Dressed for Pleasure

by D. L. Savage

  I could see a parting in the trees ahead, and when I reached it, I stepped out into another clearing, this time giving way to a huge sparkling lake, surrounded on all sides by large smooth rocks.

  I’d been told by Elizabeth that it was safe for swimming in, as long as you didn’t go too far out, and I saw that some of the larger rocks would be a good place for sunbathing too.

  This really was shaping up to be an awesome vacation, and I decided that I’d come back with my swimming stuff the very next morning. Just then, my stomach let out a large gurgle, reminding me that I hadn’t eaten anything at all since the late morning, and it must be getting on for six or seven at night.

  So I trailed back down the path, slowly acclimatizing to the stillness of the forest and getting my bearings, idly wondering what it might be like when it grew dark. And as I approached the cabin from the rear, I caught sight of a window at the back that made me stop for a moment in my tracks.

  That must be a window to the locked room, I realized.

  It had curtains pulled across it - made of a plush pink fabric, unlike all the other curtains in the cabin - and I walked towards it, hoping to maybe peek inside through a crack and finally find out what was inside that mysterious room. But of course the curtains were pulled tight and there was no way of seeing inside, the room remaining a frustrating mystery ...

  * * *

  That night, I cooked a simple meal of beans and rice on the stove. I’d picked up some food and supplies from the last town I’d passed on the drive here – maybe fifteen miles away – and I hoped it would be enough last me for at least a few days at least.

  Then, once I was done eating, I took out one of the novels I’d brought with me and curled up on the couch and started to read. Or tried to. Because for some reason, I couldn’t stay focused on the book, the text swimming on the page as my mind still seemed to latch onto the mystery of that damn room. I simply couldn’t shake my curiosity free. It was like that feeling when you’re trying to get to sleep, except an open cupboard door keeps you awake. Only this was in reverse. It was a locked door that was distracting me!

  After a few fitful minutes, I flipped my book closed again and pushed myself back up off the couch, pacing back to the door and trying the handle once more, of course having no luck. But this time I knelt down and inspected the keyhole. It looked pretty basic – the hole was cut so roughly it looked like a DIY job, certainly not some fancy top-of-the-range lock system, and I wondered how hard it might be to pick something like that.

  But should I?

  After all, this was somebody’s private stuff. Perhaps there was a damn good reason why Elizabeth’s cousin had kept that one room locked up – no doubt full of his or her private things.

  Yet at the same time, I could feel my curiosity quickly getting the better of me, my brain latching tight onto the mystery, and I knew enough about my fucked up head from all those months of therapy that I wouldn’t be able to let it go until I’d found out exactly what was behind that damn door.

  So now I had a new puzzle.

  How the hell was I going to pick the lock?

  I figured I’d need some kind of pin or wire – something I could bend into shape and slip into the hole, to try and fool around with the mechanism. When I remembered: I had some documents in the car – just a few forms and whatnot from the sale of my Mom’s house – that I’d stuffed into the glove compartment of my car ages ago, and which were held together by a paperclip, if I remembered correctly.

  The sun was just starting to set as I raced back out of the cabin, pulling open the car door, then the glove compartment, sure enough finding that single paperclip that held together the sheaf of papers I’d stuck there.

  I clutched it tight in my fingers, carrying it eagerly back into the cabin, knowing it was pretty much the only thing I had that might work to pick the lock. Once I was back in front of the keyhole, I very carefully began bending the paperclip out in what I hoped was a simple hook shape, knowing I needed to be super careful so that I didn’t accidentally snap the flimsy metal in the process.

  When I was done, I gingerly slipped the makeshift skeleton key into the hole, wiggling it around, trying to get a feel for whatever kind of locking mechanism was inside. I turned it a few times, shifted it back and forth, tilted it at angles, and I was about to give up, when all of a sudden I felt the metal of the paperclip catch onto something, and with a subtle shift of weight and a slow turn of my wrist, I heard and felt a satisfying click.

  Holy shit! Had I actually done it?!

  I couldn’t quite believe I’d succeeded, and I felt super proud of myself. But my pride was quickly replaced by curiosity as I realized that now I would find out what was inside this mysterious room.

  It’s probably nothing much, I told myself.

  But at the same time, I could feel my heart starting to boom with excitement, as if some part of me deep down knew that there would be something strange and interesting on the other side of that door.

  I reached out and turned the handle, then pushed it open and stepped inside ...

  2

  For a moment, I remained in the doorway, paralyzed with shock, totally unable to believe my eyes. Because unlike the simple, rustic décor of the rest of the cabin, this room was really beautifully decorated – set out like some high-end boutique hotel room, the walls painted in a pale pastel pink, the bed laid out with crisp white pillows and sheets, as well as a smart white mirrored dresser unit and large modern closets built into the whole back wall. In fact, the whole effect was so at odds with whatever I’d been expecting that for a moment I wondered if I was imagining it.

  But as I walked tentatively inside, pulling back the plush pink curtains, the evening sunlight flooding into the room, none of it disappeared, instead just looking even more fancy and high end now that it was fully illuminated.

  What the hell? I thought as I assessed the room, taking in other details, like the huge, free standing gilt-edged mirror that stood proudly in one corner.

  I had no idea who Elizabeth’s cousin was. For some reason, I’d been imagining a dude, but this looked like the bedroom of a fashionable young woman. But why the hell would a girl with such classy expensive tastes want to hide herself away in the middle of nowhere?

  It made no sense whatsoever, and now I had a whole new puzzle to ponder on.

  I began to investigate further, first walking towards the dresser unit, reaching out and sliding open the small drawer to reveal a whole host tubes, pots and sticks of what looked like expensive makeup brands, their glossy plastic cases gleaming back at me like jewels.

  Next I walked over to the large built in closets on the far wall, first opening the one on the left, staring in at a rack packed full of dresses, skirts and blouses, all neatly hung on plastic hangers, with a long row of shoes at the foot of the closet. I absently let my fingers rake across the row of fabric, enjoying the soft silky feel of the clothes.

  I guess I’d always had something of a curiosity about women’s clothing. Not in a weird way or anything, but I’d certainly envious growing up about how interesting and unusual it was compared to the kinds of boring, functional clothing us guys got to wear.

  I’d never actually had a girlfriend of my own, so maybe that was another part of what made it all so fascinating and unusual – the very fact that it was so far away from my own experiences and everyday life.

  But as I opened the other closet door on the right, the situation took another unexpected turn. Because this side of the closet wasn’t devoted to clothing but instead to ... well ... wigs.

  I stared in shocked amazement at the row of polystyrene mannequin heads, each sporting a different style of wig. Some were long and blonde, and some were cut in a short bob cuts. One was super curly and red, while another in glossy pitch black had severely straight bangs cut at the front.

  And beneath the selection of wigs were drawers.

  Spurred on by pure curiosity, I pulled open the first, which was stuffed
full of panties and bras, in all colors and styles under the rainbow. I felt a weird charge of excitement as my eyes took in the vast selection. Almost beyond my control, I found myself actually reaching in and sorting through the underwear to take a closer look, uncovering thongs and g-strings, simple white schoolgirl panties, and silky red booty shorts, as well as what seemed to be a whole selection of matching bras, too.

  There were two more drawers, and I pulled open the middle one, this time revealing a series of white cardboard boxes. I gingerly lifted the lid of one of them, unable to believe what was inside. Because staring back up at me were a set of super realistic looking rubber breasts, complete with small dark pink nipples. I prodded one with a fingertip and it actually jiggled a little, so I guessed it must be made of some kind of silicone substance which make it so lifelike.

  There was another slimmer box in there too, and when I lifted the lid on that, another flash of shock ran through me. Because this seemed to be some kind of elaborate silicone pussy, made of the same substance as the breasts. It had some kind of see-through strap mechanism at the back, kind of like a g-string, which I guessed was to hold it in place.

  Holy shit, I thought as the final pieces of the puzzle slotted together in my brain. So Elizabeth’s cousin must be some kind of crossdresser ...

  Suddenly I could see why the door had been locked, and I felt bad for uncovering his secret. Yet at the same time, I told myself I would make sure everything was left exactly as I’d found it, and never mention any of it to Elizabeth.

  After all, this was someone’s private thing, and who the hell was I to judge what another guy liked to do behind closed doors?

  By now, I felt pretty bad for snooping and I knew I should leave the room, but at the same time I still wanted to see what was in that final drawer.

  I crouched down and slid it open. On one side were a selection of neatly folded pantyhose, stockings and even a couple of suspender belts, while on the other were some swimwear items – a plain black full-bottomed bikini, a very skimpy white one, and a full body swimming costume, too, in a speckled peach and purple design.

  With the mystery finally solved, I knew it was time to leave, so I carefully slid the drawers back to, closed the doors of the closet, and then after a final check to make sure nothing else was out of place, I left the room, closing the door behind me, vowing never to set foot inside again – and to respect people’s privacy in future.

  It was starting to get dark outside, and instead of lighting the lamps, I decided to grab an early night.

  I was pretty tired from the long drive after all, and the idea of waking up early tomorrow and having a full relaxing day in the cabin sounded awesome, so without even brushing my teeth or washing my face, I headed through to my bedroom, feeling my sprits sink somewhat when I set eyes on the rusty metal-framed cot with its starchy white sheets and rough woolen blankets, knowing there was a much more comfortable bed I could use just on the other side of that wall.

  But I decided to stick to my promise, undressing down to my boxers and t-shirt, then climbing beneath the covers and closing my eyes, feeling the first waves of sleep quickly drifting towards me.

  As I let them envelop me, I also let my mind run free, running over the events of the day, my swirling thoughts once again returning to the mysterious room I’d discovered, full of its strange, feminine secrets ...

  3

  That night I had the weirdest dream, although I can see now, writing it down in the clear light of day, it’s kinda obvious I dreamt what I did. In my dream, I had long flowing blonde hair instead of my usual scruffy mop of mousy brown fuzz, and my legs were long and smooth. What’s more, I was dressed in an elegant black ball gown with a slit all up one side – the kind you might see a model wear to some glamorous evening function – and my feet were encased in huge stiletto heels.

  I was walking along a corridor, my whole body infused with a sense of feminine grace, so unlike my usual stooped posture when I walked, and for the first time in my whole life I felt happy and confident – like I’d finally unlocked some deep secret on how to let go and enjoy myself, the way others around me seemed to do every day.

  I held my head high and proud as I strutted along, enjoying the sexy, silky feel of that long black dress flowing elegantly around my bare legs. And as I reached a large set of double doors, I reached out and pushed them open, uncovering an endless chasm of black nothingness beyond.

  It was such a sudden, stark contrast that it woke me with a jolt, and I sat up in bed, catching my breath, for a moment wondering where the hell I even was, before I remembered I was here in the cabin, on the first full day of my vacation.

  I lay back in bed for a while, mulling over the dream, trying to make sense of it. Sure, the women’s clothes had been influenced by finding all the stuff in the secret room yesterday. But what the hell did the black, blank void mean? What’s more, the memory of how good it had felt to wear that slinky sexy stuff in the dream kind of stuck with me now that I was awake, almost as if there were some teasing, tempting voice in my head, saying: Go on ... Try on some of those clothes ...

  I tried my hardest to shake the thoughts free from my mind.

  Never in my life had I done anything weird or kinky like that – hell, I hadn’t even really done anything particularly vanilla. I was still a pathetic virgin at twenty-three, and I knew that before I even started exploring any of that sort of stuff, I first had to work on me; on getting some much needed confidence, not to mention some closure on all the shitty stuff in my past.

  I pushed myself out of bed and padded through to the living room, wondering what to do once I’d fixed myself some breakfast. It was kinda tempting just to hang out and read – after all, the idea of doing absolutely nothing was still such a thrill.

  But at the same time, I still liked the idea of a swim in the lake, and maybe dipping my body in the no-doubt chilly waters would shock all those crazy thoughts of crossdressing from my mind.

  It was decided. I set to work fixing a simple breakfast of bread, cheese and a glass of orange juice, then set about gathering up everything I wanted to take to the lake: a towel, a book, and of course my swimming shorts.

  But when I started searching through my bag, they didn’t seem to be there. It made no damn sense. I was always so ordered and careful, and I’d made sure to pack and repack everything I intended for this trip two or three times, making sure it all fit into the hold-all.

  But it was no use. No matter how many times I searched through the bag’s contents, each time I came to the same frustrating conclusion: my swimming shorts weren’t there.

  God damn it, I thought, as I tried to think up an alternative.

  The idea of skinny dipping held no appeal whatsoever. Hell, the whole reason I was here on this vacation was to escape my hang ups and nervousness, and even just thinking about stripping naked in a public place had me cringing – despite the fact that I knew I was being stupid and that there’d be nobody about for miles. Nope. No way would I be doing something as daring as that, especially on my first day here.

  Even the idea of wearing a pair of my regular boxer shorts didn’t particularly appeal. What if they got waterlogged and slid off me and I lost them at the bottom of the lake? No, I needed something tight, preferably with a drawstring around the top to keep them firmly in place.

  My only feasible alternative seemed to be getting back into my car and driving the fifteen or so miles to the last small town I’d passed, in the hope there was a shop I could buy some swim shorts from.

  I knew the chances were slim, but what else could I do?

  With a heavy heart, I threw on some clothes and shoes then made my way out of the cabin, stepping into the muggy heat of the morning before pulling open the door to my car and climbing inside – where the air was even hotter.

  I let out a sigh of frustration. This was a shitty start to my vacation, and the idea of driving all that way and back in the sweltering heat didn’t exactly fill me with e
xcitement.

  Just as I was reaching out to slip the key into the ignition, another thought entered my mind: a memory of the bikinis I’d pulled out of that last dresser drawer. Sure, most of them were super skimpy and feminine, but one of them included a pair of plain black, full bottomed briefs. In reality, how different could those be to regular swim shorts, I wondered. They were practically unisex … right?

  The more I thought about it, the more I convinced myself that this was a much better idea, and I knew I should at least try them on before I dismissed it entirely.

  So I got back out of the car and headed into the cabin, this time straight towards the very room I’d sworn never to set foot inside again ...

  4

  As I opened the doors to the closet, my gaze was distracted for a moment by the selection of colorful, glossy wigs, before I focused on the task at hand, crouching down and sliding open the bottom drawer, then rooting through the bikinis until I’d found what I was searching for: the plain black bottoms.

  I brought them out, holding them up to inspect them closely, noting that the cut was somewhat different to regular guy’s swim shorts – higher at the waist, and also cut in much more of a V-shape at the butt area than I’d remembered.

  I had the sinking feeling that I’d look totally stupid in them, but I decided the best thing to do was to try them on in front of the mirror to see.

  I felt a strange nervous excitement as I began to pull off my own clothes. I’d never liked getting undressed – even alone – mainly because I hated my skinny, pale body, which still lacked definition, when at twenty three I should be a fully grown man by now. Instead I still looked like a scrawny teenage kid, and the fact that I had hardly any noticeable body hair didn’t help matters either, save from the fuzz that grew under my arms and around my dick.