Gay Pirate Stories

212 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Pirate's Tail

by sr71plt on Aug 18, 2017
Gay Male

I am fairly certain my father knew there was more to my being apprenticed to the Dutch munitions broker Fons Hertzog when I arrived in Cape Town from London then learning a merchant's trade. He was being protective of me, I'm sure, the Great War having broken out the previous summer in Europe with the assassination of the archduke. With the war only enlargi...

Scratching an Itch

by Pirate_Guy on Aug 18, 2017
Gay Male

Boy oh boy did I ever get my itch scratched today... (A quick note: I recently posted a short recollection in the GLBT Chatter forum about the first time a guy took my ass. Just writing about it and reading several hot PMs people sent me got me itchin' to get fucked again after several years of semi-retirement from the bi world. So, I e-mailed a buddy from...

Pirate’s Overlook

by Bottomedout172 on May 12, 2020
Gay Male

I met bill at a charity golf tournament when we were paired in a cart. We became lovers that night and have been together for six years. About four and a half years ago we made a private commitment to be exclusive. We came out to our families and close friends at that time, certainly no surprise to my kids or ex wife. We did not live together because we thou...

Pirated

by sr71plt on Aug 18, 2017
Gay Male

I was just about home free with the tasty wench the lads had brought on board for me from Kingston when the attack started. After some mouth play, she hadn't objected in the least when I'd unlaced her bodice and started giving her ripe melons the attention they deserved. We were entwined together in the window seat of my vessel's fantail, and, forward lass t...

The Pirate King Ch. 01

by nakamook on Sep 19, 2017
Gay Male

First story, so bear with me here! Comments and suggests always appreciated and welcomed. A sailor finds himself falling hard for the pirate captain that captures him. But he has a plan, and this does not fit into it. Will he be able to set aside his strange desires to get to where he needs to go? When you're the captain of a pirate ship, you're used to...

The Pirate and the General

by OregonDavid on Aug 18, 2017
Gay Male

I don't know how it started. I don't know when it started. I only know when I realized that I wasn't like all the other boys. This is the true story of my first sexual encounter. Before the budget cuts, my high school used to stage an elaborate outdoor theatrical production each spring. A professional set designer would be hired and long nights and weekends...

Black Pirates of the Norfolk Broads

by Tiberius58 on Aug 18, 2017
Gay Male

When Tony Samuels asked me to go on a boating holiday with him, I was delighted; we had been friends, and sometimes lovers, for a long time. We drove from London to Norwich, took over our motor cruiser, and sailed down the River Yare towards Breydon Water. That evening we moored up at Reedham where we intended to spend the night, and went to one of the river...

The Pirate King Ch. 14

by nakamook on Sep 14, 2017
Gay Male

This is part of an ongoing series - I highly recommend you go back and read from the beginning. We'll still be here when you get back. :) Alternate title: his infernal way of being As always, comments and feedback much appreciated. Longer chapter this time; heard what you had to say and managed to get some more words on the page. Also, something new this...

The Pirate King Ch. 15

by nakamook on Sep 14, 2017
Gay Male

First things first; if you are here without reading the previous chapters, I *highly recommend* that you go back and read those first. This is a plot heavy journey, and we'd love to have you along for it's entirety. Don't worry. We'll still be here while you catch up :) Second, and most important: Wow. I have been feeling. Humbled. Awed. Like my stomach is...

The Pirate King Ch. 16

by nakamook on Oct 9, 2017
Gay Male

Long time no see. I know. I'm sorry. Things got hard, and it felt too strange to escape to a world where the power of the sea was such a romanticized thing while I watched so much of my country disappear into a hurricane. Anyway. Have some sailors, and remember love. Imagine what trust feels like when you carry it in a place deeper than your bones. Alte...