Submissive Sissy In Chastity Stories

369,928 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Mistress Chronicles Ch. 04

by MistressMtoyou on Sep 25, 2017
Fetish

Background: The next three stories involve my only long-term on-line subject who I have named Nancy. This subject passed all of the tests I described in story two ("A Few Good Subs"), but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding any in-person meets. We agreed to continue training...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

The New Routine:

by subservient_husband on Sep 17, 2017
BDSM

Saturday morning, I woke with Jennifer's warm body next to mine. It was wonderful and I did not move until she woke. We locked eyes and she gave me a morning kiss on the cheek. "Go ahead and make me some eggs and toast". I left her in bed to go get her breakfast ready. While I was, I heard the shower running and as I was putting it on the table, she came in...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

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...

Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...