Dressed for Pleasure

by D. L. Savage

  I removed the last of my clothes, then stepped into the bikini bottoms, tugging them up over my thighs, then hitching the waist band up around my tummy, feeling their elastic stretching tight over my butt and cupping my cock and balls way more snugly than I was anticipating. I actually began to wonder if I’d pulled them up a little too high, as I could feel some of the fabric disappearing into my ass crack, but I started to suspect that they were supposed to be worn this way.

  After all, I’d seen girls wearing shorts like this, and I knew that the cut was designed to accentuate a girl’s butt by cupping it tightly, while showing a little cheek.

  Truth was, I’d always kinda liked that style – to look at, anyway. But never in a million years would I have thought that I’d be wearing something like that myself!

  Even though I suspected they’d look totally ridiculous on me, I decided to go over to the mirror to see. As I approached it, I couldn’t help but notice the sensation of that tight black fabric riding high between my butt cheeks, and again my mind flashed with the strange memories of my dream that morning: of the sheer sensuality I’d felt as a woman.

  I held my breath as I reached the mirror, totally prepared to be disgusted by my own scrawny reflection, but to my surprise, I actually looked kind of okay. Sure, the cut was really high, but if anything, it flattered my figure, cinching in the puppy fat that had collected around my stomach, creating the illusion of a smooth, toned stomach.

  And when I turned to the side, to peek at my ass over my shoulder, that’s when it really hit me. From that angle, I actually looked pretty damn good! I found myself simply staring at my butt for a while, unable to believe it was even mine. I guess I’d never really looked at it so closely before, and never in black booty shorts, and maybe it was all down to the cut of the bikini bottoms but damn. I really couldn’t believe it! It looked fucking hot.

  The more I stared at myself like that, at the arch of my back and my slim but toned thighs, I began to see how naturally feminine my body really was. It was like all this time, I’d been frustrated at how scrawny and slim it looked in guy’s clothes, when all along I’d never focussed on the positives – I had curves.

  In a moment of madness, I actually considered putting on the bikini top, too, maybe even filling it with those weird fake breasts, just to see how sexy and girly I could be. But I knew that was a step too far.

  Instead, I pulled my jeans and t-shirt on over the bottoms, then bundled up a towel and my discarded boxer shorts, and headed out of the cabin, excited to take a dip in the lake on such a warm day ...

  * * *

  As I walked down the dirt path towards the sparkling water, I could feel the tightness of the bikini briefs beneath my jeans, especially the way they rode up between my butt cheeks. I’d always found it hot seeing girls in booty shorts (obviously only ever online due to my pathetic lack of experience in the real world), and it was a subtle turn on somehow to know that now I was actually experiencing exactly what it felt like when a girl wore something tight and sexy like that.

  I found myself walking a little differently too, swinging my hips a touch more than usual, as my brain once more swirled with crazy thoughts – as if a little voice was whispering to me, urging me to go even further, reminding me that I had a whole world of sexy, girly items I could explore at my leisure, back there in the cabin.

  After all, wasn’t that the whole point of my solo vacation? To learn some more about myself, to actually have a little ‘me time’? And if it turned out that something I enjoyed was dressing up in girly stuff, then why the hell shouldn’t I explore that urge in private?

  I reached the edge of the water, and set my towel down on a smooth flat rock nearby, which was already baking hot to the touch. The water of the lake looked amazingly clear and still, the surface sparkling from the sun’s rays, and I eagerly got undressed, once again feeling a strange excited shiver as I stripped down to those skimpy black bikini bottoms, staring down at them, a part of me wishing that the space between my legs was flat and smooth like a real girl’s, instead of the round bulge of my cock.

  I began to wade out into the water, my breath catching in my throat as the sharp coldness enveloped first my thighs, then my stomach. I launched forward, diving beneath the surface for a moment, then rising up again, now acclimatized to the temperature, a happy smile on my face as I began to swim out further from the shore, enjoying the contrast of the hot sun on my head and shoulders and the coolness of the lake.

  Before I knew it, I’d actually swam pretty deep into the lake, and I saw that there was another rocky area to the left hand side, where smaller pools had been created, broken up by the large pale grey rocks that jutted out of the water here and there, so I began to swim over to explore, seeing that this part of the lake opened out onto another clearing, with what seemed like another dirt road leading towards it.

  It was only as I swam even further towards it that I saw the truck. It had been shielded from view behind one of the rocks, but there was no mistaking it: a large red pickup, parked right by the edge of the lake in a small woody clearing.

  I stopped swimming and trod water for a while, wondering where the owner of the truck was. I’d considered myself totally alone here, and there was something disconcerting about knowing there was another person somewhere at the lake, too, someone who’d perhaps been watching me from a vantage point this whole time – watching me get undressed, watching me uncover my black bikini bottoms, then wade happily into the water …

  But all of a sudden, the tables turned, and I became the voyeur. Because just then I caught sight of a figure, moving from behind the truck and walking right towards the water and my breath caught in my throat.

  I knew deep down I was hidden from view, shielded by the rocks, but even so, it felt so weird to watch this stranger, spying on him as he reached the edge of the lake and then, just like me, began to undress.

  He looked like he was in his late twenties or early thirties, and unlike me, he was what you’d definitely call a ‘real’ man: his body thick set and muscular, no doubt from doing years of hard manual labor. He was dressed in dirty blue jeans and a plaid shirt, which he began to unbutton, revealing a toned tanned torso beneath, which was already glistening with a thin sheen of sweat.

  I guess he was what you’d call handsome, too, in a rugged sort of way. His face was flecked with stubble, his brows were thick and dark and he had a strong, masculine jawline – the kind I always wished I had.

  I held my breath, my body submerged beneath the water as I watched on, my heart starting to pound as he tossed off his shirt, then began to unbutton his dirty jeans, button by button, first uncovering a thick crop of jet black pubic hair and then his cock and balls.

  I found I couldn’t pull my eyes away, even though I wanted to, my gaze instead fastening onto his long fat cock and low-slung balls which hung meatily between his legs as he casually pushed his jeans down over his muscular thighs then kicked them off, leaving him completely naked.

  He looked like a textbook example or life study drawing of a naked man – everything so damn toned and in proportion, his glistening body clearly defined, his muscles glistening and rippling, his long, semi-hard cock swinging between his thighs as he strode towards the water until he was up to his knees, then pausing as he reached down and began to scoop some up with his hands, washing his body until it gleamed and glimmered in the sun.

  I knew I should turn away and leave him to it – after all, I’d hate to think someone was watching me as I bathed. Also, he looked like the kind of guy who’d kick my ass in a heartbeat if he caught me peeping at him. Yet at the same time, something simply wouldn’t let me leave and instead I found myself nestling even closer against the rocks, watching on in secret, as he turned and made his way towards a large flat rock near the water’s edge, my eyes now checking out his broad back and toned ass, as he climbed up onto the rock, then lay down, cradling his head beneath his arms, his biceps bulging and his toned stomach stretched tau
t as he closed his eyes, letting the warm sun beat down on him.

  I felt a strange pang of envy as I watched the stranger. He seemed so at peace, so easy in his skin, not a care in the world, while I had so many fucking hang ups about my body.

  And as if to prove the point, I watched in shocked amazement as he actually reached between his legs and lazily cupped his junk with a tanned meaty hand. I thought for a moment that maybe he had an itch, or perhaps he just liked the feel of his hand against his cock and balls, but soon he’d actually begun stroking his cock, working his thick, semi hard shaft slowly in his fist until it began to grow and stiffen before my eyes.

  He was still cradling his head beneath his left hand, and the whole thing seemed to play out in slow motion. He was in no rush, just slowly stroking his meat, which by now was fully hard, and way bigger than my own pathetic cock at full mast, his big full balls now tight and swollen, as his fist glided up and down his slick hard shaft, his abs tensed, and his eyes still closed.

  Even though I wasn’t even slightly gay, I had to admit, there was something hot about it – about a guy so comfortable in his own skin, enjoying his perfect body, laying out in the sun, slowly stroking his cock. And as I watched on, between my own legs, I could feel soft throbs of pleasure too, almost as if his hand were stroking my cock, as he continued at that same slow, lazy pace, his dick so damn hard and swollen now, thick and meaty, flushed a deep pinky purple color, the bulbous head glinting in the sun, slicked with pre-cum.

  All off a sudden, he tensed up, his abs rippling as he hunched forward, his eyes opening just in time to catch his cock as it came: spraying his glistening muscular chest with the biggest damn load I’d ever seen, spurting out pure white jets of cum high onto his rippling pecs and abs.

  And when he was done, he lazily wiped the cum into his chest like it was sunscreen, then lay back satisfied, closing his eyes once again, his perfect muscular body glistening.

  I finally pulled my eyes away from him, shocked to the core by what I’d seen, my own tiny prick still throbbing hard between my legs, snug and tight in those black bikini bottoms.

  I turned and began to swim back towards the edge of the lake that led back to the cabin, knowing I’d be safe from view as long as the stranger didn’t suddenly get up and stare out into the lake. But from his lazy relaxed manner, I knew I’d be safe.

  Once I’d reached the shore, I quickly toweled off then fumbled on my jeans and t-shirt, still a little shocked and confused both by what I’d seen and by how my own body had reacted. Hell, I was still turned on, and I had the urge to masturbate too, but I felt conflicted about doing it, knowing it was his body I’d fantasize about.

  Would that make me gay?

  The cold of the lake that had seeped deep into my bones, and I shivered a little as I turned and made my way back to the safety of the cabin, hoping that with time, my horny thoughts might diminish ...

  5

  By the time I arrived back, I felt consumed two conflicting feelings – the first was guilt about spying on the stranger, and the second was confusion at the desire I’d felt as I’d watched him. It all seemed tied in with dressing up somehow, too; like those skimpy bikini bottoms had somehow altered my worldview, made me feel sexy and feminine in a way I’d never really felt before. And if I was honest with myself, I knew I wanted to explore this part of myself further.

  As I made myself a fresh salad for lunch, I let my mind wander further, exploring and interrogating each feeling and thought as it appeared, the way I’d been taught in therapy.

  Was there really anything so wrong about exploring my sexuality? After all, my repression and my lack of experience I knew were the main things holding me back in life. I wanted more confidence, wanted to be freer and more open with myself, wanted to finally take life by the horns instead of hiding in the shadows, watching on, while everyone else had a great time.

  And hadn’t that been what I did, back at the lake, too? That stranger had been so comfortable and free with himself, enjoying his body in a totally natural and unashamed way, while I’d hidden behind a rock, spying on him, confused about my own reactions to what I was seeing.

  I began to think about my dream again. How sexy I’d felt in the dress, before I’d opened the door to a black chasm of nothingness. I knew that if I’d told it to my therapist, she’d have said something along the lines of: The black void represents your feelings, Cody. You’re scared of the future, scared of the unknown …

  Soon a new fantasy began playing out in my head: one where instead of hiding, I’d actually approached him. And in my fantasy, I wasn’t just wearing the bikini bottoms, either. I had cute pert breasts too, bouncing in my bikini top as I strode towards him, while my legs were shaved and smooth and my hair was long and glossy and silky, tied in a sexy ponytail, my face painted perfectly in beautiful makeup, my body shivering with desire ...

  I didn’t let my fantasy go any further than that, but I knew in that moment what I wanted to do. I set down my untouched salad on the counter, as a new desire took hold of me, one that I knew I wouldn’t be able to shake until I’d explore it further.

  And once again, I made my way towards that secret room ...

  * * *

  My hands were actually shaking as I slid open the middle drawer of the closet – the one that contained the weirdest items of all: the fake breasts and pussy. I’d been intrigued about them ever since I first saw them, but now I was planning to go one step further.

  I brought out the slim white cardboard box and opened it, again staring at the strange contraption within. It looked just like a real vagina, complete with plump shaved lips and a crop of neatly trimmed pubic hair above, and when I touched it, it felt soft and spongy, almost identical to real skin.

  I lifted it carefully from the box and turned it over, seeing for the first time that there seemed to be a specially molded compartment at the back, where I assumed you fit your junk into.

  Am I really going to do this? I thought to myself, my heart pounding as I deliberated whether or not to try it on.

  But desire and curiosity quickly won out, and before I could change my mind, I began hurriedly undressing, tossing my clothes onto the floor around me, wanting to get naked as soon as possible.

  And the moment I was, I stepped into the clear straps of the pussy, pulling it up around my thighs, then set to work trying to feed my tiny dick into the compartment, easing it slowly inside, surprised at how well the spongy skin like substance seemed to accommodate it. Before long, I had my cock and balls tucked all the way inside, and I tugged the straps tight around my hips, feeling the one at the back slide tight between my ass cheeks too, which I guessed must be similar to how a g-string felt.

  The whole sensation of having something so snug between my legs like that was kinda weird, but not bad exactly, and from where I was standing at least, I had to admit that it looked pretty realistic. Because now, instead of my cock and balls dangling between my legs, there was just a smooth mound of fake flesh.

  I took a walk to the mirror, my breath catching in my throat as I set eyes on myself. It looked so damn uncanny. I really did look like I had a pussy now, and even though the sight of me like that was turning me on and I could feel my cock beginning to throb and grow, to my amazement everything stayed tucked away, safely in place.

  Charged with excitement at the success of my experiment, I quickly wanted more, so I raced back to the closet, drawing out the smallest set of fake breasts I could find, figuring that on a skinny petite frame like mine they would probably look the most natural.

  I found that they had some sort of adhesive on the back, which clung to my pecs as I fitted them in place, but I knew I wanted to complete the illusion with a bikini. And this time, instead of the conservative black one, I found myself eagerly pulling out the skimpiest of the lot: the sexy white thong style set.

  I pulled the bottoms on first, feeling them pull tight and snug between my ass cheeks, while holding the pussy firmly in place .Th
en I carefully fed my arms and head through the stretchy top part, which fitted like a band around my chest, tightly holding the fake breasts to my skin.

  I eagerly wanted to go take another look at myself in the mirror, but before I did, I reached out and took down the long blonde wig, figuring blonde would look most natural as it was closest to my own dusky, mouse brown hair.

  I slipped the wig off the dummy head, then examined its interior, noting that there was a kind of mesh cap inside, which I assumed I just fitted onto my head like a beanie.

  So I scraped my hair from my face then carefully pulled the wig onto my head, immediately loving the feel of its silky golden strands falling around my bare shoulders and either side of my brand new breasts.

  With the wig firmly on, I eagerly skittered back to the mirror, and for a moment I couldn’t believe my damn eyes, my brain being fooled for a delicious half second by the sight that greeted me.

  Holy shit, I thought, my mouth curling into a grin as I stared in awe at myself. I really do look like a girl ...

  6

  I spent the rest of the afternoon lost in the magic of dressing up – experimenting with all kinds of looks. I tried on panties, wigs, stockings, bras, even a little makeup. And while I made a ton of mistakes and probably looked totally foolish at times, I didn’t care one bit. Because this was for me. I was finally doing what I’d always hoped I’d do: taking a leap into the unknown, striding confidently into that black chasm, and actually exploring my desires and fantasies head on instead of repressing everything to the point of inertia.

  And the more I experimented, the more it felt like a real me was emerging – not the scrawny nervous Cody I’d always been, but a cute, fun, playful girl, full of life and energy.

  I found that bright colors really suited me, and as I’d first suspected, the blonde wig looked the best. There a few hair ties and scrunchies lying around and I even fooled with a few ponytail styles, loving the way each look transformed me, spending god-knows-how long posing and grinning at myself in the mirror, moving my body into what I hoped were sexy angles and positions.