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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Had a long and lovely call with Avalon this weekend. She is a wonderful person who is fun to speak with about anything, but of course, she is especially good at the phonesex part of the conversation. She listens intently, knows what her client likes, and contributes her own ideas to the calls. I switched things up in the middle of our call and she didn’t miss a beat, figured out quickly where I was going and met me there in a way that completely fulfilled the fantasy. She is, and remains, extraordinary.
Honestly, Scarlett is absolutely incredible. She is far from an average operator. In fact, she is sexy, passionate, and mesmerizing. I never wanted the call to end, and you won’t either!
Aileen~ Awesome as Usual!
Aileen is the best! We have had quite a few date nights now and she drives me crazy each time. She knows me and what I like now and plays until I can’t take it anymore…in a good way of course. It’s also fun to laugh with her during “pillow talk”. The time always goes too fast! As always, looking forward to next time.
On our latest call Aileen deemed me to be Her sickest disciple, after previously telling me I am the most pathetic. I am so honored to be Her sickest most pathetic disciple. Aileen has brought me so far. I love ❤️ and worship Her and pray that our journey continues forever. Aileen rules!
Michelle’s voice and ideas were very exciting!! I can’t wait until our next adventure!! Everyone should give her a call she won’t disappoint you. When you call her, I’m sure you’ll be feeling the same way!!
Simply put, Vicky is and always has been amazing. She is so much fun to play with and talk to!
Zoey was amazing. The minute our call started, she knew what I needed and delivered like no other has. She is Spectacular!
This red-headed vixen blew more than my fantasy away! Talk about knowing what to do and how to do it…. This was by far the best I have had in a long time.
I feel Mistress Megan is in charge even when not online. I’m her slave.
Megan is extremely open minded. Plays along with even the most taboo fantasies. Close your eyes and enjoy!
Jamie has gotten insanely popular, so she is often “busy” or “offline,” but a call with her is well worth the wait. Sweet, attentive, and often funny as well as dirty, she has raised my fantasy role-play into something hotter than I ever imagined it could be.