Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

The Slave and the Sissy Ch. 02

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ella took the chain from their collars when they reported to her, together for the first time, in the morning. Pepper's eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation. Pepper gripped his hand tightly, lest she should suddenly wake from this beaut...

Loaned Out

by Valsslut on Sep 16, 2017
Fetish

Yesterday Lady Valerie loaned me out to her friend. Terrified beyond belief, I drove to a large hotel, rode the elevator up to a large suite and ordered to undo my pants and prove I was wearing panties at the door. I was scared about being scene in the hall worse the humiliation was turning me on so much my clit got hard. Lady Valerie had taken my chastity o...

Strawberry Milk Pt. 03

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Now I was planning on going home for Christmas but given how I was changed and changing I'd need some sort of plan and to spend some thought on this. In the meantime I have a few things I wanted to do and that's well... Milking my titties and blending that milk into some of my body lotion and then going out for a walk, get some groceries and do some clothe...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

The Midnight Archive

by CEOJeanne on Jan 28, 2019
Miscellaneous

“How many mundane advantages does it take to win a fight with a god? How much firepower, logistical fortitude, manpower, morale, diplomacy, and genius does it take to match up to omnipotence? Circe doesn’t know, and that is the issue. It may be impossible, it may not be worth trying, or perhaps it can be attained. The only way to know is through experimentat...

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The Jewelers

by mollycactus on Sep 16, 2017
BDSM

Author's note: my BDSM stories are mainly D/s in nature – there is no Literotica category for these, so if you do not like D/s, you can skip this story. ***** Molly had taken on a new submissive male, who had what seemed to her to be, a strange need. Kneeling before her, Robyn explained his desires. "Please, Miss. Cage my cock so you'll be completely in c...

Mistress Marisa's Estate Pt. 05

by keptsissy on Sep 12, 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... *************************** "Hurry up, just the things you need for the weekend, that sissy shit you do to look like a girl. Let's go." He's staring at m...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Daddy, Not Dad

by latecomer91364 on Sep 13, 2017
Transsexuals & Crossdressers

I discovered my bisexual inclinations fairly early in life, so by the time I was 19, I had done nearly everything you could do with any combination of genders and numbers. I'm a regular guy on the outside, but in private I am comfortable in both the masculine and the ultra-feminine role. I could pass on the street as a hot, high-heeled slut, blowing straight...

A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...