Got passed around the [f]rat house a little . . . and then things evolved . . .

This happened when I was in college. Names have been changed to protect the (semi-)innocent . . .

The guys at Alpha Beta had a bit of a reputation for being the bad boys on campus. One (Tom) lived on my hall freshman year and I had a class with two others (one a sophomore- Mike and one a junior- Kevin). I joked around with them all semester and had bit of a crush on all three- moreso Mike and (especially) Kevin.

Walking back form class one day with Mike and Kevin, Mike pulled me aside and asked me if I’d like to be his date to their winter semi-formal. It was cute seeing him shyly ask me and I gladly accepted. I love dressing up and was looking forward to that Saturday night. I wore my little black dress and Mike looked very nice in his suit as we went out to dinner before the band and bar at the fraternity house. Two other guys I had met once or twice before and their dates went to dinner with us. I was having a very good time and was even able to get served wine at dinner without anyone asking if I was 21. I kind of resolved with myself that if Mike made a move, I would hook up with him to one extent or another that night.

[F]inally got with a guy I had a crush on since high school (15+ years ago)

I’d always had a crush on Tom in high school. He’s this tall (6’2″), handsome guy that was the all-American type (good student and athlete, totally respectable). I was more of a theater nerd but he and I were friendly- he was the kind of guy that was sort of friends with everyone. And the kind of guy every girl in class had a thing for.

Years went by- I got married, had kids, and divorced. He was engaged but it got broken off for reasons I don’t know. He has a pretty high profile job in our area while I head up a non-profit currently. And we found ourselves at a Christmas party last December hosted by a couple we were both friends with. We chatted and had some drinks. There was a little bit of physical contact and there’s no way he could not have known I was totally into him.

As the party was winding up, he and I left at the same time and he remarked that he wasn’t really tired yet and asked if I wanted to have a drink art his place. We both knew what that really meant and got into his car. Before he could start the engine, I leaned over the console and started kissing him. He kissed me right back for a bit and then broke it off so we could head to his apartment.

I [F] gave my friend a pity fuck after he lost a parent

Tom and I have been friends since high school and I’ve always known that he had a crush on me but I didn’t feel the same way about him so we never did anything physically.

Last month, his father passed away. A group of us went to the funeral to show our support to him and his family. Like most funerals, it was pretty sad and I didn’t like seeing my friend so forlorn. There was a luncheon afterwords and I hugged him to let him know how sorry I was. But with so many family and well-wishers around him, I didn’t get a chance to speak with him much that day.

About ten days later, I got a text from a friend that a bunch of people were going out with Tom for some drinks to see how he was doing. I thought this was a good idea so we all met at a local bar on a Friday night. Tom was in about as good of spirits that one can be in after the death of a parent. I got a chance to speak to him alone and he thanked me for coming to the funeral and out that night. He said he was still processing things it was going to a be some time until he was back to his normal self. Seeing him so out of sorts got me thinking about what I could do for him to make things better. After a couple cocktails, I came up with an idea.