Male Babysitter Stories

79,949 results
Orientation
Length
Source
Infinite Scroll

I Am the Night

by Sean Renaud on Sep 13, 2017
First Time

"Don't think I don't know what you're doing here Harold." Jessica said standing in front of the mirror and putting the final touches on her make up. "You're not nearly as clever as you like to think you are." "Whatever do you mean my dear wife?" Harold called back from the bedroom. He was sitting on the edge of their bed furiously putting a few final detail...

The Babysitter Revisited

by nasty_dan on Sep 14, 2017
Mature

I didn't intend to write a sequel to The Babysitter but there were so many generous comments and emails requesting a little more to this story that I couldn't resist. I tried to incorporate all of the suggestions that you requested. So, for the good folks who appreciated The Babysitter...well, here's to you. I hope you enjoy! * Cathy Marlin crouched silent...

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...

Blackmail Bitch

by SlutProblems on Mar 26, 2019
Group Sex

Tisha was always on time. She was good with the kids. She didn't bitch about the mess that I left sometimes and she even did a bit of straightening and cleaning to help me out. I called her over about twice a week to babysit and everything had been fine until the night that she decided to show her true colors. It was a daytime barbeque at the country club th...

Banging the Babysitter

by majicman21 on Sep 19, 2017
Transsexuals & Crossdressers

The alarm clock rang, and Jenny rolled over with a groan to press snooze. Her wife of ten years, Vanessa, groaned back, moving to Jenny to nuzzle against her. They laid there for a few more minutes, the cobwebs of sleep clearing slowly from Jenny's brain. "Morning," Vanessa murmured. Jenny murmured back, turning over again, face to face with Vanessa. She...

The Adventures of Madi Ch. 02

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 a chance at another girl's beautiful feet." I glanced over my room, looking for the...

A Prophecy Come True

by ElderDirt on Mar 20, 2018
Romance

There's much to say about being a being a dirty old man. I mean that I'm not exactly good looking, hard-bodied, super-smart, or filthy rich. Yet, I've found that with Kelly none of this matter. I've watched her grow up from a child to a young woman and should feeling feel ashamed of myself for being such a pervert. But when we are making love, I could care l...

Pro-Domme and At-Home Mom

by DeniseNoe on Sep 16, 2017
Reviews & Essays

What I Learned From A Friend Who Was A Stay-At-Home-Mom And Professional Dominatrix "Brenda" told me she did not want to put her baby into day care after the child was born so she would put plans for a regular job on hold and continue as a professional dominatrix after the little one came into the world. However, she definitely wanted to protect her baby fr...

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...

Watching a Mom Jerk Him Off

by imaging on Sep 19, 2017
Exhibitionist & Voyeur

Back in the so called "Golden Age of Porn" there were adult theaters almost everywhere. Even in small towns. Once the movie companies started building multiplexes out at the mall, the old, traditional movie houses were abandoned. So porn operators could buy or lease them cheaply and they became smut emporiums. I learned pretty quickly that if you laid down...