The Babysitter Takes Over Ch. 02

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Teri the babysitter ups the ante with her sissy.
874 words
4.29
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Part 2 of the 3 part series

Updated 06/08/2023
Created 03/05/2018
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Chapter 2: The party

"Ok bitch, I'm going to invite my friends over tonight for a party. I'm going to text them an invite and I want you to do it. Now go over there and start talking. And you better make it good or I'll post the pictures on my Facebook page."

I went over to the corner and started talking while Teri got her phone out again and pointed it at me. I spoke in a high girly voice and a lisp. "Hi this is sissy sherry and I'd like to invite you to a party tonight at my house. It's going to be so much fun! We are going to play truth or dare, talk about boys and maybe have some guys come over. Please come over as soon as you can."

"Not bad bitch. I'm going to send it out now; I'll put your address in the text. When they get here you will do everything —and I mean everything — we tell you to do. Now we've got to get ready."

I spent the next hour cleaning up the house. I set up the living room and cleared out the middle of it. She told me to freshen up my makeup, especially my lipstick. I vacuumed, dusted and sprayed some feminine air freshener all around.

Meanwhile, Mistress Teri was on her phone most of that time; she looked up and giggled at me every once a while as she talked. I had a very uneasy feeling about what she was doing. She had a very evil look in her eyes. At one point she had me pose for a picture while doing a courtesy.

Just as she hung up the doorbell rang and Teri told me to answer it and to act as a sissy. I was in my pink babydoll nightie and fully made up but since she had so much on me I did as I was told.

"Hi and welcome! Come on in!"

Five teen girls came in laughing at me as they came into the living room. They were all dressed in provocative clothes and of course, they all had cell phones in hand.

"Girls, this is sissy sherry and I own her ass. We are going to have a lot of fun at this party and she's the guest of honor. I'm having a surprise visitor coming later but for now let's have some fun with her."

Teri told them that I would do whatever they told me to do so they should ask away. The more humiliating the better. "Let's see a striptease!" they all shouted.

One if the girls started playing "Style" by Taylor Swift on her phone. I didn't really know what to do but they started screaming at me to start stripping. So I seductively danced for them. I took off the top of my nightie and they told me to play with my tits. I did so as they bounced around. The girls hollared insults at me as the top part of my nightie was thrown into the group of girls. That left with just the G string on.

"Now take off the panties" they screamed and I did so. I took them and whirled them around my fingers. The laughing was immediate. "OMG she's hung like a grape!" one of them said. I was forced to stand there while they all took pictures of me naked. They told me to tuck my little dick between my thighs so it looked like I had a pussy. One of them got the whole striptease on video.

"Now let's see just how much of a sissy she really is!" said Teri. She told me to get on my knees; she had gotten on a strap on harness with a huge black dildo attached. I was told to start sucking and immediately complied. I licked the balls and ran my tongue up and down the shaft. I loved the feeling as I slid it into my mouth. I then started sucking on it. Of course the girls were capturing the whole thing on their cell phones. I was able to deep throat it with only a little gagging as I kept sucking. Teri dick slapped me while laughing at how pathetic I looked.

"Now let's warm the bitch up. Get over there to that couch and assume the "sissy slut" position. That means lean on the couch, stick your ass up in the air and arch your back. And hold your ass cheeks open bitch." After doing so, I felt something slippery on my ass and then the unmistakeable feeling of being penetrated. Teri started fucking me hard while the girls held me down. I was really starting to enjoy the feeling as I submitted to her. She hammered me from behind for quite some time. I moaned like the cheap slut I have become. But I did wonder what she meant by "warm her up?"

Just then the doorbell rang and I was told to answer it. They told me to put my nightie back on and walk like a girl over to the door.

I opened the door and standing there was my ex wife's black boyfriend...

To be continued...

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7 Comments
AnonymousAnonymous4 months ago

After reading chapter 1, I didn’t think the story could get any worse or more unbelievable, but chapter 2 proved me wrong. The 18 year old female character has to have at least a trace of conscience in order for the story to be even tolerable.

Royse69Royse69almost 3 years ago

OH shit boyfriend is going to be drilling both the wife and sissy

liz33ndliz33ndalmost 5 years ago
this could be more fun

I am not sure about the babysitter attitude. but I will keep reading. its pretty good.

cdCindy1cdCindy1almost 6 years ago
Don't like the blackmail

Not crazy about the blackmail but the public humiliation is great.

sissysherry2sissysherry2about 6 years agoAuthor
Thanks for the suggestions!

This was my first submittal here and really appreciate the suggestion. I’m thinking of a fourth part and any input is appreciated... ss

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