Sissy Captions Stories Stories

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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...

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...

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...

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 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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Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

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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My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

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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Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...