Chaperone Stories

1,440 results
Orientation
Length
Source
Infinite Scroll

Tutor My Boy

by Ashson on Sep 17, 2017
Erotic Couplings

Annie was at the mall when she ran into them. There was a bunch of school children being escorted around the mall by three adults, presumably their teachers. Now that she'd run into them, she vaguely remembered signing a permission slip. She spotted David, her son, amongst the throng, but not wanting to embarrass him amongst his friends did no more that wav...

Step Twins Ch. 02

by jane700bond on Sep 13, 2017
First Time

All characters are over 18. This story is written from three points of view * Steve, ** Lucy and *** Tanya. Whilst it makes sense by itself, it follows on from "Step Twins Ch. 1". This is my favourite sort of fantasy. My own body is a bit like Tanya's, but I just love slim girls like Lucy. I hope you enjoy reading it as much as I enjoyed writing it and pla...

My First Love/Sex

by goingstrong on Jun 11, 2019
First Time

This story takes place early 1958. At that time cross country travel was still very much by rail since air travel was comparatively expensive. The Royal Canadian Air force (RCAF) also moved new recruits by rail and I was one of those new recruits. I boarded the train in Calgary Alberta destine for a training station in Quebec. I was looking forward to a rath...

The Chaperone

by hafnium10 on Aug 30, 2017
Exhibitionist & Voyeur

If the music is to loud then you are too old. Well, I guess that makes me too old. The DJ has the music blaring and I am looking for a place with a little peace and quiet. It is hard to find in the small gymnasium where our high school is having their dance. I don't know what possessed me to chaperone this senior class dance anyway. These dances are not like...

Bad Chaperone

by Silkyvi on Mar 25, 2019
Loving Wives

"I've seen the way you look at me, even when I was dating your daughter. I know you want this." I should have denied it, but I'd been getting more and more turned on the whole night. Now, standing right in front of him, too close, it was hard to deny his primal attractiveness. His gorgeous 18-year-old body, in the prime of physical fitness, awaked every pri...

The Senior Trip Ch. 01

by SteveLee1146 on Sep 12, 2017
Erotic Couplings

In the small high school in the little town of Lynwood, Ohio, in the mid 1990's, a feeling of pleasant anticipation ran through the halls. Spring break approached and a week off from school seemed like heaven. For a small group of senior honor students, however, there was something more -- a trip for a week in Washington, cause enough for elation. The group,...

Affair of the Heart Ch. 05

by BlueJerseyGirl on Sep 15, 2017
Novels and Novellas

Jeremiah staggered back into his room. If he could rewind the last few minutes, he certainly would. He had just barged in on his sister and found her making love with, he guessed, her new boyfriend Matt. She appeared too consumed by lust when he entered. Her image was burned into his brain. Suddenly his door burst open. "What the hell is the matter with yo...

Give Some, Take Cum

by Archer2050 on Sep 11, 2017
Group Sex

This is a stand alone story, and everything you need to know to enjoy it and understand it is in here, but if you want to read about the action before the action, check out 'Chaperone Makes Three'. Penny had never had quite so much fun—or felt so much anxiety—during work as she had today. As a saleswoman in a lingerie store in the mall, there were always th...

Taking Amy Ch. 2

by assslut! on Oct 20, 2020
BDSM

The rising moon glowed eerily through the stand of trees. Shadows stretched out across the road, lengthening and shortening as the breeze roared through the forest, causing limbs to quake and the thinner trunks to bend over almost double. The night was alive. Amanda gazed in disbelief at the slack jaw of her guardian. She hummed to herself trying to block...

Teacher's Aid

by Pissfan1234 on Dec 3, 2019
First Time

True story, names have been changed to respect privacy. All characters 18 years of age or older. * Memories of senior year in high school means different things to different people. Maybe the one shy introverted kid finally got the date with the one cheerleader, or maybe the unpopular girls got invited to a party at the popular girl's house. For me. though...