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Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on Today at 01:17:44 PM »
The Pledge Strikes Back
It was Elise’s turn. “OK, Darlings,” she smiled, “Let’s see how well you know the Alexion’s Pledge.”
Elise leaned forward, her eyes sharp. “Julian, let’s start with you. Recite the first sentence of the pledge—word for word.”
Julian hesitated, then recovered, “I solemnly swear to the Sisterhood of Gamma Delta my, uhh… my steadfast devotion as a member of the Alexionian Society.”
Elise nodded, “Not bad, but don’t stumble over the words. I’ll let it slide this time. A point for you.”
Julian exhaled in relief.
Tara continued, “Milo, what do you vow to respect and follow according to the pledge?”
Milo fidgeted with his skirt and stammered, “Uh, our values.”
Tara sighed, shaking her head. “The exact words are, ‘Gamma Delta’s values.’ You lose a point.”
Cassidy looked to Owen. “Owen, the pledge mentions three qualities you must embrace. Name them.”
Owen started confidently—none of the boys could forget “chastity.” He answered, “chastity, modesty, and… and… kindness.” He finished uncertainly.
Cassidy raised an eyebrow. “It’s chastity, modesty, and GRACE,” she corrected him, "Kindness is not until the next part. Another point lost.”
Madison tapped her pen. “Nate, besides kindness, what else do you seek to embody?”
Nate blurted out nervously. “Loyalty and obedience.”
“Those are correct, Madison replied evenly, “but you got the order wrong. I’ll let you have the point, but don’t make that mistake again.”
“Milo,” Tara asked, “what are you given in the pledge?”
Milo, relieved, replied more confidently, “the privilege of service.”
Tara smiled. “And how does the Pledge tell you to feel about that privilege?” she asked expectantly.
“Thankful,” Milo replied immediately. Then he realized his mistake, No, I mean—"
“Grateful,” Tara cut him off with a disappointed look, "you are GRATEFUL for the privilege of service. So that’s a plus one and a minus one—a wash.”
Madison said, “Let’s wrap this up. Nate, impress me. Recite the last line of the Pledge please.”
Nate answered nervously. He had studied this, but the stress of the moment made him falter, “These things I pledge with all my heart, and all my soul, to Gamma Delta.”
Madison tutted slightly, “almost, but you left out perhaps the most important word: ‘Sisterhood.’ You make your pledge to the ‘Sisterhood of Gamma Delta.’ Minus one for that.”
The Sisters exchanged pointed glances, clearly unimpressed. Elise sighed, “We’re not asking for perfection on everything, but your pledge is one of the most important things you should know. If you don’t know the words, how can you live them?” The question hung pointedly in the air for an awful moment.
The questions shifted back to Gamma Delta history, facts and lore, and they got trickier. Elise, her eyes sparkling, asked for the name of the Gamma Delta house’s original architect. The boys faltered. Tara then posed a question about the significance of the Gamma Delta flower, the Cream-Colored Rose, which prompted a round of blank stares. The group’s score steadily dwindled. Historical dates tangled in their memories, facts about Gamma Delta legends grew fuzzy, and a couple of times the boys struggled to fill in gaps with wild guesses.
Madison spoke up, her tone brisk and somewhat frustrated. “These are literally some of the most basic facts about Gamma Delta—things you should know by heart if you’ve applied yourself at all,” she said, “It should be a piece of cake after having two whole days to study!”
After several more questions, the pop quiz mercifully ended. “Well…” Madison said judgingly, “I suppose we still have work ahead of us.” Then she added in disappointment, “Gamma Delta deserves… and demands… more.”
Nervous energy coursed through the room as the boys squirmed under the weight of the Sisters’ disappointment. Milo, reached down with unsteadyy hands to smooth out the pleats of his skirt. The delicate fabric fluttered beneath his nervous fingers, which seemed to betray his every effort to appear calm. He forced a deep breath, but his nerves refused to settle, making his gestures fussy and uncertain.
Beside him, Nate perched uncomfortably on the edge of his dainty little stool, his posture stiff as he self-consciously drew his knees together. He attempted to arrange his legs with awkward, almost tentative grace. The smooth, cool embrace of his white tights was ever-present—a tactile reminder of his transformation, whispering against his skin with every slight movement and making him all the more acutely aware of his unfamiliar attire.
Julian pressed his adorable navy flats against the polished floor, the soles making barely a sound. He subtly rocked, struggling to keep his fidgeting under control. Despite his best efforts, nervous energy seemed to radiate from his entire body, every shift and shuffle betraying his lack of confidence. His fingers gripped the hem of his skirt, twisting the material as he tried to ground himself in the moment.
Owen sat with his hands folded tightly in his lap, and he became increasingly aware of the slick lip gloss coating his lips. He could feel its faint, sticky sheen every time he reflexively pressed his lips together. Each little reminder of his outward appearance seemed to magnify his embarrassment.
None of the boys dared to meet each other’s eyes. Their cheeks were flushed, and whenever their gazes risked crossing paths, they immediately looked away, focusing instead on their shoes, their skirts, or the floor. They sat in a tense, silent row.
Breaking the heavy silence again, Madison straightened and fixed the boys with a level gaze. “Look at me—all of you,” she commanded firmly. Hesitantly, they lifted their eyes, faces flushed with residual embarrassment. Madison’s expression was stern. “I want each of you to understand something important. Gamma Delta isn’t just about cute outfits or quizzes. It’s about sisterhood, dedication, and respect for what this organization stands for.” She paused, ensuring their attention. “You Delta Darlings made a deal and a promise to uphold the standards of this house. Tonight, you fell short of that bargain.” Her words hung in the air ominously.
It was Elise’s turn. “OK, Darlings,” she smiled, “Let’s see how well you know the Alexion’s Pledge.”
Elise leaned forward, her eyes sharp. “Julian, let’s start with you. Recite the first sentence of the pledge—word for word.”
Julian hesitated, then recovered, “I solemnly swear to the Sisterhood of Gamma Delta my, uhh… my steadfast devotion as a member of the Alexionian Society.”
Elise nodded, “Not bad, but don’t stumble over the words. I’ll let it slide this time. A point for you.”
Julian exhaled in relief.
Tara continued, “Milo, what do you vow to respect and follow according to the pledge?”
Milo fidgeted with his skirt and stammered, “Uh, our values.”
Tara sighed, shaking her head. “The exact words are, ‘Gamma Delta’s values.’ You lose a point.”
Cassidy looked to Owen. “Owen, the pledge mentions three qualities you must embrace. Name them.”
Owen started confidently—none of the boys could forget “chastity.” He answered, “chastity, modesty, and… and… kindness.” He finished uncertainly.
Cassidy raised an eyebrow. “It’s chastity, modesty, and GRACE,” she corrected him, "Kindness is not until the next part. Another point lost.”
Madison tapped her pen. “Nate, besides kindness, what else do you seek to embody?”
Nate blurted out nervously. “Loyalty and obedience.”
“Those are correct, Madison replied evenly, “but you got the order wrong. I’ll let you have the point, but don’t make that mistake again.”
“Milo,” Tara asked, “what are you given in the pledge?”
Milo, relieved, replied more confidently, “the privilege of service.”
Tara smiled. “And how does the Pledge tell you to feel about that privilege?” she asked expectantly.
“Thankful,” Milo replied immediately. Then he realized his mistake, No, I mean—"
“Grateful,” Tara cut him off with a disappointed look, "you are GRATEFUL for the privilege of service. So that’s a plus one and a minus one—a wash.”
Madison said, “Let’s wrap this up. Nate, impress me. Recite the last line of the Pledge please.”
Nate answered nervously. He had studied this, but the stress of the moment made him falter, “These things I pledge with all my heart, and all my soul, to Gamma Delta.”
Madison tutted slightly, “almost, but you left out perhaps the most important word: ‘Sisterhood.’ You make your pledge to the ‘Sisterhood of Gamma Delta.’ Minus one for that.”
The Sisters exchanged pointed glances, clearly unimpressed. Elise sighed, “We’re not asking for perfection on everything, but your pledge is one of the most important things you should know. If you don’t know the words, how can you live them?” The question hung pointedly in the air for an awful moment.
The questions shifted back to Gamma Delta history, facts and lore, and they got trickier. Elise, her eyes sparkling, asked for the name of the Gamma Delta house’s original architect. The boys faltered. Tara then posed a question about the significance of the Gamma Delta flower, the Cream-Colored Rose, which prompted a round of blank stares. The group’s score steadily dwindled. Historical dates tangled in their memories, facts about Gamma Delta legends grew fuzzy, and a couple of times the boys struggled to fill in gaps with wild guesses.
Madison spoke up, her tone brisk and somewhat frustrated. “These are literally some of the most basic facts about Gamma Delta—things you should know by heart if you’ve applied yourself at all,” she said, “It should be a piece of cake after having two whole days to study!”
After several more questions, the pop quiz mercifully ended. “Well…” Madison said judgingly, “I suppose we still have work ahead of us.” Then she added in disappointment, “Gamma Delta deserves… and demands… more.”
Nervous energy coursed through the room as the boys squirmed under the weight of the Sisters’ disappointment. Milo, reached down with unsteadyy hands to smooth out the pleats of his skirt. The delicate fabric fluttered beneath his nervous fingers, which seemed to betray his every effort to appear calm. He forced a deep breath, but his nerves refused to settle, making his gestures fussy and uncertain.
Beside him, Nate perched uncomfortably on the edge of his dainty little stool, his posture stiff as he self-consciously drew his knees together. He attempted to arrange his legs with awkward, almost tentative grace. The smooth, cool embrace of his white tights was ever-present—a tactile reminder of his transformation, whispering against his skin with every slight movement and making him all the more acutely aware of his unfamiliar attire.
Julian pressed his adorable navy flats against the polished floor, the soles making barely a sound. He subtly rocked, struggling to keep his fidgeting under control. Despite his best efforts, nervous energy seemed to radiate from his entire body, every shift and shuffle betraying his lack of confidence. His fingers gripped the hem of his skirt, twisting the material as he tried to ground himself in the moment.
Owen sat with his hands folded tightly in his lap, and he became increasingly aware of the slick lip gloss coating his lips. He could feel its faint, sticky sheen every time he reflexively pressed his lips together. Each little reminder of his outward appearance seemed to magnify his embarrassment.
None of the boys dared to meet each other’s eyes. Their cheeks were flushed, and whenever their gazes risked crossing paths, they immediately looked away, focusing instead on their shoes, their skirts, or the floor. They sat in a tense, silent row.
Breaking the heavy silence again, Madison straightened and fixed the boys with a level gaze. “Look at me—all of you,” she commanded firmly. Hesitantly, they lifted their eyes, faces flushed with residual embarrassment. Madison’s expression was stern. “I want each of you to understand something important. Gamma Delta isn’t just about cute outfits or quizzes. It’s about sisterhood, dedication, and respect for what this organization stands for.” She paused, ensuring their attention. “You Delta Darlings made a deal and a promise to uphold the standards of this house. Tonight, you fell short of that bargain.” Her words hung in the air ominously.
2
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on January 25, 2026, 07:37:33 AM »
Pop Quiz and a Name Game
Next, the boys were unpleasantly surprised by a pop quiz on fundamental Gamma Delta facts. At first, the boys felt a flicker of confidence. They could surely recall some of the basics about Gamma Delta’s founding, traditions and alumnae.
Before starting the quiz, however, the Big Sisters had the boys sit in a neat little line in the center of the study lounge on a row of dainty white stools. These glossy white painted stools were just a little too low for them, with hard seats and no backs to lean against.
The boys, dressed in their pretty study outfits, looked even more diminutive and sweet as they settled onto the undersized stools. They had to adjust themselves delicately, smoothing their skirts over their laps, knees pressed together, hands folded primly atop their pleated skirts. The awkwardness of their posture made it impossible to forget just how exposed and childlike they seemed, lined up in their girlish outfits on display before the sorority sisters.
The sisters surveyed the scene with delighted amusement. The contrast was striking: the sisters exuded easy confidence and authority while the boys looked like bashful pupils in an unfamiliar classroom. The boys’ cheeks reddened as they sat, backs straight, acutely aware that their every move was being watched. The sisters seemed to enjoy the moment, exchanging knowing smiles as their charges squirmed.
The first questions were simple: “What year was Gamma Delta founded?” Owen, eyes wide, blurted “1928!” and earned a point for the group. Milo correctly named the first Gamma Delta President and netted another. The group celebrated these early successes with cautious smiles, savoring the momentary sense of victory after the debacle of their Alumna Spotlights. Julian correctly managed to recall Gamma Delta’s five core values without stumbling and got them two more.
“Here’s a neat one with nice points on the line,” Cassidy said teasingly, “You learned that boys like you have several formal and informal names and nicknames. I can think of at least seven we’ve told you about, not including ‘Rosebuds’ which we just discussed. You can take turns naming them by saying ‘I love being a Gamma Delta…’ and then fill-in-the-blank.” She looked at Milo. “Milo, why don’t you go first, and remember to phrase it right!”
Milo, reddening slightly, said “I love being a Gamma Delta Delta Darling.” It was somewhat of a tongue-twister to say the two “Deltas” in a row, but he was afraid to leave one out.
“Nice. Now Owen,” Cassidy said, “and say it like you mean it!”
It was immediately obvious to the boys that the point of this exercise was both to test their knowledge and also make them verbally reaffirm their new status. They saw Brianna had whipped out her phone to record them. Everyone in the study lounge seemed to be enjoying this one.
Blushing, Owen said softly but clearly, “I love being a Gamma Delta Little Sister!”
“Lovely,” Cassidy smiled, “Nate you’re next.”
Nate nearly stumbled. The two “easy” ones had already been said. Then he recovered and managed to get out, “I love being a Gamma Delta Alexion!”
“Of course you do!” Cassidy said brightly, “Julian?”
Julian was frantically stretching his brain. What were the other names? They had only been mentioned in passing, and most of them were not in the study guide. Then he said tentatively, “I love being a Gamma Delta member of the Alexionian Society.”
“Well,” Cassidy said, “That’s technically right and certainly a mouthful, but it’s sort of the same thing Nate said.” She looked back to Milo, “Do you remember one of the others, Milo?"
Milo suddenly remembered an additional term from Tuesday. He cringed as he forced a smile and said, “I love being a Gamma Delta Petal Boy!”
Cassidy grinned, “Aww, that’s so sweet! I’ll bet you do!” Then she said, “You learned about a few more. Let’s throw it out to the group. Anyone.” The boys tried to remember what the others were, but they all drew blanks.
Then, Julian was able to recall one more. Despite his nerves, he said as nicely as he could, “I love being a Gamma Delta Delta Doll!” The double ‘Deltas’ rolled off his tongue adorably as he tried to mimic how Milo had done it a few moments earlier.
Cassidy giggled at him, “That’s right sweetie! You really are a Double Delta Doll!” She looked around expectantly, “Two remaining. Who else?”
Owen had his face scrunched up trying to recall. They all knew every point counted. He thought it was “Little” something or other, but his memory failed him. He took a chance and guessed, “I love being a Gamma Delta… Little Gamma?” It came out sounding more like a question than a statement.
Cassidy chuckled, “I think you made a lucky stab, but that’s right. Why don’t you say it again properly?” she prodded.
Feeling the heat rise on his cheeks, Owen’s response this time sounded almost singsong, “I love being a Gamma Delta Little Gamma!”
“Adorable,” Cassidy said as if talking down to a child. “There’s only one left,” she said sweetly. “Anyone?” she asked. Silence. She seemed amused as she watched them struggle to think of the last one. “Doesn’t anyone remember?” she persisted. Seeing they didn’t know, she gave them the answer, “It’s Little Darlings… from the old days! Let’s all say that one together.”
As they collectively cringed, she coached them all to repeat together in a lilting way reminiscent of a nursery rhyme, “Little Darling, Little Darling! I love being a Gamma Delta Little Darling.” All the Big Sisters chuckled as she had them all say it several more times to lodge it nicely in their brains. Brianna got it all recorded on her phone.
She closed this little game by having them repeat the terms after her one by one as a sweet little call and response: “Delta Darling. Little Darling. Delta Doll. Little Sister. Alexion. Little Gamma. Petal Boy.” Then she added “Rosebud” for good measure.
They repeated the cutesy Gamma Delta terms—“Petal Boy,” “Delta Doll,” “Little Gamma,” and “Little Darling”—with palpable discomfort. As they were led through these elaborate recitations, their voices mimicked the sweet tones expected of them. They struggled to maintain their composure, shifting nervously in their darling skirts and snug tights, the unfamiliar garments only amplifying their discomfort. The heat rose on their faces, turning their cheeks a soft pink as they blushed, acutely aware of the amused scrutiny of the sorority sisters. Despite their obvious embarrassment, they obediently followed along as Brianna recorded the bashful proclamations of their love for Gamma Delta.
After “Rosebud” rolled off their tongues in unison, Cassidy exclaimed, “What fun!” Then she added, “Hopefully that will help you remember better the next time! You did manage to get six out of a possible seven points!”
Next, the boys were unpleasantly surprised by a pop quiz on fundamental Gamma Delta facts. At first, the boys felt a flicker of confidence. They could surely recall some of the basics about Gamma Delta’s founding, traditions and alumnae.
Before starting the quiz, however, the Big Sisters had the boys sit in a neat little line in the center of the study lounge on a row of dainty white stools. These glossy white painted stools were just a little too low for them, with hard seats and no backs to lean against.
The boys, dressed in their pretty study outfits, looked even more diminutive and sweet as they settled onto the undersized stools. They had to adjust themselves delicately, smoothing their skirts over their laps, knees pressed together, hands folded primly atop their pleated skirts. The awkwardness of their posture made it impossible to forget just how exposed and childlike they seemed, lined up in their girlish outfits on display before the sorority sisters.
The sisters surveyed the scene with delighted amusement. The contrast was striking: the sisters exuded easy confidence and authority while the boys looked like bashful pupils in an unfamiliar classroom. The boys’ cheeks reddened as they sat, backs straight, acutely aware that their every move was being watched. The sisters seemed to enjoy the moment, exchanging knowing smiles as their charges squirmed.
The first questions were simple: “What year was Gamma Delta founded?” Owen, eyes wide, blurted “1928!” and earned a point for the group. Milo correctly named the first Gamma Delta President and netted another. The group celebrated these early successes with cautious smiles, savoring the momentary sense of victory after the debacle of their Alumna Spotlights. Julian correctly managed to recall Gamma Delta’s five core values without stumbling and got them two more.
“Here’s a neat one with nice points on the line,” Cassidy said teasingly, “You learned that boys like you have several formal and informal names and nicknames. I can think of at least seven we’ve told you about, not including ‘Rosebuds’ which we just discussed. You can take turns naming them by saying ‘I love being a Gamma Delta…’ and then fill-in-the-blank.” She looked at Milo. “Milo, why don’t you go first, and remember to phrase it right!”
Milo, reddening slightly, said “I love being a Gamma Delta Delta Darling.” It was somewhat of a tongue-twister to say the two “Deltas” in a row, but he was afraid to leave one out.
“Nice. Now Owen,” Cassidy said, “and say it like you mean it!”
It was immediately obvious to the boys that the point of this exercise was both to test their knowledge and also make them verbally reaffirm their new status. They saw Brianna had whipped out her phone to record them. Everyone in the study lounge seemed to be enjoying this one.
Blushing, Owen said softly but clearly, “I love being a Gamma Delta Little Sister!”
“Lovely,” Cassidy smiled, “Nate you’re next.”
Nate nearly stumbled. The two “easy” ones had already been said. Then he recovered and managed to get out, “I love being a Gamma Delta Alexion!”
“Of course you do!” Cassidy said brightly, “Julian?”
Julian was frantically stretching his brain. What were the other names? They had only been mentioned in passing, and most of them were not in the study guide. Then he said tentatively, “I love being a Gamma Delta member of the Alexionian Society.”
“Well,” Cassidy said, “That’s technically right and certainly a mouthful, but it’s sort of the same thing Nate said.” She looked back to Milo, “Do you remember one of the others, Milo?"
Milo suddenly remembered an additional term from Tuesday. He cringed as he forced a smile and said, “I love being a Gamma Delta Petal Boy!”
Cassidy grinned, “Aww, that’s so sweet! I’ll bet you do!” Then she said, “You learned about a few more. Let’s throw it out to the group. Anyone.” The boys tried to remember what the others were, but they all drew blanks.
Then, Julian was able to recall one more. Despite his nerves, he said as nicely as he could, “I love being a Gamma Delta Delta Doll!” The double ‘Deltas’ rolled off his tongue adorably as he tried to mimic how Milo had done it a few moments earlier.
Cassidy giggled at him, “That’s right sweetie! You really are a Double Delta Doll!” She looked around expectantly, “Two remaining. Who else?”
Owen had his face scrunched up trying to recall. They all knew every point counted. He thought it was “Little” something or other, but his memory failed him. He took a chance and guessed, “I love being a Gamma Delta… Little Gamma?” It came out sounding more like a question than a statement.
Cassidy chuckled, “I think you made a lucky stab, but that’s right. Why don’t you say it again properly?” she prodded.
Feeling the heat rise on his cheeks, Owen’s response this time sounded almost singsong, “I love being a Gamma Delta Little Gamma!”
“Adorable,” Cassidy said as if talking down to a child. “There’s only one left,” she said sweetly. “Anyone?” she asked. Silence. She seemed amused as she watched them struggle to think of the last one. “Doesn’t anyone remember?” she persisted. Seeing they didn’t know, she gave them the answer, “It’s Little Darlings… from the old days! Let’s all say that one together.”
As they collectively cringed, she coached them all to repeat together in a lilting way reminiscent of a nursery rhyme, “Little Darling, Little Darling! I love being a Gamma Delta Little Darling.” All the Big Sisters chuckled as she had them all say it several more times to lodge it nicely in their brains. Brianna got it all recorded on her phone.
She closed this little game by having them repeat the terms after her one by one as a sweet little call and response: “Delta Darling. Little Darling. Delta Doll. Little Sister. Alexion. Little Gamma. Petal Boy.” Then she added “Rosebud” for good measure.
They repeated the cutesy Gamma Delta terms—“Petal Boy,” “Delta Doll,” “Little Gamma,” and “Little Darling”—with palpable discomfort. As they were led through these elaborate recitations, their voices mimicked the sweet tones expected of them. They struggled to maintain their composure, shifting nervously in their darling skirts and snug tights, the unfamiliar garments only amplifying their discomfort. The heat rose on their faces, turning their cheeks a soft pink as they blushed, acutely aware of the amused scrutiny of the sorority sisters. Despite their obvious embarrassment, they obediently followed along as Brianna recorded the bashful proclamations of their love for Gamma Delta.
After “Rosebud” rolled off their tongues in unison, Cassidy exclaimed, “What fun!” Then she added, “Hopefully that will help you remember better the next time! You did manage to get six out of a possible seven points!”
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:35:33 AM »
Chapter 321.
The top half of Clara, Maggie, and a ginger-haired boy were seen through the window. The whole class turned to stare. Madeline stood up to get a better view.
“Madeline! Sit down!”
The classroom door opened slowly. The girls grinning faces appeared. They advanced backwards into the room, each of them tugging at a hand belonging to the apparently reluctant trainee maid – whose hands were sheathed in a pair of glossy red latex gloves! The students gaped. Miss Taylor, who had a better view from her position at the teacher’s desk, smiled despite herself and covered her mouth with her hand. With a final concerted heave, they tumbled Tim into the room. Clara quickly let go of his hand, gave him a push, and slammed the door behind him. He stood there, like a rabbit in the headlights, regarding the rows of astonished faces with wide-eyed alarm. The was a brief pause, then the whole class gasped as one. Whatever they were expecting, the reality was beyond their wildest speculation. Clara stepped forward.
“Please welcome Tim. Tim is training to be a lady’s maid. He is multi-talented. He is also a professional boot boy at Pitt’s Wood Equestrian Centre.”
Maggie had taken a little stool from the corner and placed it in front of the blackboard.
“Tim? Come and stand up here, please, so that the class can see you.”
Tim was helpless with fright. Clara led him over and helped him up, amidst whispers, titters, and the occasional snort of suppressed laughter.
“Face the class, please, Tim…”
Miss Taylor walked over and took his hand, determined to make him feel at ease.
“Thank you so much for coming, Tim. It’s wonderful to have you for our show and share. We’re especially grateful since it sounds as though you have a very busy life at the moment. Girls, I think Tim deserves a round of applause.”
The girls responded loudly, not only clapping but cheering and whistling. Tim still looked nervous, but gratified as well.
“Well I’ll hand you over to Clara and Maggie, as you’re their personal project.”
“Thank you, Miss Taylor,” smiled Clara. She turned to face the class.
“Tim left school in the summer, having passed all his exams, and having earned a place at uni. That’s right, Tim?”
He nodded modestly.
“So he could have gone straight up and continued his studies. But instead he decided that he wanted to do some useful work. So together with his friend Bobby he volunteered to work at Pitt’s Wood, keeping all the stable girls’ boots nice and clean and shiny, and servicing customers from the neighbouring area to earn extra income to help run the Centre and feed all the horses. In return the Centre looked after him and Bobby and had lovely uniforms made for them.” She turned to Tim. “Tim? Could you give me that envelope I asked you to put in your bag?”
“Oh…y-yes… Here, Miss Clara…”
She slipped out three photographs of Tim and Bobby in their boot boy outfits, two of them showing them at work, on their knees, and gave them to Madeline.
“Here, Madeline, could you pass them round, please?”
As they circulated there were giggles of delight. Madeline looked straight at Tim.
“Can I and my friends come and get our boots polished by you and your friend?”
“Y-yes, miss…of course…”
“And you’ll have to kneel down like this and do it?”
“Y-yes…”
“Cool!”
“But he enjoyed working for all those girls and ladies so much,” continued Clara, “that…”
Here she stood aside, and let Maggie take up the story.
“…that he thought he would like to dedicate himself to waiting on all a woman’s needs – by becoming a maid! So he went into training. Washing, cleaning, waiting, cooking, serving in every conceivable way, keeping his mistress happy and contented. In a couple of weeks he should have been trained to a satisfactory standard, and then he will be put into full-time domestic service. Clara? Could we have the photos of Tim in his maid’s outfit?”
“I’ll pass them round….”
“Oh my god,” exclaimed Madeline. “All his outfits are latex, right? Wow, that’s super sexy!”
“Madeline!” snapped Miss Taylor.
“No, miss, I didn’t mean anything bad. He looks great. He’s really good looking, he's got great legs, and the uniform's so cute...”
“Thank you, Madeline. We all value your opinions, but that’s enough for now…” said Miss Taylor. But glancing at Tim, she could see he was quite pleased. He did a sort of little static swagger on the stool. She made a mental note to ask Clara if she could keep the photos to put up on the notice-board. And maybe a couple for herself…
The top half of Clara, Maggie, and a ginger-haired boy were seen through the window. The whole class turned to stare. Madeline stood up to get a better view.
“Madeline! Sit down!”
The classroom door opened slowly. The girls grinning faces appeared. They advanced backwards into the room, each of them tugging at a hand belonging to the apparently reluctant trainee maid – whose hands were sheathed in a pair of glossy red latex gloves! The students gaped. Miss Taylor, who had a better view from her position at the teacher’s desk, smiled despite herself and covered her mouth with her hand. With a final concerted heave, they tumbled Tim into the room. Clara quickly let go of his hand, gave him a push, and slammed the door behind him. He stood there, like a rabbit in the headlights, regarding the rows of astonished faces with wide-eyed alarm. The was a brief pause, then the whole class gasped as one. Whatever they were expecting, the reality was beyond their wildest speculation. Clara stepped forward.
“Please welcome Tim. Tim is training to be a lady’s maid. He is multi-talented. He is also a professional boot boy at Pitt’s Wood Equestrian Centre.”
Maggie had taken a little stool from the corner and placed it in front of the blackboard.
“Tim? Come and stand up here, please, so that the class can see you.”
Tim was helpless with fright. Clara led him over and helped him up, amidst whispers, titters, and the occasional snort of suppressed laughter.
“Face the class, please, Tim…”
Miss Taylor walked over and took his hand, determined to make him feel at ease.
“Thank you so much for coming, Tim. It’s wonderful to have you for our show and share. We’re especially grateful since it sounds as though you have a very busy life at the moment. Girls, I think Tim deserves a round of applause.”
The girls responded loudly, not only clapping but cheering and whistling. Tim still looked nervous, but gratified as well.
“Well I’ll hand you over to Clara and Maggie, as you’re their personal project.”
“Thank you, Miss Taylor,” smiled Clara. She turned to face the class.
“Tim left school in the summer, having passed all his exams, and having earned a place at uni. That’s right, Tim?”
He nodded modestly.
“So he could have gone straight up and continued his studies. But instead he decided that he wanted to do some useful work. So together with his friend Bobby he volunteered to work at Pitt’s Wood, keeping all the stable girls’ boots nice and clean and shiny, and servicing customers from the neighbouring area to earn extra income to help run the Centre and feed all the horses. In return the Centre looked after him and Bobby and had lovely uniforms made for them.” She turned to Tim. “Tim? Could you give me that envelope I asked you to put in your bag?”
“Oh…y-yes… Here, Miss Clara…”
She slipped out three photographs of Tim and Bobby in their boot boy outfits, two of them showing them at work, on their knees, and gave them to Madeline.
“Here, Madeline, could you pass them round, please?”
As they circulated there were giggles of delight. Madeline looked straight at Tim.
“Can I and my friends come and get our boots polished by you and your friend?”
“Y-yes, miss…of course…”
“And you’ll have to kneel down like this and do it?”
“Y-yes…”
“Cool!”
“But he enjoyed working for all those girls and ladies so much,” continued Clara, “that…”
Here she stood aside, and let Maggie take up the story.
“…that he thought he would like to dedicate himself to waiting on all a woman’s needs – by becoming a maid! So he went into training. Washing, cleaning, waiting, cooking, serving in every conceivable way, keeping his mistress happy and contented. In a couple of weeks he should have been trained to a satisfactory standard, and then he will be put into full-time domestic service. Clara? Could we have the photos of Tim in his maid’s outfit?”
“I’ll pass them round….”
“Oh my god,” exclaimed Madeline. “All his outfits are latex, right? Wow, that’s super sexy!”
“Madeline!” snapped Miss Taylor.
“No, miss, I didn’t mean anything bad. He looks great. He’s really good looking, he's got great legs, and the uniform's so cute...”
“Thank you, Madeline. We all value your opinions, but that’s enough for now…” said Miss Taylor. But glancing at Tim, she could see he was quite pleased. He did a sort of little static swagger on the stool. She made a mental note to ask Clara if she could keep the photos to put up on the notice-board. And maybe a couple for herself…
4
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:26:13 AM »
Chapter 320.
It was just as well he had agreed, because they had already decided he was going whether he wanted to or not, and the arrangements had already been made. Clara had called Sasha to get the low down on his history, plus a few piccies, and the girls had spoken to Miss Taylor that morning. She had snorted with laughter when she saw a picture of the boy they wanted to show and share.
“Miss…no. You mustn’t laugh,” said Clara, with mock dismay. “Tim’s quite vain, and you’ll hurt his feelings.”
“That’s right,” added Maggie, with a wink. “He thinks he’s super cute, and we want to keep it that way. Anyway, this costume’s just temporary. He’s training to be a lady’s maid.”
“A what?”
“Yes, miss,” said Clara, “a proper maid. He has a special pink latex uniform and he’s desperate to wear it again and get to work. Isn’t it sweet? My mum’s helping train him. He’s only staying with us till Sunday, then he goes back to training school.”
And she gave Miss Taylor a brief resumé of Tim’s training and what she had understood about the reason he’d been allocated his current outfit.
“Well, well. I must say this is more like it. This will make the class sit up and take notice. I’ll have to warn them not to start screaming with laughter.”
“Yes, please do that,” said Clara. “We’ll aim to arrive about fifteen minutes after the start of afternoon school, so you’ll have time to explain.”
“Perfect! Well, girls. It looks like being a fun afternoon!”
Miss Taylor was as good as her word. Once the class had settled after lunch, she called for quiet.
“Now girls, listen carefully. I have something to tell you. I hope you’ve all had a good chatter and a laugh at lunchtime, because you’re going to have to curb your natural exuberance for a while. Let me explain. Clara and Maggie have booked their show and share for this double lesson.”
“What are they going to show, miss?” asked a dark-haired girl in the front row. (She was in the front row for a reason, and not by choice.)
“If you’ll allow me, Madeline, I’ll tell you. They’re bringing a friend of theirs, a boy called Tim. Now Tim is training to be a maid…”
“A what, miss?”
“Madeline! Silence! Just be quiet and listen. As I said, Tim’s training to be a maid. Yes, boys can be maids too… And yes, I can see you’re all wondering… Yes, eventually, when he qualifies, he’ll wear a proper maid’s uniform, with a little maid’s cap, ands a maid’s dress, and an apron… Everything. Now… Shush, please. Now… Tim’s still in training, and until he passes the basic proficiency tests, he has to wear one of the special, er, trainee outfits…as you will see. Now, listen all of you! Madeline! Behave please.” She sighed. “Now, this is important, so pay attention. Madeline, how old are you?”
“Seventeen, miss.”
“Then stop behaving like a twelve-year-old, would you? As I was saying, please treat Tim with the utmost respect. I understand he’s a sensitive boy – stop smirking, Natalie! - and any negativity could be hurtful. He actually needs a confidence boost, because what he’s trying to do requires a lot of courage. It’s easy nowadays for girls to do jobs that used to be considered as boys’ only. It’s a lot harder for a boy to do what has traditionally been a girl’s job. Good – I’m glad you understand. So I’m relying on you to make him feel relaxed and accepted. Yes? Good girls. I trust you to be welcoming and warm, because I know you’re all mature adults. Then you’ll be able to ask him any questions you want about his training.”
Steps were heard in the corridor.
“Ah, I think this is them now…”
It was just as well he had agreed, because they had already decided he was going whether he wanted to or not, and the arrangements had already been made. Clara had called Sasha to get the low down on his history, plus a few piccies, and the girls had spoken to Miss Taylor that morning. She had snorted with laughter when she saw a picture of the boy they wanted to show and share.
“Miss…no. You mustn’t laugh,” said Clara, with mock dismay. “Tim’s quite vain, and you’ll hurt his feelings.”
“That’s right,” added Maggie, with a wink. “He thinks he’s super cute, and we want to keep it that way. Anyway, this costume’s just temporary. He’s training to be a lady’s maid.”
“A what?”
“Yes, miss,” said Clara, “a proper maid. He has a special pink latex uniform and he’s desperate to wear it again and get to work. Isn’t it sweet? My mum’s helping train him. He’s only staying with us till Sunday, then he goes back to training school.”
And she gave Miss Taylor a brief resumé of Tim’s training and what she had understood about the reason he’d been allocated his current outfit.
“Well, well. I must say this is more like it. This will make the class sit up and take notice. I’ll have to warn them not to start screaming with laughter.”
“Yes, please do that,” said Clara. “We’ll aim to arrive about fifteen minutes after the start of afternoon school, so you’ll have time to explain.”
“Perfect! Well, girls. It looks like being a fun afternoon!”
Miss Taylor was as good as her word. Once the class had settled after lunch, she called for quiet.
“Now girls, listen carefully. I have something to tell you. I hope you’ve all had a good chatter and a laugh at lunchtime, because you’re going to have to curb your natural exuberance for a while. Let me explain. Clara and Maggie have booked their show and share for this double lesson.”
“What are they going to show, miss?” asked a dark-haired girl in the front row. (She was in the front row for a reason, and not by choice.)
“If you’ll allow me, Madeline, I’ll tell you. They’re bringing a friend of theirs, a boy called Tim. Now Tim is training to be a maid…”
“A what, miss?”
“Madeline! Silence! Just be quiet and listen. As I said, Tim’s training to be a maid. Yes, boys can be maids too… And yes, I can see you’re all wondering… Yes, eventually, when he qualifies, he’ll wear a proper maid’s uniform, with a little maid’s cap, ands a maid’s dress, and an apron… Everything. Now… Shush, please. Now… Tim’s still in training, and until he passes the basic proficiency tests, he has to wear one of the special, er, trainee outfits…as you will see. Now, listen all of you! Madeline! Behave please.” She sighed. “Now, this is important, so pay attention. Madeline, how old are you?”
“Seventeen, miss.”
“Then stop behaving like a twelve-year-old, would you? As I was saying, please treat Tim with the utmost respect. I understand he’s a sensitive boy – stop smirking, Natalie! - and any negativity could be hurtful. He actually needs a confidence boost, because what he’s trying to do requires a lot of courage. It’s easy nowadays for girls to do jobs that used to be considered as boys’ only. It’s a lot harder for a boy to do what has traditionally been a girl’s job. Good – I’m glad you understand. So I’m relying on you to make him feel relaxed and accepted. Yes? Good girls. I trust you to be welcoming and warm, because I know you’re all mature adults. Then you’ll be able to ask him any questions you want about his training.”
Steps were heard in the corridor.
“Ah, I think this is them now…”
5
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:22:00 AM »
Chapter 319.
He got on with his chores. It was a good feeling, doing his maid duties all by himself, as Shirley had taught him. He felt responsible and trusted. He forgot all about his new outfit until he heard the front door being unlocked. The girls were home for lunch! Maybe they’d laugh at him…
But to his surprise they had the opposite reaction. They trooped through to the kitchen chattering away, but stopped dead when they caught sight of him. He was already colouring up again, when Maggie gasped.
“Tim! You look amazing! I love the new top! And the bag…”
“Wow! Cool!” cried Clara. “Look at this bag, Maggie. I bet that cost a bit… And the matching gloves and boots! I want them! Tim, lend them to me sometime, would you? Maybe Saturday night? We going clubbing down the village. They would be perfect!”
Tim was taken aback, but gratified.
“W-well, of course, Clara. I’m glad you like them. They are quite swish, ain’t – I mean aren’t – they?”
“Very!”
In his innocence he had no suspicion that the girls might have been forewarned. Nor that they had an ulterior motive for their approbation.
“Oh, and you’ve made our lunch! Look Clara, sandwiches – tuna mayo and egg mayo – a salad – looks as good as your mum’s! Drinks and fruit and chocolate bars. Thanks, Tim!”
“Yeah. Come on, Maggie, let’s eat. Tim, come join us. Come on, sit down. You’re not a maid yet.”
“But maybe when you are…” began Maggie.
“Yes. We were talking. When you’re fully qualified and everything, I want mum to employ you. We could have such fun. What do you think?”
“Yeah, great! Would you really do that?”
“Course. And you wouldn’t have to be working all the time. We could be good friends, eh, Maggie?”
“Sure. It’d be great to have a guy around. We spend all our days with a bunch of girls. Imagine… How would you like it if you saw nothing but females all day long…?”
Tim didn’t reply, but looked wistful. Clara suddenly put down her sandwich and sat bolt upright.
“I’ve had a great idea! We have Miss Taylor first two periods, don’t we Maggie? And we’re the only ones who haven’t done show and share this weekend. Why don’t we…?”
“Tim? fuc-k, yeah! He’d be perfect!”
“What? What’s that?” asked Tim, frowning.
“Right, I’ll explain,” said Clara. There are twenty girls in our class, and we’re all paired up – so there’s me and Maggie, fr’instance. Every term each pair gets to do a show and share – you know, they bring in something to show and tell the class about. It’s so boring! The last pair brought in an odd-shaped stone! Can you believe it? But Miss Taylor likes us and as its free periods today she’d definitely let us do it. Would you be our show and share? Please say you would…”
“Yes… Please, Tim…”
Tim was slightly taken aback. It was definitely scary. But the girls were looking at him pleadingly, and the last thing he wanted was to disappoint them, especially as they wanted to be friends, and in any case Shirley had told him to go along with anything they asked. And maybe, just maybe, he’d be as big a hit with the rest of the class… All these thoughts crossed his mind in a couple of seconds. He had to answer quickly, or he’d look churlish…
“Sure,” he blurted. And was immediately pounced on by the delighted girls. Clara even gave him a kiss on the cheek, which reassured him he’d made the right decision…
He got on with his chores. It was a good feeling, doing his maid duties all by himself, as Shirley had taught him. He felt responsible and trusted. He forgot all about his new outfit until he heard the front door being unlocked. The girls were home for lunch! Maybe they’d laugh at him…
But to his surprise they had the opposite reaction. They trooped through to the kitchen chattering away, but stopped dead when they caught sight of him. He was already colouring up again, when Maggie gasped.
“Tim! You look amazing! I love the new top! And the bag…”
“Wow! Cool!” cried Clara. “Look at this bag, Maggie. I bet that cost a bit… And the matching gloves and boots! I want them! Tim, lend them to me sometime, would you? Maybe Saturday night? We going clubbing down the village. They would be perfect!”
Tim was taken aback, but gratified.
“W-well, of course, Clara. I’m glad you like them. They are quite swish, ain’t – I mean aren’t – they?”
“Very!”
In his innocence he had no suspicion that the girls might have been forewarned. Nor that they had an ulterior motive for their approbation.
“Oh, and you’ve made our lunch! Look Clara, sandwiches – tuna mayo and egg mayo – a salad – looks as good as your mum’s! Drinks and fruit and chocolate bars. Thanks, Tim!”
“Yeah. Come on, Maggie, let’s eat. Tim, come join us. Come on, sit down. You’re not a maid yet.”
“But maybe when you are…” began Maggie.
“Yes. We were talking. When you’re fully qualified and everything, I want mum to employ you. We could have such fun. What do you think?”
“Yeah, great! Would you really do that?”
“Course. And you wouldn’t have to be working all the time. We could be good friends, eh, Maggie?”
“Sure. It’d be great to have a guy around. We spend all our days with a bunch of girls. Imagine… How would you like it if you saw nothing but females all day long…?”
Tim didn’t reply, but looked wistful. Clara suddenly put down her sandwich and sat bolt upright.
“I’ve had a great idea! We have Miss Taylor first two periods, don’t we Maggie? And we’re the only ones who haven’t done show and share this weekend. Why don’t we…?”
“Tim? fuc-k, yeah! He’d be perfect!”
“What? What’s that?” asked Tim, frowning.
“Right, I’ll explain,” said Clara. There are twenty girls in our class, and we’re all paired up – so there’s me and Maggie, fr’instance. Every term each pair gets to do a show and share – you know, they bring in something to show and tell the class about. It’s so boring! The last pair brought in an odd-shaped stone! Can you believe it? But Miss Taylor likes us and as its free periods today she’d definitely let us do it. Would you be our show and share? Please say you would…”
“Yes… Please, Tim…”
Tim was slightly taken aback. It was definitely scary. But the girls were looking at him pleadingly, and the last thing he wanted was to disappoint them, especially as they wanted to be friends, and in any case Shirley had told him to go along with anything they asked. And maybe, just maybe, he’d be as big a hit with the rest of the class… All these thoughts crossed his mind in a couple of seconds. He had to answer quickly, or he’d look churlish…
“Sure,” he blurted. And was immediately pounced on by the delighted girls. Clara even gave him a kiss on the cheek, which reassured him he’d made the right decision…
6
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 21, 2026, 08:15:13 AM »
Chapter 318.
ESDS divided their trainees into two streams, junior and senior. The juniors – the likes of Darren and Philip – were selected on the basis of cuteness and willingness. They received a narrow training. Their function would be, principally, to skip around looking pretty, flicking furniture with their little feather dusters, opening doors, taking coats at parties, running simple errands, and so on. They were little decorations, like tinsel on a Christmas tree, intended to do little more than provide a talking point for their mistresses and their friends – talk which often didn’t progress much past “ooh, isn’t he sweet…” or “where did you get him? I want one of those…” They had the gentlest of trainings, were rented out only to the kindest of mistresses, and in general revelled in the pretty outfits and the attention. Some of them enjoyed themselves so much, that as they grew older they wanted to be taught all the appropriate skills, and to progress into the senior stream – which of course they were encouraged to do. The seniors had a much more rigorous training, as Tim was discovering, and there was a significant drop-out rate. The tough ones – Teri was a perfect example – took it in their stride, and became valued and sought-after maids. Teri was professional, but was up for pretty much anything, which made him popular with single women and women who craved male company. In between postings he received “extra training” from Nicola, the nature of which no-one cared to enquire into. The seniors often tended to be fairly streetwise, and knew how to make the most of the perks that came with the job.
So Tim was an exception. A senior based on age, but naïve, ruled by an innocent vanity, a desire to be liked, to elicit attention and praise. From his first entry into The Pitt’s Wood ambit, his mentors had made a point of complimenting him on his appearance, his good looks and his smart uniforms, and fostering his personal pride and exploiting his credulity, making him take people’s attraction, surprise, their smiles and laughter, as compliments, and as a cue to show off all the more. Such flattery also served to tighten their grip on him, so that now it would never even occur to him to question their authority, whether Miss Poole’s or the personnel of ESDS.
So perhaps the transfer to Shirley Foster had been the plan all along. For her, he was ideal material. Her methods could not have been more different from those at headquarters. She didn’t issue orders, but taught him by working with him. She’d do a load of washing, checking the garments with him to see if they needed a separate wash or a particular temperature. She showed him how to iron, letting him take over more and more. They cleaned together and chose cleaning materials, they cooked together, took it in turns to wait on each other or on Clara and Maggie, discussed etiquette, practised curtsies. When Tim did something well, he got a cuddle. Once Shirley would took him on her lap and stroked his hair as if her were a little kid. Another time he got hugs from the girls. She taught him trust, and from trust came confidence. After only a few days, he had lost most of his nervousness, he was relaxed, and he was doing his chores with calm efficiency. On Thursday morning, after he had served breakfast and was clearing the table, and Clara had left for school, he turned to Shirley.
“Miss? Do you think I’m ready to have my maid’s uniform back yet?”
Shirley patted his cheek.
“I’ve already sent in an interim report, Mitzy. Miss Sasha says, providing you complete the week satisfactorily and without incident, she’ll let you have it back at the weekend, and you’ll be allowed to stay till Sunday morning.
“Yippee! Er, I mean, Thank you so much, Miss Shirley…”
“Tim – we should call you Tim until you’re officially a maid again - I’m really enjoying having you here. You’re a pleasure to work with. But this afternoon, I have to go to a meeting, so I’m handing you over to Clara and Maggie for obedience training. You know what that is. You follow their instructions willingly and promptly. You mustn’t question or demur, or you will fail this vital element of the course, which means I’ll have to report it, and you’ll be sent straight back to ESDS as you are. Do you understand what I’m saying?”
“Absolutely, madam,” said Tim, confidently.
“Good. They’ll be back for lunch around twelve, so prepare some sandwiches – you know what they like – and wait on them in the kitchen. When you’ve done the washing up and wiped the table, I’d like you to give their shoes a quick polish. I noticed Clara’s were a bit scruffy when she left this morning. Let me see, anything else… I don’t think so. Okay. I’m going to get ready. You should change as well – put on the outfit Sasha brought. And let me see what you look like with your new shoulder bag and your outside boots. Go on. I’ll be down to check in ten minutes.”
“Yes, miss… Of course…”
When she returned, Shirley threw up her hands in delight.
“My goodness, how smart you look! You’d turn a few heads in the village, and no mistake.”
Tim blushed, and touched his cheeks, which had been burning ever since he’d changed. He wanted to believe she meant that in the best possible way, but he suspected that this outfit, enhanced with accessories Sasha had brought, might possibly attract the wrong sort of attention…
“Surely you’re not shy! From what I’ve heard from Sasha, you love showing off. Aren’t you going to be principal pageboy at a big wedding in a few days?”
“Yes, madam… I’ll have a really cool outfit, too… I’m sorry, I can’t tell you about it…”
“Well, you look pretty cool now, I can tell you.”
“Do I, madam…?” He looked at her doubtfully.
“Yes, you do. Now I have to leave. Have a good day. The girls will have a surprise. They’re going to love your new top. I’ll see you this evening.”
ESDS divided their trainees into two streams, junior and senior. The juniors – the likes of Darren and Philip – were selected on the basis of cuteness and willingness. They received a narrow training. Their function would be, principally, to skip around looking pretty, flicking furniture with their little feather dusters, opening doors, taking coats at parties, running simple errands, and so on. They were little decorations, like tinsel on a Christmas tree, intended to do little more than provide a talking point for their mistresses and their friends – talk which often didn’t progress much past “ooh, isn’t he sweet…” or “where did you get him? I want one of those…” They had the gentlest of trainings, were rented out only to the kindest of mistresses, and in general revelled in the pretty outfits and the attention. Some of them enjoyed themselves so much, that as they grew older they wanted to be taught all the appropriate skills, and to progress into the senior stream – which of course they were encouraged to do. The seniors had a much more rigorous training, as Tim was discovering, and there was a significant drop-out rate. The tough ones – Teri was a perfect example – took it in their stride, and became valued and sought-after maids. Teri was professional, but was up for pretty much anything, which made him popular with single women and women who craved male company. In between postings he received “extra training” from Nicola, the nature of which no-one cared to enquire into. The seniors often tended to be fairly streetwise, and knew how to make the most of the perks that came with the job.
So Tim was an exception. A senior based on age, but naïve, ruled by an innocent vanity, a desire to be liked, to elicit attention and praise. From his first entry into The Pitt’s Wood ambit, his mentors had made a point of complimenting him on his appearance, his good looks and his smart uniforms, and fostering his personal pride and exploiting his credulity, making him take people’s attraction, surprise, their smiles and laughter, as compliments, and as a cue to show off all the more. Such flattery also served to tighten their grip on him, so that now it would never even occur to him to question their authority, whether Miss Poole’s or the personnel of ESDS.
So perhaps the transfer to Shirley Foster had been the plan all along. For her, he was ideal material. Her methods could not have been more different from those at headquarters. She didn’t issue orders, but taught him by working with him. She’d do a load of washing, checking the garments with him to see if they needed a separate wash or a particular temperature. She showed him how to iron, letting him take over more and more. They cleaned together and chose cleaning materials, they cooked together, took it in turns to wait on each other or on Clara and Maggie, discussed etiquette, practised curtsies. When Tim did something well, he got a cuddle. Once Shirley would took him on her lap and stroked his hair as if her were a little kid. Another time he got hugs from the girls. She taught him trust, and from trust came confidence. After only a few days, he had lost most of his nervousness, he was relaxed, and he was doing his chores with calm efficiency. On Thursday morning, after he had served breakfast and was clearing the table, and Clara had left for school, he turned to Shirley.
“Miss? Do you think I’m ready to have my maid’s uniform back yet?”
Shirley patted his cheek.
“I’ve already sent in an interim report, Mitzy. Miss Sasha says, providing you complete the week satisfactorily and without incident, she’ll let you have it back at the weekend, and you’ll be allowed to stay till Sunday morning.
“Yippee! Er, I mean, Thank you so much, Miss Shirley…”
“Tim – we should call you Tim until you’re officially a maid again - I’m really enjoying having you here. You’re a pleasure to work with. But this afternoon, I have to go to a meeting, so I’m handing you over to Clara and Maggie for obedience training. You know what that is. You follow their instructions willingly and promptly. You mustn’t question or demur, or you will fail this vital element of the course, which means I’ll have to report it, and you’ll be sent straight back to ESDS as you are. Do you understand what I’m saying?”
“Absolutely, madam,” said Tim, confidently.
“Good. They’ll be back for lunch around twelve, so prepare some sandwiches – you know what they like – and wait on them in the kitchen. When you’ve done the washing up and wiped the table, I’d like you to give their shoes a quick polish. I noticed Clara’s were a bit scruffy when she left this morning. Let me see, anything else… I don’t think so. Okay. I’m going to get ready. You should change as well – put on the outfit Sasha brought. And let me see what you look like with your new shoulder bag and your outside boots. Go on. I’ll be down to check in ten minutes.”
“Yes, miss… Of course…”
When she returned, Shirley threw up her hands in delight.
“My goodness, how smart you look! You’d turn a few heads in the village, and no mistake.”
Tim blushed, and touched his cheeks, which had been burning ever since he’d changed. He wanted to believe she meant that in the best possible way, but he suspected that this outfit, enhanced with accessories Sasha had brought, might possibly attract the wrong sort of attention…
“Surely you’re not shy! From what I’ve heard from Sasha, you love showing off. Aren’t you going to be principal pageboy at a big wedding in a few days?”
“Yes, madam… I’ll have a really cool outfit, too… I’m sorry, I can’t tell you about it…”
“Well, you look pretty cool now, I can tell you.”
“Do I, madam…?” He looked at her doubtfully.
“Yes, you do. Now I have to leave. Have a good day. The girls will have a surprise. They’re going to love your new top. I’ll see you this evening.”
7
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on January 20, 2026, 09:51:35 AM »
Oh dear! sounds like the 'Little Darlings' are slacking in their homework. Perhaps deducting points is not enough punishment to make them knuckle down. Maybe a more visible sign of punishment is needed.
8
Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on January 17, 2026, 11:12:53 AM »
Blunders and Mistakes
Nate was first up and nervously began his presentation. He quickly got a couple of dates confused and omitted key details on his chosen alumna’s roles in the sorority’s traditions. Brianna interrupted him with a sigh, “That’s not accurate, Nate. Did you check your sources?” Then, she added sharply, “You lose two points for lack of accuracy.”
As he continued, he was stopped again. Elise, sounding genuinely disappointed, posed the question, “Did you read anything outside the study booklet, Nate? These women are legends. You owe it to them to get the facts right!” Nate felt so exposed and vulnerable in his pretty tights and delicate blouse as his face turned red. He usually was prepared for his assignments, but they had been flooded with so many things so quickly that he hadn’t put in his normal effort… he hadn’t had time. To his dismay, he became strangely agitated under his confining dancer’s belt and tights as he got more flustered. He muttered a humiliated apology, but the damage was done; another point left the scoreboard. After another couple of minutes and more lost points, Nate’s presentation mercifully ended.
Julian went after Nate. As he was speaking, it was clear from their body language that the Sisters were still unhappy. Julian glanced at Owen helplessly, feeling the pressure mounting as Tara interrupted, “Julian, you’re just reading straight from the booklet. Didn’t you dig up anything new? We expect more than just the basics.” Her tone was sharper now, and several sisters exchanged knowing glances. Julian shuffled his feet nervously, feeling his skirt rustle against his tights.
As the flustered teen continued to stumble through his account of a famous alumna’s leadership, he next was interrupted by Brianna, who raised an eyebrow and asked, “Where did you even get that? That’s not in the notes.” Frustrated, she docked him a point. It would not be his last. He felt his face heat up.
The boys quickly understood their efforts were missing the mark. Each presentation seemed thinner than the last, and the sisters’ polite smiles began to fade, replaced with looks of mild irritation.
Owen was next, and he fared no better. His report was met with stony silence, until Tara finally broke it: “You know, a quick search would have told you so much more. This isn’t what Gamma Delta stands for.” The boys exchanged mortified glances.
Standing red-faced and slightly rattled in his adorable study outfit, he got his notes jumbled up. Elise tapped the table impatiently, “Owen, this is Gamma Delta’s legacy. Where’s the passion? Where are the stories that set our alumnae apart?” The other sissified boys all shifted in their seats as the room grew quieter and more tense.
The sisters grew more demanding, their voices firm and their expressions stern. Madison stood up, folding her arms. “We expect you to care about this. To be part of Gamma Delta, you need to show respect for those who came before.” The boys’ unease grew as the authority in the sisters’ voices made their own shortcomings painfully obvious.
Elise sighed, “Did any of you even try to dig a little deeper? This is your chance to show us you care about Gamma Delta’s legacy. Where are the stories, the interesting facts?” The feminized boys all flushed with embarrassment.
Tara, arms folded, chimed in with a disappointed shake of her head. “You’re supposed to go beyond what’s in your booklets. Did you even look anything up on your own?”
The sisters began docking points with increasing frequency. Milo’s segment on a celebrated Gamma Delta alumna contained only the most basic information, and Cassidy didn’t hesitate to announce, “Minus two for omitting any mention of her extensive scholarship work.”
As their presentations limped to a close, the boys exchanged worried glances, realizing they’d woefully underestimated the task. Tara finally spoke with a disappointed shake of her head, “Next time, we want effort. We want depth. You owe it to the women who built Gamma Delta.”
By the time the Alumna Spotlights were over, the damage was done. The Big Sisters made it clear that next time, they expected research, thoughtful preparation and a genuine appreciation for the traditions and stories that shaped Gamma Delta. The boys’ sorry record of points lost reflected the Sisters’ dissatisfaction. For the first time, they truly understood how easily their hard-earned points could fall away. It was becoming painfully clear that getting to 1000 would be daunting. The Little Darlings all sat meekly in their adorable study outfits and felt a sense of dread at whatever might come next.
Nate was first up and nervously began his presentation. He quickly got a couple of dates confused and omitted key details on his chosen alumna’s roles in the sorority’s traditions. Brianna interrupted him with a sigh, “That’s not accurate, Nate. Did you check your sources?” Then, she added sharply, “You lose two points for lack of accuracy.”
As he continued, he was stopped again. Elise, sounding genuinely disappointed, posed the question, “Did you read anything outside the study booklet, Nate? These women are legends. You owe it to them to get the facts right!” Nate felt so exposed and vulnerable in his pretty tights and delicate blouse as his face turned red. He usually was prepared for his assignments, but they had been flooded with so many things so quickly that he hadn’t put in his normal effort… he hadn’t had time. To his dismay, he became strangely agitated under his confining dancer’s belt and tights as he got more flustered. He muttered a humiliated apology, but the damage was done; another point left the scoreboard. After another couple of minutes and more lost points, Nate’s presentation mercifully ended.
Julian went after Nate. As he was speaking, it was clear from their body language that the Sisters were still unhappy. Julian glanced at Owen helplessly, feeling the pressure mounting as Tara interrupted, “Julian, you’re just reading straight from the booklet. Didn’t you dig up anything new? We expect more than just the basics.” Her tone was sharper now, and several sisters exchanged knowing glances. Julian shuffled his feet nervously, feeling his skirt rustle against his tights.
As the flustered teen continued to stumble through his account of a famous alumna’s leadership, he next was interrupted by Brianna, who raised an eyebrow and asked, “Where did you even get that? That’s not in the notes.” Frustrated, she docked him a point. It would not be his last. He felt his face heat up.
The boys quickly understood their efforts were missing the mark. Each presentation seemed thinner than the last, and the sisters’ polite smiles began to fade, replaced with looks of mild irritation.
Owen was next, and he fared no better. His report was met with stony silence, until Tara finally broke it: “You know, a quick search would have told you so much more. This isn’t what Gamma Delta stands for.” The boys exchanged mortified glances.
Standing red-faced and slightly rattled in his adorable study outfit, he got his notes jumbled up. Elise tapped the table impatiently, “Owen, this is Gamma Delta’s legacy. Where’s the passion? Where are the stories that set our alumnae apart?” The other sissified boys all shifted in their seats as the room grew quieter and more tense.
The sisters grew more demanding, their voices firm and their expressions stern. Madison stood up, folding her arms. “We expect you to care about this. To be part of Gamma Delta, you need to show respect for those who came before.” The boys’ unease grew as the authority in the sisters’ voices made their own shortcomings painfully obvious.
Elise sighed, “Did any of you even try to dig a little deeper? This is your chance to show us you care about Gamma Delta’s legacy. Where are the stories, the interesting facts?” The feminized boys all flushed with embarrassment.
Tara, arms folded, chimed in with a disappointed shake of her head. “You’re supposed to go beyond what’s in your booklets. Did you even look anything up on your own?”
The sisters began docking points with increasing frequency. Milo’s segment on a celebrated Gamma Delta alumna contained only the most basic information, and Cassidy didn’t hesitate to announce, “Minus two for omitting any mention of her extensive scholarship work.”
As their presentations limped to a close, the boys exchanged worried glances, realizing they’d woefully underestimated the task. Tara finally spoke with a disappointed shake of her head, “Next time, we want effort. We want depth. You owe it to the women who built Gamma Delta.”
By the time the Alumna Spotlights were over, the damage was done. The Big Sisters made it clear that next time, they expected research, thoughtful preparation and a genuine appreciation for the traditions and stories that shaped Gamma Delta. The boys’ sorry record of points lost reflected the Sisters’ dissatisfaction. For the first time, they truly understood how easily their hard-earned points could fall away. It was becoming painfully clear that getting to 1000 would be daunting. The Little Darlings all sat meekly in their adorable study outfits and felt a sense of dread at whatever might come next.
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 14, 2026, 04:50:52 PM »
Chapter 317.
Mrs Foster took Tim by the hand and led him into the kitchen.
“So you’re training to be a maid. You’ll be spending a lot of time in kitchens, then.”
“If I pass training, Mrs Foster…”
“Oh, don’t worry. You will. I’m going to give you a crash course. Me and the girls.”
“The girls…?”
“Don’t look surprised. They know all about maid training. They’ll look after you when I’m not here. You can trust them implicitly. Just follow their instructions in everything. They’re very good teachers. I trained them, after all…”
“I see…”
“Now, what would you like to eat? Relax and warm up, then we’ll go into the lounge and discuss the programme for the next few days.”
“Oh… I didn’t realise I was staying…”
“Yes, till the end of the week. The idea is to get you back on course. Now what do you like to drink? Milkshake? Chocolate, vanilla or strawberry?”
By the time he’d eaten, and they had repaired to the lounge, Tim was feeling a lot happier. Mrs Foster seemed really caring – so much nicer than some of the trainers at ESDS. But they had only been chatting for a few minutes when there was a ring at the bell. A few seconds later, Clara showed Sasha into the room. For a moment he thought she’d come to take him back. But his fears were quickly allayed.
“Hi Shirley… All right? Just come to drop off Mitzy’s clothes.”
She held up a large pink paper carrier bag.
Tim looked up expectantly. “My uniform?”
“No, Mitzy! We told you. Not till you improve.” She rolled her eyes. “If Mrs Foster gives us good reports, maybe in a week or so.” She put down the bag. “This is a just a change of your present outfit. It’s similar, but it has a nice halter top so you won’t be embarrassed to wear it out, and a change of collar. I’ve put in a shoulder bag and some boots and gloves, too. And a towel, your toothbrush, some toiletries, and a couple of nighties.”
Tim looked alarmed.
“I don’t think I’ll be going out, miss…”
“You never know.”
Mrs Foster smiled. “Say thank you to Sasha, Mitzy. How thoughtful of her.”
“Thank you, Miss Sasha…” he said, sulkily.
“Oh, and Shirley, there’s an envelope in there for Clara. She asked me to print out a few photos from ESDS and from the Centre. She’ll tell you what it’s all about. Well, I’ll be off then. Be a good girl, Mitzy.”
“I’ll be in touch,” grinned Mrs Foster.
After Sasha had left, and Tim was busy, Shirley slipped out the envelope. A4 size. She peeped inside. Photos of Tim as a boot boy and as a maid.
“Ah,” she murmured, “I think I can guess what this is about. I wondered why the girls were whispering about show and share…”
Mrs Foster took Tim by the hand and led him into the kitchen.
“So you’re training to be a maid. You’ll be spending a lot of time in kitchens, then.”
“If I pass training, Mrs Foster…”
“Oh, don’t worry. You will. I’m going to give you a crash course. Me and the girls.”
“The girls…?”
“Don’t look surprised. They know all about maid training. They’ll look after you when I’m not here. You can trust them implicitly. Just follow their instructions in everything. They’re very good teachers. I trained them, after all…”
“I see…”
“Now, what would you like to eat? Relax and warm up, then we’ll go into the lounge and discuss the programme for the next few days.”
“Oh… I didn’t realise I was staying…”
“Yes, till the end of the week. The idea is to get you back on course. Now what do you like to drink? Milkshake? Chocolate, vanilla or strawberry?”
By the time he’d eaten, and they had repaired to the lounge, Tim was feeling a lot happier. Mrs Foster seemed really caring – so much nicer than some of the trainers at ESDS. But they had only been chatting for a few minutes when there was a ring at the bell. A few seconds later, Clara showed Sasha into the room. For a moment he thought she’d come to take him back. But his fears were quickly allayed.
“Hi Shirley… All right? Just come to drop off Mitzy’s clothes.”
She held up a large pink paper carrier bag.
Tim looked up expectantly. “My uniform?”
“No, Mitzy! We told you. Not till you improve.” She rolled her eyes. “If Mrs Foster gives us good reports, maybe in a week or so.” She put down the bag. “This is a just a change of your present outfit. It’s similar, but it has a nice halter top so you won’t be embarrassed to wear it out, and a change of collar. I’ve put in a shoulder bag and some boots and gloves, too. And a towel, your toothbrush, some toiletries, and a couple of nighties.”
Tim looked alarmed.
“I don’t think I’ll be going out, miss…”
“You never know.”
Mrs Foster smiled. “Say thank you to Sasha, Mitzy. How thoughtful of her.”
“Thank you, Miss Sasha…” he said, sulkily.
“Oh, and Shirley, there’s an envelope in there for Clara. She asked me to print out a few photos from ESDS and from the Centre. She’ll tell you what it’s all about. Well, I’ll be off then. Be a good girl, Mitzy.”
“I’ll be in touch,” grinned Mrs Foster.
After Sasha had left, and Tim was busy, Shirley slipped out the envelope. A4 size. She peeped inside. Photos of Tim as a boot boy and as a maid.
“Ah,” she murmured, “I think I can guess what this is about. I wondered why the girls were whispering about show and share…”
10
Active Sissy Stories / Re: Tiffany's Date
« Last post by sissy servant 737-820-633 on January 13, 2026, 03:29:15 PM »
thanks for sending this story back to the top.. turns me on remembering a scene i had with my Mistress..
The more you give, the more I can give back.
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