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I slept with my friend's dad. (F/M)(Long)

Feels good to finally share this, but I suppose a bit of background is important here. My friend, we’ll call Cassie, and I had been friends since we were 15, did ballet together and all that girly crap. We were both friends with a girl who lived next door to me so we would hang out through said neighbour girl but weren’t all that close ourselves. Anywho, Cassie lived mainly with her dad because her mom was a flight attendant and was never around.

(M 18/F 22) My first time (long story)

Chloe had her eyes on me for some time. She was tall and nerdy. A thin body and a nice perky rack. What made her hot was how dirty she could talk. Maybe she sucked dick because she thought boys would like her because of it. For whatever reason, that girl wanted my cock.

I was not smooth or cool about it. I was awkward and 18. I wanted to fuck everything that moved but I had no idea how to get what I wanted. Luckily we went to the same school and she was as horny as I was.

Always trust a horny Dominican with quick hands

I was 23 living in Nyc and my roommate had some friends visit. It was his friend who shall be called Puerto Rico his girlfriend and her friend. They had been loitering around my apartment for a couple of days but I hadn't paid them much attention since my sister had been visiting. The day before they were due to leave. We finally hung out and it started off with some smoking a Iittle alcohol and a game of never have I ever. If your not familiar with the game you state something that you've never done and if anyone has they take a drink.

Getting more comfortable (MFFM)

Stephanie and I had a pretty interesting relationship from the first time we slept together. She knew I slept with Jeff and Craig (and occasionally Don). She didn't have a problem with it, other than she wasn't allowed to watch. I didn't ask if she slept with anyone else. We'd meet at the coffee shop, or I'd pick her up at her apartment, or she'd come over by mine. It was casual and it was without pressure.

My girlfriend's bi polar aunt

I started dating my wife when we were both 19. My wife was a hot 19 year old and I loved her but many times love is no match for hormones. When we first began dating she was living with an aunt. I didn't meet her aunt for a few months but I heard all about her. She's bi polar but back then un diagnosed. She was either in a horrible mood or extremely affectionate. I imagined a mean old lady because to me aunts were all old. When I finally met her I was kinda surprised. She was around 38. This was before we had the term milf. She was a petite woman. But with a large rack.

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