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Pushing the Limit

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Crossdresser gets far more than she knew she wanted.
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I couldn't have been happier that the day was finally over. It was basically the weekend for me, even if my next two days off were a Thursday and a Friday. Every chance I got, I checked the time on my phone. Of course, this just made the day drag on even more. I was tired of cooking, tired of the grind to earn just a little more money.

Breakfast was over. My shift was done, and I made my way out of the greasy kitchen past all of the nauseating sounds and commotion that was so commonplace to me now. Though my legs and lower back were glowing with warm pain from standing since before the sun rose, little flutters of excitement welled up within me at the thought of being home for two whole days with no commitments. I dodged around both managers and made eye contact with no one on my way out. I quickly clocked out, then made my way out of the back door of the restaurant.

When I'd arrived, it was dark. I felt like a vampire or a feral cave dweller as I emerged from the restaurant into the bright midday sun. I stretched with my apron wadded into my hand, allowing the rays of warm daylight to soak into my skin. I could only now hope that traffic wasn't going to be an absolute apocalypse. I couldn't wait to be home.

"Must be nice."

I jumped at the words. I found the owner of the voice leaning on the back wall of the restaurant, reclining without a care in the world.

I sighed but offered a weak chuckle.

"Announce yourself, Vicki," I told her.

The short girl grinned and blew out a plume of smoke from her glossed lips.

"Just did," she told me. "You off already?"

I nodded. "Y-yeah. I started picking up all breakfast shifts. I hate getting up that early every day, but it leaves my day wide open after that. If I can make it through."

I gave another nervous laugh. I had no idea why. Vicki's lips pulled to one side in a sly grin. Her eyes stared right through me. She always seemed to stare with such intensity. Or... was that just how she looked at me?

"Don't ever become a server, Al," Vicki said. "You won't get the choice. The Brady Bunch blonde with the daddy's car called out again today. And I'm here all day because I'm dumb enough to cover."

I cringed. "That sucks. Um... why do you call me Al all the time?"

Vicki's eyes remained fixed on mine. She took another drag from the cigarette in her plump lips and offered me another smirk.

"Because it bothers you," Vicki told me.

I snickered but looked away. She was right. I couldn't ever meet Vicki's gaze for whatever reason. But Vicki wasn't the only girl for which that was true. I rubbed the back of my head wearily, wondering what to say next.

"You working tomorrow, Al?" Vicki asked.

I shook my head, thankful for an easy question.

"N-no. I've got the next two days off," I said. "It's basically my weekend."

Vicki nodded. "I'm off work tomorrow. Can't come soon enough. I swear I need to fucking quit this place and work in my sister's shop. I just can't stomach her for a whole day."

My eyes were drawn to the tats on Vicki's arm. I knew very little about Vicki personally, other than she was a very straightforward girl. But I knew that sleeve had been inked by her sister. I never knew Vicki could tattoo or even draw. I was about to ask her about it, delighted that I actually was able to small talk with a girl without stuttering, when Vicki's next statement caught me completely off guard.

"We're going out tonight," Vicki said. "Some place downtown that's supposed to be rowdy. I'm pretty sure it's where Tasha finds all of her ex-husbands. Could be fun if you wanted to join. I got no one to talk to really, so I usually make a scene."

I stared at Vicki dumbfounded. It didn't seem like... she was making a pass at me. She was the kind of rambunctious soul that ate dorks like me for breakfast. I watched her dark eyes fall from mine, and a jolt of excitement traveled through my nervous system as she scanned me up and down. Was she... checking me out? No. That was stupid. But her eyes fell from mine more than a few times. And she'd invited me to something.

I'd never looked at her the way I was now. It seemed ludicrous. She was short, and her uniform t-shirt wasn't enough to hide the robust flesh that bulged from within. Her face was always made up a bit too much, though it looked exotic on her Filipino features. Her eyes were always so measuring, so penetrating.

"I... I dunno," I said. "S-sounds like a blast, but I kinda had plans...."

"So ditch 'em," Vicki said with a shrug. "You could come get shitfaced with me and embarrass my sister. Gotta be better than playing World of Warcraft or whatever you got going on."

It stung a little. I didn't really play video games, but the fact that Vicki thought I'd be cooped up like a nerd wounded my pride even more than it already was. The offer was alluring, though. Especially if Vicki was inviting me to party with her. The fact that she offered this out of the blue was odd. Like maybe there was more going on beneath the surface. It made my heart race and was intriguing for sure.

It was also terrifying.

I was already trying to open my mouth and formulate a pitiful lie when I felt a text message in my pocket. I pulled out my phone, only stammering a bit as I distracted myself with reading the message. Vicki was busy rubbing her cigarette out on the wall of the restaurant. I opened the message on the screen, and both recoiled and rejoiced at the contents of the text.

I saw the name appear, and I could only hope. I saw the stack of words and read each one with bated breath. Reading such words made me want to shrink away and hide from Vicki, but they made me want to sprint to my car with delight.

Hey I know ur probably working. Just wondering if u might be free later this afternoon. Kathy is going to be working tonight. Sry its short notice. Do u think u could drop by

I was relieved and excited all at once. It was a "get out of jail free card" that I didn't even ask for. Peter had impeccable timing. I swallowed my excitement and lifted my eyes to face Vicki with newfound confidence.

"Nah, sorry," I told her. "Another time, maybe? Can't cancel these plans."

Vicki studied me for a few seconds, and in those torturous seconds, I started to doubt my resolve again. I stared at her, wondering if I was crazy. Maybe the girl wanted to pity fuck me, or just have a random good time with a coworker. She adjusted her tight black uniform pants, and my eyes were drawn to the jiggle in her hips. Her shadowed eyes fell down my body once more. It was like trying to decipher a foreign language.

"Another time, Al," she said, stepping past me toward the back door. "Enjoy your freedom. I'm about to go get chewed out by one of my tables for not checking on them for five minutes. Fucking old people, man."

I chuckled nervously. "Good luck with that. I'll see you."

Vicki turned her eyes toward me one last time and offered me a playful smile.

"See ya, Alan," she said.

I carried the interaction with me all the way to my car and beyond. Surely I wasn't imagining things. She was... flirting? Maybe? In her own way? And she'd basically asked me out? That didn't happen to me. A zillion thoughts flew through my head. Was I stupid? I could have joined Vicki, and I could've gotten to see her at her wildest, and witnessed the crazy girl from all those morning after stories.

I sat in the driver seat of my car, thinking of Vicki. Had I really just turned her down? The silence in my car was overbearing. One part of me cursed myself, and questioned what I was even doing with my life to turn down such an obvious offer. A froth of shame bubbled up within me. I wondered what she really wanted. Maybe just to hang out? The way she looked at me... her eyes... was she wondering how I would be... that way? The same way I was wondering... what her tits looked like? How she would come on to me if she was drunk? How she was in bed?

I opened the text on my phone again. The text from Peter was there. He never texted on such short notice. That alone spoke volumes.

I started my car and pulled it into gear. A wicked sense of excitement swept through me. Pulling away from the restaurant made the decision seem so much more appealing. I was leaving the mundane everyday existence. Going out with Vicki was terrifying. It was the unknown, and I could only be let down.

Reality set back in, and I breathed a quivering breath, trying to quell my own excitement.

****

This always happened to me when I looked in the mirror. It didn't necessarily have to be when I was getting ready.

I stared for a while at my naked form in the reflection. Even with all the steam leftover in the little room, there was an extra chill that fell over my skin. It could have been my nerves. It was most likely that I was now completely hairless from my ears down. The air still smelled like the fruity lotion on the countertop next to the sink, which I'd just finished lathering across every inch of my smooth skin. The slightest touch was orgasmic. My thighs occasionally slid past one another with each step, causing my lower lips to tremble.

I must have bathed for over an hour. I kept glancing at my phone to check the time. I was locked in hesitation, staring at myself, wondering yet again if I should keep going. My long hair was clean and dried, drifting down beside my neck and shoulders. It was nice to see it removed from the usual bun that I wore and the nasty hair net that I was made to wear at work. I stared at my flat featureless chest, thinking of how I might look in just a little while.

My eyes fell further, and something inside of me sank even deeper. My little dick drooped lifelessly at my smooth crotch. I thought of Vicki again, in a way that I'd never imagined possible. What would she think of me? What would she say if she knew? In either case, she'd probably embarrass me or poke fun at me. For some reason, that didn't make me feel any worse, but it sent a wave of chills through my body.

The same thought surfaced yet again in my mind as it had so many times before.

What the fuck am I doing?

I blinked and tried to ignore the doubts and deeper thoughts. Peter was expecting me. The idea alone did nothing to settle my quivering naked body. I had time, but I needed to move if I was doing this. I blew out a determined sigh and set myself to work.

I knew what was first. I stepped into my bedroom and stared at the most expensive thing I'd purchased for myself in years. The breast plate seemed to gaze back at me, the wide areolae like pink pupils atop bulging fleshy eyes. I still couldn't believe I owned such a thing. Working carefully, I flipped it over and slipped my head through the neck hole, then my arms through the sides, and settled the heavy silicone into place. Moving again to the mirror as I adjusted the fit, I could see once more that my investment was still worth every penny. The appliance fit me like a glove. I could barely see the seams at my arms, my stomach, and my neck. The color of the faux skin matched my own so well. The effect was unreal. With each footfall, the breasts would jiggle and bounce ever so slightly.

I had to focus before let myself get swept away. I returned to my bedroom, fetching the matching black lacy bra and panties. The panties slid up through my thighs deep in between the cheeks of my ass like a knife through butter. I snugged them into place, feeling that satisfying tightness of the garment that was somehow so soft. I tucked myself down into the front of the panties carefully. Such a little bulge wouldn't be so obvious.

The cups of my bra lifted my silicone breasts and cradled them nicely to my chest. Already the weight of my tits seemed gone, and when I looked down I was greeted with a tantalizing view of the cleavage that had formed. I straightened my back, watching how the beauties bulged forth. I felt so sleek and voluptuous, where moments before I was a weak, scrawny boy.

I chose a thin white shirt and a short black pleated skirt. I was happy to see I'd achieved the effect that I wanted. The black bra was just visible under the little shirt, and my belly button just peaked out below the hem. The black skirt was not too short but airy and left enough to the imagination. My legs looked and felt incredible under the flowy fabric. I couldn't stop twisting this way and that, just to feel the skirt drift around my bare waist and thighs.

I spent an hour on my makeup and hair. Patting the foundation onto my face was simple and easy, as was the contouring on my cheeks. It was a struggle to keep my hand steady when I worked on my eyes. Watching myself in the mirror was nerve-racking. Was this really me doing this? As I slowly transformed, I began to settle down a bit. I faded the bold shadows behind my eyes to a blended perfection of darkness and color. I traced immaculate lines along my eyelids and fanned out my lashes with grace until they were flared wide. Simply blinking was enough to make my heart flutter now, and I could hardly look at my own eyes in the mirror without excitement frothing up within me.

As I curled the ends of my hair, I marveled at the girl that I'd become. My eyes... god, they were so big and exotic, accented by the dark colors. I wished that I could meet the girl I saw in the mirror. I wished she would stare at me as longingly as I gazed in at her. I wondered what my family might think if they knew who I'd become. My friends, as few as there were... what would they say? I'd gotten so good at this... would they even know it was me?

The final curl bounced away from the iron. My hair was somewhere between brown and bronze, and the thought crossed my mind to fetch the can of spray on highlights, but I remembered how badly it liked to rub off. I decided natural was enough. I began to softly brush the curls down, giving my hair a nice wavy ripple of curls. For a while, I got lost in the act and played with my hair, trading seductive glances at the girl in the mirror.

I took a second to consider the outfit. I wondered briefly if it was the right fit or if it made me look too much like a school girl. No. It was perfect. My fingertips fiddled and caressed the bare skin of my belly just under my shirt. Far below, I felt the twitch of arousal pressing against my snug lacy panties.

I took the time to paint my nails. Nothing fancy or colorful, just something to complete the look. After they dried, I found the cropped flannel shirt that I'd picked to wear with my outfit and slid it up over my bare shoulders, leaving it unbuttoned. I found the best lighting in my living room, with the afternoon sunlight pouring in from the windows. I played with my phone for quite some time, snapping selfies and little video clips, turning this way and that to find the perfect photo for today's outfit.

I didn't recognize the cute girl in the pictures. That wasn't me. The real me was a pitiful shut-in. She was nothing like that. A shriveled part of me wished that I could be her all the time. Doubts came slithering back into my mind again. Was I really doing this? Again? Was there a point of no return?

I cleared my mind, seeing the time on the display at the top of my phone. Kathy would be gone soon if she was working the late shift. I made my way around the house, finding the little purse I never got to use and stuffing my things inside. It felt like a dream just to walk around, feeling the air under my short skirt against my bare cheeks and feeling the way the lacy thong tugged between my ass. I swayed my hips just a little, letting them twist while my thighs slid smoothly against one another.

It all felt so real. I wanted to enjoy it, but it was time to go. I stepped into the short black boots and felt the heels push my ass high behind me. They were so cute and snug on my feet, and my entire outfit seemed to feel so complete all at once.

I locked up the house and hurried to my car, careful not to lose my balance in my shoes.

Peter was waiting.

****

I was so thankful that the windows were tinted on my car.

It felt freeing to drive across town while dressed, listening to music and carrying on about my day like any other person. It was also terrifying. Each car I passed looked like the car of someone I knew. Each red-light I approached felt like I was under the watchful eyes of all those people beside me, across from me, and all around. I couldn't seem to catch my breath. Sitting in my car with only the skirt to hide my thighs was incredible, but the exposure of being out like this tugged at the frayed ends of my brain. I just needed to get to Peter's house.

I made it to the far side of town, and the grid of neighborhoods and tall buildings quickly morphed into winding roads lined with new businesses, and eventually I was turning down a shady lane full of sprawling manicured lawns and huge brick houses. I saw a familiar face or two out for a walk on the sidewalk. I wondered if any of them recognized my car, or the girl driving it. I pushed the paranoid thoughts aside and took a breath.

Finally, I pulled into the driveway at one of the large brick homes with the perfect bushes. I saw the sleek grey Ford Explorer that Peter drove sitting in the driveway just to the side of the garage doors. I came to a stop and waited with my boot on the brake pedal. I held my breath. I glanced at my phone twice to check the time and make sure there were no messages. Everything was in order. I watched the house, my every thought gnawing at the insides of my skull. I used the time to dig in my purse and apply a coating of gloss to my lips, pursing them in the rear view mirror at myself to make sure they looked good.

After only a few minutes, the garage door began to rise. I stared straight ahead into the threshold as it slowly opened, looking for the bumper of a Cadillac. The garage was empty. I breathed a small sigh of relief. I waited until the garage was fully open, then eased my boot into the gas and guided my car into the empty parking spot. As soon as I parked, the garage door was closing behind me again. I gathered the little purse I carried and stepped out into the garage.

Peter was there at the garage door. He was smiling, watching me emerge from my car. It made me conscious of my every move. It was easy to put a little arch in my back with the wide heels under my boots helping to hoist my legs up high. I swept my hair around my neck and slung the purse over my shoulder.

Though my mind was screaming inside my head, I smiled at him and sauntered naturally toward the door where he waited.

"How's it going?" Peter greeted me.

I gave him a little nod, hoping my voice didn't crack.

"Hey, cutie," I said.

Peter stepped aside and motioned me in. "C'mon in, Alan."

As I stepped up into the house, our bodies came close. I felt like melting just being near him. I could smell the sweet spice of his cologne. I looked him in the eye and gave him a sly smirk. Peter bristled, his eyes darting across my face, down to my lips as I spoke.

"Alison," I told him, placing a hand gently on his chest. "Just Alison."

Peter's smile widened, revealing his perfect set of teeth. I broke eye contact and headed deeper into the house through the kitchen. I allowed my hips to sway ever so gently, aware that the pleated skirt waved just above my bare thighs in plain view. My heart was already racing, though. The thrill of being dressed in someone else's home was electric, and I did my best to keep myself cool.

I stepped into the kitchen and leaned against the huge island in the center, taking in the span of the open floor plan and glancing around the living room beyond. Peter was twice my age, but I always wondered if I'd ever reach his salary in my lifetime. I crossed my legs, allowing one smooth thigh to sit across the other while I leaned against the island.



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