Chastity Aunt Stories

18,923 results
Orientation
Length
Source
Infinite Scroll

Trapped as a sissy in a fanasy world.

by Duke Montefort on Nov 14, 2019
Fetish

Eugene has an obsession with video games almost shutting out his friends and family. Feeling they have no choice the family begs a videogame company to help them bond with him. The company agrees they test the family can beta test the game, and bond. They even promised that he could not come out until he had properly bonded with each family member seprately....

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Paige and Spalding

by justincbenedict on Jul 4, 2018
BDSM

Dear Mom, Thanks for the lemon bars. It'll help me stay awake during my property class. Tell Rylie that I'll bring back her mohair coat, don't have a cow. So you were asking me about how things are going with Spalding. I was so glad you and Dad liked him when you came up to school. I agree he's cute and has a good sense of humor, and Dad said Spal was obv...

The Spirit of Lady Macbeth Pt. 07

by alyssawinters on Oct 19, 2020
Transgender & Crossdressers

The campus still empty for holiday Tracy his backpack replaced with a catch-all purse walked across the quad gripping the strap looking to kill some time reading before returning to home and Mistress Lisbeth. Spotting the couch in the near empty coffee house he planted down in the middle of it ready to open his book of Shakespeare's 'the Tempest'. Nervous...

Letter from Barnsley Cloisters

by justincbenedict on Oct 8, 2019
BDSM

Dear Shoeblossom I have a tale for you...here in the Cloisters, they call me the "Sonic Submissive Story-Spinner" Sonic for short, and I thought you'd find this one invigorating! I have been having such a hard time sleeping. I have a chastity piercing at the end of my penis. I stay up at night because I can't cum, and having an orgasm is so relaxing. And...

OMG Mom!

by TheSecretlyUnlikelyDuck on Feb 5, 2019
Interracial

You pull into the driveway of 15 Preston Road at around 3pm on a friday afternoon. The light of the late spring sun pours over you as you come to a halt, parked behind the red BMW belonging to Mary Lange. She is a gorgeous blonde, who looks far younger than her actual age of 39, and is unarguably the head of the Lange household. You don't see her husband's c...

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Letter from Mount Chapel

by justincbenedict on Aug 20, 2018
BDSM

Dear Shoeblossom, I got into the sweetest deal. I agreed to play femdom games with my geeky male roommate. He owns the house and was renting me one of the rooms, and like so many nerds, he has the hots for us tattooed, embroidered jeans types, I guess. Oscar is the sweetest guy, you know the kind. Comes to try and ask you out when you're smoking in the sch...

Castle Slave Ep. 01: Rose Girl

by AlinaX on Sep 16, 2017
Sci-Fi & Fantasy

My father was a Brownman, a servant of the Outer Castle, as his mother had been - until she was promoted to a Greenman, and entered the Inner Castle. I never saw her again, though my father saw her from time to time. Only servants, the army and the aristocracy entered the Castle at all, the servants through the North Gate, and the aristos through the South...

Marianna and the Pirate

by BewitchingRose on Mar 20, 2018
First Time

Marianna felt watchful eyes on her as she tended to the patrons of her Aunt's Inn. The Inn was alive with the sound of chatter, but the source of the eyes on her was in a pocket of silence in the dimly lit corner of the Inn. She shot a glance towards the man watching her, and felt, as she had the first time she laid on eyes on him when he walked in, a warmt...

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

Mother Mistress Ch. 07

by JamesLacy on Sep 12, 2017
BDSM

This story is the property of the author. It is not to be changed in any way, nor published or shown at other web sites without the permission of the author. Feedback and comments to; James Lacy at the address in his profile. All comments appreciated. Earlier, Mother Mistress had called Cindy to tell her that she and Jane decided to spend another two week...