I didn't plan to start having sex with Matt. In fact, I thought he was kind of arrogant when I first met him. Yet, at times I would watch him with his friends and he seemed funny and polite and nice. That's when I first suspected it might be a front. Physically, I always found Matt kind of hot. This was confirmed when I saw him by the pool in a pair of swim trunks for the first time and it was clear that he had something impressive between his legs. He was just 16 then, so I held back on my desires. It's not like I didn't know he was sexually active. I had heard him either fucking downstairs on the couch or in his bedroom on several occasions. I even watched him fuck some girl on the couch after a Friday football game in just his jockstrap. Even then, he was muscular. I had to do everything in my power not to get too turned on watching his ass buck in that jockstrap as he fucked some girl - probably a cheerleader - after winning his football game. Ironically, he was a tight end.Other. So that was the first bet over with. The next bet was won by Jane. Again, like me, she also struggles for ideas, then she came up with the idea for an outdoor streak. Behind Janes back garden there is an alleyway that leads to a dead-end to the left and to a quiet road to the right. The dead end-is approx 50meters away. She dared me to walk to the dead-end and back totally naked apart from my shoes. Obvisously I had to wait til it was night-time. A few hours later I was at Janes. It got to about 11pm and we quietly went into Janes garden. The alley was very dark. There are no lights there. It was also a bit chilly. I had already stripped indoors and was just wearing one of Janes dressing gowns. We got to the gate. I poked my head out. It was quiet and nobody around. Suprisingly I wasnt that nervous about it. I removed the dressing gown and handed it to Jane. I then made the walk to the end and back. Brrrrr.. It was cold. I came back and put dressing gown on. Even though Jane believed.
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