Sailing Stories

4,437 results
Orientation
Length
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Infinite Scroll

A Miner and a Lady

by EgmontOriginals on Sep 16, 2017
Romance

(Set in Queensland, Australia) Walking along the main street late Saturday morning and carrying a shopping bag in each hand, lanky blond Australian Pete Rutter pushed his sunglasses back over his curls with his right wrist. That gave clearer vision of the approaching nubile woman in white shorts and wearing an eye-catching multi-colour top knotted above t...

Special Bahamian Charter

by LBMM2008 on Sep 16, 2017
Group Sex

This is the story of a young charter boat captain introduced to the swinging lifestyle and to his own bisexuality by an older experienced couple. Nick Morgan eased the boat heading to take advantage of the northerly current in the gulf stream. This heading would take his newest charter into Bimini Island for the evening. He'd been working as a charter bo...

Sailing Adventure

by hannsg on Aug 31, 2017
Exhibitionist & Voyeur

A friend provides a memorable erotic boating experience. For months I had been looking for a sailboat, I scoured all the local newspapers and could not find what I was looking for. This was before the Internet, as we know it today. Just so, you get some idea of how long ago it was, there wasn't any internet and computer were still using punch cards. I was...

Frustration of Small Cock Pt. 06

by jamtby on Jan 22, 2019
Transgender & Crossdressers

As she stood there smiling at me I said, "You are one hell of a woman. I don't why those dumb men you knew in the past let you go but they were truly dumb asses." She smiled. "Maybe they were just a warm up for the real man I am with today." Part 6 After such an active afternoon it was time some wine and cheese. I said, "It must be 5 o'clock somewhere. R...

She Wanted to Win

by SierraSprite on Sep 14, 2017
Novels and Novellas

I was in the cockpit of my boat, doing chores. I sensed someone on the dock and looked up. A small figure was looking down at me with a tentative smile. "Hi, I'm your new crew. Brian sent me." She was about five-six, slender, with dark hair and a very direct gaze. Hardly anyone except Brian, who had been stolen from me by a wealthy Swedish yacht captain,...

A Fiance's Tale of Betrayal

by livealitle49 on Sep 14, 2017
Loving Wives

Author's note: Many thanks to my readers and those of you who have encouraged me to keep sharing my stories. I am especially grateful to those women who have contacted me and shared your own experiences. Collaborating with you on this and other stories has been educational, electric, and fun. I enjoy doing the final drafts with you and getting them published...

Simon and Kelly Ch. 01

by simonwindsor on Sep 14, 2017
Loving Wives

You reach a point in your life when you feel that you need to document some of the events which have shaped your relationship and family. I am at that point and I wondered whether I could tell you about my wife, Kelly. We are now both in our late 30s and 40s and have had the odd chat about whether we would try a more open relationship but it isn't for us. W...

Cuthbert Racing

by Egmont Grigor on Sep 14, 2017
Novels and Novellas

CHAPTER 1 This story is set in Sydney, Australia * * * It was stormy when late morning the young boarding school history teacher, Sophie Cuthbert, hurried under the lashing of wind and rain, shedding her hat and coat before entering the head mistress's office where she was given the expected news. Thirty minutes earlier the school board decided to fire...

A Female Sailing Instructor

by yknow on Aug 18, 2017
First Time

I've written a couple stories on here, and met quite a few people on-line. Some of the most interesting stories and conversations are about real life experiences. I have decided to tell about a few of my own. Of course the names are changed to protect the guilty, but the story is true about how I lost my virginity. I was raised as a good Catholic boy. I act...

Gay Sail Holiday

by Sean943 on Nov 4, 2019
Group Sex

My first time on an organised solo, gay sail holiday; I joined a large 65ft charter yacht berthed in a marina in Plymouth, for a two week holiday sailing to France and back via the Isles of Scilly. It was the first time that I had done this type of holiday, but I did have some offshore sailing experience. On arrival in Plymouth I met the skipper of the yac...