Cuckold Gloryhole Story Stories

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A Cuckold's Tale

by CastleDJK on Sep 14, 2017
BDSM

Based on Chaucer's Canterbury Tales Prologue Three Mistresses are lounging around the pool, chatting and laughing, while their three sissy maids stand by to attend to them. Big breasted in a white string bikini, redhead Mistress Reeve is enjoying a foot massage from one of the sissies at the side of the pool. Lady Night, raven-haired with an alabaster whit...

Plaything Pt. 03

by niggaplz101 on Apr 24, 2018
Mature

Editor's note: this story contains scenes of incest or incest content. *** PT 3: Priya's Public Fucking what up fam, here's part 3 of plaything. It didn't take two years this time and I'm def more focused on where im taking it. This story was actually an idea i got from a forum. On another note, if you didn't like my two previous chapters, I respect your...

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...

Eat the Seed

by Digger66 on Sep 25, 2017
Erotic Couplings

My wife and I visit a porn store with another couple. We watch video called "Eat the Seed". This leads to an interesting encounter at a gloryhole. My wife, Jill, and I have known Carl & Emma for years. We have gone camping together. Once, the four of us went to a beach resort in Puerto Rico for a vacation. Jill and I have been married for a little over...

The Locksmith

by cdbrittany4bbc on Jul 18, 2018
Transsexuals & Crossdressers

I wish to thank thewinedarksea for editing this beast. Summary: Fantasy night goes awry. Let me start off by saying my wife Amy and I have been married eight years now. I must admit our love life has been waning, and sex — when and if we have it — is plain vanilla. Our anniversary weekend was coming up. I told her we needed to do something to reignite our...

Gloryhole Addiction Ch. 02

by Brittni4u on Dec 19, 2018
Fetish

It has been a several years since my dirty yet amazing gloryhole experience. At that time, I was 18 years old and still in high school. It was supposed to be a sneaky one time experimentation which turned into a nine month long, multi-visit, wonderful cock sucking experience that has never left my memory. I have always had an oral fixation when it comes to...

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...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Gloryhole Event

by carriekitty on Apr 22, 2025

Well i decided to try something new for a change, I spoke to Kerry (friend from previous stories) and she told me that there was a greedy girl event going on this Friday night, Carl was out with his friends and I had nothing planned, so I thought I'd go down and see what's going on. So Friday soon came and I got freshened up, put on some smart casual clothin...

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Celebrity Gloryhole Confessions Ch. 01

by DickThePimp on Aug 21, 2018
Celebrities & Fan Fiction

This is a parody... It is not real This is a new series about celebrities at gloryholes... It stars Kim Kardashian... Enjoy Kim Kardashian stood in a bathroom stall. She wore a skin tight, low cut, cream colored dress and cream colored stripper pumps. She's the host of my new series about celebrities at gloryholes. She's the perfect host and the perfect wo...