This story happened with my ex girlfriend. Super skinny brunette. Small tits. Gorgeous face. Long Legs. We were both in university. She was 20, I was 24. She was a super fit dancer, and I thought she could easily be a model. By the time this story takes place we had been dating for 6 months and having sex pretty much since the first night we met. She had some past relationships but was mostly inexperienced. I didn’t take her virginity and at the time it was something I felt amiss about.
I had suggested I take her anal virginity but she was not into it. I never pushed it further, but I did try and massage her butt hole whenever I got the chance. She usually pushed me away and we just moved on. I pretty much stopped asking for anal at this point.
I lived alone, while she lived in a house with 5 other people. That night, we were at her house and were playing Monopoly with her roommates. We were all drinking, and having quite a bit of fun. After an hour or two into the game, most people started setting up houses/hotels, and it was clear who was leading in the game. My girlfriend didn’t have enough matching properties to put up houses/hotels. She had 2 of the green properties, and was missing the 3rd and final piece, the one piece I had.