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I was on vacation with my family in July of 1988 when I was 14 and up to that point I had only felt the breasts of my old girlfriend. I lost my virginity the third day of vacation and by the time I went home I had fucked a gorgeous 18 year old 5 times.

I then met a girl who I would date for the next 6 years until we broke up in college. I had started bartending at a hotel when I was 21 and shortly after I was with a waitress who was going to be the first girl I fucked other than my longtime girlfriend and the beauty from vacation. When she was on her knees she took my boxers off and told me that I had a huge cock. I hadn't heard that before because I took my ex girlfriend's virginity so my cock was all she knew.

Now fast forward to a year later where I had been with a few more girls when I was alone in my bar about to close when a woman walked in that literally took my breath away. She was 5'9 and 120 lbs and had a black dress on that was worn to show off her amazing body. She ordered a dirty Absolute martini and the two of us talked for about an hour until she told me she was staying upstairs and that we should go to her room to celebrate.

I grabbed three bottles of wine at her request and took the elevator with her to the 31st floor. As soon as the doors closed I asked what we were celebrating and she responded by kissing me and placing her hand on my thigh and rubbing my throbbing cock. I couldn't believe what was ...

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