Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Recent Inactive Sissy Stories => Topic started by: Sandra B on December 06, 2021, 06:09:46 AM
-
I A Short Vacation
His name was Simon – Simon Nimmo - but his mother – and consequently the rest of his family – always called him “Simmy”, a name he had accepted when he was a little boy, but which now, at the age of twelve – (“nearly thirteen!” he protested) – he hated for its juvenility. He was in big school now, but a couple of his friends who had visited him at home had found out his secret and begun to tease him with it. He had begged his mother to call him Simon;
“Please, mum. When Jack and William come over for supper, please, please, remember its Simon…Simon, not Simmy…okay? Okay?”
“Yes, darling, I’ll remember. But I don’t know why you’re so sensitive…”
“You don’t understand…”
She didn’t, it was true. But she was as good as her word. Unfortunately, however, Simon had a sister a couple of years older than he, and Sinead – that was her name – took a certain delight in abusing her seniority, and liked to entertain herself by embarrassing him on any available occasion, and watching his face turn from its usual freckly fairness to a glowing scarlet, which it was capable of doing with remarkable quickness.
“All I said was I thought you’d look nice in a pair of my panties, and you turn as red as a beetroot! You must admit you’d make such a pretty girl, though!”
“Mum? Why does Simmy blush so easily? All I said was I thought he fancied my friend Imelda who was here yesterday and he coloured up like a traffic light. I guess maybe he does…”
“You’re blushing again, Simmy! Just because I asked you about those magazines I found under your bed.”
And of course she couldn’t resist forgetting herself in front of Jack and William.
“Simmy, darling? Sorry to interrupt, but we’ve just found the album with all your old baby photos in. Would you like to see?”
“I would!” shouted Jack.
“Me too! Can we…Simmy?” laughed William.
And so his fun evening with his friends was punctuated by half an hour of sheer humiliation, all courtesy of the evil Sinead.
It was undeniable that his friends had a little fun at his expense, but they were true friends, and the episode – and the pet name – got no farther than the house.
“Simmy?” William had said. “Why did she call you that? Imagine if I were called “Willy”, or Jack “Jackie”! I wouldn’t put up with it if I were you. I mean, you’re not six any more.”
“I know. I hate her!”
“But don’t worry…Simmy…it won’t go no further than here,” reassured Jack. “Your secret’s safe with us.”
“It’s no big deal, I suppose…but thanks, lads.”
And so things went on as before. Simon at school, but Simmy at home. And he had resigned himself to the minor domestic embarrassment. Then…it was the month before his thirteenth birthday when his mother announced she had to go abroad for a month for her work. She was a freelance translator and she had been offered an important job in Paris which she couldn’t turn down. So the children would have to go and stay with her sister until she returned.
“Don’t worry, Simmy. I’ll be back for your birthday, I promise. And you like your aunt Rosie, don’t you? She such a good cook, for one thing – be careful you don’t get so fat I don’t recognise you when I get back!”
Well, she was a good cook, that was true… thought Simon. But…how could he put it? There was something about her… That time when she had taken his sister’s word against his, and blamed him for spilling the paint, when it was that liar Sinead all the time… And once last year when they were staying there for a couple of days while mum was away, she had threatened to send him to school in a skirt, just cos he’d punched Sinead for teasing him… No, he wasn’t entirely sure of her… And she lived out of town, too.
“How am I going to get to school, mum? It’s too far to walk and it’s off my bus route.”
“Aunt Rosie has kindly offered to drive you, and pick you up every day.”
“It’ll be better for me,” said Sinead. Sinead attended a special girls school – St. Agatha’s – having won some sort of scholarship. She was clever. Too clever for her brother most of the time. There was a bus direct from Aunt Rosie’s to the school, and the stop was right across the road from the house. Moreover several of her friends lived in that area, so she’d be able to get the bus with them.
“It’ll be fun for me, instead of always travelling by myself.”
“Not for me, though. I’ll miss my mates. And I don’t much like the way Aunt Rosie drives.”
“Nonsense, Simmy! She a very good driver. Very careful.”
“Too careful. She hardly gets out of first gear. And I know her - I bet she’ll insist on kissing me when she drops me off, like I’m a little kid!”
“Well, well, if she does, so what?” said his mother, impatiently. “She is your aunt, after all. Just be a good boy and be nice to her, Simmy. I’ve told her she will be in complete charge of you. I won’t have time to sort out your problems. But I’ll call and speak to both of you every day.”
Simon frowned. He had an unpleasant foreboding about the whole thing…
-
Oh the possibilities!
-
I too have a bad feeling about this, but mine is based on all the sissy stories I've read. No clue where Simmy's sense of foreboding is coming from!
-
II Aunt Rosie
Rosie was the elder of the sisters, now in her early forties, and strong-willed enough that her junior Margaret had always let her take the lead. She had had one daughter, Stephanie, who was now away at university, and she had lived alone during term time for the past couple of years. She was tall, with an intelligent, open face and blue eyes, and wore her dark hair in a short, neat, youthful style. She looked fit and flexible – she may have been a nervous driver, but she was a fearless horsewoman, and had been something of a gymnast in her youth – and was not the sort of person to engineer a disagreement with, either physical or cerebral. She was, in short, undeniably attractive. Margaret was inclined put down her solitary state to two causes: a distrust of men generally, arising from the unfaithfulness of her husband, who had left her for some scatty blonde five years before; and the difficulty of finding one to equal her own spirit and energy. In any case, Margaret was not concerned; her sister seemed very happy, and she had noted with pleasant surprise that she had a couple of close friends of her own sex, to whom she seemed very attached.
So she was quite relaxed about letting her sister take the kids for the month. It had been Rosie’s suggestion, in fact, when she heard Margaret had been offered a short contract abroad. She was very fond of Sinead, whom her daughter had taken under her wing at school – they were both at St. Agatha’s together – and she was interested in Simon, whom she had seen less often, but about whom her sister frequently talked. She had the impression that, as he was growing up, he was becoming more of a handful. And she flattered herself that her superior strength of will may be able to guide him back to the straight and narrow path.
Margaret dropped the children off on a sunny Saturday morning at the beginning of June, on her way to Paris. She had decided to drive, as she would be likely to need to use a car to get to and from her place of work, and she didn’t want to rely on taxis. So along with her own suitcase, there was one for each of the kids and a present for Rosie. The luggage unloaded, the farewells said, she kissed all three of them goodbye, exhorting Sinead and Simon to be well-behaved and obedient to their aunt. Then she was gone.
“Welcome to my home, guys,” smiled Rosie. “Come on in and I’ll show you your rooms. Sinead, you know your way about, don’t you? But Simon, it’s a long while since you visited. I’ll give you a guided tour when you’ve got unpacked.”
The house was set back from the road, and the front garden was raised on a bank, with a big hedge all along the front. She led them in through the front door and up the stairs. At the back of the house, overlooking the lawn, were two adjacent bedrooms with the doors open. The one on the left was furnished in plain greens and greys, the one on the right a riot of different shades of pink. Naturally, Simon headed left.
“Oh, no, Simon. This one is yours.” Rosie indicated the pink room.
“That one?” He looked startled.
“Yes…well, you see, that is my daughter’s room, and when Sinead used to stay, of course she always had the one next door. So I thought she should keep the room she’s used to. I hope you don’t mind.”
“Too bad if you do,” piped up Sinead, with a laugh. “You’ve got the girl’s room, Sim, with all those lovely pink furnishings. I think they’ll suit you perfectly. Match your cheeks when you blush.”
Simon glared at her, and was about to say something rude, but thought better of it. He wheeled his case into the pink room in a huff.
“Come down when you’re ready, Simon,” said Rosie, “and I’ll show you round. Here, Sinead, let me help you.” Sinead had her case and a separate bag. Rosie took her case and let the way into her room. She closed the door.
“Do you think he minds? I didn’t mean to embarrass him. It’s just a room, after all.”
“No, auntie, he doesn’t mind. He likes girly stuff anyway.”
“He does?” Rosie raised her eyebrows.
“Oh yeah. I used to put makeup on him when he was younger. And put him in a dress. He liked it…at least, I think he did. Now he’s bigger he pretends to be so macho. Shows off to his little friends, all that - you know what they're like.”
Rosie wasn’t sure she did, but thought she could imagine.
“Oh, yes…I suppose all boys go through that phase. It’s not very healthy though, I don’t think. They lose sight of their feminine side.”
Sinead was delighted she was buying into it. “Yeah, that’s it. Mum would be so grateful if you could influence him, I’m sure. I think she has a tough time. When he swears at her and stuff.”
“He swears at her?” Rosie was horrified.
“Oh, yeah. And he’s cheeky, and won’t do what he’s told. He’s not bad, really. Just a bit…misguided. You could help, though. I think mum’s a bit soft on him, really.”
“Is she? Well, I’m not soft, Sinead. In view of what you’ve told me, I’m going to keep a close eye on that little brother of yours.”
“Oh, will you, auntie?” Sinead’s blue eyes widened with innocent gratitude. “That’s so nice of you.”
“Right, well, I’m going down to prepare dinner for tonight. You both like shepherd’s pie, I believe?”
“Yum! Your shepherd’s pie, auntie, is my favourite.”
“Good. See you in a while, then.”
“Oh, auntie?”
“Yes?”
“One thing. At home we always call him “Simmy”. He says he doesn’t like it, but he does. Makes him feel little and protected. He just doesn’t like his friends hearing, that’s all.”
“Oh, right. Thank you Sinead.”
As she closed the door, Rosie made a silent resolution. That Simon...Simmy...was going to learn some proper manners while his mother was away. Whatever it took. Behind the door, Sinead, eyes dancing, covered her mouth, suppressing a malicious snigger.
-
Well! Seems like Sinead is quite the mastermind here.
-
For an intelligent and self-reliant woman, Rosie seems to be easily led. Guess it's due to her inherent distrust of men. Looks like Simon is in for a bumpy ride.
-
III Soft Deceitful Wiles
So when Simon appeared in the kitchen half an hour later, himself slightly wary of the mystery that was his aunt, Rosie was a little curt with him. He didn’t notice, because he didn’t know quite what to expect of her, and because her curtness was of the mildest possible kind. She hadn’t made up her mind about him by any means. She had so little knowledge of young boys – her daughter’s boyfriends - (she had met only two) – were older, of course, and astonishingly mature and confident. Perhaps she expected early manifestations of the same brashness in Simon, but it soon became apparent that the seeds hadn’t even been planted yet. On the other hand, she trusted Sinead implicitly, she having been so close to Stephanie – almost like a sister. So she trod warily.
“Simon…Simmy…I hope you didn’t mind going in Stephanie’s room. I know it’s horrifyingly pink, but…”
“I don’t mind. It smells nice.” He looked at her suspiciously. “Why did you call me Simmy?”
“Why? I..er...I thought that’s what you preferred now…I mean, I think your mum usually calls you Simmy.”
Simon sighed. “Yeah…she does.”
“Don’t you like it?”
“I’m nearly thirteen.”
“Oh, of course…yes, you are, aren’t you. All right. It’s Simon, then.”
“Or Sim. My friends usually call me Sim.”
“Oh…Sim…yes.”
He was looking around the kitchen. Rosie took the opportunity to have a good stare at him. He seemed perfectly fine. Bright. Outgoing. Well-adjusted. Yes, quite mature in fact.
“This is an amazing kitchen.”
“Oh, yes, I suppose it is. It’s not very old.”
“So many cupboards! Are they all full of food?” He looked at her hopefully.
She laughed. “Well, not all of them. But there is lots of ice-cream in the freezer. If you like ice-cream, Sim.”
“You bet.”
“Well you can help yourselves after the shepherd’s pie. Now, why don’t we talk about the things we could do this month. I’ve got some ideas…”
She sat Simon at the kitchen table and gave him a drink, while she busied herself preparing the shepherd’s pie for the evening, and making a salad for lunch. They chatted away happily. He seemed a delightful kid. She would have to speak to Sinead again when she had the chance.
A few minutes later Sinead herself stuck her head into the kitchen. She could hear how well the two of them were getting on, and she didn’t like it.
“Simmy? Wanna come and play a game? There’s like a million board games in the living room cupboard.
“Not right now, Sinead. I’m just talking to aunt Rosie. We’re planning some pretty cool trips too.”
“Oh, come on. We can all discuss that together at lunch. I really want to play this Dungeons and Dragons game now.”
“Oh, okay. I’ll be with you in a moment.”
When he went into the living room, Sinead already had the board on the table, and was organising the counters. He sat down opposite her. She looked up mischievously.
“So, how’s your pretty girl’s room?”
He refused to take the bait.
“It’s fine. I like it. The bed’s so comfy.”
“Uhuh. You’d better not mess it up, that’s all.”
“I’m not going to mess it up…stupid.”
“Or start looking in Stephanie’s cupboards.”
“Looking in her cupboards? Why would I do that?”
Her voice dropped to a whisper. “All those pretty clothes…dresses…shoes…” She paused. “Panties…”
“Shut up.”
“If you want to know – I bet you do – the top drawer is her panty drawer. She’s quite slim…I bet some of them would fit you…you’d like that, wouldn’t you?”
“Shut up.” A little louder now.
“Do you remember when I made you wear my panties…? Of course you do. I know you like them. Your little thing went all…”
“Shut up!” He shouted. “fuc-k off! fuc-k off you fuc-king bitch!”
“Simon!”
Aunt Rosie had appeared at the door. “What is going on?”
Sinead feigned tears. “He swore at me again. He’s always swearing at me…and mum.”
“It’s her fault. She was saying…” His voice trailed off.
“What was she saying?”
“...Nothing…”
“So that was why you called her…what you did, Simon?” She put her hands on her hips. “I think you’d better go up to your room until you’ve cooled down. And then you can come down an apologise to your sister.”
Simon thrust back his chair and ran out and up the stairs, his eyes filling with tears. Real tears. Not the crocodile ones Sinead was wiping from her cheeks.
“Round one to me,” she thought.
-
That settles it. Sinead is wicked, but will anyone realize it before it's too late for Sim?
-
Sandra B,
I am enjoying your story. Sinead seems to be a master manipulator and seems to have Aunt Rosie wrapped around her little finger.
I'm eager to read more of the perils of Simmy.
-
IV Capitulation
Simon sat on the soft pink bed, his eyes shiny with tears, his mouth turned down, and an injured frown on his face.
“Why doesn’t she just leave me alone?” he asked himself. “What’s her problem? It’s not normal. She should be out with her friends. Why is she doing this to me? All right, it’s true, I did used to let her dress me up…and in a funny way, I suppose I did enjoy it. In those days I wanted her attention. Now…I wish she’d just fuc-k off. fuc-k off and let me lead my own life.”
That’s exactly what he wanted to say to her. “fuc-k off and let me lead my own life.” He looked up, and caught sight of his reflection in the wardrobe mirror. He looked so sulky and bad-tempered, and so highly-coloured, with his gingerish thatch and his red cheeks and eyes, he had to smile in spite of himself. He sat there a little longer, staring blankly at his reflection and being reflective at the same time. “It’s true, though. She is weird. Maybe I do have a bit of a thing for girl’s stuff” – he couldn’t bring himself to say “clothes” – “but that’s okay, isn’t it? I mean, I’m not the only kid who feels like that. But I reckon I am the only one whose fourteen-year-old sister could be bothered to torture him about it. So I’m not going to get all guilty and stuff. She’s the one with the problem, not me.”
If only Rosie could have heard the words going through his mind at that moment, her heart would have melted, not only with sympathy, but with respect. But she couldn’t. And though she was ready to give him the benefit of the doubt, and felt there was something not quite right about Sinead’s behaviour, she felt she had to insist on maintaining discipline. Nevertheless, she was pleasantly surprised when a much calmer Simon returned downstairs and addressed himself to his sister in the following terms.
“Sis, I’m really sorry I swore at you. I didn’t mean any harm. Please accept my apology.”
Then he turned to his aunt.
“Aunt Rosie, I apologise to you, too. I know it’s not an excuse, but I haven’t settled in properly yet. It feels like a sudden change, and I think I’m gonna miss mum quite a bit. I hope you understand.”
Rosie was quite taken aback at such a sincere and mature apology.
“Simon…well, thank you for that, darling. I quite understand. It must be difficult…for both of you. Let’s forget all about it now, and start fresh. Come and give me a hand with lunch, and we’ll talk about some of the things we can do while you’re here. And after dinner we’ll ring your mum, yes?”
At lunch, Simon seemed quite relaxed, and chatted happily with his aunt. He had decided this had to be the way forward. He guessed correctly that his sister was trying to goad him into bad behaviour, and was determined not to be manipulated by her. Sinead, however, was chagrined by the way he had turned things around, and was already thinking of ways to trip him up – though right now she felt she was definitely on the back foot.
The rest of the day passed off uneventfully. They played some games, planned a couple of trips out, and hung around in the garden. It transpired that Sinead was going out early the next day to meet her friends, which intelligence made Simon very happy.
After dinner they called their mum. She was in her hotel now, and excited about her trip. Nothing was said about the events of the day. They retired to bed sometime after ten. Simon went for a shower, and was met by his sister on the way back to his room.
“Bet you think you’re a right smartarse, Simmy,” she hissed, “suc-king up to aunt Rosie all day.”
“I wasn’t suc-king up. She’s all right.”
“Yeah? She doesn’t know you yet. But she will.”
Simon pushed past her, and went into the bedroom. He was delighted to find the door had a lock and key, which he turned with a grunt of satisfaction.
“I won’t be seeing any more of you for a while, anyway,” he thought. “Think I’ll have a lie in tomorrow till you’re gone.”
He put on some clean boxers, climbed under the soft duvet, and lay there, thinking about what he could do on Sunday. Jack and William would be about. He could go see them. He turned out the light, and started thinking about the things Sinead had said to him that day. The curtains were open, and moonlight streamed into the room. He couldn’t go to sleep.
“Mess up her room…why would I do that? Go through her clothes…huh. So, now I know the top drawer is her panty drawer…big deal…”
He lay there a little longer, quite still and silent.
“I bet it isn’t. I bet she was just trying to wind me up.”
He lay there, sniffing and scratching his nose, and fidgeting, turning from one side to the other.
“Why not? I bet she was joking. Why shouldn't I? No-one will know, anyway.”
He turned on the light again, and slipped out of bed. The chest was on the corridor side of the room, next to the wardrobe. He sauntered over. As softly as he could, he began to ease open the top drawer. It opened with a protesting squeak. Immediately his nostrils were assailed with a sweet perfume. She hadn’t been joking. It was stuffed full of panties. Panties of every colour and fabric. He stared for a minute, holding his breath. Then he began, very gingerly, to delve into the piles, to explore the forbidden recesses of Stephanie’s underwear. Pastel pinks, blues, yellows. Smooth satiny ones, ruched ones, lacy ones, frilly ones. And stockings! And suspender belts, with rubber clips and stretchy straps. And even a garter or two!
His heart was beating faster now. He really shouldn’t be doing this. He would have to be careful. No-one must know. He mustn’t mess up the piles. But he couldn’t resist…
He took a pair from the top. Quite plain, except for a little bow at the front. Yellow. Shiny. Very stretchy. He eased the drawer shut – another squeak – and scurried back to bed. He'd just hold them. Maybe put them on the pillow. They smelled so nice. They’d help him sleep.
But the temptation was too much. It took him no more than two or three minutes to decide. He crept out again, slipped out of his boxers, and slipped into the panties. They fitted surprisingly well, taut but comfortable. He admired himself in the wardrobe mirror for a minute or two, turning this way and that. He thought they looked pretty cool, and they felt...wow! Girls were so lucky! Then back into bed, turn out the light, and sleep. Sweet, peaceful sleep.
Which would all have been fine. Would have been, if next door Sinead hadn’t been listening, one ear pressed to the wall. When she heard that squeak – a sound she was only too familiar with – she knew he had succ-umbed.
“If only I could see in there!” she groaned. It was so frustrating.
She peered out of her window. She could see the light from Simon’s room flooding out onto the sill. The curtains were undrawn, then. She grimaced with annoyance. But suddenly she froze, and her face cleared as quickly as the sun appears from behind a cloud. An idea. A long shot, but… She went to her case, threw out some of her clothes, and found…her selfie stick! With trembling fingers she attached her phone, and turned on video mode. Then, opening her window as wide as it would go, she leant out and slowly extended her arm till her phone hovered outside Simon’s window.
“Oh my god,” she murmured. “I hope he is up to something in there…something he shouldn’t be!”
-
This might be the first story I've read where a selfie stick is a plot device! Sim's in trouble now, but which way will it go? Will Sinead show their aunt or just blackmail "Simmy" herself?
-
V A Shopping Expedition
Simon fell asleep quite quickly, but his slumber was anything but peaceful, punctuated by a series of vivid and torrid dreams. He didn’t wake till almost ten. He was so dazed he actually forgot he was wearing Stephanie’s panties until he got out of bed. Then he quickly got organised, changed into his boxers, and headed for the shower. He had a long shower and washed the panties at the same time. He returned to his room, secreted the panties behind the radiator to dry, dressed, and made his way downstairs. The house was very quiet. Clearly Sinead had departed long ago. Looking out of the kitchen door, he could see aunt Rosie at the end of the garden, cutting some flowers. She’d left his breakfast on the table. He sat down and ate, and called up Jack.
“Hi dude. What you doing today?”
“Nuffin’.”
“Shall I come round?”
“Yeah. Any time. William’s got to do some stuff for his mum. He’ll be here after lunch.”
“Okay. See you in a bit.”
After breakfast he had a chat to his aunt, and at about eleven thirty crossed over the road and waited for the bus. He got to Jack’s about twenty past twelve, and spent the day just hanging out with his friends. He was back at Rosie’s by eight – he had some homework for the next day – and Sinead walked in about half an hour after him. She seemed in a very good mood.
“Good day, Simmy?”
“Yeah, good. You?”
“Great. Florence has just moved to a new house, and me, Amy and Tessa went to her house-warming.”
“Nice place?”
“Amazing. It’s got a basement which her parents are going to let her have for her room. It’s one huge room, as big as the footprint of the house. There’s not a massive amount of natural light, but she’s already painted the walls cream and pale green. She says we can use it as our clubhouse.”
“Nice!” Especially if that means you’ll spend less time at home, he thought.
“So what did you do?”
“Oh, you know, just hung out. Nothing special.”
“You were still asleep when I left.”
“Yeah, well, that bed…”
“Simmy…aunt Rosie gave me some money today.”
“She did?”
“Yes. Remember I helped her with the gardening last month?”
“Oh, yeah. You were round here every day for a fortnight. I remember.”
“She’s given me two hundred pounds.”
“Wow!”
“I’d like to spend a few quid on you. Do you fancy a little shopping trip tomorrow?”
“Shopping?”
“Yes. I thought you could do with a new hoodie. Maybe a T-shirt too. We could go to the shopping centre after school.”
“Okay. That’s nice of you.”
“No probs. We can meet there. Find you something special…”
Brother and sister met at Middenwell Mall at five that Monday evening. Sinead took Simon’s arm, and led him straight towards one of the biggest clothes shops there.
“Now, Simmy, first things first. Underwear.”
“What? I’m not letting you buy me underwear, sis! You're joking.”
“Not at all. I’m going to get you something a little more…adventurous. More decorative.”
“Shut up, idiot! You said you were going to buy me a T-shirt, and a hoodie.”
“Oh, I am. Don’t worry about that. But look, here we are.”
“This is the kids’ section. What are you up to?”
“I told you. Let me do the talking. But go along with everything I say, understand?”
“No, I don’t.”
“Well let me help you then.”
She took out her phone, and a moment later Simon received a WhatsApp message. He pulled out his phone and opened it. He thought he was going to faint. There was a video, a video of him taking off his boxers and putting on Stephanie’s shiny yellow panties. Then admiring himself in the mirror, until eventually he turned toward the camera with a big smile on his face, not to mention other testimony of his obvious contentment. He stared at the video, played it again, and looked up at Sinead aghast.
“How did you…?”
“Selfie sticks are a wonderful invention, Simmy.”
“What are you going to do with it?”
“Nothing – as long as you’re a good boy, and do what you’re told. You’d better play your part well, or else…”
“Or else what?”
“Or else this little film will be on its way to aunt Rosie…and maybe to Jack and William too. Yes, I got their numbers off your phone.”
“No, please….Sinead…you wouldn’t…”
“You know I would, darling. All you have to do is to play along. Agree with everything I say. Got it?”
Simon was struck dumb.
“Got it?”
“Y-yes, got it…”
“Good. And be polite. And smile. Go on, smile. That’s it. Perfect.”
Sinead was totally without inhibitions. She went straight up to the nearest assistant, dragging Simon by the hand, looked her in the eye, and said,
“Excuse me? I’m looking for some girl’s panties for my brother. I’m not sure of his size.”
The assistant’s mouth fell open. For a moment she was too astonished to speak.
“Pardon?”
“Girl’s panties. For my brother here. Something pretty. Simmy? You like Hello Kitty, don’t you?”
“I-I…er…”
“Don’t you?” Sinead fingered her phone.
Simon looked despairing, but he got the message. “Oh, er…yes…Hello Kitty…my favourite.”
The assistant had recovered by now. Her astonishment had been replaced by a conspiratorial smile. “We do have Hello Kitty ones, yes. Follow me please.”
“Will you need to measure him? He’s twelve. Nearly thirteen, actually.”
She laughed. “No, I can tell exactly what size he’ll need, just by looking at him. That's experience. Now, here we are. They come in packs of three. Pink with little pussy cat faces.”
“They’re so pretty! Aren’t they, Simmy?”
Simmy’s whole face was aflame. “”Y-yes, they are…”
“Are what?”
“V-very pretty…”
“Do you have anything else he might like?”
“Oh, these ones are new, but they’re really cool. I’m going to get some for my daughter. See? They have this glittery stuff actually in the fabric. They sort of sparkle when you move. They come in packs of three too, one pink, one yellow, one blue.”
“Oh, Simmy, they’re great, aren’t they. Would you like a couple of packs of these?”
“Er…”
“You would, wouldn’t you? I can tell…”
“Y-yes please, Sinead.”
“Good boy. So we ‘ll have two packs of each, for now. Thank you.”
“Thank you, madam! I do hope you enjoy wearing them, sir.”
Sinead paid, and then headed for the tops section. She selected a couple of girl’s ruffle T-shirts, one yellow, one pink, a pink sweatshirt, and a peach-coloured hoodie, holding them up against him to make sure they would fit.
“Better to have them on the large size,” she remarked. “Last longer then.”
As she was paying, poor Simon stood there helplessly, the picture of humiliated misery. But he was powerless to object. And Sinead was not quite finished yet.
“Now, Simmy, do you know what else that have in this store? They have a personalisation service, where you can get your name – or anything you like – printed on your clothes.”
“I know what you’re going to do! You’re going to have “Simmy” printed on this stuff, aren’t you? So that everyone knows what you call me!”
“No, darling, not at all. Would I do something like that? Course not. Here, take your new panties, and go and get yourself a coffee.” She pointed at a nearby coffee bar. I’ll see you there is a short while.”
He went into the coffee bar, got himself an Americano, and sat down. The whole thing was a disaster. She had him firmly in her grasp now. He would have to do anything she demanded. He daren’t allow that video to fall into the hands of his friends – or anyone! And now he suspected he was going to have his name emblazoned all over his new girly clothes. Shit! What an idiot he had been. But then, who would have suspected her of such devious behaviour?
In twenty minutes she was back.
“I’ve had them all done. While I was waiting I went to the footwear department and bought you some trainers and socks too. They had to letter the back of the hoodie cos of the front zip. But I think that’s just as good. What do you think?” She held up one of the T-shirts. “Cute, eh? The lady suggested a couple of hearts after she’d done the first one. After I told her they were for my brother.”
He read the words with horror. Four lines of bouncy letters: “I’M WEARING MY FAVOURITE LITTLE GIRL PANTIES!”
-
Never let it be said that Sinead doesn't understand subtlety! 😂
I can only imagine the reactions he'll get wearing his new things!
-
VI Photo Session
“Put it down, for goodness sake!” he pleaded. A girl at the next table had seen, and, between giggles, was repeating the inscription to her friend.
“Okay, Simmy. Don’t be so sensitive! If you’re like that now, imagine how embarrassed you’re going to be when you’re out in town wearing it.”
“Sinead, please…”
“Please what?”
“Why are you doing this to me? You must really hate me.”
“You don’t get it at all, do you?” She sighed. “All right. I’ll explain. I’ve known Florence for years. You know that. When we were little girls, I really envied her. Know why?”
Simon shook his head.
“Because she had a kid sister. Susie’s four years younger than her. She used to get to do loads of girlie things with her. We used to play together so happily for hours. I used to wish I could have had a sister instead of you, my boisterous little brother, with your boisterous little friends. I know, it was wrong. But that was why I was always putting you in girls' clothes, and when I saw you actually liked it, I can’t tell you – I was so happy. I just wanted you to be my own little girl for ever. But you rebelled. Eventually you rebelled. But I don’t think you rebelled because you didn’t like our games. I think you were worried about your friends finding out. You still are. But now I’m taking charge. As long as you play along, no-one else need know – unless you decide you want them to.”
“Are you serious? No-one can know, Sinead. I’d be finished.”
“Well, that’s not true, actually. It wouldn’t be the end of the world, as you seem to think. But anyway, don’t try to rebuff me this time, or you can expect some unwanted publicity.”
“But these tops you’ve had made…”
“Just a bit of fun. I may make you wear them as a gentle warning in case you become disobedient. For now, though, they’re our little secret…”
“Except from the next table!”
“Our little secret, Simmy, and tomorrow, when Rosie’s out, I want to take some pictures of you wearing them.”
“Why? Why do you need to do that?”
“Just because… Because I enjoy seeing you blush, and fidget with embarrassment. I get a kick out of watching you go all shy and sulky. And maybe I want a poster for my wall…”
“No!”
“Now, now, little boy. Behave yourself… Or you never know what might happen…”
Simon looked as though he was going to cry. Sinead stroked his cheek.
“You’re so sweet when you’re like that. It gives me a funny feeling inside…”
All the next day, at school, Simon was feeling anxious. Jack noticed at once.
“What’s up, mate? You feeling all right?”
“Yes, Jack. It’s nothing. Bit of a stomach upset.”
“Okay. You look like shit, that’s all.”
That was a great help, thought Simon. He imagined if Jack ever saw that video. He had to block the idea from his mind.
He got home at four-fifteen. Rosie was out at a meeting of the garden society. Sinead was waiting.
“Ready?”
“Ready for what?”
“You know. Now put on your best jeans and your new hoodie first. These are the new trainers I got you. Wear those as well.”
“They’re pink.”
“You have amazing powers of observation. Get ready please. And hurry up. Then come into the garden. It’s lovely and sunny this evening, plus I want a nice background of flowers and bushes.”
When Simon reappeared at the garden door, Sinead had already set up her camera on a tripod. She fancied herself as a bit of a photographer.
“Over here. Stand right there. That’s it. Now smile.”
Simon grimaced.
“Smile, I said. Smile. Look happy. Relax, Simmy, for fuc-k’s sake. That’s better. Yeah, you look cool. Stick your hands in your pockets. Right. Now turn around and look over your shoulder so I can see your confession.”
“Yeah, well I’m not, anyway.”
“Not what?”
“Not wearing my panties.”
“Little girl panties, if you don’t mind. And you will be, very soon.”
After the hoodie came the sweatshirt.
“Now this time I want you to point to the words, Simmy. Go on, point. You want to make sure everyone sees what it says. That’s it. But keep your head up. Better… Now pout a little. Pout. You know what that means. Yes…yes…good…”
She was snapping away now. “Good boy, that’s really good…you look so cute!”
Finally it was time for the T-shirts.
“Right. I think we’ll use the yellow one. Now listen. Take off those jeans and change into a pair of your new yellow panties. You’ll find some long lemon socks on the sofa. Put those on. They should look great with your pink trainers. Then your yellow T-shirt. And hurry up please.”
“But…my jeans…”
“No jeans. I want to see panties and only panties. Get a move on.”
When Simon emerged from the house Sinead bit her lower lip in delight.
“Back to where you were, little boy.” She watched him reluctantly making his way across the lawn. The shop assistant had been right. Those panties did sparkle in the most delightful way. She switched to video. Stills could wait for now.
“Pull your socks up to your knees. I want them symmetrical. Good. Now, first of all, pose with you hands behind your back. Not like that, idiot. Loosen up. Relax. That’s better. Sway your hips a bit from side to side. I want to see those pretty little panties sparkling in the sun. Yes…yes. Now…pay attention. With your left hand, point at the words. Good. With your right, put a finger to your mouth, like a naughty little girl who’s been discovered stealing cakes from the cupboard. I can see I don’t need to tell you to blush, do I? Oh my god…”
Sinead’s exclamation was drawn from her by Simon’s unconscious behaviour. He was actually squirming with embarrassment, his bare thighs pressed tightly together, his feet turned slightly in, for all the world like a self-conscious little girl.
“This is going to be the fuc-king best,” she murmured under her breath; and out loud, “good - very good, Simon.”
He noticed the “Simon”, and was so grateful he actually summoned up a nervous smile.
“Now, you can take your hand from your mouth – no, keep pointing at your shirt – take your hand from your mouth, and take the hem of your panties between finger and thumb – yes, like that – and just pull it off your thigh – just an inch or two. Show how nice and stretchy the material is, and what a sweet boy you are…and how much you love your new panties…yes…perfect…”
Now she was snapping away with her phone while the video camera did its work. “I’m going to have fun editing this,” she said to herself.
By now, Simon was beside himself with confusion. The sun was bright, and it was shining into his face and getting him overheated at the same time. The lining of his snug little panties was incredibly smooth and slippery, and he could feel his body beginning to respond. He was only too painfully aware of what an embarrassing sight he must present. He bit his lip, and peeped down at the modest but noticeable bulge in the yellow satin. He could feel it uncurling itself and inching slowly along the left leg-band. He began to fidget involuntarily, shifting his weight from one foot to the other, his thighs rubbing together, but it simply made things worse. Sinead was quite aware of his predicament, but had no intention of relieving it.
“Is the sun in your eyes? It is, isn’t it. Stay right there. Don’t move. You can put your hands down, silly. Stephanie used to have a collection of baseball caps. I’ll go and find one.”
When she returned, holding a pink cap with the word “Princess” embroidered on it, it was obvious nothing had changed. Simon was standing on the same spot, his hands clasped modestly in front of him, looking very uncomfortable. Suppressing a smile, she went over and put the cap on his head. It went very well with the rest of his outfit.
“Sinead? How long is this going to take? It’s so hot out here in the sun.”
“I know, darling. Nearly finished. Just a few minutes, and we can go inside and have a drink.”
She returned to the camera. She had let it run while she’d been away.
“Okay. Now turn around and give me a back view. Hands in front of you. Look over your shoulder and smile at the camera. That’s it…so cute! Now back again…this time pinch both hems with your fingers…smile...pull a little…”
Eager to finish his routine, he tugged too hastily. The sudden stretching of the fabric precipitated such a frisson of pleasure, that he couldn’t suppress an audible gasp.
“Ooh, careful, darling…gently now…”
“Good. Now a little curtsey… You can curtsey, can't you? I showed you when you were about nine. That’s right. Now stand up straight. Face the camera. Your last pose - for this session at least. Big smile. Right. Now say, “I hope you like my new little girl panties. I love them so much.” Go on.”
Simon hesitated. “Go on. Then we can go inside.”
“I hope you like my new little girl panties. I love them so much.”
“Say it like you really mean it!”
“I hope you like my new little girl panties. I love them so much.”
“Better. Once more.”
“I hope you like my new little girl panties. I love them so much.”
“Good. Excellent. Now, “if I had a little girl skirt too, I could wear them always, and look so pretty...”
Simon was so desperate to be released from this torture, that he said the words with what sounded like real enthusiasm. Sinead turned off the camera, went over, and gave him a hug and a kiss.
“Maybe I’ll buy you a skirt, if you’re good. But you were incredible, Simon. You’re a natural at photo sessions.”
Stupidly, he felt flattered. “Am I?”
“Yes! Now come and have a drink.”
They went inside and Sinead served lemonade in the lounge. They sat on the sofa and she turned on the television. She noted with great satisfaction that her brother seemed quite content to sit there with her in his girlish outfit, and showed no signs of wanting to get changed. Sinead felt triumphant. Tomorrow she would edit the video and the photos. She had plans for them. But today she would enjoy the spectacle of her brother, dressed up at last almost as she used to have him years ago.
-
The quick updates are so wonderful because I am so excited to see what Sinead's plan is. I do think Simon/Sim/Simmy wants to wear girly things, that much is clear, probably more than he's willing to admit to himself, but Sinead's plan almost certainly is too much of a good thing for him. I'm just hoping that she's not too cruel. She's putting forth a front about caring about her brother and only wanting him to be true to himself, but these thoughts about editing and the suspicious phrases she had him say worry me and make me think there might be something more malicious in store for him.
-
VII A Surprise
Sinead prepared supper, and half an hour before Rosie was due back, she led Simon upstairs to his room, and helped him find a shelf in one of the wardrobes where he could keep his new clothes. Then she turned to him.
“I suppose you should put your jeans on before auntie gets back. You can keep your new panties on if you like. It’s up to you.”
“Okay…” He grabbed his jeans and slipped into them.
“So…what about a skirt, then? Perhaps you’d feel more comfortable if you had one to wear.”
“A skirt…?”
“Well, as long as I have control over when and where you wear panties, I was just thinking you may feel safer if there’s the option of having a skirt as well.”
Simon considered, glancing at her sideways. Was this another trick, or… But surely, it would be good to have an option…even if it were her option.
“Okay…I suppose…”
“Good. We’ll pop back to Middenwell after school tomorrow, as see if they’ve got anything suitable. We can find that nice lady who helped us with your panties.”
Simon immediately turned red.
“Sinead…let’s get one online…I don’t think we need…”
“No arguments, Simon. You can wear your sweatshirt to let her know you’re wearing your panties. Which you will be, as you’re going to wear a pair to school tomorrow.”
“No!”
“Yes. You will wear the Hello Kitty ones under your jeans. I’ll check before you get in the car. I won’t mind if you decide to give your friends a peek.”
“Shut up!”
“Seriously, though, there shouldn’t be a problem. There’s no clothing rules at your school. Now, if it were St. Agatha’s, with their fetish about the uniform, you might have cause to be worried. I’m sure they’d love to check our knickers, too, if they were allowed.”
“Serves you right for going to a posh school.”
“It wasn’t really my choice. Now, tonight. I’ll bring your sweatshirt, and you can put it on when we get there. Don’t worry, you can wear your jacket over the top, and unzip it when we’re in the shop. I want her to know you’re happy with what we bought.”
“Suppose someone at school sees them…”
“That’s your problem. I suggest you keep your jeans pulled up, instead of half way down your hips, like you usually have them.”
Simon groaned, and was about to argue, when they heard their aunt returning. So further discussion was precluded.
That evening, Sinead retired to her room early, to work on her editing. As for Simon, he was feeling so anxious about the next day, that he decided to have an early night. He vacillated about what to wear in bed, but eventually threw aside his boxers and the pyjamas his mother had put in his case, and chose a pair of the cool, blue sparkle panties, as a sort of comforter. He fell asleep in a confusion of feelings, and dreamt he was at school wearing Hello Kitty panties with a very short, lightweight flared skirt, which kept blowing up in the wind.
Sinead was occupied until after one o’clock in the morning. She reduced the stills to twenty or thirty of the best ones. Her favourite was from the last session, in T-shirt and panties. Like all the best photos, it had been taken in between formal poses. It showed her brother in mid-squirm; his right leg was straight, his foot flat on the ground; his left bent, the thigh pressed coyly over the right, the trainer vertical, the toe pressed against the side of the other trainer. His cheeks were bright red, and he was peeping out self-consciously at the camera from under the peak of his “Princess” baseball cap. He had one finger to his mouth still, but his left hand had crept down to his panties, apparently with a view to gauging the precise status of his arousal, and the picture had been snapped at the exact moment he had taken the main focus of his embarrassment delicately between finger and thumb!
Sinead gave a little whoop of delight. “Shit! How did I manage to get that one?” She exhaled slowly. “That’s going to be difficult to keep to myself. I’m going to have to show Florence. She’s going to be beside herself.”
Florence had been an accomplice to Sinead’s earlier efforts to feminise her brother. They had had a lot of fun in those days, which they sometimes reminisced about. They were close, and Florence was totally trustworthy, so it was unthinkable that she should be excluded from Sinead’s current project. Her main reason for editing her material so carefully was to give Florence a treat – a private showing. And it was definitely going to be private. Their other friends, Amy and Tessa, would have to be excluded permanently…well, for the time being, at least.
The video footage was even more hilarious. Behind the forced smiles and poses, Simon’s acute embarrassment was obvious, manifested in blushes, a reluctance to look at the camera, and continual fidgeting.
“This is priceless,” remarked Sinead. “Florence is going to wet herself laughing… What’s this…? Oh, I remember…when I went to get his cap…yeah…now what’s he up to…? Why, what a rude little…! Well, well, when the cat’s away, the mice will play…with themselves, apparently… I suppose it shows he’s really into those panties.” She hit the keys. “Right, young man. This little episode we’ll keep by itself. I think I can say with absolute certainty that this” – she hit the save button hard – “this will guarantee your compliance with whatever duties I assign to you. Yes…that makes me feel a lot better. He’s not seeing this. He can have a copy of everything else, but this? This is going to be kept in reserve in case of emergencies…”
-
There's so much to unpack here! Simon's sneaky little moments during the photoshoot, Sinead sharing with her friend, Simon's growing sissy wardrobe. Lots of fun ahead, though I am a little worried about Sinead's trust in her friend. These things have a habit of getting out.
-
VIII Conspirators
In the matter of the Hello Kitty panties, Sinead was as good as her word. She normally left for school a few minutes after her brother, so she was able to check he had obeyed instructions. He had, and he had also pulled his jeans right up to his waist and tightened his belt.
“Good boy, Simmy. Now don’t forget – meet me at the mall this evening, same time. Cheer up, kid. Maybe they’ll help you concentrate.”
“Seriously?”
“Yes. Why not? I’m sure they feel more natural to you.”
“Come on, Simon. We need to go.”
“Coming, auntie.”
At break time at St. Agatha’s, Sinead drew Florence aside.
“Florry. What are you up to Friday?”
“Nothing special. I thought you and the others would be coming round. Why?”
“I need to have a private meeting with you.”
“Sounds interesting. What’s on the agenda?”
Sinead checked they were alone. She took out her phone and showed her friend one photograph of Simon in his yellow T-shirt and yellow panties. “This is.”
Florence’s mouth fell open. “Sim? When was that taken?”
“At the weekend.”
“Sinead! How did you…?”
“Get him back in girly stuff? He slipped up, that’s all. And I took advantage.”
“You’re a genius!”
“There’s more. You’ll want to see it. I’ve got him eating out of my hand. And I’ll tell you what. He’s not completely averse to it. All that training we gave him when he was younger seems to have paid off.”
“What? He’s actually into it?”
“I think so, underneath all that shyness and embarrassment. But he’ll need careful cultivation. And I thought you might be willing to help.”
“Willing? I’d be delighted, darling. Please, please let me help!”
“I thought we might all meet up one day next week. After you’ve seen the evidence.”
“Yeah! Let’s! Bring him round to my place one evening. Tell you what, bring him Friday and you can both can stay over. My room will all be fixed up by then, and I’ll have a camp bed as well as the double.” She paused. “What does he actually have to wear? That old stuff won’t fit any more, will it?”
“So far not much. I’m taking him to get him a skirt tonight.”
“What about stockings, tights, shoes? And have you tried using makeup yet?”
“No, no, it’s early days. I was thinking he could be our long-term project.”
“Great! You know I’ve got piles of clothes which are too small for me now. You don’t really need to get him anything for the time being – not until he develops his own tastes a bit more!”
“I hadn’t thought of that. Dressing him in your clothes sounds quite exciting. It felt funny thinking of using mine, being family, like. Yeah, great idea.”
“So you’re going shopping for him tonight?”
“Yeah.”
“Can I come?”
How could she refuse? When Simon saw Sinead and Florence waiting for him at the mall his heart sank. It was now a conspiracy. Sinead was holding a carrier bag. He knew what was inside. He slouched over to them, hoping there were none of his schoolmates anywhere near to ask questions.
“You’ve told Florence, then. Thanks a lot.”
“I already know all about you, Simon,” replied Florence, with a meaningful smile. “Nothing you get up to now would surprise me.”
“I’m not getting up to anything. It’s her.”
“Well, let’s not argue. Sinead invited me because I’ve got good taste, that’s all. If you’re going to get yourself some new gear, you need me along. Right, Sinead?”
“Absolutely.”
She pulled Simon’s pink sweatshirt out of the bag.
“Here. Get this on. I’ve already been to check - your girlfriend’s waiting.”
He took the folded-up sweatshirt. “I’ll put it on in the toilet.”
“Don’t be an idiot! Do it over here, in the corner. We’ll stand around you. No-one’s going to notice.”
He hesitated, but the girls looked so determined he wilted under the power of their will, and allowed himself to be shepherded to the corner. With a sigh he took off his coat and handed it to Sinead. Florence looked at it disdainfully.
“Boys’ clothes today…” She shook her head. “They’re so…drab. Look at that thing – like a dirty olive green. I’m surprised all little boys don’t want to dress as girls – wear something a bit more colourful.”
Simon knew inside that Florence had put her finger on it. He hated the dark, depressing stuff that was available. If it wasn’t black, it was navy, or dark green, or camouflage. Yuk! It was at least one reason why he was drawn to girls’ clothes – they could be colourful, exciting, flamboyant. But he wasn’t about to confess that to his chaperones. With a look up and down, he pulled the sweatshirt over his head, worked his way into it, and pulled it down until his head popped out of the neck. He was alone. The girls had disappeared. He was seized with panic.
“Where are you?” he screamed. “Sinead! Florence!” The unfortunate result of his panic was that everyone within earshot turned to look at him. With horror, he realised their eyes were drawn to the words on his chest. A middle-aged lady nearby was squinting at them, and suddenly burst into hysterical laughter. At the same time he caught sight of his tormentors, peering round the door of the clothes shop. Sinead waved.
“Over here, Simmy!”
He needed no second bidding. Trying to cover his shirt with his hands, as if in a religious gesture, he ran towards them.
“Give me my coat!”
Sinead, clutching the coat, evaded him.
“You can have it back when you’ve asked your girlfriend about your skirt,” grinned Sinead, keeping her distance and getting ready to run off again if necessary. Simon hesitated, but the prospect of chasing his sister round the shopping centre with everyone staring at him didn’t appeal a great deal, so he summoned up his courage and headed for his “girlfriend”, the two girls following at a safe distance. The assistant was in her twenties, with short, dark hair and bright red lipstick. She had a measuring tape draped around her neck, and was folding shirts on the counter.
“Excuse me,” he began, “I…”
“Oh, hello,” she interrupted, “how nice to see you. How are the…”
She had caught sight of the legend on his sweatshirt, which he was trying ineffectually to conceal.
“What’s this…”I’m wearing my favourite…”” Her face lit up. “Oh, sir, are you really? I do hope they fit you nicely. How clever of you to let everyone know!”
“Hello,” said Sinead, coming up. “How are you?”
“I’m well, thank you. Even better now I know those pretty panties are your brother’s favourites! What can I do for you today?”
“Simon? Tell the lady what you’re looking for.”
Simon turned his brightest shade of red.
“Oh, yes, please tell me, Simon. Do you want some more panties, perhaps?”
“No…no, thank you. I was, er, wondering if, maybe…”
“What he’s trying to say is, he wants a pretty little skirt to go with his pretty little panties, so he can flash them at all his friends,” smirked Sinead.
“Shut up, Sinead! That’s not what I was going to say!”
“Oh, but sir does want a skirt, is that right?”
“Yes…maybe…”
“Please follow me, and I’ll show you what we’ve got.”
He trooped after the assistant, the girls bringing up the rear.
“Look at his ears,” whispered Florence. “They’re redder than his cheeks!”
She led them to a long rack of girls’ skirts. She slipped off the tape.
“Any of these are suitable for a twelve-year-old.”
“I’m nearly thirteen, miss, you know…”
She ignored the comment. “I’ll need to measure your waist. Hold up your shirt a moment. Thank you…right…oh, you’re wearing your Hello Kittys! They are cute, aren’t they?”
Florence spluttered with laughter.
“Now, what do you think would suit him, ladies? Have a look through this section. Any of these with blue markers will fit him.”
The girls dived in and began to riffle through the rack, occasionally taking one out for further inspection. Helped by the attentive assistant, they whittled their choice down to two: a very short flared skirt in shiny red lame, and a crisp, pleated, high-waisted tartan mini-skirt. They decided they were definitely going to take those.
“It would be nice to have one more,” said Sinead, but I think that’s our budget…”
“Tell you what,” said the assistant, “if you’re taking those two, I may be able find something amongst the old stock which we’re returning, and throw it in. Let me go and have a look.”
She was back in a couple of minutes.
“I’m so sorry, there’s nothing in his size. The only thing I could find was these, if they’re any use.” She held up a pair of tiny, yellow lycra hot pants, quite plain apart from waist and leg bands. “It says ten to twelve, but their very stretchy. Take them if you think they’re any use.”
“No,” cried Simon.
“Yes! Thank you so much, miss. I’m sure they’ll be perfect.”
“Please, Sinead…”
“Do you want your coat back, Simmy?”
“Yes, I do.”
“Then accept the nice lady’s offer.”
Simon frowned. “Thank you. You're...very kind.”
“Good boy. He does want them. He just a little shy sometimes. I bet he’ll want to come back and show you how cute they look.”
“Oh, that would be so nice, if he did. I hope the skirts suit him, too. I’ll pack everything up for you.”
As the three of them left the mall, Florence put her arm around Simon.
“Sim…it’s so nice to spend time with you again, like we used to. You and Sinead must come over for a meal, and maybe stay over. I’m free next Friday week, if you can make it…”
“I’m not sure, but thank you anyway.. “
“Of course we’re free, Florry. Thank you.” interrupted Sinead. “Simmy, wait till you see Florence’s new room - you’ll love it!”
-
I can't speak for Simon, but I'm very excited to see Florence's room
-
IX Florence’s Room
Sinead and Simon took the bus back to Rosie’s house. Florence also headed home. On the way she called up Amy.
“Amy. Hi. Look, something’s come up. Can we postpone Friday for a few days?”
“Sure. What’s happened?”
“Oh, nothing… Er, mum’s asked me to help her with something…”
“With what?”
“Oh...” She had to think quickly. Why was Amy always so nosey? “…She wants me to…help her choose some clothes for my cousin…we’ll have to go to several shops…”
“Okay. That’s disappointing. Me and Tessa were looking forward to seeing your room now it’s fixed up. Maybe we can make it the Friday after.”
“Ah, well, I’m not sure what’s happening then… Let’s talk about it later this week…”
“Hmm. Sounds like something’s going on. Not that guy you were talking to at the bus stop, is it?”
“No, no, nothing like that…you know…just family stuff…”
“Okay. If you say so. See you then.”
And she put the phone down abruptly. Florence snorted with irritation. She had obviously pissed off her friend, as well as making her suspicious. But it couldn’t be helped. The Simmy project had to take first priority.
Simon was relieved when Sinead announced she’d be going to Florence’s on Friday and staying over. He immediately asked his aunt if Jack and William could come round, which he wouldn’t have dared to do if his sister had been there as well. Rosie was only too happy to accommodate his friends, to take his mind off his mother’s absence. Simon, in his innocence, never imagined Sinead’s visit was connected with anything other than the new room.
After school on Friday, two girls hurried back to Florence’s house together. Florence let them in. Her parents were still out at work. The little door to the basement was at the back of the house, under the stairs. Florence produced a key, and winked.
“There are only two keys. One is for you. We have total privacy.”
“For me? Really? Your parents let you have the only two keys? That’s pretty cool of them.”
“Ah, well, there were three…but the third one got unaccountably lost when I threw it out with the rubbish. They think it’s in the kitchen drawer, but what they don’t know won’t hurt them.”
“I see…”
“Come on. Tell me what you think.”
They entered onto a small landing, and Florence locked the door behind them and flipped a switch, turning on two strip lights which ran almost the whole length of the room. They descended. The room itself, which must have measured about twenty metres by twelve, had been transformed since Sinead’s earlier visit. The floor was tiled, and there were three or four brightly-coloured rugs strewn about. On three sides, at ceiling level, were long, narrow awning-style windows of frosted glass, operated by handles lower down on the walls. The walls themselves were painted a uniform pale green, and decorated with framed posters. The right-hand half of the far wall was taken up by an enclosed bathroom, with a built-in wardrobe on its left side. In front of that, on the right-hand wall, was a dressing-table, and opposite, on the left-hand wall, a double-bed. The staircase ran diagonally down the near wall, and beneath it was a large triangular cupboard or room with a tiny square frosted window and a low door, in the lock of which there was a silver key. In the near half of the room were armchairs, a sofa, and an old plain oak table, and on the left wall a counter and sink with a fridge and a stove. On the right, next to the cupboard door, was a desk and laptop.
“Wow, Flo! There’s everything you need here! You could live down here quite happily. It’s like your own personal apartment!”
“That was my idea. When my dad mentioned he didn’t know what we were going to do with the basement, I claimed it straight away. In fact, I designed it… At least, I drew a plan of where I wanted everything. His mate is a builder, and he came and did it all in a few days.”
“You are so lucky!”
“These stairs and the cupboard were already here, of course, and so were the radiators, but the floor was just concrete and the walls needed plastering. It’s almost finished. Bill – the builder – is coming back on Tuesday just to finish off the bathroom, and in case I think of anything else that’s needs doing.”
“It’s amazing.”
“Well it’s yours as much as it’s mine. Remember how much time I used to spend at your house when we were younger when we were all living in that tiny flat? I’ve always been grateful to you and your mum for that.”
“No, it was fun. The best time of my life.”
“Anyway, we share it. That’s the deal. Here's your key. Come here whenever you want.”
“Where will Simon sleep when he stays?”
“I think we should put him in the cupboard – the cell, as I call it. But no, there’s a folding bed in there which we can get out.”
Sinead was still exploring. “Gosh, nice bathroom. Shower and everything.” She had a sudden thought. “What about Susie? Has she been down here?”
“A couple of times. Course, she’s desperate to stay down here with me. But she’s not allowed, unless I agree. Don’t worry – I’ll let her come down sometimes, if she's good. But she's into absolutely everything.”
“I know just what she’s like.”
“But Sinead…what about…you know?”
“The evidence! Yeah. Turn on the computer.”
Florence sat down at the desk and put on a pair of rather severe wire-framed glasses. She had dark curly hair and a pale complexion, unlike her friend who shared her brother’s light brown, verging on ginger, hair.
“Pull up a chair,” she said, and, with a grin, “show me what you got!”
“This is for you, anyway,” said Sinead, handing over a flash drive. “Let’s go through the photos first.”
As Florence scrolled through the pictures of Simon, he mouth fell open, and then she was seized with a fit of the giggles.
“Sinead! These are…how can I put it? Hilarious! How on earth did you manage to get him to pose like this? I mean, suppose one of his friends saw them.”
“Carry on. You haven’t come to the yellow panties ones yet. That’s it - these.”
“Shit! These are crazy all right! Those little panties are so tight…I mean, they don’t leave much to the imagination, do they?”
“Wait till you see the last one. Here it comes.”
Florence gasped. “What did you do to get him to pose like…like that?”
“I didn’t. I was just snapping away, and I caught him in mid-fondle.”
“Fuc-k it. I thought the one you showed me before was pretty hot. But this one...!”
“I agree.”
Florence stared at her. “You know what…with this stuff…I mean, the possibilities are endless…”
“Wait till you see the video.”
Sinead had kept back the most incriminating footage. Not even her best friend was going to see that…for the time being at least. But the rest was enough to make Florence ecstatic.
“Sinead. This is amazing. Look at him squirming. You know why he’s so embarrassed? Cos he knows it’s perfectly obvious that he simply loves his little panties! He wants to protest, to resist, but the panties have made him helpless. He’s already a natural sissy!”
“That’s all true. All we have to do is to continue his training, till eventually he gives in and accepts it. Then we’ll have a cute little boy-girl to play with. Maybe one day we could let her join our club. Anyway, that’s exactly what I want - what I’ve always wanted. A lovely little sissy girl for a brother, who I can dress up and boss around.”
“It’ll be just like before, except better! We’ll dress him, and spoil him, and cajole him, and flatter him, until he won’t know who or what he is. And if he tries to resist…”
“If he shows the slightest sign of resistance, out come the photos, or the video.”
“He doesn’t have a chance.” She paused. “Has he seen this stuff yet?
“Not yet. I was thinking I might give him a copy, to remind him to behave.”
“No, don’t. Not yet. Let’s show him when he comes over next Friday. I want to see his reaction.”
Sinead laughed. “Good thinking, Flo.”
“And what about Amy and Tessa?”
“What about them?”
“Do we let them in on it?”
“Let’s keep him to ourselves for the time being. If anyone outed him, deliberately or accidentally, it would be game over. We wouldn’t have any leverage any more, would we?”
“I guess not…”
Except for my special video, of course, thought Sinead, with a self-satisfied smile. But Florence didn’t notice. She was already making plans for the following week…
-
Simon has no idea how trapped he is. Not yet, anyway
-
X A Few Modifications
As Sinead was cunning and devious, so was Florence inventive. They shared the double bed that night, and Sinead was awakened at six in the morning by her friend tugging at her shirt.
“You awake, Sinead?”
Sinead grunted.
“Listen, I’ve been thinking. I’ve had a few ideas. Tell me what you think.” And she began to hypothesize. Sinead was quickly awake, and paying attention. Finally she spoke.
“I thought I was the one with the twisted mind…”
“It’s not twisted – just imaginative. Bill can do anything – he’s not a bad painter either.”
“No, he made a good job of the walls…”
“You know what I’m talking about! He could do it, no problem. He doesn’t have to be sodding Constable – if it looks like a stage set it’ll be all the more amusing.”
“And he’s a carpenter too?”
“Of course. That’s his main trade. That'll be simple for him.”
“Sim’s going to need some more things, then…”
“Let’s take him back to the mall straight after school Friday. There’s a toy shop there too.”
“He’ll love that.”
“Well it doesn’t matter what he thinks. This is our project, Sinead. He’s just assisting.”
“You make it sound like he wants to be involved.”
“And you know what else? I’d forgotten, but I’ve still got my first uniform from when I started at St. Agatha’s. I was as big then as Simon is now. I’m sure it would fit him.”
“That’s a brilliant idea.”
“I’d have to get the skirt shortened, of course. That was under the old regime – remember Miss Carson? “Below the knee, girls, please, and no higher!” Remember?”
“Only too well. Thank goodness the place has lightened up a bit now. But the skirt…”
“I’ll take it to the dry cleaners. We’ll need to decide how short, of course…”
They looked at each other and chuckled.
“Depends if we’re going to take him to school with us, I suppose,” laughed Sinead.
“I’ll measure the red one we bought and have it made the same length.”
“Hmm...maybe an inch shorter?”
“Okay.”
When Sinead got to school Thursday morning, Florence was waiting for her.
“Bill’s done everything. Will you be able to pop round quickly tonight and have a look?”
“You bet!”
They started giggling again. But their excitement did not go unnoticed. Their two friends were observing them from a distance.
“Those two are up to something,” said Tessa to Amy.
“Yeah. And it’s something they don’t want us to know about. Florence has blown off Friday again.”
“We need to find out what it is. Let’s follow Florence after school tomorrow. See what she gets up to.”
You’re on. I’m Holmes, and you’re my sidekick, Doctor Watson.”
“No way! I suggested it - I’m Holmes!”
That evening, Florence and Sinead caught the bus which would take them to Florence’s new house.
“I think you’re going to like what Bill’s done, Sinead.”
“I can’t wait to see it.”
At home, Florence let them in and they hurried to the basement door.
“Don’t look till you're downstairs,” said Florence, switching on the lights.
“Okay.”
They descended, Sinead keeping her eyes on her feet. At the foot of the stairs she stepped into the room and looked around. She screamed with delight.
The bathroom and built-in wardrobe occupied the right-hand corner of the far wall. The other corner had been transformed. On the back wall, and on the side wall, Bill had painted a mural of the seaside. There was yellow sand, turquoise sea with white surf, and above it a blue sky with puffy clouds and seagulls. On the horizon were a couple of sailing boats, and on the side wall a boy building a sandcastle. Sinead was aware of another mural on her left as she hurried to see it – a garden, with flowers and a tall green hedge. But the seaside was the one that really caught her interest. When she got closer she saw the whole thing.
“That’s so clever, Flo! You didn’t tell me he was going to do all this!”
Running between the corner of the wardrobe and the wall, Bill had fixed a wooden beam about a foot high, painted yellow. And the shallow box that had been created from the beam, the side of the wardrobe, and the walls, was filled with lovely yellow sand, blending into the sand on the mural!
“Like it? She flipped a switch, and the scene was lit up by a small floodlight high on the wall.
“It’s fantastic.”
“Imagine Simmy there, with his bucket and spade. We can get him those tomorrow when we’re at Middenwell. Now look at the other one.”
“You were right. He is a very good artist.”
“He is, isn’t he? It’s just a fairly ordinary garden scene. I asked him to make both of the murals big enough to form the background to any photos we might want to take.”
“I can see he likes tulips. It’s great. But the seaside one…that’s incredible.”
“Now, Sinead, look over here.”
She directed Sinead’s attention to a low, oblong wooden platform, like a box, against the wall to the left of the desk. It was about a foot high, two feet wide, and a foot and a half deep. It looked like varnished oak. In the very centre Bill had screwed a small steel plate and staple.
“That platform's fixed to the wall. It won’t move. We can put him up there, run a chain through the staple and padlock it to his ankles, and he’ll have to stay standing there as long as we want, like a living statue.”
“Oh my god. That’s so clever. And you’ve got the chain and everything?”
“Everything, yes. And if you look over on the opposite wall, you'll see a spotlight we can use to light him up. And around the walls, I also got Bill to put up a few mooring rings, so we can tether him up wherever we want to.”
Sinead stood back and looked around the room. “Honestly, Florence, I’m shocked. I had no idea you had such a flair for stagecraft and, well, bondage!”
“Well now you know. And there’s one more thing.”
“Yes?”
“You know those girlie magazines you found under Simon’s bed?”
“Yes. I brought them round here. We had a good laugh over them. You said you were going to dump them.”
“Well, I didn’t. I meant to, but I hid them under my wardrobe, and then I forgot about them. I found them again when we moved.”
“And…?”
“Follow me.”
She walked over and unlocked the door of the little room under the stairs – the “cell”. Inside was a camp bed, a bedside cabinet, and not much else. She turned on the light.
“Oh, shit! Florence!”
“I took out all the best pictures and pasted them onto the walls.”
“You’ve wallpapered the whole room! There’s not an inch of empty space! It’s…indecent!”
“There’s a few mags left – they’re in the cabinet. If he starts misbehaving, we’ll lock him in here with all his rude pictures. He won’t be able to look anywhere without seeing tits and bums!”
“…And the rest… It’ll probably drive him crazy…”
“It might. Or he might like it. We’ll find out, won’t we? There’s a bolt on the inside, so he can shut us out if he chooses.”
“Doesn’t sound like much of a punishment…”
“No. But we’re not into punishing him, are we?”
“No Flo, you’re right. We’re into playing, not punishing.”
“Quite.”
“I can’t wait for tomorrow. Let’s hope they have some pretty swimwear at the shop.”
-
XI Spies
Sinead waited till Friday morning to tell Simon the bad news.
“Simmy, darling, can you meet us at the mall again after school please? The usual place.”
“What? No! What do you want to go there again for? I thought we were s’posed to be going straight to Florence’s!”
“You’re so ungrateful! We just want to buy you a few more things, that’s all! Honestly, we spoil you, we really do.”
“Not going!” he shouted, sounding for all the world, Sinead thought, like a sulky eight-year-old.
“Oh, really? You’re not going. All right. No problem.” She took out her phone.
“What are you doing?” There was a note of anxiety in his voice.
“Nothing. Just sending a couple of pictures…”
“No! All right! All right – I’ll come to the stupid shop!”
“Are you sure? I mean, I really don’t mind… It would sort of be fun to see what Jack thought of your…”
“I said I’ll go!” He made a fishy mouth. It’s not fair, though. Please don’t make me see that lady again…”
“Well, she may not be there. Who knows? Anyway, Florence will be pleased. She’s had an idea for something you might like.”
“What?”
“Oh, I can’t say – it’s a surprise…”
After school, Florence was waiting for Sinead by the front gates of St. Agatha’s. And from a safe distance, Amy and Tessa were watching her. They saw Sinead running across the playground to join her friend. Then both headed off towards the bus garage. Amy and Tessa followed.
They had been doubtful of being able to follow Florence, without her realising, if she got on a bus. So they were relieved when their quarry went and waited at the stop for buses to Middenwell only. They were frequent, so they were able to take the next, and only be a few minutes behind. Even so, they were going to need luck.
“We’ll never find them once they get inside that place,” remarked Tessa, as they approached their destination. It gets insanely busy on a Friday night.”
“Yeah. And they must be inside by now. We’re at least ten minutes behind them.”
However, as the alighted from the bus, they were surprised to see Sinead and Florence standing together only twenty yards away. Fortunately they were so engrossed in conversation they didn’t see their friends, and they were able to dart behind the bus shelter, whence they awaited developments.
“What are they doing?”
“Waiting for someone.”
“Wonder who?”
“Wait…it’s Sinead’s little brother…”
“Simon?”
“Yeah, Simon. Now they’re all heading off towards the mall.”
“Let’s go. We musn’t lose them.”
Holmes and Watson kept their distance and kept well hidden amongst the shoppers. Sinead and Florence hurried purposefully forward, with Simon lagging slightly behind. When they entered their favourite shop, their pursuers took up positions each side of the main door, and watched them through the glass. They headed straight for an assistant with short, black hair, in the children’s section.
“Hello, guys,” she said with a big smile. “What can I help you with this time?”
“Hello…what is your name, miss?”
“I’m Alison. I know Simon, and I know you’re Sinead, but I didn’t catch your friend’s…”
“Florence,” piped up Florence. “Hello, Alison.”
“Hi. Simon, have you tried those pretty hot pants on yet?”
Simon instantly turned red and looked at the ground.
“Not yet,” grinned Sinead. “We’re saving them for the right occasion. Today we’re looking for swimwear, though.”
“Swimwear!” Alison’s face lit up. “Great! We have some very pretty things. One piece, or…?”
“Maybe a one-piece, and a bikini as well,” suggested Florence. “It depends what you have.”
“Follow me, guys. We have quite a good selection.” She led them deeper into the shop, to the very back of the girls’ section. Outside, Amy and Tessa were squinting through the glass, but they had a very restricted view.
“We need to get closer,” hissed Amy. “Come on. Keep your head down.”
They crept through the racks of clothes till they were as near as they dared, and crouched there, peeping over the rows of hangers.
“What are they doing?”
“Hold on. They’re…looking at swimwear! Is that all? That’s boring. And why do they need the boy with them?”
“They probably have to look after him for the evening. I know Sinead’s mum’s away, and they’re staying with their aunt.”
“Watch out! Sinead’s coming this way!”
“Hide! Here!”
Sinead passed by only a few yards away.
“I’ll follow her,” said Amy. “You stay here and see what happens – if anything.”
Amy followed Sinead to a nearby toy shop, and watched, puzzled, as she selected a child's bucket and spade, made of soft red plastic. Then she returned to the clothes shop. Amy sneaked back to her friend.
“Well?”
“Florence has bought some stuff. I couldn’t see quite what, but it looked like some kids’ swimwear – like a couple of one-piece swimming suits and a bikini.”
“Sinead bought a bucket and spade.”
“What?”
“Yeah. I know who they’re for.”
“Who?”
“They must be for Florence’s sister. Susie, is it? It’s probably her birthday, or for her holiday or something.”
“Right… Well that was boring. Come on, let’s get out of here before they see us.”
And Holmes and Watson departed, feeling somewhat deflated.
“It’s weird, though,” said Tessa, on the bus back into town. “I don’t understand why Florence is wasting her Friday evenings doing stuff like that. I really wanted to spend time with her in her new room.”
“Me too. It feels like she’s deliberately excluding us. If she doesn’t invite us next week, I think we should gatecrash.”
“Good idea, Amy. We are part of the club, after all.”
-
XII Uniforms
Sinead and Florence, on the other hand, were very excited by their expedition. They sat together on the bus to Florence’s, with Simon in front of them. Florence kept stroking his hair, because she knew he hated it so much.
“Stop it, Florence! Stop doing that! It’s annoying!”
“Is it? I thought you liked it.” And she started playing with his ear, much to the amusement of two middle-aged ladies sitting opposite – the type that fawn all over girls and babies, but think all boys are naughty and need to be regularly disciplined – which made Simon even more upset.
Sinead meanwhile couldn’t resist pulling the swimwear out of its bag and admiring it.
“Good choice, Flo. I love this rainbow lycra one-piece. It’s so shimmery – all the rainbow colours sort of ripple when it moves. He’s going to look so cute. And the pink one! I love those little frilly yellow wings around the legs, and the “Girl Power” logo.”
“Take a look at the bikini. The top is tiny – but then, he’s got nothing to hide, has he?”
“Yes, I see – narrow little triangles of yellow satin. He may have a problem keeping his nipples covered. And the bottoms! I’ve always liked tie-side bikinis. And I really like how they’re ruched – they look really pretty.”
“Yes. Alison said these were the best choice. The ruching will give him a bit of room, and the legs are quite tightly elasticated, so nothing will be able to escape.”
The women (who naturally had been listening to every word) were staring now, looking from Simon to the swimming costumes and back again. The nearest one covered her mouth and gasped.
“Are they really for…” And she pointed rudely at Simon, who turned red and stared out of the window.
Sinead, who was a bit miffed at their noseyness, replied “maybe..,” in a tone that said the intrusion was unwelcome. Florence was slightly more forthright.
“Mind your own beeswax, missus…”
They were not sorry to get off the bus and get to Florence’s. They went straight down into the basement. Florence put a “Do Not Disturb” notice on the door, and locked it. She had told her parents she would have guests staying over and that they’d look after themselves. Simon followed them slowly down the staircase, looking around the room open-mouthed. For a moment he even forgot the threat of the humiliations to come.
“Wow! This is amazing! It’s huge! This is all your room, Flo?”
“Yes, darling. Like it?”
“You’re so lucky! What are these big paintings on the walls? And there’s a sandbox!” His face fell. “Oh..,” he said, flatly, as the true significance of it slowly dawned on him.
“Yes, Sim – I am lucky. But I’m not going to keep it to myself. Your sister has a key too. And if you’re good, I shall let you and your friends use it now an then.”
He brightened up at this. “You will?”
“I will. But you need to be good. You know what I mean.”
“I don’t have any choice, do I?”
“None at all,” said Sinead. “And this evening we’re going to show you why. Now, we’re both in our uniforms, and I think it would be nice of you were too.” She took off her rucksack and unzipped it. “Here. I’ve brought some of your panties over, and Florence has got a little present for you.”
From the wardrobe, Florence produced her old school uniform, and from her bag, her old school skirt, suitably abbreviated. “Go and change in the bathroom. No, leave the shoes and socks and the jacket here. Put them on when you come out.”
“Which panties would you like, Simmy?”
He sighed. “It doesn’t matter.”
“Choose…”
“All right. The blue ones.”
“Good choice. Match the uniform.”
He returned after a couple of minutes, in his crisp white blouse with the rounded collar points, striped tie, and little pleated tartan skirt, that barely covered his panties. He presented himself for inspection, Sinead noticed, as if seeking approval. She may have raised an eyebrow, but she was careful not to react in any way that might spoil the moment. Florence experienced a mild surge of motherly tenderness as she held the blazer for him. Then she sat him down and helped him on with his long white socks and black school shoes. She too noticed that for the first time he wasn't looking displeased. She had set up a free-standing full-length mirror against the cell wall, and invited Simon to look at himself, which he did without demur, straightening his hair with his hand and then vainly trying to pull his little skirt down onto his hips; but it remained stubbornly belted around his waist.
“My panties are showing, Flo…”
“They’re not really. It’s only because that mirror is at an angle, so when you look down you’re looking up your skirt.”
“Oh…”
“You look very pretty.”
He turned to her and almost smiled! That was the first time that Sinead had entertained the faintest hope that her project may one day reach a successful conclusion.
“Now come on, Sim. Sit down on the sofa with us and we’ll show you the photoshoot you did with Sinead,” Florence continued, reassuringly. I’ll put the laptop on the coffee table. There. Now, would you like to see the photos first?”
“Okay.”
He paid close attention to each one.
“You look very nice there, I think,” said Florence.
“Yeah…” replied Simon, doubtfully. “I don’t mind the hoodie itself…I mean, it’s a nice colour…but I can’t wear it out, can I? Not with that on the back. Or the sweatshirt, or the T-shirt.”
“Why not? A lot of people will think you’re just having a joke, and those that take it at face value will probably think how brave you are to tell everyone.”
“Maybe…that’s what Alison said, too.”
At last they came to the series of Simon in his yellow panties and T-shirt. Florence looked across at Sinead, and she gave an almost imperceptible shake on the head. Florence knew what that meant; skip over that final picture. Even so, Simon was frowning as Florence scrolled through them. But she and Sinead kept up a very matter-of-fact commentary, in an attempt to minimise Simon’s embarrassment.
“The yellow of the T-shirt suits you so well, Sim,” remarked Florence, approvingly.
“It does,” agreed Sinead, seriously. “It goes with his sunny complexion.”
“And his sunny nature!”
Simon smiled. He was more relaxed now. Florence hadn’t even commented on his panties. Maybe it wasn’t such a big deal after all. The school uniform was comfortable, and it felt good to have his legs open to the air right up to his crotch. He sighed. He felt he wouldn’t have minded at all if he’d been born female.
The video might have been more of a problem, had not Florence put her arm around him and given him a squeeze.
“Simon! Look at yourself. You look great! What are you acting so shy for? I mean, it’s kind of cute, but…”
“Yes, you’re far too self-conscious,” added Sinead. “Stop thinking of what your friends would say, and realise what an attractive person you are.”
The flattery was beginning to chip away at Simon’s doubts.
“Am I?”
“If it weren’t for that thatch,” laughed Florence, putting a friendly hand on his knee, “you could easily pass as a girl. No, I mean that as a compliment. Isn’t that what you really want?”
“Er…” Simon looked puzzled. “I never said that…”
“No…but is it true? I’m not saying you should be a girl, but don’t you feel most comfortable when you’re dressed as one?”
Simon blushed and looked down to avoid Florence’s directness. His hands were in his lap, and unconsciously he pulled down the hem of his skirt, which had ridden up until his blue panties were visible.
“Well?”
“Don’t know, really…”
Florence stood up suddenly. She went to the wardrobe, grabbed something and came back. “This is my old school beret. Put it on.”
“Okay…”
He pulled it on clumsily. Florence adjusted it.
“Right. Let’s go.”
“W-what? Where?”
“Out. Coming, Sinead?”
“Ready when you are.”
-
XIII On the Beach
Simon retreated a pace, but the girls took one hand each, and dragged him up the stairs. In a moment, he found himself out in the street.
“Now don’t start getting embarrassed. We’re all three in uniform. You’re no different from us. Everyone’s going to assume you’re a girl, all right? Now we’re going to let go of your hands. Walk between us… And look confident, for goodness’ sake! If you want to give yourself away, just keep looking nervous like that.”
“Suppose we meet one of my friends…?”
“Don’t worry,” grinned Sinead. “In the skirt you’re wearing, they won’t be looking at your face!”
They went to the corner shop to buy some milk. “Hello, girls!” called the lady at the counter when they came in. She liked the girls from St. Agatha’s; always polite and well-behaved. They made Simon pay, and she didn’t bat an eyelid. Called him “love”.
“See? If she’d thought you were a boy, she’d have called you “sweetie”.
Simon was astonished. He’d never thought of himself as girlish-looking. But he caught sight of himself in a shop window, and the truth began to dawn.
They went into the post office, and the girls made him buy a book of stamps. He was treated, like most of the customers, with bored indifference. Then they went for a walk in the park. They actually passed a group of boys from Simon’s school, whose lecherous glances assured him they were seen only as three girls. His heart began to pound. Possibilities were opening up, things he’d never dared to dream of… Then they headed home. By this time, Florence’s parents were back. They turned to greet the girls as they walked into the lounge.
“Hi Sinead! Haven’t seen you for a while,” smiled Florence’s mother.
“And whose this, Florence? A new recruit to the club?” laughed her father.
“Oh, this is Simone.” She nudged him.
“Oh…hi…”
“Hi Simone. Have you seen Florence’s new room?”
“Y-yes…yes, I have…”
“Don’t let her lead you astray, will you? Goodness knows what goes on down there!” joked her mother.
“Anyway, we have to have a meeting,” said Florence. “Urgent business, mum. Don’t worry about supper. We’ll look after ourselves.”
“Well…actually, Florence, I was about to tell you… We’ve been invited out to dinner. We may be late back, so I’ve asked Bella to come over.”
“Oh, really? But Susie’s staying over at Harriet’s, right?”
“Yes, that’s right.”
“Mum, we’re fourteen!”
“Yes, but…well, you know, I just feel happier if…there’s an adult here…”
“An adult? Well, why have you asked Bella, then?” said Florence, sarcastically.
“Well, she is seventeen, you know, and…”
“You’ve explained the new protocol to her, I hope? No trespassers below stairs.”
“Well, not yet. But I will, of course, as soon as she gets here.”
“Don’t forget. Come on, girls.”
They filed through the little door, and Florence locked it behind her. They trooped down the stairs.
“Well? Convinced?” asked Florence.
“Maybe…it’s weird…”
“Weird? You have no idea, do you Sim?”
“No idea…?”
“No idea what a pretty face you have…”
“Oh…” Simon quickly changed the subject, despite a little thrill of pleasure. “Florence, who’s Bella?”
“Ah. Bella. The babysitter. Or used to be. You may remember her. She babysat you and Susie a couple of times. These days I thought she was just for Susie. Who is she? She’s a fu…”
“Don’t say it, Flo,” interrupted Sinead.
“No. You’re right. She’s…how can I put it? A nosey, self-absorbed, exhibitionist tart? Does that about cover it, Sinead?”
“Pretty much. Anyway, Simon would be a bit too young for her taste, I think.”
“I hope so. But she’s not getting to see him, anyway.” She turned to Simon. “Now, young lady. We’re all going to the beach. Get that uniform off and put your swimsuit on. The pink one first. Go on, off you go. I have to prepare the paddling pool, and get the camera set up.”
They sent Simon to the bathroom to change. Then Florence pulled a deflated plastic kids’ pool out from the bottom of the wardrobe, and began to inflate it with a foot pump, while Sinead filled a bucket at the sink. By the time Simon reappeared it was half full.
He skulked by the bathroom room, hands clasped discreetly in front of him.
“You took your time,” said Florence. “Does it fit?”
Simon squirmed in reply, but said nothing.
“I can see it fits perfectly. Alison knows her job all right.”
“Simmy, we want a few photos as you are, first of all,” said Sinead. “Then you’ll get wet, and we’ll do some more. Come on now, into the sand pit.”
He climbed in, reluctantly, and looked back over his shoulder. Florence was adjusting the camera and tripod. Sinead turned on the floodlight.
“Ooh, it’s good, Flo. It looks like sunshine.”
Simon was blinking in the bright light. He turned around to face the camera.
“Pick up the bucket and spade, darling,” Sinead instructed him.
As he did so, Florence noticed with satisfaction that the skimpy little swimsuit left no doubt about his real gender. The little pleated yellow wings on the legs served to focus attention on the critical area.
“Good. Perfect. Now smile….”
After the first session, Simon was told to splash about in the pool, until he was wet all over. Then the photos and videos resumed. He really looked very sweet, despite his occasional frowns of embarrassment, especially with the sand coating his legs and bottom, and the wet, semi-transparent, swimsuit clinging to him, showing off his boyish charms to great advantage. But to Florence’s delight, he slowly lost his self-consciousness, and played in the sand innocently enough, genuinely having fun, and every now and then grinning at her cheekily.
“He’s so cute,” whispered Florence. “What a pity he doesn’t have a little playmate.”
“Oh gosh, Flo, wouldn’t that be the best? Jack or William or someone. But we’d never get one of them into girls’ clothes.”
“Hmm. Maybe not…”
But the fantasy was suddenly dismissed by a loud knocking at the door.
“Florence? What are you doing down there?”
Simon froze, looking alarmed.
“Don’t worry, darling,” sighed Florence. “It’s only that bitch Bella. Stay where you are. I’ll go and sort her out.”
She ran up the stairs to the door.
“What do you want, Bella? We’re busy down here.”
There was a pause. “There’s someone at the door.”
“Someone at the door? Who?”
“They want you.”
“Who are they. Oh, shit. All right.”
She unlocked the door and opened it. Bella burst in, pushing her aside. “What’s going on down here?”
“What the fuc-k?” cried Florence, furious. “Is there someone at the door or not?”
“Only me, darling,” smirked Bella. “I just wanted to see what you get up to in your private room. I am supposed to be baby-sitting you, after all.”
Florence was seething. “Didn’t my parents tell you we weren’t to be disturbed?”
“They did. That’s what made me so suspicious.” She caught sight of Simon. “Who’s that…is that a boy?”
“Just get out, Bella, or I’ll tell my mum, and you’ll never work here again!”
But Bella was staring at the figure in the sandbox. “Is that your brother, Sinead? Why is he dressed in a girl’s swimsuit? And he’s all wet. Oh, you’re having a photo session...I see...”
“It’s none of your business, Bella. Now get out!”
“All right, if you say so. You won’t mind if I tell your parents what I saw here, I’m sure. Bye then…” And she made as if to go.
“Hold on. Why would you tell my parents?”
“No reason. Just think they might be interested…”
Florence sighed. “What do you want? Money?”
“Money? I’ve got money. Let me watch, that’s all. Let me watch what you’re doing, and I promise I won’t tell anyone.”
Florence looked at Sinead. Sinead shrugged. There wasn’t really a choice.
“All right. Come in. It’s all quite innocent. But I guess you can watch. We’re pretty much finished anyway.”
“Thanks, Florence.”
Florence took her by the arm and whispered in her ear. “But listen. Don’t you dare laugh at him. He enjoys dressing up as a girl, and we’re trying to reassure him it’s okay. Understand?”
“Perfectly. You’re reassuring him, and having a little bit of fun at the same time, right? Don’t worry, I won’t spoil your games. He looks far too cute just as he is…”
-
XIV Bella’s Plan
Florence locked the door, and followed Bella downstairs.
“Hi Sinead.” Bella gave her a self-satisfied smile, and clip-clopped over to where Simon was standing, looking puzzled. She was dressed in skin-tight black faux-leather leggings, high-heeled ankle boots, and a silver metallic crop top taut across her breasts, with a blue jewel in her navel, and a wristful of silver bangles, which jingled as she walked.
“Hello, Simon. Do you remember me?”
Simon, enveloped by a cloud of perfume, blushed and stared. His eyes were level with her chest. Her breasts, whether by nature or support was not clear to him, were of the pointed variety, the nipples clearly visible under the thin silver lycra. “H-hello, B-bella. Yes, you b-babysat me and Susie once or twice, I think. And I remember you from school.”
“That’s clever of you. I didn’t think the younger boys were interested in the sixth-formers.” She smiled innocently. “That’s a very cute swimsuit! Turn around and show me.” Simon obliged, swivelling his head so as not to lose sight of the new arrival for more than a split second. “It really suits you. I feel sorry for boys, generally. The choice of clothes! I mean, they’re so dull!”
Simon stared at her. “Y-yes…” The combination of the leggings, the proximity of the breasts, the perfume, and Bella’s full lips, was producing an involuntary reaction not lost on any of the observers.
“Do you have any other girls’ clothes?”
Before either of the girls could stop him, he blurted out, eager to impress, “Oh, yes. I have a school uniform – I went out in it today – and lots of panties, and a bikini, and…”
“Goodness! You have a whole wardrobe!”
Conscious he may have said too much, he tried to backtrack. “Course, I haven’t worn everything yet. I…”
“Would you wear some of them for me? I’d really like to see them. I know quite a lot about girls’ clothes. Maybe I could help…advise you…?”
“Yes, I think he better had change,” said Sinead, ironically, and added, under her breath, “before he stretches than swimsuit any more.”
“Sim, would you go an have a shower – wash that sand off yourself – and maybe put on one of your new skirts.”
“I’d like to see the bikini,” Bella said, pointedly.
“All right – the bikini. But put the red skirt on over the top, Sim.”
After he had disappeared into the bathroom, Bella turned to the girls.
“Why, you naughty things! What are you up to with that poor boy?”
“He’s not poor,” countered Sinead. “He’s having the time of his life doing what he likes best – dressing up. We’re merely…facilitating it.”
“I see…” said Bella, disbelievingly.
“It was all quite innocent till you gatecrashed. Not any more.”
“Oh, come on! Innocent?”
“He likes it. He likes showing off. And we’re convincing him he can, without feeling embarrassed.”
“And all the photo stuff?”
“That’s our insurance. In case he tries to change his mind.”
“Oh. And who would you show it to? To his friends?”
“Well, we’d threaten to…”
Bella looked from one to the other and shook her head.
“I don’t buy it. But I’ll tell you what. Let me come in on it, and I’ll help. Buy him clothes, foster the illusion. Everything.”
“Why?” asked Florence. “What’s in it for you?”
“Just one thing.” She giggled. “In two weeks it’s my eighteenth birthday. I’m having a party – you can come, of course. Girls only. I was trying to think of a fun treat for my friends. Now I know what it is.”
“Simon?”
“Simon. I want to dress him as a little maid – you know, uniform, apron, cap, the lot - and have him wait on everyone. Can you imagine? My friends will be so enchanted! And he’ll love it. All those girls fawning all over him…”
“No,” said Florence, doubtfully, I don’t think that’s…fair…”
But Sinead’s face had lit up.
“Flo! Just think of it. Bella’s got something there.”
“But he’ll be outed, won’t he?”
“No, he won’t. That’s the beauty. It can just be a gimmick – you know, like when boys dress up as girls at Halloween, or for one of those drag nights. No pressure. But Bella’s right – he’ll absolutely love it!”
And so it was agreed, and Bella was formally accepted into the project. When Simon came out of the bathroom, in his short red skirt and tiny bikini top, which he was continually adjusting, she took him on her knee, and tickled his tummy till he wriggled and became almost hysterical, while she introduced him to the idea.
“It’ll be the neatest little maid’s uniform you’ve ever seen! And Simon…all my friends are so pretty and nice, and they’ll all be dressed up in their very best party gear, with lots of makeup, and lovely dresses, and smooth, shiny stockings, and they’ll all want to pet you – I hope you won’t mind that – and for you I’ll make some special cakes, and there’ll be fizzy drinks, and crisps, and very expensive chocolates, and you can eat as much as you like!”
Her fingers traced little rings around his belly button, and she scratched his nipples with her nail through his top, making him shriek with laughter. His skirt rode up, revealing his bikini bottoms. Whether it was the present attentions of Bella, or the thought of the party, or both, his enthusiasm and excitement were obvious for all to see.
“Careful, Bella,” said Florence, “if one of those ties comes undone…
Sinead leant over to Florence.
“I think tonight he’s going to be happy to see how you’ve decorated his little room, Flo.”
“Yes. And I think he'd better have an early bedtime, don’t you?”
-
XV Preparations
After Bella had retreated upstairs, Sinead, not convinced of her brother’s willingness to participate in the birthday party, sat him down and interrogated him.
“So Simmy, are you really going to go to Bella’s party. Or were you just being nice to her?”
“Are you serious, sis? Do you know what her friends are like?” He looked at her disbelievingly.
“Well, no, I don’t know what they’re like. I mean, you know them from school, I don’t.” She sighed. “So you’re not going, then. And what if we insist?”
“No!” He almost screamed it. “Of course I’m going, idiot! Bella and her friends….they’re like the hottest girls in the whole school. And they're all about to leave! We're really going to miss them. My mates were always drooling over them. Not me, but… Anyway, yeah, so, like, I think I’ll probably go, to be polite, like…” he added, in a pathetic attempt to disguise his lecherous feelings.
“Oh, I see. Well, that’s nice. You should take one of your drooling mates with you,” replied Sinead, sarcastically. “I’m sure Jack would love to dress up as a maid.”
But the irony was lost on Simon. “Yeah, maybe I could ask him…”
“I wasn’t serious, Sim!”
“He once said he would do anything to get in with that crowd…” he added, thoughtfully.
“He did?” Sinead and Florence looked at each other with amusement.
“Well, ask him then,” said Florence. “Ring him now if you like. I’m sure Bella would be delighted to have two little waitresses.”
“I’ll wait till tomorrow. It’ll be easier face to face.” He paused. “Sis, I’m tired. Can I go to bed now?”
“I’m not surprised. Of course, if you want.”
“Where am I…?”
“See that door?” said Florence. “There a special little room under the stairs. It’s yours. You can bolt the door, and the bed’s all set up. There are some nice bunny pyjamas in the bedside cabinet if you want them.”
“Thanks. I’ll be fine in my bikini,” he said, without embarrassment.
“Okay. Go and brush your teeth first, darling.”
They waited for him to shut the bathroom door.
“This should be funny,” sniggered Sinead.
“Yeah. And the magazines I didn’t use I left next to the bed. Poor thing.”
“Give him what, ten minutes?”
“Ten minutes, then I’ll turn the light off. He can lay there and just think about it, without being able to see a thing.”
When Simon returned from the bathroom, he said goodnight to them, and headed for the room. He opened the door, and felt about for the switch.
“How do I turn the light on?”
“Oh, the switch is outside, darling,” said Florence. “We control the lights. We don’t want you awake all night, reading or something.”
Simon shrugged and made a face. “Okay.”
Florence flipped the switch and ushered him inside, shutting the door behind him. As the door closed they heard a gasp. There was a pause as he took it all in, then the key turned in the lock and all was silence. The girls, suppressing their giggles, gave him his ten minutes. Then Florence called out, “Time to settle down, Simmy. Good night!” And switched off the light from the outside. They heard a stifled moan of disappointment, and then left him to his misery.
During the night, however, Sinead, half asleep, heard the cell door open slowly, saw the small frosted pane of glass light up, and heard it close gently. “Oh, dear,” she thought, “He going to be wrecked in the morning...”
And so it proved. They let him sleep in, and he eventually crawled out of bed at a quarter to ten, looking as though he had just emerged from a harem – which in a manner of speaking, he had. After breakfast they said goodbye to Florence and headed back to aunt Rosie’s. Simon prepared to go and meet Jack and William, as he usually did on Saturday morning, while Sinead headed off to the mall. She wanted to see Alison, and ask her about maid’s outfits. If anyone would know where to get them, she would.
Alison was in her usual place, refolding clothes and putting discarded garments back on the racks.
“Sinead! Hi. Where’s your kid sister today?”
“He’s out with the boys. I came because I wanted some advice.”
“Go ahead.”
“What do you know about maids’ costumes?”
Alison laughed. “What? For Simon? What a great idea….”
“I’d better explain…”
And she told Alison all about Bella, the party, and her offer.
“And he’s up for it?”
“Seems to be, yeah. Apparently they’re the “hottest” girls in the school. I think it’ll be a wild one. As well as being Bella’s eighteenth, I guess it’s a leaving celebration. I don’t think he understands quite what he’s letting himself in for…”
“Are you going?”
“I plan to if I can.”
“Take me too? I think I can come up with an outfit. I know a place where I can get anything made to measure. Simon would have to come along, of course.”
“Great! And get this. He says he’s going to ask his friend to join him!”
“Oh my god…”
“I can’t believe Jack will agree. But who knows? They’re such lecherous little pigs.”
“When will you know?”
“Maybe even today.”
“Okay. Ring me, won’t you?”
“As soon as I know.”
“By the way, has he worn those little hot pants yet?”
“Not yet. There was so much else going on.”
“Pity. I found a little top that would go perfectly. And it’s totally appropriate. I put it aside.” She opened a drawer. “Here.”
She handed Sinead a little girl’s short crop top, in yellow satin, with a round neck, puff sleeves elasticated at the cuffs, and an elasticated hem. Across the front, in pink script, were the words, “Kid Sister”.
“That would go well! Same colour exactly… And I love the inscription.” She held it up. “Maybe I could take him to Florence’s again tomorrow…”
“Your friend…”
“Yes. She got the coolest room…a whole basement. You wouldn’t believe it…”
“Sounds great.”
“What are you doing tomorrow?”
“Nothing. Shop’s closed.”
“Would you like to come? We could dress Simon in his hot pants at last.”
“Could I?”
“Let me speak to Florence. Let’s swap numbers. I’ll call you later…”
-
XVI Doubles
While this conversation was going on at the mall, Simon had made his way to Jack’s house. Jack opened the door.
“Hi Sim. What’s up? You look wasted, man.”
“Oh, nothin’. Bin busy. Listen. Is William here yet?”
“Not yet. Always late.”
“I need to talk to you. In private.”
“Okay… Let’s go out to the shed.”
The shed was the boys’ centre of operations. The lock had a rusty key by means of which all outsiders could be excluded. Jack led the way, and locked the door behind them.
“So…”
“How would you like to go...to Bella’s eighteenth?”
“Bella…?”
“You know – Bella Seaman!”
Jack stared. “What?”
“Would you want to go?” he repeated, impatiently. “Her birthday party! Her and all her friends! No blokes, just all those big juicy girls!”
“What are you talking about?”
“Listen. I’ve been invited. And you could come to.”
“She’s invited you? Why?”
“Look… Never mind. She wants someone to serve the drinks, that’s all.”
“Fuc-k, yes! I’m in, dude! I’ll wait on them anytime, no probs! When is it?”
“Two weeks. Just you and me. I’m not asking William. He can’t keep a secret.”
“You’re not wrong there. We don’t need him, anyway.”
But look… There’s one little catch…”
Jack’s face fell. “What? Tell me.”
“Well, cos there’s, like, no blokes allowed…see…we would have to…like…dress up as girls…”
Jack was unfazed. “Dress up as girls? What, like wear a skirt? Is that all?”
“Well, we’re supposed to be waitresses, see? I think we’d have to wear waitress costumes…”
“Oh…I get it… That’s not a problem, Sim. I can do that. I wore that dress last Halloween, remember? I’d dress up as a warthog if I had to, to get into that party. How’d you swing it?”
“Oh, she used to babysit me when I was a kid. Then the other day I sort of ran into her, and she goes, “Hi, Sim, how are you,” an’ she gives me a kiss, like…”
“Gives you a kiss?”
“Yeah. An’ I says “fine”, like, and she goes, “how about comin’ to my birthday party…help out with the drinks…bring a friend if you like…meet all my friends…you’ll be the only blokes there…” So I says, “okay, I’ll ask my best mate Jack to come an’ help too…””
“You’re a fuc-kin’ genius Sim! Oh, shit, I can’t wait! Like, those girls…I mean, they’re all fully developed now, aren’t they… Wonder if that Deborah King’s gonna be there…I still have dreams about her tits…”
-
XVII The Statue
When Sinead heard that Jack was going to be joining Simon at the party, she first of all cleared it with Bella – who was, predictably, ecstatic at the prospect of having two maids waiting on the guests – and immediately after rang Alison.
“We’d better get a move on, then, said Alison. I’ll ring the dressmaker. Could the boys come with me after school Monday?”
“I’m sure that’ll be fine.”
“Okay. I’ll arrange it. What about tomorrow?”
“I’ve spoken to Florence. It’s all fixed. Would eleven be okay? I’ll text you the address.”
“I’ll be there, Sinead. Actually, I could measure Simon then, to save time. I'll bring my stuff.”
Simon was not best pleased to hear that he would be returning to Florence’s the next day. He flatly rejected Sinead’s offer of bringing Jack with him, especially after she’d told him she’d got him a new top. He needed to preserve the illusion that the party dressing-up was a one off. He didn’t want to scare Jack off. He was of course looking forward to the party, but the few lurking doubts his lascivious imagination had been unable to put entirely to rest needed the moral support of a good friend.
They were at Florence’s by ten o’clock. Sinead wanted to get Simon ready before Alison arrived. What a nice surprise that was going to be! They were greeted by Florence’s mum.
“Hello Sinead. Hello Simon. You approve of Florence’s new room, then.”
“It’s beautiful,” said Sinead, as they followed her down the corridor.
“I’m sure it is,” said Florence’s mother, “but since Bill decorated, we’re not allowed in!” She laughed. “Goodness knows what goes on down there!”
Just as well only goodness knows, thought Sinead.
“Florence?” she called. “Sinead and Simon are here.”
“Thanks, mum,” came Florence’s voice from below, followed by her footsteps on the stairs.
Once downstairs, the girls wasted no time. Simon was given his hot pants and top and told to change.
“Can I have some panties?”
“No, sorry, Simmy. They’d spoil the lines of these gorgeous little hot pants. Now hurry up and get ready.”
“Get ready for what?” he responded, sulkily.
“Just get ready.”
When he emerged, Sinead gave him his long lemon socks to put on, and his pink trainers. He stood up, looking very coy.
“You look a treat!” smiled Florence. “Now come with me, and stand on this platform.”
The girls had it all planned out.
“What? Why?”
“Just do as you’re told,” snapped Sinead. “That’s it.”
“Now, stand up straight. Back to the wall. Feet together. Stay like that.” commanded Florence. She fetched something jingly from the desk, and knelt down. She looped the fine steel chain around one ankle, and padlocked it. She threaded it through the staple, and did the same round the other ankle.
“There!” She stood up. “Can you move?”
“No, course not. I can’t even squat down, cos of the wall. How long am I supposed to stand here?”
“As long as we please,” said Sinead. “You should be flattered. You’re now part of the decoration. A lovely little statue everyone can admire. Here, don’t forget this.” And she produced his baseball cap from her bag, and wedged it over his gingery mop.
Simon squirmed in embarrassment, but he could hardly move. He looked down at himself, over the puffy top, over his bare tummy, to the little, shiny, skin-tight hot pants, and the little mound of his flaccid pen-is.
“Oh, you approve, I can see,” said Florence. “Just a moment. We’ll bring over the full-length mirror so you can see yourself properly.”
They placed it directly in front of him, and tilted it until he could see all of himself, increasing his humiliation further.
“You look absolutely beautiful, Simmy!” smirked Sinead. “And we have a surprise for you. In…” she looked at her phone. “In…thirty minutes, Alison is coming to visit.”
“Alison?”
“From the clothes shop. She’s been dying to see you in your hot pants, and at last she will.”
“No! Not like this! Please…”
But the girls only laughed…
Florence went upstairs just before eleven to wait for Alison. She arrived exactly on time.
“Hi Alison.”
“Hi, Florence. Thanks for inviting me.”
“You’re welcome. Follow me. The others are downstairs.”
“I brought my tape. I thought I could at least measure Simon while I’m here. I’ll do his friend later.”
“Good idea. Actually, he’s in the perfect position to be measured. Through here…mind you head.”
Alison found herself on the little balcony. She was surprised at the size of the room.
“Wow…this is amazing! You’re so luck…” She broke off. She’d caught sight of Simon on his pedestal. She couldn’t suppress a burst of laughter. “Simon! You’re wearing your hot pants! Did you put them on especially for me?”
She made her way downstairs.
“Let me give you the tour,” said Florence, and conducted Alison around the room.
“This is the garden mural. We use this for our prettiest models. They look so sweet holding a pansy, against a background of tulips…and this…this is our seaside area. Simon’s already been showing off in here in one of those lovely swimsuits we got from you. We’ll show you all the footage and snaps later on… Here we have the bathroom…now come right down here…this is what we call the cell, also known as Simmy’s bedroom. He’s decorated it with all his favourite posters.” She opened the door.
“I didn’t! It wasn’t me!” shouted Simon. “It was like that already!”
Alison ignored his outburst. “Tut, tut, boys these days…I don’t know…”
“And finally, here is our pretty statue. Simon volunteered. He was desperate to show off his new outfit to you. What do you think?”
“I wasn’t!” cried Simon. He was conscious that the thin stretchy lycra showed everything he had; and though that may have been not much, the shortness of the hot pants necessitated a diagonal orientation of the central element. He therefore attempted to casually to conceal it by clasping his hands in front of him.
“I think you’re very smart, Simon. Yellow and pink really suit you, like most little girls. Not only that, but you’re in the perfect position for me to take your measurements for your maid’s uniform.”
“Would you like a coffee first, Alison? We’ll move the mirror, and we can all sit here in the armchairs and admire the statue while we’re chatting.”
They sat in a semi-circle, with the coffee-table in the middle, facing the new adornment to the room, who blushed and wriggled helplessly, keeping his hands determinedly between his legs.
“Simon…don’t be so shy,” smiled Alison, encouragingly. “Come on, let’s see those hot pants in their full glory. They’re so sweet, after all, and they fit you…so perfectly.”
Simon made no reply, except for a sulky pout.
“Well you’ll have to take your hands away when I measure you.”
“Why?”
“Because I need to measure your body, silly, and I can’t do that with your arms in the way. She put down her coffee cup. “What do you think girls? Shall I do it now?”
“Go ahead,” said Sinead. “We’ll just sit here and watch.”
“Okay.” She took a notebook and pencil and a measuring tape out of her bag, and stood up. “First, your neck…” She threaded the tape round his neck and wrote in her notebook. “You’ll probably have a little choker, I think.”
“Definitely!” said Sinead.
“Chest next. Come on, Simon, lift up your arms please. Come on! No? Right.”
Alison slid her hands under his armpits and began to tickle. Simon squealed and immediately raised his arms.
“All right, all right. Please don’t do that…”
“He’s terribly ticklish,” grinned Sinead. “It can be very useful at times.”
She wrote down his chest measurement, then his waist, then went down to his thigh.
“Why are you measuring his thigh?” asked Florence.
“Garter.”
“Oh, yes, of course.”
“Now…hips… Simon! Keep your hands away, please! I don’t know why you’re being so coy about it. It’s very small, after all…”
Simon tuned a slightly deeper shade of red.
“In fact, I can tell you exactly how small…”
To his infinite chagrin, Alison took her tape and laid it along the little mound of his pen-is.
“Let me see…I make that five centimetres long. Nothing to get worked up about then, is it?”
Simon turned his face to one side as far as it would go, and shut his eyes tight. He didn’t know what to do with his hands.
“And that’s the only dimension I can tell you, without actually taking it out.”
Simon swivelled his head back and stared at her wide-eyed.
“Don’t worry, none of us wants to see it. But I still have to measure your hips.”
She had to thread the tape behind his bottom, which involved pressing herself close to him for a moment. He felt her breasts against his bare tummy, and was forced to inhale her perfume. Women’s perfume always had a stimulating effect on him, and he felt stirrings underneath the taut, slippery lycra. He took a sharp breath, and bit his lip.
Alison worked the tape down to the widest point of his hips, which coincided with the bulge. She tightened it so that it pressed against the five centimetres, which was now lying to the right at an angle of about forty-five degrees. She appeared to be having a problem reading the tape, or deciding how tight she should hold it. Now it was bisecting the little sausage-shaped mound, compressing the middle. Had it perhaps moved a few degrees closer to the vertical? And was it by any chance…? Yes…a little longer, and a little fatter than before. Holding the tape ends together, she slid it back and forth, feeling the slack. In doing so, it rubbed back and forth against the pen-is, rolling it from side to side. Simon gasped, and looked at her imploringly. But Alison was not going to relinquish her advantage.
“It’s this thing! I can’t get a proper measurement, because this…” – she prodded it with her finger – “this won’t stay still! Look. I’ll show you.”
She slipped off the tape and re-measured its length.
“I told you so! Nine centimetres now! And increasing! How can I work with this?”
She glared at Simon with mock annoyance. Sinead and Florence were in stitches. By this time Sinead had her phone out and was videoing proceedings.
“What am I going to do? Can’t you make it go down again, Simon?”
He was trying. Trying his hardest. But it was no longer under his control. All the attention had had its effect. Even as he fought with his feelings, it attained its fullest dimensions, and stood there, visibly throbbing under the stretched material.
“It’s hopeless!” Alison gave it a gentle squeeze, as if expecting that would somehow help it deflate. It didn’t. Instead, a flow of clear juice issued from its tip and oozed through the shiny fabric.
“Oh, dear! Simon, really! Here…”
She pulled out a tissue and began dabbing at the wet patch. Simon whimpered. He had dropped his hands to his sides, but his little fists were clenched. The more she dabbed, the more juice oozed forth. Simon closed his eyes and sighed. Soon the tissue was just a little slimy ball.
“Goodness! And I thought you were going to look so nice in these hot pants. But now they’re ruined. Sinead? I think you’ll have to keep him in skirts and dresses from now on. If he gets like this at the slightest provocation… I see now why he has those pictures all over his bedroom.”
“I didn’t…”
“Shush, Simon. Now, at least promise me you’ll behave properly when you’re wearing your little maid’s outfit. None of this…naughtiness!”
“But…”
“No buts. Promise.”
“I…ah…promise….I swear. I’ll be good…but please…no more…”
“Don’t worry. I’m done. Here’s a clean tissue – take it and clean yourself up. I need to wipe my hands.”
Simon took the tissue, and Alison resumed her seat.
“Such a naughty boy,” she whispered to Sinead, with a wink.
“Well wipe yourself, Simmy. Go on,” urged Sinead.
“I don’t think…”
“Go on. Look at the state of your lovely hot pants.”
Nervously, Simon applied the tissue to the slimy tip of his erect pen-is. But he was clumsy, and underestimated its sensitivity. The frustrations of the previous night didn’t help, either. With a gasp, followed by a loud cry of “oh, gosh”, he came, pumping wads of c-um through the lycra, which then slid down the vertical member in milky rivulets, and dripped stickily onto his thighs.
His audience, relaxing in their comfortable chairs, looked on with amused interest, till eventually his spasms subsided, and he stood there quite exhausted, helpless and gasping. Florence poured some more coffee, while they watched the little drops of c-um dripping lazily down his legs and onto his socks and shoes.
“If ever a boy needed to be girlified, he does,” remarked Alison.
“To judge by that performance, it’s not going to be easy,” responded Florence.
“No,” said Sinead. “It’s true we may never get the boy out of Simmy – but we’ll get the Simmy into panties, for sure!”
-
XVIII Reconciliation
When the little dishevelled statue was finally released from its pedestal, and given a change of clothes and conducted to the bathroom, the ladies resumed their discussion about Bella’s party.
“Well!” said Florence. “That does make you wonder…”
“How those boys are going to cope with Bella and her friends? Yes, I agree,” said Sinead. “But I don’t see what we can do about that. Alison, what do you envisage these costumes are going to be like?”
“Well, I was thinking probably what you were thinking… You know, little black satiny things with long sleeves and miniskirts, maybe crinolines to puff them up, lace trimmings, aprons, caps – all the usual stuff. But I do see the problem.”
“Maybe we should put their willies in chastity devices,” suggested Florence, with an evil wink.
“That would simply be cruel. And I don’t think Jack would stand for it. From what I hear he’s fine with the dressing up, but knowing him, I think he'd just walk away.”
“It wasn’t a serious suggestion.”
They sat there musing for a while. Then Alison spoke.
“I think that what is required here is containment. Something that will hide any, you know, unruliness.”
“What are you thinking?”
“Well, for Simon, I suggest he wear tights and that little rainbow swimsuit under his uniform. It would keep him nice and compact.”
“Yes…and protect him too, if things got…how shall I put it…out of hand. I don’t trust that Bella one inch,” added Sinead.
“Okay. That sounds sensible. And what about Jack? Would he accept something like that?” said Florence.
“You know what, Flo? When I was at the stage of merely dreaming of dressing Simon as a girl, and he was with Jack, I used to fantasize that Simon was a cheer leader and Jack…a ballet dancer.”
“Oh, that’s an excellent idea!” cried Alison. “We have some beautiful little ballet outfits in stock. There are lovely velvety ones, satiny ones, shiny metallic ones. Which do you think he’d like?”
Sinead laughed. “Better ask him, I think. You know, he might be okay with it. Last Halloween he was the only boy in the school who decided to dress as a girl. That must be significant, don’t you think?”
“Depends,” said Florence. “Did he wear panties?”
“That’s something else you better ask him,” laughed Sinead. “But I have a feeling about him. Simon told me he raised no objections to the maid’s uniform.”
“It would be great to have two little boys in our project,” said Florence, with enthusiasm. “And much easier. We could get them competing with each other to see who was the prettiest.”
“Well let’s go step by step, Flo. Don’t let your imagination run away with you.” She turned to Alison. “So tomorrow after school, Simon will take Jack to see you at the shop. Then what?”
“Well, I’ll measure him, and email both the boys’ measurements to the dressmaker. The outfits will be ready by Friday. I’m wondering…maybe I can subtly introduce the idea of ballet costumes…just to see their reaction.”
“Simon will probably want one!”
“If he showed any interest…that may give me an insight into Jack’s attitude.”
“Play it by ear, Alison.”
“I will. And I may have another idea that would help keep them under control…”
“Yes?”
“Do you think they would know what “foundation garments” are?”
“I doubt it. They may have heard the phrase, but that’s all. Why?”
“I have an idea. My dressmaker…she also makes latex clothes. I could get her to make the boys some nice little fine latex panties to wear underneath everything. That way they’d be contained and restrained and whatever happened… no one would know. And I could sell it to them under the pretext that “foundation garments” are an essential part of a woman's outfit. What do you think?”
“That’s brilliant!” said Florence. “Do you think you could?”
“If anyone could, it’s Alison. I don’t think either of us could suggest it, said Sinead. “And it sounds like the perfect solution.”
“Okay. I’ll suggest it and see what reaction I get. I think…” She stopped in mid-sentence. “Shh. I think he’s about to come out.”
Simon emerged from the bathroom. He had bare legs and feet. He had changed into his school shirt and his red skirt. They caught a flash of his favourite Hello Kitty panties.
“I hope he’s not angry with us,” whispered Florence.
He walked straight up to Alison, cheeks burning. He stood in front of her and lowered his head.
“Alison? I’m really sorry about what happened. It was an accident. Please don’t be angry with me. I tried very hard to be good, but I was…over-tired. I’ll wash my hot pants this evening. Thank you for giving them to me. Actually I really like them, and I’m going to wear them again as soon as I get the chance. Sorry…”
Alison was quite taken aback. Then she opened her arms and pulled him onto her lap.
“Darling…! Please, don’t apologise. It was nothing. If anything it was my fault. I should have been more careful measuring you. But just for a moment, I forgot you were a boy at all. I’m so used to measuring girls…”
Simon snuggled into her, with his head under her chin. She looked at the others with amazement and delight, to which they returned satisfied smiles.
-
Hi Sandra,
I love this story and am wondering if you are going to finish it?
Do you have another site where you post stories?Thanks
Dancer4Fun