Jimmy's Day of Shopping by Baby Bobby

[archives]

Jimmy's Day of Shopping

Author: Baby Bobby, May/2/2004 11:41:31 [-04]



I woke up in a strange state of arousal.

As I rolled over on my waterproof mattress cover, my hand went down to the thick front of my diapers and felt, to my surprise, that I was still dry. This was highly unusual because I had been waking up every morning for the past two months with my diapers consistently soaked. As I mused over this sudden change, I stroked the surface of my plastic panties encasing the soft diapers. It didn’t take much for my little weiner to become hard and I found myself secretly enjoying my baby soft underwear. My mom insisted on dressing me in cloth diapers rather than disposables, and when she washed them, she used a lot of fabric softener which made them get softer and softer with each washing. As a result, I found myself being constantly caressed by the fluffy diapers and despite my humiliation at having to wear the infantile clothing, my wee wee sought relief.

I had been masturbating covertly for several years now and getting away with it because I found that when I wet myself, the evidence of my misdeeds would be covered up. And so far, my mom hadn't caught on to my recently discovered sinful pleasures. Most often, my fantasies centered around my voluptuous and pretty teacher, Ms. Taylor, although yesterday’s humiliating spanking in class at her hand certainly had curbed any remaining illusions I had about her feelings towards me.

This morning, I swung my legs out of bed and sat up, to be able to stroke myself more comfortably. For some strange reason, I found my mind wandering back to yesterday’s traumatic event at school in the girl’s bathroom. That was where Melissa, a tough yet beautiful senior, and her bullying girlfriends had forced my inside and then humped me senselessly with a big strap-on dil-do.

At the time, I had found the experience to be initially painful, not to mention, extremely embarrassing. I had been forced to endure a long and slow humping as Melissa held me down and forced me to take in every inch of her dil-do. I was crying tears of shame by the time she finished, but now, in the safety of my bedroom, I recalled the experience with a strange sense of arousal. I couldn’t yet identify my feelings but somehow, when I remembered looking into the big mirror on the bathroom wall, my weiner stirred in my diaper. I thought of my tormentor, Melissa, tall, demeaning, big breasted, and dominating. I remembered her big boobs heaving within her tight, stretchy top as she pumped me from behind with her dil-do. But in my secret heart of hearts, I found myself wishing she were here right now, bending me over my bed to hump me again. I blushed at the very thought of it but I couldn't escape or deny the way I felt.

As I stroked the front of my soft diapers, I was reaching a new height of ecstasy, oblivious to my surroundings, when all of a sudden, my mom burst into the room unannounced.

“WHAT-ON-EARTH-IS-GOING-ON-HERE!!?” she demanded angrily.

My mouth dropped open in shock and surprise as I tried to stammer out a response but I couldn’t think of anything even remotely plausible.

“I-I-I…I-um…ahh…I was just…ah,” I bleated out nervously.

“Young Man. You are NOT to masturbate in this house! Do you understand me?!” she demanded as she shook her index finger threateningly at me.

“Yes Mommy!” I quickly responded, fearing her imminent wrath.

She seized my wrist and yanked me up while simultaneously reaching for the paddle, an oval instrument made of hard oak with holes drilled in its face to provide extra sting. I knew from past experience just how painful it could be when applied to a naughty bare bottom. I quaked with fear as she sat in the only chair in the room and began yanking my plastic panties down.

“No Mommy! Please! I won’t do it again!” I begged her piteously.

“Jimmy. You’ve had a good hard spanking coming for much too long now. It’s time for you to have yourself a good cry,” she said tersely as she tugged my panties down past my knees. I whimpered and pleaded but she pulled me over her knee, unpinning my diapers with practiced ease. I was all too familiar with this position and knew there was nothing that was going to save my bottom from being severely paddled. Even before the spanking began, I burst into tears, squirming on her lap as she held me firmly in place with her left hand.

SMACKK!!! SMACKK!! CRACKK!!

I wailed in response and kicked my feet wildly, gyrating on her lap as the paddle swatted my tender bottom with harsh, angry slaps. All thoughts of the beautiful but domineering Melissa vanished from my mind as I focused on the punishment being metted out to my youthful cheeks.

WHACKK!! SMACKK!! WHAPPP!!

[archives]

Jimmy's Day of Shopping, part 2

Author: Baby Bobby, May/3/2004 13:29:18 [-04]



“Naughty boy!”

SMACKK!!

“Naughty little sissy!”

WHACKK!!

“Disgusting!”

SMACKKKK!!!

I howled in pain and anguish as I struggled, kicking my feet and beating my fists against the floor. Tears streamed down my face as I cried and sobbed like a baby.

“You are NOT to use your diapers to masturbate in! Do you understand me??!” she demanded. Without giving me a chance to respond, she continued my paddling without pause.

SMACKK!!! SMACKK!! CRACKK!!

Suddenly, she stopped abruptly and rested the paddle against my blazing bottom. I couldn’t see them, but I knew my cheeks were now a bright shade of red.

“How long have you been playing with yourself?!” she demanded.

Between sobs, I tried to save myself from any further punishment.

“Ne-ne-never. I never have before,” I stammered uncertainly in response.

The paddle swooped down again and again, blistering my bottom in its avenging mission.

WHACKK!! SMACKK!! WHAPPP!!

“OW-WOW-WA-WAHHH!” I cried desperately.

“How long have you been playing with yourself!” she repeated angrily.

“A-A-A couple ye-years,” I admitted tearfully, between gasps for breath.

WHAPP!! SMACKK!! SLAPPP!!!

The paddle came down again and again, stinging my poor fanny mercilessly.

“And how often do you masturbate each week?” she asked, holding the paddle up high over my crimson behind.

“A-a-couple times,” I replied. I knew it was foolish to try and lie now.

The paddle came down again repeatedly until I was sobbing and completely defeated, my face wet with tears. She made sure that my fanny was thoroughly punished as she spanked me good and hard, swatting every square inch until the sides glowed a cherry red like the center. Finally, I felt her pin my diapers back in place over my stinging bottom and stand me up. Bawling like a baby, my shoulders heaved and I tried to rub my burning cheeks through the thick cloth of my diapers. My mom ignored my efforts and yanked my pink plastic panties back into position where they effectively sealed the fire within. I shifted my weight from foot to foot as the inferno on my backside continued to build.

After hanging my paddle up on the wall where it belonged, my mom took off my nighty and replaced it with the petticoat aunt Susie had put me into. I sniffled miserably as she followed it up with the fluffy pink taffeta dress with white lace, pulling it over and adjusted the hem. Wordlessly, she she sat me on my bed and began pulling my knee socks on, followed by my mary janes. I watched her with sinking heart, my legs bowed out at an angle from the thick diaper between my legs.

"Maybe dressing like a little sissy baby will make you want to grow up and start acting like a young man again," she said tersely.

I sniffed in self-pity as she stuffed a big pacifier between my lips and put the loop around my neck. Today, I was determined not to wet my diapers since I didn't want to prolong this treatment any longer than was absolutely necessary.

My mom took me into the kitchen and made my breakfast while I shifted in my seat. I just couldn't get comfortable despite the multiple layers of soft diapers, my bottom stung far too much.

"Quite fidgeting," she ordered me as she put my oatmeal before me. I was glad she wasn't going to feed me too. From somewhere, she produced a large baby bottle with warm milk in it. I scowled but knew better than to refuse it.

"That’s right Jimmy," she said as if reading my thoughts, "there are going to be a few changes around here that you better get used to. We're going shopping today to pick up a few items that you'll be needing."

I was afraid to ask what those would be so I said nothing.

"Before, I was prepared to keep your diapers hidden under your pants but now, it's clear that stronger measures are necessary. From now on, your diapers and plastic panties will be on display for everyone to see them. I'm going to make sure everyone sees just what a big sissy baby you are."

I cried softly to myself as I looked forward to a day full of humiliation and shame.

A moment later, the phone rang and my mom answered it. Apparently it was my aunt and after a brief amount of small talk, my mom eyed me curiously.

"Hold on Sis," she told my aunt as she dug in one of the kitchen drawers. Taking out a measuring tape, she came over to me and told me to stand up. As I did so, she measured first my waist, then the widest part around my diapered hips, then the diameter of my legs where they met the elastic of my plastic panties. My heart skipped a beat as she read the measurements to my aunt. What could she want them for, I wondered. I knew her to be skilled with a sewing machine and I could only imagine what she might be making for me.

My mom smiled at me with a 'just you wait' kind of look on her face before she said goodbye to my aunt and hung up the phone.

After I finished breakfast, my mom told me to go brush my teeth and get ready to go. I pouted in frustration as I did so, being unable to avoid looking into the mirror and seeing my embarrassing reflection. I couldn't believe how sissyish I looked, with my shiny, pink ruffled plastic panties peaking out beneath the masses of white ruffles from my petticoat and dress. There was absolutely no way I'd be able to hide them from anyone who saw me.

My mom soon joined me and she re-brushed my hair, lifting each side into a pair of sassy pigtails and securing them with pink floppy bows.

"There. Take a look at yourself," she said, turning me back towards the mirror, "now you look like the way you've been acting."

A tear formed in my eye as I looked at the diapered sissy baby staring back at me. As if to complete the picture, my mom stuffed my pacifier back into my mouth.

"Come on Baby," she said as she slapped my thickly diapered bottom, "it's time to go."

[archives]

Jimmy's Day of Shopping, part 3
Author: Baby Bobby, May/4/2004 12:54:22 [-04]

I heard the jangle of her car keys and then the realization really hit me. I was going to go out in public dressed like a baby!
"No mommy! Please! Please don't make me go out like this!" I wailed as my pacifier fell out of my mouth.
She frowned down at me before jamming the pacifier back in.
"Come along you little sissy, we're going shopping whether you like it or not."
She dragged me forcefully out the door and in my state of panic, I felt a sudden stream of warm pee escape into my diaper.
"Nooo!" I whined pathetically.
My mom yanked my forward with her left hand and at the same time, her other hand swooped down to swat my behind.
It didn't really hurt but I cried out anyway. Worse yet, another stream of pee followed the first one, creating a large wet spot in the front of my diapers.
Dragging me by my wrist, my mom put me in the back seat, securing my seatbelt like I was still a child. The seatbelt rode over the top of my diaper, pulling my dress up and completely exposing my plastic panties to anyone who should look in. Lastly, she placed my pacifier back into my mouth and warned me not to remove it unless I wanted my bottom warmed again. I certainly didn't want that, so I sat there sulkily, pouting as I suc-ked the rubber nipple.
We drove out of the neighborhood and then through town, moving in and out of slow traffic. At one point, I looked over to see a van of girls staring at me and giggling and I blushed a deep shade of red. It didn't help matters that my diapers were already wet and worse, I felt my bladder needing further relief. How was I to hold out the rest of the day? I wondered nervously.
Finally, we pulled up in front of Babys-R-Us and my mom got out to open my door. I noticed here in town, a strong breeze was blowing and no sooner did I get out of the car when the wind picked up the back of my dress and petticoats, fully exposing my diapered fanny to a family close by in the parking lot.
"OOHhmmmph!!" I squealed through my pacifier as I fought to get my dress under control. The mother of the other family looked at my strangely and I felt myself blushing again. As they walked by, her daughter, a little girl of about five pointed at me and blurted out, "Mommy, why is that boy wearing diapers?"
"I don't know Katie, now come along," she said as she took her inside of the store.
I was so ashamed I felt like crying.
We went inside and I gazed around at the vast showroom of baby furniture and supplies. There were all manner of cribs, toy sets, playpens, changing tables, not to mention a section dedicated to baby clothing and diapers. A older, matronly woman came over to assist us. She looked very severe with her hair pulled up into a bun and her conservative clothes. She eyed me with suspicion but greeted my mother warmly. I suc-ked my pacifier nervously as I was unable to hold eye contact with her.
"And how can I help you today?" she asked.
"Well, we have a small problem," my mom began, "you see, this morning I caught my little baby here masturbating. So I need a playpen that I can put him into where I can keep an eye on him."
I blushed furiously at this admission to a total stranger and when I glanced back up at her, she was staring at me harshly. I had the feeling she would spank me herself if given even the slightest encouragement and I shifted from one foot to the other in anxiety.
"A little masturbator, eh?" she said disainfully, "well I think we can find something that will keep him out of trouble. Come right this way."
She lead us down an aisle of larger baby furniture until we reached a number of playpens. She waved her hand at one that had a padded vinyl floor with nursery print characters decorating it. The sides were made up of a soft netting that went to pink padded side rails, about three feet off the floor.
"This woud be good," my mom commented, "this way I can place him in here when I'm busy around the house and keep him where he can be constantly supervised. Now, it seems to me that a baby in his playpen needs to have some toys otherwise he might be tempted to play with something else. Isn't that right Jimmy?"
Reluctantly, I nodded my head but kept my eyes downcast.
"Perhaps your little baby would like some dollies to play with?" the saleslady suggested. She took us to the toy section and they picked out a "Little Miss Wettums" doll, one that still wore diapers and would wet them at random intervals.
"Maybe that will help remind you of your own wetting habits, Jimmy," my mom informed me.
I also got a set of blocks and a rattle before the subject returned again to my masturbating activites.
"Tell me your opinion on this," my mom asked the stern lady, "I've been thinking about placing him into diapers that are scratchy and uncomfortable to discourage his naughty behaviour...what do you think?"
"Personally, I think that would be the wrong direction to go in," she said very firmly, "what's happening, is that your baby here simply can't resist temptation. You dress him up in a thick, soft diaper and he feels it's a tool for him to play with himself in. Now, you could put him into something much more uncomfortable but then you'll just be avoiding the issue. The fact is, your little sissy here is going to be confronted with temptation all his life so you need to nip his bad habits in the bud, early on. He needs to be taught that masturbation is unacceptable and will earn him a trip over your lap immediately."
"-Believe me, he got his little fanny soundly spanked this morning when I caught him," my mom assured her.
"Good. That's the first step. If this little sissy were under my roof, he'd soon be cured of his masturbating nonsense. I like to spank first, then ask questions later."
I squirmed uncomfortably at this discussion of how often and where my bottom should be paddled.
"No," she said continuing, "what you need to do is to control his environment while still exposing him to temptation. Put him in the softest possible diapers and use plastic panties that are thin and soft. Come and let me show you."

[archives]

Jimmy's Day of Shopping, part 4

Author: Baby Bobby, May/6/2004 11:01:01 [-04]



The lady took us down another aisle to a section containing rubber and plastic panties.

"This brand of plastic panties are baby soft, and they come in some wonderfully cute colors."

I watched as my mom selected numerous pink, yellow, lilac, peach and a few white ones.

"The idea is for him to be put into a position where he'll be tempted to masturbate but he won't be able to. And if he does, that's when it's time to pull his diapers down and paddle him until the little sissy is bawling like a baby. You see, he just lacks discipline in his life. When you've cured him of his masturbatory games under those conditions, you'll know that he's able to resist temptation elsewhere in life," the lady explained carefully.

"That's an excellent suggestion," my mom agreed with enthusiasm, "thank you very much."

"It's no problem at all, I've been disciplining bedwetters and masturbators for years now."

"I was wondering, perhaps you wouldn't mind babysitting for me on occasion? You seem to be just the kind of person I'm looking for and I'm still trying to find someone that can help out when I'm out of the house."

"I'd be happy to," the lady said quickly as she gave me a look of determination that made me shiver, "I'll have him singing 'the Good Ship Lollipop' by the time you get home."

My mom laughed at that and she took down the lady's phone number.

"Now, no sissy's wardrobe would be complete without nursery print panties. I like this brand because they have little plastic lace accents around the legs and waist. They're very babyish-wouldn't you agree?"

"Oh yes, very much so," my mom agreed. She took a pink pair and held it up to my diapers, imagining them on me.

"Yes, you'll definately be wearing these on a regular basis, Jimmy," she assured me.

I wilted at the thought of being dressed up in the humiliating panties.

"Now these aren't quite as soft as the previous brand I showed you but they're good when he's out in public. Under those circ-umstances, you won't have to worry about him masturbating anyway," the lady explained.

"Yes, that makes sense," my mom agreed.

The two continued to fill my mom's cart with other items as I watched with growing dismay. I was only half paying attention when I caught sight of another woman entering the store. My mouth dropped open in shock as I watched her pick up a basket and walk alongside the first row of baby toys. Even from a distance, I immediately recognized the distinctive form of my teacher from school, Ms. Taylor. Her long brown hair, her prominent bosum, flat tummy and long legs all seperated her from the average woman. And then the familiar 'click-click-click' of her high heels that was indelibly burned into my memory reached my ears. I felt the blood rushing to my ears as I saw her turn down our aisle, making her way slowly towards us as she shopped without looking up. Immediately, my heart began beating furiously as my mind scrambled with what to do as she grew closer and closer to us.

I turned slightly so I could watch her out of the corner of my eye. Please don't come down here, I silently beseeched her, PLEASE.

Ms. Taylor picked up a stuffed animal and then set it back down, slowly making her way towards us. What was I to do if she saw me? What would I say? I had no idea. I suddenly felt the need to pee stronger than ever and it didn't help that my diapers were already wet. I fidgeted around trying to postpone the inevitable.

"Jimmy, stand still," my mom chided me.

I bit my lip nervously as I turned my back towards Ms. Taylor who was now within ten feet of us.

My bladder muscles, never very strong, decided at that moment to relax. A strong rush of warm pee flooded into my damp diapers, completely saturating them before I could stop it.

"Oh!" I cried.

I shifted from one foot to another and whimpered to myself as my diapers grew heavier and started to sag from the weight. The stern saleslady noticed it too because she stopped talking to my mom and stared down at me harshly.

"Looks like your little baby just wet his diapers," she commented, louder than was necessary.

I blushed a deep red as my mom turned to me and lifted up the hem of my dress and petticoats to get a better look.

"Jimmy? Have you wet your diapers already?"

Just then, with the worst possible timing, Ms. Taylor appeared next to me and she looked down, her mouth open in surprise.

"Jimmy? Is that you?" she asked in shock.

I looked away in utter embarrassment as the warm pee started to seep into the seat of my diapers. I couldn't believe my incredibly terrible luck to be seen by my pretty teacher, dressed like a little girl and wearing a very wet diaper. During the pause in conversation, a last burst of pee streamed into my diaper, forming a puddle in my crotch before slowly soaking into the saturated cloth.

"Jimmy. Where are your manners?" my mom said insistently, "answer the nice lady."

"Jimmy?" Ms. Taylor asked again, "I didn't uh-recognize you at first," she said, suppressing a giggle.

My face was as red as an apple as I turned toward her for the first time.

"Uhm...uh," was all I could say.

"Oh, you must be Jimmy's mom," Ms. Taylor said, "I'm his teacher at school, Jennifer Taylor."

[archives]

Jimmy's Day of Shopping, part 5
Author: Baby Bobby, May/11/2004 09:32:28 [-04]

They all made their introductions as I stood there in embarrassed silence, my soggy diapers drooping heavily. I glanced up while they were talking just to steal a look at my teacher. She was wearing her long hair pulled up and behind which showed off her high cheekbones and gorgeous face. She wore a simple but snug white top, very low cut and I could easily see the curvaceous mounds of her generous breasts where they pushed together and formed a deep cleavage. I glimpsed an exposed section of tummy just above her skirt which came down just above her knees, showing off her shapely legs. Today, she was wearing a pair of white high heeled sandals with small little straps that went around her ankles. She always wore heels that were four or five inches high and impossible to ignore.
"Did you bring a change of diapers for your little Jimmy?" the saleslady asked pointedly.
Looking back down at me, my mom said yes and went out to the car to retrieve my diaper bag.
I was left standing there, fidgeting uncomfortably in front of these two women and wondering if my diapers were going to leak, I had peed so much. To my relief, my pink ruffled plastic panties were doing a good job of keeping it all in and the wetness could be clearly seen where my diapers clung to the panties.
"Jimmy, last time I saw you, you had a very sore bottom. I hope it's feeling better today," Ms. Taylor said sweetly. Her radiant smile was devastating, as always.
Before I could answer, the elder saleslady replied for me.
"I'm afraid that's not very likely, he got himself into a little trouble this morning and earned himself another spanking from his mommy," she said condescendingly.
"Jimmy! You've just become a naughty little boy recently," Ms. Taylor said in surprise, "what did he do?"
"Turns out, this little sissy is also an avid masturbator. His mom caught him red-handed this morning."
I'm not sure if it was possible to blush any redder than I already was, but if so, I just turned a deeper shade. My ears burned with shame at this humiliating discussion of my activities and at my expense. My mom returned shortly with my diaper bag.
"Excuse me," she asked the saleslady, "but do you happen to have a place where I might change his diapers?"
"Oh certainly, come right over here," she said, leading us to the area where changing tables were on display and that also happened to be in the middle of the store.
"Momm!" I pleaded in a whiney voice, "can't we just wait?" I was desperate to avoid getting changed in front of Ms. Taylor.
Without responding directly, my mom stuffed my oversized pacifier into my mouth, effectively ending the discussion.
"You know, I'm going to need one of these so we might as well select one now that I can purchase," she said, referring to the large assortment of changing tables available. She walked around eyeing them until she saw a low white table with a padded top, it's surface covered with a shiny vinyl nursery print cover.
"This one will do quite nicely, don't you think Jimmy?" she asked me in a taunting voice.
I could do little except suc-k the rubber pacifier in my mouth but my heart was racing at the prospect of getting changed right here in the middle of the store with all three women watching me. Ms. Taylor showed no signs of losing interest and she stood by eagerly as my mom pulled out the various items she needed from the bag. Sitting me down on the table, she pushed me back gently until I was on my back with my legs still off the edge. Lifting my dress and petticoats up, she reached under the elastic waistband of my plastic panties and began tugging them off the soaking wet diapers. I whimpered in embarrassment as she snaked them down my bare legs, pulling them over my knee socks and mary jane shoes. Next, she unpinned the sodden cloth and pulled it out from under me, placing it in an oversized ziploc bag before sealing it up. My little pee-wee shriveled even smaller at the unexpected attention and the saleslady stuck her finger down to tickle it.
"My, he certainly hasn't developed much, has he?" she remarked disdainfully.
"No, I'm afraid his physical development has closely followed his childish behavior, neither of which has shown much maturity."

[archives]

Jimmy's Day of Shopping, part 6

Author: Baby Bobby, May/13/2004 10:44:51 [-04]



A tear formed in my eye as she took some baby wipes and cleaned my damp bottom and crotch. Ms. Taylor had the bottle of baby lotion and she offered to apply it to my diaper area. My mom was only too happy to have her assistance and my teacher began slowing rubbing the lotion into my still pink cheeks.

"Well, looks like someone got his bottom soundly paddled this morning," she said as she smiled down at me. I squirmed and blushed anew as she rubbed the lotion slowly across my still sore fanny. Her hands were very soft and despite all my efforts to the contrary, I found myself getting aroused. It didn't help that as I looked over the multiple ruffled layers of my petticoats, I saw her immense breasts jiggling before me, barely contained within her tight top. Her hands moved from my bottom, tantalizingly slow up my crack, and then to my crotch, where I felt her slippery fingers caressing my tiny pen-is and balls. Ms. Taylor always had beautifully manicured nails and I watched as they encircled my little sex, rubbing the sweet smelling lotion in the most enticing manner. She had long, creamy fingers and they stroked me in the most sensual manner, sending electric waves of ecstasy through me. I swooned with pleasure as I gazed down her top, admiring her deep cleavage and the beautiful form of her tremendous boobs. She returned my lustful look through half closed eyes with her usual sweet smile. I grew harder by the second and I felt an orgasm quickly rising within me. My cheeks reddened and my body tensed in anticipation. I was seconds away from exploding and I shut my eyes tightly, suc-king my pacifier for all it was worth. I shuddered as I tettered on the very brink of coming.

"There. That should do nicely," she said abruptly, in her musical voice as she stepped back to allow my mom to powder me.

I gasped in frustration at the loss of what would have been the most intense orgasm of my life and my tiny wee wee flexed and twitched in unrequited pleasure. Breathing hard, I suc-ked my pacifier and bunched my fists as my mom began shaking scented baby powder all over me. A tear trickled down my cheek at the unfairness of it all.

Meanwhile, the saleslady held three thick, fluffy diapers in her hand patiently as she waited for my mom to finish. A cloud of baby powder rose up from the changing table as she took the diapers and slid them under my rump.

"Here we go Baby," she told me lovingly, "a nice soft diaper to protect you with."

I sniffled miserably at my fate while my mom tugged the thick but baby soft cloth around my hips and pulled it between my legs, snicking the large bunny pins through and locking them closed. After both sides were secured, she patted the bulging front of my diaper and smiled down at me.

"There you are. Time for your baby panties!" she exclaimed merrily.

I hated it when she said that, all the more since it was being said in front of these two women. As if things weren't bad enough, a pair of young mothers entered the store and headed in our direction. Apparently wondering who was getting changed, they came over to investigate out of curiousity.

"Now, which plastic panties shall we wear today?" my mom asked, as if she were wearing them too. Of course, she didn't really expect a response, and since I still had the pacifier in my mouth, I was in no position to reply anyway. Instead, she picked one of the pink nursery print panties from our basket and gathered the legs together in her hands. As the two ladies came up to see what was going on, my mom snaked the plastic panties up my skinny legs, wrestling them over the thick bulk of my diapers as she pulled them up and ran her fingers around the inside of the elastic waistband, ensuring that my diapers were completely covered. She did the same with the leg holes to be sure no stray bits of diaper were peeking through.

"Isn't he a little old to still be wearing diapers?" one of the ladies asked.

"Not when he can't keep his pants or bed dry for more than an hour," my mom replied without hesitation.

They looked me over with strange looks and then moved on, occasionally looking over their shoulders at me. Still pouting, I sat up, only to have my mom push me back down again.

"Let me powder between your legs Honey," she said as she shook the baby powder where my thighs rubbed against my plastic panties.

I looked up to see Ms. Taylor smiling down on me, her full, sensual lips making me want her all the more.

I stood up awkwardly, the fat bulk of my diapers forcing my legs outward in a babyish waddle. My mom took our items up to the counter and I waited impatiently as she made small talk with the saleslady.

Ms. Taylor was behind us in line with a baby toy in her hand and she looked at me as if still appraising me.

"Maybe I too, should get a playpen. I could put it in the classroom, and that way you'd be right at home, Jimmy," she suggested.

I frowned but kept suc-king on my pacifier. I was completely ashamed and now my idol had been a participant in my humiliation. She'd never look at me the same.

At last, my mom finished paying for all her items and I helped carry the playpen and changing table out to the car.

"Don't forget your plastic panties Jimmy!" the saleslady called out to me as she stood in the doorway and held the full bag in her arms.

Several people in the parking lot looked at me and stared in wonder.

"Run along Jimmy, and fetch your panties," my mom told me. She sent me off with a slap on my thickly diapered bottom.

"See you soon, Jimmy," the sales lady told me with a wicked gleam in her eyes as she handed me the bag. That was one visit I wouldn't be looking forward to.

"Bye bye Jimmy!" Ms. Taylor called out to me. As she turned away, I couldn't help gazing longingly at her trim derriere, nicely displayed in her tight skirt.

When I returned to the car, my mom sat me in back and buckled me in again, replacing my pacifier with a large baby bottle of warm milk.

"Make sure you finish that before we get to our next stop," she warned me.

Not wishing to get another spanking, I began suc-king eagerly on the bottle, unconsciously adding to my sissyish appearance as people passed us by.

[archives]

Jimmy's Day of Shopping, part 7

Author: Baby Bobby, May/16/2004 00:47:33 [-04]



We pulled into the parking lot for a strip mall, in front of a shop that said 'Candy's Fashions'. With nervous haste, I finished off the last of the warm milk just as my mom came around to undo my belt buckle.

"Good boy,' she said simply as she took the bottle and put it in my diaper bag. Taking my hand, she led me into the small shop which contained countless bolts of fabrics, along with a good selection of catalogs. A good looking woman in her mid-thirties came out from a backroom and greeted my mom warmly. They chatted briefly and then my mom stood aside to reveal me to her friend.

"And this is my sissy son that I told you about over the phone," she said by way of introduction.

"Well young man," she said looking me up and down, "from what I've been told, you're a little boy who refuses to grow up."

My mom had put my pacifier back in my mouth so all I could do was shake my head.

"But don't you worry," she said reassuringly, "we're going to fix you right up!"

She pulled out a catalog of baby and little girl's fashions, showing my mom different styles of dresses and outfits that she thought would be appropriate for a sissy still in diapers. They discussed a number of different items with my mom making sure each one would be sufficiently short in the hemline to leave my diapers fully exposed. The seamstress assured her she'd take care of that and after several designs had been selected, she showed my mom a sailor suit that could be made even more girlish than it already was with pink lace accents throughout.

"Excellent!" she agreed, "that will be perfect."

The lady took several minutes and began thoroughly measuring me, getting my chest, waist, height, arms, everything necessary to create perfect fitting dresses that would be the envy of any little girl. On our way out, she called out to me:

"Oh Jimmy?" she said in a sing-song tone of voice. When I turned around she blew a kiss at me.

"Nice panties."

I blushed red and hastened out of the store.



We pulled up a little while later in front of a salon. My mom took my empty bottle and led me inside where all the girls stopped what they were doing to openly stare at me. I blushed furiously as they gathered around me commenting on my outfit and appearance. They lifted up my dress hem and squeezed my diapers, oohing and aahing at how precious they thought I was. My mom explained that she wanted them to paint my nails and give me a little make-up, just enough to soften my features and make me look a little more girlish than I already was.

One of the prettier girls, a blonde named Barbie, volunteered to work on me. She sat me down and immediately began talking to me like I were a little child.

"Hello little boy," she said very sweetly, "do you need your diapers changed before we start?"

"Nu-uh," I replied, my face still a bright shade of red.

"Jimmy, it looks like you're blushing. But don't you worry. I'll make you the prettiest little sissy in town," she said with a giggle.

As she unscrewed a bottle of glossy pink nail polish, my eyes moved over her curvy form. She was wearing snug white jeans and a tight white halter top which showed off her perky breasts very sexily. Over that, she had on a long white lab coat but it didn't obscure her beautiful body unless she turned around.

Placing cotton between my shaking fingers, she began methodically painting the glossy lacquer to my nails, taking great care not to go over the edges. As I watched, I felt the acc-umulation of all the milk my mom had made me drink starting to press urgently on my bladder. I tried to squirm in my seat but Barbie looked up at me annoyingly.

"Quite squirming Silly, you'll make me mess up your nails."

While Barbie worked, she focused on my nails, averting her eyes downwards which enabled me to stare uninhibited at her fabulous body. I watched the swell of her breasts rising and falling as she breathed and I was completely captivated. They were perky and proud, pushing against the thin fabric of her top insistently and I could clearly see the white demi-cup bra she was wearing underneath. My eyes gazed hungrily at the soft line of her cleavage as it disappeared into the low scoop neckline of her halter top. If I craned my neck, I could just glimpse the white lace where her bra cups were joined and my heart beat excitedly.

She must have sensed my straining to look down her top because she jerked her head up and stared at me hard with her piercing, beautiful green eyes. They penetrated me like knives and I felt extremely intimidated.

“Are you trying to look down my top?” she asked accusingly, as if she had read my mind.

“Oh no!” I insisted hastily, “no Ma’am!”

She furrowed her perfectly shaped brows and my heart skipped a beat as I grew fearful.

“You’d better not,” she snapped, “because I spank little sissies like you who think they can stare at me whenever they want.”