Where it happened: Friend's boiler room
Langauge: English
Sex: Male
Rating: 2
Category: Straight
I was a senior and a junior girl who I’ll call sarah had made it abundantly clear that she was into me. This girl had a reputation as being very…uninhibited, so I figured we were going to have sex. I was pretty nervous about this and sought advice from one of my friends who was more experienced. He said use a condom and jerk off before hand so I could last longer.
The fateful day came a couple days later. I invited her to come hang out with me at a friends house that night. I took my friends advice, bought condoms and jerked off after school. She called me a little while later and said that she was ready for me to pick her up. I told her I would be there in a little while. I figured if I jerked off again I could last even longer and really impress her so I decided to try to bang another out. The combination of having already done it prior and the pressure I was putting on myself to hurry up was making for a tough process. I was faced with 2 options. Abort and go to pick her up half cocked or fight through and try to finish. I decided for the latter. I furiously pounded away until the job was done. My penis was bright red and very sore. I go to pick her up.
We get to my friend’s house where I begin drinking. My first time was going to be nerve racking already, but now I had to worry about the damage I had done to myself and how this was going to affect my transition into manhood. As it would turn out that transition was a sad, embarrassing journey. I end up getting very drunk to calm my nerves and we start fooling around a little bit. We were in my friends basement and the only place for privacy was in his boiler room. So thats where we went. On a thin rug in between a cement wall and heater I lay on the ground while she takes her clothes off. I’m very good at reading women so I see that this a sign that I should do the same. All is well for a minute and a half when she first touches my penis and I scream and recoil. She asked whats wrong and I tried to play it off, but every touch felt like hot water on a sunburn. I finally told her the story and she wasn’t exactly too turned on by this story. She still had sex with me. Out of pity I think. I managed to hold off the pain long enough to get inside her where the violent and brutal masturbation showed some benefits as I did last a long time. The events leading up to that pretty much killed any mystique I had built up with sarah. I tried to salvage the night by sarcastically saying “so was it magical?” She faked a smile and asked me to take her home.
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