Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Neighbourhood Terror to Sissy Pt. 08

by Fibaro on May 20, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 9 Once off the bus Mark snuck to his house as good as he could. Hiding behind bushes and hedges whenever he spotted someone. He really didn't want to run in any of his neighbours with this big pink shopping bag. It would mean nothing but trouble since he realised f...

The Handyman

by sammysamson4 on Jun 25, 2019
Transgender & Crossdressers

My DIY skills were limited and my new apartment needed a bit of work to freshen it up, so I decided to get a builder in. I had known Tim for a few years after going to school with him and he had a good reputation as a handyman. He also had a reputation with the girls with his good looks, lean body and, from seeing him in the showers at school, a rather larg...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

A Downtown Moment

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company. While I never went out with Loretta, we did have the od...

Mz Zen's Fabulous Birthday Pt. 01

by lushusboobs on Sep 17, 2017
BDSM

Chapter 1 Ms Zen was turning 40 in just 5 days. The prospect of 40 was depressing. The closer it got to her birthday, the more irritable she was becoming. Although she'd always had a healthy attitude towards age, she had to admit that the reality of turning 40 was far different than she expected. She was actually dreading her birthday and she had avoided ma...

Sissy Whore Ch. 04

by DebbieDublin on Mar 14, 2018
Transsexuals & Crossdressers

I stumbled to the bathroom to fix my face, my head still spinning. I reapplied my lipstick and dusted off my foundation. Wiped away the mascara stains from my cheeks and reapplied. When I was done I returned to the living room. 'These are for you.' He said when I approached. He reached into his jacket, extracted a pair of large gold coloured hoop earrings...

Wife and I Get a Roommate Ch. 05

by tonyl65 on Sep 25, 2017
Group Sex

We have all been getting along really well. David enrolled in the local community college and would be starting in September. David was also looking for a part-time job. Carol and I were going to the local State College and starting back about the same time. It was already the middle of August and we only had a couple more weeks before our schedules would ge...

All the Stops: Signs

by badgirl298 on Sep 17, 2017
Celebrities & Fan Fiction

Giles’ harsh breathing was the only sound in the old abandoned gas station. The other occupants maintained an eerie silence, all were afraid of what would happen next. They had fled Sunnydale only to be surrounded and forced off the road by the Knights of Byzantium. They had taken sanctuary in this little building, the only thing holding the knights at bay w...

A New Life Ch. 02

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

I closed my eyes and took a breath, which was far from easy. The steel boned corset, which I was made to purchase and learn to lace myself, was quite tight and pulled my body into the curvy shape that both Mistress Sally, and the men who have been encouraged to watch me on Skype, all enjoyed. The cursor moved across the screen as Mistress Sally's Skype call...

Aficionado Gets in Trouble Ch. 04

by His_fag_wife on Mar 17, 2020
Transgender & Crossdressers

Taryn told me to sit down, which I did with difficulty as I was only just getting used to breathing with the corset on. She knelt down in front of me, but this time it had no hint of submission. She was plainly completely in charge of me at this moment. She took the first shoe off, and prepared the first stocking, rolling it over her thumbs. I put my foot o...