Cuckold Vacation Stories

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The Cuckold Vacation Company Ch. 01

by a_random_user on Sep 26, 2017
Interracial Love

"It's important to me that my wife doesn't know I set the whole thing up." David was sitting in the back room of an elegant office in a suburban mall. From the front it looked much like any other high-end travel agency. In truth, this office catered to arranging erotic vacations with a very special theme. David was here because he followed up on a few rumo...

A Free Vacation Ch. 02

by jealouscuck on Nov 18, 2019
Interracial Love

The first full night there, the men had the opportunity to fuck their wives. As with Dan, the guys had no idea that unless something out of the ordinary happened, they would not be fucking them for the duration of the vacation. Dan was definitely turned on watching Valerie dancing so closely with her dance partner. Obviously, she was equally aroused and read...

Cathleen Encouraged Ch. 13

by nocluescooby on Sep 16, 2017
Interracial Love

This is the final installment in a story of Black into white interracial cuckoldry. It is hard core and this not for everyone. Don't read on if this theme offends you. It has taken my a very long time to finish this story, and I think my many readers that have been so patient. * Cathleen sat silently in Randy's Escalade as his cum leaked from her freshly f...

(Finished) The Best Vacation: A Cuckold's favourite Story

by Ed1t on Apr 22, 2025

John and Anne have been together for the last 10 years, they got married last year. This year, they've decided to go on a holiday for the first time as husband and wife. They vacationed in Greece and it was the best trip of their lives. What Anne didnt know is that John was addicted to pornography, and not just any pornography, cuckolding. Where he imagined...

Jamaican Cuckold

by pervtoo on Feb 20, 2018
Interracial Love

(A vacation that changed our lives forever) CAUTION: If you are not in cuckold stories with a cream pie ending you might want to skip this story. ***** My wife wanted to go to an all-inclusive resort for her 30th birthday, so I booked it. We were hopelessly in love and got married after graduating from high school. She was a virgin cheer leader on our wed...

Cuckold CEO Ch. 05

by drdick69 on Oct 9, 2018
Fetish

Day three of our vacation started with a thud. I woke up rolled over and my wife informed me that she had started her period. Well at least I was getting unlocked from my cock cage for a week. Usually, when my wife has her period, she unlocks my cage and lets me jerk off to relieve myself for a week. Sometimes we play sexy games with each other, but mostly i...

Cuckold CEO Ch. 06

by drdick69 on Oct 9, 2018
Fetish

Day four of our vacation was pure relaxation. We got up late and planned to do absolutely nothing, all day, except walk on the beach, talk and kiss each other. I was finally shutting off work and getting into a more normal pattern of sleep and beginning to relax. My wife and I walked the route from Tunnels Beach to Ke'e Beach and back just after sunrise. Bra...

Hotwife Vacations Are Fun

by drill9 on Sep 13, 2017
Loving Wives

My wife has been a hotwife and I have been her cuckold since just after we got married in the early 70's. During this time she has had many adventures with other men. Some were one time events, and others were real relationships that went on for years with them fucking her hundreds of times. This story is 100% true. We have had many similar fun times over t...

Sharing Feet Turns into Cuckold?

by midwestfeet on Sep 16, 2017
Fetish

My wife and I recently decided to take a vacation, just the two of us. Since our last experience Wife Finally Shared Her Feet, I've been wanting badly to have that fun again. What I did was put an ad on Craigslist for that area a few weeks before we went on vacation. I was contacted back by a few guys that I thought she would be interested in. I was able to...

Belated Honeymoon Vacation

by rockpaperscissor8 on Sep 12, 2017
Loving Wives

Note: This is another on the same theme of cuckold stories where the husband is a cuckold perv and the wife takes things to her own liking. Sometimes I've been frustrated with comments made by anonymous commenters who just don't get the genre of cuckolding, inject their own conservative puritanical opinion and I have to ask myself, then why the heck are the...