Dressed for Pleasure Read online

  It was only as Frank turned to start making it that I realized with a flash of panic that I didn’t actually have any damn cash or credit cards on me.

  “Oh my god,” I blurted out, embarrassed, making a show of patting down my skirt as he set the steaming coffee down on the counter in front of me, “I think I must have left my purse back at my apartment ... I’m going to have to leave it, I’m afraid.”

  To my total surprise, Frank’s smile widened and he said in that same weird, polite voice as before, “Don’t worry, madam. It’s on the house.”

  “Wow, thank you,” I replied, shooting him a smile of my own, then turning to walk to a table in the corner, a slutty little part of me kind of hoping he was staring at my ass. After all, I knew just how good it looked. And again, I found my mind flooding with all kinds of horny, distracting thoughts.

  As I set my coffee down, I knew that if I was going to have any chance at all of keeping focused and spotting that old woman, I’d have to take care of my current distractions first.

  So I quickly dashed off in the direction of the washroom ...

  * * *

  The moment the door was locked behind me, I gave in to the temptations that had been tearing at me this whole time, turning to the large mirror on the wall and watching myself as I slowly inched up my skirt, until I’d uncovered the bright pink fabric of my panties. I could see the soft mound my pussy made in them, and I felt my horniness increase yet further as I turned and pushed out my ass towards the mirror, gazing at my pert butt. It looked so fucking hot, the strap of the thong disappearing between my toned round cheeks like that, and I reached out with trembling fingers and tugged it to one side, then arched my back further and spread my buttocks apart with my hand, giving myself a quick flash of my puckered little butthole and my plump juicy pussy lips.

  By now I wasn’t even fully in control of my actions. I just let my hands wander where they wanted while my mind fill ed with all kinds of slutty sexy new fantasies. I let my fingers plunge into my juicy, soaking wet pussy, finger-fucking myself with one hand, while the other strayed to my left breast, cupping my aching tender flesh, my nipples feeling so damn hard it was almost painful.

  In porn, I’d always wondered if the girls who made their moans and sighs were exaggerating. After all, back when I was a guy, I’d been able to jack off and cum totally silently if I’d wanted to. But now it felt like there was no way I hell I could stop the soft moans and sighs that were falling from my glossy lips as I worked my aching pussy towards an orgasm, and as it approached I began to worry that somebody out in the shop might hear me.

  So I started to suck on my knuckle, wishing it was a big juicy cock, my mind spilling and whirring with the most depraved horny fantasies – imagining that I was surrounded by a whole group of hot, horny guys who wanted to totally ravage my aching feminine body, taking me hard and rough in all holes, then jacking their big, slick cocks until they coated me in a shower of hot, gooey cum ...

  With a final muffled whimper, my orgasm finally hit, and I felt my body shuddering and juddering outside of my control as the most intense pleasure swept through me, leaving me, once again leaving me quaking and shivering in its wake.

  When I’d finally come back down to earth, I adjusted my panties and skirt with trembling hands, then took a final look at myself in the mirror, making sure I didn’t look too disheveled. To my relief, apart from a soft rosy glow at my neck and collarbone, it was impossible to tell what naughty things I’d just been doing.

  As I unlocked the door and strode back out to my seat, the only other telltale sign was my totally soaked panties and pussy. I could feel my slick, wet swollen lips sliding together as I walked, but I found I didn’t mind the sensation – in fact, I liked it.

  I eased myself down into my seat, settling in, then shot a glance towards the counter, worrying for a moment that Jenna might have noticed I’d gone. To my relief, she was way too busy to notice, racing around, fumbling with the coffee machine, as a long line of angry customers developed.

  I smiled to myself, then lifted my coffee and took a long slow sip, glad that for once it wasn’t me behind the counter. And maybe the old woman was right; maybe this might finally teach her a lesson ...

  6

  While Jenna raced back and forth at the counter, serving coffee after coffee, I kicked back and relaxed, almost forgetting that I had a job to do. It felt so good just sitting here, enjoying my new body. I was so damn healthy; I could feel my lungs working better, my heart beating more powerfully, and even like this in a resting position, my limbs felt full of energy.

  Even the inside of my mouth tasted better! And as I moved my tongue around to explore each of my teeth in turn, they all felt perfect – no fillings or imperfections.

  I guess some people got all the luck, and Jenna had been born in what honestly seemed like a totally perfect body. I guess it was her mind that was the problem, and I just hoped that a little time behind the counter might give her a new appreciation for people like me who worked in the service industry.

  I was just finishing up my coffee when I caught sight of something through the window that made my stomach lurch. Because there, slowly walking past the store, was the old woman! It was definitely her – I recognized that distinctive purple woolen coat – and in a flash I’d pushed myself to my feet and headed out the door, my ladylike manner totally forgotten as I sprinted after her as fast as I could, calling out, “Excuse me! Excuse me!”

  Maybe she was deaf or maybe she was just distracted, but either way she just kept on walking. Luckily, with my lithe athletic body I’d soon caught up to her and I stopped her in her tracks.

  “You might not recognize me,” I began, still catching my breath a little, “and this might sound crazy, but I’m ...”

  “The boy from the coffee shop,” she replied with a knowing smile. “So? How are you finding your new body?”

  So it was true! It really was her candy that had caused us to swap!

  “I’m uh, I’m actually having fun,” I admitted, “but even so, how do we switch back?”

  “Easy,” she said, her smile widening. “You’ll switch once that bitch has learnt her lesson.”

  It felt strange to hear a kind old woman say a word like that, and I felt puzzled at what she meant exactly.

  “But how will I know when she has?” I asked, wanting more information.

  “You’ll know,” she said with a finality that left me knowing there was no point in asking any more questions.

  So we just had to wait it out? I had to admit, part of me didn’t really mind the idea of staying in this body a little while longer. But even so, what if she never learnt her lesson? What happened then? Did I just have to start a whole new life, as Jenna? I wouldn’t know where to start ...

  “If I was you,” the old woman added in a conspiratorial tone, “I’d have as much fun as you can.”

  She gave me a knowing wink, then turned and walked off down the sidewalk, leaving me standing there, totally puzzled.

  7

  “What do you mean she didn’t tell you how to swap back!” Jenna exclaimed, once her shift had finished and we were heading back to her apartment. “That’s insane. There must be a way to speed up the process. Tell me again exactly what she said to you.”

  “She just said,” I began, hoping I sounded convincing, “that we’ll both chance back in time ...”

  “That’s all she said?”

  “That’s all, I promise,” I replied, crossing my fingers behind my back.

  For some reason I couldn’t quite bring myself to tell her the whole truth – that she needed to learn her lesson and stop being a bitch first. And anyway, if I told her that, it might delay the switch even further, if she tried to fake it or whatever ...

  * * *

  “Oh my god,” she groaned, once we’d made it inside the apartment. I watched as she slowly pulled off her sneakers then flopped back onto the couch, obviously exhausted. “That was hell,” she sighe
d. “I don’t know how you do it every day.”

  “You get used to it, kinda,” I replied, wondering for a moment if a full eight hour shift at the coffee store had perhaps done the trick and made her a little less bitchy.

  But a second later, she added in a mean, entitled tone, “Fetch me a glass of white wine. It’s in the fridge.”

  Yes, boss, I thought sarcastically as I padded over to the huge open plan kitchen, chock full of gleaming, top of the range appliances that looked like they hardly even got used.

  I grabbed her a glass then pulled open the fridge, slipping out the bottle of chilled white wine and pouring it for her. I’d never been much of a drinker myself, and especially not wine, but there was something pretty enticing about it all of a sudden.

  “Hey, you mind if I have a glass too?” I called over.

  “I suppose,” I heard her mutter.

  So I poured out a second glass, then carried them back through to the living room, handing one to her before sitting down on the seat opposite. I’d still not got used to remaining ladylike at all times, and I noticed after a moment that I’d sat down with my legs wide open the way I used to, obviously giving her a flash of my silky smooth thighs and panties in the process.

  Sure enough, I caught Jenna glimpsing between my legs for a second before quickly staring at her cellphone, and if I wasn’t mistaken, there it was again: the obvious bulge of a boner, pressing out from the crotch of her pants.

  All of a sudden, a new thought crossed my mind. Would it be gay to fuck myself? I mean, if I was honest, I’d tried (and failed) a few times to suck my own dick. And surely Jenna would want to explore body from the outside, too? Wouldn’t the two of us getting it on be little more than mutual masturbation?

  And just like that, it was all I could think about. The perfect solution to my continued horniness! Now I just needed to find some way of finding out whether she was into the idea, too.

  I took a long, slow sip of the surprisingly delicious crisp white wine, hoping it might steady my nerves a little. I could feel my heart starting to pound with pure nerves as it dawned on me that even though we’d switched bodies, it would still be up to me to take control of the situation.

  If I wanted it to happen, I’d have to set it in motion. I’d have to make the first move.

  So I took another big gulp of the wine, then set it down on the glass coffee table, before pushing myself up to my feet. My movements caught her attention, and she glanced up again from the screen of her iPhone, at first confused as to what I was doing.

  I locked eyes with her, then slowly began to unbutton the blouse, all the while feeling my heart pounding and hoping my crazy, bold move wouldn’t cause her to freak out.

  “Uh, what are you doing?” she croaked unconvincingly, crossing her legs to try to hide the boner that was still pressing at her pants.

  “What does it look like?” I purred back, just as my fingers undid the last of the blouse’s buttons, letting the blouse fall open to reveal my perky little tits, framed so exquisitely by my bra, while beneath my skirt, I could feel my clit throbbing madly. “It’s not every day you get to experience life as the opposite sex,” I continued, my voice trembling a little from nervousness. “I’m sure you’ve wondered what it would feel like to have a dick – to fuck someone with a dick. And I’ve certainly wondered what it would feel like to be the one getting fucked. So come on, Jenna, why don’t we find out while we have the chance?”

  I gulped, unable to quite believe that I’d said all that out loud.

  And to my surprise, and relief, I watched her mouth curl into a grin ...

  8

  She pushed herself up from her seat, her boner now clear as day as she prowled towards me, then paused, as something flashed across her features.

  “Before we do this, we should set a few ground rules,” she said sternly.

  It was typical of her; even at a time like this, she still had to take charge, still had to make it serious.

  “Sure, sure,” I said, knowing I’d agree to anything, I was so desperate to get it on.

  “Number one, no kissing,” she began.

  “Okay,” I replied.

  “Number two, you don’t tell anyone that we did this.”

  “Of course,” I laughed. “I mean, who the hell would even believe us anyway?”

  “Good point,” she said, a half smile briefly flickering across her face. “And third, if either of us say stop, we have to stop. I’ve never, um, been with a girl before. I’m not sure I’m even going to like it ...”

  “Hey, this is my first time with a dude, too,” I replied, “and anyway, just remember, it’s us. As in, you’ll be sleeping with yourself. It’s basically just a kind of masturbation.”

  She nodded, obviously mulling over what I’d said, then turned and began to walk to the bedroom. I followed close behind, my heart starting to boom against my ribs as the realization dawned on me that soon, very soon, I was about to sleep with ... myself.

  * * *

  By the time I reached the bedroom, I saw that she was already undressing. I watched, transfixed, as the old me began peeling off his clothes, and actually, I had to admit that from where I was standing I didn’t look too bad! Again, I started to suspect that maybe my downbeat attitude had been affecting the way I perceived myself, because my shoulders actually looked pretty broad and while I wasn’t the most toned guy in the world, there was certainly a little definition on my torso and not too much fat around my stomach either. As the old me pushed off his pants and boxer shorts in one go, I saw that my dick actually looked kind of huge, too.

  I even began to wonder if it might hurt a little to take something so big inside me for my first time. But I reminded myself that this wasn’t Jenna’s body’s first time – she was obviously no virgin.

  I began to slip off my blouse, but all of a sudden, she said in a low tense voice, “Wait, stop. Let me do that. I want to undress you ...”

  To my surprise, I found I actually liked the way she was taking charge now, acting like the man, prowling towards me, her eyes burning with lust as she reached out and yanked the blouse from my arms way more roughly than I was expecting, before pushing me backwards onto the bed.

  I gasped in surprise, but a second later my gasp turned into a moan as I felt her roughly push my skirt around my waist then spread my legs apart, before pushing her face between them. I moaned again, as she began to nuzzle my aching clit through my panties, before tugging them to one side, exposing me there.

  I let out another low, shivery sigh as I felt her lips close around my clit, her tongue lapping it hungrily, circling it faster and faster, sending shockwaves of pleasure rocketing all around my slender body.

  As she worked her kisses further downwards, I felt myself spreading my legs wider, arching my hips, grinding myself into her mouth, as her hands grabbed my butt, lifting me right up off the bed as she worked my aching pussy so expertly with her tongue.

  I could feel the first flashes of an orgasm rising up inside me already, but just as I was on the brink, she pulled her mouth away, the gleeful, teasing sparkle in her eye telling me she’d stopped on purpose, leaving me gasping and begging for more.

  Slowly and confidently she got to her feet, before offering her hard cock to me.

  I pushed myself up to a seated position, so that my face was only a few inches away from it, the heat of it radiating in waves. Sure, I’d seen it thousands of times before, but never like this. It actually looked pretty good, thick and hard, with a bulbous pink head and big round balls and I felt my clit throbbing in anticipation at the thought of taking it in my mouth.

  I reached out and curled my fingers around the smooth, throbbing shaft, registering just how fucking hard it was – I only got like that when I was super turned on. And as I began to stroke it, I cupped the balls with my other hand, too, playing with them a little before leaning in and letting my outstretched tongue glide slowly and sensuously up the shaft.

  When I took th
e head deep into my mouth, I felt Jenna tense up, and she let out a groan as I began to suck on her, all the while working my hand up and down her shaft and kneading her balls, first softly and slowly, but quickly increasing in intensity, just like she’d done to me.

  I heard her breathing become shallow and as she her cock swelled in my mouth, I wondered for a moment if she was gonna cum; a part of me even wanting her to. But all of a sudden she pulled away, then pushed me back before climbing onto the bed next to me, so that our bodies were pressed together. As I threw my leg over hers, I could feel her cock right there against the entrance to my pussy, throbbing against my lips, and it would be so easy to just reach between my legs and guide it inside. I wanted to so fucking badly, but at the same time, I wondered if maybe we should be using protection, and I felt frustrated with myself that I hadn’t bought anything in advance.

  Luckily, Jenna must have been having exactly the same thoughts. I watched with relief as she pulled away from me for a moment, leaning over towards the bedside table, pulling open one of the drawers and grabbing a package of condoms.

  My heart was pounding as I waited on my back while she fit the condom over her cock, then turned and climbed above me, her hands taking my breasts for a moment as she leant in and began sucking my nipples, leaving me squirming and writhing beneath her. Back as a guy, my nipples hadn’t been at all sensitive, but now it was crazy how much pleasure I seemed to get from them. Hell, I almost felt like I could cum just from Jenna sucking on them like this if she did it for long enough.

  But again she pulled her mouth away, leaving me gasping and frustrated, then locked eyes with me as she reached down and began guiding her meaty cock between my legs. I let out an involuntary moan as the head pushed inside and a brand new sensation flashed through me: somewhere between pleasure and pain, the thickness of her dick stretching me wider and wider as she guided even more of herself inside me, until I cried out again.