shy28boy's blog post - First Time

I lost my virginity at 25, not for lack of trying but I think I was a little too shy to close the deal. Anyway, by the time I was 25 I was determined to loose the V card.

I put in a personal add in Boston Magazine (way, way per match/tinder.com) and got a view responses. I went out on one date and it was a disaster. I then went out with a second girl, a blonde who had just graduated from college and had her own studio apartment.

The first date went well, we went out to dinner and had a nice conversation and just a chaste kiss when the evening ended. The second date was much more interesting. We went to dinner or a movie and then back at her place. We started kissing on the couch which turned into breast play, her blouse coming off and eventually both our pants/skirts came off. I was naked and she was done to her nylons on (this was the 80s, the ladies were all wearing them) and panties underneith, sexy look btw. At that point i go my first blowjob to completion which also was the climax of that date.

So we set up another date which i was pretty certain i was going to loose the virginity. I believe we went to a movie, I don't remember what the film was. We got back to her place and the action began. Kissing on the couch which lead to touching and then clothes coming off. We finally ended up completely naked in her bed. At that point, she asked me are you sure you want to do this ? (I had told her I was a virgin earlier) She then went to the bathroom to put in a diaphram. While i was lying there, harder than I think I ever was, thinking to myself it is finally gonna happen.

She came back an slowly mounted me. As I slid into her the lovely feeling of warmth and tightness around my cock, I came immediately! I was so horny and young that I don't think I got soft at all! She went back to the bathroom to put in some more spermacide and then we went at it again, this time I lasted much longer. So mission accomplished in a loving and memoriable way.