Feminized Chastity Stories

7,367 results
Orientation
Length
Source
Infinite Scroll

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

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...

Jolene's Momma Pt. 03

by ValoryG on Sep 14, 2020
Transgender & Crossdressers

(All characters and most locations in this story are completely fictional, with no connection to any persons living or dead.) My wife and I settled down into our new life together. I was now so respectful of her, and appreciated the new Jolene, able to take charge, express her anger when it arose, and generally run things. Like her mother, she really did...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

A Pro-Wrestling Cuckold Ch. 02

by longhairedcuck on Jun 12, 2019
Loving Wives

Hey y'all, so I didn't add any introduction in my last story but I felt it prudent to add a couple of pointers here. I'm new here, to this site, a pro-wrestling fan , and the intersection of cuckolding and pro-wrestling has always turned me on. This story is about a loving couple, who get introduced to this kink and eventually become a dominant hotwife-cucko...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Perrin's Naive Clientele

by justincbenedict on Sep 9, 2019
BDSM

"Spud, darling, I just don't have time for your whining right now." Perrin said acidly. She admired herself in the reflection of her wine glass. Perrin noted the desperation of the sad little creature in front of her. Why she agreed to have lunch with him in the middle of the week was a mystery. She knew what he said he wanted--Spud, like so many of her ot...

College Days – Domination 101 Ch. 04

by oneguy4fun on Sep 25, 2017
BDSM

Joe woke up with a raging hard-on. All the teasing and torture from Linda and Lori over the weekend had a lasting impact on him. Even though they had milked cum out of his cock before he went to bed, he was still horny as ever. The milking relieved some of the pressure in his cock and balls, but it added to his horniness. His cock twitched on its own as he...

Lost in a Female's Pleasure Pt. 03

by LucysFox on Mar 11, 2019
Transgender & Crossdressers

Synopsis: Damien had been looking forward to a relaxing weekend free from his abusive father, but things quickly take a downward turn when he's kidnapped and wakes up in a confusingly elegant room and learns that his life is about to change forever. After a confusing few hours of fear and pleasure he collapsed, and after waking up he is dressed and led towa...