Sissy Babysitter Stories

9,467 results
Orientation
Length
Source
Infinite Scroll

Simply Friends

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

"Hey, Eli," the common law wife and mother of two spoke into her cell phone. She paused a moment then said, "We're around the corner for your place." Valencia Williams ended the call. She looked at her husband, Durrell, who was driving the cash rental car. It was a metallic white gold 2010 Volkswagen Passat station wagon. Durrell, at 34 years of age, was a...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

Twenty Questions

by silkstockingslover on Jan 7, 2018
Reviews & Essays

Summary: Jasmine responds to most common questions asked by readers. Thanks to: Tex Beethoven, thor_ph, Robert, and Wayne for editing. 20 Questions I get asked a lot of questions about myself and my writing. There was even an article by Bob_Aganoush called Literotica Authors 02: silkstockingslover. This makes me think I should go into more detail. So her...

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...

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...

The Search

by justincbenedict on Sep 17, 2017
BDSM

Benny Price rolled around on the bed with his beautiful new wife, Nora. They were necking like teenagers, which was nice, and he was feeling her up but over her snug brown tank-top, and around her denim miniskirt. This was nice, but a little ridiculous for four months of marriage. This was what you did on the second date, usually, in Benny's experience. Ben...

The Adventures of Madi Ch. 04

by sexualrelief7191 on Sep 25, 2017
Fetish

"Hi, my name is Madison, or Madi for short. I'm about 5 foot and 3 inches, brunette, cute, and like to have a good time. I'm not exactly like other girls, because I'm bi and have a foot fetish. Yes, a girl can have a foot fetish too. I love feet, and I'm always looking for chance at another girl's beautiful feet." Summer was less than 4 weeks from being ove...

Feminisation Services

by HorribleHenry on Sep 28, 2020
Transgender & Crossdressers

FEMINISATION SERVICES It's a dead give-away. The way I have spelled 'feminisation' that is. Indicates I am probably not American. I am really wary of giving anything away these days, after my experience just a while ago. A strange email heading "Feminisation Services". I know I should have assigned it to the bin straight away. On any other day I probably w...

The Werewolf's Sabbat Ch. 02

by River_willow76 on Sep 25, 2017
NonHuman

"Daddy, Daddy!" Cynthia squealed when she spotted him outside of the school. Running late, Bill had just arrived in front of the school. He smiled and waved at his little girl. She ran as quickly as her short legs would carry her, and he reached out and scooped her up in a big hug. "Hey there, ladybug!" He hugged her tightly, swinging her in circles. "I'm so...

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...