Where it happened: her bedroom
My first time was probably one of, if not the, most embarrassing experiences of my young life. Jessica and I were both seniors in high school and had been dating for a couple of months. Jessica was about 5’10”, had pretty large 36C breasts (which she always complained were too small) and a really nice, round ass. She was a very attractive girl. She had had sex dozens of times with her ex-boyfriend, so there was a great deal of pressure on me to please her the way he had. Needless to say, I was nervous as hell.
We were alone in her house that day and just started making out as usual in her bedroom. I didn’t really know what I was doing, but she seemed to enjoy me touching her. After things got really steamy, she asked me if I was ready (isn’t that supposed the be the guy’s job?) and I responded that I was. So, she runs off and steals a condom from her Dad’s room. This should have been a sign that things were not meant to be. After finally unrolling the condom onto myself, she lays back and I get on top of her. Again, I have no idea what I’m doing and am really nervous. After a bit of prodding, I slide into her and cum right on the spot. I was humiliated. Jessica couldn’t tell immediately and asked what was the matter since I suddenly stopped, got off of her and turned around. I had no idea what to do or say and become completely engulfed in shame. To her credit, Jessica never said anything really negative or seemed to mind. We tried again a couple of days later and the SAME THING HAPPENED. I have no idea what was wrong with me that month, but it just wasn’t going to happen. After Jessica and I broke up, I began seeing another girl and, amazingly, I can control myself at least adequately enough for her to reach orgasm. I guess this just isn’t my thing…