Dressed for Pleasure Read online

  But at the same time, I couldn’t quite let go of the idea either, knowing I should at least try it before I totally dismissed it. Because it was still better than nothing.

  As I lay there in bed, fretting, I could hear Mom and Steve downstairs, talking excitedly about something, the sound of their chattering voices softly driving up the stairs and into my room. They were always so damn active at the weekend, going out on hikes and trips and doing outdoorsy stuff, while I think I must have inherited my hermit tendencies from my real dad, who spent most of his life slobbed out in front of the TV, drinking beer.

  A little while later, there was a knock at my bedroom door, and when I called out, “Hello?” my mom stuck her head into my room, a big smile on her face.

  “It’s such a nice day out there,” she said. “But let me guess, you’re going to spend it holed up in here, playing video games.”

  “Probably,” I replied, knowing there was no use in lying; she always seemed to know exactly what I was thinking.

  She moved further into the room, taking a seat on the end of the bed and then fixing me with a worried look. “Honey, is everything okay?” she said tenderly. “No problems at school or anything?”

  I shook my head. “I’m just a little tired is all.”

  “And you’re sure you’re not sick or anything?” she added, reaching out and laying a hand on my forehead.

  “I’m fine, mom,” I said.

  “Okay, well, I thought I’d better let you know that Steve and I were thinking of going for a hike today, and we were planning on taking the camping gear with us and staying overnight. I don’t suppose you’d like to come, too?” she added hopefully. “Might be fun?”

  “Thanks, but if it’s all the same, I’ll just stay here,” I said, as the situation began to dawn on me.

  Holy shit … I would be totally alone in the house tonight ...

  “Sure, honey,” Mom replied. “But make sure to call us if you get into any trouble or anything. We’ll make sure to keep our cellphones charged, okay?”

  “I’ll be fine,” I smiled back.

  With that, she left the room, and my brain began whirring even faster. I knew I still had a lot of obstacles to overcome if I was going to pull this crazy stunt off, but now that I had the house to myself all night, then maybe, just maybe, it might actually work ...

  * * *

  I stayed holed up in my room, willing everyone to leave, eager to get started. Mom and Steve were first to go, calling a cheery goodbye at about midday and then setting off in Steve’s SUV for god-knows-where, and about an hour later, I heard Madison hit the shower.

  As the hiss of the water echoed into my room, I considered sneaking into her room and trying to break into her phone, to snoop through her pics like Tyler had asked me to, but it seemed too damn risky. Unlike most teenage girls, Madison didn’t actually take that long in the bathroom and I’d die of shame if she caught me snooping.

  So instead I just bided my time, trying to play video games, but my heart wasn’t in it. In reality I was just waiting, eager to put this ridiculous plan into action.

  She spent an eternity in her room, listening to some cheesy rap music at full volume as she slowly got ready, and eventually, at about four o’ clock, I heard her leave without even saying goodbye – just the heavy slam of the front door and then … silence.

  Even though I still had all evening, I sprang into action the very moment I was sure I was alone, pushing myself up off the bed and then padding out into the hall, pausing to triple check everyone had well and truly gone.

  “Hello?” I called out, my voice echoing through the empty house. “Anyone home?”

  I even gave Madison’s bedroom door a tentative knock, though I knew I was being stupid. Obviously there was no answer. And so, after a final deep breath, I reached out and turned the handle, then made my way into her room ...

  4

  I’d only ever been in Madison’s room a handful of times, and never alone, so it was weird to be able to really look at everything in detail for the first time, without her there, waiting for me to leave.

  Her room was actually pretty neat and tidy for a teenager’s, and I knew I’d have to be super careful to put back everything exactly where I’d found it once I was finished. After all, she was the kind of person that would know if something was even the teensiest bit out of place.

  I gazed around: at the bright yellow walls and rumpled neon pink bed sheets, at the white dresser unit with all her makeup set out, then at her large closet and set of drawers.

  Now that I was actually here, standing in her room, my plan seemed crazier than ever. But I knew I had to at least give it a shot. So I figured the first thing I would need were some of her clothes. I headed over to her closet and pulled the doors open. On a day-to-day basis, Madison pretty much always wore variations on the same theme: leggings and a sweater, or else mini skirts and t-shirts. But I discovered that the closet was actually packed full of tight party dresses and coats – things I’d never seen her wearing that much.

  I turned my attention to a nearby chest of drawers, figuring that must be where she kept her regular, everyday stuff. And I wasn’t really thinking when I slid open the top drawer to be greeted with a whole sea of her panties and – as if that wasn’t intimate enough – a huge purple vibrator and a tube of lube, too.

  I stared at the vibrator with shocked amazement. God damn, it really was gigantic, and I felt a flash of horny excitement despite myself, as the image of Maddy using that purple monster flashed into my head.

  I’d never really thought about her in that way before, but with her vibrator staring me in the face, how could I not?

  I tried my hardest to push the dirty thoughts to the back of my mind and stay focussed on the task at hand, knowing I’d need a pair of her panties and one of her bras to use in my photo shoot. As I began searching through her underwear drawer, I made sure to try not to mix everything up too much, in case she somehow found out what I’d been doing. I didn’t know exactly what I was looking for, but as I searched through her panties it slowly became clear that Maddy favored skimpy thongs, g-strings and cheekies, and again the idea of my stepsister wearing such slutty, skimpy underwear around the house beneath her leggings had my cock throbbing all over again.

  I tried to pick out a matching set, and in the end selected a sporty hot pink thong and matching bra, both with Victoria’s Secret written on them in shiny white lettering.

  I laid the underwear out on the floor next to me, suddenly curious what it would feel like to actually try them on. I had to admit: there was something weirdly exciting about the idea of trying on my stepsister’s sexy underwear.

  As I resumed my search through her dresser, I found that the middle drawer contained a whole bunch of vests and tops and I chose a simple white one, with a high neck, hoping it might hide my Adam’s apple a little. It was cut in such a style that my arms would be completely bare all the way up to the tops of my shoulders, and as I added it to my pile, a new thought began to dawn on me.

  I’d have to shave – and not just my armpits, either.

  Luckily, the hair that grew on my legs wasn’t actually too noticeable in the first place; it was more like a downy blonde fuzz than grown man’s hair, and I didn’t have any on my chest or belly. So hopefully it wouldn’t be too huge an undertaking to get myself totally smooth and hairless.

  Finally I selected a pair of grey leggings and a black mini skirt, figuring I could try them both on and see which looked best.

  I knew that Maddy often just wore regular sneakers, and actually I had a pair of black vans which weren’t a million miles away from the kind she always wore. So that was my outfit complete.

  My next task was hair. I could remember her pestering Steve for months to let her buy a set of super expensive hair extensions, which she’d only ever ended up wearing a couple of times, and I hoped she hadn’t thrown them out.

  So I began rooting around and in the very back of her close
t, amongst the various junk she’d stuffed back there, I found the package of hair extensions, which had been shoved carelessly into a plastic bag. I pulled one out to examine it, combing it out with my fingers. It was the same dusky blonde color as Madison’s real hair, and it attached with a small row of metal clips. There were a set of six extensions in the bag, and I hoped they’d be enough to give me the illusion of long, natural hair.

  Once I had everything gathered together, I felt a sharp pang of nervousness, knowing that it was time to put my plan into action. But of course, first I had to go grab a shower … and a razor ...

  5

  I was planning to just use my own electric razor and hope it did the trick, but as I was getting undressed in the bathroom, the shower already hissing and steaming, I caught sight of Maddie’s small pink plastic razor, laying on the side of the bath next to a tube of sensitive skin women’s shaving foam that I guessed she must use, too.

  Hoping that it might do a better job, I grabbed a hold of the can and razor, and after quickly wetting my body beneath the shower, I slathered on a generous amount of the foam, working it up my legs, then beginning to shave.

  As I mentioned, I didn’t actually have particularly hairy legs, so that part of the job didn’t take too long at all. But I could definitely see a difference as the razor dragged in smooth motions up my calves and thighs, leaving fresh pale hairless skin in its wake.

  I did the same thing to my thighs, too, then figured I’d better go the whole hog and shave between my legs. I had no idea whether Maddie shaved herself down there, but I knew most girls her age did, so I’d probably better do it, for realism’s sake.

  This turned out to be a little more tricky. The hair around my dick and balls was a lot thicker and more wiry, and in the end I decided to buzz it short with my electric razor, and then shave it. That worked out a lot better, and after some careful attention and a few gymnastic poses, I had my whole lower half completely smooth and hairless.

  It was so weird, peering down between my legs as I washed off the last scraps of foam beneath the shower, staring at my junk which was now completely bald, making me look even more like a puny little kid than normal. I just hoped that from the right angles, I’d look like a sexy chick.

  Finally I shaved under my arms and even though there was only the faintest downy blonde fuzz, I dragged the razor over my chest and belly, too, then I gave myself a good long wash, using Madison’s cherry scented shower cream, figuring I’d better smell like her, so that when I put the clothes back after I’d worn them, she wouldn’t be able to tell.

  Once I was finished, I shut off the shower, patted myself dry, and then for good measure I sprayed myself with some of her deodorant too, which was so damn sickly sweet it had me coughing and spluttering.

  With a final deep breath, I headed back to Madison’s bedroom, knowing it was finally time to get dressed ...

  * * *

  As I shrugged off the towel, I felt weirdly nervous, like I might get caught at any second. My heart was actually thudding against my ribs as I reached out and picked up the skimpy pink thong, holding it up and examining it for a moment, marveling at how damn tiny it was – so different to my baggy cotton boxer briefs.

  I’d always secretly loved it when I caught sight of a thong peeking out from a chick’s leggings at school, but never in a million years did I think I’d actually be wearing one – and my own stepsister’s, no less.

  I gingerly stepped into the panties, hoping to god that I didn’t stretch them so much that Maddy would know I’d been wearing them, as I tugged the thong up around my waist, feeling it slip tightly between my butt cheeks in the process. I mean, I knew this was how thongs worked and all, but even so, it was still something of a surprise, and for a moment I found myself instinctively reaching around and trying to pick at it like it was a wedgie.

  Once I’d adjusted it a little, I strode over to the mirror to take a peek, each step I took working the damn strap even further between my ass cheeks, then took a nervous look at myself. From the front I still just looked like me, and my cock and balls had made a frustratingly large bulge in the neon pink fabric of the panties.

  But as I turned my body around and peeked back over my shoulder, I felt a sudden flash of excitement. Because from that angle at least, I looked pretty damn good.

  I began experimenting with a few different poses, spreading my legs wider, arching my back, bending forwards, and I felt my excitement and confidence growing by the second, knowing that if I snapped a couple of pics from the right angle, I could definitely hide the bulge of my cock and balls. And best of all, my ass looked fucking amazing – even hotter than I’d hoped!

  The thong really did work wonders, framing my big round butt cheeks, making my ass look so pert and sexy that I actually felt myself getting a little horny, even though I knew that was ridiculous, seeing as I was staring at my own body.

  Spurred on, I raced back over to the bed and grabbed the bra. I somehow knew instinctively – maybe I’d seen it in a movie or something – that the way to put it on was to fasten it first around your waist like a belt, then shuffle it into place. So that’s what I did, and I have to say, it actually felt pretty good to finally have something tight and snug on my chest, scooping the embarrassing puppy fat of my pecs into two round bumps, and even pushing everything upwards, too, creating, at least from where I was standing, two small but realistic tits and a hint of cleavage.

  I could feel the excitement bubbling up inside me; a sort of strange, tingling Christmas morning anticipation, and I wanted to go further now, knowing I wouldn’t be satisfied until I could look as realistic and girly as humanly possibly. I’d always loved dressing up as a kid and this was kind of like that, only with a weird sexual element to it, too.

  I had to admit: it was addictive.

  Seeing as I’d gone to the trouble of shaving my legs so nice and smooth, I figured I’d better try on the mini skirt first, to show them off, and if that looked bad then I could swap the skirt out for the leggings. So I stepped into it, hitching it up around my waist, then tugging it into place over my thighs and butt. It was super tight and short, and even without taking a peek at myself in the mirror, I just knew it looked really slutty.

  Steve was always pissed at Madison when she went out in short skirts, and I guessed I must look pretty similar: the stretchy black fabric pulled taut around my thighs and butt, my long smooth legs on full display.

  Next I tried on the crop top, which stopped just above my belly button. Luckily I was pretty skinny around my stomach, and while I didn’t exactly look toned and ripped like some of the other boys at my school, I realized now that that was probably for the better. Because my soft but smooth stomach looked pretty girly, accentuated even further by the pert round bumps of my tits. By now I was absolutely desperate to take a look at myself in the mirror, but I figured I’d better try and put in the hair extensions, too.

  So I gathered them up, then went over to the dressing table and took a seat at it, my face and shoulders framed by the small oval mirror that stood facing me. I had no damn clue what to do with the extensions other than to try and clip them carefully onto my real hair. But then I had a brainwave.

  I knew that sometimes Maddy wore her hair scraped back and if I clipped the extensions into the back of my real hair then scraped the whole thing back and held it in place with a headband, it might look pretty good.

  So I set to work carefully clipping in the extensions one by one at the back of my head, doing it more by feel than sight and hoping to god I’d not made a total hash of it. Anyway, they didn’t need to be perfect, I reminded myself. It was only for a few photos. I wasn’t actually planning to show my face or anything – I just wanted the long hair to be visible in the corner of the frame as another convincing detail to fool Tyler and his buddies.

  Once the extensions were clipped in place, I grabbed one of the headbands I saw laying on her dresser next to a pot of makeup brushes and carefully fitted that in
place towards the back of my head, covering the join between my own scraped back hair and the start of the extensions.

  Before I stood up, I figured I might as well put on a touch of makeup, too. I stared in confusion at the many glossy sticks and tubes and pots all laid out in front of me, wondering what the hell half of them even did. But a simple stick of bright pink lipstick finally caught my eye. I knew what that was, at least.

  So I took off the top then twisted the bottom, watching as the hot pink lipstick emerged. I saw that it was actually the same identical color to my bra and panties, which was pretty cool, so I leant forwards, opening my mouth and then carefully running the stick back and forth across my lips, making sure I didn’t go past the edges. I surprised myself by actually doing a pretty good job, if I do say so myself, maybe because I had a naturally steady hand for fiddly little jobs like that.

  Spurred on by my success with the lipstick, I took out something called ‘liquid eyeliner’ which turned out to be a brush pen design. I wasn’t sure exactly what style to do, so I grabbed my phone and started searching for simple eyeliner tutorials.

  And before I knew it, a whole new plan was forming …

  Because it seemed like there were a veritable shit ton of beginners makeup tutorials on YouTube and Google and I realized with growing excitement that I had everything I needed right here this room to go the extra mile. To well and truly transform myself ...