Homeless Boy Becomes Princess 💖👗 (Crossdressing Stories) 

Robert was disgusted with everything; his landlady, Mrs. Riley, had just ejected him. She had simply closed the door on him; she wasn't usually so aggressive. For the previous four hours,

Wondering what he was going to do with himself, he wandered the filthy, crowded streets. He sought to stay dry by gathering in the doorway of a shuttered store. Two homeless people were huddled in another doorway further down the street, shielding themselves from the rain. The idea of living on the streets did not appeal to him.

He was a little man with a lot of black hair on his head that hardly ever grew any

all over his body, except for the typical bush between his facial hair and

with a thin layer covering his legs. Once more, he peered down the street and

shuddered to think about what he would have to go through to live on the

streets. With his shoulders bowed, he quickly left this area of the

direction of the better-lit portions of town. He did not look at anyone as he

felt as though someone was keeping a close eye on him. He strolled

swiftly to the more desirable area of the city and paused in front of a boutique

standing beneath the awning that covered its window display to stay dry

from the sun.crossdressing stories

As he stood there contemplating what had transpired, he began to

comprehend the reason behind Mrs. Riley's expulsion of him. Tony Harris possessed

called the previous evening, hounding Robert to go for a

a little enjoyable. He was the kind of individual who was more of a

follower because of his little size. He'd been the same way all along, and

He discovered how to prevent bullying when he was a foster child.

was to follow the older kids' lead. Tony had persuaded Robert to

joined him, and together they enjoyed some joy riding in a stolen car. They possessed

been halted by the neighborhood police, who detained Tony because he was

wanted on several charges of car theft. Robert had been set free.

Following a warning and six hours, the young man had gone back to his

by the bed.

After waiting for him, Mrs. Riley's face was drawn into a

scowled with a pinch. She waited for him to provide an explanation for his behavior.

She examined him thoroughly; his appearance left a lot to be desired.

in any case. There she had been, all business attire, and she had

went into a rant about how she would never allow someone to have a room

criminal. She had slammed the door in his face with that, not even

Permitting him to retrieve his possessions. This made him just stand there.

staring open-mouthed at the securely closed object for at least five minutes

door. Following his decision to stroll through the town, and subsequently

When the furious woman had had time to return and attempt to reclaim his property,

Calm down.

Standing beneath the awning, he examined his sodden garments and the

His hair was a mess from the rain. He pivoted to gaze downward at the

He noticed a stone the size of his fist beneath the concrete pavement. This he

He took it up and gave it a feel; the weight felt right. He

shook it in his hand and thought about his life's events.cross dressing 

He hurled the stone toward the street, the toss he

erred in judgment and fell as well. The stone flew out of his grasp and

It made a neat hole in the window's plate glass. He was standing.

For a little while, he was stunned by what he had done.

He hastened to get the word "vandal" permanently inked on his face.

The sense that something was watching him was growing stronger. He moved to

an intersection, where he paused for a few while before giving it some thought.

what he intended to do. He was standing there when a modern four by four pulled

the passenger window slid down next to him.

crossdresser stories

The voice inside said, "Hello!" with a strong yet kind tone.

Robert said, "Hello," a little unclear about the direction this was headed.

"You look as if you could do with a hand."

"Yeah life's a bitch at the moment."

"Well can I give you a lift somewhere?"

"I'm not really going anywhere."

"Any where is as good a place as any. I'm Julia Stevens."

"A pleasure Ma'am."

"Well get in."

Robert jumped into the four-by-four's passenger seat and received a

take a close look at the female. She appeared as if she was accustomed to being in

in control of the circumstance, and her attire was nice. She took a seat at the

Her meticulously manicured hands lightly resting on the vehicle's controls

steering mechanism. There was a gold bracelet on her wrist with a

strange sigil. It appeared to be an eye, and it appeared to be

glancing at Robert. It appeared to wink as he stared at it, so he did a

He gave it a second look and took his seat again. He became comfortable and he

could hardly see over the big car's dashboard, Julia

began to converse and inquired about his background.

He felt compelled to reveal his secrets since Julia appeared determined to do so.

Think about his responses. She inquired about his early years and the

kinds of games that he was formerly into. He needed to focus because there was one

something he wanted to keep private. Growing up in foster care, he

used to spend a lot of time playing with the housegirls. His greatest joy was playing.

house with the young girls; because of his stature, he was consistently chosen to be

the family's little girl. He delighted in this since it meant he wasn't

attempting to compete in a sport with the boys. He began to consider

where he had made a mistake, the companionship he was compelled to maintain while he

become an adolescent.

They continued to converse while driving through the town;

The car was obviously top of the line, thus the ride was smooth. They

drove out of town, toward the more expensive homes in the suburbs.

and Robert was beginning to worry about his future. Julia halted

asking inquiries and focusing on her driving because the routes provided

route to rural roads. She always knew what to do and drove like she looked.

she carried out. Robert focused on the woman and saw what

wtf on her. She was, he thought, what he would call

authority attired. a charcoal work suit and white shirt, also her

Legs had a decent amount of definition. She appeared as though she could pass as well.

thought of as a prosperous business family's nanny.

boy to girl

His eyes scanned the interior of the car before focusing on something on the

It was a child's booster seat in the back seat. It was positioned toward the back.

passenger side of the car; a rag doll was sitting there. Additionally, on the

Large blonde teddy bear with a set of children's books was on the back seat.

coloring pages. Julia pulled into a lay-by beside a field.

"Maybe if Robert could see where we are, he would be happier.

heading?" she inquired softly.

Yes, Ma'am, that could work better. I could then let you know when I

desire to leave."

Julia stepped out of the driver's seat and made her way to the

through the passenger door. She unlocked it and simultaneously unlocked the back.

door. Robert turned to face the back as she motioned for him to, and

discovered that he was raised onto the booster seat. He briefly displayed a crimson

while Julia buckled his seat belt. He attempted to inform her that he

might move the rear-facing booster seat to the front seat. Julia informed him.

that, unlike little children, she would not disobey the law

ride in the backseat of vehicles.

Robert argued, "Ma'am but I ain't a child!"

crossdressingstories

"Do you think a police officer would believe you are guilty if he stopped us?"

an adult?"

After doing so, she shut the door and turned to face the driver's side of

the vehicle and resumed their journey. Robert sat down in the now

He could see more from the front seat than from the back seat. He was

sitting in the back seat, growing bored, and wanting to do something he

peered through the coloring books. They were designed with young females in mind.

featured a Disney motif. Observing from the window, he noticed that they

had entered the rather lengthy driveway. They took off, and as the

As they approached the towering house, the driveway curved and he was able to view it.

in front of the dwelling.

crossdressing stories

Robert attempted to unbuckle his seatbelt as the car slowed and eventually stopped.

It appeared to be congested, so he had to wait for Julia to arrive in order to

Let him go. She turned around fast, let go of him, and without

Letting him reflect helped him get up from the chair. She additionally placed

she grabbed his free hand while he held the teddy bear in his arms. He was just getting started.

to get concerned about what he had entered when he felt a light tug, but

firmly in the direction of the home. They arrived at the staircase that led to the

Julia continued towards the front entrance of the house and

walked down the house's hallway. Julia came to a halt and let Robert

Take a peek around; it was tastefully equipped. then Julia

point Robert in the direction of the house's upstairs and a bedroom that

was nearly nude. She told him to freshen up as she would and left him there.

would send the maid to fetch him and would wish to chat to him.

cross dressing 

Sitting on the bed in the empty room, he let his thoughts come to mind.

for the first time since getting to know this confident lady. He thought about

the tone of her inquiries, and he gradually came to understand that she had

planned for him, and he questioned whether he would be able to influence those plans. He

glancing around the space, he noticed a door leading to an ensuite

restroom. He determined that it would be better to adhere to the

guidelines and give yourself a quick shower. After taking off his shirt and jacket, he

He spent some time to bathe and attempt to clean himself.

get himself back in order.

A small tap appeared on the after he had cleaned himself off.

entrance to the bedroom.

A soft voice informed him, "Sir Madam is ready to receive you now."

crossdressing stories

He noticed a maid outside wearing a somber outfit, yet

She had a smile on her face and a nice expression. The tone was

The maid noticed the teddy bear and grinned, feeling warm and pleasant. There

was concealing a secret, but it wasn't a terrible one. She held out.

Robert to accompany her, and she guided him through the hallway and down

steps. She continued to talk lightly about Miss Stevens and the mansion.

She informed him that Miss Stevens was the owner of a chain of upscale stores.

across the nation.

crossdressingstories

Following his hearing of this, Robert began to worry about the reason he

was here, he pondered the stone-related mishap. He questioned whether

The woman who had picked him up owned a several stores, including this one.

and carried him over here. Molly came to a stop in front of a door and tapped.

twice, then awaited a response. Following her apparent hearing of a voice from

She led him inside to a room filled with floor to ceiling bookshelves. Julia

A file was open on Stevens' lap as she sat in a deep recliner.

She grinned as she looked up. She gestured for Robert to have a seat on her

footstool before the chair she was seated in.

Robert crossed the room cautiously, took a seat where it was suggested, and waited.

for the female to start talking. In a matter of seconds, Julia Stevens appeared to

returning to the document she was examining, in reality, she was viewing the

The way a young man behaves. After a short while, he appeared to calm down, and her

observations kept coming as he unwinded and appeared to no longer need to

release a picture. He pulled his legs in and changed how he was sitting.

together and gently pressed his hands together in his lap. Julia

observed, thinking that when he unwinds, he seems to act like a

young lady.

boy to girl

Robert waited calmly for Julia Stevens to determine that she

was prepared to speak with him. He shifted his body so that he could

felt right for him. He noticed that he was settling into the manner of

sitting that he had learned to sit from the young females in the house. It

appeared to be a natural and comfortable position for him to sit, and he appeared to

unwind even more. Additionally, his fingers slipped to his mouth while he sat there.

then he brought a few hair strands to his lips. He began munching on

It was an instinctive coping mechanism for stressful situations.

Click here for >> New Story