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Babysitting infantile sissy baby Annie - #4

It was a Thursday afternoon, and I was sitting at my desk doing my usual school homework when my phone rang. It was sissy Baby Annie’s mother calling me to ask me if I could help her out and babysit Sissy Annie on Sunday afternoon. She had to do some work for client of hers that day. 

Sissy Annie and her friend Amy and Amy's mommy, Ms Molly were to go to the theatre that afternoon to see a production of Beauty and the Beast. Annie's mommy couldn't go so she was looking for a babysitter. I told her that I could definitely help her out.

I told my mom that I had a baby sitting job that next Sunday.  She smiled and said it will give me a chance to wear my new blue dress.

When Sunday arrived, my mother helped me get dressed. She fixed my hair and did my makeup.  She even told me I should wear nylons like a real woman does to the theater. 

Mommy drove over to sissy baby Annie’s house. When we got there Amy and her mother were already there and waiting. We walked in and greeted everyone.  Baby annie was sitting on the on the floor in her blue dress.  The one with the lions, elephants and giraffes. Such a pretty baby dress! Annie was sucking on her binky and holding her Samantha doll tightly. Her blonde hair looked so lovely in curls with a light blue ribbon and bow. Amy was wearing a dark blue crushed velvet dress with white socks and black patent leather shoes and had a red little bow in her hair. 


Amy's mommy, Ms Molly, said it was time to go to the theater  because she wanted to make sure we had a decent place to park. I helped Annie into her car seat buckled her up nice and tight. She was still clutching her Samantha doll and sucking on her binky  as we arrived at the theater.

I helped Annie out of the car and took her binky out of her mouth put it into my little purse so she would not lose it. As we walked down the sidewalk towards the theatre, she grabbed my hand and held it tightly for safety.

Once inside the usher took our tickets and escorted us to our seats. Ms Molly told the usher that she would need a booster seat for Amy. The usher looked at Annie and asked if we needed a booster seat for her also. Ms Molly and I both kind of chuckled and said no but thank you anyway

The theatre was decorated beautifully for the holiday. There were several Christmas trees on the balconies. They had sparkling lights. I could see Annie looking around and just taking it all in and enjoying herself. 

Once then the music started to swell and the house lights went down I could feel Annie grabbing my hand.  She was a little startled by it but then all of a sudden the stage lights came up. The performers entered the stage carrying their props and singing the opening song, Bonjour,  to the Beauty and the Beast musical. Belle entered from the left wearing her beautiful blue dress with the white apron carrying her book in her arm.  I could hear both Amy and Annie say to one another that Belle is so beautiful.

The show continued through the first act. Annie and Amy were engrossed in the story, the music and the pretty costumes. When the beast made his first appearance Annie grabbed my hand. I squeezes her hand as if to say that it's allright. Of course, the Beast is scary to small children.

During the second act, as the final rose petal starts to fall, I could see and feel Annie grabbing my hand even tighter. Obviously she is wondering what was going to happen to Belle and the Beast. Just then, as the final rose petal starts to fall, the Beast magically transforms himself into the Prince. Annie jumped to her feet almost dropping her Samantha dolly on the ground. I was able to help her catch Samantha. She was cheering wildly along with the rest of the audience. Both Amy and Annie were crying at the happy ending!

Once the show was over, we stood up and made our way back to the lobby. I looked at Annie and asked her if she needed to be changed because she was whimpering. She nodded "Yes". I told Ms Molly. She took Annie to the family restroom just off the lobby of the theater.

Amy and I stood in the lobby waiting for Ms Molly and Annie. The lobby was so pretty with all the decorations and lights. While we were standing there an older usher woman came up to us and asked if we needed any assistance.  Amy told her no and said we are waiting for our mommy to come out of the restroom. I was a little bit shocked but also had a very warm feeling come over me as I looked at her. She put her arm around me knowing that that's how she thought of me. 

We then walked back to the car. I put Annie back into her car seat and took her binky out of my purse and put it back in her mouth. Annie really needed the comfort. I could hear her sucking.

I told Ms Molly what the usher woman had asked  and what Amy had told her about the 2 of us waiting for our mommy. Ms Molly had a smile come over her face.  She gave me a hug and said,  well of course what do you think Amy would say? 

Halfway home I turned around to look and there was Annie, sitting in her car seat, holding her dolly, sucking on her binky, and falling fast asleep 

Arriving home I helped Annie out of her car seat.  Mommy opened the door. I helped baby Annie her into the house and laid annie down on the couch.  Mommy asked me how things went at the theater?

I told her that Annie was the perfect little girl.  That we had no problems whatsoever and I thanked her again for the tickets. I told her that we all loved the show. Mommy  helped me get Annie into her playpen. She was fast asleep. We put a little blanket over her as she sucked her on her pacifier. 

Amy was still rambunctious and wanting to run around. Ms Molly told her that they needed to go home. There was not time to play with any of the dolls as they walked out to the car. I again thanked Ms Molly for allowing me to go with her. She replied that it was wonderful having me there. That I am a good babysitter. Amy then ran up to me and hugged me around the waist and said goodbye.  She said "Claire thank you so much for going with us."  Maybe 5 minutes later my mother arrived to take me home. Annie's mommy She hugged me and then whispered gently into my ear next time you're going to have to tell me about the boy.

Love, Claire


13 comments:

  1. Sissy claire, I love your cute photos! Especially that pink and white little girl dress!

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    1. Thank you so much for the kind complement, Mistress Delores.

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  2. sissy claire that pink little girl dress is so cute! You really should be a full time little girl sissy like Annie.

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  3. Claire: I would love to get to know you better! E-mail me: prettysissydani@gmail.com

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    1. I am sure I will after the fist of the year some time

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  4. I love your reports about babysitting sissy baby Annie!

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  5. Claire is the perfect pre-teen babysitter!!

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  6. I want to thank all of you for you great comments, I love babysitting Sissy Baby Annie, she is a joy to be with and is regressing in to such a wonderful sissy baby girl. I know in this coming year her, and I and her little girlfriend Amy will have fun adventures. Please look for more in the new year. Claire

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    1. You are such a good babysitter for me. I love how you always treat me as an infantile sissy baby.

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    2. I hope you post more babysitting stories of sissy annie soon!

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  7. I love that blue dress on you, Claire! You are a darling and pretty girl! Thanks for babysitting sissy baby annie. You are the best!

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