Dressed for Pleasure Read online

  6

  After a few failed attempts and a lot of cleanup with some face wipes and makeup remover that I found in the bathroom, I was finally finished. In just under an hour, I felt like I’d gone on a full beauty school crash course. Suddenly my head was crammed to bursting with eye shadow techniques, contouring, lip liner, blusher application – the works.

  And I couldn’t have been more happy with the finished result, either! I excitedly pushed myself up from the dressing table, to finally go take a look at myself in the full length mirror, for the first time feeling truly girly.

  There was something about those tight clothes – the mini skirt, the top, not to mention the feel of the hair extensions swishing around by my shoulders, the silky smoothness of my shaved legs and of course the thong, so snug and tight beneath my skirt – that made me feel well and truly feminine. And when I finally saw the full effect in the mirror, my hopeful suspicions were confirmed.

  Holy shit, I thought, my heart flooding with excitement. I look fucking hot!!!

  It was insane; I hardly even recognized myself.

  Okay, so I didn’t look exactly like Maddy. For a start my face was a different shape, thinner and more pixie-ish. But I definitely looked like a real girl, and my body was actually pretty similar to hers, just like I’d suspected. By now I felt sure that if I took a few pics from the right angles, they’d look pretty damn convincing.

  It was finally time - time to get this show on the road.

  My heart was pounding as I grabbed my cellphone, both excited and nervous to finally put my crazy plan into action.

  I decided to start off slow with a couple of teasing, fully dressed shots – the kind any girl might take if she was feeling pretty and sexy. I’d seen enough Facebook and Instagram photos in my time to know how they went, and I began snapping away, holding the camera at various flattering angles, trying to make my tits look big and pert and making sure keep my poses girly and cute.

  Sure, some of the photos looked like total crap, but already I’d managed to snap a couple that I figured would look great once I’d added a filter and cropped them a little.

  Next it was time to increase the heat and start focusing on my best asset ... my ass. So I turned to face away from the mirror, then arched my back and bent slowly forward, pushing out my butt, spreading my legs wide, the mini skirt just starting to ride up, showing off the smooth skin of my upper thighs and the very hint of butt cheek for good measure.

  Again I snapped a couple of hot sexy pictures, and soon I found myself really getting into it, as I began teasing the skirt higher and higher, until my butt was on full display, framed by that sexy pink thong. With a little trickery and a few judicious angles, I managed to keep my throbbing boner out of shot, too.

  Before long, I’d laid down on Maddy’s bed as I began my final striptease, first by inching up the crop top until my bra was showing, then scooping my tits out, tweaking and tugging at my nipples until they were nice and hard. And even though I knew I’d never actually send a face pic to Tyler, I still found myself taking a few out of curiosity, unable to believe that the hot girl on the screen of my cellphone was really me. I tried my best to pout and smolder for the camera, and the results were pretty damn good, even if I do say so myself.

  Finally, I stripped down to my panties, squeezing my tits together to make them look extra buxom and then inching my panties slowly around my knees, before squeezing my cock tightly between my thighs so that it was hidden from view – giving the surprisingly realistic illusion of a cute shaved pussy.

  Flash!

  I was done. The photo shoot was over. But my horniness didn’t go away. In fact, I felt myself getting more turned on than ever as I lay back on Madison’s bed, scrolling back through the pictures, starting to make my selections, deleting some pics then cropping others, trying out different filters, while my mind starting to fill with weird sexy thoughts.

  What if Tyler and the twins actually got turned on looking at these pics? What if I gave them all boners? I couldn’t help but imagine their cocks growing hard at the sight of my sexy, girly body and as fucked up as it might sound, the idea of getting them off turned me on more than ever. I guess I’d never really felt sexy or attractive before, but laying there on Maddy’s sheets, my slutty pink panties around my ankles, I felt cute and naughty in a way I never had.

  The whole thing was weirdly addictive. I found I loved being like this, and I was actually kinda sad that my fun was coming to an end.

  But then a new, even naughtier idea took a hold of my swirling brain.

  What if I tried out Madison’s vibrator ...

  As soon as I considered it, I felt this intense shot of adrenaline rush through me, because I knew that I wasn’t going to be able to get the damn idea out of my head until I’d tried it.

  So I pulled the panties back up around my waist, then jumped off the bed, dashing over to Maddy’s underwear drawer and rooting through until I found the vibrator, once again marveling at how fucking huge it was. I pulled it out with shaky fingers, my whole body crackling with nervous energy as I carried it along with the lube back to the bed and lay down once more on top of the sheets.

  Was I really about to do this?

  Never in my young life before had I done anything so kinky before, but then again, I’d never dressed up as a girl before either, and that had turned out to be way more fun than I’d ever expected.

  So I let my curious fingers curiously curl around the thick hard shaft of the vibrator, wondering if I could really fit something so thick in my ass. Hell, I’d never even stuck a finger in there before, and I figured I’d better start off small and then work my way up.

  My hands were actually trembling as I took the lube and squirted a blob onto the fingers of my right hand. Then I tugged the strap of the thong to one side, before slowly teasing the cool, gooey liquid gently into my tight little butthole.

  It was a pretty odd sensation – not quite what I was expecting. It wasn’t bad exactly, but it wasn’t like oh my god amazing either. Still, I persevered, easing my finger a little deeper into my butt, and that’s when I felt the first faint flash of pleasure, catching me off guard.

  Woah!

  All of a sudden I understood. Because somehow, as if by some crazy magic, it seemed like I was stimulating the same pleasure centers that might get activated if I was touching my dick. Even though of course my cock was still totally untouched in my thong.

  As I began to ease my finger slowly in and out of my ass, I felt the sensations growing stronger, and my dick actually began to throb in my panties, aching sweetly, even though I still wasn’t touching it. It was crazy and amazing and I began to wonder what it might be like to feel that big, thick vibrator in there instead of my finger.

  So I grabbed a hold of it and squirted another generous dollop of lube onto it, working it up and down the glistening shaft, before guiding it gingerly between my butt cheeks, spreading my legs wide as I began to tease my butthole with the large bulbous head. I tried to let my whole body relax as much as I was able, taking a few deep breaths for good measure as I applied a little more pleasure and then all of a sudden, no doubt helped by all that slimy, slippery lube, the shaft actually began to ease inside me, stretching my ass so wide that I paused, shivering on top of the sheets, wondering if I could even take any more without damaging myself.

  I had to stifle a soft moan as I tried again, guiding yet more of the girthy purple vibrator inside me, filling my tight hole until I’d begun writhing and sighing on the bed, my untouched cock still rock hard and aching in my panties, while my mind swirled with all kinds of naughty, dirty thoughts.

  Then I remembered: it was a vibrator after all. The clue was in the name …

  So I let my shaky fingers fumble downwards until they were gripping hold of the circular base, and I slowly turned it, letting out a deep moan of surprise as it began to softly buzz inside my ass, sending fresh shockwaves of pleasure through my skinny body. I turned the base even f
urther and the buzzing intensified, so much so that I could no longer feel where the vibrator ended and my body began.

  By now I felt so damn overwhelmed that I was writhing and sighing, lost in ecstasy, feeling so girly and slutty and sexy, there on Maddy’s bed, dressed in her skimpy panties, my untouched cock rock hard and throbbing while my skinny body shivered and trembled as I eased even more of the buzzing purple monster into my tight little butthole.

  As I did, I found myself thinking again about those pictures I’d taken – how hot and sexy I’d looked in them, and how I hoped they’d turn Tyler and the twins on. I imagined Tyler looking at them, at me, his black eyes filled with lust and his cock growing so hard and hot that he just had to masturbate, impatiently tugging open his jeans to free himself, his big strong hand pumping up and down his slick hard shaft.

  Then my fantasy went even further, as my thoughts seemed to spin out of control. I imagined that Tyler was actually here with me, here on Maddy’s bed laying over me, and that it was his thick hard cock buried to the hilt in my quivering ass, pushing me over the edge, making me lose control ...

  With a shudder, I felt myself topple over the edge – the orgasm catching me totally off guard. I didn’t even think that guys could blow their load that way, but sure enough, I felt the most powerful orgasm of my life shudder through me, my muscles clenching and my body quivering, as my cock flooded Madison’s thong with warm gooey cum until I was totally spent.

  Shivering and trembling, I shut off the vibrator and eased it slowly from my ass, my head spinning and my breath shivering past my lips as I slowly came back to my senses.

  Holy shit.

  That was way more intense than I’d been expecting. And while I felt a strange pang of guilt as I remembered that it had been Tyler I’d thought about as I’d cum, I told myself not to worry too much about it. It was probably just because I was dressed as a girl, not to mention the crazy sequence of events that had let to this moment.

  As soon as I sent him those damn photos, things could get back to normal; I could return to my old self and pretend that none of this weird fucked up stuff had ever happened. It would be my little secret.

  I eased the sticky gooey panties off and balled them up, figuring I’d need to give them a wash and then sneak them back into Madison’s drawer. The vibrator would need cleaning, too.

  But before all that, I grabbed hold of my phone, just wanting this whole thing to be over with. I quickly scrolled through the pics I’d taken, selecting the very hottest ones, then put them all in a text message to Tyler.

  I paused for moment, before typing out, I found these on her phone, then hit send.

  I breathed a sigh of relief.

  It was over. I could finally return to normal and pretend none of this had ever happened.

  But a few minutes later, just as I was picking up the panties and vibrator to take them to the bathroom, I heard a sound that caused my stomach to flip over on itself.

  My phone was ringing.

  And sure enough, when I checked the display, it said Tyler calling.

  I reached out a shaky hand and answered the call ...

  7

  “Nice try, faggot,” Tyler growled, the moment I answered the call. “But I know for a fact that those photos aren’t of Madison.”

  I felt my heart begin to thud and I felt so woozy and sick, I had to sit down on the edge of the bed to steady myself.

  “Uh, they are, dude,” I offered weakly, hearing the jangle of nerves in my voice as I spoke.

  “Madison’s at Janey’s house tonight,” Tyler continued in the same cold, menacing tone. “I know that because Janey’s younger sister is Brandon’s girlfriend. So tell me this, faggot, how the fuck could those photos you sent me be of Madison, when the timestamp on them says they were taken tonight ...”

  I felt my stomach drop through the goddamn floor.

  The timestamp? I didn’t know too much about cellphones, but the moment Tyler said it, it triggered some distant memory of how all photos carried extra information on them, stuff like what time and date they were taken, and you needed to actively scrub that data if you didn’t want the receiver to know it.

  I was such a fucking idiot. I should have guessed Tyler would be smart enough to check on that kind of stuff.

  “Those photos weren’t of Madison,” he continued, his voice low and brimming with menace. “They were of you, weren’t they?”

  “Tyler, please,” I pleaded, knowing there was no use in denying it. “Don’t tell anyone. Just delete them. Please, I’ll do anything ...”

  My words hung in the air and I waited for what felt like an eternity before he spoke again.

  “You’ll do anything?” he repeated slowly and firmly.

  “Anything,” I shot back, totally desperate in that moment, knowing with all my heart that I would give Tyler whatever money he asked for or let him beat me up for a whole month straight, anything just so long as he promised not to show anyone those goddamn photos.

  How could I have been so fucking stupid?

  “Alright,” he said quietly, a strange new tone entering his voice, so that it sounded like he was smiling as he spoke, “if you really don’t want me to show these pictures to anyone, then meet me at midnight at the back of the field tonight. You know where.”

  “Okay …” I said hesitantly, wondering why the hell he wanted to meet me there, and what might be in store for me if I went.

  “And dress like you were in the photos,” he added in a menacing growl, before hanging up the call.

  I sat on the end of the bed, my cellphone still pressed against my ear, rooted to the spot in pure shock. Had I heard him correct? Did he really want me to go meet him tonight dressed as a girl? The idea seemed too crazy to allow myself to believe, and I began to wonder if perhaps I’d imagined it. But deep down I knew it was true.

  What’s more, I could still remember the kinky slutty things I’d fantasized about as I’d plunged that vibrator deep into my ass, and despite my total terror, a part of me wondered if perhaps Tyler actually wanted me the way I’d wanted him …

  I checked the clock on my cellphone. It was a little after ten and the high school field was a thirty minute walk away, which meant I really didn’t have too long to get ready.

  To prepare myself ... for Tyler ...

  * * *

  Just over an hour later, I found myself pacing back and forth by the front door, debating on whether or not I could really set foot outside the house dressed like this.

  I’d put on a fresh pair of panties – this time a black lacy thong – and I’d found a matching pair of black hold up stockings with lace tops. My feet were encased in a pair of simple black Vans, which were the most unisex sneakers I owned, and I’d tied back the hair extensions up in a high tight ponytail.

  I’d also watched a bunch of videos on YouTube on how to feminize my mannerisms. After all, I didn’t want anyone I might pass in the street thinking I was anything other than a real biological girl, perhaps just walking home after a night out with friends.

  It turned out the secret was to take smaller steps, to swing your hips as you walked, and to keep your head held high and your back straight.

  Which was all well and good in theory, but now I had to actually put what I’d learnt into practice and I felt sick with worry.

  The thirty minute walk seemed like miles, now that I had to make it wearing a skimpy mini skirt and crop top, and I just didn’t know how I was going to do it. I considered wrapping my body in a long jacket, but it was so damn warm outside, if anything that might draw even more attention to me.

  I reached out and gingerly pulled open the front door, staring out at the dark empty driveway and beyond it the sidewalk.

  Could I really do this?

  My heart was hammering hard, thudding against my ribs, and again I considered just going back inside, taking off all this stupid stuff, putting everything back where I’d found it and facing the consequences on Monday morning. Bu
t the thought of the whole damn high school knowing about my sexy photo shoot had me wincing with stomach churning embarrassment.

  No. I needed to do this. I needed to face up to Tyler, and hope that he was true to his word.

  So I took a final deep breath then stepped out into the warm night air, closing the door behind me. And as I began to walk, I reminded myself how real I looked. After all, I’d spent a bunch of time in front of the mirror in Madison’s room, scrutinizing myself from all angles, touching up my makeup, adjusting my hair and stockings, until I was totally happy with my appearance. Deep down, I knew I looked like a real girl, so now I just needed to act like one.

  As I walked, I made sure to keep my shoulders back and my head held high, just like I’d learnt from the videos, and I tried to tune in once again to the subtle feminine energy I’d felt, back when I first got dressed.

  I had to admit, even now, heading towards god knows what, there was still something so thrilling about being out in public dressed like this.

  Just then, I caught sight of a bus stop up ahead, with a young couple standing at it, checking their cellphones. It felt like a test, somehow: if I could walk past them both on the sidewalk, without them noticing I wasn’t a real girl, then I’d know my disguise was good enough.

  I kept my poise and grace, taking small steps, trying not to speed up or look awkward, holding my breath as I passed them. My stomach vaulted as the guy stared up from his cellphone at me for a half second, then returned his gaze to the screen, his face unchanged.

  I felt my body rush with excitement and adrenaline.

  I passed! I actually passed!

  It was such an awesome feeling, for a moment I forgot where I was even walking to, as every sense in my body seemed to heighten for a moment. I felt so utterly aware of everything: the balmy night air licking at the bare tops of my thighs, the subtle weight of my breasts cupped tight in the bra, the swish of my ponytail, and of course the tight black thong, holding my cock so snugly while the strap at the back gently flossed my butthole with each fresh step I took.