Size Bet Stories

142,710 results
Orientation
Length
Source
Infinite Scroll

Susie Ch. 18

by Susie_O on Sep 15, 2017
Romance

Advice Columnist My name is Susie O'Connell. Near the end of my first semester at the local community college my English teacher, Ms. Richards, asked me to stay after class. A girl came in and Ms. Richards introduced her as Darlene White, the editor of the school paper. Darlene told me that the paper needed an advice columnist and that I had been recommende...

Amy - The Amazon (Usually) Ch. 06

by sexgundam666 on Jan 29, 2020
Sci-Fi & Fantasy

Amanda yawned and stretched to pop her joints. She didn't have classes that day, though Amy did. Despite the Amazon's protests, Amanda convinced her to go, largely to let her body relax after last week and the subsequent nights thereafter. Turned out she could only handle so much of Amy's new size. Her pussy ached in satisfied exhaustion, still loose from la...

Hell Has No Fury Like A Drag Queen'

by Victor C. Anderson on Sep 16, 2017
Transsexuals & Crossdressers

The Morning After: Scott slowly awoke to his cock being stroked. Relishing the smooth skin pressed to his back, the silky leg thrown over his, and the lips nibbling at the nape of his neck, he was surprised that his wife was this amorous in the morning. Susan was no prude, but she also was not the sexual aggressor in their marriage. Indeed, their first sexu...

Humiliated by Boss' Daughter

by radassat on Sep 17, 2017
BDSM

"Come up, I need you upstairs," said Sarah and closed. When you work for rich people you have to do a lot of things to satisfy them. And the children are even more moody. Sarah, who started college just a month earlier, liked to give me a lot of things to do. I was sure that sometimes, she was doing that only to have fun. She was a little bit bitchy, just l...

The Advent of the White Mini-Skirt

by LeggoMyEars on Sep 12, 2017
Exhibitionist & Voyeur

Christy knew all too well that her love, Dusty, loved exhibitionism. One day she was shopping for a new skirt when she spotted a semi sheer white cotton skirt that was short enough that if she sat directly across from anyone, they would have a clear view up her skirt. She modeled it for Dusty later that day. He was pleased with her choice naturally! That we...

A Prostitute Enters The Room

by disturbingjulia on Aug 18, 2017
Fetish

I walked into the bedroom, and you were just sitting there jacking off. I don't even know why I'm wasting my time with you since you're cock is so small, I mean it was ridiculously small, I've seen bigger on dogs. and I bet you can't even get it up for me, since you're not even a man at all. just this fat ass loser. god, and you tried to come over to me and...

Lost Bet

by Kinxx on Sep 13, 2017
Anal

It was almost a Saturday afternoon ritual - Jim, one of my friends from work would come over and we'd watch the football game (or hockey if it was winter), drink some beer (ok, a lot of beer) and enjoy ourselves. Usually our wives would get together and either go shopping, out to a movie or basically be anywhere but there with us. It usually worked out ok...

The Bet Ch. 01

by StudHummingBird on Sep 17, 2017
Loving Wives

My company insisted that I take two weeks of vacation; the old; use it or lose it. Nan, my wife of 10 years, was not able to take any time off. It was a good opportunity for me to tackle those household chores I have been putting off for months. By Tuesday of week two I had repaired it, mowed and trimmed it, or painted it and was left watching the soaps, gam...

Older Neighbors Win The Bet Ch. 02

by wildp on Sep 12, 2017
Group Sex

I was sitting on my couch a couple of days after losing the bet with Sarah and Kim. I was still amazed at how great the sex was that night with them. I had never looked at big girls before but had always wanted to be with an older lady. Sarah was fourteen years older than me and Kim was thirteen years older. As I was sitting there thinking that the phone ran...

My Panty Fetish Ch. 02

by kinkyjill on Sep 16, 2017
Fetish

I had a lot of replies from men who have a heavy panty fetish and thought I'd write a fantasy involving one of these guys- I have changed the name to protect him. I never realized that so many men share this fantasy in reality, but I thought that they liked reading about it and not participating in this fetish. His name is John who confessed that he was mar...