Chastity Vacation Stories

28,540 results
Orientation
Length
Source
Infinite Scroll

Sissy Comes Clean

by Cuckyboy3 on Oct 6, 2020
Fetish

Reflections after Mystic: On the scenic drive back home from a fall getaway vacation with my lovely wife, I pondered quietly how the excursion would be remembered as a first of a kind. I had begun the trip with the expectation of a quick and routine spanking followed the next day by an epic sex experience. Three days later, however, I emerged having not onl...

A Virgin locked in Chastity

by ronron1818 on Mar 3, 2020
Fetish

I was 18 when I moved in with Ruth. Ruth was my new land lady, I moved in with her for my university studies time frame. She had a big house and leased a room. Ruth was 56, in great shape, she was about 170 cm tall and about 50 kg with small breasts and a very nice figure. I was very excited to move, I loved the idea of sharing a house with a woman. I imag...

Princess Jazmin Ch. 01

by subboy129 on Sep 14, 2017
Fetish

My name is Dave and I am a 27 year old man living in Connecticut and I have a great job, my own place, a nice car, and live a pretty normal life. Other than the fact that I am extremely kinky and love dominant women and wanted a Domme. This is a story about how I met Princess Jazmin. I was home one night and was screwing around online, looking for something...

Letter from Tulsa

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Kenyon and I walk along the beach as we vacation in California. It is not really a nude beach, just a clothing optional beach, and Keni has optioned that I walk naked, except for my chastity piercing, and she is wearing a pale blue bikini, to which her curves are magnificently displayed. I am in a bit of pain. I put regular milk in her co...

Femdom Vacation

by eatmebeatmeguy on Sep 11, 2017
BDSM

Bored with my mundane office job and my sexless marriage, I downloaded an app that allows you to vent and share your secrets anonymously. Like most things on the internet, it became over run with thirsty perverts. Myself included. With it, users can chat with people or post publicly. Through using this app, I made friends with an American woman living in L...

A Kinky Vacation Ch. 01

by SpaceBoyToy on Sep 11, 2017
Loving Wives

After 3 years without a vacation for ourselves, my wife and I were finally able to book a cruise in the Caribbean for an entire week. It was to be a much needed break from a stressful job and the full time 24/7 commitment of being parents. I was also hoping that it would be an opportunity to spice things up a bit. Our sex life wasn't bad, but the commitments...

Goddess Glitter's Happy Litter

by justincbenedict on Oct 8, 2019
BDSM

Prabu obediently was sucking away on Goddess Glitter's plastic schlong, the biggest she had. He hoped she wasn't upset with him, but even the great job he was doing with the slurping didn't seem to get a smile on her face. "Enough!" Glitter grabbed Prab's mop of ink black hair and pulled him off the dildo. It was such a gorgeous thing, hanging from the...

You Took Everything

by playplay19722 on Sep 12, 2017
BDSM

Today you told me it has been a year since we first decided to get together 24/7. In that time you have taken everything from me and I have gladly given it. When we first started dating you put me in Chastity. That was the beginning. First you took my ability to say no to you. On our first weekend together you tied me spread eagle on the bed and began teasin...

Your New Male Slave

by CoupleInExile on Sep 14, 2017
How To

So you've taken a slave. Congratulations! Chances are, you really haven't given much thought to 'What now?' It's all been fun play for a few hours. But. If you really want a *real* slave, you'll need to invest some time and effort in consummating your new property arrangement. Your new possession may be naturally submissive (or not! even more fun!), but you...

The Chastity Cube

by justincbenedict on Sep 17, 2017
BDSM

F.X. Copeland came to the Deliosse's front door, lugging the massive box, and pressed the doorbell. A moment later, Santiva Deliosse answered. "Oh, good, Cope, you're here. That's the Zero-Wave?" Cope nodded. "Yep, Miz Deliosse. Works like a microwave, but in reverse. It's an innerustin' invention of mine." Cope lugged the box into the house. It was a big b...