Cuckold Trainer Captions Stories

11,797 results
Orientation
Length
Source
Infinite Scroll

Hypno Captions

by Bogglepomp on Apr 22, 2025

// All characters in this story are at least 18 years old. Sometimes an image begs for some text to really bring out its true potential. This story is for those pictures and captions. Stories will be on the shorter side, just as some bite-sized entertainment to accentuate the pics, though if the fancy strikes, longer stories are fine as well. Mind-control st...

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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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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...

Crossing the Line

by CopyCat13 on Sep 13, 2017
Fetish

Me: Hi there. No fair wearing heels. You'll make us shorties look even shorter. :P There, that should get a chuckle I thought. I was on one of those fetish sites and had just come across a rather attractive domme. Most of the people on here open with some stupid one liner or cheesy pick up line. I always tried to be a bit more creative than that. Sometimes...

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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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...

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...

Wedding Night Cuckold

by Ericw1970 on Jun 28, 2020
Cheating Spouses

This is a story about Samantha, a young white woman in her late 20’s, and her fiancé Eric. Samantha has jet black hair that goes roughly half way down her back, blazing green eyes, and a very petite figure (think 32-22-32). Eric is a white man also in his late 20’s and has light brown hair and blue eyes, and is pretty athletic. Samantha also has a twin, Anna...

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Cuckold Status: Active

by LockedSissySubmissive on Sep 13, 2017
Fetish

Ok, so I am officially a cuckold. There is no other term which so perfectly encapsulates the role I have accepted. I was totally complicit in my wife's infidelity and am just coming to terms with the realisation that some doors, once opened, can't be closed. Hannah and I have been married for five years now. We have an amazingly open and honest relationship...

Why I Am Da Man, Ya Cucky Bitch Ya

by Wank_Gough on Oct 5, 2020
Loving Wives

Your darling sammich maker's late for her pig training, so I look her up in my phone. I don't know what pet name you have for your darling wife, but I have her in my phone as 'Gammon Wallet'. Me: 'WTF?' She has sixty seconds to answer, period. No excuses, no exceptions. And she's signed up to it. It's a respect thing; no matter what the little slag wagon's...