Chaperone Stories

1,440 results
Orientation
Length
Source
Infinite Scroll

The Dawn Chronicles Ch. 01

by YoungerM4BustyF on Jun 26, 2019
Mature

*All characters in this story are 18 years old or older* *** The bus sped down the wide-open, two lane highway, trees and brush whipping by outside. Forty year old Dawn Phillips sat in one of the rows toward the front, two seats to herself since what kid would want to sit with one of the trip chaperones. Dawn's son Tim attended Sunfield Academy and it was...

Patricia's Sexual Adventures Ch. 03

by cumn2xtc on Sep 13, 2017
Loving Wives

Patricia's Bio I get a lot of questions from readers and people who have seen my pix and movies and they have asked to know certain things about me. So I decided to put together a BIO about me to answer some of the most asked questions. So for those curious ones, here you go. What is my birth date: 12-24-63 Where was I born: Pennsylvania Where do I li...

A Story of My Slaves Ch. 1

by Anon_persona on Sep 17, 2017
BDSM

This is the beginnings of my career - the market of buying and selling female slaves. It begins, however, in my backwater college - a mere state school in the upper midwest. I'm hardly impressive physically, just your average thin runner-type. I was, however, fortunate enough to be a bit of a lady's man. Never so much that I was swarmed for dates. Rather, I...

Why Knot Tickle?

by johnthomas19692 on Dec 24, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** "Come on please?" I begged. "Why do you need to tie me up again?" "It's for that survival group I'm in. We need to learn to tie different types of knots for different situations. But mainly things get tied down to hold something in place," I explained. "And why do you need me?"...

Losing It to My Drumline Instructor

by thirstygirlll on Sep 2, 2017
First Time

I was in high school, he was in college. I was 18 and he was 27, which wouldn't have been awful outside of school, but he worked for our school. I was in front ensemble, and he was in charge of mentoring all the percussion students. Since camp started in August, I was attracted to him. He was cute, we had some things in common, and he was nice. I also like...

From Africa Ch. 10

by aislin brody on Sep 16, 2017
Novels and Novellas

Paris, 1954 'Aren't you happy to finally be passing the reins of your burdensome chaperone to Miss Peake?' Mark leered at me with a saucy grin as I moved across grass to the other side of the garden. We were attending a party thrown by one of Anna's well to do friends, out in the picturesque French countryside. 'Reins?' I looked at him, confused. 'Or, I...

Open Marriage

by Itascan on Sep 10, 2018
Loving Wives

It was during my first or second year at the university in the English Department when I met and became friends with Jim, who was also a new instructor. He taught economics, and his department was in the same building on the same floor as the English Department. Jim was 6' 2" and slender with black, curly hair. His wife, Pam, was about 5' 2" with short, ligh...

Not So Much a Stable "Boy"

by BootyLaBooty on Sep 14, 2017
Romance

Set in 1800's English countryside. A stable boy finally succumbs to his lust for the spirited young lady of the home he serves during a trip to meet her betrothed, a man whose wealth would save her financially unstable family. (modern language.) ***** Evie shoved the threadbare curtains away from the window of her small stagecoach. Her heart rate quicken...

Angie Gets Even

by Tamzarian on Sep 16, 2017
Group Sex

Angie George was gone frequently on business trips and was one of the most successful saleswomen in the state. Angie was about 5'8" with short, curly blonde hair and wore glasses with small red frames. She was in excellent shape and had great breasts. "Girl, you've got to get back at that deadbeat." "Well I'm not taking him on the trip to Nassau." "You s...

The Godsmack Concert

by thehumpman on Sep 13, 2017
Erotic Couplings

My son Chris came into the living room talking to his friend Joey on the phone, he was very excited from the tone of voice he was using. He handed me the phone telling me that Joey's mom wanted to talk to me for a few minutes about something. "Hello." I said. "Hi Tom this Julie." She said. "Hey Julie, what can I do for you?" I asked. "Well I got the boys...