Wives First Time Gloryhole Stories

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The Pump House

by AlinaX on May 11, 2020
Fetish

Inspired by an idea by enigma3 in the Forum. * They say size doesn't matter, but when you are - whether by length or girth - within the smallest five percent of the population, it's difficult not to feel self-conscious about it. It's difficult to talk to women without imagining their horror, their amusement, their mockery, their contempt. Easier to avoid r...

The Mistaken Gloryhole Ch. 01

by DickThePimp on Aug 12, 2019
Celebrities & Fan Fiction

My wife Kim Kardashian and I are coming back home from a short trip to Vegas. We're driving back in my pimped out Escalade, green and gold... pimp colors baby. My cousin Spence (The King Of Queens) is in the back seat. He came along, but lost all of his money in the casino. He's pretty bummed out about it. He's been downing Redbulls the whole way back. Don't...

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 Porn Theater

by pondcat on Oct 15, 2017
Exhibitionist & Voyeur

I was traveling to a new city for work and looking at the sex listings to find if there was any decent gloryhole action. It's getting harder to find a good ABS anymore. But not in this town. This town was full of options. The most curious option of all was what was described as a genuine old-school porno theater. A floor full of seats, sofas, even a few bed...

Sorority Gangbang Sisters

by HeyAll on Sep 25, 2017
Group Sex

Part 1 of 4: The Pledge Emily stood nervously. She was the youngest person in the room full of people. A fresh faced 18-year old who was new to the college system. Her hair was tied in a ponytail. Her thick framed glasses made her look like a nerd. But she tried to be unafraid. She tried to be strong and brave. "Why should we allow you to pledge?" Morgan...

Payback's a Bitch

by sissymaidallyson on Sep 13, 2017
Transsexuals & Crossdressers

Knelt on my knees and taking a glance to my right at the sight of a woman counting cash whilst I sucked off a guy I started to wonder how this had all happened. I had a good job and didn't have a huge problem with getting lovers. I was straight and loved women but here I was – nothing but a sissy prostitute being rented out for the oral pleasure of men I di...

Hedonism Island: A Gloryhole Heaven

by silkstockingslover on Jul 13, 2020
Illustrated

sent by online file sharingSUMMARY: NOTE: Thanks to the amazing Alison Hale for adapting my original story and creating the images that follow. This has been an amazing experience to collaborate on such a story. A fantasy many women like me have dep inside us. NOTE 2: This is the second part to a potentially lengthy series of one woman's (and to a lesser e...

Late Night at the Campgrounds

by AnthonyBlackLit on Apr 14, 2020
Mature

Uncomfortable. Again. Drew Collins had been tossing and turning in his overpriced sleeping bag for what felt like the better part of the whole night. He groans. Another uncomfortable night sleeping in a tent on the hard ground. Drew was on one of his yearly family friends camping trips. The sort of trips people take with old family friends. Drew slips on hi...

The Rental House

by PorscheKaru on Sep 15, 2017
Transsexuals & Crossdressers

I own a rental house in a city nearby. Actually its about an hour and a half away and it just became vacant. I needed to go down and inspect and clean it and fix anything needed fixing so I could rent it out again. Being so far away I planned to stay there while working on it so I brought an air mattress, blankets, pillow, and clothes. I also brought a duffl...

Beth Gets a BBC at the Gloryhole

by bethslover on Dec 9, 2019
Group Sex

[Comment: Beth is my girlfriend! We have a lot of kinky fantasies, but recognize that many of them are unrealistic/impractical for carrying out in real life. To cope, we've decided to write them out together. This story was based on two requests by literotica readers left on my previous story, 'Beth Gets Seduced by Gym-Bros'. You don't have to have read that...