Dressed for Pleasure

by D. L. Savage

  But I longed to have access to wifi; I had so much more I suddenly wanted to find out, so much more I needed to know about makeup beyond the absolute basics. I suspected that in some ways I was lucky to have such pale, smooth skin and I found that just a touch of eyeliner drawn carefully along my lids and a dash of lipstick really brought my face to life, making it so damn girly that I couldn’t quite believe it.

  I even went as far as shaving my body in the shower – using my regular guy’s razor to strip away the soft downy fuzz that grew on my legs and tummy and ass, as well as around my cock and under my arms, leaving me smooth and hairless everywhere.

  Once I’d patted myself dry, I got dressed up all over again, this time in the sexiest, sluttiest strappy lingerie I could find, before lying down on the bed and rolling around, loving the feel of the silky panties and stockings against my freshly shaven skin, while my mind flashing back to the hunky guy I’d seen by the lake, stroking his big hard cock ...

  By now, I didn’t even try to fight the urges that were tugging at me, instead letting myself give into them, laying back on the sheets and closing my eyes, a soft girly sigh escaping my pink glossy lips as I allowed my hand to stroke between my legs, playing with my aching cock like it was a clit, stroking the tingling head of my dick in small circles through the silky fabric of my thong, while in my head I imagined myself down on my knees, stroking that hunky strangers big hard dick, even taking it in my mouth and sucking on it.

  With a gasp, I felt the orgasm rushing up inside me way quicker than I was expecting, and I pressed my knees together as I felt my thong flood with warm gooey cum while my skinny body trembled and shivered in pure ecstasy as I writhed and moaned on the bed, my long hair splayed out around me, and my skinny body encased in slutty lingerie.

  As I came back to my senses, I didn’t feel guilty about what I’d done, either.

  Instead I smiled, knowing I’d reached a real breakthrough, finally leaving all that goddamn guilt and repression behind.

  The only sadness I had was that it was just a fantasy.

  If only it was real, I thought with a sigh ...

  7

  The next morning I awoke wrapped in luxurious cotton bedsheets, my eyes adjusting to the sight of the pastel pink walls of the room, as the memory of my fun yesterday came rushing back into my head. I felt so happy, so free, and I let my hand slip beneath the sheets, stroking my still smooth thigh, as if to check that the whole thing hadn’t been some crazy dream.

  The floor of the room was strewn with clothes and lingerie from my dressing up session, and I knew I’d need to tidy and put everything back at some point. But why worry about that now? I had the whole rest of the week to explore and enjoy myself further!

  I felt so damn happy it was crazy, my stomach bubbling with an almost uncontainable excitement at the thought of another whole day to explore and have fun – dressing and pampering myself, perhaps even trying on a little more makeup.

  Then a new idea began tugging at the corners of my brain.

  What if ...

  I almost couldn’t allow myself to think it, but at the same time, it kept on creeping in, no matter how I tried to distract myself, my heart beginning to drum as I seriously considered it.

  What if ...

  There it was again, gnawing at the corners of my brain until it was the overriding thought, drowning out all others.

  What if … I went down to the lake dressed as a girl?

  But could I really do something so brazen, so daring, so unlike me?

  Then again, wasn’t that the whole damn point of my trip? To expand my horizons, to explore and understand myself, to let go of all the goddamn baggage that had been weighing me down all these years …

  And the more I thought about it, the more it seemed like exactly what I had to do, if only to prove to myself that I could, to show that I was changing and growing as a person ...

  * * *

  I can’t believe I’m really doing this, I thought, as I padded once more down the dirt path towards the lake. And I couldn’t have looked more different than I did yesterday morning.

  I’d dressed in the white thong bikini and top, my cock safely tucked away inside the prosthetic pussy, while my top was filled with two small, pert breasts. I’d put on the long, blonde wig, and accessorizing my look with a tan sunhat and a pair of big black sunglasses that I hoped made me look classy and chic.

  I’d found a floaty turquoise cardigan wrap, too – after all, even in my newfound confidence as a woman, I still knew it was kinda slutty to go strutting around in just a thong! – and to my delight, I’d found a girly pair of purple sandals that fitted me just perfectly.

  I’d even painted my fingernails and toes with some bright pink nail polish, and slathered my lips in a matching tone, which I found gave them a really delicious look, making them much more plump-looking than normal. I’d put on a little eyeliner, too, and even dabbed some sparkly powder onto the apples of my cheeks, which I hoped was glittering in the morning sun as I made my way down the path, both excited and nervous to get to the lake.

  What if that stranger is there again? I caught myself thinking occasionally, my tummy flashing with pure nervous excitement each time I thought it, but I knew the chances were slim at best.

  Most likely, the lake would be deserted – which would be perfect for me to really relax and enjoy my new girly self.

  I made sure to take small, dainty steps, which actually came pretty naturally, and I found myself swinging my hips too. For maybe the first time in my life, I felt totally at ease with my body, enjoying it in a brand new way, no longer hating my skinniness or my lack of muscle definition, instead viewing these things as weird genetic blessings.

  I’d already begun fantasizing about what I’d do when I got home to civilization, too, my mind running riot with the many possibilities.

  But as I reached the edge of the trees and stepped into the clearing, I caught sight of something that made me stop in my tracks. Because there, parked just twenty feet or so away from me was the same red pickup I’d seen yesterday, over on the other side of the lake.

  I stood, frozen, my heart suddenly pounding, as I scanned the nearby rocks for any sight of the stranger. And sure enough, I soon spotted him laying totally naked again on the very same large flat rock I’d left my own clothes yesterday.

  A part of me wanted to turn around and head straight back to the cabin, but before I could even move, he’d seen me, lifting himself into a sitting position, his bare torso gleaming with a sheen of sweat, his toned pecs and abs rippling as he moved, lazily lifting one of his large meaty hands to shield his eyes from the sun, his thick sensuous lips curling into a smile as he set eyes on me, and in a low drawl, he said just one word: “Morning.”

  I felt my eyes flicking between his muscular legs for a half second, unable to stop myself from taking a quick nervous glace at his impressive cock and big low slung balls, before I snapped back to my senses, forcing a smile onto my face as I replied in the softest, most girly tone I could muster, “Hey!”

  The word leap from my mouth, and to my surprise I sounded way more convincing than I’d ever hoped – I sounded just like any nervous young girl who’d happened to stumble across some hot naked dude on a rock …

  “Goin’ for a swim?” he said, in that same low, confident drawl, obviously not caring a damn that his whole naked body was on display right now, perhaps even getting off on making me nervous.

  I stared down at the rolled up towel I was clutching for dear life, knowing there was no way of denying it or pretending I’d made some wrong turn. And although part of me wanted to run a mile – I was way outside of my comfort zone here, remember – another strange new side to me had begun to enjoy our conversation.

  Because so far at least, I could tell I had him fooled. He thought I really was a chick; it was clear from his voice, and there was no way in hell I was about to correct him.

  “Uh, yeah,” I replied, in a soft, quiet tone, the
n took a few tentative steps towards the water, my back now to him.

  With a final deep breath, I laid down the towel, kicked off the sandals, took off my hat and tied the long hair of my wig in a high ponytail using a hair tie I’d put around my wrist for just that purpose, then let the wrap slide from my shoulders and fall around my ankles, my heart booming as I knew he’d be able to see my bare butt framed in the white thong bikini, if he was still looking.

  I just hoped my ass really looked as good as I thought it did as I strode towards the water, my whole body flushing with a weird thrill at the idea that maybe, just maybe, my girly body might actually be turning him on.

  As if he could read my mind, just moments before I launched myself into the water in a breaststroke, making sure to keep my head (and wig) above the surface, I heard the stranger make a wolf whistle.

  I knew I should find that kind of behavior boorish and crude, and if I’d been my usual male self, a macho douchebag like him would be the last type of guy I’d want to spend time around. But actually, now that I was the new girly me, I had to admit that I kinda liked the attention.

  As I swam out further, my mind again returned to his perfect body, as I began to think about all the things I’d love to do to it, if I got the chance.

  It was so crazy to think how far I’d come – how much I’d changed – in such a short space of time, but I really was enjoying myself way more as a girl than I ever had done back as Cody, and I began to consider staying like this forever: actually transitioning permanently when I got back home. At the very least I’d look into it. After all, what was to stop me? The only person who’d have disapproved was my mother, and of course she wasn’t around any more.

  I was finally free ...

  After taking a long, leisurely swim in the lake, I knew it was time to return to shore, and that’s when my nerves returned in full force. As I turned back, a quick glance confirmed that the stranger was still there, sunning himself on the rock, right next to where I’d left my clothes. I knew he’d talk to me again and part of me was looking forward to it, while another was dreading it, worried that he’d suddenly see through my disguise.

  But I couldn’t stay in the cold water forever, so I swam slowly back to shore until I reached the shallower part of the lake, then stood up and walked out, knowing deep down he was watching me this whole time.

  “How was it?” he asked as I leant forward to get my towel.

  “Cold,” I laughed back, again making sure to keep my voice high and soft.

  “The sun’ll warm you right up, baby,” he drawled, and I felt another shiver of excitement when he called me that.

  Baby.

  He really did think I was a girl!

  “You want to come lie down over here with me?” he said just then, pushing himself up onto an elbow and fixing me with his big dark eyes, his naked body glistening in the sun. I saw from a quick glance that his cock was semi hard, laying meatily against his thigh, thick and swollen. “This rock’s plenty big enough for two,” he added with a wry smile.

  I knew exactly what he was suggesting, and I felt my heart drumming hard against my ribs. I’d never done anything with anybody before, and did I want my first time to be with a guy, with him?

  But even as I was still deliberating, my head swirling with nervous anxiety the way it always used to, paralyzing me, another brand new part of me seemed to be springing into action, and I actually surprised myself as I spoke, saying, “Sure, why not.”

  What the hell am I doing?! I thought, as I felt myself reaching down to pick up my towel, hat and sandals, then walk slowly over to where he was laying, making sure to take small dainty steps, all the while feeling his burning gaze latching hungrily onto my slim pale body, which was still sparkling from the water.

  Staying demure and ladylike as I could, I set out my towel a few feet away from him, then lowered myself onto it, my heart pounding hard against my ribs as I again wondered what the fuck I was doing, laying down next to this total stranger.

  “You’re very pretty,” he murmured, turning his head towards me, “but then you probably know that already,” he added with a smile.

  “Actually, no,” I admitted quietly.

  “Damn, girl,” he laughed. “You’re beautiful.”

  I felt myself flushing with pride at the compliment, and I even giggled, muttering, “Why thank you.”

  “The pleasure’s all mine ...” he said, before turning his head away again, cradling it once more in his hands, his tanned muscular naked body on full display as he lay back on the rock, sunning himself once more, leaving me alone to my racing thoughts, right there next to him.

  It was odd; I’d been terrified of him making a move on me, but actually now that he hadn’t I felt a little disappointed.

  I’d brought some sunscreen with me, and for something to do to distract myself, I sat up and squirted a generous dollop into my palm, then began working it up my legs, while from the corner of my eye, his tanned body kept on distracting me.

  “Say,” he said just then, his low voice breaking the stillness, “I sure wouldn’t mind some of that cream myself …”

  “Uh, sure,” I said, turning to offer him the bottle, but instead just closed his eyes again and lay back, like he was expecting me to put it on him.

  I took a deep breath, then shifted closer to him, so that I was kneeling right next to him.

  I can’t believe I’m doing this, I thought as I squirted some cream into my palms, then began to timidly work it into his calves. I watched my slim fingers raking through the dark hair of his legs, feeling the toned muscle beneath, my heart pounding while my movements grew more confident.

  And soon I was working my fingers right up his thighs, my gaze once more drawn to that long, thick, perfect cock, only a foot or so away from me, watching in awe as it lengthened and twitched, his balls growing a touch tighter as my fingers got closer and closer to it.

  But I pulled my hands away, squirting yet more sunscreen onto my palms, then moving my attention to his abs and pecs. They felt so taut and firm beneath my fingers as I worked the cream up and down his torso, feeling my heart thudding hard against my ribs and my breath shivering past my lips as I tried to stay focussed on my task, unable to believe this was even happening.

  Between my legs, I could feel my prick starting to throb, too, yet held snug and tight, hidden away beneath the soft mound of my pussy and the tight white thong.

  Finally I let my fingers trace downwards, almost as if they had a mind of their own, as I drew them closer and closer towards his cock, desperate to wrap them around its meaty girth. It was so big already, so much bigger than my own at full hardness, and I even found myself licking my lips as I wondered whether to be brave and just go for it.

  I paused, my fingers now only inches from his junk, shooting a nervous glance at his face, seeing that his eyes were still closed.

  “Don’t stop, baby,” he purred. “That felt so good …”

  And as he spoke, his cock twitched between his legs, growing even longer, like it was inviting me to stroke it.

  I took in another shivery breath, then finally let my skinny fingers wrap around it.

  “Mmm,” he groaned, the noise rising up from the back of his throat as I began to slowly stroke his dick up and down, eased by the cream that was still on my hands, feeling it grow even harder between my fingers, hot and throbbing as I stroked it to full mast, unable to pull my hungry eyes away from it, while my body flooded with pure adrenaline.

  “Damn that’s good,” he murmured, as I continued to stroke his cock, even letting my other hand start to caress his balls, feeling their meaty weight in my palm, as I continued to work his cock, pumping it faster and faster.

  By now I was actually trembling all over, the nervous excitement flowing hard through my veins as I began to crave yet more. And I knew he wouldn’t mind if I finally gave in to my very naughtiest desire …

  I leant forward, arching my back arched and thrusting my but
t high into the air as I lowered my face gingerly into his lap, nervously guiding that big thick cock towards my open mouth.

  I felt a powerful shiver of pure pleasure flow through me as I closed my glossy lips around its smooth hardness, the pearly head gliding against my tongue as I began to bob, my mouth filling with heat and a subtle salty taste, as the stranger let out yet another low groan, his body tensing a little as I began to suck on him, softly at first then growing in confidence, feeling my own cock throbbing and aching so damn hard in my panties, even though I wasn’t even touching myself.

  I even let out a soft girly sigh around his throbbing shaft, feeling so damn slutty and sexy, as I began to suck him faster and faster, knowing deep down that if I carried on like this, at some point he’d blow his load. And in that moment I wanted it badly. I wanted to feel his hot cum spraying into my mouth; to taste it, to gulp it back, every last drop.

  “Is that big dick getting your pussy wet, baby?” he growled just then, catching me off guard, his dirty talk sending fresh shivers of naughty pleasure through my skinny body.

  “Uh huh,” I murmured around his hot, throbbing cock.

  “Why don’t you play with it for me,” he persisted, shifting onto his elbows now so that he could watch me. “Play with your tight little pussy until you cum, baby. I want you to watch you cum with that big hard dick in your mouth ...”

  I felt powerless to refuse, and as I continued to suck on his cock I did as he asked, slipping a nervous hand into my bikini bottoms, my fingers gliding over the synthetic mound of my pussy as I began to stroke myself there, the subtle motions of my fingertips softly stimulating my aching cock beneath until I was moaning and sighing around his swollen meat, knowing it wouldn’t be long until the pleasure was too much and ...