Cheerleader Bet Stories

69,749 results
Orientation
Length
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Infinite Scroll

Detention Ch. 02

by Ashson on Sep 14, 2017
First Time

A custom had been established at Chatswood High that detentions were presided over by the coach. This was a change from the old custom where the newest teacher was the bunny in charge, and no-one knew for certain why the change had been made. Well, some people obviously knew, but they certainly weren't sharing the knowledge with anyone. Rumours however, abo...

The Big Wager

by StudHummingBird on Sep 13, 2017
Exhibitionist & Voyeur

Our betting dated back to a management seminar the two of us attended years ago. During the seminar Karen and I were pitted against each other in several of the training exercises. The trash talk over coffee and donuts led to a wager of dinner for the winning team. We took this competition between us back to the office. I guess one of the managers picked up...

Big Fat Cock: Dumb Cheerleader

by silkstockingslover on May 20, 2019
Erotic Couplings

Summary: BFC is used to dominate a hot blonde cheerleader. Note 1: This is dedicated to the real Jeni who told me about this BIG FAT COCK... although her story wasn't told in the first three stories and isn't in this one either. Note 2: This is the fourth part in a potentially lengthy story of one nerd's discovery of the power having a BIG, FAT COCK can ha...

Steven and the Cheerleaders

by RedHairedandFriendly on Sep 12, 2017
Group Sex

Author's Note: This story came from the 500 word challenge I participated in, that was posted on the Author's Forum (the title was Carpooling Cheerleaders). Later, most all the stories were collected and turned into a submission here at Lit. under the name: Coming Together and titled Transportation Challenge. It is full of 500 word stories by many talented w...

The Humiliation Of Jen Ch. 05

by Alfamann on Sep 13, 2017
Exhibitionist & Voyeur

Recapping the characters: My Ma, Pa, older brother Jethro and younger sister Trixie My Uncle Jimmy & Aunt Shirley, and their 2 sons, Stan & Billy My cousin Dirk My boyfriend Bobby Sonja, the bitch cheerleader * Saturday dawned hot and humid. It was the day of Uncle Jimmy's basketball team's first away game. Which meant it was the debut day for me as a...

Coach's Conquests Ch. 10

by MrDean70 on Sep 12, 2017
Erotic Couplings

After showering and cleaning up, Bret headed for the parking lot and his Jeep. The site was unbelievable. They there were, all the Lakeville cheerleaders, in bikini tops and denim jean shorts, washing cars and helping to serve barbecued hamburgers, hot dogs and the trimmings. The crowd was large; it was obvious the girls were rolling in the money. Pamela wa...

Darla's Games Day 03

by Panthergirl on Sep 25, 2017
Exhibitionist & Voyeur

Day 3 Monday> Sleep came quick enough. I just cried myself there. However, it was not the most restful sleep I have ever had. I felt like I tossed and turned all night. How did I get into this mess? How was I going to get out? Would the next fifty-three days leave me with any sanity at all? I woke to the sound of my mom yelling that she was leaving for wor...

High School Futa Ch. 09

by ToSexorNotToSex on Mar 23, 2020
Transgender & Crossdressers

Author Note: All characters are above the age of 18. --- Before she could make a decision about the whole Pornhub deal, Emma had one thing to take care of. A wager she'd lost. It had been a few days since everything kind of converged, and Emma wasn't particularly busy. So, in between making light-hearted fun of some "ugly" pictures Lindsey took of herself...

Never Bet with your Heart Ch. 01

by monkeytail10103 on Sep 12, 2017
Loving Wives

My wife Jill and I moved from North Carolina to New York City after I got a promotion with the investment group I worked with. We hated to leave our home state but it was a good opportunity and since we were in our late 20's and didn't want to start a family for a few more years we thought it would be fun to live in the city for a couple years and hopefully...

Friday Night Lights

by YourObedientServant on Oct 6, 2020
Group Sex

(All characters are at least 18) My girlfriend was delighted when I told her I would help her fulfill her fantasy. Ever since she admitted to me that she was submissive and got off on being told what to do, on being manhandled and compelled, we had been getting kinkier and kinkier. But I had always balked at getting other people involved. But I had, slowl...