Gloryhole Wife Stories

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Orientation
Length
Source
Infinite Scroll

Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

Mike, Pam, Pete and the Favor Ch. 02

by StackedAction on Sep 25, 2017
Group Sex

Part Four Pam showered and was drying her hair with the hotel provided blow dryer while Mike took a quick shower. As Mike exited the bathroom in his towel, he looked at Pam in the mirror. "Lose the bra, you won't need it where we're going." Mike got dressed quickly, as it seems all men can, and was sitting on the bed, texting on his phone while Pam did he...

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...

The Gloryhole

by wizard666 on Sep 13, 2017
BDSM

Brad and Janet had been together for many years and although they had an open relationship, they had never been to a party like this one before. As they drove to the house, Janet was trembling in nervous anticipation. She had never done anything this adventurous before, but despite her fear she could still feel the excitement building! Janet had worn a slink...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

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After School Ch. 02

by Faye_Skylark on Sep 25, 2017
Erotic Couplings

Crystal McLaren stood anxiously in the cramped backroom office of the local adult book shop. She could never quite work out why they were called book shops, since they she didn't see many books in the store. Instead it was mostly filled with adult DVDs, toys, outfits and miscellaneous products. Crystal was eighteen years old and a student in her final year...

First Time for Everything

by qazwaz on Sep 12, 2017
First Time

My wanting cock throbbed around my hand as I glanced down at my illuminating phone in my dark car. "Just got here" I replied, before switching internet tabs to the previously-loaded video of a blonde girl in a gloryhole. I had a long drive that day, about 3 hours to my hometown destination. Having broken up with my girlfriend a few weeks back and not having...

The Thrill is Gone

by John Connors on Oct 6, 2020
Celebrities & Fan Fiction

Disclaimer: This story is a work of fantasy, fiction, parody and satire. As such, no offence is meant to anyone who is mentioned within it as they would never act this way in real life. This is just a fictional erotic fantasy story to be read by those over 18 years of age. All characters mentioned within this text are 18 years of age or older and are theref...

Date Night with My Wife Pt. 03

by amadbaker on Aug 31, 2017
Group Sex

As we were leaving the bookstore Shawn and I were walking out together because Debbie stopped to talk to the clerk. Shawn was saying how tired he was and was thinking about heading home. After some arm twisting by me and of course another look at Debbie's fine ass in her leather skirt he was persuaded to come to our house with us. As Debbie joined us she sai...

One Gloryhole Outside Breeding, Kentucky

by targetthyself on Nov 24, 2018
Miscellaneous

Somewhere, in the cosmos, lies the truth of our existence. It's siren song drives us forward, forward into the unknowable reaches of space, and time. Hoping to boldly discover their secrets. What is it about the unknown that drives us so? What is the appeal of knowing? Is it the value of the knowledge we will gain? Is it the thrill of the risk we take? Or is...

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