Dressed for Pleasure

by D. L. Savage

  And then finally, she appeared again and said, “Alex? We’re ready for you. Just this way ...”

  I felt my stomach lurch with fresh nerves. It occurred to me as I followed her down the corridor towards another doorway that I’d never really had a job interview before; the only other place I’d worked, a part time gig at the small hardware store in my town, had been arranged through a friend of my mom’s. And I found myself wondering if there was something I was supposed to do or say, some way I was supposed to act. I figured the best thing to do was just to smile and nod and seem eager, no matter what the hell this place turned out to be.

  As we entered the room, which was bigger and looked a little like an office, I saw that there was another woman sat at a desk. She seemed older than the brunette, and she had long, straight brown hair that framed her striking features. She had a large eyes, plump lips and striking cheekbones, and as the first woman took the seat next to her, I felt my pulse quicken as I realized this interview was to be conducted by two totally hot milfs.

  “Please,” the woman in charge said, gesturing to the empty seat that faced the table. There was some kind of subtle European hint to her accent, and I found myself wanting to hear more of her elegant, low, musical voice.

  I did as I was told, slipping into the seat and making sure to keep my back straight and my shoulders back, wanting to make a good first impression.

  “So ...” the woman said, while the pretty brunette watched on, smiling, “Alex. Have you ever done this kind of work before?”

  I felt my stomach flip. Was this the moment I was supposed to say that I still had no clue what the work even was? But instead, I found myself shaking my head.

  “That’s probably for the best,” the woman murmured, more to herself than to me. Then she pinned me with her big dark eyes, adding, “I’m very particular about my girls.”

  What does that have to do with me? I thought. Unless ... Wait ... She doesn’t think I’m a girl, does she?!

  “Our hostesses are the best in the city,” she continued, as I felt a cold prickle of embarrassment creep out across my skin, “and if you’re to work here, I’ll expect a lot from you.”

  I felt numb with shock and confusion. Did I really look that much like a chick? Sure, I’d tied my hair back with Ellie’s scrunchie, and sure I wasn’t the most macho looking of guys. I was still waiting for the light blonde fuzz on my face to turn into stubble and I was definitely on the skinny side. But even so, was I really that feminine?!

  “Stand up,” the woman announced, in a voice so cold and harsh that it took me by surprise for a moment. I knew I should say something, should explain that there’d been a mistake, but at the same time, I felt kinda scared of her, and I didn’t want to anger her by telling her I’d wasted her time.

  So I pushed myself to my feet.

  “Turn around,” she said.

  Again I did as she commanded, doing a slow twirl, while I heard the woman murmuring to the brunette.

  “She’s certainly pretty, and we haven’t got any trans girls working here yet, but she’s not exactly curvy ...”

  Trans?! At least that made a tiny bit more sense ...

  “Oh Lydia,” I heard the brunette laugh, “that’s nothing a little padding can’t fix.”

  When I’d turned back to face them, the woman said matter of factly, “Is everything still working downstairs?” And as if there was any question left as to what she was referring to, she gave a nod towards my crotch.

  Still shocked into silence, all I could do was nod.

  “Good,” she smiled, her icy demeanor melting just a smidgeon. “Well, the job’s yours if you want it, Alex.”

  By now my heart was beating so hard it felt like it might burst right out of my chest and I was working up the courage to finally say no, that the whole thing had been a mistake, when she added, “How does five hundred dollars a night sound, and we’ll review your pay after a month?”

  Five hundred a night?!

  I felt my brain reeling, trying to process all the information at once. It seemed that this really was some kind of sex club, and this crazy woman thought I was a pre-op trans girl, and she was offering me five hundred dollars a night to work as a ‘hostess’ ... whatever the fuck that was …

  I knew it was totally crazy to say yes, but this whole thing just seemed like fate – the club being right on my doorstep, the interview happening just as I’d stepped outside – and a part of me knew that if I didn’t at least give it a shot, if only for one night, then I’d regret it forever.

  So I took a deep breath, then forced a smile onto my face and said, “That sounds great.”

  “Fantastic,” she replied. “Can you start tonight?”

  “Uh, sure,” I blurted out, my body coursing with adrenaline.

  “Very good,” she smiled. “Raquel will show you out. I’ll see you tonight, Alex. And maybe from now on, we’ll call you Alexa, yes?”

  I just nodded, dumbstruck, before following the brunette out of the room.

  “Don’t worry about Lydia,” Raquel said in a whisper, once we were back in the corridor. “She’s a lot of fun, really. I think she just likes to try and scare the new girls.”

  As she led me back towards the exit, she carried on talking. “You’ll get a full briefing tonight, but until then, the only things you need to remember are: wear something tight and black, and make sure to glam up a little? Oh and it might be a good idea to pad your bra, too?” she added with a grin.

  By now we’d reached the doorway, and my head was still spinning with all this new information.

  “And don’t look so scared!” she laughed. “I’m sure you’ll do great. Honestly, it’s a lot of fun. I’ll see you back here at nine tonight.”

  Then she pushed open the door and I gave her a final shy smile before stepping out onto the bright sunny sidewalk, once more just a few feet from my apartment. As the door closed behind me with a slam, I wondered what the hell I’d gotten myself into ...

  4

  I returned home a little dazed and wondering what the fuck I was going to do. Now that I was no longer in the thrall of those strange, glamorous women and instead standing in the shabby hallway of my student apartment, the idea seemed totally absurd.

  Could I really go through with something like that? And how the hell would I even get hold of the clothes and makeup, anyway? Sure, it was a lot of money – and I could definitely use five hundred dollars. But still, the idea of going downtown and buying myself a dress and makeup filled me with paralyzing embarrassment, and there was no way I could order anything online in time for tonight.

  With a frustrated sigh, I reached behind my head to release my ponytail, wondering if perhaps I should have just gone into the city like I’d planned, got a haircut and looked for real work, instead of wandering inside that weird building on a whim. But as my fingers enclosed around the soft fabric of the scrunchie, a new idea flashed through my head.

  Of course!

  I already had everything I needed, right here in this apartment ...

  * * *

  As I made my way into Ellie’s room for a second time that morning, I told myself that she’d understand. She was such a supportive friend, I knew that if I’d told her my situation and asked her for help, she’d probably even help me get ready – teaching me about makeup techniques and whatnot. But I also knew that she was currently on a nine hour flight to Europe, so wouldn’t be contactable until tomorrow at the earliest.

  Instead, my plan was to just borrow everything I needed – for one night only – and then take it from there. If it turned out I enjoyed this job, I could buy my own stuff before my next shift, even fess up to Ellie when she got home about borrowing her makeup and clothes.

  That said, I still felt kinda creepy as I surveyed her room, knowing that this time I was going to have to do some real exploring.

  I tried to remember what the friendlier woman, Raquel, had told me. Wear something tight and black ... Glam up a little ...
And pad your bra ...

  I felt my stomach lurch again in nervous dread. This idea was so fucking insane. Was I about to make a total fool out of myself? But then again, those women had seemed to think I had what it took – they’d believed I was a real trans girl, not just some dude with long hair and a slight lack of testosterone, and I knew that I should at least try and make myself over and see how I looked, before I made my final decision about whether to go back to the club tonight.

  I figured the best place to start was the large wooden wardrobe on the far wall, where I assumed Ellie kept all her dresses. Normally, Ellie was more of a leggings-and-sweater kind of girl, but I suspected she had a few glamorous items tucked away somewhere, too. So I padded nervously over then pulled open the door, staring in at a row of colorful coats and dresses, all hanging together, most of them things I’d never seen her wearing before.

  I began to gently work my way through the items one by one, from left to right, assessing each in turn. There were a couple of dresses that were certainly tight looking, but they weren’t in black – one was a cream color and the other was bright white. But towards the end of the rack, my fingers grazed across a wisp of silky, glossy black fabric and I felt my pulse quicken a little.

  I eagerly pulled it out of the closet, holding it up on its hanger to examine it, and sure enough, it totally fit the description: a slinky black dress that I knew would be tight on me – especially as my body was a touch larger than Ellie’s. That said, we were actually a pretty similar size. The only differences that I could think of were that perhaps my shoulders were a tad broader, and I was a few inches taller. And my feet of course.

  I carried the dress carefully over to her bed and laid it on top of the covers, staring at it for a moment as I wondered for the first time what it might feel like to wear something like that: to feel that silky, glossy fabric against my bare skin. I guess I’d soon find out!

  It was so weird; I’d never really had any kind of interest in girls’ clothing before, but there in Ellie’s room, as I began to pick out my outfit, I had to admit that I was kind of enjoying myself, and I felt a thrill of anticipation building inside me.

  Now that I had my dress chosen, I knew that I’d need some underwear, too. This was the part I was both dreading and looking forward to in equal measure. After all, Ellie was super hot, and the idea of taking a peek in her panty drawer – hell, of actually wearing a pair of her panties – got me pretty damn excited despite myself. At the same time, I hated the idea of turning into some stereotypical creepy housemate. I reminded myself all over again that I had no other choice at such short notice, and if Ellie were here, she’d totally help me out and let me borrow her stuff.

  So I headed over to the set of drawers next to her dresser, kneeling down and pulling open the bottom one first. It was full of a jumble of what looked like pantyhose, stockings, socks and other bits and pieces, too – headbands, scrunchies and so forth.

  I began rooting around, not really sure what I was looking for exactly, but wondering if there might be some item or two that I could add to my outfit. The first thing I found was a small lace choker, with a little jeweled bead on the front. Immediately I knew that it would look awesome – giving me some much needed ‘glam’ and also maybe covering up the soft bump of my Adam’s apple, so I set it aside on the carpet then continued rooting, a moment later coming across a black silky stocking with a matching lacy top. It had some kind of rubbery material around the inside of the top part, which I guessed was to allow it to stay in place without a suspender belt, and I began searching for the matching stocking, eventually finding it right at the back of the drawer.

  I slid the bottom drawer closed, then pulled open the middle one, which contained a stack of neatly folded t-shirts, as well as a selection of bras. I figured I’d best stick to an all-black color scheme, so that narrowed my choices to just three options – one was plain black and had straps, one was similar but with no straps, and one was more of a lacy design – and I pulled them all out and set them aside, figuring one might fit better than the others.

  Again I slid the drawer closed, then turned my attention to the final drawer, which I guessed must contain Ellie’s panties. I felt a subtle charge of excitement as I reached out and slid it open, sure enough revealing a whole bunch of underwear in a variety of different colors.

  As I said before, Ellie often wore leggings, so I guess I shouldn’t have been too shocked when it turned out that the majority of her underwear were thongs and g-strings – after all, I knew that girls often wore that kind to hide panty lines on tight fitting clothing – but even so, I felt another horny thrill at the idea that my cute housemate had been wearing these sexy, skimpy things beneath her clothing when we’d been hanging out together.

  And I felt my thrill increasing at the thought that soon I’d be wearing them, too. As I rooted through the scraps of fabric, picking out a few in black and setting them aside with the bras, I found myself marveling at just how different they were to the kinds of boring, baggy boxer shorts I normally wore. They all seemed to be made of soft stretchy fabric, and I wondered what it would feel like to have something like that against my skin.

  Once I’d picked out a few pairs: a simple plain black thong, another in a black lace design, and teeny little black g-string, I knew I was ready to start dressing.

  By now, my heart was actually pounding with excitement and I felt a little taken aback by how much I was anticipating this experience. I could feel my cock tingling and swelling a little at the thought of getting dressed up, and it was like I was unlocking some private part of myself that I didn’t even know existed.

  But as I began to hurriedly get undressed, fumbling open my skinny jeans and pushing them down over my thighs, I caught sight of something that made me pause, defeated. Because unlike my face, which wasn’t hairy at all, my legs were covered with a dusky brown fuzz of hair, which I knew I’d need to shave off if I was going to look even slightly convincing.

  So with a frustrated sigh, I had to abandon my current plan, as I turned and headed back to the bathroom for my second shower of the day ...

  5

  In the bathroom, I found myself using yet more of Ellie’s girly products. After all, her delicate pink razor looked a lot more forgiving than my crappy, cheap model – especially if I was going to try to shave my junk too. I figured it was probably best if I went completely hairless, everywhere. I knew that’s what a lot of girls my age did, and even if I wasn’t going to actually get totally naked (I hoped not!), I still wanted to make sure I had a good bikini line, or whatever it was called, just in case.

  Also, I still felt excited about seeing myself all dressed up in lingerie, and I wanted to be totally smooth and hairless to look my very best.

  Under the hot steam of the shower, I really took my time, shaving first my shins, then my thighs, then between my legs, carefully dragging the razor across my balls, taking care of all the nooks and crannies, even making sure to shave off the peach fuzz on my ass, too, as well as the tiny crop on my chest and armpits.

  I figured I’d buy Ellie a brand new razor once I got paid, as well as anything else of hers that I used and couldn’t put back – after all, I’d have plenty of spare cash if this job really paid as well as it was supposed to!

  But despite my excitement, there was another thought nagging at me: what exactly was a hostess expected to do? The job title seemed so vague, perhaps purposefully so, and the sighs and moans that I’d heard from the club last night got my stomach fluttering with apprehension.

  After all, I was pretty inexperienced when it came to sex. Sure, I’d had a couple of fumbled, drunken one-night stands in my first year of college, and I’d made out with a few chicks. But I’d never done anything sober, and without drink to steady my nerves, I was a total awkward mess.

  But I pushed the reservations to the back of my mind, spurred on mainly by excitement at the idea of dressing up in Ellie’s sexy clothes. I couldn’t wait to check mysel
f out in her large dress mirror, and I shut off the shower and quickly patted myself dry with a fresh towel, amazed at how different my skinny pale body looked, even just from shaving.

  Because apart from the obvious couple of differences (namely my dick and lack of breasts), I had to admit, the rest of me already looked pretty girly ...

  * * *

  It was finally time. Time to get dressed! I was back in Ellie’s bedroom, staring with nervous anticipation at the outfit I’d laid out on her bed. I had a roll of toilet paper ready to use for padding in my bra, and my whole body felt like it was tingling with a growing excitement, as I let the towel slip to the floor, then reached out for the first item of clothing: the black panties.

  They were so damn small and skimpy, and I gingerly stepped into them then tugged them slowly up over my thighs and around my waist, the stretchy fabric at the front cupping my swelling cock, creating a large round bulge between my legs, while the strap part at the back slid snugly between my buttocks, gently resting against my asshole.

  That certainly feels ... different, I thought. It wasn’t unpleasant exactly, but it was kinda distracting to have something right up in your crack like that, and I couldn’t help but think back on all those times when cute, playful Ellie had been hanging out with us in her tight figure hugging leggings – my cock growing even harder at the thought that she had been feeling this sensation the whole time!

  For a moment, I worried that my swelling boner would break free of the panties altogether, but to my surprise and relief, the snug stretchy fabric kept it firmly in place, holding my throbbing junk tight to my body in a big smooth bulge.

  I wanted to go take a look at myself in the mirror, but I figured I’d wait until I had the bra and stockings on too, so I selected the matching plain black bra – the one without straps, and at first just tried clipping it in place, fumbling awkwardly behind my back for a while with no real luck. But then I had a brainwave – instead putting it on like a belt first, before shuffling it into place.