Gloryhole Surprise Stories

135,828 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Mother's Day Surprise

by Scott_Heywood on Sep 13, 2017
Group Sex

Mothers Day was coming and I wasn't sure what to get Lisa. Both Her Kids had already let Us know that They wouldn't be able to be there and each had already bought Her a gift. That meant it was up to me to make Her day special. I had it all planned out... I let Her sleep in...which She really enjoyed. She woke to a nice homemade breakfast. I started a nice...

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...

The Booth

by NikkiKush on Aug 19, 2017
Exhibitionist & Voyeur

She really had no idea what she was in for, but the large dildo display that was located right inside the front door let her know it was at least going to be dirty. She liked dirty. She was dressed for dirty in a skirt that stretched across her luscious ass, and a top that dove all the way down her deep cleavage. Her body was the very definition of rubenesqu...

A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

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...

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...

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...

Visiting a Gloryhole

by BuckyDuckman on Sep 13, 2017
How To

Gloryholes. Are they real? How do I find one? What's it like to visit one? Is there an etiquette to follow? Are they safe? Are they real? Yes! I've visited several of them. How many? I didn't keep count. Ten? Fifteen? I don't know. I've visited them from Philly to St. Louis to Florida and lots of places in between. Deploy the power of the internet to search...