Sissy Glory Hole Stories

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Allyson the Sissy Whore Ch. 01

by sissymaidallyson on Sep 12, 2017
Transsexuals & Crossdressers

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn't find any problems getting what -- or who -- he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing. He was convinced he was straight and l...

Glory Hole

by GateKeeper_A on Jun 11, 2014
Group Sex

Last month, you had discovered that your local adult novelty store had a glory hole. Since that day, that glory hole has been all you can think about. Every time you close your eyes, you picture a cock sliding through a hole towards you. Every time you masturbate, your mind is filled with fantasies of strange men's cocks. You shudder with a mixture of trepid...

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A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...

Glory Days Again

by lil_raider on Sep 16, 2017
Transsexuals & Crossdressers

I just couldn't help myself. It had been years since I had a girlfriend and the last time I had gone out in full drag to a gay bar confirmed what I'd been feeling for some time -- a wig and lots of makeup could take 10 years off your age, but not 20. The bar scene was over for me and it had been a while since I'd had any real-life action. I got by with cam...

Interracial Sissy

by nancyvasquez on Sep 16, 2017
Interracial Love

Remember how I told you the story my ex wife told me - of how that white prostitute at the strip club came out of the booth after having been in there with a black guy, and how she was flushed and proud and was telling all of the other hos about how proud she was to have been with that handsome black man? Well it happened to me tonight! I almost can't believ...

Desiree's Cock Quest

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

It had only been a month or so since Suzie discovered my secret stash of letters between my alter ego Desiree and another transvestite. In them she read how we both love to suck big black cocks and our bragging on the longest cock we'd ever sucked. Needless to say, it put quite the strain on our marriage. With the fact my love for long hard cocks was all o...

Mistress Marisa's Estate Pt. 13

by keptsissy on Sep 13, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** I am taken to a club, the country club for just the type of high-end players you love to know and that LOVE to know you....

The Training of Sissy Paula Ch. 3

by submissive~pet~ on Sep 14, 2017
Fetish

My eyes were blurry still from not getting enough rest. Mistress had me go shower, and make sure I was smooth all over. The outfit she had picked out for me was a wild looking mini dress. Black latex with half moons on each side that would be over my butt cheeks. She helped me with the outfit and bondage gear. Oh my sissy you’re going to have one hell o...

Mass Sissy

by Jman236 on Sep 16, 2017
Transsexuals & Crossdressers

Well my mistress wanted me to post this short story of my latest sissy humiliation for even more humiliation so here goes... So it was a typical Saturday and I was on my way over to my mistresses' house, she wanted me there bright and early. I arrived at her house promptly at 4:00am and when I arrived I was informed that I would be spending the entire weeke...

The Locker Room Glory Hole

by Sissy_Sammi_ on May 30, 2018
Transsexuals & Crossdressers

*All characters are 18+ ***** The bell rang, rousing all of the students out of their seats. The students stuffed their books, binders, and pencils back into their bags before quickly rushing out the door to get to their next class. It was going into seventh period, the last period of the day for everyone without an after school class. Most students quickl...