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Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on Yesterday at 08:30:16 PM »
Pop Quiz Aftermath
As Thursday’s study hall came to a disappointing close, the boys moped back into “their” dressing room and began undressing. The silence between them was punctuated by the subtle rustle of delicate fabrics. They moved now with slow, hesitant motions. Their cheeks were tinged red as they all hung up their blouses and skirts, put away their Mary Janes and carefully stored their tights.
Just at that moment, there was a soft knock on the door and then it opened. Madison and all their Big Sisters stepped into the room with kinder smiles. The boys froze in their tracks as they stood startled in only their bralettes and panties. The sisters took a moment to again appreciate all their lovely new lingerie as the Delta Darlings reddened terribly. Once more, Madison appraised the boys’ selections approvingly, “So sweet and lovely.” She said with a twinkle, “Your trip to Lace & Grace was certainly worthwhile!” All the Big Sisters nodded in agreement.
Madison spoke again, this time more gently, “After all your difficulties tonight, I think you now realize how far you still have to travel. This is not a game. Rest assured, however, that we are here to help. With that in mind, we have one final surprise for you this evening… I’m certain that it will help you focus your energies and efforts as our Little Sisters.”
The boys exchanged anxious glances, eyes darting nervously as their chests tightened. Their nerves were frayed, and they could only wonder what was coming next. “Let’s end the night on a more positive note, shall we?” she asked rhetorically.
As Madison finished, each Big Sister stepped forward and presented her “Delta Darling” with a small pouch made of lavender velvet. Inside, nestled in tissue paper, the boys found sleek and unfamiliar devices. Their Big Sisters gathered closer around them, their faces alight with gentle, knowing expressions. As the boys waited in suspense, their Big Sisters explained the purpose. These were their new chastity cages! They would be worn at all times going forward as a physical symbol of their new devotion to Gamma Delta. A pained hush fell over the boys as they now understood what this meant. They cringed as they instantly recalled the line in their pledge about “chastity!”
As Thursday’s study hall came to a disappointing close, the boys moped back into “their” dressing room and began undressing. The silence between them was punctuated by the subtle rustle of delicate fabrics. They moved now with slow, hesitant motions. Their cheeks were tinged red as they all hung up their blouses and skirts, put away their Mary Janes and carefully stored their tights.
Just at that moment, there was a soft knock on the door and then it opened. Madison and all their Big Sisters stepped into the room with kinder smiles. The boys froze in their tracks as they stood startled in only their bralettes and panties. The sisters took a moment to again appreciate all their lovely new lingerie as the Delta Darlings reddened terribly. Once more, Madison appraised the boys’ selections approvingly, “So sweet and lovely.” She said with a twinkle, “Your trip to Lace & Grace was certainly worthwhile!” All the Big Sisters nodded in agreement.
Madison spoke again, this time more gently, “After all your difficulties tonight, I think you now realize how far you still have to travel. This is not a game. Rest assured, however, that we are here to help. With that in mind, we have one final surprise for you this evening… I’m certain that it will help you focus your energies and efforts as our Little Sisters.”
The boys exchanged anxious glances, eyes darting nervously as their chests tightened. Their nerves were frayed, and they could only wonder what was coming next. “Let’s end the night on a more positive note, shall we?” she asked rhetorically.
As Madison finished, each Big Sister stepped forward and presented her “Delta Darling” with a small pouch made of lavender velvet. Inside, nestled in tissue paper, the boys found sleek and unfamiliar devices. Their Big Sisters gathered closer around them, their faces alight with gentle, knowing expressions. As the boys waited in suspense, their Big Sisters explained the purpose. These were their new chastity cages! They would be worn at all times going forward as a physical symbol of their new devotion to Gamma Delta. A pained hush fell over the boys as they now understood what this meant. They cringed as they instantly recalled the line in their pledge about “chastity!”
2
Active Sissy Stories / Re: New Arrangements for Josh
« Last post by sissyboy1212 on Yesterday at 07:50:05 PM »
Thanks again BabyJay for the cute comment :) Working on the next part...
3
Active Sissy Stories / Re: PETTICOATED!
« Last post by petticoated on February 11, 2026, 08:27:07 PM »
More coming soon...
4
Active Sissy Stories / Re: New Arrangements for Josh
« Last post by sissyboy1212 on February 11, 2026, 08:10:37 PM »
PART 72
From the corner of her eye, Mrs. Smyth took a half beat to appreciate this latest correction of Josh’s deportment by Gwendolyn. Then, she continued unperturbed with her eager cataloging of Justin’s attire, “See how his skirt flares so nicely with that crinoline underneath to create the classic bell shape we all adore.” She directed the flustered and frocked boy, “spin around for us, dear, so everyone can see your lovely silhouette.” Justin’s cheeks burned as he obeyed and awkwardly turned in place. His movements were tentative and stiff, and his eyes were glued to the floor to avoid the amused gazes that followed him. The swirl of his frilly dress with its vintage bustle only heightened his embarrassment, and he looked mortified as everyone admired the elaborately feminine details of his outfit on display.
Mrs. Smyth went on, “Now, if you look closely, you can see our dear Justin’s tights have very subtle floral embroidery. So dainty!” She picked up steam, “and his shoes are classic Mary Janes. Honestly, there’s not a Victorian girl in history who wouldn’t feel like a fairy princess in those!” Then she gestured to the hairbow nestled in his boyishly short hair, “As you can see, it’s the details that pull this look together. Justin’s adorable hairbow is made of the same navy satin and lace as his dress, and the pearl beading accents are truly sumptuous!” She concluded, “But I think my personal favorite part of his outfit are those whimsical bubble sleeves… so playful and fetching… a little girl’s dream!” Mrs. Smyth beamed proudly. “Justin here is truly the picture of a prissy little Victorian lady, wouldn’t you all agree?”
The appreciative laughter and gentle applause from all the guests in response only reddened Justin’s face further. As the noise slowly abated and Justin cringed deeply, Mrs. Standish finally took back over to present his prize. She cradled in her hands an elaborately feminine little tea set: four miniature porcelain cups painted with roses and gold and a matching teapot adorned with the same pattern. As she presented the mortified boy his charming tea set, she said mischievously, “This will be perfect for hosting your own tea parties, sweetie!” Then she added cheerfully, “and our sponsor Andrea here was kind enough to donate a gift certificate for her salon, Clips and Curls!” Mrs. Standish handed Justin a pink envelope with “Clips and Curls” embossed on the front.
With a nervous look toward his mother, Justin’s lips trembled. He felt utterly exposed with his every ruffle on full display. After a long moment, he spoke, “Thank you again Mrs. Standish… and Miss Andrea.”
With a dissatisfied look, his mother spoke again expectantly, “And…?”
Justin gulped dejectedly, and then he added, “And… uh… I just love my tea set and I can’t wait to… uh… have my own tea party.” His voice was small, barely audible, and he blinked away the sting of impending tears under the room’s amused scrutiny. Justin stood sheepishly as many in the crowd giggled and then applauded him. He tried to force a polite smile, his entire demeanor still tight with anxiety. He clutched his girlish gifts with shaky hands, painfully aware of every ruffle, bow and frill on display.
As the applause died down, his mother took the pink envelope from her sissified child. As she flashed an appreciative smile at Andrea, she added, “And I can assure you we will put this gift certificate to good use tomorrow!” With a satisfied look, she wrapped her arm around her son’s shoulders and purposefully guided him back toward their table. Their body language left no doubt about who was in charge. Samantha trailed merrily behind them. Justin gingerly held his new tea set as he teetered away on his darling heels.
Watching Justin’s ordeal unfold, Josh felt a pang of empathy mixed with rising dread. The laughter and attention that followed the humiliated boy back to his seat only increased Josh’s anxiety, and the insistent ache in his abdomen made it nearly impossible to sit still. He shifted in his seat, his legs squirming ever so slightly again as he sought relief. Hesitantly, he fiddled with the frilly lace of his wrist cuff just a tad. He remained hyper-aware of the restrictive clothing encasing him so thoroughly. An uncomfortable heat radiated from underneath his crinkly diaper, rhumba panties and lush velvet knee pants. He lowered his head, closed his eyes and took in a shallow breath in another attempt to distract himself.
As if on cue, Mrs. Standish spoke again with cheerful anticipation, “All right, everyone, it’s time for our final prize today: our coveted Best Outfit award!”
From the corner of her eye, Mrs. Smyth took a half beat to appreciate this latest correction of Josh’s deportment by Gwendolyn. Then, she continued unperturbed with her eager cataloging of Justin’s attire, “See how his skirt flares so nicely with that crinoline underneath to create the classic bell shape we all adore.” She directed the flustered and frocked boy, “spin around for us, dear, so everyone can see your lovely silhouette.” Justin’s cheeks burned as he obeyed and awkwardly turned in place. His movements were tentative and stiff, and his eyes were glued to the floor to avoid the amused gazes that followed him. The swirl of his frilly dress with its vintage bustle only heightened his embarrassment, and he looked mortified as everyone admired the elaborately feminine details of his outfit on display.
Mrs. Smyth went on, “Now, if you look closely, you can see our dear Justin’s tights have very subtle floral embroidery. So dainty!” She picked up steam, “and his shoes are classic Mary Janes. Honestly, there’s not a Victorian girl in history who wouldn’t feel like a fairy princess in those!” Then she gestured to the hairbow nestled in his boyishly short hair, “As you can see, it’s the details that pull this look together. Justin’s adorable hairbow is made of the same navy satin and lace as his dress, and the pearl beading accents are truly sumptuous!” She concluded, “But I think my personal favorite part of his outfit are those whimsical bubble sleeves… so playful and fetching… a little girl’s dream!” Mrs. Smyth beamed proudly. “Justin here is truly the picture of a prissy little Victorian lady, wouldn’t you all agree?”
The appreciative laughter and gentle applause from all the guests in response only reddened Justin’s face further. As the noise slowly abated and Justin cringed deeply, Mrs. Standish finally took back over to present his prize. She cradled in her hands an elaborately feminine little tea set: four miniature porcelain cups painted with roses and gold and a matching teapot adorned with the same pattern. As she presented the mortified boy his charming tea set, she said mischievously, “This will be perfect for hosting your own tea parties, sweetie!” Then she added cheerfully, “and our sponsor Andrea here was kind enough to donate a gift certificate for her salon, Clips and Curls!” Mrs. Standish handed Justin a pink envelope with “Clips and Curls” embossed on the front.
With a nervous look toward his mother, Justin’s lips trembled. He felt utterly exposed with his every ruffle on full display. After a long moment, he spoke, “Thank you again Mrs. Standish… and Miss Andrea.”
With a dissatisfied look, his mother spoke again expectantly, “And…?”
Justin gulped dejectedly, and then he added, “And… uh… I just love my tea set and I can’t wait to… uh… have my own tea party.” His voice was small, barely audible, and he blinked away the sting of impending tears under the room’s amused scrutiny. Justin stood sheepishly as many in the crowd giggled and then applauded him. He tried to force a polite smile, his entire demeanor still tight with anxiety. He clutched his girlish gifts with shaky hands, painfully aware of every ruffle, bow and frill on display.
As the applause died down, his mother took the pink envelope from her sissified child. As she flashed an appreciative smile at Andrea, she added, “And I can assure you we will put this gift certificate to good use tomorrow!” With a satisfied look, she wrapped her arm around her son’s shoulders and purposefully guided him back toward their table. Their body language left no doubt about who was in charge. Samantha trailed merrily behind them. Justin gingerly held his new tea set as he teetered away on his darling heels.
Watching Justin’s ordeal unfold, Josh felt a pang of empathy mixed with rising dread. The laughter and attention that followed the humiliated boy back to his seat only increased Josh’s anxiety, and the insistent ache in his abdomen made it nearly impossible to sit still. He shifted in his seat, his legs squirming ever so slightly again as he sought relief. Hesitantly, he fiddled with the frilly lace of his wrist cuff just a tad. He remained hyper-aware of the restrictive clothing encasing him so thoroughly. An uncomfortable heat radiated from underneath his crinkly diaper, rhumba panties and lush velvet knee pants. He lowered his head, closed his eyes and took in a shallow breath in another attempt to distract himself.
As if on cue, Mrs. Standish spoke again with cheerful anticipation, “All right, everyone, it’s time for our final prize today: our coveted Best Outfit award!”
5
Active Sissy Stories / Re: New Arrangements for Josh
« Last post by BabyJay on February 11, 2026, 04:56:11 AM »
Oh! dear, poor Josh. I don't think He will hold out much longer. After he wets His nappy I hope His Mummy will put Him in a cute short little girls dress to show off His pretty rumba knickers.
6
Active Sissy Stories / Re: New Arrangements for Josh
« Last post by sissyboy1212 on February 09, 2026, 06:53:37 PM »
PART 71
After all the door prizes were awarded, Mrs. Standish moved to the final prizes: Best Outfits. Josh cringed when he heard the word “outfit” as he had a sinking feeling of where this all was headed. The mere mention of “outfits” reminded him of how trapped he felt in his painfully ornate Fauntleroy suit. The constricting layers of velvet, lace, and ruffles felt heavier with each passing moment, and every button and ribbon seemed to reinforce his plight. His dainty pink velvet Mary Janes, just barely large enough for his prettily stockinged feet, pinched his toes with each anxious flex.
With all the smothering attention he had gotten during the High Tea, it now seemed almost inevitable that he would get called forward. He was unable to ignore the expectant smiles and looks several of the ladies were casting his way, as if they all knew his turn was coming. By now, he was pressing his legs together tightly and trying to think of anything except the urge to go. With the elaborate way he had been buttoned, buckled, corseted, laced, fastened and tied into his Fauntleroy suit, he knew he would never get out of it without help even if he made it to the bathroom.
A few moments earlier, Josh had finally whispered to his mother, “Mommy, I need to tinkle,” cringing as he said the childish words.
She had whispered back that they couldn’t just get up and leave in the middle of the awards, and he would need to hold it a bit longer. “Besides, that’s why we took those… precautions, sweetheart,” she said quietly, alluding to the girls diaper he now wore under his rhumba panties, “we don’t want to miss it if you win something!” Her tone was sympathetic but firm. There would be no ducking out during the awarding of prizes. It began to sink in that he actually might have to resort to his diaper. At the time, the idea had seemed ridiculous to him. He was fifteen years old! But now… it seemed like a real possibility. The thought made him shudder slightly.
Meanwhile, the next prize went to an older lady at the next table who won the prize for “Most Festive Accessory.” Mrs. Standish presented her a pretty crystal brooch for her vintage hat with faux roses that had been admired by several in the crowd. The hat itself was a charming spectacle; it was wide-brimmed and trimmed with a spray of pastel silk blossoms. While the rest of the room smiled and clapped, Josh glumly watched her accept her prize. He was unable to stop his mind from drifting back to his own increasingly urgent predicament.
Mrs. Standish’s eyes twinkled mischievously again. “Now, for Best Outfit Runner-Up, let’s welcome Justin back up!”
Josh watched in sympathetic misery as once again, Justin was escorted back up by his mother to receive his prize. Samantha, ever the cheerful companion, tagged along gaily this time, her lively demeanor contrasting sharply with Justin’s hesitant steps. Mrs. Standish’s eyes gleamed with playful delight as everyone again turned their full attention to the sissified boy as he stepped awkwardly to the front of the tearoom and stood meekly next to her. His cheeks flamed as she spoke. Mrs. Standish said sweetly, “let’s take a moment to admire Justin’s gorgeous outfit! Such exceptional vintage style truly deserves this recognition.” She turned to Mrs. Smyth and said, “Dolores, would you mind telling us about his dress?”
Justin shifted uncomfortably as Mrs. Smyth eagerly got up. She began in a somewhat teasing yet affectionate tone, “First of all, let’s congratulate Justin for being so daring to embrace such a pretty outfit as a boy.” Of course, she knew full well that this was not Justin’s choice at all, but it seemed more gentle in her mind to let everyone think he chose to dress this way. She led the crowd in another short round of applause. Samantha snickered at the idea that Justin wanted to wear a dress, and Justin looked like he just wanted to sink into the floor. The blush crept up his neck as Mrs. Smyth began describing his outfit.
“As you can see, it’s a truly delightful Victorian party dress. Look how shimmery it is with those layers of organza!” she added. “And isn’t that pinafore just the sweetest thing you’ve ever seen?” she asked rhetorically. The crowd murmured their approval, some stifling giggles, others smiling in amusement at the fanciful details. Justin’s hands twisted nervously in front of him, his whole body radiating discomfort. The moment stretched on, with Justin forced to stand as the details of his elaborate, feminine attire were discussed at length.
By now, Josh was increasingly restless in his chair. He spread his legs apart and wiggled them anxiously. He pressed his palms down flat on his thighs, and he was very aware of the sensation of his velvet pants rubbing against his stockings underneath. Thoroughly encased in his sissified suit, he felt his corset pressing unrelentingly into his waist and forcing him to maintain an upright posture. Most of all, Josh felt the constant dull ache in his abdomen. He tried to focus on the spectacle before him to distract himself, but it was almost as uncomfortable having to watch Justin’s sissified humiliation as it was to think about his aching bladder. As if that weren’t enough stress, his little man was starting to become nervous and excited again in his confining pink plastic prison.
His mother took note of all of Josh’s anxious fretting and put her hand deliberately on his shoulder, silently reminding him to be still with a disapproving look. He froze in place under the weight of her unspoken expectations. She then whispered one now-familiar word: “Knees!” That word had rapidly become a trigger for the discomfited sissy. That single syllable was a recurring reminder of the restriction imposed by his new reality. Reflexively, Josh rapidly pressed his knees back together as his cheeks reddened even more. He was chagrined to be reminded how each movement he made was so closely monitored, and he was acutely aware that even the slightest slip would be met with a corrective glance or gesture from his mother or the other ladies at the table.
After all the door prizes were awarded, Mrs. Standish moved to the final prizes: Best Outfits. Josh cringed when he heard the word “outfit” as he had a sinking feeling of where this all was headed. The mere mention of “outfits” reminded him of how trapped he felt in his painfully ornate Fauntleroy suit. The constricting layers of velvet, lace, and ruffles felt heavier with each passing moment, and every button and ribbon seemed to reinforce his plight. His dainty pink velvet Mary Janes, just barely large enough for his prettily stockinged feet, pinched his toes with each anxious flex.
With all the smothering attention he had gotten during the High Tea, it now seemed almost inevitable that he would get called forward. He was unable to ignore the expectant smiles and looks several of the ladies were casting his way, as if they all knew his turn was coming. By now, he was pressing his legs together tightly and trying to think of anything except the urge to go. With the elaborate way he had been buttoned, buckled, corseted, laced, fastened and tied into his Fauntleroy suit, he knew he would never get out of it without help even if he made it to the bathroom.
A few moments earlier, Josh had finally whispered to his mother, “Mommy, I need to tinkle,” cringing as he said the childish words.
She had whispered back that they couldn’t just get up and leave in the middle of the awards, and he would need to hold it a bit longer. “Besides, that’s why we took those… precautions, sweetheart,” she said quietly, alluding to the girls diaper he now wore under his rhumba panties, “we don’t want to miss it if you win something!” Her tone was sympathetic but firm. There would be no ducking out during the awarding of prizes. It began to sink in that he actually might have to resort to his diaper. At the time, the idea had seemed ridiculous to him. He was fifteen years old! But now… it seemed like a real possibility. The thought made him shudder slightly.
Meanwhile, the next prize went to an older lady at the next table who won the prize for “Most Festive Accessory.” Mrs. Standish presented her a pretty crystal brooch for her vintage hat with faux roses that had been admired by several in the crowd. The hat itself was a charming spectacle; it was wide-brimmed and trimmed with a spray of pastel silk blossoms. While the rest of the room smiled and clapped, Josh glumly watched her accept her prize. He was unable to stop his mind from drifting back to his own increasingly urgent predicament.
Mrs. Standish’s eyes twinkled mischievously again. “Now, for Best Outfit Runner-Up, let’s welcome Justin back up!”
Josh watched in sympathetic misery as once again, Justin was escorted back up by his mother to receive his prize. Samantha, ever the cheerful companion, tagged along gaily this time, her lively demeanor contrasting sharply with Justin’s hesitant steps. Mrs. Standish’s eyes gleamed with playful delight as everyone again turned their full attention to the sissified boy as he stepped awkwardly to the front of the tearoom and stood meekly next to her. His cheeks flamed as she spoke. Mrs. Standish said sweetly, “let’s take a moment to admire Justin’s gorgeous outfit! Such exceptional vintage style truly deserves this recognition.” She turned to Mrs. Smyth and said, “Dolores, would you mind telling us about his dress?”
Justin shifted uncomfortably as Mrs. Smyth eagerly got up. She began in a somewhat teasing yet affectionate tone, “First of all, let’s congratulate Justin for being so daring to embrace such a pretty outfit as a boy.” Of course, she knew full well that this was not Justin’s choice at all, but it seemed more gentle in her mind to let everyone think he chose to dress this way. She led the crowd in another short round of applause. Samantha snickered at the idea that Justin wanted to wear a dress, and Justin looked like he just wanted to sink into the floor. The blush crept up his neck as Mrs. Smyth began describing his outfit.
“As you can see, it’s a truly delightful Victorian party dress. Look how shimmery it is with those layers of organza!” she added. “And isn’t that pinafore just the sweetest thing you’ve ever seen?” she asked rhetorically. The crowd murmured their approval, some stifling giggles, others smiling in amusement at the fanciful details. Justin’s hands twisted nervously in front of him, his whole body radiating discomfort. The moment stretched on, with Justin forced to stand as the details of his elaborate, feminine attire were discussed at length.
By now, Josh was increasingly restless in his chair. He spread his legs apart and wiggled them anxiously. He pressed his palms down flat on his thighs, and he was very aware of the sensation of his velvet pants rubbing against his stockings underneath. Thoroughly encased in his sissified suit, he felt his corset pressing unrelentingly into his waist and forcing him to maintain an upright posture. Most of all, Josh felt the constant dull ache in his abdomen. He tried to focus on the spectacle before him to distract himself, but it was almost as uncomfortable having to watch Justin’s sissified humiliation as it was to think about his aching bladder. As if that weren’t enough stress, his little man was starting to become nervous and excited again in his confining pink plastic prison.
His mother took note of all of Josh’s anxious fretting and put her hand deliberately on his shoulder, silently reminding him to be still with a disapproving look. He froze in place under the weight of her unspoken expectations. She then whispered one now-familiar word: “Knees!” That word had rapidly become a trigger for the discomfited sissy. That single syllable was a recurring reminder of the restriction imposed by his new reality. Reflexively, Josh rapidly pressed his knees back together as his cheeks reddened even more. He was chagrined to be reminded how each movement he made was so closely monitored, and he was acutely aware that even the slightest slip would be met with a corrective glance or gesture from his mother or the other ladies at the table.
7
Active Sissy Stories / Re: Babysitting For My Sister
« Last post by Baby Bobby on February 09, 2026, 11:00:14 AM »
( " 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
You can find the first chapter here; https://buffalobetties.net/storytime/index.php?topic=1311.new#new
8
Active Sissy Stories / A Visit to My Sister's House
« Last post by Baby Bobby on February 09, 2026, 10:30:09 AM »
Note to the reader; This is part one of my Sister series. The second chapter is Babysitting for my Sister, and the third is Another Visit to my Sister's House.
A Visit to My Sister's House
"Can I refresh your drink?" my sister asked as she positioned the chilled bottle of white wine over my glass.
"Sure, Sis," I answered, enjoying the well balanced Sauvignon Blanc she was serving.
The fire crackling in the fireplace added an additional warmth to my sister's pleasant living room where we were sitting this evening, catching up on gossip and family matters. I didn't often have the chance to see her, what with our different schedules, so it was nice to come over and visit when I could. She lived alone with her stepson, Brian, who had just turned thirteen last month.
"Thanks for your patience while I got Brian ready for bed," she said as she sat back in her easy chair.
"Oh, it's no problem," I replied, although I couldn't imagine what it was she needed to get him ready for.
My sister's attention was momentarily diverted as we heard softly padded footsteps approaching from behind me. Turning to look, I got a bit of a shock when I took in the sight before me.
Here was Brian, sheepishly waddling into the living room, wearing a fleece yellow one-piece footed sleeper with a nursery print design. The feet had plush bunnies with floppy ears on them and his seat had what looked like a big fluffy bunny tail attached.
Honestly, I thought it looked more like something a toddler would wear but I didn't say anything. And then, in the quiet of the room, as he drew closer, I could distinctively make out the crinkle-swish-crinkle sound that every mother knows instinctively from raising babies. Looking down, I could see the unmistakable bell shape around his hips, obviously produced by a very thick diaper.
Seeing the focus of my attention, Brian blushed red and looked anxiously to his stepmother for comfort.
"Come here, baby," she smiled at him as she held her arms open wide invitingly.
Brian waddled over and hugged her, and I watched as her hand slipped down to pat the very thick seat of his fuzzy fleece jammies, comforting the abashed youth.
Personally, I had always thought Brian was something of a sissy, and from what I could tell, my sister only encouraged his behavior. While my two similarly aged sons were in the hockey league, Brian didn't participate in any sports at all at school and he still played with "action" dolls at home.
But even knowing his mother's somewhat eccentric behavior, I was surprised by his childish appearance and thought his bed wear to be rather odd.
"Brian started wetting the bed last month," she explained patiently, as she saw me looking at his big, bulging bottom, "so I started putting him in diapers and plastic panties before bedtime."
I took a swallow of my wine as I looked him up and down. He looked to all appearances to be an overgrown toddler.
"Has it reduced the...uh...wetting?" I asked uncertainly.
"No...if anything, he's wetting even more, but at least his bedding is dry in the morning," she replied with a smile, apparently pleased, as she patted his bottom maternally, "But truth be told, I really don't mind our diapering sessions...I feel like we're bonding again closer than ever and I think Brian likes the intimacy he experiences."
I grunted in disapproval.
"In my house, if one of my boys started wetting the bed, he'd get a good, hard spanking and that would be the end of it."
My sister frowned and gave me a critical look.
"I would never spank Brian," she stated emphatically, squeezing his big bottom again and hugging him tighter.
The effeminate youth shifted his stance in his footed jammies and appeared embarrassed by all this talk of his recent bedwetting habit.
My sister encircled his waist with her arm but unfortunately, it had the unintended effect of putting more strain on the fuzzy soft fabric stretching around his hips. His sleeper had a drop seat with snaps and one of the corners suddenly popped open, exposing the colorful, babyish plastic panties covering Brian's thick diapers.
"Oh!" he squealed as he realized his waterproof panties could now be clearly seen. His hands shot down defensively to try and cover up his shameful underwear.
"It's okay, baby," my sister said reassuringly as she turned him around physically and re-snapped the flap.
Brian's face was blushing a deep red as he tried to look away from me. Clearly, he was uncomfortable being seen under these extremely humiliating circ-umstances.
"Honey--did you brush your teeth?" my sister asked him.
"Uh-huh," he said in almost a whisper, as he shifted his feet anxiously.
"Okay, go get your bottle then," she said, dismissing him with a soft swat on his generously padded, bulging bottom.
Brian looked at her pleadingly.
"B-but I'm not thirsty tonight," he whined desperately.
"Run along, baby," she replied, summarily dismissing his concerns, "You know you need your milk."
Wincing with embarrassment, Brian quickly waddled out of the room.
Did she just say 'bottle'? I asked myself, not sure I heard correctly.
My sister acted as if nothing were out of the ordinary as she smiled back at me. I looked at her oddly, wondering if she really intended to bottle feed her 13 year-old stepson.
Brian returned shortly, his crinkly plastic panties audibly announcing his presence before I actually saw him enter the room.
Sure enough, I saw him holding a baby bottle of milk, playful nursery characters decorating the container.
My eyebrow arched in surprise as I saw her take Brian onto her lap and shift his position so both his legs were on the same side. Taking the bottle from him, she pushed it past his protesting lips, holding it in place against his mouth as he squirmed and waved his hands in angst.
"Settle down now, honey," she cooed to him.
I watched him as he struggled helplessly on her lap, fidgeting and pouting as she forced him to nurse like a baby.
"Umm, don't you think it's unwise to give him liquids before bed if he's wetting during the night?" I asked.
She shrugged as she looked at her prissy stepson who was blushing hotly while he nursed from the bottle being held for him.
"I think it's helps him to relax," she replied simply, but I remained unconvinced.
Brian's cheeks buzzed with shame as his eyes darted around the room, looking everywhere but at me.
"Uh-huh," I said, taking another drink from my glass, "Sis--don't you think you're molly-coddling him?"
I hoped my disapproval didn't sound too judgmental.
"Oh no!" she replied emphatically, "I just think boys like Brian need a little more attention than others. I'm sure after a period of wearing diapers...say six months or a year, the bedwetting will disappear altogether."
I shook my head but said nothing.
Just then, her stepson started getting fussy with her--it was obvious he had had his fill and didn't want to finish the last half of the baby bottle. But she kept it pushed against his mouth, forcing him to drink the tepid liquid whether he wanted it or not. He squealed and whimpered, trying to resist her but it was obvious in a battle of wills, she was going to come out the victor.
It seemed equally obvious to me that given the fact he was going to bed at the childishly early hour of 8:00, and with a large serving of milk, it was a virtual certainty he would be wetting his diapers tonight and every night.
Finally, the over-sized bottle ran dry and my sister let him off her lap. He tried unsuccessfully to mask a burp from the quantity of milk he'd drank before averting his gaze to the floor.
"Go give your aunt a hug goodnight," she commanded him.
Awkwardly, he waddled over and gave me a halfhearted hug of affection.
"Say goodnight, Brian," she prodded him.
"Goodnight, aunt Stacey," he said, his cheeks still bright red.
To be sure, whatever respect I had held for the boy was gone now.
"Goodnight, Brian," I replied as I shook my head.
My sister took his hand and led him down the hallway to his room. With nothing else to do, I looked idly back at them, until she opened the door to his bedroom.
That's when my mouth dropped in surprise as I saw the bed she was actually tucking him into--it was a baby's crib!
THE END
A Visit to My Sister's House
"Can I refresh your drink?" my sister asked as she positioned the chilled bottle of white wine over my glass.
"Sure, Sis," I answered, enjoying the well balanced Sauvignon Blanc she was serving.
The fire crackling in the fireplace added an additional warmth to my sister's pleasant living room where we were sitting this evening, catching up on gossip and family matters. I didn't often have the chance to see her, what with our different schedules, so it was nice to come over and visit when I could. She lived alone with her stepson, Brian, who had just turned thirteen last month.
"Thanks for your patience while I got Brian ready for bed," she said as she sat back in her easy chair.
"Oh, it's no problem," I replied, although I couldn't imagine what it was she needed to get him ready for.
My sister's attention was momentarily diverted as we heard softly padded footsteps approaching from behind me. Turning to look, I got a bit of a shock when I took in the sight before me.
Here was Brian, sheepishly waddling into the living room, wearing a fleece yellow one-piece footed sleeper with a nursery print design. The feet had plush bunnies with floppy ears on them and his seat had what looked like a big fluffy bunny tail attached.
Honestly, I thought it looked more like something a toddler would wear but I didn't say anything. And then, in the quiet of the room, as he drew closer, I could distinctively make out the crinkle-swish-crinkle sound that every mother knows instinctively from raising babies. Looking down, I could see the unmistakable bell shape around his hips, obviously produced by a very thick diaper.
Seeing the focus of my attention, Brian blushed red and looked anxiously to his stepmother for comfort.
"Come here, baby," she smiled at him as she held her arms open wide invitingly.
Brian waddled over and hugged her, and I watched as her hand slipped down to pat the very thick seat of his fuzzy fleece jammies, comforting the abashed youth.
Personally, I had always thought Brian was something of a sissy, and from what I could tell, my sister only encouraged his behavior. While my two similarly aged sons were in the hockey league, Brian didn't participate in any sports at all at school and he still played with "action" dolls at home.
But even knowing his mother's somewhat eccentric behavior, I was surprised by his childish appearance and thought his bed wear to be rather odd.
"Brian started wetting the bed last month," she explained patiently, as she saw me looking at his big, bulging bottom, "so I started putting him in diapers and plastic panties before bedtime."
I took a swallow of my wine as I looked him up and down. He looked to all appearances to be an overgrown toddler.
"Has it reduced the...uh...wetting?" I asked uncertainly.
"No...if anything, he's wetting even more, but at least his bedding is dry in the morning," she replied with a smile, apparently pleased, as she patted his bottom maternally, "But truth be told, I really don't mind our diapering sessions...I feel like we're bonding again closer than ever and I think Brian likes the intimacy he experiences."
I grunted in disapproval.
"In my house, if one of my boys started wetting the bed, he'd get a good, hard spanking and that would be the end of it."
My sister frowned and gave me a critical look.
"I would never spank Brian," she stated emphatically, squeezing his big bottom again and hugging him tighter.
The effeminate youth shifted his stance in his footed jammies and appeared embarrassed by all this talk of his recent bedwetting habit.
My sister encircled his waist with her arm but unfortunately, it had the unintended effect of putting more strain on the fuzzy soft fabric stretching around his hips. His sleeper had a drop seat with snaps and one of the corners suddenly popped open, exposing the colorful, babyish plastic panties covering Brian's thick diapers.
"Oh!" he squealed as he realized his waterproof panties could now be clearly seen. His hands shot down defensively to try and cover up his shameful underwear.
"It's okay, baby," my sister said reassuringly as she turned him around physically and re-snapped the flap.
Brian's face was blushing a deep red as he tried to look away from me. Clearly, he was uncomfortable being seen under these extremely humiliating circ-umstances.
"Honey--did you brush your teeth?" my sister asked him.
"Uh-huh," he said in almost a whisper, as he shifted his feet anxiously.
"Okay, go get your bottle then," she said, dismissing him with a soft swat on his generously padded, bulging bottom.
Brian looked at her pleadingly.
"B-but I'm not thirsty tonight," he whined desperately.
"Run along, baby," she replied, summarily dismissing his concerns, "You know you need your milk."
Wincing with embarrassment, Brian quickly waddled out of the room.
Did she just say 'bottle'? I asked myself, not sure I heard correctly.
My sister acted as if nothing were out of the ordinary as she smiled back at me. I looked at her oddly, wondering if she really intended to bottle feed her 13 year-old stepson.
Brian returned shortly, his crinkly plastic panties audibly announcing his presence before I actually saw him enter the room.
Sure enough, I saw him holding a baby bottle of milk, playful nursery characters decorating the container.
My eyebrow arched in surprise as I saw her take Brian onto her lap and shift his position so both his legs were on the same side. Taking the bottle from him, she pushed it past his protesting lips, holding it in place against his mouth as he squirmed and waved his hands in angst.
"Settle down now, honey," she cooed to him.
I watched him as he struggled helplessly on her lap, fidgeting and pouting as she forced him to nurse like a baby.
"Umm, don't you think it's unwise to give him liquids before bed if he's wetting during the night?" I asked.
She shrugged as she looked at her prissy stepson who was blushing hotly while he nursed from the bottle being held for him.
"I think it's helps him to relax," she replied simply, but I remained unconvinced.
Brian's cheeks buzzed with shame as his eyes darted around the room, looking everywhere but at me.
"Uh-huh," I said, taking another drink from my glass, "Sis--don't you think you're molly-coddling him?"
I hoped my disapproval didn't sound too judgmental.
"Oh no!" she replied emphatically, "I just think boys like Brian need a little more attention than others. I'm sure after a period of wearing diapers...say six months or a year, the bedwetting will disappear altogether."
I shook my head but said nothing.
Just then, her stepson started getting fussy with her--it was obvious he had had his fill and didn't want to finish the last half of the baby bottle. But she kept it pushed against his mouth, forcing him to drink the tepid liquid whether he wanted it or not. He squealed and whimpered, trying to resist her but it was obvious in a battle of wills, she was going to come out the victor.
It seemed equally obvious to me that given the fact he was going to bed at the childishly early hour of 8:00, and with a large serving of milk, it was a virtual certainty he would be wetting his diapers tonight and every night.
Finally, the over-sized bottle ran dry and my sister let him off her lap. He tried unsuccessfully to mask a burp from the quantity of milk he'd drank before averting his gaze to the floor.
"Go give your aunt a hug goodnight," she commanded him.
Awkwardly, he waddled over and gave me a halfhearted hug of affection.
"Say goodnight, Brian," she prodded him.
"Goodnight, aunt Stacey," he said, his cheeks still bright red.
To be sure, whatever respect I had held for the boy was gone now.
"Goodnight, Brian," I replied as I shook my head.
My sister took his hand and led him down the hallway to his room. With nothing else to do, I looked idly back at them, until she opened the door to his bedroom.
That's when my mouth dropped in surprise as I saw the bed she was actually tucking him into--it was a baby's crib!
THE END
9
2011-2018 Sissy Stories / Re: The Pram Race
« Last post by Babyb on February 09, 2026, 07:50:57 AM »
No more to this one yet.
I have a plan on where the story goes but, as with my other stories, I've just never got round to writing them up.
I won't lie, but seeing certain people taking stories others have written and then selling them on Amazon as their own work doesn't inspire me to finish them off. 🙁
I have a plan on where the story goes but, as with my other stories, I've just never got round to writing them up.
I won't lie, but seeing certain people taking stories others have written and then selling them on Amazon as their own work doesn't inspire me to finish them off. 🙁
10
2011-2018 Sissy Stories / Re: The Pram Race
« Last post by babygaz on February 09, 2026, 06:56:53 AM »
Hi,
Does anyone know if there was a sequel written to this anywhere?
hugs
Does anyone know if there was a sequel written to this anywhere?
hugs
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