One night when I was sleeping over my friend Jeff's house, we decided that we were both hot, and wanted to go for a swim in his pool. Jeff is younger than me, but I've always thought he was cute. I hadn't brought my swimsuit, he loaned me one of his swim team speedos which was weird and awkward but it was dark.
While we were swimming, I had gotten a hard-on, and by the time we got out, I knew I had to jack off in order to get rid of it. Jeff went into his room to change first, and when he got out, I went in. I took off the tiny speedo, and started to jack off (hoping I could be quick, so Jeff wouldn't be suspicious), when I noticed that Jeff had a banana on his desk. I pulled the condom out of my wallet, and put it over the banana, and worked it into my asshole. In about thirty seconds, I was ready to cum, and caught it in my cupped hand. It started to drip between my fingers, but I couldn't find his bin, so I was forced to drink it. I picked up the banana off the floor, where I had dropped it, took the condom off, put it back exactly where I had got it, shoved the condom in my pocket, and quickly got dressed.
The two of us watched TV in the family room for a while, and after his parents went to bed, Jeff suggested we watch a dirty movie. He ran up to his room to get it, and came back with two tapes, one normal size, and the other one of the small camcorder tapes. The first one was of his older sister and her boyfriend (who was our age) having sex in her room. He told me how he had hidden it in a heating duct, slid the cover to one side, and run the wires through the duct to his room right above hers, where he had hooked it up to his VCR, and recorded them having sex. The tape was short, only about fifteen minutes, but it had managed to get me really hard.
He took the camcorder tape and put it in the adaptor, and put it in the VCR. I saw his room, and the date and time on the bottom corner said it was earlier in the evening. When I saw myself walk into the room, my heart started to beat a million miles a minute. As I jacked off on the TV, Jeff told me how he had set up the camcorder, hoping to catch a glimpse of me naked, and had gotten more than he bargained for. He said he had watched the tape on the camcorder when he had "gone to the bathroom", and he said that if I didn't give him a blowjob, he would make copies of the tape and spread them around. He pulled his shorts down to his ankles, and sat down on the couch, with his cock pointing straight to the ceiling.
I knelt in front of him, and started to suck, and in about thirty seconds, Jeff shot a load in my mouth. I kept it there, not sure, what to do with it. Jeff told me to swallow it, and I did, not wanting anyone to see my jacking off on tape. He told me I had to suck his cock again, but when he came, I had to keep it in my mouth.
Jeff had started to go limp after coming, and it took almost fifteen minutes of sucking before he came again. This time, he told me to kiss him, and share with him. I kissed him, and as the cum ran from my mouth to his, he started to run his tongue through my mouth. This was too much for me, and I came in my boxers, most of it running down my leg and onto the floor. Jeff told me to go clean up, I had done my part and he would destroy the tape.
Even though our first time together was under odd circumstances, Jeff and I still like to experiment together, and I hope that one day, we might be able to add Jeff's next door neighbour to the occasion some day. Jeff had told me about Andrew and how he was a member of the same swim team that he was. I could just imagine how hot both boys would be in showering in their speedos. Oh and he never did destroy that tape which came in handy with Andrew a few months later....