Sissy Anal Training Stories

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Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

Sheila's Training Ch. 01

by CeliaisAliena on Sep 15, 2017
Anal

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!! It's more than the hair,...

Mistress Jaz's Sissy Slut

by barbiboi on Aug 30, 2017
Fetish

Mistress Jaz had invited me over to give her a pedicure and provide sissy maid service. What I got was a mind blowing day of servitude I will never forget! I arrived in the morning and was greeted by a vision of beauty. I had seen pictured of Mistress Jaz before, but they paled in comparison to meeting this incredible Goddess in the flesh. Tall, curvy, wit...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

On Her Terms Ch. 04: The Party

by econut on Sep 18, 2017
Fetish

Dale was just bending over to pull the laundry out of the dryer when his ass began to vibrate. The sensation caused him to jerk back upright. The vibrating butt plug, operated by remote, was his signal to go find his Mistress. It vibrated quite often throughout the day. His Mistress, Sam, a butch lesbian, had trained Dale to be a sissy slut, and her personal...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

Dominating Ken Pt. 05-08

by oneguy4fun on Sep 26, 2017
BDSM

PART V TEASED AND ENTRAPPED! Monday evening Kareena logged on and was delighted to see an e-mail from Ken. She had instructed him not to write until her present arrived and she knew that it had not arrived. She was curious as to what he had to say. She wasn't even halfway through the e-mail and her pussy was hot and beginning to dampen. It was obvious that...

Francie and Graeme's Defloration

by skriblur on Sep 12, 2018
Erotic Couplings

The odd-numbered parts have the sex. The even-numbered parts have the love story. ~1~ Francie likes what she's seeing -- her feminized husband. All slutted-up in strappy heels and frilly socks, a cute cornflower blue skirt and white cotton blouse, kneeling in front of the living room couch, sucking off one of Francie's boyfriends. Francie (wearing nothin...

Mistress Red Fox Becoming a Devotee

by His_fag_wife on Sep 24, 2019
BDSM

A story of what might have been a dream. Names have been changed. *** One evening I was looking through profiles on a BDSM website and came across one for a local Mistress, she was developing a new dungeon and she was asking for suitable subs for her to try it out on. Someone to test the new equipment and layout on. I read the ad over and over again, this...

The Discipline of Goldilocks Ch. 02

by Quazzi on Sep 12, 2017
NonHuman

Author's Note: Just wanted say thank you all for reading and enjoying this one. Please know that through the most of this there will not be any sex really. I wanted the main part of this one to be a build up to what you can expect. I did add a little quick scene at the end for you all to enjoy. The next one will have a lot more... also should be out a lot qu...