Chaperone Stories

1,440 results
Orientation
Length
Source
Infinite Scroll

Just a Few Pics

by chas962 on Sep 12, 2017
Loving Wives

Chapter One - While It's Not Too Late My wife (Elizabeth) and I had married young and were relatively inexperienced. As the years unfurled we discovered the wonder of sex with a truly loving partner and our union gave us two wonderful healthy children. As middle age approached I began to experience physical problems which began to make lovemaking a frustra...

Kathy Goes to the Dance

by Just Plain Bob on Aug 19, 2017
Exhibitionist & Voyeur

"What's on your schedule this week?" Kathy asked her husband Mark. He looked up from the morning paper and said, "Nothing special. Why?" "It's my turn in the barrel again. I have to chaperone the Spring Dance and I was wondering if you would like to go with me." "Yeah, right! You know how I feel about those things. I still don't understand why you have to...

Dearest Ch. 01

by LittlePinkRoseBush on Sep 26, 2017
BDSM

I remember screaming. I remember running. I remember tripping and falling, being caught, breaking free, being caught again and restrained. But these are not real memories. They are the creation of my battered psyche, an attempt to make sense out of what was then to me a senseless, purposeless act of fate in which my mind refused to accept that I might not ha...

Pedigree

by Justwords on Nov 20, 2018
Sci-Fi & Fantasy

I am one of the lucky ones. That's what I've been told my whole life. In a world where all men control their own lives, and all females are bred, raised, and die as pets for the males, I am one of the lucky ones. Here's my story... I was born to my father Preston Vaughn Cox eighteen years ago through a quality female that he bought from The Mayor's Auction....

Overseer of the Harem Ch. 12

by SexyGeek on Sep 19, 2017
Erotic Couplings

Bagoas luxuriated in having no urgent duties to call him out of his bed in the early morning. He lay back against the soft pillows and enjoyed the feel of the silk sheets against his skin. The soft bed, the tinkling fountains, and the soft noises in the hallway reminded him that he was not at home. Bagoas was a person of power in his own world. He was, inde...

Romance Wars Ch. 01

by WillLyn on Sep 3, 2017
Erotic Couplings

These stories are based on and inspired by experiences with the real life Captain O'Malley, a beautiful and sensual woman who taught me much. I'm using as many stage names as I can so that only those people that were part of the story are able to tell true identities and changing real names where no stage names are available. ***** "ROMANCE WARS. A great w...

Help!

by Harddaysknight on Sep 17, 2017
Loving Wives

It seemed like a great idea at the time, but don't most cluster fucks start out as strokes of genius? Cindy's older sister, Chloe, had asked us if we would be interested in being chaperones on her daughter's class trip to the exotic Caribbean Island of Kokomo. All we had to pay for were our airline tickets. My wife quickly accepted the offer. Chloe even off...

Literotica Monthly Awards 2020: April

by Literotica on Jul 14, 2020
Erotic Couplings

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of April Reader's Choice Awards. First Place ($150 Cash Prize Winner):The Rask Rebellion by SnekguySecond Place ($100 Cash Prize Winner):Matchmaker 03: March by Sanit...

Dickgirl Tyranny

by Lusc on Mar 28, 2018
Transsexual

In this medieval/victorian fantasy world, the physical differences between men and women(also known as dickgirls) are enormous. In comparison to their male counterparts, women are taller, stronger, and better endowed. On top of all this, a dickgirl's cum has a strange drug-like effect on males. This effect's severity is mild when applied to the skin, stronge...

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Change Ch. 22-24

by BobbyBrandt on Jan 22, 2020
Novels and Novellas

Chapter Twenty-Two "Do you want to come with me when I go pick up Katie?" JR asked. She was sitting on his lap in a chair in the family room. Patty had told her to relax for a couple of hours before she would be needed to help mash potatoes and finish the other side dishes for their meal. "I would love to, but that will be when your mom expects me to be...