[MF] A nearly missed encounter leads to a 3-day weekend spent fucking.

(For less backstory skip to THE WEEKEND below)

Around 2017, I was in a stretch of traveling a lot for work, I’d been talking at conferences & universities.

My most recent relationship had sort of fizzled out, in part because I was traveling so much. When I got invited to Chicago I was glad because my friend and her husband had just moved there and it’d be nice to see some friends. I decided I’d forgo the hotel room & stay in their new guest room. (I’d come to kick myself for that decision.)

This trip was to talk to about 100 graduate students. I arrived in the morning and a student, Emma met me and gave me a quick tour. She also mentioned that there’d been a scheduling conflict and only people in her cohort would be joining, not the entire program. That meant I’d be talking to ~20 instead of ~100. I didn’t mind, it was honestly a bit of a relief, I could be much more casual & interact more with the group.

The time I got lured into dominating my girlfriend’s rich friend. [MF]

Fun stuff starts at !!!!!!!!!!!!

Nina was the first “rich girl” I’d ever met. Her dad worked in the film industry, not even someone I’d heard of but she really treated money like it was nothing.

I wasn’t in her inner circle, I didn’t get invited on the lavish trips she took people on a few times a year. I did however get to go to her catered parties and movie nights She had a home theater in her house. This was in our mid 20s when those of us that were doing pretty well were considering buying a small condo. She had a movie room. 8 or so seats in a miniature theater.

She was very into film (she later went to film school for a year or so) so this was her pride and joy, the sound system in particular. I think most people don’t justify the existence of a home theatre the way she did. It was a weekly occurrence to see the latest releases on her projector.

[MFM] “Both of you?”

(the good stuff is after ****************)

I grew up with Nick, best friends from 8 years old. We’d dated best friends in HS, gone to college together, argued like brothers, he is my best friend. At this point in our lives we weren’t seeing much of one another, living a few hundred miles apart and working a lot.

So I was really excited he was coming to town for a few days. It had been a rough few months, left a job I really cared about and a relationship ended. Nick had to call off his engagement a few months ago and he wasn’t over it. We decided without really discussing it we’d go out and get wild. That wasn’t our usual thing, we were pretty boring, fairly nerdy guys. We were both typically in relationships and hadn’t really ever been big partiers- but I think we knew we each needed a change of pace.

We went out in a fun neighborhood in my city. In all the time we’d known one another circumstances had been such that we’d never had the experience of both being single and out at bars together and we quickly started having a lot of fun with it.