Gloryhole Cum Stories

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Sherry's Adventures as a Slut Ch. 02

by BadBuzzard on Sep 13, 2017
Loving Wives

This one was really big! She had both hands wrapped around it and her mouth stretched wide as she engulfed the big mushroom-shaped head. Sherry was excited beyond belief! She loved cocks, especially big ones. The bigger, the better. Long, fat, hard, delicious, cum-spewing cocks. She loved the firm squishy feeling on her tongue as she swirled it around the he...

The Cheerleader Uniform

by pondcat on Sep 16, 2017
Fetish

Texas is known for football. From high school to college to the Dallas Cowboys, we are a one hundred percent bonafide football state. And the big college teams are HUGE draws that carry a lot of esteem. My college is not one of those colleges. Sure we have a team, but you've probably never heard of the Horns. Not the Texas Longhorns, mind you. Just the Hor...

A Cuckold's Tale

by CastleDJK on Sep 14, 2017
BDSM

Based on Chaucer's Canterbury Tales Prologue Three Mistresses are lounging around the pool, chatting and laughing, while their three sissy maids stand by to attend to them. Big breasted in a white string bikini, redhead Mistress Reeve is enjoying a foot massage from one of the sissies at the side of the pool. Lady Night, raven-haired with an alabaster whit...

Frustration Pt. 04

by kalkstein1970 on Sep 25, 2017
BDSM

We left the table and walked to the back of the club, and entered a small, narrow hallway. There were doors on both sides. Some of them were open, and inside I could see small rooms outfitted with comfortable furniture and lit with soft lighting. Behind some of the closed doors I could hear low moans, whispers, and the occasional scream of pleasure. "In he...

Dirty Chrissy Goes to College Ch. 4

by DirtyChrissy on Sep 13, 2017
Erotic Couplings

After my boyfriend Rob introduced me to the wonders of sex in video peep booths and gloryholes, our sex life heated up even more. Now, when we would fuck, Rob and I would relive the experience. One night, while fucking my pussy doggy style, he reached around and diddled my clit with his fingers and whispered in my ear, "Is this how that stranger touched your...

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...

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...

Jenny Visits the Gloryhole

by JennyfromNJ on Jul 31, 2018
Loving Wives

Yes, it happened again the other day. People, posts, chat online as well as people I come across in real life will often trigger sexy thoughts in my head. Those thoughts most often elicit memories of my many past encounters. My pussy gets wet and I get that uncontrollable urge to suck cock. As a little background, Nick, my husband of 30 years completely ow...

CD Cum Slut

by pervasive1 on Sep 16, 2017
Transsexuals & Crossdressers

I shave my body smooth and get dressed up slutty in heels, nylons, garters, panties, short skirt, tits, wig, makeup, fake nails, etc. A ripped punk rock tank top and spiked belt complete the whore look. You pick me up off a street corner near my place, I hop in your car and before we say anything, your cock is out and its buried balls deep in my throat. We...

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...