Teacher Pegging Stories

25,741 results
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Length
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Infinite Scroll

Freshman Year

by Johnrocker on Aug 25, 2020
Exhibitionist & Voyeur

Mark felt the fresh summer air as he strolled through campus. He couldn’t believe it, for the first time in his life, he would be living away from home. With frequent waves of anxiety and stress through his years at high school, Mark missed out on simply enjoying his time there. Moving to a college interstate was a scary thought for Mark but something he nee...

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The Shameless Slut Fails Her Exam

by erinyahn on Sep 12, 2017
Group Sex

This is the second story in the "Shameless Slut" series. Each of the stories is standalone, but you may appreciate this one better if you read the other one as well. The nature of these stories is that the protagonist is trying new things as she discovers her sexuality, so each story will touch on different kinks and genres. So, some stories might be your th...

School Drop Off

by daciasdesire on Apr 19, 2018
MILF

Spencer Askren leant down and hugged his daughter Amy goodbye. “Be good in class today sweetie. I know you will crush your physics test,” he told her before giving her a kiss and sending her off. “Thanks Dad,” Amy replied. “Don’t forget I have softball tryouts this afternoon,” she told him as she left the school drop off area and made her way to the entrance...

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Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

Cissy's Pegging Parlour

by Pinkmanties on Mar 18, 2020
Fetish

Fella's are you looking for a little backdoor action? Maybe you want those cheeks to feel the sting of a riding crop, or you want your boipussy filled with a firm supple dildo, or maybe you're just looking for a girl who will put your manclitty in a cage and tell you what a bad boy you've been! Come on down to Cissy's Pegging Parlour where your dreams become...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Sensitivity Training Can Mean a Lot Ch. 04

by JimAner on Sep 13, 2017
Fetish

Part IV -- The Pegging Party Ms. White woke him some time early in the afternoon. She said as she shook, him, "I wish we could keep you here. Look you have another bone. Amazing." Beercan said, "Its just a piss hardon. Can I go to the cube? Ms. White replied, "Dear, you can piss on yourself, if you choose. Lots of our clients would have no trouble watchin...

The Best Present: Pegging my Man

by silkstockingslover on Sep 25, 2017
Fetish

Summary: A wife discovers her husband is curious about pegging and.... Note 1: This is a Holiday 2016 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, Dave and goamz86 for editing this story. The Best Present Ever: Pegging my Man I was working from home, stuck with a sick child, when my whole world changed. My work laptop died and...

Interracial Pegging: Revenge

by Samuelx on Sep 11, 2017
Interracial Love

Bad company. That's what everybody says about me behind my back. And to be honest, I don't give a flying fuck. My name is Julianna McCain. A six-foot-tall, slender and athletic, red-haired and green-eyed young woman of English descent living in the City of Ottawa, Province of Ontario. And I am a Canadian porn star with a unique specialty. I am really into In...

Domestic Goddess Ch. 01

by mstqfox on Sep 13, 2017
BDSM

Jack stood naked in the bathroom doorway. It was 7 a.m. Saturday morning, and he had just finished depilating his body from the waist down, as I had instructed him. "Looking good, honey. Nice and smooth," I said. I motioned him towards the bed. We had a rustic king-size bed, the legs of which were made of polished 8-inch thick logs. The headboard consisted...