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About a year ago, maybe a little more, I had a best friend named Bret. Bret and I met in high school. We stayed friends through our college years, even though we went to schools in different states. In high school, we were both on the wrestling and track teams together, and hence both in good shape physically. Besides that, we had few secrets since in addition to being friends, and having double dated on several occasions, we always saw each other undressed, in the locker rooms, showering, etc. as most teammates have. I have fantasized lots about possibly getting together with Bret for a little friendly masturbation experience, but I wasn't sure where he stood so I never acted on it. (I found out I enjoyed guys too late in high school.)
Last summer, we had been sitting around the community pool, (in our speedos) and the topic turned to sex as a couple of nicely shaped and bikini'd girls walked past. I was having some fun with Bret when a younger guy, also in a speedo and super good looking, walked past. I said to him 'I notice you were eying him pretty good....you into the other side too? Bret seemed to get defensive and said that he could never even think of getting together with another guy, and asked me if I had since it sounded like I had some experience. I blew him off and said 'Right.....we'll talk later.....'
We went to the poolhouse, showered, and changed back into our street clothes. Again there were no partitions, so we both saw each other full nude. Bret seemed to get better looking each time I saw him, bikini tanned and with a hot 'in his prime 20's' kind of body. We got into my car and drove back to my place where he had left his car. Once in the apartment, we opened a bottle of wine and ordered a pizza. Just before we were done, Bret brought up the pool again, commenting how nice many of the girls were. I agreed, and then Bret asked me what I meant when I said 'we'll talk later.' I told him to forget it, and that he probably wasn't interested in my opinion on the subject anyway.
Bret pushed for an answer. I told him I had a little bit of a weird, not mainstream view of sex. I told him that my feeling was that as long as any two people being together didn't hurt anyone else that pretty much anything goes. I also told him I thought most people, given the right opportunity and the right person, would try a same sex experience, if only once to see what it was like. I told him too, that I was pretty sure some of our teammates in high school had even tried doing it with each other.
Bret said that was 'bullshit' and maintained that HE was 'totally straight' and could never get turned on by anything even remotely bi or gay. His confidence and assertions were unflappable. BUT.......the way he maintained he was TOTALLY STRAIGHT I felt there was something there he was trying to hide. I said that when you watch a porno movie, that at least half of the cast is male, right? ....and he never looked at the male half, even in curiosity, right???? Bret was even more defensive saying NO, HE would NEVER...... I asked if he'd ever seen a bi or gay video, and he put his finger in his mouth in a gagging type of motion.
I then told him that one time in high school, one of my other friend's brothers was gay, and that his brother found his 'stash' of porno mags and movies which were all male. I admitted that I looked at some of them, and watched a couple of movies and found them to be a pretty good turn on. Bret scoffed me off and said that he wouldn't even think of watching one of 'those' and that even if he did, he'd probably puke.
I asked him if he was serious, and he said yes. I asked him if he was willing to bet on it (that he wouldn't be turned on by watching a bi or gay movie) and he said yes...absolutely, that he would have nothing to loose! Hypothetically, I asked what he would be willing to bet? Bret said that if he lost, and was ever turned on by 'something like that,' that he would jerk me off five times, time of my choice, until I came, and then clean me up afterwards with a warm cloth, but said since that would never happen I'd just have to continue to jerk myself off. I asked him what he thought would be fair in case I might loose the bet, and he didn't get turned on? Bret thought for a minute, and said OK, since you bought it up, you put a $20.00 bill in my hand and suck me off until I cum in your mouth. Again, hypothetically we discussed what 'turned on' means, and we agreed that turned on means getting a hardon. Bret seemed to be getting into his cockiness now, and said 'but how would we know who sprung a boner? I thought for a minute, and said that since we both have speedo suits, we get into them before the movie, and 'there's no hiding anything there........Bret agreed. We talked a little more and agreed that the bet would be that I would supply three gay movies, and that Bret would have his choice of which one to have to watch. We also agreed to allow Bret to switch the three movies, but he could only switch once each, it would have to start a point of my choice, there would be no fast forwarding, and he would have to watch at least one scene to the end. Bret said OK bring it on. He had no clue what was to come next!
I stood up, told Bret to go out to his car, and get his speedo while I got the movies. Bret balked and said I shouldn't go out tonight. I agreed, and said 'go get your speedo guy, cause I have three movies in my closet! Bret balked again and said that tonight wasn't part of the deal. I called him 'chicken' and that it was OK when he thought it wouldn't happen, but NOW he was afraid that it might he was backing out. Bret said 'screw you....set up the movies! Anytime, anywhere!' I set up the three movies at a good point while he was getting his suit, and put them on the table in my bedroom. Bret came back in and as if in a show of defiance stripped naked in front of me. I did the same, and we both put on our suits. We walked into the bedroom where the TV and VCR were. We both laid on opposite sides of my king sized bed. Bret put the first movie in and said I hope you got $20.00 cause I don't take checks and 'we'll see who gets off tonight!'
The first tape scene was of two blonde guys on a beach who were just starting to strip off each other's suits and feel each others cocks. About a minute in, Bret got up and said this sucks, and switched to the second tape. The second tape was actually better, and started to show two guys in a '69' position on a bed starting to jerk each other off and playing with each other's balls. Again, about two minutes of watching this, I could see Bret was starting to grow under his suit. He got up again and put in the third tape mumbling something about this being a stupid bet. When he got up I could notice his bulge getting bigger, but not yet 'hard' The third tape was cued at a point where a hot young dude came out of the shower, drying himself off. His friend was naked on the bed starting to stroke his cock. The shower guy then laid down next to him and started to jerk off too. Bret got up one more time. I called him on it and said the bet, Bret, was only one change per tape, and you're out of changes. You have to watch this scene all the way to the end. Now lay down and relax if you can....besides 'you have nothing to worry about, right?'
The scene progressed to the point at which both guys were naked on the bed and jerking each other off.. They continued until the first guy shot a load, and I looked over at Bret, and down at his crotch. He had the outline of a throbbing hardon under his speedo,that he tried to adjust to hide it, couldn't. The tip was actually sticking out of the top and Bret looked back at me in horror. Bret said 'the bet was all a joke, right....all in fun...OK you win, I give .' Then I didn't care about the movie anymore, and stood up.. I walked around to Bret's side of the bed and pulled my speedo down. My hardon stuck straight out, and as I stepped out of my suit, I said OK Bret.....you loose. Unless you're a welcher, I'll take that first handjob now, and keep it going till I shoot my load.'
Bret called me an asshole, said he never backed out of a bet no matter how bad, and reached out and took my cock in his hand. I have to admit this was the first time I'd ever been jerked off standing up and it felt good. Bret put his other hand into his suit and I could tell he was rubbing himself at the same time. We continued like this for three or four minutes when I told Bret I was going to cum, and to stroke a little faster. He did, and I shot my load onto the bed with a few drops landing on his chest. Bret said 'now....you happy ? ' I said I'd be happy after the next four handjobs were finished, but that I didn't think since he had such a 'problem' with his cock that I should be the only one to get off tonight. I offered to 'take care of him' too, out of fairness. Bret initially said that he could take care of himself, and got up to go to the bathroom, still in his speedo. A couple of seconds later he came back to the bedroom and asked if my offer was still open. He still had his speedo on, and still had a hardon. I said that it was if he was willing to lie down and take off his suit, which he did. I took out some lube and smeared it on his cock. He was moving all over the bed and started to get tense. I knew he was close to cumming, and stroked his cock and the head a little harder. Bret arched his back, his balls pulled up tight to his dick, and he started to shoot his load. After five or six shots of cum he relaxed, and his dick softened in my hand. Bret admitted he had been jerked off by a lot of girls, but this was the best handjob he had ever gotten. I said that whatever he thought, it's because a guy knows EXACTLY what another guy likes.
I told Bret I was intending to collect on my next four installments, and he didn't put up a fight this time. I was looking forward to collecting, and I think Bret was looking forward to paying off his 'debt.' The next four times were even hotter !!