Sissy Glory Hole Stories

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Orientation
Length
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Infinite Scroll

Lorna's New Boots

by JulesC on Sep 11, 2017
Transsexuals & Crossdressers

It was a hot summers day. Lorna wasn't particularly busy at work and when her manager asked her if she wanted to take her, owed half, day off she didn't hesitate, especially, as she had received her back pay which meant she could buy those gorgeous black 4" spiky boots that she had been lusting over for weeks. Her boyfriend, Andrew, was away working in Edinb...

The Reunion

by DominantRomance1 on Sep 13, 2017
Erotic Couplings

The clock had just struck midnight when she got back to her small apartment, she just came back from a gathering of friends at one of those pubs that offer a live band. She felt tired, and loathed coming back home alone, she had a tingling that cannot be satisfied easily. She washed up the aftermath of the night and made her way to the kitchen to make some w...

A Little Refreshment

by Wattyjoy on Sep 17, 2017
Loving Wives

That day Anne's husband had gone abroad to work.. she and the children would be joining him in a few weeks, when he had found somewhere for them to live. She had put the children to bed, and had soaked herself in a bath. After she had dried herself and put on a dressing gown, she heard a knock at the door. She knew who it was. Before she had married, she...

Car Pooling Pt. 11

by TonyMA70 on Apr 17, 2018
Exhibitionist & Voyeur

I want to thank Peters1956 for editing part 11 of this story for me. * The time to depart to go to work came before the couple realized it. They slept in until noontime. They arose, showered and Martha made breakfast still nude. Hal dressed in slacks and dress shirt. Martha in dress and panties with heals to match. Hal picked up Mark and they were off t...

The Sister

by sydneycarton7 on Apr 17, 2018
First Time

Kyle made his way into the guest room after taking a shower. He wore nothing except a white towel wrapped around his waist, the skin of his body still glistening with water. He rubbed his palm across his chest as he began to open his suitcase. His skin was very pale, but it wrapped tightly across his well-muscled body. Kyle stole a glance of himself in the m...

Sue and Her Lover

by cvgreg on Apr 17, 2018
Group Sex

Sue and I have been married for 35 years and have two children, both girls, who we have gotten through college and out on their own so now should be the time for our 'glory' years. Since we are both successful in our careers, we make a very decent living and are able to live in a nice home and take several vacations per year. We live in the hills about 15 mi...

The Roommate Pt. 06 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Josh/Lori continued to endure a burning ass throughout most of the following day, but by the time he returned from teaching, the sting was more of a memory. He helped prepare the evening meal just as Miranda directed, reveling in his/Lori's long skirt, breasts, hairdo, earrings and bracelets, and slip-on sandals with heels. She had even applied a little li...

Shooting Amanda

by swellegant on Oct 13, 2017
Exhibitionist & Voyeur

Isn't it wonderful to spend time doing something you love? I have always adored erotic photography, on both sides of the camera. I value the time and attention required to arrange the pose as perfectly as possible, to be as alluring, as erotic as can be. I love the way that that pose will be captured for later viewing; and I appreciate mix of vulnerability a...

Service with a Smile Ch. 07

by dirtynaughtythoughts on May 1, 2018
Fetish

After our long embrace, Kelly crutched out of the bedroom and lowered herself carefully onto the chair in the bedroom. She then propped her crutches up against the wall beside her. I quickly read her cues and grabbed a stool and moved it in front of her chair. I then carefully lifted her casted leg and gently placed it on the stool. This was the first time I...

In the Night

by kendraskye on Sep 16, 2017
NonHuman

Greg wasn't a passionate man, but there was one thing he was passionate about: aliens. He had chased them down for years as a boy and had even joined a local network of UFO chasers as an adult. His wife thought he was crazy, but what did she know? She did nothing but watch soaps all day, while he went to work. And today was no different. He had just gotten...