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.
