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Dressed Up and Dressed Down! By THRONE
🕑 Added 2026-01-21 17:23:15 +0000 UTCDressed Up and Dressed Down!
By THRONE
© 2019-2055 QoSBookclub
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This is a work of fiction. Names, characters, places, and incidents are a product of the author’s imagination. Locales and public names are sometimes used for atmospheric purposes. Any resemblance to actual people, living or dead, or to businesses, companies, events, institutions, or locales is completely coincidental.
***DEVIN DICKIE NOTE***
All characters are OVER 18 years of AGE! This is a bullying fantasy and not real. The acts in the following written work are only consensual sexual choices and fantasy humiliation scenarios.
Bullying is NOT OKAY and If you or someone you know is being bullied, please alert the authorities.
Dressed Up and Dressed Down!
By THRONE
A devilish young woman picks a weak 18-year-old and sets out to utterly destroy him. She wants to turn him into a mindlessly devoted, celibate sissy and steal all his money.
Dressed Up And Dressed Down
by Throne
This is an unkind story about a heartless young lady who relishes
systematically feminizing and breaking a defenseless young man. She
also intends to steal his considerable wealth. It is pure fantasy. You
have been warned.
Lawrence Wimbledon was in love. Or at least, he thought he was. At
eighteen, with plenty of family money, invested for him by others, he
was financially set for life. At the same time, he had no practical
experience with the workings of the world. He was especially deficient
when it came to girls. The short and slender fellow mooned over them
from a distance. When he approached one, his shyness reduced him to a
blithering dunce. That was why, when he met Sasha, only a year older
than himself, he couldn't believe how different she was. He didn't know
that the cute girl had researched him and that their encounter was
carefully planned. Lawrence fell and he fell hard.
She would tell him, "What I like about you is that you're so eager to
please me. That's the one true way to prove your sincerity."
With subtle methods, she would undermine what little ego he possessed.
It sounded like she was concerned but somehow always left him more
insecure than previously.
Sasha would say something like, "You're so lucky that none of the
rougher sorts of boys are around. I know you'd want to protect me from
them, but that you wouldn't be able to." After letting that sink in,
she might add, "Why, even a tomboy could push you around. I wouldn't
want to see that happen."
Along with warping his self-image, she teased him sexually. The wicked
girl knew how to send visual cues and say suggestive things, both of
which aroused him. The problem was that she never followed up with any
strong physical contact. Instead, she would lightly brush her fingers
over his cheek, ruffled his full head of hair, or smooth down his
clothes. Additionally, she used tricks like asking him to smell her
perfume, touch her hair and say if it was silky enough, or hold some
item of clothing she had bought in front of him, so she could see how it
might look on her.
In a short time, she had him following her around like a neglected
puppy, starved for any additional scraps of attention she might throw
him. After he was trapped in her web of manipulation, she took him down
to the next level. That involved picking his clothes, which took on a
distinctly girlish tone. When he questioned any of her choices, she
instantly became hurt. It didn't take much of that to teach him to
never doubt her wisdom. Then she began making demands on him. They
were small at first. He might have to take off her shoes and rub her
feet. Or she would have him buy her trinkets, which rapidly escalated
into gifting her with expensive items.
At some point she was able to convince him he should wear lingerie.
Sasha would say, "With your delicate skin, panties are perfect for you."
Or it might be, "I noticed how much you relax when you have a satin
mini-slip on under your silly boy's clothes." From there, it wasn't far
to, "You really need to dress in more soft clothes that won't make you
try to be one of those macho jerks who I hate so much." He was pushed
over the line and into dresses. Those became ever more juvenile, until
he resembled a very young female. Bows in his lengthening hair and Mary
Jane shoes on his petite feet amplified that image.
She pointed out, "You'll appear ridiculous if you try to strut around
like some musclehead while you're wearing what works for you. Take
smaller steps, Larry. And don't keep your wrists so stiff."
He was so smitten with Sasha that he barely noticed the stares and
snickers he was provoking on the street. When he did become aware of
those reactions, instead of rebelling against the controlling girl, he
became more dependent on her. He found himself paying her bills and
helping her out with cash. She was thrilled. What could be better than
taking over this rich lad and robbing him of his money, masculinity, and
future?
She would drive him to the mall, where he could be seen by large numbers
of people. Lawrence would stay close to her and avert his eyes from
anyone else. On occasion she would take his hand and lead him around,
as if he required constant guidance. When they went out to dine, she
ordered for him. His diet was adjusted, with less protein and more
empty calories. Seeing the weakling mince along, obviously in thrall to
the attractive young woman, people would stare and barely try to hide
their amusement.
It was time for him to descend to the third level of the hell she was
fashioning for him. Sasha started calling her willing victim Sugar
Puff. The first few times she did it, he started to say something. It
took only the slightest frown of disapproval from her to prevent him
from actually voicing a complaint.
She took him to what might be called a bad neighborhood. They went to a
cheap restaurant. When he took his first mouthful of food, she
introduced him to the scolding technique she had been eagerly waiting to
unleash on him.
"Sugar Puff," she snapped. "What are you doing?" Her sudden anger made
his mind go blank. Upsetting Sasha was unthinkable. She continued, "Is
that how you eat? Loading up your fork, shoving it into your mouth, and
chewing like a cow with a mouthful of cud? UGH! Are you some sort of
crude slob? Have you been pretending to be something other than what
you really are all this time? Are you now going to reveal your true
self and embarrass me in public?" He got so nerve-wracked that he
couldn't chew. A bit of food fell from his mouth. That gave her an
excuse to ramp up her attack. "You must be a brainless, pathetic, poor
excuse for a real boyfriend. I wanted us to be together forever but now
you repulse me. All you are is a pitiable, useless, dishonest little
monster."
The other patrons were entertained by her display. A swarthy young guy
in a tank top and cargo shorts came to their table. He sneered down at
Lawrence, who nearly fainted from stress.
The thug asked Sasha, "Is this jerk screwing with you? Want me to give
him some schooling?"
"Oh, thank you," she gushed, to Lawrence's horror.
Sasha stood and took the guy's hand. She pressed herself against him.
Lawrence was jolted by a rush of jealousy. In his mind, so well trained
by then, he blamed himself for pushing the girl he worshipped into the
arms of someone else. A violent shudder ran through the small guy in a
dress. When he tried to say something, Sasha allowed him to get out a
few disjointed syllables.
That was when she said, "Don't try to pick a fight, Sugar Puff. You've
already made enough of a scene. Please keep your voice down. In fact,
you need to speak quietly and modulate your tone not just now but all
the time." She put her arms around the stranger. "Thank goodness
there's someone to defend me against you."
The tough suggested, "You want to see my car?"
"I do need to get away from Sugar here, at least long enough to calm
down. And maybe being left alone for a while will give him time to
think about his terrible attitude."
"Sure," the guy said. "Whatever."
Sasha wanted to give Lawrence more to fret over and another round of
upbraiding would be the ideal way to do that. She put on a face that
reflected hurt and disappointment. "I hope you're happy now, Puffy.
You've ruined a perfectly lovely evening. I see how you can be a
despicable bully toward me. Look at you. So self-centered. Thinking
you own the world. Driving me away when I'm trying to get nearer.
Think about your wretched misbehavior, your pettiness, and the fact that
I'm close to tears now."
She clung to the ruffian. Sasha made sure to get his name while they
were still in front of Lawrence. The dusky one was called Stick. She
guessed why that was and made a point to ask him before they departed.
"You know," he said with lewd pride. Stick patted his crotch and
explained, "Because I got a big one."
With that final blow to Lawrence, whose penis was laughably tiny, Sasha
and her new acqaintance left the diner. As she went, unseen by him, she
gave their server a theatrical wink. The waitress answered with a nod
of understanding. The sissy sat there in stunned disbelief. What had
he done? Would she leave him there? Was the love of his life dumping
him? He was close to a breakdown.
Sasha, meanwhile, thanked Stick for stepping in. She said, "I've been
having fun turning that idiot into a total pansy. To be honest,
wrecking him has gotten me incredibly hot. How near is that car of
yours? I need some special treatment -- Stick."
He gave her a crooked smile. "Right in that vacant lot over there. I
can fix you right up."
They got into his vehicle and did the backseat boogie. It was animated
and sweaty. She didn't care if her hair was mussed and her clothes
disarranged. Sasha wanted to look well-used when she went back to
Lawrence. Let the twerp witness what a real man had done to her.
Naturally, she intended to make him believe it was somehow his fault.
This supposed failure on his part would be used to drive him even lower.
She came back and sat across from him.
"Now you've really gone and done it," she accused.
He stammered, "I'm so sorry. I didn't mean to..."
"Do you understand how serious this is?"
"Yes. The waitress even said something."
Sasha made a mental note to leave that girl a walloping big tip. It
would be with Lawrence's money, naturally. She resumed her tirade with,
"You didn't even say anything when that brute practically dragged me out
of here."
"What?" She had flipped the script on him. He was more mixed up than
ever.
While he was still mentally and emotionally off balance, she raked him
over the coals. "Anything could have happened to me. You are nothing
but a weak-willed, cowardly, simpering failure, Sugar Puff. This might
be our last night as boyfriend and girlfriend."
"No, no, no," he whimpered, slipping into mental freefall. "Please
don't leave me. I'll do anything you say. Everything you want."
"Well..." She crossed her arms under her bust, elevated her chin, and
looked down her nose at him. "I would have to require certain signs of
good faith from you. They wouldn't be negotiable." To gain some extra
insurance, she included, "And there would have to be absolutely no
backtalk from you. Not one single word."
"I promise. I swear." He blinked back tears.
Lawrence was so cornered at that moment that it sent her decadent lust
higher and higher. She wished she could return to Stick's car for more
of his primitive but effective treatment. With that option unavailable,
she could think of the long term and seal her deal with Lawrence quickly
and finally.
"If you really mean it, I'll give you one last chance."
"Thank you, Sasha. You'll never regret this."
"We'll see about that. And until this matter is settled, you need to
call me Mistress. Is that understood?" Her tone brooked no
disagreement.
"Yes, Sasha. I mean, Mistress." Lawrence kept his voice wispy. He
fluttered his hands. His lips quivered.
"Very well," she told him, maintaining her rejecting tone.
Sasha paid with his money and then drove him to her place. He had never
been there before. What should have been a happy occasion became
several hours of shame. She made him strip off his buckled shoes, ankle
socks, dress and panties. The big bow stayed in his hair. She liked
the image of him nude except for that. His comically small male parts
added to her pleasure. But there was more to be done.
"First," she intoned, "I have to get rid of your body's hair. There's
almost none of it, since you barely qualify as a male, but I don't want
you getting the mistaken idea that you're some sort of macho type and
trying to take advantage of me. That's why I'm going to use a hair
removal device I have for myself to get rid of every bit of it."
She took her time, to prolong his ordeal. He was visibly shaken by
having to be fully undressed in front of her. His dimly defined dreams
of someday having a sexual relationship with her were dashed by her
concern that he might try to force himself on her. Even though that
possibility was nonexistent to Sasha, she relished making him think he
had prompted a fear of it in her. After he was denuded of every hair,
she stood back to admire her work. Later she would reveal that the
laser tool she had used had caused the change to be permanent.
The next step was one she had been anticipating with secret glee since
the beginning. The devilish girl went and got an icepack. She also
brought with her a device about the size of a peanut. First, she used
the refrigerated plastic item to reduce his penis to even less than it's
normally miniscule dimensions. Then she slipped a ring around the base
of his now hairless scrotum. Finally, she fitted the cage portion over
his flaccid dick, compressing it to almost nothing. When she locked the
two sections together, her heart soared. A bride on her wedding day
couldn't have been happier than Sasha was right then.
"There," she said triumphantly. "Now I won't have to worry about you
doing anything improper while we're in bed together every night."
"We...? Us...?" He couldn't comprehend what she had just said.
"Of course. It would be wrong to leave you alone. As unstable as you
are, I'll have to provide constant monitoring, 24/7, including
overseeing all of your finances. Correct?"
Without thinking about the implications of that final phrase she had
slipped in, he agreed. All that was on his mind was the news that they
would somehow be living together. After all the trouble that he'd put
her through, Sasha was forgiving him. At the same time, he knew that
his uncompromised obedience would be needed if he wanted this heavenly
development to go on. Lawrence was more than willing to do whatever it
took, so inextricably was he entwined in her net.
That first night in bed was sweet torture for him. He was close enough
to feel the warmth radiating from her divine body. He could smell her
mild perfume and even the scent of her hair. His trapped member
attempted to erect but was stymied by that pecker prison. His miniature
balls throbbed. He didn't care. What did anything else matter if he
could be with his goddess, her in a sheer nighty and him wearing pink
pajama top and bottom of satin?
The very next day, Sasha used cosmetics on Lawrence. She also signed
herself up for college courses. She would need more knowledge to handle
the incredible fortune that was going to be siphoned away from him and
redirected to her. She already had it draining but wouldn't be fully
satisfied until it was entirely hers. She additonally got Lawrence into
several courses. They were low-credit ones from the institution's non-
academic program for women who wished to either marry or work in
unchallenging areas. They included sewing, decorating, and fashion
coordination. He meekly asked Sasha if she wanted him to also take
cooking, but she patiently indicated that would be too difficult for
him. He was so firmly under her thumb that he didn't object. To do
that wasn't even conceivable to him.
Lawrence was quite a sight as he walked on campus or sat in the quad
with his mooning gaze directed toward whichever building his love was
attending a class in. Students couldn't believe they were seeing that
short guy always attired like a little girl, who swished when he walked,
talked as if he was prepubescent, and displayed the body language of
someone doing a meanspirited imitation of an effeminate homosexual. His
behavior was so extreme that there was zero sympathy for him. Even gay
students were put off by the teen, though several jocks took more than
one look at his pouty lipsticked mouth. He was simultaneously insulated
by his focus on Sasha, and yet still in touch with the real world enough
to be deeply shamed.
The remorseless girl didn't ease up on her prey. Instead, she
intensified her efforts. She constantly reminded him of what a failure
he was. Her tongue-lashings were merciless.
"Why can't you do better in your classes, you simpleton? Don't you have
enough intelligence to sew two pieces of clothe together?"
"I get d... distracted," he said, barely audible. She now had him
pronouncing 'S' sounds like 'th'. "All I can th... think about is..."
"I know. Your mind is full of me. That's right. Blame Sasha, who does
so much to help and protect you. You want to make your lack of
accomplishments my fault. Don't try that again. I'm tired of such a
cheap trick. Why do I have to be burdened with a lisping, stuttering,
prancing clown who's less concerned with me than with flirting with
every jock on campus?"
"But I'm n... not," he wailed. "I don't want those big boys touching
me."
She shook her head. "I can't tell who your lies are more meant for, me
or yourself. Be honest, Sugar Puff. You make eyes at all those locker
room lotharios, especially the football team members."
"I d... don't. I mean, I don't think I do," he sniveled. "It's just...
just..."
"It's not fair to me, that's what it is. I have a heavy class load.
You're the one taking courses for birdbrains and in danger of failing
them."
She drew back her hand, as if to slap him across the face. He flinched.
Then she slowly lowered her arm. That brief pantomime made Lawrence
think she had relented out of consideration for him. He was
speechlessly grateful. The boob even sank to his knees. He hugged her
lower legs. She allowed it just long enough for him to have some
contact. That made her imagine his puny pecker trying to stiffen inside
the unbreakable chastity. Sasha was soaking through the gusset of her
panties. She knew he could smell her sexual juices, even if only
without being aware of it.
After he'd had enough touching to leave him painfully frustrated, she
barked at him, "What are you doing down there, you puerile pervert?
Sick freak. Kinky creep. How dare you drool over my legs. Thank
goodness I put that cock lock on you. From now on, every time your
pitiable prick tries to get hard in it, you're required to thank me for
regulating your runaway sex drive."
"Yes, Mistress. Thank you, Mistress." Lawrence wept.
Sasha planted one foot in the middle of his narrow chest and pushed him
over backward. She left him like that, sprawled in an undignified pose,
the hem of his dress up, as she turned on her heel and left him alone.
He thought she was going because he was so annoying. In reality, she
left to go and make use of a new sex toy she had just acquired, a long
girthy dildo she called Big Bang. A few orgasms from that would bring
her back to Earth, so she could think clearly and subject the target of
her sadistic impulses to more manipulation and abuse.
Before the middle of the semester, Sasha had attracted plenty of
desirable guys. She settled on one named Linc, who was there on a
basketball scholarship. She had him come to her off-campus apartment so
Lawrence could experience extreme pangs of jealousy. He knew he had no
way to compete. Instead, he tried to please Linc, with the twisted
thought that he would indirectly be pleasing Sasha. The tall young man
viewed Lawrence with scorn. He openly disrespected him, which Sasha
coaxed him to do more of. Worst for the sissy, Sasha would take Linc
into the bedroom, leaving the guy she lived with out in the hall, on his
knees, to be handy 'in case we need anything'. He has to listen to
their loud and seemingly endless lovemaking. Even as naive as he was,
he understood what was happening. It did irreparable damage to his
psyche. When Linc stayed over, Lawrence was allowed to sleep by the
bed, curled up on a thin narrow mattress meant to go on a cot. He was
given Sasha's discarded panties to clutch and press against his face.
Were there limits to how utterly she could break him? His insecurities
had been exaggerated to gigantic proportions. He was sometimes reduced
to a dithering imbecile. Sasha considered that, beyond a certain point,
she might be repeating herself, or merely driving the lessons she had
already taught deeper but accomplishing no new damage. The heartless
bitch had to admit that she might be near the end of a journey that had
brought her incomparable joy, at the same time it crushed an innocent
and left him a hopeless pansy with no coping skills. As much as she
would like to drag his misery out indefinitely, there would come a time
when her great experiment was over. Besides, she had made the right
arrangements to insure that he would never again see a penny of his once
considerable wealth.
What Sasha decided was that she shouldn't be greedy. Someone else could
get their sick kicks out of inflicting new cruelties on Lawrence. They
might fixate him on some obsession, like a fetish for shoes and boots.
Or take him further along the sissy road and make him have sex with men.
So many tempting possibilities.
Her final decision was to let him finish the school year. She would
make sure he flunked all his courses, to deny him any confidence he
might have gained from passing even one. There were those on the Dark
Web who sought someone like Lawrence, already broken but still capable
of being humiliated and feeling shame. She located a spoiled rich girl,
tyrannical and possibly psycho, who was hungry for a victim to move in
with her and mistreat. Yes, that was an appropriate fate for Lawrence
or, more accurately, for Sugar Puff. After all, Lawrence was almost
gone and would soon be lost forever.
