Sissy Training Stories Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

A Sissy Saga Ch. 15

by Snurge on Sep 15, 2017
Novels and Novellas

A fine day, thick and hot making Miriam Hancock's face dewy with sweat. She gazed at the house. Was this the place? She checked the card in her hand. No mistake. It was an unimposing Edwardian terrace house in a street of equally unimposing houses, narrow fronted, three stories high, the windows heavily draped. She went up a set of steps to a porticoed door...

The Hanky Code Pt. 17

by His_fag_wife on Sep 14, 2017
BDSM

Mistress paused, to let the enormity of her comments sink in. What would Archie her husband be doing now? Would he be stripping at this point or frantically checking on the websites he'd been on and erasing his history. He was caught and if he only knew how his life was going to change, he might not have looked at some of the more extreme sites he had. "Yo...

Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. 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...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

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...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Dominating Ken Pt. 01-04

by oneguy4fun on Sep 26, 2017
BDSM

Part 1: The Online Encounter Story Overview A thread of e-mails quickly blossoms into an erotic relationship of domination and humiliation between Ken and Karena. Karena develops a growing need for power and control while Ken finds himself drawn into a state of submission and inferiority. * Ken anxiously opened his e-mail to see if Karena had responded...

Sissy Plays the Game of Thrones

by SissyKelly on Dec 1, 2017
Celebrities & Fan Fiction

Kelly Waters, fucking Waters I thought to myself as I shook my head. I think the worst part of being a bastard is knowing you could choose any last name, but having it dictated still by birth. I knew not who my parents were, in fact I only knew I was Kelly Waters thanks to the man who raised me, Lord Petyr Baelish. I was born in his house, his whore house,...