Note to Betty and the reader: This is the very first story I ever wrote, and I'm not exactly sure how old it is. I think it was originally posted online in 2003, but I'm pretty sure it was written on paper much earlier than that.
I'm not sure if it should be posted here or in the archives, but it's old, and I suspect it will be new to many here.
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 still be able to 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 sternly, ''You are to do exactly as Jennifer says, do you understand me?''
I mumbled my acquiescence 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 tip-toed down the hall and into her bedroom. I was overwhelmed with the femininity of everything from the lacy curtains to the silky bed sheets. 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 36EE 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 little coc-k 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. 36EE!
I was in complete ecstasy 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, tried 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 with 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 little wee-wee 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 shrieked 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 rhythm.
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, completely 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.
Unceremoniously, 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 alleviate 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. Obediently, 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. Not that I would ever admit that to anyone of course. My pee-pee 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 I 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 dic-k shrank back to its 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 course of action either.
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 deliciously curved hips.
''You really are just a big baby. How did your mommy ever get you out of diapers anyway?'' she asked condescendingly, shaking her pretty head.
"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 alright, 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 rumba 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 enema, now come over here and quit stalling.''
As she pulled down my plastic panties, they clung to my wet diapers and she simply pulled the saturated cloth down to my ankles. Seeing her deep cleavage I started to get a little hard-on but she ignored it as she pulled me over her lap. My stiffened wiener rubbed against her silky thigh and I felt myself becoming aroused despite my best efforts. Almost immediately, I felt her greasy finger probing my back hole and I squirmed uncomfortably on her lap.
"You better settle down if don't want another session with the paddle,'' she warned me.
I bit my lip and looked down at her spike heels helplessly as she buried her Vaseline covered middle finger all the way in and swirled it around. As she pulled it out, I felt her re-invade my hole with a warm but thick nozzle. I whimpered in panic and tried to clench my cheeks together but she slid it in effortlessly and a moment later, I felt a surge of hot water gurgling unimpeded into my rectum.
Without thinking, I let out a moan that sounded like it came from a little girl as the soapy water flowed into me. Occasionally, Jennifer would stop the flow and wait for it to settle in before resuming the enema. A bead of sweat appeared on my forehead and I squirmed as my babysitter released the clip again and the hot soapy water continued to fill me up. I felt the cramps set in and I wondered desperately how much longer I'd have to endure this torture.
I moaned helplessly and tried to rise off her lap but she easily held me down and snapped the clip shut.
"I'm afraid not, my little sissy-boy. You've still got a lot more to go. I want to make sure you get a good cleaning because you're going to be in your diapers all day and I don't want to be changing any messy ones later."
I bit my lip and squirmed uncomfortably over her lap as she released the clip again.
About ten minutes later, Jennifer finally emptied the rest of the bag into my pouting bottom and let me up. I limped to the bathroom and released the enema in a gushing torrent as I heard her call to me.
"When you're done, come into the bedroom so I can get you dressed."
I could only wonder what she had in mind but I hoped she'd allow me a little dignity since I'd been trying to be better.
After I had cleaned up, I walked into her bedroom wearing a towel around my waist. She was sitting at her vanity, applying some lipstick to her full and sensuous lips.
She caught my reflection in the mirror and stood up from her seat.
"Come on, let's get you changed, you've a big day ahead of you," you informed me tersely.
I hated the sound of 'getting changed' and I looked down at the triple thick diaper laying on the changing pad. She patted the center and beckoned me to sit on it but I clung stubbornly to my towel.
"Now, you can either do this the easy way, or I can get my paddle and we can do it the hard way--its up to you Mister," she told me with a superior smirk on her face.
My lower lip trembled as I pouted and knew I was beaten. I slowly unwrapped the towel and she guided me down on top of the soft mass of cotton.
"That's a good baby," she cooed. From somewhere I hadn't noticed, she produced a baby bottle full of warm milk and she pushed it between my lips. "Here you go Bobby, maybe this'll make you feel better."
I blushed hotly as I took the bottle and suc-ked miserably on the nipple. She powdered my fanny and crotch before pulling the thick diaper up and pinning it snugly with big, pink ducky pins. Despite my intense feelings of humiliation I couldn't help but love the baby softness that now enveloped me. I felt so comfortable and secure and I thought, as long as no one else sees me, this might not be too bad. I found myself unable to close my legs but before I could think about that, the doorbell rang.
My heart skipped a beat as Jennifer went to see who it was.
“Don’t you even think about moving,” she cautioned me with a wag of her manicured finger. Nervously, I held my breath as I heard her open the door, followed by several women’s voices as they greeted each other. They talked for a few minutes and then I thought I heard them coming down the hall.
In a panic, I looked around the room. Where could I go? The only door out of here led to the hallway and now they were coming in!
I blushed hot red as Jennifer came in with two women, one, in her late thirties, and the other, obviously her daughter. Both were very attractive with long brown hair and sexy figures and her daughter wore a short halter top that displayed her curvy breasts nicely.
I gasped in shame and looked down at the floor as the mother came over to the bed.
“So this is the baby you’re taking care of,” she exclaimed excitedly, “My, you’re a big one, aren’t you, darling,” she said as she pinched my cheek.
“I was just getting him dressed for the day when you came over,” Jennifer explained.
“What a sissy,” her daughter said with disdain, “Does he wet his diapers too?”
“Oh yes, just like any little baby. I have no idea what his mother was thinking, letting him go around with big boy underpants on. As often as he wets, I wouldn’t dare let him out of his diapers.”
I wilted as she belittled me in front of her friends.
“Tiffany, I was just about to put him into his plastic panties, would you like to pick out a pair for me? They’re over in the closet there,” Jennifer asked.
“Sure, I’ll find something for the big sissy,” she replied mockingly.
She came over with a pair of white nursery print plastic panties, the leg and waist openings lined with soft ruffles, and held them up for me to see.
“Is this what Mommy’s little sissy wants?” she asked condescendingly.
I pouted and shook my head no.
“You’d better learn some better manners than that if you don’t want your bottom paddled again Bobby,” Jennifer warned me sternly.
I looked up at her fearfully, my face red with shame.
“Please don’t Aunt Jennifer,” I pleaded.
“Then what do you say to Miss Tiffany, who has so kindly offered to get you ready for the day?” she prompted.
“Yes, Miss Tiffany,” I mumbled barely audibly.
“Speak up, Bobby,” Jennifer warned, her voice taking on an edge.
I cleared my throat.
“Yes, Miss Tiffany.”
“Yes, Miss Tiffany, what?” Jennifer prodded.
“Yes, Miss Tiffany, may I please wear those plastic pants?” I said in a shaking voice.
“Plastic panties,” Tiffany corrected me. “Baby boys wear plastic pants. Sissy babies like you, wear plastic panties.”
"Plastic panties," I repeated dutifully.
Tiffany held the leg holes open and guided my feet through them, sliding them up my skinny legs and then up and over the thick, bulging diaper I was wearing. I couldn’t help but look down her top and watch as her breasts jiggled before me. She had to tug and pull to get the panties up over the bulky cloth but she was soon tucking the last bits of it into the elastic leg and waist bands.
“There. All secure now. This baby won’t be wetting on the car seat,” she said confidently.
“Car seat?” I quaked, “Wha-what do you mean?”
“You’re coming over to our house today, Sissy, as soon as we’re finished dressing you,” she replied.
By now Jennifer had pulled off my nighty and she began lowering the pink dress from yesterday over my head. My mind was in a panic as I struggled with what I should do. Before long, Jennifer had me in my anklet socks and Mary Janes as her friend tied my hair into pigtails.
“We’re almost ready to go,” Jennifer said as she opened her dresser. “Now, we’re ready,” she said as she picked up her wooden paddle and put it into her purse. I shuddered as I saw that and they stood me up to look at their finished efforts.
“Turn around, Bobby,” Jennifer ordered me.
They made me twirl around like a ballerina and as I complied, I caught sight of myself in the full length mirror on the wall. My babyish nursery print panties could easily be seen bulging out from beneath the short, frilly hem of my party dress. I looked so sissyish and infantile, my lip trembled and I thought I was going to cry.
“Oh, quit pouting, Bobby,” Jennifer frowned, “You know you enjoy wearing frilly panties. I’m just giving you what you were afraid to ask for.
“Now come on, let’s go. I don’t want any trouble out of you today,” she warned me.
As we began walking out of the bedroom, Tiffany stopped us.
“Oh wait, we forgot something.” With that, she came over and popped a pink pacifier into my mouth.
“Now, we’re ready,” she said with a sadistic smile.
We headed for the door, Jennifer pulling me along determinedly by my wrist. As the full impact of what was about to happen hit me, I stopped in my tracks. It was one thing to be dressed up like a baby girl inside, but quite another to be taken out in public. I tried to yank my wrist free but her hand was like a vice.
“No, noo!” I squealed as the pacifier dropped out of my mouth.
“Come along, Bobby. You’re going out that door and that’s all there is to it!” she told me sternly.
“No! I can’t!” I said, the panic rising in my voice. I looked around for support but Tiffany had already scooped up my pacifier, brushed it off, and was bringing it back to my mouth.
“Do you need me to put you over my knee again, young man? Because I’m perfectly happy to do it. I’m two seconds away from pulling those diapers down and paddling your bottom until you won’t be able to sit for a week!”
My lip quivered in fear and I knew all too well she meant it.
“No, please…not that, aunt Jennifer,” I begged.
“Then let’s get going,” she said as she opened the door.
Betty Pearl's Sissy Stories 20.1
Topic: Bobby's Babysitter (Read 26159 times)
