by D. L. Savage
“Sure, why not?” she said quietly, her voice shaking a little.
Then she turned back to face the camera and announced, “We’ll do it.”
“Awesome!” Michael laughed. “That’s the spirit.”
By now my heart was in my throat, as Shawna turned to me and said, “Can you, uh, unzip my dress?”
She shifted around so that her back was to me, and I reached out, my fingers shaking a little as I took hold of the tiny metal zipper and slid it downwards, uncovering the pale smoothness of her skin beneath, quickly followed by the thin black band of her bra strap.
“Thanks,” she said, as she began to pull the dress up and over her head.
I felt my stomach vault again as her lower half came into view, charging my body with a pang of horniness as I saw that she was wearing a skimpy black thong. I guess I’d always wondered what kind of underwear Shawna wore, and from the fact that her clothes were usually pretty tight fitting, I should have guessed that she’d wear thongs. But even so, actually seeing her in one was a whole other story, and I had to force myself to pull my hungry eyes away from the vision of her perfectly butt, framed by those skimpy black panties, before it became totally obvious that I staring.
I shifted around so that I was facing away from her, tugging my shirt over my head, then fumbling with my belt buckle, dimly aware that despite my nerves and the cameras and the fact that there were two other people in the room, my dick was growing hard. I tried to will it to go down, but it was no use. The thought of Shawna right there next to me in her sexy underwear was too much to take, and all I could do was try and keep myself hunched forward, knees up near my chest, hiding my boner as best I could as I pulled my skinny jeans down over my calves then tossed them onto the bed next to me.
I saw that Shawna was sitting in a similar position too, hugging her knees, both of us obviously feeling uncomfortable about being so undressed in front of the camera. But of course, we weren’t finished yet.
“And the rest,” Michael said coldly. “You think I’m gonna pay you three hundred dollars just to switch some of your clothes? No way! I want you to swap everything.”
I found myself looking over to Sara for help, but she was grinning back at me, pointing the big black microphone in our direction, obviously enjoying this as much as Michael.
And even while I was still deliberating on what to do, to my total shock, I saw Shawna reaching around behind her back and starting to unclasp her bra. For a moment, it felt like the whole room was plunged into slow motion, as we all watched her gingerly slip her bra from her shoulders then pull it away from her chest too, exposing her breasts.
I felt a powerful charge of excitement despite myself, as I finally caught my first ever glimpse of Shawna’s tits. After all, I’d been dreaming and fantasizing about them all through my adolescence, but never in a million years would I have guessed that I’d actually see them. They were a little smaller than I’d imagined, but really pert and amazing too, with cute pale pink nipples. And maybe it was the slight chill in the room, but I could see that her nipples were actually hard too, pointing away from her breasts in two tempting, tantalizing little pink nubs of flesh.
I felt my boner throb almost painfully as she lifted her butt off the bed and quickly slipped her thong off too, tossing it casually, along with her bra, next to me on the sheets.
And now every eye in the room was trained on me, as Micheal said, in a low teasing voice, “Aiden? Are you gonna take off those boxers and give them to Shawna?”
I nodded, feeling my face flush with fresh heat as I reached down and began to slide my shorts over my legs, then passsed them over to Shawna, catching a glimpse of her totally shaved pussy in the process, which looked pink and plump, my hard cock now jutting up proudly between my legs despite my total shame and embarrassment.
“Well, well, well, what have we here?” Michael laughed. “Looks like Aiden is maybe a little more into Shawna than he’s letting on!”
As they all turned to look at me, I felt my face grow bright red, but to my surprise I heard Shawna snap, “Shut up, dude. Leave him alone. So, do we get the three hundred bucks now or what?”
“Once you’ve put each other’s clothes on, yes,” Michael replied coldly.
So we set about getting dressed again, only this time I found myself fumbling with Shawna’s thong. It actually felt warm in my fingers, and my cock was still throbbing madly as the thought entered my mind that this flimsy little scrap of fabric had been right next to Shawna’s cute shaved pussy and right between her amazing butt cheeks.
After a little puzzling, I worked out which way around it went, feeding my feet gingerly through the holes then tugging it up around my waist, glad to have something to hide my boner from view. But of course, it was so damn skimpy, it didn’t do much in that department, the stretchy black fabric cupping my balls tight, while I just about managed to fit my hard cock inside by pushing it sideways, while between my ass cheeks I could feel the strap at the back actually pulling tight against my asshole. Damn, I thought, is it supposed to feel like that? And I couldn’t help but think about how Shawna must have been aware of these tiny little panties between her own butt cheeks this whole time beneath her dress.
As she began pulling on my boxer shorts, I started trying to figure out her bra, but after a bit of struggling, I heard Michael say, “Shawna, maybe you should help Aiden out over here!”
She was still topless as she turned to me, and again I found myself just flat out staring at her amazing perky breasts, her cute little nipples still rock hard as she moved behind me then pulled the bra on, clipping it at the back. I winced a little as it dug sharply into my sides, but she managed to fasten it, before helping me pull the straps over my shoulders, too. And even though I obviously didn’t have anything to fill the cups with, to my surprise it actually seemed to fit me okay, the empty cups stretching tight across my pecs, creating round mounds that I guessed looked, at least from the outside, like a pair of small pert breasts.
“Looking good, guys!” Michael teased, as Shawna pulled on my skinny jeans and t-shirt, while I again found myself fumbling and puzzling with her dress.
Obviously, I’d never put a dress on in my life before, and even though I’d watched Shawna take it off just a few minutes ago, it was like my mind went blank and I didn’t even quite know how. In the end I guessed that yeah, I was supposed to just pull it on over my head like a huge, weird sweater or something.
With a final thought of here goes nothing, I pushed my arms through the arm holes then pulled it over my head. And wow, that thing was tight! It really clung to my body, so that I had to inch it carefully down until the skirt was sitting correctly around my waist. Staring down at myself, I saw that sure enough, the cups of the bra created the illusion of two small pert breasts.
“Congratulations,” Michael said, moving forward with the camera so that he was standing right at the foot of the bed now, the cold dark lens trained on us as we sat there nervously. “You’ve just earned yourself three hundred dollars. So what d’you think, Shawna? Does Aiden look more your type now that he — or should I say she — is all dressed up?”
“Maybe,” Shawna mumbled, but I suspected she was only saying it out of nerves, either that or because she didn’t know how else to reply. In reality, I guessed I probably looked pretty ridiculous, while she actually looked good in my clothes. The t-shirt fitted her really well, and without a bra, I could still make out the bumps of her nipples pressing through the fabric.
“Say, that gives me an idea for a second dare,” Michael continued. “How’d you like to bump your total up to five hundred dollars, with a little makeover session? Shawa, we’ve got a full selection of makeup over there on the dresser. Why don’t you make Aiden here look a little more girly?”
Again Shawna looked at me, her eyes searching out mine, as if to say, Are you okay with this? And the truth was, in that moment I didn’t really care. I just wanted the money and hell, an extra two hundred dollars just to put o
n a little makeup seemed like a pretty good deal after what we’d just been through. So I gave her a quick nod, before she turned back to face the camera and said, “Sure, why not?”
My heart was in my throat as Michael laughed and said, “Awesome! This is going to be fun. So kids, why don’t you come over here to the dresser, Aiden you take a seat and Shawna will fix you up ...”
As we pushed ourselves off the bed, it felt so weird to be wearing her clothes, and again I felt super aware of the thong in particular – the way it cupped my cock and balls so damn tightly, and the way it seemed to gently tease my ass with each nervous step I took towards the mirror.
I eased myself down into the seat, glad that it was Shawna in charge of making me over. After all, she was super good at that kind of stuff and I knew she wouldn’t do anything to make me look stupid. Hell, who knows? Perhaps I might even look okay …
I shivered a little as I felt her scrape the hair from my forehead, brushing it backwards with her slim fingers, before she quickly set to work, grabbing a tube of foundation and starting to dab it onto my face ...
8
“You can open your eyes,” Shawna said, as she finished up the last of the eyeliner.
When I did, I stared at my reflection in total amazement, for a moment even forgetting that Michael and Sara were there in the room too, watching as my now-glossy lips curled into a genuine smile of amazement.
“Wow,” I said, as I gazed at my brand new face – a face I didn’t even recognize as my own.
Shawna had done such a good job, totally exceeding my expectations, even tricking my own brain into thinking I was someone else. She’d used subtle shading on my cheeks and on my nose to accentuate my features, as well as lighter tones too, actually creating the illusion of a slim, super feminine bone structure. And she’d chosen these really amazing pale pink tones for my eyes and lips, giving me a sexy – hell, even slutty – vibe, which I loved.
“I have to hand it to you, Shawna,” Michael admitted, “that’s a pretty awesome job you’ve done there. But I think she’d look better with some lovely long hair too, wouldn’t you say? It’s a good job I brought something extra along with me ... Sara, why don’t you go grab it from the bag?”
We both turned and watched as Sara moved over to a large holdall which had been sitting in the corner of the room the whole time, opening up the zipper and flipping open the lid, then retrieving something from inside, pulling it out of a clear plastic bag then shaking it out, running her fingers through the long, pale pink strands. It was a realistic-looking wig, I realized.
And in that moment it finally clicked. Michael must have been planning this weird makeover for me right from the start. Why else would he have brought a goddamn wig?
As Sara moved around behind me, he said, “So, Aiden … or should we call you Hayley from now on? What say we bump your total up to six hundred dollars if you agree to put this on, too?”
This time I didn’t even hesitate. Hell, I’d have put it on for free. Because all of a sudden I realized I wanted nothing more than to see myself fully transformed – to see what I’d look like as a real girl, with long glossy hair to match my sexy, slutty makeup and cute black dress.
“Sure,” I croaked, my voice no doubt giving away my secret excitement at the idea. I held my breath as Sara moved closer, carefully fitting the cap over my head and then teasing the long glossy curls into place around my shoulders, the soft pink hair perfectly framing my features and completing the illusion.
Again, I couldn’t help but stare in awe at my reflection, once more unable to believe that the girl in the mirror was really me. Because I looked so fucking hot it was crazy! What’s more, I actually felt kind of turned on, too. I could feel my cock starting to throb and grow once more in my panties, and I felt kind of shocked by how much I was enjoying this whole experience.
Hell, I’d never had any kinds of thoughts about dressing in girls clothes before, but it turned out it was actually kinda ... into this. I was just glad that now I was wearing the dress, with its cute bouncy skirt, so that my erection was safely hidden from view beneath.
“If you’d like to take a seat back on the bed,” Michael continued, still pointing his camera at us, “I’ve got another dare lined up for you guys ... and this one would bring your total up to a thousand.”
I felt a flash of excitement, quickly followed by worry – because what the hell could it be? I knew that kind of money wasn’t going to come easy, and it sure as hell wouldn’t just be by answering some questions.
Sure enough, once we were sitting on the bed again, he said, “As you can probably guess, this dare is going to push things up a notch, and it’s totally up to you if you want to tap out and leave with the six hundred ... But if you do want to bring it up to a thousand, I think all our viewers would like to see you both make out.”
His words hung in the air, along with the sound of my heart, booming in my ears.
“I’ll give you a moment to decide,” he added.
I turned to Shawna, and when she looked back at me, I was shocked to see that she was smiling. She leant in, speaking in barely more than a whisper as she said, kind of shyly, “I mean, I’m cool with it if you are?”
As she spoke, I noticed that she had this weird, playful look in her eyes that I’d never seen before, not to mention the flirtatious tone of her voice, and it finally began to dawn on me: a truth I couldn’t quite believe.
Now that I’m dressed as a girl ... does she find me hot?
“If you’re sure?” I replied, my own voice no more than a whisper, no doubt conveying the nervousness that seemed to be pulsing through every part of my body at that moment.
“I’m sure,” Shawna smiled, then turned to Michael and announced with a playful smile, “We’ll do it.”
She turned back to face me, taking the lead as she leant in towards me, cupping my face gently in the palm of her hand and moved her mouth closer and closer to mine. I closed my eyes as I finally felt her soft lips touch against my own, and a powerful shiver of pure pleasure shuddered through me as the thing I’d secretly wanted most in the whole damn world finally came true.
Soon her tongue was pushing into my mouth, too, flicking against my own, as Shawna pushed her slip body close to mine, my senses filling with her — with her delicious floral perfume, with the sweet taste of her mouth, and with the feel of her breasts against me too, her hard nipples brushing my arm — as our kiss got hotter and hotter, until finally she pulled away, her eyes flashing with naughty glee and a cute smile still etched on her lips.
The sound that broke the silence was Michael’s clapping, and we both turned to face him, a little flushed and dizzy as we floated back to earth, realizing once more that this was all part of the game, and there was still more to come.
“I’m impressed, girls,” he said in a low voice. “Very impressed. In fact, I have to say, I’m a little turned on myself.”
“Now comes the truth or dare round. Each question you answer gets you another fifty dollars. So who wants to go first?”
“I will,” I said quickly, wanting to just get it out of the way.
“Okay, Hayley,” he said. “Tell me, how many people – boys or girls – have you slept with?”
I took a deep breath. I knew I could ask for a dare if I wanted to, but in the end I decided just to tell the shameful truth.
“None,” I admitted quietly, feeling my face grow hot.
But at the same time, I felt glad to win a little more money. One thousand and fifty dollars, I thought to myself, keeping track as the game continued.
“And the same question goes to you, Shawna,” Michael persisted.
“One,” she replied.
I knew this already; it was a girl she’d met at summer camp last year. They’d got it on in the dorm room, while all the others were out playing handball.
“And that was with a girl, right?” Michael continued.
Shawna nodded.
One thousand, one
hundred ...
“And another question for you, Shawna,” he said, “unless you’d like to take a dare instead?”
This time she shook her head, as I waited for him to speak, wondering what his next question would be.
“Have you done anything with a boy, other than your little make out session with Hayley, here?”
“No,” Shawna replied confidently. “Nothing. That was my first time.”
“Well, that brings us neatly to my final dare,” Michael said, speaking in a low tone,” his voice full of suggestion. “Shawna, to bring the total up to three thousand dollars, would you suck my cock?”
The shock hit me like a punch in the chest. Sure, we’d dressed in each other’s clothes, and sure, we’d made out. But this was something else entirely. This was crazy …
I was totally sure she’d say no, tell him to fuck off – especially after the hundreds of times I’d heard her say how disgusting she thought porn was – but to my total and utter amazement, she said in a quiet but confident voice, “Okay.”
I couldn’t help but speak then, turning to her and grabbing her shoulders, forcing her to face me as I said, “Shawna, you know you don’t have to do this, right?”
She nodded, giving me a reassuring grin, then replied, “I know, Hayley.”
It took me aback when she called me that, and I found I actually liked it – after all, right now I really did feel more like a girl than my old geeky male self, and I felt my palms going clammy and my heart hammering, the nerves overtaking me so powerfully in that moment at the thought of Shawna going through with the dare.
“Sara, why don’t you take hold of the camera here,” Michael said, passing it to her, “and I’ll go make myself a little more comfortable on the bed ...”
As Sara began to film, he strode confidently towards us, kicking off his sneakers then climbing up onto the bed and positioning himself between us, his huge masculine bulk so at odds with our skinny, feminine bodies. I felt so damn small in comparison to him, and it just served to reinforce how girly I was, how different to a real man like Michael.
