Dressed for Pleasure

by D. L. Savage

  “Uh, sure,” I replied, the awkward shyness in my voice so damn obvious.

  And all of a sudden I just needed to get the hell out of there. It felt so fucking stifling and claustrophobic in his cramped bedroom, so I just turned and raced off without even properly saying goodbye ...

  3

  That Saturday morning I had the weirdest dream. I was once again with Mike in his bedroom, only this time I’d actually turned into a sexy chick. Maybe it was the talk of the movie, or maybe it was a way for my subconscious to deal with everything, but either way, that’s what I was dreaming.

  I found myself dressed in a skimpy little bikini, with real boobs and a cute pert butt, and just as in the rehearsal, Mike leant in to kiss me. I shivered with pleasure at the feel of his thick sensuous lips as they pushed against mine, and I loved the way his hand had curled around my head as his tongue pushed deep into my mouth.

  And this time, I could feel my nipples growing hard as the kiss got even more intense. I let out a sigh as Mike began to stroke his fingers between my legs, until I could actually feel my brand new pussy growing wet, as sexy little moans and sighs fell from my plump glossy lips. And I began to stroke him too, working his thick hard cock through the denim of his jeans, feeling it growing so fucking hard and hot, as all the while we made out intensely, our mouths crushed together, his hand teasing my aching clit until ...

  I came with a gasp, hunching forward, waking up from my dream at the exact moment my dick pumped out a series of powerful squirts of hot gooey cum onto my tensed up abs.

  Woah, what the fuck?!

  Never in my life had I had a wet dream before, and I felt a powerful pang of embarrassment at what it had been about. I quickly grabbed a discarded sock from the floor by my bed to clean up the mess, telling myself to get a grip and push these weird, fucked up thoughts from my mind. Because I’d always thought of myself as totally straight. So why the hell was I having sex dreams about my best friend?

  Just as I was done cleaning myself up, I heard the familiar buzz of my cellphone, vibrating on the bedside table.

  I grabbed it and checked the screen, and of course it was Mike calling.

  A part of me considered ignoring the call, but at the same time, I didn’t want him to think that I was becoming affected by what was happening – especially after the way I’d left his room in such a hurry yesterday. So with a frustrated sigh I answered the call.

  “Hey dude,” I said, hoping I sounded totally normal. “What’s up?”

  “James,” he shot back, his voice brimming with excitement, “You need to get over here now.”

  “How come?” I replied. “What’s the big rush?”

  “Arial’s gone away with some of her friends for the weekend,” he said, like that should mean something. “She won’t be back until tomorrow night. And on top of that, my folks are going out of town, too.”

  “So?” I said, still confused what that had to do with anything.

  “So,” he shot back, “that means we have full access to her wardrobe! And the house! I’m moving the shoot forward. So you need get your butt over here, pronto.”

  God damn it, I thought, knowing that in typical Mike fashion, he simply wouldn’t take no for an answer. When he had his heart set on something, he’d go to any damn length to make it happen. There was nothing I could do; no way of getting out of this.

  “Alright man,” I replied. “Just let me grab a shower and I’ll be right over ...”

  “Oh, and James?” he cut in. “Make sure to shave, too.”

  “Right,” I said, figuring he meant the fact that we’d be putting makeup and whatnot on my face.

  “Legs too,” he said, before I could hang up the phone.

  “What?!” I blurted out.

  “We need this to look authentic,” he said, his voice growing serious.

  “Alright, alright,” I sighed, once again cursing myself for agreeing to be in his stupid ass movie ...

  * * *

  “James?” Mom called, her voice loud enough to hear over the hiss of the shower as she angrily jiggled the door to the bathroom. “How long does it take for you to have a shower?”

  “Just another couple of minutes and I’ll be right out,” I called back.

  I was standing, butt naked, dragging the razor up my left thigh – shaving away the very last of my leg hair. Man, what the fuck was I doing? This whole movie idea was getting out of hand. But it was too late to back out of it now.

  I finished up shaving, then jumped back under the shower, giving my now-hairless body a final rinse before shutting off the water. And as I did so, I stared down at myself, amazed at how different that one simple thing had made my body look. If I’m honest, I wasn’t the hairiest guy to begin with, but even so, my newly smooth legs and belly really did look ... well ... girly.

  “James, come on,” Mom called again, giving the door handle another pissed off rattle for good measure. “That bathroom isn’t just for you, you know ...”

  “God damn it,” I muttered beneath my breath as I patted my body down with a towel then quickly throwing on a fresh pair of boxer shorts, as well as the jeans and t-shirt I’d carried into the bathroom with me for exactly this purpose – knowing my mom would probably be waiting angrily outside the door. And I’d be damned if she was gonna find out what I’d just done in here.

  “Happy now?” I muttered as I finally stepped out of the bathroom and she rushed inside.

  “I’d be happier if you hadn’t just wasted half the god-damn water in the tank,” she snapped back, before slamming the door behind her.

  “I’m going over to Mike’s,” I added. “I’ll probably be staying over tonight, too.”

  I waited for her to answer, but gave up after a few seconds.

  If you hadn’t already guessed, our relationship wasn’t exactly the greatest. But Mom was used to me being gone all weekend, so I knew she wouldn’t freak out about me staying over at Mike’s. That said, if she knew what I was going to be doing over there, well, that would be a whole different story ...

  4

  “Are you sure Ariel’s gonna be cool with us using all her stuff like this?” I said.

  Because we were standing in the middle of her bedroom, and it looked like Mike had emptied every single one of her closets onto her bed. There was a whole mountain of clothes piled up, in every conceivable style and color you could think of.

  “Don’t worry,” he grinned, giving me a knowing wink. “She’ll never know.”

  Personally, I wasn’t so sure. There could be no way in hell Mike had taken note of where all that stuff went or how to put it back correctly, but I just reminded myself that this wasn’t my problem. I’d just make sure to get the hell out of there before she came home and discovered what he’d done.

  “So did you shave like I asked?” he said just then.

  “Uh huh,” I nodded.

  “Cool, cool,” he replied. “In that case, lets pick out an outfit for you. Cassandra’s kind of slutty, so it’s gotta be something tight ...”

  I watched as he began rooting through the mountain of clothes, pulling out various things and discarding them, when all of a sudden he said, “Oh, this! Definitely this!”

  He held it up to show me: it was a tiny white dress, no bigger than a t-shirt.

  “Dude, how is that thing even gonna fit me?” I laughed back, a part of me wishing I’d just ignored his damn phone call this morning.

  “Trust me,” he replied. “It’s gonna look great. Now, we’ll need underwear, too ...”

  “Oh my god,” I groaned, as I watched him race over to his sister’s dresser and start ransacking the drawers, pulling out great handfuls of bras and panties.

  I tried to act disinterested, but at the same time, I felt my fascination growing by the second as I got my first real glimpse of Ariel’s underwear. After all, she was hot as fuck, and I’d spent practically the whole of my uneventful teenage life lusting after her from afar. And just like I’d suspected,
it seemed like the kinds of panties she favored were all pretty skimpy and slutty: thongs and g-strings.

  “Here, catch,” Mike laughed, tossing a pair of tiny white panties at me. And then, a second later, a matching bra.

  “Oh my god,” he gasped, just then, as he pulled something else out of the drawer.

  “What is it?” I asked.

  “I think these are ... fake tits,” he said, as he fumbled open the small plastic box and removed two oval shaped skin colored discs, made of some kind of jelly like substance. “Woah, I never new my sister padded her bra.”

  “C’mon, man,” I muttered, feeling like maybe we’d overstepped the mark. “You should probably put those back.”

  “Put them back?” Mike gasped incredulously, shaking them at me. “What the fuck are you talking about? These are what we’re going to pad your bra with!”

  Pretty soon he had a whole outfit picked out for me. Hell, he’d even torn open a fresh pack of white hold-up stockings. The only thing we didn’t have was shoes.

  “What size feet are you?” he asked.

  “Six,” I admitted. I’d always been a little ashamed about my feet, which were pretty small and girly for a dude.

  He raced over to the closet and began pulling out all Ariel’s sneakers and sandals and heels, until he found a pair of heels that clearly had the size written on the bottom. “She’s a ... five,” he said. “Try them on.”

  “Really?” I groaned.

  “Really,” he shot back, giving me a look that said I had no choice but to do it.

  So with a sigh I grabbed one of the heels, then sat down on the edge of Ariel’s bed and kicked off my sneaker. I hoped to god it wouldn’t fit, but of course, my foot slipped inside. Sure, so it was a little cramped around my toes, but nothing too bad.

  “Ah, great!” Mike laughed. “Now try the other!”

  I pushed off my second sneaker and slipped my other foot into the heel, then tried to stand, but I quickly lost my balance and came flopping back down on to the bed, landing hard on my ass.

  “Don’t worry,” he said, laying a hand on my shoulder. “You’ll get the hang of it. Anyway, I’d better leave you to get changed ...”

  “What, right now?” I blurted out.

  “Absolutely,” he grinned. “We haven’t got a second to lose. You get changed, and I’ll get into my costume in my room. Just gimme a shout when you’re done ...”

  And just like that, Mike left me alone.

  Alone in Ariel’s bedroom, with all her slutty clothes ...

  5

  As I began to get undressed, I felt my heart begin to pound. I had to admit, there was something kind of exciting about the idea of putting on the sexy, slutty outfit Mike had chosen for me. Part of it was that I was actually transforming myself into the girl from my wet dream, that very same morning. But on top of that, I suppose I’d always had some secret fascination about the kinds of clothes girls wore.

  They were just so tight and figure hugging, leaving absolutely nothing to the imagination – so unlike the boring shapeless baggy jeans and oversize t-shirts I normally wore.

  Once I was fully naked, I took a quick glance at myself in the long mirror that stood in the corner of the room, assessing my skinny pale body, which was now completely hairless, save from a neat, dark brown crop of pubic hair just above my dick. I’d figured shaving that off would be a step too far, and anyway, nobody was going to actually see my junk, right? But I’d made sure to shave my balls and the peach fuzz that grew on my chest, belly and ass. And I’d made sure to shave my underarms, too, which was a good job, considering this dress Mike had picked out wouldn’t cover my arms at all.

  My cock looked so small and shriveled between my legs, and I hoped it wouldn’t make too much of a bulge in the panties.

  With nervous, shaky fingers I picked them up off the bed first. Damn, they were so skimpy, and I felt a charge of excitement at the thought that they were Ariel’s – that this very same wisp of white fabric had been sitting snugly right against her plump pussy lips and between her pert butt cheeks.

  I fumbled around with the panties until I’d worked out which way round then went, then gingerly stepped into them, sliding the soft white cotton up over my thighs, then tugging them right up around my waist. OMG. It was the strangest sensation. I could actually feel the strap at the back now sitting snugly between my ass cheeks, while at the front, to my amazement the tight stretchy cotton had cupped my dick so tightly that it actually looked like nothing more than the very faintest bulge.

  I double-checked in the mirror, my excitement spiking as my reflection confirmed my suspicions. And what’s more, when I turned and gave myself a glance over my shoulder, pushing out my butt, I had to admit – it looked pretty fucking hot! I actually had quite a peachy ass, as hot and sexy as a real chick’s, and it was hard to tear my eyes away from it to carry on dressing.

  Spurred on by the success of the panties, I grabbed the bra and pulled that on, too, but immediately it was a lot harder. For a start, I couldn’t reach around to clip it at the back, but there was no way in hell I was calling Mike back in here while I was still so scantily dressed.

  But then I had a new idea. I slipped it off my shoulders again and this time I buckled it around my waist like a belt, then shimmied it up my chest until it was in position, before pulling the straps over my shoulders. It was tight, I guessed I must be a little larger around the chest than Ariel, but it only dug in at my sides a little bit and I figured I could live with the slight annoyance. I desperately wanted to see how it looked, but before I allowed myself another peek in the mirror, I grabbed the box that contained those weird breast pads first, lifting them carefully out and giving them a little squeeze, feeling the gel-like substance moving and shifting between my fingers.

  I slipped them one by one inside the cups of the bra, then gave my brand new tits a tentative squeeze. And while I’d never actually touched real breasts to truly confirm, I still had the suspicion that they felt pretty realistic. Hell, they even bounced a little as I walked back over to the mirror to look! And when I saw myself again, I couldn’t help but smile.

  It was fucking insane what just those two little differences of the panties and padded bra made to my figure, and I excitedly pulled my hair out from its pony tail, shaking it out and letting it fall over my shoulders, glad I’d given it a full wash and condition that morning.

  Normally I hated wearing my hair that way – it always looked too fluffy and thick and girly. But now I realized it was perfect for my brand new look. I even started to suspect that my face wouldn’t need too much work in the makeup department. I already had quite prominent cheekbones and strangely full lips for a guy, and as I stared at myself in the mirror, I already knew that what I’d need to focus on most was my eyes – using whatever of Ariel’s products I could find to try and accentuate them somehow.

  But I had a lot more work to do on my costume first. I turned back to the bed, excitedly grabbing the stockings and shaking them out, wondering if there was a right way round to put them on. I found that the hold up part had a faint seam, so I figured that must go at the back.

  Then I sat down on the bed, all the while trying to ignore the oddly tight, wedgie-like feeling of the thong, as I set about rolling up the stockings and then slipping my small, girly feet into them – right one first, then left – before rolling them up my legs. And man, then felt good.

  As I watched myself sliding the silky white fabric up my slim, hairless legs, my vision framed by my long glossy hair, I actually felt like a girl – and I found myself really savoring the sensation of the stockings as they slowly but surely encased my legs in their semi-transparent fabric, right up to my thighs.

  Next I slipped my feet into the heels, which were lying nearby on the carpet. Well, I guess slipped isn’t quite the word – more like crammed. But I managed to get them inside anyway, then once again I tried to stand. And this time, I managed it ... just. I teetered a little, but held my balanc
e and as I tried out a few tentative steps, I found that if I put one foot in front of the other, and walked heel-toe, heel-toe, I actually stayed upright. Keeping my spine totally straight and my shoulders back helped a lot, too.

  Finally it was time for the dress.

  As I turned my attention to it, laying there on the bed, I wondered again if I’d even be able to fit inside it. It looked so ridiculously small and tight and I really didn’t want to rip it – pissing off Ariel in the process. I gingerly picked it up and pulled it on like a t-shirt, inching the tight stretchy fabric down over my fake boobs, then my stomach, feeling in cinching in the puppy fat I had there, giving the impression of a slim, toned waist. And to my relief I found that there was still enough fabric left to tug down over my bare buttocks, the hem finishing right at the top of my thighs – leaving a couple inches of milky white skin on show above the lacy white tops of my stockings.

  My heart was booming now as I once again approached the mirror, walking carefully, both scared and excited to see the full thing.

  And when I did, I honestly couldn’t believe it. It was such a transformation. I looked for all the world like a girl! I was slim and curvy, the dress really showing off a figure I didn’t even know I had. I even loved my hair, and I found myself reaching up and teasing and tousling it, to give it even more of the volume I normally hated.

  All that was left was makeup.

  Ugh. Where to even begin?

  I stared hard at my features, glad I wasn’t plagued by teenage zits or anything, again deciding that my eyes needed the most work. There was another smaller mirror over on Ariel’s dresser, the surface of which was littered with what looked like a whole cosmetics store’s worth of makeup. So there must be a few things there that would help, right?