Babysitter Stockings Stories

43,783 results
Orientation
Length
Source
Infinite Scroll

The Ethical Slutmaker Ch. 08

by KrisCherita on Sep 15, 2017
Group Sex

Rock a Bi Babysitter "So, what seems to be the problem?" Alexis asked Tammi, who was sitting on the couch in the interview room and having some difficulty looking the therapist in the eye. "Are you and Dan...?" Tammi hesitated. "This is probably silly, but..." Alexis waited. "He's not fucking other women... or not enough of them, anyway." Alexis raised...

Mandy's Sexcapade: The Hot Babysitter

by Syzoth on Dec 11, 2018
Group Sex

Author's note: this story was originally posted as "Mandy's Sexcapde: The Hot Babysitter". Due to overwhelming positive feedback, I've decided to make "The Hot Babysitter" into its own series, which will run concurrently to the "Sharing My Wife Amanda" storyline. Thank you for taking the time to read my works! -Syzoth **************************************...

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...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

My Naughty Babysitter Ch. 02

by Indianaboy6555 on Jun 4, 2019
Mature

My wife and I ran into a patch where we seemed to both be going different directions. It wasn't an interpersonal problem, life just pulled us that way. For example; things would come up at work that needed my attention, so I got called in. Then her Mother would call, and she'd need her there. So off she'd go, and I'd be home alone. The only saving grace at...

Pre-Birthday Party

by trixie_leigh on Sep 16, 2017
Transsexuals & Crossdressers

so, what do you want for your birthday? just you. seriously, you can ask for anything. anything. and i will make it come true ... seriously ... anything? anything. ... while i'm tied up, you want me to ask for anything? if you want me to keep playing with your cock ... yes. ... ... ouch! if you want me to take those clothes pins off, you ask fo...

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...

Our Two Year Panty Anniversary

by jennycnnn on Sep 14, 2017
Fetish

Spring was around the corner and my husband and I had our two year anniversary coming up in a little over a week. No, it was not our wedding anniversary, it was the anniversary of the first time I found out about one of Steve's fetishes and things have never been the same since. Our sex life has been on fire and I have loved every minute of it. It all star...

For Him

by ali2teaseu on Sep 2, 2017
Erotic Couplings

Work has been hard on him lately. Layoffs at the firm had him and his partners handling more cases and working more hours, and the pressure to bring in paying clients mounted. It was Friday and he called to let me know he would be home around 7:00 PM, something he never did until recently. He said he would grab a sandwich at the office so not to bother cooki...

Christmas Morning with the Kids

by dirtyjoe69 on Sep 17, 2017
Non-Erotic

My wife and I were agonizing over what to get the kids that year. They were boys ages five and eight. We watched all the ads on television, took note of all the hottest toys out there on the market, and finally decided on a few high tech toys we thought they would absolutely love. There were a few things they asked for we knew we had to get them. There were...