Sissy Age Regression Stories

91,775 results
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Infinite Scroll

Natasha in the Snow

by morethananeyeful on Sep 3, 2017
Erotic Couplings

Natasha was cross. Her supposed trip of a life time to the reputedly sunny and friendly USA was not working out how she planned. She had certainly not been told that snow was likely in New York state's Catskill mountains- in June!- nor that the boss of the law firm where she had secured a job and whose house she had to live in would hardly utter a word to he...

Right Neighborly Of You

by vividlyyours on Sep 12, 2017
Erotic Couplings

Damn, she's cute, he thought, trying to maintain his cool while conversing with his neighbor. A funny word to describe a woman approaching 50, but it fits, he told himself. Contrary to the popular wisdom about older men and younger women, he preferred them closer to his own age, with the wisdom, experience, and maturity that brought. Plus, he liked real curv...

K.U. High School Stories

by seannelson on Sep 17, 2017
Non-Erotic

(for those from less advanced cultural meccas: that's Klamath Union High School in Southern Oregon, USA) 1.) In freshman year, I went out for track and joined the long distance team. I did this because I wasn't very fast and really just did it for fitness and to see pretty girls in their track outfits. One day, I just didn't want to do the 5 mile run so I...

The Sex Survey

by flashgordon562006 on Jun 19, 2019
Erotic Couplings

My name is Lois and I am 22 years old and just graduated college. For the summer, I decided to get a job until my post graduate studies started in the fall. I went on the internet and found that the Johnson Research Foundation was hiring people to take surveys in my area so I went there and filled out an application and was hired. On my first day, they gave...

Quicksand! Ch. 01

by vietnamvet on Oct 8, 2019
Erotic Horror

This story is not true. It is a fantasy that depicts what happens when someone isn't true to a gorgeous, intelligent woman who could be mean. Anyone in the story who resembles someone in real life is only coincidental. If you're not sure you like a story with an unhappy ending find another story to read. ***** Valerie Washington was a very pretty black wom...

Peeing

by vietnamvet on Nov 18, 2019
Fetish

This story is not true and if anyone in it resembles anyone in real life it is only coincidence. * Joe had become a pants wetter and he couldn't do anything about stopping it. He can pee instantly whenever his wife gives the signal. His habit is completely controlled by her! His name is Joseph (Joe) Martin and he is 36 years of age. Joe is decently fit as...

My Hairy Dorm Room Gangbang

by jennyjeanne17 on Oct 3, 2018
First Time

My name is Jennifer, and this is a completely true story. The events told actually happened. This story took place in the year 2008, which is the year I graduated from high school and moved away for college. I was tremendously nervous about moving away from home but I felt ready for the fun that awaited me at college. Little did I know, how much fun I would...

Self-Bondage Mess Up!

by maturejohn on Mar 18, 2020
Fetish

I set up a pulley overhead and threw the cord over so it reached ground. I attached weights and keys to padlock on one end. The other end I attached a drink bottle with inserted straw. It weighted such that when the drink bottle was almost empty the keys would then descend to the floor. I used straps with "D" connections and fastened them on my wrists. I had...

The Accidental GILF

by anonymouse333 on Mar 2, 2020
Mature

It was a lovely midsummers day in Berlin. My wife and kids were away in Dresden for the week, visiting the grandparents and I had decided to visit a nude beach for the first time at the age of 45. Having grown up in the UK, it was a bit of a culture shock when we first moved here to witness the nonchalance with which East Germans get naked in public. Apparen...

Laura Roft: Piss Raider - Reboot Ch. 02

by leaky_one on Aug 6, 2019
Fetish

The woman beyond the undergrowth that shielded her from sight was possibly the most attractive person that Laura had ever seen. She was an inhabitant of the jungle, of that there was to be no doubt. Her clothing was of rough cut animal skins; a mix-mash of different beasts crudely sown together. Despite the primitiveness of her attire, the woman still radiat...