I almost fucked a friend’s mom once. I say “almost” but really, I just could have. We didn’t do anything. Instead, I fooled around with one of my mom’s friend’s who was 20 years older than me.

Another friend and I (who I’d known since high school) were sharing an apartment our senior year of college and my friend’s mom and my mom’s friend had come down for some workshop at the school we went to (they were high school administrators). They offered to take my friend and I out. Friend’s mom was divorced, mom’s friend was something of a spinster. We went out to dinner and they were having so much fun they suggested hitting a bar. Shit went off the rails pretty quick. My friend’s mom started scratching my head, running her fingers up and down my back, and leaning her head on my shoulder. I was into it. I’m not one to pass on a sexual opportunity.

But I went to the bathroom, and when I came back, she was all over my roommate. They were making out and people were staring because it was a college bar and she was 50. I felt left out and made a subtle move on my mom’s friend and she seemed receptive.

So we went home and my friend and my other friend’s mom went back to his room. After a few minutes on the couch, I was able to get my mom’s friend to come spend the night with me in my bedroom. We didn’t really have sex, but she manually brought me to completion while we made out.

The next morning was brutal. My mom’s friend pretended like nothing ever happened, “Well, thanks for letting us stay. We need to get going. You guys be careful down here.” That sort of thing. My friend’s mom was in full-blown regret. She didn’t make eye contact or say a word to me. My friend said she’d made him promise “to never say a word about this to anyone.”

Once they left, my friend came to me to put his conscious at ease. I told him it was shitty what he’d done, and he should have never done that to a friend’s mom (because I was pissed he’d swerved in when I went the bathroom). He said, “but you would have, too!” and I denied it. I would have, but fuck him.

I was one trip to the bathroom away from being able to tell one of my high school friends “I fucked your mom” and have it be true. I’ll never forgive my roommate for taking that from me.