Mature Chastity Stories

35,203 results
Orientation
Length
Source
Infinite Scroll

Spalding and The Cheerleader

by justincbenedict on Sep 17, 2017
BDSM

22 year old Spalding Tyll walked home disconsolately, his knapsack hanging off his arm. It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls. Mother was mad at Spalding... She was going to punish him through humiliation by making him jerk off in front of the hottest cheerleader at Buttermilk Fall...

Inner Demons Are In Demand!

by TrojanSnake on Sep 16, 2017
Erotic Horror

The nunnery had none, but the abbey happily had one. Was sex a sin if it was sanctioned? Based on an il-lust-ration by Pandora's Box Author's note: Pandora's Box created an extraordinary scene in one of his drawings, as described in the latter part of this tale. It has cried out for an explanatory narrative to give the viewer a back-story to the scene. Th...

Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

Interracial Extravaganza

by Yelawolf on Nov 26, 2018
Interracial

All stories in here should be about people of different races, anything else goes, you may have a single couples or contain multiple partners as long as one is of a different race to the rest. Human, Monster or Furries will be allowed if you want to start a story concerning them. Remember; all stories contained in here are fiction and the author does not con...

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Black Masters into Black Femdom

by Samuelx on Oct 16, 2018
Erotic Couplings

"How do you like my big Black dick up your ass, Rosita?" Trevor Johnson, also known as Master Tee, said as he spanked her big butt and worked his hard dick into her backdoor. Face down and ass up, the curvaceous, plump Afro-Cuban gal was in heaven, with her beloved Master going to town on her like only he could. To really shine Rosita on, Master Tee gripped...

My Old Guy Ch. 03

by anonentity on Sep 17, 2017
Mature

"Dear Mister Old Guy, Here it is Thursday and so much has happened since you tried to fuck me last Saturday that I just had to write and tell you all about it. On Monday I had to do confession with my teacher after Chastity Class. Her name is Miss Lola and by the way everyone calls her 'Luscious Lola' behind her back. Well when I told her how I began by...

Dominant Housekeeper

by justincbenedict on Sep 12, 2017
BDSM

The new housekeeper, Miss Spargrove landed the thick wooden Spencer paddle for the fiftieth time on Shawn Cirrito's reddened buttocks, and Shawn bit her tongue to keep from screaming. As the paddle, built with holes throughout to make swinging easier and more painful landed again on Shawn's ass, she wondered what Ross was doing. Miss Spargrove had had hi...

The Cuckold Life

by cuckytoher on Aug 18, 2017
Fetish

I'm sitting outside a restaurant wearing sheer to the waist pantyhose and a cb3000 chastity device waiting to pick my wife and her lover up after their dinner date. I'm excited and can feel my tiny cock straining against the device wanting to get out and play. I was told to be here at ten pm to pick them up and it's now almost forty minutes later and they st...

Femdom Future Ch. 00

by Wisdom_Seeker on Sep 15, 2017
Sci-Fi & Fantasy

PROLOGUE In the early part of the 20th century there was women's liberation and feminism took hold. Women strove for equality, or rather equal opportunity with their male counterparts. There were many changes made for the better. In the later part of the 20th century and the start of the 21st century, most women felt they had achieved equal opportuni...

Letter from Augusta

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom Deuce, my second son is finally beating me at Ping-Pong. The ball flies over my head! When I was a kid the balls were just white, but now they come in neon orange! Deuce looks relieved, I wonder why. Is it because I have always punished him, taking his pants down and spanking him hard with my paddle when I beat him at table tennis...what a...