Gloryholes Stories

144 results
Orientation
Length
Source
Infinite Scroll

Lissy the Gloryhole Stripper

by rick_oh on Sep 16, 2017
Fetish

Lissy showed up on time for her interview. She is a slender blonde female, about 23, with an engaging, sweet smile. Her yellow hair nicely framed her young-college-girl face. She wore a white blouse, jeans, and sandals. her attractive feet showed off her red-polished toenails. She told me that her name is Melissa, and she prefers that to her stage name of L...

Crossdresser Visits ABS

by iwant2suckabig1 on Oct 12, 2020
Transgender & Crossdressers

Thought I would post another one of my true adventures. Those of you who may have read my other adventures know that I enjoy dressing super slutty and being shocking in public. Nothing gets me more worked up than people watching me enjoy myself. With that in mind many of my adventures are dressing up and flashing my hard cock to people. While I enjoy both...

Public Relations Ch. 01

by melodylynnxx on Jan 7, 2020
Novels and Novellas

Alex's office was very normal, or, as some might say, boring. She worked as a "public relations officer" (read: receptionist) in a small town. There was nothing particularly interesting about her town, and there was nothing particularly interesting about her job. Come to think of it, was there anything interesting about her? No, don't go down that rabbit hol...

A First Time for "Hannah"

by HannahUndercover on Sep 16, 2017
Transsexuals & Crossdressers

First story, please enjoy and feel free to leave any feedback! Thanks for checking it out and I hope to write more! * At age 24 and after years of dressing in private, I finally decided I needed to get out. I had been scouring online personals for some time but never got further than exchanging a few emails and trading pics. I had been in touch with other...

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...

Jamie the Gloryhole Slut Ch. 03

by jr0777 on Sep 16, 2017
Transsexuals & Crossdressers

As you know from my previous stories, I am a "normal" person during the day and a crossdressing slut at night who loves to be on her knees. Her name is Jamie. Cocksucker Jamie loves servicing complete strangers at gloryholes. Nothing is more exciting than seeing a hard naked cock slip through the hole in the wall waiting to be kissed and sucked. I love havi...

Turning 50

by pondcat on Nov 27, 2017
Exhibitionist & Voyeur

Does one celebrate their 50th birthday...or mourn it? I guess I'd chosen the latter. What's to celebrate? I'm divorced...my ex-husband ran off with a girl half his age and has since burned through her AND married a third time...our kids have moved on and don't so much as call anymore, even for birthdays, and nobody so much as stepped up to throw me a party....

Laurel, Twins, The Vidset Pt. 02

by DCBelga on Oct 5, 2020
Sci-Fi & Fantasy

Laurel, the Vidset, and the Twins Part 2 "Can we masturbate each other's sticky pussies while you watch?" The Twins asked, like they were begging for a treat. You have got to be kidding me, this is great. "Hell, yes, you can! Please don't let me stop you." The Twins both put their bare feet up on the coffee table, spreading their legs as far as they could...

The Sissy in the Loft

by Sissy_Sammi_ on Dec 31, 2018
Transgender & Crossdressers

*All characters are 18+ *** James grit his teeth and walked through the door, a bell ringing as he entered the store. It was getting late and the sun was setting outside. He had been waiting in his car for nearly 20 minutes, waiting for people to leave the shop and no longer be near the store. The lady running the shop looks at him with a strange look fro...

Secluded Bliss Ch. 02

by Liquor69 on Sep 13, 2017
Group Sex

Marv and Annette had just finished their swim as they walked into Marv's suite. They heard giggling and moaning coming from one of the bedrooms. They went to look and saw Patti together with her concierge Ron. They were joined by another smokin hot woman, who was with another young, well-built stud. Marv had not met them before. Patti was apparently having a...