Dressed for Pleasure

by D. L. Savage

  As I was heading over to it and sitting down in front of it, I heard a knock at the door.

  “How are you getting on in there, dude?” Mike called through.

  “Almost ready!” I shouted back, feeling strangely nervous and excited about the idea of him seeing me like this, and wanting it to be perfect when he did.

  I stared again at the many sticks and tubes of powder and cream, wondering where to even start. A black stick with a golden band caught my eye. I picked it up and read the tiny white lettering: mascara. Then I picked up another and examined it: liquid eyeliner. I picked out a third smaller stick, realizing it was lipstick, in a hot pink color that I figured would be right for the character of Clarissa.

  I took a deep breath and set to work ...

  6

  “James, how long are you going to be in there, dude?” Mike called, doing a pretty good impression of my mother.

  I was just as I was finishing up my lipstick, and what’s more, I’d actually done what I hoped was a pretty good job on my eyes, too. I had a surprisingly steady hand, and I’d found that if I took my time and held my breath and made sure not to blink, it wasn’t too difficult to rim them with eyeliner. The mascara had been pretty straightforward, too. I’d just used the brush to dab a little onto my upper eyelashes, and maybe it was good quality stuff or something but it immediately made them look so much thicker and darker.

  I even found a stick of something called ‘concealer’ – which turned out to be skin colored cream that I dabbed onto my face, smoothing it in with my fingertips, creating an even, pale skin tone.

  And now, with the pink lipstick plumping out my lips adding to the effect, making them look full and glossy, I guessed I was done.

  I felt my my nerves crackling as I pushed myself once more to my feet and made my way as steadily as I could to the door to pull it open. I wasn’t really sure how Mike would react, and a part of me was terrified that he’d just laugh in my face or grimace with total disgust. But when he set eyes on me, it was obvious that he was as shocked – and excited – by my transformation as I was.

  “Woah,” he said quietly, looking me up and down, wide-eyed and open mouthed.

  “You like?” I grinned, finding that I was naturally speaking in a slightly softer, more feminine voice than usual. It just seemed the thing to do, somehow, now that I was dressed like this. And I made sure to stand tall and straight, pulling my shoulders back and pushing my fake boobs out at him, hoping he’d say something about how hot I looked.

  “What can I say?” he said finally, shaking his head. “You’ve done a really great job.”

  But even though he was trying to stay cool, I noticed that he kept on staring at me, his eyes travelling furtively up and down my body, almost like he couldn’t control himself. And I could actually feel a weird tension building between us, as my mind cast back to the kiss – knowing how much sexier it would feel like this, now that I was truly feminine. Because as crazy as it sounds, I was actually looking forward to it now.

  “Well, uh, I guess we should get to work,” Mike said just then, as if snapping out of a trance.

  “Sure, sure,” I smiled, kind of enjoying how flustered I was making him. “So where are we filming the first scene?”

  “Out in the yard,” he said.

  And as I strutting past him, I found myself making sure to put a wiggle in my hips, secretly hoping he was checking out my ass ...

  * * *

  It was only as we actually reached the set of large glass double doors that led out into Mike’s parents back yard that I began to get cold feet. I paused, shooting him a nervous glace, my heart suddenly booming.

  “What’s up?” he said, obviously picking up on my unease.

  “I don’t know if I can go out there dressed like this,” I said. “What if someone sees? Your neighbor or someone?”

  “And what if they do?” he shot back. “All they’ll think is that I’ve cast some smoking hot chick in my movie. Honestly dude, you look so convincing it’s scary. I have to keep reminding myself that it’s you.”

  I didn’t know if he was only saying it to make me feel better, but it worked, and I felt my heart flushing with warmth and gratitude that I had such an awesome, supportive friend.

  “Thank you,” I smiled.

  “C’mon, lets do this,” he said, catching me off guard by reaching out and taking my hand, then leading me out into the yard ...

  7

  We actually got a whole bunch of stuff filmed that afternoon, barreling through the meticulous shooting schedule Mike had planned out, and I found myself really relaxing into the role. The lines and voice came pretty naturally, and my fears about being seen by one of his neighbors soon melted away.

  I was even getting excited at the idea of watching myself back once we were done, hoping my portrayal of sexy, carefree Clarissa was as good on screen as it was in my head.

  Mike was really throwing himself into the role of Clarence, too, acting way more gruff and masculine than he normally did, and the two of us were really vibing off each other, getting more and more into it with each passing scene.

  And pretty soon, we’d reached that moment in the movie again – the scene where we made out. I could feel myself tingling with anticipation and nervous excitement as I waited for Mike to hit record on the camera, making sure to hold my posture, pushing out my tits and ass, while keeping my back straight.

  “It’s rolling,” Mike called, before racing back into shot and taking his place next to me, his face only a few inches away from mine.

  I took a deep breath, then said my line, “I’m so scared, baby. I’ve never done anything like this before ...”

  In the movie, I was talking about the fact that we were planning to steal a bag of drug money, but I could so easily have been talking about the kiss, and I found myself speaking with real emotion, my voice trembling as I looked deep into his big brown eyes.

  “Don’t worry, Clarissa,” Mike replied, reaching out and taking my face tenderly in his hand, just moments before he leant in to kiss me.

  I closed my eyes as I felt his lips touch against mine, and this time I didn’t hesitate or pull away. I kissed him hard, putting my heart and soul into it, feeling my body flushing with such pure feminine energy to took me by surprise. As his other hand slipped behind my back, coming to rest on my waist, I found my own hands moving into his hair, as if some sexy girl inside me were truly taking control.

  As the kiss heated up even more, I actually felt him starting to push his hips against mine, and I swore I could feel the hot hardness of his cock brushing against my bare thigh while beneath my skimpy dress, my own cock was throbbing hard in my panties, sending delicious waves of pure pleasure through my skinny trembling body.

  I could have kissed him like that forever, but after what felt like only a few moments, he pulled away, obviously a little flustered.

  “Okay, um ... cut,” he said, not looking me in the eye.

  And when I glanced down at his pants, sure enough there was no mistaking the bulge of his boner, pressing against his jeans.

  “I don’t think we need to do another take of that,” he joked awkwardly, and I forced a smile onto my face in agreement, even though secretly I wished we could make out some more.

  “So what’s next?” I asked, trying to sound normal, even though my voice was still trembling a little.

  “How about we go watch some of the rushes?” Mike said, still not quite able to meet my eye.

  “Okay, cool,” I said, but the disappointment was clear in my voice.

  “We could, uh, watch them in my room?” he ventured shyly.

  And just like that, I felt my excitement spike again. Sure, it made sense – Mike had a huge flat screen TV in his bedroom, and often watched back his movies on it, but I also hoped it was because his bed was in there, too. Was that crazy? I knew I should be feeling weirder about all this – after all, I’d just made out with my best friend, dressed like a chick. But the tr
uth was, I’d really fucking enjoyed it and now I wanted more.

  “I’d like that, Clarence,” I joked, once again affecting a soft, sexy tone.

  And as finally he shot me a glance, I saw the hunger in his eyes.

  Holy shit, I thought. Maybe I’m not the only one that wants this to happen ...

  * * *

  We walked up the stairs to his room in tense silence, the electric atmosphere growing more and more intense with each step. Mike was carrying the movie camera with him, and I wondered if perhaps I’d mistaken the situation. It was so damn confusing. I’d never had any experience in this department, and wasn’t sure if I was reading the signals correctly. But if we really were just going to watch what we’d filmed so far, then why was he being so tense and silent?

  We reached his room, and Mike went in first.

  My heart was pounding as I realized that if this was going to happen the way I wanted it to, then I had to be the one to take control.

  So as Mike knelt down with his back to me and began connecting the video camera to the TV, I decided to throw caution to the wind, and with trembling fingers, I reached down and took the hem of the dress, then peeled it upwards, pulling it off my skinny body in one quick motion, leaving me now in just my stockings, bra and panties, my smooth hairless body on full display.

  My heart leapt into my throat as he got to his feet then turned around, his eyes widening as he saw me.

  I took a deep shaky breath, then said in my softest, sexiest voice, “I was thinking, maybe we could have a little fun ...”

  8

  For a heart-stopping moment, I waited for Mike to reply. His expression was unreadable, his dark eyes fixed onto me, as he obviously wrestled with all the conflicting thoughts and desires that must be spinning around in his head, just like they were swirling through mine.

  But all of a sudden he strode towards me, grabbing hold of me and crushing his lips against mine in such a hungry, passionate kiss it took me off guard. I quickly gained control of myself, pushing back into him, sighing as I felt his hands start to explore my body, moving to my ass as he pulled me even closer against him, so that we were grinding together.

  He pulled his mouth away from mine and stared deep into my eyes as he murmured, “You look so fucking hot ...” And I felt myself shivering with girly pride at his compliment.

  “You too,” I whispered with a shy smile, watching as he began to tug his t-shirt over his head, uncovering his surprisingly muscular body beneath.

  Damn, he’s actually pretty ripped ...

  I’d never really paid close attention to Mike’s body before, and it felt like I was really seeing him for the first time, my desire growing into pure hunger as I stared at his toned chest, his clearly defined pecs with their small dark nipples that I wanted to kiss and lick, and of course the delicious ridges of his six pack, leading my eye down towards his pants, and the impressive bulge of his cock beneath.

  I took his hand, pulling him down with me onto the bed, and soon we were making out again hungrily, both of us sighing as we once again explored each other’s bodies.

  Without even quite being aware of what I was doing, it seemed like my hands had gravitated on their own to Mike’s pants, and with shaky fingers I began tugging them open, while his fingers had moved between my legs too, gently stroking my aching cock through my panties until I was sighing and writhing with pure pleasure.

  Soon, I’d fumbled his jeans open and tugged down his boxer shorts, and as I my fingers finally closed around his dick, I felt a jolt of surprise at just how damn big and hard it felt compared to my own. Whenever I got a boner, it got pretty stiff, but this was on a whole other level! It was like his dick was carved out of wood - smooth and hard - and deep within it I could feel the powerful throb of his heartbeat.

  He let out a low groan as I began to stroke him, working his impressive dick in slow sensual movements with my fingers, just the way I’d like mine played with. It felt so weird to be touching someone else’s cock, but I found I really enjoyed it, and soon I could feel his shaft growing slick and wet with the precum that was oozing from the tip.

  “That feels so good, baby,” he growled, as all the while his fingers were gently working my cock through my panties, teasing it like a clit, like we both wanted to keep up the illusion that I was a real girl.

  Because I sure felt like one. My body was so skinny and slight compared to Mike’s big muscular bulk, and even my tiny little dick seemed girly in comparison to his. And as I really looked at it for the first time, at its smooth dark skin and huge hairy balls beneath, not to mention that big bulbous head, all slick and swollen and purple, I just knew I had to taste it, too.

  My heart was booming hard as I began to kiss his pecs, letting my eager tongue lick and lap at his nipples, before slowly working my nervous kisses down his broad chest, along his abs and then following the dark trail of fuzz that led between his thighs.

  As my face got closer, I felt the sheer heat that was radiating from his cock, and a fresh girly shiver fluttered through my body in anticipation. I reached out, taking hold of it in my skinny fingers, then brought my mouth towards it, first licking the tip then letting the glistening head slip slowly past my lips, until I’d taken it deep into my mouth.

  I let out a soft groan of pleasure, surprised at how much I was enjoying the sensation of his throbbing meat filling my mouth, and as I began to work my lips up and down his shaft, Mike too let out a deep sigh. Spurred on, I began to suck faster, stroking his shaft with one hand while kneading his big full balls with the other, until soon I felt lost in a trance.

  Never in my life had I felt so sexy, so slutty, laying there on his bed, sucking dick like my life depended on it, and I let out another muffled whimper of pleasure as I felt Mike’s fingers tug my thong to one side, finally releasing my aching cock. He began to fondle it lazily as I continued to slobber and slurp on his dick, until I’d got it all shiny and wet with my saliva. Then all of a sudden, I felt his hands pulling my head away.

  I gazed up at him. He looked so sexy, lying there on his back, his muscular chest tanned and broad, and he locked eyes with me as he said, “I have some condoms in my drawer if you wanna take this a little further?”

  “Sure,” I whispered, my heart once again hammering with nervous anticipation as I watched him lean over and pull open his bedside drawer, then grab the box, quickly tearing open a small gold package and fitting the rubber sheath over his impressive dick in one easy motion. Then he grabbed a bottle of lube and squirted a generous amount onto his sheathed dick.

  I realized I didn’t know which way he wanted to do this – me on all fours? But to my relief he quickly took control of the situation, gesturing for me to climb up on top of him.

  I felt so nervous and on display as I did as he asked, positioning myself so that my thighs were resting either side of his and my butt was only inches from his throbbing cock.

  “Don’t worry,” he whispered, as he guided the head of his cock between my cheeks, so that I could feel the slick hot tip pressing gently against my hole. “I’ll take it slow ...”

  And as he said that last word, he took hold of my buttocks, spreading them wide as he slowly eased me down onto his dick. The sensation was like nothing I’d ever felt before. My ass was stretching so fucking wide I almost couldn’t take it and there was even a flash of pain. But there was pleasure mixed in too; a deep kind of pleasure that was so much more intense that anything I’d ever felt, and found myself quickly craving more.

  I could hear myself making soft moans and sighs as Mike fed even more of his girthy cock inside me, but it was like some out of body experience or something. I was utterly lost in the sensations, giving myself up to him completely, as he gently began to fuck my ass, pumping that big thick rod in and out of my hole, a little deeper with each thrust.

  By now, I’d lost all inhibitions and I began to move in time with him, riding his big dick and bucking my hips, my hands resting on his shoulders and our
eyes locked, my hair falling in my face, as we both found a steady rhythm.

  I found myself concentrating on the bubbling sensations of pleasure that seemed to radiate out from my stomach and flutter around my body with each fresh stroke of Mike’s cock, and I’d almost forgotten my own dick entirely. But when I gazed down at it, I saw that it was semi hard, flushed pink and flopping around as I moved, slapping against his abs, while I could feel my tight balls grazing against the fuzz of his pubic hair and the root of his cock.

  And then something crazy happened. As Mike began to pick up pace, gripping my hips and starting to jackhammer my ass with his cock, I actually began to feel the first throbs of an orgasm, even though I wasn’t even touching myself! What the hell?! I almost couldn’t believe it was happening, but as he fucked me faster and faster, I felt it rushing up from inside me, and soon I’d reached the point of no return.

  “Oh god,” I murmured, staring deep into his burning brown eyes, in a mixture of amazement and also panic. “I think I’m going to … cum ...”

  I gazed down at my cock, which was quickly swelling, growing fully hard now, jutting proudly away from my body, flushed and glistening, and I let out a last breathy moan as my orgasm hit with such force it knocked the air from my lungs. I could feel my ass clamping tight around Mike’s dick and all my muscles clenching as my cock began to unload, pumping out squirt after squirt of pure white cum which shot high up onto Mike’s abs and pecs.

  “I’m sorry,” I murmured, worrying he’d be grossed out, but he locked eyes with me and growled back, “No, that’s fucking hot.”

  I leant in towards him, and he took my face in his hands, our mouths meeting in a hungry passionate kiss, just as I felt him tense up too. He moaned deep into my mouth, and then I felt his cock begin to throb and pulse deep inside my ass as he too started to cum, as the last shivers of my own orgasm flashed through me.