Cuckold Gloryhole Stories

7,501 results
Orientation
Length
Source
Infinite Scroll

I Dare You Ch. 3

by Digger66 on Sep 12, 2017
Exhibitionist & Voyeur

The following is intended for ADULTS ONLY. If you are under 18 or are offended by stories of a sexual nature, STOP NOW. This story takes place in a FANTASY world with no AIDS or STDs. In the REAL world AIDS and STDs can kill you. Protect yourself!!!! ***************************************** Several months had past. Work started picking up for Kay and me....

First Pt. 02 of 03

by sex4every1 on Jan 22, 2019
First Time

Thanks to Iris_Untangled for editing. You're amazing! ***** That Friday night, Amber picked me up at my place. As soon as I laid eyes on her, I was a goner; my cock was an iron bar before I had even said hello. She wore a short, black dress, sleeveless with a sultry open back, and black suede lace-up heels. My god, she looked hot! Although she was a bit e...

Neighborly Gloryhole

by tabber on Sep 25, 2017
Group Sex

Dave's wife Sue was going to be out of town for the weekend, so he invited several of his buddies over for poker night. They had played for about two hours, and downed half of a keg of beer when Dave mentioned that instead of smoking cigars after the game, he had an alternative activity. Everyone was curious and when he told them the plan, they all agreed t...

Pavlov's Bell - Round 01

by DirtyyDom on Apr 3, 2018
Loving Wives

If my friends want a bite, they can have it. Am I overly generous? I don't love this slut. Let her cut a gloryhole into the bedroom wall. Every time I walk down the hall I'll see a dick-less man glued to that sad layer of sheetrock. Addiction says, "this is exactly what your body needs right now" as an addict wraps an elastic band around their bicep, scrumm...

The Wish

by Fangslover on Jan 16, 2019
Fetish

—This is my first public story, my plotlines are usually quite lacking... I tend to get straight to the point of this kind of writing, which is erotica. I know it’s probably not the best, but I hope someone else may find it enjoyable. All characters in this story are fictitious and are at least 18 years of age.— “I wish I would be seduced, bitten, and turned...

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Sissy Whore Ch. 04

by DebbieDublin on Mar 14, 2018
Transsexuals & Crossdressers

I stumbled to the bathroom to fix my face, my head still spinning. I reapplied my lipstick and dusted off my foundation. Wiped away the mascara stains from my cheeks and reapplied. When I was done I returned to the living room. 'These are for you.' He said when I approached. He reached into his jacket, extracted a pair of large gold coloured hoop earrings...

Gloryhole Sex Toy Fun

by winterknights on Sep 12, 2017
Exhibitionist & Voyeur

I'm a young 23 year old and as you can imagine I do tend to get excruciatingly horny pretty much on a daily basis. I'm currently single to so it drives me insane, having to sneak off for a secret wank while in work, while watching TV, riding on the the bus. Well not really on the bus, it's not that bad yet. OK, OK I did do it on a bus once when I was younger...

Bukkake Box of Infinite Glory

by fastandsloppy on Sep 12, 2017
Group Sex

It was weird. I used to hate those women who were always checking themselves in the mirror; inspecting their hair; reviewing their make-up; examining their curves and cleavage. Get the fuck over yourself, I'd think. But on the day after we got back from vacation I found myself doing the exactly same thing. Well, not exactly the same thing. I was worse. I had...

Captain's Choices

by CaptainX on Dec 22, 2020
Cheating Spouses

Chapter 1 - The Beginning Your name is Captain, well that is what you prefer to be called, and this is your story, your life has been a crazy rollercoaster living a double life and most people on the surface think, You're just this normal guy who doesn't know much but if only they knew how wrong they really were. After having a fallout with your ex, You nev...

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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...