Cuckold Island Stories

24,566 results
Orientation
Length
Source
Infinite Scroll

Atlantic City Ch. 01

by ggkcmw4m on Sep 14, 2017
Loving Wives

George and Kat had been married for 17 years. Last year, she had survived breast cancer and the physical scars — if not the mental ones — were beginning to fade. This was to be their "celebration" weekend. Alone. Away. In Atlantic City. They left Long Island a little after dinner so they wouldn't have to drive through New York City during rush hour. They c...

Taming Edy Ch. 01

by eroswizard on Sep 13, 2017
Group Sex

Being recently separated from my Wife of twenty years was rough on me. After we had parted, I set her up with a friend of mine. Knowing she was in the arms of another man eased my burden for needing to continue to look after her. I myself needed time by myself. For the first time in my life, I did not look at every pretty girl with thoughts of bedding her. T...

The Island Ch. 02

by TheCandyManCan13 on Jun 12, 2019
Transgender & Crossdressers

I had just been fucked by a tall, big-titted, older Danish woman named Runa with her 10 inch dick after meeting her the same day. I had never had such an experience before and it had been amazing. I lay in her arms, my head resting on her tits, looking down at the cock that had given me multiple orgasms before filling me with a massive load of delicious cu...

Locked Out on My Honeymoon

by SevMax2 on Jul 14, 2020
Interracial Love

So, there I was, on my fucking honeymoon, locked out of the main bedroom in the grand suite, because my new bride got drunk and took some guys back with her to fuck her there. The guys didn't like that I was present and felt deceived or betrayed or whatever that she was married, so they took it out on me and locked me out of the main room in the suite until...

Vacation Awakening Pt. 02

by tyler990 on Jul 6, 2020
Loving Wives

Rebecca hadn't been herself lately. She was smiling less and from time to time I heard her weeping for seemingly no reason at all. She wouldn't tell me what was wrong. She kept saying I couldn't understand. Even our Saturday night arrangements were affected. When the group of black men came over to ravage her violently, she usually let them have their way...

Wife, Her Cousin, and Old Boyfriend

by combook on Sep 16, 2017
Loving Wives

Three years ago, I'd encouraged my wife Marilyn, then 25, to date others. Although reluctant at first, she relented after a few months. I have no interest in seeing other women. I guess you could call me a watcher. My wife says, with a gracious laugh, that I'm a "cuckold." I'm just four and a half inches erect, and I wanted her to experience "real" cocks....

Black Cuckolding in New Orleans

by Samuelx on Mar 14, 2018
Interracial Love

Lana Franks is a mean bitch, ladies and gentlemen. Not to sound crude or loutish, but there is seriously no other way to describe this lady. At first glance, the five-foot-ten, curvy young Black woman with the deep chocolate skin and thick Afro looks quite lovely, pleasant and nice. She's attractive, but in a nonthreatening way, like those women at your loca...

Cuckold

by CuckoldGuy on Sep 12, 2017
Reviews & Essays

The true stories that I've posted here on Literotica.com about my cuckolding have generated many emails to me. Some hateful and some asking me to coach or mentor them but most with questions or comments so I thought I would post some of them here. Anyone seeking advise from me, I make it clear that I'm not a psychiatrist or psychologist. I'm an engineer but...

Male Chastity Device

by CuckoldGuy on Sep 12, 2017
Toys & Masturbation

Janice and Mike (not their real names) are a married couple in their mid forties. Married about twenty years. About ten years ago they started playing with a male chastity device and discovered they were having a lot of fun with it. They have been using it ever since. The device is a stainless steel or plastic tube about three and a half inches long and abo...

Slut Wife - Wild Weekend First Night

by policywank on Sep 12, 2017
Loving Wives

Before proceeding please read the title, story tags and my profile to determine if the subject matter is to your liking. .......................................................... It was later afternoon on a Thursday. Heather and Bill had just flown into Chicago for their weekend with Roxanne and Peter - an experienced slut wife and cuckold. Roxanne, Hea...