Teacher Upskirt Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Detention

by jansen_jan on Dec 16, 2017
Mature

This is a fucking nightmare... I am supposed to concentrate during class, and here's this woman prancing around the room in a pencil skirt and stockings. My high school days had gone by without much trouble until a few weeks ago. I had a best buddy, there was a girl having the hots for me ... Good grades, et cetera On the day our economy teacher Mr Stockton...

Business Model

by cruiser_2015 on Sep 14, 2017
Erotic Couplings

I regard myself as a professional providing a quality service to my clients. I choose my clients carefully, and like to think they've chosen me with discernment and taste, not just for the rather specialised things I'm happy do for them. That's what I was thinking as I walked to my meeting with a new client. We'd arranged to meet in the bar of a rather smar...

The High School Teacher

by WifeANympho on Mar 2, 2020
Group Sex

"It will be great, Maria, I promise," Tony insisted. "There will be plenty for you to do and we will get to spend time with our son before he leaves for college." "Our son and his friends, you mean," Maria countered. "Well, yes, that's true. But he wants to have guys his age on the trip, which will allow you and I to have some couple time during the week,"...

White Buddha: ESL, Melvin in China

by KIMCANCER3040 on Jul 2, 2019
Humor & Satire

White Buddha: Portrait of an ESL Teacher in China "Melvin..." "Where was he from?" "Portland, Oregon." "That's weird." "It's a weird place..." "But he hated Portland, like, really, really hated Portland, always shitted on its hipsters, and politically correct, passive aggressive people..." "He certainly was not passive aggressive." "Wasn't he...

All Day Tease Ch. 01

by Eteoclus on Sep 13, 2017
Exhibitionist & Voyeur

In which Rob, a college teacher in his 30s is teased first by a student and then by an increasing number of beautiful women as the day progresses. ************************************** Chapter 1 - 3:00 AM to 1:00 PM - The Morning in which we are introduced to Rob and each of the ladies he will encounter, as they all get ready for the day ahead. ********...

Exotic Pussy Cum Extortion

by Alluring_Crimson_Shifter on Sep 14, 2017
Anal

Leon struggled in his science class and was almost giving up at the idea of graduating from high school. As an 18 year old he did not see good prospects as an adult. His teacher coached him and encouraged him. She was his science teacher and sometimes spent time after class helping him with his studies. He admired her intelligence and her looks, and grew fon...

How to Voyeur Women

by BOSTONFICTIONWRITER on Sep 14, 2017
Exhibitionist & Voyeur

How To Voyeur Women Without Having Anyone Thinking You Are Perverted. Ah, the birds are singing, the weather is warmer, and women are wearing fewer clothes. Spring is in the air, skirts are shorter and blouses are lower cut. There is nothing like the sight of an upskirt of white cotton panties in the morning, well, in the afternoon, okay, and in the evening...

Exhibitionistic Woman Meet Voyeuristic Man

by BOSTONFICTIONWRITER on Sep 12, 2017
Exhibitionist & Voyeur

Several years ago, I joined an online dating service and contacted women all over the world. As fate would have it, I connected with a woman, Christina, who lived only a few miles from me, which was convenient for us to meet, if our online romance developed and we wanted to take it to the next level and meet in person. By the photos that she sent me through...

St. Ursula's School for Naughty Girls

by DJDanDan on May 22, 2020
Amateur

'Remember, this is your last chance Poppy,' said her dad as she got out the car with her suitcase, 'if you get expelled from this school, thats it - no qualifications, no job, no life prospects. Your mother and I have signed the agreement saying that they can discipline you in whatever way they deem necessary to get you to do as you're told. You're eighteen...

Open in Reader

Lucy Strays Ch. 02

by xxavi on Jun 1, 2020
Loving Wives

This is a direct continuation of Chapter 1 so please read that first. Also, there will ultimately be 4 Chapters. I broke the story up to help my editor, without whom this would never have been published. Thanks for the positive feedback; hopefully everyone likes this one as much. Enjoy! Chris Eventually our guests left and we finally started putting the...