Teacher Upskirt Stories

25,010 results
Orientation
Length
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Infinite Scroll

A Panty Party at St. Matilda's

by cruiser_2015 on Jul 9, 2019
Group Sex

I'm one of the few male teachers at St. Matilda's Academy for Young Ladies, an expensive English private school. I'm early thirties and still single, and for me it's a voyeur's paradise. I teach a final year class of about twenty girls aged eighteen to nearly nineteen and all very much aware of their ripening sexuality. They all seem to be trying to outdo ea...

Kingdoms of Jocasta

by WinkingOtter on May 14, 2018
Fantasy

The Kingdoms of Jocasta are a realm full of magic and wonder. It has sights to take your breath away and tearfully thank the Three Gods for their almighty creations. From the twisting spires of Oedipolis, the floating island of the Tempest Sea, the Flaming Golem of Amethyst River, the ash deserts of The Forsaken East. It is a land of opportunity and adventur...

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Downfall

by Moot on Dec 3, 2018
Fetish

Vanessa Sinclair is the CEO of a large corporation which sells electronic products. She is seen by her employees as a stuck-up "rich bitch" who only cares about her looks and her money. She is constantly rude to her employees, who despise her. Vanessa has a stunning body, which she uses to her advantage. With her D cup breasts, hourglass figure and...

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Art Class Got Something Special

by MFFM on Aug 7, 2019
Exhibitionist & Voyeur

After two modeling sessions at the local college, I had one more to go. The second session had ended up with the class tricking me into giving them an erection, by the attractive instructor putting me in a comfortable reclining pose and then quietly and slowly giving me a pantiless upskirt view. This brought me to a raging erection, but then class was over a...

Lunch on the Bench

by BiancaOldman on Aug 19, 2017
Exhibitionist & Voyeur

I had decided to pack my lunch, since there was roast beef left over from Sunday dinner. Didn't do it much, usually ate at an overpriced restaurant. Noon time was sunny, so I hauled my lunch and a can of Coke to the park to soak up some rays and watch the ladies. It was a glorious October day with just a bit of a chill in the air. Not so much that I had to k...

Naive And Erotic Roommates

by BBBlooster on Jan 27, 2020
Amateur

ALL CHARACTERS DEPICTED IN THIS STORY ARE THE AGE OF 18 OR OLDER. Welcome to my first story on Chyoa! Im a somewhat inexperienced writer, so all feedback is welcome. This story was originally intended to have a far more linear intro, having the main character meet his initial roommates in the first chapter, however i saw wider potential in the idea and ha...

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A New World! Your Party of Hopeless Hotties

by Fiftyfiftyfifty on Apr 4, 2020
Fantasy

Obligatory Patreon link is here. This story uses conditions to utilize the information gathered throughout the story, so please click "Start Game" in the top right corner under "Score" or else some of the pages might not make any sense, and you may fill in information about the protagonist (you) on the side of the screen under "Custo...

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Little Bo Peep

by Sinestro on Sep 14, 2017
Fetish

Martha: Don't you think she's too big to play Little Bo Peep? Henry: I like big gals besides she's perfect for the part. Little Bo Peep was out in the meadow watching her sheep. Martha: There stuffed. Henry: Yeah well we couldn't afford real sheep and it might not be a good idea to have them around the studio. Martha: Why? Henry: You've heard the exp...

Panty Man Ch. 03

by BOSTONFICTIONWRITER on Sep 14, 2017
Fetish

"Panty girl? I can't believe your Literotica screen name is Panty Girl? How weird is that?" "And I can't believe that I found Panty Man," she said laughing. "What are the odds of that?" "I'll show you my panty collection, if you show me your panty collection," said Norman with a nervous laugh. "Why do I get the feeling that I would be amazed by your panty...

The Coast Trip

by magichands on Sep 14, 2017
Exhibitionist & Voyeur

Things finally slowed down a little around our house, so Lee and I decided on a short run to the Coast. We like to get away from the day to day grind, and we really enjoy finding some unsuspecting guy and giving him an "accidental" peek at Lee! It was the middle of last week, and hotter than the hubs of hell in Portland, so running around Newport in the co...