Category: babysitter

Ronnie's Confessions

Ronnie 844-332-2639 Ext 443

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” →

I've Got Little Sisters

Kinky Krysta 844-332-2369 Ext.410

People say a sister is a friend for life, and I know that’s true because all three of my little sisters are like my best friends. They look up to me so much, and I love teaching them new things. Watching them struggle at first and then master a task makes me so proud.

Almost like a little Mama, ya’ know? They all look a little like me and a little like themselves. But you can definitely tell we’re related by our long dark hair and our chunky cheeks. Daddy says he loves that his little girls are all healthy.

Continue reading “I’ve Got Little Sisters” →

Valerie 844-332-2639 Ext 243

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.

Continue reading “Pretty Sissy Ballerina” →

Hot Teen Babysitter

Avery 1-844-332-2639 ext. 228

I’ve always loved being a hot teen babysitter, especially if the dad is fuckable. But around this time last year I had a really scary experience while babysitting one night. I figured that since it’s almost Halloween I would tell you about the scary yet sexy night.

It was one of those spooky nights where you just feel on edge and keep looking behind you to see if anyone’s there. The wind howled through the trees as I sat nervously on the couch, trying to distract myself with a book. I was babysitting the Andersons’ two kids, Jessica, and Max, for the first time, and the old, creaky house seemed to have a life of its own. I normally wouldn’t venture to this side of my town, but Mr. Anderson was so fucking hot I made an exception.

Continue reading “Hot Teen Babysitter Has A Scary Night Part 1” →

Babysitter Secrets

Valerie 844-332-2639 Ext 243

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.

Continue reading “Babysitter Secrets” →

Babysitter Valerie Is Here

Call Girl Valerie 1844-332-2639 Ext 243

*Knock, knock* Hello! Guess who’s here! Babysitter Valerie has come to save the day! I know how scary it is for a baby when Mommy goes out for the night. Whether it’s for work or play, the baby gets so sad and lonely whenever she is away. However, there’ll be no tears tonight! It’s okay to be nervous, though; Babysitter Valerie understands how strange it can be to trust a stranger. Will you just promise to try to be brave for me as we get to know each other? After tonight, we’ll no longer be strangers!

I’ve read over your Mommy’s to-do list, and it appears like we have a few things to accomplish before we start having all kinds of fun. We have to make and eat dinner, then clean up from dinner and clean you!

Continue reading “Babysitter Valerie Is Here” →

Anna 1-844-332-2639 EXT 203

Are you a good little boy or a naughty little boy?

Come and tell me about all your cute little outfits. I want to hear about alllllll of them, what colour are they? how many do you own? And which one is your favorite special one to wear? Do you wear them every day? Or will you only wear them for me? Do you fold them neatly in your drawers, or are they all nicely hung in your closet? I’ll take good care of you, you just have to trust me.  If you’re really good, you’ll get a nice treat at the end.  I promise I’ll make you blush.

Continue reading “Where are all the good little boys?” →

Kayla Cumsalot 1844-33-CANDY ext 357

My sweet Davey is such a good reader, but sometimes, reading out loud makes him nervous. I thought it would be a good idea if instead of Mommy reading Davey a bedtime story, it would help him practice if Davey reads to Mommy. After he’d showered and got into his nighttime Diapee and PJs, Mommy sat at the head of the bed, and Davey snuggled back between my legs.

His back rested against my tits, and he held up his e-reader. We picked a dirty erotica story about a hot mommy in shiny pantyhose who took a stranger home and forced him into pampers. My hands played in Davey’s hair as he began and at first, he was okay. Then the story started to affect sweet Davey, and he began to trip and stumble over his words.

Continue reading “Davey Reads To Mommy” →

Sylvia * 844 332 2639 * 428

Lil Jack and Jill are twin siblings who enjoy being around Nana Sylvia any time she will take them.  At an early age, I would love to show them off to my friends.  My daughter would never dress them alike and didn’t want me to.  They were like dolls to me; so of course I dressed them as such.  They loved climbing up into my lap in the big rocking chair by the picture window so they could see out.  In the summertime, I had a special pool just their size rather than the big one out back.  After kicking and enjoying the pool outside we would relax in the rocking chair where I would cuddle them and give them their dinner when they were young.  As Jack and Jill aged, I noticed they were more aware of each other.  Jill was the most curious and asked the most questions. 
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Sylvia * 844 332 2639 * 428

Stormy weather really upsets Bobby.  He is my neighbor’s boy which I care for sometime when they go away.  We play games on his IPad and I read him stories from his favorite storybooks.  As we finished dinner the thunder started.  He started being concerned right away and started asking me questions about the thunder and what was going to happen.  Pulling him up onto my lap I tried to express to him about the weather and that everything would be fine.  Assuring him that Sylvia would always protect him from any harm seemed to calm him down.  Giving me a big hug he told me he knew I would.  He is just a loving boy; with the biggest blue eyes.  Deciding he was way too excited to finish his dinner; I suggested getting our baths and getting ready for bed.  His boats and ducks were waiting on him.
Continue reading “Stormy Weather” →