Babysitter Stockings Stories

43,783 results
Orientation
Length
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Infinite Scroll

She's Early

by Levon on Sep 25, 2017
Fetish

"I'm early," she discreetly whispered to me as we stood up to welcome our friends who had just come through the restaurant doors and saw me waving to catch their attention. I didn't really have time to process her statement before our friends, Rob and Amy, approached our table to greet us. My first thought was confusion, and perhaps I misheard her. Our frie...

Tammy and the Gold Anklet Ch. 01

by jackfntammyf on Sep 12, 2017
Loving Wives

(Hello again everyone! I've taken a little bit of a "sabbatical" from writing because I've been living some very interesting real life adventures. I'm going to start writing about one now (very slightly embellished), but I will continue the Tammy's Public Display Adventure series at a later time. And I'm still going to write the Tammy's Torture Weekend serie...

Mr. D and the Babysitter Pt. 06

by Holophernes on Jun 1, 2020
Erotic Couplings

(For readers outside Australia, a few notes: Mobile = Cell Phone. Summer begins on December 1. In Australia we wear thongs on our feet = flip flops. That is 'thongs' plural. 'Thong' could be one of those items of footwear but increasingly is also used for that item of underwear which has barely a string between the bum cheeks and a tiny triangle of cloth in...

My Babysitter Ch. 03

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a wo...

It's Simple!

by Kantor on Sep 13, 2017
Erotic Couplings

It’s not been a good few weeks. The kids, work, bills, the usual things. We said that we would try to get some time together and talk about how things were going. How we were feeling about ourselves. We had to go out to a party on Friday and we were out late. The babysitter wasn’t too happy about being brought home at 3 am, but she gets well paid. I gave h...

The Reawakening of Dr. Clark Ch. 05

by The_Maestro_Braddock on Sep 12, 2017
Erotic Couplings

Dr. Greg Clark sat at his desk, letting the individual in front of him respond to an interview question and willing himself to not yawn or blatantly check his watch. He was no fan of hiring people because of moments like this. The inevitability of turning away some qualified applicants along the way for things as simple as being as deadly boring as this guy...

Caught-Out

by littleginger on Sep 13, 2017
Group Sex

Nathan Thomas came home early from work that night. He murmured a greeting to the baby-sitter and went upstairs to look at his sleeping baby. After kissing him on the cheek, he went back downstairs and told the babysitter that she could go home. "Oh, it's okay," she replied, "My mom can't pick me up until 10 anyways." Nathan shrugged and plopped down on t...

It's a Small World

by sweet_angelic_one on Sep 17, 2017
BDSM

The restaurant was dimly lit, candles on the tables and sconces on the walls lending atmosphere. It wasn't a fancy place, but one she enjoyed on a night out. As much as she loved her child, an adult night out was called for every now and then. When her friends said it was her turn to pick a place for dinner she'd chosen a restaurant with atmosphere and no ki...

Wife's Threesome with Babysitter

by Hotzforgulz on Feb 26, 2019
Loving Wives

All characters in this are above 18 years old. This is fictional story and doesn't resemble anyone in real life. Please comment as this is my first story. *** Shaju is a perfect full figured woman with a bouncy, milky, natural tits, and firm ass with a figure of (38DD-34-40). She wears a 34dd low cut sports bra whenever she works out, this makes her milk...

The Babysitter's Control

by moreblabber on Sep 14, 2017
BDSM

Will wrote a list of emergency numbers on the chalk board in the kitchen for the babysitter and left her to watch TV, the kids already being asleep. She was a definite cutie before, and since she had come back from college, a big flirt. Madi often teased him by dressing provocatively. She knew that Will thought she was attractive, and that he must have had...