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Active Sissy Stories / Re: The Portrait of Edward Gray
« Last post by sissyboy1212 on Yesterday at 01:14:37 PM »
A Charming Visit to the Museum
By the time they reached the museum, Edward felt as though he had entered a world completely separate from his normal life. A couple of banners fluttering outside announced the exhibition they were here to see. Edward felt his stomach sink the as they walked up the stone steps to the entrance. He felt so visible arriving in his yellow party dress as he minced behind his aunt and mother. The sun caught the satin sash at his waist, the little embroidered flowers near the hem, and the bright yellow bow in his hair. Seeing those boys in their baseball uniforms at the coffee shop had only made him feel even more formal and sissyish than before, and he cringed to be dressed this way in public.
Aunt Patricia took charge the moment they entered the museum, consulting the map to head straight to the special exhibition rooms. Edward’s eyes drifted toward signs for the military history wing and a sunlit corridor that seemed to lead to a sculpture garden, but his aunt drew them briskly past both. “Those might be very interesting another day,” she said as she bypassed them, “but this exhibition will literally be gone tomorrow, so will spend our time there.”
Inside, the exhibit drew them at once into a suite of softly lit rooms where mannequins stood in careful rows like silent guests at an old-fashioned ball. There were walking dresses in dove gray and moss green, evening gowns with pearl-trimmed bodices, striped silk day dresses with tiny waists, velvet capes, lace collars, embroidered gloves, feathered hats, and slippers so small and delicate Edward could hardly believe anyone had once crossed real streets in them. Aunt Patricia was enchanted. She began moving with Edward in tow from case to case with shining eyes, reading the labels aloud and murmuring over the workmanship. “Look at the hand stitching, sweetie,” she breathed. “And that pleating! Imagine the patience. Bespoke, every inch of it.”
Edward followed exactly as he had known he would, dragged along from one display to the next while Aunt Patricia marveled at all the dresses and styles. The exhibit was somewhat crowded, and he soon noticed something that made his cheeks grow warmer. Nearly everyone there was female. Ladies stood in careful clusters, pointing at details through the glass. Mothers guided daughters from mannequin to mannequin. A pair of teenage girls studied a velvet bustle gown and whispered. Edward saw no boys at all. Even the few men present were museum guards or attendants standing discreetly near doorways.
Of course, his darling yellow dress made him stand out. More than once, a woman smiled at him as they passed. “What an adorable dress,” one older lady said warmly, nodding toward him with a smile.
A girl of perhaps nine stared openly at Edward in his frock before telling her mother, “Her dress is as pretty as the ones in the cases.”
Another visitor leaned down and said, “You look like you belong in the exhibit yourself, dear.”
Each comment seemed kindly meant, but Edward felt them land with painful force. They made him feel as though the dress had grown brighter and wider around him. He was so conscious of his daintily puffed sleeves, shiny polished nails, frilly anklets and snug corset. The ladies were trying to be pleasant, but it just reinforced how much he looked the part of a pretty little girl. He felt an unwanted stirring in his panties, and he felt cool air in the museum on his bare legs. His glossy Mary Janes clicked softly on the marble floor with each step.
Of course Aunt Patricia made sure he showed his gratitude to every compliment, and Edward’s face burned as he murmured thanks each time, his voice small and careful.
Aunt Patricia accepted the comments as if they confirmed her best judgment.
“Doesn’t he look sweet?” she would say, gently but unmistakably emphasizing the word. “My nephew is helping with a very special portrait project.”
This revelation always produced a surprised pause, followed by widened smiles and fresh compliments that made Edward feel even more exposed. It was bad enough when strangers complimented the dress. It was worse when Aunt Patricia made sure they knew the blushing child was in fact her nephew.
In the second gallery, a docent in a navy jacket approached them after noticing Aunt Patricia lingering before a breathtaking cream silk gown trimmed with tiny glass beads. Aunt Patricia needed no encouragement. Within moments, she was explaining the whole situation of the old photograph, Edward’s resemblance to his great-great grandmother, and the portrait. Edward stood meekly beside her, wishing the polished floor would open beneath his shiny Mary Janes.
The docent listened with professional interest, then turned to him with a kind smile. “That is quite an undertaking,” she said, “and may I say, you look very lovely today.”
Edward’s blush deepened until he could feel it in his ears. “Thank you,” he whispered.
Aunt Patricia beamed as though the docent had praised them both.
Edward stood very still, terribly aware that the docent, his mother, Aunt Patricia, and several nearby visitors were all looking at him. A girl standing with her mother whispered, not quietly enough, “Is that really a boy?”
Her mother hushed her at once but then smiled apologetically at Edward. “It is a very cute dress,” she said gently, as if hoping to repair the moment.
Another woman added, “The color suits you beautifully.” The words made Edward’s stomach flutter with shame and confusion. He wanted no one to notice him, yet every polite smile seemed to indicate that they had noticed everything.
As they continued through the stuffy rooms, Aunt Patricia became more animated. She compared the dresses to the gown Edward was wearing for the portrait sittings. She admired the narrow waists, full petticoats and ornate collars. Edward listened because he had no real choice, though he found himself recognizing details despite himself. A lilac afternoon dress reminded him of “his” portrait gown. A yellow silk visiting dress, displayed near the end of the gallery, drew Aunt Patricia to a stop. “There now,” she said delightedly. “Look, Edward, this one has a delicate floral motif just like yours! It’s lovely, isn’t it?”
Edward glanced at the mannequin and then down at himself. The museum dress was older, and grander, but the echo of design was obvious enough. Nearby, two girls about his age looked at him and giggled behind their hands. “Yes, Aunty,” the befrocked teen muttered.
In the final room, the exhibit included a set of interactive displays. Three large glass-fronted installations stood along one wall, each built around an elaborate dress with a camera and mirror arrangement positioned before it. A museum sign explained that visitors could stand on the marked spot, look into the mirror, and align their reflection with the gown, as if they were wearing it themselves. The first display held a little girl’s pink dress with tiny pleats, a beribboned sash, and lace cuffs no wider than Edward’s thumbs. The second showed a white Victorian bridesmaid’s dress with a wreath of silk flowers suspended above it. The third was a pale blue evening gown with a dramatic hourglass shape, wide shoulders emphasized by puffed sleeves, a full skirt, and a waist so slim Edward could scarcely believe the silhouette was real. The mirror softened the edges of the dresses so that each visitor seemed, for a moment, to step into the past.
Aunt Patricia was delighted. She insisted they try the displays, though Edward would have been happy to view them from a distance. An attendant explained that the camera could take a souvenir photograph and print it at a small kiosk nearby. Edward stood stiffly on each marked spot while the mirror lined him up first with the pink child’s frock, then the bridesmaid dress, and finally the pale blue evening gown. He found the effect disorienting. The reflection was obviously an illusion, yet the sight still made his cheeks warm.
It seemed Aunt Patricia was seeing not a museum novelty, but further proof of what she already wanted to believe about him. When the three little printed photographs slid out of the kiosk, Aunt Patricia clasped them as if they were treasures. The computer had added in the background of a crowded Victorian street behind him in the photos, and the software had edited his head onto the gowns in the scene. “Oh, these are perfect,” she said. “A sweet little memento of our educational afternoon.”
In the gift shop, there were custom souvenir pewter frames for sale for the photos with three small openings arranged beneath a scrollwork heading engraved with the museum’s name. Of course, Aunt Patricia bought one. “You can keep it in your room and remember today,” she smiled. To Edward’s dismay, his aunt also a rack of replica Victorian accessories. Among them was a yellow parasol with a carved handle, scalloped edging, and lace-like trim that almost exactly matched the shade of Edward’s dress. Aunt Patricia picked it up with a delighted gasp. “How could we possibly leave without this?” she said. Edward’s heart sank.
So, when they left the museum, Edward carried his yellow parasol folded against his shoulder, feeling even more conspicuous than when he had arrived. The afternoon sun shone on the museum steps, and Aunt Patricia immediately decided it was too perfect an opportunity to waste. “Just a few photographs, darling,” she said, guiding him to stand beside one of the stone columns. “Open your parasol. There! Chin up.” Edward obeyed, mortified as passersby watched him posing so girlishly in front of the museum in his yellow dress with a matching Victorian parasol. Aunt Patricia took several pictures while praising how sweet he looked.
Standing so daintily in his darling frock, Edward felt completely sissified as his Saturday was overtaken by smothering girlishness. With a pained feeling, he thought of how much fun those boys must be having at their baseball game.
“Just one or two more, darling,” his aunt instructed, “and smile for me!”
“Yes, Aunty,” he replied. He forced a weak smile.
By the time they reached the museum, Edward felt as though he had entered a world completely separate from his normal life. A couple of banners fluttering outside announced the exhibition they were here to see. Edward felt his stomach sink the as they walked up the stone steps to the entrance. He felt so visible arriving in his yellow party dress as he minced behind his aunt and mother. The sun caught the satin sash at his waist, the little embroidered flowers near the hem, and the bright yellow bow in his hair. Seeing those boys in their baseball uniforms at the coffee shop had only made him feel even more formal and sissyish than before, and he cringed to be dressed this way in public.
Aunt Patricia took charge the moment they entered the museum, consulting the map to head straight to the special exhibition rooms. Edward’s eyes drifted toward signs for the military history wing and a sunlit corridor that seemed to lead to a sculpture garden, but his aunt drew them briskly past both. “Those might be very interesting another day,” she said as she bypassed them, “but this exhibition will literally be gone tomorrow, so will spend our time there.”
Inside, the exhibit drew them at once into a suite of softly lit rooms where mannequins stood in careful rows like silent guests at an old-fashioned ball. There were walking dresses in dove gray and moss green, evening gowns with pearl-trimmed bodices, striped silk day dresses with tiny waists, velvet capes, lace collars, embroidered gloves, feathered hats, and slippers so small and delicate Edward could hardly believe anyone had once crossed real streets in them. Aunt Patricia was enchanted. She began moving with Edward in tow from case to case with shining eyes, reading the labels aloud and murmuring over the workmanship. “Look at the hand stitching, sweetie,” she breathed. “And that pleating! Imagine the patience. Bespoke, every inch of it.”
Edward followed exactly as he had known he would, dragged along from one display to the next while Aunt Patricia marveled at all the dresses and styles. The exhibit was somewhat crowded, and he soon noticed something that made his cheeks grow warmer. Nearly everyone there was female. Ladies stood in careful clusters, pointing at details through the glass. Mothers guided daughters from mannequin to mannequin. A pair of teenage girls studied a velvet bustle gown and whispered. Edward saw no boys at all. Even the few men present were museum guards or attendants standing discreetly near doorways.
Of course, his darling yellow dress made him stand out. More than once, a woman smiled at him as they passed. “What an adorable dress,” one older lady said warmly, nodding toward him with a smile.
A girl of perhaps nine stared openly at Edward in his frock before telling her mother, “Her dress is as pretty as the ones in the cases.”
Another visitor leaned down and said, “You look like you belong in the exhibit yourself, dear.”
Each comment seemed kindly meant, but Edward felt them land with painful force. They made him feel as though the dress had grown brighter and wider around him. He was so conscious of his daintily puffed sleeves, shiny polished nails, frilly anklets and snug corset. The ladies were trying to be pleasant, but it just reinforced how much he looked the part of a pretty little girl. He felt an unwanted stirring in his panties, and he felt cool air in the museum on his bare legs. His glossy Mary Janes clicked softly on the marble floor with each step.
Of course Aunt Patricia made sure he showed his gratitude to every compliment, and Edward’s face burned as he murmured thanks each time, his voice small and careful.
Aunt Patricia accepted the comments as if they confirmed her best judgment.
“Doesn’t he look sweet?” she would say, gently but unmistakably emphasizing the word. “My nephew is helping with a very special portrait project.”
This revelation always produced a surprised pause, followed by widened smiles and fresh compliments that made Edward feel even more exposed. It was bad enough when strangers complimented the dress. It was worse when Aunt Patricia made sure they knew the blushing child was in fact her nephew.
In the second gallery, a docent in a navy jacket approached them after noticing Aunt Patricia lingering before a breathtaking cream silk gown trimmed with tiny glass beads. Aunt Patricia needed no encouragement. Within moments, she was explaining the whole situation of the old photograph, Edward’s resemblance to his great-great grandmother, and the portrait. Edward stood meekly beside her, wishing the polished floor would open beneath his shiny Mary Janes.
The docent listened with professional interest, then turned to him with a kind smile. “That is quite an undertaking,” she said, “and may I say, you look very lovely today.”
Edward’s blush deepened until he could feel it in his ears. “Thank you,” he whispered.
Aunt Patricia beamed as though the docent had praised them both.
Edward stood very still, terribly aware that the docent, his mother, Aunt Patricia, and several nearby visitors were all looking at him. A girl standing with her mother whispered, not quietly enough, “Is that really a boy?”
Her mother hushed her at once but then smiled apologetically at Edward. “It is a very cute dress,” she said gently, as if hoping to repair the moment.
Another woman added, “The color suits you beautifully.” The words made Edward’s stomach flutter with shame and confusion. He wanted no one to notice him, yet every polite smile seemed to indicate that they had noticed everything.
As they continued through the stuffy rooms, Aunt Patricia became more animated. She compared the dresses to the gown Edward was wearing for the portrait sittings. She admired the narrow waists, full petticoats and ornate collars. Edward listened because he had no real choice, though he found himself recognizing details despite himself. A lilac afternoon dress reminded him of “his” portrait gown. A yellow silk visiting dress, displayed near the end of the gallery, drew Aunt Patricia to a stop. “There now,” she said delightedly. “Look, Edward, this one has a delicate floral motif just like yours! It’s lovely, isn’t it?”
Edward glanced at the mannequin and then down at himself. The museum dress was older, and grander, but the echo of design was obvious enough. Nearby, two girls about his age looked at him and giggled behind their hands. “Yes, Aunty,” the befrocked teen muttered.
In the final room, the exhibit included a set of interactive displays. Three large glass-fronted installations stood along one wall, each built around an elaborate dress with a camera and mirror arrangement positioned before it. A museum sign explained that visitors could stand on the marked spot, look into the mirror, and align their reflection with the gown, as if they were wearing it themselves. The first display held a little girl’s pink dress with tiny pleats, a beribboned sash, and lace cuffs no wider than Edward’s thumbs. The second showed a white Victorian bridesmaid’s dress with a wreath of silk flowers suspended above it. The third was a pale blue evening gown with a dramatic hourglass shape, wide shoulders emphasized by puffed sleeves, a full skirt, and a waist so slim Edward could scarcely believe the silhouette was real. The mirror softened the edges of the dresses so that each visitor seemed, for a moment, to step into the past.
Aunt Patricia was delighted. She insisted they try the displays, though Edward would have been happy to view them from a distance. An attendant explained that the camera could take a souvenir photograph and print it at a small kiosk nearby. Edward stood stiffly on each marked spot while the mirror lined him up first with the pink child’s frock, then the bridesmaid dress, and finally the pale blue evening gown. He found the effect disorienting. The reflection was obviously an illusion, yet the sight still made his cheeks warm.
It seemed Aunt Patricia was seeing not a museum novelty, but further proof of what she already wanted to believe about him. When the three little printed photographs slid out of the kiosk, Aunt Patricia clasped them as if they were treasures. The computer had added in the background of a crowded Victorian street behind him in the photos, and the software had edited his head onto the gowns in the scene. “Oh, these are perfect,” she said. “A sweet little memento of our educational afternoon.”
In the gift shop, there were custom souvenir pewter frames for sale for the photos with three small openings arranged beneath a scrollwork heading engraved with the museum’s name. Of course, Aunt Patricia bought one. “You can keep it in your room and remember today,” she smiled. To Edward’s dismay, his aunt also a rack of replica Victorian accessories. Among them was a yellow parasol with a carved handle, scalloped edging, and lace-like trim that almost exactly matched the shade of Edward’s dress. Aunt Patricia picked it up with a delighted gasp. “How could we possibly leave without this?” she said. Edward’s heart sank.
So, when they left the museum, Edward carried his yellow parasol folded against his shoulder, feeling even more conspicuous than when he had arrived. The afternoon sun shone on the museum steps, and Aunt Patricia immediately decided it was too perfect an opportunity to waste. “Just a few photographs, darling,” she said, guiding him to stand beside one of the stone columns. “Open your parasol. There! Chin up.” Edward obeyed, mortified as passersby watched him posing so girlishly in front of the museum in his yellow dress with a matching Victorian parasol. Aunt Patricia took several pictures while praising how sweet he looked.
Standing so daintily in his darling frock, Edward felt completely sissified as his Saturday was overtaken by smothering girlishness. With a pained feeling, he thought of how much fun those boys must be having at their baseball game.
“Just one or two more, darling,” his aunt instructed, “and smile for me!”
“Yes, Aunty,” he replied. He forced a weak smile.
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 19, 2026, 03:00:36 PM »
Chapter 396.
There were screams of laughter and a little ripple of applause from the customers.
“Beautiful! Like them, Tim? These are the proper panties that go with your outfit. Surely you wouldn’t want to keep your unicorn and rainbow ones when you can wear these? Maria thought it would be a nice surprise to keep them back until she saw you. Oh, sweetie… I can see you love them just from the look on your face. Well? Take them, then. Maria will show you where you can change.”
Blinking and blushing he took the proffered gift. Maria ushered him into the back. When he returned a couple of minutes later the café was buzzing with expectancy.
“I bet they fit you perfectly,” exclaimed Connie. “Of course they do. They were made just for you, after all. Well, aren’t you going to show everyone? Stand over by the window. Back a bit. Yes, there. Now, let’s have a little flash of panties, shall we?” She gasped. “Oh, they look gorgeous on you! No, keep your skirt up. Let everyone see how pretty you look. Stay like that, now, while I ask everyone’s opinion.”
He had to stand showing his panties while the whole room engaged in a discussion. Eventually Connie addressed Maria again.
“So Maria – what’s the plan? Did you manage to get the noticeboard ready? You did? Wonderful.”
“Yes, Connie. I’ll explain to everyone. This afternoon we have a special offer. If you spend ten pounds or more I gave you a ticket from this roll. This entitled the ticket-holder to a panty-flash from our new assistant Popsi. He’ll be stationed right outside the door, and will be handing out ESDS leaflets to anyone who wants one. I’m hoping the promotion will generate lots more custom, and of course Popsi will get ten percent. As you leave, just show him the ticket, and he lift his skirt and give you a flash of his new panties! Won’t you, darling?”
Thank you, Maria. Such a brilliant idea. Now, Frieda, would you help me get him in position? And Bridget, perhaps you could bring the A-board, as Maria’s quite busy. Lovely. We’ll get him all ready, then we’ll leave you to it, Maria. Oh, hi Gwen. You’re here. Just in time to see Maria’s new promotion.”
“Ooh, yes… She told me all about it,” said Gwen excitedly. She was a young woman with bleached blonde hair, long pink nails, and a slightly startled expression. “Is this Popsi? He’s so good looking…”
“Show Gwen your panties, dear,” said Maria. “There. Fit him perfectly, don’t they?”
“Ooh, yes…” mused Gwen, with a slightly lecherous lowering of her eyelids, “like a glove…”
So it was that Tim found himself chained up outside Penny’s, holding a handful of leaflets next to an A-board inviting punters to get a “Popsi Panty-Flash” voucher. Connie checked the padlocks were secure, then the three ladies waved to Maria and Gwen through the window, and departed, leaving him to the mercy of the local female community.
Poor Tim. His eyes filled with tears of – well, not sadness. No. Irritation. Frustration, and Helplessness.
“May be they’ll just take a leaflet and go,” he thought, determined to brave it out.
There were screams of laughter and a little ripple of applause from the customers.
“Beautiful! Like them, Tim? These are the proper panties that go with your outfit. Surely you wouldn’t want to keep your unicorn and rainbow ones when you can wear these? Maria thought it would be a nice surprise to keep them back until she saw you. Oh, sweetie… I can see you love them just from the look on your face. Well? Take them, then. Maria will show you where you can change.”
Blinking and blushing he took the proffered gift. Maria ushered him into the back. When he returned a couple of minutes later the café was buzzing with expectancy.
“I bet they fit you perfectly,” exclaimed Connie. “Of course they do. They were made just for you, after all. Well, aren’t you going to show everyone? Stand over by the window. Back a bit. Yes, there. Now, let’s have a little flash of panties, shall we?” She gasped. “Oh, they look gorgeous on you! No, keep your skirt up. Let everyone see how pretty you look. Stay like that, now, while I ask everyone’s opinion.”
He had to stand showing his panties while the whole room engaged in a discussion. Eventually Connie addressed Maria again.
“So Maria – what’s the plan? Did you manage to get the noticeboard ready? You did? Wonderful.”
“Yes, Connie. I’ll explain to everyone. This afternoon we have a special offer. If you spend ten pounds or more I gave you a ticket from this roll. This entitled the ticket-holder to a panty-flash from our new assistant Popsi. He’ll be stationed right outside the door, and will be handing out ESDS leaflets to anyone who wants one. I’m hoping the promotion will generate lots more custom, and of course Popsi will get ten percent. As you leave, just show him the ticket, and he lift his skirt and give you a flash of his new panties! Won’t you, darling?”
Thank you, Maria. Such a brilliant idea. Now, Frieda, would you help me get him in position? And Bridget, perhaps you could bring the A-board, as Maria’s quite busy. Lovely. We’ll get him all ready, then we’ll leave you to it, Maria. Oh, hi Gwen. You’re here. Just in time to see Maria’s new promotion.”
“Ooh, yes… She told me all about it,” said Gwen excitedly. She was a young woman with bleached blonde hair, long pink nails, and a slightly startled expression. “Is this Popsi? He’s so good looking…”
“Show Gwen your panties, dear,” said Maria. “There. Fit him perfectly, don’t they?”
“Ooh, yes…” mused Gwen, with a slightly lecherous lowering of her eyelids, “like a glove…”
So it was that Tim found himself chained up outside Penny’s, holding a handful of leaflets next to an A-board inviting punters to get a “Popsi Panty-Flash” voucher. Connie checked the padlocks were secure, then the three ladies waved to Maria and Gwen through the window, and departed, leaving him to the mercy of the local female community.
Poor Tim. His eyes filled with tears of – well, not sadness. No. Irritation. Frustration, and Helplessness.
“May be they’ll just take a leaflet and go,” he thought, determined to brave it out.
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 19, 2026, 12:24:56 PM »
Chapter 395.
He had hardly put the plate down when he felt a tugging and the back of his skirt.
“Don’t go…please…I just wanted to ask…”
It was the woman at the opposite table.
“Is this latex? It’s so…sensual…”
Connie replied for him.
“Yes. Best quality. Would you like to know where we get it?”
“Very much…if you don’t mind…”
Connie passed a Fantastex business card. “They can do amazing things with latex. You’ll be amazed at the range. It’s really worth a visit.”
“Popsi?” it was Maria calling. “Order waiting here. Table three.”
He scurried off.
“That boy…”
“He’s in maid training. He can be a maid or a pageboy. Or just a houseboy if necessary, but he’s a bit too pretty for that really.”
The woman looked curious.
“It’s a company called ESDS. Egerton’s Special Domestic Services. You can hire from them by the day or week. The boys are properly trained to be polite and efficient and, usually, obedient. You should try them.”
“I shall…”
“Me too,” said her friend, enthusiastically.
“I’ve run out of cards…” She turned to Maria. “Maria? Do you have any ESDS cards?”
“I have leaflets. A whole stack of them.” She reached under the counter. “Popsi? Take these. Hand them out to anyone who wants one.”
Of course, everyone wanted one.
“I’ve got so many of these,” grinned Maria. “After that time I hired a boy maid as a waitress – what was his name? Danny, I think…something like that - I used to hand them out. But then it became too much hassle, and I stopped. I must have several hundred here…”
“Why don’t you put one in every menu?” suggested Connie. “Or get someone to hand them out in the street.”
“Good idea, Connie. Popsi? Perhaps you could do that this afternoon. Gwen’s back at one, so I won’t need you inside.”
“Of course he will,” said Connie. “Then we can go and have a drink somewhere and relax.”
“But mayn’t he run off instead,” said Maria, doubtfully.
“Oh! What a coincidence, Maria!” Connie replied, with a wink. “I just happen to have a length of chain and a couple of padlocks with me. If I’m not mistaken, there’s an old tethering ring on your wall. And my chain is just the right length to attach his collar to that ring!”
“There is! How perfect. Then I won’t have to worry at all.”
“Super!”
Tim looked at them with dismay. It slowly dawned on him that this was all a put-up job. Everyone in the café was now enjoying the joke. The joke at his expense. And things were about to get even worse.
“What about that special offer you had in mind,” continued Connie. “Did you manage to get the things ready…?”
“I did, as a matter of fact. I hope Popsi – I mean Tim - will be okay with it…”
“Of course he will. He loves the attention. Don’t you Tim? Maria, show him what you got for him.”
“Shall I?”
“Go on…”
By now everyone in the teashop had stopped eating and drinking and were paying attention. Maria smiled a mischievous smile, and reached under the counter.
“A little present for my special boy waitress.” And she held them up. “Taraa…!”
He had hardly put the plate down when he felt a tugging and the back of his skirt.
“Don’t go…please…I just wanted to ask…”
It was the woman at the opposite table.
“Is this latex? It’s so…sensual…”
Connie replied for him.
“Yes. Best quality. Would you like to know where we get it?”
“Very much…if you don’t mind…”
Connie passed a Fantastex business card. “They can do amazing things with latex. You’ll be amazed at the range. It’s really worth a visit.”
“Popsi?” it was Maria calling. “Order waiting here. Table three.”
He scurried off.
“That boy…”
“He’s in maid training. He can be a maid or a pageboy. Or just a houseboy if necessary, but he’s a bit too pretty for that really.”
The woman looked curious.
“It’s a company called ESDS. Egerton’s Special Domestic Services. You can hire from them by the day or week. The boys are properly trained to be polite and efficient and, usually, obedient. You should try them.”
“I shall…”
“Me too,” said her friend, enthusiastically.
“I’ve run out of cards…” She turned to Maria. “Maria? Do you have any ESDS cards?”
“I have leaflets. A whole stack of them.” She reached under the counter. “Popsi? Take these. Hand them out to anyone who wants one.”
Of course, everyone wanted one.
“I’ve got so many of these,” grinned Maria. “After that time I hired a boy maid as a waitress – what was his name? Danny, I think…something like that - I used to hand them out. But then it became too much hassle, and I stopped. I must have several hundred here…”
“Why don’t you put one in every menu?” suggested Connie. “Or get someone to hand them out in the street.”
“Good idea, Connie. Popsi? Perhaps you could do that this afternoon. Gwen’s back at one, so I won’t need you inside.”
“Of course he will,” said Connie. “Then we can go and have a drink somewhere and relax.”
“But mayn’t he run off instead,” said Maria, doubtfully.
“Oh! What a coincidence, Maria!” Connie replied, with a wink. “I just happen to have a length of chain and a couple of padlocks with me. If I’m not mistaken, there’s an old tethering ring on your wall. And my chain is just the right length to attach his collar to that ring!”
“There is! How perfect. Then I won’t have to worry at all.”
“Super!”
Tim looked at them with dismay. It slowly dawned on him that this was all a put-up job. Everyone in the café was now enjoying the joke. The joke at his expense. And things were about to get even worse.
“What about that special offer you had in mind,” continued Connie. “Did you manage to get the things ready…?”
“I did, as a matter of fact. I hope Popsi – I mean Tim - will be okay with it…”
“Of course he will. He loves the attention. Don’t you Tim? Maria, show him what you got for him.”
“Shall I?”
“Go on…”
By now everyone in the teashop had stopped eating and drinking and were paying attention. Maria smiled a mischievous smile, and reached under the counter.
“A little present for my special boy waitress.” And she held them up. “Taraa…!”
4
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 19, 2026, 05:22:50 AM »
Chapter 394.
It was a very pretty village, and they spent nearly an hour just wandering around the streets looking at the houses and cottages, and standing on the old bridge watching the river flow sluggishly by. Tim attracted quite a bit of attention, and as is customary in these rural communities, a number of people stopped them to say hello and ask if they needed directions, or if they liked the village, or what they thought of the weather – all a pretext for getting a closer look at Tim.
“Oh, that’s such a pretty outfit,” exclaimed one woman. “So nice to see a young man not dressed in a T-shirt and old jeans! I wish I could get my son to wear something like that. He insists on wearing his most worn-out clothes, he lays about all day and then disappears half the night! He barely talks to me. He’s either looking at his phone, or talking to his girlfriend – his “gf” he calls her. He can’t get a job. Then there’s not much here… I swear he’ll be the death of me…”
She rattled on a bit more, until Connie raised a hand. She pulled out an ESDS card and handed it to the woman.
“Give these people a call. If he’s good-looking enough, he may be qualified to be a male model, or even get some regular employment. Send him for an interview and assessment. If he’s lucky he may get a contract.”
“Oh, really? Thank you so much! I can’t wait to tell Paul – that’s his name. He is good looking… Well, that’s a mother’s opinion, of course. He has lovely curly blond hair.”
“Sounds like the perfect material,” smiled Connie. “Mention my name – Connie Brookshaw - and they’ll fast-track him.”
“Connie Brookshaw… I shall. Thank you so much, Ms Brookshaw. May I take a photo of your, er…”
“My nephew. Certainly. But don’t show it to your son, will you? He may not appreciate the finer points of couture.”
“No, right… By the way, he’s nothing to do with Penny of Penny’s Pantry, is he?”
“Oh, yes. Maria sponsored him. We’re going there later this morning.”
“Oh, really? Maybe I’ll see you. My friend and I usually pop in for a coffee…”
“Maybe later, then…”
“Do you think she will? Persuade her son, I mean…” asked Frieda.
“Oh, I hope so. Maybe ESDS should put up a recruitment poster here. Maybe in Penny’s…”
They strolled on along the main street. A woman had stopped to stare and her daughter was pointing at Tim.
“Mummy – look. That boy’s wearing a dress!”
“Yes, darling… I can see…”
“Oh, look!” cried Bridget. “This is the village museum someone mentioned. Let’s go in.” She peered through the door. “It’s quite busy though…”
“All the better,” said Connie. “Come on, Tim…”
He shook his head and made a protesting grunt. But Connie was in no mood for sulks, and gave him a smart slap on his behind.
The museum was full of old things, Roman glass, Roman coins, old farm implements, and so on. Tim attracted more attention than the exhibits, and generated quite a lot a giggles and suppressed laughter. So by the time thy left, and made their way to Penny’s Pantry, he was in quite a bad mood.
Penny’s was a cheerful little place, and quite busy. There arrival was accompanied by gasps and suppressed squeals. Connie introduced Tim to Maria, a cheerful woman in her thirties, who greeted him so warmly that it was impossible for him to remain grumpy.
“You’re even more handsome than in your picture!” Maria exclaimed, in that embarrassing way women have. “Ladies, why don’t you take a seat while I have a word with Tim.”
They sat at the only free table, while Maria took Tim by the arm and drew him behind the counter.
“Tim, would you do me a favour? Gwen – that’s my regular waitress – has taken the morning off. Could you possibly…? All you have to do is take stuff to whichever table I tell you. They’re all numbered. It’s easy. I’ll pay you, of course.”
As Tim couldn’t reply, every request made of him could be taken as answered in the affirmative.
“Thank you so much. I’ll just do the ladies drinks…”
He delivered the drinks without mishap. He could feel every eye in the place focussed on him. There was a murmur of conversation, punctuated by giggles. Several people passing in the street also stopped to stare. He was soon busy delivering drinks and food. As he brought the ladies a plate of pastries, the woman behind him murmured, “that’s such a cute outfit…”
He placed the plate on the table. “Thank you, Popsi!” grinned Frieda. They were enjoying themselves hugely. It wasn’t fair!
It was a very pretty village, and they spent nearly an hour just wandering around the streets looking at the houses and cottages, and standing on the old bridge watching the river flow sluggishly by. Tim attracted quite a bit of attention, and as is customary in these rural communities, a number of people stopped them to say hello and ask if they needed directions, or if they liked the village, or what they thought of the weather – all a pretext for getting a closer look at Tim.
“Oh, that’s such a pretty outfit,” exclaimed one woman. “So nice to see a young man not dressed in a T-shirt and old jeans! I wish I could get my son to wear something like that. He insists on wearing his most worn-out clothes, he lays about all day and then disappears half the night! He barely talks to me. He’s either looking at his phone, or talking to his girlfriend – his “gf” he calls her. He can’t get a job. Then there’s not much here… I swear he’ll be the death of me…”
She rattled on a bit more, until Connie raised a hand. She pulled out an ESDS card and handed it to the woman.
“Give these people a call. If he’s good-looking enough, he may be qualified to be a male model, or even get some regular employment. Send him for an interview and assessment. If he’s lucky he may get a contract.”
“Oh, really? Thank you so much! I can’t wait to tell Paul – that’s his name. He is good looking… Well, that’s a mother’s opinion, of course. He has lovely curly blond hair.”
“Sounds like the perfect material,” smiled Connie. “Mention my name – Connie Brookshaw - and they’ll fast-track him.”
“Connie Brookshaw… I shall. Thank you so much, Ms Brookshaw. May I take a photo of your, er…”
“My nephew. Certainly. But don’t show it to your son, will you? He may not appreciate the finer points of couture.”
“No, right… By the way, he’s nothing to do with Penny of Penny’s Pantry, is he?”
“Oh, yes. Maria sponsored him. We’re going there later this morning.”
“Oh, really? Maybe I’ll see you. My friend and I usually pop in for a coffee…”
“Maybe later, then…”
“Do you think she will? Persuade her son, I mean…” asked Frieda.
“Oh, I hope so. Maybe ESDS should put up a recruitment poster here. Maybe in Penny’s…”
They strolled on along the main street. A woman had stopped to stare and her daughter was pointing at Tim.
“Mummy – look. That boy’s wearing a dress!”
“Yes, darling… I can see…”
“Oh, look!” cried Bridget. “This is the village museum someone mentioned. Let’s go in.” She peered through the door. “It’s quite busy though…”
“All the better,” said Connie. “Come on, Tim…”
He shook his head and made a protesting grunt. But Connie was in no mood for sulks, and gave him a smart slap on his behind.
The museum was full of old things, Roman glass, Roman coins, old farm implements, and so on. Tim attracted more attention than the exhibits, and generated quite a lot a giggles and suppressed laughter. So by the time thy left, and made their way to Penny’s Pantry, he was in quite a bad mood.
Penny’s was a cheerful little place, and quite busy. There arrival was accompanied by gasps and suppressed squeals. Connie introduced Tim to Maria, a cheerful woman in her thirties, who greeted him so warmly that it was impossible for him to remain grumpy.
“You’re even more handsome than in your picture!” Maria exclaimed, in that embarrassing way women have. “Ladies, why don’t you take a seat while I have a word with Tim.”
They sat at the only free table, while Maria took Tim by the arm and drew him behind the counter.
“Tim, would you do me a favour? Gwen – that’s my regular waitress – has taken the morning off. Could you possibly…? All you have to do is take stuff to whichever table I tell you. They’re all numbered. It’s easy. I’ll pay you, of course.”
As Tim couldn’t reply, every request made of him could be taken as answered in the affirmative.
“Thank you so much. I’ll just do the ladies drinks…”
He delivered the drinks without mishap. He could feel every eye in the place focussed on him. There was a murmur of conversation, punctuated by giggles. Several people passing in the street also stopped to stare. He was soon busy delivering drinks and food. As he brought the ladies a plate of pastries, the woman behind him murmured, “that’s such a cute outfit…”
He placed the plate on the table. “Thank you, Popsi!” grinned Frieda. They were enjoying themselves hugely. It wasn’t fair!
5
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 19, 2026, 03:13:35 AM »
Chapter 393.
“Now, are you going to behave? Or do I have to get my whip out? That’s better. What do you think of those pretty gloves? Gorgeous, aren’t they? Hold them up so we can see them. That’s it. There, they really are just the perfect finishing touch, don’t you think? What was that, Tim?”
With his new ball gag, poor Tim could do little more than grunt. Excellent, thought Connie. She’d be able to tease him mercilessly all day. And for punishments she’d think about some special mitts so he wouldn’t be able to pull at anything – or even pleasure himself properly! How amusing. This evening she’d update Cassandra. She’d loved the videos. Everyone at ESDS had. If Tim knew they were going to be available to subscribers… She smiled to herself. Well, it was his fault for being so cute, for being such a show-off, and being such an easy dupe.
“Well, we might as well get going. We’ll be early, but we can have a nice walk round the village first. It’s very pretty. Looks olde-worldy, but there’s plenty of money there, take it from me, girls. Anyway…”
They got there coats and headed for the door. Tim was having to be cajoled along. Finally Connie got him outside. She had to accompany him to the car, and return to shut the door.
“What a fuss!” she murmured as she went down the path for the second time. “But once we’re there, he won’t have any choice…”
“Now, are you going to behave? Or do I have to get my whip out? That’s better. What do you think of those pretty gloves? Gorgeous, aren’t they? Hold them up so we can see them. That’s it. There, they really are just the perfect finishing touch, don’t you think? What was that, Tim?”
With his new ball gag, poor Tim could do little more than grunt. Excellent, thought Connie. She’d be able to tease him mercilessly all day. And for punishments she’d think about some special mitts so he wouldn’t be able to pull at anything – or even pleasure himself properly! How amusing. This evening she’d update Cassandra. She’d loved the videos. Everyone at ESDS had. If Tim knew they were going to be available to subscribers… She smiled to herself. Well, it was his fault for being so cute, for being such a show-off, and being such an easy dupe.
“Well, we might as well get going. We’ll be early, but we can have a nice walk round the village first. It’s very pretty. Looks olde-worldy, but there’s plenty of money there, take it from me, girls. Anyway…”
They got there coats and headed for the door. Tim was having to be cajoled along. Finally Connie got him outside. She had to accompany him to the car, and return to shut the door.
“What a fuss!” she murmured as she went down the path for the second time. “But once we’re there, he won’t have any choice…”
6
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 18, 2026, 05:32:38 PM »
Chapter 392.
But the look in Tim’s sad little eyes was too much even for Connie.
“Ah, don’t look so miserable, Tim. Actually there’s been a change of plan. We’ll postpone houseboy duties for a day or two. I was chatting to my friend Maria this morning – she runs a little café in Bowersford village, just up the road. Well, I guess “café” isn’t the right word. She calls it a teashop. Penny’s Pantry – named after her mum, who started it. It’s quite twee. Attracts all the women from the area – somewhere they can sit and drink tea and exchange gossip for hours on end. This may be a small, out-of-the-way place, but gossip seems to proliferate in inverse proportion to the population. Anyway, she’s invited us along. We’ll go in the morning. According to the forecast it’s going to be a nice day. It’s still really mild for the time of year. Afterwards we could go on somewhere else. Make a day of it. What do you think?”
Tim nodded slowly. Anything was better than being treated live a slave. He wondered what he would be wearing. Connie seemed to have read his mind.
“When Maria first saw your picture she immediately offered to sponsor you. So she’s paid for your next outfit. So we agreed we’d visit her tomorrow, as Tuesday’s usually a quietish day in the café.”
He looked at her questioningly.
“It’s nice, don’t worry. You’ll like it. No hotpants, though. Lately it seems as though they just make you horny. In fact…”
She took a step back and regarded him critically. She frowned.
“Are you getting horny now? Girls? Am I imagining things, or is he…?”
“Yes! He’s got a little erection!” cried Frieda, delightedly.
Tim clapped his hands to his shorts.
“Not already…” smiled Connie, shaking her head. “Tim, take your hands away, there’s a dear, and let us check.”
Tim shook his head fearfully.
“No? Well, bed time, then. Let’s get you unlocked and ungagged. If you want to play you can do so in your bedroom. I haven’t printed your poster yet, but you’ll find a nice framed piccy of Kit on your bedside cabinet. Oh, you like that, don’t you? Well make sure you don’t oversleep. Breakfast at eight thirty, all right?”
Tuesday morning. Tim slept through his alarm, but Connie playfully flicked water on him till he got up. He was very grumpy, and his mood didn’t improve when she showed him his outfit, a pretty pink latex dress with the words “Penny’s Popsi” across the chest.
“Popsi? What’s a Popsi?”
“It’s a cute girl, Tim. Just like you’re going to be today. Maria’s a good friend, and you’d better not be rude to her.”
“Why do I have to wear all these stupid outfits? And be photographed and videoed? Suppose ESDS really takes off one day. My pictures will be all over the internet.” He had a sudden panic attack. “What about those ones of me…”
“Masturbating? Well, if they ever came out, they would certainly make you famous. Don’t you want to be a celebrity? You’ve always loved attention…”
“Miss. Please. Promise me…”
“No promises, Tim. Just be a good boy, and I’ll look after you… Now, breakfast…”
But Tim wouldn’t let go of his anxiety, and was complaining all through breakfast.
Connie looked at the others. “Time for his new outfit, I’m thinking.”
“Can’t be too soon,” agreed Bridget.
Connie brought it in, the dress, matching shoes and white stockings. And his favourite panties. As they helped him into it, he was still mouthing off. Connie fetched the hood which he had worn the day before.
“I’m not wearing that. Not if we’re going out. What will people think?”
Connie sighed. You know what, Tim? I’ve had enough. The only think that seems to keep you in order is a nice fat butt plug. Well, this outfit doesn’t lend itself to that, but we do have a temporary replacement. Today we proceed to the next stage of gag training, with a medium ball. Yesterday was a small. And it’s pink, to match the rest of your outfit. So stand still while we get it on you.”
The ladies were strong, and there were three of them.
“No! Miss! Stop it! Okay…but not the gag, please… Miss…? Mmph…”
Connie tightened the straps of the ball gag and locked his collar. “There. That’s better. Peace at last! Now, stand back over there So I can get a quick snap… Tim! Stop sulking. Stop sulking or else! Thank you. Now a close-up… Good boy!”
But the look in Tim’s sad little eyes was too much even for Connie.
“Ah, don’t look so miserable, Tim. Actually there’s been a change of plan. We’ll postpone houseboy duties for a day or two. I was chatting to my friend Maria this morning – she runs a little café in Bowersford village, just up the road. Well, I guess “café” isn’t the right word. She calls it a teashop. Penny’s Pantry – named after her mum, who started it. It’s quite twee. Attracts all the women from the area – somewhere they can sit and drink tea and exchange gossip for hours on end. This may be a small, out-of-the-way place, but gossip seems to proliferate in inverse proportion to the population. Anyway, she’s invited us along. We’ll go in the morning. According to the forecast it’s going to be a nice day. It’s still really mild for the time of year. Afterwards we could go on somewhere else. Make a day of it. What do you think?”
Tim nodded slowly. Anything was better than being treated live a slave. He wondered what he would be wearing. Connie seemed to have read his mind.
“When Maria first saw your picture she immediately offered to sponsor you. So she’s paid for your next outfit. So we agreed we’d visit her tomorrow, as Tuesday’s usually a quietish day in the café.”
He looked at her questioningly.
“It’s nice, don’t worry. You’ll like it. No hotpants, though. Lately it seems as though they just make you horny. In fact…”
She took a step back and regarded him critically. She frowned.
“Are you getting horny now? Girls? Am I imagining things, or is he…?”
“Yes! He’s got a little erection!” cried Frieda, delightedly.
Tim clapped his hands to his shorts.
“Not already…” smiled Connie, shaking her head. “Tim, take your hands away, there’s a dear, and let us check.”
Tim shook his head fearfully.
“No? Well, bed time, then. Let’s get you unlocked and ungagged. If you want to play you can do so in your bedroom. I haven’t printed your poster yet, but you’ll find a nice framed piccy of Kit on your bedside cabinet. Oh, you like that, don’t you? Well make sure you don’t oversleep. Breakfast at eight thirty, all right?”
Tuesday morning. Tim slept through his alarm, but Connie playfully flicked water on him till he got up. He was very grumpy, and his mood didn’t improve when she showed him his outfit, a pretty pink latex dress with the words “Penny’s Popsi” across the chest.
“Popsi? What’s a Popsi?”
“It’s a cute girl, Tim. Just like you’re going to be today. Maria’s a good friend, and you’d better not be rude to her.”
“Why do I have to wear all these stupid outfits? And be photographed and videoed? Suppose ESDS really takes off one day. My pictures will be all over the internet.” He had a sudden panic attack. “What about those ones of me…”
“Masturbating? Well, if they ever came out, they would certainly make you famous. Don’t you want to be a celebrity? You’ve always loved attention…”
“Miss. Please. Promise me…”
“No promises, Tim. Just be a good boy, and I’ll look after you… Now, breakfast…”
But Tim wouldn’t let go of his anxiety, and was complaining all through breakfast.
Connie looked at the others. “Time for his new outfit, I’m thinking.”
“Can’t be too soon,” agreed Bridget.
Connie brought it in, the dress, matching shoes and white stockings. And his favourite panties. As they helped him into it, he was still mouthing off. Connie fetched the hood which he had worn the day before.
“I’m not wearing that. Not if we’re going out. What will people think?”
Connie sighed. You know what, Tim? I’ve had enough. The only think that seems to keep you in order is a nice fat butt plug. Well, this outfit doesn’t lend itself to that, but we do have a temporary replacement. Today we proceed to the next stage of gag training, with a medium ball. Yesterday was a small. And it’s pink, to match the rest of your outfit. So stand still while we get it on you.”
The ladies were strong, and there were three of them.
“No! Miss! Stop it! Okay…but not the gag, please… Miss…? Mmph…”
Connie tightened the straps of the ball gag and locked his collar. “There. That’s better. Peace at last! Now, stand back over there So I can get a quick snap… Tim! Stop sulking. Stop sulking or else! Thank you. Now a close-up… Good boy!”
7
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 14, 2026, 04:21:22 AM »
Tim may not be feeling quite so impatient, RibbonBound...
8
Active Sissy Stories / Re: His Aunt Nicole
« Last post by RibbonBound on August 13, 2026, 06:39:46 PM »
Oh my! This is getting so good!!! The manipulation and gaslighting is top notch. And Timmy in his little 'Piggy Pageboy' outfit! Perfection! You are just so delightfully creative! Can't wait for the next chapter!
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 12, 2026, 06:35:05 PM »
Chapter 391.
For a moment there was no reply – only a faint sniffling sound. Then,
“Oh… Miss Brookshaw… Yes, thank you. I…” But she collapsed in giggles.
“What do you think?”
“He… Haha, he looks so cute… Tim, you look… It suits you perfectly. Now I have a new pet name for you… My little piggy…. Hahaha…”
Jenny had been slightly suspicious her so-called boyfriend might have been flirting with members of the staff. These pictures had totally reassured her. Tim himself, however, was not so amused.
“It’s just one outfit, Jenny. It’s supposed to be a joke, see?”
“Is that why you’re chained up?”
“No… That’s just…”
“Because he has trouble staying in one place,” laughed Connie. “I could send pics of some of the other outfits if you’re interested…”
“No!”
“Miss Brookshaw? I’d love any pictures you can spare… That aren’t secret, you know…”
“I’ll see what I can do, Jenny. We’ve rather overrun for now. Do you need another minute or two with Tim?”
“No, that’s all right. I need to transfer these onto my laptop so I can see them in their full glory…”
“Of course. Goodbye for now, Jenny. Sorry about tonight. I’ll make sure he isn’t late tomorrow. Maybe you should have a video call to make up…”
Tim was furious, but also afraid too afraid of Connie to express his anger, so he resorted to whining.
“Miss… Why did you do that… What will Jenny think…? I look like an idiot…”
“You look like what you are… Pageboy Piggy. I’m sure she’ll love you all the more for being so sweet. If she does think you’re a fool, it’s your own fault.”
“How is it my fault?”
“You really don’t get it, do you. If you’d smiled and made a joke of it, she would have thought you were being a good sport. But no, you had to get all embarrassed, blushing and wriggling like a little kid caught getting up to mischief.”
Tim realised she was quite right, but still couldn’t bring himself to admit it.
“You had no right… You shouldn’t mess with my relationship like that. You shouldn’t even have been listening in to my private phone conversation…”
“Mess with your relationship?” Connie gave a cynical laugh. “After you’ve spent the last couple of days smooching with Kit? Are you for real? I’m fed up with this. I’m fed up with your whining. Fortunately I’ve got the perfect thing to put a stop to it.”
She pulled the latex hood out of the bag, strode over to him, and, ignoring his protests, and thrust it over his head. She had to unlock and remove his collar temporarily to roll down the neck. It fitted him perfectly. Once neatly in place, she thrust the rubber ball unceremoniously into his mouth, and buckled up the mouth strap. She stood back. He was trying to speak, but could only make an inarticulate moaning sound. She took out her phone and took a snap.
You look so funny with that indignant look on your face. Is diddums cross? Is piggy disgruntled? Disgruntled – get it? Oh, I love it.”
“All he needs is a little snout…” added Bridget.
“Yes! Piggy’s first ball-gag!” taunted Connie. “Don’t worry – there’ll be plenty more!”
She took a close-up of his surprised, helpless face.
“I bet Jenny would love this one…”
He shook his head vigorously, and made muffled pleading noises.
“That’s it – beg for mercy. You’ve had it too easy, master Timothy. It’s going to get harder from now on, though… Right girls?”
“Right!” They chorused.
For a moment there was no reply – only a faint sniffling sound. Then,
“Oh… Miss Brookshaw… Yes, thank you. I…” But she collapsed in giggles.
“What do you think?”
“He… Haha, he looks so cute… Tim, you look… It suits you perfectly. Now I have a new pet name for you… My little piggy…. Hahaha…”
Jenny had been slightly suspicious her so-called boyfriend might have been flirting with members of the staff. These pictures had totally reassured her. Tim himself, however, was not so amused.
“It’s just one outfit, Jenny. It’s supposed to be a joke, see?”
“Is that why you’re chained up?”
“No… That’s just…”
“Because he has trouble staying in one place,” laughed Connie. “I could send pics of some of the other outfits if you’re interested…”
“No!”
“Miss Brookshaw? I’d love any pictures you can spare… That aren’t secret, you know…”
“I’ll see what I can do, Jenny. We’ve rather overrun for now. Do you need another minute or two with Tim?”
“No, that’s all right. I need to transfer these onto my laptop so I can see them in their full glory…”
“Of course. Goodbye for now, Jenny. Sorry about tonight. I’ll make sure he isn’t late tomorrow. Maybe you should have a video call to make up…”
Tim was furious, but also afraid too afraid of Connie to express his anger, so he resorted to whining.
“Miss… Why did you do that… What will Jenny think…? I look like an idiot…”
“You look like what you are… Pageboy Piggy. I’m sure she’ll love you all the more for being so sweet. If she does think you’re a fool, it’s your own fault.”
“How is it my fault?”
“You really don’t get it, do you. If you’d smiled and made a joke of it, she would have thought you were being a good sport. But no, you had to get all embarrassed, blushing and wriggling like a little kid caught getting up to mischief.”
Tim realised she was quite right, but still couldn’t bring himself to admit it.
“You had no right… You shouldn’t mess with my relationship like that. You shouldn’t even have been listening in to my private phone conversation…”
“Mess with your relationship?” Connie gave a cynical laugh. “After you’ve spent the last couple of days smooching with Kit? Are you for real? I’m fed up with this. I’m fed up with your whining. Fortunately I’ve got the perfect thing to put a stop to it.”
She pulled the latex hood out of the bag, strode over to him, and, ignoring his protests, and thrust it over his head. She had to unlock and remove his collar temporarily to roll down the neck. It fitted him perfectly. Once neatly in place, she thrust the rubber ball unceremoniously into his mouth, and buckled up the mouth strap. She stood back. He was trying to speak, but could only make an inarticulate moaning sound. She took out her phone and took a snap.
You look so funny with that indignant look on your face. Is diddums cross? Is piggy disgruntled? Disgruntled – get it? Oh, I love it.”
“All he needs is a little snout…” added Bridget.
“Yes! Piggy’s first ball-gag!” taunted Connie. “Don’t worry – there’ll be plenty more!”
She took a close-up of his surprised, helpless face.
“I bet Jenny would love this one…”
He shook his head vigorously, and made muffled pleading noises.
“That’s it – beg for mercy. You’ve had it too easy, master Timothy. It’s going to get harder from now on, though… Right girls?”
“Right!” They chorused.
10
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on August 12, 2026, 07:13:21 AM »
Chapter 390.
The particular item Connie had in mind was the first resort when dealing with a complainer. It was true that Tim had hardly ever complained, but Connie had become impatient with indulging him, and had been looking for an excuse to apply some punishment. After all there was only a few days left in the session, and she’d hardly made him squirm so far. This was not her usual practice. The arrival of Kit had rather changed the dynamics in Tim’s favour. But she was determined to reverse the trend.
She was rummaging through one of the drawers in one of the cabinets in one of the spare rooms. There was a lot of interesting equipment stored in that farmhouse, and in its cold, gloomy cellars.
“Ah. Here we are.”
She pulled out a small sealed black plastic bag, opened it, and drew forth a piece of folded pink latex. She unfolded it and held it up.
“It should fit. I’ll make it fit if necessary.”
The object in question was a smooth whole-head rubber helmet, open-faced, with a black leather strap at the level of the mouth, and a black ball-gag. She also fingered a pink leather head-harness and ball-gag lying in the drawer.
“That would be nice too, but all in good time. He’ll look pretty in this today.”
She replaced the hood in its bag, closed the drawer, and went to leave. As she did so, she heard a phone ringing in an adjacent room.
“That’s not mine… Goodness!”
She looked at her watch. Almost a quarter to ten!
“I completely forgot about Jenny! We were so carried away…”
She hurried to the spare room where she had hidden Tim’s phone. It was on charge. She picked it up.
“Jenny? I’m so sorry! Tim was a bit tied up, and the photo session overran… I’ll get him right away. Are you well? Good…that’s nice…oh, really? Tim? He’s fine, yes. Working hard. Today? Oh, a long session, yes. But great fun. He really makes an excellent model. He is, yes. A fine figure of a boy… Well, not a boy any more. To us oldies he seems just a boy…”
She had made it back to the living room.
“Ah, Tim. There you are!” (As if he could be anywhere else.) “It’s Jenny. I’m sorry, we were so busy I completely forgot.”
Tim, alarmed, stated shaking his head vigorously. But Connie had seen the humour of the situation. She went to give him the phone, but changed her mind. Instead she put it on speaker and placed it on the coffee table out of his reach.
“Say hi, Tim. We’ll leave you to chat. Fifteen minutes, don’t forget…”
She gave the others a warning glance, finger to lips, and quietly took her seat. Tim was furious, but couldn’t say anything.
“Tim? Are you there?”
“Oh… Yeah. H-hi, Jenny… H-how are you?”
“You couldn’t ring me on time… You must have been busy.”
“Oh…yeah…sorry. We were right in the middle of a project…”
“What project was that? What about?”
“Oh, you know…”
“No, I don’t. That’s why I’m asking.” Jenny sounded slightly irritated.
“Er… oh, just a new outfit…” Tim was a useless liar. He reverted to diluted truth. “Just, you know, pageboy stuff…”
“A new pageboy outfit? What’s it like?”
“I’m, er, not supposed to say…” He glared at his tormentors, struggling to smother their mirth.
“What, you can’t even tell me that? Surely it can’t be that big a trade secret.”
Tim was struggling now. “You know how it is… I’m not allowed… Miss is very strict…”
“Have you finished?”
Tim was desperate to get off the phone. “No. Nearly, though. Just a few more shots. So I can’t talk for long…”
“Ooh. Can I have a little peep? We could have a video call – or just send me a photo? Promise I won’t tell…”
“No, I said I can’t…”
“Ask Ms Brookshaw. Maybe she wouldn’t mind…”
Connie seized the opportunity. “Tim? Did someone mention my name?” she called, as if from a distance.
“No, it’s all right…” he replied, in a panic.
“It was me,” said Jenny as loud as she could. “Are you there, Ms Brookshaw?”
“Oh, hi Jenny. Yes, I’m right here. What was it you wanted?”
Tim was madly shaking his head, pleading with his eyes. Connie ignored him.
“I was just asking Tim if I could have a sneak peek at the uniform he’s modelling…”
“Oh, is that all? Of course, dear. Here, I’ll send you a snap…”
She picked up the phone and prepared to take his picture.
“No! Miss, please…” whined Tim. But to no avail.
“Done. Now turn round and show Jenny your cute little tail…”
“Miss…”
“Or else…”
He obeyed.
“There. Did you get those, Jenny?”
The particular item Connie had in mind was the first resort when dealing with a complainer. It was true that Tim had hardly ever complained, but Connie had become impatient with indulging him, and had been looking for an excuse to apply some punishment. After all there was only a few days left in the session, and she’d hardly made him squirm so far. This was not her usual practice. The arrival of Kit had rather changed the dynamics in Tim’s favour. But she was determined to reverse the trend.
She was rummaging through one of the drawers in one of the cabinets in one of the spare rooms. There was a lot of interesting equipment stored in that farmhouse, and in its cold, gloomy cellars.
“Ah. Here we are.”
She pulled out a small sealed black plastic bag, opened it, and drew forth a piece of folded pink latex. She unfolded it and held it up.
“It should fit. I’ll make it fit if necessary.”
The object in question was a smooth whole-head rubber helmet, open-faced, with a black leather strap at the level of the mouth, and a black ball-gag. She also fingered a pink leather head-harness and ball-gag lying in the drawer.
“That would be nice too, but all in good time. He’ll look pretty in this today.”
She replaced the hood in its bag, closed the drawer, and went to leave. As she did so, she heard a phone ringing in an adjacent room.
“That’s not mine… Goodness!”
She looked at her watch. Almost a quarter to ten!
“I completely forgot about Jenny! We were so carried away…”
She hurried to the spare room where she had hidden Tim’s phone. It was on charge. She picked it up.
“Jenny? I’m so sorry! Tim was a bit tied up, and the photo session overran… I’ll get him right away. Are you well? Good…that’s nice…oh, really? Tim? He’s fine, yes. Working hard. Today? Oh, a long session, yes. But great fun. He really makes an excellent model. He is, yes. A fine figure of a boy… Well, not a boy any more. To us oldies he seems just a boy…”
She had made it back to the living room.
“Ah, Tim. There you are!” (As if he could be anywhere else.) “It’s Jenny. I’m sorry, we were so busy I completely forgot.”
Tim, alarmed, stated shaking his head vigorously. But Connie had seen the humour of the situation. She went to give him the phone, but changed her mind. Instead she put it on speaker and placed it on the coffee table out of his reach.
“Say hi, Tim. We’ll leave you to chat. Fifteen minutes, don’t forget…”
She gave the others a warning glance, finger to lips, and quietly took her seat. Tim was furious, but couldn’t say anything.
“Tim? Are you there?”
“Oh… Yeah. H-hi, Jenny… H-how are you?”
“You couldn’t ring me on time… You must have been busy.”
“Oh…yeah…sorry. We were right in the middle of a project…”
“What project was that? What about?”
“Oh, you know…”
“No, I don’t. That’s why I’m asking.” Jenny sounded slightly irritated.
“Er… oh, just a new outfit…” Tim was a useless liar. He reverted to diluted truth. “Just, you know, pageboy stuff…”
“A new pageboy outfit? What’s it like?”
“I’m, er, not supposed to say…” He glared at his tormentors, struggling to smother their mirth.
“What, you can’t even tell me that? Surely it can’t be that big a trade secret.”
Tim was struggling now. “You know how it is… I’m not allowed… Miss is very strict…”
“Have you finished?”
Tim was desperate to get off the phone. “No. Nearly, though. Just a few more shots. So I can’t talk for long…”
“Ooh. Can I have a little peep? We could have a video call – or just send me a photo? Promise I won’t tell…”
“No, I said I can’t…”
“Ask Ms Brookshaw. Maybe she wouldn’t mind…”
Connie seized the opportunity. “Tim? Did someone mention my name?” she called, as if from a distance.
“No, it’s all right…” he replied, in a panic.
“It was me,” said Jenny as loud as she could. “Are you there, Ms Brookshaw?”
“Oh, hi Jenny. Yes, I’m right here. What was it you wanted?”
Tim was madly shaking his head, pleading with his eyes. Connie ignored him.
“I was just asking Tim if I could have a sneak peek at the uniform he’s modelling…”
“Oh, is that all? Of course, dear. Here, I’ll send you a snap…”
She picked up the phone and prepared to take his picture.
“No! Miss, please…” whined Tim. But to no avail.
“Done. Now turn round and show Jenny your cute little tail…”
“Miss…”
“Or else…”
He obeyed.
“There. Did you get those, Jenny?”
The more you give, the more I can give back.
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