[jackqx4]

Many, many times to my dismay.

The first time was with a girl I was sleeping with and sort of dating. We fooled around one night (mostly fondling and light oral) and she wanted to show me something special. I was on my back at the moment and she was straddling me. I could feel her heat through our underwear. Without expectation, she pulled the band of my boxers over the top of my erect penis and started to slide the head inside her extremely hot and wet vagina. I stopped breathing the minute she did that. I had never felt anything so electric. I had had sex before, but this was the first time I was completely naked inside a girl’s pussy. I told her we had to stop or I was going to explode. She stroked me very slowly with just the tip of my penis inside of her and then she got up.

Being young and stupid, we evolved from condoms to broken condoms to the skeet method. I knew she liked feeling me unsheathed as much as I liked feeling her, but I had a lot of anxiety about our relationship and about my attractiveness as a person, so I was almost always tense with her. This meant many, many incidents where I would be inside of her for about a minute, two at the most, and suddenly have to pull out and shoot my load on her. There was never any followup. I felt immensely disappointed in myself as a man. Eventually, this lead to the breakup (in retrospect, thank God).

It was the first time I ever got to feel a pussy completely with my dick.