Jimmy's New Babysitter
Author: Baby Bobby, Sep/6/2004 14:20:50 [-04]
I could've died of embarrassment.
Melissa, the bossy, buxom senior from my school strode into Aunt Suzie's living room boldly, looking me up and down disdainfully. She wore a tight pink halter top with a low scoop neckline, generously revealing her deep cleavage. Below that was a bouncy white mini-skirt and her usual high heeled pumps. It was obvious from the look on her beautiful face that she held me in contempt and it was easy to see why.
I was still wearing the pink taffeta dress my mom had put me into this morning, not to mention my hair was in pigtails with pink floppy bows and my face and nails were still made up from visit to the salon. My shiny black mary janes contrasted with the pale pink knee high socks I had on my feet but worst of all was the thick, bulging diaper that was clearly visible under the lacy hem of my dress. It was soaking wet for the second time today and it clung stubbornly to my bottom and around my crotch thanks to the snug, shimmery, rhumba panties Aunt Suzie had made for me.
"Sis, meet my favorite babysitter, Melissa," my aunt said to my mom.
"Nice to meet you Ma'am," Melissa said in voice that was more polite than I had ever heard from her.
"It was so good of you to come over on such short notice Melissa. I'm glad to have the opportunity to finally meet you. Suzie's told me so much about you," my mom gushed.
"It's no trouble, I can always use a little extra money," Melissa replied.
"We'll I hope you don't mind, but I've got a bit of a special case here. You see, my son here is a bedwetter and a masturbator--and I've had it up to here with his childish behaviour. I've got him dressed the way he's been acting-like a little three year old girl, which I think is appropriate."
"I couldn't agree more," Melissa said smugly, "he's known as the biggest sissy in school, so it's about time he started dressing like one."
"Oh, one thing," my mom said almost as an afterthought, "if he should give you any trouble, any trouble at all, you have my full permission to take down his diapers and paddle his fanny."
Melissa pulled out of her bag a large flat wooden hairbrush and wielded it in her hand menacingly.
"Don't you worry about that, I'll make sure this little sissy knows who's in charge."
"Good, and please give me a behaviour report tommorow so I can discipline him myself when I get home," my mom added.
I quivered with dread at the thought of being entrusted to the care of this person who knew never liked me and constantly sought out ways to humiliate me.
"Make sure he's in bed by seven," my mom said as Aunt Suzie and her went out the door.
"No problem, Ma'am," Melissa said.
I felt some small relief since seven was only a half hour away. At least there wouldn't be too much time left for her to torment me.
"Melissa, there's a change of diapers for him in the bedroom closet, the one's he has on are soaked. You don't mind changing him do you?" Aunt Suzie asked from the door.
"Not at all! I'll get our little bedwetter changed into some nice dry diapers and then it'll be straight to bed for him," she answered eagerly.
They said their goodbyes and then I was alone with her. Standing with her hands on her hips, she towered over me in her high heels as she glared down at me coldly.
"Let's get a few things straight Baby-boy," she said sternly, "YOU are a sissy. You are the biggest sissy I've ever met in my life and that's saying a lot. I intend to humiliate you like you've never been humiliated before and if that means your bottom gets blistered along the way-so be it."
I quaked in fear and a little pee trinkled out into my already soaking wet diaper.
Without a word, she turned on her heel and walked out of the living room towards my aunt's bedroom. Her five inch heels clicked distinctly across the floor, purpose filled with determination. A moment later, she returned with a handful of thick cloth diapers, powder, diaper rash cream, and a changing pad, the latter of which she spread out on the floor.
"Sit down Sissy," she ordered me curtly.
"M-M-Melissa?" I asked tentatively.
"You will address me as 'Ma'am', Sissy boy," she said firmly as she tugged my glittery panties down my legs.
"Yes Ma'am," I answered meekly, "but aren't I going to bed soon?"
"I've got other plans for you," she said as she began peeling my clinging plastic panties down off my wet diaper and then down my legs. She left them around my ankles and then looked down at me with a frown creasing her pretty features.
"Just LOOK at you. Wetting your diapers just like a little toddler. How old are you? Fourteen? My three year old nephew is more mature than you," she scolded me.
I hung my head in shame, unable to maintain eye contact with her.
"Believe me, I'm going to make sure everyone knows what a big sissy you are," she said as she unpinned the sodden diapers that were now hanging from my hips. They fell to the floor with a splat and she pushed them aside.
Doing only a cursory job of wiping my damp bottom and genitals with a baby wipe, she held my legs up in the air and slid the thick stack of fresh diapers under me. But before letting me back down, she picked up her hairbrush from the floor and swung it harshly, smacking each of my bottom cheeks soundly.
"OWWW!! OW-HOWW!!" I wailed.
Her big boobs jiggled within her top with each stinging slap of the hairbrush.
"THAT was just for being a sissy," she announced with a cruel smile.
I howled in pain and kicked but she held my legs while I struggled as if I were just an infant. I couldn't believe how strong she was!
Taking a big handful of diaper rash cream, she smeared it across my pink bottom with little care taken to ensure it was an even coating. At last she let my legs down and she powdered my pen-is and between my legs until a white cloud filled the air around me. Grasping my diminutive white pee-wee in between her thumb and index finger, she held it like it with obvious disgust.
"What the hell is this?" she asked mockingly.
I didn't know what to say and I feared a spanking if I said the wrong thing so I just kind of shrugged.
"I'll tell you what it is...it's pathetic! But then, it goes with your prissy personality," she laughed scornfully, showing off her beautiful teeth and sensual lips.
"But don't worry, I've got just the thing you can prove to me that you're good at." Reaching into her bag, she pulled out her monster sized strap-on dil-do, its fleshy veins bulging from around its thick shaft.
I whimpered in fear as she pulled the thick, constricting cloth between my legs and pinned it tightly on either side. The bunny soft diaper caressed my skin as she yanked my still damp plastic panties up my legs. She had to wrestle with them to get them over the fat, bulging diaper but at last, it was all contained.
"There, at least you won't be wetting on the furniture now," she said scornfully.