Gloryhole Surprise Stories

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X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

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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...

First Time for Everything

by qazwaz on Sep 12, 2017
First Time

My wanting cock throbbed around my hand as I glanced down at my illuminating phone in my dark car. "Just got here" I replied, before switching internet tabs to the previously-loaded video of a blonde girl in a gloryhole. I had a long drive that day, about 3 hours to my hometown destination. Having broken up with my girlfriend a few weeks back and not having...

Visiting Another Gloryhole

by rand0m on May 14, 2019
Fetish

Since writing my last story about my first glory hole experience I've been getting quite a few messages from other users telling me about their experiences or some asking how they could go about finding one. Corresponding with them just made me realize how many similar guys there are out there like me. I still consider myself more "straight" on the sexuality...

Victoria Justice: Dirty Girl

by MrMaxLord on Dec 17, 2017
Celebrities & Fan Fiction

All of the following is complete and total fiction. Not a single word of it ever occurred. Victoria Justice: Dirty Girl by MrMaxLord (MF, MFM, oral, anal, DP, DVP, gloryhole, cons) ***** The night was dark. The only illumination of this long stretch of desert highway being the occasional gas station or roadside diner. And to Victoria Justice, that was j...

Gloryhole First Timer

by SluttyChrissy on Oct 5, 2020
Transgender & Crossdressers

This is a true story of an experience I had a few years back. I hope you enjoy! It all started on a random Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store. I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel...

Mike, Pam, Pete and the Favor Ch. 02

by StackedAction on Sep 25, 2017
Group Sex

Part Four Pam showered and was drying her hair with the hotel provided blow dryer while Mike took a quick shower. As Mike exited the bathroom in his towel, he looked at Pam in the mirror. "Lose the bra, you won't need it where we're going." Mike got dressed quickly, as it seems all men can, and was sitting on the bed, texting on his phone while Pam did he...

The Heather Files Ch. 02

by Indianaboy6555 on Jan 20, 2020
Erotic Couplings

After fucking and sucking several complete strangers on our last road trip, you could safely say that my sex life with Heather had become rather interesting. By outward appearances, we were just two young married people. It was the unseen that made things interesting. We'd checked out the rest of the porn I'd gotten at that stop in Illinois. Only one oth...

Eat the Seed

by Digger66 on Sep 25, 2017
Erotic Couplings

My wife and I visit a porn store with another couple. We watch video called "Eat the Seed". This leads to an interesting encounter at a gloryhole. My wife, Jill, and I have known Carl & Emma for years. We have gone camping together. Once, the four of us went to a beach resort in Puerto Rico for a vacation. Jill and I have been married for a little over...

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...