Sissy Babysitter Stories

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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...

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

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...

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...

Teen Cocktease Babysitter

by CharlotteUnicorn on Jan 22, 2020
Fetish

What a day! Project meetings all day long, from 9am to 9pm, with really intense demo testing, barely half an hour for lunch, and I was on point for the whole day as the lead system analyst. I was sooo tired when I got home. Opening the door, I hoped my kids were asleep and there would be no crises to deal with. I couldn't hear a sound. Yay! April had co...

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...

Ted and Lindy Ch. 01

by R410a on Oct 3, 2018
Interracial Love

This is not the standard boiler plate interracial story of black dominance or cuckolded sissy's. It is a romance between a white widower and a black girl from the ghetto. Thank you for all of the great comments I've received on other stories, I trust this will be to your liking as well. ***** As I stood in front of my dresser struggling to put in cufflink...

Earning His Keep

by Compliant1 on Sep 19, 2017
BDSM

I punched in the code and waited. I knew that I was being charged $1.99 for each minute, but I didn't care. I listened to the recorded music until a woman's voice came over the phone. "Tell Mistress Monica, have you been a naughty little sissy?" "No, but apparently my husband has." There was a long pause on the other end. "I just spoke to the manager. He...

Long Haul

by Spencerfiction on Sep 13, 2017
Non-Erotic

Alice was so beautiful she took my breath away every time I saw her. I asked her out a couple of times and she turned me down on both occasions. The second time was just after she split with Dougie Laughery and I thought I had a real chance this time. Dougie was an asshole, I had been competing with him toe-to-toe since junior high. I couldn't see what Alice...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...