I Dated a Cuckold

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My iPhone screen lit up as I lay awake in my hotel room. I was on tour, and my band was all asleep, but for a few months, I’d been texting with another musician I would name Florida. We spent one night together in Austin at SXSW, where we stayed up until 7 a.m. and fooled around all morning until I left, frazzled and braless, to play a daytime showcase. Since then, we’d both been on the road, and so we’d been sexting: the ever-so-intimate telegraph of modern solo jerk-offs.

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“I want to tell you something,” Florida wrote. “It’s my fetish…”

“Go on,” I typed. “You can tell me. No judgment.”

“My ex-fiancée was not into it. It’s kind of weird.”

I waited for his incoming message, peeking around the room at my bandmates, half of whom were snoring. It was 4 a.m.

“If you were my girl, I wouldn’t be upset if you got with other guys and told me everything about it. Everything.”

Nowhere in my brain was there a particle that wanted to be anyone’s girl. Earlier that year my boyfriend and I had broken up, and with that, my decade-long attempt at monogamous relationships came to an end. But now, I was confident enough to be truly single. My career was going well. All I wanted to focus on was my band.

No longer would I be bound to a boyfriend back home who drained me with his need for my love and attention. I was going to put myself first. I was going to live like Robert Plant: Screw whoever I wanted, when I wanted. A shameless embrace of my promiscuity. Men were just going to be these nice sidebars and no longer primary characters in my life story. Finally.

“OK,” I typed. “I’m listening.”

My new lover is a cuckold!

Florida went on about how he got off on jealousy. He liked knowing the woman he was with was sleeping around on him. The newly single part of my mind got excited. I had scored a cuckold (definition: the husband of an adulteress, often regarded as an object of derision, but in the fetish sense, cuckolds were willing).

Florida wanted to watch me seduce, tease, and flirt with random men. He wanted me to screw whoever I wanted when I wanted, and explicitly detail my sex life. As someone who had always struggled with infidelity, I felt as though I had hit the jackpot.

I have cheated on every single boyfriend I have ever had. I used to think it was because I never truly loved any of them, but now I realize it was more about the reality of my ego and confidence. I am a flirt by nature. I seek attention from both sexes. When I was 15, my Aunt Marissa gave me a novel called “Cheat” about a British woman who had seven sexual relationships going at once, with both men and women. I always wanted that. I wanted to be in control. I wanted to be the one who got to do whatever I wanted while my partner stayed obedient and faithful to me.

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My twisted dream on a silver platter

My one downfall was jealousy. I was not good at sharing my partner with others, which is why I would only guest star in three ways and resorted to cheating instead of an open relationship. I wanted my partner to be faithful to me while I could get my kicks elsewhere. It was completely unfair, ludicrous, and selfish.

But here was Florida, handing me my twisted dream on a silver platter.

“I am so into this,” I typed to Florida.

“Tell me something now” he pressed. “Something that will make me jealous.”

I thought for a minute.

“There’s this big construction worker type with a huge cock,” I wrote. I told him I’d had sex with the guy the last time I was home for a friend’s wedding. “After the party, I made him carry two vases of flowers and my shoes while we caught a cab. I also made him pay for that. We got to my house, then we fucked for hours. He fisted me until I cried. I thought about you occasionally but it didn’t last because he is better than you.”

“This is so hot,” Florida responded. I imagined him trying to masturbate while typing on his shitty phone and laughed a little.



Mistress Delilah Collars Me

The Night That Changed My Submissive Life


3 thoughts on “I Dated a Cuckold”

  1. Story sounds like I told it Why do I want that? I have a woman now who is doing that to me through internet I want the real thing I find it so hot my mistress fucking who ever she wants an ordering me to serve her
    This woman Im texting with,I dont no how but she somehow has brainwashed me into doing whatever she orders me to do I have done things I never thought I would do in a million years I will leave it there before I say to much
    But I would love to be involved with a mistress just like the story

  2. A great read! Open relationships, polyamory definitely isn’t for everyone! Same goes with cuckolding. It’s always about compatibility 🙂

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