Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Counceling

by seeingifthismakessearchwork on Mar 2, 2020
Transgender & Crossdressers

****** Forward: This story is an expanded version of a story I read and with the author's permission I revised and added to it. ***** Dr. Lidia Vega let her eyes briefly dart to the clock on the wall. Her newest patient hadn't said anything for nearly ten minutes, but that's okay it was his process and she was only here to lead him through his grieving. S...

Backdoor Man - The Missing Chapter

by SevMax2 on Jul 14, 2020
Group Sex

Having settled the matter of who owns whom by everyone agreeing that I owned them all, I was very much engaged in what turned into the Orgy To End All Orgies, or so it seemed that evening, as we fucked our way far enough into the evening that by the time that we were all hungry, we didn't have time to cook. It was partly the fault of those blue pills, which...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

Sarah Visited an Adult Book Store

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

Since I've been reading the stories here, I've learnt a new acronym, ABS, Adult Book Store. Reading these stories has made me very curious to experience a glory hole myself. At a gay beach I had sucked off a complete stranger but an ABS sounded even more fun. I picked out the sleaziest, run down store I could find around here. I've bought books there befor...

A Sissy in Need is a Sissy Indeed

by JamieMichelle on May 12, 2020
Transgender & Crossdressers

Part I: A Sissy in Need Is a Sissy Indeed Jamie Michelle "Hello, ma'am. I do yard work and I noticed that you might need some help with yours," the man said in a deeply sonorous voice when I opened my front door upon hearing someone knock. He stood there before me in the light of the mid-morning Sun, and I had to catch myself from showing amazement, as I...

Cucky Trained by CD DOM Pt. 01

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

It was Friday afternoon as you and your wife pull into my driveway I finished putting my lipstick on and adjusted my long, tight, pencil skirt. You can clearly see the outline of my bulge which was the look I was going for. You got out of the car and your wife handed you an overnight bag which doesn't seem to contain much, although I did tell her beforehand...

The Cause

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Often I've wondered why the only thought to stir my sissy cock, some 40 years into life, is the vision of a hard, throbbing, blue veined cock arched just before my eager lips. Was it the spiked heels I pranced around the house in younger years or perhaps the love for the pale yellow slip I stole from my sister and wore secretly under my jeans and shirt while...

Glory-Filled Hole

by femboyslut on Sep 12, 2017
Transsexuals & Crossdressers

Ever since I was little, I always enjoyed dressing up in my sisters' clothes despite being a boy. This may have been because my dad left before I was born and so I had a big female influence due to my 3 elder sisters and my mum. When I was about 11, my sister Alice, 14, and my other sister Izzy, 16, decided to dress me up as a girl using all sorts of make-up...