� 
Recent Posts
1
Active Sissy Stories / Re: The Second Floor (#29)
« Last post by petticoated on Today at 11:50:56 AM »
Emily laughed. "I love it when you call him(?) 'Sissy,' Dorian. I just love it!" Leighton swallowed hard. "Now, sissy," Dorian addressesd Allen, " The real test." "Go ahead. You know what to do." She took Her left hand and put it (almost ~masculinely~) into Her White Wool MiniSkirt pocket and pointed at him(?) deliberately with Her Feminine right hand. "And it better be perfect." This Feminine, powerful Blonde Goddess stared directly at Her shaking, quivering "Administrative Assistant," forcing him(?) to obey Her every order, no matter how much humiliation he(?) was forced to endure. "Curtsy for me, sissy." Still looking submissively, in his(?) 4-inch black heels, he(?) daintily took his(?) perfectly painted and manicured (Feminized) fingers and delicately took his(?) exposed lavishly lace-trimmed white tulle ~~Petticoats,-~~, displaying his Pettis by spreading them out, dipped in docile reverence, and then, in his(?) highest squeakiest (sissyish) Feminine voice possible, responded, "Yes, Mistress Dorian." Dorian coldly responded, "NOT...GOOD...ENOUGH, sissy. You look like a pretty boi in a Dress. Now...bring us our drinks before I ~~Petticoat~~ you..."
2
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on June 30, 2025, 08:33:04 AM »
Chapter 200.
The programmes for the October Show were delivered to reception as promised on Friday afternoon. As soon as Miss Poole heard, she came out of her office and checked through one carefully, to make sure there were no errors. It was an eight-page booklet, with the Centre logo on the cover over a photograph of one of the top senior dressage horses and rider, Charlotte Macilveney. Both inside covers and one side of one page were devoted to full-page commercial adverts, including the Centre’s sponsors, whilst each of the remaining five pages was given over to details of the events. There was a page for the main arena programme, with a timetable for all the senior events, showing, showjumping, dressage, and so in in their various classes, culminating with the dressage final; a page for the gymkhana and junior events, including showjumping, races, show ponies, best rider, best turned out pony and rider; two pages for the timetable of events in the main field, with classes for things like best piebald or skewbald, best lead rein pony, best ridden pony, best veteran, cutest filly or mare, and even a class simply called “think pink”! The final inside page contained a list of all the stallholders and their locations. There would be stalls all around the field, and intermittently around the perimeters of the arenas. The smaller ones would be selling food, drink, and anything horsey, from keyrings, earrings, bangles and stuffed animals to clothing – though there were two large stalls adjacent to the main arena run my major retailers with a full range of clothing, tack and accessories. (Anything that might spook the horses, like balloons or anything noisy, was strictly forbidden.) But out of the whole programme, what immediately caught the attention of Evelina and Gabby was the back cover. Below “Boot Boys at Pitt’s Wood!” in bright shiny red letters like inflated balloons, it featured four small photos: top left, the inner sanctum, top right, Timothy in his superhero outfit, culled from the picture on Miss Poole’s phone, bottom left, one of Bobby in his blue and yellow outfit, courtesy of Clarissa, his face hidden under the peak of his baseball cap, and bottom right….an indistinct one of Mélisande perched on what appeared to be a diminutive bay pony!
Evelina held it up and looked at Miss Poole enquiringly.
“Ah, yes. A little teaser. No-one will understand what that is until after the senior dressage. And I don’t want anyone to see these until we hand them out tomorrow. Timothy’s coming in for a training session at one, and I have a little surprise in store for him. Excellent! The weather’s going to be good. I think we should have a really great day.”
Miss Poole had dropped into stable thirteen earlier that day to see how Timothy’s training was progressing. He had already spent hours on his knees in front of Jasmin or Ellie or both of them together receiving instruction and slaving away on various types of riding and fashion boots, with mixed results.
“Well girls? How’s our new recruit doing?”
“Not bad, Miss Poole,” said Jasmin, unenthusiastically. “He’s learning the techniques, but he still doesn’t comport himself well…”
“His attitude suc-ks,” clarified Ellie. “I’ve explained to him again and again that he needs to show politeness and subservience. He understands all right, miss, but I think it’s just that he can’t bring himself to do it. He’s got this stupid macho thing in his head that men should never defer to women or girls. It’s really annoying. Maybe he’ll be better with the customers, but sometimes with us he’s just plain rude.”
Miss Poole frowned. “I see… Is that right, Timmy?”
Timothy looked flustered. “Well, I don’t see why I ‘ave to crawl to them, any of ‘em. Some of these stable girls are younger than me for one, and I ‘ear that some of the women are, like, old enough to be my muvver. It seems to me…”
“Don’t say another word. You clearly don’t understand the meaning of respect. So, since you are already under contract, I’m going to invoke one of the penalty clauses.” She looked around, Her gaze alighted on a dressage whip propped in one corner of the stable. “Right. Girls, hold him face-down across that bale, would you?”
“Yes, miss.”
“Oi! Get yer ‘ands orf me! I said…”
“And I said, not another word, Master Timmy. From now on, every word you utter will earn you an extra stroke of the whip.”
Timothy wasn’t weak, but those girls were older and used to manual labour. They held him firmly while Miss Poole yanked down his shorts and underpants, picked up the whip, and gave him such a stoke that he yelped with pain, and a thin read weal appeared across his white buttocks.
“No – please!”
“That’s two extra, then.”
She administered another twelve well-aimed strokes, which left his bottom criss-crossed with livid red lines, and him sobbing and moaning. He wanted to plead, but now he was too frightened to do so. She threw down the whip.
“If you don’t quickly adjust your attitude, my boy, you’ll get another twelve tomorrow. I do not tolerate misogyny in my staff. So now you’ll come in tomorrow as well, and practise on some of the other stable girls until I’m satisfied. Ellie, you’re not involved in any of the events tomorrow, are you?”
“No, miss, but…”
“I know. I’m sure you’d like to watch. So I’ll make sure he’s fitted with a collar and chain so he can be tethered up here for some of the time. And I’m going to appoint you as Boot Boy Supervisor going forward. You will be in charge of reports, complaints, discipline, and costume rotation. We can discuss and agree your new duties in due course. And of course you’ll have a substantial pay supplement.”
“Thank you, miss,” said Ellie, delightedly. She couldn’t think of anything nicer than being totally in charge of two big, rebellious sissies like Timothy and Bobby.
“And you – have you learnt your lesson, or do I have to…”
Timothy, completely cowed, struggling to wipe the tears from his cheeks and pull up his pants and the same time, looked up at meekly.
“Yes, miss…I’m sorry…I didn’t mean…I promise…I’ll be nice to all the ladies…everyone…I will…”
“Good. That’s most reassuring. Make sure you are. Tomorrow at one, then. And in the afternoon Cynthia will return with your superhero uniform. She’s made the few adjustments necessary and is confident it’ll fit you like a glove. I’m sure you’re happy about that.”
“Oh, yes, Miss Poole. Fank you. I can’t wait to, er…put it on again…”
Though oddly the expression on his face didn’t betray quite the same level of enthusiasm…
The programmes for the October Show were delivered to reception as promised on Friday afternoon. As soon as Miss Poole heard, she came out of her office and checked through one carefully, to make sure there were no errors. It was an eight-page booklet, with the Centre logo on the cover over a photograph of one of the top senior dressage horses and rider, Charlotte Macilveney. Both inside covers and one side of one page were devoted to full-page commercial adverts, including the Centre’s sponsors, whilst each of the remaining five pages was given over to details of the events. There was a page for the main arena programme, with a timetable for all the senior events, showing, showjumping, dressage, and so in in their various classes, culminating with the dressage final; a page for the gymkhana and junior events, including showjumping, races, show ponies, best rider, best turned out pony and rider; two pages for the timetable of events in the main field, with classes for things like best piebald or skewbald, best lead rein pony, best ridden pony, best veteran, cutest filly or mare, and even a class simply called “think pink”! The final inside page contained a list of all the stallholders and their locations. There would be stalls all around the field, and intermittently around the perimeters of the arenas. The smaller ones would be selling food, drink, and anything horsey, from keyrings, earrings, bangles and stuffed animals to clothing – though there were two large stalls adjacent to the main arena run my major retailers with a full range of clothing, tack and accessories. (Anything that might spook the horses, like balloons or anything noisy, was strictly forbidden.) But out of the whole programme, what immediately caught the attention of Evelina and Gabby was the back cover. Below “Boot Boys at Pitt’s Wood!” in bright shiny red letters like inflated balloons, it featured four small photos: top left, the inner sanctum, top right, Timothy in his superhero outfit, culled from the picture on Miss Poole’s phone, bottom left, one of Bobby in his blue and yellow outfit, courtesy of Clarissa, his face hidden under the peak of his baseball cap, and bottom right….an indistinct one of Mélisande perched on what appeared to be a diminutive bay pony!
Evelina held it up and looked at Miss Poole enquiringly.
“Ah, yes. A little teaser. No-one will understand what that is until after the senior dressage. And I don’t want anyone to see these until we hand them out tomorrow. Timothy’s coming in for a training session at one, and I have a little surprise in store for him. Excellent! The weather’s going to be good. I think we should have a really great day.”
Miss Poole had dropped into stable thirteen earlier that day to see how Timothy’s training was progressing. He had already spent hours on his knees in front of Jasmin or Ellie or both of them together receiving instruction and slaving away on various types of riding and fashion boots, with mixed results.
“Well girls? How’s our new recruit doing?”
“Not bad, Miss Poole,” said Jasmin, unenthusiastically. “He’s learning the techniques, but he still doesn’t comport himself well…”
“His attitude suc-ks,” clarified Ellie. “I’ve explained to him again and again that he needs to show politeness and subservience. He understands all right, miss, but I think it’s just that he can’t bring himself to do it. He’s got this stupid macho thing in his head that men should never defer to women or girls. It’s really annoying. Maybe he’ll be better with the customers, but sometimes with us he’s just plain rude.”
Miss Poole frowned. “I see… Is that right, Timmy?”
Timothy looked flustered. “Well, I don’t see why I ‘ave to crawl to them, any of ‘em. Some of these stable girls are younger than me for one, and I ‘ear that some of the women are, like, old enough to be my muvver. It seems to me…”
“Don’t say another word. You clearly don’t understand the meaning of respect. So, since you are already under contract, I’m going to invoke one of the penalty clauses.” She looked around, Her gaze alighted on a dressage whip propped in one corner of the stable. “Right. Girls, hold him face-down across that bale, would you?”
“Yes, miss.”
“Oi! Get yer ‘ands orf me! I said…”
“And I said, not another word, Master Timmy. From now on, every word you utter will earn you an extra stroke of the whip.”
Timothy wasn’t weak, but those girls were older and used to manual labour. They held him firmly while Miss Poole yanked down his shorts and underpants, picked up the whip, and gave him such a stoke that he yelped with pain, and a thin read weal appeared across his white buttocks.
“No – please!”
“That’s two extra, then.”
She administered another twelve well-aimed strokes, which left his bottom criss-crossed with livid red lines, and him sobbing and moaning. He wanted to plead, but now he was too frightened to do so. She threw down the whip.
“If you don’t quickly adjust your attitude, my boy, you’ll get another twelve tomorrow. I do not tolerate misogyny in my staff. So now you’ll come in tomorrow as well, and practise on some of the other stable girls until I’m satisfied. Ellie, you’re not involved in any of the events tomorrow, are you?”
“No, miss, but…”
“I know. I’m sure you’d like to watch. So I’ll make sure he’s fitted with a collar and chain so he can be tethered up here for some of the time. And I’m going to appoint you as Boot Boy Supervisor going forward. You will be in charge of reports, complaints, discipline, and costume rotation. We can discuss and agree your new duties in due course. And of course you’ll have a substantial pay supplement.”
“Thank you, miss,” said Ellie, delightedly. She couldn’t think of anything nicer than being totally in charge of two big, rebellious sissies like Timothy and Bobby.
“And you – have you learnt your lesson, or do I have to…”
Timothy, completely cowed, struggling to wipe the tears from his cheeks and pull up his pants and the same time, looked up at meekly.
“Yes, miss…I’m sorry…I didn’t mean…I promise…I’ll be nice to all the ladies…everyone…I will…”
“Good. That’s most reassuring. Make sure you are. Tomorrow at one, then. And in the afternoon Cynthia will return with your superhero uniform. She’s made the few adjustments necessary and is confident it’ll fit you like a glove. I’m sure you’re happy about that.”
“Oh, yes, Miss Poole. Fank you. I can’t wait to, er…put it on again…”
Though oddly the expression on his face didn’t betray quite the same level of enthusiasm…
3
Active Sissy Stories / Re: The Second Floor (#28)
« Last post by petticoated on June 29, 2025, 11:07:47 PM »
"Don't move, pretty boi," Dorian ordered. To be sure, Emily stood directly beside leighton, Her UltraFeminine minidress still powerfully enveloping him. Leighton obeyed Dorian's order to stand still while the tall Blonde beauty removed the cap from the tube of Lipstick, turned the narrow cylinder slowly, and in no time, the Red Lipstick appeared. Leighton's eyes widened. He started shaking as Dorian approached him, the Red Lipstick just inches away now from its intended target. "Stay perfectly still while I apply a first coat. Don't move. And stop shaking. It's only Lipstick," She said, almost casually. And then, purposely and meticulously, with Emily watching intently, Dorian applied the "Blood Red" Urban Decay lipstick. The taste immediately increased leighton's little soldier's arousal even more. "Now, purse your lips.. gently...like a Girl...go ahead...do as I say. That's it! Good boy! Doesn't it taste just scrumptuous? Stay still while I apply a second coat." Leighton never moved. Total acquiescence. "Good boy!" Dorian looked at Emily, commenting, "Em, just imagine how pretty he would look with a full face of ~Makeup~!" Emily replied, "I told you, Dorian!" Emily smiled at Leighton, "My very own pretty boi." Dorian turned Her attention to Allen, who had remained in his subservient position while the Girls had fun with leighton. "Allison'," Dorian addressed Allen, "Attend to our drinks. Two Scotch on the rocks and a Shirley Temple for leighton. And be quick about it, ~sissy.~"...
4
Active Sissy Stories / Re: The Second Floor (#27)
« Last post by petticoated on June 29, 2025, 09:37:31 PM »
Leighton's knees buckled at what he saw in the corner of the spacious and Feminine living room area. Emily exclaimed, "Oh! You're back, leighton. Now we can start to have some real fun!" Making delicious Feminine Frou Frou with Her five-tiered white Tulle Minidress, Her silver five-inch slingback stilettos click clacked across the marble floor while Her Tulle rustled and swished musically. She towered over Her little (boi)friend(zone). Swishing Her skirts back and forth, Emily then planted a long and lasting kiss directly on leighton's submissive quivering mouth while Her minidress enveloped him. As She slowly and skillfully moved Her tongue inside and around the stunned little man's(?) Small mouth, She made certain that Her Pettilayers of stiff white tulle continued to tease him mercilessly. His little soldier was wriggling helplessly in its own Emasculating satin and lace panty pouch. Emily had purposely and skillfully transferred Her Lipstick to poor leighton's mouth. Pulling away, She Femininely feigned "surprise" at leighton's now colored lips. "Oh my! You really look rather sweet in my Lipstick. Pretty...actually." When leighton realized what She had done to his mouth, he indtinctively moved his right hand up towards his face with every intention of removing Her Lipstick...until She firmly grabbed his arm and stopped him. Then She immediately and purposely took Her right index finger and started to blend Her Lipstick more evenly over his shaking lips. Then Dorian, resplendent in Her Authoritarian white wool miniskirted skirt suit, moved quickly to the Feminine bathroom, Her 5-inch heels Femininely click clacking on the white marble surface. In a few seconds, the tall Stunning Blonde had returned and told Emily to hold leighton in place. Standing directly in front of him now, and towering over the little man(?), Dorian reached into the right side pocket of Her white wool miniskirt and removed a tube of Urban Decay "Bad Blood" Red lipstick...
5
Active Sissy Stories / Re: The Second Floor (#26)
« Last post by petticoated on June 29, 2025, 05:21:26 PM »
Tentatively opening the Feminine bathroom door, leighton swallowed hard. Hearing the two Beautiful Women laughing, he soon saw the reason. Standing in the corner of the luxuriously spacious main living room was Allen. His head was looking down, very subserviently. He looked scared. Embarrassed. Defeated. And leighton knew this poor man(?), Dorian's so-called "Administrative Assistant," looked more like, dare leighton think this, a Feminized male maid. To be honest, a ~sissy maid.~ Allen's (?) Frilly maid's dress was Pinafore-Styled. And it was anything but costumish. It was luxurious! Feminine. Black Taffeta, leighton guessed. Mini-length, several inches above Allen's knees. The three layers of stiff snow white Tulle, lace-trimmed ( at least two inches) weren't concealed at all. And the Satin and Taffeta Dress must have had maybe (leighton surmised) a stiff black Crinoline underskirt sewn into the taffeta skirt to add to its poufiness. His(?) Long-sleeved white sheer chiffon blouse did nothing to conceal his(?) Lacy white camisole. The high ruffled white lace collar was topped off with a little black satin men's(?) style bow tie. (The obvious "masculine" contradiction that Dorian had personally requested.) But Allen wasn't all alone in his little corner. Oh no. Directly to his(?) right was a very realistic (definitely AI influenced) androgynous-looking man-nequin. Essentially, a very pretty sissy boi. Blonde pixie-style haircut. Tasteful makeup, mostly pinkish. Pretty hands (all the way down to its stylishly long pink nails) sissyishly placed on its hips. The expression on the very realistic sissy mannequin's face was one of mocking disdain. But what really stood out, literally and figuratively, was what the sissy mannequin was wearing! Dorian had called it a "Special ~~Intensive Sissification Petticoat~~ from Cinderella." And now...EVERYONE in the room knew why...
6
Active Sissy Stories / Re: The Second Floor (#25)
« Last post by petticoated on June 29, 2025, 08:05:15 AM »
Two more Lichtenstein nudes adorned the walls of the Feminine bathroom. Adorning the white marble Vanity top, a Feminine assortment of Makeup Brushes, all pale Pink and White, Dior Eyeshadow and Blush Palettes and Compacts, Lipsticks, Mascara...all directly and temptingly teasing poor leighton, beckoning his (sissy) infatuations. As leighton slid his trousers back on and over the Emasculatingly Feminizing Ruffled White Lace encrusted double-satin pouch, his aroused little soldier struggled to contain itself. Struggling to pull the zipper of his trousers over the stiff white ruffled French lace, without damaging it, his little soldier's arousal only heightened. Then, startled by a gentle knock on the door amid the swishing and rustling of Emily's Dress, She whispered thru the door, "Don't worry, little man. If you get too excited, I have a backup Panty just for you. It IS a bit frillier.. and it does have a Baby Girly Pink Bow. Do you need my help?" She asked, giggling. "N...n...noooo. I've got it. I...I...I'll........be......out...in a second." "Okay, if you're sure." The sibilant swishing of Her Tulle Skirts and the click clacking of Her Heels were heard as She returned to the spacious and exquisitely Feminine living room, sharing a laugh with Dorian. Finally securing the zjpper of his pants, the bulge from his Emasculating panty pouch would be shamefully obvious to both of these two Beautiful Women who were in total Feminine control of both bois...and They knew it...
7
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on June 26, 2025, 07:32:52 AM »
Chapter 199.
The following day, Thursday, Lavinia picked up Timothy at seven-thirty and drove him back to Pitt’s Wood to begin his crash course in boot boy training with Jasmin and Ellie. He wasn’t looking forward to it – but they definitely were. It was also Bobby’s final training day before the show. Friday would be a rest day. Mélisande took him out for a gentle trot round the forest in the morning, and popped him over a couple of poles. Her only worry was how the new pony suit would affect his action. She had discussed this with her mother and Nicole, and they had decided to try it on him that afternoon, to check it was going to be okay. If there were any doubts they would stick to the old one. But Mélisande, having seen the new one, was desperate for him to wear it on Saturday. It was so pretty, sort of speckled grey and white, and the hood had a real mane and furry ears, and there was a new bridle in lovely tan leather, and because he would be a little taller it would allow her longer stirrup leathers and a more upright seat.
In the event it was a total success. Bobby was shocked when he saw it, but once he was all strapped in he pronounced it much more comfortable than the old one. That was a good first step. Of course they couldn’t show him the new open-face hood, so they used the old one, and they dispensed with the new tail for the time being, and Mélisande took him round the little course in the back garden. She needn’t have worried; in the event he found it easier to cross the pole with his longer legs, and she found the extra height gave her more control. She walked him, trotted him, and made him do a few half-passes, till she was quite satisfied there would be no issues on Saturday. Nicole had thoughtfully brought her a new whip. The heavy one given her by Diana Murchison was nothing like a dressage whip, so Nicole had had a standard riding whip modified, the leather flap replaced with a short braided flick, which she presented to her. Mélisande was very happy. Everything was in place for their performance in front of a big audience.
There had been some debate about whether Mélisande and Bobby and should open or close the Unaffiliated Dressage competition, but it was eventually agreed they should do their turn after all the medals and rosettes had been presented, that is to say after both the Junior and Senior classes had taken place, and then Miss Poole could also make the announcement about the new boot parlour. She would have loved to have Mélisande and Bobby appear in the junior class as a late declaration, but her respect for the rules overcame the temptation. She also had another idea in mind, which she had discussed with Nicole over a drink about ten days before the show.
“How does Mélisande feel now Bobby’s training is coming to an end?”
“Oh - well it isn’t, really, Violet. We’ve told her she can go on riding him as long as she wants. Part of the thinking behind investing in the new pony suit was to allow her to carry on riding him as she grows up. And Bobby himself seems quite to enjoy his pony role. Apart from demonstrating his strength and fitness, I get the impression he actually enjoys the challenge. I’ve noticed whenever she praises him, he gets this pleased expression of his face – sort of contented and proud of himself. And she’s told her mother she’d really like to teach him new skills.”
“Really? Such as?”
“Well, she believes that she can eventually have him jumping a low hurdle. Wouldn’t that be something? According to Mélisande it’s just a matter of coordination.”
“Wow. Well they do seem to have a mutual respect. It’s unusual, of course, but I find it rather touching. I do hope they stay friends in the long term.”
“I think they will.”
“Well… What I wanted to ask was…” – she lowered her voice – “do you think Mélisande would be amenable to, well, letting someone else ride him occasionally…?”
“Oh. Well, Violet, I’m not sure. She’s very possessive of him. Actually she has a rival for his attention, but at the moment she seems to be winning that battle.”
“Well, I didn’t mean she’d have to share him with another girl. No. Let me explain…”
The rest of the conversation was conducted in whispers, and ended with Nicole promising to consult Mélisande about the matter. So by the time of the final training session, and after a number of conversations involving Nicole, Miss Poole and Mélisande, an arrangement had been worked out which, within certain parameters, would allow Miss Poole to put her plans into practice. The only person involved who was not privy to them was, of course, Bobby himself.
[The author is indebted to Gabby for drawing the appended rough sketchmap of Pitt's Wood, and apologises that it did not appear earlier.]
The following day, Thursday, Lavinia picked up Timothy at seven-thirty and drove him back to Pitt’s Wood to begin his crash course in boot boy training with Jasmin and Ellie. He wasn’t looking forward to it – but they definitely were. It was also Bobby’s final training day before the show. Friday would be a rest day. Mélisande took him out for a gentle trot round the forest in the morning, and popped him over a couple of poles. Her only worry was how the new pony suit would affect his action. She had discussed this with her mother and Nicole, and they had decided to try it on him that afternoon, to check it was going to be okay. If there were any doubts they would stick to the old one. But Mélisande, having seen the new one, was desperate for him to wear it on Saturday. It was so pretty, sort of speckled grey and white, and the hood had a real mane and furry ears, and there was a new bridle in lovely tan leather, and because he would be a little taller it would allow her longer stirrup leathers and a more upright seat.
In the event it was a total success. Bobby was shocked when he saw it, but once he was all strapped in he pronounced it much more comfortable than the old one. That was a good first step. Of course they couldn’t show him the new open-face hood, so they used the old one, and they dispensed with the new tail for the time being, and Mélisande took him round the little course in the back garden. She needn’t have worried; in the event he found it easier to cross the pole with his longer legs, and she found the extra height gave her more control. She walked him, trotted him, and made him do a few half-passes, till she was quite satisfied there would be no issues on Saturday. Nicole had thoughtfully brought her a new whip. The heavy one given her by Diana Murchison was nothing like a dressage whip, so Nicole had had a standard riding whip modified, the leather flap replaced with a short braided flick, which she presented to her. Mélisande was very happy. Everything was in place for their performance in front of a big audience.
There had been some debate about whether Mélisande and Bobby and should open or close the Unaffiliated Dressage competition, but it was eventually agreed they should do their turn after all the medals and rosettes had been presented, that is to say after both the Junior and Senior classes had taken place, and then Miss Poole could also make the announcement about the new boot parlour. She would have loved to have Mélisande and Bobby appear in the junior class as a late declaration, but her respect for the rules overcame the temptation. She also had another idea in mind, which she had discussed with Nicole over a drink about ten days before the show.
“How does Mélisande feel now Bobby’s training is coming to an end?”
“Oh - well it isn’t, really, Violet. We’ve told her she can go on riding him as long as she wants. Part of the thinking behind investing in the new pony suit was to allow her to carry on riding him as she grows up. And Bobby himself seems quite to enjoy his pony role. Apart from demonstrating his strength and fitness, I get the impression he actually enjoys the challenge. I’ve noticed whenever she praises him, he gets this pleased expression of his face – sort of contented and proud of himself. And she’s told her mother she’d really like to teach him new skills.”
“Really? Such as?”
“Well, she believes that she can eventually have him jumping a low hurdle. Wouldn’t that be something? According to Mélisande it’s just a matter of coordination.”
“Wow. Well they do seem to have a mutual respect. It’s unusual, of course, but I find it rather touching. I do hope they stay friends in the long term.”
“I think they will.”
“Well… What I wanted to ask was…” – she lowered her voice – “do you think Mélisande would be amenable to, well, letting someone else ride him occasionally…?”
“Oh. Well, Violet, I’m not sure. She’s very possessive of him. Actually she has a rival for his attention, but at the moment she seems to be winning that battle.”
“Well, I didn’t mean she’d have to share him with another girl. No. Let me explain…”
The rest of the conversation was conducted in whispers, and ended with Nicole promising to consult Mélisande about the matter. So by the time of the final training session, and after a number of conversations involving Nicole, Miss Poole and Mélisande, an arrangement had been worked out which, within certain parameters, would allow Miss Poole to put her plans into practice. The only person involved who was not privy to them was, of course, Bobby himself.
[The author is indebted to Gabby for drawing the appended rough sketchmap of Pitt's Wood, and apologises that it did not appear earlier.]
8
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on June 26, 2025, 07:22:21 AM »
Chapter 198.
They stopped at The Shire Horse for lunch – the travails of the morning had given Timothy an appetite – and grabbed a table under the shade of an elm. Timothy expressed an interest fish and chips, accompanied by a large fizzy drink, and Lavinia went off to order.
As he sat in the pub garden waiting for Lavinia to return, Timothy was wondering how he’d got himself into this mess. He was trying to grasp the fact that, in a few days’ time, he was going to find himself wearing a latex superhero uniform, kneeling in front of some girl or woman he didn’t know, polishing up her boots like a slave, and probably being admonished for his sub-standard workmanship. Well, it was the money, right? He’d been blinded by the thought of a guaranteed income for the whole year! Idiot! Or was he? It would be more dosh than he’s ever had… Maybe it wouldn’t be so bad… He bit his lip. This was a strange world he’s strayed into. Those girls at Nicole’s house. What was that about? That girl in the hood… Latex, again! And she looked like some sort of slave, too… He mustn’t end up like her, whatever happened. No, he would need to be careful from now on. And he must read that contract! What else had he signed up for, that he wasn’t aware of? A cold sweat broke out of his forehead…
“Timmy? Are you okay? You look pale… Here’s your drink. The fish and chips will be ten minutes, she said…”
Had Timothy known what Nicole did for a living, he would have been even more worried than he was. Had he just read the penalty clauses in his contract, which imposed various punishments for quite minor offences, such as lateness, rudeness, or minor acts of disobedience, involving various humiliations or strokes of the whip (riding or dressage, in varying numbers, depending on seriousness), he would have been seriously alarmed. And that evening, as he studied the small print, and it dawned on him that he was now under the thumb of Miss Poole, and the sinister authority that was the committee of Pitt’s Wood Equestrian Centre, and that there was no escape for at least a year, he was seized with something verging on panic. He grabbed his phone and dialled Bobby’s number.
“Bobby! It’s me.”
“Hi, Tim. How’s it goin’?”
“Did you sign a contract with Pitt’s Wood?”
“Yeah…”
“Wiv all them penalty clause fings?”
“Oh… Yeah. Didn’t have a choice, mate…”
“But…they can do all sorts of stuff…”
“Yeah, but if you behave yourself and do a good job… So have you signed it?”
“Yeah… I fought if you’d signed it must be okay, see?”
“Well don’t say I didn’t warn you.”
“You never told me about all this…”
“Why didn’t you read it, stupid? Oh, I saw a piccy of you in your uniform. So cute…”
“You knew, didn’t you? You bleedin’ knew and never said a word! Well, wait till you see yours! The joke’s on you, Bobby.”
“What do you mean? Mine’s not gonna be any different from yours...is it?”
“Oh, a little bit different, maybe.”
“How? How different?”
“Wait an’ see…stupid!”
And he ended the call.
“That…idiot! Wait till ‘e sees it. Pink and mauve! Ha ha. Big sissy! “I told you so!” What a laugh…”
They stopped at The Shire Horse for lunch – the travails of the morning had given Timothy an appetite – and grabbed a table under the shade of an elm. Timothy expressed an interest fish and chips, accompanied by a large fizzy drink, and Lavinia went off to order.
As he sat in the pub garden waiting for Lavinia to return, Timothy was wondering how he’d got himself into this mess. He was trying to grasp the fact that, in a few days’ time, he was going to find himself wearing a latex superhero uniform, kneeling in front of some girl or woman he didn’t know, polishing up her boots like a slave, and probably being admonished for his sub-standard workmanship. Well, it was the money, right? He’d been blinded by the thought of a guaranteed income for the whole year! Idiot! Or was he? It would be more dosh than he’s ever had… Maybe it wouldn’t be so bad… He bit his lip. This was a strange world he’s strayed into. Those girls at Nicole’s house. What was that about? That girl in the hood… Latex, again! And she looked like some sort of slave, too… He mustn’t end up like her, whatever happened. No, he would need to be careful from now on. And he must read that contract! What else had he signed up for, that he wasn’t aware of? A cold sweat broke out of his forehead…
“Timmy? Are you okay? You look pale… Here’s your drink. The fish and chips will be ten minutes, she said…”
Had Timothy known what Nicole did for a living, he would have been even more worried than he was. Had he just read the penalty clauses in his contract, which imposed various punishments for quite minor offences, such as lateness, rudeness, or minor acts of disobedience, involving various humiliations or strokes of the whip (riding or dressage, in varying numbers, depending on seriousness), he would have been seriously alarmed. And that evening, as he studied the small print, and it dawned on him that he was now under the thumb of Miss Poole, and the sinister authority that was the committee of Pitt’s Wood Equestrian Centre, and that there was no escape for at least a year, he was seized with something verging on panic. He grabbed his phone and dialled Bobby’s number.
“Bobby! It’s me.”
“Hi, Tim. How’s it goin’?”
“Did you sign a contract with Pitt’s Wood?”
“Yeah…”
“Wiv all them penalty clause fings?”
“Oh… Yeah. Didn’t have a choice, mate…”
“But…they can do all sorts of stuff…”
“Yeah, but if you behave yourself and do a good job… So have you signed it?”
“Yeah… I fought if you’d signed it must be okay, see?”
“Well don’t say I didn’t warn you.”
“You never told me about all this…”
“Why didn’t you read it, stupid? Oh, I saw a piccy of you in your uniform. So cute…”
“You knew, didn’t you? You bleedin’ knew and never said a word! Well, wait till you see yours! The joke’s on you, Bobby.”
“What do you mean? Mine’s not gonna be any different from yours...is it?”
“Oh, a little bit different, maybe.”
“How? How different?”
“Wait an’ see…stupid!”
And he ended the call.
“That…idiot! Wait till ‘e sees it. Pink and mauve! Ha ha. Big sissy! “I told you so!” What a laugh…”
9
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on June 26, 2025, 07:16:01 AM »
Chapter 197.
With the appearance of Timothy at the stables, the rumours that had been flying around Pitt’s Wood for weeks began to resolve themselves into concrete news, supported by photographic and video evidence, which by that evening had circulated throughout the staff – and beyond. Siblings and mothers unconnected with the Centre gasped, goggled and giggled at the images of a very cute but distinctly unhappy and red-faced latex-clad superhero standing squirming in front of the stables, trying to wrap himself in his cape, which sadly for him was not quite wide enough to be a lot of help, even when stretched. When Evelina, the Pitt’s Wood receptionist, returned from lunch that day, she found a heap of notes on her desk, and the phone was ringing off the hook.
“Sorry,” said Gabby, her assistant, “but all these people want to make bookings for the boot parlour. I didn’t even know if we were taking bookings yet. So I just took the names and phone numbers and said we’d ring them back.”
“Oh! Neither did I. Let me ask Miss Poole…”
But at that moment Miss Poole appeared from the direction of her office.
“Oh, Miss Poole…”
“I know, Evelina. Bookings for the boot parlour? Yes, I’ve just heard one of the boys has been having a fitting for his first uniform, and it seems to have generated some degree of interest.”
“That’s an understatement. We’ve been inundated!”
“Well, sounds like a good start. We should start logging them. You have the book, you know the terms. It will be open from nine next Monday. Gabby, do you think you could be responsible for the boot parlour bookings today? Evelina will show you how to do it. The scale of charges is in the front of the booking ledger.”
“Yes, Miss Poole, of course.”
She leant over the counter and flicked through the notes.
“Most of these are older women – though a lot of these names I don’t recognise. Let me see… Yes, I think initially we should reserve nine to eleven each day for staff. If they’re not staff, book them in from eleven on. Give the boys one to two for lunch…but we’ll keep them at work till six. I’m sure this initial rush will soon slow down, but we need to deal with as many as possible as quickly as possible. So half an hour max for the first few weeks, until the rush slackens off…”
“I’ll make a start ringing these back,” said Gabby. “Gosh…quite a response…”
Miss Poole laughed. “Yes, all thanks to Timothy, it seems. Everyone’s happy – except him, to judge from the photo I’ve been sent.”
She held up her phone for them to see. Evelina laughed, and Gabby squealed.
“Oh, the poor boy! What a face! And he looks so cute…”
“Yes. I’ll make sure he smiles when he’s on the job. Or I may have to invoke a penalty clause… But I came out to talk to you about another related matter. The programmes for Saturday. You know there was a delay in the printing because of some problem with one of the machines.”
“Yes, I heard,” said Evelina. “Has it been resolved?”
“Yes, thank goodness. But it turned out it was a godsend, because it’s allowed me to update the boot parlour info inside the back cover. I’ve redone the artwork to include Timothy, using this photo.”
“He won’t be very happy about that!”
“Well it’s the only one we have. He shouldn’t have looked so miserable, should he?”
Evelina laughed. “No, I guess not. What about Bobby? Are you showing his face? I thought he was supposed to be anonymous.”
“It’s too late for that. In any case, by Saturday afternoon everyone’s going to know exactly who he is.”
“Oh, really?”
“Really. Now, Evelina, I have a meeting with our sponsors this afternoon about promotions at the show. So I need you to get onto the printers – give them a couple of hours before you call – and check that there’s no more problems, either with the machines or the new artwork.”
“Yes, Miss Poole. Leave it to me.”
With the appearance of Timothy at the stables, the rumours that had been flying around Pitt’s Wood for weeks began to resolve themselves into concrete news, supported by photographic and video evidence, which by that evening had circulated throughout the staff – and beyond. Siblings and mothers unconnected with the Centre gasped, goggled and giggled at the images of a very cute but distinctly unhappy and red-faced latex-clad superhero standing squirming in front of the stables, trying to wrap himself in his cape, which sadly for him was not quite wide enough to be a lot of help, even when stretched. When Evelina, the Pitt’s Wood receptionist, returned from lunch that day, she found a heap of notes on her desk, and the phone was ringing off the hook.
“Sorry,” said Gabby, her assistant, “but all these people want to make bookings for the boot parlour. I didn’t even know if we were taking bookings yet. So I just took the names and phone numbers and said we’d ring them back.”
“Oh! Neither did I. Let me ask Miss Poole…”
But at that moment Miss Poole appeared from the direction of her office.
“Oh, Miss Poole…”
“I know, Evelina. Bookings for the boot parlour? Yes, I’ve just heard one of the boys has been having a fitting for his first uniform, and it seems to have generated some degree of interest.”
“That’s an understatement. We’ve been inundated!”
“Well, sounds like a good start. We should start logging them. You have the book, you know the terms. It will be open from nine next Monday. Gabby, do you think you could be responsible for the boot parlour bookings today? Evelina will show you how to do it. The scale of charges is in the front of the booking ledger.”
“Yes, Miss Poole, of course.”
She leant over the counter and flicked through the notes.
“Most of these are older women – though a lot of these names I don’t recognise. Let me see… Yes, I think initially we should reserve nine to eleven each day for staff. If they’re not staff, book them in from eleven on. Give the boys one to two for lunch…but we’ll keep them at work till six. I’m sure this initial rush will soon slow down, but we need to deal with as many as possible as quickly as possible. So half an hour max for the first few weeks, until the rush slackens off…”
“I’ll make a start ringing these back,” said Gabby. “Gosh…quite a response…”
Miss Poole laughed. “Yes, all thanks to Timothy, it seems. Everyone’s happy – except him, to judge from the photo I’ve been sent.”
She held up her phone for them to see. Evelina laughed, and Gabby squealed.
“Oh, the poor boy! What a face! And he looks so cute…”
“Yes. I’ll make sure he smiles when he’s on the job. Or I may have to invoke a penalty clause… But I came out to talk to you about another related matter. The programmes for Saturday. You know there was a delay in the printing because of some problem with one of the machines.”
“Yes, I heard,” said Evelina. “Has it been resolved?”
“Yes, thank goodness. But it turned out it was a godsend, because it’s allowed me to update the boot parlour info inside the back cover. I’ve redone the artwork to include Timothy, using this photo.”
“He won’t be very happy about that!”
“Well it’s the only one we have. He shouldn’t have looked so miserable, should he?”
Evelina laughed. “No, I guess not. What about Bobby? Are you showing his face? I thought he was supposed to be anonymous.”
“It’s too late for that. In any case, by Saturday afternoon everyone’s going to know exactly who he is.”
“Oh, really?”
“Really. Now, Evelina, I have a meeting with our sponsors this afternoon about promotions at the show. So I need you to get onto the printers – give them a couple of hours before you call – and check that there’s no more problems, either with the machines or the new artwork.”
“Yes, Miss Poole. Leave it to me.”
10
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on June 26, 2025, 07:10:10 AM »
Chapter 196.
The next half hour or so was the worst of Timothy’s life – so far, at least. Cynthia took him by the wrist and led him onto the grassy field, where she proceeded to examine him from different sides and angles, making the occasional note on her phone, till she appeared satisfied she had collected all the information she needed. Nicole and Lavinia remained on the path, chatting and watching, whilst more stable girls and the occasional visitors gathered around the group in a circle chattering , laughing and taking snaps.
“She’s such a perfectionist,” remarked Lavinia.
“Totally,” replied Nicole. “And you realise there are more outfits in the pipeline she’s still working on.”
“Gosh… I do hope it all pays off in the end… You must have spent a fortune.”
“Money well spent, Lavinia – just look at him! Imagine him and Bobby working as a pair – cuteness on steroids. I’ll be surprised if they don’t have the women flocking here. Though they need to do a good job at the same time. Bobby’s the best, of course. He loves clean, shiny boots, as we well know. Timmy? He will need some intensive training, but I’m working on that.”
Once Cynthia was satisfied, Timothy was allowed to return to the privacy of the stable and change into his everyday clothes. When he emerged he was surprised to find about twenty or thirty of his original audience were still hanging around, and raised a cheer at his reappearance. He heard a whisper of “he’s so handsome!” from one of the younger ones, which did wonders for his ego. And then someone shouted, “we love you, Timmy!” and everyone laughed. Lavinia had packed away his superhero outfit, and handed it to Cynthia so she could make some final adjustments. The four of them walked back to the car park together.
“Well I think that was a success, don’t you Timmy?” said Lavinia. But she got no reply. To tell the truth, Timothy was feeling slightly confused. There was a battle going on within that large area of his psyche called his ego. He hated the outfit but loved the attention.
In the car park Nicole ruffled his hair. “Great job, Timmy. You looked fab! I’ll send you some pics to show your mum. She’s going to be so proud…”
Nicole drove off with Cynthia, while Timothy got into Lavinia’s car.
“Do you want to go straight home, or shall be stop at the pub for a drink and a snack? Or lunch, even?”
“Pub, please.”
“Okay. Cheer up. It wasn’t that bad, was it?”
“It’s just…that outfit… I feel, like, a total sissy. It’s ten times worse than I fought it would be.”
“Oh, come on. It looks great on you, actually. The trouble is you see it with a man’s eyes. The girls at the Centre loved you. Didn’t you see them ogling you? I mean, you have a super body, darling. Make the most of it. It’s a great excuse to show it off.”
Timothy felt slightly mollified.
“Yeah, well, I may ‘ave, I guess.”
“So what’s the problem? I could see from the expressions on some of those girls faces that, given the chance, they would have been fighting each other over you!”
He glanced up at her, checking if she was serious. There wasn’t even the hint of a smile.
“D’you reckon?”
“Of course! For some of them I bet a nice-looking bloke in a superhero costume is just about their wildest fantasy.”
He denied it, but looked pleased. “Nah… I mean, maybe if it was all black, or somefink…”
“Well, I’m sure Cynthia could make you one in black – black with a coloured trim would be cool...”
“Really?”
“I’ll ask. Anyway, red and yellow’s not sissy. Now Bobby’s outfit – that’s proper sissy colours!”
That caught Timothy’s attention. He looked at her eagerly. “What do you mean?”
“Well, don’t tell him, will you? Promise?”
“No. Course not. I swear.”
“What is little girls’ favourite colour combination? Do you know?”
“Well…pink…”
“Pink and mauve! They love pink and mauve! Look at their toys. And little girls love pink and mauve dresses. So guess what colours Bobby’s superhero outfit is!”
“Pink…and mauve?”
“Yes! Pink top, pink pants, mauve cape and frills! Oh my god, he’s going to be so embarrassed! He’ll be like, little miss superhero! I can’t wait to see him.”
Timothy was ecstatic. “Yes!! And he don’t know?”
“No idea. He doesn’t need a fitting, because Cynthia’s makes stuff for him all the time.”
Timothy laughed, and shook a fist in the air. So Bobby was going to be the sissy, and he, Timmy the Boot Boy, would be the cool one. That was fair. Yes, perfect. He’d always thought Bobby was a bit girlish. Yes, pink and mauve…perfect. Now the girls would really have something to giggle at…
The next half hour or so was the worst of Timothy’s life – so far, at least. Cynthia took him by the wrist and led him onto the grassy field, where she proceeded to examine him from different sides and angles, making the occasional note on her phone, till she appeared satisfied she had collected all the information she needed. Nicole and Lavinia remained on the path, chatting and watching, whilst more stable girls and the occasional visitors gathered around the group in a circle chattering , laughing and taking snaps.
“She’s such a perfectionist,” remarked Lavinia.
“Totally,” replied Nicole. “And you realise there are more outfits in the pipeline she’s still working on.”
“Gosh… I do hope it all pays off in the end… You must have spent a fortune.”
“Money well spent, Lavinia – just look at him! Imagine him and Bobby working as a pair – cuteness on steroids. I’ll be surprised if they don’t have the women flocking here. Though they need to do a good job at the same time. Bobby’s the best, of course. He loves clean, shiny boots, as we well know. Timmy? He will need some intensive training, but I’m working on that.”
Once Cynthia was satisfied, Timothy was allowed to return to the privacy of the stable and change into his everyday clothes. When he emerged he was surprised to find about twenty or thirty of his original audience were still hanging around, and raised a cheer at his reappearance. He heard a whisper of “he’s so handsome!” from one of the younger ones, which did wonders for his ego. And then someone shouted, “we love you, Timmy!” and everyone laughed. Lavinia had packed away his superhero outfit, and handed it to Cynthia so she could make some final adjustments. The four of them walked back to the car park together.
“Well I think that was a success, don’t you Timmy?” said Lavinia. But she got no reply. To tell the truth, Timothy was feeling slightly confused. There was a battle going on within that large area of his psyche called his ego. He hated the outfit but loved the attention.
In the car park Nicole ruffled his hair. “Great job, Timmy. You looked fab! I’ll send you some pics to show your mum. She’s going to be so proud…”
Nicole drove off with Cynthia, while Timothy got into Lavinia’s car.
“Do you want to go straight home, or shall be stop at the pub for a drink and a snack? Or lunch, even?”
“Pub, please.”
“Okay. Cheer up. It wasn’t that bad, was it?”
“It’s just…that outfit… I feel, like, a total sissy. It’s ten times worse than I fought it would be.”
“Oh, come on. It looks great on you, actually. The trouble is you see it with a man’s eyes. The girls at the Centre loved you. Didn’t you see them ogling you? I mean, you have a super body, darling. Make the most of it. It’s a great excuse to show it off.”
Timothy felt slightly mollified.
“Yeah, well, I may ‘ave, I guess.”
“So what’s the problem? I could see from the expressions on some of those girls faces that, given the chance, they would have been fighting each other over you!”
He glanced up at her, checking if she was serious. There wasn’t even the hint of a smile.
“D’you reckon?”
“Of course! For some of them I bet a nice-looking bloke in a superhero costume is just about their wildest fantasy.”
He denied it, but looked pleased. “Nah… I mean, maybe if it was all black, or somefink…”
“Well, I’m sure Cynthia could make you one in black – black with a coloured trim would be cool...”
“Really?”
“I’ll ask. Anyway, red and yellow’s not sissy. Now Bobby’s outfit – that’s proper sissy colours!”
That caught Timothy’s attention. He looked at her eagerly. “What do you mean?”
“Well, don’t tell him, will you? Promise?”
“No. Course not. I swear.”
“What is little girls’ favourite colour combination? Do you know?”
“Well…pink…”
“Pink and mauve! They love pink and mauve! Look at their toys. And little girls love pink and mauve dresses. So guess what colours Bobby’s superhero outfit is!”
“Pink…and mauve?”
“Yes! Pink top, pink pants, mauve cape and frills! Oh my god, he’s going to be so embarrassed! He’ll be like, little miss superhero! I can’t wait to see him.”
Timothy was ecstatic. “Yes!! And he don’t know?”
“No idea. He doesn’t need a fitting, because Cynthia’s makes stuff for him all the time.”
Timothy laughed, and shook a fist in the air. So Bobby was going to be the sissy, and he, Timmy the Boot Boy, would be the cool one. That was fair. Yes, perfect. He’d always thought Bobby was a bit girlish. Yes, pink and mauve…perfect. Now the girls would really have something to giggle at…
The more you give, the more I can give back.
Website, forum design, software, & security on this site is copyrighted. It was made personally by Betty Pearl, of Betty Pearl's Pubs, Sissy Stories, buffalobetties, pearlcorona. Betty's Pub is a non-profit organization & support group for the transgendered, & Fetware community. We don't sell anything, & we don't data mine your personal information & habits to sell like MOST other sites do. We respect your privacy & won't sell it out for a few bucks.
Site for: Sissy Stories, ABDL Stories, Sissy Art, Crossdressing, Transgender