The Sitter's Weekend - Diaper Sissy

The Sitter’s Weekend

I stood outside the house listening to Mrs. Forte yelling at her eight year old son for almost a full twelve minutes. “NO JASON, PUT THAT DOWN JASON, JASON STOP IT!!” Poor Mrs. Forte, she couldn’t find anyone else who would even consider watching her little terror of a boy. I walked up to the door and rang the bell. There was some scuffling and some whispered warnings in a hushed stern voice right on the other side of the door. It swung open to reveal a very tired and harried looking Mrs. Forte and a very energetic overly rotten little kid. I tried my best to hide my smile; I didn’t want Mrs. Forte to think that I was laughing at her predicament. She grabbed Jason by the arm and led him into the living room. It was a mess, toys everywhere, most of them broken, scribble marks on the walls, crayon marks on the coffee table. She gave me an apologetic look and started giving me the contact information I would need incase anything were to happen. I smiled slightly and reassured her that nothing was going to happen and everything would be fine. She gave Jason a kiss on his forehead to which Jason screamed in reply. What a lovely little child this is I thought to myself. I waved goodbye to Mrs. Forte from the bay window in the living room and then turned to face this angelic little thing sitting on the floor before me.

“What are you looking at?!?!?” he said from behind his chocolate covered smirk. “What? Or who?” I asked back from behind a steady gaze. He didn’t say anything back he just looked at me and went back to playing with his matchbox cars. I walked away and went to the guest bedroom to put my stuff away. I heard a noise behind me but I didn’t turn around because I knew it would be Jason. “What is all that stuff?” he asked walking into the room. I turned around and said, “This STUFF as you call it is my clothes and few other, uh, treats for tomorrow. Go back to what you were doing, I’ll be out soon.” He didn’t move, and neither did I. We must have stayed like that for a good 20 minutes before he finally said, “I didn’t wanna see your stupid stuff anyway.” He walked away and I turned to finish unpacking, laughing to myself.

The rest of the night was like that. I would ask him to do something, he would say no and hold out for as long as he could before showing just how much of a little boy he actually was by giving in with the words, “I didn’t wanna do that anyway” or “I didn’t wanna play with that anyway.” Around 8:30 p.m. I told Jason it was time for bed, and to my surprise he actually went, no whining, and no back talk, just him walking to his room. I went in fifteen minutes later to find him drawing a stick figure of me with what looked to be a tank firing at my head. I leaned against the door way and said, “My eyebrows are not that bushy.” Jason jumped about two feet in the air. “Are you going to go to sleep or stay up all night planning military coups against my freakishly round head?” He giggled a little bit and kept on drawing. I walked away, went into my room and went to bed. Tomorrow held so many wonderful surprises for my little man Jason.

5:30 a.m. came quickly; I dressed and went to wake up Jason. He had fallen asleep with the marker in his hand. I studied his work on the wall and found out that I had been conquered by what looked to be a squadron of really fat F-14’s. I tapped him on the shoulder and sweetly whispered “Jaaaaaaaason, oh Jaaaaaaaaaaason.” He sat up rubbed his eyes and stated, “Hey, it’s still dark outside, Mom lets me sleep as long as I want.” To which I replied, “I am NOT your Mom. Get up, get dressed and meet me in the living room, you have 10 minutes, miss the deadline and you WILL be sorry.” Apparently Jason didn’t believe me; thirty minutes later he arrived at the table in the same clothes on. Jason thought this was the best thing ever judging by the smile on his face. It was the “HA, HA, I won face.” Little did he know that the only thing he won was punishment, “Jason? Didn’t I tell you that you would be sorry if you didn’t do as I asked?” “Yeah so what?” he shot back at me. I shook my head a couple of times and went to get my bag from my room. “Come here Jason, I want to show you something.” He pushed his chair back away from the table and ran over. “Look inside there, I have a gift for you.” I said this with a very warm and inviting smile on my face. As Jason leaned over to peer into the bag I quickly grabbed him by his upper arms, pulled him screaming between my legs, and sat down on the sofa. I clamped my legs tightly against his and forced him down onto my lap, I roughly pulled his jeans down so his little butt was sticking out. Then he did the worse possible thing he could do, he tried to cover up his butt with his hands.

I grabbed his wrists and pulled them up his back so his elbows were bent, he thought he was strong, but I’m much stronger. I grabbed my bag as Jason started to really wiggle, and pulled out my dear old friend Mr. Blister. I pulled my free hand back as far as it would go, and heard that familiar sound of the air moving around the face and through the holes of the paddle and WHAP! It connected with Jason’s butt, he let out a sound that was part Oh My God and wolf howl, another and another until Jason was nothing more then a red butted whimpering mass on my lap. I put the paddle down, pulled up his jeans and said very softly, “Are you going to listen to me now?” There wasn’t an answer, so I gave him one harder whack with my hand on the outside of his jeans. He gave a little yelp and I asked again, “Are YOU going to listen now?” He shook his head yes. I released my grip on his wrists and pushed him off my lap. Jason stood there teary eyed watching me put the paddle back in my bag rubbing his slightly red wrists.

For the next two days Jason put all his toys away, scrubbed the walls and furniture, got a bath, changed his clothes, started saying please, thank you and may I and going to bed when told. It only took three more spanking to get him to that point. Not that bad if you ask me. Mrs. Forte came home and was in shock. She asked me what I had done, I told her nothing special, just introduced Jason to a very good friend of mine. She paid me and I left, but I will be back Jason, don’t you worry little man, your mom has a business trip this next weekend. See you then!