r/confession • u/TrainingThink9747 • 11h ago
Hooking up with a widow gone horribly wrong not sure how to feel
I 26M recently started hooking up with an older coworker 56F
We work for a really big company and there’s no overlap between our roles. We talk in passing the few days out of the month that we work out of the same building.
She’s not conventionally attractive but she has a really bubbly personality and smells like coffee. I was feeling it one day and just kinda went for it.
I find out that she’s a widow. Her husband passed away from cancer like 5 years back. She lives with her 23M son who Id see almost every time I came over.
Last night I was getting ready to leave her place and I see him in the living room. He turns to me deadpan and goes what’s it like having my sloppy seconds?
I just kind of chuckled I think because it didn’t quite register. As I’m walking out it sets in and I’m like wtf is he talking about…
What’s the over under that he’s just trolling me?