Chastity Vacation Stories

28,540 results
Orientation
Length
Source
Infinite Scroll

Delving into Femdom Ch. 02

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 4. Navigating the Next Step The next day I awoke and had to go to the mirror to confirm if my ass was red or if this was all really a dream. However I had actually had my first FemDom experience and my head was racing. The encounter with Mistress Veronica was so vivid I could recall every step that occurred last night. I wasn't sure what my next m...

Chianti Cares...

by justincbenedict on Apr 9, 2019
BDSM

"I'm not even sure why I'm here." Reba said, trying to smile. In her early forties, Reba had curly dark hair and was somewhat curvaceous, but the sort that dressed sensibly to avoid the censure of her peers. Chianti had met Reba when they'd been taking an Italian cooking course together at Mallard Creek Community College, just across Buttermilk Bridge. It...

Sami

by Tricker126 on May 5, 2018
Fetish

You've known her for years. A blonde-haired, brown-eyed girl who always had the energy to for just about anything. As far as you know, she's just an ordinary girl doing ordinary things. Studying macroeconomics at an expensive college you couldn't afford (Her parents were both lawyers), she left just after you told her how much you were into her at the airpor...

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Always Safe

by redem89 on Sep 14, 2017
Erotic Couplings

Well just now, the memory of a lady I knew in the mid-80s keeps coming back. In between my travels, I would visit my hometown for a short break, like a vacation. On one occasion, when I was about 24, I was introduced to this lady who was a year younger than me then. She was slight of build with lovely dark skin. Well, we saw each other a few times and so...

Chastity Resort Pt. 01

by handyrandy9 on Sep 25, 2017
Exhibitionist & Voyeur

I couldn't believe my luck. My wife Anna was next to mein bed and we were talking about our day before drifting off to sleep when she broke the news. "I think it could be fun." She had said. I had brought up the idea of a vacation to a nudist resort a couple years back. Anna had been adamant about her initial response. "No way!" She'd said. "No way I'm par...

The Perfect Pair Pt. 06

by ChangeYourPassword on Jul 20, 2020
Fetish

The Perfect Pair, Part 6 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and...

Marabogo: Cuckold Island Ch. 02

by eeric on Aug 29, 2017
Fetish

"Hold the elevator please." Megan and Joshua heard a woman's voice just as the elevator doors were about to close. Joshua quickly held out his arm to so the doors wouldn't close. Through the small crowd of newly arrived guests, they saw a very scantily clad and rather chubby young woman coming at them. She was slightly jogging, her huge chest and big belly...

Pledging Virginity

by Carol1973 on Sep 12, 2017
First Time

I took a pledge in high school to remain a virgin until I was married. I came from a conservative religious family and the church was my harbor in the stormy sea of adolescence. Frankly, it didn't seem like a big decision at the time. My best friends were members of the same church and several of us took the pledge together. We bolstered our pledge by prayer...

Australian Ascendency

by harvey333 on Sep 13, 2017
Fetish

On vacation with my wife, we were visiting Australia. We didn't know much about the country, but rather liked the idea of going to a strange place with no set agenda. Relaxing on the sand in a couple of fold-out recliners, my wife suddenly stopped talking in mid-sentence. I turned to follow her gaze and saw a man about my age of 45. He was setting up his own...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...