First Time Femme Read online

  And while she was obviously trying her hardest to remain professional, I could tell from the occasional little smirk that she was enjoying this fucked up game almost as much as Tawna.

  In fact, it seemed as if the two women had had some kind of unspoken agreement right from the moment we’d first walked into the salon and Clara had said, “Ah, this must be the new client you were telling me about,” an impish look dancing in her blue eyes as they’d both laughed and nodded.

  I let out a loud involuntary wail, tears pricking my eyes, another jolt of red-hot pain flashing around my puny body as Clara tore away the strip of muslin from my taint.

  “Don't worry, sweetie,” Tawna teased back as Clara began to work yet more warm gooey wax deep between my ass cheeks and right into my butthole, “you're going to look so pretty when we’re finished with you. Then it'll be time for your twelve o’ clock at the hair salon …”

  “My what?” I gasped, eyes widening.

  After all, despite all the shit that I got for it, my top knot was my pride and joy. But before I could even start to articulate all that to Tawna, I felt my mind flash blank with another jolt of white hot pain as Clara tore another strip of fabric from my tender, burning ass ...

  4

  “I have a lunch reservation for two, for Tawna Andrews?”

  As the waiter checked the reservation book, I shuffled my weight awkwardly from foot to foot. From Tawna’s high-flying executive lifestyle, I guess it should have been no real surprise to me that she felt just as at home in swanky restaurants like this as she did in the scruffy dive bar where we’d met, but even so, I couldn’t help but feel a little out of place.

  “Ah yes, Miss Andrews, we have your table waiting,” the waiter said, looking up from the book with a polite smile before beckoning us out of the lobby and into the main room of the restaurant, which was huge and high ceilinged, with a black and white marble floor and black and white photos on the wall of old time film stars, staring down at us.

  As we wove through the tables, I felt weirder than ever, in part because it seemed like everybody except me had been given a secret dress code. On top of that, my body was still tingling from the waxing, my scruffy clothes now brushing strangely against my baby-smooth skin, while the panties continued to floss my now-silky-smooth butthole. But sitting like a cherry on the top of all that was the fact that I felt super self-conscious about my new hairstyle, too.

  You see, we’d come here fresh from Tanwa’s favorite hair salon, where she’d coaxed me into a chair and thrust a glass of bubbling ice-cold champagne into my clammy palm, before convincing the stylist to untie my topknot and coax my chin-length chestnut brown hair down over my face while the two discussed my options like I wasn’t even there.

  I just sat awkwardly in the chair, sipping champagne and listening in as Tawna and the stylist eventually settled on what could only be described as a ‘pixie cut’.

  And byt the time they’d finished with me, I looked androgynous at best. Sure enough, as we weaved through the crowded restaurant, I caught a few of the other diners glancing up us, my face reddening as they no doubt thought that I was some kind of gender fluid ‘they/their’, or perhaps even partway through a full male-to-female transition.

  “Looking good,” Tawna remarked as I eased myself into the seat opposite her.

  “Shut up,” I murmured, feeling my face flush even redder.

  “Seriously,” she insisted, nodding emphatically. “That haircut really suits you. It brings out your eyes and frames your face just perfectly ...”

  Deep down I knew she was just fucking with me, and I found myself sinking even deeper into my chair, wishing all over again that I'd never opened my big mouth in the first place. At least once her stupid game was over I still had enough hair left to tie in a top knot, I consoled myself. And my body hair would grow out in a few weeks.

  Yep, I just had to make it through today and everything could go back to normal ...

  Just then the waiter handed us two heavy, leather-bound menus, and as I flipped mine open, my gaze immediately latched onto the Kobe beef cheeseburger, my stomach letting out an embarrassingly loud gurgle.

  “Would you like a few minutes to decide?” the waiter asked politely.

  But Tawna shook her head, confidently announcing, “A superfood salad and a glass of house white ... Oh and she’ll take the same,” she added, nodding in my direction.

  I watched the waiter’s eyes widen as Tawna called me ‘she’, but he was obviously well-trained in such situations, regaining his composure in lightening fast time, saying, “Very good, madam, I'll be back shortly with your drinks, ladies,” before scuttling off across the busy restaurant.

  “What?” Tawna asked innocently as I shot daggers at her across the table.

  And I was about to tell her that she’d really gone too far when the expensive rose gold iPhone that she’d laid out in front of her on the table let out a loud chime. She snatched it up, tapping at its screen with her glossy fingernails, then let out a loud sigh of annoyance.

  “Ugh, this guy keeps on messaging me,” she explained, “and I don’t know what to do. Julio. I met him on Bumble and he’s super cute but we have like nothing in common. He hardly even speaks English. What d’you think? Should I bother seeing him again?”

  As she spoke, she slid the phone across the table towards me and as I stared down at his photo I felt my spirits sink. I guess I’d known on one level that Tawna was out of my league, but now that I was actually staring the kind of guy she dated in the face, I realized that I didn’t have a snowball in hell’s chance of ever getting with her.

  Because this dude was like male model levels of attractive: a full head of thick, black hair, strong full eyebrows, a cartoonishly chiseled jaw, tanned swarthy skin, bright white teeth, the works. And just to rub it in, as I swiped across to the second picture of his dating profile, I saw that he was super buff too, his shoulders so broad and his biceps so huge it was actually kinda ridiculous.

  “So?” Tawna asked, emasculating me even further by treating me like one of the girls. “What d’you think I should do?”

  “Maybe I’m being clueless here,” I began, deciding to just give her my honest opinion, “but what’s the point of seeing him a second time if like you say you have nothing in common?”

  “You seriously wanna know?” she grinned, arching an eyebrow.

  I watched on as she snatched back her phone and tapped at the screen.

  “This is why,” she said a second later with a devilish grin, once again sliding the iPhone in my direction.

  As my eyes focused on the screen, I felt my stomach lurch, my mouth falling open in shock. Because there on the screen of her phone was a cock: huge and thick, the meaty shaft ridged with veins, the bulbous head a shiny purple color and the big full balls round and smooth beneath. It looked like something straight from a porn movie – way more impressive than my own puny five-incher.

  “Now d’you understand?” Tawna chuckled, tapping a glossy pastel pink nail against the screen. “He’s amazing in bed and oh my god, that big dick feels so fucking good in my ...”

  “Your drinks ladies.”

  The waiter’s voice snapped me back to attention, and I reached out to flip Tawna’s cellphone face down on the table. But it was too late.

  The waiter’s disdainful glance he’d seen everything: Tawna and I both ogling that big, hard cock like a couple of total sluts.

  My face burned with shame, and when I reached out for my wine, my hand was shaking. And there was something else, too; something I didn’t quite dare admit.

  Because as I took a nervous sip of the wine, I realized with a fresh pang of humiliation that I was turned on by the thought of Julio’s cock, my own pathetic dick throbbing hard in my panties …

  5

  “You seriously telling me that puny salad was all I’m allowed?” I groaned as we stepped out of the glass doors to the bistro and onto the busy sidewalk about an hour or so later.
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  I still felt starving (not to mention a teensy bit buzzed from the wine).

  “Of course,” Tawna replied. “Like I said, us girls are always watching our figures. And now that we’ve got some fuel in our stomachs, it’s finally time to update that tired old wardrobe of yours ...”

  With that, she grabbed a hold of my arm and dragged me a few feet further down the sidewalk then through the bustling entrance to the nearby shopping mall. Practically the moment we’d set foot inside the cool air conditioned interior, my situation seemed to go from bad to worse. Because Tawna began to march us straight towards the familiar pink and black signage for Victoria's Secret.

  Even before we’d stepped inside the store, I could feel my face glowing with shame, suspecting that this was gonna be another humiliating exchange. And sure enough, she grabbed the first available store assistant and announced – in a voice loud enough for the whole goddamn store to hear – “My friend here is in need of a bra fitting!”

  “Tawna,” I hissed beneath my breath, trying to escape. But I winced as I felt her long nails digging painfully into my arm through my shirt as she held me firmly in place.

  Just like the waiter at the bistro, the pretty young sales assistant affected an air of cool professionalism despite her obvious shock at the idea of a dude getting fitted for a bra, saying, “In that case if you’d like to come right this way, I’ll get you measured up ...”

  It felt like I was in some kind of fucked up anxiety dream as I began to follow the two women off into the depths of the fitting room for my very first bra fitting …

  * * *

  So began a whole afternoon of humiliation. Because it seemed as if Tawna had cherry picked the absolute most embarrassing experiences humanly possible.

  After we’d waltzed out of Victoria’s Secret (with a generously padded 34a bra that matched the thong I was currently wearing), we headed on over to the nearby branch of Sephora, a sprawling open-plan makeup store.

  Once inside, Tawna took the exact same tact as before, announcing to yet another friendly sales assistant that I was in need of a new foundation and as such wanted to get color-matched (whatever the hell that meant).

  The two women had sit on a high stool while I’d endured yet another humiliating, perched there right in the goddamn middle of the busy store as they tried out various swatches of foundation on my cheeks and forehead until they’d identified one which seemed to match my skintone.

  And after that, she’d bustled me into a sprawling three-story department store that was even busier than the rest of the mall, where we’d headed straight to the shoe department to pick out what seemed like a comically huge pair of glossy, patent black stilettos.

  “You wanna know the reason us girls always wear high heels?” Tawna asked as we sat there waiting for a girl to return with the heels in my size.

  “Why?” I muttered, still feeling like I was trapped in some kind of nightmare; just wanting this whole ordeal to be over with now.

  “Well it’s certainly not because they’re comfortable,” she explained. “Trust me, an hour in those babies is going to be murder. Nope, we wear them simply because they make our legs and asses look great ...”

  6

  “Home sweet home,” Tawna exclaimed a few hours later, as we finally returned to her apartment a few hours later, loaded down with what felt like our own body’s weight in shopping bags.

  She’d put the spending spree on her gold Amex card, and I knew for sure that she’d racked up way more today than the hundred-dollar wager of our bet.

  Which got me wondering: why the hell was she going to all this trouble? It obviously wasn’t for the money. Nope, it seemed more important for to her to punish and humiliate me, to make me see the error of my ways, to call out my bluff than it was to gain a hundred bucks ...

  It even seemed a little like she was enjoying the process of humiliating me, her eyes lighting up with impish glee as she’d picked out my stilettos, my make-up, the bra, not to mention the little black dress (which she’d made sure to take home in two different sizes in order to make absolutely sure that one of them fitted me).

  And now here we were back at her apartment, which was flooded with late afternoon light from the huge floor to ceiling windows. The whole place was so swanky it was crazy, large and open plan with a delicious floral scent in the air, I guessed from the many candles dotted around.

  It made me feel ashamed of my own crummy place. After all, I took home a pretty decent salary, but I spent most of it at the bar and gadgets, and looking around at Tawna’s tan leather sectional sofa and impressive glass coffee table made me realize that I’d been living like a broke college student this whole time.

  A quick glance at the huge chrome wall clock told me it was just after five, and I felt woozy and lightheaded after a whole day’s shopping on nothing more than a few salad leaves and a glass of white wine.

  But Tawna seemed like a dynamo, brimming with an almost inhuman amount of energy, and barely the moment my ass touched the sofa she’d grabbed me by the wrists and pulled me back to my feet again.

  “No rest for the wicked!” she laughed. “It’s time to get this show on the road ...”

  “What the hell are you talking about?” I sighed. “Surely we must be almost done by now?”

  “Done?!” she exclaimed, her big brown eyes widening in horror. “Done? We've barely started! It’s time to get you into all this stuff. It’s time for your makeover, Cleo.”

  Cleo?

  I felt my stomach lurch afresh as she said the name.

  Yet at the same time I figured that if I'd come this far, I might as well see this crazy ride through to the end. Hell, maybe I might even show this crazy bitch that I was man enough to take her crazy punishment, after all.

  “Alright,” I said through gritted teeth, nodding down at the sea of shopping bags that lay waiting for me on the floor of her apartment. “Let’s get this over with ...”

  7

  “Promise you won’t laugh?” I called out, my shaky voice betraying my nerves as I waited out of sight by the doorway to the living room, the black dress clinging to my body like a second skin, the bra hugging my pecs, the thong wedged tight between my ass cheeks, and my feet crammed painfully into the sky-high stilettos.

  “I promise,” Tawna laughed back, the relaxed tone to her voice suggesting that while I’d been getting ready in her bedroom, she’d been making light work of the bottle of white wine she’d uncorked. “C’mon, c’mon,” she added, “let me see what you’ve got!”

  “Alright,” I sighed, tottering unsteadily on the heels as I made to enter the room, my toes crammed painfully into the ends of the shoes.

  I sucked in a deep breath then began to walk, placing one foot in front of the other as confidently as I could, willing myself not to fall on my ass as I stalked unsteadily into the room, trying – and failing – to keep my back straight and my head held high like Tawna had taught me.

  But it was no use. I just couldn’t seem to get the hang of it and I let out a disgruntled sigh, my hands flopping down by my sides, weirdly frustrated. All the pop stars and actresses and models and even businesswomen – women like Tawna, in fact – made strutting around in heels look like a piece of cake. But me?

  “I look like an idiot,” I sighed, overcome by an oddly powerful sadness mingled in with a frustration so strong it almost brought me to tears. “I’ll never be sexy,” I added quietly.

  I shot a glance at Tawna, expecting her face to be lit up in an evil grin – my humiliation now complete. But to my surprise she was staring back at me with what looked like genuine compassion, and a second later she set down her wine and jumped to her feet, striding over to me and taking hold of my shoulders, staring deep into my eyes as she spoke, her big brown pupils burrowing right into me.

  “Alright, I’ll admit,” she began gently, “this whole thing started as a joke. I wanted to give you a taste of what it was like to be a girl – to make you see how hard, how pa
inful, how difficult it was. But at the same time,” she paused for a moment, “at the same time I guess that I’ve begun to care about this little project of ours and whenever I start something I always want to do it right ... Understand what I’m saying?”

  “I think so,” I replied solemnly.

  “Good,” she smiled. “Because now? Now I want you to truly feel like a woman, to know what that’s like to feel sexy and feminine and free ...”

  I had to admit, there was something addictive about the way Tawna was talking, like she was letting me in on a real girly secret, and I found myself nodding excitedly and saying “Okay, let’s give this another shot ...”

  * * *

  “Perfect!” Tawna exclaimed later an hour or so later, letting out a loud whoop of delight and clapping her hands together in enthusiastic applause as I acted out her instructions to the letter – strutting into the middle of her living room like a catwalk model, setting one leg confidently in front of the other, all the while making sure to walk just as she'd instructed: heel toe, heel toe.

  I’d even thrown a little swing into my hips, and as I struck a pose before her I made sure to push out my right hip, letting my hand rest loosely on it and freezing for a moment before spinning so fast that I felt my bob flick out from my face, as I paced rhythmically back toward the doorway again, loving the sheer tightness of the dress as it clung to my hips and butt. And beneath the dress I could feel the naughty secret of the thong too, teasing my ass with each step I took, a sensation I’d grown to enjoy ...