Gay Cuckold Captions Stories

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Wife's Exploration

by cpandy on Jul 5, 2009
Cheating Spouses

John sat in front of his PC trawling through Imagefap, his latest search for cuckold captions had uncovered a goldmine of unseen pics and his cock was stiff in his pants as he immersed himself in their delicious humiliation. He clicked quickly to those of a well built blond that paid a passing resemblance to his wife Doe. Stroking his cock through his pant...

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Tales from the Oedipal Zone

by crazydorian on Mar 24, 2019
Fetish

The Oedipal Zone idea is a creation of Squelchapron, from his old “freeusecaptions” Tumblr. The original captioned stories (Field Observations and Paragon Magazine) have been used here with his permission. An Oedipal Zone is an area within a more general free use world. The normal free use tropes apply in most parts of the world: society functions more or le...

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What is This on Your Computer

by mgablea on Sep 25, 2017
Loving Wives

"Barry, what is this on your computer?" My startled wife Lori asked. Oh shit! Oh shit! Oh shit! I had royally fucked up. How could I have been so stupid? I had been browsing through my collection of pornographic pictures with cuckold/hotwifing captions and had accidentally left a picture up showing a blonde woman, who looked a lot like Lori. The woman was...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

The Perfectly Adequate Cuckold

by WendyHott on Jul 31, 2019
Loving Wives

Show me a man who hasn't wondered how he'd react if he walked in on his wife fucking another man, and I'll show you a liar. I can tell you this. You're never prepared for it. I came home from work that day at my usual time, five PM, just like clockwork. I get off at the store I manage at four forty-five, and it takes fifteen minutes to drive home, so it wa...

Fan Fiction Captions

by pornsleuth6 on Apr 29, 2025

I have been making a lot of captions lately, so I thought it made sense to split the captions off from my short story collection (https://chyoa.com/story/Short-Fanfics.46075). They are similar things of course but different enough that I don't want to disappoint people looking for one and finding the other, update to update. The grouping on these will be fai...

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Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Farewell from Randydaughter

by randydaughterreborn on May 15, 2018
Reviews & Essays

I've been writing my erotic stories on and off for almost 10 years now, and I think my well of creativity may finally be running empty. I might post the occasional story here if the muse strikes me with a good enough story, but I think overall I might be done with actively writing erotica. Before I go, I thought I might write a kind of farewell letter to my...

Wren Likes to Dance...

by make me watch on Mar 12, 2019
Loving Wives

"Okay... to be honest, ummm, yeah Joel is actually really hot." My girlfriend had had too much to drink. Friday night had become Saturday and we were now back home and in bed after an interesting night out. Earlier, Wren had wanted to dance so we went to a crowded club with loud music. Not my kind of place but it worked for dancing (and drinking too). More...