Cuckold Vacation Stories

28,460 results
Orientation
Length
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Infinite Scroll

Susan's Day in the Sun

by ctdans on Dec 2, 2019
Loving Wives

Not a BTB Not exactly a cuck story yet some will disagree Does he keep her? Yes Did I have a proofreader? Yes Are their mistakes? Yes ***** My wife Susan and I, David Jackson, were on a vacation in the U.S. Virgin Islands. Once a year we liked to get away from New England and would travel someplace warm. Sometimes it's a cruise and other times we just...

Dear, We Have to Talk Ch. 03

by dr13bone on Sep 25, 2017
Interracial Love

The Dance My wife had gone on my computer and had found my stash of cuckold porn, now she was exploring the fantasy with me, but how far would it go. I worried would it break us up like what had happened to her girlfriend Karen, or would it make our relationship stronger? I bought the tickets for the dance half not believing my wife would go through with...

Letter from Providence

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- I love your letters, but noticed you had nothing from our humble Rhode Island. During corner time after a painful discipline session, I turned my phone's recorder on. I love my stepdaughter, and wouldn't embarrass her, but she is so wild she doesn't care, and of course she is of age. This is for your "Taped Confessions" Eugene Scobrinks...

Cynthia's Joy

by sinisterout on Sep 13, 2017
Transsexuals & Crossdressers

Many thanks to CKQuail for editorial input and proofreading. ***** In the beginning I knew her by her screen name, Goddess4u2serve. Later I learned her name was Cynthia, but I usually called her 'My Goddess'. She knew I was a cuckold before we'd even met. She'd read the stories I'd posted here on Literotica where I explored my dark fantasies. I can't e...

Jamaican Holiday Ch. 14

by jayewatcher on Sep 19, 2017
Interracial Love

Aftermath This brings us up to Dec 2010 and our most significant event - and introduces Robert, our Bull and future Master Dec 2010 -- It's been 6 years since that vacation to Jamaica. When we got back we intended to return to our normal Vanilla existence. But we couldn't -- too much had happened. As Jaye put it, the door had been opened to something dee...

Need For Revenge Ch. 01

by DG Hear on Sep 12, 2017
Loving Wives

Thank you to Estragon for editing my story. I had to go with multiple chapters because of the length. Hope you stay around for the entire story. It could go in a number of categories. I will do my best to submit a chapter a day. Chapter 1 Sometimes you never really know how you're going to react until the situation actually happens. I always read where ev...

Edge of No Control

by the_harmless on Aug 13, 2019
Loving Wives

[We're coming to the sad and weepy part of the story soon, my little brothers, where your humble narrator gets to feel some of the pain for a change. I'm sure that's only fair given how much he is usually dishing out. This is the point where it began to become apparent (and it definitely gets worse in later chapters) that this couldn't be sustained.. Anyway,...

Courtesan Ch. 42

by Goodhusband on Sep 19, 2017
Loving Wives

This is the forty-second episode in a series entitled "Courtesan". If you have not read the previous forty-one episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alterna...

Companion Fare Ch. 07

by evals22 on Sep 17, 2017
Loving Wives

The room became suddenly silent. I had sat and listened to my wife's description of her exploits these past five days. When I looked at her I saw her hand was playing with her clit, her nipples were erect and she was sitting with thighs splayed. I tried to control my anger as I spoke. "Lori, listen very carefully. I want you to leave. Now," she looked up wi...

Death Do Us Part

by CrustyBumhole97 on Jun 13, 2017
Cheating Spouses

Sometimes you never really know how you're going to react until the situation actually happens. I always read where everyone seems to have the answers but yet they are on opposite sides of the subject. I grew up in a broken home. Mom and Dad argued all the time and one day Dad walked out on us. I was nine at the time and I really didn't understand it all. I...

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