I’ve posted here before but it’s been a very long time. Today, I’m dwelling in the past for some reason. For starters, I have had two affairs during my previous marriage. I’ve mentioned some things before about this… my wife was stricken with a rare and terrible disease at a young age and she actually knew I needed more in my life that she couldn’t provide. She even suggested we divorce but I couldn’t do that. Anyhow, those are two different stories for another day or for anyone who wants to listen.

I remarried and have a great outgoing wife. And while the sex has subsided over the last few years, we still have incredible bedroom time. But for some reason, I want to wander, I want more. Enter one of my wife’s former coworkers.

I ran into her on occasion and at first, she simply seemed very nice and chatty. Come to find out, she thought I was incredibly handsome and actually told my wife. I was immediately flattered because this woman was younger and beautiful and sexy. I started making it a point to see her as often as I could, at work of course. Then there was a dinner for a coworker that we all attended, and she made it a point to sit next to me. We flirted all night, even though our significant others were next to us. I even caught her just staring at me longingly. She even told me I was like the red headed Channing Tatum! That may have been the alcohol talking but I ate it up.

I guess some of the other coworkers were telling her she should probably cool it, but it was all friendly harmless stuff. She did tell one of them that she’d definitely fuck me if I wasn’t married and would consider swapping partners! She was a wild one.

So lately, I’ve found myself looking at her pictures on social and thinking, why didn’t I take advantage of this opportunity?! Probably because it wasn’t exactly a secret of how she felt and what she wanted to do. But I’m still kicking myself. And for a guy who’d like that extra sizzle that only an affair brings, the regret is overwhelming.

What regret stories do you have?