What Am I Wasting My Time On?

I typically have no more than one day per week to indulge in my fantasies. I can't read sissy blogs or look at pictures of transsexuals when I'm at the office, and when I come home I have to do family stuff. That leaves the one day I work from home: I close the door to my home office, and while my wife runs errands with our toddler, thinking I'm hard at work, I can't help but secretly feed my fetish.

Ideally, if I had ample free time alone as I did when I was single, or if my wife knew and approved of my predilections, I'd be more able to get some writing done. Instead, I have to rush through my favorite sites to find something to wank to, and get it over with quickly before she comes home. I spend the rest of the day going back and forth between actual work and these idle fantasies.

So what exactly do I wank to?

As with most crossdressers, I am keenly interested in beautiful women. I've read about sex addicts who need to see something extreme before they can even come close to climax. I'm the opposite: I can wank to just about any picture if it's of a pretty enough woman. It's what goes on in my head that makes me come.

For example, this is what I jerked to today:

I found this by accident while price-checking some beauty product my wife asked for for Xmas. I've been obsessing over her most of the week. What makes her so unbearably hot is the notion that I could buy that dress, and those boots, and I could become that feminine.

I don't spend as much time as I used to window-shopping lingerie and swimsuits online. I've made all kinds of goo contemplating and even actually purchasing and wearing such things. In the last couple of years, I've found myself drawn to pictures of convincing crossdressers and transsexuals, and of genetic girls given photoshop penises. This all used to repulse me, but now it fills me with admiration, envy, and hope: how incredibly lucky they are to have become feminine! How I wish that could be me!

Insatiable

While writing that last post, I mentioned knowing that if I had no boundaries, I would wank myself to death. I thought I had written about this before, but searched for it throughout my writings, to no avail. I wanted to link to the article I thought I had written, as a case in point. But there is no such article. Therefore, here's a little story about my insatiability when it comes to feminizing myself.

One evening, with my wife out of town for a bachelorette party or some such, I had decided to make full use of her absence to engage in as much girlish debauchery as I could handle. There was so much that I wanted to wear, and in only one night, that I hardly knew where to start. I have limited ability to recuperate at my age, so every wank must count.

Usually, when she's not far away, I have limited time to enjoy my femininity. I browse around the web for things that interest me for a while, which normally feeds some specific fantasy. I then fulfill it by wearing whichever girlie item fits the fantasy best. Sometimes, I'm already obsessed with some specific garment, and develop an elaborate fantasy around it. In any case, it's over after one wank, so I prefer my fantasy to match what I'm wearing, to maximize my pleasure. At times, this isn't enough to satisfy me, for various reasons. I actually keep a diary of every "incident", including what I wore, how much I enjoyed it on a scale of 1 to 10, and a brief description of the circumstances. Merely documenting this after the fact often launches me into another fantasy, so I find myself wanking again in another garment. This second orgasm is usually much harder to achieve. Interestingly, when making love to my wife, I can never muster the lust to come twice.

On this particular evening, I knew that I had all night. I was ravenous for femininity. I had a plan. Since I had no fear of interference, and total privacy for many, many hours, I decided that I would spend the evening wearing nothing but women's clothes, and sleep in my wife's little slip dress that she left behind under her pillow. I had fantasized many times about doing this, but inevitably my playtime would end after succumbing to the temptation of orgasm. This time, I was determined to at least see how long I could go, and try to avoid masturbating.

I whet my appetite browsing the web for the usual: pictures, stories, captions, videos, and so on. I probably wore swimwear while doing so (my records are sketchy, so I'm not sure). I tried to hold out, but probably lasted only an hour or so. In spite of my ambitions, I achieved my first climax quite quickly after all that preparation. In fact, it was too quick to be fully satisfactory. Thinking of my original plan, rather than giving up right then and there, I changed into a bikini. The thought of actually executing on my plan was so arousing that I couldn't resist coming again, soon after putting it on.

By now, I was already tired. My penis was sore from having climaxed twice. With resignation, I cleaned up the mess, and thought my valiant attempt had no hope of continuing. But there again was that thought: now that I've gotten it out of my system, I can surely wear women's clothes without having to masturbate. This would be somewhat less fun, but satisfying nonetheless, on an entirely different level. I slipped into my corset, stockings and high black boots, figuring that if I was going to do this, I might as well challenge myself.

I settled onto the sofa in my lingerie to watch a movie. I spoke to my wife on the phone. The whole time, I counted my blessings that I could wear such an outfit. I lounged happily in my feminine attire, fondling the lace of my panties and the smooth nylon of my stockings, snapping my garters, and adjusting my bodice. Before long, and much to my delight, I gave in to temptation yet again.

At this point, I would normally start feeling a little ill from all the strain, and more than a little over-satiated. And so it was then. But I had a seed in my head. I felt like I could go no further, but by now I was wondering if I even could cum if I tried. I struggled a bit to think of what I'd want to wear, but the very idea of being such a sissy that I could still climax after everything I had already done, spurred me on. I chose my favorite swimsuit, and carried on, knowing that I still had to somehow sleep wearing panties and a nightie.

It was less difficult than I had thought. It was somewhat painful, as with an overworked muscle, and it hurt to even have an erection, but the overload of femininity was too much to keep me from succeeding. I came again!

It was late by now, and I was exhausted. I felt like there was no amount of masturbation that would cure me of this fetish. All I had to do was allow myself to fantasize, and I could keep cumming over and over again. The idea that this dirty little fetish was impossible to satisfy made me want to come yet again! Somewhat unnerved, I slipped into the nightie and panties as planned, brushed my teeth, and went to bed, excited about sleeping en femme. I was drifting off to sleep, and just wanted to enjoy some sweet girlish dreams. I tried not to think about what I was doing.

It was no use. I woke up in the middle of the night with a massive erection, throbbing with the dull pain of muscular fatigue. I would not be able to sleep until I wanked it out, so I once again satisfied my urges.

By now there was no longer any doubt. I had discovered that there is no practical limit to my arousal when indulging my feminine fantasies. I could literally wank myself to death if I allowed myself to. It was also both arousing and disconcerting to confirm that my ample appetite for straight heterosexual intercourse was far smaller than that for feminization. This was not surprising. That the latter was limitless, was.

By morning, I was so worn out and so sore that I couldn't imagine how I would explain to my wife why I wasn't eager to fuck her when she returned. I schlepped around all day in a fog from my exertions of the night before. I had only now, after all these years, discovered the magnitude of my problem.

Various Girlie Dreams, and Consequences in Real Life

I've been going crazy with deprivation lately. It's going to blow up soon, and it'll be incredibly fun, but I have to wait for now.

Because of my runaway fantasies, I dreamed last night that I was walking around something like a Las Vegas casino resort, with lots of people around and long distances between places. I was wearing knee-high black boots with pointy toes and high heels, and maybe some sort of lingerie or little black dress. I was light on my feet, and proud of my outfit. I didn't at all care what anybody thought about it.

Some time later, I was playing with eye makeup in my hotel room, when I heard my wife arriving. I had thick black mascara and eye shadow on my right eye, and I was desperate to remove it before she could see me. I managed to rinse it off in the sink just as she arrived, and I had to hide the mascara from her, in my hand, desperate to hide it somewhere. Then the whole dream just devolved into some other events that I only vaguely remember, but all while trying to hide from my wife the fact that I'm wearing something feminine.

As a tribute to my dreams, I'm wearing my black lace-up panties all day, and damn the consequences.

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: Las Vegas

"I like to crossdress every now and then.  I especially love swimsuits.  I'm certainly not gay or anything.  I just like the way it feels on my body."

"I crossdress because I like the feel of nylon, satin etc."

"Bras don't do much for me. I am a leg man."

"It's not that I want to emulate women; I am me, a guy who happens to like wearing certain female garments."

Now, just think about that for a moment.

What goes through your mind when you wear panties?  Does it make you feel manly?  How gay is that?  Think about it: you've worn women's underwear, and you liked it.

The fact is, it makes you want to be a girl.  Trust me, you're this close to sucking cock.

I was like you once, but things got a little out of hand one time, and I ended up experiencing things that I never even knew I longed for.  I bet you're one of those closet queenies who sneaks around his wife's back, wearing her underwear when she's not around.  You might even be lucky enough to have a woman who understands your needs (partly, at least) and lets you indulge now and then with her.  But deep down, and you don't even know it, it never goes far enough.  When you're prancing around in a garter belt and stockings, even though you think you're just being a guy who likes to wear girlie things, you're really striving to become a woman.

But don't worry, you'll get it someday.  I for one didn't realize it until I tasted penis for the first time.

I was on a business trip in Vegas.  I was horny.  I couldn't stop thinking about wearing something girlish.  Up until then, I was just like you: I'd wear my wife's stuff sometimes, when she wasn't around.  I focused on the panties, cuz that's where the fun parts are.  I had tried on her bras once in a while, but it just wasn't as big a deal.  Anyway, I was bored and lonely and horny, so I looked through the yellow pages.  Sure enough, there are plenty of escort services, which are perfectly legal, which cater to any need imaginable.  I noticed a few that offered feminizations, and I bit.  I'd never crossdressed in front of anyone else before, and this excited me.  I was in Vegas, and I got caught up in the spirit of the place.

She came over with a little suitcase.  She was incredibly sexy and hot.  This kind of woman usually intimidates the hell out of me.  We went over the rules: what she does, my safety word for when I want to stop it from going any further.  She was clearly a pro, given the way she opened my eyes about my secret habit.

That first night, she asked me how long I was staying, and what I was in the mood for.  She was feeling me out, asking me questions, acting coy, acting bossy, acting playful.  She eventually settled on an abusive playfulness.

I was extremely shy.  She wasn't getting much out of me.  I was trying to cop a feel, but I was afraid of her.  So she got fed up, and called me a faggot.  I told her, I'm not gay, I just like wearing girlie stuff now and then.  What the fuck?

And she told me what I told you: think about what you're doing.  You want to dress like a girl, and not just a girl, but a skank.  You want to be a hottie like me.  She undid her blouse and showed me her sexy lingerie.  She moved very seductively towards me and asked me if it wasn't true that I wanted to wear her underwear.

Of course, I said yes.

"You like the way it feels on you?  It makes you feel sexy?"

"Yes", I answered.

"Well," she said, putting her hand on my knee, "that's because you want to be just like me."

"Yes!" I exclaimed, surprised at myself.  She was getting me hot.

She instructed me to take my clothes off, all of them, and pick out some undies from her suitcase.  She had all kinds of goodies in there.  I was nervous and shy, but I figured I was paying for it, so I might as well go through with it.  I told her I was hankering for a bathing suit, but she didn't have any swimwear.

She played with me a bit after I put the panties on.  I was getting a huge kick out of her seeing me.  Then she called me a homo.  I protested, but she pointed out that I had just voluntarily put on some of her panties, and that it was giving me a serious boner.  This made me even hotter.  But why?

She told me that it was ok with her that I was being gay.  "Just look at the fun you can have when you're being girlish," she said.  And she was right!  I was having a ball in spite of her.  "You'll be sucking cock and take it in the ass before you go home," she said.  But I didn't care.

I was prancing around and rubbing my cock.  I wanted to masturbate.  But I couldn't ignore her.  She was incredibly hot.  She was taking off her clothes, too, and showed me the garter belt and stockings she was hiding under her skirt.  "Wouldn't you love to have some of these?"

And with that, I put on a garter belt and stockings.  This wasn't new for me.  It was one of my favourites.  This was as far as I wanted to go.  In fact, I'd planned to only wear panties with anyone, but she made a good argument for more.

"Look at you!"  She said.  "Are you feeling feminine enough now?"

I said yes.  I wanted to come.

"Nonsense!"  She admonished.  "How can you be a proper girl if you're not wearing a bra?"

As I told you, I didn't normally wear bras.  They don't really do much for me.  I shyly declined.  "Are you sure," she asked.  I told her I was.

"Well," she said, "that's a shame."  She slunk over to me, in her underwear.  "You feeling all girly and all, yet you're not even close to being like me.  Look at my bra.  Don't you like it?"

I told her I did, I liked it very much.

"Then why are you afraid of it?"

I told her I wasn't afraid, I just didn't like wearing bras.

"But look how sexy it is," she said, fondling her breasts.

"OK," I said, relenting.  I was feeling kinky about, like I never had before.  "I'll wear it."

"Don't do it for me," she said. 

"No, I want it."

"You want what?"

"I want a bra."

Why?

"Because."

"Is it because you want to feel sexy and feminine?"

"Yes."

"Why?"

"Because I like it."

"You like being feminine?"

"Yes."

"Is it because you're gay?"

I could feel my face flush with anger and embarrassment.  "Why do you say that?"  I asked.

"Are you serious?"

"About what?"

"You're seriously asking me why I'm calling you a fag, while you prance around in front of me begging me for a bra to wear?"

I was terribly ashamed.  I wanted to take off my panties and garter belt and stockings, and kick her out of my room.  But when I felt the panty waist on my fingers, I couldn't.  I was wearing women's lingerie!  She was right, it was incredibly gay of me.  My crotch gushed with pleasure.  I wanted more.

"So do you still want the bra?" she asked.

"Yes!"

"OK," she said, "but I won't give it to you unless you admit that you're a flaming faggot who desperately wants to be a girl."

"Fine," I said.  "I'm a flaming faggot."  I was blushing as I said this.  "I'm a flaming faggot, and I desperately want to be a girl."

"And?  Why do you want to wear a bra?"

"Because I want to be a girl.  And I'm a faggot."

She gave me a bra to match the rest of my outfit, and I was ecstatic.  I was rubbing myself frantically.

"You don't want to be gay, do you?"  She asked.

"No," I whimpered.

"But you want to be feminine, right?"

"Yes!"

"You know, the more girlie stuff you wear, the more feminine you get?"

"Oh God!  I hope so!"

"With you wearing that bra, you're much more feminine than you were before."

She flatters me!

"It's going to get worse and worse you know."

The idea appeals to me.  Enormously.

"And the more feminine you become, the more you'll want to sleep with boys."

I suddenly felt ultra-feminine.  Just what I wanted!  I was picturing her fucking and sucking.  I was staring at her crotch.  I wanted one just like it.  She swung it around a bit in front of me, and said,
"Look at my pussy.  You want one just like it, and you want to do things with it that only girls do."

"Yes!"

Before she left, she had me in a patent leather minidress, fuck-me boots, and makeup.  I was totally effeminated, and she kept telling me so.  I came five times.  I had never gone so far.  She left me a silky nighty and a fresh pair of lacy panties, and told me I could sleep in them.

The next morning, I woke up in them feeling randy.  I loved the way the skirt of the nightie brushed so lightly and softly against my thighs.  I felt utterly feminine, again.  I thought about what she said: that the more I wore, the worse it would get.  I wanted it to get worse!  I now fantasized about wearing nothing but girl clothes forever!  I wore my panties under my suit all day.  It was fun, but it wasn't enough!  I wanted to have a bra to match it, and maybe have it just a little bit visible.  Just for kicks.

That night, she knocked on my door again, unexpectedly.  I suppose she wanted her clothes back.  She confirmed this, and I was crestfallen.  I asked her if she was busy, and she started to indicate that she should be with another client.  I paid her twice as much for her company, and she gladly accepted it.

She was proud of me for wearing panties all day under my clothes.  But, she said, she suspected I wanted to go further.  I sheepishly agreed.  So we went shopping.  "You wanted a bathing suit, right?" She asked.

We browsed around together for a while, and we settled on a light blue bikini with little red flower print.  She forced me to tell the cashier that it was for me.  I was so embarrassed, but thrilled.  I was telling other people about my secret!  Then she had me go to another store and buy a fantastic one-piece suit in bright orange with a zipper in the front.  Again, I had to proclaim that I would be wearing it.  So I did, in great anticipation.

We went back to my room, and she had me put on the one-piece.  It was even better than I had imagined.  I'd worn bathing suits before, but this was incredible.  Somehow, she made me feel even more feminine.  I suppose because I could look at her and imagine myself like her.  Then I put on the bikini and pranced around some more.

"Aren't you the little prancing gaylord!" she said.  

"Yes I am!"  I admitted.  "I love feeling feminine!  This is incredibly gay of me!  I've worn girl stuff all day long, and I want more!  I love how gay this is!  I wish I had a pussy!"

"And what would you do with it?" she asked.

"I would fuck boys with it, I whispered, blushing like a schoolgirl."

With that, she led me into the bathroom, where we applied depilatory cream all over my body.  Oh my god, I thought, this is going much too far!  How will I explain this?  But it was too late.  I wanted it.

I slept in the one piece, and wore the bikini all day under my clothes.  It was easily visible under my shirt, especially the tie around my back and the back of my neck.  It made me feel so sassy!  But I longed for some stockings on my bare legs.  At least I had a bra on!

So that evening, I paid her again, and we went shopping for club wear.  I had my very own outfit now, including gorgeous fuck-me boots, a very short miniskirt, and a sexy blousy top.  I also bought plenty of panties and bras for myself, since I decided I would never wear men's clothes again.  And of course, stockings and a garter belt.

We went back to my room to put them all on, and head out.  I wanted everyone in the world to see me as the girl that I am!  She took me to a gay nightclub.  At first, I resisted, but she convinced me that it would be safer from punks who don't understand trying to kick the shit out of me.

I enjoyed the attention I was getting.  A guy struck up a conversation with me, and we talked quite a bit.  I had never hung out with gay people before, and I realized then that they're quite nice.  Besides, there I was dressed like a slut.  He invited me to his room to hang out a bit, and I accepted, naively.

Once in his room, he put the moves on me.  At first, I was shocked, and a little bit disgusted.  But he kept fingering the tops of my stockings.  I felt so fantastically feminine. I could just picture my cunt forming in my clothes.  It made me horny to think that I was wearing such slutty girlie clothes, and flirting with a guy!  I did not resist when he kissed me. 

To make a long story short, she was right.  Before I knew it, I had his dick in my hand.  It didn't even occur to me what I was doing.  I wanted so badly to taste it.  I was picturing her as I put my mouth on it.  When he came in my mouth and all over my face, I thought to myself, how gay is that?  I had gone so far that it didn't even phase me to have his hard penis pump into my ass, like the girly faggot that I am.

I now fantasize about cock all the time.  My wife left me, and I wear nothing but girls' clothes.  I have become transsexual, and I can't wait for my operation.

That, my friend, is what is really going on in your head.