Sissy 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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Poor and Proud

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to techsan for his editing of this story. * I was in my best mood at a beautiful sunny Friday morning in May with no clouds visible in the blue sky over our village outside a Scandinavian town. The time was exactly 9.12 when I took the phone call, which within a short time would mean such serious problems for so many people in our village. I w...

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...

Furthering My Education

by jimmysub on Sep 15, 2017
Fetish

Well I had to go back to Community College to take some child development courses as my wife and her lover are planning on having a child together. This is part one of the adventure. I really don't like this idea but what my wife says go. Her biological clock is ticking and she has been with the same lover, Mr. Steve for about 3 years. So Debbie is going to...

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...

Mandingo Row Ch. 02 - Discovered

by scatwoman on Jun 1, 2020
Interracial Love

Editor's note: this story contains scenes of non-consensual or reluctant sex. *** 2. Discovered One night, after she left, I snuck down to my own car and followed her. I'd seen enough detective shows (mostly on those lonely nights while she was out alone) to know how to hang back far enough to not alert her to my presence. I felt pretty proud of myself wh...

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...