Chaperone Stories

1,440 results
Orientation
Length
Source
Infinite Scroll

Please Remove Your Underwear

by AceStroker on Sep 25, 2017
Exhibitionist & Voyeur

Embarrassment is a part of life, and so is getting a physical. For most of us the former usually happens as a result of the latter. When the exam is watched by members of both sexes, not only is the embarrassment multiplied, but unwanted sexuality sneaks its way into the non-sexual, clinical exam room. For the patient on display and those watching his nakedn...

Weekend Plans Ch. 01

by Logan Shaw on Sep 14, 2017
Erotic Couplings

She comes to me, my Butterfly, every fortnight's Friday evening, and each Wednesday between. On the weekends, those weekends, Our Weekends, we often have a chaperone whose sensibilities we wish not to offend. The sunlit hours and twilight, then, become a whirl of teasing touches and seductive stares. She has beautiful legs, milady does, and I encourage her t...

Chaperone Services...

by MagicDragon2 on May 15, 2019
Erotic Couplings

It started as I was on an airplane flight and travel to a semi-fancy resort type hotel. Checking in I was welcomed into an engineering conference and training program, exactly what was being discussed or educational subject covered is to be discussed. I am taken to my room/suite and it is somewhat fancy, comfortable and nice, but I have no view, except for...

Shaving Debate

by JohnnyMax on Sep 16, 2017
Humor & Satire

I'm Mona and I write for a local news service -- a social commentary page. Doesn't pay much but it's interesting reading the feedback and comments. This topic came to a head after that Irish authoress displayed her unshaven pits on television. Gross, well done, etc were the range of responses but one comment caught my eye. "You girls just don't get it do y...

The Chaperone

by Couture on Sep 17, 2017
BDSM

"I've got an important project for you Rebecca," Mrs. Stone said. Finally, a real project, Rebecca thought. She had accepted a job as Mrs. Stone's PA after becoming unemployed. The pay was good. The hours were horrible. And Mrs. Stone was very demanding. Most managers didn't expect to work personal assistants like they did in the old day. But, Mrs. Stone d...

I Am On The Menu

by TopflightWife on Sep 17, 2017
Loving Wives

Margaret had just left for the party. I admired myself in the mirror. If I do say so, I looked fabulous! The cobalt blue cocktail dress clung to my hips and shoulders. The leg slit showed off plenty, but not as much as the cowl neckline, of course. The neckline plunged and my bare breasts rested in its folds, supported by the fabric, nipples hard and dabbed...

Mom & Me Ch. 37

by Yechesem on Apr 20, 2020
Romance

Planning & Preparing For The Fall Dance While I was walking toward the school, it occurred to me that the Fall Dance was only two weeks away. I need to talking with all my girlfriends, and Ginny, to make sure I'll be able to dance at least a couple of times with each one of them. I needed to know if they were going to go as someone's date or just show up by...

Chaperone

by PhRedSonya on Apr 9, 2019
Erotic Couplings

As you enter the Seattle Aquarium with Michelle and her classmates, you can't believe that you actually volunteered to be a chaperone for her class field trip. Here you are surrounded with 27 hyped up kids wanting to see everything at once and not a single one of the mom's that volunteered is hot either. So, there you are looking at the Window on Washington...

Fun Before The Trip

by football_stud on Sep 16, 2017
Toys & Masturbation

This story is 100% fictional and any likeliness to a real person or place or event was not intended and I apologize. Jennifer is a new teacher at Big Mountain high school and is a beautiful Filipino who stands at 5' with long brown hair that goes to her beautiful round ass and weighs a very sexy 150 lbs which she carries very sexily with beautiful full and...

Annette

by EJSimpson on Sep 1, 2017
Group Sex

Despite the descriptions and the paintings that had made their way to England, nothing had prepared Annette for her first glimpse of Versailles. Fountains played in the ornamental gardens while ladies with large fans sat on fine stone benches taking the air. The scent of the numerous rose bushes tantalized her nostrils with its perfume and the beautifully sh...