Before I get into this episode, I would like to cover an administrative detail. Many of my readers have been unable to locate my other stories. The following is a list of the story titles and they can all be found under Prolific Authors / Twonight:
Black Dorm World's Hottest T-Girl The Awakening Star Cruiser The Inmate Shocking Encounter Olympiad Turning 18
Please send feedback to twonight@excite.com. I really enjoy hearing about a guy's first sexual encounter so tell me about it.
Ok, on with the story:
My name is Harry and I am a 28 year-old straight man, living in Chicago with my girlfriend. It was a Friday night and a bunch of guys were over for a night of Texas Hold 'Em Poker. My girlfriend was out of town, visiting her parents, so I was doing the bachelor thing for the weekend. There were nine guys when we started and, within an hour, four of them were already headed home. I pulled a flush, then a straight on the river to take out two more guys and the field was narrowed to three. At that point, I was up $430 dollars and using my chip advantage to lean on the remaining guys.
The remaining guys were my buddy Sam, a pretty good player, and Carl, a guy that had never played with us before. Sam is 29 and a real chick-magnet type who always dates gorgeous women. Carl is a dark-haired jock-type, about 25 and 6'2", who obviously works out. We had been playing for about three hours and had all been drinking steadily. After trading chips for a while, Carl finally eliminated Sam and Sam went into our guestroom and crashed. By this time it was after midnight and I asked Carl if he wanted to continue or go home with his winnings. He smiled and said that it was supposed to be winner-take-all and he was ready to finish it. That was music to my ears. I was holding $525 and Carl had $375.
We continued until I was holding $710 and he had $170 of his remaining $190 in the pot. I was holding a pair of aces and the board had an ace, four, five, nine, and jack. His only real chance of beating me was if he was holding a two and three. I didn't see much chance of that since he probably would have folded when I began raising his bets. When he checked on his last turn, I immediately bet enough to put him all-in and end the game. He considered his options and I expected a fold. Instead he gave me a funny look and said, "How would you like to really put it all in?" At first I was sure he was propositioning me, but then he added, "I have four hundred dollars in my wallet that I will raise, if you let me." I wasted no time in calling and flipped over my aces.
His eyes grew wide and he said "Holy shit! I figured you for a pair of aces and I had three jacks."
"Guess it's not your night my friend," I replied. "I'll have to take that $400 off your hands."
With that he pulled out his wallet and looked inside. It was empty.
"Oh crap," he said. "I guess I left the other $400 at home. I can go get it for you."
"Go get it for me? Is that like 'The check is in the mail' or 'I won't cum in your mouth'? I want my fucking money."
"I'm sorry man. I don't know what to do. I can't give you what I don't have with me."
"Well you better think of something."
"Maybe I could do something for you."
"Like what?"
"I could suck your dick."
At first I thought I had misunderstood and made him repeat it, which he did. I told him I wasn't gay and, even if I was, a blowjob wasn't worth $400. He told me that I could just close my eyes and pretend it was a woman. I have to admit that my cock was getting hard thinking about a blowjob, but I wasn't giving up $400 for a blowjob and I told him so. He thought about it for a minute and then offered to let me fuck him too. This really shocked me and I was speechless for a minute. While I thought of a response, he dropped to his knees and began to rub his lips up and down my growing cock through my straining jeans. At that point, the little head took control and I agreed to his terms, but only after he agreed to let me cum in his ass and his mouth. I wanted to leave him with an assful and mouthful of cum to remind him of how badly I beat him.
He had my cock out in no time and began a world-class blowjob. He took my thick eight-incher to the hilt and licked my balls with each thrust. No woman had ever been able to deepthroat me the way Carl did. I sat back in my chair and he really began to work my cock over. His tongue was everywhere and his lips caressed my shaft like a tight pussy. I tried everything I could to hold off and enjoy even more of this talented mouth, but nature took over and my cum began to shoot into his mouth. I grabbed his head and forced every inch of my schlong down his throat. He gagged but had no choice but to keep swallowing my load. My orgasm seemed to last forever and I came more than I ever had before. When I finally released his head, he continued to suck me, swallowing each and every drop. For ten minutes he just stared up at me as my cock rested in his mouth, leaking the last of my cum onto his hot tongue.
Finally, my cock began to recover and it slowly stiffened and grew to its previous lengths. Carl lightly ran his tongue on up and down the underside of my shaft until my prick was as hard as a rock again. He reached in his pocket and pulled out some lube, dropping his pants in the process. As he removed his pants, I noticed he wore no underwear. I was stunned to see a gigantic cock swinging from his crotch. He leaned over the Poker table and reached back to grease his ass in preparation for my entry.
"Ok buddy, I raised you, now go all in," he said with a chuckle.
I had never fucked a woman in the ass, although I had tried a couple of times. My girlfriend just couldn't handle my thick cock. I was afraid that Carl would not be able to take it either.
"Come on Harry, put that ace in the hole," he joked. These puns were getting even worse.
I placed my cockhead at his entrance and he maoned as I pressed forward, but it did not break through.
"Stop messing around and fuck me, dammit," he hissed.
"You asked for it," I replied as I rammed four inches of thick meat up his ass. He gasped briefly than shoved back taking the remaining eight inches in his tight tunnel. I wasted no time in beginning a hard fucking motion, giving him no time to adjust to the log that was reaming his butt out. He didn't seem to mind, panting and pushing back as I plumbed the depths of his butt. Faster and faster I pounded his hot hole and he took it like a man. For five minutes I just held his hips as I hammered him. Then I decided to further explore this new experience and I told him to lie on his back and raide his legs. I quickly crawled on top and began to fuck him just like a woman. It was excting watching the look of total pleasure on his face as my cock filled him over and over again. His hard cock flopped between his tight abs and mine as his hands reached behind to cup my ass. He squeezed my butt and pulled me even deeper inside him until I could hold back no longer.
With little warning my balls exploded and cum shot into the depths of his ass, filling it with steaming jizz. When he felt it, he stroked himself a couple of times and shot his own load all over his chest and mine. I had shot many loads inside my girlfriend's pussy, but I had never had such an amazing orgasm or feeling of satisfaction as I did at that moment. When I finally pulled out, he took my cock in his mouth and sucked me until every drop was down his throat. Then he licked my chest clean.
At that point, I began to feel guilty and I was afraid that Sam would wake up and catch us. I scooped up my winnings, told Carl to see himself out, and went to bed. As I lay in bed, trying to sleep, all I could think of was how exciting it had been to fuck Carl. I also wondered what it would be like to feel his big dick in my mouth. I finally gave up on going to sleep and went to the kitchen to get a glass of water. As I passed the Poker table, I decided to put the cards and chips away. I saw Carl's last hand still face down on the table. I flipped the two cards over and was stunned to see a 2 of clubs and 3 of hearts. That lying bastard had set me up. He was holding a winning hand and gave it up to seduce me. I couldn't decide whether I was more angry or flattered. While I was struggling to grasp what had happened, I heard a loud groan from the guest room.
I decided to check on Sam, because he was pretty drunk when he went to bed. I opened the door and my jaw almost hit the floor. Sam was on his hands and knees with Carl's huge dick buried in his ass. At first I thought that Carl had taken advantage of poor drunk Sam until I heard Sam begging him to "fuck my ass like a whore." Then it hit me. Sam had been in on the whole thing. He had brought Carl to the game and they set me up.
Carl smiled when he saw me and asked if I'd like another turn in his ass. Once again, lust ruled the day and I was balls-deep in his butt within seconds. His cock was still buried in Sam's butt and we quickly found a three-way fucking rhythm as two thick slabs of meat filled two hungry asses. Before I came, we switched and Sam filled Carl's hole while I gave Sam a hot injection of manjuice up the ass. He followed that up with his own load up Carl's ass. That left Carl as the only one still needing release. Sam started to swallow that big dick, but I pushed him away and took as much of it as I could in my mouth. Carl groaned with pleasure and, with just a few more strokes, flooded my mouth with hot cum. At first the pungent, salty flavor surprised me, but the erotic scene around me made me want every drop and I drained his hose dry.
Needless to say, Sam and Carl spent the rest of the night and all the next day introducing me to every aspect of man-to-man sex. I finally worked up the nerve to let them fuck me and, when my girlfriend returned on Sunday, I still had cum dripping from my butt. I will be back for more.
As always, send comments to twonight@excite.com. Check out my other fiction stories, Olympiad, The Awakening, The Inmate, Turning 18, and Star Cruiser - and my nonfiction Shocking Encounter and Tess' story - World's Hottest T-Girl.