Guys and Dolls

Note: This story is a bit of a slow burn and is longer than my earlier submissions. I hope you enjoy.

Disclaimer: All of the characters depicted in this story are fictional and above the age of 18.

*

Pt 1. If I were a bell

The heat had been stifling in the packed lecture theatre. The air conditioning had broken down in the old building again and the collective thermal output of 150 bodies crammed together in the tight confines created an environment akin to a sweatshop.

As I stepped out of the dimly-lit sandstone building into the warm afternoon sun I sighed deeply. I had been in classes since 8 AM and I was fried. My political science course may not have been the most intellectually demanding curriculum on campus, but I had a high credit point load this semester and my classes were running back-to-back most days. Sitting in that lecture theatre, with minimal breaks for the best part of four hours had been exhausting.

My reverie was disrupted by something hard clipping the back of my head and I lurched forward from the impact. I turned around in annoyance to find out what hit me and chew out whoever was responsible. Standing behind me was my best friend Jason, with a shit-eating grin across his face.

"Hey G," he smirked.

"Shit Jase, take it easy, hey," I murmured, my glare softening as I rubbed the back of my head.

Jase and I had been friends since high school where we had been inseparable. While I had been a short, scraggly kid, Jase had been tall and a bit pudgy. As the years went on, no matter how much exercise I did, I never seemed to bulk up. Nor did I have a late growth spurt and I was a little embarrassed by my paltry 5 foot eight inches.

By contrast, adolescence had transformed Jase. The puppy fat was gradually replaced by muscle as he began to fill out his large frame. Girls began to sit up and take notice. For the longest time that had annoyed me as I had secretly cultivated a huge crush on Jase. My first 'nocturnal emission' had been caused by a vivid dream of Jase slipping down my boxer shorts at night during a sleep-over and easing his cock into me.

However, I had come to accept a few years back that Jase was 100% straight and would never be interested in me. Not that he would know that I was receptive to an advance because I zealously guarded the secret of my sexuality.

"Have you seen the theme for the next campus party?" Jase said. He gestured at the pamphlets that had been pinned to the noticeboard outside the lecture hall. I rolled my eyes at him.

Having gone to an all-boys school, with a discipline code that would make Pol Pot blanch, the freedom and inhibition of campus life had proven the catalyst to bring Jase out of his shell. He had taken to college life with a vengeance, revelling in the party scene. It wasn't that I didn't like a good party, but Jase hit every gig, rave and soiree that was going and frankly, it was tiring keeping up with him on top of my lecture load.

It wasn't as if I didn't enjoy campus life. I loved the independence of living away from my conservative parents and the ability to make my own schedule. It was just that I didn't quite get the same kick out of the over the top college party themes that Jase did.

"Sorry man, not now. I need a beer and air conditioning." I said not wanting to get into a long-winded conversation about a party. Jase just shrugged, "OK, well I have to get to class anyway. Catch you later on?"

"Sure."

As Jase turned to go to the boiler room that passed for a lecture theatre, I made a bee-line for the campus bar.

Upon entering the spacious bar with its panoramic view of the university playing fields from its perch on top of the hill, I was struck by an invisible wall of cool air. The bar was mostly empty as most people were in classes and it was still pretty early in the day. I breathed in the cool air and headed straight to the nearest beer tap.

Moments later I walked over to a vacant lounge with my pint of lager and collapsed wearily into the soft worn leather. I took a long draw from the beer and closed my eyes relaxing. I must have lost track of time because the next thing I knew I was roused from my torpor by someone standing to my side.

"That looks good," came a voice with a hint of Spanish accent.

My breath caught instantly in my throat as I turned to see Sebastian standing there looking down at me with a warm smile, indicating to my beer.

God, he was gorgeous, with his lightly tanned complexion and the tight t-shirt showing off his chest and arms to great effect. He didn't have the same bulk that Jase possessed, but he was athletic and his body was well-defined. He casually brushed back his light brown hair revealing his expressive hazel eyes.

I had instantly been attracted to Sebastian when he appeared in my classes at the beginning of the semester. I mean, how could I not.

"Can I sit with you," he inquired, not having received a reply to his first comment.

"S...Sure," I fumbled as I tried not to openly stare at him.

"I'll just get a beer," he announced, turning and walking to the bar.

Oh God, that ass, I groaned internally, as I enjoyed the unobstructed view of his perfect bubble butt

Shit! Get a fucking grip, I thought to myself taking a long draw of the cold lager.

I had never mustered the courage to talk to him, outside of a few short conversations in class about assignments. Being slightly shy, I just found myself getting tongue-tied in his presence.

As he came back with his beer and settled into the plush recliner across from me, he sighed deeply. "Man, I'm half Brazilian and I found it hot in that theatre today," he said looking over at me with a grin on his face.

I struggled to keep eye contact with him. My natural shyness and the fear that I would betray my attraction to him conspiring to make me awkward in his presence. I simply mumbled my agreement.

He started talking about the lectures and his major and little by little I relaxed and became an active participant in the conversation. He was a really nice guy and easy to talk to.

In an ebb in the course of the conversation he sat back drinking his ale, studying me. "Is your girlfriend meeting you here?" he inquired.

I nearly choked on my beer. "My girlfriend?" I responded raising my left eyebrow in confusion.

"I thought the pretty redhead was your girlfriend. I see you together a bit," he noted.

"Jen? No, she isn't my girlfriend. I'm not seeing anybody." I responded.

"What about you Sebastian? Do you have a girlfriend on campus?" I asked trying to seem casual to disguise my interest.

Sebastian was pensive for a moment before responding, "no, I'm not seeing anyone. I recently broke up with someone."

"I'm sorry. Did she attend our uni?" I probed, uncertain whether I was crossing into uncomfortable territory for him.

Looking into my eyes Sebastian replied, "No he didn't."

Now, I've never been much of a poker player, and I'm sure my physical reaction to Sebastian's admission was not my finest hour. But hey, I was about 10 minutes away from realising that I didn't have a shot with him and in the meantime I was in raptures that the guy I had a serious crush on was available and gay.

Sebastian suddenly looked down at his watch and indicated that he had better be off as he had another lecture to attend.

I was left to ponder our conversation over the last part of my pint. I became increasingly concerned that my reaction to his news may have led him to believe that I was taken aback by him admitting that he was gay. Of all the ironies! I decided that I would have to try to find a delicate way of amending that situation when I next saw him. Though I had no idea how to bring that up casually.

Another two lectures were endured that afternoon. Thankfully, both were in a lecture hall in a newer wing of the campus that had a functioning air conditioner. As I got back to my dorm room I saw a flyer for the next college party taped to my door. Clearly Jase was a tad over-eager.

It turned out that Wesley College were hosting a 'Guys and Dolls' themed night. But the kicker was that the guys had to come dressed as 'dolls' and the girls had to come dressed as 'guys'. Typical, I thought.

At least there would be alcohol, I consoled myself. The last college affair had been the annual toga party. It is rumoured that more children have been conceived at the university toga party than at Woodstock and Burning Man combined. By comparison, this was likely to be a relatively sedate affair.

I looked to my left to see Jase chuckling to himself.

"What are you laughing at? They haven't made a dress yet that you are gonna be able to squeeze into." I quipped.

"Ah, not true Gav. If Steph Harris can get those delectable double D's of hers into a cocktail dress, I have nothing to worry about."

I had to concede the point. Steph Harris had quite the rack and surely Jase's broad chest wouldn't have a circumference any bigger than Steph's sizeable bust.

"But where the hell are we going to get two dresses from anyway, J?" I asked as the logistical challenge finally struck me. "I don't want to blow my pay packet on something I wear once as a gimmick for a college party."

"That's easy. We borrow them from the girls in college." He offered.

"I don't see any of the girls letting us near their coveted wardrobes," I countered.

As it happened, I was proven wrong on that score. It turned out the girls had really gotten into the spirit of the party. They were fighting it out to come up with the most absurd, slutty ensemble for us to wear.

At least the 'size 8' girls were safe as none of the guys could fit into their clothes.

Because I only stand 5' 8" tall, the girls were lining up to set me up in their clothes. At a statuesque 6' 3", Jase had the opposite problem, as there just weren't many girls who stood anywhere near that tall.

Jen Simmons, a close friend from my college dorm, and the one who Sebastian suspected to be my girlfriend, brought in a sexy mid-thigh, navy blue Manhattan dress with spaghetti straps. She also brought a shit-eating grin as she left it for me to try on. I rolled my eyes and took it into the bathroom to try on.

I slowly disrobed feeling somewhat awkward knowing that a girl was waiting outside my bathroom door for me to try on one of her dresses. Only in college!

In truth, my hesitation had little to do with Jen. It had more to do with the fear that I was opening Pandora's Box.

My conservative up-bringing and schooling had made my undeniable attraction to men difficult to accept and impossible to share with those close to me. However, it was the specific nature of my predilections that had me so apprehensive about putting on a revealing cocktail dress.

You see, I didn't just want to have sex with a guy. I had a powerful, almost primitive desire to be taken and used. I yearned to completely submit to the carnal desires of another. I wanted them to take their pleasure with me in any way they saw fit.

The raw intensity of these desires scared me. They would consume me leaving me incapable of coherent thought or reason. While a lack of opportunity and my inherent shyness meant I was still a virgin, when aroused I would make reckless decisions, abandoning reason to slake my desires. The sensation would come on me and overtake my senses as if I was in heat.

Last year, when the urge to submit myself became overwhelming, I had gone to my older sister's room and spent 3 hours trying on her lingerie and dresses. I had raided her make-up as well, applying lipstick, make-up and perfume. While my efforts at cross dressing were amateurish, I had felt so damn sexy and slutty.

The act of making myself into a woman was like pouring accelerant on a raging fire. I was rendered senseless in my urge to be taken. While looking through her lingerie drawer I had found her 6.5-inch vibrator. Driven by desire, I took the smooth metallic device and put the tip between my lips. I moaned deeply as I sunk down on the hard device, my tongue whipping over it.

All reason abandoned I raced to my sister's bed and placed the wet instrument facing up. I moved aside the thin strip of the g-string between the cheeks of my ass and pressed myself down on the vibrator. Being dry down there I was unable to penetrate myself, but the sensation of pressure on my entrance drove me insane with desire.

With an insistent, immediate need to be penetrated and not knowing where Tracy kept the lube, I hastily applied saliva to my hole and re-positioned myself over the vibrator. Rather than taking my time to adjust to the size of the instrument, I simply drove myself down with all my weight and the resistance was broken as the hard rod rammed deep into my bowels. The instant pain as my anal muscles reluctantly gave way to the force of the incursion was mixed with a heady, euphoric sensation of being filled.

"Oh God, yessss," I groaned loudly into the room.

I raised up and plunged down over and over feeling the fake phallus split me apart. My eyes clenched tight, focusing on the incredible sensations. I imagined myself riding the naked, glistening cock of a muscular, athletic stud. Maddened as I was, my whole being was focused on milking his cock and having him breed me.

In only a few minutes I felt my head grow light, my balls tighten and I came hard in Tracy's g-string from the sensation of being fucked. Everything went white and I lay there, my cum leaking through the front of her panties onto the comforter on her bed, the vibrator buried deep in my ass. Unable to move I panted heavily in my prone position while my addled mind attempted to register what had just happened.

I returned time and again to Tracy's room, fucking myself with her 'little helper' while wearing her clothes.

For reasons passing understanding, the simple act of putting on a provocative dress - an outward symbol of femininity and sensuality - seemed an unconscious trigger to my submissive desires. While many women could assert dominance through an outfit like that, when I wore them it had a very different effect. To my confused brain, the act of putting on a dress symbolised my acceptance of my effeminate alter-ego and the sexual servility that I fought so hard to control.

It was the fear of betraying this side of my nature to all that I knew that had me so hesitant about wearing the dress.

Standing in just my underwear I unzipped the back of the dress and reluctantly slipped it on. The fabric felt smooth as it fell over my body, kissing my skin. A shiver ran up my spine as I shimmied the material into place. As I straightened it out and my eyes rested on my reflection in the mirror I was left momentarily stunned. I looked...... beautiful.

The dress was unlike any that my sister had owned. It was sexy, stylish and designed to show off to best effect a woman's figure. Sure, my short hair was a bit tomboyish, and the light hair on my arms was out of place, but my diminutive physique and the subtle, almost feminine curve to my hips was accentuated nicely by the elegant garment.

I didn't look scrawny as I did in men's clothing, and although the dress was a little large for me, I did not look the least bit out of place in it. Quite the contrary, actually. My thin, but toned arms, chest and legs were startlingly matched to the outfit I now wore.

I had always had youthful, good looks, but it wasn't until the dress was in place that I could see that, in fact, those features were quite feminine. My jaw and chin were not angular and my lips were quite full. There was a symmetry to my profile that looked natural when they were viewed framed by a seductive dress.

I ran my hands down my side from my waist over the curve of my hip to my thigh. A warmth radiated from my chest outward, rippling through my limbs and face and making me feel slightly dizzy. I longed to be touched and held. My reflection seemed foreign to me. It exuded a strong sexuality in the skimpy outfit. A smile creased my lips. I enjoyed this!

My attention, rapt as it was in my appearance, failed to notice Jen easing the bathroom door open.

"Oh my fucking God!" She gasped, placing her hand over her mouth in disbelief. She stood there stunned for the longest time just staring at me through the mirror. Stepping into the small room she moved behind me and slowly zipped up the dress.

"You look gorgeous!" She whispered.

"Thanks.....I guess," I stammered in reply, not quite knowing how to take the compliment.

"My God, my dress is too big for you. You bitch," she laughed swatting my backside with her hand. "Shit Gavin, I never realised what a sexy ass you have. Even though it doesn't quite fit you, you actually look better in my dress than I do."

"I'm going to have to call in a favour from Jess or Sarah," she mused, referring to her friends who lived off campus.

"Don't go doing that," I begged. "I will just pick something up at a rental shop."

"Relax, the girls will be OK with this and they have outfits in your size," Jen explained.

Before I could object again, Jen grabbed her phone and placed a call.

"Hi J, I need a favour and it is kind of strange," she began. "I need to borrow one of your 'special' dresses for a night."

"No, I know I don't fit them, thanks for reminding me," she muttered rolling her eyes. "It is for Gavin for the Guys and Dolls bash that Wesley are hosting."

"No, I tried him in one of mine but it was too big," a blush crept across my face as Jen continued. "No babe, he looks really fuckin' good. I mean REALLY good."

"Yes, I'm serious. I want something that you would wear out if you wanted to do the walk of shame next morning."

"Yes, trust me, he can pull it off." she said earnestly. "You have no idea."

"Oh God yes! I forgot about that one. Yes, that is perfect." She squealed. Looking straight at me she asked, "when can I come by and pick it up?"

"Gavin, what size shoes do you take?" Jen asked turning to me.

"Ah, size 8 men's, why?"

"Jess' feet are smaller than that but I'm a women's 9.5 so you can probably borrow something from me," she said.

"OK J, thanks for that. I'll swing by later and pick it up." Jen said, returning to her conversation with Jess.

Ending the call, Jen turned her attention back to me. "I can help with make-up if you like," she offered.

"I don't think I really need make-up, Jen," I said nervously.

"The other guys in the dorm are going all out for this party. A number of them have already enlisted the help of one or other of the girls to 'fix' them up." She replied. "It's just harmless fun. Besides, you are going to look good!"

"I don't know that I want to look good, Jen" I said hesitantly.

"I think you do," she smiled knowingly, looking down at my hands unconsciously running over the silky fabric at my hips.

Shit, I've got to stop doing that, I chastised myself.

*

Pt. 2 I'll know

The buzz generated among the girls in the dorm at the prospect of making guys over for the party seemed to catch like a wildfire. I was getting seriously nervous about what was being discussed. I had expected that a bunch of us would dress up in ill-fitting dresses, get wasted and have a laugh at our own expense.

I had never for a second thought that I could look the way I did in female clothing. My earlier amateurish attempts at dressing up had been hasty and not revealed to me the femininity that I had seen when wearing Jen's dress. There was a real risk that if I turned up looking like that the guys would think I did this regularly, or worse, see that I liked it.

I was still confused by the visceral reaction I got to putting on a dress. I may have been gay and I knew that I was submissive, but despite my physique I never considered myself to be 'girly'. It was as if a dormant part of my personality had awakened in my sister's room.