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21
Active Sissy Stories
/ Re: Babysitting For My Sister
« Last post by RibbonBound on February 08, 2026, 04:05:58 PM »
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.
22
Active Sissy Stories
/ Re: Babysitting For My Sister
« Last post by Baby Bobby on February 08, 2026, 01:02:37 PM »
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
23
Active Sissy Stories
/ Babysitting For My Sister
« Last post by Baby Bobby on February 08, 2026, 12:55:08 PM »
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.

24
Active Sissy Stories
/ Another Visit to My Sister's House
« Last post by Baby Bobby on February 08, 2026, 12:33:42 PM »
Note to the reader; This is the third part in a series, the first being A Visit to My Sister’s House, followed by Babysitting For My Sister.

Another Visit to My Sister’s House

“Sis?” I called out as I knocked on the front door and opened it, letting myself in.      
  “In the nursery, Stacey,” she called from the back of the house.
  Setting my keys and purse down, I made my way down the hallway to the open door at the end.
  Walking into the brightly lit room, I was taken aback at the scene before me; my nephew Brian was bent over my sister’s lap, his colorful plastic panties around his calves and his thick, soaking wet nighttime diapers pulled back between his legs. A fat rubber nozzle was buried in his back hole, held firmly in place by my sister Julie, and from it, a white hose led up to a red rubber enema bag that looked like it was close to bursting, hanging from a stand.
  The effeminate sissy was squirming helplessly on her lap, moaning from the torrent of soapy water flowing steadily into his bowels.
  I moved around them to get a better look at him, and Brian glanced up at me, his face blushing deep red with humiliation. Clearly, he was mortified to be seen in this compromising, emasculating position.
  He was still wearing his jammies from last night, a fuzzy pink top with a design of Strawberry Shortcake across the bodice and white lace around the short, puffy sleeves. His feet, which kicked aimlessly from time to time, were adorned with white, lacy anklets.
  “Um, so what’s going on here?” I asked awkwardly.
  My sister smiled pleasantly up at me as she closed the clip shut on the hose, temporarily halting the flow of liquid into her sissy son’s rectum.
  “Just giving Brian his usual daily enema,” she said, as if it were the most normal thing in the world.
  My brow furrowed in frustration and lack of understanding.
  “Um, I don’t get it—he gets one of these every day?”
  “Yes, I find it’s the best way to ensure he doesn’t have any number 2 accidents in his diapers—I like my little boy to be squeaky clean, inside and out,” she said as he patted his bare bottom affectionately.
  “Well...I knew he was wearing diapers for his bedwetting--how often is he wearing diapers now?” I asked incredulously.
  “Oh, all the time,” she replied simply.
  “All the time? You mean during the daytime too?”
   Brian’s cheeks flushed and he looked away anxiously. It was apparent he was deeply ashamed to have this humiliating information revealed to me.
  “Yes, well, you see--last week, Brian wet his pants while we were at the mall. I think he just got a little excited and lost control. And then last Tuesday, he had another accident while we were in the car going over to Jane’s place. There have been several times when he wet his trainers at school. And truth be told, there have been other times when I’ve found his pants with a little wetness from time to time...
   "So...I’ve decided it’s time to keep him diapered during the day as well for the foreseeable future. I really think he needs them, because he’s wet himself several times since we started doing it and I don’t think he was even aware of it.
  “I’m going to take him to the store this afternoon to get him some more diapers and plastic panties...cause my little boy wets a lot—don’t you, babykins?” she said in her cloying, sugary voice as she bent over to speak to him.
  I shook my head in dismay.
 â€śIf he were my boy—"
  “—Yes, I know very well what you would do,” she interrupted me with surprising vehemence, “And I’ll thank you kindly to refrain from spanking Brian ever again.”
  I crossed my arms over my chest in defiance.
  “-Served the little sissy right for lying to me,” I retorted, “At my house, little boys that lie get paddled.”
  My sister sighed as she opened the clip to the enema hose, causing Brian to moan weakly as the water began flowing again.
  “Stacey, we’ve had this conversation before—I have different methods in the way I raise Brian. You may not agree with them, but I’m doing what I think is best for him.”
  It frustrated me that my sister seemed to encourage Brian’s sissyish behavior but I didn’t want to argue with her about it. He was, after all, her son, not mine.
  Looking around the room, I could see that there had been many changes over the last few months. The walls were decorated now in a feminine nursery style, with elephants and lambs playing amongst baby rattles and building blocks. Of course, the pink and white crib that Brian now slept in dominated the room, with its soft, cozy Disney Princess blankets and barred sides that prevented him from getting out during the night. And his diaper changing supplies had only been added to with large stacks of cloth diapers, plastic panties, diaper rash cream and baby powder surrounding the raised, vinyl covered table. I saw that in addition to the other infantile items in the room, Julie had added a toddler style playpen as well.
  It looked to me like the little sissy was going through a second babyhood.
  Needless to say, Brian’s nursery smelled of lingering, stale pee and there could be no disguising that an incontinent bedwetter lived in this room.
  “That’s quite a big enema...can he really take all that in?” I asked, changing the subject.
  “Oh yes, it just takes patience. He’ll protest and claim he can’t take any more but in the end, I know he can take all two quarts.”
  I watched the squirming sissy as more and more soapy water gurgled into his bottom but to be honest, I really didn’t feel any sympathy for him. He was such a prissy pantywaist that this seemed like just what he deserved.
  “Ohhhh,” he moaned weakly as another powerful surge flowed deep into his bowels. 
  “This is just what my little baby needs,” my sister told him cheerfully, patting him affectionately on his bare bottom, “Mommy’s happy to change your wet diapers but she doesn’t want any messy ones.”
  Brian bit his lip in angst, unable to stop another moan escaping from him. Like it or not, this was the price he was being made to pay for his lack of control.
  Taking a seat on the edge of his crib mattress, I watched patiently, the emasculating spectacle as Brian was forced to take two full quarts of warm, soapy water, squirming and whimpering helplessly on her lap. Although originally I had been skeptical that he would be able to take so much liquid, to my surprise, I watched as the rubber bag was eventually drained flat and Brian lay bent over, fidgeted uncomfortably, his bowels churning with all that warm, soapy water.
  “This also does a good job of draining my little boy of all his naughty juices,” Julie explained, “I’ve read that they tend to build up for boys that wear chastity devices.”
  This, at least, was one change that I was in complete agreement with her on. I could think of no one more deserving of permanent chastity than her sissy son Brian. After enduring years of his lustful stares at my body, I was immensely pleased to see his tiny genitals locked up for good. To be sure, he would not be experiencing an erection at my expense any time soon.
  Carefully and slowly, my sister pulled the long, fat rubber nozzle out of Brian’s pouting bottom. I was surprised at the size of it, and I had to imagine it must have taken a bit of effort to get it inside him.
  “Okay babykins,” she told him as she helped him up, using her new pet name for him, “you go release that and I’ll get your daytime diapers ready for you.”
  Brian limped off to the bathroom, his cheeks blazing with shame, and I watched as Julie dumped his heavy wet diapers in the pail and began preparing another set. Taking three of the fluffy cotton rectangles, she arranged them on the changing table and placed a soaker pad between each layer. This made for a very thick, babyish diaper for the young teenager and I watched as she silently debated which set of prissy plastic panties would go over them. Finally, she decided on a pink satin pair of rumba panties, lined with practical waterproof vinyl and having three dainty rows of white ruffles across the bottom.
  “How long do you think Brian will have to wear diapers during the day?” I asked her.
  “Oh, probably not too long...maybe six months or a year. I think it’s just a phase he’s going through,” she replied, obviously unconcerned, “It really is for his own good.”
   This seemed to be her original explanation for putting him in diapers at night time but I didn't point that out to her.
  “Has his bedwetting improved at all?” I asked out of idle curiosity.
  “Oh no, in fact, I can’t even remember the last time Brian had a dry night,” she replied, “He’s really becoming more and more like a toddler all the time,” she added with a smile.
  “No argument here,” I quipped.
  I knew it was pointless to argue with my sister about discipline methods so I steered the conversation to safer grounds.
  “So what have you got planned for this morning?”
  “Brian is hosting a tea party for some of the neighborhood girls, and I thought it was best if he started socializing with people who were less...um...judgmental of him.”
  “A tea party?” I asked, not sure what to make of her announcement. Personally, it sounded about as sissy an activity as was possible.
  “Yes,” Julie said absentmindedly as she was sifting through a collection of babyish dresses in the closet, “his other friends seemed to have abandoned him for some reason.”
  Gosh, I can’t imagine why, I thought to myself but I kept my sarcasm silent.
  She finally pulled out a pink and white baby dress with delicate touches of lemon yellow. It had a very short, but wide hem with a built-in petticoat that flared it out away from the high waist.
  By now, the subject of our discussions had returned and he kept his gaze averted shyly downward as he silently entered the room.
  “Ready for your diapers, baby?” Julie asked solicitously.
  Brian nodded silently, too embarrassed to actually respond.
  Taking his hand, my sister gently led him over to the changing table and set him down on the thick stack of fluffy diapers.
  “That’s my good boy,” she commended him as she grasped his ankles together and raised them over his head. Brian couldn’t look me in the eye as my sister lovingly smeared diaper rash cream across his bare bottom, making sure it was coated with a nice, sticky white layer before gently lowering his legs and applying baby powder over his chastity device and front area. Pulling the thick front of his diapers up between his thighs, she pinned the sides together with pink duckie pins. Standing him up, she had him step into the pink satin rumba panties and she slowly pulled them up his skinny legs, fitting them up and over his fat diapers as he whimpered softly with embarrassment.
  Removing his Strawberry Shortcake top, she replaced it with the toddler-style dress she had chosen earlier, turning him around to face me as she did up the small buttons in the back. Brian flashed a furtive glance at me before averting his gaze-he knew that I thought of him as nothing more than a childish, bedwetting sissy.
  Fitting a pair of glossy pink Mary Janes on his feet, Julie pulled his longish blonde hair into two pigtails, securing them with some matching pink satin bows.
  Standing him before a full-length mirror, Julie patted his fat, diapered bottom proudly as they gazed at his babyish reflection together. With his dress barely coming down past the waistband of his shiny rumba panties, it left his bulging, humiliating diapers fully exposed.
  “Don’t you look just precious?” she cooed.
  Brian was blushing furiously but I could tell that deep down, he too, secretly liked what he saw.
  “You’ll always be my little baby,” Julie said lovingly as she hugged him close.
  Just then, the doorbell rang, and Julie took Brian’s hand, leading him out of the nursery. I followed them and watched as they greeted a pair of young girls. They looked about nine or ten to me, and I reflected that they were certainly dressed more maturely than 13 year-old Brian. Nevertheless, they greeted him excitedly and the three went into the living room where a low table with a tea set had been arranged. After making sure everyone was settled, Julie left them to their fun and we retired to the dining room to catch up on our own interests.
  A couple hours passed with giggles and childish laughter coming from the other room and after a while, Julie decided to check on Brian. Walking into the living room, we saw one of the young girls combing the sissy’s hair into a girlish style. Julie bent down behind him, lifting the back of his frilly dress and silently slipping her hand past the waistband of his satin baby panties.
  “Wet again,” she sighed, “Oh well, let’s feed you your lunch and then I’ll change your diapers.”
  The other girls giggled as she took Brian into the dining room, sitting him in an over-sized high chair. Taking a safety strap, Julie secured it around his waist, effectively trapping the pantywaist in the chair but it also served to lift the lower part of his dress, fully exposing his shiny satin rumbas.
  The other girls came in and lent a helping hand, tying his plastic bib around his neck and spooning out baby food into a multi portion plate. Standing on a kitchen stool, they took great delight in taking their part with the sissy, eagerly feeding him with typical child-like patience, hastily thrusting spoon after spoon of bland slop into his mouth where much of it spilled down on his chin and bib. They giggled at his babyish appearance and helped him drain a bottle of warm milk.
  Finally, with lunch finished, Julie wiped off his messy face and let him out of his high chair. His diapers were visibly sagging now, showing just how much the budding teenager had soaked them. With Julie taking the lead, everyone filed into Brian’s nursery where the red-faced sissy found his sopping wet diapers being pulled down and his tiny, caged genitals revealed to all.
  “What is that?” one of the curious young girls naturally asked as she giggled at Brian’s exposure.
  “That’s Brian’s chastity device,” Julie explained, “It’s there to make sure he can’t get any big-boy erections.”
  Everyone laughed as Brian blushed hotly with shame.
  Soon, the red-faced sissy was on his back again, his Mary Jane-clad feet being held over his head as Julie first cleaned his bottom, then coated it with Desitin. Baby powder came next, surrounding the little pansy in a cloud of infantile scent. He kicked his sissy feet as Julie drew up his thick, fluffy diapers and pinned them around his soft, slim hips.
  “Let’s see,” she mused as she sifted through a tall stack of plastic panties, “which naptime panties should we pick for mommy’s little baby?”
  Although Brian’s sissyish nature had enjoyed the tea party with the neighbor girls, it was clear that he was deeply ashamed to be getting his soaking wet diapers changed in front of them. He squirmed in humiliated silence as Julie pulled a pair of white nursery print waterproof panties up his smooth, hairless legs, working them over his fat diapers until all the bunny soft cotton was finally contained inside.
  “Okay babykins—say goodbye to your little friends, it’s naptime,” Julie announced.
  Brian blushed sheepishly as the girls giggled at his childish predicament. They watched as he was led into his crib and tucked in, his pacifier pushed into his quivering mouth and his teddy bear tucked under his arm.
  The lights were turned off and the bedwetting pantywaist was left with his Cinderella nightlight and the mobile above his head playing a babyish lullaby to help him to drift off to sleep. Indeed, it was just a typical afternoon in the day of this diaper-dependent sissy.


THE END
25
Active Sissy Stories
/ Re: New Arrangements for Josh
« Last post by sissyboy1212 on February 08, 2026, 12:04:33 PM »
Thank you RibbonBound! I've enjoyed playing with the AI images. (I have to credit Simonssister's excellent work for making me try some of my own.)

This is one that shows the scene in Mrs. Smyth's dress shop where Josh sees himself fully dressed in his Fauntleroy suit for the first time. He was so lucky to get the boy's outfit he was eager for!  :)
26
Active Sissy Stories
/ Re: New Arrangements for Josh
« Last post by RibbonBound on February 07, 2026, 09:04:50 PM »
I check occasionally to see if there's any new chapters of this amazing story.  Imagine how delighted to not only find a new chapter but some actual pictures of Josh!  Thank you so much for the double gift!
27
Active Sissy Stories
/ Re: New Arrangements for Josh
« Last post by sissyboy1212 on February 07, 2026, 01:54:23 PM »
PART 70

       In that moment, as the room grew quiet, Josh suddenly realized he would need to use the restroom soon. The urge descended on him with surprising speed. The fragrant tea he had been sipping all afternoon was making its presence known. He shifted discreetly in his chair, the frilly layers of his panties and stockings rustling against the crisp, soft velvet of his Fauntleroy suit. Every movement made the lace at his collar and cuffs brush delicately against his skin as a constant reminder of how elaborately he had been dressed. 

       Josh glanced toward his mother, hoping she might understand his predicament without drawing a lot of attention. He tried to mouth his request, “I need to tinkle,” but before he could finish, his mother pressed a finger to her lips to shush him and gave him a gentle but firm look. She clearly wanted him to remain poised, especially as Mrs. Standish stood and began to speak.

       Mrs. Standish announced, “Attention everyone, it’s time to give out some prizes!” As her voice rang through the lively tearoom, the clatter of conversation gradually faded, drawing everyone’s attention to her cheerful presence at the front.

       Josh tried to compose himself and shifted in his seat, hoping to ease his discomfort. His stockings whispered against each other as he nervously crossed and uncrossed his ankles. The urge to go had seemed to emerge from nowhere. He hoped against hope that at least for a moment the attention would shift away from him, and above all that these awards would be handed out quickly. The room brimmed with curiosity. Josh, however, felt a dual sense of dread about the pressure in his bladder and also about what these prizes might entail. He squirmed in his seat again.

       Mrs. Smyth, ever the watchful matron, leaned over and quietly whispered a gentle admonition, “Sit up straight, dear, and remember to be ladylike.” Josh felt his cheeks flush as he quickly adjusted his posture, trying not to fidget as much, though the urge to move was nearly overwhelming. 

       Mrs. Standish continued, “Before we begin our prizes, I want to give a special thanks to all our wonderful sponsors who made today possible. Special thanks go to Mrs. Dolores Smyth for her generosity and creativity, and to Andrea for her tireless help in organizing and decorating. Without you, none of this would have been nearly so delightful!”

       The room responded with a round of applause, warm and genuine, as the two women exchanged smiles and a subtle nod of pride. The applause seemed endless to Josh, who tapped his dainty slipper anxiously under the table, silently willing the proceedings to press on.

       Mrs. Standish then began to read from her list, starting with a prize that brought a ripple of adoring coos: “For our youngest guest in attendance, we have a very special prize!” A mother in a pastel dress gently lifted her toddler daughter, who wore a frilly, rose-colored party dress. The little girl was the very picture of sweetness in her party dress, delicate lace-trimmed socks, and shiny white patent shoes. The little girl blinked shyly as she was guided to the front, and Mrs. Standish knelt to present a small toy—an adorable stuffed bunny with satin ears and a bow. The audience “awwed” as the toddler hugged the bunny tight, her mother beaming with pride and gratitude.

       Mrs. Standish next handed out a series of charming door prizes. It turned out that each seat had a number taped under it, and Mrs. Standish called out the winning numbers one by one. Several ladies were delighted to win floral-patterned decorative teacups. An older gentleman and a college-aged girl both won ribbon-tied boxes of gourmet tea blends. Every prize was presented with a flourish and a kind word from Mrs. Standish.

       Next, Justin was mortified when his number was called to be among the winners for a small bag of chocolates prettily tied up in pink tulle favor bags with darling pink ribbons. His mother smiled and firmly took his hand to lead him up to Mrs. Standish, her eyes sparkling with satisfaction. The voluminous bustle of his confining dress made every step a production as he minced forward in his heels. He took small, dainty steps as the constricting folds of satin and tulle swished with each stride. The ladies in the crowd especially watched with delight, their faces lighting with knowing smiles and suppressed giggles. The handful of titters made Justin’s cheeks flush, and the unmistakably girlish sway of his walk drew everyone’s attention. His mother’s grip was unyielding as she guiding him to the front where Mrs. Standish waited with his prize. Surrounded by admiring glances and playful giggles, Justin meekly accepted the daintily wrapped sachet of chocolates.

       Then his mother leaned in, her voice unmistakably coaxing. “Now, what do we say, sweetheart?” she prompted, patting his shoulder softly.

       Justin turned beet red, glancing at Mrs. Standish as he spoke in a cowed voice, “Thank you, Mrs. Standish.”

       But his mother wasn’t satisfied with that and continued to nudge him gently, “Oh you can say more than that can’t you dear?” 

       The ladies in the crowd watched with delighted anticipation as Justin squirmed, clutching the pink tulle bag of chocolates. In a slightly louder and nervous voice, he tried again, “Th-thank you very much, Mrs. Standish, for the pretty chocolates.” His voice cracked, and a few guests giggled behind their hands.

       Mrs. Standish smiled warmly and replied, “You’re most welcome, Justin.” Turning to the crowd, she added sweetly “Isn’t he just precious?”

       Justin felt a hundred eyes on him and shuffled his feet nervously while his mother beamed. She gave him a gentle squeeze and began leading him back to his seat.

       Josh watched all this glumly as Justin returned to his table. A wave of secondhand embarrassment washed over him as he knew all too well how mortified Justin must have felt. He felt a sense of resignation as he feared his own moment was inevitably coming to be paraded in front of everyone. His spirits sank further as the prizes dragged on, and the omnipresent pressure under the confining layers of his adorable Fauntleroy suit steadily grew. It was increasingly difficult to focus on anything but his own discomfort and nagging dread. Just then, he also felt a different kind of unwanted tingle in his little cage. Josh let out a soft sigh and fought the impulse to squirm again. His cheeks warmed as he pressed his knees together, praying that the festivities would hurry along. 
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Active Sissy Stories
/ Re: New Arrangements for Josh
« Last post by sissyboy1212 on February 07, 2026, 01:48:14 PM »
Thank you very much BabyJay.  That's supposed to be Josh's sister Kathy. Not exactly how I envision her appearance, but the image turned out cutely I think.

Decided to add another part.
29
Active Sissy Stories
/ Re: New Arrangements for Josh
« Last post by BabyJay on February 07, 2026, 10:22:59 AM »
Delightful photos. He looks so cute and adorable. Who is the pretty girl with them? I think Josh would look even more adorable wearing a dress like Hers, only much shorter. Look forward to continuation.
30
Active Sissy Stories
/ Re: New Arrangements for Josh
« Last post by sissyboy1212 on February 06, 2026, 08:04:06 PM »
And here he is walking by the baseball players in his Fauntleroy suit.
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