I’m not new to cheating; I’ve had several experiences that keep me coming back to the dark side. But since I’ve been married (10 years - M36), I’ve always been very careful to ensure I’m not caught. I usually meet women online which enables more discretion and control over the situation than an in the wild hookup. And I usually have sex with my cheating partners while I’m traveling for work.

An opportunity came up this weekend that has me rethinking my cautious approach. I’m kicking myself for not just going for it.

Friday night I joined my wife at a party hosted by her co-worker. There were lots of people there from her work, and some brought their spouses. There was also a pair of recently divorced women at the party. One, I’ll call her Michelle, has known my wife longer than I have as they’ve worked together forever.

Michelle is an alpha. She is a manager, though not my wife’s boss. And despite this being a party full of her white collar colleagues, Michelle was totally uncensored, bringing up topics that are maybe normally taboo among coworkers like politics, drug use, and sex.

My wife has a kind of hot/cold relationship to Michelle. They were peers for a long time before Michelle started climbing the corporate ranks. My wife was definitely jealous and sometimes expressed how she thought Michelle was undeserving of her promotions. I think my wife has also felt threatened at times by her coworker. She can be an anxious person, sometimes reading too much into what someone says about her. She’s felt bullied or socially ostracized by Michelle and other coworkers in the past.

Anyways, back to the party. We had been there for about an hour, and drinks were flowing. Michelle and I were talking while my wife was engaged in a conversation elsewhere. Michelle was giving me these looks every once in a while, a kind of intense stare whenever our eyes met. I noticed immediately how much I felt drawn to her. She was also not afraid to touch my arm or back as we flirted.

Suddenly she suggested that we test drive each other’s cars. We both have newer sports cars, so the request seemed reasonably innocent. Before I could second guess, we were off. There was some hooting and hollering from the other people at the party when she linked arms with me as we walked to my car. I briefly thought of what my wife might be thinking as we walked away from the party and her coworkers (jokingly) suggesting there might be some impropriety about the situation, but that thought quickly passed.

I climbed into the passenger seat to let her drive my car first. Michelle quickly started talking about her divorce with allusions to a drop off in her sex life being the cause. I knew this rendezvous was a setup. Her intentions were clear; she was seeing what I would do given the opportunity. She pried about my sex life as we cruised around too. Several intense, flirty looks were exchanged. I could feel the tension between us.

But I never fell for her bait. Although I was tempted, I couldn’t pull the trigger. I kept thinking about what she could do if I gave her the power of influence over me. I didn’t know for sure if she was trustworthy to keep it between us. There were too many variables out of my control to make a move.

So that was it, for now. There were some other moments later in the night that confirmed for me that I could have had my way with her. This all happened Friday. I spent all weekend thinking about ways our drive played out differently. So there’s some regret on my end. I have to admit I’m looking forward to the next time I’m invited to my wife’s after work outings.