Sissy In Chastity Fucked Anal Stories

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My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

His Fantasy Brought To Life

by ksha on Sep 16, 2017
Anal

To my surprise, my first story was received quite well! So thank you to everyone who read and liked it, hopefully I can continue to make enjoyable stories. As per a request in the comments on the last story, I am writing this. It's a stand alone from the other story, but follows similar lines. It's also going to have a long build up, but I'm hoping the end...

Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...