Guys and Dolls

That night as I slept lightly, the tumult running through my mind, I had a dream that shocked me with its vivid intensity. In the dream I was dressed in a diaphanous black cocktail dress, my dark hair long and falling to the curve of my back. My hips swayed seductively as I sauntered across the ballroom where the party was being held.

Every eye was on me as I moved, the alluring sensation of the tight dress against my body acting as a catalyst for my sense of feminine sensuality. I moved to the dance floor and stood among the crowd, dancing alone. My hips swayed to the rhythm, guided by the bass reverberating through the floor. My eyes closed enjoying the erotic sensuality of the moment.

I suddenly felt a pair of strong hands gently grasp my waist and a body press up against me. The subtle scent of cologne carried to me as I raised my arms above my head and moved to the music against the stranger at my back. My ass pressed against his groin and I could feel a swelling pressing into me.

His hands moved up and down my body as he leant further in, his warm breath on my neck. My hands reached down behind me and caressed his hip, holding him close to me. As his lips found the nape of my neck, I felt us being jostled by the crowd on the dance floor.

My eyes opened and I found that we were surrounded by a sea of bodies moving in a surreal, trance-like state to the hypnotic music. The dance floor was swallowed in darkness, the brief flashes of choreographed lighting, only making my surroundings more disorienting and difficult to discern.

I suddenly froze as I felt a hand slide along my exposed upper thigh. A pair of teeth lightly grazed my neck and I succumbed to the sensations, melting into the stranger at my back. The tent in his pants rubbed along the crack of my ass, my moan drowned out by the cacophony of sound on the dance floor. I rocked my ass against his groin, smiling wickedly as I felt him press more firmly into me.

Fingers raised the hem of my mid-thigh dress and I felt the cool air on my panty-clad ass. Firm hands pulled my panties down to fall at my feet which were no longer moving. The seething mass of bodies and the dark light acted to conceal me. I felt wet fingers spreading my ass and tracing over my entrance. I spread my legs slightly inviting his exploration. My hands reached back finding the stranger's neck and I pulled him in to maul my neck.

My body was alight with new sensations. His fingers withdrew briefly, only to return again applying more saliva to my waiting hole. The tip of his finger slid into me and I squeezed my eyes shut tight as intense pleasure surged through my body, stoking a primitive hunger in me. I pressed back on his finger, craving the feeling of being forced open.

His finger withdrew from my body and I cried out in dismay. My hands reached down, finding the zipper to his pants. I urgently slid it down and reached in clumsily to extract his rigid phallus. The warm sensation and weight of his cock in my hand was electrifying. I pulled him forward by his thick shaft and slid him between my now slick ass cheeks. Taking a firm hold of my waist the stranger at my back pressed forward, my hand guiding him to my eager hole. As the head of his cock found my centre, my silent lover thrust forward into me.

The alarm brought me awake abruptly. It took a few moments to adjust to my surroundings. I felt an instant frustration at being pulled away from my dream, especially given the cruel timing of the interruption. Then, as the implications of that thought dawned on me, I realised that I was wishing to return to a scenario in which I was being fucked by a random stranger while dressed as a woman.

The all-consuming power of the dream was difficult to deny. Not that there was much point trying to deny it with the sheet above my groin tenting lewdly. I lay there in my semi-conscious state trying to reconcile these feelings. Strangely though, given my earlier apprehension about the dress, I was not conflicted by this development. Rather, my submission took on a new complexion.

Eventually, I dragged myself from bed, showered, dressed and headed down to the dining room. Seeing the hulking figure of Jase at a table by the windows, I grabbed some yoghurt and granola and headed over to sit with him.

Sliding in across the table from him I mumbled my hello and stared bleary-eyed out the window to the courtyard beyond.

"Good sleep, huh?" Jase asked smirking.

"Yeah," I offered, playing disinterestedly with my breakfast.

"How's the prep going for the party?" Jase asked out of the blue.

"Fine, I guess," I muttered non-committally.

"Cassie said you actually managed to pull off a dress," he smirked over his half-finished piece of toast.

"Fuck off," I said mildly annoyed. "And how the fuck does Cassie know anyway, she wasn't there?"

"Girls, dude," he offered shaking his head. "Nothing goes on here that doesn't end up being shared among that bunch."

"How are you going finding a dress?" I asked, changing the subject.

"I'm just hiring one," he grumbled. "I couldn't get any of the bigger girls to part with their kit. Probably thought I'd get drunk and rip it."

"Jase, this thing seems to be getting a life of its own," I suggested warily, wanting to maintain the appearance of disinterest. "The girls are talking about doing make-up for all of us. I don't get why we bother with all of this effort."

"It's just a bit of fun, Gav," he said. "Most of the girls are hiring 20's era suits. Some are going all out with monocles, Panama hats and walking canes."

"For fuck's sake," I groaned.

"What's the problem, Gav?" Jase asked, suddenly curious at my negativity.

"Just tired I guess. Who is doing your make-up?" I asked, redirecting the conversation.

"Cassie said she would do it," Jase said smiling.

"You still have a thing for her, huh?" I queried.

"Gav, she is a knock-out," he said. "I'm not going to knock back her offer. I may even ask her to escort a lady to the party so that I feel safe."

I rolled my eyes at that. As I finished my food I tried to dismiss thoughts of the party and dresses.

Despite full days of soporific lectures, the remainder of the week disappeared quickly. I hadn't had a chance to speak with Sebastian and I was worried about where things stood between us.

Before I realised it, I was sitting in my room on the afternoon of the party feeling the constricting grasp of nervous expectation.

A knock at the door stirred me from my stupor and I opened the door to Jen. She was beaming as she bounced into my dorm room carrying a covered garment on a clothes hanger and a bag in her other hand. I stared at the concealed dress with a sense of resignation and a disquieting excitement.

Jen ran her fingers over my smooth forearm. "So, you did shave," she purred. Grinning conspiratorially, she asked, "all over?"

"Not all over," I lied. In fact, I had found the experience of shaving my body so deeply erotic, knowing that it would accentuate the experience of wearing the cocktail dress, that I had run the razor over my 'downstairs' as well, leaving me completely bare. The feeling of baby-smooth skin and the desire to give myself over to this urge to feel feminine sending a shiver through my body.

Jen broke my concentration as a flimsy piece of pink fabric landed in my lap. "You better put that on," she smiled, her eyes alight.

I looked down to find a pretty pair of pink lace underwear in my lap.

Suddenly scared I looked up into those twinkling eyes. "There is no fucking way I'm wearing that!" I spat. "I have to wear a dress but I don't have to wear a thong. And what the fuck is it covering anyway?"

Jen chuckled at my discomfort. "When you wear a dress like this you can't wear normal underwear. It leaves a panty line and you will be able to see your underwear through the slit."

"Be that as it may.....wait....what the fuck do you mean you could see my underwear through the slit?" I asked, with a growing sense of unease.

Jen unzipped the cover over the garment to reveal possibly the most insubstantial dress I had ever seen. As she held it up to my inspection, I stood paralysed with shock. The silver, metallic item looked more like a halter top than a dress.

Choking on my words I spluttered, "I can't wear that!"

"Trust me Gavin, you can." She whispered earnestly.

Taking the dress and thong in shock I walked in a daze to the bathroom. I placed the coat-hanger on the towel rack and stared disbelievingly at the dress. God, it looked so fucking sexy. But how could I possibly wear that in public?

Feeling numb, I began to strip out of my clothes. Completely nude, I picked up the thong, marvelling at the delicate, lacy slither of fabric. I eased them slowly up my legs, a thrill coursing through me at the seductive feel of the garment and the knowledge that I was going to be walking around in public wearing such a quintessentially girly pair of panties.

"Jen, is this your thong?" I asked suddenly through the closed bathroom door.

"God no, Gav. I draw the line at sharing dresses. That pair I picked up for you at a local store." She replied.

"Well....thanks, I guess." I offered.

Laughter came from the other side of the door. "No problem, babe," she chuckled.

Easing the thong into place I was immediately taken by the way that the thin strip of lace crept into the crack of my ass. God, it felt so deliciously naughty. Conscious of the bulge at the front, I tucked my flaccid member down into the thin crotch of the panties. When I looked up into the mirror there was no longer a discernible bulge.

I turned admiring the way the panties sat, showcasing my ass. Jen was right, I really did have a curvy, womanly derriere. My hands traced along the cheeks admiring the smooth feel of my freshly shaved skin. I had to stop as my arousal stirred.

Taking the dress off the hanger, I looked for the zip without luck. The tag on the inside of the dress indicated that it was a polyester, spandex blend, presumably allowing it to stretch over the body.

I slipped the garment over my head and gently pulled it down. Despite the stretch in the garment, it took some effort to ease it over my hips. The thin halter neck in place, I straightened the material around my midriff and thigh. That is, I pulled down what little fabric there was. The slit in the thigh went to just below the thin panty line of the thong. I could now see why Jen had been so insistent on the choice of underwear.

For all intents and purposes, the dress was little more than two broad, rectangular 'vanity' patches running to mid-thigh, with a gaping slit opening as the dress fell over my upper leg. The material felt like a second skin and showed off my toned, lean body to great effect. While I clearly lacked cleavage, the cowl top helped conceal this. The dress was backless which served to draw the eye to my shapely ass. It sat snugly across the top of my hips accentuating the curve. I stared open-mouthed at myself in the mirror.

This dress had definitely ruined me. Any vestige of hope that my attraction to dressing as a woman was a momentary fetish flew out the window when I saw myself in that dress. I could absolutely see why girls liked wearing dresses like this.

"Oh fuck!" Jen whispered in poorly concealed disbelief. "Gav, you look fucking amazing!"

"Don't you ever knock?" I said, trying vainly to disguise the pleasure I took in her comment and the blush that suffused my face.

"You like it don't you?" She whispered into my ear as she came up behind me.

"No....I mean, look....." I stumbled over my words.

"You don't have to be ashamed," she purred. "You look better in that outfit than even Jess does. I can't believe how stunning you are!"

I stood there silently, not knowing what to say.

"I know you like guys, Gavin," she murmured uncertainly, holding my gaze. "I see the way that you look at Jase sometimes."

My blush turned a deeper red and I felt more exposed by her comments than in that dress.

"It's OK. There may not be any future with Jase, but there are no shortage of guys at this party who are going to take a long hard look at you tonight," she smirked.

"But first we need to finish getting you ready. Did you get the hairpiece?" She asked looking at me through the mirror. I nodded pointing to the wig box in the corner.

With obvious excitement, Jess picked up the box and took out the wig. She held the piece in the air running an approving eye over the mid-length, dirty blonde locks.

I leaned down for her to affix the hairpiece and brush any errant strands into place. The A-line bob curved naturally in to fall across my neck and cheek.

"Oh Gav, it's perfect," she gushed.

Taking a pair of tweezers, she carefully plucked some stray eyebrow hairs and then applied a moisturiser to my skin. Then came successive applications of primer, foundation, blush, eye shadow, eye liner and mascara. Jen ferreted around in her make-up kit looking through various shades of lipstick, finally settling on a bright, wine red colour. She scrunched her eyes in concentration as she carefully applied the lip-liner and glossy lipstick. She grabbed a bottle of setting spray and told me to close my eyes as she sprayed it four times across her work.

"You can open your eyes," she whispered to me. I opened my eyes to see her smiling broadly at me.

"My God, you are gorgeous. I am so fucking jealous."

She stepped to the side and my mouth hit the floor as I saw a stunningly beautiful young woman staring back at me.

"Gav, I had no idea," Jen muttered in utter disbelief.

The transformation was so profound that I had difficulty recognising myself. Jen had done an incredible job with the make-up and the wig sat naturally, with the blonde hair and cut matching my face shape and complexion.

No longer self-conscious in front of Jen, I turned so that I could see the way the slit sat on my hip. There was certainly more gap than dress, but God it looked so sexy.

Jen interrupted my train of thought to let me know that she needed to get ready. She told me that she would stop by with the girls to pick me up on the way.

I just stood in front of the mirror taking in each detail.

*

Pt 3. Luck be a lady

The girls swung by at the agreed time and I blushed profusely as I was met with disbelieving squeals and much chatter. Hands ran over me like I was just another one of the girls.

The girls, for their part had really taken to this theme. A number of them had chosen to dress like gangsters. A few had fake moustaches and others had used what looked like mascara to draw a pencil line mo. There were pin stripe suits, tweeds, long-tails and smoking jackets. The suits were accompanied by fedoras, boaters, panamas and just about every other type of period hat you could imagine.

As we arrived at the venue a crowd was congregating at the entrance. There were plenty of guys in slim dresses with more back hair than wolverine. Even more comical were the fellas who had done their make-up and turned out like Heath Ledger in The Dark Knight. But for all of those, there were some guys who had made pretty respectable efforts at being women.

Despite his size and bulk, Jase had done a surprisingly good job with his appearance. I put much of that down to Cassie, who was standing beside him as if joined at the hip.

Seeing Jen, Jase sauntered over to our group with a comically-exaggerated swing of the hips, clearly enjoying the pantomime. His eyes gave me a pretty unsubtle once over as he approached. Turning to Jen he asked if she knew who I was coming with. Jen smiled, biting back a laugh. Others in the group were not quite so restrained and giggled with mirth. Jase had a confused look on his face, like he knew he was the butt of a joke, but just couldn't figure out why.

"It's OK big fella," I said in my usual voice. Jase recoiled in shock.

"Gav?" he managed to force out. "No fucking way."

"You weren't checking me out were you, Jase?" I asked slyly.

"Course not," he stammered, the colour change in his cheeks attesting to his lie.

I patted him on the shoulder, good naturedly and he softened. "Damn, Gav. For a mate, you make one sexy chick," he murmured ruefully.

I laughed and we talked with the rest of the group until a bell announced that it was time to enter the ballroom.

As we walked in, I noticed that most eyes were fixed on me. Rather than being nervous as I had anticipated, I discovered that I enjoyed the attention. My hips began to swing just a little more than was strictly necessary.

It dawned on me that I had been looking at this from entirely the wrong perspective. Rather than worrying that people would think I was queer and liked to dress in women's clothes -- ironically, both of which were true -- I realised that I was in the one place where I could parade around in the sexiest little cocktail dress I'd ever seen and it wouldn't be considered out of place. So, I resolved to enjoy myself and this rare opportunity.

With this in mind I sauntered to the bar and ordered a champagne. Thank God that the wet bar was covered in the exorbitant up-front cost for attending the party, because this dress didn't give me anywhere to put my wallet and I didn't have a clutch.

However, the issue with offering students unlimited drinks is that there were more bodies around the bar than the mosh pit at a Pantera concert.

I half stumbled out of the mass of bodies 20 minutes later carrying my two glasses of cheap sparkling wine above my head and walked to the table where my friends were sitting. I marvelled that I was starting to get the hang of walking in the three-inch heels that I had borrowed. I walked a straight line, my hips swaying with the exaggerated movement.

A smile crept onto the corner of my mouth. I felt so damn sexy in this dress. The frequent looks that I attracted only serving to increase my confidence and feeling of femininity.

Sitting down presented the first challenge of the night. I spent much of my time pulling the skimpy dress down as I moved in the seat. I also would catch myself forgetting to keep my legs together. Thank God for table cloths.

As the entrée was brought around, I found that I wasn't hungry and instead sat there sipping my wine, scanning the lavish ballroom, curious to see what the other party-goers were wearing. As my eyes cast around the room for the fourth or fifth time my gaze was met by a striking pair of green eyes staring at me.

A silent thrill ran through me as I saw Sebastian's gaze boring into me.

Had he been watching me the whole time? I silently mused. A faint flush spread across my cheeks at the thought.

My God, he was stunning. He was standing at a table across the room in a black, high-neck, bodycon mini dress that sat high on his toned, muscular thighs. The figure-hugging dress contoured to his defined abdomen and chest. He wore no makeup or wig and his light brown hair was tousled with strands falling across his eyes.

The intensity of his gaze made my pulse quicken. Feeling the blush rise in my cheeks, I turned back nervously to my friends who were eating their meals in between ribald remarks about the outfits being worn by one party-goer or another. To calm myself I downed my drinks quickly.

Jen looked over at me, a strange smile on her face. Damn, that girl was too bloody observant. Feeling self-conscious I got up and returned to the crush of bodies at the bar to get another drink.

Man, it was crowded in there. Everyone was jostling and jockeying to place an order. I stood in the queue not seeming to make any real progress towards the bar. As bodies parted to let a guy take his drinks away from the throng, I got pushed to the side and lost my balance. Strong hands seized my waist and prevented me from falling. I looked around gratefully to thank the good Samaritan and found myself looking into Sebastian's eyes. He smiled at me and I nervously smiled back.