Well, trust me, as every family in the neighborhood’s favorite sitter, I have plenty of naughty babysitter stories to share. When I was saving up for college, I needed a job that would pay well. Most of my friends were servers at local restaurants. But I wanted to do something different. So when my dad’s coworker mentioned to him that he was joining a pool league and needed a responsible nighttime babysitter, my father suggested me.
I was thrilled! I can’t lie, Mr. Johnson was a looker. Sure, he was my dad’s age, but he was still hot. And his wife had left him for some investment banker. So I knew he was just a lonely dad trying to make things work. Sometimes, I’d watch from my bedroom window when he’d be in his backyard, shirtless, mowing the lawn. I’d slide my hand down to touch myself. And I’d cum right there imagining Mr. Johnson’s hands all over my body.
One night, when I was babysitting for the family, I put everyone to bed very early. That way I could do a little snooping around his house while he was gone. And if you ever wondered if your babysitter does it, the answer is yes! I didn’t find anything terribly exciting, just a box of condoms and some lube on his bedside table and a few porn DVDs hidden in his underwear drawer. Mr. Johnson seemed like a pretty vanilla guy, and seemingly lonely. I knew I’d have a slew of naughty babysitter stories that summer, and I decided I wanted him to be my first.
So, I popped one of the DVDs in. And sat back and watched, pulling my pleated skirt up around my waist so I could start rubbing myself. By the time Mr. Johnson got home, I had my fingers deep in my juicy pussy, watching a blonde MILF with giant tits ride on a massive cock. Of course, he was surprised to catch me. But instead of disciplining me, he just sat down on the couch next to me. Without a word, he pulled his cock out and started stroking. Soon, we were both masturbating together, our eyes locked on the screen. That was until I couldn’t take it anymore. And I took his hand off his dick and slipped my cum-coated fingers around it instead. He sighed and put his head back, clearly enjoying a hand other than his own stroking his throbbing cock.
It didn’t take long before cum was shooting out and dripping down my fingers. Determined to make this experience one for my naughty babysitter stories, I leaned over and began lapping his cum up. I sucked the tip and took the last drops of cum into my mouth. Then I climbed on top of him, lowering my tight wet pussy down and pressing my lips against his, letting him taste himself on my tongue. Soon, he had his hands gripped on my tiny waist, helping me ride him while moaning the name of his ex-wife. Needless to say, Mr. Johnson had me babysitting for him every night of the week.
Then there was Mr. Baker a few blocks over. On my first day of snooping around his house, I found his naughty toy chest, complete with butt plugs and strap-ons! Or Mr. Daniels, who had a laptop full of some very hardcore, and very homemade, videos. I learned that Mr. Matthews really enjoyed young men. So much so that I surprised him one night with my friend, Johnny, whose favorite hobby was sucking off older men in dark parking lots. I’ll never forget the look on Mr. Matthews’ face when Johnny was sitting completely naked at his kitchen table, ready to give him a special treat. And I’ll always remember Mr. Smith, who had a closet full of women’s dresses and panties, despite never having been married or even seen with a woman.
And there’s so much more than that! Don’t you want to hear more of my naughty babysitter stories? Or maybe you have one of your own…
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