It was a slow night at the bar. Summer can be dead, too much to do besides going to a bar. Even if you have the best male strippers in town.
David was feeling his oats, and there just were not enough customers too keep him entertained. Yeah, I know the strippers are supposed to entertain the customers, but the customers help psych us into better performances. It's really hard to give your best to a small crowd. Or a crowd of regulars, who've seen most of what we have to show. Our regulars weren't getting into our routines. We weren't getting tips. The bar wasn't selling drinks. The night sucked.
That's when David got his idea. He bet me, Kevin and Brad, that he could rake in more tips then the rest of us. I shrugged it off, because David usually made more than the rest of us. He had beautiful Mediterranean features, smooth olive toned skin and a whopper in his g-string. Compared to the rest of us, corn fed Midwesterners, he was exotic and exciting. Blondes and redheads were pretty common around our area. Brad and Kevin weren't biting either. Frustrated, David kept at us until, I broke down and asked what the stakes were.
David totally flabbergasted me, when with a gleam in his eye, he offered up his ass to the winner. In all of the time we'd danced together, I'd never heard of him bottoming for anyone. Brad and Kevin weren't very interested. Now if David had offerred to plow them, they'd have been all over it. So David turned to me. Now, I was ready to give it a whirl, because I'd secretly wanted David's ass, for as long as I'd known him.
Then he upped the ante. If he won He got to fuck the ass of whoever went against him. Brad and Kevin brightened right up, me, not so much. I'm not much into bottoming, and frankly David's monster scared the hell out of me. Still, the chance to get into David had never come along before and might not ever again. Besides, I was as bored as he was.
Since he made the bet, he laid down the rules. If he thought any of us were throwing the game, just to ride his dick, all bets were off. Both Brad and Kevin turned red, pretty obvious what their plan was. They both backed out of the bet.
So it was down to me. David knew I'd give him the fight he wanted. So I stepped up to the table. Our few customers were in for a showdown.
David and I pulled out all of the stops we could get away with. (There were laws that were not in our best interest to break) Somehow, word of the bet got around and our customers really got with the program. Every regular has their favorites. The trick was to get them rooting for you.
To my surprise, David and I were pretty close to neck and neck. Then out of nowhere a whole crowd of guys showed up to party. They came in at our last set. They were tucking bills like they had found a money tree. It was almost impossible to tell who was winning. Then, one of my regulars, looked me right in the eye and planted a fifty in David's g-string. I knew he was making me pay for my not fucking around with customers rule. My ship was sunk.
After the last set, I was ready to concede defeat, but David insisted we count out the money. We both knew I wasn't going to beat that fifty. Guess he wanted to bask in his win.
To noone's surprise David won. I shrugged and asked when and where. David laughed and said he wasn't waiting and I was coming home with him.
I had no choice, a bet was a bet and I don't renege.
When we got to David's, I was already to grit my teeth and get it over with. David had other plans. He kissed me and cuddled me. I had no idea he was such a romantic. He made love to every part of my body. I had no idea that having my feet kissed and fondled would be so wonderful.
Then he was pushing my legs up and his monster was pushing against the back door. I did my best to relax, but nothing that big had ever tried to get in before. I'm telling you, it hurt like the blazes. But David took his time and let me get used to the invader. I felt like he was going to bust through my belly button, and my hole felt like a semi was stuck up there. Finally I felt him begin to move in me. And it began to feel good. Part of it was pride. I was proud I could take that whole thing and not split apart. Then it began to feel real good. Before I knew I was raising my ass to meet him, and he was starting to slam into me. I liked it, no I loved it. Before, getting fucked was no big thrill, but tonight I wanted nothing more than that big dick working me into climax.
When David came he thrust into me with such force, I thought he would tear me apart. I came while he was still filling the condom within me.
We lay like that for what semed like forever. Then finally we pulled apart, and David held me in his arms. It was then that he told me he had cheated. It was his fifty that my customer had given him. He thought I'd be pissed, but I guess I was more flattered that he wanted me that much. However I did vow to myself, that I was going to plant my dick up his ass someday. But that's another story for another time.