Sissy Fem Cuckold Captions Stories

13,565 results
Orientation
Length
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Infinite Scroll

VooDoo Doll

by OathkeeperPath on Apr 22, 2025

The sun was setting over the horizon, painting the schoolyard in hues of orange and pink. Graduation caps littered the ground, reminders of the euphoria that had swept through the air just hours earlier. Amidst the abandoned caps, there was a lingering sense of farewell, a mixture of excitement and melancholy. In this bittersweet setting, you found yourself...

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Powerless

by siscuc on Sep 16, 2017
Transsexuals & Crossdressers

I was alone in the house, Tina was at work. It was 4 in the afternoon and i was looking over some pictures when the phone rang. It was Tina, "Hi Sweetheart" i said. The tone of her voice was harsh "Start getting ready, tonight you will be my sissy, you can choose to wear any of my clothes except the ones in the top drawer, I'll be wearing them." That was all...

Neighbors Sissy Son Ch. 02

by newfield1981 on Nov 21, 2017
Transsexuals & Crossdressers

This is a prequel to 'Neighbors sissy son'. It's a stand alone story but trust me it will be a better read if you've read the first chapter. ***** Looking back Charles remembered always being the smallest kid in the class. Even now at 18 years old he was still the smallest. When other boys were just starting to notice girls and their changing bodies, Ch...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

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...

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....

He Looks Like His Father

by RainStevens on Sep 13, 2017
Interracial Love

WARNING! This fictional story isn't for everyone. It involves cuckolds, male feminization, submission, interracial sex and breeding. If you're not interested, go find another story. * I am a white fifty something year old married cuckold and a proud member of the W.B.A. My wife is twenty years younger than I and we have four children (with one on the way),...

My Cuckold Story Pt. 02

by ohsubmale on Sep 14, 2020
Transgender & Crossdressers

Wife Plants Her Ownership Pole - It's been a little while since I last shared about my experiences, so I am sharing my second experience I believe worth sharing in my deep dive into the submissive cuckold I have become. This is based on my real-life experiences, so please keep that in mind if it doesn't tick off all of your fantasies at once... I know our li...

His Sissy Bitch Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It started after a transvestite walked into the bar. Sounds like the start of a bad joke but it's not, we were in a party bar after work, me and my boss. My boss and I were having a drink after work; he was more than a little high. An obvious cross dressed man with several friends came in and sat at the bar. 'She' was very cutely dressed, stylish and sexy. M...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...