babysitter phone sex Archives

August 31, 2015

Published by Girly Kisses at August 31, 2015

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Caught in the act!

I never knew how much I liked being caught in the act until the day I had casually invited a friend over while babysitting. The kid was in bed and we had finished our lackluster study session. We looked at each other and smiled. She was one of my closest friends and I felt a surge of affection for her as she sat cross-legged across from me on the worn carpet. I flashed her a toothy smile and pulled her into bear hug. She returned the hug with equal force and ran her hands along my back. I pulled her torso to mine and slowly moved my head so my cheek rubbed along hers, finally stopping where our mouths were practically touching. Her tongue shot out of her mouth and ran along my lips while I continued to smile. As she licked my lips and my front teeth, I let my hand stray under the fabric of her old t-shirt, finally resting on her pert breast, feeling her breathing become heavier and faster. Her nipple was hard and called to my questing fingers. But then, Mr. Johnson came home! He walked in and stood, flabbergasted by his front door. She and I scrambled to cover our obviously flushed cheeks and erect tits. I hung my head and smiled shyly and said, “I didn’t expect you back so soon, Mr. Johnson. I’m sorry and this won’t happen again.” “That’s right, it won’t. Not without me here to supervise, young lady.” I was shocked! He started moving towards us with a sly smile on his face. I stared at my shoes and held my dear friend’s hand; as he approached I could feel my panties dampen with unexpected excitement. Be the next Mr. Johnson for me, Rachel: 1*888*430*2010

July 19, 2014

Published by Madison at July 19, 2014

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Sissy

Today I think I’m in the mood for some sissifacation phone sex. I love getting sissie calls. They’re just so submissive and cute! Plus the fact that they let me dress them up in any cute little outfit I desire doesn’t hurt either! Sometimes I can’t even decide what I want to put them in! So so many choices. Everything from garters, stockings, panties, lace panties, latex, rumba panties, dresses, skirts, short shirts, boots, heels, the list is endless! Sometimes the fun comes from just picking something out! What does my sissy want to wear today? Tell Mommy so she can get your outfit ready for you. Maybe after we dress you up we can take a trip to the mall to show off your new outfit? I’m sure everyone would love that! It’s just one of the things that gets me excited about sissy phone sex. Janey 888*430*2010

April 8, 2013

Published by Madison at April 8, 2013

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Two Sitter Humiliation

Well Cali told you all the boring stuff hahaha! All about dumb little Brian. He always pulls that same crap, behaves himself for a while, and then he starts being a defiant little shit! Oh but I know his tricks, and I know exactly how to get him back in line… and have a little fun!! I spent just enough time upstairs with my boyfriend to let lil Cali turn Brian into Brianna haha. See, my boyfriends got a special taste for sissified ABies! So I got him all good and ready while we were upstairs. I laid back and let him watch me finger myself while he got his cock ready. Once I heard sissy Brianna crying I knew it was time… We dragged our sissy slut upstairs and presented her to my boyfriend. As soon as sissy babie Brianna opened her mouth to cry he shoved his cock in! Brianna’s eyes just about popped out of her head! I showed Cali how to punish Brianna every time she tried to get away from my boyfriends cock and how to make her lick pussy while she got her sissy ass fucked!! It’s a good thing I’m teaching Cali how to be a good adult baby sitter. Pretty soon she’ll be as good as me!! Jenna 1.888.430.2010

October 19, 2012

Published by Madison at October 19, 2012

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CBT Sitter

Here we go again, but ya know, I can’t complain, this is makes for fun babysitting! Apparently when I told you what I would do if you kept being bad you thought I was kidding. I tried everything I could think of. No play time or treats, time out, spanking, paddling, nothing seems to work. But don’t you worry, I have something very special planned for you. I should have known that the best way to go is always humiliation… and pain. Let’s get you upstairs. You’re always saying you’re too old for diapers, so let’s get that off. And we’ll get you into a pretty little dress. HAHAhahaa, aren’t you a pretty sight! You just go ahead a lay down on the carpet there. Now about these restraints, they’re just so you don’t try to squirm away, this is very delicate business ya see. Squirming might lead to permanent damage. We’ll start with the clothes pins. One, two, three, four… all around the sissies little jingle balls. Shhhh, quiet now, we wouldn’t want to bother the neighbors. Oh but that’s my fault. Silly me! I forgot the gag! That’s better. Soooo, I thought I would try some new techniques out. See what’s the most effective. See, I have all these fun little toys to test drive. Pliers, needles, and knives – oh my! But first I think we’ll start something light and easy. Toe of the shoe first… then the heel. Pressure increasing slowly just a teeny tiny bit at a time. OOOH! That’s a pretty color red you’re turning! Oh I love this kind of babysitting fun! xoxo Samantha 1.888.430.2010

July 1, 2012

Published by Madison at July 1, 2012

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Sissy Phone Sex With Princess Jenna

Sissy phone sex with teasing Princess Jenna is something every diapered sissy should experience… You look left and right, rummaging for things you might find cool or interesting. Your heart races knowing at any moment you can get caught. A knock comes at the door. You freeze, shoving all the contraband into your pockets before the door opens. “Jenna? Is that you making all that noise-What are you doing in the guest room young man?” Your mother looks at you with stern eyes, her hands on her hips, tapping her foot. “You know your cousin Jenna is staying with us for a couple of days. She would be really upset if she found you going through her things.. “Jenna! Get in here!” she calls. You become so nervous the only thing you can hear is the frantic beating of your heart. “Yes Miss?” Jenna walks into the door way and turns to see you standing there pathetically in front of her suit cases. “Jenna since its your stuff, I’m going to let you handle this one. I’m going to the store to pick up a couple things for dinner. I’ll be back in a bit.” Oh no you think, your Mommy was your only source of protection. Now she’s leaving. What if Cousin Jenna finds the panties hanging out of your back pocket? What will you do then? Ironically, her eyes go straight to the top of her panties peeking out of your pocket. “Put them on” she simply says. Your face goes beet red, and you glare at her saying no. “Either you do it or I’ll do it for you.” She closes the door, locking it behind her. Her eyes look you over. “You really are a filthy pest aren’t you little cousin? The first 3 times I’ve visited I’ve caught you doing the same exact thing. At first I brushed it off, thinking boys would be boys. But this is the forth freaking time. I’m tired of going home with missing garments. Why do you like my panties so much? Not even my panties, my whole wardrobe for that fact. And don’t give me that “what are you talking about” bs. I’ve seen you wearing them. In fact, I have pictures. I bet you if i were to pull your pants down right now you would be wearing some of my panties wouldn’t you?” You look down, […]