Bisexual
2005-10-16

Well after some misguided directions I finally arrived at his place. He was standing outside waiting for me. He had the old school short short gym shorts on and had some kind of tight assed walk to his step. I found my self in his room talking to this person I thought I hit it off with but as we talked I couldn't picture my self doing anything with this person sexually. I had only experimented with bisexual men before and they were definately not as feminine as this person was. After about an hour of conversation I said I had to leave. I didn't talk to him until a few months later after that day. I said I was pursuing someone else. It was actually a few that ended up in some fun and some awkward situations that I will save for another story. Well when I finally had a good conversation with Brian (the name of my fem friend) I told him about my mishaps with some guys and a few girls and wanted to meet up with him and talk. I arrived at his house this time with and open mind and a clearer idea of what to expect. We started to talk as we did before then I felt some sexual urges come over me. I asked if he had some porn for us to watch together. He immediately popped in some vintage looking gay vid of a few guys going at it. Then I figured I sort of owed him for leading him on before so I asked if he could massage me. He said he was training to become a professional and was willing to practice.

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He tried to do his best with me lying on my stomach on his couch but it seemed to become a difficult task.

He then said he needed to get out his massage table. At first I said it was not necessary to go to the trouble of getting it out but he insisted that it would be worth it. As he proceeded to unfold the table out of the custom carrying case I slipped out of my clothes and greeted him with my naked bod. He was somewhat shocked but I just said it was the best way. He began to work on my shoulders and seemed to be enjoying him self as well as the view of my bare ass. I asked if he could take his clothes off too since I was naked. He obliged me and saw he had a very proud erection of a good 6 inches. He went back to work on my back and thighs and I noticed his hard on was still rock hard after a good half an hour. I couldn't resist and reached out and started to stroke him as he stroked my entire body. He seemed surprised at my desire to massage him but didn't object. After some time he asked if I could flip over so he could massage my front. As I did what he instructed he went straight for my stomach and worked his way to the front of my thighs and my cock. Being so relaxed from a great massage I became very horny and pulled him ontop of me and started to 69 each other. After a few minutes he wanted to go solo on my cock and proceeded to bob up and down on my thick cock for what seemed like hours.

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I got so turned on by his skills I wanted to return the favor and made him go on his back. I began to work on his cock and looked to see if he was paying attention. He was in so much pleasure he had is head back and his eyes were rolling. I began to masturbate slowly, rubbing my balls and also fingering my ass a little. I then felt a need I hadn't felt in a long time. It had been a long time since I had a cock in my ass. The last time was with one of those flings I mentioned and it wasn't very enjoyable.

Mostly cause I wasn't into the moment and had only had it from one other guy featured in previous stories. Well at that moment I climbed up and mounted him. He was in such shock he just asked what I had planned. I began to work his cock head over my ass opening. He stopped me and said that he needed protection. I tried to convince him other wise since I have a senstivity to latex. But he insisted and put condom on made of a non latex material ( i think urethane). He grabbed some lube and was waiting for me to work his cock in.

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As I proceeded to push his cock into my ass I asked when was the last time he did this and he said it was a good 12 years back in high school. He also said he usually only gave bjs or occationally got fucked but usually didn't allow people to touch him. With that I slowly sunk down on to his hard cock. It hurt a bit since i wasn't exactly experienced as most. Like I said I only had 2 guys in my ass. The first was only 4 inches and the other was average. My current anal intruder was average but I swear he was so hard that it hurt like he was hung like a horse. I tried my best to ride him but after 18 minutes or so I was wishing he came already. The condom was not agreeing with my sensitive skin and instead of pure bliss I was in some pain but also a little pleasure because he was into the moment so much. You could really tell he forgot what Fucking someone else felt like. He moved me into the missionary position and began to work my ass harder. I tried to enjoy the moment for him but after about half an hour I said it was too much. After he pulled out I said perhaps next time we could do it with out the condom. He said maybe or maybe I could fuck him instead. Since we have both been busy, the second round had been put on hold.