Sissy Stories Porn Captions 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...

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...

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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Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

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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Farewell from Randydaughter

by randydaughterreborn on May 15, 2018
Reviews & Essays

I've been writing my erotic stories on and off for almost 10 years now, and I think my well of creativity may finally be running empty. I might post the occasional story here if the muse strikes me with a good enough story, but I think overall I might be done with actively writing erotica. Before I go, I thought I might write a kind of farewell letter to my...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...