Chastity Shrink Stories

14,310 results
Orientation
Length
Source
Infinite Scroll

Got Milk? Pt. 01

by macktosh on Mar 3, 2020
NonHuman

This story was written for the following prompt: "A young man works at a holstaur ranch, milking the breasts and cocks of the gorgeous and horny livestock that prefer the human touch over machines." (Note: Holstaurs are a kind of monster girl with horns and a propensity to produce milk, similar to cows.) This is quite different to my normal content, so ple...

The Snuck Orgasm

by Exlibro on Aug 20, 2018
BDSM

There you are! I was expecting you waiting at the door. I know, I know. I'm late, but I had to run another unexpected errand. My, your cheeks are flushed and your breathing is as fast as if you were running a mile. Is there anything you'd like to tell me, anything you'd like to confess? No? Well then let me tell you something, instead. You do know that you...

Cuckolded by Kate Ch. 01

by cuckytoher on Sep 12, 2017
Loving Wives

It's 7:45 am and I'm sitting outside Target waiting for them to open while my wife Kate and her lover Michael are home snuggled up in bed sleeping. I can barely keep my eyes open considering I didn't get to bed until after 3:00 am. My CB3000 chastity device is making my cock shrink smaller than it already is due to the cold air this morning. I have a lot to...

Arin's Inheritance Pt. 02

by mollycactus on Sep 18, 2017
BDSM

(continued from part 1) Arin's heart fluttered in relief and excitement as she heard Molly's voice on the phone. "Molly, I am so glad that you answered. Please come over to my house as quickly as you can." "Arin? Is that you? I have not heard from you in ages, but I'm glad to be back in contact with you. Why do you need me to come over so suddenly?" "I'...

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...

A Freshman's Summer Class Ch. 06

by CapnSteelBoy on May 13, 2020
Transgender & Crossdressers

**All characters are of legal age for adult content.** Trying to get these out faster, and writing more, but sometimes life just doesn't play along. Please enjoy, will probably wrap up around Chapter 9 before our hero heads back to school with all that new training! Chapter 6 The next few weeks went by pretty quickly. Nothing much changing in my life f...

Seven Lessons Ch. 01

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

(1) - Acceptance Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it was off to another company. Talking of bi...

My Wife and Her Boyfriend Pt. 02

by Anthony1965 on Jan 21, 2020
Loving Wives

This story is a continuation from my first story. How I sink further into humiliation and lose my wife even more, if that's possible. Now the continuation... I sat in the living room on the couch and couldn't believe what happened. Did I really lose my beautiful wife? Was this just a game on their part? I was snapped out of my thoughts with the sound of s...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

Mistress Elva Laughs Again!

by justincbenedict on Jul 3, 2018
BDSM

Alma sat in silence as the two other women talked animatedly. She was blushing hotly, and her panties were soaked. Why, why do I have to be this way? Lynn had just told Elva the story of how she chased poor Alma while Alma was Rollerblading naked and whipped her with a cane, and by some miracle, Alma hadn't fallen over. "I do love embarrassing her!" "That...