Jamaica Vacation Stories

23,161 results
Orientation
Length
Source
Infinite Scroll

Risking Judy Ch. 02

by Chris Seagate on Sep 18, 2017
Loving Wives

The next morning as I left for work, a crazy impulse struck me and I grabbed the "WeddingX" CD from its hiding place. I knew the idea was completely insane, but I had decided to show Jason the nude photos of Judy! My self-esteem needed for him to know that my wife was hot. I walked into Jason's office with the CD - nervous but determined. "Jason, would you...

A Desire Finally Achieved Ch. 01

by sunshine5930 on Sep 13, 2017
Interracial Love

Author's note: Names where changed to prevent embarrassments to my friends. Any similarity to living person is purely co-incidental. A special thanks to jlo24601 for proofing and very helpful suggestions. * Sunday - February 12, 2006 Introduction Hi, my name is Heather. The root of this story is a ten year fantasy turning into a fabulous real life exper...

Penis Size - Separating the Boys from the Men

by TX_Fun_Dr on Sep 13, 2017
Reviews & Essays

There are many many stories posted on Literotica that some readers (especially those cowards signing their comments as Anonymous) complain that the author exaggerated penis size to an entirely unbelievable length Now that is not to say there isn't the possibility of penises being that size in the US. But for now let's just agree to call that artistic license...

Fantasy Island

by NineIsFine67 on Sep 9, 2019
Interracial Love

“I’m sorry Kathy, I can’t go.” It was the words I dreaded to hear but had actually expected. “I’m really sorry but a week is just too long to get away right now.” My friend was right, we really didn’t think she was going to be able to come with me on the trip, but I had no one else to invite. You see, I am a widower of 4 years, my husband died in a car acc...

Marking My Women Ch. 06

by SirenSeeker on Sep 13, 2017
Loving Wives

As I had expected the week of Mary Ann and Steve's trip to Hedonism in Jamaica was one of pure hell for me, yet shaded with a thrilling angst that only a cuckold can experience. Yet, was I really a cuckold or simply a guy who had lost his girl to another man? I had listened and learned that night at Steve's house of Mary Ann's intense craving for his sex, wh...

Backyard Gangbang

by sunshine5930 on Sep 13, 2017
Interracial Love

I was feeling on edge one night desiring a black cock being that it had been sometime since I had a black cock give me pleasure. I logged into a black chat site to see where it would lead more or less, to kill some time and satisfy some curiosity. After many screens and typing "sorry busy" because of not desiring to chat because of not liking their nick nam...

Jamaican Holiday Ch. 14

by jayewatcher on Sep 19, 2017
Interracial Love

Aftermath This brings us up to Dec 2010 and our most significant event - and introduces Robert, our Bull and future Master Dec 2010 -- It's been 6 years since that vacation to Jamaica. When we got back we intended to return to our normal Vanilla existence. But we couldn't -- too much had happened. As Jaye put it, the door had been opened to something dee...

Naked Hedo Sex Vacation Ch. 04

by TheNekkidUn on Mar 3, 2020
Exhibitionist & Voyeur

This is part four of our trip to Hedonism resort in Jamaica. As I've written in prior stories. I'm a nude model and my girlfriend is a nude dancer. I made the switch from a regular job to being a nude model so that I could be naked as close to 100% of the time as I could. She and I dated a few years ago but reconnected one night when I went to an Atlanta...

Man in the Chair!

by MormonChicks on Sep 26, 2017
Interracial Love

Man in the Chair! A Jamaican Vacation/Cheating wife Story. ************************************* If you don't believe in the unfaithfulness of wives or interracial sex you should click black and select another story. ************************************* Jesus H. Christ! How did this happen? I couldn't believe it was me in the chair. I'd read a hundred s...

All-Inclusive

by PAPATOAD on Jun 1, 2020
Loving Wives

This is a re-post of a 2009 story that has been re-edited and lengthened. There is no sex in this story. Linda and I had been married for twenty-three years. We raised two daughters and I thought that we had a good marriage, but what did I know. I tried everything I could to be a good husband. I was attentive. I was not rude or overbearing. I didn't ignor...