It took me several months before I ventured onto the chat sites again. I was so overcome with the guilt of what I had done and I continued to fight the urge to seek out other men to chat about our experiences. As much as I wanted to forget what I had done be faithful, the draw was just too much. I found myself going back again and again. This began a long string of frustrating experiences with guys who talked a good game but had no intention of meeting. Then there were the one time players like me who were so scared after they actually had sex with a man for the first time, they were too freaked out to do it again for a long time.
It was probably a year later when I started talking to B&W. They lived about 20 minutes away from me and were on my way home from work which would be convenient for meeting. I was really nervous about talking with B because he was my first "gay" connection. He and his partner lived in a small community where he was a teacher and his partner worked in manufacturing. Neither of them were out in the community because it was a very small, Southern town and it was just easier for them to be room mates.
We talked for weeks before I had enough courage to actually meet them. I think they were as cautious of me as I was of them. I still refused to give up my pictures and that made it very hard to meet anyone. However, they offered to meet me at McDonald's on my way home one evening. They would be waiting in the parking lot and we could meet and decide what would happen from there. I was incredibly nervous about meeting them both (always thinking that it was some kind of set up). I was pleasantly surprised when I pulled into the parking space beside them. They both looked like guys that I would hang out with back home. They had on khaki shorts, t-shirts, flip flops and ball caps. Both were nice looking guys, B was a little bigger at 175lbs and 5'9 with a shaved head. W looked to be about 150lbs and 5'8 with a beard and full head of hair. I got out of the car and walked over to the truck where they were standing and introduced myself. We chatted for a few minutes and then B said that I had passed inspection. He would be back in touch with me and we could set up a meeting. I agreed but I was disappointed. On my drive home I figured that had been his way of saying "thanks but no thanks".
A few days later, I was pleasantly surprised when he started chatting with me and asking me about when we could meet again. I guess I passed the inspection after all. We set up time to meet when I could "work late" and they would meet me at the McDonald's again to bring me to their house. Again, I was extremely nervous about going to someones house - especially two guys - but I did it anyway. The little head always wins out over the big head.
Our first time together was slow and easy. B was definitely the dominant one in the relationship. He took the lead, helped me get undressed and initiated our play. B's dick was a nice size, maybe 7 inches but it was W that was hung with at least 8 inches and thick. W was there but he was in the background, mostly watching us as we played but occasionally offering a hand here and there. As expected and as we had chatted about we did a lot of sucking with a lot of body contact. W would sometimes join in and he and B kissed a good bit since I was not up for that yet. I had not kissed a man at this point and did not think I would enjoy it. B would suck my dick and get me worked us and then pull off before I shot my load. I liked the way he let me edge and he was good at that. I don't remember exactly how it happened but I found myself underneath him with him sitting on my pelvis. My dick was straight up in the air and was rubbing along the crack of his ass. Up to this point in all my experiences with guys I had never considered playing with a guys ass. He asked if I had ever fucked a guy in the ass knowing that I had not. My dick was still wet from his mouth where he had been sucking me. He reached behind and moved my dick to touch his hole. It was an electric feeling. Something that I had read about but never experienced. My dick became even harder, if that was possible, and I could feel him pushing against the head of my cock. He was pushing his hole down onto my cock head. OH MY GOD! What a feeling! A man hole is a lot different than pussy. I had fucked my wife thousands of times and I don't remember it feeling like this. As he pushed further down on my dick and started to slide up and down, he pushed me over the edge. I cried out, "I'm cumming" and he pulled off of me while my cum shot up his back. It was an intense orgasm, probably one of the best I had up to that point in my life.
It was a couple of weeks before we had a chance to play again. I have to admit that all I could think about was fucking him again. Getting my dick in his ass and fucking his brains out. I didn't have a lot of control the first time so I wanted the next time to go slow and easy so I could enjoy the whole experience. I was not disappointed!
It was another electric experience with me fucking him for a long time and him shooting his load while I was fucking him in the ass. It was an incredible feeling and I was hooked.
The next time we played I was expecting the same kind of experience. We always had a lot of body contact and playing around, sucking each other and jacking off. Then B started playing with my ass. I enjoyed sucking cock and being sucked but I had never done much more than that. I also did not kiss at this point either. We played around and sucked each other and then B found my man hole. I told him I didn't think I was ready for that but he said just relax. First it was his finger, he was pretty cool about it and took his time and I did begin to relax. Then he had me lay on my stomach while he rubbed his cock against my ass crack. I told him I wasn't ready but we continued like this for a while.
He eventually slid his dick into the crack to find my hole. He worked around it for a little while before he tried pushing his way in. When he pushed against my sphincter and got inside, it hurt like HELL! He kept saying just relax, and breathe. It will be alright when you relax but I could not relax and I thought I was going to DIE. He continued trying to work it in slowly but I couldn't handle it and had to pull away. He was cool about it and said we could try again another time. We finished off that night sucking each other off with W jacking off and shooting his load on my chest.
When I left them that evening, I was sure I was not ready to be a bottom. But I had enjoyed playing with them and was hoping that they might invite me back to play again....
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