When I was single, I had a very good friend, and she used to make it easier for me to hook up with some of her friends. One specific friend, lets call her M, was an attractive blonde with toned and tanned body and around my age (28-29 yr old). I hook up a few times with her and also had a great sex woth her. She seemed interested in me, but - let's just say - I was going through a phase where I wanted to hook up with as many girls as possible. Not long before, I was in a very dull relationship. It explains why my interest on M was slowly fading at that time.
Fast forward over one year later, my friend invited me on a long holiday trip to a resort; and share a room with her and two other friends. This time her friend were not for me: one was attractive, but as in a serious relationship; the other one was not attractive at all, even though she was a nice and funny girl. I was still single at time time, and I knew M was dating another guy.
One night, just around the time we were going to sleep, I was almost falling asleep, and the girls were chatting in their beds. My friend started talking about M. I realized it was M because she mentioned her name and where she lived. This made me interested in the conversation. I pretended to be asleep, but my eyes were only closed. Then, my friend say that M loved anal sex and spanking. She said also that M had anal sex regularly with her boyfriend. They talked about this without noticing I was listening to everything.
In the following morning, I asked my friend about the story. She was surprised that I was listening, and confirmed the whole story. I felt like an idiot. I had sex with M only two times, but there wasn't enough time to realize I might end up having anal sex with her.
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