Teacher Wedgie Stories

25,219 results
Orientation
Length
Source
Infinite Scroll

Kellie and Brad Ch. 11

by drteetho on Sep 13, 2017
Romance

AUTHOR'S NOTE: This is the eleventh chapter of a multi-part story. Please read the first ten chapters before this one to understand the whole story. Please enjoy. ****** Three years after the events of Chapter 10... Today was a big day in the Galenchuk household. In the evening, Kellie had a meeting planned with teammates Jennifer, Heather and Amber. The...

Leave Me Breathless

by StangStar06 on Sep 25, 2017
Loving Wives

Hey folks, I know the past two weeks have been a murder fest, but sometimes fictitious people have to die. I promise you that there will be no fictitious deaths in this story, so those of you who can't stand it when imaginary people die are safe. I did borrow the results of the car accident from one of my favorite classic LW stories. Those of you who've been...

Summer of Slut: MILF Challenge

by silkstockingslover on Sep 26, 2017
Illustrated

"Summer of Slut": MILF Challenge SUMMARY: 4 MILF's decide to see who is the biggest slut over July long weekend. CREDIT & THANKS: A super special thanks to legendary artist Rebecca (of the Housewives at Play series and many more) for giving me permission to use a few of her plethora of illustrations for this story. We collaborated in 2014 on Straight H...

Playing Favorites

by JustJaney on Apr 3, 2018
Romance

Although this story contains characters that are minors, all characters engaging in sexual activity are above the age of 18. ***** The day that Khan left me was both the worst and best day of my life. Things hadn't been going well with us for quite some time, but we'd been together for almost eight years so I guess I was surprised that it ended as suddenly...

TCCS Pt. 01 Ch. 02: One Hot Librarian Researches BBC

by Stormbringer on Nov 20, 2017
Interracial Love

The Mrs. Kindle encounter with Melvin is based on three pinups drawn by the Pit. The Betty and Samantha encounter with the slave Prospero is based on The Plantation comic written and drawn by the Pit. It is unfinished, ending with the two sisters sneaking back to the barn at night. With the Pit's permission, I incorporated the Plantation and pinups into our...

Anatomy of a Teacher's Affair

by Bluepen451 on Sep 13, 2017
Loving Wives

A September Day at the Motel It was a warm day in early September. The air conditioner in the dodgy old motel was doing its groaning, rattling best, but the temperature in the room was still approaching eighty. Lynette was lying on her back, her legs spread as far as she could get them as her lover supported his upper body above her on his elbows and pound...

Loosening Up Bk. 08 Ch. 31-35-End

by SteveWallace on Mar 16, 2020
Group Sex

Chapter 31 -- College Onsite Dave peered through the glass door into part of the core that was usually used by the younger school children in the Circle's home-schooling program. He was surprised to see room full of college aged men and women peering at the teacher at the front of the class. The teacher was Marie Thereaux. The hieroglyphics on the white boa...

The Making of a Man Ch. 02

by Imakewetspots on Feb 10, 2020
BDSM

Nick lay in the bed alongside Mistress Elyse, completely exhausted. They had been going at it for a couple hours this particular session and while Mistress Elyse had many climaxes so far, she had not yet permitted him to have his. Nick wasn't complaining though. He knew his place well since day one. He enjoyed giving his Mistress pleasure and he knew he was...

Lucas and the Library Girl

by Voboy on Sep 13, 2017
Erotic Couplings

This is a companion piece to the stories of Seaborne Memorial High School. It's Lucas' turn this time. He turned out to be a little more introspective than I was expecting, but then he is an English teacher. He's a slow, cautious guy; this ain't a quick spank story, though most of mine aren't. Enjoy! * * * Until that Thursday, I thought of her as "Liz...

Above

by Ooshnafloot on Jun 4, 2019
Exhibitionist & Voyeur

W.F. Stuart Teaching College is in the foothills, overlooked by the elite suburbs. It's the closest that ordinary folk can get to high living. Above the college are winding leafy roads with mansion after estate after villa. Deckings stilted above slopes, infinity pools cut into rock. Below the college was suburbia; rows of mostly untidy little boxes with sim...