Ok, the standard disclaimer applies, Be of legal age, don't be offended by the beautiful thing that is love between two men, yada yada yada. Anyway, Many of you may have read my "My date with a boy" story in the college section. This story is a little different than that one in that it is more driven by simple sex and not self discovery and love like the Date story was. Currently I have no plans to continue this story here, but if I get enough feedback, who knows, there could be more. Anyway, I hope you enjoy it.
I was never one of the cool kids in school. From day one I got picked on by all the popular kids. I can't say I blame them though. I was a prime target, I was terrible at sports, I used to play with the girls on the playground, or spent my free time reading books against the wall. I may as well have just worn a t-shirt with a target on it.
But what really made it harsher was that my sister, Kayla, who was 2 years younger than me, had it so much easier out there. She was popular with everyone. The hardest thing about it, was that when I was a junior, and she was a freshman, I didn't have a date to the prom, and she had plenty of guys willing to take her.
I wasn't too depressed that there weren't any girls in the school who wanted to take me to prom, because I had realized during my sophmore year that I was homosexual. The only people who knew this were me, my sister, and a few female friends of mine who would have gone to prom with me anyway, but had boyfriends so they weren't free. Even though I wasn't out of the closet, I didn't want to blatantly be something I wasn't by pretending to be a nice normal straight guy anyway.
Even though I was immensely jealous of her popularity, I was very close with Kayla. That was why she knew I was gay when even our parents didn't. She was great at helping me avoid the issue whenever mom would ask me questions about my lack of a love life.
What depressed me the most about the prom situation was that the guy who was lobbying the most to be Kayla's escort, Tyler Vaughn, was the guy who I had been fantasizing about since I admitted my sexuality to myself. I finally confessed to Kayla, when she asked me which of her suitors I found the most appealing, that I had often thought about Tyler and me in the sack together. It was then that she got her idea.
Kayla accepted Tyler's offer and made arrangements to go with him to the prom, and to his after-prom party, as long as he invited me to the party too. I thought he would get mad because he had to have me there in order to get the sister, but suprisingly he didn't care at all that I had to come.
Everyone knew what happened at Tyler's parties. His parents were loaded, and there were 5 different bedrooms upstairs where people could have sex. Thats what happened at Tyler's parties. Tyler was rumored to keep a tally somewhere of all the people who had lost their virginity at his house. No names or anything malicious, just a tally. His brothers had started the tally back when they had gone to high school, and Tyler was the last of them, and he was looking to make his after-prom party the highest number yet. And I knew that had to include Kayla.
But Kayla had other plans. She told me she really wan't all that attracted to Tyler, though I personally think she's crazy. She said not only did she not want to lose her virginity while she was only 15 years old, but she also didn't want to lose it to Tyler.
But she would make him think she would. This was her plan. She was going to tell Tyler to go to his bedroom and turn off all the lights, and get undressed. After he lay there for about 5 minuts, I was going to creep into the room in the darkness, and perform whatever for him that he had planned for her to do, and then before he turned the lights back on, I would slip out, and he would never know the wiser.
I was worried as hell about this, How the hell would I be able to pull off a scam like that? Kayla said not to worry about it. She would make sure that Tyler had several drinks before she sent him to wait for me. Also she would lend me a pair of her panties and a camisole top to wear so that i would look more feminine if he caught a view of me in the dark a bit, or if he started to feel his was down my back, he wouldn't find my boxer shorts. Every single rational thought in my mind told me that this was a bad idea.
But this was my only chance to be with Tyler.
By the night of prom I was a nervous wreck. I hardly paid any attention at the dance itself because I was too busy freaking out about what we had planned for later on that night. Before I knew it, the DJ made the last dance call and the students were being herded out of the building like cattle.
Tyler dropped Kayla and me off at our house after the prom so that we could go change for the party. He lived about a block away from us so we would just walk to his place afterwards. As soon as we got in the house Kayla and I ran upstairs. She handed me the underwear she had promised me and she told me to wear jeans and a greenish shirt. She said that'd be close enough to what she was wearing that a drunk guy in the dark couldn't tell the difference.
It took me a few minutes to get comfortable in the underwear, before I buttoned up my shirt and pulled on my jeans and met Kayla at the door. She smiled and asked me if I was ready, I just looked at her with my nervous face and asked her if she was kidding. How could I EVER be ready for this? she kissed me on the cheek and said everything would be ok, and we headed to the party.
The party was ok, I guess. Like I said before, I'm not incredibly popular so no one really wanted to talk to me except for some other losers who needed someone to talk to. If my sister and I hadn't already been planning our bedroom switch on Tyler, I may have tried to get one of these guys drunk to see if maybe they too had some alternative ideas, several of them did hit some points on my gay-dar, but my mind was already picturing Tyler in a dark bedroom.
Finally the time came. Kayla came by and slipped her arm through mine. the nerves I had earlier were multiplied as much as they could be, I would have been frozen had it not been for the comforting arm of my little sister guiding me along. Finally we got to the room. I looked around to make sure none of Trent's buddies were around to rat me out to him, and finally, I nodded to Kayla, who walked away.
Slowly, I let the door creep open. I could hear Tyler move himself around in the bed a little bit. I heard him ask "is that you baby?" but rather than risk my voice sounding too male, I simply pressed my fingers to my mouth and shushed him while closing the door behind me. I slowly undid my pants and shirt and dumped them on the floor as I slithered over to the foot of the bed. I felt my hand raise up against his thigh and go inward. My nerves had vanished and my pure desire for this boy took over. He started to jump a bit, and in the most feminine voice I could muster, I whispered
"just relax."
Slowly I licked my way up and down his thighs and legs. as I worked my way down his leg I tickled his toes with my tounge before moving my way back up again. I began to push his shirt up and I felt my lips press against his belly. I began to give him several little kisses on his stomach, and then I felt his hand stroking my back through the microfiber of the camisole.
"Did you get dressed all sexy for me?" he asked
"Shhh" was all I responded with. I continued to kiss his belly as his fingers found their way to the elastic waistband of my breifs. "naughty naughty" I whispered as I felt his finger begin to lift the band and go deeper, and try to work their way around front. I knew I had to act fast or my secret would be out. "you'll get your turn." somehow he seemed to like the idea of waiting for a prize so he ceased his attempt to finger me.
Finally as I pressed my lips against his six-pack stomach, I brushed the waist of his pants with my chin. I slid off the bed a little bit untill my knees and shins were on the floor, and I began to unbuckle his belt and undo his fly. I heard him start to moan a bit as I pulled his pants down to his knees.
He was wearing a pair of breifs, instead of boxers, and i decided to be a little randier. I pressed my teet on the waistband and pulled back untill he was almost exposed. I wanted this to last as long as I could make it so instead of going right for the gold, I begain to kiss and lick the skin around it, I could feel his pelvis begin to thrust with sensantion and anticipation and finally I decided to go for it,
I pulled the underwear down to his knees with the pants and got myself a good look at Tyler's penis. It wasn't one of those 8 inch ones you see in porno movies or read about in supermarket erotica... but it was beautiful to me. I began to tease him by licking around the head untill I could taste a bit of precum. Before I knew it though, my lips were around the head and I could feel is hand begin to run through my hair. and for the first time in my life, I began to give a blow job.
As I let him slide further into my mouth and toward my throat, all the while licking the shaft as it grew and pulsated. I begin to let it slide up and down along the walls of my mouth and licking the sides of it. Tyler began to moan and I could tell it was about to expode. Suddenly the shaft began to pulsate and tylers hand was pressed firmly against the back of my head, and I felt that warm salty come start to shoot its way against the back of my mouth.
I had been thinking before this about whether or not I would spit or swallow once he came... but the next thing I heard out of Tylers mouth suprised me so much that I swallowed the whole wad of it...
Tyler was calling out my name.