Babysit Stories

1,618 results
Orientation
Length
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Infinite Scroll

Wife Swapping Combinations Ch. 01

by Bodington on Sep 19, 2017
Group Sex

When I was a graduate student at Wayne State University, my wife Leah was a nurse at one of the major hospitals in Detroit. One day when Leah arrived from work she was clearly flustered but excited. She told me that within the past month she had struck up a friendship with a co-worker, a black nurse named Octavia Brown. As the girls became better acquainted...

Melissa Ch. 01

by gummidurango60 on Sep 19, 2017
Transsexuals & Crossdressers

"Melissa," my mom called from the kitchen. "Yes," I answered from my bedroom. "I want to talk to you for a moment," "Okay," "What's wrong?" my mom said as I walked into the kitchen. "Even with my scholarship I'll never be able to afford the tuition to..." I began as I plopped on a stool at the island. I'm eighteen and a week out of high school; all I w...

BabySitter Bribe

by Ashson on Sep 12, 2017
First Time

When I was sixteen I had a perfect figure. The trouble was that the number assigned to that figure was the number one. Flat of chest and flat of bottom, that was me, while all my friends were blossoming with boobs and butts and noticeable hips. I did what all girls my age do in such a situation. I ate. By the time I reached seventeen my figure was heading fr...

Bonus for the Nanny

by will_4_rp on Sep 12, 2017
Mature

As the warmth of my last orgasm slowly faded from my body, and I relaxed my torso, which had been stretched like a cat to concentrate the impact of each shudder, I closed my eyes, slowly let out my breath, and finally relaxed. Will wasn't due back from his date for two or more hours, after all. His kids hadn't stirred all night, either, and I was, frankly,...

Her Babysitter, His Teenage Whore

by bbw4youngercocks1 on Sep 19, 2017
Erotic Couplings

My wife and I had been married for five years and had some good sex before our twin daughters were born, then our life in the bedroom began to taper off some. It wasn't that Lisa wasn't attractive any more; she was hotter than ever with the few extra curves she put on after she had the girls. I don't know if she was self-conscious about the ten extra poun...

Aliandre's Story Ch. 02

by aliandre on Sep 2, 2017
First Time

Part II -- A Weekend with Nathan As you can well imagine, after that exciting ride home, I eagerly awaited another call to babysit for Jennifer and Nathan. And every time I was in town -- to go to work, or to do some shopping, or to go for coffee with the girls at the cafe -- I found myself constantly watching for Nathan's old truck. Overnight it seemed t...

The Familiar Gaze

by ilovebananas on Apr 1, 2020
BDSM

D I V O R C E What does that spell out to you? Divorce, of course. Excuse for me my shit poetry, but I do have a story to tell about an experience I had after I divorced from my nasty ex-husband. What did I do? I did something stupid. That was to go back to my home town and set up a business. It was not just any business. In the interim period between the...

Stepping Out with Steph Ch. 02

by SEVERUSMAX on Sep 19, 2017
Group Sex

Having enslaved Stephanie, Blair and Joanna still had to deal with the fact that she was probably pregnant with Blair's child, and the fact would soon get out to his staff. True, he was the boss, but would his employees ever respect him after this episode of incest? The couple agreed that Stephanie would stay at home to babysit Oscar during the day, and th...

Helping Out a Friend

by kooky123 on Sep 26, 2017
Mature

Miss Penny was a lovely woman, and she just didn't deserve all of the difficult times she had been through over the past several years. Her husband had left her, choosing to chase after younger women. It wasn't even one woman in particular, he just didn't want to admit that he was getting middle-aged, so off he went to try and be young forever. Miss Penny...

My Best Friend's Wife Babysits

by jsk04988 on Jul 31, 2019
Loving Wives

This story is true, on the names have been changed to protect the guilty, and one of my fondest sexual memories. It is also my first attempt at any type of writing, so please leave comments, try to be gentle. ***** My name is "Billy", and my wife, "Janice" and I were not legally married, but we were living together with our toddler and infant girls. She h...