Gaping Hole Stories

122,731 results
Orientation
Length
Source
Infinite Scroll

Hedonist Ch. 06

by Abelard7 on Sep 17, 2017
Loving Wives

I did not have to wait long to pay my debt to Alex. He had a friend who owned a small art gallery, we were invited to the opening of an exhibition of; 'Primitive African Art.' This was a private collection of artefacts from a small country in West Africa. A former French colony. Much of it was highly erotic. I was examining a display of carved ebony phalli....

Ruined?

by veryopenmind on Sep 13, 2017
Interracial Love

Damn! It was ruined! Would it ever be the same??? Red, swollen, stretched and gaping open. But wow was it HOT! I obeyed her as she said lick it clean but go easy I'm sore. On my knees I bathed her used pussy with my tongue. Sucking the 2 big loads of come out of her loose hole. So let me tell you how her once little pussy got this beat up. With my permissio...

My First Anal Lesson

by Ginger_Sparkle on Jun 5, 2019
Anal

You demand I take my clothes off. You kiss me as you pull my shirt over my head. You lead me over to a chair & have me kneel down on it backwards. You secure my wrists to the back of the chair. You take the lube & drizzle a thin stream down the crack of my ass. With a sharp crack you smack one of my ass cheeks. I moan as you rub the red mark your hand left....

The Making of an Angel Pt. 06

by AngelLawrence on Sep 24, 2019
Transgender & Crossdressers

The wait for Wednesday dragged... I'd gone clothes shopping and had decided on a red silk blouse with an above the knee pencil skirt with my black patent shoes and barely black stockings. I'd decided to go with my bob wig and full 90s style make up. I was looking forwards to seeing the final look and to tasting Zoe's delicious cock! I headed over to Zoe's...

This Is My Ass Now Ch. 02

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

It had been about a week since the WWE diva simply known as Paige had lost her anal cherry to AJ Lee and Paige swore it was only now she was back to her usual self. After a long night of anal pounding her back hole had felt like it would never stop gaping, and while it had looked completely closed by lunchtime Paige swore she felt loose back there for the re...

Jessica Trailer Park Whore

by JessicaTV on Sep 15, 2017
Transsexuals & Crossdressers

It was a late spring evening when Jessica and Phil sat down at the table for their evening meal. It had been a cold but busy winter and the weather was now improving rapidly as the nights grew longer. They sat discussing what Jessica would be doing later that night and also tomorrow night. This was when Phil told Jessica that from now on Saturday nights unt...

A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...

Stretching Pt. 04

by ggerard87 on Sep 19, 2017
Fetish

Circa 2004 There was a perfect storm brewing, and my little Amy was undergoing a transformation. While Amy was spending hours stuffing herself with the big dildo or both, I would now only watch big dildo porn. The more I watched girls stretching themselves with huge dildos, the more I became obsessed with it, and the more I liked doing it to Amy, or watchin...

Wide Open: An Examination

by francypants on Sep 19, 2017
Anal

I was waiting for the doctor to come in, looking at my legs on the table. My stomach was churning, as I wasn't sure what was going to happen. I had been having stomach problems lately and finally broke down to get it checked out. I had to get a new doctor because I switched HMOs and the old one wasn't on my new plan. The new doctor, Dr. Giovanni, was a nice...

Lots of Sex Lots of Ways Ch. 01

by Penisleeve2020 on Apr 15, 2020
Fetish

Lots of sex, Lots of ways Bec loves LOTS of sex in LOTS of ways, we both do. We worked remote a long way from the entertainments of a city and population centre so we decided to have a break and got a great deal on a suite, top floor, executive lounge middle of the city, on the strip! Woo Hoo. We drove there, about 6 hours normally but we took eight and we...