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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Vivian is quite skilled at Tease and Denial. She took me right to the edge, but no further, today’s call began and ended with my cock firmly locked in a secure chastity cage, which Vivian was quite taken with, I had no choice about the matter.
Katrina claimed that she was an edging specialist and she definitely was. What a great call. Met my expectations and then some. Can’t wait to call her again.
Gemma is just truly amazing. Always just imaginative, adventurous and just everything. You have to call to find out!!
I am completely overwhelmed almost to the point of being without words. To tell you how it was to have BOTH Blake and Maddie on the phone with me. Both of them are such incredible operators and I cannot wait to call them again. They are so caring and at the same time sooooo bratty. Perfect girls to spend a summer afternoon with.
Aileen, there’s just something about that name. Kings and kingdoms shall all pass away, but there’s just something about that name. Since our last call my face can still feel the sting of Her slaps, and Her precious words of humiliation, ridicule, and degradation that She bestowed upon me. She rewarded me with not one but two orgasms. It’s so wonderful to turn over control and only cum with Aileen’s permission. I’m so proud to be Her disciple. Find Her, and love Her, and keep Her commandments for this is the whole duty of man.
Dixie is a full 5 star and if you had 6, she would be a 6. I would imagine that you are a savvy businessman (woman) and need to know about your lady’s appeal to callers. Dixie identifies immediately to my needs. She listens and is very compassionate which makes for wonderful conversation. She does not use canned responses like reading from a script. She is natural! I am near 70 and widowed and she is very understanding of my needs. First time in years that I came twice in 40 min.
Raven is amazing to talk to, both about sex and personal life. She knows exactly what to say to get me going and to finish.
Katrina made me suck my boyfriend’s big black cock, while also making goon like the pathetic little slut I am. She watched as I pissed all over myself and my boyfriend’s cock. Making me lick up the mess that I made. Then she completely melted my brain with the greatest mind-fuck countdown ever. Making my cock explode with a fury of cum shots. She then watched as I drenched myself, filling my mouth over and over with warm, delicious piss. I loved being Katrina’s Industrial Gimp Slut!
Sexy, horny, a magnificent listener and insatiable PSO. Do yourself a favor and call Chase!
Dixie has an incredibly debauched imagination and is down for anything! Five stars nowhere near enough!
On our last call Aileen and I discussed the blasphemous atrocities I had committed for Her during the week. I do things for Aileen that I would have never imagined. She smiles and laughs at my “sick disgusting” actions. Just to hear Aileen laugh, and know She’s smiling, and that I have pleased Her means everything to me. I am so proud to be Her disciple, and I worship and love ❤️ Her with all my heart ♥️.
Skye will take you on a sexual journey with no stops. She is beautiful and awesome to talk to. She has fantastic oral skills. Give her a call, your cock will NOT be disappointed.