Literotica Holiday Experience Stories

352,670 results
Orientation
Length
Source
Infinite Scroll

How To Write a Holiday Contest Story Entry

by sack on Sep 16, 2017
How To

Note: With 2 weeks left to submit stories to Literotica's 2004 Winter Holiday Story Contest, there is still plenty of time to create your own precious masterpiece. As for myself, I've never won a holiday contest; some of my other stories have done very well, others have been perceived as quite mediocre. I figure I've made every mistake twice, so am trying to...

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...

My Wife Is Satisfied Now - And So Am I!

by ARGEE on Sep 17, 2017
Loving Wives

My youngest daughter had just turned 18 and I was quite surprised to see just how much she had developed over the last year. She had been a rather quiet girl, very pretty but never comfortable letting people see just how pretty she was. Until she was 17 she had no figure at all. She had skinny legs which seemed to be shapeless and her breasts just weren't th...

Fair Exchange Is No Robbery

by werebare on Aug 19, 2017
Exhibitionist & Voyeur

We'd come out in Pete's car, since he knew the way; and for the trip back, the girls had insisted that I should join them in the back seat – sitting in between them, of course. You might say that Pete wasn't exactly delirious at being left out! However, he admitted that he probably wouldn't be able to concentrate on his driving all that well if one of our...

A Gift for Her...

by stag4life74 on Dec 25, 2019
Exhibitionist & Voyeur

It was the holiday season, and work had been crazy, as has the shopping, but now it's all over as Jen arrives at home, on her first day of the holiday break. She'd spent the day shopping, baking and preparing every little last thing for Christmas. She was so excited to spend time with her loved ones, and that special new guy in her life, who just happens to...

Blackmailed Pretty Wife

by Winterfrog on Sep 17, 2017
Loving Wives

I was sitting in my office in a small Scandinavian town and it was a nice lazy sunny Thursday morning at the end of June. Like everybody else, I was looking forward to a four week summer holiday, which began at noon on Friday. Then I got the mail and shit hit the fan. No business mail today and the only mail was an anonymous letter, which read: "Dear friend...

Please, Don't Call Me Renie

by beesol on Sep 13, 2017
Fetish

Oscar felt that his wife Irene should experience a full orgasmic experience, even if it meant with another man. I "How was it, darling?" asked Oscar as he dismounted from his wife, Irene, having just had a wonderful orgasm. "It was lovely. It's always a lovely experience for me. Why do you always ask me? "Because you just don't seem to get as much out o...

1972

by lookingback on Sep 17, 2017
Loving Wives

all myself "lookingback" because these days that is mostly what I do and, luckily, there is no shortage of memories. Most, but not all, are happy; most, but not all, are repeatable and here is the first (and possibly the last, depending on the response) which I have named after the year in which it happened. Names have been changed of course but not much els...

The Holiday Ch. 01

by Kellylifestory on Sep 16, 2017
Mature

Part One - The Old lady When I was 18, me and some female friends went to Cyprus for a holiday. The holiday for me completely changed me. Before the holiday I was very sexual and started to experiment, but there were about 6 events on this holiday that completely changed me sexually. The first one happened because on the second day while walking up to the r...

Lost Luggage

by Tomsparty on Sep 18, 2017
Transsexuals & Crossdressers

As usual my mum took great delight in telling my new girlfriend the lost luggage story. I took Clare to her house for Sunday lunch and told mum specifically not to embarrass me with any of my childhood stories or old photographs. She was on her best behaviour during the meal but afterwards as we sat down in the lounge for coffee she was true to form. She qui...