Incredible beginning, and i hope you will continue soon. Having her acting as sweet as syrup but with the feel of devious control really works because you don't know when she will turn.

Chapter 185.

“What’s going on?”
“Not sure.  Miki says he’s getting changed.”
Nicole made her way to the bedroom, where she found her nephew sitting on the floor in a rather dishevelled and exhausted state.  She looked at Miki, who was standing behind him.
“Ah.  I see you made some progress,” she remarked with a wry smile.
Miki nodded, and looked at Nicole cautiously, trying to gauge her reaction.
“Right young man.  Into the shower first.  Get all your things off and put them in a plastic bag – here, this’ll do.  Off you go!”
Having despatched him, she turned to Miki.
“To judge by the state of him, he must have needed that…”
“Yes, I think so.  He did everything himself, actually…”
Nicole raised an eyebrow.  “Clever girl!  I must say…”
But she was interrupted by a cry from the living room.  One of the girls.
“Yuk!  Mrs Burlington?  What all this slimy stuff on the floor?  It looks disgusting…”
“Oh.  I’d better go.  Could you put him in something suitable and bring him back when he’s recovered?  Thanks, Miki.”

When Bobby emerged half an hour later he was wearing a girls white shirt with the tails knotted at the waist, his boot boy pants, and long white socks.  He seemed slightly dazed, but relaxed.  Supper was a success, the cake was delicious, and everyone had a good time.  The mothers came to collect their girls.  Nicole noticed that Miki took Bethany and Natasha aside and apparently shared a photograph, with which they both seemed highly delighted.  After they had left, she asked Miki what it was.  Miki showed her the original photo of Bobby in all his glory in front of the cherry tree.
“Just this.  I hope you don’t mind.  They seemed so disappointed that they didn’t see his new outfit.”
“Not at all.  It’s a beautiful photo.  I’m sure they’ll treasure it.”
“I told them he’s going to be pageboy at Deborah’s wedding.  They were delighted.  They know Trixie’s mum so apparently they’ve got invitations.  They weren’t going to go, but I’m sure this’ll change their minds…”
“I’m sure it will…  So, Miki?  Are you two dating now?”
“Not yet.  He wants to.  I said I’ll tell him if he can on his birthday.  I want to consult my best friend Estelle first.”
Nicole laughed.  “Yes, get a second opinion.  Good idea.  Especially as you only know half the story so far…”
Miki looked puzzled, but Nicole declined to offer further explanation.

Such a lovely story, I hope there is more to come. Would love to see him having to wear diapers for example.

Just one minor timeline correction. It says it he was 5 the last time he saw her and its been over 10 years since which would make him 15+ now not 12.

Tinkydrew Part 6

The air in the pink-drenched room feels thick, almost suffocating, as Aunt Margaret claps her hands with a gleeful flourish, her eyes sparkling with that feverish excitement I’m starting to dread. My bouffant curls, now locked in place with coconut-scented hairspray, bounce slightly as I shift uncomfortably on the vanity stool, the cold metal of the chastity belt a constant reminder of my vulnerability. The engraved words—“Tinkydrew,” “Auntie's Sissy,” “Delicate Doll,” “Princess in Training”—burn in my mind, especially “Tinkydrew,” etched right where my boyhood used to be. It’s as if the belt is rewriting me, erasing Andrew and leaving only her little Tinkydrew in his place. My stomach churns, but I’m too overwhelmed, too exhausted, to argue as Margaret turns to the wardrobe with a purposeful stride.

“Oh, Tinkydrew,” she says, her voice dripping with anticipation, “I’ve been dreaming about this moment ever since I heard you were coming to live with me. I’ve had one particular outfit in mind, just for you.” She glances back at me, her smile wide and unyielding, and I feel a prickle of unease. “It’s perfect, you’ll see.”

She opens the wardrobe doors with a dramatic flourish, and my breath catches as she pulls out the most over-the-top outfit I’ve ever seen. It’s a fairy princess dress, but not the kind you’d see in a store for kids—it’s too juvenile, too feminine, even for a five-year-old girl. The dress is a frothy explosion of pale pink and lavender tulle, layered with shimmering organza that sparkles like starlight. The bodice is fitted, adorned with tiny silver sequins and embroidered with delicate roses and vines, each petal edged with glitter. Ruffles cascade from the shoulders, forming puffed sleeves that look like they belong in a storybook. The skirt flares out in a bell shape, so voluminous it seems to float, with a petticoat underneath that rustles with every movement. A wide satin sash, tied with an oversized bow at the back, cinches the waist, its ends trailing like ribbons on a gift.

But the wings—they’re what make my heart stop. Attached to the back of the dress are large, translucent fairy wings, framed in delicate wire and covered in gossamer fabric that shimmers with iridescent pinks and purples. Tiny rhinestones dot the edges, catching the chandelier’s light, and I can almost hear them tinkling like chimes. They’re the kind of wings I wore as a five-year-old, when Margaret called me Tinkydrew and twirled me around her living room. But these are bigger, more elaborate, and unmistakably meant for me now.

“Aunt Margaret,” I stammer, my voice barely above a whisper, “that’s… it’s too much. I can’t wear that. It’s for a little girl.”
She laughs, a bright, tinkling sound that fills the room, brushing off my protest like it’s nothing. “Nonsense, Tinkydrew! It’s perfect for you. You’re my little fairy princess, and this is your castle.” She steps closer, the dress draped over her arm, the wings swaying slightly. “Let’s get you dressed. We’re going to have so much fun today.”

I want to argue, to tell her I’m Andrew, not Tinkydrew, not a princess, but the weight of the past few months—losing my parents, the long train ride, the locked door, the chastity belt—presses down on me. My mind keeps drifting to the engravings on the belt. “Delicate Doll”—am I just a toy to her, something to dress up and play with? “Auntie's Sissy”—is that how she sees me, fragile and small, not a man at all? And “Tinkydrew,” that name carved where my identity as Andrew should be, feels like a brand, a claim that I’m hers to shape. The thought makes my chest tighten, but Margaret’s already moving, her hands gentle but insistent, and I’m too overwhelmed to resist.

She starts with the petticoat, a frothy white thing with layers of tulle that she slips over my head. It settles around my waist, making me feel like I’m drowning in fluff. Next comes the dress itself, and she guides my arms through the puffed sleeves, the fabric cool and silky against my smooth, hairless skin. The bodice hugs my slim frame, the sequins catching the light as she zips it up the back, the sound sharp and final, like the click of the chastity belt. The skirt flares out, the petticoat giving it a life of its own, and I feel ridiculous, like a doll being posed. She ties the satin sash tightly around my waist, the bow at the back so large it brushes the floor. The wings come next, attached with hidden straps that she fastens around my shoulders, their weight surprisingly light but impossible to ignore. They sway with every movement, a constant reminder of the role she’s casting me in.

Margaret steps back, her eyes gleaming with satisfaction, and kneels to slip a pair of accessories onto my feet—sparkly pink Mary Janes with tiny bows and rhinestone buckles, the kind a little girl would wear to a birthday party. They fit perfectly, just like the chastity belt, and a flicker of suspicion crosses my mind again—how does she have all this, sized exactly for me? But before I can dwell on it, she’s adding more: a delicate silver tiara, studded with pink rhinestones, which she nestles into my bouffant curls, pinning it in place so it won’t budge. She clips matching rhinestone earrings to my ears—clip-ons, thankfully, but they pinch, their weight tugging at my lobes. A choker follows, a thin band of pink velvet with a heart-shaped pendant that reads “Tinkydrew” in curling script, echoing the engraving on the belt.

She’s not done. From a drawer in the vanity, she pulls out a makeup kit, and my heart sinks further. “Just a little touch-up,” she says, her tone soothing but unyielding. “To make my fairy princess shine.” I want to protest, but her hands are already moving, dabbing foundation on my cheeks to smooth my already pale skin. She brushes on pink blush, high on my cheekbones, and dusts my eyelids with shimmery lavender shadow. A touch of mascara makes my lashes look impossibly long, and she finishes with glossy pink lipstick, the sweet taste lingering on my lips. Each stroke feels like another layer of Andrew being painted over, replaced by Tinkydrew, her creation.

Finally, she adds a pair of fingerless lace gloves, white with tiny rosebuds, and a wand—yes, a wand—sparkly and topped with a star that glitters under the chandelier. “Hold this,” she says, pressing it into my hand, and I clutch it, my fingers trembling. The outfit is complete, and I feel like I’m drowning in it, every ruffle, every sparkle, every accessory screaming “little girl” in a way that makes my stomach churn.

Margaret steps back, her smile so wide it’s almost manic. “Oh, Tinkydrew, you’re perfect,” she says, her voice trembling with excitement. “Come, let’s see you in the mirror.” Before I can protest, she lifts me—her strength still startling—and carries me to a full-length mirror in the corner of the room, setting me down gently in front of it. The wings sway behind me, the petticoat rustles, and I brace myself for what I’ll see.

The reflection is a shock, even though I knew it was coming. I look like a five-year-old girl dressed for a fairy-tale tea party, not an twelve-year-old boy. My bouffant curls, still glossy from the mousse and hairspray, frame my face in a halo of feminine bounce, the silver tiara glinting like a crown. The makeup transforms me—my cheeks are rosy, my eyes wide and sparkly with lavender shadow, my lips glossy and pink, making my face look even younger, softer, unmistakably girlish. The dress is a cloud of tulle and sequins, the puffed sleeves and massive bow exaggerating my slight frame, making me look delicate, almost ethereal. The wings shimmer behind me, their iridescent glow catching the light, and the Mary Janes sparkle at my feet, the rhinestone buckles winking with every shift. The choker’s “Tinkydrew” pendant sits at my throat, a mirror to the chastity belt’s engraving, and the wand in my hand completes the picture—a perfect, prissy fairy princess, too young, too feminine, too everything I’m not.

I stare at myself, my heart pounding, and all I can think is what this means. The chastity belt, hidden under the dress, feels heavier now, its engravings burning in my mind. “Tinkydrew,” carved where my manhood should be, feels like a declaration, a final overwrite of Andrew mocking my small frame, my lack of strength, my inability to resist her. “Princess in Training” suggests this is just the beginning, that she has plans for me, plans I can’t see. I can’t look away from the mirror, from the little girl staring back at me.

Margaret’s hands rest on my shoulders, her reflection looming behind mine. “Isn’t it wonderful, Tinkydrew?” she says, her voice soft but intense. “You’re my little fairy princess, just like I always dreamed.” Her fingers brush the wings, making them shimmer, and I feel the weight of her dream pressing down on me, reshaping me into someone I don’t recognize.

I open my mouth to protest, to say I’m Andrew, not Tinkydrew, not this, but the words won’t come yet. I'm still too overwhelmed.  The outfit, the makeup, the chastity belt—they’re all too much, and I’m too small, too lost, to fight it. For now, I’m her Tinkydrew, caught in her fairy-tale castle.

Tinkydrew Part 4

The bathroom’s warmth still clings to my skin as Aunt Margaret wraps the fluffy pink towel around me, but the way she does it catches me off guard. Instead of just draping it over my shoulders like I’d expect, she tucks it under my armpits and wraps it tightly around my chest, the ends secured high like I’ve seen women do in movies. It feels strange, foreign, the fabric hugging my slim frame in a way that makes me hyper-aware of my body. I’ve never done it this way, but she’s already ushering me out of the bathroom, her hand on my back, so I go along with it, my cheeks warm with embarrassment.

Back in the pink-drenched room, she guides me to the vanity, its gold-framed mirror reflecting the soft glow of the chandelier. “Let’s get that beautiful hair ready for bed, Tinkydrew,” she says, her voice bright, almost musical. She sits me down on a cushioned stool, the towel still wrapped tightly around me, and starts brushing my damp, dirty blond hair with a silver hairbrush. Her fingers move with practiced ease, parting my hair and weaving it into what she calls a Dutch braid crown. Each tug is gentle but firm, her hands shaping my hair into a tight, intricate pattern. “This will keep it from tangling while you sleep,” she explains, her tone matter-of-fact. “No knots for my Tinkydrew.”

I sit still, letting her work, the rhythmic motion oddly soothing despite the strangeness of it all. “A crown, huh?” I mumble, trying to lighten the mood, but she giggles, a sound that’s too bright for this quiet room.

“Oh, yes,” she says, her eyes sparkling in the mirror’s reflection. “A crown for my little princess, sleeping in her castle.” She teases, but her words make my stomach twist. I’m not a princess, I want to say, but her fingers are still moving, and I don’t want to upset her. Not when she’s all I have.

When she finishes, she steps back, and I catch my reflection. My hair is woven into a tight, elegant braid that circles my head like a crown, the strands gleaming under the chandelier’s light. It does look regal, almost magical, but it’s so… feminine. I reach up, curious, my fingers brushing the braid. It’s so tight, so intricate, I have no idea how to undo it. The thought makes my chest tighten, but Margaret’s already moving, distracted, rummaging through the wardrobe across the room.

She returns with a small bundle of fabric in her hands, her smile wide again. “Here, Tinkydrew, put these on,” she says, handing me what I think are undershorts. They’re soft, pale pink, with tiny embroidered crowns and sparkly thread that catches the light. I hesitate, but she’s watching me, so I step into them, pulling them up under the towel. The fabric is snug, smoother than any boxers I’ve worn, and as I adjust them, my heart sinks. These aren’t undershorts—they’re panties. Delicate, lacy, unmistakably feminine, with a little bow at the waistband and those crowns stitched in a pattern that screams “girl.”

“Aunt Margaret,” I say, my voice sharp, “these are… they’re panties. I can’t wear these.”

She tilts her head, her smile unwavering. “Oh, Tinkydrew, they’re perfect for you. Look, there’s barely a bulge—see? They fit just fine.” Her tone is so casual, like she’s commenting on the weather, but her words hit like a punch. I glance down, my face burning, and she’s right—my slight frame, my small… everything… makes the panties look as if they belong on me. The embarrassment is overwhelming, a hot wave that makes me want to disappear.

Before I can argue further, she’s holding up something else, and my breath catches. It’s a not like anything I’ve ever seen. It looks like a bag, pale lavender, covered in ruffles and lace, with “Princess in Training” embroidered in curly gold letters across the front. The fabric shimmers, soft and silky, but it’s so girlish, so over-the-top, it makes my head spin. “What’s that?” I ask, my voice barely above a whisper.

“Your sleepwear, silly,” Margaret says, her eyes glinting with that same feverish excitement. “It’s cozy, perfect for a good night’s rest.” She steps closer, unfolding it, and I see it’s like a giant, padded bag with a zipper up the front and a ruffled neckline. I’ve never seen a sleepsack before, let alone one this feminine, but before I can protest, she’s guiding my arms into hidden slots inside, her hands gentle but insistent. My legs follow, slipping into their own compartments, and then she zips it up, the ruffles at the neck tickling under my chin. The fabric is soft but restrictive, hugging my body like a glove.

I squirm, testing the fit, but my arms and legs are trapped, the slots keeping them snugly in place. Margaret pulls at something on the back—laces, I realize, like a corset—and starts tightening them. The sleepsack cinches around me, squeezing my chest, my waist, my legs, until it feels like I’m in a full-body corset. I can barely move, the fabric holding me in a firm, unyielding embrace. “Aunt Margaret,” I say, my voice rising, “I can’t move. This is… it’s too tight.”

She laughs softly, her hands still working the laces. “It’s just like swaddling, Tinkydrew. Babies sleep better when they’re snug, and so will you. It’s comforting, isn’t it? A nice, safe hug.” Her tone is soothing, but it’s the kind of soothing that makes me feel smaller, younger, than I am.

I want to argue, to tell her this isn’t right, that I’m not a baby or a princess or whatever she thinks I am. But the sleepsack, the room, the braid—it’s all so overwhelming, and I’m exhausted. Maybe this is just what she has, I tell myself. Maybe this is her way of coping with her own loneliness, dressing me up in these things. I decide to go along with it, just for tonight. Tomorrow, I’ll talk to her, set some boundaries.

She lifts me again—her strength still startling—and places me gently in the prissy bed, the ruffled bedspread crinkling under me. The sleepsack’s grip doesn’t loosen, but as she tucks the covers around me, pulling them up to my chin, I have to admit it does feel like a hug, warm and secure. She brushes a hand over my braided hair, her smile soft but intense. “Sleep well, my little Tinkydrew,” she says, turning out the chandelier with a flick of a switch. The room plunges into darkness, the only sound the faint howl of the wind outside.

I hear her footsteps retreat, then the click of the door locking behind her. My heart skips. I try to sit up, to move, but the sleepsack holds me fast, the laces and slots keeping me immobile. I almost laugh—why the lock? Why the bars on the windows when I can't even get out of bed? But the thought doesn’t stick. The sleepsack’s embrace is tight, almost comforting, like a whole-body hug, and despite everything, it soothes me. My eyelids grow heavy, the exhaustion of the day pulling me under. The scent of lavender and roses lingers on my skin, and soon I drift off.