First Time Gloryhole Stories

351,036 results
Orientation
Length
Source
Infinite Scroll

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...

Sex Funhouse

by DickThePimp on Dec 11, 2018
Celebrities & Fan Fiction

This is a perverted funhouse fuck parody... It ain't real "This is great babe... It looks like so much fun." "Yeah babe... it's wild... It makes me horny." I was in the control room to my newest perverted idea... a Sex Funhouse. I built it in my backyard. It's two floors of perverted sex fun. There are different rooms and fun places to get off sexually......

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...

Freak Daddy

by DickThePimp on Jul 6, 2020
Celebrities & Fan Fiction

Keeping it simple... And freaky... Parody... Offensive, but fun... For perverted entertainment purposes only... It's fuck time, bitches... You ever freak a bitch while your sweet mama makes you breakfast? I did just now. My girl Rosario Dawson strolled her fine Puerto Rican ass into the kitchen all nude and shit... Except for her gold and diamonds FREAK ch...

Adult Shop

by LucyFrance11 on May 7, 2019
Transgender & Crossdressers

As you will have noticed from my previous stories, I am gay. But for the last 20 years I have also been crossdressing and I now spend over half my time dressed. Over the years I have become more adventurous and now regularly dress in public. I live in the South of France not far from Cap D'Agde which during the summer is the sex capital of Europe. There is p...