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Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:50:45 PM »
Chapter 250.
It took Cynthia less than ten minutes to find a plain blue satin dress which fitted. The matching panties, tights and shoes were no problem. May rather coyly mentioned the pink latex panties.
“Oh, naturally he should have some latex,” smiled Cynthia. I’ll find some him very fine light ones he can wear under the satin ones – okay?”
“Perfect, thank you, Cynthia. Tim could hardly ask for more.”
“We’ll give him a padded training bra. He’s coming on, but I guess it’ll be a while yet. I’ll box up a handbag and some little spandex gloves as well, in case he goes out somewhere posh. Now, come with me and let’s see what Trish has in mind.”
Trish turned out to be a rather cool-looking young lady with short dyed blonde hair, multiple ear-piercings, dressed in torn jeans and a black vest, and with tattoos of Japanese warriors on both arms. She looked at Bobby critically.
“Blue satin party dress, puff sleeves, white tights,” said Cynthia, matter-of-factly.
“Traditional,” said Trish. “Cute. I get it.” In that case I’d suggest a tint. Blonde and blue – too predictable. Maybe some extensions? Pale eye shadow, subtle makeup. I’ll need to see the dress.”
“I’ll have it sent in.”
“Okay. Let’s go, mate.”
“Can I watch?” asked May.
“Please yourself.”
“Do you mind, Bobby?”
“No. I’d feel better if you were there.”
So she followed Trish and Bobby through a back door, leaving Cynthia smiling after them.
The makeover took over an hour. First Trish found a pair of light brown extensions which she said would suit him, they washed and tinted his hair to match. She dried his hair and attached the extensions, shaping and pinning and texturizing so his real hair and the extensions looked as one.
“I’m using clip-ins, which I wouldn’t normally do, but I understand he may need to take them off for work. They’ll still look good, don’t worry.”
She finished with mousse and a big blue ribbon that went perfectly with the party-style of the dress. Then she did his nails with a pale blue translucent polish, and did his makeup – subtle eye-shadow, mascara and lip-gloss. She gave him a spray of scent, and he was done. She gave May a bottle of the same scent.
“Here – pop this in his handbag. Cynthia’s already put in a little makeup set and a couple of bangles, I see.”
May couldn’t take her eyes off him. To all intents and purposes, he was a girl. The tension between his appearance, and the knowledge he was actually a boy, affected her quite profoundly. She felt a physical pain, in her chest, a sort of yearning – but for what, or why, she couldn’t say.
They left hand in hand. As she drove, she kept taking peeps at the happy person sitting next to her. He was ecstatic. The satin dress was so light and crisp, the feeling of his shiny nails and glossy lips so exciting, he couldn’t stop talking, eulogising about Fantastex, and speculating about what other dresses may be in the pipeline. He looked so pretty, May considered pulling off into a lay-by and snogging him. But she didn’t want to muss his perfect makeover, so she resisted the temptation. “Later,” she thought. Since Tim would still be working, she stopped at a café a couple of miles from the Centre, and they sat there chatting for some time. The only people that noticed them were a few young guys – who all seemed more interested in Bobby than in her. “If only they knew,” she thought, with a smile. “Tim’s gonna have a heart attack!”
When they finally got back to Pitt’s Wood, she took him down the back of the new stable block, so no-one would see them. Before they went in, she took one photo of him posing outside the boot parlour, beaming with delight. It was her favourite snap of all time…
It took Cynthia less than ten minutes to find a plain blue satin dress which fitted. The matching panties, tights and shoes were no problem. May rather coyly mentioned the pink latex panties.
“Oh, naturally he should have some latex,” smiled Cynthia. I’ll find some him very fine light ones he can wear under the satin ones – okay?”
“Perfect, thank you, Cynthia. Tim could hardly ask for more.”
“We’ll give him a padded training bra. He’s coming on, but I guess it’ll be a while yet. I’ll box up a handbag and some little spandex gloves as well, in case he goes out somewhere posh. Now, come with me and let’s see what Trish has in mind.”
Trish turned out to be a rather cool-looking young lady with short dyed blonde hair, multiple ear-piercings, dressed in torn jeans and a black vest, and with tattoos of Japanese warriors on both arms. She looked at Bobby critically.
“Blue satin party dress, puff sleeves, white tights,” said Cynthia, matter-of-factly.
“Traditional,” said Trish. “Cute. I get it.” In that case I’d suggest a tint. Blonde and blue – too predictable. Maybe some extensions? Pale eye shadow, subtle makeup. I’ll need to see the dress.”
“I’ll have it sent in.”
“Okay. Let’s go, mate.”
“Can I watch?” asked May.
“Please yourself.”
“Do you mind, Bobby?”
“No. I’d feel better if you were there.”
So she followed Trish and Bobby through a back door, leaving Cynthia smiling after them.
The makeover took over an hour. First Trish found a pair of light brown extensions which she said would suit him, they washed and tinted his hair to match. She dried his hair and attached the extensions, shaping and pinning and texturizing so his real hair and the extensions looked as one.
“I’m using clip-ins, which I wouldn’t normally do, but I understand he may need to take them off for work. They’ll still look good, don’t worry.”
She finished with mousse and a big blue ribbon that went perfectly with the party-style of the dress. Then she did his nails with a pale blue translucent polish, and did his makeup – subtle eye-shadow, mascara and lip-gloss. She gave him a spray of scent, and he was done. She gave May a bottle of the same scent.
“Here – pop this in his handbag. Cynthia’s already put in a little makeup set and a couple of bangles, I see.”
May couldn’t take her eyes off him. To all intents and purposes, he was a girl. The tension between his appearance, and the knowledge he was actually a boy, affected her quite profoundly. She felt a physical pain, in her chest, a sort of yearning – but for what, or why, she couldn’t say.
They left hand in hand. As she drove, she kept taking peeps at the happy person sitting next to her. He was ecstatic. The satin dress was so light and crisp, the feeling of his shiny nails and glossy lips so exciting, he couldn’t stop talking, eulogising about Fantastex, and speculating about what other dresses may be in the pipeline. He looked so pretty, May considered pulling off into a lay-by and snogging him. But she didn’t want to muss his perfect makeover, so she resisted the temptation. “Later,” she thought. Since Tim would still be working, she stopped at a café a couple of miles from the Centre, and they sat there chatting for some time. The only people that noticed them were a few young guys – who all seemed more interested in Bobby than in her. “If only they knew,” she thought, with a smile. “Tim’s gonna have a heart attack!”
When they finally got back to Pitt’s Wood, she took him down the back of the new stable block, so no-one would see them. Before they went in, she took one photo of him posing outside the boot parlour, beaming with delight. It was her favourite snap of all time…
92
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:45:19 PM »
Chapter 249.
Saturday lunchtime, the boot parlour. Bobby in his civvies, Tim in full uniform, butt-plug set to zero – to avoid startling Phillipa – sulking quietly that he had to stay and work whilst Bobby went off having fun.
“Where you goin’ anyway?”
“No idea, Tim. Some sort of surprise, May said.”
“Well fink of me slavin’ away ‘ere while you’re enjoyin’ yerself, won’t you?”
“The image won’t leave my mind for a second, I promise you.”
“Yeah right. Now shove off before I kick yer out…”
With which fond farewell, Tim disappeared into the waiting-room on the way to check all his equipment was ready. A moment later May walked in.
“Ready, Bobby?”
“Yes. You’re not going to tell me…”
“No. You’ll find out. You’ll be happy – I think.”
It was half an hour’s drive. As they pulled into the estate, Bobby twigged.
“Fantastex! Why are we here today?”
“Cynthia has something for you.”
“Not my dress?”
“Not the dress. But a dress, at least. It’s as much a surprise for Tim as for you.”
“Wow. That’s cool. Do you know what it’s like?”
May parked outside the Fantastex building, an unostentatious single-story affair that had years ago been a manufactory of cardboard boxes, and still sported frosted windows along one side. The front, though, had long clear glass pains and a colourful sign in puffy letters. They climbed out of the car and entered.
Daphne was on reception as usual, sitting behind a till, on the phone to a customer.
“Yes, Wednesday. Come early if you can – we get busy after about eleven. I’ll tell Cynthia about the modifications. Yes. Yes. Thanks, Mrs Cooper. My pleasure.”
She put down the phone and smiled at them. “You’re Bobby, aren’t you?”
“Yes. This is my friend May.”
“Nice to meet you. Cynthia’s in her office.” She pointed. “Follow the wall and you can’t miss her.”
May led the way, taking her time and taking in the racks of latex outfits, catsuits, dresses, all sorts of things, with great interest. They spotted Cynthia sitting at her desk in a utilitarian alcove lined with grey filing cabinets and swatches of latex. She jumped up when she saw them.
“Bobby! You made it. And you must be May. Nice to meet you.”
“And you, Cynthia. I’ve heard a lot about you.”
“Good or bad? Never mind, I don’t care. Now, Bobby, I understand from May here that you and your colleague Tim are interested in finding you a dress. Right?”
“Well, yes… But I thought it was still in the design stage…”
“Oh, it is. I should say, they are… But we have so much stock, I’m sure I can find you something for now. Blue satin, is it?”
“Er…yes…”
“Your choice, or…”
“Tim’s,” grinned May. “He thinks Bobby’ll look nice in blue satin and white tights. I think he’s probably right.”
“Me too, Bobby – though you’d look good in anything. But I’ll tell you what we’re going to do. As a surprise for Tim, we find you the clothes, yes, but we’ll also give you a complete makeover. So when you go back to the Centre, you can give him the surprise of his life…”
“Really?”
“Oh yes. You wait. I’m as excited as you are. You’re going to make such a pretty girl. May? We’re going to need your advice. Let’s go into the back and finds the outfit first, then I’ll introduce you to Trish. She’ll take care of everything else…”
Saturday lunchtime, the boot parlour. Bobby in his civvies, Tim in full uniform, butt-plug set to zero – to avoid startling Phillipa – sulking quietly that he had to stay and work whilst Bobby went off having fun.
“Where you goin’ anyway?”
“No idea, Tim. Some sort of surprise, May said.”
“Well fink of me slavin’ away ‘ere while you’re enjoyin’ yerself, won’t you?”
“The image won’t leave my mind for a second, I promise you.”
“Yeah right. Now shove off before I kick yer out…”
With which fond farewell, Tim disappeared into the waiting-room on the way to check all his equipment was ready. A moment later May walked in.
“Ready, Bobby?”
“Yes. You’re not going to tell me…”
“No. You’ll find out. You’ll be happy – I think.”
It was half an hour’s drive. As they pulled into the estate, Bobby twigged.
“Fantastex! Why are we here today?”
“Cynthia has something for you.”
“Not my dress?”
“Not the dress. But a dress, at least. It’s as much a surprise for Tim as for you.”
“Wow. That’s cool. Do you know what it’s like?”
May parked outside the Fantastex building, an unostentatious single-story affair that had years ago been a manufactory of cardboard boxes, and still sported frosted windows along one side. The front, though, had long clear glass pains and a colourful sign in puffy letters. They climbed out of the car and entered.
Daphne was on reception as usual, sitting behind a till, on the phone to a customer.
“Yes, Wednesday. Come early if you can – we get busy after about eleven. I’ll tell Cynthia about the modifications. Yes. Yes. Thanks, Mrs Cooper. My pleasure.”
She put down the phone and smiled at them. “You’re Bobby, aren’t you?”
“Yes. This is my friend May.”
“Nice to meet you. Cynthia’s in her office.” She pointed. “Follow the wall and you can’t miss her.”
May led the way, taking her time and taking in the racks of latex outfits, catsuits, dresses, all sorts of things, with great interest. They spotted Cynthia sitting at her desk in a utilitarian alcove lined with grey filing cabinets and swatches of latex. She jumped up when she saw them.
“Bobby! You made it. And you must be May. Nice to meet you.”
“And you, Cynthia. I’ve heard a lot about you.”
“Good or bad? Never mind, I don’t care. Now, Bobby, I understand from May here that you and your colleague Tim are interested in finding you a dress. Right?”
“Well, yes… But I thought it was still in the design stage…”
“Oh, it is. I should say, they are… But we have so much stock, I’m sure I can find you something for now. Blue satin, is it?”
“Er…yes…”
“Your choice, or…”
“Tim’s,” grinned May. “He thinks Bobby’ll look nice in blue satin and white tights. I think he’s probably right.”
“Me too, Bobby – though you’d look good in anything. But I’ll tell you what we’re going to do. As a surprise for Tim, we find you the clothes, yes, but we’ll also give you a complete makeover. So when you go back to the Centre, you can give him the surprise of his life…”
“Really?”
“Oh yes. You wait. I’m as excited as you are. You’re going to make such a pretty girl. May? We’re going to need your advice. Let’s go into the back and finds the outfit first, then I’ll introduce you to Trish. She’ll take care of everything else…”
93
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:28:23 PM »
Chapter 248.
They had passed through a curtain which had fallen into shreds behind them, as through it had never existed. There was no going back. Without the prurient impositions of Diana and Eleanor it may never have happened, but that wasn’t important. They both knew they weren’t really gay, and they jibbed at Eleanor’s whispered “sissy-boys”, though they could understand her justification in saying it. But they felt no guilt or shame, and when they were finally released from their bondage, and had stretched and exercised for a minute or two, they looked at each other and grinned.
“Wow, Bobby…that were intense, yeah?”
“What a pervert you are, Tim. I should have realised that four years ago.”
“If I am one, so’s you…”
“Yeah, I know…”
It was on the surface a simple relationship, but after all the years they’d known each other there was a lot more under the surface. Tim had had a crush on his friend since secondary school, and whereas such childish affection between boys normally fades as the girls grow and become more appealing, in this case Bobby actually possessed more feminine allure than they. Moreover he depended on Bobby in many ways, for comradeship, for loyalty, for guidance in life. He respected Bobby’s intellectual powers, and relied on him to help him make the right decisions. Reciprocally, Bobby liked Tim for his openness, his honesty, his habit of saying what was in his mind, his total lack of filters – the absence of the “persona”. This he regarded as a rare psychological strength, and it was backed up by Tim’s physical strength. When they were younger, before Bobby’s pony-work had built and hardened his muscles, Tim had been his protector on several occasions, when others sought to exploit his delicacy. But there was more to Bobby’s feelings than a mere objective regard for Tim’s masculinity; the feminine element in his psyche also responded emotionally. Their affection was mutual, as was the inclination to express it physically.
“We’re leaving, boys,” smiled Diana, and she and Eleanor put away the last aids in the special cupboards and locked the doors. “Full marks for what you did today. It opens up all sorts of possibilities…”
“We heard something about a dress, Bobby…” remarked Eleanor.
“Yeah, That a way down the line, though. Cynthia’s still working on the design, I believe.”
“What do you think about that, Timothy?”
“Yeah, well, if ‘e wants to wear dresses, let ‘im. Suit ‘im, I reckin…” he said, evasively.
“Hmm…” was Eleanor’s only reply.
They were in a mess. The parlour was in a mess. They were wondering how to start, when Ellie arrived. She took one look at them, and another at the floor, and burst out laughing.
“What’s been going on here? Boot parlour? Looks more like a milking parlour! Look at the state of you two. And why are your lips swollen like that…?”
The boys looked at the ground.
“Well, never mind,” she said, suspiciously. “Just go get showered and changed. I’ll mop up here. Go on. Off you go.”
“Thanks, Ellie…”
“Yeah, fanks…”
“Oh, and by the way, Saturday. Tim, you have one customer in the afternoon, by yourself.”
“By meself?”
“Yes. Phillipa. She’s new so it would be intimidating to have both of you together.”
“Why me? Why not…”
“We drew lots. You lost. Don’t look like that, please. It’ll be Bobby next time. So Bobby, you’re free. May wants to take you out somewhere. She’ll come pick you up at lunchtime.”
“Where does she…”
“No idea. It’s a surprise, I think. Okay?”
“Sure…”
When she’d finished she paid a call on the girls.
“I don’t know what That Murchison woman and her friend had them doing, but they looked like they’d spent a night in a brothel! I’m telling you, May. It’s true. There was c-um all over the fronts of their shorts, all down their legs and all over the floor. And they both had swollen lips, like they’d been snogging – I mean serious snogging! So you may want to give them a break from their, you know, education, tonight…”
Jessica and May looked at each other.
“Do you think…?” began Jessica.
“Well they weren’t snogging the ladies, cos I met them earlier when they were coming down the path. Giggling a lot, but quite unruffled.”
“Then they must have been…”
“They must. We’ll get it out of them. That would be so cute…”
They went down straight after work. Sure enough, the boys seemed rather low-key. Happy, but for them, rather quiet. May opened the conversation.
“So… How was work today? We were really busy.”
“Fine, May… Yeah, fine, eh Tim?”
“Er, yeah… Fine…”
“So were you busy?”
“Oh, quite busy…”
“Yeah, sorta quite busy…”
They were getting nowhere.
“I ran into those two women from the committee…what are their names? Murkyditch and Bowson or something? Coming from your direction. Was it them?”
The boys exchanged glances.
“Oh, yeah, I fink so…”
“You think so, Tim? Don’t you know?”
“Oh, Tim doesn’t know them very well…”
“But they were here before.”
“Were they? Oh, yes, they were. Weren’t they, Tim?”
“Guys – cut the crap,” interjected Jessica. What happened? Come on, spill it.”
The girls, by means of endearments and threats, they extracted the truth bit by bit. They even insisted on inspecting the crime scene, and forcing the boys to duplicate their positions. What the boys didn’t mention was the snogging.
“I always thought those two were perverts,” said Jessica, delighted, “but imagine dreaming up that sort of scenario.”
“It must have been planned for when they were building the place,” said May. “Which means Miss Poole was also the instigator. The entire committee must be in on the whole thing!”
“Did they take any photos?”
“Photos and videos,” admitted Bobby, reluctantly.
“Oh my god, they’re all going to be leching over them!” cried May; adding, “wish we could see them…”
“So boys,” said Jessica, slyly, “how did your lips get all swollen, then?”
“What?”
“Ellie told us, when she found you, your lips were swollen. How come?”
“I… No they weren’t… She must have… I mean, everything was swollen, cos of being in that position…”
“Bobby, tell the truth. Ellie knows all about snogging – no-one more so. So admit it. You snogged each other. You were forced to, I get it. But that’s the truth, isn’t it?”
Their faces were enough admission.
“Show us how you did it.”
“Yeah, come on. We want to judge how good you are. Don’t be so shy. Afterwards you can snog us.”
Eventually the boys gave in, and, sitting side by side on the sofa, exchanged some half-hearted pecks.
“What’s that?” asked Jessica, incredulously. “Tim – you know how to kiss. Now kiss Bobby how you did earlier. Or I’m leaving.”
“Oh, fer fuc-k’s sake…”
He grabbed Bobby in both arms, put a hand behind his head, and gave him a Timothy Painyer one-minute special.
“Satisfied?” he asked, coming up for air.
“Bobby is, anyway,” remarked May, looking at her boyfriend’s dazed face and tousled hair.
They had passed through a curtain which had fallen into shreds behind them, as through it had never existed. There was no going back. Without the prurient impositions of Diana and Eleanor it may never have happened, but that wasn’t important. They both knew they weren’t really gay, and they jibbed at Eleanor’s whispered “sissy-boys”, though they could understand her justification in saying it. But they felt no guilt or shame, and when they were finally released from their bondage, and had stretched and exercised for a minute or two, they looked at each other and grinned.
“Wow, Bobby…that were intense, yeah?”
“What a pervert you are, Tim. I should have realised that four years ago.”
“If I am one, so’s you…”
“Yeah, I know…”
It was on the surface a simple relationship, but after all the years they’d known each other there was a lot more under the surface. Tim had had a crush on his friend since secondary school, and whereas such childish affection between boys normally fades as the girls grow and become more appealing, in this case Bobby actually possessed more feminine allure than they. Moreover he depended on Bobby in many ways, for comradeship, for loyalty, for guidance in life. He respected Bobby’s intellectual powers, and relied on him to help him make the right decisions. Reciprocally, Bobby liked Tim for his openness, his honesty, his habit of saying what was in his mind, his total lack of filters – the absence of the “persona”. This he regarded as a rare psychological strength, and it was backed up by Tim’s physical strength. When they were younger, before Bobby’s pony-work had built and hardened his muscles, Tim had been his protector on several occasions, when others sought to exploit his delicacy. But there was more to Bobby’s feelings than a mere objective regard for Tim’s masculinity; the feminine element in his psyche also responded emotionally. Their affection was mutual, as was the inclination to express it physically.
“We’re leaving, boys,” smiled Diana, and she and Eleanor put away the last aids in the special cupboards and locked the doors. “Full marks for what you did today. It opens up all sorts of possibilities…”
“We heard something about a dress, Bobby…” remarked Eleanor.
“Yeah, That a way down the line, though. Cynthia’s still working on the design, I believe.”
“What do you think about that, Timothy?”
“Yeah, well, if ‘e wants to wear dresses, let ‘im. Suit ‘im, I reckin…” he said, evasively.
“Hmm…” was Eleanor’s only reply.
They were in a mess. The parlour was in a mess. They were wondering how to start, when Ellie arrived. She took one look at them, and another at the floor, and burst out laughing.
“What’s been going on here? Boot parlour? Looks more like a milking parlour! Look at the state of you two. And why are your lips swollen like that…?”
The boys looked at the ground.
“Well, never mind,” she said, suspiciously. “Just go get showered and changed. I’ll mop up here. Go on. Off you go.”
“Thanks, Ellie…”
“Yeah, fanks…”
“Oh, and by the way, Saturday. Tim, you have one customer in the afternoon, by yourself.”
“By meself?”
“Yes. Phillipa. She’s new so it would be intimidating to have both of you together.”
“Why me? Why not…”
“We drew lots. You lost. Don’t look like that, please. It’ll be Bobby next time. So Bobby, you’re free. May wants to take you out somewhere. She’ll come pick you up at lunchtime.”
“Where does she…”
“No idea. It’s a surprise, I think. Okay?”
“Sure…”
When she’d finished she paid a call on the girls.
“I don’t know what That Murchison woman and her friend had them doing, but they looked like they’d spent a night in a brothel! I’m telling you, May. It’s true. There was c-um all over the fronts of their shorts, all down their legs and all over the floor. And they both had swollen lips, like they’d been snogging – I mean serious snogging! So you may want to give them a break from their, you know, education, tonight…”
Jessica and May looked at each other.
“Do you think…?” began Jessica.
“Well they weren’t snogging the ladies, cos I met them earlier when they were coming down the path. Giggling a lot, but quite unruffled.”
“Then they must have been…”
“They must. We’ll get it out of them. That would be so cute…”
They went down straight after work. Sure enough, the boys seemed rather low-key. Happy, but for them, rather quiet. May opened the conversation.
“So… How was work today? We were really busy.”
“Fine, May… Yeah, fine, eh Tim?”
“Er, yeah… Fine…”
“So were you busy?”
“Oh, quite busy…”
“Yeah, sorta quite busy…”
They were getting nowhere.
“I ran into those two women from the committee…what are their names? Murkyditch and Bowson or something? Coming from your direction. Was it them?”
The boys exchanged glances.
“Oh, yeah, I fink so…”
“You think so, Tim? Don’t you know?”
“Oh, Tim doesn’t know them very well…”
“But they were here before.”
“Were they? Oh, yes, they were. Weren’t they, Tim?”
“Guys – cut the crap,” interjected Jessica. What happened? Come on, spill it.”
The girls, by means of endearments and threats, they extracted the truth bit by bit. They even insisted on inspecting the crime scene, and forcing the boys to duplicate their positions. What the boys didn’t mention was the snogging.
“I always thought those two were perverts,” said Jessica, delighted, “but imagine dreaming up that sort of scenario.”
“It must have been planned for when they were building the place,” said May. “Which means Miss Poole was also the instigator. The entire committee must be in on the whole thing!”
“Did they take any photos?”
“Photos and videos,” admitted Bobby, reluctantly.
“Oh my god, they’re all going to be leching over them!” cried May; adding, “wish we could see them…”
“So boys,” said Jessica, slyly, “how did your lips get all swollen, then?”
“What?”
“Ellie told us, when she found you, your lips were swollen. How come?”
“I… No they weren’t… She must have… I mean, everything was swollen, cos of being in that position…”
“Bobby, tell the truth. Ellie knows all about snogging – no-one more so. So admit it. You snogged each other. You were forced to, I get it. But that’s the truth, isn’t it?”
Their faces were enough admission.
“Show us how you did it.”
“Yeah, come on. We want to judge how good you are. Don’t be so shy. Afterwards you can snog us.”
Eventually the boys gave in, and, sitting side by side on the sofa, exchanged some half-hearted pecks.
“What’s that?” asked Jessica, incredulously. “Tim – you know how to kiss. Now kiss Bobby how you did earlier. Or I’m leaving.”
“Oh, fer fuc-k’s sake…”
He grabbed Bobby in both arms, put a hand behind his head, and gave him a Timothy Painyer one-minute special.
“Satisfied?” he asked, coming up for air.
“Bobby is, anyway,” remarked May, looking at her boyfriend’s dazed face and tousled hair.
94
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:19:46 PM »
Chapter 247.
Needless to say, the two female libertines observing this little tableau were ecstatic. They didn’t take their eyes off the boys till they were quite spent, slumped against each other exhausted, their legs down to their shoes slimy with their secretions. Then, ignoring the boys, they got themselves coffees and sat down in the visitors chairs to review the video. There was much sniggering and whispering, and, at the climax, little whoops of delight.
For the boys their behaviour was very irritating. It was clear they couldn’t care less how they were feeling after their exertions, as they sat there comfortably sipping their drinks and reliving the whole performance at their leisure.
“What abou’ us?” cried Tim, turning his head round as far as he could. “When you gonna let us go?”
Diana looked up, surprised.
“Let you go? It’s not even been an hour yet, Timothy, and we’ve booked the whole afternoon. No, young man, you’ve got a lot of work to do yet. And look at the mess you’ve made! The floors all sticky now. After we leave you two are going to be here cleaning up till Ellie says you can leave.
“That ain’t fair…”
“Tim, be quiet. It won’t do any good.”
“See? Bobby understands.,” said Eleanor. “We’ve paid for you and we’re going to get our money’s worth.”
Diana stood up, sidled over and stood by the boys’ side, one hand against the wall. She regarded them with an amused smile, and ruffled their hair.
“You’re going to have to get used to things that “ain’t fair” Tim. We – I mean us, Miss Poole, the committee – we own you now, and we can do whatever we like with you. If you don’t understand that yet, you’re going to be very disappointed. Now we acknowledge that you’re both very cute young men, and you’ll turn heads wherever you go – especially in outfits like these.” She looked them up and down. “That’s why we’re allowing you to enjoy you’re celebrity – to show off at weddings, to have girlfriends, and shortly, to attend parties. Yes, parties – there are several coming up, and you’ll be well-paid too. When you have a few more outfits, we’d like to host a fashion show for you.”
The boys pricked up their ears. “Fashion show?” asked Bobby.
“Yes. Oh, you like that idea, don’t you? I can see it in your faces! All that attention – you’d be able to show off to your hearts’ content. Bobby, you might even have some girly stuff. Imagine! And on top of this amazing job, you’ve got all the perks - your own personal flat, free food and drink, access to all the Centre’s facilities. Also – and this is a secret, so don’t mention it outside this room – if you continue to be good boys, you may be getting driving lessons and eventually your own vehicle. We’ve had requests for home visits from far and wide, and it would make things a lot easier.”
“Cor… really, miss?” said Tim, immediately forgetting his complaints.
“Don’t quote me, but we can make it happen. Provided we get cooperation. So please don’t complain about merely doing your job.”
“Sorry, miss. I wuz, like, outa line…”
Bobby looked at him with disgust. Diana and Eleanour exchanged sly glances.
“So can we continue? I think you’ve proved your physical empathy… But we mustn’t ignore the emotional element. This time express your true affection for each other. Tim, from what I’ve heard, your feelings for Bobby exceed mere friendship. Don’t be afraid to show them, will you?”
So saying, she picked up the vibrator again and got to work. No lube was needed this time.
Protest was pointless, and would probably have been counter-productive. Eleanor resumed her previous position just on their right, resting her shoulder against the wall to steady her hand. In two or three minutes they were both fully tumescent in their slimy shorts. To relieve a slight itchiness in his member, Tim ground it hard against his friend, and then started planting little soft kisses on Bobby’s cheeks, which he had no way of escaping.
“Hey, Tim…don’t do that…”
“I want to though…”
“But…”
Tim had kissed him on the lips, with a gentleness Bobby would have thought him incapable of. At first he wasn’t sure whether Tim was expressing his affection, or trying to curry favour with the ladies with a view to material gain. But the kiss was too tender to be ambiguous. Taken by surprise, Bobby allowed him to continue. It didn’t feel inappropriate. After all they were virtually making love. After a minute or so he began to reciprocate, slipping his tongue into Tim’s mouth. His consciousness of the onlookers faded, and he became lost in mutual pleasure. This time it was he who clasped Tim’s hands, he who moved against him in sympathetic rhythm, and he who initiated the eventual, inevitable, double orgasm…
Needless to say, the two female libertines observing this little tableau were ecstatic. They didn’t take their eyes off the boys till they were quite spent, slumped against each other exhausted, their legs down to their shoes slimy with their secretions. Then, ignoring the boys, they got themselves coffees and sat down in the visitors chairs to review the video. There was much sniggering and whispering, and, at the climax, little whoops of delight.
For the boys their behaviour was very irritating. It was clear they couldn’t care less how they were feeling after their exertions, as they sat there comfortably sipping their drinks and reliving the whole performance at their leisure.
“What abou’ us?” cried Tim, turning his head round as far as he could. “When you gonna let us go?”
Diana looked up, surprised.
“Let you go? It’s not even been an hour yet, Timothy, and we’ve booked the whole afternoon. No, young man, you’ve got a lot of work to do yet. And look at the mess you’ve made! The floors all sticky now. After we leave you two are going to be here cleaning up till Ellie says you can leave.
“That ain’t fair…”
“Tim, be quiet. It won’t do any good.”
“See? Bobby understands.,” said Eleanor. “We’ve paid for you and we’re going to get our money’s worth.”
Diana stood up, sidled over and stood by the boys’ side, one hand against the wall. She regarded them with an amused smile, and ruffled their hair.
“You’re going to have to get used to things that “ain’t fair” Tim. We – I mean us, Miss Poole, the committee – we own you now, and we can do whatever we like with you. If you don’t understand that yet, you’re going to be very disappointed. Now we acknowledge that you’re both very cute young men, and you’ll turn heads wherever you go – especially in outfits like these.” She looked them up and down. “That’s why we’re allowing you to enjoy you’re celebrity – to show off at weddings, to have girlfriends, and shortly, to attend parties. Yes, parties – there are several coming up, and you’ll be well-paid too. When you have a few more outfits, we’d like to host a fashion show for you.”
The boys pricked up their ears. “Fashion show?” asked Bobby.
“Yes. Oh, you like that idea, don’t you? I can see it in your faces! All that attention – you’d be able to show off to your hearts’ content. Bobby, you might even have some girly stuff. Imagine! And on top of this amazing job, you’ve got all the perks - your own personal flat, free food and drink, access to all the Centre’s facilities. Also – and this is a secret, so don’t mention it outside this room – if you continue to be good boys, you may be getting driving lessons and eventually your own vehicle. We’ve had requests for home visits from far and wide, and it would make things a lot easier.”
“Cor… really, miss?” said Tim, immediately forgetting his complaints.
“Don’t quote me, but we can make it happen. Provided we get cooperation. So please don’t complain about merely doing your job.”
“Sorry, miss. I wuz, like, outa line…”
Bobby looked at him with disgust. Diana and Eleanour exchanged sly glances.
“So can we continue? I think you’ve proved your physical empathy… But we mustn’t ignore the emotional element. This time express your true affection for each other. Tim, from what I’ve heard, your feelings for Bobby exceed mere friendship. Don’t be afraid to show them, will you?”
So saying, she picked up the vibrator again and got to work. No lube was needed this time.
Protest was pointless, and would probably have been counter-productive. Eleanor resumed her previous position just on their right, resting her shoulder against the wall to steady her hand. In two or three minutes they were both fully tumescent in their slimy shorts. To relieve a slight itchiness in his member, Tim ground it hard against his friend, and then started planting little soft kisses on Bobby’s cheeks, which he had no way of escaping.
“Hey, Tim…don’t do that…”
“I want to though…”
“But…”
Tim had kissed him on the lips, with a gentleness Bobby would have thought him incapable of. At first he wasn’t sure whether Tim was expressing his affection, or trying to curry favour with the ladies with a view to material gain. But the kiss was too tender to be ambiguous. Taken by surprise, Bobby allowed him to continue. It didn’t feel inappropriate. After all they were virtually making love. After a minute or so he began to reciprocate, slipping his tongue into Tim’s mouth. His consciousness of the onlookers faded, and he became lost in mutual pleasure. This time it was he who clasped Tim’s hands, he who moved against him in sympathetic rhythm, and he who initiated the eventual, inevitable, double orgasm…
95
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:15:30 PM »
Chapter 246.
Eleanor ran a hand down the backs of Tim’s bare thighs.
“You’ve got such nice legs, Tim. Straight and strong and smooth.”
Leaving her hand resting on the very top of his right thigh, she craned round and peered into his face.
“Are you blushing, darling? You’re not…embarrassed, are you? I really don’t see how you could be, considering how brazenly you parade around in those tiny little latex shorts…”
Tim turned his head to the other side, but Eleanor slipped round and confronted him again, this time caressing his other thigh.
“I do believe you are! Oh, I know. Being so close to your best friend Bobby… Is it making you a teeny bit…” – she lowered her voice to a whisper – “excited?”
She stroked his bottom for a few seconds, then gave it a push, pressing the boys abdomens momentarily together, and eliciting a gasp from each of them.
“Oh, dear!” she giggled. “Did I accidentally cause a slight collision? I didn’t mean to…”
“More of a “coc-k-lision” perhaps, dear?” interjected Diana, archly. At which they both snorted with mirth.
When she had recovered, Eleanor slipped her fingers between his legs and tickled the inside of his thigh with her nails, making him squirm, and generating even more friction between the boys’ swelling members. Now they were getting worried. As they should have been.
“Eleanor, I don’t think they want to be played with. I’m sure they’d rather be left alone to enjoy their intimacy in peace. We can help them with that. Look, I’ve just the thing. Perhaps you could you give me a hand?”
“Of course, dear.”
Diana was holding two pink straps, each about eighteen inches long. She gave one to Eleanor, and they exchanged winks. The boys wondered what was coming next. Not for long. They felt the points of the straps being inserted between their thighs. Bobby squeezed his together, but to no avail. The women drew them through between the boys legs, worked the up till they were a high as they could get them, pressing against their balls and lying above the leg-bands of their shorts. They adjusted them till the buckles were midway between their outer thighs, then fed the points through the buckles and drew them tight, pulling the boys abdomens firmly together, and squashing their coc-ks against each other! As the straps were buckled the boys felt the shafts slip neatly side-by-side, pressed together like two sausages in a packet and held fast between their tummies!
“No, stop!” Tim cried out in protest.
“Please, Miss Murchison, Miss Bowditch, don’t do that…” begged Bobby, trying to maintain his manners, but knowing they were unlikely to relent. Tim was more forthright.
“Watcher doin’? Let us go, now, or we’ll…”
“Yes? What will you do?” asked Diana, curtly, tucking the point of her strap into its loop and standing back. “Tell Miss Poole, perhaps? You’re in no position to… No, I correct myself. You’re in the perfect position - for Miss Poole to give you a dozen strokes of her whip! Would you like that?”
Tim remembered what that felt like.
“No… Sorry, I didn’t mean no disrespec’…”
“Good. Glad to hear it. Now, Eleanor. Anything else in our cupboard that may be of use?”
“Well, I don’t know, Diana… There are these… Whatever they are…” she added innocently.
She took out a clear plastic box and held it out in both hands for Diana to see. It contained a selection of vibrators, maybe nine or ten, different shapes and sizes, ranging from ones eight or nine inches long down to one no bigger than a lipstick. From the door Bobby was the only one who could see.
“Shit…”
“Oh, how useful!” cried Diana. “Let me see… How about this one? No, too bobbly… I think we’ll have to go for…”
“This nice slim pink one?” suggested Eleanor.
“Yes. That’ll do nicely.” She took it out. It was activated by turning the base. She tried it. It buzzed vigorously into life. “Seems to be fully charged.” She switched it off and turned back to the boys.
“You look so tense! Just relax, guys. Don’t be so uptight. This will help you, believe me. Don’t fight it – go with the flow…”
She turned on the vibrator again.
“It’s on number one. You’ll hardly feel it.” She ran the tip over Tim’s behind. He wriggled and clenched his buttocks. “See? What can you feel?”
“It tickles,” said Tim, sulkily.
“Keep still!” hissed Bobby. “Don’t squirm like that! That’s what they want.”
“I can’t help it! It tickles!” Tim whispered back, irritably. “Ooh…”
Diana had inserted the point of the vibrator between his upper thighs, and was trying to push it in. Tim pressed his muscular thighs together as hard as he could. Diana frowned.
“Oh well, if that’s how you want it… Eleanor dear, could you squeeze a bit of lube on it?”
She held it out. Eleanor picked up a tube, and lubed the end. Diana turned back. Now it slipped in easily. She pushed it in until it touched his balls, then turned it up to number two. Soon both boys’ balls were vibrating in harmony – and so were their coc-ks. It felt so strange. Their pen-ises were pressed together, into what felt like a single thick shaft, vibrating between their tummies. Neither of them could tell where his own ended and his friend’s began. Both were fully tumescent, the head of Tim’s not far short of his belt, and both were oozing freely, lubricating the taut latex and facilitating the effects of the vibrator. Diana moved the head of the vibe gently around, or worked it slowly in and out, watching with a satisfied smile as the boys squirmed against each other, moaning in pleasure. Eleanor stood to one side recording their oscillations and their pleadings on her phone.
“Please, Miss M-Murchison,” whimpered Bobby, “please stop. If you don’t…”
“Yes, what will happen?” she asked, innocently.
“P-please…”
For each of them, the personal physical arousal, the constant friction of slippery coc-k against slippery coc-k, was difficult enough to resist, but being forced to share your friend’s pleasure as well, to listen to his gasps and groans, was too much to bear. Bobby had considerable self-discipline; but Tim was much more subservient to his feelings and emotions – or perhaps his were just stronger. Either way, he was the first to crack, to surrender to his lust. Having done so, there was no longer any reason to hold back. So, clasping Bobby’s hands in his own to forestall any resistance, and taking full advantage of his complete immobilisation, he began - as much as the thigh straps allowed - to pound Bobby’s firmly-muscled tummy, thrusting against it until he was overtaken by a massive climax, so intense that he cried out, and in his passion even bit the lobe of Bobby’s ear.
Bobby himself had been teetering on the brink for a minute or two, and Tim’s orgasm predictably triggered his own. He cried out in pain when Tim bit him, but he was already c-umming. The two of them pummelled each other furiously, like two passionate lovers reunited after a long absence, flooding their shorts with hot c-um.
Eleanor ran a hand down the backs of Tim’s bare thighs.
“You’ve got such nice legs, Tim. Straight and strong and smooth.”
Leaving her hand resting on the very top of his right thigh, she craned round and peered into his face.
“Are you blushing, darling? You’re not…embarrassed, are you? I really don’t see how you could be, considering how brazenly you parade around in those tiny little latex shorts…”
Tim turned his head to the other side, but Eleanor slipped round and confronted him again, this time caressing his other thigh.
“I do believe you are! Oh, I know. Being so close to your best friend Bobby… Is it making you a teeny bit…” – she lowered her voice to a whisper – “excited?”
She stroked his bottom for a few seconds, then gave it a push, pressing the boys abdomens momentarily together, and eliciting a gasp from each of them.
“Oh, dear!” she giggled. “Did I accidentally cause a slight collision? I didn’t mean to…”
“More of a “coc-k-lision” perhaps, dear?” interjected Diana, archly. At which they both snorted with mirth.
When she had recovered, Eleanor slipped her fingers between his legs and tickled the inside of his thigh with her nails, making him squirm, and generating even more friction between the boys’ swelling members. Now they were getting worried. As they should have been.
“Eleanor, I don’t think they want to be played with. I’m sure they’d rather be left alone to enjoy their intimacy in peace. We can help them with that. Look, I’ve just the thing. Perhaps you could you give me a hand?”
“Of course, dear.”
Diana was holding two pink straps, each about eighteen inches long. She gave one to Eleanor, and they exchanged winks. The boys wondered what was coming next. Not for long. They felt the points of the straps being inserted between their thighs. Bobby squeezed his together, but to no avail. The women drew them through between the boys legs, worked the up till they were a high as they could get them, pressing against their balls and lying above the leg-bands of their shorts. They adjusted them till the buckles were midway between their outer thighs, then fed the points through the buckles and drew them tight, pulling the boys abdomens firmly together, and squashing their coc-ks against each other! As the straps were buckled the boys felt the shafts slip neatly side-by-side, pressed together like two sausages in a packet and held fast between their tummies!
“No, stop!” Tim cried out in protest.
“Please, Miss Murchison, Miss Bowditch, don’t do that…” begged Bobby, trying to maintain his manners, but knowing they were unlikely to relent. Tim was more forthright.
“Watcher doin’? Let us go, now, or we’ll…”
“Yes? What will you do?” asked Diana, curtly, tucking the point of her strap into its loop and standing back. “Tell Miss Poole, perhaps? You’re in no position to… No, I correct myself. You’re in the perfect position - for Miss Poole to give you a dozen strokes of her whip! Would you like that?”
Tim remembered what that felt like.
“No… Sorry, I didn’t mean no disrespec’…”
“Good. Glad to hear it. Now, Eleanor. Anything else in our cupboard that may be of use?”
“Well, I don’t know, Diana… There are these… Whatever they are…” she added innocently.
She took out a clear plastic box and held it out in both hands for Diana to see. It contained a selection of vibrators, maybe nine or ten, different shapes and sizes, ranging from ones eight or nine inches long down to one no bigger than a lipstick. From the door Bobby was the only one who could see.
“Shit…”
“Oh, how useful!” cried Diana. “Let me see… How about this one? No, too bobbly… I think we’ll have to go for…”
“This nice slim pink one?” suggested Eleanor.
“Yes. That’ll do nicely.” She took it out. It was activated by turning the base. She tried it. It buzzed vigorously into life. “Seems to be fully charged.” She switched it off and turned back to the boys.
“You look so tense! Just relax, guys. Don’t be so uptight. This will help you, believe me. Don’t fight it – go with the flow…”
She turned on the vibrator again.
“It’s on number one. You’ll hardly feel it.” She ran the tip over Tim’s behind. He wriggled and clenched his buttocks. “See? What can you feel?”
“It tickles,” said Tim, sulkily.
“Keep still!” hissed Bobby. “Don’t squirm like that! That’s what they want.”
“I can’t help it! It tickles!” Tim whispered back, irritably. “Ooh…”
Diana had inserted the point of the vibrator between his upper thighs, and was trying to push it in. Tim pressed his muscular thighs together as hard as he could. Diana frowned.
“Oh well, if that’s how you want it… Eleanor dear, could you squeeze a bit of lube on it?”
She held it out. Eleanor picked up a tube, and lubed the end. Diana turned back. Now it slipped in easily. She pushed it in until it touched his balls, then turned it up to number two. Soon both boys’ balls were vibrating in harmony – and so were their coc-ks. It felt so strange. Their pen-ises were pressed together, into what felt like a single thick shaft, vibrating between their tummies. Neither of them could tell where his own ended and his friend’s began. Both were fully tumescent, the head of Tim’s not far short of his belt, and both were oozing freely, lubricating the taut latex and facilitating the effects of the vibrator. Diana moved the head of the vibe gently around, or worked it slowly in and out, watching with a satisfied smile as the boys squirmed against each other, moaning in pleasure. Eleanor stood to one side recording their oscillations and their pleadings on her phone.
“Please, Miss M-Murchison,” whimpered Bobby, “please stop. If you don’t…”
“Yes, what will happen?” she asked, innocently.
“P-please…”
For each of them, the personal physical arousal, the constant friction of slippery coc-k against slippery coc-k, was difficult enough to resist, but being forced to share your friend’s pleasure as well, to listen to his gasps and groans, was too much to bear. Bobby had considerable self-discipline; but Tim was much more subservient to his feelings and emotions – or perhaps his were just stronger. Either way, he was the first to crack, to surrender to his lust. Having done so, there was no longer any reason to hold back. So, clasping Bobby’s hands in his own to forestall any resistance, and taking full advantage of his complete immobilisation, he began - as much as the thigh straps allowed - to pound Bobby’s firmly-muscled tummy, thrusting against it until he was overtaken by a massive climax, so intense that he cried out, and in his passion even bit the lobe of Bobby’s ear.
Bobby himself had been teetering on the brink for a minute or two, and Tim’s orgasm predictably triggered his own. He cried out in pain when Tim bit him, but he was already c-umming. The two of them pummelled each other furiously, like two passionate lovers reunited after a long absence, flooding their shorts with hot c-um.
96
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:10:24 PM »
Chapter 245.
Wednesday. An uneventful morning. Three sessions, all girls from the staff. The first pair were Evelina and Gabby from reception. They’d got permission to take the first hour off. Miss Poole diverted her secretary to look after reception for them. They had heard about the pageboy uniforms and simply couldn’t wait to see how the boys looked. There was a fair amount of flirting on both sides, which put the boys in a good mood for the rest of the morning. But after lunch they were in for a shock.
“Next session, two customers,” Ellie stated blandly. “You know them. They’ve booked the entire afternoon. Enjoy.”
“Who is it?” asked Bobby.”
“Go see. Specials. Remember boys – absolute obedience. Yes?”
When they found Diana and Eleanor sitting simpering in the waiting room after lunch, their faces fell. Uncharacteristically the ladies were dressed casually, in shirts and jeans.
“Oh, dear,” said Diana sarcastically, “aren’t you pleased to see us?”
“Why, of course, Miss Murchison… No, I mean… It’s just that lunch was a bit disappointing…”
“Oh, is that all? Well, let’s see if we can offer you something more inspiring, shall we? Follow us, please.”
They rose and went to the parlour door, waiting for Bobby to open it. It operated on a coded electronic lock, one keypad on the outside wall, one on the inside. He unlocked the door and let them in, he and Tim following behind, and locked it on the inside, as was his habit. When you entered the parlour itself there was a wall immediately on the right, on which was a cupboard, a couple of visitors’ chairs, and at the end, adjacent to the professional chairs, washing facilities, whilst on the left was a bay containing the single professional chair, a coffee machine and a water dispenser, and on the wall a row of cupboards for the boys’ equipment, plus two, one tall and one shorter, which were locked.
The door to the parlour was thick and soundproof, a timber four-panel door with a heavy frame and cruciform design, and a sealing strip around all four edges, designed to muffle proceedings from anyone sitting in the waiting room. There was a faint whoosh of air when you opened or shut it. And on the inside was a feature Bobby had taken to be either decorative or reinforcement – a steel track set into the central vertical running almost the length of the door. In fact this had a very specific purpose, as did other steel wall fitments at the far end, for the realisation of which access to the private cupboards, whose key was lent only to special customers, was necessary. Today Diana and Eleanor had that key in their possession, as well as certain information which had so far been imparted by Miss Poole to them alone.
Diana turned to the boys.
“Go and sit there, you two. Go on,” she ordered, curtly, indicating the visitors’ chairs. Then she went straight to one of the locked cupboards and unlocked it, and proceeded to rummage inside. She took out a small plastic box containing something metallic, an array of pink straps, and a few short lengths of steel chain with end clips. Then she summoned Bobby.
“Stand here.”
She took him by the arm, quite forcefully, and stood him by the right side of the door. Then she produced three steel devices, like thumbscrews Bobby thought. She inserted the first into the track on the level of his neck. She pushed it in, turned it sideways so a flange engaged with the sides of the track, then screwed what looked like a flattened D-ring several times using a tool like a fork until it was firmly fixed in place, and the ring was vertical. She repeated the exercise at the level of his waist and ankles, so there were three tethering points on the door in the form of narrow vertical rectangles.
“Chin up.”
First she buckled a broad pink leather collar around his neck. It had a buckle with a D-ring at the front, and another free D-ring at the back. Then matching ankle-cuffs.
“Now stand in the middle…”
The first thing she did was to unbuckle the belt of his shorts, unthread one side from the belt loops, thread it through middle tether, and back through the loops, and buckle it up again, thus securing his waist to the door. She allowed herself a little smile at the success of this first operation. Next she secured the rear D-ring on his collar to the top tether with a short double-clip chain. And finally she went down on one knee and attended to his ankles. A short chain with a carabiner clip at each end was attached to one ankle-cuff, passed through the tether, and attached to the other. She stood up, looking very pleased with herself.
“Try and move, Bobby. Difficult, eh? Very good. Nearly finished.”
Finally, she buckled on a pair of pink leather wrist-cuffs, which she attached together with a second clipped chain which she passed behind his back.
“Excellent!”
He was now fully immobilised, standing to attention fastened securely to the door of his own boot parlour. Tim looked from Bobby to Diana, and then to Eleanor, for some sort of explanation.
“Don’t worry, Timmy,” smirked Eleanor. “we haven’t forgotten you. Here, let’s get these on you.”
He stood helplessly as they fitted him with wrist- and ankle-cuffs. The wrist-cuffs they attached directly to Bobby’s with screw-links, the ankle-cuffs to the bottom tether, on a slightly longer chain than Bobby’s.
“Feet slightly apart, Timmy,” ordered Diana. “You’re an inch or two taller than Bobby. That’s better. Now your belts are quite level.”
She connected their belt-rings with a single screw-link, so their stomachs were touching. Then on went Tim’s collar, and another short length of clipped chain attached it to Bobby’s. Now they were looking straight into each other’s faces. Bobby looked concerned, Tim distinctly alarmed. With their wrists also clipped together, they were quite helpless.
“There,” laughed Diana, “I hope you’re both comfortable. I understand you two are quite close, emotionally. So I don’t imagine you’re too upset. Feel free to have a little kiss and cuddle if you want. Don’t mind us…” And they both sniggered like schoolgirls.
They left them in this uncomfortable position for a few minutes, while they took a few snaps from different angles. The boys felt annoyed and awkward. They tried to avoid each other’s eyes, and Tim planted his feet as far back as he could, and stuck out his rear, in an effort to prevent contact between them below the waist. But their coc-ks were already brushing against each other, and were soon responding with predictable exuberance. If matters had ended there it would have been embarrassing enough. But the ladies weren’t quite finished.
Wednesday. An uneventful morning. Three sessions, all girls from the staff. The first pair were Evelina and Gabby from reception. They’d got permission to take the first hour off. Miss Poole diverted her secretary to look after reception for them. They had heard about the pageboy uniforms and simply couldn’t wait to see how the boys looked. There was a fair amount of flirting on both sides, which put the boys in a good mood for the rest of the morning. But after lunch they were in for a shock.
“Next session, two customers,” Ellie stated blandly. “You know them. They’ve booked the entire afternoon. Enjoy.”
“Who is it?” asked Bobby.”
“Go see. Specials. Remember boys – absolute obedience. Yes?”
When they found Diana and Eleanor sitting simpering in the waiting room after lunch, their faces fell. Uncharacteristically the ladies were dressed casually, in shirts and jeans.
“Oh, dear,” said Diana sarcastically, “aren’t you pleased to see us?”
“Why, of course, Miss Murchison… No, I mean… It’s just that lunch was a bit disappointing…”
“Oh, is that all? Well, let’s see if we can offer you something more inspiring, shall we? Follow us, please.”
They rose and went to the parlour door, waiting for Bobby to open it. It operated on a coded electronic lock, one keypad on the outside wall, one on the inside. He unlocked the door and let them in, he and Tim following behind, and locked it on the inside, as was his habit. When you entered the parlour itself there was a wall immediately on the right, on which was a cupboard, a couple of visitors’ chairs, and at the end, adjacent to the professional chairs, washing facilities, whilst on the left was a bay containing the single professional chair, a coffee machine and a water dispenser, and on the wall a row of cupboards for the boys’ equipment, plus two, one tall and one shorter, which were locked.
The door to the parlour was thick and soundproof, a timber four-panel door with a heavy frame and cruciform design, and a sealing strip around all four edges, designed to muffle proceedings from anyone sitting in the waiting room. There was a faint whoosh of air when you opened or shut it. And on the inside was a feature Bobby had taken to be either decorative or reinforcement – a steel track set into the central vertical running almost the length of the door. In fact this had a very specific purpose, as did other steel wall fitments at the far end, for the realisation of which access to the private cupboards, whose key was lent only to special customers, was necessary. Today Diana and Eleanor had that key in their possession, as well as certain information which had so far been imparted by Miss Poole to them alone.
Diana turned to the boys.
“Go and sit there, you two. Go on,” she ordered, curtly, indicating the visitors’ chairs. Then she went straight to one of the locked cupboards and unlocked it, and proceeded to rummage inside. She took out a small plastic box containing something metallic, an array of pink straps, and a few short lengths of steel chain with end clips. Then she summoned Bobby.
“Stand here.”
She took him by the arm, quite forcefully, and stood him by the right side of the door. Then she produced three steel devices, like thumbscrews Bobby thought. She inserted the first into the track on the level of his neck. She pushed it in, turned it sideways so a flange engaged with the sides of the track, then screwed what looked like a flattened D-ring several times using a tool like a fork until it was firmly fixed in place, and the ring was vertical. She repeated the exercise at the level of his waist and ankles, so there were three tethering points on the door in the form of narrow vertical rectangles.
“Chin up.”
First she buckled a broad pink leather collar around his neck. It had a buckle with a D-ring at the front, and another free D-ring at the back. Then matching ankle-cuffs.
“Now stand in the middle…”
The first thing she did was to unbuckle the belt of his shorts, unthread one side from the belt loops, thread it through middle tether, and back through the loops, and buckle it up again, thus securing his waist to the door. She allowed herself a little smile at the success of this first operation. Next she secured the rear D-ring on his collar to the top tether with a short double-clip chain. And finally she went down on one knee and attended to his ankles. A short chain with a carabiner clip at each end was attached to one ankle-cuff, passed through the tether, and attached to the other. She stood up, looking very pleased with herself.
“Try and move, Bobby. Difficult, eh? Very good. Nearly finished.”
Finally, she buckled on a pair of pink leather wrist-cuffs, which she attached together with a second clipped chain which she passed behind his back.
“Excellent!”
He was now fully immobilised, standing to attention fastened securely to the door of his own boot parlour. Tim looked from Bobby to Diana, and then to Eleanor, for some sort of explanation.
“Don’t worry, Timmy,” smirked Eleanor. “we haven’t forgotten you. Here, let’s get these on you.”
He stood helplessly as they fitted him with wrist- and ankle-cuffs. The wrist-cuffs they attached directly to Bobby’s with screw-links, the ankle-cuffs to the bottom tether, on a slightly longer chain than Bobby’s.
“Feet slightly apart, Timmy,” ordered Diana. “You’re an inch or two taller than Bobby. That’s better. Now your belts are quite level.”
She connected their belt-rings with a single screw-link, so their stomachs were touching. Then on went Tim’s collar, and another short length of clipped chain attached it to Bobby’s. Now they were looking straight into each other’s faces. Bobby looked concerned, Tim distinctly alarmed. With their wrists also clipped together, they were quite helpless.
“There,” laughed Diana, “I hope you’re both comfortable. I understand you two are quite close, emotionally. So I don’t imagine you’re too upset. Feel free to have a little kiss and cuddle if you want. Don’t mind us…” And they both sniggered like schoolgirls.
They left them in this uncomfortable position for a few minutes, while they took a few snaps from different angles. The boys felt annoyed and awkward. They tried to avoid each other’s eyes, and Tim planted his feet as far back as he could, and stuck out his rear, in an effort to prevent contact between them below the waist. But their coc-ks were already brushing against each other, and were soon responding with predictable exuberance. If matters had ended there it would have been embarrassing enough. But the ladies weren’t quite finished.
97
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:04:46 PM »
Chapter 244.
The next morning Ellie was just coming down the path between the two stable blocks as the girls were leaving the boot parlour for work.
“Good morning!”
“Hi, Ellie!”
“Have a nice evening? Did they behave?”
“Oh, yes. They were really good. Bobby even took the initiative at one point…” said Jessica, with an enigmatic smile.
“I won’t ask what you mean by that. You can tell me later.”
“Ellie? We wanted to ask you something,” said May. “It’s right that Bobby’s going to get a dress soon, yeah? He’s really desperate to have one. Tim too. No, Tim especially! Do you know when it’s likely to happen? And what sort of dress might it be?”
“I don’t – but I can have a word with Cynthia, who’s responsible for all his gear. I’ll ring her this morning. Do you know what Bobby’s looking for?”
“Blue satin, puff sleeves. Party dress sort of thing.”
“Okay – I’ll run it past her.”
Great. Thanks. We want to give them a surprise. They work so hard.”
“I know. Going to the canteen for lunch today?”
“Yes.”
“Okay. See you there. About twelve-thirty?”
“Yeah fine… ”
After getting the boys ready, despatching them for their first session, and tidying up, Ellie sat down and called Cynthia.
“Hi Cynthia. It’s Ellie. How are you?”
“I’m fine. You?”
“Yes, good. I’ve been asked by the boys’ girlfriends to ask you about Bobby’s dress. Is there one in the pipeline?”
“There is…but it’s not ready yet. Why?”
“Apparently they’re both quite excited by the idea.”
“Both?”
“Bobby and Timmy.”
Cynthia laughed. “Oh, really? That’s so cute. We haven’t fully discussed the design yet. But I can probably find him one off the peg. He’s a standard size. What did you have in mind?”
“Apparently the flavour of the month is a party dress - blue satin with puff sleeves.”
“Blue for a boy, eh? I’m sure we can find something suitable. But he’d have to come here. I wouldn’t send something out without trying it on him. When does he need it by?”
“Not sure. I’ll find out. They’re busy this week, too. How are you fixed? There’s only one booking Saturday afternoon, and it’s a single. Tim could handle that by himself. Might you be around?”
“Sure, any time after two. Let me know if he needs accessories. I could even get Trish to give him a makeover…”
Ellie reported back to the girls. May immediately volunteered to drive him to Fantastex.
“I don’t have to work Saturday. Whereabouts is the shop?”
“Off the Kennett road, about six miles past South Kennett. Wylye Marsh Trading Estate.”
“I can take my mum’s car. She’s going into London for the day. Don’t anyone tell Tim, right? We can’t tell Bobby either. It can be a surprise. He can leave as a bloke and come back as a girl!”
“What will you say?” asked Jessica.
“I dunno. I’ll think of something. Maybe I’ll say I’m going to buy some clothes and I want him along for his opinion.”
“Cynthia said they can give him a complete makeover too, if you wanted.”
“Wow. Why not? Let’s go for it. By the way, what about money? What’s this going to cost us?”
“Don’t worry, May. It’s all goes on the account. I’ll clear it with Miss Poole.”
“Would you? Thanks, Ellie…”
The next morning Ellie was just coming down the path between the two stable blocks as the girls were leaving the boot parlour for work.
“Good morning!”
“Hi, Ellie!”
“Have a nice evening? Did they behave?”
“Oh, yes. They were really good. Bobby even took the initiative at one point…” said Jessica, with an enigmatic smile.
“I won’t ask what you mean by that. You can tell me later.”
“Ellie? We wanted to ask you something,” said May. “It’s right that Bobby’s going to get a dress soon, yeah? He’s really desperate to have one. Tim too. No, Tim especially! Do you know when it’s likely to happen? And what sort of dress might it be?”
“I don’t – but I can have a word with Cynthia, who’s responsible for all his gear. I’ll ring her this morning. Do you know what Bobby’s looking for?”
“Blue satin, puff sleeves. Party dress sort of thing.”
“Okay – I’ll run it past her.”
Great. Thanks. We want to give them a surprise. They work so hard.”
“I know. Going to the canteen for lunch today?”
“Yes.”
“Okay. See you there. About twelve-thirty?”
“Yeah fine… ”
After getting the boys ready, despatching them for their first session, and tidying up, Ellie sat down and called Cynthia.
“Hi Cynthia. It’s Ellie. How are you?”
“I’m fine. You?”
“Yes, good. I’ve been asked by the boys’ girlfriends to ask you about Bobby’s dress. Is there one in the pipeline?”
“There is…but it’s not ready yet. Why?”
“Apparently they’re both quite excited by the idea.”
“Both?”
“Bobby and Timmy.”
Cynthia laughed. “Oh, really? That’s so cute. We haven’t fully discussed the design yet. But I can probably find him one off the peg. He’s a standard size. What did you have in mind?”
“Apparently the flavour of the month is a party dress - blue satin with puff sleeves.”
“Blue for a boy, eh? I’m sure we can find something suitable. But he’d have to come here. I wouldn’t send something out without trying it on him. When does he need it by?”
“Not sure. I’ll find out. They’re busy this week, too. How are you fixed? There’s only one booking Saturday afternoon, and it’s a single. Tim could handle that by himself. Might you be around?”
“Sure, any time after two. Let me know if he needs accessories. I could even get Trish to give him a makeover…”
Ellie reported back to the girls. May immediately volunteered to drive him to Fantastex.
“I don’t have to work Saturday. Whereabouts is the shop?”
“Off the Kennett road, about six miles past South Kennett. Wylye Marsh Trading Estate.”
“I can take my mum’s car. She’s going into London for the day. Don’t anyone tell Tim, right? We can’t tell Bobby either. It can be a surprise. He can leave as a bloke and come back as a girl!”
“What will you say?” asked Jessica.
“I dunno. I’ll think of something. Maybe I’ll say I’m going to buy some clothes and I want him along for his opinion.”
“Cynthia said they can give him a complete makeover too, if you wanted.”
“Wow. Why not? Let’s go for it. By the way, what about money? What’s this going to cost us?”
“Don’t worry, May. It’s all goes on the account. I’ll clear it with Miss Poole.”
“Would you? Thanks, Ellie…”
98
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 18, 2025, 12:01:11 PM »
Chapter 243.
It had been a good day. Everyone had been impressed by their new uniforms, and they had received lots of compliments, and what was just as important, tips, from all their customers. They were feeling popular, they were getting to know the stable girls and some of the paying members, they were beginning to rake in the cash – though they wouldn’t get their first month’s salary for a couple of weeks yet – and their loves-lives were looking up. May and Jessica were coming over after work, and they were hoping for at least a good snogging session, if not more…
They were in their sitting-room, about to change out of their uniforms, when Ellie walked in.
Tim frowned. “Ever ‘eard of knockin’ before you come bargin’ in?”
“Knocking? Why? Is there someone important in here?”
“You’re so rude sometimes, Ellie…” remarked Bobby.
Ellie sighed. “Look. You work here, I work here. None of us is better than the others. I have a lot of work to do looking after your needs, which means I’m gonna be around this place as much as you. I’m not your slave, and you’re not international celebrities, - so get used to it.”
“We’re more celebrities than you are,” said Tim, trying – and failing – to look important.
“Well, Timmy Painter, I know you’ve had girls drooling all over your magnificent body all day, but to me you’re just a boot boy. Some come down to earth, okay?”
Tim was about to respond, but Bobby stopped him.
“Come on, Tim. She’s right you know. We need Ellie more than she needs us. Sorry, Ellie.”
Ellie looked surprised. “Thank you Bobby. I’m glad one of you gets it at least.”
“Sorry, Ellie,” echoed Tim, . “I didn’t mean nuffink bad …”
“Okay, Tim. No offence taken. I’m only here to bring you your alternative outfits. Instructions from May and Jessica. Something about continuing your “education” – whatever that means.” (Though she had a pretty good idea.) “So get showered and I’ll help you into them.”
After work May and Jessica had gone up to the main building to shower and change. It was six-thirty by the time they got back to the boot parlour. Ellie was just leaving.
“They’re all ready. Hoods and everything. Vibes on number two.”
“Any problems?”
“Nope. Seems they’ll do anything if you guys want them to. You have them well trained.”
“We’ve only just started, Ellie,” grinned Jessica.
They found the boys sitting side by side on the sofa, each dressed exactly as they had requested – shorts with flies, white socks, Mary Janes, red ribbon choker, pink hood with tunnel gag, shirtless, but wearing red latex gloves. Jessica nodded towards Bobby’s little budding breasts. May smiled approval. The plugs were out and lying on the coffee-table, next to their baseball caps.
“Hello boys,” said May, gaily, picking up the caps and putting them on over their hoods. “Ooh, that looks quite weird…” she exclaimed, “caps and blank pink faces… But quite cool…”
“All dressed up ready for your lesson. What good little boys,” said Jessica, patronisingly. “You’re learning fast. Follow Ellie’s instructions and you won’t go far wrong.”
She winked at May. Ellie was right. They seemed to have accepted the girls’ authority already. That would make their job much easier.
“Have you eaten?” Shakes of heads. “No? Neither have we. Let’s continue with your lessons first, shall we? We can eat in an hour or so. Now what’s on the agenda today, May?”
“Well, why don’t we carry on from where we left off? Tim was fantasizing about Bobby’s dress, I believe. Is that right, Tim? Are you blushing under that hood?” She put her hand near his face. “Goodness, I can feel your cheeks burning!” she joked.
She set her phone filming on the coffee-table, and they took their seats either side of it. They began by stroking the front of the boys shorts, while May reminded them of Tim’s fantasy, rehearsing every little detail and adding a few observations of her own. By the time she was half way through an imaginative description of how Bobby might look in his latex panties, they were both beginning to fidget, their breathing had become deeper, and the fronts of their shorts were beginning to show signs of strain.
“You remember all that, Tim?” said Jessica. “You were really very specific. Perhaps some time we’ll be able to realise your little fantasy. Would you like that?”
No reply.
“Would you?”
Tim stiffened, and made an inarticulate sound.
She popped open his fly, and his coc-k sprang out, erect and quivering.
“I’ll take that as a yes. So, I want you to imagine Bobby in his cute little dress with his white stockings and his” – she lowered her voice – “his little panties…”
Tim squirmed, making his coc-k tremble. Jessica reached out and took it delicately between finger and thumb. It was satisfyingly hard. She continued.
“Today imagine he’s done his hair up in pretty red ribbons, with a matching ribbon choker - like the one he’s wearing right now - and put on a little makeup. Lovely bright red lip gloss, red eye shadow, and mascara. And to hold his little breasts – I’m sure you’ve noticed them – he’s wearing a cute little training bra. You know why he’s taken all that trouble? Well I’ll tell you. He’s hoping you’ll ask him out! Yes! He wants to go on a date with you! Isn’t that sweet? Do you think you’d be brave enough to do that?”
Tim shuddered. His was breathing faster now, the air making a faint whistling sound in his gag.
“Maybe in a week or so, when he gets his new dress, you’ll take the plunge. You can tell him how you feel – he’s right next to you now. Oh, I forgot. You can’t speak, can you. Never mind. At the moment, like you, he’s not even wearing a shirt. He looks even more like a pretty girl. Shame you can’t see. You’ll just have to contain yourself for now…”
She broke off, leaving the narrative hanging in the air, giving him a chance to compose himself. But with all the talk of dresses and makeup, and with his thigh pressed against Tim’s, which was trembling slightly, Bobby was also feeling aroused. The thought of red ribbons and glossy red lipstick was very exciting. May regarded his little bulge with amused satisfaction, then reached over and flipped the press-stud. Out jumped the little sausage, gleaming and eager in its scarlet skin, like Tim’s slightly smaller twin.
So there they were, side by side, hands on knees. Jessica gave May a thumbs-up. What next? They’d not really made a firm plan, but were thinking they’d play it by ear. May looked thoughtful for a moment, then leant over and whispered in Jessica’s ear. Jessica looked doubtful, but shrugged. She turned back to Tim.
“Bobby fancies you as well, Tim. Do you know that?”
Tim gave a slight doubtful shake of the head.
“Shall I show you? Here, give me your hand…”
She took his left hand, lifted it over Bobby’s right arm, wrapped his fingers around the top of Bobby’s coc-k, and withdrew her own hand. Bobby gasped. Tim tensed, but didn’t let go.
“See how excited he is?” she said, blandly. That’s all down to you, young sir.”
Bobby squirmed. There was a sharp intake of breath through Tim’s gag, but his fingers stayed where they were. He could feel the heat of Bobby’s coc-k through its condom and his gloves. In the darkness behind the latex mask Tim was in his own little fantasy world, and vibrating with excitement. This was on a different level from the boys’ earlier sexual encounters. The way the latex hood clung to his face, its powerful reassuring scent, made him feel safe and free. He abandoned himself to his feelings, and began gently to massage Bobby’s twitching boyhood, eliciting a faint moan of pleasure. Jessica put a finger to her lips, and the girls stayed quiet, and sat back to observe. Bobby’s hands were gripping his knees, his head resting on the back of the sofa. His bare chest was rising and falling faster as his breathing quickened. Every now and then he would tense, as if staving off orgasm. Then, quite unexpectedly, he reached across and gripped Tim’s erection, making him squeak with surprise. The girls wanted to scream out loud, but they forced themselves to stay quiet and watch while Bobby and Tim proceeded to engage in an enthusiastic mutual masturbation competition.
“They’re really going for it,” whispered May delightedly. “Who do you thinks going to win?”
“My money’s on Bobby. Tim’s ready to pop at any moment.”
The words were hardly out of her mouth when Tim was convulsed with orgasm, jerking and moaning as Bobby milked away mercilessly, until his friend’s spasms induced his own shuddering climax.
Their ecstatic frenzy gradually subsided, leaving them limp and spent, leaning against each other. They were incapable of resisting as the girls carefully removed their full condoms, and having exchanged them, fed them the contents despite some ineffectual resistance. It had been a most satisfactory lesson. But Jessica had a theory.
“This isn’t their first time, May,” she whispered. “Bet you anything you like. Wait…” – she raised her voice – “Tell us the truth, boys. Have you done this before?”
No response.
“Just nod your heads if you have. Don’t be shy about it. You seemed too good at it…”
Tim remained silent, shaking his head, but Bobby was too honest to deny it. He nodded slowly, and held up two fingers.
“So this is the third time?”
Tim dug his elbow into Bobby’s ribs, but he nodded again.
“I thought so. Well, if you’ve swallowed your treats – have you? – good, then we can take off your hoods.”
They stood behind the boys as they had done the day before and rolled them off, making sure to capture their faces on the video in case it was needed for future use. They didn’t notice, seeming mainly intent on avoiding each other’s eyes.
“Don’t be embarrassed,” said Jessica. “That’s the whole point of these exercises – to dispense with unnecessary embarrassment and get you in touch with your true feelings. That was an expression of true friendship - and don’t try to tell us you didn’t enjoy it! I bet you enjoyed it more than the first two times, right?”
They couldn’t deny it. The previous time, after they had finished, they felt a little bit awkward. This time, with the girls in charge, there was an initial embarrassment, but they felt much more relaxed. Actually, it had been quite fun – and a lot more exciting and intense.
Bobby grinned. “You came first again, Tim That’s two-one, isn’t it?”
“That ain’t fair! I weren’t ready for it! If I’d ‘ad a warnin’ you was gonna do that as well…”
“Stop bickering, you two!” scolded Jessica. “Listen. Why don’t I order some food, there’s beer in the fridge, and we can have a kiss and cuddle until it arrives. Yes?”
Their sexual needs satisfied – for the time being – they were suddenly overwhelmed with the desire for food and drink. “Yes please!” they chorused.
It had been a good day. Everyone had been impressed by their new uniforms, and they had received lots of compliments, and what was just as important, tips, from all their customers. They were feeling popular, they were getting to know the stable girls and some of the paying members, they were beginning to rake in the cash – though they wouldn’t get their first month’s salary for a couple of weeks yet – and their loves-lives were looking up. May and Jessica were coming over after work, and they were hoping for at least a good snogging session, if not more…
They were in their sitting-room, about to change out of their uniforms, when Ellie walked in.
Tim frowned. “Ever ‘eard of knockin’ before you come bargin’ in?”
“Knocking? Why? Is there someone important in here?”
“You’re so rude sometimes, Ellie…” remarked Bobby.
Ellie sighed. “Look. You work here, I work here. None of us is better than the others. I have a lot of work to do looking after your needs, which means I’m gonna be around this place as much as you. I’m not your slave, and you’re not international celebrities, - so get used to it.”
“We’re more celebrities than you are,” said Tim, trying – and failing – to look important.
“Well, Timmy Painter, I know you’ve had girls drooling all over your magnificent body all day, but to me you’re just a boot boy. Some come down to earth, okay?”
Tim was about to respond, but Bobby stopped him.
“Come on, Tim. She’s right you know. We need Ellie more than she needs us. Sorry, Ellie.”
Ellie looked surprised. “Thank you Bobby. I’m glad one of you gets it at least.”
“Sorry, Ellie,” echoed Tim, . “I didn’t mean nuffink bad …”
“Okay, Tim. No offence taken. I’m only here to bring you your alternative outfits. Instructions from May and Jessica. Something about continuing your “education” – whatever that means.” (Though she had a pretty good idea.) “So get showered and I’ll help you into them.”
After work May and Jessica had gone up to the main building to shower and change. It was six-thirty by the time they got back to the boot parlour. Ellie was just leaving.
“They’re all ready. Hoods and everything. Vibes on number two.”
“Any problems?”
“Nope. Seems they’ll do anything if you guys want them to. You have them well trained.”
“We’ve only just started, Ellie,” grinned Jessica.
They found the boys sitting side by side on the sofa, each dressed exactly as they had requested – shorts with flies, white socks, Mary Janes, red ribbon choker, pink hood with tunnel gag, shirtless, but wearing red latex gloves. Jessica nodded towards Bobby’s little budding breasts. May smiled approval. The plugs were out and lying on the coffee-table, next to their baseball caps.
“Hello boys,” said May, gaily, picking up the caps and putting them on over their hoods. “Ooh, that looks quite weird…” she exclaimed, “caps and blank pink faces… But quite cool…”
“All dressed up ready for your lesson. What good little boys,” said Jessica, patronisingly. “You’re learning fast. Follow Ellie’s instructions and you won’t go far wrong.”
She winked at May. Ellie was right. They seemed to have accepted the girls’ authority already. That would make their job much easier.
“Have you eaten?” Shakes of heads. “No? Neither have we. Let’s continue with your lessons first, shall we? We can eat in an hour or so. Now what’s on the agenda today, May?”
“Well, why don’t we carry on from where we left off? Tim was fantasizing about Bobby’s dress, I believe. Is that right, Tim? Are you blushing under that hood?” She put her hand near his face. “Goodness, I can feel your cheeks burning!” she joked.
She set her phone filming on the coffee-table, and they took their seats either side of it. They began by stroking the front of the boys shorts, while May reminded them of Tim’s fantasy, rehearsing every little detail and adding a few observations of her own. By the time she was half way through an imaginative description of how Bobby might look in his latex panties, they were both beginning to fidget, their breathing had become deeper, and the fronts of their shorts were beginning to show signs of strain.
“You remember all that, Tim?” said Jessica. “You were really very specific. Perhaps some time we’ll be able to realise your little fantasy. Would you like that?”
No reply.
“Would you?”
Tim stiffened, and made an inarticulate sound.
She popped open his fly, and his coc-k sprang out, erect and quivering.
“I’ll take that as a yes. So, I want you to imagine Bobby in his cute little dress with his white stockings and his” – she lowered her voice – “his little panties…”
Tim squirmed, making his coc-k tremble. Jessica reached out and took it delicately between finger and thumb. It was satisfyingly hard. She continued.
“Today imagine he’s done his hair up in pretty red ribbons, with a matching ribbon choker - like the one he’s wearing right now - and put on a little makeup. Lovely bright red lip gloss, red eye shadow, and mascara. And to hold his little breasts – I’m sure you’ve noticed them – he’s wearing a cute little training bra. You know why he’s taken all that trouble? Well I’ll tell you. He’s hoping you’ll ask him out! Yes! He wants to go on a date with you! Isn’t that sweet? Do you think you’d be brave enough to do that?”
Tim shuddered. His was breathing faster now, the air making a faint whistling sound in his gag.
“Maybe in a week or so, when he gets his new dress, you’ll take the plunge. You can tell him how you feel – he’s right next to you now. Oh, I forgot. You can’t speak, can you. Never mind. At the moment, like you, he’s not even wearing a shirt. He looks even more like a pretty girl. Shame you can’t see. You’ll just have to contain yourself for now…”
She broke off, leaving the narrative hanging in the air, giving him a chance to compose himself. But with all the talk of dresses and makeup, and with his thigh pressed against Tim’s, which was trembling slightly, Bobby was also feeling aroused. The thought of red ribbons and glossy red lipstick was very exciting. May regarded his little bulge with amused satisfaction, then reached over and flipped the press-stud. Out jumped the little sausage, gleaming and eager in its scarlet skin, like Tim’s slightly smaller twin.
So there they were, side by side, hands on knees. Jessica gave May a thumbs-up. What next? They’d not really made a firm plan, but were thinking they’d play it by ear. May looked thoughtful for a moment, then leant over and whispered in Jessica’s ear. Jessica looked doubtful, but shrugged. She turned back to Tim.
“Bobby fancies you as well, Tim. Do you know that?”
Tim gave a slight doubtful shake of the head.
“Shall I show you? Here, give me your hand…”
She took his left hand, lifted it over Bobby’s right arm, wrapped his fingers around the top of Bobby’s coc-k, and withdrew her own hand. Bobby gasped. Tim tensed, but didn’t let go.
“See how excited he is?” she said, blandly. That’s all down to you, young sir.”
Bobby squirmed. There was a sharp intake of breath through Tim’s gag, but his fingers stayed where they were. He could feel the heat of Bobby’s coc-k through its condom and his gloves. In the darkness behind the latex mask Tim was in his own little fantasy world, and vibrating with excitement. This was on a different level from the boys’ earlier sexual encounters. The way the latex hood clung to his face, its powerful reassuring scent, made him feel safe and free. He abandoned himself to his feelings, and began gently to massage Bobby’s twitching boyhood, eliciting a faint moan of pleasure. Jessica put a finger to her lips, and the girls stayed quiet, and sat back to observe. Bobby’s hands were gripping his knees, his head resting on the back of the sofa. His bare chest was rising and falling faster as his breathing quickened. Every now and then he would tense, as if staving off orgasm. Then, quite unexpectedly, he reached across and gripped Tim’s erection, making him squeak with surprise. The girls wanted to scream out loud, but they forced themselves to stay quiet and watch while Bobby and Tim proceeded to engage in an enthusiastic mutual masturbation competition.
“They’re really going for it,” whispered May delightedly. “Who do you thinks going to win?”
“My money’s on Bobby. Tim’s ready to pop at any moment.”
The words were hardly out of her mouth when Tim was convulsed with orgasm, jerking and moaning as Bobby milked away mercilessly, until his friend’s spasms induced his own shuddering climax.
Their ecstatic frenzy gradually subsided, leaving them limp and spent, leaning against each other. They were incapable of resisting as the girls carefully removed their full condoms, and having exchanged them, fed them the contents despite some ineffectual resistance. It had been a most satisfactory lesson. But Jessica had a theory.
“This isn’t their first time, May,” she whispered. “Bet you anything you like. Wait…” – she raised her voice – “Tell us the truth, boys. Have you done this before?”
No response.
“Just nod your heads if you have. Don’t be shy about it. You seemed too good at it…”
Tim remained silent, shaking his head, but Bobby was too honest to deny it. He nodded slowly, and held up two fingers.
“So this is the third time?”
Tim dug his elbow into Bobby’s ribs, but he nodded again.
“I thought so. Well, if you’ve swallowed your treats – have you? – good, then we can take off your hoods.”
They stood behind the boys as they had done the day before and rolled them off, making sure to capture their faces on the video in case it was needed for future use. They didn’t notice, seeming mainly intent on avoiding each other’s eyes.
“Don’t be embarrassed,” said Jessica. “That’s the whole point of these exercises – to dispense with unnecessary embarrassment and get you in touch with your true feelings. That was an expression of true friendship - and don’t try to tell us you didn’t enjoy it! I bet you enjoyed it more than the first two times, right?”
They couldn’t deny it. The previous time, after they had finished, they felt a little bit awkward. This time, with the girls in charge, there was an initial embarrassment, but they felt much more relaxed. Actually, it had been quite fun – and a lot more exciting and intense.
Bobby grinned. “You came first again, Tim That’s two-one, isn’t it?”
“That ain’t fair! I weren’t ready for it! If I’d ‘ad a warnin’ you was gonna do that as well…”
“Stop bickering, you two!” scolded Jessica. “Listen. Why don’t I order some food, there’s beer in the fridge, and we can have a kiss and cuddle until it arrives. Yes?”
Their sexual needs satisfied – for the time being – they were suddenly overwhelmed with the desire for food and drink. “Yes please!” they chorused.
99
Active Sissy Stories / Re: Proof of Intent
« Last post by Baby Samantha on September 17, 2025, 07:19:15 AM »
I’m loving this story and the possibilities it offers for continuation. I hope we will see som more chapters soon x
100
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 11, 2025, 04:48:24 AM »
Chapter 242.
Ellie had hung around to check Frankie wasn’t too shocked by her experience, and was quite surprised to see her emerge from the waiting-room with a smile on her face.
“Hi, Frankie? Okay, sweetie?”
“Oh, yes, Ellie. That was quite a show, thank you. Quite an eye-opener.”
“Oh…well, good. I’m pleased you’re…satisfied. Your boots look lovely and shiny now…”
“My boots? Oh, yes…of course, my boots. Yes, they did a good job on those too. Very smart boys. I shall definitely be back.”
“Really? You liked their uniforms, then…”
“Oh my god, they’re just perfect, Ellie. I never imagined Miss Poole… I mean to say, the boys are so good. Polite and obedient. And such an amazing service. I can’t wait to show my friends the photos I took.”
“Photos? You took some photos?”
“Lots and lots, actually, Ellie. Especially of Tim. He’s quite a big boy, isn’t he? I mean, to be wearing those cute little shorts. Bobby too – so pretty. They’re going to cause a sensation at that wedding…”
“Oh, they told you…”
“Boasting about it, yes, bless them. To think I had to be persuaded to come here…”
She looked thoughtful for a moment, then turned on her heel and headed for the door.
“See you again soon, Ellie.”
The door had barely shut behind her when Tim burst out of the waiting-room.
“Has she gone?”
Ellie frowned - then noticed his erection. She refrained from smiling. “Yes…”
“Ellie, what’s wiv these plugs? They were goin’ mad today. Did you alter the settin’s or somefink?”
“Settings, Tim? There are no settings. I told you, the vibrations are completely random. I have no control over them. What, did it feel different today?”
She lied convincingly. Future pranks depended on them believing it.
“Different? Stronger, yes. Like my whole lower body feels like it bein’ vibed…”
“Oh… Yes, I see. You too, Bobby?”
“Yes… It was quite embarrassing. I hope we didn’t scare her away…”
In view of her recent conversation with Frankie, she didn’t think they had, but she made a mental note to be more careful with the butt-plugs. “If they can do that setting three,” she thought, “what effect must the higher ones have?”
She would have offered to change their shorts, but at that moment the next booking arrived. The boys dodged back inside and tried to calm themselves, but it was clear they were in for a torrid morning…
At lunchtime Ellie arranged for the boys to change into clean shorts – and she made sure the vibes were on the lowest setting.
“There. I’ll have the others checked out. It may be an internal fault.”
Tim looked suspicious, but as nothing toward had happened after fifteen minutes or so, apart from some minor fluttering, he accepted her explanation.
“Who’s next,” asked Bobby. “Anyone we know?”
“You don’t know them. It’s Faith and Jamilah. They’re members, and their horses are in livery hear. Experienced riders. They started here together when they were kids. Won a good few medals between them. They’re here out of curiosity. They told me they’d heard some pretty lurid rumours about the new boot boys, so they decided to come and check them out. And get their boots polished.”
Almost as soon as they opened the waiting-room door and saw their customers sitting chatting and sipping coffee, Bobby and Tim knew this was going to be one of their more pleasurable sessions.
“Hi boys! Lovely to see you! We’ve heard so much about you,” cried Faith, with a big smile.
“Don’t tell us,” grinned Jamilah. “You’re Tim” - she pointed at Tim – “and you’re Bobby. Yes, everyone’s talking about you, you know. Your quite famous – and not only in Pitt’s Wood. I’ve heard some of the girls from Fleetford have booked sessions too.”
The boys relaxed at once.
“We do our best…” began Bobby.
“Come and sit down for a minute” said Faith. “Let’s get to know each other. Here…”
She moved along two seats, and beckoned them to sit between her and Jamilah. They made their way over and sat down rather awkwardly, hands in laps, Tim next to Jamilah, Bobby next to Faith.
“So these are you new uniforms,” said Jamilah. “Very smart! We were lucky, Faith – we got the first day of their pageboy outfits. They really suit you. Do you like them?”
“Oh, yeah… Fanks, miss.”
“Yes, thank you for saying so. We’re very proud of our new uniforms. We’re grateful to Miss Poole for paying for them, for our boot parlour, and all our equipment. She’s been really good to us all along.”
“That’s because she knows a good thing when she sees it,” nodded Faith. “She’s a very good businesswoman as well as knowing everything there is to know about equitation. But boys – how did you get into this occupation – cleaning boots?”
“’E started it,” said Tim, pointing a thumb at Bobby. “’E was the one what was inter it from the start, eh, mate?”
“Is that true, Bobby?”
Bobby reddened slightly. “I guess… I used to clean all my aunt’s boots for her – she’s got stacks and stacks of them – and she knows Miss Poole, and the idea just sort of grew from there…”
“So do you enjoy what you do?”
“Oh, yes, very much!” he blurted. Then perceiving he may have dropped his guard a little, he added, “I, er…that is to say… What I mean is, it’s very satisfying to provide a useful service to all the riders. They may not have time to clean their boots, and with us they don’t even have to take them off. They can sit and relax while we do all the work.”
“You sound as though you love what you do, Bobby. How about you, Tim?”
“At first ‘e talked me inter it. But now I’m getting’ to like it. We get well paid, and…”
“And you get to chat up all the girls…” put in Jamilah, with a wink.
Tim gave a sheepish grin.
“So, what sort of boots do you like best?” asked Faith.
“I don’t mind,” said Tim, frankly. “’E likes figh-boots, don’cher Bobby?”
“Really, Bobby? Is that true?” gasped Jamilah. “I wish I’d known. I would have worn mine today. They come right up to here!” She indicated a point high up on her thigh. Bobby gulped and pressed his hands more firmly in his lap. The mere thought was enough…
“Yeah, it’s true, ain’t it mate?”
“Shut up, Tim…”
“You should’a seen ‘im when we ‘ad that Serena lady in ‘ere…”
“Serena?” Faith laughed. “You serviced Serena?”
“Yeah,” continued Tim, enjoying Bobby’s embarrassment, “we did. An’ she was wearin’ this amazin’ latex outfit…”
“Ah, yes. We’ve seen that,” said Faith. “That little flirt. Well, if she’s heard about your new outfits she’ll be back, I can guarantee that.”
“Yes. There’s nothing she likes better than handsome young men,” grinned Jamilah. “Eats ‘em for breakfast. Better watch out, boys!”
“How do you feel about being eaten by Serena?” asked Faith seriously. The boys looked at her, alarmed, making the girls explode with laughter.
“Anyway,” said Jamilah, “I think it’s time you attended to us. Do you like our boots?”
Both girls wore tan riding boots over black leather breeches, a look that had been trending at Pitt’s Wood for some months. They had been leaning into the boys, so that the leather was pressing against their bare thighs. Beneath his hands Bobby was already hard, and Tim wasn’t far behind. It was a relief to get down on their knees and get to work…
It was an enjoyable session. The boys felt they had made two good friends. The girls left a good tip, kissed them goodbye, promised to come again soon – and Jamilah promised to wear her thigh-boots. They left the boys in the waiting-room, walked down the corridor and out of the main door. And only then did they release their suppressed feelings, and collapse in laughter…
Ellie had hung around to check Frankie wasn’t too shocked by her experience, and was quite surprised to see her emerge from the waiting-room with a smile on her face.
“Hi, Frankie? Okay, sweetie?”
“Oh, yes, Ellie. That was quite a show, thank you. Quite an eye-opener.”
“Oh…well, good. I’m pleased you’re…satisfied. Your boots look lovely and shiny now…”
“My boots? Oh, yes…of course, my boots. Yes, they did a good job on those too. Very smart boys. I shall definitely be back.”
“Really? You liked their uniforms, then…”
“Oh my god, they’re just perfect, Ellie. I never imagined Miss Poole… I mean to say, the boys are so good. Polite and obedient. And such an amazing service. I can’t wait to show my friends the photos I took.”
“Photos? You took some photos?”
“Lots and lots, actually, Ellie. Especially of Tim. He’s quite a big boy, isn’t he? I mean, to be wearing those cute little shorts. Bobby too – so pretty. They’re going to cause a sensation at that wedding…”
“Oh, they told you…”
“Boasting about it, yes, bless them. To think I had to be persuaded to come here…”
She looked thoughtful for a moment, then turned on her heel and headed for the door.
“See you again soon, Ellie.”
The door had barely shut behind her when Tim burst out of the waiting-room.
“Has she gone?”
Ellie frowned - then noticed his erection. She refrained from smiling. “Yes…”
“Ellie, what’s wiv these plugs? They were goin’ mad today. Did you alter the settin’s or somefink?”
“Settings, Tim? There are no settings. I told you, the vibrations are completely random. I have no control over them. What, did it feel different today?”
She lied convincingly. Future pranks depended on them believing it.
“Different? Stronger, yes. Like my whole lower body feels like it bein’ vibed…”
“Oh… Yes, I see. You too, Bobby?”
“Yes… It was quite embarrassing. I hope we didn’t scare her away…”
In view of her recent conversation with Frankie, she didn’t think they had, but she made a mental note to be more careful with the butt-plugs. “If they can do that setting three,” she thought, “what effect must the higher ones have?”
She would have offered to change their shorts, but at that moment the next booking arrived. The boys dodged back inside and tried to calm themselves, but it was clear they were in for a torrid morning…
At lunchtime Ellie arranged for the boys to change into clean shorts – and she made sure the vibes were on the lowest setting.
“There. I’ll have the others checked out. It may be an internal fault.”
Tim looked suspicious, but as nothing toward had happened after fifteen minutes or so, apart from some minor fluttering, he accepted her explanation.
“Who’s next,” asked Bobby. “Anyone we know?”
“You don’t know them. It’s Faith and Jamilah. They’re members, and their horses are in livery hear. Experienced riders. They started here together when they were kids. Won a good few medals between them. They’re here out of curiosity. They told me they’d heard some pretty lurid rumours about the new boot boys, so they decided to come and check them out. And get their boots polished.”
Almost as soon as they opened the waiting-room door and saw their customers sitting chatting and sipping coffee, Bobby and Tim knew this was going to be one of their more pleasurable sessions.
“Hi boys! Lovely to see you! We’ve heard so much about you,” cried Faith, with a big smile.
“Don’t tell us,” grinned Jamilah. “You’re Tim” - she pointed at Tim – “and you’re Bobby. Yes, everyone’s talking about you, you know. Your quite famous – and not only in Pitt’s Wood. I’ve heard some of the girls from Fleetford have booked sessions too.”
The boys relaxed at once.
“We do our best…” began Bobby.
“Come and sit down for a minute” said Faith. “Let’s get to know each other. Here…”
She moved along two seats, and beckoned them to sit between her and Jamilah. They made their way over and sat down rather awkwardly, hands in laps, Tim next to Jamilah, Bobby next to Faith.
“So these are you new uniforms,” said Jamilah. “Very smart! We were lucky, Faith – we got the first day of their pageboy outfits. They really suit you. Do you like them?”
“Oh, yeah… Fanks, miss.”
“Yes, thank you for saying so. We’re very proud of our new uniforms. We’re grateful to Miss Poole for paying for them, for our boot parlour, and all our equipment. She’s been really good to us all along.”
“That’s because she knows a good thing when she sees it,” nodded Faith. “She’s a very good businesswoman as well as knowing everything there is to know about equitation. But boys – how did you get into this occupation – cleaning boots?”
“’E started it,” said Tim, pointing a thumb at Bobby. “’E was the one what was inter it from the start, eh, mate?”
“Is that true, Bobby?”
Bobby reddened slightly. “I guess… I used to clean all my aunt’s boots for her – she’s got stacks and stacks of them – and she knows Miss Poole, and the idea just sort of grew from there…”
“So do you enjoy what you do?”
“Oh, yes, very much!” he blurted. Then perceiving he may have dropped his guard a little, he added, “I, er…that is to say… What I mean is, it’s very satisfying to provide a useful service to all the riders. They may not have time to clean their boots, and with us they don’t even have to take them off. They can sit and relax while we do all the work.”
“You sound as though you love what you do, Bobby. How about you, Tim?”
“At first ‘e talked me inter it. But now I’m getting’ to like it. We get well paid, and…”
“And you get to chat up all the girls…” put in Jamilah, with a wink.
Tim gave a sheepish grin.
“So, what sort of boots do you like best?” asked Faith.
“I don’t mind,” said Tim, frankly. “’E likes figh-boots, don’cher Bobby?”
“Really, Bobby? Is that true?” gasped Jamilah. “I wish I’d known. I would have worn mine today. They come right up to here!” She indicated a point high up on her thigh. Bobby gulped and pressed his hands more firmly in his lap. The mere thought was enough…
“Yeah, it’s true, ain’t it mate?”
“Shut up, Tim…”
“You should’a seen ‘im when we ‘ad that Serena lady in ‘ere…”
“Serena?” Faith laughed. “You serviced Serena?”
“Yeah,” continued Tim, enjoying Bobby’s embarrassment, “we did. An’ she was wearin’ this amazin’ latex outfit…”
“Ah, yes. We’ve seen that,” said Faith. “That little flirt. Well, if she’s heard about your new outfits she’ll be back, I can guarantee that.”
“Yes. There’s nothing she likes better than handsome young men,” grinned Jamilah. “Eats ‘em for breakfast. Better watch out, boys!”
“How do you feel about being eaten by Serena?” asked Faith seriously. The boys looked at her, alarmed, making the girls explode with laughter.
“Anyway,” said Jamilah, “I think it’s time you attended to us. Do you like our boots?”
Both girls wore tan riding boots over black leather breeches, a look that had been trending at Pitt’s Wood for some months. They had been leaning into the boys, so that the leather was pressing against their bare thighs. Beneath his hands Bobby was already hard, and Tim wasn’t far behind. It was a relief to get down on their knees and get to work…
It was an enjoyable session. The boys felt they had made two good friends. The girls left a good tip, kissed them goodbye, promised to come again soon – and Jamilah promised to wear her thigh-boots. They left the boys in the waiting-room, walked down the corridor and out of the main door. And only then did they release their suppressed feelings, and collapse in laughter…
The more you give, the more I can give back.
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