Sissy Slut Spanked Stories

93,430 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Slave History

by timeagain93 on Sep 17, 2017
BDSM

These are my recollections of my slave history. Four Goddesses have dominated me. I'm writing this to let my current Mistress understand my story. Mistress D read "Variations" magazine and spanked me with a wooden spoon. She tied me naked to a chair and blindfolded me. She made me sit there in silence. I was wearing her panties while talking on the phone w...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Sissy Training Vol. 01

by depositdutchess on Nov 27, 2017
Fetish

Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Girl's Night Pt. 02

by DifferentBreed on Sep 14, 2017
Fetish

Fisher was upstairs, making the bed when he heard the front door opening, signaling Sophie's arrival home. He looked down at the list on her dresser, frowning. He had not completed four tasks. He reapplied his pink lipstick and kissed the paper above the words "make bed with gold satin sheets" as he was instructed. He then scurried downstairs, incomplete lis...