School Bet Stories

141,638 results
Orientation
Length
Source
Infinite Scroll

Costume Party Switch

by jackie_em on Oct 24, 2018
Transgender & Crossdressers

I should know better than to bet on football games, even when there's no money on the line. I am Mike, 25 years old and a guy. My girlfriend is Michelle, the same age as me. We had been dating for some time, and had moved in together, after sleeping together pretty regularly. There was a Halloween party coming up that we planned to go to. I am 5'6" and 135...

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...

I Wish I Had Never Met Him Pt. 01

by AliHomeygrass on Sep 16, 2017
Loving Wives

This is the story about how someone fucked up my life and I didn't even realise until it was too late and I was left with nothing but bittersweet memories and a real burning hatred for him and the worst part is I know he got away with it. To understand my story, I will go back to when I met the bastard at teacher training college in the 1980s. I am Francis...

Driver's Education

by tommcgee on Sep 14, 2017
Erotic Couplings

Learning to drive is one of the great pleasures of high school. Tom, Lisa, and Fred were all in the same "on-road" driving class. These three would go out with their instructor for an hour at a time each day. Twenty minutes each and this eventually satisfied the state's requirements. The class was a total of three months long, so the three students would be...

The Homecoming Date

by CrashOverride on Sep 16, 2017
Romance

They were so excited. It was their first night together. "My god, she looks so beautiful," Matt thought as she peeled the bra from her bountiful breasts. But please forgive me; I am getting ahead of myself. They had been talking to each other for a little bit now. They met in high school, in their junior year advanced chemistry class. Neither of them really...

How I Became A Girly Slut Ch. 02

by richfun71 on Sep 13, 2017
Transsexuals & Crossdressers

Copyright 2008 I couldn't believe what was happening to me. Here I was a normal straight guy dressed in a tight pink t-shirt, stockings and suspenders and black lacy panties under my jeans, wearing bright red lipstick and with a transvestite's cum dried onto my face, and the taste of another man's cum in my mouth. I had a piece of paper with an address on i...

14 Hours Pt. 11

by CaffeineFetish on Nov 22, 2017
Humor & Satire

-Will- I thought a lot about how to break the news to Kori. I know her well enough to know this is not ending with understanding and forgiveness. We've officially reached the end of my rabbit hole. In all fairness, I should feel even worse about having sex with Samantha before we were truly over, but I just don't. We are all always told that there is some...

Maid The Wrong Bet...

by Lea1234 on Sep 25, 2017
Transsexuals & Crossdressers

Part 1 Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn't explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years... A friend of mine, Peter, was into the same video games as I was, and we made a bet on who would win the next ga...

I Don't Want to Spoil the Party

by Harddaysknight on Sep 12, 2017
Loving Wives

It was New Year's Eve and I was really enjoying myself. In my entire life, I had made two solid friends and they were standing in the room with me. We were in Tom's basement shooting pool and drinking beer while our wives chatted upstairs. I had moved back to Allentown a year ago, after living and working in Philly for fifteen years. Ray had gone to Stanfor...

Bar Bet Weekend

by LiseKLord on Feb 7, 2018
BDSM

Joly and Rina had been friends since elementary school, through high school as well. They had been college roommates and now, five years after graduation, thanks to good jobs, they still chose to share a very nice condo in the heart of downtown. They knew everything about each other, and despite the occasional annoyances any living together relationship migh...