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Winning Is Everything

by Alan Katz

S/M

About five years ago four of my friends and I decided to buy and operate a local bar. We had scouted the area and felt it would make a lucrative investment. Just how lucrative, time would tell. The bar was located near the docks and when ships from the Navy landed in port, we were guaranteed a large clientele--sailors on temporary leave. My friends and I enjoyed watching sports and so when we rebuilt the bar, we added some private soundproof rooms where a group of guys could sit around with some beers and watch professional sports on large TVs. There was even a room for playing cards, and a room with a ring to hold amateur boxing matches. After laying out a large initial investment, our business thrived almost from the very beginning. We were packed every night during the six weekday nights we were open. We were closed Monday night. Monday night was card night--a night away from our wives and kids. Most of us were in our late thirties and were married. We enjoyed being with our families, but needed a night with the guys. And our wives were really very understanding. The card games were usually played with just the five of us attending. It was your typical poker game with beer, pretzels and lively conversation. I guess after a while no matter how much fun something is, if you do it week in and week out it starts to get boring. I don't remember who brought up the subject or when it was first brought up about finding something more exciting to do on Monday nights. But the subject did come up. At first, it was just some mouthing off by some of the guys, then it became more serious. I recall one of the guys saying that he was even getting tired of watching professional sports since there was no real incentive for the highly paid athlete to win. I remember him saying something like, "Only when the athlete knows that losing has real consequences, would the contest have meaning." We asked him what he meant by 'real consequences'? And he had to think a while before laughing out loud, "If a guy knew that if he lost, he'd be fucked by the winner." Boy did that ever get the group's attention. Trust me when I tell you that all of us were straight as arrows and certainly had not tried swinging the other way. Yet I had to admit, the idea seemed to excite as of us. After a few more rounds, we decided to end our poker game early and think about how we could set up such a competition. What would the contest be about, where we would hold it and who would we get to participate? It really didn't take long for someone to suggest holding a nude oil wrestling match in the room that had the boxing ring. The last question as to who would we get to participate was another matter. We wanted our contestants to be evenly matched and real macho dudes. Real men who would fight to the bitter end to save their manhood and avoid getting fucked up their ass. It didn't take long for us to realize that we could scout out the sailors who regularly visited our bar and then lure them into this battle. We had mapped our plan, now we had to implement it. We decided that once we gave thumbs up to our choice of which sailors we wanted in the contest, we would invite them to join our Monday night card game. About a week later on a Sunday night, the bar was hopping and all of us were eyeing out the crowd. There were at least 25 sailors in the bar that night and finding two who fit the bill wasn't difficult. The two guys we selected, were more than flattered to be invited to our card game. We told them to come back the following night at 7:00 and knock at the back entrance to the bar and we would let them in. The trap had been set. Sure enough our two macho sailors knocked at the back door and we let them in. They sat down and began to drink the cold glasses of beer we had laid out for them. We began playing cards. In about 15 minutes they started to get drowsy and fell quickly to sleep. We had drugged their drinks. We dragged both of them into the room with the ring. We stripped off their uniforms and chained them buck naked to the wall. Both were well built. Evidently they both worked out a lot. They were of the same height and weight. The contents of their wallets revealed that both were married, one of them had a 3-yr-old son, and they were both around 25 years of age. We couldn't have selected two more evenly matched contestants. As they slept off the effects of the drug, we shaved off their chest hairs. We then poured baby oil all over their bodies. We wanted this wrestling match to be a real slippery and intense battle. John was the first sailor to wake up and was stunned at what had happened. He started to scream to let him go, but those were futile efforts. Soon his buddy Jim awakened and he too had a similar reaction. They eventually calmed down and let us do the talking. We explained to both of them that in order for us to release them, they would have to hold a nude wrestling match. We further explained that in order for the match to end, one guy had to get his big cock up the ass of the other and shoot his wad inside. Almost simultaneously they both said that they weren't gay and wouldn't cooperate. We sort of expected this response. So we took turns persuading them that it was the best of the alternatives they faced. Our method of convincing them was thrashing both their soft white asses with a leather whip we had recently purchased. Just a few snaps of the whip across their buttocks caused searing pain and made them howl, and they quickly agreed to enter the ring. Our dream contest was ready to begin. We placed bets on who we thought would be the victor, confident that we'd get our money's worth. We placed each of them at opposite ends of the ring. We repeated the simple rules that they were to follow. When the bell rang, the match began. They would continue to fight until one guy had successfully ejaculated his manjuice inside his opponent. Once we were satisfied that this had happened, the match was over and they would be free to go. We were honorable men and we meant what we said. We rang the bell and watched as John and Jim cautiously moved closer to each other. They clearly had been buddies before entering the ring. Now they knew that in order save his own virgin ass from being violated, each would have to win this battle. Jim made the first abrupt move, he went for John's legs. But he slipped as he dove for them. John was able to move to the side and Jim temporarily lost his balance. As Jim turned around to face John, John had wrapped one arm on top of Jim's shoulder. He managed to get Jim down on one knee and was trying to use this advantage to get Jim face down on the ground. John's hands slipped over Jim's well oiled body, and Jim then was able to gain the upper hand. He gave John a chop to the midsection that stunned John. He then grabbed John by the balls and squeezed them so that John fell to the ground wincing in pain. Jim had learned fast about doing whatever it takes to win. Jim soon had gotten behind John and was able to get on top of his back and push him facedown into the mat. He then mounted John and wrapped both his hands around John's waist. John tried to fight Jim off and for a while it looked like a cowboy riding a wild bronco. But Jim was determined and held on, until John fell back down fully exhausted by his efforts. The match was already a good ten minutes old and had been more exciting than any contest any of us had ever experienced. All that was left was the 'climax'. Jim was able to position his cock which now was a hard 8 in long at John's crack and after a futile effort by John to keep his hole closed, we could see Jim's cock bury itself deep inside John's manhole. John cried out as Jim began humping him. The back and forth, in and out motion of his cock and the pendulous swinging of Jim's balls as they smacked against John's ass, aroused all of us. After about five minutes of humping you could see Jim release his manjuice inside John's spent ass. Jim pulled his cock out of John's ass and we saw the remains of the white creamy liquid that coated his still hard rod. He then fell onto the mat completely spent by his efforts, but relieved that he was the one who did the fucking, not being the one getting fucked. John, the defeated opponent lay slumped in the corner, a whimpering shell of a man. We wiped off both contestants and thanked them for giving us such a fine performance. We let them get dressed and leave the bar the same way they had entered it. That night set up what was going to become a frequent Monday night event. Oh sure, we still play cards on Mondays most of the time. But at least once a month we staged another wrestling match, 'where winning is everything, and losing is unthinkable'. The matches sure weren't boring, no matter how many we held.


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18 Gay Erotic Stories from Alan Katz

A Lesson Learned The 'Hard' Way'

Rich, Jeff and I had been buddies since childhood. Our parents lived on the same block and we grew up going to the same junior high and high schools. We played sports together, and for a while even formed our own rock band. As we grew up, got married and each started a family, we always found time to spend together. We had an annual vacation in the summer where

A Long Dry Spell Ends

After having such an incredible run of luck during the last month, the gang and I began to believe that it would never end. It started when we had ambushed a pair of young cops and after taking turns brutally sodomizing them, forced the cops to help us find other cops with tight virgin asses to explore. It wasn't long before we had added, another young cop and two tough

A Reverse Sting

I was heading out of town. About a half-hour north I got routed around an incredible chain-reaction pile-up: cars, trucks, vans, from jus dented to shreds of tiny metal; police cars, fire trucks, ambulances, tow-trucks were everywhere. I was sorry for anyone who got hurt but I was getting antsy, and with all the cops tied up in the accident, didn't think I'd have to worry about

Ambushed

It had been a few weeks since we had gang raped our two macho cops, Brad and Bill. Having forced them to fuck each other and then having the action videotaped, we had the perfect way to force these dudes to help us find more raw virgin ass to have fun with. Both those guys wanted to keep their jobs and they sure didn't want their fellow cops knowing that they had gotten it up

Justice Is Served

Randall and I had been best friends during most of our days at college. We had come from different parts of the country, and certainly had completely different backgrounds. Randall's parents were wealthy and he had always led a pampered life. My parents had scrimped and saved to see that I could get a decent education. We met one day in our freshman year, when we

Learning To Be A Cowboy

I'm always excited when the new summer cattle drive starts. I've been doing this drive with a bunch of the same guys for over ten years. The season starts in early June and we're finished the 2nd week in August. The crew is usually made up of about ten guys. There are 8 of us so-called 'veterans' and then we usually hire two college age kids who we 'train' each summer. Most of

My Brother--Too Big For His Britches

I had always known that my brother, Tommy and his best friend, George were perfect assholes. But just how perfect was only learned later when I was 23 years old. Tommy and George are a year older than me and quite the jocks. They both are over six feet tall and well built. In fact they look more like brothers with their coal black hair and almost identical builds than

My Roommate Brad And I Made Love

Brad and I have been college roommates for over a year. I've wanted to fuck that cute bastard for as I long as I could remember. He's such a hunk-with a chest covered with cute short brown hair. Unfortunately, Brad is straight right down to the tips of his toes. How many nights I had to stay away as he brought some gorgeous chick to our apartment and humped the living daylights out

Opportunity Knocked Again

If you read my earlier story 'When Opportunity Knocks', then you saw how we took full advantage of an opportunity when it presented itself. We hadn't really had time to prepare, but nevertheless the fucking episode was self-satisfying. Little did we expect another opportunity to present itself so quickly afterwards. But it did, and now I'd like to tell you how we took

Rookie Cops Get Nailed, Part 1

Rookie Cops Get Nailed - Part 1 Our prey were two young very macho cops, Brad and Bill. Both had been on the force for a few years. They had been our friends until they joined the force. Things started to change slowly after that. But soon they started hassling us and one day we started talking about this. We stated talking about how tough a guy

Rookie Cops Get Nailed, Part 2 - The Conclusion

Rookie Cops Get Nailed - The Conclusion I had just had Brad come into my hands and could tell by his body language how this straight macho cop had experienced his first taste of humiliation. But I could tell he was far from being broken. I had, in fact hoped for this to be the case. There's really no fun to break a young stallion that doesn't

The Long Cattle Drive

I was about 19 that summer that I spent out on the range, working with Dad's ranch hands, driving cattle across the Texas flatlands. Dad's ranch was in New Mexico, and the nearest cattle shipping point was in Abilene. It was a grueling drive, and the hot, dry winds kicked up a lot of dust and made it uncomfortable. However, I looked up quite a bit to the older cowhands, young

The Professional

I'm a professional and I'm the best at what I get paid to do. I'm hired to teach a lesson to some punk who has dissed someone or failed to make payment on a loan. My clients pay me well, quite well. And they should because I always deliver the goods. I don't know many other guys who are professionals in my field. I've been doing this for over ten years and my business is

The Sting

I was heading out of town. About a half-hour north I got routed around an incredible chain-reaction pile-up: cars, trucks, vans, from just dented to shreds of tiny metal; police cars, fire trucks, ambulances, tow-trucks were everywhere. I was sorry for anyone who got hurt, but I was getting antsy, and with all the cops tied up in the accident, I didn't think I'd have to worry about

The Surprise Video, Part 1

It had started out as a prank. A few of us wanted to make a video of our dorm buddies as they showered. We were planning to show the surprise video at a dorm party and watch their faces as everyone saw them naked and playing with one another as guys tend to do when they shower. Little did we know that we would catch on tape was something far more serious. But as it

Three Guys And A Van

Disclaimer: Please remember that this story is fictional--pure fantasy and written for entertainment purposes only. Safe and consensual sex is strongly encouraged! We think of ourselves as three normal guys who just like to have some man-to-man fun once in a while. We're all married and love our wives, but need some times to ourselves. Greg is a cop, Tommy who owns the van we

When Opportunity Knocks

We were just sitting in the living room of one of the guys apartment, talking about our score so far--three cops taken, Ken the most recent just last week. We started to act 'cocky'. We decided to set a goal of how many tough macho dudes we'd like to fuck their asses. After much debate we settled on trying to snatch roughly a dude a month. So far, we had always

Winning Is Everything

About five years ago four of my friends and I decided to buy and operate a local bar. We had scouted the area and felt it would make a lucrative investment. Just how lucrative, time would tell. The bar was located near the docks and when ships from the Navy landed in port, we were guaranteed a large clientele--sailors on temporary leave. My

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