Sissy Permanent Chastity Stories

27,304 results
Orientation
Length
Source
Infinite Scroll

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

The Sexy Cuckold Couple Pt. 04

by cuckcpl4play on Sep 19, 2017
Fetish

Miss Jenny and I entered the home and there was a sense of relief to be in our own house and only then did we communicate. I asked simply...did you enjoy yourself and Miss Jenny smiled broadly...his cock is so huge and he felt so amazing inside me...the experiences we are all going to share will be amazing slave and she hung on that last word for a bit. It w...

Tina Rules! Ch. 3

by jimmysub on Sep 16, 2017
Fetish

(In the first two chapters jimmy is discovered to have visited some fem Dom sites on his computer. Tina his wife with her young co-worker Lydsay begins to train and emasculate him. In this chapter jimmy's past comes back to haunt him.) Tina sent me to my room after I had satiated her. She gave me instructions on how I should be up earlier then her so that I...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

Husband's Transformation Ch. 02

by Prematurelimphubby on Jul 3, 2019
Transgender & Crossdressers

Brett woke up the next day with the sun shining in through their bedroom noticing his wife wasn't in the room with him. He stepped out of bed, put his panties from last night on and walked downstairs for coffee. He saw a note on the counter. "Good morning Britt, I had to run and get a few things from the office. I should be home soon. Take a relaxing ba...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...