Active Sissy Stories / Re: Proof of Intent
« Last post by Baby Samantha on Yesterday at 07:19:15 AM »
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 11, 2025, 04:48:24 AM »
Ellie had hung around to check Frankie wasnât too shocked by her experience, and was quite surprised to see her emerge from the waiting-room with a smile on her face.
âHi, Frankie? Okay, sweetie?â
âOh, yes, Ellie. That was quite a show, thank you. Quite an eye-opener.â
âOhâŚwell, good. Iâm pleased youâreâŚsatisfied. Your boots look lovely and shiny nowâŚâ
âMy boots? Oh, yesâŚof course, my boots. Yes, they did a good job on those too. Very smart boys. I shall definitely be back.â
âReally? You liked their uniforms, thenâŚâ
âOh my god, theyâre 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 canât wait to show my friends the photos I took.â
âPhotos? You took some photos?â
âLots and lots, actually, Ellie. Especially of Tim. Heâs quite a big boy, isnât he? I mean, to be wearing those cute little shorts. Bobby too â so pretty. Theyâre going to cause a sensation at that weddingâŚâ
âOh, they told youâŚâ
âBoasting about it, yes, bless them. To think I had to be persuaded to come hereâŚâ
She looked thoughtful for a moment, then turned on her heel and headed for the door.
âSee you again soon, Ellie.â
The door had barely shut behind her when Tim burst out of the waiting-room.
âHas she gone?â
Ellie frowned - then noticed his erection. She refrained from smiling. âYesâŚâ
âEllie, whatâs wiv these plugs? They were goinâ mad today. Did you alter the settinâs or somefink?â
âSettings, 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?â
She lied convincingly. Future pranks depended on them believing it.
âDifferent? Stronger, yes. Like my whole lower body feels like it beinâ vibedâŚâ
âOh⌠Yes, I see. You too, Bobby?â
âYes⌠It was quite embarrassing. I hope we didnât scare her awayâŚâ
In view of her recent conversation with Frankie, she didnât think they had, but she made a mental note to be more careful with the butt-plugs. âIf they can do that setting three,â she thought, âwhat effect must the higher ones have?â
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 morningâŚ
At lunchtime Ellie arranged for the boys to change into clean shorts â and she made sure the vibes were on the lowest setting.
âThere. Iâll have the others checked out. It may be an internal fault.â
Tim looked suspicious, but as nothing toward had happened after fifteen minutes or so, apart from some minor fluttering, he accepted her explanation.
âWhoâs next,â asked Bobby. âAnyone we know?â
âYou donât know them. Itâs Faith and Jamilah. Theyâre 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. Theyâre here out of curiosity. They told me theyâd heard some pretty lurid rumours about the new boot boys, so they decided to come and check them out. And get their boots polished.â
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.
âHi boys! Lovely to see you! Weâve heard so much about you,â cried Faith, with a big smile.
âDonât tell us,â grinned Jamilah. âYouâre Timâ - she pointed at Tim â âand youâre Bobby. Yes, everyoneâs talking about you, you know. Your quite famous â and not only in Pittâs Wood. Iâve heard some of the girls from Fleetford have booked sessions too.â
The boys relaxed at once.
âWe do our bestâŚâ began Bobby.
âCome and sit down for a minuteâ said Faith. âLetâs get to know each other. HereâŚâ
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.
âSo these are you new uniforms,â said Jamilah. âVery smart! We were lucky, Faith â we got the first day of their pageboy outfits. They really suit you. Do you like them?â
âOh, yeah⌠Fanks, miss.â
âYes, thank you for saying so. Weâre very proud of our new uniforms. Weâre grateful to Miss Poole for paying for them, for our boot parlour, and all our equipment. Sheâs been really good to us all along.â
âThatâs because she knows a good thing when she sees it,â nodded Faith. âSheâs a very good businesswoman as well as knowing everything there is to know about equitation. But boys â how did you get into this occupation â cleaning boots?â
ââE started it,â said Tim, pointing a thumb at Bobby. ââE was the one what was inter it from the start, eh, mate?â
âIs that true, Bobby?â
Bobby reddened slightly. âI guess⌠I used to clean all my auntâs boots for her â sheâs got stacks and stacks of them â and she knows Miss Poole, and the idea just sort of grew from thereâŚâ
âSo do you enjoy what you do?â
âOh, yes, very much!â he blurted. Then perceiving he may have dropped his guard a little, he added, âI, erâŚthat is to say⌠What I mean is, itâs very satisfying to provide a useful service to all the riders. They may not have time to clean their boots, and with us they donât even have to take them off. They can sit and relax while we do all the work.â
âYou sound as though you love what you do, Bobby. How about you, Tim?â
âAt first âe talked me inter it. But now Iâm gettingâ to like it. We get well paid, andâŚâ
âAnd you get to chat up all the girlsâŚâ put in Jamilah, with a wink.
Tim gave a sheepish grin.
âSo, what sort of boots do you like best?â asked Faith.
âI donât mind,â said Tim, frankly. ââE likes figh-boots, donâcher Bobby?â
âReally, Bobby? Is that true?â gasped Jamilah. âI wish Iâd known. I would have worn mine today. They come right up to here!â She indicated a point high up on her thigh. Bobby gulped and pressed his hands more firmly in his lap. The mere thought was enoughâŚ
âYeah, itâs true, ainât it mate?â
âShut up, TimâŚâ
âYou shouldâa seen âim when we âad that Serena lady in âereâŚâ
âSerena?â Faith laughed. âYou serviced Serena?â
âYeah,â continued Tim, enjoying Bobbyâs embarrassment, âwe did. Anâ she was wearinâ this amazinâ latex outfitâŚâ
âAh, yes. Weâve seen that,â said Faith. âThat little flirt. Well, if sheâs heard about your new outfits sheâll be back, I can guarantee that.â
âYes. Thereâs nothing she likes better than handsome young men,â grinned Jamilah. âEats âem for breakfast. Better watch out, boys!â
âHow do you feel about being eaten by Serena?â asked Faith seriously. The boys looked at her, alarmed, making the girls explode with laughter.
âAnyway,â said Jamilah, âI think itâs time you attended to us. Do you like our boots?â
Both girls wore tan riding boots over black leather breeches, a look that had been trending at Pittâs 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 wasnât far behind. It was a relief to get down on their knees and get to workâŚ
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 â 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 laughterâŚ
Active Sissy Stories / Re: New Arrangements for Josh
« Last post by Dancer4Fun on September 10, 2025, 07:39:30 PM »
I have just finished re reading Josh for the umteenth time.
I hope there is some way you can find a suitable conclusion to this wonderful story.
I'm hoping Josh is so traumatized by his High Tea experience he willingly becomes another daughter and little sister as a more modern but younger girly even asking mummy if he can take the tablets she suggested, so he grows little boobies to fill his training bras so he never again has to experience the humiliation of the Fauntleroy Suit again.
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 10, 2025, 09:38:44 AM »
Frankie Meering sat in the waiting-room in a state of contained nervous uneasiness. She had never intended to make a visit to the boot parlour. She was an only child, and had been brought up by a single mother with anxiety issues, who had taught her to be wary of everyone, but especially men. As a result she was still as timid as a little mouse in mixed society, and was only really comfortable in the company of her few friends or her horses. But two of those friends, who had already visited, had coaxed and teased her until she felt ashamed of her cowardice, and consented to take the plunge. Having agreed and allowed them to book a session for her, she immediately regretted her decision. But they had made sure she attended, accompanying her to the boot parlour entrance and handing her into Ellieâs custody. Even then, had it not been for Ellieâs detaining her with aimless gossip, at which she excelled, she may well have fled.
She had seen the boys about the Centre in their civvies, and the sight of them brought a flush to her cheeks, and, when on one occasion they passed close by and looked at her, almost gave her a panic attack. Tim especially seemed so tall and masculine that the mere idea of being in his company, especially wearing one of those superhero uniforms she had seen at the show, made her heart flutter with terror.
She waited, trembling, as the clock ticked towards nine. On the dot, the door opened, and the boys appeared - their first appearance before customers as pageboys. She took in the little latex shorts with pink frills, the frilled latex gloves, the Mary Janes, the ribbon chokers â and nearly laughed out loud. Her hand went to her mouth, and she emitted an involuntary snort. The boys, anticipating quite the opposite reaction, stopped in their tracks. Was this the shy, delicate girl Ellie had warned them about? Had there been a change of booking? Why wasnât she staring in admiration at their amazing cool uniforms?
Bobby took charge.
âEr, good morning, miss. Iâm Bobby, and this is Timmy. Boot boys at your service. Please instruct us as to what you require, and weâll do our bestâŚâ
Frankie had quickly recovered her self-control. âThank you, boys. I must say you look veryâŚsmart. Smart, yes.â She was fighting the desire to burst out laughing. So these were the boys she had been frightened of! How could they possibly thinkâŚ? But it didnât matter. They believed it, and she wasnât going to disabuse them. Sheâd take her cue from them.
âWow! What amazing uniforms! You look so cool. Iâm so glad I came to see you at last.â
The boys looked at each other with satisfied smiles. She must have been taken aback at first. Too much of a shock for her, probably.
Tim immediately went into swaggering mode.
âGlad you like âem, miss. Do you like the colour? Cos we got uvvers in the pipeline, like, in different styles and colours.â
âWherever did you get them?â
âWe got our own supplier, see? Big internashânal company. Make us whatever we want.â
âReally? But I like these ones. I love them, in fact. Can I seeâŚ?â
She leant forward. Tim strolled over to give her a better view. She reached out and touched the side of his shorts, then ruffled his frills. She noted with delight the vertical bulge at the front, and the neat separation of his balls. She bit her lip, determined to stay serious.
âTheyâre so well made⌠And the fitâŚâ
âAll our uniforms are made to measure,â piped up Bobby.
âGosh, is that a fact?â Frankie leant back again. âDo you only wear them in here? Itâs a pity you canât wear them outside for everyone to see.â
âWell, no, weâre not allowed,â continued Bobby. âI think Miss Poole is worried they might get damaged if we did thatâŚâ
âYeah. Theyâre âspensive, seeâŚvery âspensive,â boasted Tim.
âBut next month,â said Bobby, excitedly, âwe have permission to wear them to a big wedding. Itâs like a friend of a friendâŚâ
âGosh, how exciting! Youâll be a big hit, Iâm sureâŚâ
There was a short pause, while Frankie looked both of them up and down. She took out her phone.
âWould you mind ifâŚ?â
âNo, not at all,â said Bobby. âGo ahead.â
âCould I have one of each of you separately, then one with both of you together?â
âSure.â
âBobby? Could you stand by the door? Just stand naturallyâŚâ
She rose from her chair and stood opposite him. Bobby hooked his thumbs into his belt and grinned. Frankie took a number snaps in various poses, keeping him busy for about five minutes, during which time he became conscious of the increasing intensity of the vibrations deep inside, and the consequent effect on his level of arousal. By the time she was satisfied, the pressure in the front of his shorts was palpable. He blushed slightly, and was relieved to when she called on Tim to take his place.
But Tim was already in a worse state. His plug had been twitching and pulsing all the while Bobby was being photographed, and now, despite his best efforts, his coc-k was quite out of control, and flaunting its length shamelessly as if determined to do its best to reach his belt buckle. At Frankieâs summons he looked around, as if to say, âwhat, me?â but Frankie, delighted at his obvious embarrassment, was having no procrastination, and gestured to him to take Bobbyâs place by the door. She went down on one knee to make sure of the best angle.
âCome on, Timmy. Your turn. Good boy. No, not like that â hook your thumbs in your belt like Bobby did. Thatâs it. That a much cooler pose. Smile, Timmy⌠Come on now, show how happy you are in your brand new pageboy outfit. Thatâs right! Hold itâŚâ
Timâs cheeks were burning as he faced her. His coc-k was as now firm and fat as a bratwurst sausage, standing proud and vertical in his shorts, pressing against his tummy. There was a noticeable narrowing half way up the shaft, marking the position of the latex tether. Every now and then it twitched visibly in response to the relentless vibrations of his butt-plug. But Frankie had no mercy, ordering into a variety of cute poses, enhanced by finger gestures â peace sign, finger to lips (naughty-boy style), hand over mouth (oops! What have I done?), and so on. She even tricked him into one, making him stand with his right thumb hooked into his belt, and then telling him to close all his other fingers except the index finger, leaving him pointing right at that which he most desired to conceal; but he realised just too late!
When she had finished with him, she took a brief time out to scroll through her pictures. Yes, these were going to make her quite a reputation amongst her friends, no doubt about that. She wound up with a few snaps of the boys together, arms in arm, wearing sickly smiles. The boot-cleaning came almost as an afterthought, but she felt the boys had done everything she had asked of them, and they deserved the respite of being on their knees for a few minutes instead of on show.
She looked down at them as they knelt, side-by-side, working on the leather. These were the sort of boys she liked. Sweet, innocent, and easily tamed. The shyness was all theirs; she felt quite at ease around them now, and indeed, the whole session had made her feel a much more confident person. She knew this wouldnât be her last visitâŚ
As she walked away from the parlour, past a couple of waiting customers, she felt calm and contented. Thinking of the photos on her phone, and the pleasure she would have editing them and showing them off to her friends, there was an uncharacteristically satisfied smile on her faceâŚ
Active Sissy Stories / Re: Sissy goes shopping
« Last post by WetPampers on September 09, 2025, 12:27:30 PM »
âDo you think Pauline would give me a kiss? I consider my clients' children to be a bit like family. I am a caring auntie, selecting their dresses, their underwear, and their punishment equipment. So, in return, I ask each of them for a kiss.â
Mrs. MacNab turned to her son and said, âWould you like to give Madame a big, juicy kiss? After all, we should be grateful to her for having this lovely shop where we can buy your cute things!â
What could poor Pauline do? âYes, Mom, I'd love to give her a big kiss.â And he held out his face to Madame's wet lips. She grabbed his head with both hands and pressed her mouth against his, inserting her tongue deep between his lips. He hated it, but he knew what he had to do: he suc-ked on Madame's tongue. Pauline was tortured by this breathtaking kiss because, although he hated it in his mind, his masculine nature was attracted to it, and he felt his excitement growing under his diapers.
The lady turned to Mrs. MacNab and said, âPauline is very well trained; that was a wonderful kiss he gave me. He will be very good entertainment for the ladies. But it is very hot in here; I will take off his coat and cap, and you can both walk around.â
Mrs. MacNab replied, "Yes, Pauline will make a delightful companion for the ladies when I'm done with him. He is being trained to be completely submissive and to provide lesbian services to women who desire a docile and enslaved male. But he will never be allowed to use his jewels in the manner of males. He knows that pleasure is forbidden to him forever. His jewels are there for the sole purpose of being handled by ladies, as is his little hole, for that matter. Yes, please, you may undress Pauline.
Pauline fidgeted and, turning to her mother, begged, âPlease let me keep my cape on, Mom, I'm not too hot.â âBut Pauline,â said Madame, âit's very hot in here. I'm turning up the temperature because many of the pupils have to undress. Look at those pretty twins, a boy and a girl. They're naked and are going to try on their corsets.â
It was true, on the other side of the living room there were two naked children, a boy and a girl of about fourteen years old and almost indistinguishable, except for their shaved private parts, as they both had long hair, slim waists, and budding breasts. Mrs. MacNab intervened harshly, âPauline! I won't say it twice! Keep still while Madame takes off your coat.â
Madame removed his cap, undid the buttons of his pea coat, and helped him take it off. The reason why the boy was so agitated and reluctant became obvious. He was wearing an adorable high-waisted baby dress with puffed sleeves that flared out from the waist, held out by a starched petticoat. The dress and petticoat were so short and flared that they revealed the adorable pink rubber panties the boy was wearing.
The pants were obviously lined with voluminous terry cloth diapers. With his long, shaved legs, white ankle socks, and buckled shoes, Pauline was a charming curiosity, and several customers marveled at the delightful sight of this tall boy (soon to be eighteen) who looked so much like a big baby.
The lady asked, âIs there anything special I can do for you?â
âOh, we'll start by window shopping at this wonderful salon,â said Mrs. MacNab, âthen Pauline has a long list of items he needs. I've given him permission to ask for them himself, and I know he's very excited and feels like a grown-up being able to shop on his own!â
âDo as you please, look around the large salon and also in the small special rooms such as the corset room or the rubber room...â said Madame, "and remember that there are no privates allowed for my clients' children and you can observe any of them trying on a garment or an instrument of discipline. Perhaps it would be good to take Pauline to the punishment room to see a child being whipped; it's always a salutary experience! Then, when you're done, I'll take care of you personally. Or better yet, I'll ask Yvonne, my fifteen-year-old assistant, to be at your disposal. Perhaps Pauline will be less intimidated asking a girl his own age, and in this case even younger than him, for his things. It's very thoughtful of you to allow him to ask for what he needs on his own; it helps him gain confidence.
The two women smiled, and Pauline felt her heart beat faster in the face of such falseness and hypocrisy. How could he feel âbigâ dressed up as a baby like that? And how could his shame at having to ask for the awful things on his list give him confidence? That was the last thing these women wanted to give the boys under their wing. He was going to feel even more foolish having to ask for these childish and intimate items from a girl younger than him. Would there be no end to this life of being a boy-girl reduced to the status of a tiny child?
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 09, 2025, 03:18:36 AM »
It was an unconventional relationship, but as none of them had ever experienced a âconventionalâ one â if such a thing can be said to exist â it troubled them not in the least. That night May and Jasmine shared one bed And Bobby and Tim the other, for no other reason than that the girls had to be at work by six-thirty on a Monday. By the time the boys woke they were gone.
Ellie ran into them on her way to the boysâ apartment, and received a brief account of events the previous evening, illustrated by a glimpse of the video. There was a smile on her face as she laid their pageboy uniforms out and called to them to rise.
âEight oâclock, boys! One hour to get ready and have breakfast.
âWhose firstâŚ?â came a sleepy voice from within.
âLet me see⌠AhâŚFrankie Meering. Do you know her?â
âDonât think soâŚâ
âSheâs a sweet girl. Rather shy. Quite surprised she turned up, actually â especially by herself. Two of her friends â they saw you guys in the first week â have been trying to persuade her to book a session. Be nice to her, wonât you?â
Despite this apparently well-meaning advice, the mischievous Ellie had decided Frankie deserved a little treat to reward her for taking the plunge, and she had set the vibes to mark three again. âThat should easily set her blushing,â she said to herself, with a smile. She delayed getting the boys into their uniforms till the last minute, pretending to have forgotten to charge their butt-plugs.
âGood news, Tim,â whispered Bobby. âLooks like we may have a quiet time of it today.â
Tim frowned. âIt ainât like her to forget somethink like thatâŚâ he said, suspiciously.
âOh, sheâs here, boys. In the waiting room. Let me give you one more check over⌠Yes, you look great! Lucky Frankie. Sheâll be the first to see you in your pageboy outfits. Right, off you go. I have to go see Miss Poole. Remember what I said. Be very polite and well-behaved, wonât you?â
âWe always are,â remarked Bobby. âItâs the customers thatâŚâ
But Ellie was gone.
Miss Poole relied on Ellie for reports on the boysâ conduct. Monday mornings were a good time for her to get updated with the latest intelligence. Ellie knocked, and Miss Poole called her in at once.
âEllie, thank you for coming. Just give me a moment, would you? Iâve just asked to be connected to Deborah Cresswell about her wedding.â
A moment later the phone on her desk rang. âAh, hello? Is that Deborah? Good morning. This is Violet Poole from Pittâs Wood Equestrian Centre. Yes⌠Bobby⌠Thatâs right. Yes, heâs now our permanent resident boot boy. Yes, very exciting! Now I wanted to ask you, have you seen the photos I emailed of Bobby and his friend Timmy? You have? What do youâŚ? You do? Really? Both of them? Theyâll be so happy! Bobbyâs so looking forward to showing off his pageboy outfit, and Timmyâs been so jealous! I know. I know! Isnât it wonderful? Did you see the specs of their outfits from Fantastex? No, they really do. It is a little teeny bit naughty, of course but⌠Oh, Iâm so glad you approve! Yes, I know. They can be⌠Yes, quite dull. But a little bit of spice⌠I can see weâre on the same page. Now, I have to ask⌠The boys have a supervisor. Sheâs very nice, and very smart, in both senses of the word. Oh, she can? And she mentioned two attendants. Really? Sheâll be so pleased⌠Excellent, yes⌠Now I wanted to ask⌠Please say no if Iâm overstepping the mark⌠Apart from the in-house service, we are now offering home visits. They can not only attend to footwear, but any domestic duties. Sorry? Well of course Iâm using the term in its widest⌠Oh, yesâŚabsolutely anything. Parties? Of course. Well the thing is, Deborah, we are printing flyers in the hope we can reach a wider⌠I can? Oh, thatâs so good of you! No, Iâm sure some of your guests will be interested⌠And of course, Iâll give you vouchers in case you decide youâd like to visitâŚor be visited⌠No, no problem. Only too happy⌠Youâve been so kindâŚ. Yes, well, weâll speak again soon, Thank you again. Yes, letâs. Bye, Deborah!â
Miss Poole smiled. She loves them.. Theyâre both welcome, as are you, and your two friends. Now, Ellie⌠Any updates?â
âThank you, miss. May and Jessica will be pleased. Especially since they found out some things about the boys last night.â
âOh, really? Like what exactly?â
âLike Tim has a terrible crush on Bobby, and wishes he was a girl. And Bobby would like to be a girl â or at least, heâd like to wear girlsâ clothes. And he will do pretty much anything to please Timmy. And May and Jessica have the pair of them eating out of their handsâŚâ
âGoodness, stop right there, Ellie. Thatâs enough for me to take in a one sitting. So your surmise was correct. We have a pair of potential, dare I say it - sissy-boysâŚon our hands.â
âSeems so, miss.â
âI was hoping that would be the case. I wish all boys of that age could have at least an element ofâŚshall we say, feminine softness? And how are the new uniforms?â
âOh, amazing, Miss Poole. Those little plugs are so effectiveâŚâ
âHmm. Excellent. Cynthiaâs come up trumps again. Remember to turn them on for the wedding, wonât you? We want the boys to put on a good displayâŚâ
âOf course, miss. And for the time being May and Jessica are going to continue their, er, education. Iâll report any developments.â
âThank you, Ellie. You can always email me if thereâs anything you would like me to know urgently. And attach any visual evidence at you discretionâŚâ
âYes, Miss Poole â absolutely.â
âAnd I must tell Diana and Eleanor what youâve just told me. They have another session on Wednesday â donât give the boys any forewarning, will you? They also spotted a certain, ah, empathy between them, and I think they said they might push things a little further this timeâŚâ
Active Sissy Stories / Re: His Aunt Nicole
« Last post by Simonssister on September 09, 2025, 03:09:00 AM »
As their spasms gradually subsided and their bodies relaxed, they sank back on the sofa. Bobbyâs head slowly tilted sideways till it was resting on Timâs shoulder. Their erections were softening slowly, and from the tip of each condom hung a spherical teat heavy with c-um. The girls left them for a minute or two, then carefully removed the each one, pinching the end above the teat to conserve as much as possible while stretching open the lip and gently pulling it off. Giggling, they held them up to compare.
âNot much in it,â remarked May, in an undertone. âBobby I think. He may have lost the size competition, but he made up for it in quantity.â
âWhat are we going to do with these?â whispered Jessica.
The both looked at the inviting round lips in front of them, and smiled.
âItâs too good to waste,â whispered May back.
Jessica raised her voice again. âBoys? Stay where you are and donât move. You deserve a treat after that.â
She pulled out the mouth plugs and hooked the rings over her little finger. Jessica was about to feed Tim his own c-um, but May raised her finger. She held out Bobbyâs full condom and winked. Jessica grinned. Without a word, they exchanged condoms. They pushed the lips into the boyâs mouth holes, poking them in with their fingers, then, holding the teats up, used thumbs and forefingers to inject the contents into their mouths. Then they pulled out the condoms, Jessica passed May one of the plugs, and they popped them in.
âHands down, Bobby!â
The boys sat there obediently, presumably enjoying their little treats. The girls shook hands silently, then made the boys decent and refastened their shorts.
âWas it nice, boys?â teased Jessica. âItâs good for you, too.â
The blank pink latex hoods betrayed no hint of emotion. They looked so comic with their little plugged red lips, as if they were pouting for a pretend kiss. Bobby hands lay helpless by his sides. Tim was clinging to the frills on Bobbyâs shorts with one hand, the other in his lap.
âThey look so sweet now,â whispered May. âWhat cute little sissies! But that was some performance.â
âI think the hoods helped,â replied Jessica, quietly. âI think they help them lose their inhibitions. If so, it gives us lots of options.â
âYes, but letâs take our time.â
âTotally,â agreed Jessica. She looked down at Mayâs phone. âWe should finish the videoâŚâ
âOh, yes. Stay where you are boys, and weâll take off your hoods.â
The girls went round behind the sofa. âOpen wide,â said May, for the second time. They worked the tunnel gags out of their mouths, then simultaneously stretched the fronts of the hoods out and rolled them up off their heads. The boys sat there blinking in the light. May moved in front of the phone so they wouldnât see it, stopped the video, and slipped in into her pocket.
The boys were allowed to change into their casual clothes for the rest of the evening. When they emerged from their rooms they were very sheepish, unable to look at each other or the girls. Jessica and May had to coax them back to normality, to their usual confident, sociable selves. May fetched a ten-pack of beers from the fridge.
âCome on, guys, sit down and letâs have a drink. Are you okay? We didnât mean to hurt your feelings or anythingâŚâ
âOh, no, itâs nothing like thatâŚâ began Bobby, happy to see the girls werenât going to make fun of them. âItâs justâŚâ he glanced at Tim. Tim glanced back. âWell, it was kind ofâŚfunnyâŚâ
âLook, guys,â said Jessica. âHow can I explain? Weâd really like to be your girlfriendsâŚâ May nodded. âWe really like your company. Youâre good fun. But, well, to be honest, it would never be a âtypicalâ boyfriend-girlfriend relationship. Cos you know we have our own bondâŚâ
âYeah, we totally get it,â blurted Tim, âbut we donât care about all that. We really like you bofe â donât we mate?â It was Bobbyâs turn to nod. âSee we ainât ever âad no girlfriends before, so we donât âave no expectationsâŚâ
âWe like you partly because of that,â said May. âNeither of you pretends to be tough or macho â but actually youâre very brave and strong. Youâre confident enough to do this job, to wear whatever uniforms Miss Poole decides to give you. What blokes would be tough enough to do that? None that I know. But we canât do all the traditional sex stuff. We like to be a bit adventurous. And I can see you do too. It makes us feel good about ourselves when we see you accepting your own feelings for each other. See, we donât need constant emotional reassurance like a lot of girls. Weâre not going to play emotional games, weâre not going to stop liking you on a whim, weâre not going to look at other guys â though we may occasionally glance at another girl! â weâre not going to disapprove of anything you do. Provided you acknowledge your own feelings, as we do ours.â
âYes,â added Jessica, âand sexually all we want to do is to give you a good time, whilst enjoying ourselves. So far weâve only scratched the surface. So if you decided to stay with us, we can at least promise you some fun. I think this evening we started uncovering some rather interesting things about you twoâŚâ
Tim and Bobby blushed, and giggled like a pair of shy girls.
âAnd it was a fantastic turn-on for us. So thatâs one of the things we want to explore further.â
âYeah. A lot further,â said May, taking another swig of beer. âSpecially when Bobbyâs got his new dress. What was it, Tim? Blue satin with pink latex panties? You naughty boy!â
Tim hid his face in his hands. Bobby grinned.
âIâd really like one like that,â he said, giving Tim a poke in the ribs.
Active Sissy Stories / Re: Proof of Intent
« Last post by antonia on September 06, 2025, 05:20:59 AM »
James woke up feeling sore, he had a bad case of nappy rash beginning, not helped at all by the excessive rubbing to the front of his nappy on the previous day. His nappy was soaked, his bib wet from a night of drooling as he nursed on his dummy. His hand clutched tightly to the woollen shawl which he had caressed to his face and luxuriated in the fragrance the entire night.
The continual subliminal messaging had him unperturbed by the thought that he had wet his nappies during the night. He knew that his (do di) dummy and his (shoo-shoo) baby shawl were a vital part of his life and he would be very nervous if they were to leave his sight.
Lisa came in with a warm bottle of milk which he grabbed hungrily and began to suc-k vigorously on the bottle teat. As he enjoyed his bottle, she removed his wet and rather odorous nappy and threw it in the wet nappy bucket. In no time at all she had him in the bath and enjoying a happy time splashing and laughing as he played with a few bright yellow plastic ducks. She pulled the reluctant boyfriend out of the bath and carefully dried him off.
The special cream was applied generously to his little sissy stick which she could have sworn was already looking smaller that it had the day before. A heavy layer of zinc and castor oil cream was applied to his nappy area, with particular attention to the areas where small pimples were erupting in patches of redness where nappy rash was beginning to appear. The coolness of the cream induced a tumescence into his little member and Lisa smiles at how the erection was speeding up his downfall as the drugs were absorbed into his blood stream.
She decided not to use his plastic pants in an attempt to allow some air to get to his skin. She laid him in his cot on top of three night time nappies and loosely pinned two regular nappies around him to allow his skin to recover. James wanted to get out and was not cooperating, so Lisa put him in a fresh little smocked night dress and then put him in his reins, which she attached firmly to the restraining rings on the cot. Now he was lying on his back and unable to sit up or do anything other than stare at the ceiling. She picked up his unfinished bottle and he resumed his feed. He was asleep in ten minutes, legs wide apart, shawl against his ear and his bottle hanging out the side of his mouth.
The door bell rang and Lisa ran down to greet her new guest. A very smart tall girl stood before her dressed in the traditional Norland nanny uniform which was a pale grey/beige. Her hair was tied neatly into a bun leaving her features looking a little severe. She was dark haired with a gently tanned complexion and she was tall and slender. She looked athletic, here muscles were well developed and she clearly looked after herself, as well as she cared for her little charges. She paid her taxi driver, who had lined her suit cases in a row on the doorstep.
âCaroline Fortiscueâ she announced with a clear diction of a lady who had been well educated and came from a very good family âI am here to be the nanny to Jamesâ
âWonderfulâ enthused Lisa who was looking quite flushed and radiant from her dash to the door âI am so pleased you have decided to join me. James is in his nursery, he has had his wet nappy removed, been given a bath and put in a clean nappy, fed his bottle and is now having a nap. Let me help you to your room.â
Lisa took one of the cases and Caroline easily picked up the other two. The went up to the nursery and opened the adjoining door. Carolineâs new room was bright and airy, it had a comfortable double bed topped with a patchwork quilt. The bedside table had a baby monitor on its top which showed a green light. The sound of James suc-king on his dummy could be heard clearly.
In the room were ample fitted wardrobes, in the middle of which was the door that led in to the nursery. On the wall with the window was a small table that had two large packets of unopened terry towelling nappies, a pile of bibs in their cellophane wrappers, plastic pants of various colours, styles and sizes in plastic bags and several different coloured dummies also in their original packaging.
They dropped the cases and went through to the nursery. âHe has nappy rashâ confessed Lisa âso I am trying not to use his plastic nappy covers this morning. Good grief, I changed his nappy just ten minutes ago and he has wet himself alreadyâ she whispered with a slight giggle.
James was sound asleep, the nappies covering him were clearly yellowed by his wetting, but he was blissfully unaware as he suc-ked on his dummy. His freshly washed hair shone in the sunlight that came through the nursery window, his pink bonnet was hung over the corner post of his crib ready for use later.
Caroline explored the nursery, approving of the kitchenette and nappy changing facilities, and at the thought that had been paid to the storage of his babyish supplies and clothes. She wandered over to a door on the other side of the nursery and peeked inside. It was a sluice for dirty nappies and had a specially designed bathing area for a large baby. It was clear from the wet towels and disorder, that it had been used recently.
âLook, you get settled in and unpack your things and we will have a meeting this afternoon, once the other staff have arrived and are on board. I would be grateful if you could change the little one when he wakes up. I bet he will be thrilled to know that he now has a nanny!â said Lisa
Active Sissy Stories / Re: Proof of Intent
« Last post by sweet baby katie on September 04, 2025, 09:56:36 AM »
Active Sissy Stories / Re: Proof of Intent
« Last post by sissytrilly on September 04, 2025, 05:28:17 AM »

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