Sissy Pantyhose Stories

12,794 results
Orientation
Length
Source
Infinite Scroll

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Domme Club Humiliation

by NancyPan on Sep 19, 2017
BDSM

I would never say that life was routine with Mistress Monica. She kept me on my toes—or, more literally, on my heels—at least around the house. On days when I got home from my law office before she got home from her corporate job, I would immediately take off my suit and tie and put on one of the frilly aprons Mistress preferred me to wear at home, and a pai...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Fine Tuning

by cathynylons on Jun 19, 2018
Transsexuals & Crossdressers

As I served my wife Dominique a brandy in the living room, I noticed that she was looking me up and down with her famous wicked smile. After finishing washing the dinner dishes I returned to the living room to see if she desired another glass of brandy. Again, I noticed her looking me over. I worried that perhaps there was a run in my nylons or that my masca...

Suggestions from Her Kinky Sister

by timeagain93 on Sep 16, 2017
BDSM

Mistress Patty had a kinky sister. She had been dominating her husband for years and according to my Mistress the man was her complete slave. Naturally they gossiped and soon I received a text listing questions regarding limits, safe words and playtime. The safe word was her hometown. At any time I could say it and break out of the scene. Playtime was desi...

Controlling Sissy Janice Pt. 01

by sissy_janice on Jul 6, 2020
Fetish

I was uncertain which category I should post this story under. I love the crossdressing stories most, and this would certainly fit there. But the main action really is about cuckolding, so I've put it in the Fetish section. *** I had thought that my wife was unaware of my crossdressing. Not only was I wrong but, as it turns out, I was the one unaware - -o...

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...

Erika Blossoms Ch. 06

by SmoovB on Sep 13, 2017
BDSM

Note: This is chapter six of a very long story. 28 chapters so far. It is wide ranging and will eventually touch on interracial sex, dom women, lesbian sex, true love, revenge and much, much more. I hope you enjoy it. ***** CHAPTER SIX – Sunday Night I walked over to unlock the door. As soon as it unclicked, Jana was coming through. I held my finger to my...

Female Erotic Police Squad Pt. 03

by mattpantyhose on Sep 14, 2017
Fetish

Most of the officers of Female Erotic Police Squad enlist in the service to catch criminals. But there are also some who do it for sex. Physical love is the modern way to fight crime, but it does not necessarily mean that sex should be considered merely a tool. As long as an officer fulfilled her duties properly there was no reason for her not to take additi...

Wife in Control Ch. 04

by wifetoy on Sep 25, 2017
Fetish

This is the fourth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please review the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I did not think she would actually perform all of these cruel punishments on m...