Sissy Milking Stories

28,345 results
Orientation
Length
Source
Infinite Scroll

Isabella's Reversion Pt. 04

by silverbackteddy on Sep 11, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

Jack and Jill Pt. 04: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

He looked in the mirror, clean shaven with blonde wig and full make up, he was unrecognisable to himself, his false eyelashes fluttered back at him, his shoulders, his hands and his Adam's apple all gave him away on close inspection, but from a distance he was passable as a woman. He couldn't believe he was doing this, he was terrified of going out in public...

Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...

Creating Ginger Ch. 06

by Ms_Allison on Jun 9, 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. In the below story I refer to the male character several ways but try to maintain a consistent in referr...

Sorry Sissy You Lose Pt. 03

by LittleDickSissy on Feb 11, 2019
Fetish

"Mmmm that felt great" George said as she released his thick cock from her mouth. "Thank you". She looked up at him and smiled. She could still taste his cum in her mouth. She'd never had cum in her mouth before let alone swallow it! "Kiss it. Kiss my cock" George instructed her. She did as she was told, she puckered up and kissed the head of his cock a...

Mistress Marisa's Estate Pt. 19

by keptsissy on Sep 14, 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... ******************************** The two of you sit in your study, big over-stuffed chairs. You sip scotch, just a leisurely evening with your lover by the...

Laurie's Cam

by writedoctor on Sep 16, 2017
Transsexuals & Crossdressers

Laurie was on the brink of tears. Slender, manicured fingers fiercely gripped the leather bound steering wheel of her sky blue Porsche. Fuck it, Laurie thought, it's all about power. Why should I fight? She replayed the heated, ulcerous tête-à-tête with the owner of the large real estate firm. However Laurie knew she was right and the rewards made up for the...

Sissy Downfall Ch. 02

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Revised version. all characters are adults. Part two. All Characters are over 18. * My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really...

The Lustful Labyrinth

by HYjaCK on Jun 3, 2020
Fantasy

Christ, you think, can't believe he made an easy job a shit one. You were walking home after work, finding yourself incredibly irritated by your boss, who seemed to have a knack for forcing you to do more work than you would usually have to. Today, for example, he ordered you to help him fix the water dispenser in the office, yet you found yourself being the...

Open in Reader