Sissy Robber Porn Caption Stories

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The Guy in My Wife's Panties

by Candyboi on May 1, 2018
Transsexuals & Crossdressers

The catalyst for the paradigm shift in the relationship with my wife of twenty years was something that happened at the beginning of December - though, truth be told (as you'll see), there were several other naughty escapades throughout the autumn that really should have awoken me to the realisation that Carla was becoming the dominant one in our relationshi...

A New Life Ch. 03

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

"Click on this link, sissy. I want to show you something," Mistress Sally said. And I happily followed instructions believing it to be some aspect of sissy porn like a caption, or little GIF video. I couldn't have been more right...or more wrong. My newly painted red lips parted in shock as my computer opened a new browser that showed what seemed to be an a...

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...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

The Birthday Suit Club - The Beginning

by Jamie753 on Jan 14, 2019
Exhibitionist & Voyeur

Editor's note: this story contains scenes of incest or incest content. ***** EVERYTHING IN THIS STORY IS FICTION, EVERYTHING. All characters are eighteen or older. ***** First let me set the scene for you. My name is Jamie. I call myself Jamie753 because when I was seven I received a very stern lesson that small children should be not allowed near gas c...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Hero Losing Himself

by lol159 on Jan 8, 2019
BDSM

Since Mark was a kid he dreamt about being a hero. He wanted to be someone who did the job on his own. He wanted to be the macho just like his hero The Jaguar Man. He was the proudest man about himself. Having been grown up in an orphanage after his parents were both killed by a robber, he knew best that no kid deserved to lose his family. That's the reason...