Male Babysitter Stories

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The Babysitter Has A Dick

by mr.z on Feb 29, 2020
Transsexual

Ricky Sampson is your average 18 year old boy. He lives with his parents and baby brother in a house in Nevada where he goes to school and works part time at a water park, it's Nevada the town gets really hot all year round. Ricky looks like a typical computer science nerd, with his glasses, black hair and pasty white skin but he wants to be anything but a s...

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Emma Rehearses Her Part

by stb6060 on Sep 13, 2017
Erotic Couplings

Emma Kirby had enjoyed acting from her first steps on stage at her primary school. She played in all the Christmas shows, and had acted Mary in her local Cathedral, when her class was chosen to perform on Christmas Eve. But that was eight years ago, and now she was sixteen (nearly seventeen – as she said to her friends), and she was now at sixth form colleg...

Send in the Clone

by RejectReality on Sep 13, 2017
Toys & Masturbation

Ryan grabbed a towel, having just finished a quick shower. With their son off at his parents' house for a few days, he knew what his wife's suggestion to take a shower right after dinner meant. They were both a couple of days overdue for some alone time, and breaking that fast always resulted in mind-blowing sex. He toweled off, gave his hair a cursory blow...

The Reawakening of Dr. Clark Ch. 03

by The_Maestro_Braddock on Sep 12, 2017
Erotic Couplings

"Alright, I dropped the kids off at your parents' house so that's all set," Gina told Greg as he walked through the door, kissing him on the cheek, "Sally should be here in like 30 minutes to pick me up for the casino. What time are you heading out?" With some amount of regularity, Gina and Greg would leave Martin and Shelly with his parents and go out with...

Rachel Goes to the Movies

by dkgooner on Sep 13, 2017
Erotic Couplings

After finishing school she had decided to try her luck in Los Angeles, exactly what she would be doing she hadn't planned. Which were where she was now, standing in front of the apartment block where she had rented a small apartment, she just had to find the landlord Mr. Robert's office to get the key and arrange some other stuff, such as when and where the...

Up Late

by LorenzoAbajos on Sep 14, 2017
Erotic Couplings

I was up late, driving around the countryside. I would need to get home before daybreak. It'd been an interesting night, and it might get more interesting before it was over. We'd arrived home at around midnight. Our babysitter, Aubry, was waiting for us. She was an eighteen year-old Senior in high school. This was the first time she'd sat for us. With just...

College Shemale babysitter

by tomf15 on Sep 15, 2017
Transsexuals & Crossdressers

Disclaimer: All characters are 18 and over. Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet. "This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her f...

Pussy, Peckers, and Pizza Ch. 15

by LIVINRFANTASIES on Sep 15, 2017
Exhibitionist & Voyeur

OUR FIRST BIKE WEEK PIZZA AND PUSSY. Sounds like a meal fit for a king. But the pizza was for eating and the pussy for showing. I'd recently sold my Harley and some of my old cars, replaced with a used standard roof line Chevy van to pull a flatbed trailer from Illinois to Florida. Seven trips, each one just over a thousand miles each way, to haul cars and...

The Reawakening of Dr. Clark Ch. 11

by The_Maestro_Braddock on Sep 12, 2017
Erotic Couplings

Dr. Greg Clark gritted his teeth and tried to focus on Ms. Bristol's words. It wasn't that she was boring; he was genuinely interested in how Shelly was adjusting to life as a kindergarten student. Mallory, however, was making it damn hard to concentrate on anything but how hard he was and how good her hand felt— slipped through his open fly and unbuttoned b...

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...