In college I [M] had an on-again/off-again FWB [F]. Essentially if we were both single, we would hook-up (sometimes one of us wasn't single). Plus, we came from the same state and could continue to hook-up over breaks. We liked each other but never wanted to date, and the sex was great. Plus, I had a reputation as a fuck boy and she didn't want to be seen as dating someone like that.

Fast forward a few years and we've graduated and living in different states. I was in our home state and she was 500 miles away. I was going through Match.com one night (early 2000s) when I came across a girl that looked familiar. I reached out and we chatted, but couldn't make the connection. We were in different towns. She was in a local college (21) and I was working (25). We decided to meet up for a date and it went well, and she offered to split paying for the date. When I saw her last name on her credit card, it clicked: she was the younger sister of my FWB.

When I got home, I scrolled my former FWB's social media to confirm it. I had met the little sister once or twice before in passing over a summer break, but she had been in high school. She had grown up, lost the baby fat, and looked much different now. I had lost my frosted tips and douche goatee, so looked different enough that she didn't recognize me, either.

We went on a few more dates, and the 3rd date ended up with her blowing me in the car while parked down the street from her parent's house. When I dropped her off I could see the FWB's bedroom window, where we had fucked in the past.

By the 5th date, I had her bent over my couch while I fucked her from behind. I kept doing the things I knew her sister loved, and most of them worked on her. I can't really confirm, but I want to believe they tasted very similar.

It all came crashing down when she posted a pic on her FB of the two of us and her sister freaked out. I played it off to the little sister that I never made the connection, but my FWB was pissed at me, knowing that I was the type of person that would try to fuck sisters. She was right. Too bad I never got a chance at the mom.