Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My girlfriend Christina has been staying with me for the past sev...

Sissy_World 03

by JDBones on Sep 16, 2017
Transsexuals & Crossdressers

Billy rode in the front seat of the car, staring out the window, and watching the world go by. His mind swam and his body already hurt, but he knew better than to protest his pain to his Husband. If he did, he would be punished with a Bare ASS Spanking and he didn't want that. He stood at 5'6 and weighed maybe one hundred pounds soaking wet, but he doubted...

What Every Sissy Knows

by BelissimaSissy on Jul 31, 2018
Transsexuals & Crossdressers

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy! ***** I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could he...

Subliminal Obsessions Ch. 07

by Sissyhalo on May 28, 2018
Transsexuals & Crossdressers

*Before... But this, this is the big turning point because this, this as hot and as intense as it because it settled into lovemaking and being made love to by this amazing guy that honestly could have all the pussy he ever wants and he's with me. With me making love to me and it's so much more than sex to me right now. And honestly. Really fucking honest...

Being a Sissy for Viv Ch. 01

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I." "Oh, what was so interesting about it?" I asked. Viv paused for a moment, her eyes on the wine glass in her hands. "It was about turning men into maids....

Bukakke Sissy/Angel

by hyperpress on Sep 14, 2017
Fetish

He's wearing his favorite outfit. A nylon/spandex blended thong that encased his fullness, shaved and smooth in a delightful caress. A bustier girdle with four straps (he wanted six but the cost was exponentially increased for those two extra straps), and wolford thigh high stockings, his legs and bottom were completely shaved...he was delighted with how fem...

The Doll's House

by Velvety on Sep 14, 2017
BDSM

He stopped the car on a deserted country road, calmly turned the ignition off, then turned to look at her. His eyes trawled over her. She was wringing wet, and her dress clung to her skin, clearly outlining the shape of her slim, shivering thighs. Push-starting a car in the dead of night was not her idea of fun. 'I'm cold,' Sissy said, wrapping her arms aro...

Mistress Marisa's Estate Pt. 21

by keptsissy on Sep 15, 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... ******************************** As I enter your bedroom I see the box on your bedside table. THE box. My face flushes. You are at your makeup table, che...

Futa Island

by Kazza on Nov 18, 2019
Transsexual

This story is designed to be played as an interactive erotic adventure. For the best reading experience, please select the 'start game' button over on the right of the screen --> Futa Island was considered a myth for decades, a tall tale whispered amongst tipsy sailors in the dark corners of port taverns. The rumors spoke of a hidden island filled with...

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Mother Dear Pt. 09

by keptsissy on Sep 13, 2017
Fetish

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful." She winks at me over her wine glas...