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.