The Principal's Booty Bump Literotica Stories

369,465 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Whitewash High Ch. 02

by EnglishTeacher on Sep 25, 2017
Interracial Love

"Gawd, Massa, ram me with your perfect cock. Gape my slutty holes that were made and bred for you. Thinking about you makes my cunt drip like a waterfall," Michelle screamed out in her bedroom. The busty, fit teacher invited her new master home after the school day was over the following day. It took them nano-seconds for their clothes to be torn off, and...

Sissy College Ch. 02

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All Characters 18+. Sorry for the delay. Life gets in the way sometimes. This is a sissy/interracial themed story - if these themes offend you, or you are unable to separate fantasy from reality, please read no further. Special thanks to Puzziboi for all her input. I love hearing about the mess you make in your panties, so please do leave feedback. ~~~~~ L...

Claire's First Time Penetration Ch. 04

by ostinatobravado on Sep 12, 2017
First Time

Here is the 4th and last part of this story line. Recall that Claire is a 19 year old high school student so there is no underage content in my stories. ========= Claire's First Time (Part 4 and final) Claire lay motionless with her stomach flat on the principal's desk, her head facing to the side resting her cheek, tied at the wrists and blindfolded. She...

Angel's Education

by GeorgeTyerbyter on Sep 16, 2017
Fetish

Angel's Education: The Epiphany, The Video, Her Emerging Fetish, And The Vice-Principal. -A Tale of Smoking, Clothed Sex, Masturbation and Facials. [An addendum to a previously published erotic story, by the author "Luthor," entitled "The Reverend's Little Angel."] A Short Story (with a long title) By George Tyerbyter—aka Mick Carlo. ****************...

Out of This World Ch. 02

by LuckyMeOriginalStories on Apr 17, 2018
Sci-Fi & Fantasy

School of Debauchery 10, September 5018, 9:00 AM Lincoln, Nebraska **Lincoln High School** Arriving to work late again, Shayna parked her car in the parking lot located behind the school. She pulled her keys out of the ignition and took one last look at herself in the rear view mirror of her car. She stepped out and walked quickly around to the front of...

Students Rule II Ch. 05

by linkznut on Sep 14, 2017
BDSM

Chapter Five -- A New Mistress It'd been three weeks since the oil wrestling debacle against Miss Goodman; three weeks in which Ms. Lee had lost all control of her situation. What had started out as a slow, boring school year -- one that didn't even get interesting until Brian Bitner staked his claim to her in early January -- had suddenly gotten totally ou...

Somali Queen In Ottawa Ch. 03

by Samuelx on Sep 12, 2017
Erotic Couplings

Right now, I've got Yasmin Hussein, my favorite Somali goddess on all fours, face down and ass up, and I'm worshipping her gorgeous, heart-shaped ass just like a real man should. And I've got my tongue buried so far up her asshole, you can't tell where she ends and I begin. And you know what? That's exactly how I like it. My name is Steve Salomon, a Haitian...

Starting from Scratch Ch. 22: YOOHOO OVERHEAR

by SZENSEI on Oct 5, 2020
Exhibitionist & Voyeur

Piper Cherry, in her daily wanderings subjected herself to overseeing classroom participations, just to understand the bonding techniques each Teacher had with their students. Starting with History Teacher Dewey Knowles class in session, she stood in his doorway just to witness his approach. Long before he noticed her he divulged a personality that caught he...

A Jock in the Machine Ch. 04

by ProdigalCookie on Aug 24, 2020
Transgender & Crossdressers

Chapter 04: Head to Head, Heart to Heart Disclaimer: All characters mentioned in the story are over eighteen years old. Most of the main cast is exactly 18, but none are younger than that. Cassie's skin tingled. She felt her knees getting weaker. Her breath got more irregular. If this had been due to any other reason, especially a Tim shaped reason, she wo...

Catholic Corruption Ch. 01

by Irish_Dude on Sep 14, 2017
First Time

Characters: Principal Voyeur, Amy * Hello. My name is Amy. I am a senior at Clairmont Catholic School for girls and I have recently been accepted to Harvard University. To the rest of the world, I have everything I need. I am Class valedictorian, Varsity cheerleader, and class president. I recently celebrated my 18th birthday and had one of the biggest par...