Sissy Milk Stories

38,319 results
Orientation
Length
Source
Infinite Scroll

Chrissy's Trip

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: Trouble in Paradise It has been seven months since Chrissy and Miriam had their memorable first date, and things are going well. Every night Miriam is in town she falls asleep with her giant futahood buried in Chrissy's cum filled ass, and most every night she is away Chrissy heads to Futanari Palace to sate his hunger for cock and hot futa juice....

Jock Princess Ch. 04

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

Logan carries me down the hall of his place like i'm some little feather making me feel definitely thrilled and small but he's a really huge guy honestly like one of those guys that was big in high school but he really worked out and got bigger still in college. I like the way that all feels. I like that he carries me all the way into his bedroom and sets...

Ultimate Sissy Weekend Ch. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 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...

Chrissy's Night Out

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: A Snack Before Dinner Four days have passed since Chrissy's adventure at Futanari Palace. Since that glorious night he only goes by Chrissy, he no longer identifies with the name Chris. He has begun dressing only in women's clothes, with full makeup and a wig. His coworkers weren't all that surprised by his change in behavior, they have suspected hi...

The Snow Sissy Ch. 01

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

Somewhere, in the frozen northern regions of our great globe, in the shivering mountains, there is a school of demon. Now, we all know what demons look like – they are creatures of immense, horrifying beauty. Even with their skin (which can range from Jet black, through fiery red, to the purest alabaster white) they possess inhuman and powerfully seductive b...

Transforming Brent Pt. 04

by sissymissyct on Dec 2, 2019
Fetish

In the morning I showered and dressed casually as directed by Mistress Wendy. My new black skinny jeans and a plain blouse with light day make up and my cork wedges. Some jewelry and my handbag and I was ready. Mistress wore leggings and a tunic top with her long hair tied up in a bun. Wearing flats, she was still much taller than me. We had a light breakfa...

Strawberry Milk Pt. 04

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Once I figured out how I wanted to experiment with this revelation on my nanos I decided on Dr. Corey as the start and Jill my porn store sissy. Dr. Corey was fucking me everytime I seen him and I started trying to concentrate as he breastfed from my huge titties. Not out loud but like mentally to my nanos. ~Harder, a harder bigger cock...more sperm, more...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

Nilla

by Fire_Fairy on Sep 16, 2017
NonHuman

Hi everyone! This is my very first story. Please vote and comment. All constructive criticism is welcomed. ------ It was a Friday night and I was a little mad. My friend Mayella (liked to be called May or Sissy) had dragged me here to this club called "The Raven." It opened about a week ago and Sissy wanted to give it a try. Now I'm not really one to go...