The Babysitter Takes Over

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A closet Sissy is discovered by a teen babysitter.
971 words
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Part 1 of the 3 part series

Updated 06/08/2023
Created 03/05/2018
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"I know your secret."

These were the words that I had both dreaded and longed to hear from my babysitter.

Let me start at the beginning. I am single and have a couple of kids at home who aren't quite old enough to be on their own when I have business obligations. I share custody with my ex, who left me to be with another man, who happened to be black. I get the kids during the week, my ex gets them over the weekend. Teri had answered a babysitting ad for watching them after school and sometimes during the evening. She is the answer to an older man's dream- 18, hot as hell, very athletic body. I noticed lately she had been wearing tight clothing; perhaps to make her more attractive to me. Whenever she would leave, I would take the next opportunity to go to my bedroom to masturbate.

One Saturday, after dropping off the kids for the weekend, I answered a knock on the door. It was Teri.

"Hey Teri, you know the kids aren't here. I don't need you this weekend."

"Oh that's where you're wrong, you do need me." She walked in without asking.

I didn't say anything as she just walked in; she is just so damn hot.

She said "Let me get right to the point. Last night I got curious about you so I let myself into your bedroom." I froze and just about passed out. One of my fetishes is dressing in nighties and I hoped she hadn't found them.

"I know your secret" she said and smiled. "Now lets go upstairs and play!"

So we went upstairs and into my bedroom. She sat on the bed and got her phone out.

"Now you are going to do whatever I tell you, right?"

"Wait, do we really have to do this?" I protested.

"Oh come on, you KNOW you want to do this. You want to be my bitch, don't you? I can tell by the way you look at me. Now take off all your clothes."

I decided this was my chance to play out one of my fantasies so I decided to go along. I took off my shirt first.

"OMG, check our those man boobs. They are bigger than mine, you know. Play with them for me, bitch." I complied and she started giggling. "OK, now for the pants, take them off."

Again, I complied. Then she walked up to me and felt my tits. She put her hands on my boxers and pulled them down. That's when the real laughing started.

"Holy shit! Look at that micro dick. No wonder your wife left you for that black guy! And you can't even get it up with a hot chick right in front of you. Are you a sissy?"

"Yes" I stammered.

"I knew that already because last night I went to your dresser." She then recreated the scene by walking over to my dresser. She pulled out on of the babydolls that I had hid at the bottom of the drawer. It was the pink one. "I found this—put on this nightie on for me sissy."

She handed my the pink babydoll nightie and I slipped the panties on first. I didn't think I had much of a choice. It was a G string that barely covered my dick. She then told me to pose and started taking pictures on her phone.

"Now for the top" she said. I complied and felt the smooth fabric cascading over my body. It fit perfectly and I was instructed to pose for her as she took more pictures on her phone. I think I'll call you 'sissy sherry' from now on, bitch." Then she told me to go into the bathroom.

"I noticed that you have some of that disgusting body hair. I brought a bottle of nair and I want you to spread it all over your body. I want it on all over from the shoulders down, including your chest, underarms, arms, back, shoulder, around your clit and your legs." While we were waiting for the nair took hold, she took more pictures of me and instructed me to smile for the camera. She told me to talk like a sissy and captured a video of me telling her my sissy name. After ten or so minutes she had me go into the shower and wash it all off. I watched all my body hair go down the drain. I stepped out of the shower silky smooth. She handed me a bottle of feminine moisturizer and had me spread it over my entire body. I must admit it felt fantastic!

"Time for makeup; lets get you nice and pretty." She had me sit in front of a mirror and applied foundation, blush, lipstick, mascara, eyeliner and eyeshadow. I posed once again for pictures and videos.

"You probably know this, but I own your sissy bitch ass now, don't I? Tell me you are now my property."

"You own me Mistress Teri! I am your sissy slave."

"Good little bitch. I am now going to take control. I'm going to start by having you sign on to your bank accounts, then leave the room. I am going to change the username, password and all your contact information. I am going to link them to my bank account and take what I want. I will also do that to your 401(k) account and your other investment accounts. We are going to have soooo much fun playing; I'm going to invite some of my friends over for a little party tonight. And don't you dare embarrass me bitch!"

I couldn't see my way out of this so I agreed, not knowing what the future held. But I was excited to find out!

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Royse69Royse69almost 3 years ago

so far its good start, I will wait to see what happens

The minute it became a money thing, any single father would have taken the phone away and thrown her little ass out, that money is for his kids welfare and future as much as his.

a lot of times these stories start a certain way and then goes somewhere different

besides that it was a good start

Thank you

Tootight1Tootight1over 4 years ago
Good story

Yes it is, as an example to other CD/TV's what can happen when you trust someone who doesn't deserve it. 18 yo female, she doesn't know what she wants yet, other than your money. Did anyone get even a hint that she actually had any feeling for him, no.

Wait till dark, keep her phone, and what ever else she has, put her in the trunk, and take her fishing. Problem Solved.

cdCindy1cdCindy1almost 5 years ago
good story

I'm a married closeted sissy Cd - and I love this story. A hot young girl becoming my Mistress turns me on so much. I can't wait to suck cock in front of her. Tell us more. Please.

AnonymousAnonymousabout 6 years ago
Shit

Pure unadulterated shit!

AnonymousAnonymousabout 6 years ago
Gay sissie

Good for your gay ass wants to suck a studs dick you gag.

Who asked you?!

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