I finally [f]ooled around with my handso[m]e older friend/former boss.

I first met Chet 5 years ago at a work related event at a bar. I was a cute little 24 year old in ripped tights and a short dress, and he was a very handsome 40 year old man, well dressed in a casual suit. We chatted for a bit while I smoked a cigarette, thinking I was being so charming and adult, and we’ve been friends ever since.

Im tall, long legs, a bit of a belly but nothing crazy, perky smallish boobs, long dark hair and a pretty face. With these features I’m certainly not everyone’s type, but the guys who are into it think I’m hot haha. I’m in a creative field and am used to hooking up with guys who are like me, grungy and disheveled, which I love! But Chet is different, an executive at a financial company, he wears suits and nice clothes, combs his full head of thick gray hair back and parted, and he looks a lot like a less-heavy Alec Baldwin in 30 rock. It drives me crazy. The first few years I knew him it was as a casual friend. He’s interested in my creative field and would show up to lots of my work related events to drink with me and my friends in the same field.

A [f]ew days ago I hooked up with [m]y boyfriend’s boss.

So, I wrote this out more briefly as a response in nsfwiama, but I enjoyed recounting it so I thought I'd go into more detail here.

My boyfriend, Sam, and I have a more or less open relationship. (More detail in my history.) Sam works at a small local brewery and is friends with the owner of the company, Adam. Adam just went through a divorce last year, and from what Sam has told me, had a dead bedroom for years before that. He also hasn't dated since his divorce. He's pretty shy and has been out of the game so long I don't think he even knows where to start, despite being a kind and successful guy. In the past Sam mentioned to me I should fuck Adam, to give him a bit of an ego boost after the divorce, but I felt weird that it was Sam's boss, and hadn't really pictured it before, not to mention had no way of knowing if Adam even wanted to, so I said no.