A Man Asked Me To Be His Mistress

I recently went to a local bar to grab a drink with a few of my friends. While waiting for the bartender to make my Malibu Bay Breeze, the man next to me started talking to me (about my hair, of course). I humored him for a few minutes, listening to what profession he’s in and how old he is (in his forties). That’s when things got interesting.


“So, listen, I have a lot of money and I’m bored with my life. Don’t get me wrong, I love my beautiful kids and my wife, but I’m looking for someone on the side.”


I sat there, jaw dropped, staring at this guy, waiting for him to say, “Just kidding.”


He didn’t. Instead, he continued to make his case.


“I’ve traveled all around the world; I’ve been to every country.”


“Really? Have you been to Italy?” I asked.


“No, not Italy,” he said, and tried making up an excuse like he was going to go to Italy but ended up in Spain or he wants to go but his wife won’t let him. Something ridiculous like that.


I let him go on and on before finally saying, “I don’t think it’s a good idea to cheat on your wife. It sounds like she really loves you and you have beautiful children.”


“I know, I know, but…” and he went off again telling me why he should have a mistress — and why that mistress should be me. I eventually walked away from this old whackjob and danced with my friends.


When he was leaving, he walked over to me and said, “Okay,so I’m getting out of here. How will I get in touch with you?”


I touched his arm and said, “We are so connected that you can do so telepathically. Have a great night and kiss your family when you get in.”


“Aww, come on, that’s how you’re gonna be?” he whined.


“That’s how it’s gonna be,” I said, smiling. And then I added, “Dude, I’d give you a heart attack,” and walked away.


Has anyone ever straight-up asked you to be their piece on the side? What happened?

4 thoughts on “A Man Asked Me To Be His Mistress

  1. Hmmm, I wonder what the odds of this actually working is, are there girls that would actually be cool with this approach… I mean, there must be because we hear all the time in the news of these rich old dudes cheating with their young sexy mistresses. I may have to experiment and test this out for myself…

    Sooo, Jen, want to be my mistress?

    Actually, this wouldn’t work since the experiment would be biased, given that I’m neither rich (yet) nor old (yet). I’ll give it some time before testing again :)

  2. You handled the situation properly.

    It has happened to me before but not exactly like yours. An older man asked me out on a date. Before I made an answer I looked at his hand and saw a wedding ring. I asked him if he was married and he said yes. All I remember telling him is, I don’t want any drama. Something like that.

    It’s messed up they their are cheating on their spouse but atleast they were honest. I rather a guy tell me straight out his intentions rather than being caught in a web of lies.

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