School Bet Stories

141,638 results
Orientation
Length
Source
Infinite Scroll

The Bet

by KittyandBear on May 20, 2019
Transgender & Crossdressers

Chapter 1 What on earth was Charles thinking? I was only giving him some good-hearted teasing, and then he challenged me with this bet. And the result seems to be pretty obvious. No offense to Charles, but there is no way he could win. There had to be some trick, and Charles was always the clever one. And the worst part is, there is no walking back from thi...

Rivalry

by race_1962 on Sep 17, 2017
Loving Wives

This story may not be reproduced or posted anywhere without the author's express permission. Hi, my name is Don and this is a story based on events that happened last summer. It took me nearly a year to be able to write about it, but I had to share it with someone, so thanks for reading this. The events that happened that summer afternoon were based on even...

Dealing with Jessie

by carvohi on Sep 24, 2019
Loving Wives

A note from the author: This is a long story, nine parts. I'll submit a part every other day so things won't get stale as you read. Most 'Loving Wives' readers like the "first person", but this is in the "third person". The concept and the story came upon me only gradually so it took a long time to write. The events below begin on a Friday night in Decemb...

Having Fun with Dycke and Payne Ch. 10

by Prolonged_Debut10 on Sep 25, 2017
Novels and Novellas

47. A Very One-Sided Battle. Grigory stood in the turret of the Greyhound, holding the fifty-caliber machine gun. He was waiting for the first Humvee to reach the intersection of Appian Way. He could not believe his luck when he saw it stop for the traffic signal. He gave the go signal to the driver and his men and they converged on the small convoy. His m...

"I bet..."

by Jake_Knight on Sep 19, 2017
Erotic Couplings

I admit I'm not the sharpest tool in the box. I can't say I was surprised when I got to Ed's house at 8 when he had said 9, and I'm not in a good mood when I'm awakened early. Finding that my buddy wasn't home worsened my mood. "I bet that guy is a hello kitty fan." "Fuck off, Bree," I mumbled, "this stopped being fun when I was in high school." "No, no,...

Run In With Mom

by lengthylarry on Sep 12, 2017
Mature

Let me give you a little background: I'm a junior at a major state university. In high school, I ran cross-country. I still love to run. Since I've been running six days a week for the last 7 years I've developed a pretty decent body. I don't have huge muscles, but I'm somewhat well defined and I'm pretty thin. I'm about 6'1" and weight about 185. I met my...

Double or Nothing

by SPEN STERLING on Sep 12, 2017
First Time

It was bowling night for Jeff Tailor and his friends from the football team, and the crew was making the most of their first week of freedom as high school graduates. There was so much whooping and high-fiving going on that Jeff didn't notice the girl in the lane beside him until they were halfway through the first game. It was Melody Spincer, his next door...

Boarding School Blowjob

by HaskellHacker on Dec 12, 2018
First Time

Tom and Charles had been best friends since they were 9. They had met playing for the same school rugby team. Through this, they spent a lot of time together and formed a bond that had lasted. They both left primary school and joined the same secondary school, which happened to be a boarding school. There, again they were both accomplished players and so spe...

Zoe Parker Ch. 06

by BrokenMasterpiece on Sep 16, 2017
Non-Erotic

Chapter 6-The Companion Zoe awoke the next morning not remembering when or how she had fallen asleep. Glancing at her alarm clock she noted the time being thirty minutes after six o'clock in the morning. Even with a rudimentary estimation she deduced that she had slept for a minimum of thirteen hours. Usually when one sleeps for over half of an entire day t...

Susie Loves Football

by motbitro on Nov 2, 2020
Exhibitionist & Voyeur

It was a normal Saturday during football season. I was in my apartment with Susie, my very cute and very sexy girlfriend, who simply loves being a playful cock-teaser. We were drinking Bloody Mary's watching the early games, getting "fired up" for the 5:00 game when our favorite team was playing. I began dating Susie in high school. As time went on and we...