Sissy Baby Stories

124,889 results
Orientation
Length
Source
Infinite Scroll

Girl's Night Pt. 11

by DifferentBreed on Sep 14, 2017
Fetish

The applause from the gallery died as abruptly as it started and Fisher looked to Sophie, searching her face for an indication of what she was feeling. He stood, hand in hand with Eve, growing increasingly uneasy with her silence. "Mistress?" he finally managed to blurt, "What do I do now?" "Now?" Sophie said, "now, you get to cum. Aren't you excited Candi...

The Darkness

by littlemissnaughtygal on Sep 12, 2017
BDSM

Kim was always the good girl, even when Darnell and Kim were into their Domination nights, Kim always submitted to Darnell, she had worked with him for so long little by little trying to pull his dominant side out in him, she knew it was there, she could see it in his eyes, and she had seen it in her dreams so many times. Each night they did this, he becam...

Daddy's Little 'Girl'

by keptsissy on Sep 16, 2017
Transsexuals & Crossdressers

The noises he makes, the sound of it all, it's my favorite part. I love the feel of him in my hand but to hear him moan, grunt, make all the 'man sounds' men make when they are being driven sexually crazy makes my little thing wet. The slippery sound of him sliding back and forth through my hand, I love all of it. Masturbating him is one of the most erotic...

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

Sissy's Shopping Trip Pt. 01

by SissyFaye on Jul 13, 2020
Transgender & Crossdressers

"You finally got paid, Sissy!" my mistress says with excitement. "Yes, I did, my love," I say. "Well, I think in celebration of your first paycheck from this new job, we need to go shopping!" she says. "Oh really, shopping for what? I ask. "Clothes for me, and maybe some for you," she says. "Mmm, sounds like fun!" I say with excitement getting hard...

Night Out at the Pinky Finger Ch. 03

by Cap_N_PieSissy on Sep 13, 2017
Transsexuals & Crossdressers

He felt a little dizzy going over the night in his head. She is a he, but she...he...it...is really cute. And it felt so good holding...her, he anchored that word firmly in his mind, in his lap. He was starting to get a headache trying to process everything that had happened in the last...how long had it been. Before he could lose himself even further down...