Sissy Cage Stories

19,847 results
Orientation
Length
Source
Infinite Scroll

Sorry Sissy You Lose Pt. 03

by LittleDickSissy on Feb 11, 2019
Fetish

"Mmmm that felt great" George said as she released his thick cock from her mouth. "Thank you". She looked up at him and smiled. She could still taste his cum in her mouth. She'd never had cum in her mouth before let alone swallow it! "Kiss it. Kiss my cock" George instructed her. She did as she was told, she puckered up and kissed the head of his cock a...

Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

Oh, Mr King! Pt. 06

by exaucer on Apr 18, 2018
Transsexuals & Crossdressers

I leaned towards Mr King's fat, hairy cock and sticking out my tongue, lapped softly at the tip of his cock head. I knew not to use my hands. I placed my arms around him and cupped his bum cheeks. While I was lapping at his engorged cock head, I let my fingers playfully rove up and down the crack of his ass. From his reaction I knew he liked me doing that to...

The Awakening of a Sissy Pt. 11

by sissyjolie4u on Jul 13, 2020
Transgender & Crossdressers

We had been driving in silence for about 10 minutes, with me reflecting on the changes to my home and the 2 men I was going to be meeting. I was both excited and nervous about meeting with Roy and Ronald. Mistress Di broke my thoughts stating "I think Nikki has done an excellent job with her house transformation work, don't you agree Jolie?" I looked over a...

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...

A Virgin locked in Chastity

by ronron1818 on Mar 3, 2020
Fetish

I was 18 when I moved in with Ruth. Ruth was my new land lady, I moved in with her for my university studies time frame. She had a big house and leased a room. Ruth was 56, in great shape, she was about 170 cm tall and about 50 kg with small breasts and a very nice figure. I was very excited to move, I loved the idea of sharing a house with a woman. I imag...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

Natalie on Sunday evening

by natalieukcd on Oct 19, 2020
Transgender & Crossdressers

I spent the rest of Sunday cleaning the house and myself and removing Natalie from the male me, yet again, putting her away in all the little hidey-holes i had. I couldn't hide the lack of my body hair, nor the cock cage from my wife. She had seen the cage so knew it existed but she didn't like it. It 'made my cock look like a mugger' she said. After that I...

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...