Fantasy: Hair of the Dog

How about this scenario: I am me.  I wear women's underwear every now and then just for fun, but it stays in the closet.  I'm found out by my girlfriend, who dumps me.  I am alone, and ashamed.  I truly loved her, and I feel awful about her leaving me.  And I miss her lingerie, too.  So I vow to never wear women's clothes again.

Of course, as always, I fail.  I know that it's impossible to change this proclivity.  I keep succumbing to the urge.  Until one day, I finally decide to do something drastic about it.  So, I say to myself, you want to wear women's clothes for fun, eh?  Well, we'll see how fun it is if you wear them all the time.  So I start wearing women's underwear exclusively, hoping that I'll get sick of it and stop.  Only it has the opposite effect.  I wear it all the time, and I get so used to it, that I can't do without it.  I come out of the closet forever as a girl, just because it's just too fun to give up.

Fiction: After the Harem

Or worse (to continue the above idea): the girls get a two-headed dildo, and they all get to fuck me up the ass with it.  The ultimate revenge!  They get to rape me and demean me even worse than I did to them.  Some are violent, some are tender, some are clumsy, some are expert, but all of them do it at least once.  I get no chance to rest: as soon as one is done, and she extracts her dildo from my ass, another comes right back in.  It's the most incredibly outrageously demeaning experience that any human being has ever lived through.  And it affects me deeply: once it's done, and I become a prissy little faggot willingly wearing women's clothes, I slowly work my way back to the top of the heap.  I am one of the girls now.  I convince them that I should be an example to all rapists.  They should all suffer as I have, and that's the only way they'll learn to respect women.  I work as hard as I can to effeminate myself, taking even the most extreme measures.  I take hormones and grow my own tits.  I conceal my dick as much as I can.  I am a total she-male.  I start to look like an Amazon sex-goddess.
Eventually, we start capturing convicted rapists.  We dress them up and fuck them up the ass.  I am usually the first to get in there.  I don't need a dildo, and I resent that; I make sure that these men feel it worse than I ever did.  I make them so effeminate and so docile that I have them competing for who gets the privilege of sucking my dick.

And it grows from there.  Our ranks swell so high from all of our rapist converts, who are forced to undergo sex-change operations and become girls too, that we decide to expand.  Our vigilantism grows to include all criminals, as far as jaywalkers and litterers, and even parking ticket offenders.  Then it's all men.  All men must learn to respect women.  All men must become girls, feel silk and satin on their nipples and cocks, and get dildoes and penises up the ass.  There is no longer any excuse: everyone must wear women's lingerie, and strive to be a beautiful woman.  To do otherwise is a crime.  I become even more powerful than ever, and I do it as a girl.

Fiction: Revenge of the Harem

I'm rich.  But I don't like to go out much.  That's why I keep my harem.  They're here for life.  They never leave.  I have my way with them whenever I want, and they can bitch all they want about it, it won't change.  They're my little sex slaves.

Typically, I tie them up naked, spread eagled and gagged on this contraption that I've got. It's like a roof on my bed.  I tie them to it so that they face the mattress, and come down to get fucked whether they like it or not.  I've even climbed up and hung off of them as I fuck them, so that they're fucking in mid-air.  It's quite a bit of fun.  They all hate it at first, but they eventually start loving it.

Then one day, the tables turn.  They somehow organize a revolt, and they capture me.  But they don't want to kill me.  They'd rather embarrass me.  They disable me, remove all my body hair, and strap me into some of their lingerie and then into the machine, where I can't move.  I'm wearing silky undies, a matching bra and garter belt and black stockings.  They take pictures of me, stare at me and laugh, and hurl insults at me.  They call me a sissy.  Then they bring in the real torture.

They bring in some strapping young faggot.  Essentially he does to me what I did to the girls.  And they all watch and hoot and holler and love the show.  He fucks me up the ass, in the mouth, the whole bit.  He even fondles my nipples.  He keeps my panties on, so that I don't forget who the girl is in this relationship.  He even whispers in my ear that I'm his little pretty girlfriend.  As he fucks me, he fondles my pantied crotch.  The girls cheer the loudest when I finally come.  I just feel so effeminate.

This goes on infinitely.  I'm imprisoned, and I'm forced to wear women's clothes only.  And every day, I get strapped in and fucked, just like my girls used to.  I start really enjoying it, too.  I start looking forward to it.  I start making myself as sexily effeminate as I can.  I start dressing myself up, rather than being forced to.  I willingly suck his dick.  I become his little private sex whore.  And I feel very feminine and proud.  The girls have their revenge.  

Diary: Deep Questions about Limits

I think that's about finished.  It was pretty exhilarating to write.  For the first time, I managed to make myself come using my hands.  And I did it more than once, too.

This story brought to mind one of those interesting deep questions: if you could experience the most prolonged and intense sexual experience conceivable, knowing in advance that it would be 100 times better and longer than any sexual experience you've ever had, and knowing that it would destroy your sexuality irrevocably so that you could never have sex again, would you do it?

I can't even answer that myself.  It's a very difficult question.  I'm leaning towards quantity right now, rather than quality.

One thing I had thought of as a kid when I used to fantasize about becoming a girl by wearing women's clothes: literal emasculation.  I had this fantasy that girls would capture me and force me to wear their clothes to effeminate me a bit.  To add injury to insult, they would then chop off my genitals in preparation for a sex change operation, and force me to eat my own penis.  I don't remember anything about my balls, but I do remember having to eat my own dick.  Cooked like a sausage.  I ate it, too, and became a girl.

It's a bit raunchy, isn't it?  Not too stimulating, either.  How could I be mortally embarrassed if I didn't still have my dick swishing around in effeminate silk?

More raunchiness: homosexuality.  There was a time when I fantasized about fucking men as a girl.  It doesn't really turn me on all that much, but there's that guilty aversion to the effeminacy associated with homosexuality.  In other words, I started thinking about having a cock up my ass, or in my mouth, as I acted like a girl, and it made me feel that much more effeminate.  Because that's what girls do.  But I felt guilty that it turned me on, and so it turned me on even more-much as wearing lingerie does.  Right now I can picture myself all dolled up in lingerie, feeling all proud, and even horny, as a man snaps the elastics on my panties.  I get all excited as I suck him and fuck him.  Even though I'm still male, and I'm only wearing women's clothes.


Finally, there's another story in me, one that combines all sorts of very nasty, sordid, and most unsavoury sexual acts...