True Vacation Sex Stories

258,915 results
Orientation
Length
Source
Infinite Scroll

No, Not A Schreibtischtater

by steamer5139 on Sep 17, 2017
Mature

The two of us, her a middle-aged divorcee, me much younger, were coupled amidst muddled sheets, wrapped in murky shadows skulking about her bedroom in a tropical vacation bungalow near a white sand beach. Her ruby cum fuck me pumps unshackled, on the floor; my young man's practical, proper, in fashion shoes nearby. Her red lace panties, the crimson balconet...

Our Vacations In Greece Ch. 01

by newlatincpl on Sep 13, 2017
Loving Wives

This is a true story that happened to us while we had our vacation in Greece back on October 2009. Our names are Javier and Maria Yolanda; Mayo for short. We have been married for 6 years and have no kids. I am 36 years old, 5'10" and weight 192 lbs, my wife Mayo is 34 years old, 5'7" 135 lbs blonde, 34d 28 34, shaved smooth, she is a beautiful Colombian...

Chet's Two Special Ladies

by stoneypoint on Sep 14, 2017
Romance

Chet's family had been waiting for this opportunity for more then 13 months to go on an overdue vacation. Finally, in August of this year, Chet demanded time off, even though he had it coming, he couldn't get it due to one project after another. Sally, his assistant, was devoted to her work and Chet. Sally cared for her work and was completely dedicated to...

Maiden Voyage

by jessicaj64 on Sep 16, 2017
Transsexuals & Crossdressers

Note to the reader – this is not a work of fiction. It is the story of how one woman found herself, in spite of the odds, and in spite of being born with a male body. It is entirely autobiographical, sometimes painfully so. But having read many tales of transsexuals, which end up being, in most cases, little more than tales about the cross-dressing fetish, a...

The Outsider Ch. 22

by caligula97236 on Sep 15, 2017
Novels and Novellas

Chapter 22 -- Extra income When Mike went to work the following Monday, his mood had not improved from the way he had felt over the weekend. He was very angry about what had happened to Doña Lisette, partly because he was worried about the effect it might have on Ruthie and her temperament, and partly because of his concept of fairness. Ruthie was depressed...

Fantasies Cum True Ch. 01

by sex4u4647 on Sep 19, 2017
Group Sex

Fantasies Cum True Ch. 01: Sue "What's your most secret sexy desire?" Jan asked Sue. "What all would you do if anything you wished for sexually could come true. What's your biggest sex fantasy?" The six friends were sitting around the pool in Jan and Ron's back yard. Sue and Jim were next door neighbors. Ralph and Jan were co-workers at a halfway house, a...

Give and Take Ch. 02

by Lizzy_B on Sep 24, 2019
Sci-Fi & Fantasy

I kept busy for about a month grinding on closing the deal. The appointed day came and went without incident and then work dried up. I kept trying to find the next project but the work just wasn't there. I was chasing my tail and it was starting to wear on the people below me and the people above me. After a couple of weeks of that, one of the partners gave...

Blame It on Barbados

by jamboman on May 22, 2019
Loving Wives

I could hear the hair-dryer being used in the bathroom, so I knew that my wife, Stacey, didn't need any privacy. Nevertheless, I wanted to be courteous so I called through the closed door. "Honey, may I come in? I need to pee." The hair-dryer went silent for a moment as she answered "Yep", then it started up again. I opened the door and walked in. Stacey...

The Weekend in Tennessee

by UnomeasBob on Sep 16, 2017
Romance

As I alluded to in my first story, sharing my experiences on here is just as much for myself as for the reader. The average person would brag and tell their friends of their conquest, but due to the nature of my career I am unwilling to allow them to know the real me. Writing my stories and posting them where anyone could read them is a rush for me. Again I...

Mandie Becomes a Woman

by baby_cakes on Sep 12, 2017
First Time

She had never had sex before. She wanted to, however, very very much, but she did NOT want to give herself to the first guy who came along. At 21, Mandie was still quite innocent, although not as innocent as she led most of her family and friends to believe. She often fantasized about many different sexual scenarios while lying in bed at night, and this woul...