Sissy Cuck Captions Stories

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Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

Captions and Kink Support

on Apr 22, 2025

This post collection is to help... A) Deepen your corruption into your kinks and fetishes B) Corrupt you into discovering new kinks and fetishes C) Train your body and mind to succumb harder and faster to your kinks and fetishes Each fetish will have post containing either a picture or a gif. And some text below. The text consist of either a short erotic sto...

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Birthday Party Pt. 01

by JamieMcKafee on Jan 22, 2020
Transgender & Crossdressers

**First public story submission, so apologies if things are a bit jankey. Contains lots of nastiness, including but not limited to: futadom, futa on female, cuckold, SPH, bondage, etc. All character are over the age of 18. Hope you enjoy :) ** ***** "Harder!...Ughh! Harder, fuck my dripping pussy harder, Skye! I love you, keep fucking me, baby! Oh god,...

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...

Mistress Morgan's Sissy Husband Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Robin arrived home from work about 5:30 on Thursday, he still felt a little apprehensive about what happened Tuesday night with his sissy friend Patty, and he hoped he might get to talk about it with his wife Morgan. He really enjoyed wearing the corduroy skirt outfit she bought for him, and he loved being a sissy whore for his wife and Patrick, her "boyfrie...

A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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Making a Sissy Jock Pt. 01

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

My life changed about a year after I was done college. I'm Mason, or I was and I used to be a football jock all through high school and played all through college and after all that I kind of just never got picked up. So...what do you do with a physical education degree? Most guys taught gym or coached some places. Me? I got a massage job at a spa. There...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

Carol, Candy & the Ex Pt. 02

by corduroysissy on Mar 26, 2019
Transgender & Crossdressers

(Will Candy make a good cuck?) Davie was standing at Carol's front door dressed in a pair of copper brown wide-wale corduroy dress trousers, and a beige polo shirt. Oddly enough, he felt more nervous than he did the night before when he was in full drag, and he attributed it to the ex-factor. Last night Davie as "Debbie" was there to meet Robbie as "Candy"...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...