Lost Bet Cuckold Stories

185,194 results
Orientation
Length
Source
Infinite Scroll

A Woman's Story

by CuckoldGuy on Sep 14, 2017
Fetish

Based on a true story * "Wow! You drain me. Between your mouth and that big guy between your legs, my pussy is so sore. I think I'm going to call you, 'Bruce the Bull'. Wow!" Bruce: "Oh, I bet you tell all the guys that." "Just the well endowed guys like you." Bruce: "Have you had many experiences? Oh, maybe that's not a proper question?" "Oh, that's o...

Am I Ready to be a Cuckold?

by cheekybrit on Sep 12, 2017
Fetish

WARNING: This is a cuckold story involving a loving husband and wife. If you dislike cuckold stories, find them insulting, threatening or vile then DO NOT READ THIS STORY. I understand it is not for everyone. Please do not post comments regarding your opinions of the genre. If you leave a comment expressing your hatred of cuckolding then I will assume you ar...

My Ex Sister-in-Law's Cuckold

by Naf_Noparts on Sep 19, 2017
Toys & Masturbation

(Author's Note: This story contains a cuckold-theme and a man eating his own cum. If this element does not appeal to you, neither will this story. Love to receive feedback. Thanks for reading!) * I was house-sitting for my former sister-in-law, who went on a two week vacation with her sister Stacy (my ex-wife) and some friends. Kelly and I had always been...

On a Beautiful Summer Day Ch. 02

by CuckyJimmy on Sep 16, 2017
Fetish

As you may remember, I divulged my secret cuckold desires to my neighbor after an coincidental meeting on a nearby walking trail. During subsequent "work outs" as we called them, he saw more and more of my wife's treasures. I have not only accepted that he never made good on his gentleman's promise to share glamour photos of his wife, but somehow grew accust...

Pie - I Just Love Them

by DiggerDave on Sep 11, 2017
Fetish

This is a story of my own private relationship with my wife and the start of my journey into becoming a cuckold. This story contains graphic description of cream pies and how I enjoy cleaning them up. If a story regarding adultery and cream pie eating is not for you then please move on and find a story to read more to your particular liking. I just love...

Circle of Cuckolds Pt. 04: Conclusion

by senorlongo on Oct 26, 2020
Loving Wives

I find most cuckold stories tedious and repetitious. After all, how many different themes can there be on "I wanted my wife to cuckold me?" But, occasionally there's one that shows originality, depth of character development, and is well written. All of those traits were exhibited in "Circle of Cuckolds," written and posted here in January of 2006. The endin...

This Cock Tastes Like My Wife

by Turned on Sep 13, 2017
Loving Wives

Because the following story is so long, it will be submitted in multiple chapters. This story is a cuckold story. If you do not like those stories or all of the "faggy" things they entail, do yourself the favor and stop reading now. You have a fair warning. Any negative comments about the subject matter will be ignored and deleted. You were already told wha...

Hidden Porn, Converts My Life Ch. 01

by rocket32 on Sep 14, 2017
Fetish

Last month my wife, Becky and I were taking a much-needed long weekend away with a long dive to a beach resort. I drove and my wife reclined in the passenger seat with her very sexy feet on the dashboard. Knowing that we would be driving for several hours, she was as comfortable as possible and wore very little which drove me crazy from the start. This is no...

Paula: An Unfaithful Wife? Ch. 02

by OpenMouth on Sep 16, 2017
Interracial Love

*Many thanks to MelnMe for allowing me the opportunity to write a follow-on to their story. Be sure to check out their work! Also thanks to the authors of some wonderful cuckold stories, that provided the inspiration to write on this fascinating subject... ____________________ As I turn the corner into our street, I see Paula, framed in the light of the be...

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...