Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

Tee and Gino

by gin0aki56 on Sep 16, 2017
Transsexuals & Crossdressers

Tee: You knock on my door, and I let you in my place. I am dressed in lingerie -- stockings, garter, and a lace thong -- and wearing heels. You smile when you see me, which makes me feel sexy. Once inside my house, I lead you to the bed. You sit on the bed and pull me to you. You grab my exposed smooth butt cheek and squeeze it, while you pull me close and...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...

It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...

The Office Ch. 05

by EasilyConfused on Sep 24, 2019
Transgender & Crossdressers

Tom had lost count of the number of times Hamilton had struck his ass with the wooden paddle. His cock ached for release but his unwitting periods of mental manipulation had embedded a control in his psyche. He knew that whenever he was in the presence of his Mistress he should seek her approval before acting. And that very much included ejaculating from his...

Creating Ginger Ch. 07

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. Hopefully you've read the previous chapters to understand the nuances of this storyline. ~~~~~~~~~~~~~~~...

Creating Ginger Ch. 09

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~ To say ginger was in hell would be an understatement, although it would be more accur...

Mistress Marisa's Estate Pt. 33

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 covered in welts, sobbing uncontrollably, restrained and naked over the whipping horse. You paid specific attention t...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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