Category: baby sitter

Under Female Supervision

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When boys are in trouble, I’m a true believer in making the punishment fit the crime. One of my bad little boys has been busted, touching himself in the shower! Such a naughty little perv! His Mom and I decided that his punishment for the next three months would be to only jerk off under female supervision!

He pouted and cried, saying that that would be humiliating and embarrassing, but he had no idea just how bad it would actually be. His mom works so much, it isn’t like he’d be able to ask her to supervise a jerk-off session, and well, I can be a bitch. So I would make sure I wasn’t always available when he was horny.

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Your Big Beautiful Nanny Has Arrived

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Smarten up, you bad little boy! Yo Mama is gone, and she left me in charge. Your big, beautiful Black Nanny is here to make sure you learn your lesson and be on your best behavior. I won’t stand for no lip, so don’t try to fucking sass me. If you do, I’ll send you right on out to that tree in the front yard and have you break off a switch to beat that smartass with.

It won’t be no twig neither. I’ll make sure you pick a nice flexible sapling that’ll whip through the air and leave pretty pink lines on your ale bare ass. That’s if you get to being bad now, but we can have some good fun if you know how to mind your p’s and q’s.

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Mr. Johnson Fucks My Satin Panties

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Whenever I’m sitting at the Johnson’s house, I get so horny. Mr. Johnson is the perfect man. He’s a great dad, a good husband, and so funny. As soon as I put the kids to bed, I go into their bedroom and get naked. Then I take one of his business shirts from the closet and pull it over me. I love how the collar smells, and for a few hours, I pretend I’m his wife.

Once I had his shirt on, I lay on his side of the bed and inhaled his pillow. The man smells like sin and sex, and I can’t help but rub my fingers over the crotch of my satin panties as I fantasize about what it would be like to be with him. I was so wrapped up in my daydream the last time I did this that I didn’t hear his car pull into the drive. Nor did I hear him walk up the stairs and into the bedroom.

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I'm A Bad Girl

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I’m a bad girl. Really bad. I don’t want to get in trouble or have anyone do anything about it, but I think if I don’t confess, I’ll burst. The things I think about are shameful and dirty. Things that put people behind bars for long periods of time. If anyone knew the types of things I desired, what kind of filth lurks behind my innocent demeanor, they’d lock me away.

How else would they keep society safe from a monster like me? My darkest secret is that I don’t want to be an accomplice and give someone else the forbidden fruit. I want to take it for myself.

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Secret Nanny Cam Catches Naughty Sitter

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Something came over me last time I was sitting for this little boy. Lately, I’d been consumed with thoughts of spanking little bottoms! Just the way a squirmy bad boy feels as I drape him over my lap and peel back his pants to swat my hand on his bare bottom! I’m telling you, I’d become obsessed! It was all I could think about, all I wanted to do.

One of the naughty boys I sit for was actually behaving when I was over last night. It was infuriated! I just wanted a reason to bend him over my lap and listen to his cries for mercy. There were no thoughts other than that in my head. I didn’t for a second think I would get caught by the secret nanny cam his Dad had set up.

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Dirty Auntie Naomi 844-332-2639 ext 216

Who loves Dirty Family Fun Phonesex? I think we all share deep dark fantasies and thoughts we would never tell anyone! Well, except for your favorite phonesex operator. lol.  Those dirty, nasty, illicit fantasies are my favorites.

I like being the Naughty Auntie. Whether I am teaching Mom and Dad how to train their daughters to be good little family sluts, or turning the family’s prized son into a cock-loving faggot. It’s just so fun! We can be gentle and fun, teaching a young boy that his dick is special, to hard-core fantasies of turning out the whole family of sluts. Continue reading “Dirty Family Fun Phonesex” →

Double-Diaper The Downstairs Neighbor

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The couple that live below me are constantly fighting. Unfortunately, our apartment walls are thin, and I can hear everything they argue about. The guy stays home all day, playing video games and never cleaning up after himself. His partner asked him to take out the trash and do the laundry before she got home from her twelve-hour shift as an ER Nurse, but guess who forgot?

She was extra mad tonight and threatened to leave for good if he didn’t grow the fuck up. I heard their front door slam hard and peeked out my window to see her stomping across the parking lot. As soon as she sped off, I grabbed my diaper bag and knew this was a job for Babysitter Val! I’d double-diaper that big baby and see if he wanted to grow up then.

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Ronnie's Confessions

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Welcome to Ronnie’s Confessions

I thought this was only fitting since I’m learning so many new things about the deviant world of lust and arousal. As I’m exploring, I should keep you updated on which kinks and fetishes I learn that turn me on. And wowie, did this one turn me on!

 

I shared that a teacher spanked me and that I spanked the snot-nosed twerp I was babysitting for, but what I didn’t explain was how much I liked spanking that bare bottom. I liked it a lot. Now, I’m finding excuses, any freakin’ excuse, to pull his pants down and spank him! Continue reading “Ronnie’s Confessions” →

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My favorite friend to play dress up with called again today! We’ve been having so much fun trying on different girlie outfits and exploring how they make my friend feel. Remember, he’s little, and I’m his babysitter. I love how much he trusts me to guide him through our fun.

Today I thought it would be exhilarating to let him dress up as a pretty sissy Ballerina! His whole face lit up when I held up the pink tutu. “Have you ever worn tights like this?” I asked, and his little head shook excitedly. I had him remove all his clothing and boy undies, then rolled the toe of the pink pantyhose up his legs. The waist rested at his belly button, and I noted how cute his little bits looked all wrapped in soft pink.

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Babysitter Secrets

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Over on phonesexcandy, I shared with you how I became someone’s diaper chastity keyholder, but here, I wanted to not tell you about the babysitting secrets I learned on my first day! In an age regression session, a boy a little younger than me was interested in playing dress-up. However, he didn’t want to explore his mom’s or sister’s closet; he wanted to see what I brought in my bag of fun.

I showed him some soft nylon pantyhose and a bra and panty set I’d brought just for him. As I started to help him put everything on, I realized how uncomfortable the stockings would be if he didn’t shave his leg! We agreed it would be best If I taught him how to shave his legs so he could fully enjoy the secret we were sharing. It wasn’t long after he was silky smooth and dressed that he confessed another secret I probably shouldn’t tell you.

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