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Active Sissy Stories / Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on Yesterday at 09:56:08 AM »
The Evening's Close
Later, when their first study hall finally ended, the boys packed up their things and made sure to take their new Gamma Delta study guides with them. The newly minted Delta Darlings dejectedly went back to change into their regular clothes. They were each acutely aware of the soft swish of their skirts and the gentle cling of lace against their skin. Nate gave a small sigh of relief as he tugged on his familiar jeans and hoodie. The coarse denim and loose cotton felt reassuringly ordinary, but the ritual of changing back into his regular clothes suddenly felt far from routine. The delicate lace beneath his clothes reminded him that he was still in uncharted territory, and it not for the first time of the evening he found himself having an unwelcome physical reaction to his frilly panties. Although they didn’t discuss it, he was not the only one. Milo, always one to maintain a brave facade, moved with more composure. On the surface, he appeared somewhat less self-conscious as he neatly hung up his Gamma Delta study clothes.
Julian moved deliberately and seemed to linger a bit, hanging his skirt and blouse on their hangers with gentle care. His fingers traced the soft fabric almost wistfully. He blushed as he realized what he was doing. Owen changed rapidly, his face set. His motions were almost mechanical. He tried to ignore the persistent tickling of his lacy bra beneath his shirt, and his heart beat rapidly as the events of the evening crashed down on him.
As they left the Gamma Delta house, the boys walked in near silence as they became lost in their own thoughts. By going through tonight’s “initiations,” they had each been awarded 10 points. They should have had 40 points, but their group total stood at 39 toward the goal of 1000 after Owen’s lost point. It seemed hollow, however, as they realized all the potential ways in their future to rapidly lose ground. The boys had the distinct impression that the Sisters had taken it easy on them since it was the first night.
Still trying to make sense of what they had gone through, Owen broke the quiet with a pointed question, “Does anybody still think this is going to be over in a month?”
The silence that followed provided a clear answer.
Nate finally sighed quietly, “Don’t forget to do your journals tonight, guys.”
Their first study hall evening had left them all feeling exhausted and spent. They seemed to heave a collective sigh to be reminded of yet another task ahead. They drifted slowly apart and trudged to their own rooms, trying not to be noticed in their still made-up faces. Each boy was acutely aware of the unfamiliar feel of mascara on their lashes and the faint shimmer of gloss on their lips. The fear of being recognized or called out by the other guys in the dorm sent their hearts racing. Every distant laugh, every creak of a door, made them tense, worrying that someone would catch sight of their prettily made-up faces. Once back in their own rooms, they all soon discovered that removing their makeup was a chore in itself. Even after some wiping, they found their cheeks still tinged with stubborn color and felt all the more exposed for it. Their makeup seemed to determinedly hang on despite their efforts. Then, they all reluctantly sat down to process their emotions and begin writing in their journals about being transfomed into “Delta Darlings.”
Later, when their first study hall finally ended, the boys packed up their things and made sure to take their new Gamma Delta study guides with them. The newly minted Delta Darlings dejectedly went back to change into their regular clothes. They were each acutely aware of the soft swish of their skirts and the gentle cling of lace against their skin. Nate gave a small sigh of relief as he tugged on his familiar jeans and hoodie. The coarse denim and loose cotton felt reassuringly ordinary, but the ritual of changing back into his regular clothes suddenly felt far from routine. The delicate lace beneath his clothes reminded him that he was still in uncharted territory, and it not for the first time of the evening he found himself having an unwelcome physical reaction to his frilly panties. Although they didn’t discuss it, he was not the only one. Milo, always one to maintain a brave facade, moved with more composure. On the surface, he appeared somewhat less self-conscious as he neatly hung up his Gamma Delta study clothes.
Julian moved deliberately and seemed to linger a bit, hanging his skirt and blouse on their hangers with gentle care. His fingers traced the soft fabric almost wistfully. He blushed as he realized what he was doing. Owen changed rapidly, his face set. His motions were almost mechanical. He tried to ignore the persistent tickling of his lacy bra beneath his shirt, and his heart beat rapidly as the events of the evening crashed down on him.
As they left the Gamma Delta house, the boys walked in near silence as they became lost in their own thoughts. By going through tonight’s “initiations,” they had each been awarded 10 points. They should have had 40 points, but their group total stood at 39 toward the goal of 1000 after Owen’s lost point. It seemed hollow, however, as they realized all the potential ways in their future to rapidly lose ground. The boys had the distinct impression that the Sisters had taken it easy on them since it was the first night.
Still trying to make sense of what they had gone through, Owen broke the quiet with a pointed question, “Does anybody still think this is going to be over in a month?”
The silence that followed provided a clear answer.
Nate finally sighed quietly, “Don’t forget to do your journals tonight, guys.”
Their first study hall evening had left them all feeling exhausted and spent. They seemed to heave a collective sigh to be reminded of yet another task ahead. They drifted slowly apart and trudged to their own rooms, trying not to be noticed in their still made-up faces. Each boy was acutely aware of the unfamiliar feel of mascara on their lashes and the faint shimmer of gloss on their lips. The fear of being recognized or called out by the other guys in the dorm sent their hearts racing. Every distant laugh, every creak of a door, made them tense, worrying that someone would catch sight of their prettily made-up faces. Once back in their own rooms, they all soon discovered that removing their makeup was a chore in itself. Even after some wiping, they found their cheeks still tinged with stubborn color and felt all the more exposed for it. Their makeup seemed to determinedly hang on despite their efforts. Then, they all reluctantly sat down to process their emotions and begin writing in their journals about being transfomed into “Delta Darlings.”
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 21, 2025, 04:14:54 PM »
Chapter 283.
Lady Middiford led the way out of the office, which was on South Kennett High Street. She turned left and walked briskly, saying nothing. Thomasina caught up with her and took her arm.
“Mummy… Please don’t be angry. I’m really sorry…”
“No you’re not. And I ‘m not angry. Actually I’m rather pleased. You stood up for yourself. You showed strength I hadn’t recognised. I’m rather proud of you, darling.”
She stopped and gave her daughter a hug.
“We’re going to Roberts’ Tack Shop. I want you to buy a couple of new outfits. Nothing fancy, just good quality standard stuff. You want to stay at Pitt’s Wood, right?”
“Very much…”
“I thought so. So no more showing off. Just fit in. Do you get on with Miss Poole?”
“I think I do…now.”
“Then she doesn’t hold grudges?”
“Oh, no. She’s not that sort at all. She’s quite nice and ordinary… Very down-to-earth.”
“Yes. I see. I think I need to pay her a visit… Explain myself. Apologise.”
“Would you do that?”
“She sounds like someone I could do business with. Also, I’m interested. I’ve heard some lurid rumours about that place. It rather intrigues me…”
A phone call was all it took to arrange a visit, and at three that afternoon the two ladies found themselves facing each other across Miss Poole’s desk.
“It’s good to meet you, Lady Middiford. You have a very talented daughter.”
“I know. You received my solicitor’s letter, I suppose?”
“Yes. I’m very grateful…”
“You shouldn’t be. What I did was unforgiveable. I realise that now, since my daughter opened up about it all. Miss Poole, I sincerely apologise for my actions, for which I take full responsibility. Also for the tone of my lawyer’s first letter, which was sent without my approval.”
“Please, forget it. Let’s put it in the past. And please, call me Violet.”
“I appreciate your understanding more than I can say, Violet. And please call me Edith. Now, what about the girl who was dismissed?”
“Oh, I let her resign, and gave her a good reference, and three months pay in lieu of notice. Don’t worry about her. There had been other incidents. And she’s working at another centre now.”
“I see. That does make me feel a little better. I was going to offer some money as compensation.”
“Not necessary, I assure you.”
“Well, in that case I’ll direct it elsewhere. I understand you have a fund for less well-off children, for lessons and clothing. How can I donate?”
“That’s very kind, Edith. I can send you a link.”
“Please do.” She paused. “Can I ask you something?”
“Of course, Edith.”
“I’ve heard some quite unusual things about Pitt’s Wood. I read in the paper about a Ponyboy? Is that the correct term?”
“Ah…our Ponyboy…yes, that’s right.”
“He gets ridden like a pony?”
“Yes… He’s the nephew of a good friend of mine. He has a regular rider, a girl called Mélisande, the daughter of another friend. They have a real rapport…”
“I see… When I heard about it I found the idea rather appealing. And then, Thomasina tells me, you also established something called a boot parlour? Run by a couple of boys…?”
“Well, yes, we did. Actually it’s doing rather well…”
“Is it true that these boys…how old are they?”
“Seventeen.”
“ Yes, seventeen. It is true that these seventeen-year-old boys are employed just for the purpose of cleaning and polishing boots?”
“Yes…”
“Which they do while the owners are wearing them?”
“Usually, yes…”
“On their knees like servants?”
“Well…yes…”
“And they are required to wear special uniforms, I believe…”
“What are they like?”
“The boys?”
“Well, the boys, yes. But the uniforms?”
“Well, Edith, if you care to look at that photograph on the wall behind the door… Yes, that one… You’ll be able to see both the boys and their uniforms…”
Edith rose and approached the picture. Bobby and Tim, both in their pageboy outfits, holding hands outside the boot parlour, and looking rather self-conscious. She stared at it for a long time...then turned and smiled.
“What a fantastic idea! I can’t think of a better way for two good-looking young guys to spend their time. That’s such a sweet photo.”
“I’ve got copies. Would you like one?”
“I’d love one! Thank you. So this was your idea, Violet?”
“Yes. It’s been good for the Centre, and the boys are well-paid, and that’s aside from the tips. Why don’t you book a session? Just call at reception and book a date.”
“Oh, don’t worry. Now I’ve seen them, I intend to. So good to see big strong boys like that usefully employed. And so good that they dedicate themselves to the service of the opposite sex. Some would baulk at that. I wonder… Do they offer any other services?”
“Well I like to leave that entirely to the discretion of the customer. They also do home visits.”
“Really? I wish I’d known about this earlier. I have to confess, as a single woman, I’ve always wondered what it would be like to have a male domestic. Most of them aren’t very presentable, but these guys…”
“Well, funny you should say that, but I do know of an agency… ESDS – Egerton’s Special Domestic Services – which might be just up your street. This is run by another friend of mine, Cassandra Egerton. Actually I’m a sort of partner. The website’s private – you’d need to be an approved member – of course we can easily arrange that - but I can show you a brochure…”
She reached into a drawer I her desk and produced a leaflet, which she handed to Lady Middiford. On the front was a picture of a boy in maid’s uniform holding a feather duster. She stared.
“Oh my god… He’s so cute… What’s his name? Philip! And this one inside… Darren! They’re so sweet! So, I could actually hire these as maids?”
“What, Edith? You want two?”
“No… You know that’s not what I mean Violet. Either one would be lovely. And they look so happy! It would brighten my day just to have either one around. They wouldn’t actually have to do anything. Just their presence would be enough…”
“I’ll speak to Cassandra and get you access to the site. She’s away for a few days, so it won’t be till the end of the week. Actually Tim - he's the one on the right of the picture I gave you - Tim's just starting maid training there. It take about a month to get them to a sufficient standard, but then I hope he'll be on the website too. Oh, I’m so glad you called in, and that you approve of our little projects.”
“Oh, Violet, so am I. It’s been such a pleasure to meet you. We seem to have so much in common. We must get together soon for a good old chinwag. I’ll invite you for dinner, if that’s okay.”
“I’d love to come. And don’t worry about Thomasina. We’re going to take very good care of her…”
Lady Middiford led the way out of the office, which was on South Kennett High Street. She turned left and walked briskly, saying nothing. Thomasina caught up with her and took her arm.
“Mummy… Please don’t be angry. I’m really sorry…”
“No you’re not. And I ‘m not angry. Actually I’m rather pleased. You stood up for yourself. You showed strength I hadn’t recognised. I’m rather proud of you, darling.”
She stopped and gave her daughter a hug.
“We’re going to Roberts’ Tack Shop. I want you to buy a couple of new outfits. Nothing fancy, just good quality standard stuff. You want to stay at Pitt’s Wood, right?”
“Very much…”
“I thought so. So no more showing off. Just fit in. Do you get on with Miss Poole?”
“I think I do…now.”
“Then she doesn’t hold grudges?”
“Oh, no. She’s not that sort at all. She’s quite nice and ordinary… Very down-to-earth.”
“Yes. I see. I think I need to pay her a visit… Explain myself. Apologise.”
“Would you do that?”
“She sounds like someone I could do business with. Also, I’m interested. I’ve heard some lurid rumours about that place. It rather intrigues me…”
A phone call was all it took to arrange a visit, and at three that afternoon the two ladies found themselves facing each other across Miss Poole’s desk.
“It’s good to meet you, Lady Middiford. You have a very talented daughter.”
“I know. You received my solicitor’s letter, I suppose?”
“Yes. I’m very grateful…”
“You shouldn’t be. What I did was unforgiveable. I realise that now, since my daughter opened up about it all. Miss Poole, I sincerely apologise for my actions, for which I take full responsibility. Also for the tone of my lawyer’s first letter, which was sent without my approval.”
“Please, forget it. Let’s put it in the past. And please, call me Violet.”
“I appreciate your understanding more than I can say, Violet. And please call me Edith. Now, what about the girl who was dismissed?”
“Oh, I let her resign, and gave her a good reference, and three months pay in lieu of notice. Don’t worry about her. There had been other incidents. And she’s working at another centre now.”
“I see. That does make me feel a little better. I was going to offer some money as compensation.”
“Not necessary, I assure you.”
“Well, in that case I’ll direct it elsewhere. I understand you have a fund for less well-off children, for lessons and clothing. How can I donate?”
“That’s very kind, Edith. I can send you a link.”
“Please do.” She paused. “Can I ask you something?”
“Of course, Edith.”
“I’ve heard some quite unusual things about Pitt’s Wood. I read in the paper about a Ponyboy? Is that the correct term?”
“Ah…our Ponyboy…yes, that’s right.”
“He gets ridden like a pony?”
“Yes… He’s the nephew of a good friend of mine. He has a regular rider, a girl called Mélisande, the daughter of another friend. They have a real rapport…”
“I see… When I heard about it I found the idea rather appealing. And then, Thomasina tells me, you also established something called a boot parlour? Run by a couple of boys…?”
“Well, yes, we did. Actually it’s doing rather well…”
“Is it true that these boys…how old are they?”
“Seventeen.”
“ Yes, seventeen. It is true that these seventeen-year-old boys are employed just for the purpose of cleaning and polishing boots?”
“Yes…”
“Which they do while the owners are wearing them?”
“Usually, yes…”
“On their knees like servants?”
“Well…yes…”
“And they are required to wear special uniforms, I believe…”
“What are they like?”
“The boys?”
“Well, the boys, yes. But the uniforms?”
“Well, Edith, if you care to look at that photograph on the wall behind the door… Yes, that one… You’ll be able to see both the boys and their uniforms…”
Edith rose and approached the picture. Bobby and Tim, both in their pageboy outfits, holding hands outside the boot parlour, and looking rather self-conscious. She stared at it for a long time...then turned and smiled.
“What a fantastic idea! I can’t think of a better way for two good-looking young guys to spend their time. That’s such a sweet photo.”
“I’ve got copies. Would you like one?”
“I’d love one! Thank you. So this was your idea, Violet?”
“Yes. It’s been good for the Centre, and the boys are well-paid, and that’s aside from the tips. Why don’t you book a session? Just call at reception and book a date.”
“Oh, don’t worry. Now I’ve seen them, I intend to. So good to see big strong boys like that usefully employed. And so good that they dedicate themselves to the service of the opposite sex. Some would baulk at that. I wonder… Do they offer any other services?”
“Well I like to leave that entirely to the discretion of the customer. They also do home visits.”
“Really? I wish I’d known about this earlier. I have to confess, as a single woman, I’ve always wondered what it would be like to have a male domestic. Most of them aren’t very presentable, but these guys…”
“Well, funny you should say that, but I do know of an agency… ESDS – Egerton’s Special Domestic Services – which might be just up your street. This is run by another friend of mine, Cassandra Egerton. Actually I’m a sort of partner. The website’s private – you’d need to be an approved member – of course we can easily arrange that - but I can show you a brochure…”
She reached into a drawer I her desk and produced a leaflet, which she handed to Lady Middiford. On the front was a picture of a boy in maid’s uniform holding a feather duster. She stared.
“Oh my god… He’s so cute… What’s his name? Philip! And this one inside… Darren! They’re so sweet! So, I could actually hire these as maids?”
“What, Edith? You want two?”
“No… You know that’s not what I mean Violet. Either one would be lovely. And they look so happy! It would brighten my day just to have either one around. They wouldn’t actually have to do anything. Just their presence would be enough…”
“I’ll speak to Cassandra and get you access to the site. She’s away for a few days, so it won’t be till the end of the week. Actually Tim - he's the one on the right of the picture I gave you - Tim's just starting maid training there. It take about a month to get them to a sufficient standard, but then I hope he'll be on the website too. Oh, I’m so glad you called in, and that you approve of our little projects.”
“Oh, Violet, so am I. It’s been such a pleasure to meet you. We seem to have so much in common. We must get together soon for a good old chinwag. I’ll invite you for dinner, if that’s okay.”
“I’d love to come. And don’t worry about Thomasina. We’re going to take very good care of her…”
3
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 21, 2025, 07:25:39 AM »
Chapter 282.
Monday. Thomasina’s appointment was at ten. It was a chilly day, and she dressed herself warmly in leggings, boots, and a thick roll-neck jumper. Her mother drove her. The car warmed up. Lady Middiford sniffed.
“What’s that smell?”
“Smell?”
“Sort of rubbery smell.”
“Probably something in the heater.”
“Hmph.”
Caspar, Pugilmain and Snipe was a typical provincial firm of solicitors; three partners, two assistants, an articled clerk, the partners all with a self-satisfied auras of superiority and more or less unimaginative. They couldn’t, for instance, imagine a client who thought she knew better than they, or who dared to challenge their decisions. For them, even the great and noble, even the rich – especially the rich – should come to them hats in hand, pleading for advice. Today their illusions of invincibility were about to be shattered.
The senior parter, Archibald (never dare to call me Archie) Pugilmain, showed them into his office with a cool motion of his well-manicured hand.
“Lady Middiford, a pleasure to see you…and your fair daughter…” (He had already forgotten Thomasina’s name.) “Please…take a seat. I trust you are both well…?”
“Thank you, Mr Pugilmain… Very well.”
“May I ask…have you heard anything from, er…” He consulted his file. “Ah, yes, Miss Poole, is it? As I said, we have had nothing as yet…”
“Of course not. Not a word from that woman – horse-trainer, whatever she is. Didn’t expect it. Lowest of the low. Probably a gypsy, by the sound of her.”
“Ah, yes…quite. Well, then, let us proceed. Your daughter here, er…”
“Thomasina,” piped up Thomasina, looking at Pugilmain with an amused expression, which for a moment confused him slightly.
“Ah, yes, Tommer…”
“Sina.”
“So, er, Tommerseener, all we need is your statement of the unfortunate events of that day in September.” He tried to assume an expression of empathy, but as that was a quality entirely absent from his character, the attempt failed. “I hope the recollection will not be too distressing.”
Lady Middiford was beginning to look impatient, no doubt recalling Mr Pugilmain’s hourly rate, so he started recording.
“Please go ahead.”
“I have to make a confession. I apologise for wasting everyone’s time – and your money, mummy.”
This was said in the most unapologetic tone imaginable. Indeed, it appeared that Thomasina was actually smiling. Lady Middiford’s eyes widened slightly Pugilmain looked mildly surprised, but as yet unconcerned.
“I was probably rather distressed that day. I may have exaggerated. That’s my excuse, anyway. But mummy? I think you also over-reacted. I know you must have wanted to defend me, so I understand. But whatever, I want to put the record straight. I was pushed around a bit, but upon reflection I think I probably provoked the whole incident. Those girls were always jealous of my expensive gear. It wasn’t unnatural, considering how hard up most of them are. I did nothing to appease them. On the contrary, I flaunted my greater wealth and made them even more resentful. It was stupid and crass and mean, and I regret it sincerely. I got one of them sacked. At the time I was pleased. Now I realise that perhaps that was the outcome I was unconsciously hoping for. I feel responsible for the whole thing. If anyone is guilty, it’s me. As for Miss Poole, she took immediate action. It’s quite unfair that we should seek to take legal action against her or the Centre. I apologised to her yesterday. We should withdraw that horrible letter that Mr Plugilman wrote.” (She particularly enjoyed mispronouncing his name, especially as that seemed to upset him even more than the substance of her statement.) “Mummy, I’m sorry if I bent the truth that evening when I told you what had happened. I wanted to put things right, but I was frightened that you would be angry with me. And then things sort of…got out of hand… Please understand…”
She hung her head. Her mother peered at her. She couldn’t tell whether she was about to cry…or whether there was a faint smile on her lips. The rubbery smell seemed to have pursued them into Mr Pugilmain’s office. Perhaps it had got into their clothes…
Pugilmain looked at Lady Middiford with a sort of “who can tell what goes on in young girls’ heads” expression. It was a pity. But at least he’s be able to charge for the letter of retraction. That would cost more than the letter of intent, involving as it would subtle, lawyerly rhetoric withdrawing threats whilst avoiding apologies. As to the daughter’s statement, he was interested how Lady Middiford would react. He anticipated an explosion.
But she wasn’t stupid. Pugilmain had sent the letter without running it past her. She was not happy about that, and she didn’t like him much anyway. His smugness reminded her of her ex-husband, who she had divorced eight years before. And she couldn’t help feeling proud of Thomasina for having a conscience and being so courageous. It seemed she had been growing up with her noticing.
“Right. Now we know the position. Mr Pugilmain, please send a letter of retraction. A simple letter to Miss Poole asking her to ignore your first one – which I didn’t like anyway.”
Pugilmain looked offended, but she ignored him.
“And this time please copy me the draft before you send it. It’ll be a short letter, so please do it this morning, email it to me, I will approve or amend it immediately and you can email it to Miss Poole. I’ll deal with the rest.”
“But Lady Middiford, I think we need to be very careful what we say…”
“No. Don’t be careful. Just do as I’ve asked. Come, Thomasina. We need to do some shopping before lunch. By two, please, Mr Pugilmain. No later than two. Good morning.”
Monday. Thomasina’s appointment was at ten. It was a chilly day, and she dressed herself warmly in leggings, boots, and a thick roll-neck jumper. Her mother drove her. The car warmed up. Lady Middiford sniffed.
“What’s that smell?”
“Smell?”
“Sort of rubbery smell.”
“Probably something in the heater.”
“Hmph.”
Caspar, Pugilmain and Snipe was a typical provincial firm of solicitors; three partners, two assistants, an articled clerk, the partners all with a self-satisfied auras of superiority and more or less unimaginative. They couldn’t, for instance, imagine a client who thought she knew better than they, or who dared to challenge their decisions. For them, even the great and noble, even the rich – especially the rich – should come to them hats in hand, pleading for advice. Today their illusions of invincibility were about to be shattered.
The senior parter, Archibald (never dare to call me Archie) Pugilmain, showed them into his office with a cool motion of his well-manicured hand.
“Lady Middiford, a pleasure to see you…and your fair daughter…” (He had already forgotten Thomasina’s name.) “Please…take a seat. I trust you are both well…?”
“Thank you, Mr Pugilmain… Very well.”
“May I ask…have you heard anything from, er…” He consulted his file. “Ah, yes, Miss Poole, is it? As I said, we have had nothing as yet…”
“Of course not. Not a word from that woman – horse-trainer, whatever she is. Didn’t expect it. Lowest of the low. Probably a gypsy, by the sound of her.”
“Ah, yes…quite. Well, then, let us proceed. Your daughter here, er…”
“Thomasina,” piped up Thomasina, looking at Pugilmain with an amused expression, which for a moment confused him slightly.
“Ah, yes, Tommer…”
“Sina.”
“So, er, Tommerseener, all we need is your statement of the unfortunate events of that day in September.” He tried to assume an expression of empathy, but as that was a quality entirely absent from his character, the attempt failed. “I hope the recollection will not be too distressing.”
Lady Middiford was beginning to look impatient, no doubt recalling Mr Pugilmain’s hourly rate, so he started recording.
“Please go ahead.”
“I have to make a confession. I apologise for wasting everyone’s time – and your money, mummy.”
This was said in the most unapologetic tone imaginable. Indeed, it appeared that Thomasina was actually smiling. Lady Middiford’s eyes widened slightly Pugilmain looked mildly surprised, but as yet unconcerned.
“I was probably rather distressed that day. I may have exaggerated. That’s my excuse, anyway. But mummy? I think you also over-reacted. I know you must have wanted to defend me, so I understand. But whatever, I want to put the record straight. I was pushed around a bit, but upon reflection I think I probably provoked the whole incident. Those girls were always jealous of my expensive gear. It wasn’t unnatural, considering how hard up most of them are. I did nothing to appease them. On the contrary, I flaunted my greater wealth and made them even more resentful. It was stupid and crass and mean, and I regret it sincerely. I got one of them sacked. At the time I was pleased. Now I realise that perhaps that was the outcome I was unconsciously hoping for. I feel responsible for the whole thing. If anyone is guilty, it’s me. As for Miss Poole, she took immediate action. It’s quite unfair that we should seek to take legal action against her or the Centre. I apologised to her yesterday. We should withdraw that horrible letter that Mr Plugilman wrote.” (She particularly enjoyed mispronouncing his name, especially as that seemed to upset him even more than the substance of her statement.) “Mummy, I’m sorry if I bent the truth that evening when I told you what had happened. I wanted to put things right, but I was frightened that you would be angry with me. And then things sort of…got out of hand… Please understand…”
She hung her head. Her mother peered at her. She couldn’t tell whether she was about to cry…or whether there was a faint smile on her lips. The rubbery smell seemed to have pursued them into Mr Pugilmain’s office. Perhaps it had got into their clothes…
Pugilmain looked at Lady Middiford with a sort of “who can tell what goes on in young girls’ heads” expression. It was a pity. But at least he’s be able to charge for the letter of retraction. That would cost more than the letter of intent, involving as it would subtle, lawyerly rhetoric withdrawing threats whilst avoiding apologies. As to the daughter’s statement, he was interested how Lady Middiford would react. He anticipated an explosion.
But she wasn’t stupid. Pugilmain had sent the letter without running it past her. She was not happy about that, and she didn’t like him much anyway. His smugness reminded her of her ex-husband, who she had divorced eight years before. And she couldn’t help feeling proud of Thomasina for having a conscience and being so courageous. It seemed she had been growing up with her noticing.
“Right. Now we know the position. Mr Pugilmain, please send a letter of retraction. A simple letter to Miss Poole asking her to ignore your first one – which I didn’t like anyway.”
Pugilmain looked offended, but she ignored him.
“And this time please copy me the draft before you send it. It’ll be a short letter, so please do it this morning, email it to me, I will approve or amend it immediately and you can email it to Miss Poole. I’ll deal with the rest.”
“But Lady Middiford, I think we need to be very careful what we say…”
“No. Don’t be careful. Just do as I’ve asked. Come, Thomasina. We need to do some shopping before lunch. By two, please, Mr Pugilmain. No later than two. Good morning.”
4
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 21, 2025, 04:48:54 AM »
Chapter 281.
Tim’s Sunday was a lot less tiring than Bobby’s, but almost equally uncomfortable. Back inside, it was time for him to receive some basic instruction in the duties of a housemaid. Nicola instructed Teri to leave them alone with him for an hour.
“Teri – you can go make all the beds, clean the toilets, and then it’ll be time to for our coffee-break and for you to start preparing lunch. So after you’ve done the chores you can change into your kitchen maid outfit, there’s a good boy.”
“Yes, miss.”
He departed. She winked at Tim. “I know I should call him “girl”, but sometimes “boy” is more embarrassing for him. A lot of his mistresses call him boy. One of them – Mrs Baker, I think – she’s a regular – always calls him “boy” or “little boy”, accompanied by a disparaging sneer. It’s very effective. He hates going to hers. She always has her mates round, and some of them are really horrible to him! He tells me all about it when he gets home. Sometimes he’s almost in tears! I pretend to sympathise, but when I hear the things they’ve done… I find it quite exciting. Do you think that makes me as bad as them, Tim?”
“No, miss. I fink Teri likes you betterer than any of ‘em…”
“Did he tell you that? Good boy…”
“That’s because most of them are so nasty,” laughed Priscilla. “Nicola here’s an angel in comparison. Remember that lesbian woman? The tennis player? He made some minor faux pas – they were out shopping in some posh clothes shop, Teri wearing his maid’s outfit with a chastity device and no panties – and she stopped, pulled a butt-plug out of her handbag, bent him over the counter, and calmly popped it in in front of everyone!”
“Of course we remember,” said Serena. “That was out of order, though.”
“Maybe – but I bet he was on his best behaviour for the rest of the day!”
Tim was beginning to feel seriously alarmed. This didn’t sound like the rather embarrassing dress-up game he had hoped. His expression must have said it all, because the ladies all looked at him and sniggered.
“Don’t worry, Tim,” said Serena. “It won’t always be as bad as that. It just depends who you get sent to. In any case, you won’t be put on the website until we’re satisfied you’ve been trained to a sufficient standard. I’m sure you’re a quick learner, so it shouldn’t be long. And if you always keep in mind the basic principles of politeness, total obedience and efficiency, your mistresses will have all the less reason to punish you.” She turned to the others. “Shall we get started?”
While Priscilla, Nicola and Margaret sat down in a row on the sofa in front of the French doors, Serena left the room briefly and returned carrying a shiny circular steel disc about half a metre across. It looked quite heavy. She placed it in the middle of the room.
“Come stand on this please.”
Tim complied. In the centre of the disc was a little depression across which was a steel bar flush with the surface. Serena knelt down, attached pink leather ankle cuffs to his ankles, and joined with a fine steel chain which she slipped under the bar. She attached the ends to the cuffs with tiny padlocks.
“There. This is our basic immobiliser. It keeps you in one place so you can’t shift about or fidget or misbehave.” She retreated to a armchair near the sofa and sat down. “Now first of all we’re going to test your suitability for the post of housemaid. Please answer our questions promptly and honestly. We’ll take it in turns. Nicola, would you like to begin?”
Nicola looked him in the eye, frowning.
“Boy? Lift your skirt and show me your bloomers.”
“Wh…what?”
Nicola sighed. “You heard. Do it now!”
“But…”
She jumped up, walked over to him, lifted his skirt and slapped him hard on his bare thigh.
“Ow!”
She resumed her seat. It was Margaret’s turn.
“What sort of butt-plug would you like today, boy? Egg-shaped or pen-is-shaped?”
Tim stared at her open-mouthed.
“I…” was all he could say.
“Wrong answer!”
It was her turn to approach him. Tim tried to hold down his skirt, so she smacked his arm, then lifted his skirt and delivered an even harder smack, right on the same spot as Nicola. She resumed her seat. Now it was Priscilla’s turn.
“Do you like to suc-k coc-k, Tim?”
Tim blushed and began to stammer.
“S-suc-k…?”
“suc-k coc-k. Do you like suc-king coc-k?”
“Er…”
Priscilla went to rise. Tim’s thigh was stinging. He chose the easier option.
“Y-yes,” he said, hurriedly.”
Priscilla leant back again.
“Yes what?”
“Y-yes… I like to…s-suc-k coc-k…”
It was Serena’s turn.
“Do you suc-k Bobby’s coc-k?”
Tim took a deep breath. “N-no…”
“But you are going to, aren’t you?”
A pause. “Y-yes…”
“Will you wear one of your maid’s outfits?”
“Y-yes…”
“And may we watch?”
“Y-yes…”
“Good boy. Then we’ll book a session at the boot parlour, and bring you a maid’s dress. Maybe the one you’re wearing, maybe a cuter one, with a little skirt that lets you show your pretty bloomers. Would you like that?”
“Y-yes, miss…”
“Would you like it a lot? How much?”
“Y-yes…a lot…”
“Because you often think about it, don’t you?”
Tim turned bright red. But they all misunderstood. What Tim had fantasized about was the not him going down on Bobby, but on the contrary, Bobby....in his pretty dress...
“I’ll take that as a yes.”
And so it went on, for an hour. More, since Teri seemed to be busier than anticipated. Tim soon learned to return positive and obliging answers. It was soon to become habitual. “Yes, miss.” “Right away, miss.” “Anything you say, miss.” “Thank you for punishing me, miss.” It was the first test of obedience, and training in total submission.
Eventually, Teri returned, wearing a slightly different blue uniform and blue latex gloves. Nicola ordered him into the kitchen, and followed behind. Tim was left standing on his plate like some sort of exhibit, and was ignored while Teri served coffee and cakes to the ladies. He was sure they hadn’t finished with him yet…
Tim’s Sunday was a lot less tiring than Bobby’s, but almost equally uncomfortable. Back inside, it was time for him to receive some basic instruction in the duties of a housemaid. Nicola instructed Teri to leave them alone with him for an hour.
“Teri – you can go make all the beds, clean the toilets, and then it’ll be time to for our coffee-break and for you to start preparing lunch. So after you’ve done the chores you can change into your kitchen maid outfit, there’s a good boy.”
“Yes, miss.”
He departed. She winked at Tim. “I know I should call him “girl”, but sometimes “boy” is more embarrassing for him. A lot of his mistresses call him boy. One of them – Mrs Baker, I think – she’s a regular – always calls him “boy” or “little boy”, accompanied by a disparaging sneer. It’s very effective. He hates going to hers. She always has her mates round, and some of them are really horrible to him! He tells me all about it when he gets home. Sometimes he’s almost in tears! I pretend to sympathise, but when I hear the things they’ve done… I find it quite exciting. Do you think that makes me as bad as them, Tim?”
“No, miss. I fink Teri likes you betterer than any of ‘em…”
“Did he tell you that? Good boy…”
“That’s because most of them are so nasty,” laughed Priscilla. “Nicola here’s an angel in comparison. Remember that lesbian woman? The tennis player? He made some minor faux pas – they were out shopping in some posh clothes shop, Teri wearing his maid’s outfit with a chastity device and no panties – and she stopped, pulled a butt-plug out of her handbag, bent him over the counter, and calmly popped it in in front of everyone!”
“Of course we remember,” said Serena. “That was out of order, though.”
“Maybe – but I bet he was on his best behaviour for the rest of the day!”
Tim was beginning to feel seriously alarmed. This didn’t sound like the rather embarrassing dress-up game he had hoped. His expression must have said it all, because the ladies all looked at him and sniggered.
“Don’t worry, Tim,” said Serena. “It won’t always be as bad as that. It just depends who you get sent to. In any case, you won’t be put on the website until we’re satisfied you’ve been trained to a sufficient standard. I’m sure you’re a quick learner, so it shouldn’t be long. And if you always keep in mind the basic principles of politeness, total obedience and efficiency, your mistresses will have all the less reason to punish you.” She turned to the others. “Shall we get started?”
While Priscilla, Nicola and Margaret sat down in a row on the sofa in front of the French doors, Serena left the room briefly and returned carrying a shiny circular steel disc about half a metre across. It looked quite heavy. She placed it in the middle of the room.
“Come stand on this please.”
Tim complied. In the centre of the disc was a little depression across which was a steel bar flush with the surface. Serena knelt down, attached pink leather ankle cuffs to his ankles, and joined with a fine steel chain which she slipped under the bar. She attached the ends to the cuffs with tiny padlocks.
“There. This is our basic immobiliser. It keeps you in one place so you can’t shift about or fidget or misbehave.” She retreated to a armchair near the sofa and sat down. “Now first of all we’re going to test your suitability for the post of housemaid. Please answer our questions promptly and honestly. We’ll take it in turns. Nicola, would you like to begin?”
Nicola looked him in the eye, frowning.
“Boy? Lift your skirt and show me your bloomers.”
“Wh…what?”
Nicola sighed. “You heard. Do it now!”
“But…”
She jumped up, walked over to him, lifted his skirt and slapped him hard on his bare thigh.
“Ow!”
She resumed her seat. It was Margaret’s turn.
“What sort of butt-plug would you like today, boy? Egg-shaped or pen-is-shaped?”
Tim stared at her open-mouthed.
“I…” was all he could say.
“Wrong answer!”
It was her turn to approach him. Tim tried to hold down his skirt, so she smacked his arm, then lifted his skirt and delivered an even harder smack, right on the same spot as Nicola. She resumed her seat. Now it was Priscilla’s turn.
“Do you like to suc-k coc-k, Tim?”
Tim blushed and began to stammer.
“S-suc-k…?”
“suc-k coc-k. Do you like suc-king coc-k?”
“Er…”
Priscilla went to rise. Tim’s thigh was stinging. He chose the easier option.
“Y-yes,” he said, hurriedly.”
Priscilla leant back again.
“Yes what?”
“Y-yes… I like to…s-suc-k coc-k…”
It was Serena’s turn.
“Do you suc-k Bobby’s coc-k?”
Tim took a deep breath. “N-no…”
“But you are going to, aren’t you?”
A pause. “Y-yes…”
“Will you wear one of your maid’s outfits?”
“Y-yes…”
“And may we watch?”
“Y-yes…”
“Good boy. Then we’ll book a session at the boot parlour, and bring you a maid’s dress. Maybe the one you’re wearing, maybe a cuter one, with a little skirt that lets you show your pretty bloomers. Would you like that?”
“Y-yes, miss…”
“Would you like it a lot? How much?”
“Y-yes…a lot…”
“Because you often think about it, don’t you?”
Tim turned bright red. But they all misunderstood. What Tim had fantasized about was the not him going down on Bobby, but on the contrary, Bobby....in his pretty dress...
“I’ll take that as a yes.”
And so it went on, for an hour. More, since Teri seemed to be busier than anticipated. Tim soon learned to return positive and obliging answers. It was soon to become habitual. “Yes, miss.” “Right away, miss.” “Anything you say, miss.” “Thank you for punishing me, miss.” It was the first test of obedience, and training in total submission.
Eventually, Teri returned, wearing a slightly different blue uniform and blue latex gloves. Nicola ordered him into the kitchen, and followed behind. Tim was left standing on his plate like some sort of exhibit, and was ignored while Teri served coffee and cakes to the ladies. He was sure they hadn’t finished with him yet…
5
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 20, 2025, 02:05:45 PM »
Chapter 280.
From the point of view of popularity the pony-rides were a great success. Only fifty tickets had been issued, though idle spectators outnumbered participants by a ratio of about four to one, and their attention seemed to be about equally divided between the pony and the rather attractive girl in shocking pink stewarding the participants. A nice lady from a local paper took lots of pictures, and promised Thomasina, despite her desperate pleas for anonymity, to feature her in a quarter-page photograph in the events section. Mélisande was busy helping the younger ones, demonstrating the correct use of the aids or leading Bobby around by the bridle. He didn’t appear very sprightly that afternoon, and had to be given a good deal of encouragement, by way of whipping, kicking and spurring, to perform his duties.
“What’s the matter with you today?” hissed Mélisande, between customers. “You had a rest. Wake up, please. If you don’t, it’ll only be worse for you.”
The event finally wound up about half-past five, and Thomasina, who still hadn’t been able to retrieve her clothes, made straight for Miss Poole’s office. Miss Poole wasn’t back yet, and she was left with a choice of sitting in reception or standing outside her door. She chose the latter, thinking it would be the quieter place, though as it turned out it was unusually busy that evening, with people passing to and fro every minute, all pretending not to be looking at her. But eventually Miss Poole reappeared.
“Thomasina, dear! Do come in. I’m late? Oh, so I am. Sorry. Busy day, you know…”
She unlocked the door and ushered her in.
“Take a seat. Now what an I do for you?”
“But… You asked me to come to see you…”
“Oh, dear. So I did.”
“And Miss Poole? I asked my friend to go and collect my clothes, but she came back and told me the Old House is all locked up! I can’t go home on the bus like this. And what will mummy say?”
“She might say how pretty you look, mightn’t she?”
“My mother? You don’t know her. She insists I always dress modestly, to avoid unwanted attention. She would have a heart attack if she saw me in this!”
Miss Poole raised an eyebrow, and inwardly expressed the hope that that might be true.
“Don’t you think you’re making a fuss over nothing? Several of our members wear latex for riding out in bad weather. You should try it. It’s practical and really quite innocuous.”
“But it’s rather…fetishistic, isn’t it?”
“Look at what you normally wear. Everything just so, all that designer stuff, the most expensive boots and breeches, Chanel gloves… Isn’t that fetishistic in its own way? That’s why that incident occurred. That, and because you always capitulate when challenged.”
Thomasina’s face wrinkled up again, and her eyes gleamed with tears.
“Now Thomasina, darling… Please don’t cry. You can swear at me, call me an old bitch, if you like – I don’t care. Just show some spirit.”
Thomasina looked up, startled. For a moment she just stared, then she burst out laughing.
“Miss Poole… I didn’t think I’d ever hear you…”
“Oh, I’m nothing special, dear. I’m human too. Chill out. I’d really like to have you on my side. I can see that under all that shyness and modesty you’re rather fun – and you could be quite feisty if you wanted. Look, I have a problem. Your mother is suing us for that incident…”
“I know! I’m sorry. I wish I’d never told her!”
“It’s all right. It’s not your fault. But it’s a problem for the Centre. The last thing we need is to be accused of not looking after our members or staff. I don’t quite know what to do. In the back of my mind I had some idea of threatening your mother back using the video. But I don’t want to get you into trouble…”
“You don’t have to. I can fix this.”
“You can? How? Can you persuade her…?”
“No. It’s very simple. Tomorrow I have an appointment with the solicitor. I have to make a statement about the incident. I’ve been worrying about it for days. Now I know just what to do. I will make a statement, but I’ll say I provoked it. I’ll say I hated that girl and wanted to find a way to get her sacked.”
“But that’s not what happened.”
“I know. But that’s what I’ll say. I’ll say I lied to mummy. That it was my fault. No, I’ve decided. You’ve been straight with me. It’s the least I can do. This way they’ll have to withdraw their threats. I hate those lawyers anyway. Disgusting smooth bastards. It’ll be a pleasure to see their smug faces drop.”
“Are you sure…?”
“Sure and certain. You can stop worrying, Miss Poole.”
“Well… I’m…very grateful. It would be a load off my mind. And the committee will be so relieved…”
“No problem.”
“Well then... I guess we should get your clothes. Shall we walk round to the House together?”
“Okay.”
They rose. Miss Poole opened the door for her. As they walked, Miss Poole figuratively opened another door for her.
“Thomasina… I don’t know if this would interest you… We have a sort of informal women’s club here, with Ellie and certain members of the committee and a couple of my friends and one or two of the stable staff. We like to have a little illicit fun, now and again. It often involves certain boys who shall for the time being be nameless. If you would like to be a part of it…”
“Do you think I’d be useful, then?
“With your looks – and spirit? I’m sure of it.”
“It sounds interesting… Do we get to mistreat them a little…?”
“A little, yes…”
“Then…why not?”
“Excellent!”
“And don’t forget my video, will you?”
“I’ll do it tomorrow. Ah, here we are. I’ll get your clothes.”
“Thanks. But you know what? I’m going to keep this on underneath! It feels kind of sexy, actually…”
From the point of view of popularity the pony-rides were a great success. Only fifty tickets had been issued, though idle spectators outnumbered participants by a ratio of about four to one, and their attention seemed to be about equally divided between the pony and the rather attractive girl in shocking pink stewarding the participants. A nice lady from a local paper took lots of pictures, and promised Thomasina, despite her desperate pleas for anonymity, to feature her in a quarter-page photograph in the events section. Mélisande was busy helping the younger ones, demonstrating the correct use of the aids or leading Bobby around by the bridle. He didn’t appear very sprightly that afternoon, and had to be given a good deal of encouragement, by way of whipping, kicking and spurring, to perform his duties.
“What’s the matter with you today?” hissed Mélisande, between customers. “You had a rest. Wake up, please. If you don’t, it’ll only be worse for you.”
The event finally wound up about half-past five, and Thomasina, who still hadn’t been able to retrieve her clothes, made straight for Miss Poole’s office. Miss Poole wasn’t back yet, and she was left with a choice of sitting in reception or standing outside her door. She chose the latter, thinking it would be the quieter place, though as it turned out it was unusually busy that evening, with people passing to and fro every minute, all pretending not to be looking at her. But eventually Miss Poole reappeared.
“Thomasina, dear! Do come in. I’m late? Oh, so I am. Sorry. Busy day, you know…”
She unlocked the door and ushered her in.
“Take a seat. Now what an I do for you?”
“But… You asked me to come to see you…”
“Oh, dear. So I did.”
“And Miss Poole? I asked my friend to go and collect my clothes, but she came back and told me the Old House is all locked up! I can’t go home on the bus like this. And what will mummy say?”
“She might say how pretty you look, mightn’t she?”
“My mother? You don’t know her. She insists I always dress modestly, to avoid unwanted attention. She would have a heart attack if she saw me in this!”
Miss Poole raised an eyebrow, and inwardly expressed the hope that that might be true.
“Don’t you think you’re making a fuss over nothing? Several of our members wear latex for riding out in bad weather. You should try it. It’s practical and really quite innocuous.”
“But it’s rather…fetishistic, isn’t it?”
“Look at what you normally wear. Everything just so, all that designer stuff, the most expensive boots and breeches, Chanel gloves… Isn’t that fetishistic in its own way? That’s why that incident occurred. That, and because you always capitulate when challenged.”
Thomasina’s face wrinkled up again, and her eyes gleamed with tears.
“Now Thomasina, darling… Please don’t cry. You can swear at me, call me an old bitch, if you like – I don’t care. Just show some spirit.”
Thomasina looked up, startled. For a moment she just stared, then she burst out laughing.
“Miss Poole… I didn’t think I’d ever hear you…”
“Oh, I’m nothing special, dear. I’m human too. Chill out. I’d really like to have you on my side. I can see that under all that shyness and modesty you’re rather fun – and you could be quite feisty if you wanted. Look, I have a problem. Your mother is suing us for that incident…”
“I know! I’m sorry. I wish I’d never told her!”
“It’s all right. It’s not your fault. But it’s a problem for the Centre. The last thing we need is to be accused of not looking after our members or staff. I don’t quite know what to do. In the back of my mind I had some idea of threatening your mother back using the video. But I don’t want to get you into trouble…”
“You don’t have to. I can fix this.”
“You can? How? Can you persuade her…?”
“No. It’s very simple. Tomorrow I have an appointment with the solicitor. I have to make a statement about the incident. I’ve been worrying about it for days. Now I know just what to do. I will make a statement, but I’ll say I provoked it. I’ll say I hated that girl and wanted to find a way to get her sacked.”
“But that’s not what happened.”
“I know. But that’s what I’ll say. I’ll say I lied to mummy. That it was my fault. No, I’ve decided. You’ve been straight with me. It’s the least I can do. This way they’ll have to withdraw their threats. I hate those lawyers anyway. Disgusting smooth bastards. It’ll be a pleasure to see their smug faces drop.”
“Are you sure…?”
“Sure and certain. You can stop worrying, Miss Poole.”
“Well… I’m…very grateful. It would be a load off my mind. And the committee will be so relieved…”
“No problem.”
“Well then... I guess we should get your clothes. Shall we walk round to the House together?”
“Okay.”
They rose. Miss Poole opened the door for her. As they walked, Miss Poole figuratively opened another door for her.
“Thomasina… I don’t know if this would interest you… We have a sort of informal women’s club here, with Ellie and certain members of the committee and a couple of my friends and one or two of the stable staff. We like to have a little illicit fun, now and again. It often involves certain boys who shall for the time being be nameless. If you would like to be a part of it…”
“Do you think I’d be useful, then?
“With your looks – and spirit? I’m sure of it.”
“It sounds interesting… Do we get to mistreat them a little…?”
“A little, yes…”
“Then…why not?”
“Excellent!”
“And don’t forget my video, will you?”
“I’ll do it tomorrow. Ah, here we are. I’ll get your clothes.”
“Thanks. But you know what? I’m going to keep this on underneath! It feels kind of sexy, actually…”
6
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 19, 2025, 03:25:44 PM »
Chapter 279.
After a few minutes they went inside, Clarissa leading the exhausted Bobby.
“I’m sorry darling, I had no idea this would happen,” she whispered. “Whatever was that all about? Do you like that girl or something? Anyway, I’ll get you sorted out. There’s about forty minutes before we have to head to the pony rides, so you can get a little bit of rest…”
Bobby’s only response was a tired groan.
Thomasina was sitting on the bench, frowning, her flushed cheeks stained with tears.
“Miss Poole, I want to get changed. The door seems to be locked. Please unlock it so I can get to my proper clothes.”
“Proper clothes? I don’t know what you mean. What you’re wearing is your proper outfit for the rest of the day.”
“Miss Poole. When my mother hears about this…”
Miss Poole sat down beside her on the bench.
“Your mother? Oh, yes. Lady Middiford. I’d quite forgotten. We must send her the video, mustn’t we? She’ll be so impressed. Zeta, could we have a look at some of the footage please? Come and sit with us.”
Zeta took her seat on the other side of Thomasina, who all of a sudden had become silent. She sat with hands clenched. Her anger and confidence had evaporated. She looked worried and frightened. Zeta held the camera in front of her and played some clips.
“There we go,” said Miss Poole, cheerfully. “Ah… There, that’s the beginning. See how pretty you look in pink latex? You have a sweet body, my dear. Isn’t it nice to show it off sometimes? Oh, now this is where…there! What did you do to make it do that? I think it was your spurs… You used your spurs, and out it popped!”
Thomasina gasped. “No! I didn’t do anything…”
“Well you were riding him rather hard, Thomasina. I think he was enjoying it in some rather perverted way. Or maybe he’d just taken a liking to you and he had no other way of expressing his feelings. Look at it bouncing up and down! You must have heard it spanking against his belly. We all could.”
“P-please… I didn’t mean to… I mean, truly, I didn’t… Please, Miss Poole, please… Please don’t let my mother…”
“Thomasina, look. Don’t miss this bit. This is where it happens. He stops, and… Oh my god, just look at it pumping! You really didn’t realise? I find that a little hard to believe…”
“I had no idea… I swear…”
“I just love the way you sit there holding on, while he’s, well… I mean, what an exhibition! How long was that, Zeta?”
“Let me see… From the moment he stopped till he finally wilted… About a minute and five seconds.”
“Wow! Thomasina! And you really don’t even have a boyfriend? Goodness! Just don’t ask to ride any of the stallions, will you, or goodness knows…”
“Miss Poole, you know I had no intention…none whatsoever… I mean, how could I possibly have foreseen…w-what was going to happen…”
Miss Poole gave her a sly wink. “It can be our secret, dear. No-one here will say a word, I can assure you.”
“No, you have to believe me… I would never… Not anything like that…”
Her brow wrinkled, as if she was going to start crying again. “That video…”
“Oh, yes… You’ll be wanting the video, of course. Look, we need to get on. Could you pop into my office this evening? Any time after six. And we can discuss all this at our leisure.”
“Of course, Miss Poole. But what about this afternoon?”
“Oh, yes. Let’s see…one-twenty. We have a good half hour before the pony rides. Ellie? Are you ready for Thomasina?”
“Yes, Miss Poole.”
“R-ready…?”
“Just do what Ellie tells you, and there won’t be any need for you to worry about anything…what you did just now, what’s going to happen to the video… I’ll take care of everything.”
Thomasina looked at her questioningly. Miss Poole returned he gaze. There was a smile on her lips, but a warning in her eyes. Thomasina understood perfectly.
“Yes, Miss Poole.”
Five minutes later she found herself standing on the crate. Ellie had called her friends, and the stable girls started arriving in groups of three, four or five. As each group caught sight of Thomasina, there were catcalls, whoops, whistles and laughter. Soon the courtyard was noisy with chattering, giggling girls, and the clicking of phones. Ellie stepped forward.
“You all know Thomasina. Thomasina confessed to me that she’s always secretly wanted to wear cool latex riding outfits like this, but never had the confidence. She asked me to arrange this show to see what you all thought. If you approve, who knows where it will lead? If you think it suits her, please raise your hand.”
The response was overwhelming, and accompanied by cheers, and shouts of “go, Thomasina!”.
“Thank you all so much. There, Thomasina. Unanimous. Brave girl! Now just stand there until it’s time for the pony rides, so everyone can get a good look. Come on girls. Come and check her out, come feel the quality of this amazing latex!”
After a few minutes they went inside, Clarissa leading the exhausted Bobby.
“I’m sorry darling, I had no idea this would happen,” she whispered. “Whatever was that all about? Do you like that girl or something? Anyway, I’ll get you sorted out. There’s about forty minutes before we have to head to the pony rides, so you can get a little bit of rest…”
Bobby’s only response was a tired groan.
Thomasina was sitting on the bench, frowning, her flushed cheeks stained with tears.
“Miss Poole, I want to get changed. The door seems to be locked. Please unlock it so I can get to my proper clothes.”
“Proper clothes? I don’t know what you mean. What you’re wearing is your proper outfit for the rest of the day.”
“Miss Poole. When my mother hears about this…”
Miss Poole sat down beside her on the bench.
“Your mother? Oh, yes. Lady Middiford. I’d quite forgotten. We must send her the video, mustn’t we? She’ll be so impressed. Zeta, could we have a look at some of the footage please? Come and sit with us.”
Zeta took her seat on the other side of Thomasina, who all of a sudden had become silent. She sat with hands clenched. Her anger and confidence had evaporated. She looked worried and frightened. Zeta held the camera in front of her and played some clips.
“There we go,” said Miss Poole, cheerfully. “Ah… There, that’s the beginning. See how pretty you look in pink latex? You have a sweet body, my dear. Isn’t it nice to show it off sometimes? Oh, now this is where…there! What did you do to make it do that? I think it was your spurs… You used your spurs, and out it popped!”
Thomasina gasped. “No! I didn’t do anything…”
“Well you were riding him rather hard, Thomasina. I think he was enjoying it in some rather perverted way. Or maybe he’d just taken a liking to you and he had no other way of expressing his feelings. Look at it bouncing up and down! You must have heard it spanking against his belly. We all could.”
“P-please… I didn’t mean to… I mean, truly, I didn’t… Please, Miss Poole, please… Please don’t let my mother…”
“Thomasina, look. Don’t miss this bit. This is where it happens. He stops, and… Oh my god, just look at it pumping! You really didn’t realise? I find that a little hard to believe…”
“I had no idea… I swear…”
“I just love the way you sit there holding on, while he’s, well… I mean, what an exhibition! How long was that, Zeta?”
“Let me see… From the moment he stopped till he finally wilted… About a minute and five seconds.”
“Wow! Thomasina! And you really don’t even have a boyfriend? Goodness! Just don’t ask to ride any of the stallions, will you, or goodness knows…”
“Miss Poole, you know I had no intention…none whatsoever… I mean, how could I possibly have foreseen…w-what was going to happen…”
Miss Poole gave her a sly wink. “It can be our secret, dear. No-one here will say a word, I can assure you.”
“No, you have to believe me… I would never… Not anything like that…”
Her brow wrinkled, as if she was going to start crying again. “That video…”
“Oh, yes… You’ll be wanting the video, of course. Look, we need to get on. Could you pop into my office this evening? Any time after six. And we can discuss all this at our leisure.”
“Of course, Miss Poole. But what about this afternoon?”
“Oh, yes. Let’s see…one-twenty. We have a good half hour before the pony rides. Ellie? Are you ready for Thomasina?”
“Yes, Miss Poole.”
“R-ready…?”
“Just do what Ellie tells you, and there won’t be any need for you to worry about anything…what you did just now, what’s going to happen to the video… I’ll take care of everything.”
Thomasina looked at her questioningly. Miss Poole returned he gaze. There was a smile on her lips, but a warning in her eyes. Thomasina understood perfectly.
“Yes, Miss Poole.”
Five minutes later she found herself standing on the crate. Ellie had called her friends, and the stable girls started arriving in groups of three, four or five. As each group caught sight of Thomasina, there were catcalls, whoops, whistles and laughter. Soon the courtyard was noisy with chattering, giggling girls, and the clicking of phones. Ellie stepped forward.
“You all know Thomasina. Thomasina confessed to me that she’s always secretly wanted to wear cool latex riding outfits like this, but never had the confidence. She asked me to arrange this show to see what you all thought. If you approve, who knows where it will lead? If you think it suits her, please raise your hand.”
The response was overwhelming, and accompanied by cheers, and shouts of “go, Thomasina!”.
“Thank you all so much. There, Thomasina. Unanimous. Brave girl! Now just stand there until it’s time for the pony rides, so everyone can get a good look. Come on girls. Come and check her out, come feel the quality of this amazing latex!”
7
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 19, 2025, 03:05:35 PM »
Chapter 278.
“Could you ride him?”
“Huh. Of course I could, but…”
“Show me then. If you can really ride him, you’ll be the only one apart from Mélisande who can. You’re a lot older than her. If you don’t have the confidence, of course…”
The only thing that could elicit a passionate response from Thomasina was a disparaging comment about her riding.
“Get him outside and I’ll show you how much confidence I have.”
“All right. Riding boots, helmet and whip. You’re wearing spurs, I see. Excellent. You may need them.”
Zeta had already been filming. Now, as Thomasina pulled on her boots and hat, and picked up her whip, and everyone began to make their way out into the courtyard she paused the video and waited for the next chapter.
When everyone was outside Thomasina, blushing more than ever, climbed astride Bobby, fitted her feet into the stirrups, gathered up the reins, which she wound round her left hand, and gave him a smart whack with her whip. He shot forward at a brisk trot. Thomasina, still smarting from Miss Poole’s comments, and feeling humiliated by her proximity to such a boy, employed heels and whip with unwonted vigour. Zeta had clear space to film the exciting spectacle, and she knelt down to get the best angle. But while Thomasina spurred Bobby on, Violet spurred her on.
“Is that the best you can do? Mélisande has him going much faster - eh Clarissa?”
The first circuit was completed without incident. Whether it was the feeling of having a grown girl on his back for the first time, or whether he had a bit of a thing for her, Bobby’s growing erection suddenly became too much for the zip, and it popped out, long and shiny and red, waggling beneath his tummy. Everyone gasped, but Violet gave them a look, and they hid their surprise. Thomasina was pushing hard now, and Bobby’s erection was bouncing in rhythm with his paces, slapping audibly against his tummy. Thomasina must have heard, because once she looked down, but she probably assumed it was just his thighs brushing together.
“There,” she said, breathlessly, as she embarked on the fourth circuit, “still think I don’t have the confidence?”
“I think you’ve proved your expertise,” said Violet. “A couple more circuits, perhaps… Bobby seems to have a lot of energy today…”
It was at this point that Ellie remembered something. She slipped a hand into her pocket. There it was! The remote! Almost too late! As quickly as she could she dialled it up to maximum and hit the start button.
Bobby stopped dead. Thomasina lurched forward.
“Stupid animal!”
She gave him three hard strokes, forcing him into a walk.
“What’s the matter with you? Go! Come on!”
She swung her heels back and dig her spurs into his flanks, He made a whining sound through his bit. And speeded up a little. As he passed Zeta she was amazed to observe his erection apparently vibrating visibly! She looked up at the others, standing in line with their backs to the stable. Ellie smiled and gave her a wink. She returned a delighted grin.
It was on the final circuit. He was directly opposite the spectators. He stopped suddenly, and made a strange muffled trumpeting noise, like a baby elephant in distress. Both he and Thomasina stared questioningly at the onlookers. Thomasina as if to say, “what’s going on with him?” Bobby as if pleading, asking, “why are you doing this to me?” Then his eyes closed and his lips parted in silent ecstasy. For a moment he was motionless, despite a jab from Thomasina’s spurs, then he lurched, and his body undulated violently and rhythmically with wave after wave of orgasm. Thomasina had to gather up the reins and clamp her thighs around him, or she would have been unshipped. He stood there, shuddering and pumping c-um, filling the teat of his scarlet condom till it was swinging and dancing like a hooked fish, while Thomasina, tossed about helplessly in the saddle, looked at her grinning audience with bewilderment. Zeta had already moved in front of them, and was virtually lying on the ground, her eyes fixed on the display of her camera.
“This is so cool….” she murmured, in the tone of a professional who has captured a scene to perfection.
As for Thomasina, it was only as Bobby’s climax began to subside that the awful truth dawned on her. With a cry of disgust she leapt off his back and retreated to the side of the courtyard, her eyes fixed on her discarded mount, now quite spent and panting, with horrified disbelief.
Ellie turned off the remote in her pocket, and winked at Violet, who had watched the whole performance with calm, though smug, absorption. She turned to Thomasina.
“That was a masterful exhibition of equestrian control, my dear. I commend you for your faultless technique – though I think you may perhaps have over-stimulated your mount. Please resume, if you would like – he seems to have almost regained his composure…”
Thomasina’s response was a glance, half of anger, half of fright, followed by a dash back into the stable to hide her burning cheeks and the tears welling in her eyes.
Clarissa went to follow her, probably with the idea of consoling her and blaming everything on Bobby, but Violet restrained her.
“Give her a few minutes. Then we’ll get Bobby inside, and we can move onto phase two.”
“Phase two?” asked Clarissa, puzzled.
“She’s going to spend the last half-hour before the pony rides begin standing on that little crate,” said Ellie, pointing at it. “I’ve invited some of the girls to come around and see her, when I give them the word. It’s the second phase of her training to overcome her shyness.”
“Oh…I see… But surely there’s no way she’ll stand up there like some exhibit in a museum…”
“Oh, she will, Clarissa,” said Violet. “You’ll see. Phase three will be the stewarding of the pony rides. She should have no alternative but to overcome some of her shyness. If not, we have other strategies.”
“Gosh, Violet. You had this all planned out. What if she just ups and leaves, and never comes back?”
“That is not an option, Clarissa. I assure you, she will stay. Indeed, she will stay for as long as I wish…”
“Could you ride him?”
“Huh. Of course I could, but…”
“Show me then. If you can really ride him, you’ll be the only one apart from Mélisande who can. You’re a lot older than her. If you don’t have the confidence, of course…”
The only thing that could elicit a passionate response from Thomasina was a disparaging comment about her riding.
“Get him outside and I’ll show you how much confidence I have.”
“All right. Riding boots, helmet and whip. You’re wearing spurs, I see. Excellent. You may need them.”
Zeta had already been filming. Now, as Thomasina pulled on her boots and hat, and picked up her whip, and everyone began to make their way out into the courtyard she paused the video and waited for the next chapter.
When everyone was outside Thomasina, blushing more than ever, climbed astride Bobby, fitted her feet into the stirrups, gathered up the reins, which she wound round her left hand, and gave him a smart whack with her whip. He shot forward at a brisk trot. Thomasina, still smarting from Miss Poole’s comments, and feeling humiliated by her proximity to such a boy, employed heels and whip with unwonted vigour. Zeta had clear space to film the exciting spectacle, and she knelt down to get the best angle. But while Thomasina spurred Bobby on, Violet spurred her on.
“Is that the best you can do? Mélisande has him going much faster - eh Clarissa?”
The first circuit was completed without incident. Whether it was the feeling of having a grown girl on his back for the first time, or whether he had a bit of a thing for her, Bobby’s growing erection suddenly became too much for the zip, and it popped out, long and shiny and red, waggling beneath his tummy. Everyone gasped, but Violet gave them a look, and they hid their surprise. Thomasina was pushing hard now, and Bobby’s erection was bouncing in rhythm with his paces, slapping audibly against his tummy. Thomasina must have heard, because once she looked down, but she probably assumed it was just his thighs brushing together.
“There,” she said, breathlessly, as she embarked on the fourth circuit, “still think I don’t have the confidence?”
“I think you’ve proved your expertise,” said Violet. “A couple more circuits, perhaps… Bobby seems to have a lot of energy today…”
It was at this point that Ellie remembered something. She slipped a hand into her pocket. There it was! The remote! Almost too late! As quickly as she could she dialled it up to maximum and hit the start button.
Bobby stopped dead. Thomasina lurched forward.
“Stupid animal!”
She gave him three hard strokes, forcing him into a walk.
“What’s the matter with you? Go! Come on!”
She swung her heels back and dig her spurs into his flanks, He made a whining sound through his bit. And speeded up a little. As he passed Zeta she was amazed to observe his erection apparently vibrating visibly! She looked up at the others, standing in line with their backs to the stable. Ellie smiled and gave her a wink. She returned a delighted grin.
It was on the final circuit. He was directly opposite the spectators. He stopped suddenly, and made a strange muffled trumpeting noise, like a baby elephant in distress. Both he and Thomasina stared questioningly at the onlookers. Thomasina as if to say, “what’s going on with him?” Bobby as if pleading, asking, “why are you doing this to me?” Then his eyes closed and his lips parted in silent ecstasy. For a moment he was motionless, despite a jab from Thomasina’s spurs, then he lurched, and his body undulated violently and rhythmically with wave after wave of orgasm. Thomasina had to gather up the reins and clamp her thighs around him, or she would have been unshipped. He stood there, shuddering and pumping c-um, filling the teat of his scarlet condom till it was swinging and dancing like a hooked fish, while Thomasina, tossed about helplessly in the saddle, looked at her grinning audience with bewilderment. Zeta had already moved in front of them, and was virtually lying on the ground, her eyes fixed on the display of her camera.
“This is so cool….” she murmured, in the tone of a professional who has captured a scene to perfection.
As for Thomasina, it was only as Bobby’s climax began to subside that the awful truth dawned on her. With a cry of disgust she leapt off his back and retreated to the side of the courtyard, her eyes fixed on her discarded mount, now quite spent and panting, with horrified disbelief.
Ellie turned off the remote in her pocket, and winked at Violet, who had watched the whole performance with calm, though smug, absorption. She turned to Thomasina.
“That was a masterful exhibition of equestrian control, my dear. I commend you for your faultless technique – though I think you may perhaps have over-stimulated your mount. Please resume, if you would like – he seems to have almost regained his composure…”
Thomasina’s response was a glance, half of anger, half of fright, followed by a dash back into the stable to hide her burning cheeks and the tears welling in her eyes.
Clarissa went to follow her, probably with the idea of consoling her and blaming everything on Bobby, but Violet restrained her.
“Give her a few minutes. Then we’ll get Bobby inside, and we can move onto phase two.”
“Phase two?” asked Clarissa, puzzled.
“She’s going to spend the last half-hour before the pony rides begin standing on that little crate,” said Ellie, pointing at it. “I’ve invited some of the girls to come around and see her, when I give them the word. It’s the second phase of her training to overcome her shyness.”
“Oh…I see… But surely there’s no way she’ll stand up there like some exhibit in a museum…”
“Oh, she will, Clarissa,” said Violet. “You’ll see. Phase three will be the stewarding of the pony rides. She should have no alternative but to overcome some of her shyness. If not, we have other strategies.”
“Gosh, Violet. You had this all planned out. What if she just ups and leaves, and never comes back?”
“That is not an option, Clarissa. I assure you, she will stay. Indeed, she will stay for as long as I wish…”
8
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 19, 2025, 02:58:08 PM »
Chapter 277.
“Come in!”
Thomasina opened the door half way, and peered nervously around. She hesitated when she saw so many people.
“Come in, girl – and close the door behind you.”
“I-I’m not late, am I…”
“Of course not.”
Then her gaze fell on Bobby, standing next to Clarissa by one of the benches. She gasped, and backed away.
“For goodness’ sake, girl… What are you frightened of? It’s just a boy.”
“B-but…”
“Don’t you believe me? Clarissa, please take off his bridle, pony hood and mask.”
“What?”
“Do it please. Let’s demystify him once and for all.”
As Thomasina and the others watched, Clarissa methodically removed the layers, till there was Ponyboy, his face and tousled hair revealed for all to see.
“Oh… It’s…B-Bobby!” exclaimed Thomasina, staring.
“Yes. So now you know,” said Miss Poole, matter-of-factly. But you must never tell, Thomasina dear – do you understand?”
“Oh…Oh, yes…perfectly, Miss Poole. I would never…”
“Yes, all right. Now leave your kit here. Ellie will take you next door and help you with your uniform. Off you go.”
Ellie opened the connecting door, smiled encouragingly, and ushered Thomasina in.
“Will she go for it?” asked Zeta.
“We’ll soon find out,” smiled Miss Poole.
The words were barely out of her mouth when there was a short scream from next door. A second later the door opened and Thomasina appeared in the doorway.
“Please… Miss Poole, please no… I can’t go out there in…that!”
“Can’t? You can and you will, my dear. You’ll look very nice, I’m sure…”
“B-but…it’s rubber!”
Miss Poole sighed. “To be accurate, it’s latex. Lovely soft pink latex, made especially for you. Now put it on and stop complaining.” She looked at her watch. “If you delay proceedings I’m going to be quite annoyed. Go!”
Thomasina was distressed, “Can I keep my panties…”
“No! Of course not! It’s designed to fit your body perfectly. So don’t be so silly. Now for the last time, go. If you’re not dressed in five minutes I’ll put you out there naked!”
That seemed to do the trick. Five minutes later the door opened, and Ellie appeared. She held it wide open.
“Come on Thomasina. Good girl.” She might have been talking to a puppy.
Thomasina appeared in the doorway, but seemed reluctant to advance any further. Ellie took her arm and pulled her into the centre of the room.
“Well! You look absolutely gorgeous, dear,” enthused Miss Poole.
“I already told her,” laughed Ellie. “You look fantastic. If you’re looking for a boyfriend, there’ll be plenty of takers today.”
“I’m not!” cried Thomasina, cheeks on fire, with the first exhibition of spirit anyone had seen. “I hate boys!”
“Ooh…” cried Zeta, adding hopefully “do you like girls by any chance?”
“What?”
“Nothing…”
Miss Poole had a strange smile on her face.
“Ellie tells me you’re a very accomplished rider, Thomasina.”
No reply.
“She said you could ride anything. Is that true?”
“I guess…”
“Could you ride…him?” She gestured towards Bobby.
“What?”
“We’d need to lengthen the stirrups an inch or two. Could you do that Clarissa? No mask, just his pony hood and bridle. Make sure the bit-strap’s nice and tight. Oh, and don’t forget to… Okay?”
Clarissa looked askance, but nodded. She lowered the stirrups a notch, tacked Nobby up, and surreptitiously loosened the zip on his pouch. But as she did so, she became aware that he was already semi-tumescent! Well, he may not have had any sort of sex for a while… Maybe it was just being back in his pony suit. But he was also staring at Thomasina… Surely he didn’t fancy her… Though in that catsuit she did look rather enticing. So she left the zip half open. If he did get an erection, that would certainly do the rest…
“Come in!”
Thomasina opened the door half way, and peered nervously around. She hesitated when she saw so many people.
“Come in, girl – and close the door behind you.”
“I-I’m not late, am I…”
“Of course not.”
Then her gaze fell on Bobby, standing next to Clarissa by one of the benches. She gasped, and backed away.
“For goodness’ sake, girl… What are you frightened of? It’s just a boy.”
“B-but…”
“Don’t you believe me? Clarissa, please take off his bridle, pony hood and mask.”
“What?”
“Do it please. Let’s demystify him once and for all.”
As Thomasina and the others watched, Clarissa methodically removed the layers, till there was Ponyboy, his face and tousled hair revealed for all to see.
“Oh… It’s…B-Bobby!” exclaimed Thomasina, staring.
“Yes. So now you know,” said Miss Poole, matter-of-factly. But you must never tell, Thomasina dear – do you understand?”
“Oh…Oh, yes…perfectly, Miss Poole. I would never…”
“Yes, all right. Now leave your kit here. Ellie will take you next door and help you with your uniform. Off you go.”
Ellie opened the connecting door, smiled encouragingly, and ushered Thomasina in.
“Will she go for it?” asked Zeta.
“We’ll soon find out,” smiled Miss Poole.
The words were barely out of her mouth when there was a short scream from next door. A second later the door opened and Thomasina appeared in the doorway.
“Please… Miss Poole, please no… I can’t go out there in…that!”
“Can’t? You can and you will, my dear. You’ll look very nice, I’m sure…”
“B-but…it’s rubber!”
Miss Poole sighed. “To be accurate, it’s latex. Lovely soft pink latex, made especially for you. Now put it on and stop complaining.” She looked at her watch. “If you delay proceedings I’m going to be quite annoyed. Go!”
Thomasina was distressed, “Can I keep my panties…”
“No! Of course not! It’s designed to fit your body perfectly. So don’t be so silly. Now for the last time, go. If you’re not dressed in five minutes I’ll put you out there naked!”
That seemed to do the trick. Five minutes later the door opened, and Ellie appeared. She held it wide open.
“Come on Thomasina. Good girl.” She might have been talking to a puppy.
Thomasina appeared in the doorway, but seemed reluctant to advance any further. Ellie took her arm and pulled her into the centre of the room.
“Well! You look absolutely gorgeous, dear,” enthused Miss Poole.
“I already told her,” laughed Ellie. “You look fantastic. If you’re looking for a boyfriend, there’ll be plenty of takers today.”
“I’m not!” cried Thomasina, cheeks on fire, with the first exhibition of spirit anyone had seen. “I hate boys!”
“Ooh…” cried Zeta, adding hopefully “do you like girls by any chance?”
“What?”
“Nothing…”
Miss Poole had a strange smile on her face.
“Ellie tells me you’re a very accomplished rider, Thomasina.”
No reply.
“She said you could ride anything. Is that true?”
“I guess…”
“Could you ride…him?” She gestured towards Bobby.
“What?”
“We’d need to lengthen the stirrups an inch or two. Could you do that Clarissa? No mask, just his pony hood and bridle. Make sure the bit-strap’s nice and tight. Oh, and don’t forget to… Okay?”
Clarissa looked askance, but nodded. She lowered the stirrups a notch, tacked Nobby up, and surreptitiously loosened the zip on his pouch. But as she did so, she became aware that he was already semi-tumescent! Well, he may not have had any sort of sex for a while… Maybe it was just being back in his pony suit. But he was also staring at Thomasina… Surely he didn’t fancy her… Though in that catsuit she did look rather enticing. So she left the zip half open. If he did get an erection, that would certainly do the rest…
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 19, 2025, 02:52:11 PM »
Chapter 276.
Clarissa led Bobby back into stable 13. He had less than half an hour to recover. They took off his mask, he rested, used the toilet, and had an energy drink. Much to his relief, Ellie then put on his standard mask. Several stable girls, friends of Mélisande, had gathered outside, eager to ask her where she had taken Ponyboy and what they had done. Clarissa relieved Mélisande of her hat and whip, and left her chatting with her friends. Ellie and Clarissa led Bobby up the hill, round the offices, and out of the gate to the Old House. The House had a spacious enclosed courtyard, and was divided into two parts, on the left the living quarters, on the right a spacious stable. Ellie noted a little wooden upturned crate in the courtyard, and smiled. The plan was afoot! She opened the stable door and Clarissa led Bobby in. The floor was a big plain stone flags, and there was little furniture – only a couple of benches and a big cupboard. Ellie shut the door and called out “we’re here”. The adjoining door opened, and who should appear but Miss Poole herself, with the familiar face of Magda’s sidekick Zeta following on behind!
“Hello Ellie. Hi Clarissa. I’m not sure if you know Zeta.” Zeta smiled and inclined her head. “Zeta is Magda’s best friend. And she’s an ace photographer.”
“Violet! Hi, Zeta. But… What are you doing here on a Sunday?”
“Well I’m here to witness the pony rides, of course, Clarissa. To watch your charge at work.”
“Oh, yes. Of course…”
“And to have a bit of fun. Perhaps I’d better explain. We have a few minutes before our other guest arrives, I think?”
“About fifteen minutes,” said Ellie.
“Good. Right. Clarissa, I’ve explained everything to Zeta, Ellie’s in on this too, so now I just need to tell you. Ellie, got the ear plugs?”
“Right here, Violet.”
She took Bobby by the bridle, stretched open his hood, and plugged both his ears.
“Thank you. As I was saying, Clarissa, today I need to make an example of a certain person who will be arriving here shortly. Bobby is going to help me, though he doesn’t know it yet. Please just go along with anything we do. After the filming Ellie’s going to call a few of the girls. But before that, our guest is going to have a little ride round the courtyard. So I have to ask…is Bobby fully, er, equipped, today?”
She pointed at his pink pouch. Clarissa looked startled.
“Does he have his nice red…?”
“Yes, of course…”
“Excellent. Then at the appropriate time, maybe his zip could slip undone…?”
Clarissa's eyes widened slightly. “If...you say so…”
“Good! We’re all set, then. All we have to do is wait for…”
She was interrupted by a faint double knock at the stable door…
Clarissa led Bobby back into stable 13. He had less than half an hour to recover. They took off his mask, he rested, used the toilet, and had an energy drink. Much to his relief, Ellie then put on his standard mask. Several stable girls, friends of Mélisande, had gathered outside, eager to ask her where she had taken Ponyboy and what they had done. Clarissa relieved Mélisande of her hat and whip, and left her chatting with her friends. Ellie and Clarissa led Bobby up the hill, round the offices, and out of the gate to the Old House. The House had a spacious enclosed courtyard, and was divided into two parts, on the left the living quarters, on the right a spacious stable. Ellie noted a little wooden upturned crate in the courtyard, and smiled. The plan was afoot! She opened the stable door and Clarissa led Bobby in. The floor was a big plain stone flags, and there was little furniture – only a couple of benches and a big cupboard. Ellie shut the door and called out “we’re here”. The adjoining door opened, and who should appear but Miss Poole herself, with the familiar face of Magda’s sidekick Zeta following on behind!
“Hello Ellie. Hi Clarissa. I’m not sure if you know Zeta.” Zeta smiled and inclined her head. “Zeta is Magda’s best friend. And she’s an ace photographer.”
“Violet! Hi, Zeta. But… What are you doing here on a Sunday?”
“Well I’m here to witness the pony rides, of course, Clarissa. To watch your charge at work.”
“Oh, yes. Of course…”
“And to have a bit of fun. Perhaps I’d better explain. We have a few minutes before our other guest arrives, I think?”
“About fifteen minutes,” said Ellie.
“Good. Right. Clarissa, I’ve explained everything to Zeta, Ellie’s in on this too, so now I just need to tell you. Ellie, got the ear plugs?”
“Right here, Violet.”
She took Bobby by the bridle, stretched open his hood, and plugged both his ears.
“Thank you. As I was saying, Clarissa, today I need to make an example of a certain person who will be arriving here shortly. Bobby is going to help me, though he doesn’t know it yet. Please just go along with anything we do. After the filming Ellie’s going to call a few of the girls. But before that, our guest is going to have a little ride round the courtyard. So I have to ask…is Bobby fully, er, equipped, today?”
She pointed at his pink pouch. Clarissa looked startled.
“Does he have his nice red…?”
“Yes, of course…”
“Excellent. Then at the appropriate time, maybe his zip could slip undone…?”
Clarissa's eyes widened slightly. “If...you say so…”
“Good! We’re all set, then. All we have to do is wait for…”
She was interrupted by a faint double knock at the stable door…
10
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on November 19, 2025, 02:46:04 PM »
Chapter 275.
A week after she had received the threatening letter, and a week before pony rides Sunday, Miss Poole asked to see Thomasina in her office.
“Y-you wanted to see me, Miss Poole…?”
“Yes, come in, dear. Sit down. Now, I’ll tell you what this is about. Next Sunday afternoon I’m going to organise pony rides in the main field. We’re preparing the flyers now, and it’ll be announced in the newsletter.”
“Oh… That’s nice…”
“Yes. But there’s a twist. Only one pony. Can you guess who?”
“Only one? No… Who?”
“Ponyboy! Ponyboy from the show. You must have seen him.”
Thomasina blushed scarlet. “Oh… Oh, yes, I see… P-Ponyboy…”
“The thing is, I need a steward to sell and collect tickets, keep the queue in order, and make sure each rider has their allotted time. Would you be able…”
“M-me? Oh, I’m not sure, Miss Poole… You see….it’s rather difficult…so much work…”
“Nonsense, Thomasina. I’m asking you because I know how diligent you are. I’ll give you a forty pound bonus, and you’ll have a special uniform so that everyone will know who’s in charge. Okay?”
Well, I…”
“Good. That’s settled then. Oh, and if you could pop back at about ten this coming Wednesday – you normally ride Wednesday mornings, don’t you - my colleague will get you measured up. Good girl. Keep up the good work. See you Wednesday, then. Ten o’clock.”
It took Cynthia about three minutes to take the salient measurements. Then Thomasina heard nothing more until the Saturday, when Ellie took her aside to explain her duties, and told her report to “the Old House”, a wooden building, half house and half stable, behind the indoor school, on the edge of one of the paddocks - so called because years ago the owner of the estate used to live there.
“Be there at one sharp. Bring your riding boots, whip and helmet.”
“Why will I need…”
“Just do as you’re told. You will change into your uniform, and I believe… Well, if you’re lucky, you may get to meet Ponyboy himself.”
Thomasina’s eyes widened in terror. Ellie supressed a smile, and pretended not to notice.
A week after she had received the threatening letter, and a week before pony rides Sunday, Miss Poole asked to see Thomasina in her office.
“Y-you wanted to see me, Miss Poole…?”
“Yes, come in, dear. Sit down. Now, I’ll tell you what this is about. Next Sunday afternoon I’m going to organise pony rides in the main field. We’re preparing the flyers now, and it’ll be announced in the newsletter.”
“Oh… That’s nice…”
“Yes. But there’s a twist. Only one pony. Can you guess who?”
“Only one? No… Who?”
“Ponyboy! Ponyboy from the show. You must have seen him.”
Thomasina blushed scarlet. “Oh… Oh, yes, I see… P-Ponyboy…”
“The thing is, I need a steward to sell and collect tickets, keep the queue in order, and make sure each rider has their allotted time. Would you be able…”
“M-me? Oh, I’m not sure, Miss Poole… You see….it’s rather difficult…so much work…”
“Nonsense, Thomasina. I’m asking you because I know how diligent you are. I’ll give you a forty pound bonus, and you’ll have a special uniform so that everyone will know who’s in charge. Okay?”
Well, I…”
“Good. That’s settled then. Oh, and if you could pop back at about ten this coming Wednesday – you normally ride Wednesday mornings, don’t you - my colleague will get you measured up. Good girl. Keep up the good work. See you Wednesday, then. Ten o’clock.”
It took Cynthia about three minutes to take the salient measurements. Then Thomasina heard nothing more until the Saturday, when Ellie took her aside to explain her duties, and told her report to “the Old House”, a wooden building, half house and half stable, behind the indoor school, on the edge of one of the paddocks - so called because years ago the owner of the estate used to live there.
“Be there at one sharp. Bring your riding boots, whip and helmet.”
“Why will I need…”
“Just do as you’re told. You will change into your uniform, and I believe… Well, if you’re lucky, you may get to meet Ponyboy himself.”
Thomasina’s eyes widened in terror. Ellie supressed a smile, and pretended not to notice.
The more you give, the more I can give back.
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