Screwed my secretary after she resigned
For around 4 years I had a secretary who was a single mom. I helped her out every now and then because she had a child and she didn’t earn very much.
She eventually found another job and I asked her for dinner before she left. We were able to admit to each other that if only the circumstances were different (like if we werent co-workers or if she was single and childless), maybe we could have dated.
Had a few drinks at the bar after and we went to my apartment. She said she also wanted to have a good memory of us before she left and wanted to thank me in some way for all the help I gave her without asking for anything in return.
It was one of the most intense hook ups I had maybe because there was also years worth of unspoken attraction built up. We did it raw and she let me finish inside since she was on birth control pills.
Now that she’s gone we still chat once in a while. As much as I wish we were able to do it earlier and more often.