Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

Camboy's New Mistress

by pluggedforlife on Jun 5, 2018
Transsexuals & Crossdressers

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate. He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs. His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver ho...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...

Milking Her Husband

by ringmaster92 on Sep 12, 2017
Transsexuals & Crossdressers

This is a fictional story. If you are not an adult, please leave right now. If you're an adult, then I would say this story contains female domination. If it is not your taste then kindly move on. I would like you people to comment on the text here. Criticism is welcome though only constructive criticism. Any tips or suggestion on grammar, plot and character...

Humiliation Journey The Beginning

by Subkoksukr4u on Jul 16, 2019
Transgender & Crossdressers

It felt like a bad dream. My body was sore from been used by the staff. seems like I'd been fucked constantly the past 24 hours. I was getting used to my large breast implants now, however, the cage on my new huge penis prevented erections but kept me aroused and dripping pre-cum. Madeline arrived and entered my room arm in arm with the doctor. I noticed...

Happy Together

by Fafantasiz3 on Feb 12, 2019
Transgender & Crossdressers

-*ring ring* -... -*ring ring* -... -*ring ring* -... *clic* Hey there! (She speaks in a deeper voice, she sounds tired, she's probably been at it again, and for a while, by the sound of it) -Hey you. Busy? (His voice is as usual deep and melodious and terribly sexy -- she usually says she fell for his cock first, and his voice second -- the slight ec...

Forgiving Wife Pt. 03

by manatdawnrise on Feb 1, 2018
Transsexuals & Crossdressers

The night was still early but with the combination of travelling, drinking on an empty stomach and the emotion of talking about my interest in crossdressing, I was exhausted. I suggested going to bed to which Mandy agreed. I stood behind her brushing my teeth wondering what was going to happen now my sordid secret was out. I caught Mandy's eye in the mirro...

The King's Secret

by KittyAshleyy on Apr 22, 2020
Transgender & Crossdressers

King Mike was a great king, the people loved him, he had a beautiful queen, he ruled firmly but fairly and, at the age of 24, had a great reign ahead of him. He was tall and well built, keeping his lovely blonde hair short. He had blue eyes and a gentle smile. But he also had a secret. That secret was me, his concubine. He had picked me up off of the street...

A Sissy is Born Ch. 02

by gtanya on Oct 13, 2020
Transgender & Crossdressers

Author's note: This story is the second chapter of "A sissy is born" series. Please note that it is a very slow build up and if you are looking for some hardcore sex right away, it is not for you. Please leave your comments to help me improve. It was a fairly uncomfortable couple of hours of the train ride with the constant staring of Mr. King. His gaze som...