A Grown Boy

[Andlat]

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.

[Sandra B]

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…”

[Andlat]

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.

[Sandra B]

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!”

[Andlat]

I can't speak for Simon, but I'm very excited to see Florence's room

[Sandra B]

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…

[Andlat]

Simon has no idea how trapped he is. Not yet, anyway