Dressed for Pleasure

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Dressed for Pleasure Page 26

by D. L. Savage


  Shaking my head at the total absurdity of the situation I found myself, I gingerly stepped into the panties then pulled them up over my thighs and around my waist. They were cut in a low rise style, sitting just below my hips, but I guessed that Adrina must have paid attention to the measurements I’d written down on that form yesterday, because they fit me like a glove. A very tight, snug glove, but a glove nonetheless.

  Since I’d been old enough to buy my own clothes, I’d always favored boxer briefs, so this was a whole new world for me. Sure, I knew that a lot of chicks wore them, and I liked seeing a girl in a sexy thong as much as the next guy, but actually wearing one myself? Well, it was what you might call ‘intimate’ – what with the strap at the back sitting so damn tight and snug between my ass cheeks, while the stretchy white fabric cupped my cock and balls so tightly it was crazy, creating a soft round bulge between my legs that almost looked like plump pussy lips.

  Next I turned my attention to the bra. Inspecting the cups, I saw that it was padded, like really padded, and when I squished the cups with my thumb and forefinger it felt like they were filled with some kind of squidgy gel.

  I can’t believe I’m actually doing this, I thought as I began trying to get the bra on, fumbling behind my back for a while until I finally got it to clasp, before slipping the straps over my arms then tugging the padded cups up into what I hoped was the correct position.

  There was no mirror in the room, but in a way I was glad, knowing I probably looked a total fright – like some hideous nightmare image of a girl.

  But as I sat down on the chair to begin pulling the white stockings on, balling them up and then rolling them slowly up my freshly shaved legs, I had to admit, at least from where I was sitting it did look pretty realistic.

  Because from my field of vision, I could now see the pert round bumps of the bra, the snug white panties, and once the stockings were both in place, pulled all the way up to the tops of my thighs, they really did make my smooth hairless legs look kind of girly.

  I’d always hated how skinny my body was, never wanting to wear shorts or go swimming or in any way call attention to my slight, boyish frame. But oddly, like this, encased in stockings, my legs actually looked pretty good and I found myself focusing on different details, like the fact that my thighs were actually kinda thick, at least in comparison.

  Once I’d put on the underwear, it was time for the dress. As I pushed myself up from the chair, I was again made aware of the thong, as it seemed to tease my butthole each time I moved or took a step, and I wondered if all the hot chicks I saw walking around in the city in their tight leggings and yoga pants and mini skirts, were all secretly aware of the same sensation.

  I had to admit, despite my nerves and confusion and downright embarrassment at the situation I found myself in, there was something else I was feeling too: horny. Only subtly, but it was definitely there.

  I’d never really done anything kinky in my life before. Whenever I watched porn, I always seemed to just gravitate to the most boring, vanilla, boy/girl stuff imaginable, just wanting to get it over and done with. But this was different. It was a subtle kind of thrill, a weird whole body pleasure, both at the feel of the snug, silky underwear, and also at the very idea that I was dressing up in the same kinds of things that hot, slutty girls wore.

  I turned to the dress, figuring I’d better get it on quick, in case somebody came bursting in and caught me in just my underwear. For a moment I found myself puzzling, trying to work out how the hell to even get it on me, before eventually figuring out that you pulled it on like a sweater.

  So I shoved my head and arms through the appropriate holes and then inched it down over my body until it was snugly in place, the hem siting just below the tops of my stockings. And again, I guessed that for it to fit this well, Adrina must have paid close attention to the measurements I’d given her.

  As if to confirm my suspicions, when I slipped my stockinged feet into the simple flat white shoes, they too fitted me just perfectly.

  I’d never worn a dress before, and I could kinda see the attraction. I’m probably stating the obvious but it felt much freer than a shirt and pants – both secure but loose, too – and I found myself enjoying the odd sensation of the gap at the bottom, and the kinky knowledge that if I wasn’t careful, I’d accidentally give someone a flash of my panties.

  Now dressed, I paused, wondering what to do. Was I supposed to wait here? Or go out and to find Adriana again? The thought of leaving the room and wandering back to the lobby dressed like this filled me with total embarrassment, and again I found myself wondering what the hell I was even doing here.

  The whole thing felt like some kind of practical joke or hidden camera show, and a part of me began debating whether or not to just get changed back into my regular guy clothes and hightail it the fuck out of there, when all of a sudden the door opened again and in stepped a familiar face: Clara, the cute girl from reception.

  The moment she set eyes on me, I heard myself trying to frantically explain what was happening, desperate for her not to think I was some total weirdo, the words racing from my mouth in a garbled rush: “Oh hey ... I just ... This isn’t what it looks like … Adriana asked me to ... She chose the clothes and ...”

  “It’s okay,” Clara cut in with a reassuring smile, not at all disgusted by the sight of me dressed like this. “Adriana’s explained everything to me already. Actually, that’s why I’m here! To fit your wig and do your makeup ...”

  For the second time that morning, I felt like I was in some kind of crazy dream.

  “My wig and makeup?” I repeated in shock.

  “Of course,” she smiled back, like it was the most normal thing in the world. “After all, you want to look pretty don’t you?”

  6

  I have no idea how long it took Clara to do my makeup. It could have been five minutes, it could have been an hour. I just sat there, dazed, as she dabbed and patted and brushed at my face, wondering if this was even happening, or if I’d suddenly wake up.

  As she worked, I couldn’t help but sneak glances at her. She was so cute – really pretty in a fresh girlish way, her slim face fixed in concentration as she worked at my makeup – and I guessed she was probably about my own age.

  Occasionally she’d ask me a question, but most of the time she just worked away in silence. But at one point, I decided to say the thing that had been bugging me.

  “Adriana’s been calling me Petra,” I admitted. “But my name’s Peter.”

  At this Clara paused, staring at my face for a moment, then wrinkling her cute button nose, her plump lips curling into a grin as she shook her head and said, “Nah, you definitely look more like a Petra.”

  Eventually she was finished, and as soon as she had my makeup done, she set about fitting the wig. It was blonde and wavy, shiny and lustrous and surprisingly real looking, too. I couldn’t take my eyes off it as she brought it carefully out of a clear plastic bag then began shaking it out, running her slim fingers through it, before gently fitting it to my head.

  The sensation was actually a little like wearing a beanie, and I found I really liked the feel of all that thick glossy hair falling about my face and onto my shoulders.

  By now, I was pretty curious to take a peek at the finished look and it was like Clara could read my mind when she grinned and said, “You wanna see?”

  I nodded, feeling a surprisingly powerful flash of excitement in my stomach.

  “In that case, follow me ...”

  As she turned and led me out of the room, I again found myself sneaking a quick hungry glance at her butt – shown off in that tight dress. And now I knew exactly what she must be feeling, because it was the very same make and design of dress to the one I was wearing. I guessed she was most likely wearing the same style of panties and bra beneath it, too.

  “The washrooms are just through here,” she said, gesturing to two doors at the ends of the corridor – one on the left, one on the right.
“Take your time, and I hope you like what I’ve done. When you’re finished, I think Adriana wants you to go to her office ...”

  “Thanks,” I smiled, finding myself much more relaxed around her now that I was dressed like this. Weirdly all my nervous energy was gone, replaced instead with a strange calm. Maybe it was because the wig, dress and makeup felt kinda like a disguise; like I was in costume, and like I could do whatever I wanted, without anyone knowing it was me ...

  Clara gave me a final friendly smile then headed back to the reception, while I turned and stepped into the nearest washroom, excited to see what she’d done to my face. But as I stepped inside, glancing over at the faucets, I saw a dude standing there – an expensively dressed businessman who looked back at me in total horror – and that’s when it first dawned on me. I must look pretty realistic, because this guy definitely thought I was a real girl.

  “I’m sorry,” I said in my softest, most ladylike voice, before quickly exiting the washroom, realizing that out of pure habit I must have stepped into the guys’. So I headed across the hall, tentatively stepping into the female washroom, now scared that the same thing would happen here too, that there’d be a girl just washing her hands, who’d freak out about some dude in drag walking in on her.

  But thankfully the washrooms were empty and I was able to head over to the large mirror above the faucets to finally check out my own reflection for the first time.

  I can still remember the pure jolt of energy and shock that crashed through me when I first set eyes on myself. It was crazy. I looked totally authentic and nothing at all like myself. Sure, if I really scrutinized, I could see that it was still me underneath all that makeup, but fuck, Clara had done such an awesome job – accentuating aspects of my face while subtly pulling focus away from others – that I really and truly looked like a girl. A hot girl.

  The blonde wig helped a lot. It was obviously expensive, perhaps even made from real human hair, and I found myself pouting and posing in the mirror, my confidence and excitement growing by the second.

  Out of nowhere, Adriana’s voice floated back into my head: there is something about you ...

  That was the phrase she’d kept repeating during my interview. I’d thought nothing of it at the time, but now, staring at myself in wonder, at my big eyes, my crazily plump lips, and my figure – the body I’d hated ever since I was old enough to care, which in that white dress suddenly looked amazing – and I realized Adriana was right. She’d obviously seen something in me, something I didn’t know existed. And what’s more, for the first time, I was actually kinda excited, looking forward to stepping out of the washroom and starting my trial shift.

  Because I no longer felt like myself – like boring old Peter.

  It was like I was in a disguise.

  Now I really was Petra, and Petra was ready to start work ...

  7

  “Oh wonderful!” Adrina said when she saw me, pushing herself up from her desk to get a better look, striding towards me then taking hold of me by the shoulders for a moment as she looked me up and down before remarking, “Clara has done an excellent job.”

  “Yes, she has,” I replied, my new soft girly voice seeming to come so naturally to me when I was dressed like this.

  “But you will have to learn to do all this yourself, you know,” Adrina added seriously.

  I nodded; in actual fact, I felt eager to learn how to do it, for Clara to share her makeup secrets with me, so that I could really transform into a girl any time I wanted.

  “Yes, I think the gentlemen will like you very much,” Adrina added.

  “The gentlemen?” I asked nervously, still unsure whether or not this really was a legit massage parlor or something else. “What actually happens here, Adrina?” I added gently. “If you don’t mind me asking.”

  “I don’t mind at all,” she smiled back. “But come, it’s much easier if I show you.”

  With that she took my hand and led me towards a small door on the back wall of her office, a door I hadn’t even noticed the first time I’d been in here, a door that, when she opened it, seemed to lead to a series of secret corridors ...

  * * *

  “From here,” Adrina explained as we walked down the small dark passageways, “I have access to all the massage rooms, so I can make sure my girls are doing a good job ...”

  She paused at what looked like a small spy hole, putting her eye to it for a moment, then saying, “Ah yes, it looks like Clara is ready to receive her eleven o’ clock appointment. Come, Petra, why don’t you take a look? I always think it’s better for my new staff to see what happens, rather than to try and explain ...”

  I could feel my heart starting to pound as I moved my face towards the spy hole, placing my eye against it, then peering in at another clean, professional looking massage room, just like the one I’d got changed in. Only now there was a guy lying on the bed on his back, naked save for a small white towel that lay across his crotch.

  A moment later, Clara stepped into view, still wearing her simple white dress, just like the one I had on. I could see that she was talking to him, but I couldn’t hear what they were saying. This corridor was obviously sound-proofed, and I wondered how the spy hole worked, before remembering that in the room I’d got changed in, there’d been that modern art print hanging on the wall. Suddenly it clicked; the spy hole must be hidden by the painting!

  I watched in silence, a weird tension building inside me as Clara took a bottle of massage oil and began squirting it into her palms, rubbing them together to warm it, before she began what looked like a professional deep tissue massage, working her slim pale fingers first around the guy’s broad shoulders and then down across his toned stomach, before switching to his legs, kneading his calves then his thighs.

  I couldn’t see his face from where I was standing, but from his body, he looked maybe in his late twenties, obviously in pretty good shape, his skin a golden honey color and his body perfectly proportioned – the kind of body I’d always wished I had.

  And while deep down some part of me suspected what was coming next, it was still kind of a shock when Clara’s hands slipped under the towel, obviously starting to gently massage his cock and balls. As her motions grew faster, the towel began to slip away, and sure enough, I saw that she was stroking his cock with one hand, her fist gliding up and down his slick hard shaft, eased by the massage oil, while her other hand was massaging his full round balls.

  Her pretty face was fixed in concentration, her mouth a little parted, her eyes gazing down hungrily at his large hard cock as she stroked it in a steady rhythm, until the pearly pink head began to ooze with clear beads of pre cum.

  And somehow, I could tell that she was enjoying this. Her eyes were sparkling with a subtle, naughty glee and occasionally she’d lick her lips, almost like she was imagining taking that big hard cock in her mouth as she stroked it.

  As I watched on, I could feel my own horniness rising up, too. It was such an intense turn on, watching someone as cute and pretty and innocent as Clara working away at a big hard cock, and as I imagined her pussy getting wet and her panties growing damp, I could feel my own cock throbbing hard, aching in my thong.

  There was something else too, something I almost didn’t want to admit to myself. Because as I watched, growing more and more turned on, I knew that I wasn’t imagining that I was the guy on the bed, letting Clara jack me off. No. I was imagining that I was her – that I was the one stroking that big, glistening cock.

  Even though I couldn’t hear what was going on in the room, I knew somehow that things were growing more intense, that the guy was getting closer and closer to cumming. I could see that Clara was picking up pace, and I could see that his muscles were tensing, his glistening abs growing taught as he leant forward a little on the bed. And just moments before he came, to my total shock, Clara actually bent forward, as if unable to stop herself, taking the head of his cock in her mouth, her plump lips wrapping tight around his shaft j
ust moments before it began to pulse.

  I watched the shaft throb and I watched Clara’s throat as she obviously gulped back his load, keeping her lips wrapped around his cock and swallowing two or three times, before pulling her mouth away from his glistening cock – no drop of cum left behind.

  She turned and took hold of a fresh towel, dabbing it at the corner of her lips and then turning back to the bed, beginning to wipe off the oil on his body, and chattering away, a polite friendly smile on her pretty face, like she hadn’t just gulped down a total stranger’s cum.

  “Now do you understand what I expect from you?” Adrina said in my ear just then, causing me to jump.

  I’d been so caught up in watching the scene play out, I’d forgotten that she was even there.

  I turned to face her, my body shivering, coursing with adrenaline, knowing deep down that dressed like this, in my new disguise as Petra, something had been awoken inside me. A new kind of curiosity. A new kind of lust …

  There was no point in denying it.

  I wanted to try it myself.

  “Yes, Adrina,” I said solemnly. “I do ...”

  8

  She led me back through the corridors and out of her office, then showed me to another room at the back of the parlor – which I guess you might call a lounge. It was a plush, expensively furnished room, where the girls who worked could hang out between jobs.

  “There’s just you and Clara working today,” Adrina explained. “We get most of our business in the week, when our clients come to unwind after work. But I thought I’d start you off on a quiet shift. So please, take a seat, and help yourself to any of the refreshments ...”

  As I eased myself down onto the cool leather sofa, making sure to keep my movements as fluid and graceful as I could, crossing one stocking clad leg over the other, I could sense a subtle dampness in my panties, no doubt from the pre-cum I must have been leaking as I’d watched Clara jacking off her client.

 

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