Dressed for Pleasure

by D. L. Savage

  Because it turned out Cassidy wasn’t joking; I really did have a pretty good ass! Now that it wasn’t just some hairy guy’s butt, I could see that it was actually pretty pert looking, and not that much smaller than hers, either. What’s more, my toned thighs looked kind of thick in a good way, too. For a split second, I even found myself getting excited about seeing what it would look like in some skimpy pair of panties, before I quickly pushed the fucked up thoughts from my swirling brain.

  God damn it, she’s really screwing with my head ... What does she want to do? Turn me into a fag or something?!

  “I think these will do just nicely!” she exclaimed at that moment, holding up a skimpy white thong with a little pink bow on the front, a naughty grin curling on her plump glossy lips.

  Despite everything, I felt my dick once more throbbing in its cage, as a weird private thrill fluttered through me despite myself. Because the truth was, all of a sudden, a fucked up part of me really did want to try on that thong, even though I’d be damned if I was ever going to admit that to her.

  So I forced an expression of disgust onto my face, hoping my real feelings didn’t show as I grumbled, “You can’t be serious.”

  Of course she shot back with, “I’m deadly serious, Josh,” striding towards me and pushing the balled up panties into my hand, then hissing beneath her breath, “Put ... them ... on.”

  My hands were actually shaking a little as I fumbled with the panties, my nervous excitement made all the more intense by the fact that I could feel Cassidy’s big green eyes watching me the whole time, a sexy grin playing on her glossy lips as I unfurled the panties, staring down at them.

  They looked so damn skimpy – just a tiny wisp of silky white fabric – and I wondered for a moment if they’d even fit. After all, my body was a little bigger than hers, and of course I had a lot more to pack into them, too.

  When I finally I had them the right way around, I gingerly stepped first one foot then the other inside them, before sliding them slowly up over my thighs and then hitching them right up around my waist, feeling their snug tightness quickly enclose my caged cock and balls in a surprisingly good and satisfying way.

  Never in a million years had I thought that one day I’d actually be wearing my girlfriend’s panties. Sure, I enjoyed seeing her in them – and she always favored the skimpier kind, strutting around in sexy thongs and g-strings, even when she was just hanging out at home – and sure, I’d idly wondered what it might feel like to wear something like that. But even so, that was as far as my curiosity had ever gone.

  But now, here I was, standing in our bedroom, dressed in a pair of her slutty white panties. And the idea of it was turning me on way more than I ever thought it would. I even found I liked the weird wedgie sensation between my butt cheeks, and again I found myself turning around to check out my ass in the mirror, a fresh flash of excitement running through me as my suspicions were confirmed: my butt really did look fucking hot in a thong!

  “See Josh?” she laughed. “You really do have a pretty cute ass!”

  When I turned back to face her, I couldn’t stop myself from smiling and nodding proudly.

  “I think you’re finally starting to enjoy this little game, too,” she added, raising a carefully plucked eyebrow. “Isn’t that so?”

  “Shut up,” I murmured, a flush of embarrassed heat rising to my face.

  “C’mon, why don’t we give you a cute pair of titties to match,” she giggled, excitedly grabbing a white bra from the bed, with a matching little hot pink bow on it between the cups.

  “But I, uh, haven’t got anything much to fill a bra,” I said confused. After all, I knew that Cassidy was a c-cup and the puppy fat of my pecs certainly wasn’t as big as that.

  “Oh, baby!” she laughed, grabbing her breasts in both hands and jiggling them at me. “You think I was born with these? Hell, I was wearing bras before I had anything to fill them with. And you wanna know what girls do when they’ve only got itty bitty titties?” She leant towards me, lowering her voice to a playful whisper. “They pad.”

  She gave me a wink, and I felt another rush of excitement despite myself at the idea of seeing myself with pert breasts, just like Cassidy’s, even if they were just made tissue paper or whatever.

  “Now hold out your arms,” she instructed, and I did as she said, as she slipped the bra on over my arms then moved around behind me to fasten it. “You might have to breathe ... in,” she added, as she hitched the thing so damn tightly it made my eyes water and I gasped in surprise. “Sorry, it’s probably a little tight!” she giggled.

  “You’re telling me,” I groaned, feeling the straps digging in sharply at my sides.

  “But trust me,” she continued. “The pain you’re feeling now will be worth it when you see yourself. And anyway, who said beauty came easily? That’s another thing you have to remember, Josh. Us girls have to put up with a lot of pain to look this good. Just wait until you try heels. Those things fucking hurt!”

  I didn’t know if she was joking about heels or not; after all, where the hell would she have found a pair in my size? But then again, she’d obviously bought that chastity device in secret from somewhere, and I began to wonder just how far she was planning to take this little game.

  She quickly dashed off to her underwear drawer again, returning a moment later with a couple of pairs of her small white sports socks, which she carefully folded then stuffed into the cups. The bra was already stretched pretty tight across my pecs, what with it being too small for me, and with the socks in place, the cups actually looked full, at least from where I was standing.

  “Okay, now you can put this on!” she said, grabbing the baby doll negligee and handing it to me.

  I looked at it for a moment, kind of puzzled as to how exactly I got into it, when Cassidy cut in, “You pull it over your head like a sweater, dumbass.”

  “I knew that,” I lied, as I followed her instructions, pulling it over my head and feeding my arms through the straps. As I let it fall about my waist, I found I enjoyed the soft silkiness of the flimsy fabric dancing against my skin, sending fresh secret flutters of pleasure through my body, despite myself. And it felt so naughty too. After all, it was practically transparent – my bra, thong and smooth hairless body was on full display beneath – and it finished right at the very tops of my thighs, showing off the smooth round bulge of my cock in my panties, too.

  By now I was enjoying myself so much I could feel my dick throbbing madly, and in that moment I was actually glad I was wearing that stupid chastity device, because if Cassidy had seen how much her little game was turning me on right now, I knew I’d never hear the end of it.

  “Are we done yet?” I said in what I hoped was an annoyed sounding voice, while a private part of me actually kind of hoped there was more to come.

  And when she shot me a look and said, “Baby, we haven’t even started,” I had to try hard to fight back a smile ...

  5

  “Now a real lady wouldn’t get all dressed up like that and not put on a little makeup too, would she?” Cassidy taunted.

  I shook my head, my heart starting to pound as it dawned on me that what she was going for here was a full transformation. And what was even crazier was that I had to agree – I hadn’t dared take a peek at myself since I’d put on the negligee and I suspected that I’d look kinda silly with my body all girly but with a guy’s head. I was even a little curious (and hell, why deny it, excited) to see what I’d look like made up.

  Before the tanning salon, Cassidy had worked at a makeup counter, so I knew she was a whizz with that kind of stuff – always doing crazy things to bring out her eyes and cheekbones and whatnot.

  “Why don’t you take a seat over here,” she said, breaking me out of my thoughts as she patted the back of the chair that was set up in front of her makeup table, “and we’ll get started ...”

  As I walked towards the table, I don’t think I’d ever felt so aware of my body before. I coul
d feel the cool air against my tingling, freshly shaved legs, and I could feel the thong strap between my buttcheeks, teasing my ass with each step I took, sending weird little flutters of pleasure directly to my caged dick, causing it to throb hard in my panties. And as before, I found myself moving more gracefully and daintily than I normally did too, accentuating my movements to make them more fluid and girly, somehow knowing instinctively that it would look better that way, now that I was all dressed up.

  Cassidy seemed to share in my excitement, clapping her hands and exclaiming, “Oh my god, this is going to be so much fun! You have no idea how long I’ve wanted to do this ...”

  My heart was positively booming as I eased myself into the chair, giving myself up to the situation, no longer resisting, my curiosity building with each second as Cassidy set to work ...

  * * *

  “There,” she announced, after what felt like an hour in the chair. “I think we’re done.”

  In reality I had no idea how long had passed, all I knew for sure was that I was something of a fidget – pissing her off a number of times when I’d shifted even imperceptibly. Also, apparently I had ‘really good bone structure’; she’d complimented my cheekbones in the past, and as she’d made me over, she’d seemed to spend a lot of time on them, working in all kinds of powders with various brushes and whatnot.

  In fact, she’d spent what felt like an age on every part of my face – my lips, my eyes, even my nose, brushing yet more dark powder along the sides of it, telling me that it would help thin it out and make it look more girly.

  By now I was desperate to see the result. But when I tried to turn around to peek at myself in the mirror behind me, she grabbed my shoulder.

  “Uh uh uh!” she scolded. “Not just yet! Don’t you think you’d look better with lovely long hair, too?”

  I felt my stomach flip in surprise.

  “You didn’t,” I said quietly, unable to believe it.

  “I sure did!” she laughed, dashing over to the closet and pulling open the doors, then removing something in a large clear plastic packet. The moment I saw the glossy blonde hair through the packaging, I felt my excitement spike afresh. She’d actually bought a fucking wig?! How long had she been planning this crazy stunt, anyway?

  She carefully removed it from the packet, shaking it out and running her fingers through the long shiny strands. It looked to be cut in a similar style to Cassidy’s own hair – with long bangs at the front and masses of silky, shiny hair – only unlike her hair, it was blonde. Like really blonde.

  She walked around behind me, telling me to hold still as she carefully fitted the cap part over my head then adjusted it a little, before brushing the bangs into place, sweeping them around my forehead, then stepping back, a strange smile on her face.

  “Y’know?” she said in a quiet voice that sounded charged with a similar excitement to the one I felt. “I think I’ve done a pretty fucking good job, if I do say so myself. Oh, I almost forgot! A few finishing touches!”

  She raced once more to the closet and this time drew out a pair of silky white holdup stockings with lacy tops, and a pair of matching white slippers – the kind a kitschy ‘50s housewife might wear, with fluffy white pom poms on top.

  “Here you go, Cinderella!” she said, handing me the stockings and slippers.

  I didn’t even speak, just balled the stockings up like socks, then pushed my feet inside, rolling them slowly up my legs, one by one, amazed all over again at how these simple little touches really did create the illusion of true femininity. I tugged the tops of the stockings into place, adjusting them at the tops of my thighs until they were level, then slipped my feet inside the slippers, no longer even surprised that she’d obviously snuck a look at my shoe size before buying them.

  And then I just sat for a moment in the chair, my body tingling and my heart in my throat, before I finally pushed myself up to my feet and slowly approached the mirror. It was only as I walked towards it that the doubts began to creep in.

  What if I looked hideous?

  What if she was just pretending I looked good to make a fool out of me, and this was all part of some even more devious scheme?

  But when I set eyes on myself, my negative thoughts evaporated in an instant. Because to my total and utter amazement I looked ... amazing.

  I know that might sound vain, but it was all down to Cassidy’s hard work and expertise that I looked that good, not mine. There was hardly any of me left. It was all an illusion. The stockings, the padding, the hairless skin, and of course the makeup and wig, which obliterated any last fragments of my male self.

  It was like I had a whole new face! Thanks to whatever voodoo she’d done, I now had huge plump lips and a slim petite nose, while my eyes looked so fucking large and cartoonish it was crazy, rimmed in all that powder and eyeliner. And like she’d said, my cheekbones really did look great, too. She’d used dark powder to give the illusion of shadows, and of course my pretty, girly face was framed by the glossy blonde locks of the wig. I actually looked like the kind of girl I always wanted to bang back in college, the kind of girl I’d lusted after all my damn life. But she was me.

  “You like?” Cassidy said, coming up behind me, then locking eyes with me in the mirror, and I knew there was no use in even hiding how much fun I was having any more.

  “I have to admit,” I said in a softer, more feminine tone than my usual voice, not wanting to break the spell, “when you first started in on this, I thought you were insane. But yeah, I do look pretty good don’t I!”

  “You look fucking hot,” she grinned. “Which reminds me! It’s almost eight o’ clock. I’d better start getting ready too ... After all, it won’t be long now until the boys arrive!”

  As she said the words, I felt my stomach drop through the goddamn floor.

  In all the excitement, I’d totally forgotten that tonight was Movie Night, and there was no way in hell I’d ever let the guys see me like this. These were my old college buddies remember, the most macho, straight men I knew. I’d never fucking hear the end of it if they knew I was into wearing makeup and panties!

  “Holy shit,” I exclaimed, awkwardly fumbling with my wig and stockings, trying to get all this damn girly stuff off me as fast as humanly possible, just in case one of them showed up early.

  “Woah, woah, woah,” Cassidy said, causing me to stop and look up at her. “What the fuck d’you think you’re doing?”

  “I’m getting changed,” I said weakly.

  “Oh no you’re not,” she shot back, her tone suddenly cold and venomous. “You think dressing you up like this was the end of my little game? Think again, baby. Because boy have I got some fun lined up for you tonight ...”

  6

  A cold dread swept over me, as Cassidy paced up and down the bedroom, outlining her plan for the rest of the night, while I just listened on in stunned, horrified silence, feeling like I was trapped in some kind of waking nightmare.

  “Here’s what’s going to happen,” she began. “Your buddies are going to arrive, one by one, and I’m going to tell them that you’re sick in bed upstairs, that it was something so last minute — food poisoning or whatever - that you didn’t even have time to call and cancel. Then I’m going to lead them through to the den and get them all nice and comfortable. And then you’re going to ...”A cruel grin spread across her face and her big green eyes latched on to mine, flashing with bitchy feminine glee. “Well, you can wait and see.”

  “Why are you doing this?” I asked weakly, still unsure what she actually expected me to do, dressed like this.

  “I’ve seen the kind of things you and your buddies like to watch on movie nights,” she laughed cruelly, obviously referring to the fact that as well as some normal action movie, part of the tradition was to throw on a porno, too. “Always sluts, down on their knees, sucking dick. That’s what you like, Josh, isn’t it? That’s what really turns you on. Well, now I want you to know what it’s like to be the slut for once
– to get a taste of it for yourself ...”

  “But that’s crazy … I can’t,” I croaked weakly, every atom in my body trying to fight back, to take control. “What are you saying? That you want me to blow them?”

  “Maybe,” she teased.

  “I can’t!” I repeated in a pathetic moan. “And anyway, they’d never even let me near them in the first place. They’d laugh in my fucking face the moment they saw me like this ...”

  “Oh trust me,” Cassidy shot back. “If my little plan goes of the way I want it too, they certainly won’t be laughing. You have two options, Josh. You can either do exactly as I say and I promise I’ll keep this little game between us, and trust me, but I can assure you your buddies will never know it’s you. Or we can do things the hard way ...”

  With that, she reached into the pocket of her hoodie, pulled out her iPhone and before I could even turn my head away, she’d snapped a photo of me, the flash blinding me for a half second.

  “Forget your college buddies,” she threatened. “What would your boss think if he saw you like this? Wasn’t he complaining to you just last week about all that gender inclusive washroom bullshit? All those transgender girls who he believed were actually just creeps in dresses who wanted to infiltrate women’s washrooms to spy on them? Well, wouldn’t he be pretty interested to know that one of his own staff members like to dress up all sexy in her spare time?”

  I felt my stomach sink yet further. There was no way in hell I could let my boss see me like this — he’d let me go in an instant — and I knew then that I had to go along with Cassidy’s cruel plan, whatever it entailed. All I could do was hope that she really meant what she said, and that she had some way planned out that my buddies wouldn’t find out it was me.

  “Alright, I’ll do it,” I said miserably, my stomach churning, knowing I had no other goddamn choice.