Where it happened: A hotel in Louisville, Kentucky
Langauge: english
Sex: Male
Rating: 5
Category: Straight
Yes, I was a 25 year old virgin. Yes, it bothered me that I was. I wasn’t a complete oaf, but a mixture of luck, naivete, and shyness kept leading to frustration. I started dating a girl in August. She was cute, and we shared several interests, but she turned out to be kind of psycho. After an unusual for me make out session on the first date, I decided that come hell or high water she was going to be my first conquest. It turned out that there was a lot of hell to go through to get there. We did have some nice times, and often got naked and did things to each other, but she refused penetration, even though she was not a virgin herself. She really didn’t have a great reason like coming out of some long term relationship. I think she just liked having that over me. She was a sales rep and traveled a lot for work. One day in January (yes, 5 months after we started dating) she invited me on one of her trips to Louisville. I think we both realized that this would be it. She had sprung for an upgrade in hotel rooms from what her company paid for, and after a few business stops, we settled into the hotel room. She told me to close my eyes and after a few tantalizing moments allowed me to open them. She had lit some candles and taken off her business wear to show off a nice piece of lingerie that I had no idea was under there. She asked if I was ready, and I knew exactly what she meant. She retrieved a condom out of her suitcase and rolled it on for me. After a brief time of foreplay, she again asked if I was ready. I again knew just what she was talking about. We got into the missionary position, and finally…penetration (AHHH)! It was very nice. I ended up being pretty impressed with myself if I do say so. I was able to last until after she orgasmed. The condom certainly helped my stamina. It wasn’t mind blowing, but it was good. We proceeded to have some more mind blowing times throughout the rest of that night. I have always appreciated that night and that she did want to make it special for my first time. Unfortuantely soon after the sex dried up much more quickly than it should have, and she started getting a little psycho, but that’s another story. I am very glad I didn’t marry her, but I am also appreciative of that night.
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