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6
The engaged woman
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Several years ago, when I had my first job after graduating from college, I had an experience that might fit here. I lived in an apartment building across the hall from a guy who was a big dude, the starting tight end for the local university's football team. Rob was about 6'5", 240-ish.

He was engaged to Annie, this alternative-type woman. Shaved head, a couple of tats and piercing. Not classically beautiful, but one of those people who had that charisma. She had "it," whatever it is. Her voice itself kind of dipped sex.

Rob and Annie seemed to be an odd couple. He was huge, she was thin and slight. Not short, probably 5'6" or so, but maybe 100 pounds soaking wet. He also kind of presented as the all-American jock type, pretty mainstream looking. A nice guy, not a toxic jock, and not dumb. Annie was another level, probably a genius IQ.

Annie was a part-time student and also worked part-time. She lived in a city about an hour away, but came to visit Rob most weekends and days she had off. She and my roommate Erik, a student at the local tech school, would often sit in the hall and smoke, because neither Rob or I wanted them to smoke in our apartments. I'd often get home from work and sit and chat with them or join them to chat on a Saturday afternoon.

It was clear there was a bit of a spark between Annie and I. I love smart alterna-chicks, and she seemed to think I was smart and funny.

So one weekend, I think it was around Halloween, Rob's football team was playing on the road. Annie, Erik, and I decided to avoid the college bars and sat around and drank and got high. Lots of conversation about life goals and even some light sex talk. At some point in the evening, Annie and I were sitting on a couch, and she lay down with her head on my lap.

Erik went to bed about 2 a.m., and almost immediately, Annie straddled me on the coach, so we were sitting face to face. She knew what she wanted. We started kissing within seconds and started touching each other soon after. I had her shirt and bra off and my fingers inside her when we decided to go to my bedroom and fuck three times.

The weird thing was this was technically how I lost my virginity. I had a long-term girlfriend in college who wanted to save vaginal sex until marriage, and we had just broken up a few months earlier.

Annie and Rob stayed engaged for several months, but she finally broke it off. Annie and I stayed friends with benefits for a couple of years.

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2 days ago