So It was the summer after my senior year of high school when it happened. This local comic book shop owner I had known forever must have known. He must have seen me peek at his little corner of adult books a bit too long. Especially the gay magazines.

He invited me to his buddies poker night. I had never really played poker so I declined. But then he said I didn't have to play poker, just be there to help serve drinks and stuff. He even said he'd pay me $20 to be there.

I figured it would be OK to do that. I knew he had video games to play (I didn't) and thought it would be easy money getting beers and chips for these guys.

So the night comes when I had agreed to help and I show up at the comic book shop owners house. He shows me the table and all the stuff I'd need and then he tells me. He says that - if I want to - I could earn more money by serving naked. And even more if I put myself up as the nights prize.

I was shocked. Well not shocked. But felt a little weird. I asked him what he meant. He said that whoever has the biggest pot at the end of the night would share half of it with me to fuck me. All if I was still a virgin. I knew then that he must have caught me looking at the gay comics in his shop. (might have seen the hard on in my shorts, too)

I asked about his friends. and he described each one that was showing up that night. They all sounded like average guys. One was a little heavyset. Another on the thin side. But, by that time I was all aroused with young man hormones. So I agreed.

The first guy shows up but the owner, well, I might as well call him my pimp for the night, wants me to wait until they are all there before I see them. So I go to his bedroom and wait for about 15 more minutes. I hear the other two come in.

Now they are waiting for me when the pimp comes and asks me to serve the first beers to them and then do a little strip tease to get them worked up. I agreed and brought in four beers.

The pimp introduced me to each guy and I handed them each a beer. When my hands were empty, I pulled off my shirt then my shorts. And as I was reaching for my underwear, the guy closest to me said stop! He'd do that for me. So I let him.

He pulled my short down low, slowly. "Accidently" touching my ass. Each of them seemed to like what they saw, and obviously, me being completely naked in front of four men had me aroused as I was sticking straight up. they each asked if they could touch my ass or cock. Which I did let them For a $1 a touch.

I made like $10 right then and there. Throughout the night I got beers for the guys when they asked. Let them touch me when they asked (probably $40). One even asked me to sit on his lap for a hand. For $5 I did it.

So as the night progressed, I could tell who was most likely going to win. The first guy to show up. He was also the guy to ask me to sit on his lap. So at the appointed hour of 10 o'clock. The cash was counted and the winner was named. Sure enough it was the taller, thinner guy.

He counted up his money and gave me half. As he stood up he grabbed my ass and said, "can't wait" and headed off to the bathroom. I heard him letting out all that beer he had. The three others went to the living room each with a fresh beer and I went to the only bedroom in the house to wait.

I was there for about 5 minutes, laying on the bed stroking my cock, thinking of what it was going to finally be like. Getting fucked. That's when the pimp opened the door. He smiled and said I had to be out in the living room. Puzzled I asked "why?" He said so they could all watch.

I went out there and sure enough, they were all naked with the nights winner sitting on a chair in front of the couches. Each of them had the beginning of an erection. But that grew as I knelt before the winner and took his cock in my mouth. I didn't know this stereotype about tall thin guys having huge cocks at the time, but this was my first, and it was likely one of the biggest I'd had.

So I'm there sucking cock for the first time. Trying to emulate what I had seen in the gay comics, which is not a good place to try to learn to suck cock. The winner was OK with the fact I was new. He was gentle, but still tried to force his at least 10 incher (with huge balls, too) as far down my throat as he could. Which wasn't far. (Now I could probably take the whole thing easily)

I could see the others each stroking their dicks in my peripheral vision. They seemed to like what they were seeing, even if I was new to it. That's probably why they liked it. Since I was s cocksucking virgin.

Then the winner pulled me up. I could barely catch my breath before he had me laying on the edge of the couch with my legs up in the air. My ass was scooted forward so that my anus was really exposed. he grabbed a tube of KY jelly and smeared it both on my ass and his cock.

Before he put it in, he looked me in the eyes and said "It will hurt, there's no way around it." At that he started to push his head in. Sure enough, it felt like my ass was on fire. But he was really gentle about it and didn't just shove it in (like some assholes I've met since)

he just kept working it in a little at a time. Eventually, I was clawing for anything I could to pull me away it hurt so badly. But he had me pinned. Soon he was sliding all the way in and out of me. It seemed like forever. But I am sure it wasn't more than a few minutes.

Then he turned me around. Had me get on my hands and knees in the middle of the room. On the shag carpet. I stayed there, biting my lip. Sure that my ass was bleeding a little (10 inches the first time, it's gonna bleed). He lubed himself up a bit more before taking position behind me. This time he did it slow. But went all the way in the first time. I must have been stretched out enough from before.

At this point he started pumping me a bit harder.
And faster. I was bouncing quite a bit. My cock was no longer hard as all I could think about was being fucked by a huge cock. And that cock hurt.

I couldn't think of anything else besides that cock. So that's why I didn't notice it when one of the other players was standing over me cumming on my ass. Then the pimp was on the other side doing the same. Finally the third guy was in front of me and he jizzed a TON all over my back.

That must have been the catalyst because just as the third guy was finished drizzling cum all over my back (and the previous two cumloads were sliding down my asscrack and no doubt being pumped into my anus) is when the winner decided it was time to explode in my ass.

Now, I have been with lots of guys since this first time. And I've had probably a couple of hundred loads pumped up my butt in the last few years alone (not a couple hundred different guys), but this load was so huge, so massive, that he wasn't even half done and it was squirting out of my ass. You should have seen the puddle of jizz on the floor.

At that, the winner collapsed on me. I leaned forward and he just laid right there on top of me, cock still in my ass. He then passed out for at least 20 minutes. Which is fine since it gave me time to recover. I could feel the warm puddle of jizz between my legs and could tell that it was soaking into the carpet. The other guys cum on my ass and back was drying, sticking the two of us together.

After a bit the other guys had left and there was only me and the pimp. He handed me a big stack of money and said that they get together every other week and that I was welcome to come back. Which I did. I also got the number of the winner and we hooked up about 5 more times. Each time his load was huge! One time when he wanted to cum in my mouth, it literally filled my mouth! And I'm sure some of it spilled over.

Anyway, over the next few months I would be their little bitch cum dumpster for money. And when I was back in town from school, I would come by for old times and get fucked. (none of those guys were bottoms, so I never got to fuck any of them) I probably paid for a semester of school with what I got from them.