A Grown Boy

[Andlat]

That settles it. Sinead is wicked, but will anyone realize it before it's too late for Sim?

[dolly bo peep]

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.

[Sandra B]

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!”

[Andlat]

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?

[Sandra B]

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!”

[Andlat]

Never let it be said that Sinead doesn't understand subtlety! 😂

I can only imagine the reactions he'll get wearing his new things!

[Sandra B]

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,   â€œgood - 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!”
 â€œI 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.