The Baby Sitter:
Now Robert I want you to know that I have decided on the girl who is going to baby sit you for a week while I go on vacation with my boyfriend James. You may remember her. Her name is Christine. She’s a fourteen year old.
She was that little freckle faced red headed girl, who seemed to be enjoying herself with you so much during the tryouts last week. Remember how red faced you got when I told you to drop your pants and underwear and bend over and pull your cheeks apart to show her your ass hole? And how she giggled when I squeezed your balls and you let out a scream? And she asked me if she could do it too? Well she’s going to be able to do it any time she wants to for a week because I have told her you have got to do absolutely anything she asks and she can do anything she wants to you!.
I spoke to her and her mother just this morning and they are both very pleased that she’ll be staying over here to look after you. Of course they both know you will have to obey every command that she gives you or she has a full right to spank you without mercy on your bare behind..
Her mother agreed that it’s an exciting opportunity for a teen aged girl to learn how to really keep a man under her control. Initially though, I suggested she’d follow the program you have been trained in, so at first you can expect from her pretty much the same thing you get from me these days.
That means when you get home from work the first thing you are expected to do is take off all your clothes and fold them neatly, with your pink lace panties that you have to wear to your office every day on top. You will then bend over and spread your legs and grasp your bottom cheeks and pull them wide apart like she saw you do the other day. You know the reason for this. Yes, it’s so she will have a good view and easy access to your anus. She will stick her finger in to see if there is any brown, and she will also of course check your panties for shit streaks and if she finds any, the next step is a punishment enema followed by a good sound spanking. I told her to give you the enema and spanking the first night whether she finds anything or not, just to make sure you know what you can expect. And she is to do the same thing the first time her mother comes over to see how things are going. Her mother says she is just dying to spank you herself, with her own leather strap. And of course she will get the chance.
Well you’ll eat dinner naked of course and then it will be beddy bye time for you unless Christine has something special she wants to do to you. I don’t know what you can expect but I can tell you she loved squeezing your balls and may want to do the same with your tiny little pee pee. And of course if she wants your help with cleaning up, like getting down on the floor and licking her feet, you just do whatever she asks, understand?
And when you do go to bed she will help you put on that pretty lace baby doll nightie that I and my girl friend Alicia bought you last week, remember?
Oh, and Alicia may come over too. I told her you get a guaranteed spanking and punishment enema when Christine’s mother comes over, and Alicia may want to help. At least with the spanking part. And she can show them how we have taught you to crawl around naked on the floor with your behind high up in the air and beg us not to hurt your tiny pee pee too much.
Well, I want to make sure that Christine understands everything that’s expected of you, so I have asked her to come over here tonight for a rehearsal. And James will be here also to enjoy watching your total humiliation. And don’t worry, we all know how much you love it!
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Hello Mrs. Fulsome, I am so excited about being here tonight and getting this awesome job. Is he already naked or do I get to undress him first thing? I do! Oh that’s wonderful. My mom will be over a little later but she said the first thing I should do is see how fast he can get naked and into position so I can check his heinie hole and if he isn’t fast enough he gets an extra punishment.
So Robert you heard me didn’t you? Good. Now I am going to start counting and you do just what your wife has you do every night. Off with all your clothes and fold them neatly and bend over and spread those bottom cheeks for me.
Oh and Mommie says you must call me Miss Christine not just Christine. Understand? OK? And I’m warning you I just can’t wait for a chance to squeeze that little peepie and those balls of yours so let’s get started!
One…two…three…four….five…six….my I thought you’d be faster than that…seven…eight….. OK OK I think 25 is way too slow and just look at how messy your clothes are. You have to do it much faster than that. So just stay just like you are now and let me give those balls of yours a good tight squeeze. Now you can scream your head off as far as I’m concerned but no jumping up in the air like that. You get right back into position like you were. And here, I’m going to take your pink panties and shove them in your mouth so the next time I squeeze your balls I won’t hear you screaming so loud…
Now that was much better. Now let me shove my finger up your asshole and let’s see if it’s dirty or not. Hmm. Actually it’s pretty clean. But like Mrs. Fulsome said you are getting an enema and a spanking tonight anyway when my mom get’s here which should be pretty soon. In the mean time, go crawl into the bathroom and lick the toilet clean and then get your biggest spanking paddle and crawl back in here with the paddle handle in your mouth.
Wait, there’s somebody at the door. Go get it. And be quick about it too.
Hello you must be Mrs. Fulsome’s boyfriend James. I’m Christine the baby sitter. How do you like Robert with his panties in his mouth. Isn’t that cute? I’m waiting for my Mom to get here so she can watch me give him an enema but for right now I’ve got him cleaning the bathroom toilet with his tongue. Want to watch? Mrs. Fulsome should be ready any moment now.
That’s a good idea, why don’t you go spend some time with Robert’s wife while I take a few more practice squeezes on his balls.
Robert! You pay attention to me now. Bend over and spread your legs so I can get a really good squeeze going! Oh my goodness. What a little cry baby you are. Wait til my mom sees that. Ahah, there’s the doorbell. Let’s go down and see who is there.
Well Hello Mama. This is Robert. Isn’t he cute? What do you want to do first? Give him the enema and then whack him with that big leather strap or whack him first with the strap. Great. OK Robert, you heard what my Mama said. Bend over and grab your ankles. No. spread your legs just a little bit wider so she can spank your bottom and and whack your balls and pee pee at the same time. That’s it! Oh Mama you are so good with that thing. Isn’t he a cry baby though? Just watch him cry. Robert! You get down and let my Mama smack you a few more times, hear? Then it’s enema time. Oh what fun!
Oh this is so nice. Mama this is Mrs. Fulsome and her boyfriend James. I guess they are going to watch while I give him the enema. Now Robert you just bend over and pull your heinie cheeks apart and I’ll just stick this in while you are standing up. OK everybody. Do you think I’m doing a good job. You do? That’s nice. But why is Robert crying? Oh I see. He always acts like a big baby huh? Well, that’s OK with me. Robert you go in the bathroom now and empty your bowels and then come back here for another spanking. You hear me? Now march!! How am I doing Mrs. Fulsome? Oh I’m so glad you approve. I can tell you I am going to just love this assignment!
