Babysitting For My Sister

[Baby Bobby]

Note to the reader; This is part two of my sister series the first being A Visit to My Sister’s House, and the third is Another Visit to my Sister's House.

The front screen door closed with a loud clatter, signaling the arrival of my sister's stepson, Brian, home from school.
I was over visiting in the afternoon, having agreed to babysit the boy while she went out to a company function that evening.

Wiping her hands on her apron, my sister stepped out of the kitchen to see her stepson standing just inside the door, sobbing uncontrollably, his face wet with tears.

She rushed forward to embrace him, throwing her arms around him and holding him tight.

"What's the matter, sweetie?" she asked him, full of concern.
He didn't answer immediately, but instead buried his nose into the protective cushion of her bosom, as I had often seen him do when he was distraught.

"Hey baby, can you tell me what happened?" she asked in her most soothing, motherly voice.

He wiped his face and sniffled, looking up at us for the first time.

"It-it w-was T-Tiffany again," he sobbed, "she was teasing me."

I sighed to myself and rolled my eyes, although my sister seemed unfazed by the news. Clearly, she didn't seem surprised that her boy of 14 could be brought to tears by a mere girl.

Ever since his parents had been killed in a car accident and he had come to stay with Julie, she had told me that Brian had been a godsend and yet, also a challenge to her limited parenting skills.
On one hand, having been without children previously, she seemed to cherish having a precious little boy of her own to mother over. He had never spoken a harsh word in his life, and she said she had never had a need to discipline him.

On the other hand, the boy, due to his timid and delicate nature, was frequently the target of bullies, both at school and around the neighborhood. They saw him (as did I), as being a delicate sissy and an easy target.
Tiffany Johnson, who had something of a reputation in our neighborhood and was about the same age as Brian, was one such bully.

As Julie hugged her traumatized stepson, her hand carefully reached down the back of his pants, apparently feeling for something. I was confused by this move until she pulled her hand out and rubbed her fingers together.

"Looks like mommy's baby soaked his trainers today," she announced.
"Come on baby," she said soothingly, "let's get you into some dry underwear."

"You have him wearing training pants during the day now?" I asked incredulously.

"Yes, sometimes Brian has accidents at school, so I've found this is the best solution," she replied casually, as if it were perfectly normal for a teenager to be wetting his pants during the day.

I shook my head in frustration.
"Have you ever tried disciplining the boy, instead of molly-coddling him?" I snapped.

I didn't mean for that to sound harsh and judgmental, but sometimes my sister frustrates me with the way she handles her boy. In my house, I've solved a lot of problems with a good old-fashioned, over-my-knee spanking. My paddle doesn't get used that often, but when it does, I make sure it leaves a lasting impression.

My sister sighed with exasperation.
"He's just going through a rough period right now--I know you don't always agree with my methods, but in Brian's case, I just feel he needs a softer approach."

I shook my head as she took him by the hand, carefully leading him down the hallway and into his bedroom, which looked to me more like a baby's nursery. Already, Brian seemed to have calmed down, and his crying had been reduced to intermittent sniffles.

Taking him over to a two foot high changing table, Julie sat him down gently and began undoing his sneakers along with the snap on his trousers. In just a few moments, his pants had been removed and were folded neatly, laying on the floor, ready to be put away.
He looked away from me in embarrassment as he sat there, his wet trainers and plastic panties now fully exposed to us. I shook my head again as I looked down at his prissy plastic panties, which were yellow nursery print, just like that of a baby's.

Hooking her fingers inside the elastic waistband of his waterproof panties, Julie pulled them down along with his soaking wet trainers, depositing them in the large diaper pail next to the table. The pungent smell of stale, pee-soaked diapers surrounded us as she lifted the lid.

Looking down at his nearly hairless crotch, my brow rose in surprise as I spied a diminutive chastity device locked around his tiny, insubstantial package.

"Umm, what is that?" I asked in confusion.

"Oh, it's just a little something I got him for his 13th birthday. Back when I first started putting Brian into diapers again, I soon discovered that he liked the soft Birdseye cloth a little too much and he was...well, masturbating in them on a regular basis. After a little research online, I found just what he needed--a secure chastity device, and now it prevents him from being able to play with himself anymore. It also won't allow him to get an erection so he's my good little boy again."

Brian's face blushed a bright red and he bit his lip in embarrassment as he anxiously looked away, bunching his fists in mute frustration.

Quite frankly, I was at a loss for words and I watched silently as Julie gently grasped his ankles and raised them up over his head to smear a thick, sticky coating of Desitin on his round little rump. Still blushing, Brian tried to keep his balance, and he reached over to pick up his teddy bear that was lying on the floor next to him, clutching it to his chest for comfort.

Taking three fluffy thick diapers from the cupboard next to the table, Julie positioned them under her stepson's upraised bottom before lowering him back down on the soft, waiting stack.

"Isn't it a little early to be putting him in diapers?" I asked finally, no longer able to keep my silence.
I knew about her son's bedwetting habit but I didn't think he needed them during the day too.

"Well, I've found that when Brian's had a hard day at school, it makes him feel better when I put him into his diapers when he gets home. I guess it's a sense of safety and security for him."

I shook my head but said nothing. If ever there was a bigger sissy in this world, I certainly didn't know of one.

"That Tiffany is a very bad person," Julie stated to no one in particular, as she sprinkled baby powder over Brian's private area, surrounding us with its fragrant, albeit infantile aroma, "she's nothing but trouble in this neighborhood."

Her effeminate stepson nodded in agreement as he clung tightly to his teddy bear.
While I didn't have a high opinion of her myself, I thought it was ridiculous that she could bring a boy like Brian to tears so easily.

"She always calls me a sissy," he whined in his high, prepubescent voice.

She's got that right, I reflected ruefully.

"I know baby," Julie said as she pulled the bunny soft cotton cloth up between his legs and gently pulled the corners around his narrow hips, "but now you're home and you can forget all about her."

I shook my head as I pictured the tall brunette girl in my mind.
I disliked her for skimpy, slutty clothing and her budding, adult figure, even though she was only 15. To be sure, her body was very mature for how old she was and I knew she used it to her advantage at school.
Brian was completely intimidated by her, and from what I had heard, she used her womanly figure and feminine wiles to push him around, along with a number of other weaker males.

"Here you are sweetie," Julie said as she began snaking a colorful pair of nursery print plastic panties up his smooth legs, "this will keep my baby dry for the afternoon."
He whimpered a little but dutifully lifted his bottom, allowing her to pull the crinkly waterproof panties up and over his big, bulky diapers. She took a little time to run her fingers all the way around the leg openings and his waistband to make sure all of the fat, absorbent cloth was contained within the shiny pink panties.
Lastly, she powdered between his thighs and the wide crotch of his diapers that were preventing him from being able to bring his knees together.

"Okay honey, I think you can put your shoes back on for yourself," she told him as she busied herself putting away his diapering supplies.
Her stepson, anxious to get away from my disapproving glare, hurriedly put his sneakers back on and made ready to leave the room. As he slipped past us to go out the door, Julie slapped him playfully on his thickly diapered bottom, smiling with affection at her babified boy.
She beamed with satisfaction as he waddled down the hallway.

"Thank you for agreeing to watch him tonight," she said as we walked out of his nursery, "He may be almost 15, but I don't feel he's ready to be unsupervised yet."

I rolled my eyes and shook my head.
"Looks to me like he's not ready to be potty trained yet," I replied sarcastically.
"Stacey," she said in a tone of voice that did nothing to hide her annoyance with me, "you can raise your own boys in the way you want to and I will raise mine in my own way."

I said nothing and bit my tongue, not wishing to hurt my sister's feelings who I loved, even if I didn't agree with her methods. It's just that I felt she was only encouraging Brian's natural sissyish tendencies. Maybe part of the problem was that Julie was still a single parent. I was sure that if Brian had the firm hand of a father figure in this house, things would be quite a bit different.

Our methods of raising our children were not the only differences between my sister and myself. Physically, we were also quite different. Whereas Julie had kind of let herself go over the last 10 years or so, I had worked hard to keep the body that I graduated high school with. I worked out regularly, and I still sported a 24 inch waist.
And I have to say, I still get a lot of looks when I wear my skinny jeans out in public, despite being in my late 30s.

So it was that after Julie left for her meeting, I changed into my workout outfit and began doing my yoga exercises in the living room.

I've always suspected that Brian had some sort of childish crush on me, based on the surreptitious glances I would catch him making whenever he was around. This was particularly true when I happened to be wearing any kind of clothing that was revealing or snug fitting. His chastity device not withstanding, I would often catch him staring at my breasts in particular, a perverted habit I found extremely annoying.

[Baby Bobby]

This afternoon, I was stretching backwards with my arms over my head in a pose that I knew thrust my chest out in a prominent way. Out of the corner of my eye, I could see Brian blatantly staring at me, apparently unaware that I could see what he was doing.

My head spun around and I snapped my fingers sharply at him.

"Stop staring at my breasts!" I barked angrily, "Or you'll find yourself with a very sore bottom."

His mouth, which had been hanging open as he gaped at me, snapped shut and he blushed hotly.

"I-I wa-wasn't staring," he stammered, but his bright crimson cheeks said otherwise.

"Why don't you go outside and play," I told him brusquely as I changed poses and put my back to the prissy, diapered teen.
Looking down at his shameful underwear, he shifted his feet and stared at the floor.
"Um, that's okay," he mumbled.
It was hardly surprising that he wouldn't want to be outside, what with his fat diapers and pink plastic panties so obviously exposed.

Still, I felt very self-conscious as I switched to Downward Facing Dog, knowing he was probably leering at my backside.

"Umm, aunt Stacey?" he inquired uncertainly.
"Yes, what is it," I replied curtly.

"Umm, I was wondering if, um, you could...you know...ah, maybe unlock my um...device?" he asked in a halting, unsure voice.

I didn't answer him immediately, although I knew deep down there was no way in hell I was going to do anything that would lead to his ultimate sexual gratification. Nevertheless, as I sat there stretching, a germ of an idea began to form in my head and I was quick to suppress a small smile before it had the chance to show on my face.

"You'd like me to unlock it?" I asked, as I turned around to face him.

Unconsciously, his gaze automatically dropped down to stare at the line of cleavage disappearing into my workout top before he realized I had caught him once again.

"Yes--please," he replied in his meek voice, staring at the furniture now.

"What do you think your mommy would say?" I asked him pointedly.

He blushed again, but did his best to try and cover his lapse.

"She-she wouldn't mind," he answered me, although his voice lacked conviction.
He must have thought I was born yesterday.

"Really," I quipped, the doubt obvious in my voice.

"Oh yeah, she really wouldn't mind," he said quickly, the excitement rising in his voice. Apparently, he really did believe I was foolish enough to take his word for it.

I looked at the sissy, with his big pink diapers bulging around his hips, making him look like an overgrown toddler. Here was an opportunity to give him the strict discipline he was so sorely lacking.

"Okay," I said nonchalantly, "I'll just go get the key."

"R-really?" he squeaked. He smiled big, looking barely able to contain his anticipation.

"Then again..." I said toying with him, an uncertain look on my face, "...Maybe I should just give your mom a call to make sure."

The color drained from Brian's face and his excitement vanished as if I had just poured a bucket of ice water over his head.

"Oh--you don't have to do that," he said emphatically.

"--But you just said that she wouldn't mind," I reminded him, "so you shouldn't have any objection to my calling her."

He shook his head and bit his lip, a small bead of sweat appearing at his brow.

"I-I changed my mind, you don't have to unlock it now."

"Oh no, I'm happy to unlock it. Just let me call your mom right now and we'll get this all settled," I insisted as I picked up my cell phone and quickly dialed the number to my sister.
Brian was looking around the room, desperately seeking a solution to the dilemma he had inadvertently created.

Julie answered after the first ring.

"Hey Sis...oh yes, everything's fine...yes, he's right here...Oh, he's just fine," I said, reassuring my overprotective sister regarding her boy.
"Look--I'm sorry to bother you but...Brian just asked me if I would unlock his chastity device and he said that you were okay with that. Is that true?..."

I eyed her stepson as he squirmed in front of me, plainly uncomfortable at having his lie called out. He was shifting his feet, clasping and unclasping his hands nervously, looking like he wanted to run away at any moment.

"No?...It's not okay?" I responded, my eyes narrowing at her diapered, sissy boy, "Very well...yes, I can take care of it--no, I've got it...okay, thanks again--sorry to bother you."

I ended the call and put my cell phone down with great deliberation.

"Brian, I don't tolerate little boys who lie to me," I said gravely, "Your mom may put up with that kind of misbehavior, but I certainly won't."

Reaching into my purse on the couch, I pulled out a wooden paddle that I keep for occasions just like this.

He put his hands up before him and began backing away.

"Y-you can't sp-spank me," he quaked, his voice brittle with fear, "My mom never spanks me!"

"I'm not your mommy," I replied tersely as I rose to my feet.

"N-n-no, please," he stammered as waves of panic swept over him.

"Brian, this is something you've had coming for a long time," I said firmly.
Snatching his wrist, I swiftly took a seat on an armless chair in the dining room and yanked him over to my side.

"No--please--please don't spank me!" he quailed in terror, stamping his feet in a show of petulance.

"This is what happens to little sissy boys who think they can fool me," I growled as I tugged his shiny pink plastic panties down off his diaper.
It was then, that I looked down to see the big wet spot in the center of his crotch.

"Brian--did you wet your diapers??" I demanded.

With a sob of shame, he nodded his head, his eyes brimming with tears.

"That's only going to add to your punishment," I told him as I jerked him over my lap. He squealed like a little girl and kicked his feet while I quickly unpinned the thick cloth of his diapers. In no time at all, his soft, baby bottom was exposed, twitching in anticipation of the paddle.

"You should be ashamed of yourself," I scolded him, "A grown boy still wearing diapers like a little baby. It's bad enough that you're a bedwetter but now your wetting them during the day too?"

Brian sobbed and struggled, weakly trying to escape from his prone, compromising position.

Before he could answer my question, I brought the paddle down good and hard, smacking his bare bottom with every ounce of my strength.
He howled at the top of his lungs, kicking his feet wildly now.

Again and again, I swatted his lily-white cheeks, leaving hot, angry imprints from the paddle. In no time at all, I brought his buns from bright pink to a blistering shade of deep red.
Brian cried like a baby, slapping the floor and wailing as I gave him the punishment he so richly deserved. All the years of frustration and resentment boiled over and I took it out on his blotchy, swollen red bottom. The hard, unforgiving wood of the paddle flattened his baby soft, tender cheeks, leaving them an even deeper shade of stinging crimson before bouncing back up to receive yet another harsh swat.
Brian was kicking his feet frantically, but his efforts were hampered by the fact that his pink plastic panties were tangling around his ankles. He flailed them miserably and struggled to get up off my lap but I easily held him in place, smacking his bottom even harder with the paddle.

The sounds of Brian's high-pitched crying, combined with the loud, unremitting swats of the paddle, filled the room and spilled out through the open window to the outside. Part of me was pleased with the thought that his neighbors would now know that Brian was finally getting a good, hard spanking that was so long overdue. I felt certain that they would agree with my methods of discipline for the bedwetting sissy.

I was smacking the pink sides of his bottom when all of sudden, the doorbell rang, momentarily interrupting Brian's punishment.
Pausing my efforts and looking out the window, I could vaguely see a teen-aged girl standing outside the front door.

"Come in!" I called out to her.

The door opened and who should come in, but Tiffany Johnson!

Brian immediately tried to get up to escape but I held him in place, forcing the struggling sissy to remain in his humiliating position even as he continued to sob like a baby.

"Hello, Mrs. Taylor," Tiffany said politely, a coy smile on her pretty face, "I'm sorry to interrupt here, but Brian left his school books in class so I thought I would bring them over."

Taking a moment to look the young woman up and down, I could certainly understand why so many of her male peers lusted after her. Her big breasts were barely contained in the form-fitting buttoned top that looked like it had been practically spray painted over her slim torso. Her jeans were no less tight, and I saw that she was already wearing heels that I thought were much too tall for a girl of her age. In the back of my mind, I idly wondered what sort of mother would allow her daughter to dress this way.

In any case, I couldn't help but be skeptical of her statement. Other than her small purse, I didn't see any books in evidence, which contrasted with what she said her purpose for coming over was. More likely, I suspected that she was just walking by and heard Brian being spanked, thinking she would come and investigate it.

Nevertheless, despite my rather low opinion of her, I found her unexpected arrival to be fortuitous. I was only too happy to pile yet more humiliation on top of Brian's existing punishment and I knew Tiffany's presence would add richly to it.

"Hello Tiffany. I'm almost finished here," I explained as I rested the paddle on Brian's blazing red bottom, "I caught him lying today so he's getting a spanking to teach him a lesson.
"And if you don't mind waiting, I also have to change his diapers," I added.

"Oh, not at all," she said, barely suppressing a giggle, "Take your time."

I smiled and then swung the paddle upwards, bringing it back down with a deafening swat across both of Brian's hot, candy apple cheeks. He wailed loudly and slapped his hands on the floor bitterly as I continued his harsh spanking.
Ten more, well-delivered swats and I finally set the paddle down.
Brian was crying uncontrollably as I helped him to his feet, his wet diaper remaining on my lap. Tiffany's eyes dropped down to stare at his crotch, even though he quickly tried to hide his embarrassing chastity device with his hands.

"Are you ready to have your diapers changed?" I asked the sobbing sissy.

He nodded his head, unable to articulate a coherent response through his crying.

"Come along then," I said as I took his hand and began leading him down the hall to his nursery. His plastic panties were still around his ankles but I didn't give him the opportunity to take them off. As a consequence, he was forced to make a humiliating shuffle, stumbling along as his waterproof panties inhibiting his gait.

As we came into his nursery, Tiffany's eyes were everywhere, trying to take it all in. While she had always thought of Brian as nothing but a big sissy, seeing the evidence here of his baby's nursery was the final nail in the coffin.

"Wow...I had no idea..." she marveled, "I didn't know he wore diapers."

"Yes he does," I remarked sourly, as I led the sobbing youth over to his changing table, "And he can't seem to keep them dry for any length of time."

"Wow, what a total sissy," she exclaimed.

Brian's face and chest were bright red with shame and he cried out the moment his scorched, stinging bottom made contact with the vinyl covered changing table.
Taking three of his thick diapers as I had seen his mother do, I slid them under his buns and drew the bulky cloth up between his legs. Looking down at the crying sissy, I powdered him all over before pinning the corners of his diapers together.

"Would you like to put his plastic panties on?" I asked Tiffany.

"Sure," she giggled.

Taking a white pair of very babyish nursery print panties, she gathered the leg holes together and positioned them around his feet.

"Here you are sweetie," she said in a very condescending voice, "Plastic baby panties for a big sissy baby."

With a smug smile on her pretty face, she slowly, teasingly, pulled the waterproof panties up his legs and began wrestling them over his big, bulging diapers. To be sure, this was a day I knew he wouldn't soon forget.
Brian burst into fresh tears, the shame and humiliation overwhelming him.

Personally, I didn't feel any sympathy for him. After all, his own mother told me just hours before that he enjoyed wearing diapers because they made him feel safe and secure. I was simply giving him what he wanted.

Pulling him to his feet, I slapped him on his fat, diapered bottom, eliciting a yelp from him and making him buck forward in the direction of the door.

"Run along and play, Brian. But you can expect to have an early bedtime tonight," I informed him.
With a sob, he fled the room, waddling as fast as he could.


Tiffany left about an hour later, but not before we'd had a little chat, just girl to girl. I got to know her much better and I have to admit, I agreed with much of what she had to say about the opposite sex. She's a smart young woman with a lot of promise.
Oh, and she never did say anything further about Brian's books.



THE END

[RibbonBound]

Note to the reader; This is part two of my sister series the first being A Visit to My Sister’s House, and the third is Another Visit to my Sister's House.

Is this story, "My Sister and Her Sissy Son" the first part of the series? 

A note to the reader; This isn't necessarily a new story, although it is new for this site (it was formerly known as A Visit to My Sister's House). However, recently, I decided to add a sequel to it, so I thought I would post the whole thing here.

[Baby Bobby]

 ( " at " ) Ribbonbound;  My bad--I thought it was already posted here but I had posted it on my Tumblr blog.
You can find the first chapter here; https://buffalobetties.net/storytime/index.php?topic=1311.new#new