Sissy Glory Hole Stories

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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...

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...

A Sissy's Lifestyle

by nancyvasquez on Sep 13, 2017
Anal

When I go out to the adult bookstore, I am always dressed as a woman. And not just as a woman, but a whore. I tease my hair up big and high, and will have either a dress, skirt, or butt baring short shorts; and, of course, high heels. It's a 15-minute walk from my apartment to the arcade, and my route runs me through an industrial area along a fairly wide av...

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...

Jesse's Journey Down a Rabbit Hole Ch. 19

by sadkins116 on Sep 15, 2017
Illustrated

Jesse and Marcus tried to sleep, it was difficult with the ball and chain still attached to their butt plugs. They would drift off to sleep but then wake with a shock whenever they moved. The balls were heavy and slippery, weighing almost twenty pounds. The stainless steel finish was polished with a thin coating of something very slippery, like Vaseline. Whe...

Jesse's Journey Down a Rabbit Hole Ch. 13

by sadkins116 on Sep 14, 2017
Illustrated

I want to thank everyone for reading, voting and commenting on our story. I submitted the first six chapters, and Rebeccasm submitted chapter 6 through 12. I will be submitting chapters 12 through 18. We have both worked hard on this series and as such both deserve to share the postings. Hopefully you will visit both of us and enjoy the series. As I mention...

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

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....

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

College Boy All Grew Up

by Applebottom1 on Jul 31, 2019
Exhibitionist & Voyeur

I have two other stories of my college years of starting to wear panties, flashing my thong and eating my cum. From there I did all those things along with buying dildos, doing some glory holes and finally getting with girls. Those would all be fantastic stories that I one day will write. If there are any comments on what you would like to hear about please...