Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Pre-2011 Sissy Stories => Topic started by: archives on February 20, 2006, 01:46:17 AM
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Jimmy's Day at School
Author: Baby Bobby, Mar/14/2004 14:58:32 [-04]
Jimmy’s day at School
“Jimmy! You’re going to be late for school!” my mom called from out in the hallway.
I rolled over in my bed sleepily, before swinging my feet out to get up. My thick, nighttime diapers were soaked as usual but the snug plastic pants kept my sheets dry. I had been wetting the bed ever since I was six, when my dad left us and my mom had decided that diapers were the best solution to my nightly problem. My mom, never one to take chances, had also replaced the mattress cover with a vinyl waterproof sheet years ago and it crinkled loudly as I got up. I was dressed only in my diapers and nightshirt, the latter of which was more of a nighty, than a pajama top. When my mom first started diapering me for bed, she initially consented to allowing me to continue wearing my pajama bottoms but after several weeks, I had managed to rip the back seams out in every one because of the thickness of the diapers. Eventually, she dispensed with them entirely and threw the ruined pajama bottoms in the trash. As time went on, she replaced my tops more and more with decidedly feminine wear, telling me she didn’t want to waste money on pajama bottoms that would just be thrown out.
Today’s top was a short hemmed, puff sleaved frock, with a flower print that I prayed no one would ever see me in. Besides the fact that it looked like it belonged to a little girl, it did nothing to hide my embarrassing diapers which remained humiliatingly exposed.
Waddling out into the dining room, I sat down and began eating the breakfast that my mom had prepared for me. I was thirteen years old and attending a private school but my mom often treated me like I was still four. Instead of serving my juice, she always gave me a tall glass of milk in the morning and rather than call me by my given name, Jim, she referred to me as Jimmy, much to my chagrin.
As I ate my cereal, I felt a stream of warm pee further saturate my already soaked diaper, seeping down between my legs and collecting in the soggy cloth under my rump. While it's true that perhaps I didn't make enough of an effort to keep my diapers dry as I should have, I reasoned that since they were already wet, I might as well just use them anyway. But despite the humiliation I felt wearing them, I sure was glad I had on a snug pair of plastic pants.
After breakfast, I met my mom back in my bedroom where she had my changing pad laid out, along with a fresh diaper. Unfortunately, my mom had gotten tired of my half-hearted attempts to control my daytime accidents and she finally settled on diapers and plastic pants for that problem as well. I probably wore the baggiest pants at school but so far as I knew, no one had caught on yet about my “situation.” My mom said I was just lazy, and I could stop wetting my pants whenever I wanted, but I always hotly denied it.
Sometimes, when I was frightened suddenly, or laughed too hard, I’d let out a trickle of pee before I could stop it. I hated wearing diapers but my mom was convinced that they were the only remedy for my problem. I was helpless to stop her once her mind was made up, and I knew only too well that she would show no hesitation in pulling them down and putting me over her knee for a good hard spanking if I were to put up too much of a fuss.
This morning, I was anxious to get my wet and sagging diapers changed so I sat down without argument while she busied herself pulling down my clinging waterproof pants. With expert efficiency, which came from doing this day after day, she soon had my diapers off and was wiping my damp bottom with baby wipes. I said nothing as she scooped up some diaper rash cream and smeared it across my bottom until it was coated with a thick, white layer of the goop. She slid my fresh diaper under me and powdered my front area generously, perhaps a little too generously, I thought nervously, since I feared that someone might smell it on me later at school. I had a reputation among some of the kids that I was a sissy and the last thing I needed was for them to smell baby powder on me.
“That’s enough!” I protested in a whiny voice but my mom only stopped briefly, before wordlessly shaking some more on me.
“Someone will smell it on me!” I complained vehemently.
“Hush Dear,” my mom said, blithely dismissing me. She pulled up the soft but thick cloth and held each corner firmly as she pinned them securely with two big bunny shaped pins.
Gathering the leg holes of some plastic pants, she began sliding them up my skinny legs but I realized to my shock that they weren’t the usual white ones. Instead, they were a pink nursery print with small frills around the leg openings that I had never seen before.
“Hey! What are you doing? Where are my normal pants?” I asked in a panic.
My mom was no pushover, and despite my frantic kicking, she easily slid them up my legs and over the bulging cotton cloth of my diapers.
“I’m sorry Honey, but all your other ones are in the laundry. This is all you’ve got for now,” she said sympathetically.
“Bu-bu…Then I’ll just wear what I had on last night,” I cried as I stared down at the babyish plastic pants covering my diapers. The infantile bunnys and clowns decorating the vinyl seemed to shout out baby, loud and clear.
“Oh Jimmy…honestly,” she said as she began putting away the rest of the supplies, “you can’t wear the others because they’re wet and need to be washed. And I’m not going to send you to school with soiled plastic panties. What kind of mother would that make me?”
I hated when she called them panties, it sounded so sissyish.
“They’re pants not panties, I protested bitterly.
“Yes Dear,” she replied tiredly. She always said ‘yes Dear’ when she didn’t feel like arguing with me but she never changed her mind. I think my mom thought I was a sissy too but she didn’t actually come out and say so.
I hurried to get dressed and soon we were on our way to school. It seemed like my jeans were tighter than usual but no amount of trying to compress my padded middle would change my appearance. It was frustrating but I just hoped that no one would notice.
As usual, I had my Scooby–Doo lunchbox with me which I felt very self conscious about but my mom refused to get me another. I had gotten bullied at school but she could never see why it was an issue for me.
But my main fear today was that one of the older kids would decide to pull my pants down as a prank, as they had done to my friend Johnny last week. That would be mortifying. I shuddered as I thought of the humiliation I would feel if people were to see not just my diapers, but the babyish nursery print plastic pants I had on.
“Mom?” I started anxiously, “I was wondering…do you think I could start wearing training pants to school?”
“Training pants?” she said incredulously, like it was the silliest thing in the world, “I don’t think so Jimmy. You’d just wet through them if we were to do that.”
“But I’d really try hard to keep them dry!” I insisted.
“No Dear,” she said simply, which clearly indicated she thought such a thing was ridiculous, “No, I think diapers and plastic panties are better suited for you. Maybe someday you can graduate to training panties but for now I think we’ll just stick with the diapers.”
Her tone indicated the discussion was over and I sulked as I sat back in my seat.
Soon, we reached my school and she let me out, giving me a kiss on the cheek before saying goodbye.
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Jimmy's Day at School, pt 2
Author: Baby Bobby, Mar/16/2004 23:17:05 [-04]
“Bye-bye Jimmy!” she called out, much louder than I would have liked. A couple of girls nearby giggled and began whispering about me as I turned and rushed inside.
I walked into my classroom, praying as usual, that no one would notice the thick bulkiness of my diapers pushing against my jeans. Sitting down at my desk, I watched as Ms. Taylor, our teacher came in.
She was a goddess as far as I was concerned and I was totally in love with her. She was in her mid-twenties, drop dead gorgeous, tall and slim, with a generous bustline that I estimated to be double D in size. She had a habit of wearing provocative outfits and today was no exception. In keeping with the warm spring weather, she had chosen a light colored dress of a breezy material that went about mid-thigh and showed off her smooth, sexy legs, particularly when she sat down. In addition, her big, curvy breasts were tightly encased in a scoop necked, low cut dress that made it impossible to concentrate on my schoolwork. I found myself staring at her unbelievable figure as she stood before the class and brought the class to order.
While she talked, she made a point of walking slowly around the room and I admired the practiced ease in which she moved in her stiletto high heels. I was oblivious to what she was saying but I felt my wiener stirring within my diaper as I stared at her incredible profile. Her big bust was further accentuated by her flat tummy but my eyes were riveted to the long line of cleavage that disappeared into the low cut of her dress. I blushed at the thought of kissing the exposed soft skin of her breasts that were literally bursting out of her dress. I thought I caught sight of a flash of lace from the cups of her bra and my heart beat with lustful desire.
I had tried desperately to be the teacher’s pet and had made a point of ingratiating myself with her at every opportunity. From time to time, she graced me with her devastating smile which only fueled my fantasies and made me think she felt the same way about me. I was certain that I could do no wrong in her eyes and I felt a confidence that was perhaps misplaced. I was to find out just how misplaced it was later…
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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."
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Jimmy's Day at School, part 4
Author: Baby Bobby, Mar/21/2004 01:52:24 [-04]
The classroom of kids let out a collective gasp as they took in the babyish looking diaper and pink plastic nursery pants I was now openly displaying. My ears filled with the sounds of giggling all around me and I could see Ms. Taylor was clearly shocked. She recovered quickly however and she stared me in the eye with firm determination.
“Jim, are you wet?” she asked, eyeing the colorful nursery characters decorating the panties.
I felt the blood rushing all the way from my cheeks to the tips of my ears.
A tear formed in my eye as I slowly nodded yes. I had never been so humiliated in my entire life. I thought that maybe if I admitted to being wet that she would spare me the additional humiliation of a spanking. After all, wasn't this punishment enough? But the look on her face indicated she had every intention of spanking me, wet diapers or not.
In response, she pulled the hem of her dress up to the top of her thighs, probably so that the wet diaper wouldn’t stain her dress. Her smooth, silky thighs were perfect in every way and I gazed at them admiringly, even as I anxiously contemplated the coming spanking. She reached forward to pull my waterproof panties down and her breasts were pushed together, creating a curvy Y of two joining cleavages. It was breathtaking to behold but I became panicky as she started to snake the panties off my diaper and down my legs. I shifted nervously and tried to stop her but she simply pushed my hands away and continued until they were gathered around my ankles. I saw her eyes staring at the yellowish wet spot in the front of my diaper and I blushed an even deeper shade of red, if that were possible. She looked me back in the eye with a look of disappointment and shook her head.
I was so ashamed. Here, the idol of my life was now fully aware that I needed to wear diapers and plastic pants like a baby to keep my pants dry. All my efforts were for naught! And now she was going to spank me like a naughty little boy, in front of the entire class!
All too suddenly, she pulled me over her lap and began unpinning the thick folds of my diapers.
“No Ms. Taylor! Please! I didn’t do it!” I pleaded desperately, “It wasn’t me!”
“I don’t like little boys who lie to me,” she said as she pulled the cloth back and exposed my fanny to the rest of the eagerly attentive class, “but my paddle usually brings out the honesty in them.”
I began whimpering and crocodile tears filled my eyes as I stared down at her curved calves and the small straps that held her high heels on.
“Please don’t spank me! Please? Please?!” I begged her pathetically. I had never been spanked in public before and tears of shame streamed down my face.
The rest of the class craned their heads forward for a better view as they waited eagerly to watch my punishment.
Looking up, I saw the face of Kelly Kendall smiling back at me. She was the cutest girl in our class and head of the cheerleading team. She appeared very amused with my situation and if I was looking for sympathy, there was none coming from her.
Before I could dwell on that however Ms. Taylor shocked me with the first, crisp slap of the paddle on my upraised bottom.
SMACKK!!!
I yelped in pain and the paddle came down again, even harder. Maybe I really am just a sissy because I immediately burst into real tears and began crying like a baby.
SMACKK!! SMACKK!! SMACKK!!
Ms. Taylor delivered the spanking with fierce determination, swatting my tender cheeks with harsh, angry slaps. I gasped in pain and kicked my feet wildly, no longer concerned about maintaining any pretence of dignity.
SMACKK!! SMACKK!! CRACKK!! SMMMACK!!
I wailed loudly and beat my fists on the ground in futile impotence. The hard wooden paddle left its searing impression on my bottom again and again and I knew it was a bright shade of red, matching the flushed color of my face. I sobbed and wailed but Ms. Taylor never eased the pace or the severity of her spanking.
SMACKK!! CRACK!! SMACKKK!!!
“Are you ready to be a good boy?” she snapped at me harshly.
“Ye-yes-yes!” I cried between sobs. My face was wet with tears and my nose was runny but I cried like a baby.
SMMACKKK!!!
I bawled and bawled, my dignity forgotten as I howled over her lap, gasping for air between sobs.
“That’s better,” she said as set the paddle down on the desk with a clatter. My bottom was blazing and hot as she pulled my diapers up snugly and repinned them. Helping me up, I rose to my feet shakily, my crying still unabated. When it became apparent that she wasn’t going to pull up my plastic pants, I reached down and hurriedly yanked them up which only sealed in worse the fire crackling on my punished fanny. When I reached down to do the same with my trousers, she put the toe of her high heeled sandals over the middle of them, holding them down on the floor.
“No, those can stay down for awhile,” she said firmly, “I want you to put your nose in the corner and think about just what you’ve done.”
I sobbed with embarrassment and shuffled over to the corner by the blackboard, knowing my colorful plastic pants were now on full display for everyone to see. It would be years, if ever, before I lived this day down.
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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."
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Jimmy's Day at School, part 6
Author: Baby Bobby, Mar/24/2004 11:48:10 [-04]
I winced and did my best to pull my jeans up and over the diaper but it was just too fat. No amount of effort was going to get my pants to cover them, never mind, allow me to zip them up.
"See! It's too big!" I whined petulantly.
Both women looked at me unsympathetically. Ms. Stern just shook her head and the nurse put her hands on her hips, making no effort to alleviate my predicament.
"I know!" she said suddenly, "I think I've got a pair of shorts you can borrow. They were left by an older student last week."
I felt a small sense of relief but I was also sure that nothing short of a poncho was going to be able to hide the obvious bulk of the diapers I was presently wearing. Ms. Jones dug around in a drawer and then pulled out some silky gym shorts that were pink with white trim.
"Here we are!" she said brightly, "these should fit perfectly!"
"I can't wear those!" I cried, " they're for girls!"
"Now Jimmy, I know these aren't exactly what you had in mind, but I think it's best that you give it a try. It's all I have. And your alternative is to go without any pants at all. You don't want that do you?"
I pouted and felt tears in my eyes as I shook my head no.
"That's a good boy. Now let me help you put these on-"
"-I can do it myself!" I interrupted defiantly, angry and resentful.
"Well!..Fine then," she said rather insulted, "I can see now how you got your spanking today."
"Sounds to me like you need a little attitude adjustment, Young man," Ms. Stern said ominously.
I bit my lip nervously as I hiked the shorts up and over my diapers. They were stretchy and snug enough that they left absolutely no doubt as to what I was wearing beneath. Indeed, they could almost pass for rhumba panties if they had had ruffles across the seat. I sniffled with embarrasment as Ms. Jones folded my jeans into a neat package and set them next to the bag that had my wet diaper in it.
"Am I done now?" I said, as a tear trickled down my cheek.
"Yes Jimmy, you can go back to class now," she told me.
Without another word, I shuffled back down the hall, waddling because of the thick bulk between my legs. I stood outside my classroom door for ten minutes before I had the courage to open it and step inside. Everyone's eyes, including Ms. Taylor's, immediately looked up at me and stared openly as I tried to walk normally to my seat. All of the girls were giggling and began talking amongst themselves until Ms. Taylor shushed them and brought the class back to attention.
I was ready to die of embarrassment.
At the next break, I was walking down the hall, trying desperately to be inconspicuous but I felt the stares of everyone around me, looking at me and in particular, the silky pink shorts that were clinging to my thick diaper. In quieter moments, the unmistakeable crinkle-swish of my plastic pants could be plainly heard, bringing further ridicule upon me.
A group of girls called me a diaper sissy and some others asked if I needed changing.
Since I was keeping my eyes downcast in embarrassment, I didn't notice when Tara suddenly appeared and took hold of my arm. With her strong grip, she ushered me into the girl's bathroom where Melissa and Michelle were waiting. My nemesis was dragging on a cigarette as she looked me up and down contemptuously.
"Well diaper boy," she said with a sneer, "so you thought you'd try and blame the fire alarm on me, huh?"
I looked around in panic but the tall high school girls had a firm grip on my skinny arms.
"Let go of me!" I squealed imperiously.
Tara yanked my pink gym shorts down revealing my nursery plastic pants again.
"You really look more natural with your diapers exposed, Sissy boy," Michelle said condescendingly.
I stamped my feet in frustration which only made me look more like the sissy weakling they were calling me.
Melissa was wearing a short black skirt and a snug striped top that hugged her generous bosom. I watched in amazement as she unzipped the back of her skirt and began sliding it down, revealing a pair of high cut black lace panties. She stepped out of the skirt with her high heel pumps and taking a tall trashcan, she upended it, placing it upside down in the middle of the bathroom.
"Today we're going to have a little fun with you Baby boy," she said in a threatening tone of voice. I was at loss to understand what was going on until I saw her reach into her gym bag and produce a big rubber dil-do, that was securely attached to a series of staps, like a harness. As she stepped into the device, I watched breathlessly as she pulled it up her long thighs and began cinching up the straps. When she was done, the big dil-do stuck out boldly, it's eight inches of fat rubber contrasting with Melissa's very feminine body.
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Jimmy's Day at School, part 7
Author: Baby Bobby, Mar/26/2004 13:02:10 [-05 EST]
I wasn't sure what she had in mind but I knew I didn't like the look of it. I struggled mightily against my captors but they easily forced me down on my knees.
"You might as well get used to this Sissy boy," Melissa said with a gleam in her eyes, "'cause this is where you belong-on your knees, suc-king coc-k."
The others laughed heartily as Melissa guided the big dil-do toward my mouth.
"No! no-please!" I pleaded, "I don't wanna-"
She cut short my frantic pleas by stuffing the fat rubber coc-k past my lips, throttling me with it as I choked, unprepared for the massive pen-is being thrust into my mouth.
"suc-k it sissy," she warned, "suc-k it good."
Obediantly, I slobbered and slurped on the dil-do, keenly aware of the humiliating position I was in. I blushed hot red as my cheeks were stretched wide to accomodate the thick coc-k, and Melissa guided my head up and down, moaning in mock exctasy.
"That's it, show everyone what a good little coc-ksuc-ker you are," she said admiringly.
I whimpered meakly, as my head bobbed up and down on the dil-do and I was so embarrassed, tears of shame trickled down my cheeks.
Melissa pulled it out of my mouth and I gasped for air as I stared at the saliva covered coc-k.
"Kiss it Sissy," she ordered me.
Doing as she told me, I gave the wet bulbous head a big kiss and she pushed it past my lips again. I found myself deep throating it as she slid it in and out of my mouth, guiding my rhythm with her hands.
Just as my jaws were starting to get sore, she pulled it out.
"Okay Baby boy, enough fun for you. Now it's time for me to show what you can look forward to, the rest of your life."
The other girls picked me up off my knees and Tara began yanking my plastic pants down.
"Don't you worry, Sissykins," she said with mock concern, "I won't harm your pretty little plastic panties."
I squirmed and fidgeted while they unpinned my diapers and bent me over the trash can. Michelle moved around the front to hold me in place and keep my bare bottom exposed in back.
"My my," Melissa said as she gazed down at my pink fanny, "Ms. Taylor certainly knows how to use a paddle doesn't she?"
"Let go of me!" I squealed pitifully, "let go of me!!"
"Spread your legs Sissy," she ordered me sternly. Using the toe of her high heels, she kicked my feet outwards, making me spread my legs apart as I remained bent over at the waist.
"Please Melissa, I'll do anything you want," I implored her, "please, please let me go!!"
She ignored me as she dipped the big head of the strap-on into a jar of vasoline, coating it liberally. Then she brought it up behind me, rubbing the head teasingly against my puckering anus.
"This is what all big sissies need Diaper boy," she said, stroking the head against my hole.
"Nooo!" I wailed, "I want my mommy!"
With an abrupt move, she slapped my right butt cheek painfully hard, leaving a stinging impression of her hand on the already pink skin. I yelped in pain and felt as she pulled my cheeks apart and began pushing firmly and determinedly with the strap-on. Instinctively, I tried to move forward to escape the fat rubber invader but the trashcan and Michelle kept me in place.
"It's too biiigg!!" I cried as Melissa wiggled it around, pushing harder and harder against my sphincter. She slapped my buttcheek again and kicked my feet out farther, forcing me to keep my balance by grasping the sides of the can.
"Oww!" I wailed in a girlish voice, smarting from the sting on my bottom. This sensation was quickly replaced with the feeling of the dil-do sliding in past my opening.
"OHHH!!" I moaned as I felt the thick coc-k filling me up. Michelle and Tara smiled at me satisfied as they watched the dil-do get buried in my backside. My mouth was open and I lay there gasping as Melissa waited long enough to allow me to get accustomed to it. Then, she began slowly pumping me, in and out. I moaned like a little girl, no longer concerned about trying to act like a big boy. Slowly, and with great deliberation, she pumped me from behind, forcing every inch of the big dil-do into my pouting bottom. I sighed everytime it eased out and moaned when she'd push it back in. Taking her time, she humped me with long, patient strokes, grasping my hips and forcing the dil-do in as far as it would go. She'd hold it there while I squealed and squirmed, trying desperately to escape the fat rubber invader but to no avail. Melissa was going to make sure that I got every bit that I deserved and she was in no hurry to ease my punishment.
Off to my right, I could see our reflections in the mirror. Me, the sobbing sissy bent over and getting humped relentlessly and Melissa, the tall senior, her beautiful face a mask of determination and satisfaction. Everytime she thrust forward, her breasts would heave within the confines of her top, jiggling and swaying in an erotic display. She looked so powerful with her firm, long legs, as she stood confidently in her high heels, a vision of strength and superiority as she plunged the strap-on into my waiting bottom. Her brows were furrowed on her forehead from her efforts and she grasped my hips with hands of steel.
Even though by now, the slippery dil-do was sliding in and out with ease, my hole was becoming sore and I whimpered like a girl. I gave up struggling against my tormentors and just lay there, taking my punishment submissively.
At long last, she eased the dil-do out and began wiping it clean with some wet wipes she had in her bag.
I was exhausted and lay panting as Michelle pulled the back of my diapers up and repinned them. She pulled my plastic pants up and hitched them over the bulk of my diapers but left my shorts in place.
"Maybe that will teach you a lesson next time you try and squeal on me," Melissa warned me as she caught her breath.
"Yes Ma'am," I whispered in defeat.
"Run along now, Sissy boy, before I call in one of the guys from the football team and have you suc-k him off," she said as she slapped my diapered bottom.
"Yes Ma'am," I replied obediently and hurriedly pulled up my silky shorts. I dried my tears and rushed out of the bathroom as quickly as possible.
-
Jimmy's Day at School, part 8
Author: Baby Bobby, Apr/10/2004 22:50:31 [-04]
After school, my mom came by to pick me up as she always did. I was dreading getting my diapers changed since it would be obvious I had been spanked and then I’d have to come up with an explanation that would keep her from giving me more of the same.
I stepped into the car with my pink silky shorts which immediately got my mom’s attention.
“Where’d you get those?” she asked as she pulled away from the curb.
“The school nurse,” I mumbled as I put my wet diapers and jeans on the floor in front of me, “she changed me at lunch.”
“Well that was nice of her,” she said as she ran her hands over the front of my bulky crotch, “looks like she did a good job.”
I said nothing but noticed a bag on the floor. Picking it up, I saw three pairs of new pink plastic panties, with three rows of ruffles across their back.
“Oh. Those were on clearance so I picked them up for you. It’s getting harder and harder to find plastic panties in your size so I was lucky to get those at such a good price,” she said cheerfully.
My heart sank as I pictured the flouncy white ruffles gaily adorning the shiny pink plastic across my rump.
“But Mom!” I burst out in protest, “these are for girls!”
“Oh Jimmy, Honestly. No one’s ever going to see them on you so what are you worried about?”
I didn’t tell her about the dozens of people who had seen my nursery print panties today and I felt my eyes filling with tears.
Then I noticed we weren’t headed in the usual direction of home and I became a little panicky.
“Whe-where are we going?”
“Don’t worry Honey. We’re going over to Aunt Suzie’s house-“
“-But she’ll see my diapers!” I cried.
“Jimmy. I had a long talk to her about your wetting and she knows all about your diapers. And there’s nothing to worry about, I brought over a change for you,” she explained as if that were my concern.
Aunt Suzie was my mom’s younger sister, a buxom woman in her late twenties who I liked a lot. If it weren’t for the fat diapers I was wearing I would have been eager to go over to her house, but now…I was thoroughly soaked from such a trying day and I wasn’t looking forward to having her change me.
As if reading my mind, my mom reached over and slid her finger inside the leg of my shorts and plastic panties.
“My, you’re becoming quite a little wetter aren’t you?” she remarked.
I blushed but said nothing, biting my lip in embarrassment.
Before long, we pulled up in front of Aunt Suzie’s house. I waddled out of the car and followed my mom up the driveway, carrying the bag that had my diaper change and the new panties in it.
We rang the doorbell and my aunt showed up, beautiful as ever. I blushed again as she hugged me and reached down to squeeze the seat of my soggy diapers. In my hightened state of anxiety, I let loose with another stream of pee and squirmed uncomfortably.
“Well hello baby cousin,” she said brightly.
My face was mashed into her tremendous breasts as my cheeks turned a shade of crimson.
“Jimmy’s change of diapers is in the bag,” my mom explained.
“Well, we better get our little baby taken care of then,” Aunt Suzie gushed as she pulled me into her house, “feels like mommy’s little boy wet himself.”
“Suzie, I’ve got to go but it looks like you’ve got everything under control. I’ll see you tonight,” my mom told her.
“Okay, see ya Sis,” she replied.
When the door closed, aunt Suzie pulled me into her bedroom. She was wearing a snug blouse that hugged her full bust closely and a pair of tight jeans that showed how well she maintained herself. She sat me down on the floor and pulled my pink gym shorts down, tugging them over my shoes.
“These are cute shorts, Jimmy,” she said.
“They’re not mine,” I countered, “the school nurse gave them to me because my jeans wouldn’t fit over these diapers.”
My aunt giggled.
“Yes, I can see that,” she said, “well don’t you worry about that, I’ll get you changed and into a nice fresh diaper in no time.”
I blushed while she busied herself peeling down my nursery print plastic panties and unpinning my wet diaper. With a warm washcloth, she wiped my damp crotch and bottom, taking a good look at my still pink fanny.
“Looks like you were a naughty boy at school today Jimmy.”
“Nuh-uh!” I stammered, “it wasn’t my fault!”
“Well, I suspect you had it coming” she said unsympathetically, “and sometimes little boys just need to have their bottoms spanked. But I’m afraid I’m still going to have to tell your mom about it.”
I shook my head in frustration as she slid three fresh diapers under my rump. After coating my tender fanny with diaper rash cream and sprinkling baby powder over my front, she pulled the ends of the diaper snug and pinned them up.
“There you are Baby. A nice soft diaper to keep you safe and protected,” she cooed as she pulled my new plastic rhumba panties out of the bag, “and here are your baby panties!”
I blushed hot red as she gathered the legs of the shameful panties and inched them up my legs, pulling them gently over my bulging diapers.
“Oh, aren’t those just darling,” she exclaimed admiringly as she stroked the shiny front of the pink panties, “ but this ugly shirt won’t do.”
With that, she got up and went to her dresser, opening her drawers until she found what she was looking for.
“This’ll be much better,” she said as she held out a frothy nighty.
“No, I don’t want to wear that too!” I protested.
She ignored me as she pulled off my shirt and tossed it aside.
“But I don’t wanna wear that!” I repeated.
I’ll give you a surprise, Jimmy,” she said trying to tempt me.
Taking my hesitation for agreement, she pulled my arms through and brought the nighty over my head. It was a frilly pink, semi- transparent frock that was short enough to leave my diapers fully exposed.
“Oh yes, that’s much better,” she said agreeably.
-
Jimmy's Day at school, part 9
Author: Baby Bobby, Apr/18/2004 01:35:36 [-04]
I didn’t think so and I sat sulking until she pulled me up by my wrist, sitting me down on the bed. She had a number of pillows arranged against the headboard and she sat down against them, making herself comfortable. Giving me a coy look, she began unbuttoning her blouse, revealing a deep cleavage and my first view of a woman’s bra. Her tremendous bosom looked as if it were bursting out of her cups and the tops of each breast was deliciously curved.
I gulped with nervous excitement as she slowly undid the clasp on the front of her bra, releasing her heavy boobs before me.
“Come here little Sissy boy,” she said invitingly, giving me a seductive wink.
I crawled forward and she situated me so that I was looking up into her pretty face, her big boobs a mere inch before my face. With graceful moves, she pulled back the lace cup of her bra from her right breast and brought my eager mouth up to her nipple. I instantly began suc-kling eagerly and I was rewarded with her strange, but pleasant milk. I swooned with pleasure as she reached down and began softly stroking the front of my diaper over my plastic panties. My little weiner quickly became hard and my vision was filled with her big soft breasts and her smiling face. I nursed for several minutes in exctasy before she switched me over to her other boob. I took my fill as she continued to gently rub my diapered wee-wee and moments later, I had a shuddering orgasm.
As I slowly opened my eyes, my aunt Suzie pulled her breast from my mouth and snapped the clasp on her bra, kissing my forehead as she did.
“And now it’s naptime little baby,” she said sweetly as she pulled back the covers and tucked me in. In a state of relaxed bliss, I quickly drifted off to sweet sissy slumber.
My dreams were filled with tall, powerful women dressing me and treating me like a baby. I woke up a couple hours later only to find a squishy wet bulk between my legs. I felt my plastic pantied crotch and was rewarded with the familiar feel of a soaked diaper. As I realized how soggy it was, I heard my aunt Suzie in the other room talking with my mom.
“He really is just a big baby,” she was explaining to her, “I think some little boys just never grow up.”
“You’re right of course,” my mom replied, “it seems like I’m having to start his potty training all over again. And I’ve been putting him back into diapers during the daytime now.”
“Perhaps stronger measures are warranted.”
“What do you mean?”
“I think you should start dressing him like the baby he’s been acting like. And treating him like one as well.”
“What did you have in mind?”
“He’s such a sissy, I would suggest dressing him like a little baby girl, complete with a short frilly dress and Mary Janes.”
“Jimmy?” my mom laughed, “he would hate that!”
“Maybe that’s what your little boy needs, to get him to start acting more his age.”
“But, where would I find clothes for him?”
“Leave that to me, I have a nice collection from my niece that will fit him nicely. They may be a little short but I think that’ll be just fine.”
“Sounds like you’ve got it all planned out,” my mom said agreeably.
“Let’s just say I know a sissy when I see one and he’s the biggest sissy I’ve ever seen. Would you like to see what I can do?”
“Oh, very much. Shall we wake him up?”
“Why not? Let me get a few things out of the other room,” Aunt Suzie replied.
After listening to this conversation, I grew very anxious as I realized they were going to turn me into a little sissy baby girl. But what could I do? Either one was strong enough to put me over their lap and spank me. I could easily visualize my pretty aunt taking me across her knees, pulling up my short frilly dress, and pulling my diapers down for a hard, stinging spanking. I shuddered at the thought!
The two entered my room and I saw my Aunt was carrying a large pile of items.
"Well, I see our little baby is up," she said cheerily.
"Pulling back the covers, she immediately felt the front of my diapers.
"Soaked again. You really are just a big baby aren't you?" she asked.
I said nothing but looked down in shame.
"Well, we're just going to dress you up in the same way you've been acting Sissykins," she told me, "but first we're going to need to change those wet diapers. You're lucky your mommy brought over another change for you."
Her tone of voice had taken on a condescending edge and I felt like she were talking to a four year old.
Sitting me on the floor, she peeled my clinging waterproof rhumba panties down and off my feet. Next, she unpinned the sodden cloth of my diapers and pulled them aside, wiping my tiny pen-is and balls as well as my damp bottom with a warm washcloth.
"I think we're going to have to start all over from the beginning," she informed me as she slide three fresh diapers under my rump, "we're going to start treating you like the little sissy baby you so obviously want to be."
"But I don't want to be that!" I whined.
Ignoring me, she shook a generous amount of powder over me and I took in the familiar scent as she pulled the sides of my diaper up and pinned them closed. Taking another pair of the rhumba panties from my mom, she shook them out and snaked them up my legs and then over my big, bulging diapers.
"There, that should hold you for awhile," she said satisfied.
"Now, let's just see what we have here for a little girl who still wets her diapers."
From the pile of clothes she brought in, she selected a frilly petticoat, a white frothy mass of soft layers that formed a wedge where the hem flared out. She put it over my head and adjusted it until she was satisfied of the fit. Next, she took what looked like a little girl's Sunday school dress and put it over my head.
"Nooo!" I squealed in protest as I put my hands up to ward off the humiliating garment.
"Young man!" she snarled, her voice becoming suddenly harsh, "in this house, you will do as you're told. Otherwise I will put you over my knee and paddle that bottom of yours. Do you understand me?"
"Ye-yes, Aunt Suzie," I said shakily.
-
Jimmy's Day at School, the end
Author: Baby Bobby, Apr/19/2004 10:28:39 [-04]
"By the way," she said as she continued putting the dress over my head, "it looks as if your little sissy here had gotten himself into some mischief at school. When I was changing his diapers earlier, I noticed his bottom was still red from a spanking."
"Well, well, well," my mom said as she crossed her arms and looked down at me, "looks like you'll be going over my lap when we get home, Young Man," she told me squarely.
"But it wasn't my fault!" I pouted stubbornly.
"We'll finish this discussion when you're over my knee, Jimmy," she assured me.
My Aunt smiled down at me as she pulled some white knee socks up my legs and fit some pink mary janes to my feet.
"I can't believe how well these fit you," she said brightly, " I was afraid they'd be too small. Stand up so I can see how the dress fits."
I stood up, the bulky diaper forcing my legs out a bit and the soft petticoat rustling silkily around me. My Aunt pulled a bit around the hems adjusting the fit to suit her.
"Well, it doesn't quite hide your diapers but I think that'll be just fine," she chuckled.
Taking a brush from her vanity, she brushed my longish hair into pigtails and clicked a big pink bow over each one.
"You actually make quite a cute little girl," she told me as she looked over the full effect, "here, look for yourself."
Taking me over to a full length mirror, she stood me before it and my mouth dropped in disbelief. I looked completely like a little baby girl and no amount of tugging on my dress would hide my embarrassing diapers. Tears formed in my eyes and as I twirled around, I could clearly see the shiny pink plastic and ruffles covering my thickly diapered bottom.
"Mommy! I don't wanna wear this!" I cried in shame.
"You'd better start getting used to it Jimmy, because this is how you'll dress from now on. You couldn't handle your responsibilities as a young man so now you'll be treated like the little sissy baby you've been acting like," my mom told me.
I stamped my feet in frustration as the tears spilled down my face. Just then, Aunt Suzie sprayed my with a bottle of perfume, a sweet, childish scent, suitable for a little girl.
"There, now you smell like a baby too, Sissy-boy."
After my mom gathered my wet diapers and old clothes, we said goodbye to Aunt Suzie and headed home. I sniffled and sulked on the way there, wondering how humiliating my new life was going to be. It was late when we finally pulled up into the driveway and I was glad it was dark out. Nonetheless, as soon as I got out of the car, a breeze came and blew my dress and petticoats up around me, exposing my diapers even more clearly.
"Oh!" I cried, as I fought to bring the frothy layers under control. The breeze was chilly on my bare legs and I felt a small trickle of pee escape into my diaper.
"Come along, Jimmy," my mom said as she took me by the wrist and pulled me inside.
"I want you to get ready for bed, you've got a long day ahead of you tomorrow," she said as she slapped my diapered bottom, "if you're going to be dressed like a little sissy girl, we'd better go shopping."
"But I don't wanna dress like this!" I protested.
"And I think we'll start out tomorrow with a nice, hard spanking. That should do wonders for your attitude, Jimmy."
THE END