Sissy Cage Stories

19,847 results
Orientation
Length
Source
Infinite Scroll

One Friday Night Ch. 02

by skinnysailor on Sep 23, 2019
Transgender & Crossdressers

"Don't take all day honey. Alisha and Keron want to see them." As soon as they had boarded the charter cat in Prickly Bay, they'd dropped the mooring and set sail. Captain Keron was at the helm. His mate, Alisha, was mixing a big pitcher of rum punch in the galley. James and Helen went to their separate cabins to change out of the clothes they worn on the f...

The Nemesess Ch. 02

by ProfessorPlums on Sep 15, 2017
Fetish

Correspondence from older (50-70), dominant ladies most welcome. * The next few weeks passed slowly for Chris. He was initially terrified of his new Mistress, - after the ordeal of his 'breaking in'! However, his new Mistress (Theresa) didn't want a simpering bundle of nerves to play with. Dominance for her was a varied and protracted feast; full of spice...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Creating Ginger Ch. 07

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. Hopefully you've read the previous chapters to understand the nuances of this storyline. ~~~~~~~~~~~~~~~...

The Dominatrix Order Pt. 04 Ch. 04

by Jwwsmith on Apr 23, 2019
Fetish

Slave boy departed the docks and stumbled back to Femininus, dazed and in despair. He had no idea what to do. He had made the arduous journey, both physical and emotional, to becoming a slave of Femininus, suffered so much heartbreak and rejection to finally find his perfect Mistress, only to get to spend such a brief time with her before she was taken so ve...

Sissification 101: Ch. 04

by silkstockingslover on Jul 14, 2020
Transgender & Crossdressers

Sissification 101 Ch 04 Summary: Eric sucks his first BBC in a threesome with Joan. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by his...

Truth or Dare Takes a Turn Pt. 02

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

Morning rises and I must have eventually fallen asleep during the night as I am awoken by a swift and stubborn kick to the stomach. "Rise and shine sissy boy, you've got a lot to do today" sprooked Luke as he looked down at my filthy curled up body. I peel myself off the hard cold concrete of the patio and instantly feel the pain of my cock being squeezed...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...

The Entertainment Ch. 02

by econut on Sep 16, 2017
Fetish

I had just finished cleaning up after dinner when the doorbell rang. Master and Mistress's guests were here. I had been instructed to let them in when they arrived. I was nervous as I walked to the front door. Gary and Lana, my Master and Mistress, had never had guests over while I was here. And until today, they had never made me dress in drag, and now I wa...