Chastity Cage Sissy Stories

23,357 results
Orientation
Length
Source
Infinite Scroll

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...

Turning into His Toy Ch.03

by vaultdweller111 on Sep 13, 2017
Transsexuals & Crossdressers

My heart raced as I saw the tray one of daddy's maids held. On it were a wooden paddle, a pair of handcuffs, a pair of nipple clamps, and a pair of white cotton lace panties. "Alright Ashley come wait with the tray by my side and Lilly put your hands on top of your head so I can get a good look at you." He commanded us both. "Yes daddy." We both answered...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

Made to Obey Ch. 11

by madetoobey on Aug 21, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

Miss A's New Play Thing Pt. 03

by Pornenthusiest on Dec 2, 2019
BDSM

Alex, the 23 year old virgin, had just left his first session with his new Mistress, Miss A. He left chastised, blackmailed and with a new obsession with feet. Chapter One: The Envelope Alex had gotten on the bus, it was his first time in public wearing his chastity cage and he was very self conscious about it. He thought he could hear the lock click agai...

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...

Road Dog

by TwistedPanties on Mar 3, 2020
Erotic Horror

It all started with a bit of fun on his road trip. Bryan was en route to San Francisco to hang out with an old female work colleague, as "friends". She was a couple years older than him, 32 to his 29, and she had a great apartment downtown. Of course Bryan had wondered if she would let him put the moves on. It didn't matter if he got to hookup with her or n...

Sandra and Stevie Ch. 31

by Goodhusband on Sep 13, 2017
Loving Wives

Note: This story is the thirty-first installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongl...