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My bottom was still stinging from the paddling I had received from my mother earlier this morning when she had found I had wet the bed for the second time this week. She was getting impatient with me since I was now 14 and my bedwetting episodes were becoming more and more frequent. As a result, I found her treating me more and more like a child and today we were on the way over to one of her friends who was going to be babysitting me during the summer days. I chafed at the idea of having to be babysat like I was still a little kid but I resolved to be defiant to whoever she had in mind for me and make them realize I was someone they couldn't control. My mom might be able to still spank me but I was determined to establish my authority with this new person, whoever she was.
We pulled into the driveway of a very tidy house and got out to ring the doorbell. I was stunned by the woman who answered the door. She was gorgeous with long brown hair cascading over her shoulders, a tight, low cut top that revealed huge round breasts threatening to spill out. Her flat tummy was visible above the short skirt she wore and her legs were long and perfectly smooth. As I gaped at her incredible breasts, I realized just how tall she was. She looked easily over six feet, and even more with the high heels she was wearing.
"Hello Bobby," she greeted me sweetly.
Being inherently shy, my initial bluster immediately deflated and I blushed as I stammered clumsily.
"Um, ah, uh, hi," I said as I shuffled my feet and looked downward.
"Bobby's a little bashful but he'll warm up before long," my mom told her. "Now young man," she said stearnly, "You are to do exactly as Jennifer says, do you understand me?"
I mumbled my aquiesence and looked away, at the same time stealing glances back at my new babysitter's incredible figure.
My mom made small talk with Jennifer before bidding her goodbye and warning me again to behave. After she left, Jennifer showed me around her house but instructed me never to go into her bedroom without her permission which I agreed to but secretly found myself drawn to.
For the rest of the afternoon, I kept myself busy but inside, I fantasized about my beautiful babysitter. Later that day, I saw Jennifer doing some work in the kitchen and figured I would have the chance to sneak into her room without her knowing it.
Quietly, I tiptoed down the hall and into her bedroom. I was overwhelmed with the feminity of everything from the lacey curtains to the silky bedsheets. I moved to the dresser and opened the top drawer. Inside I found sexy bras in various colors and I imagined Jennifer's massive breasts filling them up.
My little wiener stirred as I looked at the label and saw the size 40DD on it. My heart began beating hard within my chest and reluctantly, I folded it back and put it where I found it. The next drawer was full of panties, silky and high cut and I swooned with visions of Jennifer's sumptuous derriere encased in them.
On a sudden impulse, I unbuttoned my pants and dropped them to the floor. Stepping over to the hallway, I saw no sign of Jennifer so I pulled out a pair of her frilliest pink panties and stepped into them. The panties felt wonderful and my cock strained against the soft fabric. Taking out another pair, I laid them on the bed beside me and began stroking myself with no thought as to the risk I was taking. I couldn't get Jennifer's fantastic breasts out of my mind, the way they jiggled and swayed as she walked around and my head was swimming at the discovery of their true size. 40DD!
I was in comeplete ectasy and was about to reach orgasm when suddenly Jennifer strode into the room.
"What is going on here?!" she demanded in an angry voice.
I jumped to my feet and blushed furiously, trying desperately to stammer out some kind of response.
"I-I-I, I um I was uh..."
"I told you specifically to stay out of this room and what did you do? You came in here behind my back and started trying on my underwear!" she said shaking her beautifully manicured finger at me. Her other hand was supported on her curvy hips and her tremendous breasts shook provocatively as she scolded me.
"So you like to wear women's panties do you? Well I've got just the thing for you young man, but first we're going to take care of some business."
I gulped nervously at that remark and hurried to take the embarrassing panties off.
"Oh no you don't Buster," she stated as she grabbed my hand, "You wanted to wear those, you're going to wear them until I make other arrangements-but first you're going to find out what happens to little boys who disobey me."
With that she pulled me behind her roughly as she went to another drawer and yanked it open. Pulling out a wooden paddle, she sat down on the bed and positioned me next to her lap. By now, a wet spot was obvious in the front of the panties and Jennifer stared at it in disgust.
"Your mother had told me you were bedwetter but I didn't know you were a little panty pervert as well. What do you have to say for yourself?" she demanded.
My cheeks burned wih shame as I looked down at the long line of cleavage that disappeared into the V of her top. I had nothing to say but I couldn't stop the stimulation I felt when I gazed at her big beautiful breasts.
"You have nothing to say? Well, I have a solution that will take care of both problems, but first, I'm going to blister your bottom."
With that, she yanked me roughly across her lap and I felt my cock pressing against her bare legs. Her thighs were firm and large and I found myself dangling over them as I looked down at her spike heels. Halfheartedly, I struggled to get up but was interrupted by the harsh impact of her paddle searing itself on my cheeks.
"OWWWW!!" I shreiked in surprise and pain.
SMACK!! SMACK!! SMACK!!!
Jennifer brought the paddle down upon my pantied bottom with a vengeance, slapping my youthful globes in a stinging continuous rythm.
In moments I had burst into tears and I kicked frantically as the paddle slapped my bottom without pause. In an instant, my fantasies about Jennifer evaporated as I was reduced to a blubbering child caught wearing panties.
"So you like to wear frilly panties do you?" she said, punctuating each word with a fierce slap of the paddle. "Well if it's panties you want-then panties you shall have!"
The tears streamed down my face and I bawled like a baby. My mother had never spanked me like this!
At last she stopped and stood me up on my shaking feet. My knees were weak as I sobbed uncontrollably before her, comepletely defeated.
Setting down the paddle, she got up and went to her closet, opening it up and bringing back an armful of items, amongst them, a pair of pink plastic nursery print panties, a thick cloth diaper and a changing pad. Setting down the latter item, she spread it out and beckoned me over to it. For a moment, I thought about resisting but the inferno blazing on my bottom warned against it and I sat down in the middle of the cool plastic pad. Despite it's coolness, I winced as my burning cheeks settled down on it.
Uncerimoniously, Jennifer tore the silk panties off me and threw them aside. I whimpered as she grabbed my ankles, lifted them up abruptly and slid the diaper underneath me. I was amazed at how thick it was as she sprinkled baby powder over my privates. Her massive breasts swung before me as she pinned up either side with a snug click of the diaper pins. I tried to allieviate the stinging pain of my bottom by lifting myself off the pad while Jennifer shook out the plastic panties.
"These are the panties you'll be wearing from now on little boy," she said as she pulled them up my legs and over the fat diaper. I blushed all over again and found I couldn't put my legs together, so thick were the diapers.
"Take your shirt off," she told me as she walked over to the closet again.
"But...why?" I asked meekly.
Without answering me, she brought back a frothy pink dress with white ruffles and a big pink bow in back. Pulling my shirt off, she threw it in the corner and brought the dress down over my head. Obediantly, I held my hands up as she guided it down over me, buttoning it up in back up to my neck.
"You obviously like dressing like a sissy so I'm going to help you out. And you'll wear these diapers because I don't trust you not to wet your pants."
I blushed in shame and looked down at the floor.
"Now go out in the living room and behave yourself," she commanded me.
Thoroughly chastised, I waddled out of the room but not before seeing my reflection in the full length mirror. With the thick diapers bulging out from beneath my dress, I looked just like a little toddler girl who needed her mommy. With a sob of shame, I fled the room.
I had to admit, after the stinging had subsided from my bottom, my diapers felt pretty good. They were bunny soft and extremely comfortable and the plastic panties fit me like glove. My dick was constantly being caressed in the thick white folds and I felt a strange mixture of shame and erotic pleasure.
I did my best to behave myself the rest of the afternoon and later, Jennifer went out to the back yard to work on her tan. I watched in awe as she unbuttoned her shirt to reveal her massive boobs, straining urgently against a tight white bikini top. They jiggled sexily and I glanced at her perfectly trim bottom as she settled down on her lawn chair.
Without thinking, I began stroking the front of my diaper, the plastic crinkling beneath my hands as luxuriated in pleasure. I took in Jennifer's incredible body, her breasts rising and falling as she breathed. Before long, I came with a delicious orgasm, filling the front of my diaper with warm creamy goo.
Unfortunately, as my dick shrank back to it's original form, the feeling of pleasure was quickly replaced with an urgent need to urinate.
Biting my lip, I debated what I should do. I could try and get Jennifer to take my diapers off but then she'd see what I'd done and paddle me all over again. Rubbing my still sore bottom over the plastic panties, I knew that wasn't an option.
Alternatively, I could try to remove it myself but that wouldn't do any good because she had locked the bathroom and her bedroom, preventing me from using that option.
Pacing in the kitchen, I struggled with the problem as my need to go became more and more critical. At last I couldn't hold it any longer but I figured if I could just let out a little, maybe that would relieve the pressure and Jennifer wouldn't notice when she checked me later.
Relaxing for just a moment, I felt a stream of pee saturate the front of my diaper. I gasped in despair as another, even stronger surge followed the first, soaking the cloth and causing the diaper to sag. I quickly realized there was no way I'd be able to hide what I'd done so I relaxed and just let it go. The pee seemed endless and I felt it soak into the seat as I emptied my bladder into my diaper. With a sob of despair, I sat miserably, the sopping wet diaper squishing against my bottom. I dreaded what Jennifer would do when she caught me, a 14 year old teenager, having soaked his diapers like a baby.
An hour later, Jennifer came back in, looking fabulous in her white bikini. I tried to busy myself but she came up behind me and squeezed the seat of my diaper, instantly feeling the wetness inside.
"I cannot believe it. You really are a sissy aren't you?"
I cowered in shame before her as she towered over me, her hands on her hips.
"You really are just a big baby. How did your mommy ever get you out of diapers anyway?" she demanded.
"Well come on baby," she said as she reached down and grabbed my wrist.
"Let's get those wet diapers changed."
Taking me to her bedroom, she unlocked the door, pulled me inside and sat me down on the changing pad.
"Looks like I'm going to have to keep a good supply of diapers whenever you come over," she said caustically as she pulled a fresh pair from the closet. Yanking my panties down roughly, she exposed the pee soaked cloth causing me to blush hotly.
"Look at you-you should be ashamed of yourself! " she said as she unpinned my diaper and pulled it out from beneath me. "I've babysat some childish boys before but never such a sissy baby as you."
With little effort, she held my legs up in the air, exposing my damp bottom in the most humiliating way.
"I'm going to call your mommy and tell her you need to be put back into diapers and plastic panties-what do you think of that?"
"I couldn't help it," I squeaked.
Jennifer powdered me until a cloud of scented baby powder rose around me.
"You couldn't help it? Why didn't you just call me?" she demanded, "It must be because you LIKE wearing diapers. I think you're mother will be very interested to know that." she told me as she pinned my diapers up snugly.
"Please don't tell her-Please!" I begged her desperately.
"Oh, I'll tell her allright, and I think you can depend on getting another spanking when you get home." she assured me as she shook out a fresh pair of pink plastic panties. I whimpered in defeat as she pulled them up my legs and over the fat diaper, snapping the waistband as a final touch.
Going back to the closet, she brought back some knee high socks and a pair of white patent leather mary janes.
"These should fit you, if not, I have some pink ones that will," she said as she pulled off my socks and replaced them with what she had. I wilted with embarrassment as she buckled the straps on the girlish shoes.
Taking a brush from her vanity, Jennifer brushed my longish hair into pigtails and clipped a pair of pink bows on either side. Her big breasts hung inches before my face, tightly encased in the thin white fabric of her bikini top and I could easily make out her pert nipples.
"And since you get such a pleasure out of wearing girly panties, I think I've got just the thing." she said as she went to her closet again.
"These should be right up your alley," she said boldly as she held forth a pair of pink satiny rhumba panties. A soft row of ruffles surrounded the leg openings and graced the seat with another three.
She held them out for me to step into and I meekly obliged, steadying myself on her shoulders as she drew them up my legs. It took a little tugging to get them up and over the thick bulging diapers but they fit fine and the ruffles kind of tickled my leg.
"Now. Try to behave yourself," she told me.
As I waddled out of the room, she swatted me on my ruffled bottom.
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 enama, 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 cock rubbed against her silky thigh and I felt myself becoming aroused despite my best efforts. Almost immediatly, 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 vasoline covered middle finger all the way in and swirled it around. As she pulled it out, I felt her re-invade my hole with 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 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 wwearng 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 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 sucked miserably on the nipple. She powdered my fanny and crotch before pulling the thick diaper up and pinning it snug with big pink duckie 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 that 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 affirmed.
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, "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 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 frilly hem of my party dress. I looked so sissyish and feminine, 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 lacey 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 man’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 relived 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 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 cascaded over her shoulders and my eyes wandered down, taking in the sensuous curves of her 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 fanny 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 stop myself 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 sucked 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 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 cock," 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 suck cock. 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 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 diaper. 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 makefully 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 butt, 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 desperately, 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 fresh diaper 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 sucked 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 sucked 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.
An hour later, unknown to me, Tiffany and her friends snuck into my room. They suppressed their giggles as they walked on tip toe, carrying a bowl of warm water towards the bed.
With utmost care, they pulled my hand away from my teddy bear and laid it carefully into the bowl of water. A minute later, they were rewarded with a hissing sound under the covers as I proceeded to soak my diapers. When they were satisfied I had peed all I could, they removed the bowl and snuck back out of the room, their giggling following them.
Later on, when I woke up, Jennifer checked my diapers and she wasn't pleased to find them soaking wet again.
"Well little Sissykins. I guess I overestimated, once again, your maturity level. Looks like you’ll just have to wear your wet diapers home, since I don’t have any more to change you into."
I looked down, too ashamed to speak. It seemed like I was totally losing control over my bladder and reverting back to the days when my mom kept me in thick training pants. In those days, she made me wear plastic pants over them, long into the fourth grade before I finally learned some measure of potty training. They were humiliating days when the other kids teased me mercilessly, saying I was still wearing diapers. Actually, that was true, but only at night where my mom knew I'd wet the bed if I wasn't kept pinned into a thick pair of fleecy diapers and plastic pants. It wasn't until sixth grade that I finally graduated from my nightly "protection" and began sleeping in just my pajamas.
And now, I was right back where I started from, having reverted to my former babyish lack of control. As I looked up at her enormous breasts and deep cleavage I could only mumble out, "I guess I had an accident."
Jennifer scoffed at that and pulled me out of bed.
"Melissa was kind enough to leave her curler set here so you’ll be happy to know you didn’t get out of getting your hair permed. I agreed that it was a wonderful idea and I think a Shirley Temple hairdo will compliment the short dresses and diapers I’ll be keeping you in for the rest of the summer."
I cringed at the thought of three more months of nonstop humiliation.
Needless to say, my hair did get permed with tight curls and everyone agreed that I looked adorable peeking out from a frilly baby bonnet.
As the summer wore on, I got used to the baby treatment but there wasn’t a day that went by that Jennifer didn’t go out of her way to humiliate me, often in front of others. From somewhere, she got me a lacey diaper top that said, ‘Diapers are my best friend.’ What she couldn’t make on her sewing machine, she ordered from the internet and I soon had a sizable collection of baby and sissy clothes to wear.
Tiffany would often come over to baby sit since Jennifer refused to leave me by myself and I found her to be cruel and strict. On average, I found myself over one of their laps two to three times a week, getting my bottom paddled until my face was wet with tears. The daily enemas also continued and I forgot what it was like to have a normal bowel movement.
Between the diapers and the constant baby treatment, whatever fragile potty training I had acquired soon vanished and I feared what would happen when I returned home. Would I ever be able to wear regular underwear again?
Jennifer told me a sissy is always the last to acknowledge the fact that he is one and I guess that’s the way it was with me too. However, over the course of those months, even I noticed the subtle changes in me. I would begin to cry if I didn’t get my way or when my diapers had been wet for a particularly long time. And secretly, I began to take longer looks in the mirror at the frilly confections they would dress me in, noting the way my ruffled rhumba panties were always on display, my fat diaper bottom bulging out from under the dresses and sissy tops.
But somewhere in the back of my mind, I figured my mom would put a stop to all of it and then it would be Jennifer who would be the one in trouble.
On the last day of summer, the day I was to finally go home, I looked forward to finally wearing my jeans and regular underwear, t-shirt and tennis shoes. I figured Jennifer would never dare to show my mom how she'd kept me dressed the entire summer, in diapers and dresses.
The first sign that things weren't going to go as I planned was after she'd administered my usual morning enema. When I came out of the bathroom, I saw the same triple thick diaper waiting for me on the changing pad as always. I grumbled as she powdered me and pinned me into it, pulling on a pair of white nursery print plastic panties to cover the big diaper. After that, she dressed me in a frilly baby blue sailor suit whose lacy hem just came down to the waistband of my baby panties. A big floppy white bow graced the bodice and the sleeves were short and puffy, rows of lace decorating the edges. She put me in some white knee high stockings and shiny black mary janes. Her crowning touch was a pair of white ruffled rhumba panties, pulled up snug over my thick, embarrassing diapers. As much as I resented having to dress like a total sissy, I only hoped I could keep dry until I got home, so weak had my bladder control become.
The ride over was long, made longer by the fact Jennifer had insisted I finish two jumbo size baby bottles of warm milk. By the time we reached my old neighborhood, my bladder was straining and ready to burst.
We drove over a bumpy section of road and my muscles surrendered to the inevitable. As I proceeded to soak my diapers, a tear of frustration trickled down my cheek.
So much for proving to my mom I didn't need diapers, I thought sullenly. Once again, Jennifer had managed to trick me into humiliating myself.
Before long, the front of my diapers were completely saturated and I felt the wetness seeping up into my seat, giving me a constant reminder of my infantile lack of control.
We pulled into my mom's driveway and I waited as Jennifer got out and came around to unlock my seatbelt. My mom came out of the front door and I feared an extended greeting that would leave me exposed outside. On the other hand, I felt sure that when she finally saw the way Jennifer had dressed me, she'd explode and demand an apology from her sister for the way she'd been treating me.
Feeling a little smug at what I thought was going to be my coming revenge, I hopped out of the car and ran to my mom.
"Bobby!" she exclaimed as she held out her arms.
I embraced her eagerly and felt as her hand reached down to squeeze the thick seat of my ruffled and pantied bottom.
"My, my. Looks like my sister has done a good job of keeping you protected," she observed, "And someone's wearing a very wet diaper."
I blushed hotly but said nothing. Obviously my mom was anything but angry at the way I was dressed and my plans for revenge quickly evaporated.
They remained outside chatting while my mom clung stubbornly to my hand, preventing me from going inside. I paced impatiently as several of my neighbors began staring at me. Filled with shame, I could only turn away as they took in my sissy attire.
Finally, we went inside where my mom led me to my old bedroom. If I was surprised by her attitude before, I was shocked when I saw what she had done to my room.
The walls had been repainted in pink with colorful nursery characters, and frilly lace curtains framed the window. My dark dresser had also been repainted in pink and my bed had been replaced with a big sturdy crib, the bars about three feet high and a plastic vinyl sheet covering the mattress. A little girl's vanity with lighted mirror was against one wall and a collection of dolls sat in the corner.
But perhaps the most humiliating piece of new furniture was the pink plastic covered changing pad with the double stacks of thick cloth diapers piled high and waiting to be used.
I let out a cry of despair as I ran to the dresser and pulled open the first drawer. Inside, where I once kept my underwear, were stacks of baby panties in feminine pastel colors, some with nursery print, some with ruffles and others in solid pink, yellow or lilac, all neatly arranged.
"Where-where's my underwear?" I stammered in a panic.
"Right here, Honey," my mom said as she held up a pretty pair of pink nursery print plastic panties.
"These and a thick set of diapers are all the underwear you'll ever need from now on."
"Don't worry Honey, you'll never have to go poking around in ladies drawers for panties anymore, you have a drawer of your own, full of them," Jennifer assured me.
I stumbled over to the closet in a daze and looked at where my jeans and shirts used to hang. In their place were frilly party dresses, rompers and onesies, all generously trimmed with ruffles and lace and cut short enough to display my embarrassing diapers.
"Yes, there will be some charges around here you'll need to get used to. You obviously belong in dresses and sissy clothes and you certainly can't be trusted without diapers and plastic panties. Your bedtime is now seven pm sharp so I'll be serving you your dinner at 5:30 every evening. I hope you like baby food and formula, ‘cause that’s all you’ll be getting. In the morning I'll give you a nice full enema since that’s worked so well for Aunt Jennifer, and then I'll dress you for the day in something appropriately babyish. In the afternoon, I'll put you down for your nap but you'll keep busy during the morning cleaning up around here. I expect you to wash your diapers and plastic panties daily and hang them up on the clothesline outside to dry.
"I spent a bit extra and got the super soft brand of diapers. These are called 'supersoakers' by Bedwetters and they have extra padding down the middle for heavy wetters like you. Because they're bunny soft, I know you'll be tempted to masturbate in them but I'm telling you now, if I catch so much as a dribble of gunk in them, I'll paddle your bottom so hard you won't be able to sit for a week.
"And just to make sure you stay out of trouble, I've arranged for a nanny to keep an eye on you when I'm not around.
"Meet Miss Johnson."
I gulped when I turned around to meet the intimidating figure standing in the doorway. She wore black high heel pumps, dark silky hose and skirt, and a nearly sheer white blouse that was stretched tight to accommodate her massive cups. With her hair in a severe bun and a no nonsense look on her face that said that she wouldn't tolerate misbehavior, I knew my goose was cooked.
"Bobby, I'm here to tell you that your masturbating days are over," she said with finality, "I've disciplined more than my share of sissys and bedwetters so I'm very familiar with all your little stunts. And just so there’s no confusion as to who’s boss around here, I like to start things off with a nice, good old fashioned, over the knee spanking."
I trembled with fear as she walked over and took the hard oval shaped paddle hanging from the wall.
"Mommy!" I squealed pleadingly, "Please don’t let her spank me."
"It’s only for your own good, Bobby," she said firmly, "A good cry will do you good."
I wailed and stomped my feet in frustration as the buxom nanny took me by the wrist and led me to the only chair in the room.
A moment later, I was in my all too familiar position: wet diapers down, dress pulled up, and tears streaming down my face as my fanny was getting the severe paddling it so richly deserved.
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