Babysitter Turned Into Sissy Baby Story Stories

367,655 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

The Babysitter Takes Over

by sissysherry2 on Mar 13, 2018
BDSM

"I know your secret." These were the words that I had both dreaded and longed to hear from my babysitter. Let me start at the beginning. I am single and have a couple of kids at home who aren't quite old enough to be on their own when I have business obligations. I share custody with my ex, who left me to be with another man, who happened to be black. I ge...

Cam Slut Pt. 01

by GavinIsaNuisance on Oct 26, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Eighteen year old Jeremy Briarstein is forced to remain home while his parents go on an extended twenty year anniversary vacation. He is further dismayed to dis...

My life

by Monalott on Apr 29, 2025

Note - This story is told from a submissive sissy/femboy/tranny perspective and I try to write it so you, the reader, are the protagonist. So if you are more into being a top or domineering character, this probably won't be for you. Note - As always the way I write is rather erratic and I'll often return to and amend already published chapters to fit in with...

Open in Reader

The Babysitter Takes Over Ch. 02

by sissysherry2 on Mar 20, 2018
BDSM

Chapter 2: The party "Ok bitch, I'm going to invite my friends over tonight for a party. I'm going to text them an invite and I want you to do it. Now go over there and start talking. And you better make it good or I'll post the pictures on my Facebook page." I went over to the corner and started talking while Teri got her phone out again and pointed it at...

The Babysitter Takes Over Ch. 03

by sissysherry2 on Mar 19, 2018
BDSM

All of a sudden it became quiet in the room as I was instructed to open the front door. There were half a dozen teenage girls, including my Mistress Teri, watching and waiting. There I was, in my pink nightie, fully made up and completely hairless on my body. There stood my ex wifes lover. "Well what do we have here?" he sneered. The contempt in his voice w...

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Discovering Amber Ch. 06

by Ms_Allison on Feb 12, 2019
Transgender & Crossdressers

Mistress notes: Once you understand them sissies are rather easy to manipulate and control. It's just a matter of finding which buttons are the ones that need to be pressed and when to press them. amber has a weakness for lingerie, heels, and humiliation. Additionally, she was very easily brought to her knees at the promise of an orgasm. Getting dressed up...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Driving Her Home

by bored_doe on Sep 16, 2017
BDSM

Alan smiled at the perky blonde college student in the passenger seat of his sedan. "So Catelyn, have you figured out what your major is going to be yet?" "Mister Denny, are you wearing makeup?" It wasn't a question, it was a challenge. Her brown eyes watched him without flinching, waiting to see how he'd respond. The question was so unexpected, it knifed...