Sissy Age Regression Stories

91,775 results
Orientation
Length
Source
Infinite Scroll

Momdom a sissy son's wish

by Viking973 on Jun 20, 2020
Transsexual

Intro: You never had much luck with the girls in high school. You had a few girlfriends early in high school but the last 2 years before college was rough. It had come and gone, you enjoyed it, you weren't an outsider and had many friend groups but you never went out to parties or out of school to meet up with friends. You enjoyed video games and porn too mu...

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Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Three Old Tarts and a Sissy

by Sissy Adele Howells on Oct 13, 2017
Fetish

At 50 years old, I have started to have kinky thoughts about older women. This fantasy that I am about to narrate to you concerns three neighbours of mine. Between them their ages total 200 years. They have found out that I'm a kinky sissy, but this seems to make them crave for more sexual activity. The eldest of the three Joan Harries, encourages the other...

Sissy Jessica Kinky Office Shagging Ch. 03

by Sissy Adele Howells on Aug 18, 2017
Fetish

It was a lovely sensation to be a member of the Howells family. At 18 years of age, I was now the foster daughter of Adele Howells. Her gorgeous daughter Francesca was my sister, to play kinky games with. Also I had the added pleasure of Joanne Harper, who had been persuaded to join us for the evening. Having exactly the same blonde hairstyle as Joanne, made...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...