Teacher Upskirt Stories

25,010 results
Orientation
Length
Source
Infinite Scroll

Workplace adventures

by lexist on Apr 21, 2016
Erotic Couplings

I had just been transferred to a new department at work. I'd come up with a new idea, and the big wigs liked it, so I'd been given the somewhat staggering task of actually leading the project. Along with the new responsibilities came a new office in another part of the building. I decided to get a head start and came in early to move my stuff over into my ne...

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No Game No Panties

by Fiftyfiftyfifty on Feb 28, 2020
Fan Fiction

(If you don't click "Start Game" before reading, things might look confusing at times due to some pages requiring certain conditions.) "This is the Utopia that you guys dreamed of, the world on top of a game board, [Disboard]--everything here is decided by a game, even one's life and country borders!" ― Tet, the One True God In the land o...

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Servicing Celebs

by superman07 on Oct 6, 2012
Fan Fiction

DISCLAIMER: This is all a work of fiction and does not reflect any real individuals or situations. AUTHOR'S NOTE: This story is going under a soft reboot after 8 years. My last update was in 2013 so needless to say things have changed. You can still find the original story paths if you're interested, though to be frank they aren't anything worth noting. As m...

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It's All About the Panties

by wellworn on Mar 7, 2018
Transsexuals & Crossdressers

This is a redacted version of a longer story removing discussion of how and when a life long fetish may have developed. Although no underage sexual correspondents were described in the original, other than perhaps kissing at the age of 16, because the story is all about a fetish which is sexual in nature, I acknowledge it must have contained an underage sexu...

Houseboy Blues Ch. 02

by heavenlyKK on Oct 7, 2019
Exhibitionist & Voyeur

Houseboy Blues - Ch. 02 "Let's talk," Herman said. He pleaded and begged - the penis clamp was breaking him, he couldn't take it anymore. He'd do anything, and he meant anything, to get it off. Jane was open to discussion, but she insisted on two conditions. "Anything," he said. "First, no beating off in public, in front of other people...unless they a...

My Whorish Revenge Night

by promiscuousgirl on Sep 13, 2017
Loving Wives

My boyfriend was supposed to come home tonight after work but he called and said he was going to grab a few beers at the pool hall with some of his co-workers. I got jealous because I rented a movie he wanted to see and cooked his favorite dish. I got even more jealous because I know what he does at the pool hall when he gets drunk. He is very flirtatious ev...

UpSkirt, Sitting Uppie, Downblouse

by BOSTONFICTIONWRITER on Sep 12, 2017
Exhibitionist & Voyeur

UpSkirt, Sitting Uppie, and Downblouse Paradise Heterosexual man pretends to be gay for voyeuristic pleasure in seeing an endless parade of panties, bras, tits, and pussies. It took me a while but I found a loophole in the sexual nonsense that exists between men and women. Here I was all these years unsuccessfully trying to pickup women in bars to have sex...

A Voyeur's Dream

by uksnowy on Sep 1, 2017
Exhibitionist & Voyeur

I was mesmerised. She sat opposite me in the café in the huge new shopping mall. Her crotch which was exposed to me in all it's bare-naked glory had dissipated the drained pissed off mood I was in and had turned it into elation at the sighting. Frustrated at the lack of upskirt opportunities in this admittedly early day in the year, but it was a spring sunsh...

30th Birthday Party

by haleyandjames on Sep 25, 2017
Exhibitionist & Voyeur

This next story is a little while after my first exhibitionist experience on the bus. This is when I started becoming more daring and actually flashing myself opening in public. So about a year and a half ago James and I went to the city for a 30th birthday at a bar. Being at a bar on a Friday night, James and I decided to have a little fun after the party....

James - 10 Years After Pt. 05

by doubledigit on Sep 26, 2017
Exhibitionist & Voyeur

James returned to the main lounge. His penis was at ease, resting comfortably. It had shrunk to 9 inches and being a softie never felt as good as it did right now. The Viagra had worn off; either that or the five orgasms had worked it out of his system. And another thing. James was no longer shy about wandering about nude in the bathhouse in front of all t...