This is a follow-up story to 'Two Guys - One Bet.'
Two Guys - One Bet
It had been about 10 days since Bret lost the bet and he and I had our first male to male experience together. Bret still owed me four more handjobs, which according to the bet was 'at the time of my choice...and then he would clean me up afterward.' I was getting pretty horny and wanted to collect on my next of four installments. Since our first time, we only made one or two nervous comments about what happened, but we had only seen each other a couple of times. Bret knew I still intended to collect, though.
It was Friday night, and we both agreed to meet for a game of racquetball and maybe go out afterward. It was about 7:00 when we started, and after three long games, we called it quits around 8:00. We were both drenched with perspiration, and went to the locker room to shower and change. We both took showers in the men's area (gang showers) and then stepped into the steam room. We both walked in with towels around us, and dropped them to be naked and enjoy the steam. Once again, the sight of Bret naked was a real turn on, and I had looked over at him several times with quiet thoughts of a night of sex. After several minutes of this, we both took a second shower, dried off, dressed, and got ready to go out.
We went to a local pub and had dinner. We finished, paid the tab, and agreed to go over to Bret's house for a while. I finally brought up the subject on the way home that I was feeling really horny tonight. Bret said 'I suppose that means you're gonna want another handjob, right....?' And I said let's wait a little and see what happens. Bret surprised me when he said that he wouldn't mind getting off tonight. We drove the last 5 minutes in silence. Once at Bret's house, we started to talk a little more freely about the first night. Bret said that he had been thinking about what happened, and that he was now pretty much OK with it, so long as no one else ever found out. I promised him I certainly wouldn't tell if he didn't, and that seemed to give him a feeling of relief. Bret admitted he had jerked off a couple of nights thinking of what had happened.
I could tell Bret was getting a little randier, and so was I. Bret asked if I wanted to collect on my winnings since he didn't want to be owing anyone from a bet. I said 'sure, the next installment would be appreciated tonight, and if he hadn't suggested it I would have.' I could feel my cock getting hard under my jeans, and I could tell Bret was starting to tug at his jeans getting hard too. This time Bret walked over to me, and said 'well, what are we waiting for.......it's not like I don't owe you, and it's not like we haven't done this before...His all of a sudden brashness surprised, but pleased me. Bret had an fold down futon in his living room, and dropped the back to make it into the size of a flat full-size bed. He then walked over and unbuttoned my top snap on my jeans. I did the same to him, stroking his cock through his jean material. He was already hard as a rock as was I. We pulled our shirts off and stripped to our jockey's/ The outline of both our cocks, stiff and ready, filled the fronts of our jockeys. He had on black and I had on red. We both lay down on the open futon. Bret asked if this meant I was going to give him a hand tonight too, and I said sure, I know I don't have to, but why not. Fair is fair, right?
With that, I reached under the waistband of his underwear and took his dick in my hand. Bret was already leaking some pre-cum, and that made stroking it easier. Bret again surprised me and reached into the end table next to the bed and pulled out a nearly new bottle of astro-glide lube. Bret spread his legs, and I sat between them after pulling his underwear from his body. Bret surprised me when he held up the bottle and said 'Man, your lube felt so good last time, I went out an got some for me too. He said up until that time he had always jerked dry. ' I took the bottle from him and slowly dripped some on the underside length of his dick. I had my right hand underneath it and caught what dripped off. I told him I wanted him to come first tonight, started to slowly stroke his silky, shiny lubed dick. I was playing with his balls with my left hand, and I noticed when I got a little lower, Bret started to groan. I started to massage the area between his balls and anus, and he squirmed all over the bed. Just as Bret said 'slow down, I'm.......cumming..........' I could feel his dick harden and out shot several shots of cum. Bret took his right hand and massaged his cum into his belly.
By now, I was so hard it almost hurt. Bret got up and had my underwear off in a second, and sat on the right side of the futon. He quickly pinched my nipples, and said 'want some lube?' I said 'sure.....make me cum for you.' Bret, instead of just lubing up my cock, also put some on my balls and even some underneath. With that he said, which surprised me, ' you have a really nice cock. I want to make it feel good for you like you did for me......I want to see you cum. I want you to cum while I jerk you off. ' Bret then started to slowly stoke me with his right hand, and a little later brought his left hand up to play with my balls. I was getting pretty close, and told Bret that I wanted him to slow down, which he did. Bret surprised me again, and asked me if I wanted to try something his girlfriend does to him that feels great. I said to 'go for it...' and his left hand left my balls. His left index finger began to massage under my nuts near my anus, and slipped down a little bit lower. I asked him what he was doing, and Bret told me just to relax. All of a sudden I could feel his finger around my anus, and he gently slipped his lubed finger in while he continued to stroke me. I have to admit, it felt AWESOME, and even better when he moved it in and out just in short strokes. He had been jacking me for about 6 or 7 minutes now, but between the sloshing sound of him jerking my lubed dick, and the finger in the butt, was more than I could take. I wanted it to last longer, but I could feel that I was now past the point of no return. I shouted for Bret to 'watch me - watch me while I cum for you....' And I did, shooting my load of cum further and shooting more of it than I can ever remember. Bret asked me if it was good, and I said it was probably the best jerkoff session I had ever had.
Bret said 'I think I'm getting the hang of this handjob stuff,' and then massaged my cum into my stomach, sides, and chest. He told me to just lie back and he'd be back in a minute. And he was.......with a warm washcloth.