Sissy Boarding School Fiction 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

A Sissy Saga Ch. 10

by Snurge on Sep 15, 2017
Novels and Novellas

"Disgusting!" exclaimed Miriam Hancock lightly as she examined the photographs Emma Twist handed her. It had taken Hardwick most of the day to produce the prints, but they were well worth waiting for. The headmistress went through them as if shuffling cards, and having glimpsed each one viewed them a second time, more slowly and with greater concentration. "...

Revenge! Ch. 03

by Magnificat on Sep 19, 2017
Celebrities & Fan Fiction

Revenge is a dish best served hot; very hot! Pt. 3 (This is the third chapter in a series of six. Those of you who have read the first two chapters, know what you can expect. However the scenes depicted in this particular episode may not be to everybody’s taste. There’s BDSM, cuckolding, non-consent, anal rape and extreme violence so be warned! I recommend...

TNQF Slightly Secret Six & A Half

by pop_54 on Sep 17, 2017
Celebrities & Fan Fiction

The not quite famous slightly secret six and a half: By pop_54/2003. With acknowledgement to the marvellous Enid Blyton for the inspiration for this small attempt at an 'adult parody' of a children's story based loosely around the style of children's novels written by EB. I must add at this point that any childlike mannerisms associated with the character...

Becoming the Man He was Meant to Be Pt. 01

by fantasyhunter2 on Sep 12, 2017
Novels and Novellas

Author's Introduction. This is the first book in the chronicles of the life and loves of Anthony Madison. This is my first attempt at crafting a multivolume novel and I hope that I will somehow find the time to complete these chronicles with additional books. However, I believe this book stands alone as a complete story even though there will be a few linge...

Hugo From Pode Hole

by egmontgrigor2010 on Sep 13, 2017
Romance

CHAPTER 1 The ruggedly handsome guy with long black hair and very pale complexion leaned back on the chair in the half-empty Starbucks and wished he'd chosen a coffee that tasted like coffee. Idly he studied three under thirties women at a table who were dressed like businesswomen. He winked at one and she turned away embarrassed and their heads went togeth...

Mike & Karen Ch. 15

by BiscuitHammer on Sep 24, 2019
Romance

Disclaimer: Welcome to my one-hundredth chapter published here on Lit. Quite a milestone for me! And as usual, all characters are 18 years of age or older while actively engaging in sexual activity. This story is a prequel/sequel (sprequel?) to my other work, Alex & Alexa. As always, many thanks and gratuitous panty shots from Freja and Jeanie to my long...

Diary of a Punk Rock Band

by Darksider on Sep 17, 2017
Celebrities & Fan Fiction

9/27/02 Avril's diary- Friday morning Dear diary, Hey! It's my birthday! Yay! Happy Birthday to me! I'm finally 18! But that means I'm no longer a minor so I'm going to have to start to behave myself! It's been a long time since I've been able to find the time to stop and write in here. My dream is finally coming true, I'm able to do what I love and stay tr...

Edward Lane's Argosy Ch. 06

by Ian_Ironwood on Sep 15, 2017
Sci-Fi & Fantasy

"Are you ready to depart then, Captain Becker?" Baron Amadahy asked Gideon on his penultimate day in service to the Kingdom of Oklahoma. They were meeting in the Foreign Minister's opulent office, easily as posh as any in England, though some of the decorations might have raised an eyebrow in London. But his ship's recent heroism had earned Gideon the privil...

Edward Lane's Argosy Ch. 04

by Ian_Ironwood on Sep 15, 2017
Sci-Fi & Fantasy

Air Captain Gideon Becker watched the skirmish line of airships bearing the enemy's colors – in this case, the red, gold and green of the Atlan Empire – bearing down on his position with a mixture of dread and excitement. He swung the periscope across the southern horizon and counted . . . five, no six ships. He noted with relief that they were not the three...

Secrets of The New World Order Ch. 06

by bjmichaels on Sep 16, 2017
Sci-Fi & Fantasy

Your child's eighteenth birthday marks a significant rite of passage every mother faces with ambivalent feelings...soon, the child will be out of the house on their own, meeting new challenges every day, and all you can do now is hope you've prepared them for the highs and lows the real world will throw at them. In my case, it meant I had just one child rem...