(This story is inspired by the art of Fabulous Tasha and is dedicated to her.)
The taxi left Tommy at the front of his Aunt Hilda's country estate house. Despite his 21 years he was small and slight, and had to struggle to carry his two suitcases up the steps to her front door. To see him, you would never guess his age. He had fine features and no sign of facial hair, and was often mistaken for a boy of 14 or so. But really he was 21. Honest. Anyway, he reached up and lifted the heavy door knocker with an effort and let it fall. After repeating that exertion twice more he heard someone coming. The young man (okay, maybe he could pass for 15) took a step back and waited.
The heavy oak door was opened by a pert housemaid, quite young, with delicate Asian features. She looked at him inquisitively and he hesitated, taken by her beauty. She had an almost flat chest and narrow hips. Her hair was glossy black and worn in bangs, the rest swept up into a tight bun behind her lacy cap.
At last Tommy found his voice and said, "I'm Tommy Quayle, here to see my Aunt Hilda." When she didn't respond he added, a bit testily, "About my inheritance." Still she was silent. He snapped at her, "She's the executor of my late Uncle Hubert's will." Realizing his emotions were making him act rudely, and not wanting to distance the lovely maid, he added haltingly, trying to sound calm, "He was her brother." To impress her he added, "I'm due to receive the bulk of hisconsiderable wealth. I just need to learn the terms of his will." She curtsied prettily and waved him inside. Since she was as short as him, and a girl, he took the suitcases himself, struggling under their weight, trying not to look as weak as he felt, and followed her.
They came to a sitting room and she gestured him to a couch. He puffed
as he set down his bags and dropped onto the antique piece of furniture.
Mentally he was toting up all the valuable items around him, imagining
happily what it would be like to own them all and be fabulously wealthy.
The maid had left the room. Tommy envisioned a large-screen TV opposite
him and a state of the art video game system with it. No more worrying
about every dollar for him. His private dream was interrupted as the
maid returned with his middle-aged aunt following. Hilda was a handsome
woman, tall and imposing, with a thrusting bosom and wide hips. She
dressed in a somewhat old fashioned style. As a child he had found her
overbearing and demanding but now he was ready to take control. She
nodded curtly and said, "Hello, Tommy. Welcome to my home." He wanted
to remind her that soon the entire place would be his, but instead stood
and shook her hand formally, saying, "It's so nice to see you again,
Aunt Hilda. How long has it been?" "Too long. I'm going to enjoy
having you here," she said as she sat in a wingback chair. "Oh," he
told her bluntly, "I won't be staying."
"No?" She paused and went on, "Oh, yes, you don't know the terms of my
dear brother's will." Tommy suddenly felt cold inside. He said,
sounding more confident than he felt, "I can get a room at a motel until
tomorrow, if that's necessary."
"Not at all, dear. I insist that you stay here tonight. And your uncle
Hubert insists as well." She turned to the slender maid and said,
"Ming, please go and fetch those legal papers in the blue folder on my
desk." When the girl simply nodded, Hilda added, "You don't need to
remain silent. I give you permission to speak." Ming said, "Yes,
Ma'am," her voice soft, and went to get the documents.
Tommy squared his shoulders and said, "She can only speak when you allow
it? That's terrible. She's not your slave, you know." Hilda smiled
inscrutably and asked, "Isn't she?" He didn't want to anger his aunt
but, at the same time, he felt protective toward her servant. The woman
shouldn't treat the girl that way. Besides, he felt attracted to Ming.
His past failures with females made him overreact and he told his aunt,
"No, she is NOT your slave, not any more than I am, so please treat her
AND me accordingly." He brushed his longish blond hair off his
forehead, pushed it back on the sides, where it tended to fall over the
tops of his ears. Hilda didn't appear flustered at all by his words.
She waited patiently until Ming returned with the folder, then took and
opened it. Hilda extracted a sheet of paper and gave it to the girl,
telling her to hand it to 'my ill-mannered nephew'. He didn't like
being referred to that way, especially in front of Ming, but forgot all
about that as he read the first paragraph. His eyes went wide and he
stared at his aunt, saying, "B... but, this gives you total control over
me. I mean, it must be wrong. Uncle Hubert..." When his voice failed
him she completed the sentence with her own words, reminding him that
Uncle Hubert "... thought you were a brat. He recognized you for the
immature, overemotional, misbehaved child you were and still are.
That's why he stipulated that I should control your inheritance totally
until such time as I deemed you ready to receive it."
The young man was dumbstruck. He turned to Ming and the girl appeared
mildly amused by his predicament, though trying not to show it. He
checked the papers again. They were written in layman's terms so he was
sure of what they said. As of right now, unless he wanted to forfeit
all the money and property, his Aunt Hilda owned him. It was completely
unfair. He set the pages down gingerly and forced himself to look at
her. She appeared smugly satisfied as she announced, "As your uncle
wished, I am going to help you to mature and not act like a ninny.
Understood?"
He started to protest but saw at once that it would be useless, so he
simply replied, "Yes." She gave him a harsh look and said, "For
starters, you can address me with more respect. Please try again." He
swallowed with difficulty and then said, "Yes, Ma'am," as he had heard
Ming say. Aunt Hilda gave him a small nod of approval. She went on,
"My main technique will be to have you dress in a manner that will
remind you not to be arrogant, that will teach you not to look down on
females. With that in mind..." She paused theatrically. "...please
strip yourself naked." He froze. His mouth worked but no words came
out. With numb fingers he unbuttoned the top of his expensive shirt.
Then he stopped, unable to make himself go further. As if confronting a
minor problem his aunt said, "Oh my." Then, to him, she offered, "Would
it help you if I put you over my lap and gave you a good hard spanking?
It would be me taking down your pants, if that would make this easier."
He shook his head dumbly and then had the presence of mind to say, "No,
Ma'am. I'll do it myself." She smiled and observed, "See, you're
learning already."
Ming stepped close to him and held out her hand as he finished getting
out of the shirt. He gave it to her reluctantly. She eyed his narrow
smooth chest. Then he got out of his shoes and socks, setting them
neatly aside, afraid of angering his aunt. She watched him closely,
confidently, as he undid his belt and unfastened his pants, then lowered
his fly. Tommy stepped out of them and passed them to the maid. In
only his jockey shorts, with two sets of female eyes on him, he blushed
all over. Then he hooked his fingers under the elastic waistband, took
a deep breath, and slid the final garment down his slender legs and
stepped out of them. As Ming took them out of his hand he could only
remain where he was, on display. Aunt Hilda tilted her head down
fractionally as she focused on his crotch. In a detached tone she said,
"You have almost no pubic hair, boy. But I still want to get rid of
what little is there." To the maid she said, "Ming, dear, please go to
the bathroom closet and get the depilatory I purchased." As the girl
was leaving but still in earshot, Tommy's aunt told him, "Your genitals
are extremely small, aren't they?" He bit his lower lip and then
admitted, "Yes, Ma'am." She went on casually, "Do you think that's why
you've never been able to get a girl to have sex with you?" Distracted
by his nudity and her level voice, without thinking he conceded, "That's
probably the reason. Whenever I..." Then it struck him what he had
just confessed. Even though he was naked he felt suddenly warm. His
aunt said, "So you're a virgin, then." It was a statement, not a
question. He hung his head and told her that was true. She suggested
that he had been about to tell her that whenever he got a girl near a
bed she would see his inadequate endowment and lose interest, maybe even
laugh at him. Shamefaced, he verified that as well. "So," she
concluded, "you must masturbate to get relief." Beaten down and close
to tears, he told her, "Yes, Ma'am," but she wanted more. Aunt Hilda
wasn't happy until he recited in a slow clear voice that, "Yes, I
masturbate to get relief. Girls aren't interested in sex with me once
they see my tiny dick. I have to -- " She suggested the word for him
to use. " -- to wank myself regularly, at least three times a week."
"Well," she declared with finality, "that won't be happening under MY
roof. No wanking for you, boy. None at all. Swear that you won't
abuse yourself." He sniffled and pledged, "I will not wank my little
dick, Ma'am, while I am living here with you. I promise."
The maid returned with a plastic bottle of hair remover. Hilda
mentioned that it would keep hair from returning for at least a month
after one application. With continued use it would last even longer
each time. Then, instead of having Ming give him the container, she
ordered the girl to apply it herself, starting with his barely hirsute
armpits. Tommy shuddered with humiliation, but also from excitement at
the thought of having those delicate hands touching him. Wordlessly she
put a heavy dollop of cream on her fingers and set aside the bottle.
Then she indicated his underarm by pointing with her chin. He raised
his arm and she spread the cream where it was needed, then did the same
to the other side. It stung slightly as he had to stand there, hands in
the air, while the chemicals did their work. At last Ming took some
tissues and wiped away the lotion and his scant underarm hair. Next,
Tommy's aunt said, she would do the same to his crotch. He quaked with
nervous anticipation. She knelt in front of him and unhurriedly put
more lotion on her hand. Ming gently rubbed it all over the area just
above his little penis, covering what hair there was. Tommy couldn't
keep himself from getting an erection. Ming tittered at it and Hilda
said, "It doesn't get much bigger when he's excited, does it?"
"No, Ma'am," Ming answered. "Smallest I've ever seen." She also
smeared some of the substance on his immature balls. It began to sting
in both places and he stood there squirming with discomfort. They let
him stay that way for several extra minutes, while they savored his
discomfort. Then, at last, the cream was removed, leaving his crotch
and testicles as smooth as a baby's bottom. He cringed mentally at how
unmanly it made him appear.
"Next," Aunt Hilda decided out loud, I want you dressed in something
that will keep you from getting any ideas about giving me trouble.
Ming, why don't you select an outfit? After all, you did help me select
my nephew's new wardrobe." With enthusiasm the maid declared, "I'd be
happy to, Ma'am. In fact, I have some choices in mind already." She
went to a wardrobe along the wall and opened its double doors. Inside
were a variety of feminine articles, none of which Tommy wanted to wear.
He stood there shifting nervously from foot to foot. Ming took almost
no time to select a pair of lacy pink stockings with elastic tops. She
brought them to him and held his upper arm as he unsteadily slipped one
onto his foot and drew it up his leg, and then did the other. His aunt
made him walk around the room, instructing him to make his gait more
girlish. Then the maid brought him a red mini-dress with a corset
waist. He put it over his head, got his hands out the armholes, and
worked it down. He felt humiliated as Ming snugged the built-in corset
tighter and tighter, until it felt like it was cutting him in half.
There were puffs of see-through material at his shoulders and frills
around the hem of the snug bottom, which went only to mid-thigh. Worse,
there was a narrow opening in the front, a slit through which Ming
deftly tugged his undersized parts. Then she tightened laces at the top
of the opening so his genitals were forced to remain exposed. This time
when he moved around the room he was totally embarrassed by the picture
he made. Ming next decided that his protruding organ needed decoration,
so she tied a ribbon around his dick's base. Then she made a bow with
the remainder of the material. He wished his hard-on would subside but
it refused to cooperate. After that she picked out a pair of red shoes
with stacked three-inch heels. After he slipped his feet into them and
did the buckles himself, he had to totter around, learning to walk in
such unfamiliar footwear.
There was a wooden frame in the corner, on a wheeled stand, and Ming
turned it to reveal a full-length mirror. Tommy gasped at the image
that confronted him, of a foolish looking he/she who was more 'she' than
'he'. Still not done, Ming fussed with his hair and gave it a pixie-ish
style. Then she returned to the wardrobe one last time to choose a
wide-brimmed, flat-topped hat, with a ribbon that tied under his chin,
giving him a second bow to echo the one below his pinched-in waist. He
had to made a further circuit of the room, with the his Aunt Hilda
complimenting the fine job Ming had done of dressing him. But then,
when Hilda ordered him to stop in front of the dresser and she opened a
drawer and began taking out cosmetics, Tommy finally rebelled. He told
them, "Enough. I won't let you put make-up on me. I'm still a guy,
dammit."
"Are you?" Hilda said without losing her aplomb. "Really? A guy with a
tiny dick that has never been inside a girl is hardly a guy by any
definition I know. He is a sissy, what is what you are and will
continue to be the entire time you are here." He tried to summon up
courage to go on but now, denuded of body hair, dressed in such feminine
clothes, his underdeveloped male equipment on show, he couldn't find the
backbone to say more. Instead he let his shoulders droop and said, "I'm
sorry, Ma'am. I shouldn't have said anything."
"Well," she informed him sternly, "because you DID speak that way, you
must be punished. Do you understand?"
"P... p... punished?" he said uncertainly. She told him, "That's right,
boy. Or should I say 'girl'. Yes, it will be girl from now on. And
for punishment, Ming will push that tight dress up in the back to bare
your cute bum, and I will apply the crop to it until I believe you have
had enough."
"C... c... crop?" he asked disbelievingly, unable to stop stuttering.
And then, thinking of what it might cost him if he didn't get back into
line, he said, "Yes, Ma'am. You should do what you think is right. I
earned a p... p... punishment." As an afterthought he added, "Thank
you, Ma'am."
"Good girl," she congratulated. And then he felt Ming adjusting his
dress in back.
Suddenly his backside was bare and Hilda was taking a crop from a hook
inside the wardrobe. She gave it a few swings through the air that made
him tremble. She had him in a hopeless situation. He told himself that
he had to hang on for the days or even a full week that she intended to
keep him there. But once she had her gloating triumph he would take his
money and be gone. And with this home in his possession he could even
evict her. Yes, that was what he would do. Just as he was feeling a
rush of power the first slash of the crop landed across both of his
vulnerable buttocks. He yelped and stumbled forward on the heels until
Ming steadied him. She held on while the next trio of blows struck,
above and below the first. He was by then wailing like a schoolgirl,
unable to stand still, clutching his hands prayerfully together in front
of him and blinking back tears. His face got red and then his eyes
overflowed. Weeping and wailing, he gracelessly endured a total of 24
strokes. By the end he was sniffling and his lower lip wouldn't stop
quivering. All thoughts of defeating his aunt had fled. He only wanted
to avoid more punishments. That was the state of mind she wanted him to
stay in, too afraid to object to anything she demanded. Combined with
his new appearance, it should make it easy for her to remold him from
annoying nephew to sweet niece. Keeping him indoors, as if he was under
house arrest, would also help. And there was more to her plan. Much
more.
But for right then she let him regain some composure and allowed the
color in his face to normalize. Then she applied his first make-up,
working on his eyes, mouth and cheeks, going a touch heavy on the bright
magenta lipstick to exaggerate his new look a bit. This time when he
looked into the mirror he was horrified to see Tommy gone and a striking
girl in his place. Ming sprayed perfume on him as Hilda nodded
approvingly. The older woman announced, "You will be kept like this all
of the time. Ming will be in charge of your make-up and hair. If you
give her any trouble I'll take it out on your ass -- or elsewhere.
Right?" Unable to take his gaze off that mesmerizing reflection, he
said, "Yes, Ma'am, I'll be a good girl." Had he just referred to
himself as a girl? He couldn't believe it. But he had. Tommy told
himself he would hold on to his male persona, no matter what was done to
him. He would, he reassured himself, as he patted a stray lock of hair
back into place and noticed how well the shade on his lids brought out
his blue eyes.
This is a fabulous start to what is already an incredible start. And i certainly will be reading the rest
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