Cuckold Holiday Stories

23,534 results
Orientation
Length
Source
Infinite Scroll

Roman Holiday Ch. 08

by Miguel59 on Sep 19, 2017
Loving Wives

Richard woke up before I did. He grabbed his clothes, dressed, and headed out the door, but not before kissing me. "Call me." he said. "At work or home?" "Either one." "I don't have your home phone." "I'll write it down for you. And Jeanette I had a wonderful time last night. Thank you." "Richard, I should be the one thanking you. That was the best se...

My Wife and the Older Man Pt. 03

by Krista16 on Dec 2, 2019
Loving Wives

6 Years Later... Lucy and I were still happily married in the same family home in Cardiff. 9 Months from the holiday, Lucy gave birth to a beautiful baby girl which we named Penelope. She was now 26 weeks pregnant with our second child. Lucy obviously did not accept Carl's offer of employment and continued to build her career in the school. She made it as...

The Spirit of Lady Macbeth Pt. 07

by alyssawinters on Oct 19, 2020
Transgender & Crossdressers

The campus still empty for holiday Tracy his backpack replaced with a catch-all purse walked across the quad gripping the strap looking to kill some time reading before returning to home and Mistress Lisbeth. Spotting the couch in the near empty coffee house he planted down in the middle of it ready to open his book of Shakespeare's 'the Tempest'. Nervous...

Dark Rescue Ch. 03

by TheKeith on Feb 6, 2018
Loving Wives

Despite all the sex and sex talk, you can't build a loving relationship on screaming, orgasming sex alone. So I cooked for Shayla. Retrieved her single, pitiful suitcase from storage and washed everything in it for her. She slept in our bed, made up daily by her... made up several times, as we screwed on it as often as possible. I took her shopping for repla...

Contributions

by Nils Huim on Jul 18, 2018
Sci-Fi & Fantasy

45 minutes after masturbating into the special receptacle condom (reputedly lamb's skin) I was still sitting in a chilly waiting area with about a dozen other men. Nobody looked at one another or said anything. Everyone wore the same dour expression as they played with their phones. Finally my name was called and I was led down the hall again to another, ev...

Once Upon a Time Pt. 02

by B_Bailey on Sep 14, 2017
Non-Erotic

Some of my readers have asked for a follow-up of the original Once Upon a Time... So here is my attempt at just that. Fill in the blanks for some of the unanswered questions. Thanks for voting and your input on these stories. B_Bailey ***** Chapter One Recap As mentioned in the first story of what had happened to me one night that when I awoke the next m...

Counselling Changed Our Marriage Ch. 02

by Quietoldie on Dec 1, 2017
Transsexuals & Crossdressers

I am grateful to another member of Literotica for the story line and about half the content of this story. I have thoroughly enjoyed the collaboration and have found working with a woman has informed my own writing. Chapter 3 will follow shortly. ***** Third Joint Interview Emily and I arrive at their marriage counselling session a bit earlier than their...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Cuckold Chronicles 15; Sam Pt 4

by deltonaman2man on Sep 15, 2017
Loving Wives

Cuckold Chronicles 15: Sam PT 4 Heather & the bird get stuffed from both ends The month of November seemed to fly by. Before I realized it, it was Thanksgiving week. Heather was only going to be working 2 ½ days this week. She would be off starting around noon on Wednesday. I was getting into holiday mode when I remembered that Heather's birthday was the d...

The Road to Ruin

by Spoox on Apr 14, 2020
Cheating Spouses

This story is written in 1st person. So if you add a chapter please be sure to state which character you're using like I have. Deena's Story Before I was an escort, I never had anal. Now it's my bread winner. I never had a potty mouth either. I used to be a classy girl from a conservative British Asian family. The world of sex was something only shared betwe...

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