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31
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 02, 2026, 04:31:48 AM »
Chapter 303.
The last time Tim had seen Nicola was that day he'd met Teri. On that occasion she’d seemed very casual and friendly. He remembered she was wearing a cute little black dress. This time she seemed rather different. She was sitting in a chair waiting for him.
“He’s all yours,” said Lucille, shortly, and left without another word, heading back towards the kitchen. Nicola stood up. The little dress had been replaced with faux leather leggings and a leather jacket. A short bamboo cane lay on a desk near at hand.
“G-good afternoon, Miss N-Nicola…”
Nicola ignored the greeting.
“Stand up straight, please. You’ve just had deportment instruction, and you dare to come here slouching?”
He jerked himself upright.
“Tell me what you’ve learned so far.”
“L-learned?”
Nicola gave a short, impatient snort. “Learned! Yes. Do you not understand the word?”
“Oh, yes… Er, I learned ‘ow to walk proper…”
Nicola glared and held up her hand. “Enough! “You learned ‘ow to walk proper”? You seriously dare to come in here – to an elocution class – and speak to me like that? Well?”
“I’m sorry, miss…”
“Oh, you will be, I can tell you now…”
She picked up the cane, and took a step towards him. She raised a finger and used it to emphasize each sentence.
“Stand still! Don’t you dare flinch. Now listen to me, Tim, Mitzy, whoever you are - actually I don’t care who you are. I’m here for only one reason. To teach you a simple lesson. To speak reasonable English, so you don’t disgrace yourself and your employers. That means polite, well-modulated words, no roughness, no hesitation, no crass grammatical mistakes, and no dropped aitches! Do you understand?”
“Yes miss.”
“And you’ll learn these lessons either with quiet attention and progress… Or by having them thrashed into you!”
Tim trembled. He bit his lip. Tears formed in his eyes.
“Now. I was listening to you when you were talking with Teri. You must know what your most obvious faults are. In case you don’t, I’ll tell you. One, you drop your aitches. Two, you substitute “f” for “th”. Now I’m going to make a statement, and you repeat it. Simple. Okay?”
“Yes miss.”
“Have you thought how to handle a hedgehog without hurting your hands?”
“S-sorry, miss…?”
“Just repeat it, silly! Have you thought how to handle a hedgehog without hurting your hands!”
“Oh… ‘Ave…no…Have you f…I mean, thought, ‘ow….”
“Stop. Again. And every time you make a mistake I’m going to give you a little tap with this, until you can say it properly.”
The “little taps” started gently, but grew in strength with Nicola’s impatience. After a while, she moved on to Shakespeare, hoping the poetry would inspire him.
“No, Mitzy, not “O, ‘ow shall summer’s ‘oney bref ‘old out…” I want to hear – to hear (she emphasized the aitch) – all those lovely aitches… But poor Tim got so confused he said “hout” instead of “out”, and got a smart smack on his thigh as a reward, making him whimper and shed tears. But at the next try he was word perfect. Nicola took this achievement as an endorsement of her methods, and employed them with greater frequency and vigour until, though the simple application of pain, not unsatisfactory results were, between sobs, eventually obtained.
Tim’s first proper training day was at an end. He remembered his promise to Ellie, and returned to Pitt’s Wood in his dress and without erasing his makeup. She was so impressed that, after taking multiple photos, she gave him a big hug and several kisses. Which almost made up for all the distress.
The last time Tim had seen Nicola was that day he'd met Teri. On that occasion she’d seemed very casual and friendly. He remembered she was wearing a cute little black dress. This time she seemed rather different. She was sitting in a chair waiting for him.
“He’s all yours,” said Lucille, shortly, and left without another word, heading back towards the kitchen. Nicola stood up. The little dress had been replaced with faux leather leggings and a leather jacket. A short bamboo cane lay on a desk near at hand.
“G-good afternoon, Miss N-Nicola…”
Nicola ignored the greeting.
“Stand up straight, please. You’ve just had deportment instruction, and you dare to come here slouching?”
He jerked himself upright.
“Tell me what you’ve learned so far.”
“L-learned?”
Nicola gave a short, impatient snort. “Learned! Yes. Do you not understand the word?”
“Oh, yes… Er, I learned ‘ow to walk proper…”
Nicola glared and held up her hand. “Enough! “You learned ‘ow to walk proper”? You seriously dare to come in here – to an elocution class – and speak to me like that? Well?”
“I’m sorry, miss…”
“Oh, you will be, I can tell you now…”
She picked up the cane, and took a step towards him. She raised a finger and used it to emphasize each sentence.
“Stand still! Don’t you dare flinch. Now listen to me, Tim, Mitzy, whoever you are - actually I don’t care who you are. I’m here for only one reason. To teach you a simple lesson. To speak reasonable English, so you don’t disgrace yourself and your employers. That means polite, well-modulated words, no roughness, no hesitation, no crass grammatical mistakes, and no dropped aitches! Do you understand?”
“Yes miss.”
“And you’ll learn these lessons either with quiet attention and progress… Or by having them thrashed into you!”
Tim trembled. He bit his lip. Tears formed in his eyes.
“Now. I was listening to you when you were talking with Teri. You must know what your most obvious faults are. In case you don’t, I’ll tell you. One, you drop your aitches. Two, you substitute “f” for “th”. Now I’m going to make a statement, and you repeat it. Simple. Okay?”
“Yes miss.”
“Have you thought how to handle a hedgehog without hurting your hands?”
“S-sorry, miss…?”
“Just repeat it, silly! Have you thought how to handle a hedgehog without hurting your hands!”
“Oh… ‘Ave…no…Have you f…I mean, thought, ‘ow….”
“Stop. Again. And every time you make a mistake I’m going to give you a little tap with this, until you can say it properly.”
The “little taps” started gently, but grew in strength with Nicola’s impatience. After a while, she moved on to Shakespeare, hoping the poetry would inspire him.
“No, Mitzy, not “O, ‘ow shall summer’s ‘oney bref ‘old out…” I want to hear – to hear (she emphasized the aitch) – all those lovely aitches… But poor Tim got so confused he said “hout” instead of “out”, and got a smart smack on his thigh as a reward, making him whimper and shed tears. But at the next try he was word perfect. Nicola took this achievement as an endorsement of her methods, and employed them with greater frequency and vigour until, though the simple application of pain, not unsatisfactory results were, between sobs, eventually obtained.
Tim’s first proper training day was at an end. He remembered his promise to Ellie, and returned to Pitt’s Wood in his dress and without erasing his makeup. She was so impressed that, after taking multiple photos, she gave him a big hug and several kisses. Which almost made up for all the distress.
32
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 01, 2026, 06:23:25 PM »
Chapter 302.
“Follow me.”
She led Tim – or Mitzy - through the kitchen. The house was large, and at the back a long two-storey extension jutted into the garden, the door to which was reached by a covered walkway running along the back of the house. She opened the door and showed him in. The lower storey housed a modern office with big picture windows. Opposite the door, a staircase led up to the second storey. He followed her up the stairs and found himself in at the end of a corridor with a polished wooden floor. At the far end of the corridor was a door with brass locks. On the left wall was another door, and on the right big windows overlooked the garden.
“I want to see how you walk. Walk down to the end and back again, please.”
“Yes, miss.”
When he reached the end of the corridor and saw the door with the double locks close up, he wondered what lay behind it. But he turned without hesitating, and walked back with what he thought was a dignified and graceful manner. Lucille, however, wasn’t impressed.
“Goodness! What sort of animal are you impersonating, Tim? A hippopotamus? You’re a young maid, a fairy girl, a sylph! Please try to remember that and act like one. Small, dainty steps – not great clumpy strides, Again, please.”
The next attempt was little better. After that he completely lost his confidence, and Lucille lost her patience.
“No, this won’t do. It really won’t.” She threw open the door on the side wall. “Go in there and wait.”
He found himself in a sort of ballroom, with a big window at the far end, a polished floor, pictures on the walls, and a row of tables along the far side and across the ends, some round, some square, like in a restaurant. The pictures were mainly of horses, lady horse riders, and maids. The maids looked like girls at first glance, but looking closer he realised there were all boys dressed as maids. Yes, there was Teri! These must all be ESDS maids. And this place… Maybe to entertain prospective clients?
Lucille returned. She looked irritable.
“Sit down there. Yes, there!”
She was holding something. A silver chain hung from one hand, and she held a short riding whip in the other. She knelt. It was two leather straps on each end of a short length of steel chain. She buckled the straps to his ankles.
“This is called a hobble. Wearing this you will learn to take small steps, until it becomes second nature. Unfortunately it’s the only way for boys like you, Mitzy. Now stand up and let’s get on. We’ve got till three. Then Miss Nicola takes over.”
He had an hour of training in the hobble, tripping along (sometimes actually tripping!) withy Lucille behind him encouraging him with little stinging slaps of her whip on his calves. Once he actually shed tears. Shockingly, she seemed pleased.
“Ah, I think you’re learning…”
The hobble stayed on whilst he was instructed in the correct way to stand – straight as a reed, chin up, eyes down – the niceties of curtseying, how to welcome guests, how to take their coats, how to introduce and announce them, when to bow, how to kneel when something was dropped or a shoe or boot needed attention, how to serve at table (without showing off one’s panties), and so on. By the time three o’clock came round, he was quite exhausted, but at least his hobble was removed, and Lucille sent him straight downstairs to the office for his next lesson - Elocution with Miss Nicola.
“Follow me.”
She led Tim – or Mitzy - through the kitchen. The house was large, and at the back a long two-storey extension jutted into the garden, the door to which was reached by a covered walkway running along the back of the house. She opened the door and showed him in. The lower storey housed a modern office with big picture windows. Opposite the door, a staircase led up to the second storey. He followed her up the stairs and found himself in at the end of a corridor with a polished wooden floor. At the far end of the corridor was a door with brass locks. On the left wall was another door, and on the right big windows overlooked the garden.
“I want to see how you walk. Walk down to the end and back again, please.”
“Yes, miss.”
When he reached the end of the corridor and saw the door with the double locks close up, he wondered what lay behind it. But he turned without hesitating, and walked back with what he thought was a dignified and graceful manner. Lucille, however, wasn’t impressed.
“Goodness! What sort of animal are you impersonating, Tim? A hippopotamus? You’re a young maid, a fairy girl, a sylph! Please try to remember that and act like one. Small, dainty steps – not great clumpy strides, Again, please.”
The next attempt was little better. After that he completely lost his confidence, and Lucille lost her patience.
“No, this won’t do. It really won’t.” She threw open the door on the side wall. “Go in there and wait.”
He found himself in a sort of ballroom, with a big window at the far end, a polished floor, pictures on the walls, and a row of tables along the far side and across the ends, some round, some square, like in a restaurant. The pictures were mainly of horses, lady horse riders, and maids. The maids looked like girls at first glance, but looking closer he realised there were all boys dressed as maids. Yes, there was Teri! These must all be ESDS maids. And this place… Maybe to entertain prospective clients?
Lucille returned. She looked irritable.
“Sit down there. Yes, there!”
She was holding something. A silver chain hung from one hand, and she held a short riding whip in the other. She knelt. It was two leather straps on each end of a short length of steel chain. She buckled the straps to his ankles.
“This is called a hobble. Wearing this you will learn to take small steps, until it becomes second nature. Unfortunately it’s the only way for boys like you, Mitzy. Now stand up and let’s get on. We’ve got till three. Then Miss Nicola takes over.”
He had an hour of training in the hobble, tripping along (sometimes actually tripping!) withy Lucille behind him encouraging him with little stinging slaps of her whip on his calves. Once he actually shed tears. Shockingly, she seemed pleased.
“Ah, I think you’re learning…”
The hobble stayed on whilst he was instructed in the correct way to stand – straight as a reed, chin up, eyes down – the niceties of curtseying, how to welcome guests, how to take their coats, how to introduce and announce them, when to bow, how to kneel when something was dropped or a shoe or boot needed attention, how to serve at table (without showing off one’s panties), and so on. By the time three o’clock came round, he was quite exhausted, but at least his hobble was removed, and Lucille sent him straight downstairs to the office for his next lesson - Elocution with Miss Nicola.
33
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on January 01, 2026, 06:16:49 PM »
Chapter 301.
“Ideally, we’d like to have you ready by the weekend before you’re booked to go to Mrs Brookshaw’s. That gives us a total of seven days, including today. Failing that we could still use the Sunday after the wedding and even the Wednesday. Whether we need to do that depends entirely on the progress you make. You’ll have the best professional help available. I think you’ve met all our staff. Each one has a speciality. I will be in charge of your deportment, and today will be devoted to instruction about how you should move and comport yourself generally. Elocution – very important. You will need to make a special effort there, Timothy, as I’m sure you know. That is Nicola’s province. Nicola looks very sweet, but I have to tell you she is quite a severe disciplinarian, as you will no doubt discover. As to discipline itself – that is to say, not only applying it, but teaching you what it means for a domestic, what total obedience involves – that’s for Priscilla. Sasha will train you in the basics of household duties, cleaning, washing, preparing your mistresses clothes, and so on. Then there’s food and drink. How to prepare basic dishes, how to make coc-ktails, the names of drinks, and so on. It’s a huge subject. Margaret will be your mentor. Starting from scratch, we can’t expect to instil any more than a basic familiarity in the short time available, so your training in this area will continue indefinitely. What else? You know Carly is our makeup specialist. You’ll have to learn to do your own makeup eventually. Ah, yes. Clothing and accessories. That’s Doreen. Basically, her task is to teach you taste. Taste is something you have or you don’t. From what I’ve seen of you, your appreciation for your uniform, your concern for neatness and your appearance, I think you have taste, even if it may need refinement. We’ll find out, anyway. She’ll also be in charge of your chastity device, so if I were you I would try to stay in her good books!”
Serena had sidled into the room. “All this training will help you put on a good show at the wedding, too, Tim. Did you think of that?”
“Oh… I hadn’t, Miss Serena… But I can see…”
“Ah, the wedding,” smiled Lucille. “I’ve heard about this. You’re going to be a pageboy, is that right?”
“Yes, miss. I’ll be the only pageboy.”
“And you have a uniform?”
“Oh, he does, Lucille. Fantastex are making him some special new shorts, but it’s all top secret. He won’t even tell me the colour!”
“How exciting! Timothy, I want to see you in it before the day. Will you show me?”
“Yes, miss. If you want. I fink it’s gonna be really cool…”
“Where’s this wedding?”
“South Kennett,” said Serena. St. Michael’s church, then the reception at the Gate Hotel.”
“Oh… You seem to know all about it…”
“I’ve been invited. I know some friends of the bride. And I wouldn’t miss Tim the pageboy for anything.”
“Take some photos to show us…”
“Don’t worry, Lucille…”
“So, Tim… Any questions?”
Tim shook he head slowly, “No, miss…”
“Right. Follow me then. We’ll get started. But just before we do, I should explain that once you’re in training you will need a new name, something appropriate to a young maid.”
“A n-new name…?”
“Yes. Just like Teri with an “i”. We discussed it at length, and we’re agreed.” She smiled. “Mitzy. Like it?”
“M-Mitzy…?”
“We think it’ll suit you perfectly. Sort of cute and zippy. And it begins m, i, t – Tim backwards. You’ll go in the brochure under Mitzy. So get used to it. Okay?”
“Y-yes, miss…”
“Ideally, we’d like to have you ready by the weekend before you’re booked to go to Mrs Brookshaw’s. That gives us a total of seven days, including today. Failing that we could still use the Sunday after the wedding and even the Wednesday. Whether we need to do that depends entirely on the progress you make. You’ll have the best professional help available. I think you’ve met all our staff. Each one has a speciality. I will be in charge of your deportment, and today will be devoted to instruction about how you should move and comport yourself generally. Elocution – very important. You will need to make a special effort there, Timothy, as I’m sure you know. That is Nicola’s province. Nicola looks very sweet, but I have to tell you she is quite a severe disciplinarian, as you will no doubt discover. As to discipline itself – that is to say, not only applying it, but teaching you what it means for a domestic, what total obedience involves – that’s for Priscilla. Sasha will train you in the basics of household duties, cleaning, washing, preparing your mistresses clothes, and so on. Then there’s food and drink. How to prepare basic dishes, how to make coc-ktails, the names of drinks, and so on. It’s a huge subject. Margaret will be your mentor. Starting from scratch, we can’t expect to instil any more than a basic familiarity in the short time available, so your training in this area will continue indefinitely. What else? You know Carly is our makeup specialist. You’ll have to learn to do your own makeup eventually. Ah, yes. Clothing and accessories. That’s Doreen. Basically, her task is to teach you taste. Taste is something you have or you don’t. From what I’ve seen of you, your appreciation for your uniform, your concern for neatness and your appearance, I think you have taste, even if it may need refinement. We’ll find out, anyway. She’ll also be in charge of your chastity device, so if I were you I would try to stay in her good books!”
Serena had sidled into the room. “All this training will help you put on a good show at the wedding, too, Tim. Did you think of that?”
“Oh… I hadn’t, Miss Serena… But I can see…”
“Ah, the wedding,” smiled Lucille. “I’ve heard about this. You’re going to be a pageboy, is that right?”
“Yes, miss. I’ll be the only pageboy.”
“And you have a uniform?”
“Oh, he does, Lucille. Fantastex are making him some special new shorts, but it’s all top secret. He won’t even tell me the colour!”
“How exciting! Timothy, I want to see you in it before the day. Will you show me?”
“Yes, miss. If you want. I fink it’s gonna be really cool…”
“Where’s this wedding?”
“South Kennett,” said Serena. St. Michael’s church, then the reception at the Gate Hotel.”
“Oh… You seem to know all about it…”
“I’ve been invited. I know some friends of the bride. And I wouldn’t miss Tim the pageboy for anything.”
“Take some photos to show us…”
“Don’t worry, Lucille…”
“So, Tim… Any questions?”
Tim shook he head slowly, “No, miss…”
“Right. Follow me then. We’ll get started. But just before we do, I should explain that once you’re in training you will need a new name, something appropriate to a young maid.”
“A n-new name…?”
“Yes. Just like Teri with an “i”. We discussed it at length, and we’re agreed.” She smiled. “Mitzy. Like it?”
“M-Mitzy…?”
“We think it’ll suit you perfectly. Sort of cute and zippy. And it begins m, i, t – Tim backwards. You’ll go in the brochure under Mitzy. So get used to it. Okay?”
“Y-yes, miss…”
34
Active Sissy Stories / Re: Tiffany's Date
« Last post by babyian on December 31, 2025, 07:36:08 PM »
yes please continue, lets see how his mother reacts, is tiffany going to help further regress him and will he get sent to school in locking nappies and locking plastic baby pants, will he ne nappied 24/7 365 days a year, will he be fully regressed
35
Active Sissy Stories / Re: Tiffany's Date
« Last post by sidbaby on December 31, 2025, 08:50:11 AM »
From here was born the best ABDL story writer the world has ever seen.
36
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on December 30, 2025, 09:28:05 AM »
Chapter 300.
Serena opened the door and motioned Tim inside. Carly appeared at the end of the corridor.
“Hi. Lucille’s here. I need to get him changed and give him a quick makeover, then she wants to see him.”
“Go ahead. I’m going to get coffee.”
“This way, darling…”
Carly led him into the bedroom where he had slept at the weekend.
“Your outfit’s on the bed. Get changed as quickly as you can. You remember Lucille? She wants to speak to you before she goes.”
Tim changed into the maid uniform. This one was slightly different from before, with long sleeves. Carly helped him zip up, then sat him in front of the dressing table and began to attend to his makeup.
“You’ll soon realise that being well made-up is essential. In fact, you mustn’t appear in public in your uniform until you’ve done your makeup, or someone’s done it for you. I’m going to do it for the time being, but I’m also going to train you to do your own. It needn’t take long – clean your face, a little powder if you like, but you don’t need it. Blusher? Maybe, if you want to look super cute. But eye shadow, mascara and lipstick are indispensable. For you, pink eye shadow. You can choose whatever lipstick you want, provided it’s appropriate – pink goes with your outfit. And later I’m going to tint your hair. It’s lovely, but I want to bring out that gingery-bronze colour. Little is more. It makes such a difference, especially for special occasions. And being a maid is always a special occasion.”
“In a couple of weeks I’m goin’ to a weddin’,” said Tim; and added, proudly, “I’m gonna be a pageboy – I mean, the pageboy. The bride wants me to lead the procession in the church.”
Carly held back with the lipstick.
“Seriously? How did you swing that? Are you family?”
“No. I was recommended and she asked me.”
“Lucky you.” She continued her work. “What are you going to wear?”
“I’ve got a special pageboy outfit,” Tim said, excitedly. “Cool shorts in next year’s colours.”
“Next year’s colours? Which are?”
“Oh, I ain’t allowed to say. It ain’t generally known.”
“Oh, I see… The fashion industry’s so secretive, isn’t it? Anyway, your done. Look in the mirror.”
“I look so different wiv makeup an’ stuff…”
“You look really striking. And much more smiley. It seems to being out your natural sparkly personality. You look nothing like that grumpy boy we dragged to the nail parlour.”
“I didn’t understand, then. I was finkin’, Miss Carly…”
“Yes, Tim?”
“Would you… I mean, could you give me a makeover for the weddin’? I know you must be busy an’ all…”
“Of course! For something that important, of course I would.”
“Wow! Franks…”
“We can discuss it later. Now you must hurry to see Miss Lucille. She’s in the living room. Put on your gloves, darling. Always be properly dressed. Okay? Off you go, then…”
And she sent him on his way with a friendly pat on the bottom.
“What a sweetie,” she murmured.
Tim made his way nervously along the corridor to the living room. Peeping in, he found Serena and her mother chatting to Lucille.
“Hello, Tim,” said Cassandra. “Come in. You know Lucille, don’t you?”
“Hello Miss Cassandra…Miss Lucille…” He made an effort to pronounce the aitch.
“I hope we didn’t interrupt your routine too much… But we really need you to be ready by the end of the month. Lucille will fill you in. Would you like a drink? I’m sure you would. Lemonade okay? Great. We’ll leave you two to talk, then…”
She took Serena's arm, and they went into the kitchen, leaving Tim alone with Lucille. She smiled.
“I just need a word, Tim, to set the scene as it were. Don't be nervous - relax and listen. I'll explain the plans for the next couple of weeks. After that it'll be up to the staff and to your own initiative. You're a bright boy. I have full confidence in you. I know you're going to make a success of the project, and be suitably rewarded. So this is what's going to happen...”
Serena opened the door and motioned Tim inside. Carly appeared at the end of the corridor.
“Hi. Lucille’s here. I need to get him changed and give him a quick makeover, then she wants to see him.”
“Go ahead. I’m going to get coffee.”
“This way, darling…”
Carly led him into the bedroom where he had slept at the weekend.
“Your outfit’s on the bed. Get changed as quickly as you can. You remember Lucille? She wants to speak to you before she goes.”
Tim changed into the maid uniform. This one was slightly different from before, with long sleeves. Carly helped him zip up, then sat him in front of the dressing table and began to attend to his makeup.
“You’ll soon realise that being well made-up is essential. In fact, you mustn’t appear in public in your uniform until you’ve done your makeup, or someone’s done it for you. I’m going to do it for the time being, but I’m also going to train you to do your own. It needn’t take long – clean your face, a little powder if you like, but you don’t need it. Blusher? Maybe, if you want to look super cute. But eye shadow, mascara and lipstick are indispensable. For you, pink eye shadow. You can choose whatever lipstick you want, provided it’s appropriate – pink goes with your outfit. And later I’m going to tint your hair. It’s lovely, but I want to bring out that gingery-bronze colour. Little is more. It makes such a difference, especially for special occasions. And being a maid is always a special occasion.”
“In a couple of weeks I’m goin’ to a weddin’,” said Tim; and added, proudly, “I’m gonna be a pageboy – I mean, the pageboy. The bride wants me to lead the procession in the church.”
Carly held back with the lipstick.
“Seriously? How did you swing that? Are you family?”
“No. I was recommended and she asked me.”
“Lucky you.” She continued her work. “What are you going to wear?”
“I’ve got a special pageboy outfit,” Tim said, excitedly. “Cool shorts in next year’s colours.”
“Next year’s colours? Which are?”
“Oh, I ain’t allowed to say. It ain’t generally known.”
“Oh, I see… The fashion industry’s so secretive, isn’t it? Anyway, your done. Look in the mirror.”
“I look so different wiv makeup an’ stuff…”
“You look really striking. And much more smiley. It seems to being out your natural sparkly personality. You look nothing like that grumpy boy we dragged to the nail parlour.”
“I didn’t understand, then. I was finkin’, Miss Carly…”
“Yes, Tim?”
“Would you… I mean, could you give me a makeover for the weddin’? I know you must be busy an’ all…”
“Of course! For something that important, of course I would.”
“Wow! Franks…”
“We can discuss it later. Now you must hurry to see Miss Lucille. She’s in the living room. Put on your gloves, darling. Always be properly dressed. Okay? Off you go, then…”
And she sent him on his way with a friendly pat on the bottom.
“What a sweetie,” she murmured.
Tim made his way nervously along the corridor to the living room. Peeping in, he found Serena and her mother chatting to Lucille.
“Hello, Tim,” said Cassandra. “Come in. You know Lucille, don’t you?”
“Hello Miss Cassandra…Miss Lucille…” He made an effort to pronounce the aitch.
“I hope we didn’t interrupt your routine too much… But we really need you to be ready by the end of the month. Lucille will fill you in. Would you like a drink? I’m sure you would. Lemonade okay? Great. We’ll leave you two to talk, then…”
She took Serena's arm, and they went into the kitchen, leaving Tim alone with Lucille. She smiled.
“I just need a word, Tim, to set the scene as it were. Don't be nervous - relax and listen. I'll explain the plans for the next couple of weeks. After that it'll be up to the staff and to your own initiative. You're a bright boy. I have full confidence in you. I know you're going to make a success of the project, and be suitably rewarded. So this is what's going to happen...”
37
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on December 30, 2025, 08:50:17 AM »
Chapter 299.
He slipped on an old parka over his dress, and ran to the car park as fast as he could, leaving puzzled faces in his wake.
“Wasn’t that Tim? Where’s he off to? And what was he wearing?”
“He’s acting a bit odd these days…”
Serena was waiting. He jumped into the car, out of breath. She climbed in beside him.
“Are you okay?”
“I [gasp] didn’t wanna be [gasp] late…”
“Glad to see you’re so eager.”
“Why…today…?”
“Well, you’re lucky. One of our clients – Connie Brookshaw – happened to catch sight of one of the pictures we took of you during the photoshoot. She took an instant shine to you. She wants you for a party she’s giving at the beginning of December. So we need to speed up your training. From now on it’ll be weekends and Wednesdays.”
“What? But the weddin’…”
“Don’t worry about the wedding. Miss Poole spoke to Deborah to confirm a few days ago. Deborah’s really looking forward to meeting you. Unfortunately Bobby may have to miss it.”
“Why?”
“Because with your maid training the boot parlour bookings are getting backed up. Miss Poole can’t afford to lose both of you that Saturday. So she’s going to ask Bobby to stay and work at the Centre. Is that a problem?”
“No…”
Not at all, thought Tim. All the more attention for me.
“Yes, so it’s all arranged. Deborah says she’s thinking of letting you lead the procession in the church, with the bridesmaids behind. Would you be able to do that? I understand it’s asking a lot. It’s quite a responsibility, and you’ll have everyone staring at you. Don't feel you have to if it’s too, you know, difficult…”
“Course not! I ain’t scared. I’ll be, like, right at the front, yeah?”
This is great, he thought. Just me, no Bobby getting’ in the way, an’ I’ll be like, the main one…
“Oh, you’re such a brave boy, Tim. She’ll be so happy. She was hoping you might agree. I’ll let Cynthia know.”
“Cynthia?”
“You know, Cynthia at Fantastex. She’s promised to make you are special pair of shorts. A bit flashier than your usual red ones.”
“Yeah?”
“Yes. Specially for the wedding. She says the iconic colours for next year are purple and pink. She knows all these people in the trade, and she’s been told this is going to be the hip combination. You’ll have new shorts in purple and pink. You’ll be way ahead of the trend. What do you think of that?”
“Fantastic! Purple and pink, yeah? Cool…”
“Very cool. But don’t tell anyone, will you? Cynthia is buying up lots of purple and pink latex before the secret gets out.”
“I won’t Serena. I swear. I was getting’ worried I might miss the wedding. But it’s only Bobby who’ll miss out… And I’ll get a cool new outfit. Oh… But will I still be able to wear my baseball cap? The red vinyl one?”
“Of course! The idea is for you to wear a nice crisp white shirt, a red bow-tie, red shoes, and your red cap. You’ll look amazing…”
“Great! I can’t wait…”
“But this is all conditional on your completing your maid training by the end of the month. If you’re up to a sufficient standard by the time of the wedding, then you can have the Sunday off to do whatever you want. That’s the thirtieth. Then you’ll work for Connie the following weekend. Can I rely on you to study and practise hard for the next couple of weeks?”
“I promise! I’ll be the best maid you’ve ever seen!”
“Good boy. Now, we’re nearly at home. Then the ladies will take over. Carly will get you dressed and made up. My mum is here with Lucille, her business partner. One of them will have a chat with you to explain the schedule for the next couple of weeks. Listen carefully and remember what they tell you, yeah? You’ve already had an introduction, but it’ll become more intensive from now on. Just do what you’re told, focus, and practise. It won’t be easy, but I believe in you, Timothy. I would like to think you’ll be able to go to the wedding knowing you’re a fully-fledged maid as well as the smartest pageboy ever.”
They drew up outside Serena’s house. Tim was looking thoughtful.
“Everything okay, Tim? Any questions before I hand you over to the ladies?”
“This lady I’m gonna work for…”
“Mrs Brookshaw?”
“Yeah… What’s she like?”
“Oh, she’s nice. Strict but fair. Teri’s worked there a couple of times. He didn’t complain – not that he would. She’s in her forties. She has a big house just outside Bayleigh village. She’s single now, but sociable. Throws regular parties. Chairs the Bayleigh Women’s Institute. Rides. Runs a horse and donkey sanctuary. Nice lady. And a regular client.
“I see…”
“She’ll expect willingness, politeness, and efficiency. Strict obedience, of course – that goes without saying. So we need to get you up to speed as quickly as possible.”
“No problem,” said Tim, carelessly. He was confident he could make a great maid. As long as he got his new outfit for the wedding, that was all he cared about. “Pink and purple,” he mused. “Cool. And no Bobby getting’ in my way…”
He slipped on an old parka over his dress, and ran to the car park as fast as he could, leaving puzzled faces in his wake.
“Wasn’t that Tim? Where’s he off to? And what was he wearing?”
“He’s acting a bit odd these days…”
Serena was waiting. He jumped into the car, out of breath. She climbed in beside him.
“Are you okay?”
“I [gasp] didn’t wanna be [gasp] late…”
“Glad to see you’re so eager.”
“Why…today…?”
“Well, you’re lucky. One of our clients – Connie Brookshaw – happened to catch sight of one of the pictures we took of you during the photoshoot. She took an instant shine to you. She wants you for a party she’s giving at the beginning of December. So we need to speed up your training. From now on it’ll be weekends and Wednesdays.”
“What? But the weddin’…”
“Don’t worry about the wedding. Miss Poole spoke to Deborah to confirm a few days ago. Deborah’s really looking forward to meeting you. Unfortunately Bobby may have to miss it.”
“Why?”
“Because with your maid training the boot parlour bookings are getting backed up. Miss Poole can’t afford to lose both of you that Saturday. So she’s going to ask Bobby to stay and work at the Centre. Is that a problem?”
“No…”
Not at all, thought Tim. All the more attention for me.
“Yes, so it’s all arranged. Deborah says she’s thinking of letting you lead the procession in the church, with the bridesmaids behind. Would you be able to do that? I understand it’s asking a lot. It’s quite a responsibility, and you’ll have everyone staring at you. Don't feel you have to if it’s too, you know, difficult…”
“Course not! I ain’t scared. I’ll be, like, right at the front, yeah?”
This is great, he thought. Just me, no Bobby getting’ in the way, an’ I’ll be like, the main one…
“Oh, you’re such a brave boy, Tim. She’ll be so happy. She was hoping you might agree. I’ll let Cynthia know.”
“Cynthia?”
“You know, Cynthia at Fantastex. She’s promised to make you are special pair of shorts. A bit flashier than your usual red ones.”
“Yeah?”
“Yes. Specially for the wedding. She says the iconic colours for next year are purple and pink. She knows all these people in the trade, and she’s been told this is going to be the hip combination. You’ll have new shorts in purple and pink. You’ll be way ahead of the trend. What do you think of that?”
“Fantastic! Purple and pink, yeah? Cool…”
“Very cool. But don’t tell anyone, will you? Cynthia is buying up lots of purple and pink latex before the secret gets out.”
“I won’t Serena. I swear. I was getting’ worried I might miss the wedding. But it’s only Bobby who’ll miss out… And I’ll get a cool new outfit. Oh… But will I still be able to wear my baseball cap? The red vinyl one?”
“Of course! The idea is for you to wear a nice crisp white shirt, a red bow-tie, red shoes, and your red cap. You’ll look amazing…”
“Great! I can’t wait…”
“But this is all conditional on your completing your maid training by the end of the month. If you’re up to a sufficient standard by the time of the wedding, then you can have the Sunday off to do whatever you want. That’s the thirtieth. Then you’ll work for Connie the following weekend. Can I rely on you to study and practise hard for the next couple of weeks?”
“I promise! I’ll be the best maid you’ve ever seen!”
“Good boy. Now, we’re nearly at home. Then the ladies will take over. Carly will get you dressed and made up. My mum is here with Lucille, her business partner. One of them will have a chat with you to explain the schedule for the next couple of weeks. Listen carefully and remember what they tell you, yeah? You’ve already had an introduction, but it’ll become more intensive from now on. Just do what you’re told, focus, and practise. It won’t be easy, but I believe in you, Timothy. I would like to think you’ll be able to go to the wedding knowing you’re a fully-fledged maid as well as the smartest pageboy ever.”
They drew up outside Serena’s house. Tim was looking thoughtful.
“Everything okay, Tim? Any questions before I hand you over to the ladies?”
“This lady I’m gonna work for…”
“Mrs Brookshaw?”
“Yeah… What’s she like?”
“Oh, she’s nice. Strict but fair. Teri’s worked there a couple of times. He didn’t complain – not that he would. She’s in her forties. She has a big house just outside Bayleigh village. She’s single now, but sociable. Throws regular parties. Chairs the Bayleigh Women’s Institute. Rides. Runs a horse and donkey sanctuary. Nice lady. And a regular client.
“I see…”
“She’ll expect willingness, politeness, and efficiency. Strict obedience, of course – that goes without saying. So we need to get you up to speed as quickly as possible.”
“No problem,” said Tim, carelessly. He was confident he could make a great maid. As long as he got his new outfit for the wedding, that was all he cared about. “Pink and purple,” he mused. “Cool. And no Bobby getting’ in my way…”
38
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on December 30, 2025, 08:28:05 AM »
Chapter 298.
When the ESDS had finished with Tim that Sunday evening, they sent him home in the pretty yellow dress he had been given the day before, and with his chastity device firmly locked in place - telling him it was a compulsory accessory and that he should get used to it. Serena dropped him in the car park. Fortunately it was already dark, and he managed to make it back without being recognised. Bobby was surprised to see him in a dress – but impressed by how pretty he looked.
“Wow, Tim! What’s with the dress? I never thought I’d see you of all people…”
“Whatcher mean? It’s just a blinkin’ dress. You wear one whenever you can, so ‘oo are you to say I can’t?”
No, I didn’t mean it like that... I mean, you look really nice – I mean cool – in it. It’s was just a bit of a shock…”
“You didn’t fink I could carry it off, right? Well now you know I can. I can look just as good as you in anyfink.”
“Of course. Did you have a good day? I heard you went off with Serena and her mates…”
“Yeah…”
Bobby waited for elaboration.
“Yeah… Like, I must ‘ave made an impression on ‘er when she came ‘ere. … Met ‘er mum too, and ‘er friends…”
“Oh, I see. That’s nice.” Bobby could sense Tim didn’t want to talk about it, and decided not to question him further, certain that he’d spill everything when he was ready.
Tim was eager to change the subject. “You ‘ad a busy day, I ‘ear. Mellie in the mornin’, and pony rides in the afternoon. You must be knackered, mate…”
“I am… Some of them were definitely too heavy. I’m sure they were over the weight limit. But there was this girl…”
And he told Tim all about the surprise supervisor in a pink latex catsuit who had totally stolen Mélisande’s thunder. But Tim was still distracted, and hardly listening…
His humiliation at the hands of the ESDS weighed on him during the succeeding days, making him irritable and anxious. He had so been looking forward to the wedding, parading about in his pageboy outfit, but now that wasn’t happening for another two weeks, and he had weekend maid training hanging over him. Things took another turn for the worse on the Wednesday - the day of Thomsina's hack. At seven-thirty that morning Ellie rapped sharply at his bedroom door.
“Tim? You awake?”
“Wha’? What is it…?”
“Miss Poole says you have to wear your dress – btw, I didn’t know you had a dress – anyway, she says you have to put on your dress and meet Mrs Egerton in the car park at quarter to nine.”
“What? But it’s a work day… Why?”
“No idea. I’m just the messenger. Better get up and shower.” She sniggered. “I’m not going anywhere till I see this dress!”
“Shit…”
Ellie was annoyingly impressed by Tim’s Dress.
“Darling! You look gorgeous! Doesn’t he Bobby? A real sweetie!”
“I know. You should have seen him Sunday night, with all his makeup on. I thought my luck hand changed!”
“Didn’t you get a picture?”
“Nah. Wouldn’t let me. He was so grumpy…”
“Oh my god… Shame. I’ll have ask Serena for a few when I see her…”
“Don’t you dare, Ellie!” cried Tim, terrified his secret would come out.
“Why not? You look so cute. I can put it on the big noticeboard…”
“No… Please don’t…”
“What are you so worried about? Bobby’s not ashamed of his dress.”
“Okay. Don’t ask her, though. Look, I’ll let you take one of me in my dress and with makeup. Okay?”
“Okay… If you will… It would be easier for me to ask Serena…”
“No! Don’t do that. She’s so busy… I promise to come back with makeup on tonight…”
“All right.” Ellie looked suspicious. “But I’ll hold you to that.”
“Fine.”
Tim couldn’t explain. But if Ellie spoke to Serena, then his maid training project would end up being the talk of the Centre. He had somehow to keep it separate…
When the ESDS had finished with Tim that Sunday evening, they sent him home in the pretty yellow dress he had been given the day before, and with his chastity device firmly locked in place - telling him it was a compulsory accessory and that he should get used to it. Serena dropped him in the car park. Fortunately it was already dark, and he managed to make it back without being recognised. Bobby was surprised to see him in a dress – but impressed by how pretty he looked.
“Wow, Tim! What’s with the dress? I never thought I’d see you of all people…”
“Whatcher mean? It’s just a blinkin’ dress. You wear one whenever you can, so ‘oo are you to say I can’t?”
No, I didn’t mean it like that... I mean, you look really nice – I mean cool – in it. It’s was just a bit of a shock…”
“You didn’t fink I could carry it off, right? Well now you know I can. I can look just as good as you in anyfink.”
“Of course. Did you have a good day? I heard you went off with Serena and her mates…”
“Yeah…”
Bobby waited for elaboration.
“Yeah… Like, I must ‘ave made an impression on ‘er when she came ‘ere. … Met ‘er mum too, and ‘er friends…”
“Oh, I see. That’s nice.” Bobby could sense Tim didn’t want to talk about it, and decided not to question him further, certain that he’d spill everything when he was ready.
Tim was eager to change the subject. “You ‘ad a busy day, I ‘ear. Mellie in the mornin’, and pony rides in the afternoon. You must be knackered, mate…”
“I am… Some of them were definitely too heavy. I’m sure they were over the weight limit. But there was this girl…”
And he told Tim all about the surprise supervisor in a pink latex catsuit who had totally stolen Mélisande’s thunder. But Tim was still distracted, and hardly listening…
His humiliation at the hands of the ESDS weighed on him during the succeeding days, making him irritable and anxious. He had so been looking forward to the wedding, parading about in his pageboy outfit, but now that wasn’t happening for another two weeks, and he had weekend maid training hanging over him. Things took another turn for the worse on the Wednesday - the day of Thomsina's hack. At seven-thirty that morning Ellie rapped sharply at his bedroom door.
“Tim? You awake?”
“Wha’? What is it…?”
“Miss Poole says you have to wear your dress – btw, I didn’t know you had a dress – anyway, she says you have to put on your dress and meet Mrs Egerton in the car park at quarter to nine.”
“What? But it’s a work day… Why?”
“No idea. I’m just the messenger. Better get up and shower.” She sniggered. “I’m not going anywhere till I see this dress!”
“Shit…”
Ellie was annoyingly impressed by Tim’s Dress.
“Darling! You look gorgeous! Doesn’t he Bobby? A real sweetie!”
“I know. You should have seen him Sunday night, with all his makeup on. I thought my luck hand changed!”
“Didn’t you get a picture?”
“Nah. Wouldn’t let me. He was so grumpy…”
“Oh my god… Shame. I’ll have ask Serena for a few when I see her…”
“Don’t you dare, Ellie!” cried Tim, terrified his secret would come out.
“Why not? You look so cute. I can put it on the big noticeboard…”
“No… Please don’t…”
“What are you so worried about? Bobby’s not ashamed of his dress.”
“Okay. Don’t ask her, though. Look, I’ll let you take one of me in my dress and with makeup. Okay?”
“Okay… If you will… It would be easier for me to ask Serena…”
“No! Don’t do that. She’s so busy… I promise to come back with makeup on tonight…”
“All right.” Ellie looked suspicious. “But I’ll hold you to that.”
“Fine.”
Tim couldn’t explain. But if Ellie spoke to Serena, then his maid training project would end up being the talk of the Centre. He had somehow to keep it separate…
39
Active Sissy Stories / Re: Proof of Intent
« Last post by mikeh1993 on December 25, 2025, 01:19:28 PM »
Another great Antonia story. I loved it. Thanks for shaving it
40
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on December 24, 2025, 07:30:38 PM »
Thank you, RibbonBound, and I hope you have a great Christmas!
The more you give, the more I can give back.
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