore her lingerie in private with her.  To wear it in public is a public gesture, and can be seen as jest.  In private, alone with her, it has an entirely different connotation.  In her inner sanctum, I wear her panties and bras and corsets and stockings not as an easily dismissible joke, but as a sincere, intimate preference.  She could tell that I honestly adored wearing her clothes.  It felt like such a privilege to me to even touch garments that she wore, much less her skin-tight undies, least of all wear them!  To wear them was almost bliss.  I felt so much closer to her when I wore them.  I even felt sexy, in a dirty, feminine way that I kept secret from her.  Eventually, I thought it wise to throw away my own underwear and wore only her hand-me-downs, to show my devotion.

Still, Heidi, my precious Goddess, was not satisfied with me.  She wanted nothing less than complete uninhibited surrender.  I was more than happy to comply.  The hormones I had started to take to better shape my body into her lingerie were beginning to kick in around this time.  My brassieres began to become fuller, and I became quite adept at arousing her boyfriends with my skill at fellatio.  It had become quite clear that I could only do one thing to prove to her that I am not doing this just for sex.  They say that imitation is the sincerest form of flattery; I naturally began abandoning my inhibitions and devoting myself to her worship.  I proudly began to eradicate any vestige of myself, and dedicated myself to becoming her.  I changed all my makeup and began to style my hair like hers.  

The plastic surgery molded my face into hers.  I walked and talked and moved just like her.  If not for the little nub of my pathetic little dick, which she wouldn’t allow me to remove, we are practically twins now.  She has sent me to stand in for her in some of her shoots, and nobody knew the difference.

Only after they replaced my genitals did she trust me enough to fuck me.