Grindr Stories In Jamaica' Stories

370,057 results
Orientation
Length
Source
Infinite Scroll

Public Fetish

by Jamie9919 on Apr 22, 2025

Your name is Jamie you are about 5’7 and 180 lbs you weren’t necessarily fat or skinny just average but curvy for a boy you had a very plump round ass and you were just barely 18 when you had experienced your first real cock. It was an older gentleman about 38 that you met through an ad on Craigslist in which you posted “18 yo wants to suck cock first time”...

Open in Reader

My First Crossdresser

by Jay876 on Jul 31, 2019
Transgender & Crossdressers

Monday A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera....

El-E's Anthology of Very Dirty Poems

by El-E on Apr 22, 2025

Contents The poems / poem sequences are linked here. Mine focus on transformation and my usual themes. Add your own if you want other topics.What's next? Sonfucker Sequence Transforming with an Ex-Girlfriend's Family I Short Poem I Short Poem II Dad Dres...

Open in Reader

Mediterranean Holiday

by The Doctor on Jan 12, 2021
Bisexual

Tom was tired and bored. Overdose of Netflix, overdose of Call of Duty, overdose of Facebook... He tried to get his wife in the mood for sex, but she was hopelessly "exhausted" again. He ended up, as too often, frustratedly watching some porn on Amazon Sex. He kept clicking through ads like a robot, from sales of billionaire mansions to cheap eleph...

Open in Reader

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...

The 3rd wheel with Benefits - Part 1

by pisslover on Apr 29, 2025

I was 24 y/o Indian boy who had recently moved to a new city due to new job. I was looking for a place to stay on rent when I found an ad in classifieds about a homeowner letting a small place attached to their apartment for rent. It was a small place with a corner kitchen, cozy bathroom and a bed. I met this man Mr. Deepak who owned the place, he was 36 y/o...

Open in Reader

Jamaican Beauties Jaunt Ch. 01

by TB_OrNot2B on Sep 13, 2017
Novels and Novellas

Chapter 1 -- Beginnings: Their love of Jamaica brought them together. Introduction: A naïve, insecure, and inhibited 26-year-old, mulatto, Jamaican woman trying to get over her European boyfriend who cheated on and then dumped her, goes online and meets a mature, sophisticated, and experienced 41-year-old Caucasian American man who recently separated from t...

Coming Home

by Cinner on Sep 19, 2017
Romance

Nadine knew that staying at Sandals Negril was not the most realistic reintroduction to her island homeland, but she had left Jamaica twenty years before and her childhood memories had seemed magical the more she had indulged them. So, she had not hesitated when the opportunity to return to the island had come up. She got into the coach at the Donald Sangste...

Jamaican Getaway Ch. 02

by Wahoo_1991 on Feb 5, 2018
Exhibitionist & Voyeur

This is the fourth in a series of stories that describe the few times my wife has uncharacteristically exposed herself in public. If you have read the previous three stories you might think she is a wanton exhibitionist, but it really is the furthest thing from the truth. In our day to day lives she goes out of her way to wear oversized clothes to disguise h...

The Biggest Mistake

by arkrebel on Sep 14, 2017
Loving Wives

A while ago I posted a story called Cuckold Landing, that tale was mostly fiction with some actual real life story in it. Part of the real life story included a situation that happened on one of our many trips to an infamous resort in Jamaica. In one of the comments on the other story someone said they would love to hear more of that story. Like any story w...