Best Friends, Family Vacation
While I was in high school, family friends of ours had a son my age who went to a different school. The summer we were first introduced, we hooked up a few times, but there was nothing more than a few steamy make out sessions, and it never amounted to much. As that year progressed, we went to our separate schools and began to talk quite a bit on the phone. He lived about an hour and a half away, but we saw each other occasionally and our families were close. We had our own lives and he had a girlfriend, but he would call me every weekend, sometimes after midnight, and we would talk for hours. It was not rare to watch the sun come up while on the phone. In any event, our families decided to go on a ski vacation to our place in New England. The first night, we sat watching TV for a while on the couch when suddenly he started pulling at my sleeve. He said he was cold but pulled me close to himself. Next thing I knew, I was on top of him and we were making out. As he took my shirt off, it hit me that he had a girlfriend. I had a pang of guilt and got up to leave. A few minutes later, I immediately regretted it and grabbed him back. We were half undressed and since the living room was very open-spaced, we knew we needed to go somewhere else more private. The only place was the bathroom, so we went in and started making out again. Soon, I had nothing but a tiny thong on, and he was in his boxers. The hookups continued for the next three nights. The fourth night, we were on the couch when his hand went to my thigh. We hooked up in the bathroom but slowly my hands drifted and were pulling at his boxers. I realized I shouldn't be doing this and went back to the couch. He followed, began kissing my neck, and soon I was playing with him and he was playing with me. In the middle of the living room, I went down on him. You could tell he was trying so hard not to make noise, but it was impossible. Suddenly, he grabbed me. I wrapped my legs around him, and we began having passionate sex up against the wall as we moved towards the bathroom. We had sex most of the night. I woke up to him kissing me and pushing my hair behind my ears. We quickly got dressed and sat in front of the fire with coffee while everyone else slowly got up. To this day, no one knows, but they always recall "how cozy and fun" that ski vacation was, and "how well we got along". We just smile.
— Jill, 28