Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Lance's Seven Sins 01: Envy

by Lethal_Erection on Jul 14, 2020
Transgender & Crossdressers

Author's Note: This is the first of seven chapters that will be exploring the sexual escapades of an extremely well-endowed cis bisexual male named Lance. This story is told in first person past tense, and it has semi-ridiculous proportions and cumflation. Lance is now in his late 20s, and he is a spectacle of a man. 6'3" tall (190cm), a toned athletic fram...

My Wife Entertains My Friends

by lustdarkly on Jul 27, 2020
Loving Wives

"Bully Instructs My Wife To Tease My Friends." by Lustdarkly. A follow-up to - "Bully Introduces My Wife to the Executives." Looking good, smelling great, I arrived at James Thompson's apartment at seven and dashed up the stairs with a spring in my step. I hadn't seen Karen in three days! The Prick had taken my wife to Milan on a business trip. Tonight th...

A Twofer

by ironicchef on Sep 13, 2017
BDSM

I'm going to tell you a story. It's the story of how, improbably, I ended up sexually controlling two women. It all began when my ex-girlfriend hired me for a job when I got out of college. It was a temporary position, working for a marketing campaign. But if it was successful, it promised a lot of future work. My ex's name was Bridget. She had a slutty...

Busty Adventures of Brittany Ch. 09.3

by kimberlykitten on Sep 12, 2017
Group Sex

It was a Sunday afternoon and just a few hours before the big football game later on tonight. Brittany was taking a warm shower to clean herself of her own brother’s cum. The two have been fucking like wild animals since Saturday afternoon. This was the first time Brittany had some rest from their continuous fucking. But that was soon to change. Jeff walks...

I Dream of Jeannie

by seigar101 on Sep 13, 2017
Celebrities & Fan Fiction

Jeannie awoke slowly, stretching her lithe, sleek body on the silky, sensual satin sheets. Another frustrating day was about to begin. She had been stuck in this bottle for so many centuries. She was one horny little genie and was getting frustrated with getting herself off every night. (Not that, that wasn't fun) While she loved making love to her magnifice...

Fun for the Gang

by dave_jones_50 on Sep 12, 2017
Interracial Love

"Darling, do you remember Leroy?" Of course I remembered him. He introduced us to married sex with a black man a few months after we were married. "What about Leroy?" "He called to ask whether we might spend next weekend together at a resort in the mountains." "That sounds like fun. What do you think? Can you get away? Cindy worked as a fashion consult...

Cross-Country Road Trip Ch. 04

by MrFalkirk on Sep 11, 2017
Group Sex

From Pueblo we turned south on Interstate 25 headed for first Albuquerque and then to Las Cruces. The mountains near Raton were steep for the Midget, but it purred its way up the hills and coasted down the other side. Our laughter and delight in each other were evident as we rolled our eyes at each other and teased. For once our lust was not so hot that we h...

4 Seasons of a Life Ch. 01

by bb1212 on Aug 30, 2017
First Time

Chapter 1: Spring Spring is the time in a young man’s life, Where he first looks for a mate. He’s young and he’s green, But he’s mighty keen, And he goes like a bull at a gate. * Gippsland, Australia 1945. I was eighteen the day the war ended and had just missed out on joining up. To be honest I was quite disappointed. When our side was winning the men i...

23 Ways to Get Laid 01

by chaniseaustin on Mar 25, 2019
Interracial Love

MISCHA "I ordered a woman." I stand in the doorway of my hotel room glaring at a tall, blonde white guy. I tighten the belt of my terry cloth robe. His full upper lip curls in a slight sneer. "You reserved an appointment with Abbi." I can't pinpoint the light accent. Nordic, maybe? "I'm Abbi." Who names their son Abbi? "Obviously, I thought you were a wom...

Finding Ivy Ch. 07A

by Lcpce on Oct 31, 2017
Sci-Fi & Fantasy

Ivy sat at the kitchen table eating her breakfast, she had a small bowl of cereal. Her mother had just left for work. She was struggling internally with keeping her secret from her mother. She loved her mom and had mostly shared everything with her. Lately she had barely spoken to her. Her mother had suggested she see a therapist, because her mother thought...