Chasing Skirts

When I entered college, I was a virgin. Not to say it was particularly unusual; I was a quiet, nerdy kid. I wasn't ugly by any stretch of the imagination, but a little short, not very masculine, a little self conscious and not hugely used to interacting with girls.

I was eager to change this fact, but I felt like something of a romantic; I didn't want a random hook-up, and besides, I wasn't sure I had the confidence or knowhow to make anything happen that way.

What I was sure of, was that there was a girl I had in mind to pursue.

She was sort of a long time crush of mine. I'd known her since the last few years of high school, when my social circle had expanded to include my guy friends' girlfriends, and their friends in turn. We'd ended up at the same university entirely by accident, to my delight.

Her name was Heidi.

She had a sort of goth or scene style, with the looks to match; dark black-brown hair down past her shoulders, pale white skin, beautiful bright eyes, with a blue-green colour. She was slim, of a similar height to me, with a chest that drew men's attention without being distracting.

We'd bonded a little back home at various house parties. Knowing we were heading off to the same town served as a good ice breaker and we turned out to have some similar interests. She was something of a closet nerd, so we talked a little about games, comic books, anime and manga; not typically thought of as the best way into a girl's pants, but she talked so passionately about her geeky interests that it sort of seemed like she rarely got the chance to discuss them at all.

By the time the summer was up, we'd made plans to hang out during freshers week, and to generally keep in touch so that there would be a friendly face from back home among all the strangers in a strange new place.

Nothing much happened those first few weeks - I told myself that I needed the right opportunity, that if I acted rash I'd just put her off.

-

One night, out of the blue, I got the chance to change my relationship with Heidi. It didn't seem like it at the time, but it could very well have changed the course of my whole life, though it didn't feel that way at the time.

The night was winding down, such that we were technically in the early hours of the morning, and the others we'd been drinking with had stumbled back to their various dorms and rooms. I had a small room to myself, a little cell of a thing with just about enough room for a bed and a desk, with communal bathrooms and a shared kitchen. We sat on the edge of the bed, beers in hand, buzzed and blathering on about shows we'd been catching up on, one of which must have prompted a question I thought I'd misheard.

"You ever think about trying crossplay, Sam?"

She looked at me earnestly, and I imagine in return I just looked somewhat baffled.

"Cosplay? I've seen some cool ones online. It never seemed like the kind of thing I wanted to try. Lots of work to get it looking good and all that."

Heidi slapped my arm playfully.

"No, you dope. I'm not slurring. I said crossplay. You know, more specific. Dressing up as a character of the opposite gender. I was just thinking it could really suit you."

I put my hand to my smooth chin as if to pretend I was deep in thought. Honestly the question had thrown me.

I had seen that online too; both obvious bearded chubby dudes in too-tight Sailor Moon outfits, and what appeared to be cute girls that commenters were eager to point out had more going on downstairs than one might expect.

"I never really thought about it, to be honest. I don't think I'd be able to pass... and I don't think I'd get anything out of it..."

As I trailed off, she bit her lip a little. It sent something inside me, behind the tipsiness, fluttering.

"I think you could pull it off, easily, with a bit of a helping hand..."

Heidi leant in closer, her dark hair dancing in front of her face as she glanced around almost conspiratorially.

"...and maybe you could get something out of it. I for one find the whole... gender play thing... kinda hot."

She was so close my vision was full of her, and my nose was full of the sweet, fruity smell of her perfume. My mouth took over the talking, not giving my brain time to process anything I was saying.

"I suppose... I could be persuaded to try it out..."

She smiled mischievously.

"...but I wouldn't know where to start."

Heidi waved a hand dismissively as she finished taking another sip of her drink.

"You don't need to worry about that, silly. I have everything we'd need, you just have to show up to my place on... let's say next Sunday."

I stopped to think, and to drink. I had no personal interest in crossdressing, but the idea of it didn't disgust me or anything like that. And if it got me closer to Heidi, made her see me in a sexual light...

"I guess I'm up for trying new things, but-"

Our gazes met as she raised a dark eyebrow over her smiling eyes.

"But?"

"But I still don't see myself getting much out of it. I'm not into that sort of stuff myself."

She sighed and slowly pulled herself to her feet. I thought I'd ruined the mood but after she put down the bottle she was holding she placed a hand on each of my shoulders.

"How about this; you come over on Sunday and we'll see how things go from there. In exchange... I'll give you a little show now."

There was probably not much I would have disagreed with at that point, but I swallowed nervously and stammered out my reply.

"s...sure!"

Heidi grinned at me, gave me a flirty wink and moved over to the desk, where my phone was plugged in to some speakers, playing some low background music. She turned it up a little and changed the track to something with a little more rhythm.

She sashayed back the small distance towards me, moving a little clumsily at first, but quickly getting into the beat. She shrugged off her black leather jacket and tossed it onto the bed. As she swayed her hips, her breasts bounced playfully beneath her dark tube top. Heidi ran her hands through her hair, pulling it back as she turned in a full circle, gyrating all the way. Her hands flowed gracefully down her side, and she lifter her short denim skirt teasingly, giving just a flash of her black thong before pulling it down again.

Still moving to the beat, her hands crossed in front of her belly, drawing my eyes to her flat, toned stomach, to her milky white skin. As I admired her tiny navel, her hands dropped again, to her belt this time.

I glanced up to her face as I heard the click of the buckle. Her cheeks were slightly flushed, but she was smiling, watching me intently.

She turned again as she shimmied the skirt down her legs and onto the floor, giving me a solid look at her ass. In the moment I was enraptured, knowing all that stood in the way of her most secret parts was what amounted to little more than simple string.

Heidi kicked off the skirt as it reached her feet, and toyed with her thong, pulling the straps tight against her skin, thrusting her hips slowly as she let the elastic snap with a slap back into place.

She moved onto her top, skating her fingers over her ribs before slipping them under the fabric and lifting, taking her time, as if to give me a chance to stare at her whole body, now standing before me clad only in black underwear, a striking contrast to her pale complexion.

I was not the most qualified to judge, but I would've guessed she was somewhere between a B and C cup. Whatever the actual size, to me her breasts seemed like two ideal handfuls - I wanted now more than ever to touch her - I could feel the pressure of my dick pushing against my jeans, but I felt like she wanted me to keep my hands to myself.

Her bra was simple, black to match her lower half. It pushed her boobs together and up, such that it seemed her cleavage would hold up even a piece of paper if one were to slide one down in between her breasts. They jiggled hypnotically as she went to toss her top aside.

Heidi turned her back to me, glancing over her shoulder as she shook some more, smiling before wriggling backwards toward me, bending her knees a little.

"Lend a girl a hand, would you?"

She seemed to have positioned herself so that I could reach out and unclasp her bra. Eager to oblige, but nervous, I raised my right hand and pulled on the strap. Letting go, the elastic sprang open and Heidi danced forward, swaying as she reached back to peel the underwear off. As it dropped to the floor in front of her, she crossed her arms over her chest and turned bashfully back to face me.

She uncovered herself cautiously, and she giggled a little looking at my face; I noticed then that my jaw was wide open, so I shut it quickly, nearly biting my tongue. Hers were the first real tits I'd ever seen, and I was hard pressed to find flaws with them; they were practically porn star perfect. Amply sized, perky, and snow-white, with tiny pale pink nipples.

She stood there for what seemed like both forever and no time at all, and suddenly, the song, a distant memory to me, stopped.

It was like a spell had broken.

Heidi gathered up her clothes, pulling them on much less gracefully than she'd taken the off. I was stunned speechless, and she seemed too embarrassed to break the silence. Until she was fully dressed, at least.

"I should call it a night."

"Ah... uh... yeah."

I got up to walk her back to her place; it wasn't far, we were both on campus. I walked in silence and she quietly hummed the tune of the song she'd been dancing to, bringing me back to the image of her stood mostly bare before me.

"My place. Sunday. We have a deal?"

I nodded vigorously as she moved to open her door.

"I'll be there."

She waved briefly as her door closed, and I headed back to my cell.

I had to jerk off a good couple of times before I was able to sleep that night.

-

Over the next couple of days I played that scene over and over again in my head whenever I let my mind wander. It had me excited but apprehensive. A small part of me was worried this was some sort of trap, or trick; Heidi would get me in a dress and chuck my own clothes out a window or something, but I reasoned that she wouldn't be so needlessly cruel, she wouldn't go to such lengths for some petty humiliation I could reasonably laugh off.

We'd set up a time over text, and Heidi had said I didn't need to bring anything but myself, so when Sunday evening rolled around, I showed up at her door, a little early and dressed in a pretty simple jeans and t-shirt combo. Heidi answered the door, herself in a casual sweatpants and shirt, a light pink dressing gown on top of them. She beckoned to follow her through the corridors to her room, making idle small talk as we went.

She'd gone for more expensive housing; she had a much bigger room with it's own en-suite bathroom, a variety of clothes littered the double bed, posters lined the walls, there was a plethora of makeup accessories cluttering the desk. The room looked homey, much more lived in than my own little dorm room.

Heidi clicked the door shut and turned the lock.

"I still need to organise a few odds and ends - do you wanna jump in the shower? Best to work on a clean slate."

I hadn't expected this, but it made sense. I'd showered this morning but that was a good number of hours ago now.

"Uh, sure, yeah."

She'd moved to give the pile of clothes on the bed an inquisitive look, and she gestured to the room's other door.

"There's a clean towel in there, the blue one. You don't need to get dressed again when you're done."

I nodded and slipped into the bathroom, pushing the door shut behind me. As I undressed I felt very aware that I was in unfamiliar surroundings, felt somewhat exposed even though I was alone in the small room. I hopped in the shower, not wanting to dawdle, and got the water running, not even bothering to play with the temperature settings.

There was a much bigger variety of bottles dotted around the shower's base than I was used to, but I quickly found a basic hair and bodywash to work into a lather and scrub all over, focussing on the problem areas - groin and pits. I let the water wash away the last of the suds before switching it off and stepping onto the bathmat, grabbing the light blue towel off the rack and drying myself as I took a look in the mirror over the sink.

My damp dirty blonde hair looked a little long clinging to my face. Back home I would've been instructed to get it cut a couple weeks back. I rubbed a hand over my smooth chin; unlike many of my peers I had never yet needed to shave, but I was still pretty confident that as I was, I was unmistakably a boy. Part of me wondered if Heidi would get the result she was looking for.

I made sure my body was dry, not wanting to drip all over her room, before wrapping the towel around my waist. I braced myself to walk out, and be functionally naked in front of my crush.

Heidi had her laptop out, her attention on the screen as I came into the room, but she shut it as she saw me and stood up, clapping her hands together.

"Ok! Let's get started. Stand here for a bit, Sam."

I obliged, one hand on the towel, not holding in place but just ensuring it was not about to unravel itself. Heidi grabbed what looked like a white ribbon and came up to me; it turned out to be a tape measure.

"Really should have done this before today but... well, worth checking my estimates are close."

She had me stick out my arms and wrapped the tape around my chest, pulling it tight behind me. Muttering to herself, she slid it down to my waist, tightening it once more. She took some other measurements, from the front, the length of my legs, the length of my torso, before nodding to herself and setting the tape down on her desk.

"Right, clothes first. Arms up, please."

Heidi grabbed from the bed what looked like a white vest with no midriff, but it had a padded chest. She pulled it over my head and checked it fit snugly.

"Sports bra, with a little help for those who find themselves... wanting. Next is the lower half..."

She went to pull the towel off, and I made no move to stop her, despite any reservations I had. A mix of excitement and trepidation filled me as I stood there, my by no means impressive junk twitching as Heidi looked me over. She made no comment, but I was watching her intently and a curious smirk flashed briefly across her face. Whatever it meant, it passed and she went back into business mode, squatting down to stretch out a pair of white and blue striped cotton panties, holding them out for me to step into.

She drew them up my legs, stopping when they were in place, letting the elastic snap into my hips and then picking at them, making sure they didn't bunch.

Next she bought over a pleated grey skirt, holding it out in a similar fashion, pulling it up to my waist before zipping it up at the side. She followed the skirt with long black socks which went all the way up to my thighs. Next was a white collared shirt; I would guess a women's but I had no idea how one would tell.

In place of a necktie, she looped a light blue ribbon through the collar, tying it into a bow. From behind, she slid me into a dark blue blazer. I was a little glad she'd decided to dress me up in what appeared to be an uncomplicated girl's school uniform rather than something more complicated or outlandish.

She sat me in the desk chair and I realized that she'd positioned me so I couldn't see the large mirror in the room - I guessed she wanted me to only see the final product. Once I was in place she took a headband from the desk and slid it over my ears and up my forehead, holding my slightly damp hair out of the way. She wasted no time on pleasantries, jumping straight to the makeup.

She started with what looked like a large lipstick tube, but the substance in it was a creamy white. She applied it in in liberal patches all over my face, in a symmetrical pattern. Putting the tube aside, she gently smudged and massaged the stuff into my skin, like sunscreen. She took out a bushy brush after that, dipping it in some container outside my field of view - she'd told me to keep still while she was 'working' and brushed it lightly over my cheeks, my forehead.

Next she went to work on my eyebrows, tracing over them with a long, thin, bristly brush covered in something dark. All the different creams and powders and waxes and oils might as well have been forbidden alchemical concoctions for all I knew.

The parade of brushes and potions continued for some time, At times Heidi looked like an artist lost in her painting; brush in one hand, palette of 'paints' in the other and a focussed look in her eyes.

When she got to the lipstick, which even I could identify, she had been going for what felt like hours. It seemed like it was the final touch, or almost anyway; she removed the headband and replaced it with a hairnet, which she topped with a wig of long black hair.

"I think I could do something with your natural hair but - this is better for now. Anyway, time for the big reveal."

She offered a hand to help me out of the chair, a look of almost smug pride on her face. I let her pull me to my feet. She placed her hands on my shoulders, guiding me to turn, and again I obeyed, letting the mirror come into view.

My breathing stopped, my mouth fell open a little. I knew I was looking into a mirror, but there was a stranger stood there, mimicking my every move. I could see Heidi peering curiously over the shoulder of this young woman in front of me, but she was also there behind me.

The girl in the mirror looked like she could be a cousin of Heidi's or perhaps some other distant relative, at a glance. She had longer hair, with skin that was not as pale, and under more scrutiny not even much in common with her when it came to facial structure; Her eyes were also not that bright blue-green, but a familiar brown - The eyes were the one thing that broke the spell, to me at least. I could not help but recognize my own eyes.

I raised a hand slowly, and waved it gently in front of me, the stranger following my every move - because, as I knew, it was just a mirror. Heidi rested her chin on my shoulder, her whole demeanour now more relaxed, more content.

"So, what do you think?"

She spoke softly into my ear, and there was something in her tone, something a little husky, that sent a tingle down my spine. I could feel my dick start to shift in its unfamiliar cocoon.

"It... It's shocking, really. I really do look like..."

Heidi slid smoothly out of her dressing gown, letting it drop to the floor in a small heap, and moved in right behind me, wrapping her arms around me, cupping her hands around the suggestion of breasts the sports bra provided. Her voice lowered even further, to a whisper.

"Like a girl."

I watched as her hand traced down the side of the strange girl in the mirror; down my side, as hard as it felt to believe. I could feel her breath on my neck as she moved to lift the skirt, further breaking the illusion; the person in the mirror was not some cute innocent girl but a male pervert with a growing erection.

The striped cotton panties bulged outwards, throbbing slightly as I strained to control myself; I wanted to touch myself, to get release, and even more than that I wanted Heidi to touch me, to touch her, to run my hands over every inch of her ivory skin, to tease those perfect pink nipples, to ease myself inside her.

With these thoughts racing through my mind I turned my head slowly, my eyes filled with begging, hoping Heidi would see my desperation and show me some mercy.

She had her gaze turned to the mirror, eyes dancing up and down the length of my body, admiring her handiwork. Almost as if she'd been waiting for me to turn away, I suddenly felt her fingers through the underwear fabric, gently grazing my head and then my shaft, quickly but softly taking the whole bulge into her palm.