Babby Sitter Milf First Anal Story Stories

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Evenings With Diane

by LeeHamilton on Sep 16, 2017
Interracial Love

If you've read Tim-Andre's story "Thinking with My Dick," you know that his fondest wish was to get a certain white MILF pregnant. First, he convinced himself he was in love and that she loved him as well. Before he successfully got her knocked up, he made sure to introduce Diane to me on an evening out with some of the rest of the guys from work. We met the...

Furry farm

by Wolfpup28 on Apr 29, 2025

It was a beautiful day on the wolfheart farm when Amanda wolfheart awoke to her mothers kiss on the forehead "good morning Mama" "Happy birthday babby" Samantha says as she moves to sit on the edge of the bed "Oh shit I forgot about that" Amanda says unconvincingly. " Ok sure Ill believe that when pigs fly" Samantha sa...

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Babysitter Rin

by Sean Renaud on Sep 12, 2017
First Time

"Hurry up Honey; we don't want to be late for the play." Kevin was standing in the doorway adjusting his tie and making a few last minute adjustments to his tuxedo. It had been a few years since the last time he'd been able to take in a musical and everybody who'd seen Wicked had simply raved about it. "Coming!" Susan appeared at the top of the stairs in h...

The Dog Sitter

by Tosshhh_ on Sep 23, 2019
Erotic Couplings

A few months ago myself and my long term submissive celebrated our 3 year anniversary. We have evolved past our original Dom sub dynamic and are now more or less a couple. For our 3 year anniversary we decided to go away so we got a dog sitter. That was the first time we met Tina. Tina was 18 years old. She was a petite thing with almost no tits. She was b...

MILF Summer

by NobodyImportant on Aug 4, 2018
MILF

It's summer but there is definitely something in store for you from spring break. Even though you have a college degree in [use fantasy], it's become pretty pointless since your wives are taking in large amounts of money from their divorce settlement, investing it wisely, and making it so you never have to work a day in your life. All of you have come to liv...

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My Korean Wife Ch. 04

by khatch46 on Sep 26, 2017
Loving Wives

The beautiful Kansas sun was high in the morning sky when we woke. More often than not the day after returning from field maneuvers was an off day. This fortunately was one of those days. Hea rolled toward me and played with my cock, but I was all fucked out from the night before. More proof that it was unlikely that I would be able to satisfy my wife's se...

The Baby-Sitter Diaries Ch. 02

by OregonDavid on Sep 12, 2017
Anal

I got to be honest, having sex with an eighteen year old, with a hard tight body and firm upright tits is really a lot of fun while your doing it. But if you are a married guy with a beautiful, loving wife, and three growing sons, when you finish screwing the baby-sitter, there is bound to be some guilt. Add the fact that the baby-sitter in question is someo...

Fireworks Pt. 01

by Secret_Passion2018 on Mar 21, 2018
Exhibitionist & Voyeur

It was the night of the fire show and Nick was lucky enough to be meeting Claire. He had offered to take her as she was recently single and needed a night out. Baby sitter arranged for her kid, he had driven to pick her up. She was the definition of a MILF for him. Short (around 5ft tall), with some of the biggest tits he had ever seen. She had long brown ha...

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...

The Baby-Sitter Diaries Ch. 03

by OregonDavid on Sep 12, 2017
Erotic Couplings

Chapter 3 Five years ago, in twenty-four hours I had the most intense sexual experiences of my life. First, I had sex with my eighteen year old baby-sitter, which was fantastic. Then I had anal sex for the first time with my wife, who at the time had been married to me for seventeen years. My wife followed it up with a blow job in the shower and I had slept...