Babysitter Stories

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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...

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...

When I Came Home Early

by unowen1987 on Sep 12, 2017
Erotic Couplings

I was finally going home. It was about 10:00 at night, I had just gotten off work, early if I recall, and was heading back to my house for a night of easy sleep. A bit about myself though, I am 22 years old, and I work on call, 24/7. I am 6'6" and weigh in at about 200 lbs. I work out regularly and because of my on call status I get paid even when I don't h...

My best friend's sister, the babysitter

by darkwindofchaos on Aug 7, 2008
Erotic Couplings

Hi. My name's Aaron Silversten, and when I say I have a story to tell, I’m not kidding. You see, when I was in high school, my friend Jarod had this younger sister. Well, she's still his younger sister, only she's not so young anymore. Allow me to explain. When first I knew Allison, she was fourteen when I was eighteen, but boy, even then, she had a killer b...

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Babysitter Spends the Night

by The Duke on Sep 12, 2017
Erotic Couplings

I got married at 20 years old to my High-school sweetheart. Now at the age of 35 I have 2 sons, one is 4 and one is 2. I am as happy as can be. My wife is gorgeous and the boys are terrific. Both of our careers bring in a lot of money and we live very comfortably. The only problem we have is that her job requires her to leave on trips quite frequently. Not...

The Babysitter

by Tara_Neale on Aug 18, 2017
First Time

It was the summer I turned eighteen and it was unforgettable. My parents separated before I can even remember. My mom remarried and moved to London. My dad would not allow her to take me with her...and smart lady that she is she did not want me caught in the middle of a very nasty custody battle. Instead they compromised. And I got the best of both worlds, L...

Monique-My Big Black Sister Ch. 05

by hotpup on Sep 12, 2017
Interracial Love

pt. 5 The Babysitter Vera, the babysitter, met me at the door and told me to be quiet as all four kids had just fallen asleep. As I followed her to the front room a tent formed in my trousers. When she turned around she noticed it and seductively licked her lips. Clearing my throat I asked, "So, young lady, what is tonight going to cost me?" "Well, Matt,...

SMS: Single Mothers Servicing

by HotnHornyGuy on Jan 12, 2017
MILF

She arched her back and cried out as you thrust your cock into her pussy again and again. Your balls slapped off her thighs as you took the single mother from behind, admiring the fine peachy arse before you. You still could not believe how your life had changed to the point where you were now on a bed plowing your cock into a horny mother as part of a local...

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Driving the Sitter Home

by splitlapper on Sep 14, 2020
Erotic Couplings

My wife, Sheila was one of the best fucks that I had ever had, but male curiosity can keep us looking for new pleasures. She was still tight after the baby and she loved everything I did to her. Her favorite position was riding me, sometimes facing me and sometimes facing my feet. She always loved 69, especially if I paid enough attention to her clit. Someti...