Winner Taes All

I'm sorry it's been years since my last story. But since many have asked, I've finally finished this and decided to submit it to Literotica. Both boys featured are of legal-age (18 or over). If gay sex isn't your thing, please take a pass. I'd love to hear from guys who can tell me if I well-demonstrated the physical and psychological aspects of an emerging top/bottom, dominant/submissive. All the best and happy reading!

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It was nearing the end of my senior year of high school and one of the last big social events was the Senior Prom. Of course, being a bit socially inept, I hadn't gone to my Junior Prom and, not having dated, I hadn't taken any steps to rectify the situation. To be honest, I hadn't even thought of asking a girl to go out with me at all let alone to the Prom. Realistically, I'm not sure any would have accepted even if I did. It's not that I wasn't reasonable looking. I was just a little less than average in my mind -- you know, about 5'8", 130 pounds, brown hair, light colored eyes. You get the picture. And, I was really more of a geek and definitely NOT a jock. And then there was the sexuality issue. I just wasn't sure what mine was. Like anybody in their right mind, I wanted to be straight. While enjoying jerking off, I was otherwise totally without experience. It didn't help that access in our home to the internet was totally restricted leaving little options to "research!"

My best friend in all my mediocrity was Joey Chen. Joey's dad brought the family over when his Chinese company started manufacturing in my home town. My dad worked for the company on the production line while Joey's dad was one of the senior managers. The fact that his dad was senior to mine never really entered into my thinking. I just always liked Joey. He was about an inch taller than me at 5'9", had pitch-black hair and piercing dark eyes. He had initially been a bit shy having not learned English until his family moved to my rural, Georgia town.

Perhaps that's why we got along so well. I know most of the locals could be a bit standoffish, but I, in my untraveled mind, had always found Joey and his family to be a bit on the exotic side. And then, Joey was smart....being pushed by his family to succeed academically. He was certainly smarter than I was but never made an issue out of it, seeming to enjoy me being his American side-kick.

Because Joey's family stressed academics, Joey had not played on any team sports. Unlike me though, he probably had the innate ability and coordination necessary but since we were both not jocks by either choice or ability, it always made us feel like outsiders in terms of our school's social hierarchy.

Perhaps it was because of circumstance or fate, but Joey and I had a deep bond. Despite his being the newcomer, he always seemed to be the leader, determining what we'd do when we were together. I never really minded it nor even thought about it much. It just was the way things were for us. Perhaps that's why I guess I didn't question it when Joey announced, "We're going to the Prom!"

"How, Joey? Who are we going with?" was the first question out of my mouth. You see, given all their inherent prejudice, the local white Southern girls hadn't shown any interest in Joey at all having rebuffed any and all attempts he'd made to ask them out. And there was no way Joey would ask one of the black girls in their stead. Unlike me, at least Joey had tried. However, his own lack of experience made him seem to naïve to the local crowd.

As for me, the girls never gave me the time of day. They were simply way beyond me. I thought I was just a late bloomer but I'd soon learn that wasn't exactly the case. I could never figure it out but, if I was honest, I wasn't all that interested in them either....except that I knew I should be.

"Well," Joey said, "well simply go stag. Dad trusts me and said he'd let me drive and will arrange for a hotel room for us to use in case we get lucky."

"That will be the day," I responded, even as I noted Joey's hopeful eyes.

I had been working at a local fast-food joint on most Saturdays and had saved enough to rent a tux, buy new shoes and pay for my own ticket. At least I didn't have to pay for a date's as well as being stuck paying for her dinner and maybe a corsage!

My parents were thrilled I was going to the Prom. I wonder if that was simply wishful thinking that I wasn't gay after all. It wasn't something that was ever discussed but my lack of athleticism and interest in sports didn't always go down well with my rather blue-collar Dad. Still, Mom hoped I might have enough brains to get a scholarship to a modest college knowing there was really no place for a sensitive boy like me in my home town.

Given Joey's Dad's rather senior position with the town's major employer, my parents were always supportive when I asked if I could go with him on outings or to participate in activities. My parents certainly had no problems with him taking me to the Prom and knew we were both very unlikely to do very much given our lack of experience and the reality that neither of us belonged to the in crowds.

So after they took a few pictures of Joey and me in our tuxes and my Dad jokingly telling Joey to treat me right and protect my virtue, whatever that meant, we were off in his Dad's Mercedes to the Prom.

I really don't know why we went. The kids that ignored us before didn't miraculously change. Almost everyone else came as a couple and the others that came alone were a clump of pathetically ugly girls with zits. Joey and I quickly came to the realization that we would have far more fun simply being together than with a bunch of immature high school kids that wouldn't give us the time of day.

By 10:30 p.m., we were ensconced in the rather nice hotel room his dad had reserved for us downtown. The view was rather striking and I think we both felt better being on our own. "Man," Joey said, "My Dad said to get laid and lose my virginity before I come home and you're my only chance!"

Of course, I thought he was joking and said sarcastically, "Sure, I'll just drop my trousers and bend over for you!"

"It doesn't have to be like that," Joey responded, causing me a bit of confusion. "Look, we're going off to College soon and neither of us even knows how to kiss. If you play your cards right, this could really be good for both of us. Just play along and I'll make it right for you." I wasn't sure exactly what Joey meant, but as I more or less always did what he wanted, I soon found myself willing to cooperate.

"Hey Billy, I've got an idea! One of us could play the role of a girl so at least one of us can get some experience."

"What do you mean?" I replied. "How would we do that? How could one of us be like a girl?" I asked, rather stupidly.

"Well," Joey replied, "I saw a deck of cards in the desk drawer when I checked things out while you were in the bathroom. So why don't we play black jack. Whoever wins the first two out of three rounds gets to be in charge and will have the right to determine how things go from now on. Or, we could simply see who has the biggest cock and that person would, by natural right be the man," Joey added.

I wasn't sure which option was best from my vantage point. I kind of assumed Joey, being Asian, would have the smaller cock so that option was 50/50 and perhaps slightly in my favor. However, Black Jack at least sounded fair to me since it would be a game of chance in which neither of us would have a competitive advantage, or so I thought, forgetting that Joey always seemed to win!

Joey seemed pleased that I didn't reject his suggestion outright as any other so-called heterosexual male would have done. But then, I always did go along with everything he suggested so why would I get the balls to stand up to him now? Anyway, sensing my uncertainty, he said, "look, let's just play black jack. I'm sure I'm bigger than you anyway so this will give you a fighting chance to take the lead!"

That pissed me off and led me to respond, "I thought Asians were supposed to be smaller than Caucasians!" to which Joey replied, "What, have you been studying sex on the Internet?"

Of course I turned red with shame to which Joey said, "Look, time is money, let's just play cards and see what happens! I'm better than you at shuffling the deck so I'll be the dealer," Joey announced, after retrieving the cards, never really allowing me the opportunity to back out of his plan. I should have realized that from the beginning, Joey Chan had every expectation that tonight would be his lucky night and that he would end up, as usual, calling the shots!

Joey motioned me over to the little round table, pointed to the opposite chair, and, after taking the deck out of the box, proceeded to shuffle them with the precision of a Vegas card shark. He then dealt our cards. My bottom card was a queen followed by a two. I motioned for another and Joey dealt me a six. I held at 18 knowing the dealer would have to have the same or better to win and the odds of me getting another Ace, two or three were very slim.

Flipping his cards over, Joey had a King and a nine. He had won the first hand. When I showed my cards, Joey seemed to find amusement that his King topped my Queen. I have to admit, my naiveté didn't allow me, at the time, to understand the basis for his mirth!

The second hand became more serious, at least for me. This time, my bottom card was a five and the top, a seven. I really had no choice but to ask for a third. Joey dealt me a Jack! I was finished before he even looked at his cards. I should have realized the advantage Joey had from the outset being the dealer!

"Looks like I get to call the shots," Joey gleefully informed me as if I didn't already know. However, what I didn't realize was how he intended to play the rest of his hand, so to speak!

I'm not sure if Joey had planned the whole thing out or not. Regardless, I could see in his eyes that his mind and furtive imagination were working overtime.

"Billy, why don't you get out of that Tux for me," Joey suggested.

I guess I thought he'd be taking his off, too, and had my shoes, jacket and shirt with those darn cuff-links off before I realized he was just sitting in the comfy chair he had switched to after winning at black jack before watching me strip.

"Don't stop yet, Billy," he directed. "Go ahead and lose your trousers, too," he added.

That's how I found myself in my underwear, standing in front of a still, fully-clothed, Joey Chen.

"You know, Billy, I never paid much attention to your looks before but you are kind of cute which will make this rather nice for me. You hardly have any body hair unlike some of the guys at school. Also, while not fat, you don't have massive muscles. You know, you look kind of soft, almost girlish. Why don't you lose that undershirt for me next," Joey ordered.

Almost like a zombie, I now stood nearly naked in front of my best friend. It was all rather surreal and I began to feel as if we were no longer the equals I had begun the evening thinking us to be. Joey, however, seemed to be turned on by the possibilities that were playing out in his mind and my submission to his, so far, rather innocuous suggestions.

Not wanting to lose any momentum or allow me time to start thinking too deeply about the oddity of our situation, Joey stood up, took off his tuxedo jacket then removed his cuff links and bow tie before sitting back down on the rather plush chair.

At this point I was feeling a bit chilled and my nipples were hardening even though my cock wasn't sure what it should be doing. Seeing this, Joey said, "I have an idea. I need to run to the 24-hour K-Mart and get a few things. I want you to go take a shower and wash yourself thoroughly and then soak in the bath until I get back. That will help prepare you for what I have in mind and will, at least, warm you up."

With that, he was quickly out the door. I was only in my underwear so going in the bathroom to take a hot shower seemed like a good idea. It seemed like I had only just finished in the shower and then started soaking in the tub a little while before Joey was back. When he came into the bathroom, I quickly covered my privates in embarrassment causing him to laugh. "Don't worry, tonight's not about your junk but mine. Anyway, yours looks pretty small and shriveled up," he said, before ordering me to stand up.

Still fully clothed, Joey had me stand naked and lift first one foot than the other on the side of the tub. Joey then lightly dried me before putting some cream he had purchased all over each leg. Then he had me turn around and rubbed more on my ass before adding some on the area around my navel just above my pubic hair. It all seemed so surreal as I had never been naked around another boy or man!

After standing there a few moments, Joey said, "Billie, is your skin feeling a bit itchy?" I indicated affirmatively. "Good, just stand there for a few minutes more." When he was satisfied, Joey said," I want you to get back in the bath and rinse off. I know you don't have much body hair, but the cream I bought helps to get rid of unsightly hair. Women use it all the time to keep themselves nice and smooth. And I'm sure you want to be smooth for me like a woman too, don't you, Billie?"

At this point, my skin was itchy all over and all I could think was to wash whatever Joey had put on me, off! When I was finished washing, I could see hair floating in the tub, the fine hair that was on my legs and ass. It wasn't much because I didn't have much but still, it was gone. Joey then had me stand up and had me hold on to the shower curtain bar and proceeded to shave my armpit hair. Using some scissors, he lightly trimmed my little bush, too. When he was done, he had an almost gleeful look as he surveyed the results of his efforts. From the neck down, except for my now limited pubes, I was virtually hairless.

I felt so odd, standing there, naked and hairless in front of my best friend. Joey then surprised me by saying, "I bought you something special to wear for the rest of the night, and placed your clothes on our bed. Finish drying, come out and get dressed!"

What Joey had bought at K-Mart was a pair of red woman's panties and a 34 B-cup bra. Seeing what was on the bed left me speechless! "What are these for?" I asked. "I'm not a girl; I can't wear a bra and panties!" I added.

"Well, remember our bet," Joey said, "You lost and tonight I'm going to lose my virginity by taking yours. I'm not gay so I thought it would seem less awkward if you at least seemed a little bit like a girl. That's why I had you get rid of your body hair and why I want you to wear a woman's underthings!"

Joey said all this so matter of factly like it was completely logical.

At that point, I felt too shell-shocked by what had already happened to my body hair to think so Joey went and picked up the bra and went behind me. "Look, I'll help you this first time. Just lift up your arms for me, ok?"

Dumbly, that's exactly what I did. The bra felt weird against my skin as he clasped it for me. Next, he handed me the panties which I stepped into and pulled up covering my now deflated cock. "Oh, I've got one more thing. Here's some glossy red lip stick. Put this on like all the girls do when they're dressed up!" Joey directed.

I looked in the mirror as I took the tube from him and tried to apply lipstick for the first time. When I finished, Joey stood behind me, wrapped his arms around my waist and gazed upon the two of us looking back out the mirror. With his shoes on he was about two inches taller than me. I had to admit he looked so much more the man in his white, tux shirt and black pants. As his lips began sucking on the lobe of my left ear, his hands made their way underneath the bra to my nipples and, through the thin slacks he wore, I could suddenly feel his hardening cock rubbing between my panty-clad and now smooth ass-cheeks!

As I gazed on the image in the mirror of Joey Chen with his eyes closed fondling a rather homely looking "girl" that looked like me as he dry-humped my ass, I felt almost light-headed. If I had been a real man, I would never have allowed myself to have been manipulated into this position. Joey had transformed me from his friend into his first conquest and I just stood there unable to resist.

"God, Billie," Joey said with a smirk, "your tits feel almost real and your nipples are getting hard just like the women in porn!"

I felt suddenly hot and could see the flush rising in my face. I had never played with my nipples and, therefore, had no idea how erogenous they were when in the right hands. Given Joey's intensity of both need and demand, and my own reaction to his stimulus, any hope of escaping the inevitable was quickly diminishing for me.

By now, Joey's cock had become surprisingly prodigious and constrained in his form-fitting dress slacks. Joey must have realized the same and guided me back into the bedroom. After turning me around and pushing me to my knees, Joey moved back and sat on the bed.

"Billie, I want you to crawl over here and take off your man's shoes and socks!" he said, with a steely determination as he looked down upon me.

As commanded, I crawled forward and untied and removed his left shoe first and then moved to his right. Before I could take off his socks, Joey lifted his foot and ordered me to inhale the scent emanating from his insoles. It was strangely intoxicating, which Joey immediately noticed.

"Baby, I see your clit likes the smell of my feet," causing me to turn red with shame.

"What do you mean when you said 'my clit'? I don't have a clit" I responded, rather meekly.

"Billie, Billie, Billie," Joey said with amused condescension while looking down on me, "look at your panties and then look at my crotch. A girl has a clit which is like a small dick. It helps her to orgasm when she's being fucked. A boy has a penis which he inserts into a woman to bring her to happiness. Clearly by size what I have and what you have are different. Anyway, don't worry, Billie, I have everything that you need tonight right here," he added as he hefted the obscene bulge that was now pushing fiercely out in his crotch.

Having let me remove his socks, he had me massage his feet. His were a perfect size ten to my smaller, size nine. There were a few, dark hairs on the top of his feet which seemed almost perfectly formed.

In retrospect, I'm amazed at Joey's self-control. Here was a barely 18 year-old guy with a rampantly hard cock dying for his first fuck, yet he had the self-control to pace both his and my deflowering without either cuming from the excitement of it all or losing his nerve in the process.

But now, Joey was getting close to a teenage stud's edge. Quickly lifting his ass off the bed, he pulled his slacks and boxer shorts off leaving me to remove them from his impressive, albeit slightly hairy legs. Joey told me to hang his trousers up and to come right back and assume my place at his feet. When I did, he handed me his boxers and told me to sniff. The aroma was truly intoxicating and went right to my groin. Joey spread his legs wide, leaned forward, and taking his hands, grabbed my head pulling me in to his now rampant crotch.

As I looked up, I could see his taut balls covered in thick, black fur and his Chinese cock pointing up towards the sky oozing pre-cum. What amazed me most was the immense size of his cock-head. It seemed to have a dark red, almost purplish hue and was pulsing with his thick, red, blood.

Joey was consumed with the power he had in his groin and over me and started to taunt me by smacking the sides of my face with his weighty spear. Joey began rubbing his cock across my lips wetting them with his pre-cum. I couldn't help but lick it off.