Timmy
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"Timmy"
Timmy had been spending summers with his aunt Madge for several years.
She had caught him in her lingerie drawer when he was nine and after a
spanking and a severe scolding she had thought the episode was now in
the past. But the next summer when he was ten it happened again!
After another scolding and a few threats to expose him as a little
sissy Madge was confident her nephew was now back in line. And for the
next few summers it seemed so. But now, this year with little Tim now
thirteen and the summer vacation at Madge's only two weeks old she
began to notice that someone was going into her closets once again.
She immediately realized that Timmy was still getting into her things.
She even noticed he had adjusted some of the straps on her slips and
brassieres! She knew a spanking at his age was out of the question,
and instead of directly confronting him for yet another scolding that
probably wouldn't work Madge decided to make a few plans of her own and
then wait until she could catch him in the act.
Several more days went by and then another week. Timmy was still
getting into Madge's things but finally on one Friday morning she
returned unexpectedly and found to her suspicions that Timmy was indeed
the culprit!
She entered her bedroom to catch him mincing around the room in a
brassiere, a pair of her nude support pantyhose, her pink satin panties
and a pair of her pink high heeled bedroom slippers! She noticed he
was wearing her lipstick and some eyeshadow and he had combed his long
brown hair and had added a pink satin hair ribbon! He wasn't wearing
the clothes quite properly and his amateurish makeup and hairstyle were
ill fitting as well.
He gasped when he saw Madge standing there speechless, her anger
growing then tried to stammer an apology but before he could start
stripping away the clothes and make a hasty escape back to his bedroom
Madge grabbed little Timmy by the arm and marched him forcibly from the
bedroom with Timmy apologizing all the way! Little did he know that it
was now aunt Madge's turn!
It took an hour or so, maybe two but it didn't matter because little
Timmy wasn't going anywhere now. And soon he found himself back in
Madge's feminine bedroom! The shiny rayon and taffeta floral party
dress hung from the open closet door and the dresser drawers hung open
now brimming with frothy, lacy lingerie. Little Timmy wasn't
apologizing anymore and except for the quiet sniffling sobs all that
could be heard in the bedroom was the sound of swishing lingerie and
rustling skirts as Madge continued looking through her outfits. She
then found a small white satin corset and turned her attention back to
Timmy!
It didn't take her long to get the corset hooked around Timmy's waist
and properly centered. She then began pulling and tightening the white
silk laces. Timmy felt the corset tighten, he could smell the strong
floral and feminine scent of the perfume that surrounded him. His look
now was anything but amateurish! A gasp and another sob came from his
glossy red pouting lips. He batted his eyes not being used to the long
false eyelashes and sobbed again as he caught his heavily made up
reflection in Madge's full length mirror. He sobbed and sniffled once
again to notice his hair was now a mass of feminine curls complete with
a pretty satin bow that had been expertly fitted and applied.
Madge didn't say anything as she continued. Timmy didn't say anything
either, he knew he was being punished. The corset laces swished and
zipped through the stainless steel eyelets at the back of the corset as
Timmy wobbled on the white patent leather ankle strap stiletto pumps
with the five inch heels. He noticed the delicate little white leather
bows at the back of his heels and could see his glossy red toenails in
the open toed pumps even through the sheer beige nylon stockings he now
had on. He wobbled again as Madge pulled the laces tighter still
causing Timmy to gasp in surprise as his waist continued to shrink into
a more feminine hourglass shape. He felt the heavy silicone breast
forms that Madge had affixed to his hairless chest and how they filled
the white lace trimmed satin brassiere and how they swung and jiggled
in front of him. He became a bit dizzy and swooned as he fell against
the corner post of Madge's four poster bed but soon regained his
footing and held on tightly to the post, his manicured nails lengthened
by an inch with salon nails were also done up in a high gloss red that
matched his pedicure and lipstick perfectly. He felt the long dangle
earrings in his newly pierced ears as they swung and brushed against
his neck with every move.
He closed his eyes and quietly sobbed as he held the bed post. He
didn't have to look anymore to realize what was happening. He could
feel his large bust jiggling in his brassiere and felt the tightness of
his now girdled crotch and had noticed that after Madge had finished
pulling and tucking once she had the heavy paneled white nylon and
lycra spandex panty girdle up high and tight on his waist there was no
longer a trace of Timmy's little bulge! His tightly puckered girdled
crotch now resembled a woman's trim little mound, the padded hips added
width and roundness to his hips while the white satin corset now
gleaming tight shrunk his waist which further emphasized his now wide
and womanly hips!
He felt Madge finish with the lacing then felt her tie the laces into a
tight double bow at the back. She stood back momentarily to survey her
work then without a word she went to the dresser then returned with a
white, lace trimmed nylon full slip and two white nylon chiffon
petticoats. Madge put the trembling little Timmy into the white full
slip and quickly fitted him into the fluffy petticoats tying them
tightly around his now tiny corseted waist. He heard the swish and the
rustle of the floral patterned dress as Madge brought it over from the
closet. He heard the swish of the zipper as she took it off the
hangar. After setting the satin covered hangar aside he heard the
material swish once again as she held it open for him.
He felt Madge fluffing out the dress and straightening it then heard
the whisk as she pulled up the long back zipper and he felt the dress
tightening around him fitting to his new form. She quickly tied the
white satin sash around his waist into a large and feminine bow at the
back. She then clasped a pearl necklace around his neck, fussed with
his curls and added a bit more hair spray and perfume. She looked him
over once more then checked the white scalloped collar and finished
smoothing out the shiny floral dress as Timmy stood silently wobbling
on the high stiletto heels.
With Madge now satisfied he watched as she quickly closed the dresser
drawers and closet doors straightening the room. She moved to the
vanity and put away all the makeup then paused as she checked her hair
then added a bit of perfume. Satisfied with her refreshed look Madge
then turned and left the bedroom.
Timmy stood in stunned silence for a moment not knowing what to do. He
knew for certain though that after all the work Madge had gone through
that he had better not try and take anything off. But what could he do
now? He couldn't go outside, he couldn't hang out with his friends.
He began moving, wobbling on the high stiletto heels. He gasped as the
shoes forced him into short mincing steps that caused his hips to
wiggle and his jutting bust to swing and jiggle. He heard the crisp
silken rustle of the dress and petticoats and smelled the perfume that
floated around him like a cloud. He felt the tightness of the tiny
corset, tasted the lipstick on his lips and felt the earrings as they
brushed his neck with every step. Then finally too embarrassed to face
his aunt Madge and with nowhere to go he made his way to the edge of
the bed and sat down. Now in a feminine sensory overload Timmy gasped
yet again and could only bury his face in his salon nailed hands as his
head spun in disbelief.
Madge had only scolded him and sent him to his room after catching him
in her things that first time. The second time she scolded him then
told him if he ever did it again he would really be punished. Maybe
she would tell all his friends or make him go shopping to be seen by
everyone outside! The thought of going out dressed as he was now made
him shiver with fear because not even little girls dressed this way
anymore and he would be sure to stand out to be laughed at and
ridiculed! And he knew he couldn't take the intensity of being forced
into a dress shop to browse the dress and lingerie racks either but he
knew that was a possibility now. Madge had also mentioned making him
stay dressed every day for the rest of the summer and become the "lady
of the house" and do all the cooking, cleaning and housework for an
added punishment! He waited a few more minutes sitting on the bed
worrying which punishment his aunt would choose. But then as a few
more minutes passed and nothing happened he figured that after Madge
let him worry for a while that it would be sufficient and it would once
again be over, his latest lesson finished. He had already made it up
in his mind to stay out of his aunt Madge's things from now and on and
promised himself that this would be the last "lesson" he would ever
need!
A few moments later as he cowered on the bed he heard Madge enter the
room and looked up with tear stained eyes to see she had on a scarf, a
light spring coat and was carrying her purse as if she was going
somewhere. She also carried another coat, a feminine styled white one
that would compliment the floral rayon dress he now had on. Then he
noticed the white gloves, the little hat and the matching white purse
she held as she stood in front of him with a vengeful smile.
She explained her plan as she quickly fixed his makeup and added more
perfume then bobby pinned the little flowered hat to his now curly
feminine hair style and put him into his coat. After hooking the
straps of the little white purse through his right arm and forcing him
to take hold of the little white gloves in his right hand she began
marching him out of the bedroom and towards the back door!
Timmy could already hear his friends gathered and talking outside on
the back porch that led to the garage. He began to whimper and pull
away as he squirmed and struggled now but it was no use. He gasped in
terror and felt the blinding reality as his head spun! His knees
buckled as he stumbled on the high heels but Madge only continued,
pulling him towards the back door and outside to fully realize his
punishment! He could see two of his friends already looking into the
kitchen window now as Madge opened the kitchen door that lead outside.
He felt his stomach tie in knots and felt the dizziness of his panic as
his mind reeled! He was told to be quiet, there would be no escape
now. He knew he would be taunted by his friends but he knew that was
only the beginning. And he was told that if he acted like the perfect
little lady he might just get by but either way Madge had decided to
put an end to Timmy's little habit once and for all, at least with her
things. And then Madge opened the screen door and pulled Timmy
outside!
He gasped as he felt the cool morning air swirling around his shaved
and nylon stockinged legs and felt the breeze as it fluttered his dress
and petticoats. His face flushed under the makeup as he heard the
gasps, the disbelief and then the laughter and taunts from his friends
on the back deck looking on while Madge led him to the car. "Little
Timmy caught wearing his aunties clothes just like a little sissy!"
One of his friends jeered as the others taunted and pointed and laughed
as Madge led Timmy down the steps and across the sidewalk. He felt
himself gasp and struggle to click a swallow through a dry throat as he
struggled and minced on the high heels. The boys saw it all now, the
makeup, the hairstyle, the flowered hat, the pretty floral print dress
and the little car coat and how little Timmy held his little white
purse and gloves just like a girl and how his skirts swished and
billowed in the breeze and how his smooth nyloned legs shined in the
sunlight and how he minced and wiggled in quickstep as Madge pulled him
along!
The laughter continued and echoed in Timmy's ears as Madge let him into
the garage and put him into the car. There might have been a fight if
Timmy had been out on his own but the boys knew better with him being
escorted by his now determined aunt Madge.
The boys, now Timmy's former friends drifted away, some on bicycles
some afoot but all still laughing, talking about what had happened
knowing it all now as they watched Madge and Timmy back down the
driveway. Timmy's head spun, his heart pounded and his stomach churned
as she headed the car downtown. He now knew what was in store. His
aunt Madge was taking him shopping, shopping to get enough dresses,
lingerie and high heels to last him for the rest of the summer! There
would also be a trip to the beauty parlor to have his hair dyed blonde
and done up in a feminine styled permanent that couldn't be combed out!
Everyone on the street would now be able to watch and notice as Madge
led her little Timmy on their shopping spree into the dress shops the
lingerie and the shoe stores where there would be more people to see
him, corsetieres to fit him into more lingerie and dresses and shoe
salesmen to fit him into shoes. Would they act professionally or did
Madge make further arrangements so they'd comment, giggle and maybe
take sadistic pleasure in seeing a little sissy of a boy being well
punished as they feminized him to the limit? They would also see her
leading him into the beauty salon where all the ladies inside would get
their turn to look and point and comment on the little sissy that was
Madge's nephew and then he would be put into a salon chair where still
more work on his look would continue. He cringed at the thought of
what might happen, a woman hairstylist actually getting to work on a
boy in a ladies salon! He felt sick now, beside himself with a panic
he had never felt before as he squirmed on the seat then felt his long
lashed eyelids flutter as his mind reeled. He could only lay his head
against the headrest in disbelief as he awaited his fate!