Chessie Kay Sissy Caption Story Stories

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Rebirth of a Hero? Ch. 04

by Tbcody on Feb 10, 2020
Sci-Fi & Fantasy

Hello folks and sorry about the delay in posting this story (holidays and family passing) I would like to give everyone a small warning that there is a non human/monster with human near the end incase that's not your thing. Have a good day and happy readings. ¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤¤ "Yes I do, I can't keep something like this a secret as it...

Three At Last

by penncd on Sep 1, 2017
Group Sex

George and Emmy had made this drive to Atlanta before and it was always fun. Just getting away from all the stress at work and at home was so relaxing. They had known each other for a while and been lovers for almost as long as they'd known each other. There was easy conversation between them and even easier silences as they drove down I-85. There were lots...

Finding Francesca

by Rollinbones on Feb 10, 2020
Romance

My daughters friend Francesca is one of those lovely quiet women who underestimates her own beauty. She has been a loyal friend to Delia since the two met at university. Delia is twenty-three and the spitting image of her late mother, Nessy. Vanessa died to leukemia two years ago. One day she was feeling run down, the next she went to hospital to get some bl...

Sissy to Military School Pt. 03

by Tranylvr on Dec 2, 2019
Transgender & Crossdressers

The continuing story of Sissy Steffi at military school. If you haven't read the previous chapters, please do for context and back story. All characters in this story are of legal age. This story depicts the explicit erotica of a transgender nature. If this material is offensive to you; or forbidden in your area, or you are a minor, please stop reading! All...

The Life and Fantasies of a Sissy!

by gasissynora on Nov 6, 2018
Transgender & Crossdressers

The following story is partly true and partly fiction. The names have been changed to protect the guilty. I hope you enjoy the story as much as i did living parts of it and wishing i had lived the rest of what is here. ***** A number of years ago i saw an ad from Mistress Kay and was fascinated by what i saw and read. After thinking about it for a while i...

Overwhelmed

by LP1957 on Sep 17, 2017
Loving Wives

I guess it's mostly my fault. I had things perfectly my way and wasn't satisfied. My wife Kay and I had been married for 8 years. Guess we lasted one year past the "7 year itch" before things started getting routine. A little about Kay, she is 36. 28 when we married 8 years ago after dating for a year. She was quite inexperienced in the man department when...

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...

Aztec Art - The Path to Submission Ch. 05

by Sputnik57 on Dec 23, 2017
BDSM

Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

Rebirth of a Hero? Ch. 05

by Tbcody on Mar 16, 2020
Sci-Fi & Fantasy

Nataly stretched as she woke up, her hand brushed against Vals back, Nataly smiled as she slowly crawled over to Vals hips and rolled her over slowly. Val moaned as she opened her eyes slowly while smiling as she noticed a reddish gold head of hair was wiggling between her hips. Val reached down and gently pulled Natalys head up, "Well good morning to you t...

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...