Cuckoldress Stories

117 results
Orientation
Length
Source
Infinite Scroll

Mentoring a Cuckoldress Pt. 01

by That_Guy71 on Mar 9, 2020
Loving Wives

I had enjoyed a fortunate youth and finished a career early in life. I was able to retire and "restart" a new life after a bitter divorce and a few other issues. I started taking college classes to get a different degree and that was how I met Carmen. We were close to the same age. She was married and taking classes so she could re-enter the work force with...

A Cuckold's Diary Ch. 35

by Paul Pines on Sep 19, 2017
Loving Wives

Chapter 35 - "I Love You, and I Know..." A Love Story in Two Acts February 2017 NOTE: This story involves cuckolding, infidelity, humiliation, heavy-duty submission, gratitude and LOVE. If you're not into all of these, or if you think they cannot exist together, you might want to click elsewhere. Or read on and perhaps learn something new. ***** OVERTUR...

Chance Encounter Ch. 30

by Miguel59 on Feb 12, 2019
Loving Wives

Only immediate family and a couple of close friends attended the wedding and reception. It wasn't meant to be so solemn, but it was also meant to send a message to Jean. She did wear white and Miguel wore a suit. From the smile on Jean's face you would never know she was being punished because she was too busy thinking about her wedding night. Jean's mom a...

Don't Stereotype Cuckolds

by eviltwin52 on Apr 27, 2020
Loving Wives

Let me start by saying that I am a cuckold and a happy one. It was my choice and I found a Woman that would lead me down the path to unbridled satisfaction. Unfortunately too many Lit readers either disregard our lifestyle altogether or deride those of us who are strong enough to give our Women what they want and thereby meeting our own needs. But what are...

Creampie Lover Ch. 03

by jealouscuck on Sep 26, 2017
Fetish

In the previous chapter I finally got a fresh creampie from my wife, Cynthia. I had encouraged her to seduce a nice looking man from South America. This was a watershed moment for it gave Cynthia a chance to experience a big cock and gave me a chance to eat another man's cum from her pussy. The following morning, I asked her if she had any regrets. She sai...

Heidi's Ideal Marriage

by BrianinSuffolk on Sep 13, 2017
Loving Wives

I first met my wife whilst I was on a break in Durban, South Africa five years ago. I was based in Lusaka in the final year of a four year assignment in Zambia and I needed a week or two in a somewhat normal country and found a small but elegant beachside guest house on the internet and booked in for a week. The owner promised to send her daughter to meet me...

Sarah's Journey Pt. 04

by georgekaplan on Oct 30, 2018
Fetish

Note: This contains an element of oral sex on a woman during her period. Pass this story by if it offends you. ***** For the next two weeks Sarah was tattooed nearly every day, Wei Jinn inked both her upper arms, thighs and her breasts, with vines and flowers. There were skulls, and a clock interspersed too. Sarah began to crave the drugs she was given an...

From Cheating Wife to Cuckoldress

by FrostShard on Oct 30, 2018
Fetish

"Don't be silly, my dear," my wife Shrutika said to me as she pulled up her full-fashioned black stockings and attached them to her garter belt. "It's just a simple work dinner. I.. just want to look good is all." I gaped at her openly. "But honey," I said, "You haven't worn stockings in over a year! Not since Valentine's Day last year." Shrutika seemed di...

St. Paddy's Day Party

by cuck2serveU on Sep 2, 2017
Fetish

Being a true Irishman I always enjoyed St. Paddy's Day. I grew up on corned beef, boiled potatoes and the Irish Rovers singing the Unicorn song. I never did do my part of being the beer drinker though. Once I got involved with the cuckold group the holiday just was not the same. This year's event would be no different. It always takes a great deal of mental...

Redundant Cock and Pussy Takeover

by realvelvetglove on Oct 6, 2020
BDSM

1. Steve's Story: I was made redundant a couple of years ago when I was 51. The large company I'd spent the previous three decades working for had been taken over and, as usual, layers of management got stripped out during the restructuring process. Fortunately I got a modest lump sum payoff and my pension will kick in when I'm 55. I'm also lucky enough to...