For the rest of the evening, I managed to stay out of trouble and I found out later that my mom was going have me stay much longer than earlier anticipated, perhaps as much as a week. This was partially good because she was furious when she found out about the panty incident.
I went to bed without getting in any further trouble but in the morning, I awoke to a soggy mass between my legs. Rolling over, I felt the wet diaper squish against my bottom inside my plastic panties.
Getting out of bed, I went to the wall mirror to look at my reflection. The frilly nighty Jennifer had made me wear barely covered my sagging diapers and I looked very sissyish. With a heavy sigh, I went out of the bedroom to find Jennifer preparing something in the kitchen. She was wearing some thin tight shorts and a striped top with a very low cut V in front.
"Are your diapers wet?" she asked by way of greeting.
"Uh-huh," I mumbled, embarrassed.
"Well sit down at the table, I'll change you after breakfast.''
I didn't feel it wise to protest so I sat down with another cold and wet squish. After eating some cereal, she brought out a big red rubber bag with a long white tube attached to it.
"Do you need to go poo-poo?" she asked.
"Um, no Ma'am,'' I said as I squirmed in my soggy seat.
"Well, I don't want to take any chances,'' she said as she hung the glistening bag from a hook on the ceiling, ''this will prevent any messy diapers today.''
She took a seat and beckoned me over.
"Are you g-going to spa-spank me?'' I asked fearfully.
"No. I'm going to give you a nice soapy enema, now come over here and quit stalling.''
As she pulled down my plastic panties, they clung to my wet diapers and she simply pulled the saturated cloth down to my ankles. Seeing her deep cleavage I started to get a little hard-on but she ignored it as she pulled me over her lap. My stiffened wiener rubbed against her silky thigh and I felt myself becoming aroused despite my best efforts. Almost immediately, I felt her greasy finger probing my back hole and I squirmed uncomfortably on her lap.
"You better settle down if don't want another session with the paddle,'' she warned me.
I bit my lip and looked down at her spike heels helplessly as she buried her Vaseline covered middle finger all the way in and swirled it around. As she pulled it out, I felt her re-invade my hole with a warm but thick nozzle. I whimpered in panic and tried to clench my cheeks together but she slid it in effortlessly and a moment later, I felt a surge of hot water gurgling unimpeded into my rectum.
Without thinking, I let out a moan that sounded like it came from a little girl as the soapy water flowed into me. Occasionally, Jennifer would stop the flow and wait for it to settle in before resuming the enema. A bead of sweat appeared on my forehead and I squirmed as my babysitter released the clip again and the hot soapy water continued to fill me up. I felt the cramps set in and I wondered desperately how much longer I'd have to endure this torture.
I moaned helplessly and tried to rise off her lap but she easily held me down and snapped the clip shut.
"I'm afraid not, my little sissy-boy. You've still got a lot more to go. I want to make sure you get a good cleaning because you're going to be in your diapers all day and I don't want to be changing any messy ones later."
I bit my lip and squirmed uncomfortably over her lap as she released the clip again.
About ten minutes later, Jennifer finally emptied the rest of the bag into my pouting bottom and let me up. I limped to the bathroom and released the enema in a torrent as I heard her call to me.
"When you're done, come into the bedroom so I can get you dressed."
I could only wonder what she had in mind but I hoped she'd allow me a little dignity since I'd been trying to be better.
After I had cleaned up, I walked into her bedroom wearing a towel around my waist. She was sitting at her vanity, applying some lipstick to her full and sensuous lips.
She caught my reflection in the mirror and stood up from her seat.
"Come on, let's get you changed, you've a big day ahead of you," you informed me tersely.
I hated the sound of 'getting changed' and I looked down at the triple thick diaper laying on the changing pad. She patted the center and beckoned me to sit on it but I clung stubbornly to my towel.
"Now, you can either do this the easy way, or I can get my paddle and we can do it the hard way--its up to you Mister," she told me with a superior smirk on her face.
My lower lip trembled as I pouted and knew I was beaten. I slowly unwrapped the towel and she guided me down on top of the soft mass of cotton.
"That's a good baby," she cooed. From somewhere I hadn't noticed, she produced a baby bottle full of warm milk and she pushed it between my lips. "Here you go Bobby, maybe this'll make you feel better."
I blushed hotly as I took the bottle and suc-ked miserably on the nipple. She powdered my fanny and crotch before pulling the thick diaper up and pinning it snugly with big, pink ducky pins. Despite my intense feelings of humiliation I couldn't help but love the baby softness that now enveloped me. I felt so comfortable and secure and I thought, as long as no one else sees me, this might not be too bad. I found myself unable to close my legs but before I could think about that, the doorbell rang.
My heart skipped a beat as Jennifer went to see who it was.
“Don’t you even think about moving,” she cautioned me with a wag of her manicured finger. Nervously, I held my breath as I heard her open the door, followed by several women’s voices as they greeted each other. They talked for a few minutes and then I thought I heard them coming down the hall.
In a panic, I looked around the room. Where could I go? The only door out of here led to the hallway and now they were coming in!
I blushed hot red as Jennifer came in with two women, one, in her late thirties, and the other, obviously her daughter. Both were very attractive with long brown hair and sexy figures and her daughter wore a short halter top that displayed her curvy breasts nicely.
I gasped in shame and looked down at the floor as the mother came over to the bed.
“So this is the baby you’re taking care of,” she exclaimed excitedly, “My, you’re a big one, aren’t you Darling,” she said as she pinched my cheek.
“I was just getting him dressed for the day when you came over,” Jennifer explained.
“What a sissy,” her daughter said with disdain, “Does he wet his diapers too?”
“Oh yes, just like any little baby. I have no idea what his mother was thinking, letting him go around with big boy underpants on. As often as he wets, I wouldn’t dare let him out of his diapers.”
I wilted as she belittled me in front of her friends.
“Tiffany, I was just about to put him into his plastic panties, would you like to pick out a pair for me? They’re over in the closet there,” Jennifer asked.
“Sure, I’ll find something for the big sissy,” she replied mockingly.
She came over with a pair of white nursery print plastic panties, the leg and waist openings lined with soft ruffles, and held them up for me to see.
“Is this what Mommy’s little sissy wants?” she asked condescendingly.
I pouted and shook my head no.
“You’d better learn some better manners than that if you don’t want your bottom paddled again Bobby,” Jennifer warned me sternly.
I looked up at her fearfully, my face red with shame.
“Please don’t Aunt Jennifer,” I pleaded.
“Then what do you say to Miss Tiffany, who has so kindly offered to get you ready for the day?” she prompted.
“Yes, Miss Tiffany,” I mumbled barely audibly.
“Speak up Bobby,” Jennifer warned, her voice taking on an edge.
I cleared my throat.
“Yes, Miss Tiffany.”
“Yes, Miss Tiffany, what?” Jennifer prodded.
“Yes, Miss Tiffany, may I please wear those plastic pants?” I said in a shaking voice.
“Plastic panties,” Tiffany corrected me. “Baby boys wear plastic pants. Sissy babies like you, wear plastic panties.”
"Plastic panties," I repeated dutifully.
Tiffany held the leg holes open and guided my feet through them, sliding them up my skinny legs and then up and over the thick, bulging diaper I was wearing. I couldn’t help but look down her top and watch as her breasts jiggled before me. She had to tug and pull to get the panties up over the bulky cloth but she was soon tucking the last bits of it into the elastic leg and waist bands.
“There. All secure now. This baby won’t be wetting on the car seat,” she said confidently.
“Car seat?” I quaked, “Wha-what do you mean?”
“You’re coming over to our house today, Sissy, as soon as we’re finished dressing you,” she replied.
By now Jennifer had pulled off my nighty and she began lowering the pink dress from yesterday over my head. My mind was in a panic as I struggled with what I should do. Before long, Jennifer had me in my anklet socks and Mary Janes as her friend tied my hair into pigtails.
“We’re almost ready to go,” Jennifer said as she opened her dresser. “Now, we’re ready,” she said as she picked up her wooden paddle and put it into her purse. I shuddered as I saw that and they stood me up to look at their finished efforts.
“Turn around, Bobby,” Jennifer ordered me.
They made me twirl around like a ballerina and as I complied, I caught sight of myself in the full length mirror on the wall. My babyish nursery print panties could easily be seen bulging out from beneath the short, frilly hem of my party dress. I looked so sissyish and infantile, my lip trembled and I thought I was going to cry.
“Oh, quit pouting, Bobby,” Jennifer frowned, “You know you enjoy wearing frilly panties. I’m just giving you what you were afraid to ask for.
“Now come on, let’s go. I don’t want any trouble out of you today,” she warned me.
As we began walking out of the bedroom, Tiffany stopped us.
“Oh wait, we forgot something.” With that, she came over and popped a pink pacifier into my mouth.
“Now, we’re ready,” she said with a sadistic smile.
We headed for the door, Jennifer pulling me along determinedly by my wrist. As the full impact of what was about to happen hit me, I stopped in my tracks. It was one thing to be dressed up like a baby girl inside, but quite another to be taken out in public. I tried to yank my wrist free but her hand was like a vice.
“No, noo!” I squealed as the pacifier dropped out of my mouth.
“Come along, Bobby. You’re going out that door and that’s all there is to it!” she told me sternly.
“No! I can’t!” I said, the panic rising in my voice. I looked around for support but Tiffany had already scooped up my pacifier, brushed it off, and was bringing it back to my mouth.
“Do you need me to put you over my knee again, young man? Because I’m perfectly happy to do it. I’m two seconds away from pulling those diapers down and paddling your bottom until you won’t be able to sit for a week!”
My lip quivered in fear and I knew all too well she meant it.
“No, please…not that, aunt Jennifer,” I begged.
“Then let’s get going,” she said as she opened the door.
I winced as the sunlight hit me and my eyes darted around, looking to see if anyone was outside that would be able to see me. As I stumbled out behind Jennifer, I caught sight of her neighbor, a women in her twenties who was washing her car in a pair of shorts and a bikini top. She saw me and immediately began giggling.
All of a sudden, in the midst of my panic, I felt a stream of pee surging out into the front of my diaper. I felt the blood redden my face as I blushed deeply again. Quickly I rushed around to the other side of her car in a vain attempt to hide myself. As I waited for my aunt to unlock the door, I tried to pull down the lacy hem of my dress to hide my exposed diapers but it was futile. No amount of tugging would cover the colorful nursery characters decorating my plastic pantied bottom as a daughter and her mother soon pointed out.
“Look Mommy! That guy’s wearing diapers!” the little girl practically shouted.
Tears of frustration and shame trickled down my cheeks as I tried the door again frantically. Jennifer leisurely opened her door and got in behind the wheel and in my agitation, another stream of pee escaped into my waiting diapers. The others chatted patiently as they waited for my aunt to unlock the doors. Finally, I heard the sound of the doorlocks being released and I yanked mine open and tumbled inside. Tiffany appeared beside me and she stuffed the pacifier back in my mouth.
“There you go, Bobby,” she said in her syrupy demeaning tone of voice, ”Isn’t dat better for little snookums?”
I hung my head in shame and wondered what would happen when they found out I had already wet my diapers. I re-lived in my mind, the stinging spanking I had received yesterday and wondered uneasily if there would be a repeat today.
The drive over was relatively short except for an incident we had when we pulled next to a truck with a pair of men in it. They could easily see down into the back seat of our car and the seatbelt I was wearing had pulled the hem of my dress back, exposing the front of my fat diapers for everyone to see. I could only chew the rubber nipple in my mouth helplessly as they made lewd comments about my sissyish appearance.
Tiffany giggled at my discomfort and taking her cell phone out of her purse, began dialing a number for a call.
“Hey Melissa, what’s up?” I heard her talking with her friend and for the moment, I was ignored.
While Tiffany was distracted, I found myself carefully stealing a look at her very adult figure. Her long brown hair spilled over her shoulders and my eyes wandered down, taking in the sensuous curves of her young, but full breasts, straining at the thin fabric of her pink halter and her flat belly beneath. What I would give to kiss those perfect boobs, I thought, but dressed in diapers, plastic panties, and a sissy dress, she was as unattainable as the moon to me.
“What are you staring at??” she said accusingly, interrupting her call and my reverie.
“I-I, uh, nothing,” I stammered, turning to look out the window.
“You better not or I’ll have your aunt paddle that bottom of yours,” she warned.
I cursed myself for my indiscretion as she jammed the pacifier back into my mouth.
“The next time I see that out of your mouth, I’ll turn you over my own lap. Do you understand me, Sissy?” she said with a menacing voice.
I nodded my head fearfully and tried to ignore her as she pulled her top down to smooth out some nonexistent wrinkles. In doing so, her breasts pushed forward displaying her cleavage and her nipples poked out erotically. My little wee-wee stirred in the damp confines of my thick diapers and I had to fight the urge to keep from stroking it.
“Yeah, c’mon over, you and Barbie, I’ve got a surprise for you,” she told her friend with a devilish smile, “and bring your curler set.”
We arrived at Tiffany's house a little later and I was taken to the living room while Jennifer and her friend Heather went to retrieve some clothes. While I suc-ked on the pink pacifier in my mouth, they brought out a pair of dresses for me to try on.
One was white with pink lace and ruffles and had a built in petticoat, soft and fluffy. The other was pink satin, very frilly and feminine. Both had short, puffy sleeves and a hem that would clearly show off my bulging diapers. Amidst giggles and teasing, I tried on the dresses and was made to model them, twirling around and striking several humiliating poses.
Eventually, Jennifer and Heather left us, giving Tiffany free reign over me. Fortunately, no one had discovered my wet diapers which were clinging miserably to my damp bottom.
The doorbell rang and Tiffany jumped up expectantly. As she opened the door wide, I froze as I took in the two hot cheerleaders that were her friends. Besides the short, short skirts that showed off their sexy legs, their tops were a clinging, shiny material that pushed their breasts into an alluring cleavage. Just as I started to feast my eyes on these two sexy babes, they caught sight of me and began laughing uncontrollably.
I wished the earth would open up and swallow me but instead I turned beet red and kept my eyes downcast in humiliation.
After a lengthy explanation of why I was wearing diapers and sissy dresses, Tiffany led the three of us into her bedroom.
''Oh my gawd,'' Barbie said, ''He is such a sissy! You mean he just lets his aunt dress him like this? Without a fight?''
"Yep. It's because he likes dressing like a baby--that's why he doesn't complain,'' Tiffany explained.
I tried to protest but the pacifier in my mouth made everything sound babyish and muffled.
"I know! Let's give him a sissy makeover!'' Barbie exclaimed, ''I have just the lipstick!''
Enthusiastically, they sat me down on the vanity stool where I landed with a squish and they began making up my face. Tiffany put a foundation on while Melissa began painting my nails in a bright glossy pink enamel. Barbie applied several coats of bubble gum pink lipstick to my puckered lips while Tiffany emphasized my long eyelashes with a tool I was unfamiliar with, making them more pronounced and feminine.
"He's already blushing up a storm but I say we give him some pink blusher anyways,'' Barbie suggested.
"Absolutely, '' Tiffany agreed, ''Let's make him as sissyish as possible.''
When they had finished, they stood back and admired their efforts.
"You look just like a little sissy toddler,'' Melissa remarked with a smug look.
"With those pouty pink lips and batting eyelashes, you're sure to snag a big macho stud,'' Tiffany commented.
I turned crimson at the suggestion but said nothing.
"Oh, definitely, I could easily see those lips wrapped around some hunk's big coc-k,'' Barbie agreed.
"I'll bet you'd love that wouldn't you, Bobby?'' Melissa asked.
"No!'' I protested unconvincingly.
"Oh yes you would,'' Tiffany insisted, "All sissies love to suc-k coc-k. I'm sure you fantasize about it all the time while you play with your pathetic little pee-pee, don't you Diaper Boy?''
I was about to offer some opposing remark when Melissa interrupted me.
"And now, it's time to do something with that hair,'' she said testing the temperature of her curler set.
"Wha-what are you going to do now?'' I asked apprehensively.
"I'm going to give you a Shirley Temple permanent. But don't worry, it'll grow out in four or five months,'' Melissa laughed heartily.
The others laughed with her but I stood up and made ready to escape.
"Oh no, you don't,'' I said defiantly.
"Bobby! You sit that diapered butt of yours down right now or you'll be sorry!'' Tiffany snapped angrily.
"No! I won't!'' I cried petulantly.
"What’s going on in here!''
I froze instantly and all eyes went to the hallway. Jennifer stood framed by the door, tall and intimidating, her big breasts thrusting forward proudly.
''Bobby won't let us use curlers on him,'' Tiffany quickly explained.
Before I could utter a reply, Jennifer glared down at me, her hands resting on her curvy hips.
"You girls hold him there, I'll be right back,'' she said as she spun on her high heel and left the room.
The girls grabbed each of my wrists and held them tightly.
"You're going to get spanked now,'' Barbie gloated.
''Someone's gonna get paddled, someone's gonna get paddled,'' Melissa said in a sing-song voice.
I bit my lip fearfully but soon heard the familiar 'click, click, click,' of Jennifer's heels approaching from down the hallway.
As I quaked with fear, a strong burst of pee flowed into my already wet diapers. I whimpered in despair as Jennifer strode in with Heather, the wooden paddle in her hand. Grabbing my wrist, she pulled me over to a straight backed chair forcefully and stood me next to her.
"Bobby, you've been asking for this all day and now you're going to get it,'' she snapped.
"Please--please don't, Aunt Jennifer,” I begged pathetically.
As I looked into her beautiful but stern face, I was filled with panic and I helplessly let loose with another stream of pee. Jennifer could hardly fail to notice and she looked down at the growing yellow stain inside my plastic panties with unconcealed disgust.
''Bobby! What is the matter with you? Can't you keep your diapers dry for one hour?!'' she demanded angrily.
''I-I... I,'' I stuttered.
"Never mind, I'm going to blister your bottom,'' she said as she tore my nursery print panties off of my clinging diapers and down to my knees. Pulling her skirt up to prevent it from getting wet, she yanked me over her lap where I landed with another humiliating squish. Her thighs were firm and strong and she supported my light frame easily as she wrenched the pins out of my diapers.
From where I dangled over her lap, I looked up anxiously to see the other four women smirking with looks of satisfaction. I felt a chill breeze over my dampened cheeks as the warm, wet diaper was pulled back and the flouncy hem of my dress pulled up. My bare fanny tingled in frightened anticipation of the spanking I was about to receive.
''Bobby,'' Jennifer paused, "Are you a mature young man, or a sissy little boy who needs his bottom paddled?''
"I'm a ma-mature young man,” I quaked uncertainly.
The paddle crashed down hard on my behind, making me jump from the impact.
"YEOWWW!!'' I cried pitifully.
SMACK!! SMACK!! SMACK!!
Jennifer slapped my quivering cheeks fiercely, the hard wooden paddle quickly changing their color to a hot, angry red.
"Are you a mature young man or a sissy little boy who needs his bottom paddled?'' she asked again, holding the paddle poised high over her head.
"I-I'm a sis-sissy little boy who n-needs his bottom spa-spanked,'' I blubbered.
"That's right,'' she agreed.
The paddle swooped down again on its avenging mission to land squarely in the middle of both cheeks, leaving a searing and painful impression on my tender fanny. I cried out in anguish and kicked my legs frantically as my shiny Mary Janes beat a jerky rhythm on the floor. The spanking continued without respite, and my kicking and flailing only tangled the wet plastic panties around my ankles. In seconds, I was bawling like a baby, the tears streaming down my face. I sobbed and wailed but Jennifer only increased the tempo of the spanking, slapping my bottom with what seemed even greater severity. I could hardly catch my breath between each stinging smack of her paddle and my cries came out a stuttering 'ah-ha-ha-wah.' By now, my entire bottom had been transformed into a blazing, hot inferno like a stove top and my bunched fists shook impotently.
Finally, at long last, the spanking was over. I lay over her lap heaving, trying desperately to catch my breath as I sobbed deeply and profusely.
Jennifer stood me up on wobbly legs and looked into my crying eyes.
"There, there,'' she consoled me as she held me closely. She cradled my head to her immense bosom and patted me on the back.
As I hugged her, I buried my head into the comforting softness of her immense breasts and blubbered like a little girl. I could plainly see the lace of her bra underneath the thin fabric of her top which strained to contain it all. I was close enough that my tears dribbled off my face onto her exposed chest, to trickle down her deep cleavage.
''Tiff, can you reach into my diaper bag and get me the bottle of baby oil?'' Jennifer asked.
Tiffany handed it to her who proceeded to fill her cupped hand and then apply it to my blazing behind. I cried miserably as she rubbed it repeatedly over my stinging cheeks until they glistened with a slick, slippery sheen. With my face pressed against the soft, forgiving cushion of her breasts, I felt her slip a greased middle finger into my anus and helplessly, I let out a girlish moan. My crying subsided and my pecker stirred to life as I was stimulated in front and back. As she supported my slippery bottom with her hand, she buried the finger all the way in and twirled it around, making me blush with ecstasy.
''There, there baby, your spankings all over,'' Jennifer said consolingly, ''Let's get you back into a soft, fluffy diaper and then it's naptime for our little sissy.''
Reluctantly, I released my hold around her waist as she turned me around unsteadily. I blushed anew as Tiffany and her friends took in my tiny erection and giggled, bringing forth fresh tears of shame. Ignoring my distress, Jennifer unfolded the plastic vinyl changing pad and laid it out on the bed. From her voluminous diaper bag, she took out a stack of fresh diapers and baby powder and set it down as well.
"Here you go baby,'' she told me, ''Dry your eyes, Aunt Jennifer's got a nice fresh diaper for you.''
She patted the thick, soft center of the cotton cloth, beckoning me to sit upon it. Totally defeated, I set my still stinging bottom onto the diaper and let her powder my wee-wee area. Soon a baby scented cloud surrounded me and she pulled the sides up, pinning them securely and once again, I was locked into my baby soft prison.
Heather plopped a waiting bottle of warm milk in my mouth and I suc-ked on it obediently as Jennifer shook out a pair of pink plastic panties. After removing the damp pair from around my ankles, she pulled the pink pair up my shaky legs and wrestled it over the triple thick diaper.
"There,'' she said brightly, ''All safe and secure like a sissy should be.''
I blushed again as I looked down at my fat, bulging diapers and then around at the other girls looking at me.
"Tiff, do you happen to have a nighty our little diapered princess can wear for his nap?'' Jennifer asked.
"Sure thing,'' she replied.
A moment later, my ruffled dress was being replaced with a frilly white and pink nighty and Tiffany gave me a big teddy bear to hold.
"Here you go Sissy, here's a teddy that'll help dry your tears,'' she told me.
I held it close as I suc-ked the last bit of the milk from my bottle. Tiffany's mom was all ready with another and she popped it in between my lipstick covered lips. After the severe spanking, I was exhausted and I let them lead me into a guest room where they tucked me into bed. In moments, I was asleep, clutching my teddy bear and nursing from my bottle like any diapered toddler would.
Betty Pearl's Sissy Stories 20.1
Topic: Bobby's Babysitter (Read 20861 times)
