A Casual Threesome with a Coworker?

Chai Steeves
2 min readSep 24, 2022

Is that a really, really bad idea?

Photo by Roman Khripkov on Unsplash

Have you felt destined to have a relationship with someone? We all have.

But what about the opposite? A person with whom that destiny seems to be actively conspiring to assure you never get into bed?

That is my current dilemma. For over six years, my wife and I have had a wonderful, flirtatious relationship with a young lady. There is great chemistry on all sides and, at a conceptual level, a great desire to have a little sexy fling.

But destiny can be a bitch.

I initially met her as a student — a graduate student. I was not her professor or direct supervisor but her ultimate boss. She was bright, fun, and mature. I liked her a lot, but to be honest, as a student, I had not even considered there could be a sexual connection. I genuinely don’t feel that way toward students, so it was not a consideration then. But she was really fun, with great energy.

I thought the world of her and, upon graduation, arranged for her to work for my wife’s firm. My wife and I got to know her better as a colleague and learned we had many similar interests, including a pretty liberal view on sex with friends. Over the years of working with my wife, she often alluded to how fun it would be if we all — my wife, me, and her — could go out and cut…

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Chai Steeves

eclectic guy - likes sexuality, politics, business, relationships, celebrity trivia...