Dressed for Pleasure Page 4

  “Stop,” I gasped. “Stop, I think I’m too tight ...”

  “You’re definitely not,” she smiled back. “Trust me, I’ve taken some pretty huge cocks in my time. You just need to relax into it. Here, I think this will help ...”

  She licked her finger tip then reached between my legs, resting it against my clit, applying just enough pressure to make me moan in ecstasy, and at the same time, I felt her slide her long hard cock deep inside me in a single delicious motion.

  And holy fuck! It was like nothing I’d ever experienced before. I felt so full … Like the yearning inside me had finally been quenched.

  She took things slow to begin with, rocking her hips in a gentle but steady pace, easing her cock in and out of my pussy, and soon I was grabbing her buttocks, urging her to fuck me faster, wanting finally to feel what I’d been fantasizing about for so long and take me hard and rough.

  Sure enough she did, slamming her cock so hard into my aching pussy that I could feel her balls slapping against my asshole, my breasts bouncing and the involuntary sighs and moans falling from my lips. And soon I could feel my orgasm starting to approach; I tensed in anticipation, suspecting it would be even more intense than the ones I’d experienced on my own. And holy shit. I was right.

  As the first flashes of pleasure hit, I let out a low trembling moan, my nails digging into her back as my body began to quake and shudder, the sensations swarming inside me, growing so damn intense that I had to throw my legs around her, holding on for dear life as my whole body bucked and thrashed from the force of my orgasm, while my mind splintering into what felt like a million electric pieces.

  I’d hardly had time to recover when Jenna pulled her cock from my pussy and tugged off the condom, her face set in a grimace like she was about to cum, too.

  “Where d’you want it?” she growled, and I surprised myself my quickly moving onto all fours, offering my open mouth to her.

  I only just about had time to wrap my lips around the swollen head of her cock and stroke it a couple times before she let go, her hands moving into my hair as she let out a low moan. I felt her cock swell against my tongue and then a moment later the cum started to blast into my throat and flood my mouth. She held my head in place as her body shuddered and her meaty cock pulsed, and I gulped back every last drop of her load, surprised that it didn’t actually taste too bad at all, just a little salty.

  I even found myself licking and lapping at the shaft, cleaning up any extra that had dribbled from of my mouth, before flopping down next to her on the sheets, flushed and satisfied, my whole body tingling.

  We lay there together in silence for a moment, catching our breath, before Jenna began to speak.

  “That was amazing,” she said quietly..

  “It was,” I agreed. “It was incredible.”

  “I was wrong about you, Matt,” she added gently, turning to face me. “I’m truly sorry I was such a bitch when we first met. I shouldn’t have taken it out on you like that at the coffee shop. Y’know, somehow I feel like that’s part of what got us into this stupid mess in the first place. Like karma, or something. I probably sound crazy, but then this whole damn situation is crazy, right? I mean, I just had sex with myself!”

  She began to laugh, and I quickly joined in, both of us enjoying the easy, relaxed vibe that had grown between us.

  “Come here,” she said all of a sudden, leaning in to kiss me.

  “Woah, wait,” I said with a grin, “I thought that was rule number one? No kissing, remember?”

  “I changed my mind,” she whispered, pushing her lips hard against mine, her tongue pushing into my mouth as my body charged all over again with horniness, my clit throbbing and my nipples hardening ...

  But all of a sudden, I felt another sensation mingling in with my passion. Sure enough, I felt the same drowsy, woozy feeling begin to sweep over me just like it had when I’d eaten the candy, back on the bus.

  Before I knew it, I was struggling to even keep my eyes open and Jenna obvious felt the same way, her eyelids closing as she fell into a deep, heavy sleep just moments before I did ...

  * * *

  I woke slowly, and once again the sunlight was streaming through the huge windows of Jenna’s beautifully furnished bedroom. The sheets felt just as soft and luxurious as before, only now when I reached down between my legs, my fingers curled around the throbbing hardness of my cock.

  I shifted over in bed, and sure enough, there was Jenna – back to her old self, her face so damn pretty as she slumbered next to me. I reached out and gently shook her awake.

  “Jenna,” I murmured, “Wake up. It’s happened. We’ve switched back ...”

  Her eyes flashed open in surprise and excitement, and she immediately did the same thing I’d just done, pushing her hands beneath the sheets to check, cupping her breasts for a moment before letting out a whoop of pure joy.

  “Thank fuck for that!” she laughed. “Oh my god, I was worried I’d stay that way for ever ...” She paused, obviously not wanting to hurt my feelings. “Don’t get me wrong, in the end I did have some fun in your body,” she added with a soft smile, no doubt referring to what had happened between us in bed last night. “But even so. I’m glad it wasn’t permanent.”

  “Me too,” I replied, honestly. I mean, sure, I wished it had lasted just a little longer but …

  Just then, I felt her hand curling around my cock.

  “I see someone’s awake,” she whispered playfully, as her fingers began to slide up and down my throbbing shaft.

  Wait, what the fuck?

  This experience really had changed her, and who was I to turn down her advances? What’s more, now that I’d been in her body, I felt like I knew exactly what to do to bring her pleasure. I wasn’t sure if it was just going to be some crazy one-off thing or whether this was the start of something bigger between us, and truthfully right there and then, I didn’t even care.

  As I leant in to kiss her, I was simply excited to enjoy her amazing body all over again ...

  Tyler’s Girl

  1

  “Holy shit, are you Madison White’s brother?” Tyler asked, his rugged face flickering with surprise as he wrestled with the idea that she could have a younger brother as dorky as me.

  Truth was, Madison was my step sister – her dad had married my mom, way back when I was ten and she was eleven – but I didn’t want to get into the specifics of it, especially with someone as mean and scary as Tyler, so it was easier to just nod and mumble, “Uh huh.”

  “That’s insane,” he grinned, looking me up and down with his big dark eyes, taking in my skinny body, bad posture and unfashionable haircut, then shaking his head in pure amazement.

  I just shrugged and muttered, “I guess it is,” hoping he and his two cronies, Daniel and Brandon, might let me go soon.

  They’d approached me as I was walking across the field, backing me into a corner by the old crumbled down hut that used to store gym equipment, and there was seemingly no escape.

  I’d hated Tyler ever since I first started at this high school. It seemed like his whole goal in life was to make other kids’ lives a misery. He was the meanest boy in the whole of our year by a mile and everywhere he went, he was always flanked by his two burly cronies, Daniel and Brandon, who were twins, and who’d kick a guy’s ass at the drop of a hat, if Tyler told them to.

  But instead of kicking my ass right now, the three of them still just seemed to be trying to process the idea that a girl as hot and popular as Madison White could possibly have a brother as uncool and nerdy as me.

  “You ever, like, peek on her getting changed?” Tyler grinned, taking a step even closer to me, so that he was towering right over me, reminding me how scrawny and weak I was in comparison to his lean yet strong physique.

  “Dude, he’s her brother, that’s like insect or whatever it’s called,” Daniel cut in.

  “Wait, I’ve just had an awesome idea,” Tyler continued, ignoring Daniel’s commen
t, his lips curling into an evil grin and one of his thick dark eyebrows raising.

  Watching him smile that way, I felt my heart sink, knowing that whatever this ‘awesome idea’ was, it probably involved me somehow.

  “The fappening,” he announced, like we should all know what the hell that meant.

  “The what-ening?” Brandon replied.

  “You know,” Tyler said, punching Brandon on the arm, “that thing that happened where all those hot celebrity chicks got their cellphones hacked,” Tyler explained, “and someone leaked their nudes online.”

  “So?” Brandon persisted, as I felt the queasy dread increase in my stomach as I began to guess what Tyler was about to suggest. “What’s that gotta do with anything?”

  “So,” Tyler shot back, “imagine if we could get a hold of Madison White’s nude pics? Tell me you wouldn’t wanna see those?”

  “Oh man, of course I would,” Brandon laughed. “But how the hell are we gonna get them?”

  Which is when Tyler nodded at me, widening his eyes, and the idea finally clicked in Brandon’s empty skull.

  “Ohhh!” he grinned, the three boys all staring straight at me now. “Yeah, man! That’s a fucking great idea.”

  “C’mon, guys,” I muttered, backing away from them until my back was pressed right up against the brickwork, and a second later I felt Tyler’s hand clamp down hard on my shoulder, rooting me to the spot. “I mean, how am I meant to even get them ...” I added.

  “You sneak into her room while she’s in the bathroom or whatever,” Tyler hissed, his dark eyes narrowing and his voice full of threat and menace. “You take her cellphone and you go through her photos and then you send whatever nudes you find on there to me. And you do it this weekend.”

  “But what if there aren’t any, uh, nudes on her phone?” I countered weakly.

  “Then you fucking set up a spy cam or whatever and take some,” he growled. “Seriously, dude. I’m not fucking around here. You either send me some goddamn nude photos of your sister by like Sunday night, or ...”

  He let the sentence trail out. After all, it was totally obvious what would happen to me if I didn’t follow through: I’d get my puny ass well and truly pounded.

  “I’ll try,” I said quietly, staring at the floor.

  “You’d better,” Tyler replied, finally letting go of my shoulder.

  He told me his cellphone number, watching like a hawk as I typed it into my phone, even making me call him to show that I had it set up correct.

  And then finally they let me go.

  “What was all that about?” my buddy Michael asked, as I walked over to join him on the other side of the field.

  “Don’t ask,” I sighed, a gloomy cloud hanging over me now, the weekend ahead suddenly transformed into something I really wasn’t looking forward to.

  Just then the bell rang to signal the last class of the day, and as we all trudged back inside, I felt my stomach sinking even further, my mind spinning and swirling, as I wondered what the hell I was gonna do ...

  * * *

  “You okay, honey?” Mom asked that same evening, as we all sat at the dining table. “You’ve hardly touched your food.”

  “I’m fine,” I replied unconvincingly, moving my untouched macaroni cheese around my plate with my fork.

  “C’mon, smile,” she persisted. “It’s Friday night! And I thought mac n’ cheese was your favorite?”

  “It is,” I said, trying to smile back, then forcing a forkful of the gooey pasta into my mouth, even though I felt sick to my stomach.

  Just then, the chime of a cellphone rang out beneath the table, and all eyes turned to Madison, who’d obviously been trying to sneakily send texts to one of her many girlfriends.

  “Maddy,” Steve snapped, “what did we say about using our phones at the dinner table?”

  “C’mon, dad,” she replied, batting her long lashes at him, widening her big blue eyes and giving him one of her trademark pouts. “It was just one message and anyway, it was super important ... I promise won’t do it again.”

  She was always trying to get away with bullshit like this, but for once Steve didn’t seem to be falling for it.

  “Damn straight you won’t,” he said, holding out his hand. “Give it here.”

  “Really?” Madison pleaded, her blue eyes widening even further.

  “Really,” he replied sternly.

  With a sigh, she handed over her phone – a shiny rose gold iPhone, which she was always tapping away at. As Steve laid it face down in the middle of the dinner table, I couldn’t take my eyes off it, as the memory of my run in with Tyler flashed back through my head.

  I’d never gone snooping through Madison’s stuff the whole time we’d been living together as a family, even though a couple of times I guess I’d been tempted. After all, she was hot – in a slutty, blonde, bratty kind of way. But even so, we’d been a family for so long that I really did consider her my sister, at least most of the time, and it felt plain wrong to go rooting through someone else’s things. I’d hate it if anyone went snooping on my computer or cellphone without my knowledge.

  But that Friday night, it seemed like the only choices I had left were either do exactly as Tyler wanted, or get my puny ass whooped on Monday morning.

  I sank lower in my seat, my stomach filling with pure dread. I’d never even been in a fight before, and I had no desire to take a beating, especially from those guys. Deep down I knew I was going to have to at least try to sneak my way onto Madison’s phone. But of course, there was no damn chance with it right there in the middle of the dining table.

  Sure enough, the moment Mom cleared our plates away, Steve handed it back to her.

  “Thanks, Daddy,” Madison said in a sarcastically sweet tone, before pushing herself up from her chair and heading up the stairs to her room, giving us all a flash of her insanely short miniskirt and long tanned legs in the process.

  “Oh, by the way,” she called out, pausing halfway up the stairs, “is it okay if I stay over at Janey’s tomorrow night?”

  “I don’t see why not,” Steve replied.

  And with that Madison (and her cellphone) were gone ...

  2

  I spent the rest of Friday night in a gloomy funk, unable to relax or enjoy myself. Normally I’d have spent the evening playing Fortnite online with my buddies, but instead I just lay on my bed, wondering what the fuck to do.

  The biggest problem was that Madison and her cellphone were almost surgically attached. She was never without the damn thing, so how in the hell would I even have a chance of sneaking photos off of it? And anyway, I didn’t even know the damn unlock code!

  I considered tiptoeing into her room while she was asleep – after all, I knew she left it charging by her bed, and I had at least a couple of guesses for what the code might be – but what if she caught me?

  She’d tell Mom and Steve for sure, and then I’d be in a whole world of trouble, both at home and at school.

  The more I thought about it, the more futile the whole thing became, until I felt well and truly screwed. With a sigh of frustration, I decided to get undressed, get into bed and hope to god that I’d think of something tomorrow: some way of wriggling out of this stupid fucking mess.

  I unbuckled my pants and then pushed them, along with my boxer shorts, down around my thighs, but as I did so, something made me pause: a glimpse of myself in the dressing mirror that was built into the door of my closet.

  My heart began to quicken as I stared over my shoulder at the reflection of my own butt in the mirror, as a crazy new idea swept over me. You see, I’d always hated my ass. I even got teased about it at school when I was younger, namely because it was so big for a guy.

  And that wasn’t all. I guess I should tell something else about me too, something kinda important that I forgot to mention. Ever since I’d hit puberty, I had tits, too. They weren’t super large or anything, more like small extra bumps of flesh on my chest, but they were de
finitely visible when I took off my shirt – which was why I always made sure to wear a tight vest under my school shirt, in order to keep them as flat as I possibly could.

  I’d so far made it through high school without anyone really noticing, but I still felt super self-conscious about them, as you can probably imagine, and it did little to boost my self esteem.

  If you’re wondering why I had them, it’s a medical condition called gynecomastia, which is something to do with an imbalance of estrogen and testosterone that some guys get when they hit puberty. Luckily mine was a pretty mild case compared to some of the grizzly photos I’d seen online, and I was hoping it would sort itself out as I got older – otherwise I’d need surgery.

  So anyway, there I was, my boxer shorts pulled down around my thighs, staring back at my skinny body in the reflection, at the curve of my hips and my big round ass and the soft bump of my right tit, showing through my vest, and a crazy idea began to form in my head.

  Madison had said she was going to be staying over at Janey’s tomorrow night, right? Well, that meant her room would be free for me to sneak into. Which of course was where she kept all her clothes. So what if I put some on, took a few candid photos of myself in her underwear or whatever, and maybe if I was luck, I’d take a couple that looked realistic that I could send those to Tyler ...

  After all, Madison was actually about the same height as me, and her body shape wasn’t all that different either. Sure, she was a little more tanned and toned, but I figured I could try and add a few filters and whatnot and who knows ...

  Sure, it was totally insane, but what was the alternative?

  3

  The next morning I woke early and of course the first thing that popped into my head was the plan I’d concocted the night before. In the harsh morning light it seemed even crazier than ever, and I doubted I had the guts to actually see it through. There were so many ways I could potentially fuck it up. Maybe Madison would know somehow that I’d been snooping through her things. Or maybe Mom or Steve would burst in and catch me in the act. Or – worst of all – maybe Tyler and the twins wouldn’t even be fooled by my photos, and instead kick my ass for attempting to trick them, while dressing up like a faggot in the process.