Chastity Vacation Stories

28,540 results
Orientation
Length
Source
Infinite Scroll

Cross-Dressing Vacation with Wife Ch. 01

by Wifesbicagedsissy on Sep 16, 2017
Transsexuals & Crossdressers

This is my first attempt at a story. Hope you all like it. Comments are very welcome. ***** It all started when my wife (Staci) and I had a conversation about how comfortable women's clothes looked and we both laughed and I boldly said, "I would wear women's panties and satin pajamas because they look really comfortable." Now keep in mind that I have alway...

Femdom Vacation Ch. 04

by eatmebeatmeguy on Sep 25, 2017
BDSM

*** Part 4 - Please read chapters 1-3 for the full story *** ************************************** I parked at the strip club and Mistress Alana and Goddess Jana got out of the van. I followed them to the door. A large muscled black man was doing security. "He's with us" they said as we all walked in, not paying a cover. We entered the club and it was r...

Letter from Providence

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- I love your letters, but noticed you had nothing from our humble Rhode Island. During corner time after a painful discipline session, I turned my phone's recorder on. I love my stepdaughter, and wouldn't embarrass her, but she is so wild she doesn't care, and of course she is of age. This is for your "Taped Confessions" Eugene Scobrinks...

The Perfect Pair Pt. 08

by ChangeYourPassword on Oct 6, 2020
Fetish

The Perfect Pair, Part 8 (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...

Anklet Adventure Pt. 03

by dometoo on Oct 30, 2018
Interracial Love

Editor's note: this story contains scenes of incest or incest content. ***** Our plane touched down at three PM on a Sunday, as scheduled, and while my family rejoiced, ready for a fun vacation, my heart sank. We were only here in Panama at my wife's insistence. She couldn't turn down her bull's offer of an all-expense paid family vacation; one that promis...

Fun Sex Games with My Wife

by wandabanghammer on Sep 13, 2017
BDSM

My wife and I have been married for about a year. We moved in together 7 or 8 years ago after dating off and on for some time. Our sex life has always been pretty great. That exciting new couple sex when we were dating was some of the best I have ever had. My wife is hot. Really hot. She's the type of woman you see on the train and think .. 'oh, the things...

Scott's Story Pt. 07

by DeanaBard on Jun 8, 2020
Fetish

Chapter 7 - Going with the FLOW December 12, 1979 Chastity was born. I was there when my pride and joy popped out of Ann's freshly shaved pussy. My wife may have recently turned 18, but as I took pictures I thought to myself: [Aside from Ann's enlarged tits, this looks just like one young GIRL is giving birth to a smaller version of herself!] The birth of...

The Perfect Life for Davey Ch. 07

by PeterOmez on Sep 16, 2017
BDSM

Since I always had to get Tyler's permission for every little thing I did, I asked him, one day in April, if I could call one of the factories in Bellewood to ask about summer work. His reply shocked me. He said, "No, you're not gonna be in Bellewood this summer, Davey, you're comin' home to Keenesburg with me." "What? No. No, I... I can't do that, no... u...

Gwenny's Puppy Boy Ch. 01

by atrickofthelight on Sep 15, 2017
Fetish

A year ago in June I came in contact with Miss Gwenny on an alt personals website, while on vacation. The e-mail history has been lost, but the chat sessions from that time remain--somehow we had come to the conclusion that I would be the best submissive I could be as a servant to a man. I had never been with (and have yet to be with) a man and so, despite...

Erotic Games Ch. 03

by jealouscuck on Jul 17, 2018
Fetish

MEREDITH'S STORY When Brad and I got married, I was intending to leave my wild side behind. I was a nurse and really enjoyed it. I had made it up to the position of a personal nurse to a very nice doctor. Brad called on my doctor and that is how we got to know each other. I had been in several relationships, but I was not ready to settle down just yet. I am...