First Time Femme

by D. L. Savage

  “Maybe,” she admitted, tilting her head and staring at me with a furrowed brow, as if trying to picture what I’d look like as a girl. “You’re definitely skinny enough,” she admitted thoughtfully. “And you do have good bone structure. It’s going to take a hell of a lot of work but yeah, I think I could maybe pull it off.”

  “So you’ll do it?” I asked excitedly.

  “Ah, fuck it, why not?” she shrugged. “It’ll be like old times!”

  4

  The next day I woke full of energy, and for the first time in what felt like forever I actually made it out of bed while it was still technically classed as morning. The reason for my sudden enthusiasm was that my big sister Sophia had agreed to come around after her shift in the vintage store in order to give me a full makeover, and I had a whole shit ton of stuff to get ready before her arrival.

  Number one was a full spring clean of the apartment, which I just couldn’t let her see in its current state. So I began racing around like a headless chicken, stuffing all manner of junk into black trash bags and then carrying it all outside (along with Rosco’s full litter tray), before setting to work scrubbing the floors and surfaces until they were gleaming. I even went as far as to change my sheets, knowing that it had been months since I’d last done so and they were probably the reason for the weird musty smell in my bedroom.

  Then, once the apartment had been fully scrubbed and polished, I knew it was time for the task that I’d been putting off.

  You see, while Sophia had agreed to help me with my makeover (even promising to bring over a whole bunch of clothes and whatnot for me to try on) she’d also made me promise to ‘get ready’ in advance of her arrival.

  And what she meant by that was shaving my goddamn body from head to toe.

  I hated shaving my face at the best of times, and over the last couple years, I’d avoided it as much as I could, preferring to simply buzz back my stubble every few weeks rather than going for a full clean shave. But I knew that today called for way more drastic measures.

  With a sigh of resignation and a shake of the head, I trudged into the bathroom and began to get undressed, glancing at my scrawny body with distain as I slowly revealed it in the small bathroom mirror. I’d always been skinny as a rake, ever since I was a little kid. Back when I’d first hit puberty, I’d assumed that eventually I’d fill out, but for some reason that never happened. I just hoped that after my makeover my slim physique might actually work to my advantage for once in my life.

  As I pushed my boxer shorts down around my ankles, I caught a quick glimpse of my dick too, which was so fucking tiny it was pathetic – two inches soft and maybe four or five when fully hard. And for some reason I found myself wondering what it might feel like to have a big flopping monster cock like Pete Anderson’s and whether it might boost my self-esteem any. Because all my life, I’d felt shy and unconfident, and I wondered if maybe deep down that was the reason why.

  I tried to shrug off the gloomy thoughts, reminding myself that if I could pull off this crazy stunt then I was set to make ten grand – enough cash to finally give me the time and breathing space I needed to get out of the paparazzi game once and for all …

  One night, I told myself. One night of humiliation and then a whole new future awaited me.

  Spurred on, I grabbed a hold of my electric razor and set going, buzzing it slowly up my shin, leaving smooth pale skin in its wake ...

  * * *

  Just after seven, I heard the sound I’d been anticipating: the buzzer to my apartment. And as I leapt to my feet and raced to the intercom, I felt super nervous but also glad to be finally getting this crazy show on the road.

  As I moved I could feel the strange sensation my jeans swishing against my baby-smooth legs, but what was even stranger was that I kinda liked it.

  “Hey, Soph, c’mon up,” I said into the intercom, pressing the button that allowed her inside the apartment block, before turning and giving the living room a final quick glance, actually impressed by my cleaning abilities.

  “Wow, Cody, is that you?” she said in amazement when she finally showed up at my door, her face breaking into a grin as she set eyes on me. “No offense, but now that you don’t have a beard you look about twelve,” she added, as I felt my face flushing with embarrassed heat.

  Instead of shooting an insult straight back, I forced myself to bite my lip, reminding myself that she was doing me a huge favor. She was dressed as usual in skinny jeans and a plain black top, her hair tied in a tight ponytail, but I knew that during her teenage years and early twenties especially she could really glam it up at times. I could remember all those arguments with our mom about Sophia going out in a super short skirt or whatever. And as I noticed the bags she was carrying - I just hoped it contained all the stuff necessary to transform me into a hot chick.

  “I still can’t believe we’re doing this,” she chuckled, shaking her head as she made her way inside and dumped the bags on the floor.

  “Me either,” I replied, curious if my idea would even work or whether I’d just look totally hideous. But I figured there was only one way to find out.

  “Oh, hey, look what I found!” Sophia added, excitedly pulling open one of the bags then reaching inside to remove a long glossy brown wig that glimmered and shone as she brought it out of the bag and into the light.

  “Holy shit,” I gasped. “Where the hell did you get that?”

  “I sent out a few texts and one of the girls at work had it laying around spare,” she grinned back. “And before you ask, don’t worry, I didn’t say it was for my freaky crossdressing brother or anything …”

  “Thanks,” I replied, glad that my secret was safe. “And just for the record,” I added, “this is strictly professional, alright? I’m not getting off on this in any way whatsoever.”

  “Yeah right,” Sophia replied with a knowing smile, arching an eyebrow. “You used to love getting makeovers when you were little.”

  “I used to love the candy bars you gave me,” I insisted, shaking my head at her crazy insinuations.

  But as I again felt that strangely enjoyable swish of my pant leg against my freshly shaved skin, I had to wonder if maybe, just maybe I would enjoy this experience after all …

  5

  “So how d’you feel?” Sophia asked, a couple hours later, after what felt like the mother of all makeovers.

  I tried to think about it, but it was impossible to put it all into words. Because every single part of me felt different, right from the ground up:

  My feet were now crammed into a pair of shiny black heels that Sophia had raided from work, while my legs were now encased in silky black stockings too - complete with lacy, elasticated tops that hugged the tops of my thighs so damn tightly it was crazy.

  My cock was tucked tight between my legs, held firmly in place by a nude g-string that Sophia insisted I wore (telling me in no uncertain terms that a hot chick would rather die than be seen with panty-lines) and which I could feel riding tightly between my ass cheeks like the mother of all wedgies. My pecs were hugged just as tightly by one of Sophia’s bras which she’d bundled me roughly into, instructing me to hold my breath as she clipped it in place, before stuffing with a pair of my socks to give the illusion of two small but pert breasts.

  Next had been the dress: a black ‘bodycon’ number, which hugged my figure like a second skin, its silky fabric so damn flimsy that it felt almost invisible.

  Last (but by no means least) had been the makeup and wig. I still couldn’t quite get my head around what a difference they made – the illusion scarily realistic. Because as I stared back at my cartoonishly large eyes, my pink glossy lips and my flawless porcelain skin, all framed by the most luxuriously silky brown hair, I couldn’t help but grin and shake my head, my mind totally blown by the results of all Sophia’s hard work.

  “I feel ... different,” I replied eventually, knowing that no word in the English language could truly sum up the crazy transformation I’d
just undergone.

  “Well you look hot,” she grinned, coming up behind me and throwing her hands around my shoulders. “Seriously Cody,” she added, “if I were you, I’d seriously think about transitioning. You make a way better chick than you ever did a guy!”

  “Thanks ... I think,” I laughed back. “But really, thank you so much for everything, Soph,” I added genuinely. “I really do appreciate it.”

  “Hey, what are sister’s for?” she chuckled. “You sure you don’t want some moral support this evening?” she added.

  “Nah, I’m good,” I replied.

  After a final hug goodbye, I showed her out of the apartment. I felt a little bad that I’d lied about what I’d be doing next. But seriously, could I tell my sister that I was about to take out my phone and catfish some dude in the hope of getting a dick pick?!

  And as the door closed behind her, I felt this strange tingling excitement startling to burble up inside me, as I realized that I was eager to go back and take another look at myself in the mirror - this time alone. As I headed back through the apartment to my bedroom, I found myself savoring the feel of the silky wig dancing against my bare shoulders, and the tightness of the stockings hugging my thighs, the subtle weight of the bra tugging at my chest, not to mention the strangely pleasurable sensation of the g-string teasing my butthole and holding my cock and balls so damn tightly in place.

  My body was trembling all over with a weird excitement as I finally arrived in my room and made a beeline for the mirror, letting out a gasp of pure excitement as I once again set eyes on myself, the reflection confirming all over again just how fucking good I looked. It was truly crazy. Sophia had done a way better job than I could ever have imagined, and I found myself posing and pouting, moving my body this way and that, almost outside of my own control, unable to believe that the sexy little minx in the mirror was really me.

  It seriously felt like I’d been transported out of my own body and into a brand new girly physique, and for the very first time it was like my skinny body made sense.

  Before I could change my mind I snatched up my cellphone and set it to camera mode, knowing it was finally time to put my crazy plan into action. Then I turned away from the mirror, looking back over my shoulder as I inched up my dress just enough to expose a flash of my bare buttocks, before hitting the button.

  FLASH!

  I stared in wide-eyed excitement at the screen unable to believe how realistic the shot looked – my ass looked no different to a real girl’s and spurred on, I began to take even more, first pulling my dress up further, fully exposing the smooth roundness of my bare butt …

  FLASH!

  Then turning and holding the camera in front of me, pressing my elbows together so that the bumps of my breasts, my skinny shoulders and neck, and my big juicy lips were all in shot …

  FLASH!

  … capturing the image forever, unable to believe that it was really me there on the screen.

  There was no use in denying it: I was turned on, so much so that I could actually feel my cock throbbing in my panties, and as I let my fingers explore between my legs, I discovered that the tightness of the thong had held everything in place, creating nothing more visible than a subtle throbbing mound in my panties, hardly different to what you might get if a girl had an untrimmed bush or puffy pussy lips. For the first time in my life, I actually felt glad that I’d been born with such a small dick.

  I lowered myself down on the edge of the bed, crossing my long legs, my body trembling with horny excitement as I began to scroll back through the pics, trying to decide on one to send to Pete Anderson, in the end choosing to play it safe with the first shot I’d taken – the one from behind, of my long legs and just a hint of ass.

  I can’t believe I’m actually doing this, I thought, sucking in a final shaky breath and then hitting Send.

  It was only after the whooshing sound effect rushed out of the cellphone’s speaker that I began to consider the possibilities. What if he didn’t respond? What if the number I’d been given wasn’t even for him? Or worse, what if my intuition was totally out of whack and he could tell somehow immediately that I wasn’t actually a chick?

  As the gloomy thoughts came crowding in I pushed myself back to my feet as I began to pace up and down the room, worrying that I’d made a huge mistake.

  But just as my panic reached a crescendo I heard the familiar chime that signaled a new message received, and I raced back over and snatched my iPhone from where it lay on the sheets to see that sure enough, I had a reply:

  Very nice. Who is this?

  I felt my stomach lurch, a naughty grin starting to tug at the corners of my mouth as I typed my reply:

  Just an admirer. Thought maybe we could trade some pics? ;)

  I hit send and this time I immediately saw the set of dots that indicated he was typing a reply. A second later it flashed up on the screen:

  Show me some more of you first baby

  I rolled my eyes, figuring that wasn’t really fair, but knowing I couldn’t exactly argue too much. He was practically a celebrity after all, and I knew I’d need to hook him in if I was going to get what I was after.

  So after a little more deliberating, I sent another of the shots I’d taken – this time the one from the front that included my mouth, neck and shoulders, not to mention a cascade of silky brown hair (which I knew he liked).

  This time, there wasn’t even a delay before his next message popped up onto the screen: Damn girl. Now I need to know what’s under that dress.

  No fair, I typed back, unable to resist flirting with him, finding myself weirdly enjoying the conversation as strange as that might sound. It’s your turn, I added before once again hitting send.

  This time there was a pause, maybe a minute or so, during which I began to wonder if I’d pushed things too far and scared him away. But I felt my stomach lurch as a picture message flashed onto the screen: of his ripped torso. It looked like he was standing in some kind of expensive hotel suite and he was pulling up his t-shirt to expose a perfect six-pack beneath.

  I had to admit, he was in pretty awesome shape. But it was a rather different part of his anatomy that I wanted to see.

  Not bad, I found myself typing, but I was hoping for something a little … naughtier?

  I couldn’t believe how easy these messages came, almost like there was some naughty kinky girl inside, taking me over.

  If THATS what you wanna see baby, he replied in a flash, it will have to be IRL.

  I felt my heart start to thud as the realization dawned on me of exactly what he was asking. But before I could even reply another message quickly followed: I’ll be at the Panama until 1. Room 318.

  I stared at the screen in total shock, a cold sweat prickling out across my skin, wondering if I could really do that …

  6

  My heart felt lodged in my throat as I stepped out of the taxi and into the cool night air, staring up at the frontage to the Panama; all chrome and glass, with a set of elegant steps leading up to the dimly lit lobby within.

  I’d hung out here so many times with the other paparazzi, waiting for some celeb or other to emerge so we could jockey for the best shot. But never in a million years would I have imagined myself strolling inside, and definitely not dressed like this.

  I felt my heart starting to boom as I made my way up the steps and into the lobby, keeping my head held high and my back straight, taking small dainty steps so that I didn’t totter on my heels. There was a guy working the reception desk - handsome, dark skinned, his big black eyes burning with hunger as he stared back at me, openly checking me out, a leery smile flickering on his full lips.

  Never in my life had I felt so on display before, as I strode past him in my tiny little figure-hugging dress that left practically nothing to the imagination. But from the look on his face, I felt my confidence soar as it dawned on me that he thought I was actually a chick.

  I even threw in a little smile and a flutter
of my false eyelashes for good measure, feeling his hungry eyes watching me as I made my way toward the elevator in the corner. I punched the button and waited what felt like forever, breathing a long sigh of relief as it finally arrived and I stepped inside.

  And as I reached out and hit the button for floor three, I felt my head starting to spin and my heart flushing with nervous excitement, like I’d just been locked into a rollercoaster that had begun cranking its way along the start of the track, before the first big drop …

  You can do this, I told myself as the doors swished open again and I made my way along the silent corridor, finally pausing and knocking on the door to room 318.

  You can do this ...

  Just then the door to the suite opened, and when I first caught sight of Pete Anderson, dressed in a plain white tee and black jeans, I felt so knocked back I almost couldn’t breathe. He looked just like he did in the magazines - perhaps even more handsome in real life. And his sheer size and rugged good looks made me feel even more girly than ever. I felt shocked most of all by his easy confidence; it seemed to radiate off him, oozing out of his pores. And unlike the other day, when he’d threatened to kick my ass, now he was all charm, all smiles.

  “Let me guess,” he murmured, his blue eyes piercing right into me, “you’re my anonymous admirer.”

  I swallowed back my nerves, forcing a smile onto my face as I nodded, gazing back up at him with what I hoped was a cute girly expression on my face. “I might be,” I replied in what I hoped was a soft, feminine voice.

  “In that case, why don’t you come on in for a drink?” he grinned back, standing aside to let me pass.

  As I headed into the sumptuous suite of rooms, I could feel my wig dancing against my shoulders and the tight hem of my mini dress threatening to ride up around my butt at any moment, the sheer tightness of it the only thing that seemed to keep it in place, hugging the tops of my thighs.