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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 10, 2025, 09:38:44 AM »
Chapter 241.
Frankie Meering sat in the waiting-room in a state of contained nervous uneasiness. She had never intended to make a visit to the boot parlour. She was an only child, and had been brought up by a single mother with anxiety issues, who had taught her to be wary of everyone, but especially men. As a result she was still as timid as a little mouse in mixed society, and was only really comfortable in the company of her few friends or her horses. But two of those friends, who had already visited, had coaxed and teased her until she felt ashamed of her cowardice, and consented to take the plunge. Having agreed and allowed them to book a session for her, she immediately regretted her decision. But they had made sure she attended, accompanying her to the boot parlour entrance and handing her into Ellie’s custody. Even then, had it not been for Ellie’s detaining her with aimless gossip, at which she excelled, she may well have fled.
She had seen the boys about the Centre in their civvies, and the sight of them brought a flush to her cheeks, and, when on one occasion they passed close by and looked at her, almost gave her a panic attack. Tim especially seemed so tall and masculine that the mere idea of being in his company, especially wearing one of those superhero uniforms she had seen at the show, made her heart flutter with terror.
She waited, trembling, as the clock ticked towards nine. On the dot, the door opened, and the boys appeared - their first appearance before customers as pageboys. She took in the little latex shorts with pink frills, the frilled latex gloves, the Mary Janes, the ribbon chokers – and nearly laughed out loud. Her hand went to her mouth, and she emitted an involuntary snort. The boys, anticipating quite the opposite reaction, stopped in their tracks. Was this the shy, delicate girl Ellie had warned them about? Had there been a change of booking? Why wasn’t she staring in admiration at their amazing cool uniforms?
Bobby took charge.
“Er, good morning, miss. I’m Bobby, and this is Timmy. Boot boys at your service. Please instruct us as to what you require, and we’ll do our best…”
Frankie had quickly recovered her self-control. “Thank you, boys. I must say you look very…smart. Smart, yes.” She was fighting the desire to burst out laughing. So these were the boys she had been frightened of! How could they possibly think…? But it didn’t matter. They believed it, and she wasn’t going to disabuse them. She’d take her cue from them.
“Wow! What amazing uniforms! You look so cool. I’m so glad I came to see you at last.”
The boys looked at each other with satisfied smiles. She must have been taken aback at first. Too much of a shock for her, probably.
Tim immediately went into swaggering mode.
“Glad you like ‘em, miss. Do you like the colour? Cos we got uvvers in the pipeline, like, in different styles and colours.”
“Wherever did you get them?”
“We got our own supplier, see? Big internash’nal company. Make us whatever we want.”
“Really? But I like these ones. I love them, in fact. Can I see…?”
She leant forward. Tim strolled over to give her a better view. She reached out and touched the side of his shorts, then ruffled his frills. She noted with delight the vertical bulge at the front, and the neat separation of his balls. She bit her lip, determined to stay serious.
“They’re so well made… And the fit…”
“All our uniforms are made to measure,” piped up Bobby.
“Gosh, is that a fact?” Frankie leant back again. “Do you only wear them in here? It’s a pity you can’t wear them outside for everyone to see.”
“Well, no, we’re not allowed,” continued Bobby. “I think Miss Poole is worried they might get damaged if we did that…”
“Yeah. They’re ‘spensive, see…very ‘spensive,” boasted Tim.
“But next month,” said Bobby, excitedly, “we have permission to wear them to a big wedding. It’s like a friend of a friend…”
“Gosh, how exciting! You’ll be a big hit, I’m sure…”
There was a short pause, while Frankie looked both of them up and down. She took out her phone.
“Would you mind if…?”
“No, not at all,” said Bobby. “Go ahead.”
“Could I have one of each of you separately, then one with both of you together?”
“Sure.”
“Bobby? Could you stand by the door? Just stand naturally…”
She rose from her chair and stood opposite him. Bobby hooked his thumbs into his belt and grinned. Frankie took a number snaps in various poses, keeping him busy for about five minutes, during which time he became conscious of the increasing intensity of the vibrations deep inside, and the consequent effect on his level of arousal. By the time she was satisfied, the pressure in the front of his shorts was palpable. He blushed slightly, and was relieved to when she called on Tim to take his place.
But Tim was already in a worse state. His plug had been twitching and pulsing all the while Bobby was being photographed, and now, despite his best efforts, his coc-k was quite out of control, and flaunting its length shamelessly as if determined to do its best to reach his belt buckle. At Frankie’s summons he looked around, as if to say, “what, me?” but Frankie, delighted at his obvious embarrassment, was having no procrastination, and gestured to him to take Bobby’s place by the door. She went down on one knee to make sure of the best angle.
“Come on, Timmy. Your turn. Good boy. No, not like that – hook your thumbs in your belt like Bobby did. That’s it. That a much cooler pose. Smile, Timmy… Come on now, show how happy you are in your brand new pageboy outfit. That’s right! Hold it…”
Tim’s cheeks were burning as he faced her. His coc-k was as now firm and fat as a bratwurst sausage, standing proud and vertical in his shorts, pressing against his tummy. There was a noticeable narrowing half way up the shaft, marking the position of the latex tether. Every now and then it twitched visibly in response to the relentless vibrations of his butt-plug. But Frankie had no mercy, ordering into a variety of cute poses, enhanced by finger gestures – peace sign, finger to lips (naughty-boy style), hand over mouth (oops! What have I done?), and so on. She even tricked him into one, making him stand with his right thumb hooked into his belt, and then telling him to close all his other fingers except the index finger, leaving him pointing right at that which he most desired to conceal; but he realised just too late!
When she had finished with him, she took a brief time out to scroll through her pictures. Yes, these were going to make her quite a reputation amongst her friends, no doubt about that. She wound up with a few snaps of the boys together, arms in arm, wearing sickly smiles. The boot-cleaning came almost as an afterthought, but she felt the boys had done everything she had asked of them, and they deserved the respite of being on their knees for a few minutes instead of on show.
She looked down at them as they knelt, side-by-side, working on the leather. These were the sort of boys she liked. Sweet, innocent, and easily tamed. The shyness was all theirs; she felt quite at ease around them now, and indeed, the whole session had made her feel a much more confident person. She knew this wouldn’t be her last visit…
As she walked away from the parlour, past a couple of waiting customers, she felt calm and contented. Thinking of the photos on her phone, and the pleasure she would have editing them and showing them off to her friends, there was an uncharacteristically satisfied smile on her face…
Frankie Meering sat in the waiting-room in a state of contained nervous uneasiness. She had never intended to make a visit to the boot parlour. She was an only child, and had been brought up by a single mother with anxiety issues, who had taught her to be wary of everyone, but especially men. As a result she was still as timid as a little mouse in mixed society, and was only really comfortable in the company of her few friends or her horses. But two of those friends, who had already visited, had coaxed and teased her until she felt ashamed of her cowardice, and consented to take the plunge. Having agreed and allowed them to book a session for her, she immediately regretted her decision. But they had made sure she attended, accompanying her to the boot parlour entrance and handing her into Ellie’s custody. Even then, had it not been for Ellie’s detaining her with aimless gossip, at which she excelled, she may well have fled.
She had seen the boys about the Centre in their civvies, and the sight of them brought a flush to her cheeks, and, when on one occasion they passed close by and looked at her, almost gave her a panic attack. Tim especially seemed so tall and masculine that the mere idea of being in his company, especially wearing one of those superhero uniforms she had seen at the show, made her heart flutter with terror.
She waited, trembling, as the clock ticked towards nine. On the dot, the door opened, and the boys appeared - their first appearance before customers as pageboys. She took in the little latex shorts with pink frills, the frilled latex gloves, the Mary Janes, the ribbon chokers – and nearly laughed out loud. Her hand went to her mouth, and she emitted an involuntary snort. The boys, anticipating quite the opposite reaction, stopped in their tracks. Was this the shy, delicate girl Ellie had warned them about? Had there been a change of booking? Why wasn’t she staring in admiration at their amazing cool uniforms?
Bobby took charge.
“Er, good morning, miss. I’m Bobby, and this is Timmy. Boot boys at your service. Please instruct us as to what you require, and we’ll do our best…”
Frankie had quickly recovered her self-control. “Thank you, boys. I must say you look very…smart. Smart, yes.” She was fighting the desire to burst out laughing. So these were the boys she had been frightened of! How could they possibly think…? But it didn’t matter. They believed it, and she wasn’t going to disabuse them. She’d take her cue from them.
“Wow! What amazing uniforms! You look so cool. I’m so glad I came to see you at last.”
The boys looked at each other with satisfied smiles. She must have been taken aback at first. Too much of a shock for her, probably.
Tim immediately went into swaggering mode.
“Glad you like ‘em, miss. Do you like the colour? Cos we got uvvers in the pipeline, like, in different styles and colours.”
“Wherever did you get them?”
“We got our own supplier, see? Big internash’nal company. Make us whatever we want.”
“Really? But I like these ones. I love them, in fact. Can I see…?”
She leant forward. Tim strolled over to give her a better view. She reached out and touched the side of his shorts, then ruffled his frills. She noted with delight the vertical bulge at the front, and the neat separation of his balls. She bit her lip, determined to stay serious.
“They’re so well made… And the fit…”
“All our uniforms are made to measure,” piped up Bobby.
“Gosh, is that a fact?” Frankie leant back again. “Do you only wear them in here? It’s a pity you can’t wear them outside for everyone to see.”
“Well, no, we’re not allowed,” continued Bobby. “I think Miss Poole is worried they might get damaged if we did that…”
“Yeah. They’re ‘spensive, see…very ‘spensive,” boasted Tim.
“But next month,” said Bobby, excitedly, “we have permission to wear them to a big wedding. It’s like a friend of a friend…”
“Gosh, how exciting! You’ll be a big hit, I’m sure…”
There was a short pause, while Frankie looked both of them up and down. She took out her phone.
“Would you mind if…?”
“No, not at all,” said Bobby. “Go ahead.”
“Could I have one of each of you separately, then one with both of you together?”
“Sure.”
“Bobby? Could you stand by the door? Just stand naturally…”
She rose from her chair and stood opposite him. Bobby hooked his thumbs into his belt and grinned. Frankie took a number snaps in various poses, keeping him busy for about five minutes, during which time he became conscious of the increasing intensity of the vibrations deep inside, and the consequent effect on his level of arousal. By the time she was satisfied, the pressure in the front of his shorts was palpable. He blushed slightly, and was relieved to when she called on Tim to take his place.
But Tim was already in a worse state. His plug had been twitching and pulsing all the while Bobby was being photographed, and now, despite his best efforts, his coc-k was quite out of control, and flaunting its length shamelessly as if determined to do its best to reach his belt buckle. At Frankie’s summons he looked around, as if to say, “what, me?” but Frankie, delighted at his obvious embarrassment, was having no procrastination, and gestured to him to take Bobby’s place by the door. She went down on one knee to make sure of the best angle.
“Come on, Timmy. Your turn. Good boy. No, not like that – hook your thumbs in your belt like Bobby did. That’s it. That a much cooler pose. Smile, Timmy… Come on now, show how happy you are in your brand new pageboy outfit. That’s right! Hold it…”
Tim’s cheeks were burning as he faced her. His coc-k was as now firm and fat as a bratwurst sausage, standing proud and vertical in his shorts, pressing against his tummy. There was a noticeable narrowing half way up the shaft, marking the position of the latex tether. Every now and then it twitched visibly in response to the relentless vibrations of his butt-plug. But Frankie had no mercy, ordering into a variety of cute poses, enhanced by finger gestures – peace sign, finger to lips (naughty-boy style), hand over mouth (oops! What have I done?), and so on. She even tricked him into one, making him stand with his right thumb hooked into his belt, and then telling him to close all his other fingers except the index finger, leaving him pointing right at that which he most desired to conceal; but he realised just too late!
When she had finished with him, she took a brief time out to scroll through her pictures. Yes, these were going to make her quite a reputation amongst her friends, no doubt about that. She wound up with a few snaps of the boys together, arms in arm, wearing sickly smiles. The boot-cleaning came almost as an afterthought, but she felt the boys had done everything she had asked of them, and they deserved the respite of being on their knees for a few minutes instead of on show.
She looked down at them as they knelt, side-by-side, working on the leather. These were the sort of boys she liked. Sweet, innocent, and easily tamed. The shyness was all theirs; she felt quite at ease around them now, and indeed, the whole session had made her feel a much more confident person. She knew this wouldn’t be her last visit…
As she walked away from the parlour, past a couple of waiting customers, she felt calm and contented. Thinking of the photos on her phone, and the pleasure she would have editing them and showing them off to her friends, there was an uncharacteristically satisfied smile on her face…
82
Active Sissy Stories / Re: Sissy goes shopping
« Last post by WetPampers on September 09, 2025, 12:27:30 PM »
She congratulated Mrs. MacNab on her visit and asked how dear little Pauline was doing today. Pauline shuddered at the hypocritical and disgusting tone, but politely replied, “I'm doing very well, thank you, ma'am, and you?” The lady smiled and replied, “Very well, thank you, dear,” then, turning to Mrs. MacNab,
“Do you think Pauline would give me a kiss? I consider my clients' children to be a bit like family. I am a caring auntie, selecting their dresses, their underwear, and their punishment equipment. So, in return, I ask each of them for a kiss.”
Mrs. MacNab turned to her son and said, “Would you like to give Madame a big, juicy kiss? After all, we should be grateful to her for having this lovely shop where we can buy your cute things!”
What could poor Pauline do? “Yes, Mom, I'd love to give her a big kiss.” And he held out his face to Madame's wet lips. She grabbed his head with both hands and pressed her mouth against his, inserting her tongue deep between his lips. He hated it, but he knew what he had to do: he suc-ked on Madame's tongue. Pauline was tortured by this breathtaking kiss because, although he hated it in his mind, his masculine nature was attracted to it, and he felt his excitement growing under his diapers.
The lady turned to Mrs. MacNab and said, “Pauline is very well trained; that was a wonderful kiss he gave me. He will be very good entertainment for the ladies. But it is very hot in here; I will take off his coat and cap, and you can both walk around.”
Mrs. MacNab replied, "Yes, Pauline will make a delightful companion for the ladies when I'm done with him. He is being trained to be completely submissive and to provide lesbian services to women who desire a docile and enslaved male. But he will never be allowed to use his jewels in the manner of males. He knows that pleasure is forbidden to him forever. His jewels are there for the sole purpose of being handled by ladies, as is his little hole, for that matter. Yes, please, you may undress Pauline.
Pauline fidgeted and, turning to her mother, begged, “Please let me keep my cape on, Mom, I'm not too hot.” “But Pauline,” said Madame, “it's very hot in here. I'm turning up the temperature because many of the pupils have to undress. Look at those pretty twins, a boy and a girl. They're naked and are going to try on their corsets.”
It was true, on the other side of the living room there were two naked children, a boy and a girl of about fourteen years old and almost indistinguishable, except for their shaved private parts, as they both had long hair, slim waists, and budding breasts. Mrs. MacNab intervened harshly, “Pauline! I won't say it twice! Keep still while Madame takes off your coat.”
Madame removed his cap, undid the buttons of his pea coat, and helped him take it off. The reason why the boy was so agitated and reluctant became obvious. He was wearing an adorable high-waisted baby dress with puffed sleeves that flared out from the waist, held out by a starched petticoat. The dress and petticoat were so short and flared that they revealed the adorable pink rubber panties the boy was wearing.
The pants were obviously lined with voluminous terry cloth diapers. With his long, shaved legs, white ankle socks, and buckled shoes, Pauline was a charming curiosity, and several customers marveled at the delightful sight of this tall boy (soon to be eighteen) who looked so much like a big baby.
The lady asked, “Is there anything special I can do for you?”
“Oh, we'll start by window shopping at this wonderful salon,” said Mrs. MacNab, “then Pauline has a long list of items he needs. I've given him permission to ask for them himself, and I know he's very excited and feels like a grown-up being able to shop on his own!”
“Do as you please, look around the large salon and also in the small special rooms such as the corset room or the rubber room...” said Madame, "and remember that there are no privates allowed for my clients' children and you can observe any of them trying on a garment or an instrument of discipline. Perhaps it would be good to take Pauline to the punishment room to see a child being whipped; it's always a salutary experience! Then, when you're done, I'll take care of you personally. Or better yet, I'll ask Yvonne, my fifteen-year-old assistant, to be at your disposal. Perhaps Pauline will be less intimidated asking a girl his own age, and in this case even younger than him, for his things. It's very thoughtful of you to allow him to ask for what he needs on his own; it helps him gain confidence.
The two women smiled, and Pauline felt her heart beat faster in the face of such falseness and hypocrisy. How could he feel “big” dressed up as a baby like that? And how could his shame at having to ask for the awful things on his list give him confidence? That was the last thing these women wanted to give the boys under their wing. He was going to feel even more foolish having to ask for these childish and intimate items from a girl younger than him. Would there be no end to this life of being a boy-girl reduced to the status of a tiny child?
“Do you think Pauline would give me a kiss? I consider my clients' children to be a bit like family. I am a caring auntie, selecting their dresses, their underwear, and their punishment equipment. So, in return, I ask each of them for a kiss.”
Mrs. MacNab turned to her son and said, “Would you like to give Madame a big, juicy kiss? After all, we should be grateful to her for having this lovely shop where we can buy your cute things!”
What could poor Pauline do? “Yes, Mom, I'd love to give her a big kiss.” And he held out his face to Madame's wet lips. She grabbed his head with both hands and pressed her mouth against his, inserting her tongue deep between his lips. He hated it, but he knew what he had to do: he suc-ked on Madame's tongue. Pauline was tortured by this breathtaking kiss because, although he hated it in his mind, his masculine nature was attracted to it, and he felt his excitement growing under his diapers.
The lady turned to Mrs. MacNab and said, “Pauline is very well trained; that was a wonderful kiss he gave me. He will be very good entertainment for the ladies. But it is very hot in here; I will take off his coat and cap, and you can both walk around.”
Mrs. MacNab replied, "Yes, Pauline will make a delightful companion for the ladies when I'm done with him. He is being trained to be completely submissive and to provide lesbian services to women who desire a docile and enslaved male. But he will never be allowed to use his jewels in the manner of males. He knows that pleasure is forbidden to him forever. His jewels are there for the sole purpose of being handled by ladies, as is his little hole, for that matter. Yes, please, you may undress Pauline.
Pauline fidgeted and, turning to her mother, begged, “Please let me keep my cape on, Mom, I'm not too hot.” “But Pauline,” said Madame, “it's very hot in here. I'm turning up the temperature because many of the pupils have to undress. Look at those pretty twins, a boy and a girl. They're naked and are going to try on their corsets.”
It was true, on the other side of the living room there were two naked children, a boy and a girl of about fourteen years old and almost indistinguishable, except for their shaved private parts, as they both had long hair, slim waists, and budding breasts. Mrs. MacNab intervened harshly, “Pauline! I won't say it twice! Keep still while Madame takes off your coat.”
Madame removed his cap, undid the buttons of his pea coat, and helped him take it off. The reason why the boy was so agitated and reluctant became obvious. He was wearing an adorable high-waisted baby dress with puffed sleeves that flared out from the waist, held out by a starched petticoat. The dress and petticoat were so short and flared that they revealed the adorable pink rubber panties the boy was wearing.
The pants were obviously lined with voluminous terry cloth diapers. With his long, shaved legs, white ankle socks, and buckled shoes, Pauline was a charming curiosity, and several customers marveled at the delightful sight of this tall boy (soon to be eighteen) who looked so much like a big baby.
The lady asked, “Is there anything special I can do for you?”
“Oh, we'll start by window shopping at this wonderful salon,” said Mrs. MacNab, “then Pauline has a long list of items he needs. I've given him permission to ask for them himself, and I know he's very excited and feels like a grown-up being able to shop on his own!”
“Do as you please, look around the large salon and also in the small special rooms such as the corset room or the rubber room...” said Madame, "and remember that there are no privates allowed for my clients' children and you can observe any of them trying on a garment or an instrument of discipline. Perhaps it would be good to take Pauline to the punishment room to see a child being whipped; it's always a salutary experience! Then, when you're done, I'll take care of you personally. Or better yet, I'll ask Yvonne, my fifteen-year-old assistant, to be at your disposal. Perhaps Pauline will be less intimidated asking a girl his own age, and in this case even younger than him, for his things. It's very thoughtful of you to allow him to ask for what he needs on his own; it helps him gain confidence.
The two women smiled, and Pauline felt her heart beat faster in the face of such falseness and hypocrisy. How could he feel “big” dressed up as a baby like that? And how could his shame at having to ask for the awful things on his list give him confidence? That was the last thing these women wanted to give the boys under their wing. He was going to feel even more foolish having to ask for these childish and intimate items from a girl younger than him. Would there be no end to this life of being a boy-girl reduced to the status of a tiny child?
83
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 09, 2025, 03:18:36 AM »
Chapter 240.
It was an unconventional relationship, but as none of them had ever experienced a “conventional” one – if such a thing can be said to exist – it troubled them not in the least. That night May and Jasmine shared one bed And Bobby and Tim the other, for no other reason than that the girls had to be at work by six-thirty on a Monday. By the time the boys woke they were gone.
Ellie ran into them on her way to the boys’ apartment, and received a brief account of events the previous evening, illustrated by a glimpse of the video. There was a smile on her face as she laid their pageboy uniforms out and called to them to rise.
“Eight o’clock, boys! One hour to get ready and have breakfast.
“Whose first…?” came a sleepy voice from within.
“Let me see… Ah…Frankie Meering. Do you know her?”
“Don’t think so…”
“She’s a sweet girl. Rather shy. Quite surprised she turned up, actually – especially by herself. Two of her friends – they saw you guys in the first week – have been trying to persuade her to book a session. Be nice to her, won’t you?”
Despite this apparently well-meaning advice, the mischievous Ellie had decided Frankie deserved a little treat to reward her for taking the plunge, and she had set the vibes to mark three again. “That should easily set her blushing,” she said to herself, with a smile. She delayed getting the boys into their uniforms till the last minute, pretending to have forgotten to charge their butt-plugs.
“Good news, Tim,” whispered Bobby. “Looks like we may have a quiet time of it today.”
Tim frowned. “It ain’t like her to forget somethink like that…” he said, suspiciously.
“Oh, she’s here, boys. In the waiting room. Let me give you one more check over… Yes, you look great! Lucky Frankie. She’ll be the first to see you in your pageboy outfits. Right, off you go. I have to go see Miss Poole. Remember what I said. Be very polite and well-behaved, won’t you?”
“We always are,” remarked Bobby. “It’s the customers that…”
But Ellie was gone.
Miss Poole relied on Ellie for reports on the boys’ conduct. Monday mornings were a good time for her to get updated with the latest intelligence. Ellie knocked, and Miss Poole called her in at once.
“Ellie, thank you for coming. Just give me a moment, would you? I’ve just asked to be connected to Deborah Cresswell about her wedding.”
A moment later the phone on her desk rang. “Ah, hello? Is that Deborah? Good morning. This is Violet Poole from Pitt’s Wood Equestrian Centre. Yes… Bobby… That’s right. Yes, he’s now our permanent resident boot boy. Yes, very exciting! Now I wanted to ask you, have you seen the photos I emailed of Bobby and his friend Timmy? You have? What do you…? You do? Really? Both of them? They’ll be so happy! Bobby’s so looking forward to showing off his pageboy outfit, and Timmy’s been so jealous! I know. I know! Isn’t it wonderful? Did you see the specs of their outfits from Fantastex? No, they really do. It is a little teeny bit naughty, of course but… Oh, I’m so glad you approve! Yes, I know. They can be… Yes, quite dull. But a little bit of spice… I can see we’re on the same page. Now, I have to ask… The boys have a supervisor. She’s very nice, and very smart, in both senses of the word. Oh, she can? And she mentioned two attendants. Really? She’ll be so pleased… Excellent, yes… Now I wanted to ask… Please say no if I’m overstepping the mark… Apart from the in-house service, we are now offering home visits. They can not only attend to footwear, but any domestic duties. Sorry? Well of course I’m using the term in its widest… Oh, yes…absolutely anything. Parties? Of course. Well the thing is, Deborah, we are printing flyers in the hope we can reach a wider… I can? Oh, that’s so good of you! No, I’m sure some of your guests will be interested… And of course, I’ll give you vouchers in case you decide you’d like to visit…or be visited… No, no problem. Only too happy… You’ve been so kind…. Yes, well, we’ll speak again soon, Thank you again. Yes, let’s. Bye, Deborah!”
Miss Poole smiled. She loves them.. They’re both welcome, as are you, and your two friends. Now, Ellie… Any updates?”
“Thank you, miss. May and Jessica will be pleased. Especially since they found out some things about the boys last night.”
“Oh, really? Like what exactly?”
“Like Tim has a terrible crush on Bobby, and wishes he was a girl. And Bobby would like to be a girl – or at least, he’d like to wear girls’ clothes. And he will do pretty much anything to please Timmy. And May and Jessica have the pair of them eating out of their hands…”
“Goodness, stop right there, Ellie. That’s enough for me to take in a one sitting. So your surmise was correct. We have a pair of potential, dare I say it - sissy-boys…on our hands.”
“Seems so, miss.”
“I was hoping that would be the case. I wish all boys of that age could have at least an element of…shall we say, feminine softness? And how are the new uniforms?”
“Oh, amazing, Miss Poole. Those little plugs are so effective…”
“Hmm. Excellent. Cynthia’s come up trumps again. Remember to turn them on for the wedding, won’t you? We want the boys to put on a good display…”
“Of course, miss. And for the time being May and Jessica are going to continue their, er, education. I’ll report any developments.”
“Thank you, Ellie. You can always email me if there’s anything you would like me to know urgently. And attach any visual evidence at you discretion…”
“Yes, Miss Poole – absolutely.”
“And I must tell Diana and Eleanor what you’ve just told me. They have another session on Wednesday – don’t give the boys any forewarning, will you? They also spotted a certain, ah, empathy between them, and I think they said they might push things a little further this time…”
It was an unconventional relationship, but as none of them had ever experienced a “conventional” one – if such a thing can be said to exist – it troubled them not in the least. That night May and Jasmine shared one bed And Bobby and Tim the other, for no other reason than that the girls had to be at work by six-thirty on a Monday. By the time the boys woke they were gone.
Ellie ran into them on her way to the boys’ apartment, and received a brief account of events the previous evening, illustrated by a glimpse of the video. There was a smile on her face as she laid their pageboy uniforms out and called to them to rise.
“Eight o’clock, boys! One hour to get ready and have breakfast.
“Whose first…?” came a sleepy voice from within.
“Let me see… Ah…Frankie Meering. Do you know her?”
“Don’t think so…”
“She’s a sweet girl. Rather shy. Quite surprised she turned up, actually – especially by herself. Two of her friends – they saw you guys in the first week – have been trying to persuade her to book a session. Be nice to her, won’t you?”
Despite this apparently well-meaning advice, the mischievous Ellie had decided Frankie deserved a little treat to reward her for taking the plunge, and she had set the vibes to mark three again. “That should easily set her blushing,” she said to herself, with a smile. She delayed getting the boys into their uniforms till the last minute, pretending to have forgotten to charge their butt-plugs.
“Good news, Tim,” whispered Bobby. “Looks like we may have a quiet time of it today.”
Tim frowned. “It ain’t like her to forget somethink like that…” he said, suspiciously.
“Oh, she’s here, boys. In the waiting room. Let me give you one more check over… Yes, you look great! Lucky Frankie. She’ll be the first to see you in your pageboy outfits. Right, off you go. I have to go see Miss Poole. Remember what I said. Be very polite and well-behaved, won’t you?”
“We always are,” remarked Bobby. “It’s the customers that…”
But Ellie was gone.
Miss Poole relied on Ellie for reports on the boys’ conduct. Monday mornings were a good time for her to get updated with the latest intelligence. Ellie knocked, and Miss Poole called her in at once.
“Ellie, thank you for coming. Just give me a moment, would you? I’ve just asked to be connected to Deborah Cresswell about her wedding.”
A moment later the phone on her desk rang. “Ah, hello? Is that Deborah? Good morning. This is Violet Poole from Pitt’s Wood Equestrian Centre. Yes… Bobby… That’s right. Yes, he’s now our permanent resident boot boy. Yes, very exciting! Now I wanted to ask you, have you seen the photos I emailed of Bobby and his friend Timmy? You have? What do you…? You do? Really? Both of them? They’ll be so happy! Bobby’s so looking forward to showing off his pageboy outfit, and Timmy’s been so jealous! I know. I know! Isn’t it wonderful? Did you see the specs of their outfits from Fantastex? No, they really do. It is a little teeny bit naughty, of course but… Oh, I’m so glad you approve! Yes, I know. They can be… Yes, quite dull. But a little bit of spice… I can see we’re on the same page. Now, I have to ask… The boys have a supervisor. She’s very nice, and very smart, in both senses of the word. Oh, she can? And she mentioned two attendants. Really? She’ll be so pleased… Excellent, yes… Now I wanted to ask… Please say no if I’m overstepping the mark… Apart from the in-house service, we are now offering home visits. They can not only attend to footwear, but any domestic duties. Sorry? Well of course I’m using the term in its widest… Oh, yes…absolutely anything. Parties? Of course. Well the thing is, Deborah, we are printing flyers in the hope we can reach a wider… I can? Oh, that’s so good of you! No, I’m sure some of your guests will be interested… And of course, I’ll give you vouchers in case you decide you’d like to visit…or be visited… No, no problem. Only too happy… You’ve been so kind…. Yes, well, we’ll speak again soon, Thank you again. Yes, let’s. Bye, Deborah!”
Miss Poole smiled. She loves them.. They’re both welcome, as are you, and your two friends. Now, Ellie… Any updates?”
“Thank you, miss. May and Jessica will be pleased. Especially since they found out some things about the boys last night.”
“Oh, really? Like what exactly?”
“Like Tim has a terrible crush on Bobby, and wishes he was a girl. And Bobby would like to be a girl – or at least, he’d like to wear girls’ clothes. And he will do pretty much anything to please Timmy. And May and Jessica have the pair of them eating out of their hands…”
“Goodness, stop right there, Ellie. That’s enough for me to take in a one sitting. So your surmise was correct. We have a pair of potential, dare I say it - sissy-boys…on our hands.”
“Seems so, miss.”
“I was hoping that would be the case. I wish all boys of that age could have at least an element of…shall we say, feminine softness? And how are the new uniforms?”
“Oh, amazing, Miss Poole. Those little plugs are so effective…”
“Hmm. Excellent. Cynthia’s come up trumps again. Remember to turn them on for the wedding, won’t you? We want the boys to put on a good display…”
“Of course, miss. And for the time being May and Jessica are going to continue their, er, education. I’ll report any developments.”
“Thank you, Ellie. You can always email me if there’s anything you would like me to know urgently. And attach any visual evidence at you discretion…”
“Yes, Miss Poole – absolutely.”
“And I must tell Diana and Eleanor what you’ve just told me. They have another session on Wednesday – don’t give the boys any forewarning, will you? They also spotted a certain, ah, empathy between them, and I think they said they might push things a little further this time…”
84
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 09, 2025, 03:09:00 AM »
Chapter 239.
As their spasms gradually subsided and their bodies relaxed, they sank back on the sofa. Bobby’s head slowly tilted sideways till it was resting on Tim’s shoulder. Their erections were softening slowly, and from the tip of each condom hung a spherical teat heavy with c-um. The girls left them for a minute or two, then carefully removed the each one, pinching the end above the teat to conserve as much as possible while stretching open the lip and gently pulling it off. Giggling, they held them up to compare.
“Not much in it,” remarked May, in an undertone. “Bobby I think. He may have lost the size competition, but he made up for it in quantity.”
“What are we going to do with these?” whispered Jessica.
The both looked at the inviting round lips in front of them, and smiled.
“It’s too good to waste,” whispered May back.
Jessica raised her voice again. “Boys? Stay where you are and don’t move. You deserve a treat after that.”
She pulled out the mouth plugs and hooked the rings over her little finger. Jessica was about to feed Tim his own c-um, but May raised her finger. She held out Bobby’s full condom and winked. Jessica grinned. Without a word, they exchanged condoms. They pushed the lips into the boy’s mouth holes, poking them in with their fingers, then, holding the teats up, used thumbs and forefingers to inject the contents into their mouths. Then they pulled out the condoms, Jessica passed May one of the plugs, and they popped them in.
“Hands down, Bobby!”
The boys sat there obediently, presumably enjoying their little treats. The girls shook hands silently, then made the boys decent and refastened their shorts.
“Was it nice, boys?” teased Jessica. “It’s good for you, too.”
The blank pink latex hoods betrayed no hint of emotion. They looked so comic with their little plugged red lips, as if they were pouting for a pretend kiss. Bobby hands lay helpless by his sides. Tim was clinging to the frills on Bobby’s shorts with one hand, the other in his lap.
“They look so sweet now,” whispered May. “What cute little sissies! But that was some performance.”
“I think the hoods helped,” replied Jessica, quietly. “I think they help them lose their inhibitions. If so, it gives us lots of options.”
“Yes, but let’s take our time.”
“Totally,” agreed Jessica. She looked down at May’s phone. “We should finish the video…”
“Oh, yes. Stay where you are boys, and we’ll take off your hoods.”
The girls went round behind the sofa. “Open wide,” said May, for the second time. They worked the tunnel gags out of their mouths, then simultaneously stretched the fronts of the hoods out and rolled them up off their heads. The boys sat there blinking in the light. May moved in front of the phone so they wouldn’t see it, stopped the video, and slipped in into her pocket.
The boys were allowed to change into their casual clothes for the rest of the evening. When they emerged from their rooms they were very sheepish, unable to look at each other or the girls. Jessica and May had to coax them back to normality, to their usual confident, sociable selves. May fetched a ten-pack of beers from the fridge.
“Come on, guys, sit down and let’s have a drink. Are you okay? We didn’t mean to hurt your feelings or anything…”
“Oh, no, it’s nothing like that…” began Bobby, happy to see the girls weren’t going to make fun of them. “It’s just…” he glanced at Tim. Tim glanced back. “Well, it was kind of…funny…”
“Look, guys,” said Jessica. “How can I explain? We’d really like to be your girlfriends…” May nodded. “We really like your company. You’re good fun. But, well, to be honest, it would never be a “typical” boyfriend-girlfriend relationship. Cos you know we have our own bond…”
“Yeah, we totally get it,” blurted Tim, “but we don’t care about all that. We really like you bofe – don’t we mate?” It was Bobby’s turn to nod. “See we ain’t ever ‘ad no girlfriends before, so we don’t ‘ave no expectations…”
“We like you partly because of that,” said May. “Neither of you pretends to be tough or macho – but actually you’re very brave and strong. You’re confident enough to do this job, to wear whatever uniforms Miss Poole decides to give you. What blokes would be tough enough to do that? None that I know. But we can’t do all the traditional sex stuff. We like to be a bit adventurous. And I can see you do too. It makes us feel good about ourselves when we see you accepting your own feelings for each other. See, we don’t need constant emotional reassurance like a lot of girls. We’re not going to play emotional games, we’re not going to stop liking you on a whim, we’re not going to look at other guys – though we may occasionally glance at another girl! – we’re not going to disapprove of anything you do. Provided you acknowledge your own feelings, as we do ours.”
“Yes,” added Jessica, “and sexually all we want to do is to give you a good time, whilst enjoying ourselves. So far we’ve only scratched the surface. So if you decided to stay with us, we can at least promise you some fun. I think this evening we started uncovering some rather interesting things about you two…”
Tim and Bobby blushed, and giggled like a pair of shy girls.
“And it was a fantastic turn-on for us. So that’s one of the things we want to explore further.”
“Yeah. A lot further,” said May, taking another swig of beer. ‘Specially when Bobby’s got his new dress. What was it, Tim? Blue satin with pink latex panties? You naughty boy!”
Tim hid his face in his hands. Bobby grinned.
“I’d really like one like that,” he said, giving Tim a poke in the ribs.
As their spasms gradually subsided and their bodies relaxed, they sank back on the sofa. Bobby’s head slowly tilted sideways till it was resting on Tim’s shoulder. Their erections were softening slowly, and from the tip of each condom hung a spherical teat heavy with c-um. The girls left them for a minute or two, then carefully removed the each one, pinching the end above the teat to conserve as much as possible while stretching open the lip and gently pulling it off. Giggling, they held them up to compare.
“Not much in it,” remarked May, in an undertone. “Bobby I think. He may have lost the size competition, but he made up for it in quantity.”
“What are we going to do with these?” whispered Jessica.
The both looked at the inviting round lips in front of them, and smiled.
“It’s too good to waste,” whispered May back.
Jessica raised her voice again. “Boys? Stay where you are and don’t move. You deserve a treat after that.”
She pulled out the mouth plugs and hooked the rings over her little finger. Jessica was about to feed Tim his own c-um, but May raised her finger. She held out Bobby’s full condom and winked. Jessica grinned. Without a word, they exchanged condoms. They pushed the lips into the boy’s mouth holes, poking them in with their fingers, then, holding the teats up, used thumbs and forefingers to inject the contents into their mouths. Then they pulled out the condoms, Jessica passed May one of the plugs, and they popped them in.
“Hands down, Bobby!”
The boys sat there obediently, presumably enjoying their little treats. The girls shook hands silently, then made the boys decent and refastened their shorts.
“Was it nice, boys?” teased Jessica. “It’s good for you, too.”
The blank pink latex hoods betrayed no hint of emotion. They looked so comic with their little plugged red lips, as if they were pouting for a pretend kiss. Bobby hands lay helpless by his sides. Tim was clinging to the frills on Bobby’s shorts with one hand, the other in his lap.
“They look so sweet now,” whispered May. “What cute little sissies! But that was some performance.”
“I think the hoods helped,” replied Jessica, quietly. “I think they help them lose their inhibitions. If so, it gives us lots of options.”
“Yes, but let’s take our time.”
“Totally,” agreed Jessica. She looked down at May’s phone. “We should finish the video…”
“Oh, yes. Stay where you are boys, and we’ll take off your hoods.”
The girls went round behind the sofa. “Open wide,” said May, for the second time. They worked the tunnel gags out of their mouths, then simultaneously stretched the fronts of the hoods out and rolled them up off their heads. The boys sat there blinking in the light. May moved in front of the phone so they wouldn’t see it, stopped the video, and slipped in into her pocket.
The boys were allowed to change into their casual clothes for the rest of the evening. When they emerged from their rooms they were very sheepish, unable to look at each other or the girls. Jessica and May had to coax them back to normality, to their usual confident, sociable selves. May fetched a ten-pack of beers from the fridge.
“Come on, guys, sit down and let’s have a drink. Are you okay? We didn’t mean to hurt your feelings or anything…”
“Oh, no, it’s nothing like that…” began Bobby, happy to see the girls weren’t going to make fun of them. “It’s just…” he glanced at Tim. Tim glanced back. “Well, it was kind of…funny…”
“Look, guys,” said Jessica. “How can I explain? We’d really like to be your girlfriends…” May nodded. “We really like your company. You’re good fun. But, well, to be honest, it would never be a “typical” boyfriend-girlfriend relationship. Cos you know we have our own bond…”
“Yeah, we totally get it,” blurted Tim, “but we don’t care about all that. We really like you bofe – don’t we mate?” It was Bobby’s turn to nod. “See we ain’t ever ‘ad no girlfriends before, so we don’t ‘ave no expectations…”
“We like you partly because of that,” said May. “Neither of you pretends to be tough or macho – but actually you’re very brave and strong. You’re confident enough to do this job, to wear whatever uniforms Miss Poole decides to give you. What blokes would be tough enough to do that? None that I know. But we can’t do all the traditional sex stuff. We like to be a bit adventurous. And I can see you do too. It makes us feel good about ourselves when we see you accepting your own feelings for each other. See, we don’t need constant emotional reassurance like a lot of girls. We’re not going to play emotional games, we’re not going to stop liking you on a whim, we’re not going to look at other guys – though we may occasionally glance at another girl! – we’re not going to disapprove of anything you do. Provided you acknowledge your own feelings, as we do ours.”
“Yes,” added Jessica, “and sexually all we want to do is to give you a good time, whilst enjoying ourselves. So far we’ve only scratched the surface. So if you decided to stay with us, we can at least promise you some fun. I think this evening we started uncovering some rather interesting things about you two…”
Tim and Bobby blushed, and giggled like a pair of shy girls.
“And it was a fantastic turn-on for us. So that’s one of the things we want to explore further.”
“Yeah. A lot further,” said May, taking another swig of beer. ‘Specially when Bobby’s got his new dress. What was it, Tim? Blue satin with pink latex panties? You naughty boy!”
Tim hid his face in his hands. Bobby grinned.
“I’d really like one like that,” he said, giving Tim a poke in the ribs.
85
Active Sissy Stories / Re: Proof of Intent
« Last post by antonia on September 06, 2025, 05:20:59 AM »
Chapter 9
James woke up feeling sore, he had a bad case of nappy rash beginning, not helped at all by the excessive rubbing to the front of his nappy on the previous day. His nappy was soaked, his bib wet from a night of drooling as he nursed on his dummy. His hand clutched tightly to the woollen shawl which he had caressed to his face and luxuriated in the fragrance the entire night.
The continual subliminal messaging had him unperturbed by the thought that he had wet his nappies during the night. He knew that his (do di) dummy and his (shoo-shoo) baby shawl were a vital part of his life and he would be very nervous if they were to leave his sight.
Lisa came in with a warm bottle of milk which he grabbed hungrily and began to suc-k vigorously on the bottle teat. As he enjoyed his bottle, she removed his wet and rather odorous nappy and threw it in the wet nappy bucket. In no time at all she had him in the bath and enjoying a happy time splashing and laughing as he played with a few bright yellow plastic ducks. She pulled the reluctant boyfriend out of the bath and carefully dried him off.
The special cream was applied generously to his little sissy stick which she could have sworn was already looking smaller that it had the day before. A heavy layer of zinc and castor oil cream was applied to his nappy area, with particular attention to the areas where small pimples were erupting in patches of redness where nappy rash was beginning to appear. The coolness of the cream induced a tumescence into his little member and Lisa smiles at how the erection was speeding up his downfall as the drugs were absorbed into his blood stream.
She decided not to use his plastic pants in an attempt to allow some air to get to his skin. She laid him in his cot on top of three night time nappies and loosely pinned two regular nappies around him to allow his skin to recover. James wanted to get out and was not cooperating, so Lisa put him in a fresh little smocked night dress and then put him in his reins, which she attached firmly to the restraining rings on the cot. Now he was lying on his back and unable to sit up or do anything other than stare at the ceiling. She picked up his unfinished bottle and he resumed his feed. He was asleep in ten minutes, legs wide apart, shawl against his ear and his bottle hanging out the side of his mouth.
The door bell rang and Lisa ran down to greet her new guest. A very smart tall girl stood before her dressed in the traditional Norland nanny uniform which was a pale grey/beige. Her hair was tied neatly into a bun leaving her features looking a little severe. She was dark haired with a gently tanned complexion and she was tall and slender. She looked athletic, here muscles were well developed and she clearly looked after herself, as well as she cared for her little charges. She paid her taxi driver, who had lined her suit cases in a row on the doorstep.
“Caroline Fortiscue” she announced with a clear diction of a lady who had been well educated and came from a very good family “I am here to be the nanny to James”
“Wonderful” enthused Lisa who was looking quite flushed and radiant from her dash to the door “I am so pleased you have decided to join me. James is in his nursery, he has had his wet nappy removed, been given a bath and put in a clean nappy, fed his bottle and is now having a nap. Let me help you to your room.”
Lisa took one of the cases and Caroline easily picked up the other two. The went up to the nursery and opened the adjoining door. Caroline’s new room was bright and airy, it had a comfortable double bed topped with a patchwork quilt. The bedside table had a baby monitor on its top which showed a green light. The sound of James suc-king on his dummy could be heard clearly.
In the room were ample fitted wardrobes, in the middle of which was the door that led in to the nursery. On the wall with the window was a small table that had two large packets of unopened terry towelling nappies, a pile of bibs in their cellophane wrappers, plastic pants of various colours, styles and sizes in plastic bags and several different coloured dummies also in their original packaging.
They dropped the cases and went through to the nursery. “He has nappy rash” confessed Lisa “so I am trying not to use his plastic nappy covers this morning. Good grief, I changed his nappy just ten minutes ago and he has wet himself already” she whispered with a slight giggle.
James was sound asleep, the nappies covering him were clearly yellowed by his wetting, but he was blissfully unaware as he suc-ked on his dummy. His freshly washed hair shone in the sunlight that came through the nursery window, his pink bonnet was hung over the corner post of his crib ready for use later.
Caroline explored the nursery, approving of the kitchenette and nappy changing facilities, and at the thought that had been paid to the storage of his babyish supplies and clothes. She wandered over to a door on the other side of the nursery and peeked inside. It was a sluice for dirty nappies and had a specially designed bathing area for a large baby. It was clear from the wet towels and disorder, that it had been used recently.
“Look, you get settled in and unpack your things and we will have a meeting this afternoon, once the other staff have arrived and are on board. I would be grateful if you could change the little one when he wakes up. I bet he will be thrilled to know that he now has a nanny!” said Lisa
James woke up feeling sore, he had a bad case of nappy rash beginning, not helped at all by the excessive rubbing to the front of his nappy on the previous day. His nappy was soaked, his bib wet from a night of drooling as he nursed on his dummy. His hand clutched tightly to the woollen shawl which he had caressed to his face and luxuriated in the fragrance the entire night.
The continual subliminal messaging had him unperturbed by the thought that he had wet his nappies during the night. He knew that his (do di) dummy and his (shoo-shoo) baby shawl were a vital part of his life and he would be very nervous if they were to leave his sight.
Lisa came in with a warm bottle of milk which he grabbed hungrily and began to suc-k vigorously on the bottle teat. As he enjoyed his bottle, she removed his wet and rather odorous nappy and threw it in the wet nappy bucket. In no time at all she had him in the bath and enjoying a happy time splashing and laughing as he played with a few bright yellow plastic ducks. She pulled the reluctant boyfriend out of the bath and carefully dried him off.
The special cream was applied generously to his little sissy stick which she could have sworn was already looking smaller that it had the day before. A heavy layer of zinc and castor oil cream was applied to his nappy area, with particular attention to the areas where small pimples were erupting in patches of redness where nappy rash was beginning to appear. The coolness of the cream induced a tumescence into his little member and Lisa smiles at how the erection was speeding up his downfall as the drugs were absorbed into his blood stream.
She decided not to use his plastic pants in an attempt to allow some air to get to his skin. She laid him in his cot on top of three night time nappies and loosely pinned two regular nappies around him to allow his skin to recover. James wanted to get out and was not cooperating, so Lisa put him in a fresh little smocked night dress and then put him in his reins, which she attached firmly to the restraining rings on the cot. Now he was lying on his back and unable to sit up or do anything other than stare at the ceiling. She picked up his unfinished bottle and he resumed his feed. He was asleep in ten minutes, legs wide apart, shawl against his ear and his bottle hanging out the side of his mouth.
The door bell rang and Lisa ran down to greet her new guest. A very smart tall girl stood before her dressed in the traditional Norland nanny uniform which was a pale grey/beige. Her hair was tied neatly into a bun leaving her features looking a little severe. She was dark haired with a gently tanned complexion and she was tall and slender. She looked athletic, here muscles were well developed and she clearly looked after herself, as well as she cared for her little charges. She paid her taxi driver, who had lined her suit cases in a row on the doorstep.
“Caroline Fortiscue” she announced with a clear diction of a lady who had been well educated and came from a very good family “I am here to be the nanny to James”
“Wonderful” enthused Lisa who was looking quite flushed and radiant from her dash to the door “I am so pleased you have decided to join me. James is in his nursery, he has had his wet nappy removed, been given a bath and put in a clean nappy, fed his bottle and is now having a nap. Let me help you to your room.”
Lisa took one of the cases and Caroline easily picked up the other two. The went up to the nursery and opened the adjoining door. Caroline’s new room was bright and airy, it had a comfortable double bed topped with a patchwork quilt. The bedside table had a baby monitor on its top which showed a green light. The sound of James suc-king on his dummy could be heard clearly.
In the room were ample fitted wardrobes, in the middle of which was the door that led in to the nursery. On the wall with the window was a small table that had two large packets of unopened terry towelling nappies, a pile of bibs in their cellophane wrappers, plastic pants of various colours, styles and sizes in plastic bags and several different coloured dummies also in their original packaging.
They dropped the cases and went through to the nursery. “He has nappy rash” confessed Lisa “so I am trying not to use his plastic nappy covers this morning. Good grief, I changed his nappy just ten minutes ago and he has wet himself already” she whispered with a slight giggle.
James was sound asleep, the nappies covering him were clearly yellowed by his wetting, but he was blissfully unaware as he suc-ked on his dummy. His freshly washed hair shone in the sunlight that came through the nursery window, his pink bonnet was hung over the corner post of his crib ready for use later.
Caroline explored the nursery, approving of the kitchenette and nappy changing facilities, and at the thought that had been paid to the storage of his babyish supplies and clothes. She wandered over to a door on the other side of the nursery and peeked inside. It was a sluice for dirty nappies and had a specially designed bathing area for a large baby. It was clear from the wet towels and disorder, that it had been used recently.
“Look, you get settled in and unpack your things and we will have a meeting this afternoon, once the other staff have arrived and are on board. I would be grateful if you could change the little one when he wakes up. I bet he will be thrilled to know that he now has a nanny!” said Lisa
86
Active Sissy Stories / Re: Proof of Intent
« Last post by sweet baby katie on September 04, 2025, 09:56:36 AM »
Pleased to see that you are back. you have always been one of my most favorite authors. The story is perfect. Perhaps the near future will see increasing sissyfication: some cute baby dresses and rumba panties, breastfeeding, playpen time? In any event, Whatever direction your muse takes this will be fine.
87
Active Sissy Stories / Re: Proof of Intent
« Last post by sissytrilly on September 04, 2025, 05:28:17 AM »
I love it when a sissy associates a full diaper with arousal. Hope for more soonish!
88
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 03, 2025, 04:32:23 PM »
Chapter 238.
Ordering the boys to stay put, Jessica and May went out into the corridor for a moment. They had a whispered conversation.
“We were right, Jessica.”
“They’re like a pair of shy lovers. Bobby’s definitely into dresses, and Tim’s into Bobby in dresses! They’re a perfect match!”
“We can’t leave them like that. Let’s give them some relief at least.”
“I’m going to get a couple of hoods. I have an idea.”
“Oh, yeah. They might find that easier…”
May returned to the room, while Jessica went to find the hoods. The boys looked at her nervously, awaiting instructions. She obliged.
“Bobby, come and sit next to Tim on the sofa. That’s right. Here, let me take the pressure off a little.”
She popped open Bobby’s fly, allowing his erection to jump out. She had to suppress a smile, seeing them side by side, red-faced, with their little stiff coc-ks standing proud and straight in their red latex sheaths. She couldn’t resist a photo.
“Smile, boys… Hands by your sides please…”
They looked up at her, not with smiles but big frightened doe eyes.
“Okay…that’ll do.”
Jessica returned, clutching two pink latex hoods. She smiled to see the boys side-by-side.
“Oh, that’s better. Togetherness. Let me take a quick snap. Hold hands, now…”
The boys erections were as hard as ever. Occasionally they would twitch or quiver. Clearly the accessories were doing their work well.
“W-what have you got there…?” asked Bobby, seeing the pink latex in her hand.
“These are little hoods, boys. Lovely soft, fine latex. Now…”
“Why…?” began Tim.
“Shush. I’m about to tell you. These are designed to be worn with your uniforms, if you want to remain anonymous, or even if you’re just feeling a bit self-conscious. We’re going to make you both feel better in a minute, and they’ll help you relax while we do so. So lower your heads a bit and let’s get them on.”
Jessica had chosen the hoods without eyeholes, and little circular red rubber lips, the hole little more than an inch and a half in diameter, fitted with a pink rubber plug on a steel ring, like a sink-plug. In the absence of any other features the mouth gave the wearer a comical, slightly surprised expression. Cynthia had thoughtfully had them marked “B” and “T” in small red letters on the forehead, so they couldn’t get mixed up. They were different from Bobby’s open-mouth hood, because welded to the inside of the mouth was a short tunnel-gag with a stiff rubber flange which fitted behind the wearer’s teeth. There was a band of reinforcement around the hood at the level of the mouth, making sure the gag was held firmly in place and couldn’t be expelled.
“Open your mouths wide, please,” ordered May. And with a slight effort they pushed in the gags, and rolled down the necks of the hoods until they snapped firmly in place. The girls adjusted and smoothed the latex until there were no wrinkles, and sat back to admire their new companions, like a pair of alien beings, with smooth, oval pink heads, blank and featureless save for the round plugged mouths. Apart from some muffled indignant noises, all was silence.
“Good. I think we’re ready, don’t you, May?”
“Yes.” She raised her voice a little, to check whether the boys could hear through the thinner latex that covered their ears. “Boys, can you hear us? Nod if you can.”
The heads nodded.
“Excellent.”
The girls seated themselves on the coffee table, May in front of Bobby and Jessica in front of Tim. May put her phone camera on video and placed it between her and Jessica. They took hold of the boys’ erections.
“They’re so hard…” mouthed May silently, screwing up her face in delight. Jessica responded with a peace sign.
“Now, where were we?” she said, out loud. “Ah, yes. We’d settled on pink latex panties, hadn’t we. A little short blue satin dress with crinolines and a big bow at the waist, puff sleeves, white hold-up stockings… Shall we say blue Mary Janes, and Bobby’s hair in bunches with blue ribbons?”
Tim’s bloated coc-k quivered in her hand. She gave it a gentle encouraging squeeze.
“That seems agreeable. Keep holding hands, boys. Now, makeup. Bobby will need a little subtle makeup to make him the perfect girl. I’m going to suggest a touch of blue eye shadow, a little mascara – he’s already got lovely long lashes – er, I think a touch of blusher, and pink lip gloss – to match the panties you chose, Tim. Tim…? Oh my goodness…”
He had suddenly tensed, his head jerked back, and he gave a muffled sob. The coc-k in her fingers reared, and then it was pumping violently, the big teat inflating as it filled with c-um. His body shuddered with the force of his climax. Bobby, close beside him, felt every spasm, which was all he needed to set him off as well, and the next second the two of them, holding hands tight, were jerking and grunting in unison! Things had turned out even better than the girls could have hoped. They exchanged delighted glances, each diligently milking her own spurting coc-k, intent on prolonging the boys’ orgasms as long as possible, and making sure they were drained of every last possible drop.
Ordering the boys to stay put, Jessica and May went out into the corridor for a moment. They had a whispered conversation.
“We were right, Jessica.”
“They’re like a pair of shy lovers. Bobby’s definitely into dresses, and Tim’s into Bobby in dresses! They’re a perfect match!”
“We can’t leave them like that. Let’s give them some relief at least.”
“I’m going to get a couple of hoods. I have an idea.”
“Oh, yeah. They might find that easier…”
May returned to the room, while Jessica went to find the hoods. The boys looked at her nervously, awaiting instructions. She obliged.
“Bobby, come and sit next to Tim on the sofa. That’s right. Here, let me take the pressure off a little.”
She popped open Bobby’s fly, allowing his erection to jump out. She had to suppress a smile, seeing them side by side, red-faced, with their little stiff coc-ks standing proud and straight in their red latex sheaths. She couldn’t resist a photo.
“Smile, boys… Hands by your sides please…”
They looked up at her, not with smiles but big frightened doe eyes.
“Okay…that’ll do.”
Jessica returned, clutching two pink latex hoods. She smiled to see the boys side-by-side.
“Oh, that’s better. Togetherness. Let me take a quick snap. Hold hands, now…”
The boys erections were as hard as ever. Occasionally they would twitch or quiver. Clearly the accessories were doing their work well.
“W-what have you got there…?” asked Bobby, seeing the pink latex in her hand.
“These are little hoods, boys. Lovely soft, fine latex. Now…”
“Why…?” began Tim.
“Shush. I’m about to tell you. These are designed to be worn with your uniforms, if you want to remain anonymous, or even if you’re just feeling a bit self-conscious. We’re going to make you both feel better in a minute, and they’ll help you relax while we do so. So lower your heads a bit and let’s get them on.”
Jessica had chosen the hoods without eyeholes, and little circular red rubber lips, the hole little more than an inch and a half in diameter, fitted with a pink rubber plug on a steel ring, like a sink-plug. In the absence of any other features the mouth gave the wearer a comical, slightly surprised expression. Cynthia had thoughtfully had them marked “B” and “T” in small red letters on the forehead, so they couldn’t get mixed up. They were different from Bobby’s open-mouth hood, because welded to the inside of the mouth was a short tunnel-gag with a stiff rubber flange which fitted behind the wearer’s teeth. There was a band of reinforcement around the hood at the level of the mouth, making sure the gag was held firmly in place and couldn’t be expelled.
“Open your mouths wide, please,” ordered May. And with a slight effort they pushed in the gags, and rolled down the necks of the hoods until they snapped firmly in place. The girls adjusted and smoothed the latex until there were no wrinkles, and sat back to admire their new companions, like a pair of alien beings, with smooth, oval pink heads, blank and featureless save for the round plugged mouths. Apart from some muffled indignant noises, all was silence.
“Good. I think we’re ready, don’t you, May?”
“Yes.” She raised her voice a little, to check whether the boys could hear through the thinner latex that covered their ears. “Boys, can you hear us? Nod if you can.”
The heads nodded.
“Excellent.”
The girls seated themselves on the coffee table, May in front of Bobby and Jessica in front of Tim. May put her phone camera on video and placed it between her and Jessica. They took hold of the boys’ erections.
“They’re so hard…” mouthed May silently, screwing up her face in delight. Jessica responded with a peace sign.
“Now, where were we?” she said, out loud. “Ah, yes. We’d settled on pink latex panties, hadn’t we. A little short blue satin dress with crinolines and a big bow at the waist, puff sleeves, white hold-up stockings… Shall we say blue Mary Janes, and Bobby’s hair in bunches with blue ribbons?”
Tim’s bloated coc-k quivered in her hand. She gave it a gentle encouraging squeeze.
“That seems agreeable. Keep holding hands, boys. Now, makeup. Bobby will need a little subtle makeup to make him the perfect girl. I’m going to suggest a touch of blue eye shadow, a little mascara – he’s already got lovely long lashes – er, I think a touch of blusher, and pink lip gloss – to match the panties you chose, Tim. Tim…? Oh my goodness…”
He had suddenly tensed, his head jerked back, and he gave a muffled sob. The coc-k in her fingers reared, and then it was pumping violently, the big teat inflating as it filled with c-um. His body shuddered with the force of his climax. Bobby, close beside him, felt every spasm, which was all he needed to set him off as well, and the next second the two of them, holding hands tight, were jerking and grunting in unison! Things had turned out even better than the girls could have hoped. They exchanged delighted glances, each diligently milking her own spurting coc-k, intent on prolonging the boys’ orgasms as long as possible, and making sure they were drained of every last possible drop.
89
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 03, 2025, 04:17:45 PM »
Chapter 237.
Jessica hooked a finger in his belt and drew him back to the sofa. She pushed him down and sat down beside him. She placed her hand on his bare thigh.
“Do you like the idea of Bobby in a pretty dress? Be honest, now.”
Tim had turned bright red. He turned his head away. In response, Jessica slid her hand up, over the frills of his shorts, and closed her fingers softly around the bulge of his erection. He gasped and looked for a moment as though he was going to pull away.
“No… Stay where you are. Sit on your hands, please. That’s right. Now Timothy,” she said, stroking him gently, “just relax. I want you to imagine that Miss Poole decides Bobby is going to present as a girl. That would be funny, wouldn’t it? Poor Bobby. He’s already quite pretty, isn’t he? Well, isn’t he?”
“Y-yes… I guess…”
“Of course he is. There’s no denying it. So…as I was saying… I’m sure he’ll be put in a dress, sooner or later. Ellie and us, we could advise Miss Poole what sort of outfit would look best on him. What do you think?”
Tim was trembling slightly now. Jessica applied gentle pressure to his erection, whilst her index finger traced little circles on the very tip.
“I mean, how about a cute little satin dress, with a waistband and a short bouncy skirt?”
Tim stiffened.
“Maybe a crinoline underskirt, Jessica,” suggested May, with a wink.
“Yes, perfect. That would be really cute, wouldn’t it Tim?”
“Y-yes… I s'pose...”
“Hmm. What colour, do you think?”
A short silence. “M-maybe b-blue…?”
“Good idea. Shiny pastel blue satin. It always looks good on blondes. Maybe with a big bow at the waist?”
“A b-bow?” He blinked, and stole a glance at Jessica’s face. Was she for real? She seemed quite serious. “Yeah…w-why not?” Distracted by Jessica’s absent-minded caresses he was slowly beginning to lose his earlier embarrassment. He leered at Bobby and laughed mockingly. “A big bow…for a big girl…”
“Oh, he’s going to look so cute, eh, Tim? What about sleeves? They could be long with cuffs - or little short puff sleeves? What do you think?”
Under the influence of Jessica’s ministrations Tim was becoming increasingly less able to self-censor or disguise his deepest and most secret feelings. The thought of Bobby as a pretty girl was something he dreamt about, and Jessica’s realisation of his dream couldn’t but arouse him. He tried to pretend he was only interested in Bobby’s humiliation, but it was obvious to all the others – Bobby included - he was profoundly excited by the whole idea.
“Oh, puff sleeves, I fink. Yeah, little puff sleeves, wiv lace trims…”
“That a sweet idea, Tim. Now, what else do we have to decide on? Oh, yes. Stockings or tights? Which do you think would be cutest with that little dress?”
She spoke in the same disinterested tone she might have used if she were asking him what he’d like to drink. She looked sideways at him, her slim fingers ceaselessly teasing his straining erection. She could see he was still trembling. He licked his dry lips. On the other side of the coffee-table, Bobby himself wasn’t in a much better state. He had kept his propensity for girls’ clothing secret from Tim. He had perhaps suspected Tim liked him in other ways than just as a friend. But here he was now, almost drooling over the idea. May, thrilled at the boys’ mutual arousal, took advantage of Tim’s temporary silence to guide Bobby into an armchair facing his friend. She perched on one arm and, pushing his hands aside, began to play with his smaller, but equally firm, erection. He blushed. This was not at all how he had imagined his first sexual encounter with May. But he couldn’t suppress a faint moan of pleasure. Jessica looked over approvingly.
Tim felt like he was intoxicated, or high. The vision of Bobby in a sweet little blue dress danced before him. He had a sort of yearning inside, almost a pain. Stockings or tights? Tights or stockings? In his mind he was trying them on the vision, deciding which would look best. To help him decide, Jessica pushed a finger under the flap of his straining fly. The press-stud immediately popped open, and his erection sprang out, hard and quivering. He gasped, panicking, then sighed with relief.
“There. Does that feel better, darling? “
Tim nodded, chest heaving. Jessica closed her fingers around the shaft – as best she could. She raised an eyebrow, and gave May a little smile. However, freeing his coc-k had also freed his tongue.
“T-tights. White t-tights… No, wait… Stockings! White ‘old-ups.”
“Stockings! Good choice! We’ll make the skirt short enough for you to see the tops, shall we? You’re getting there, Tim!” As he most certainly was. “So then, at last, we come to” - she lowered her voice – “Bobby's panties!” She giggled. “Tim. What sort of panties would you like? Any ideas?”
Tim swallowed. He felt as if he were choking. He was holding on by his fingertips. Bobby squirmed in his armchair.
“Any ideas, Bobby?” asked May. “They’re your panties, after all…”
Bobby could only look away in confusion. But Tim, fearful he would suggest something out of sync with his own imaginings, blurted out “sa’in! Blue sa’in!”
“Satin. To match his dress. Of course.”
“No, ’old on…”
“Changed your mind, Tim?”
Tim was collecting his thoughts. He had said the first thing that came into his head. But now his fantasy was becoming clearer.
“Latex. Yeah, pink latex wiv little blue latex frills around the legs, an’ a blue bow on the front…”
“Goodness, that very particular…but nice…”
May snorted with laughter. Bobby squirmed.
“Well, it seems you’re both in agreement,” smiled Jessica, letting go of Tim’s coc-k. “In which case we’ll talk to Ellie and then go see Miss Poole, and in a few weeks, if you’re lucky, Bobby will have an alternative outfit, and maybe you, Tim, will have an alternative girlfriend…”
Tim looked alarmed. “No, but I ain’t gay…or a sissy… Truly…”
“No-one said you were. But you like Bobby a lot. That’s fine. I like May a lot, and she likes me. But we don’t get flustered about it. We just accept it. You and Bobby should do the same.”
“But…”
She silenced further discussion by placing a finger on his lips.
Jessica hooked a finger in his belt and drew him back to the sofa. She pushed him down and sat down beside him. She placed her hand on his bare thigh.
“Do you like the idea of Bobby in a pretty dress? Be honest, now.”
Tim had turned bright red. He turned his head away. In response, Jessica slid her hand up, over the frills of his shorts, and closed her fingers softly around the bulge of his erection. He gasped and looked for a moment as though he was going to pull away.
“No… Stay where you are. Sit on your hands, please. That’s right. Now Timothy,” she said, stroking him gently, “just relax. I want you to imagine that Miss Poole decides Bobby is going to present as a girl. That would be funny, wouldn’t it? Poor Bobby. He’s already quite pretty, isn’t he? Well, isn’t he?”
“Y-yes… I guess…”
“Of course he is. There’s no denying it. So…as I was saying… I’m sure he’ll be put in a dress, sooner or later. Ellie and us, we could advise Miss Poole what sort of outfit would look best on him. What do you think?”
Tim was trembling slightly now. Jessica applied gentle pressure to his erection, whilst her index finger traced little circles on the very tip.
“I mean, how about a cute little satin dress, with a waistband and a short bouncy skirt?”
Tim stiffened.
“Maybe a crinoline underskirt, Jessica,” suggested May, with a wink.
“Yes, perfect. That would be really cute, wouldn’t it Tim?”
“Y-yes… I s'pose...”
“Hmm. What colour, do you think?”
A short silence. “M-maybe b-blue…?”
“Good idea. Shiny pastel blue satin. It always looks good on blondes. Maybe with a big bow at the waist?”
“A b-bow?” He blinked, and stole a glance at Jessica’s face. Was she for real? She seemed quite serious. “Yeah…w-why not?” Distracted by Jessica’s absent-minded caresses he was slowly beginning to lose his earlier embarrassment. He leered at Bobby and laughed mockingly. “A big bow…for a big girl…”
“Oh, he’s going to look so cute, eh, Tim? What about sleeves? They could be long with cuffs - or little short puff sleeves? What do you think?”
Under the influence of Jessica’s ministrations Tim was becoming increasingly less able to self-censor or disguise his deepest and most secret feelings. The thought of Bobby as a pretty girl was something he dreamt about, and Jessica’s realisation of his dream couldn’t but arouse him. He tried to pretend he was only interested in Bobby’s humiliation, but it was obvious to all the others – Bobby included - he was profoundly excited by the whole idea.
“Oh, puff sleeves, I fink. Yeah, little puff sleeves, wiv lace trims…”
“That a sweet idea, Tim. Now, what else do we have to decide on? Oh, yes. Stockings or tights? Which do you think would be cutest with that little dress?”
She spoke in the same disinterested tone she might have used if she were asking him what he’d like to drink. She looked sideways at him, her slim fingers ceaselessly teasing his straining erection. She could see he was still trembling. He licked his dry lips. On the other side of the coffee-table, Bobby himself wasn’t in a much better state. He had kept his propensity for girls’ clothing secret from Tim. He had perhaps suspected Tim liked him in other ways than just as a friend. But here he was now, almost drooling over the idea. May, thrilled at the boys’ mutual arousal, took advantage of Tim’s temporary silence to guide Bobby into an armchair facing his friend. She perched on one arm and, pushing his hands aside, began to play with his smaller, but equally firm, erection. He blushed. This was not at all how he had imagined his first sexual encounter with May. But he couldn’t suppress a faint moan of pleasure. Jessica looked over approvingly.
Tim felt like he was intoxicated, or high. The vision of Bobby in a sweet little blue dress danced before him. He had a sort of yearning inside, almost a pain. Stockings or tights? Tights or stockings? In his mind he was trying them on the vision, deciding which would look best. To help him decide, Jessica pushed a finger under the flap of his straining fly. The press-stud immediately popped open, and his erection sprang out, hard and quivering. He gasped, panicking, then sighed with relief.
“There. Does that feel better, darling? “
Tim nodded, chest heaving. Jessica closed her fingers around the shaft – as best she could. She raised an eyebrow, and gave May a little smile. However, freeing his coc-k had also freed his tongue.
“T-tights. White t-tights… No, wait… Stockings! White ‘old-ups.”
“Stockings! Good choice! We’ll make the skirt short enough for you to see the tops, shall we? You’re getting there, Tim!” As he most certainly was. “So then, at last, we come to” - she lowered her voice – “Bobby's panties!” She giggled. “Tim. What sort of panties would you like? Any ideas?”
Tim swallowed. He felt as if he were choking. He was holding on by his fingertips. Bobby squirmed in his armchair.
“Any ideas, Bobby?” asked May. “They’re your panties, after all…”
Bobby could only look away in confusion. But Tim, fearful he would suggest something out of sync with his own imaginings, blurted out “sa’in! Blue sa’in!”
“Satin. To match his dress. Of course.”
“No, ’old on…”
“Changed your mind, Tim?”
Tim was collecting his thoughts. He had said the first thing that came into his head. But now his fantasy was becoming clearer.
“Latex. Yeah, pink latex wiv little blue latex frills around the legs, an’ a blue bow on the front…”
“Goodness, that very particular…but nice…”
May snorted with laughter. Bobby squirmed.
“Well, it seems you’re both in agreement,” smiled Jessica, letting go of Tim’s coc-k. “In which case we’ll talk to Ellie and then go see Miss Poole, and in a few weeks, if you’re lucky, Bobby will have an alternative outfit, and maybe you, Tim, will have an alternative girlfriend…”
Tim looked alarmed. “No, but I ain’t gay…or a sissy… Truly…”
“No-one said you were. But you like Bobby a lot. That’s fine. I like May a lot, and she likes me. But we don’t get flustered about it. We just accept it. You and Bobby should do the same.”
“But…”
She silenced further discussion by placing a finger on his lips.
90
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 03, 2025, 04:10:31 PM »
Chapter 236.
Back in their pad, Bobby and Tim were admiring themselves in the full-length wardrobe mirror.
“We’re gonna ‘ave different gloves an’ stuff, ain’t we Bobby? Cos, like, at the moment you’ve got frills on your gloves and I ‘aven’t. And I like them red shoes what you’re wearin’…”
“Don’t worry, Tim! Cynthia said we each have the same range of accessories, and within limits we can choose which ones we wear at any given time.”
“Oh, that’s good, then. I really like the pink belt and those cool matchin’ frills, don’t you?”
“Yeah… The pink frills on your shorts are bigger than mine.”
“Oh yeah…you’re right. Yours are smaller but you got more of ‘em…”
“We both look cool, right?”
“Yeah… I don’t even mind the butt-plug thing now. I can ‘ardly feel it. Just a faint ticklin’, like…”
“Yes. It’s nice actually…” Bobby was comparing it to his pony suit tail.
“Girls will be ‘ere soon. I’ll order some grub. Chicken?”
“Fine… Oh, hi, Ellie…”
“Hi. Well, happy?”
“Yeah, these outfits are excellent!”
“Good. But I’m going to need them so I can get them washed for tomorrow.”
“But Miss Poole said…”
“Yes, I know. You could wear them for the rest of the day. Don’t worry. You can try the others out instead. Here.” She held up a pair. “Just the same but with a fly. You only need to change your shorts. I’ve got tons of clean accessories.”
“Okay…”
“Come on then. Get them off while I lube these up. Now these come with a special condom.”
“Condom?”
“Yes. You’ll see. Come on, hurry up. You’ve got a date tonight, I heard…”
Ellie lubed their new shorts, helped them into them, slipped in the plugs, and then made them hold open the fronts while she arranged the loops and fitted the condoms. The extra-long opaque condoms had special round teats at the ends, capable of holding several orgasms-worth of c-um, since they were intended to be worn for longer periods.
“Why do we ‘ave to wear these? What’s the point?”
“Shush, Tim,” whispered Bobby. “It’s perfect. S’pose the girls…you know… I mean, we don’t have any normal condoms here, do we?”
“Oh…right… I ‘adn’t fought of that. Perfec’!”
Ellie hid her smile. “Right. I’m going to get these ones washed, hang them up at back, and go. Enjoy your evening, boys. First appointment tomorrow nine o’clock.”
“Thank, Ellie!”
“Yeah… Fanks, Ellie…”
The boys sat around waiting for the girls. After about ten minutes, Tim stood up.
“Hey, Bobby mate…”
“Yeah?”
“This plug feels different. I can feel it more, if you know wha’ I mean…”
“Yes. I thought it was my imagination…”
“It ain’t. It’s definitely different. Slow, then fast, then slow again. Sometimes it stops, then it starts up again more than before. It’s makin’ me…”
“What?”
“You know. I’m getting’ ‘orny…”
“That’s good then. Jessica will be pleased.”
“You reckon? Yeah, when she sees wha’ I got…”
“It’s nothing special, Tim,” laughed Bobby.
“No? It’s bigger ‘n yours, anyway. Yeah, you know it is, don’t yer?” he added triumphantly. “You found that out the uvver night, right?”
“Size isn’t everything,” said Bobby, chagrined.
“Be’’er ask May that!” replied Tim, with a careless laugh.
“They’re here! Quick. I’ll go.”
“No, I’m goin’”
There was a brief struggle, which Tim won. He went to the door.
“Come in, darlin’. Hi, May…”
The girls went to the shower and changed their clothes. By the time they returned, the food had arrived, and they sat down to eat. The vibes had kicked in now, albeit at a low level, but it was enough to provoke growing erections. The boys became flushed and nervous, and both were fidgeting as they tried to control their arousal.
“You two seem a bit distracted this evening,” ventured May. “What’s going on?”
“Yeah, what’s up? Tim, where’s that boy who was showing off to all our friends earlier? Don’t we get some sort of show too?”
“No, er… I mean, I weren’t showin’ off…”
“Yes you were. Come on, stand up and let’s see how cute you look…”
“Yes, go on Tim. You too, Bobby. Pretend we’re customers. Look, we’re both wearing boots tonight. Maybe we could have a free shoeshine…”
“But…” began Bobby.
“No buts,” cut in May. “On your feet, both of you, or we’ll go get some entertainment elsewhere.”
The boys looked at each other, then reluctantly rose to their feet. They tried to hide their erections, but there was no way, especially in Tim’s case. However, by tacit agreement, the girls made no comment about them.
“Those outfits are so cool – don’t you think, May?”
“Yeah. Actually I wouldn’t mind wearing something like that myself.”
“Nor me. We could start a pagegirl trend. Know what? I’m going to ask Ellie for the contact details of that Cynthia woman. At least we could find out what something like that would cost.”
But Tim, forgetting for a moment about his now quite impressive erection, was not happy.
“You can’t do that, Jessica. These outfits are our exclusive designs.”
“No such thing as exclusive, Tim.”
“What yer mean? She wouldn’t let yer ‘ave them anyway. They’re, like, copyright…”
“Clothes can’t be copyright, silly!”
“Well these are! Find yer own gear! Girls’ stuff. This are boys’ clothes…”
“Really, Tim? Do you really think like that?” Jessica stood up and approached. He took a step back.
“What yer doin’…?”
“Have you ever seen us wear girly stuff? We’re not into it. For your information we prefer “boys’” clothes, as you put it. Right, May?”
“Every time…”
“Well, I only meant…”
“And what about Bobby’s dress?”
Tim looked startled “What?”
“I heard you were looking forward to Bobby being put in dresses.”
Tim gulped. “How…?”
“Come with me.”
Back in their pad, Bobby and Tim were admiring themselves in the full-length wardrobe mirror.
“We’re gonna ‘ave different gloves an’ stuff, ain’t we Bobby? Cos, like, at the moment you’ve got frills on your gloves and I ‘aven’t. And I like them red shoes what you’re wearin’…”
“Don’t worry, Tim! Cynthia said we each have the same range of accessories, and within limits we can choose which ones we wear at any given time.”
“Oh, that’s good, then. I really like the pink belt and those cool matchin’ frills, don’t you?”
“Yeah… The pink frills on your shorts are bigger than mine.”
“Oh yeah…you’re right. Yours are smaller but you got more of ‘em…”
“We both look cool, right?”
“Yeah… I don’t even mind the butt-plug thing now. I can ‘ardly feel it. Just a faint ticklin’, like…”
“Yes. It’s nice actually…” Bobby was comparing it to his pony suit tail.
“Girls will be ‘ere soon. I’ll order some grub. Chicken?”
“Fine… Oh, hi, Ellie…”
“Hi. Well, happy?”
“Yeah, these outfits are excellent!”
“Good. But I’m going to need them so I can get them washed for tomorrow.”
“But Miss Poole said…”
“Yes, I know. You could wear them for the rest of the day. Don’t worry. You can try the others out instead. Here.” She held up a pair. “Just the same but with a fly. You only need to change your shorts. I’ve got tons of clean accessories.”
“Okay…”
“Come on then. Get them off while I lube these up. Now these come with a special condom.”
“Condom?”
“Yes. You’ll see. Come on, hurry up. You’ve got a date tonight, I heard…”
Ellie lubed their new shorts, helped them into them, slipped in the plugs, and then made them hold open the fronts while she arranged the loops and fitted the condoms. The extra-long opaque condoms had special round teats at the ends, capable of holding several orgasms-worth of c-um, since they were intended to be worn for longer periods.
“Why do we ‘ave to wear these? What’s the point?”
“Shush, Tim,” whispered Bobby. “It’s perfect. S’pose the girls…you know… I mean, we don’t have any normal condoms here, do we?”
“Oh…right… I ‘adn’t fought of that. Perfec’!”
Ellie hid her smile. “Right. I’m going to get these ones washed, hang them up at back, and go. Enjoy your evening, boys. First appointment tomorrow nine o’clock.”
“Thank, Ellie!”
“Yeah… Fanks, Ellie…”
The boys sat around waiting for the girls. After about ten minutes, Tim stood up.
“Hey, Bobby mate…”
“Yeah?”
“This plug feels different. I can feel it more, if you know wha’ I mean…”
“Yes. I thought it was my imagination…”
“It ain’t. It’s definitely different. Slow, then fast, then slow again. Sometimes it stops, then it starts up again more than before. It’s makin’ me…”
“What?”
“You know. I’m getting’ ‘orny…”
“That’s good then. Jessica will be pleased.”
“You reckon? Yeah, when she sees wha’ I got…”
“It’s nothing special, Tim,” laughed Bobby.
“No? It’s bigger ‘n yours, anyway. Yeah, you know it is, don’t yer?” he added triumphantly. “You found that out the uvver night, right?”
“Size isn’t everything,” said Bobby, chagrined.
“Be’’er ask May that!” replied Tim, with a careless laugh.
“They’re here! Quick. I’ll go.”
“No, I’m goin’”
There was a brief struggle, which Tim won. He went to the door.
“Come in, darlin’. Hi, May…”
The girls went to the shower and changed their clothes. By the time they returned, the food had arrived, and they sat down to eat. The vibes had kicked in now, albeit at a low level, but it was enough to provoke growing erections. The boys became flushed and nervous, and both were fidgeting as they tried to control their arousal.
“You two seem a bit distracted this evening,” ventured May. “What’s going on?”
“Yeah, what’s up? Tim, where’s that boy who was showing off to all our friends earlier? Don’t we get some sort of show too?”
“No, er… I mean, I weren’t showin’ off…”
“Yes you were. Come on, stand up and let’s see how cute you look…”
“Yes, go on Tim. You too, Bobby. Pretend we’re customers. Look, we’re both wearing boots tonight. Maybe we could have a free shoeshine…”
“But…” began Bobby.
“No buts,” cut in May. “On your feet, both of you, or we’ll go get some entertainment elsewhere.”
The boys looked at each other, then reluctantly rose to their feet. They tried to hide their erections, but there was no way, especially in Tim’s case. However, by tacit agreement, the girls made no comment about them.
“Those outfits are so cool – don’t you think, May?”
“Yeah. Actually I wouldn’t mind wearing something like that myself.”
“Nor me. We could start a pagegirl trend. Know what? I’m going to ask Ellie for the contact details of that Cynthia woman. At least we could find out what something like that would cost.”
But Tim, forgetting for a moment about his now quite impressive erection, was not happy.
“You can’t do that, Jessica. These outfits are our exclusive designs.”
“No such thing as exclusive, Tim.”
“What yer mean? She wouldn’t let yer ‘ave them anyway. They’re, like, copyright…”
“Clothes can’t be copyright, silly!”
“Well these are! Find yer own gear! Girls’ stuff. This are boys’ clothes…”
“Really, Tim? Do you really think like that?” Jessica stood up and approached. He took a step back.
“What yer doin’…?”
“Have you ever seen us wear girly stuff? We’re not into it. For your information we prefer “boys’” clothes, as you put it. Right, May?”
“Every time…”
“Well, I only meant…”
“And what about Bobby’s dress?”
Tim looked startled “What?”
“I heard you were looking forward to Bobby being put in dresses.”
Tim gulped. “How…?”
“Come with me.”
The more you give, the more I can give back.
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