Trans Trainer Cuckold Stories

13,402 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sucking Her Cock

by vividhallucinations on Sep 28, 2020
Transgender & Crossdressers

It had been years since Natalie had been to the gym. In fact, it had been more than five years, when she first began transitioning. She had tried to attend yoga and pilates classes, but the whispers and looks of disgust didn't stop and eventually she gave up. She was seeing a personal trainer for a private session at the recommendation of one of her best fr...

Femdom Scenarios

by unknown156 on Apr 29, 2025

Live through your wildest femdom fantasies as these sexy girls dominate and humiliate you to orgasm. Anyone can feel free to add their own storylines but they must abide by the following simple rules: Every character involved with the JOI or any other sexual activity MUST BE 18+. You can have characters who are under 18 but they can not be in any way involv...

Open in Reader

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...

Open in Reader

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...

Hot Wife Alycia

by KSBerry on Oct 13, 2017
Loving Wives

Gary and I have been married for 21 years. When we got together we were young and stupid. We didn't know shit about anything. He got me pregnant when we were 20 with our first child Steve. We decided to get married before Steve's birth. Despite our early adversity, we worked our way through it, and both Gary and I are successful at our jobs. Gary is an IT Op...

Cuckolds' Chat

by dickE on Sep 17, 2017
Loving Wives

The following is a letter of reply to my friend who just wrote about his wife's first 'date'. Fellow cuckold, I enjoyed your tale. I know that it was true because I could have written it exactly as you did. Like you, at around 40 my petite wife of 23 years who'd had 6 kids and was into her 'sexual peak years' also took on lovers at my request and encourag...

The Arranged Marriage Game

by remysloane on Jul 29, 2020
Interracial

3/2021 update: I'm enjoying the writing and will keep adding chapters. My request to you is this: give me feedback! Authors love comments, good or bad. I can go back and change stuff that sucks, or maybe change/add stuff at the request of readers. Join me as I navigate the oppressive Indian arranged marriage culture while exploring my sexuality. Your objecti...

Open in Reader

A Teacher's Way Out of a Dilemma Ch. 09

by SubBabs on Sep 12, 2017
Loving Wives

Last of Chapter eight John stood up and told the announcer that he did not want the woman and he was sitting with his wife. Kevin stood up on the table and told everyone that John was a cuckold and would rather eat out the used pussy of the first woman. A couple men grabbed John and forced him down between the legs of the woman that had just been fucked. Wi...

Lisa's New Body

by LiteRuby on Sep 17, 2017
Loving Wives

If you read my story How I Cuckold Myself, you know that I am married to a fantastic woman named Lisa. Well, after that very special night where we were visited by our "Mystery Man" I was not sure how our sex life was would evolve, if at all. Well things did change, but only for the better. Lisa did not get pregnant and I was relieved that she did not hold...

Your sammich maker; my fuck-pig!

by Wank_Gough on Jul 14, 2020
Fetish

Wank Gough, aka 'The Goughster' here, with some guidelines to help all you WASPs (White Ango-Saxon protestants) out there fulfil your cuckold status. Now, as I'm all about the love, here's a little warning: tetchy WASPs who don't think they're natural and willing cuckolds might want to stop reading here, as you're likely to not be able to cope with ideas w...