I am wearing my Speedo

It's certainly much too small and tight, but the sensation is excruciatingly sexy. I have it stretched as much as it can, and it's cutting into my crotch a bit, but the leg cut goes above my hips. When I walk in it, it forces me to swing my hips girlishly because of the way it moves on my body. I'm tempted to run around town wearing it under my boy clothes, just to enjoy the sensation of it. I want to go for a swim in it.

I sure wish I looked more feminine.

Anticipation

Yesterday evening, I found myself with a bit of spare time and some freedom. On an impulse, I decided that this would be the time to buy the damn swimsuit already.

I had just eaten dinner with my fiancee. She was off to do some homework, and I had an appointment an hour later. The moment we parted ways, I knew that I had a golden opportunity to execute my plan.

I had already scouted the wares of a sporting goods store near my home. I had images of a black and red racing swimsuit, and I was excited about it. I had a twenty minute drive, and lots of time to ponder my coming adventure. I twitched with nervousness. My stomach bubbled and churned. All the same, I was determined to fulfill my twisted little fantasy.

I strode purposefully, my legs shaking, through the mall and into the store. As I walked in, a hot, shapely young store clerk walked in front of me, crouched down, and folded some clothes, exposing the upper part of her butt crack. I wandered around the men's clothing section, pretending to be interested in a shirt. I considered leaving, but I took a closer look at the women's swimwear section, and boldly headed in that direction. I slowly walked past it and into another display of discount men's t-shirts, no more than ten feet away from what I was really interested in.

The store was virtually empty. There were a couple of teenagers looking at baseball equipment, but quite far from my position. I snuck furtive glances at the object of my desire. Slowly, I made my way towards them, pretending that I wasn't interested. Finally, I dropped my pretenses, and started pawing at the swimsuits.

At first, I felt like an idiot standing there, fondling women's swimwear. But nobody was near, and I decided that I didn't care anymore. I took my time. I had no idea which size to take. I inspected a fiery red one, but rejected it for fear of drawing too much attention. The black and red I thought I had seen did not exist. There was a red and navy, but I didn't care for it. I needed black, primarily, and there were plenty of those. Finally, I settled on a black Speedo, size 6, fearing that it would be a bit too large. I folded it in my hand, trying to cover up my shameful purpose, and made my way to the cashier's counter.

I asked the girl at the counter a question about their return policy. It was the perfect cover. She gave no indication of finding it strange. I paid for it and walked out, less nervous but sick with anticipation.

I had little time to examine my purchase, much less try it on. I stuffed the shopping bag into the bag I was taking to my appointment, for fear that my finacee would find it if I left it behind. I anticipated that I would have time to play when I returned, imagining that my fiancee would not be coming over.

When I arrived, I shook with eagerness. Still, I had to resist. I had no idea whether or not she was coming. I started developing my fantasy. An hour into it, she suddenly walked through the door. I was shocked, and thanked my stars that I hadn't exposed my secret. Moments later, I fucked her in the bedroom, and we went to sleep. I had trouble keeping it up, because I was so much more interested in my secret stash.

All day today, I dreamed about the tiny amount of time I could have with my precious swimsuit. I was feeling somewhat disappointed that it wasn't the black and red I had originally imagined. I felt ridiculous for risking my relationship with my fiancee for a piece of clothing, a sex toy. Still, I couldn't help but reminisce on all the lovely things I had worn in the past, and how often. I looked forward to trying it on.

I had dinner with my fiancee again, but it was very difficult to free myself of her. When I finally succeeded, I rushed home, aching to complete my adventure. I tried it practically the moment I walked through the door. It was incredibly tight, especially around the waist. Somehow I managed to squeeze into it. I luxuriated in it for a few moments before struggling out of it again, afraid of being caught. I would have to be careful. I hid it in a secret place, and started writing this.

Unfortunately, I'm not very horny right now. I don't know why. Now that I have my swimsuit, I'm not particularly keen on it. I want another one.

I would love nothing more at this moment to repeat the exhilaration I felt browsing for women's bathing suits. I want to take more time, try a few on, find the right colour. It was fantastically exciting to do something so plainly perverted. I would rather have a slightly larger swimsuit.

Really, I just want more. I'll wear it again when I have some time to really concentrate on it. It should be fairly soon. Or maybe I'll play with some panties, or the bikini, which I have had access to all along, and come to it later. The beauty of it is that I have my own swimsuit now, and I can wear it whenever it's convenient.

Maybe I'll buy more, just for the thrill of it.

The Trouble With Having a Secret Identity

I've been obsessing about one-piece swimsuits for the last few weeks. I get like this when I don't have access to something I want to wear. I can't get it out of my mind, and it dominates my fantasies. Somehow, I always come back to this. I have a bikini dangling in the closet, just begging to be worn, but I'm not interested. I'm sick of it, having worn it no less than a couple dozen times. I'll wear it again, but I want something different now.

Like all feminine clothing, I want to wear it because it accentuates women's shapes. I want to morph into that shape myself. I want to feel what it's like to be female, inside that stretchy, soft fabric. I sweat just thinking about it. My fantasies take off like a rocket: fast, and straight up into the heavens, without a thought about practicality.

The main problem is that I don't have any access to a one-piece swimsuit. My fiancee doesn't have one (although she does have five bikinis, all of which I've secretly worn) so I'm unable to indulge. I'm formulating a plan to buy one, but it's not at all easy for me to do it. I can't allow anyone to know what I like to wear. I know that it's not all that big a deal, but I'm incredibly shy about buying my own girlie outfits. I've done it so many times by now, that you'd think I'd have no problem doing it. Only twice has anyone ever given me any kind of indication that they suspected what I was up to -- a terribly disheartening experience -- and one of those incidents occurred when I bought one of the many one-piece swimsuits I've owned (the other was about a bikini). Oddly enough, it's ok for men to buy lingerie for their lady friends, but not swimwear. Therefore, it's harder to explain. Nonetheless, I have bought as many as three swimsuits at one time for myself, and the clerk was completely convinced that I was buying them for a woman.

There's simply no way to escape questioning glares from clerks and other customers. I can spend many minutes circling the women's swimwear section of a store until I can summon up the courage to enter it. By then, I've already aroused suspicion from store employees wondering what I'm doing. Then there's the long, painful moments while I walk around the racks, looking for whatever it is I'm fantasizing about, not touching anything. Finally, if I've managed to get even that far, I'll start picking things out of the rack, my mouth dry like a towel, my face burning with embarassment. I'll look at colours, styles, prices, and will have a very difficult time deciding which one I like best; even more difficult is making the decision to pick it up off the rack, walk to the cashier's counter, and buy it. More often than not, I'll be standing in line with a bathing suit in my hands, obvious to anyone within fifty feet of me. Even if I buy something masculine to cover it up, it always shows. Finally, since there's no turning back once I'm in line, I'll reach the counter, where the cashier will confront me. Usually, there's no trouble. But sometimes, I'll get a dirty look, or a blush and a giggle. All that remains from there is the trip to the car with the swimsuit in a hopefully opaque bag.

Today I wandered around a sporting goods store, and didn't have the balls to browse the swimsuits. I made note of the section's location when I walked in, took the most roundabout route to get there, and just pretended that I wasn't interested. I did, however, notice that all of them were shaped just perfectly, with the racer back that I so desperately want. A black and red one even caught my eye, but I just walked right past it. I don't even know the price.

I could be wearing a sleek black and red racerback one-piece girlie swimsuit right now. But I'm not, because I'm a coward, and I'm ashamed of my secret fetish.

Eventually, my desire will be so overpowering that it will conquer my fear, and I'll have my precious swimsuit.

A Strange Dream

The other night I had a strange dream. I entered a bedroom at a house party, and on the bed was what I first thought to be a thin woman with a long manly nose, wearing a black teddy, and barely containing her ample, alabaster breasts. Then somehow, I recognized her to be myself. I asked her if she liked being female, and she answered softly, 'Yes.' I pressed her to confirm, because I knew that she used to be a man. 'I love it!' she answered, purring like a big cat. I then proceeded to make out with her.

I'm not sure that she was really me, but I felt like I was controlling her like a puppet. The words she spoke were mine. The thoughts and ideas behind them were mine. These thoughts were much more complex than the words might imply. They paused on how my Mistress would feel if I said anything but yes, and added that I loved it not only to please her, but because I realized that it was true. That's when I started necking.

Then the dream dissolved, and I don't remember anything else.

I think that while I fucked my fiancee that night, I imagined sucking cock.

Bathing Suits

There's something particularly sexy and feminine about women's swimwear. I could never quite put my finger on it. Lingerie is wonderful and sexy, too, but somehow, it doesn't make me quiver with desire like a nice bathing suit.

When I was a bachelor, I used to have no fewer than 5 bathing suits. I had a blue one-piece, which I wore more often than anything else, a red one-piece which was quite a bit too small, a hot pink string bikini, a silver bikini meant for serious swimmers, complete with a full bra, and a white thong bikini with lacy trim that covered practically nothing. I had lots of other stuff, too, including panties, a corset, stockings, garter belts, and a patent leather mini-dress. I wore all of it extensively, if privately, but especially the blue bathing suit.

There was nothing special about it. For some reason, I always went back to it. I don't think it necessarily made me feel more feminine than, say, the outfit I wore with the mini-dress (usually my black corset, black satin panties, garter belt, and fishnet stockings), but it was much more simple. It was a single item of girlie goodness that I could slip into and instantly feel like I was betraying my gender. The other stuff always made me feel like I needed to put on more: panties alone were never enough without a bra, and the garter belt would always get messy when my feminine fantasies became too much to bear. The one-piece bathing suit was excruciatingly, unmistakably female with very little effort.

Sadly, I had to dispose of all of it when my girlfriend moved in. I certainly didn't want her to find it. Now I secretly wear her stuff, but unfortunately, she has only two-piece bathing suits. Granted, when we met she only had two, and now she has five, but I desperately miss wearing a one-piece. There's something amazing about that soft, tight fabric, stretched over my waist, shaping me like a girl. Someday, I will have another.

Getting in the mood

It seems that every time I'm alone at home, I can't help but get excited. My first impulse is to rummage through my girlfriend's dainties for something sexy to wear. If I know I have lots of time, I'll fantasize about it for hours, usually by writing dirty stories. You've probably guessed already that she's gone now. I think I'm going to wear her bikini again. I swear that I've worn it much more often than she has!

Hello, world.

Welcome to casualtranny. Just remember, all of this is a big secret. I would never admit publicly to anything I'm going to say here. This is a testbed for some kinky ideas I have always had. This is the painful first post.

Enjoy!

Fantasy: Contrived Innocence

(A contrived situation where I somehow find myself innocently in women's underwear)

So here I am, wearing this one-piece women's swimsuit.  It's not even remotely masculine.  It can't in any way be mistaken for anything but a woman's swimsuit.  The shape, first of all, is meant to accentuate hips, butt, and tits.  The leg is so high-cut it's almost to my waist.  My cock and balls are squashed snugly by the crotch, which is meant to contain nothing at all.  The lycra is soft.  It's got wires where my boobs should be, for support.  And the colour doesn't help me much, either: it's primarily pink, with little flowers.

The first time was innocuous enough.  I didn't know the speedos I had on were actually a female bikini bottom.  I should have known from the lack of drawstring, and the way it hung off my hips, and seemed so high-cut.  Otherwise, it was just simple navy blue.  I hammed it up when I was told.  I pretended that I wasn't mortally humiliated about being out in public wearing nothing but a woman's bikini bottom.  I pretended that my manhood wasn't permanently and irrevocably destroyed.  I don't think that I knew, however, how much I loved the idea.

I guess the fact that I didn't immediately change out of it didn't help.  I tried to keep my composure.  Not that it would have mattered, though.  The seed was planted.  I wondered immediately how it would feel to wear the matching top.  The thought put a weird itch in my cock.  I felt like I was the centre of attention, and I liked it.  Above all, I loved the way the bikini panties felt on my body.  Maybe keeping it on had less to do with keeping composure than with girlish pleasure.

When we got home from the beach, me still in my bikini panties, I thought about how it would feel to slip into some silk panties after my shower.  With lace trim.  And a bustier.  Stockings.  3-inch heels.  I wanted more.

So now as I prance around in this floral swimsuit, at the beach once more, gushing with pride as I explain how wonderfully erotic it is to be feminine, envying all the pretty girls for their sexy outfits, I can't help but think: damn it, this swimsuit, in spite of its feminine cut, girlish colours, and luxurious softness, isn't anywhere near feminine enough!

At first I denied it, but it only made me want it even more.  It started that first day, when they asked me if I was going to make a habit of wearing bikini bottoms.  I vigourously denied it, but the thought aroused me.  By the time I heard the 20^th joke about my mistake, I angrily defended myself, while at the same time inwardly swearing to never wear anything masculine again.  I practically pictured it fitting me the way it was meant to, if you get my drift.

Naturally, I tried to return the faulty panties to the store, but they informed me that they don't accept returns of bathing suits that have been worn.  I begged them to let me exchange it, but they refused.  I ended up buying the matching top, and a one-piece that I tried to exchange it for.  I couldn't wait to get out of my boy briefs!

It didn't take more than a couple of days to get used to walking in heels.  Finding my size was a hassle, but it was worth it.  I couldn't be feminine enough.

Now I tell people, in between mouthfuls of cock, that I fantasize about having my own pussy.

Fantasy: Tricked

To be tricked...

There's something to be said about the idea of being tricked into wearing something feminine, and immediately becoming ultra-obsessed with becoming a super-sexy ultra-feminine girl.

I want to beg for a scrap of feminine attire.  I want it so bad.  I want it to transform me.  I want to utterly forsake my manhood, and become all soft and curvy.

I slip into the bathing suit, feminine as it is.  She giggles.  By the time I've strapped myself into it, I know that something's gone horribly wrong.  It feels like nothing I've ever worn before.  It's soft, and tight all over my crotch and hips and especially my waist.  It's incredibly high-cut, compared to anything I've ever worn.  It's snug around my chest, and the straps on my shoulders keep me snugly inside it.  It clings to my body.  Much to my surprise, it actually feels feminine.  I am picturing her in this very swimsuit, and getting very excited.  I am extraordinarily aroused.  It suddenly occurs to me that what I'm doing is incredibly gay.  As if on cue, she comes to me, and presses her gorgeous panty-clad body against me.  She slaps my ass.

Some inhumanly powerful urge comes over me.  I want to rub my penis all over her.  But at the same time, I don't want it there at all.  I want her to fondle my nipples.  I giggle like she did earlier.  I'm rubbing my crotch over the bathing suit, and squirming around like she does when I finger her.  I want to wear her lingerie.  I want to wear her fuck-me boots.  I am ecstatic with feminine pleasure.

She asks me if I want to be a girl, and to my shock and horror, I answer affirmatively.  And I mean it.  My shock is mainly from the surprising realization that I love the idea.  In a split second, I fantasize about wearing bikinis, panties, bras, stockings, nightgowns, mini-skirts, and all sorts of glorious shoes, all of which aren't nearly feminine enough.  She lets me try on some stockings, even though they clearly don't match my swimwear.  She offers me a corset and a thong, and I take them reluctantly, unwilling to remove this glorious bathing suit.  But I give in, suspecting that this new outfit will be even sexier.

By the end of the night, I've impulsively thrown all of my masculine attire in a garbage bag, and ostentatiously walked it out to the curb, in full view of my neighbours.  I have promised her that from this moment forward, I will wear nothing but the skankiest clothes imaginable, and strive to become as feminine as possible.  She has me ritually forsake my penis, and all manhood, forever.  I moan the words emphatically.  I fall asleep in a silk nightgown, and dream of sucking cock.

When I wake up, I regret what I've done.  I feel ridiculous in my feminine outfit.  I have nothing to change into.  I lament how incredibly gay I've been, and suddenly become aware again of how much I loved it.  Soon I find myself trying on boots again. 

Fiction: Photo Shoot

The fantasy is the same as always.  Different articles of women's clothing make me succumb to become ultra-feminine.  I become a cheerleader for the LA Clippers.  I am coerced into competing to become feminine.  I single-handedly betray my entire gender when I chose femininity over masculinity. 

For whatever reason, I find myself in the position of having to choose, and I can't help but choose womanhood.

No, here it is:

I'm walking around in public, minding my own business.  Some guy comes up to me and asks me if I'm there for the photo shoot.  "Photo shoot?" I ask.

"Yeah, aren't you one of the models?"

"Um, no..."

"Oh, I'm sorry.  I thought you were here for the shoot.  We've been waiting 40 minutes for our guy to show up, and so far no sign of him.  Say, would you want to try it out yourself?  We'll make you a big star!"

"No, thanks."

"Seriously, you're even better looking than the guy we actually were gonna pay to do this."

"Whatever, pal.  See ya."

"Come on!  We'll give you his money!  All you have to do is pose!"

"How much money?"

"Five grand."

"Guaranteed?  No strings attached?"

"No way!  We don't just pick up anybody off the street.  Come on, we're desperate, we're late, and we just want to get this done already.  Are you in or not?"

"Wait a minute.  You promise there won't be any bullshit?  I want half the money up front, or I walk.  You're just some salesman trying to trick me into some bullshit that I'll end up having to pay for."

"Fine," he says, counting twenty-five hundred dollar bills in front of me, and putting them in my hand.  "Now just go stand over there, and Tracy will take care of you."

Dumfounded, I do as he says.

Tracy sends me down the hall.  But I spot a ridiculously sexy woman in lingerie up ahead.  I figure, what the hey, even if it's not where I'm supposed to be, I've already got $2500.  All I want to do is look.  I'll just pretend that I'm there for the shoot.

She looks so hot in her stockings and bustier and undies.  She even has a feather boa.  Inside are a whole bunch of other scantily clad ladies.  I stand there for a full minute staring at all the pussy lounging around in that room.  A photographer has one girl on a bed, striking bawdy poses.  It takes a while to register that some guy with a clipboard is trying to get my attention.  "Hey, buddy, if you're not part of the shoot, then get the hell outta here!" he says.

"Um," I stammer, "I am part of the shoot."  I hand him a slip of paper that I got from Tracy, who sent me in this general direction in the first place.

He glances at it for a while, and sizes me up.  "Ok, sweetie, then you'd better get into costume quick."  With that, he shuffles me to a dressing room.  Inside are Betty and Monica, who are middle-aged but trying hard to be pretty.  Betty wears a thick black apron, and Monica has a blow dryer in one hand, and a measuring tape around her neck. 

"Come in, come in, sit!" beckons Monica.  So I come in and sit.

"It's truly amazing," says Betty.  "You'd never suspect some of these guys, would you.  Honey, we'll make you a superstar."  They immediately go to work on me.

It doesn't take long for me to realize that they're trying to apply makeup.  I try to stop them.

Monica scolds me.  "Listen, honey, just because you're getting paid $50 grand to show off your girlie side doesn't mean you get to treat me like a peon.  Just tell me what you want me to do, but don't give me this bitchy attitude, ok?"

"Fifty grand?!?"

"Oooh, sorry if it's more.  I didn't realize the caliber of superstar we're dealing with here."

I look at the slip of paper.  I am shocked to discover that it is, in fact, a contract for fifty thousand dollars.  As well as for five.  It appears that I have indeed infiltrated the wrong photo shoot.  There are two items on the schedule.  The first offers five thousand dollars for a standard men's magazine aftershave feature.  The second offers fifty thousand dollars for transvestites for an adult website. 

I am faced with a rather interesting dilemma.  Do I flaunt my boyish good looks, and increase my chances to score with ladies when I tell them I am a model, and pocket a month's worth of pay?  Or do I abandon my manhood for just a brief moment and take home a whole year's worth?  Not much of a dilemma, really.

Nobody will ever know about it, except the people here.

"You know," I say, "I'm a little unprepared.  I'm sorry, I haven't done this in a while.  I don't even know where to begin.  Why don't you two girls just go to town on me, and hopefully I'll turn out ok?"

They grumble, but they start to work.

First, they demand that I strip down.  They shake their heads and tsk-tsk at me.  Before I know it, I'm covered in depilatory cream.  They rinse it all off after the requisite amount of time has passed.  My body hair and facial hair are gone, without a trace.  My body feels chilly from the lack of insulation.  I am suddenly ridiculously smooth and sleek.  I'm beginning to wonder if this is such a wise decision.  But then I remember the payoff.

"Why don't you choose your outfit?" asks Betty.  "You fellas are usually pretty picky about this kinda thing."

I am surrounded by racks upon rack of lingerie.  I don't even know what to choose.  I am aroused at the sheer femininity around me, but too nervous for it to show.  I hesitate around a poofy lacy white bra.  I even hold its hanger in my hand for a minute.  "Hurry up, we ain't got all day," admonishes Monica.  That's when I notice that it's actually a bustier, with straps for stockings, and a matching full-cut boyshort type panty that's so lacy it's an insult to call it boycut.  Before I know it, they're helping me into it.  The bustier is acts as a corset, so it's difficult for me to strap myself in.  Betty hands me a package of white nylon stockings.  I put them on clumsily, and marvel at the sensation on my legs.  Betty hands me some white heels, which I slip onto my feet daintily, in spite of myself. 

I look into the mirror, and find myself shockingly sexy.  When I tuck my cock between my legs, I look positively female, from the neck down.

Betty sits me down in the chair and starts working on my face.  Monica starts working on a blonde wig on the sidelines.  In the end I look like a juicy little whore with far too much makeup.  I can't believe what a great job they did making me look like a woman.  I'm actually sexy!

"My, aren't we the little princess!" says Monica.  I'm not sure whether she was mocking me or not.  There was a tone of respect in her voice.  "Now go out there and knock 'em dead!"  She places a sheer robe over my shoulders and pushes me out the door.

The guy with the clipboard ushers me to a bevy of women such as those I had previously observed.  "You're number 19.  Just stay here and wait your turn."  Of course, upon closer inspection, I can see that these women are actually men in drag.  I'm not sure whether to whistle or cringe.  Two of the five look at me jealously.  The others are much too happy in their outfits to be anything but welcoming.

I can't help but look at myself, and admire what I'm wearing.  This is the kind of outfit that I've only ever dreamed of having one of my girlfriends wear.  And here I am, decked out in it like a strumpet, looking every bit as sexy as any girl I ever dated.  I can't help but rub my thighs together when I walk, for the sheer pleasure of the sensation.  I'm very nervous.  I never thought I'd allow myself to be caught dead wearing women's underwear.  The idea always seemed so revolting to me.  But in the end, it's not so bad, especially since I'm getting fifty G's out of it.

I can feel all kinds of eyes on me.  The other "ladies" are talking amongst each other about their favourite outfits and so on.  I have nothing to offer.  They're such flamers.  Their every gesture is so unerringly feminine.  I feel out of my depth.  I keep my distance, hoping that none of them will come on to me.  I concentrate on thinking of what I will do with the money I'm making.  Even though I'm standing around in women's lingerie with a bunch of flaming transvestites, and at least a dozen others, too.

I get to watch all of the other "girls" pose.  A few others show up behind me.  They're disturbingly awkward as they camp it up, trying to be girlish.  The photographer acts like it's a real photo shoot, with real hot girl models.  At least I get some ideas for what I'm supposed to do when it's my turn.  I hope they can't tell that I'm just a straight guy doing this for the money.

Finally, it's my turn.  I stumble onto the platform, since I've never walked in heels before.  I'm horribly embarrassed.  Everyone is looking at me!  And I'm dressed like a girl!  I'm standing there, immobile, petrified. 

"Come on, baby," cajoles the photographer.  "Don't be shy.  Just be yourself, feel natural!  Show me what a sexy little tramp you are!"

He starts snapping photos.  "Yeah, I get it.  You're the shy little debutante, aren't you?  Yeah, that's it baby!  I like it!  Yeah, be coy, look away from me like you're afraid of me!  Yeah, that's working, baby!"

I notice that I'm not even looking at the camera, and I'm shyly covering up my shameful outfit.  I'm crossing my legs, and feeling the stockings on my thighs.  Everywhere I touch, there's silk or lace.  Oh my God, what have I done!  Is this worth fifty thousand dollars?

"Yeah, baby!  Touch yourself some more!  That's what I want to see!"

I'm gently moving my hands over my hips, over the gentle elastic of the lace.  I've never felt anything like it.  I'm picturing Vanessa's body in my mind.  I'm touching all of her best parts, like her waist, her hips, her flanks, her boobs, her butt.  I'm shaking my hips to the beat of the music. 

"Oh yeah!  That's it!  Get into it now!"

I'm dancing around a bit now, barely moving my feet, but rubbing my silky legs together.  I'm feeling it now.  I can't stop it.  I'm moving my body delicately, pretending I'm Vanessa, doing the little striptease I've always wished she'd do for me.  I'm luxuriating in this fancy lingerie.  I feel dirty.  This is so wrong!  Not only am I dressed like a girl, never mind a skank, and not only am I being photographed, but I am actually enjoying it!  To think that I'm getting a small fortune for it to boot!

Finally, the photographer puts a stop to it, having used up a roll on me.  Some other clipboard guy ushers me off the stage, and directs me to Jen, who stands by a table, handing out cheques.  I stride over to her confidently, and put out my hand.  It is with great disappointment that I notice a zero missing from the sum.

"Five thousand?  I thought I was supposed to get fifty!" I squeal.

"Well then, you shoulda gone to the aftershave shoot like you were supposed to!"

"What the Hell!  It says on the schedule that transvestites get fifty!"

She shows me the little checkbox on the contract that shows that I signed on for five thousand dollars.  "It's in your contract, sweetie.  Better luck next time."

She turns around, and I'm about to shout back some witty retort, when I realize that I'm standing around, arguing with a woman while wearing sexy lingerie and a wig. 

Mortified, I skitter back to my dressing room, clopping along in my pretty white heels, almost in tears.  I whip out of my clothes as fast as I can, ashamed that I'd been tricked into compromising my manhood for a mere five thousand dollars.  I want to rid myself of every trace of my error.  Only I struggle to get out of the corset, and Betty and Monica have to stop working on some other, more seasoned trannie to help me.

Even after I put on my pants, I don't feel quite right without my body hair.  It looks like It'll be a while until I can forget all about this. 

I'm about to storm out the door when Betty hands me a bag.  "Don't forget your clothes," she says.

"What clothes?"

"Duh!  You get to keep your lingerie, you know.  You think anybody else wants to wear it after you?"

I sheepishly accept it and go on my way.  I toss it in a dumpster behind the mall.

[A few weeks later, as I rummage through my closet for a particular sweater, I notice an unfamiliar white bag.  I peek inside it, and am shocked to discover my lingerie from my photo shoot fiasco.  I almost faint from the rush of shame.  I hold up the panties, and admire the flowery lace design, and the sexy cut.  I shudder to recall the greed that led to me prancing around for a camera in something that feminine.  Could it be a coincidence that Vanessa and I aren't getting it on so well ever since?  It was very difficult to explain the loss of hair.  I never did own up to what I did.

With heavy heart, I toss the panties back into the bag, and walk out to the kitchen, and]

A few weeks later, I notice a large manila envelope with an anonymous return address, sent to me, in my mailbox.  Inside is a set of five photo contact sheets of what appears to be a scantily clad woman.  Upon closer inspection, it becomes clear that it's not a woman, but me.  These are the photos from my shoot!

Along with the contact sheets is a note from the photographer, offering me prints of any size for a fee.  He also mentions that I've been a hit on the website, and that they'd be happy to photograph me again for "another cool $50 K". 

Again, my face reddens, but this time with rage.  How dare they rip me off like that!  And rub my face in it by offering me proof of my shame at a price!  I throw down the offending documents and storm off to my computer.  I want to see what they've done with my photos.

I turn up a little ways down their front page.  Apparently, I was the "Sissy of the Day" for July 23rd.  I rated a 7.3 from viewers of the site, which is crawling with images of shemales and transsexuals.  I must admit, I do look awfully feminine.  I look far better than most of the other "girls" on the site, although some of them are astoundingly beautiful.  But I can only see one photo, as the other 12 are available to members only.

I don't feel so bad if my photos are not particularly widely available.  Thank God Vanessa still knows nothing of this.  We've been having so much trouble since then.  I just haven't felt quite like the man I used to, and she's gotten antsy.  I don't think she bought my excuse for the loss of my body hair.  I guess I'm still depressed about having been tricked so badly.

I lost out on forty-five thousand dollars!  Giving up my manhood for five thousand certainly wasn't worth it, but I doubt I would feel so badly if I had actually gotten paid properly.

Now, I know that I should know better, but they are offering to pay me fifty to shoot me again.  I've done it once before, and it's my own blunder that cost me the full amount.  What harm could there be if I did it again, and got the full amount?  I might as well get my due.  Consider the first incident a loss, but the second makes up some of it.

Naturally, Vanessa is not to know.

Lucky for her, I'm uncommonly horny that night, and fuck her brains out.

In the days leading up to my appointment, I excitedly scout around for some sexy outfits.  I look at all sorts of pictures from lingerie vendors' websites.  I get excited thinking about how sexy those girls are.  I know that I have to take a hit to my manhood, but for fifty grand, it's cake.  I'll have them in mind when I prance around on the stage, and it'll be over before I know it.  Easy money.

The same people are set up in the mall.  The guy who shanghaied me into this to begin with doesn't even recognize me, but he does a double-take when he sees what I'm signed up for.

"Didn't you do an aftershave ad for us?"

"Um, no.  I mean, yes."

"Heh, well here it has you signed up for the transvestite lingerie shoot.  Somebody's clearly fucked up somewhere."  He says this loud enough for everyone within a ten foot radius to hear him.

"No, that's right," I whisper.

"OK, I'll switch you over to the deodorant ad."

"No, I mean it was right before."

"What?"

I'm straining to keep my voice low, but he's not hearing me.  "The lingerie," I say with clenched teeth.

"You're here for lingerie?!?"

"Yes."

He looks at me for a long time.  A few other people are staring.

"OK," he says, finally.  "Lingerie it is.  Now go see Tracy by that door over there."

I walk timidly over to Tracy, who is trying not to laugh.  "OK, Lingerie is suite 233.  Here's your contract."

I look at it closely this time, and sure enough, they are trying to rip me off again!

"Hey," I shout, "this is for only ten thousand.  I thought I was getting fifty!"

"In one shoot?" she replies, incredulously.  "What are you, nuts?"

"That's what it said in the letter you sent me!  And that's what you were going to pay the first time when you ripped me off!"

"Read the contract!  It says you'll get up to fifty after four shoots, if your site gets the enough hits.  According to our records, you're only a tier 3, so that means ten grand.  Take it or leave it!"

Another difficult decision.  They're certainly tricking me again.  But it's also better than five.  I'm already here, and all these people already know why I'm here.  I'm not happy about it, but I didn't come all this way for nothing.

"Fine.  I'll do it."

This time, I take more time to pick out an outfit.  I was particularly smitten with a photo of Carmen Electra in a silver teddy with a furry trim, but they had nothing like it.  I had so many hot women in mind, but the selection of lingerie was somewhat limited.  I felt like I was shopping for Vanessa.  I couldn't help but remind myself that I would be wearing it.  I settled for a sheer black babydoll, silk string bikini panties, fishnet stockings, all with red bows, and knee-high black fuck-me boots.  Betty and Monica removed all my hair again, and I got dressed.  I felt like I had everything under perfect control until I zipped up the last boot.  Oh my God, I thought, what the Hell am I doing?  I stood up and looked at myself in the mirror.  My hair and makeup had yet to be applied.  This is so fucking flaming gay, I thought to myself.  I trembled as I walked to the chair and sat down for my makeover.  I'm turning into a girl! I thought.  I sold my manhood for ten thousand dollars!

By and by, the women finished their work, and I was gorgeous.  My heart pounded in my chest like a jackhammer.  I couldn't walk away now.  In fact, I didn't even need to be ushered to the side of the stage.  I was psyching myself up, thinking about how Carmen Electra would look in this outfit. 

At the stage, there was no sign of the coy debutante.  Instead, I was a raunchy, horny little slut.  I felt so wonderful acting like a girl.  I was imagining that my outfit was so feminine that my penis shrank into my body and became a pussy.  I didn't want to stop.  I went home with my panties on instead of my boxers, knowing that Vanessa wouldn't be home.  I even got to keep the boots!

I hid the outfit in my closet.  I thought I'd put it where Vanessa would never find it.  It was buried under all sorts of junk, where it could do no harm.

For weeks I marvelled at the huge sum of money I had made, just for wearing lingerie, and having some pictures taken!  I couldn't wait for the next shoot.  I didn't especially need the money, but I figured it was so easy, and so harmless, that I might as well go back another three times and collect my cool fifty.  I was still embarrassed enough to not want Vanessa to know.  She didn't trust me at all anymore.

Unfortunately, the shoot didn't go as well as I thought.  My ratings on the website had dropped to a 6.5.  I clearly didn't look curvy enough.  I looked like a man in drag.  I could only conclude that I hadn't prepared enough, so I started to practice when Vanessa was out.  Since it's worth so much money, I thought I might as well put some effort into it.  I might make more.

When she found my stash from the last shoot, she thought there was another woman.  I tried to tell her that it was for her, but I didn't know how to present it to her because she always resisted this kind of sex play.  She then confronted me about the shemale website in the browser history.  She called me a sick pervert, although she still didn't quite make the connection between the two.  So I had to give her the outfit, even though the boots didn't fit her at all.

Imagine my disappointment when Tracy told me that my 6.5 rating dropped me into tier 4, and that I'd only be making five thousand for the third shoot.  I accepted it, because I knew that there was only one way to get my rating back up.  I chose a sexy little pink camisole, a thong, and slippers with straps all the way up to my knees.  This time, I knew how to pose.  I made sure to accentuate all the good girlie parts.  I posed like a pro.  Sure enough, when my pictures showed up on the site, they were worth an 8.

Of course I wasn't satisfied.  I had only gotten five thousand. I took it as a challenge.  A rating of 8 made me a tier 2 trannie, which would be worth fifteen thousand dollars at the next shoot.  As much as I wanted to stop, for Vanessa's sake, the money was just too good.

That's how I explained the whole thing to her when she caught me wearing her bikini.

I figured I needed to expand my horizons a bit, and try some new things.  I was horribly ashamed when she found me.  She was in tears.  I told her the truth: that I was doing it just for the money, that it was harmless.  After a while, she forgave me.

She said she'd stay with me, but only if I would split my earnings with her.  She would help me out by showing me the proper way to do my own makeup, and how to walk and talk.  After the final shoot, it would all have to stop.  I readily agreed, to save our relationship.

She had me dressing up every other day by the end of it.  She had me try on just about everything.  I was getting really good at being female.  The third shoot was a smashing success.  I wore a one-piece bathing suit, and looked every bit like Carmen Electra.  They gave me fifteen thousand dollars, as expected.  I split it evenly with Vanessa.

For the fourth shoot, we decided that I'd have enough time to grow my hair.  It would be a crucial factor.  My rating went up to 8.6 based on the swimsuit pictures.  I practiced every day in preparation.  I even started going out to buy my own lingerie and swimwear and skirts and dresses and shoes, while dressed en femme.  I spent the week before the final shoot as a girl.  I even showed up this time already dressed in a miniskirt and a tight little blouse.

When it was over, I had decided to break it off with Vanessa.  By now, she was holding me back.  My wardrobe had become sexier and more feminine than hers.  Plus I wanted all the payoff to myself.  Besides, she was horrified about the hormones I started taking to keep the hair off my body and put some natural volume in my brassiere.

Fiction: How I Turned Into A Girl

Innocent beginnings

It all started very innocently.  I was 5 years old.  We had a kindergarten class pantomime, in which all the children were to dress up as flowers.  Everyone had to get white tights as part of the costume.  All the boys got to wear girls' tights.  I don't know how anybody else felt about it, but I liked it.  In my primitive sexual mind, at that young age, I liked the way it felt on my penis.  That's when I learned that it's bad for boys to wear girls' clothes.  But the seed was planted.

Tentative experiments

Years later, I got up the nerve to borrow some pantyhose.  I had never forgotten my experience with the white tights.  I liked the idea of being dominated by a woman.  Before the pantyhose, I would fantasize that a woman was making me kiss her boots.  Somehow, I was heavily attracted to women.  But it was all very bad.  I knew somehow that it would be wonderfully naughty to be turned into a girl.  So I played with pantyhose.  At first I wore it over my underwear, for fear of it really making me a girl.  Pretty soon I was all naked inside it, unprotected from its sheer femininity.

Shocking fantasies of being utterly feminized

The fantasies became elaborate scenarios of metamorphosis.  And it had a lot to do with my own free will.  I would imagine resisting for as long as possible, but in the end succumbing to the extreme pleasure.  I imagined what it must be like to wear bathing suits, or even lingerie.  Just the thought of it made me incredibly horny.  I made excuses, believing that if I dared to go that far, there would be no turning back.

Experiments become more daring

I couldn't resist.  I moved on to whatever I had available.  I dared to put on a one-piece bathing suit.  It was heaven!  I knew I was in trouble, but while I wore it, I didn't care.  I wanted to go all the way, by wearing even panties and brassieres.  But I could only do it gradually, given that I had virtually nothing to work with at my immediate disposal.

The collection

I started to steal things from friends' sisters, from Mom.  I needed it.  Pretty soon I had a little collection that I thoroughly adored.  And I wanted more.  I fantasized about stealing underwear from clotheslines.  I had even acquired a bikini!

Busted

I had gotten too bold.  Mom found out.  She was shocked and didn't know what to make of it.  She quickly gathered her things that I had stolen, and I begged her not to let anyone know.  I swore to never do it again.

Purge

I was so ashamed of myself, that I even got rid of the things she didn't find.  I cursed myself for what I had done.

The inevitable relapse binge

I denied myself for so long that the urge to wear something female became uncontrollable.  I stole a bathing suit again, and fell off the wagon.  I binged more than ever with girls' clothes, and loved every second of it.

Denial and abandon

Then I would become ashamed and throw everything away again, vowing to never do it again.  But each time, I could only go so long.  Realizing that I was giving in only made me hornier, because it made me understand that every time I wear an article of girls' clothing, I become more and more addicted to it; which leads to the inevitable conclusion that at some point, I will become a girl from doing it so much.  This only fed the pleasure I got from it more, because the whole point was to make myself feel like a girl.  Then, as soon as I was done, my shame would lead me to renounce my habit yet again, and the cycle would start over.

Caught again

The next time I was caught, I was in the middle of masturbating with a bikini.  I was mortified.  Before, I had only had my stash of girlie clothes discovered.  By now I was in my mid teens, and I was seen by my parents wearing a bikini.  I was so embarrassed that I couldn't speak.  I covered myself up in my shame, and my parents tried to console me, rationalizing it to themselves more than anything.  I swore, once again, to quit forever, but I knew that I had a problem.

Acceptance

My problem wasn't that I was wearing girls' bathing suits and underwear; it was that I wouldn't admit to myself that I loved doing so.  This I discovered when having a little chat with my father.  I didn't tell him so, but he could certainly tell that I was not going to quit.  I would, however, keep it secret.

The gift

On my seventeenth birthday, I was shocked to discover lingerie under my pillow.  I had never been able to steal anything so sexy.  I knew that it didn't belong to my Mom.  Somebody knew of my habit, and was now actively condoning it.  I wore it under my boy clothes all day the next day to celebrate.  Only later did I find the note that was meant to be attached to it.  It read, “I just want to know, for sure, whether you have quit your dirty habit or not.  I know it must be very hard for you.  If you leave this under your pillow tomorrow, I'll know that you want to quit.  If not, then please take these.  I'd rather have you own your own than borrowing all the time.” 

The realization of the enormity

Things started appearing in my dresser at random intervals.  There were many pleasant surprises for me.  Within a year, I had a small collection of just about everything a girl could want.  I was wearing it almost every night.  Only when a girl became interested in me did I realize the enormity of what I was doing.  I couldn't possibly let her know about my collection, which sat openly in the top drawer of my dresser.  I could never tell her that I not only have worn fishnet stockings, a garter belt, a brassiere, many bikinis, and all sorts of satin and lace panties and nightgowns; but I also own some!  I thought of how my initial fears of becoming feminized were becoming totally true.  And I masturbated at the thought.

Busted – for good

By the time I went away to college, I had been with a few girlfriends, and always kept my secret to myself.  But I also secretly borrowed their things whenever the urge struck me.  I was incorrigible.  Annie outsmarted me, though.  She suspected that something was awry.  We were living together, and she noticed that some of her undergarments would shift.  She set up a hidden camera, and caught me red-handed putting on her bathing suit.  She confronted me with the video, and I was contrite, ashamed, and extremely fearful.  She threatened to tell everyone.  I begged her not to.  She relented, but things would change dramatically between us from that point on.

Manipulation

She majored in psychology.  She manipulated me like a handful of putty.  She immediately became dominant, with the threat of exposing my habit to the world hanging over my head.  She was curious more than anything else.  She wanted to understand what got into me.  She wanted to explore the phenomenon.  She had me dress up for her.  At first, it was extremely awkward.  She was only the third person to ever see me wearing women's underwear.  She asked me to go about my routine, and tell her what I was thinking.  I couldn't do it for days, but eventually, I succeeded.  I was wearing a bikini, and she decided to play along, rather than spectate.  We frolicked together, both of us wearing sexy women's swimwear.  I purred to her how I wanted to be just like her, how I wanted to be as sexy as her when I wore her bikini.  I told her that I longed to be worthy of the clothes I play with. 

She tried different tricks, but it became part of the routine.  I would cavort around in lingerie for her every night, under threat of being exposed to the world.  She soon discovered how uncomfortable I became about the whole situation when I wasn't horny.  She had me tell her that I wanted to shave my legs while I was hot with desire, and she talked me into doing it, in spite of the fact that it would be terribly easy for anyone to notice.  I was so horny that I enjoyed doing it, in spite of the consequences.  After I came, she asked me if I would wear makeup, and she couldn't get me to agree to it without threats.

This led to a phenomenal escalation of my habits, which, as long as I was still aroused, I gladly agreed to.  Before I knew it, I had beautiful long hair, easily stylable into a feminine look; I had become an expert at applying makeup; I kept most of my body hair shaven at all times; and I could walk in high heels.  She only let me come just before I went to sleep.  I said all sorts of incriminating things.  I signed documents attesting to my desire to become a girl.  I professed my dissatisfaction with my lack of womanhood to her video camera.  I was giving her more and more material to incriminate me with, to the point where it became almost moot.  I swore to her, on tape and on signed documents, that I gladly give up my own penis in a heartbeat, and even suck someone else's and swallow all the semen.

Exposure

The weight of her threats lay in my desire to keep my femininity secret.  Unfortunately for me, not only had the changes to my appearance become noticeable during the day, but I became indifferent to my reputation as a man.  I was wearing women's underwear under my clothes, to keep me horny all day long.  I felt so good that I wanted people to know what I was wearing.  Many people suspected it.  Eventually, there was no doubt: Annie coerced me into dressing up as skankily as possible with her, and going for a walk in public.  I agreed readily, but became extremely nervous when we actually went outside.  Everyone recognized me.  In a way, I felt extremely sexy and proud; in other ways, I felt deeply embarrassed.  But I got used to it.  Within weeks I was clubbing in my girl clothes.  Luckily, I could still fight.  I was still manly enough for men to want to kill me.

Slavery

With the threat of exposure nothing more than a quaint memory, Annie found other ways to manipulate me.  She made me realize just how deep my desire to be female really went.  I had always kept it to a subtext that I wouldn't even admit to myself, but she hypothesized correctly that I wanted to fuck boys.  She would get me so hot and horny that I would be practically female; then she introduced me to some gay man she knew from college, and encouraged me to explore my urges.  She made me feel so thankful to her that her threats had changed: now she threatened to take away my girlishness.  I became her sissy slave.  I would stay home and be her maid, and she would bring home boys for her own pleasure, and show me off to them as her creation.  I was permitted to suck cock from time to time, and even to get a dick rammed up my ass.  I was a time of great and exciting discovery for me.  But she wouldn't allow me to enjoy it as much as I could have.

Privation

Soon she realized that her hold on me was entirely based on preventing me from having orgasms.  She kept me tied in a penis constraining device so that I would behave better.  I was extremely horny at all times, and I became an insatiable cock whore.  She kept me in her power by promising more cock.  But I was not allowed to come!  I physically could not ejaculate.  I so desperately wanted to. 

Emancipation

I broke my bonds from her at last and came wildly for days.  She was appalled, and threatened to deny me from getting any more cock.  But I discovered that I was fully able to get some by myself.  I was now passable enough to get it, or else brave enough to go to a gay bar and bag myself some easy action.  I laughed when she threatened to expose me.  My transformation was now complete!  I hadn't worn any article of men's clothes in many months, even in public; and I bought my own lingerie and club wear.  I was a little tramp!  I moved out in a huff and got my own place.

A taste for cock

I ditched all my men's clothes that I was no longer wearing.  I became a fixture at gay bars.  My parents found out, and disapproved.  I laughed in their faces, too. 

My fate was sealed from the very first moment

So now I'm scheduled for my pre-operation hormones.  I'm growing my own breasts, and giving up my worthless penis for a glorious pussy.