Authors note: Given the lack of female to male cross-dressing stories, I decided to dive into this genre. Scant few authors seem to handle the topic appropriately. Only one handles it properly, and to her/ him, I kozmically tip my hat.

To further spur interest in the topic, I'd like this story to be a thought started for a female to male cross-dressing universe called 'The Wishing Stone' . I realize that the story here is lightweight as are the characters. Therefore, I offer the characters and situations to others expand upon. However, as I hold my characters very dearly, I impose only the following rules:

The stories must be female to male cross-dressing (with emphasis on underwear) in nature and not body swap/ transformation. No male to female cross-dressing with these characters. The female characters must never actually have penises.

2) No sexual situations

No abuse or harm or humiliation must ever come to the characters

If other characters are introduced the above rules apply to them too.

Thank you -- enjoy!

 

Like Brother Like Sister

by

Trapper Jock McIntyre

 

Stephanie-Anne Hunter sat in her bedroom staring out the window. Her brother was in the driveway bouncing a basketball. Lazily he lofted it into the air scoring a basket. He made it look all so easy, she thought. But then again, everything about being a boy was easy.

Her brother Joseph was 15 years old and everything she wanted to be. At night she'd lie in her bed and hope that when she was 15, she'd be just like him. But as Stephanie-Anne was a 13-year-old girl, this was of course impossibility.

She went downstairs and out onto the front porch. She sat on the steps and watched her brother. Stephanie-Anne wished that she could be the little brother instead of the little sister and join him in a game of hoops. She imagined standing next to Joseph in bathroom, her face all lathered up in shaving cream as he taught her how to shave. She could seem them both standing there both wearing a pair of boy's white fly-front briefs.

She sighed. Stephanie-Anne didn't necessarily want to be a boy; she really just wanted to be treated like one.

"Hey Joseph, can I shoot a few baskets, too," she hollered.

"Nah, go away! You're a girl. Scram!" he answered back.

"But I can play too, can't I," Stephanie-Anne insisted.

Joseph tossed the basketball to the basket "Nope, you're a girl."

"Well, couldn't we just pretend that I was a boy?" she asked.

"Duh! You're a girl, now scram," Joseph replied.

Stephanie-Anne went back into the house and to her bedroom. At least she could pretend on her own. She slowly and quietly closed the bedroom door behind her then crept over to the old teddy bear that sat on her bed. The bear had a rip in the one seam under its arm. Stephanie-Anne dug a finger in the seam and began pulling something from inside the stuffed animal. Once extracted, she snapped the item in the air to shale out the wrinkles. The secret item was a pair of boy's underwear.

Stephanie-Anne set them on her bed and began to smooth out the wrinkles. She had stolen them from her cousin Mark last summer when she went her family went to visit her aunt and uncle. Mark was her age and she spent the visit imagining what it was like to be him. When no one was around, she would look into his bedroom and imagine what it was like to sleep in a room that wasn't all girly-girl.

On the morning that her family was getting ready to return home, Stephanie-Anne decided that she needed one last look around Mark's bedroom. Everyone was packing things into the car, so she made up an excuse about needing to use the bathroom. While everyone was outside, she snuck into Mark's room. She opened the door to his closet and ran her hands long Mark's shirts and pants. Stephanie-Anne then moved from the closet to his chest of drawers. She opened the top drawer and looked over his socks, all neatly folded and arranged. Then she pulled open the second drawer. Mark's briefs were all perfectly arranged. She ran her hands over them, and closed her eyes. Her mind drifted off to thinking about what it was like to wear underwear like this, so soft and cottony, not like those nylon panties her mum bought for her. She tried to imagine what that fly opening on the front boy's underwear felt like when you wore them. Her mother yelling for her and her father tooting the horn on the car interrupted her fantasies.

"Stephanie-Anne, hurry up, we're ready to go."

She heard the door to the house open, and just as quickly she grabbed a pair of Mark's underwear and stashed them in her back pocket. She then slide the drawer shut and went running down the steps.

It was this pair of boy's underwear that she was now smoothing the wrinkles out of. Once they were her cousin Mark's underwear, now they were her boy's underwear.

Stephanie-Anne took off her jeans and the t-shirt was wearing and tossed them on the bed. Then she removed her panties and threw them across the room. Standing there in just her knee socks, she picked up HER boy's underwear and stepped into them. She slowly pulled them up her legs and snuggled them around her waist. She then walked over to the mirror that was attached to the back of her bedroom door.

Stephanie-Anne never ceased to feel a little thrill at the sight of the reflection that she was now looking upon. Her boy's underwear was white with little grey lizards all over them. The wide grey waistband had a red stripe and the words Fruit of the Loom on them. It was about and inch wide, unlike that wimpy lacey waistband on her panties. And those lizards looked so much cooler than the flowers on the panties. And then there was that all-important fly opening, the thing that made these so unlike panties. She ran her fingertip along the stitching of the fly, the fly of her boy's underwear.

She smiled as she looked at herself. Dressed in her panties and training bra, Stephanie-Anne definitely looked like a girl with her long fingernails and her long hair cascading about her shoulders. But when she was wearing her boy's underwear, Stephanie-Anne thought that she looked a little bit like a boy, albeit one with long hair and nails like a girl and small girlish boobs.

Then feeling a bit bold, she decided that she was going to wear them in front of her parents. She pulled her t-shirt on and looked in the mirror. She could she boy's underwear peeking out below her t-shirt. The t-shirt was white with powder blue sleeves. A playful kitten adorned the front of it.

She then picked up her jeans and pulled them on. They had flowers embroidered on them. Finally she pulled on her sneakers. As she sat on the edge of the bed she looked around her room. Her mum had made it all look all feminine with ruffled curtains and flowery wallpaper. Stephanie-Anne's Junior Girl Scout uniform hung on the doorknob to her closet, a closet filled with dresses and skirts.

Giving herself one last check she nervously went downstairs to join her parents on the patio. She wondered if they'd know that she was wearing boy's underwear.

She plopped down in a chair on the patio and sat with her legs spread apart.

"Stephanie-Anne!" her mother scolded. "Sit more ladylike! Only boys sit like that."

The evening passed uneventfully and when it was time for bed, Stephanie-Anne undressed and tossed her jeans and t-shirt on the floor next to the pair of panties she had taken off earlier. She kicked off her sneakers and put her bunched-up knee socks in them. She grabbed a nightshirt from her chest of drawers. It was filled with girlish panties and all a jumble. She paused to grab a pair of panties and then stopped.

"No," she thought. "Tonight I'm going to wear my boy's underwear to bed."

Stephanie-Anne pulled the nightshirt over her head and climbed under the covers. She reached into the drawer of the nightstand next to bed and pulled out a small flat stone. She called it her wishing stone. Stephanie-Anne rubbed it as made a wish. From the smooth surface of the stone it was obvious that she had been doing this for a while.

"I wish that they would treat me like a boy." she wished. She continued quietly repeating her wish as she drifted off to sleep.

At 8 o'clock the next morning, she was awakened by the sound of her brother banging on her bedroom door.

"Hey dude! Stephanie-Anne! Wake up!" Joseph yelled.

Why was her brother calling her to wake up? He was never interested in her. Stephanie-Anne stretched and shook the cobwebs out of her head. Something felt funny when she did this. She reached up to scratch her head and it hit her. Her hair. It was short! Stephanie-Anne pulled her hands away and held then in front of her face. The long girlish nails that had previously adorned her fingertips where now stubby short fingernails like a boy's.

She bolted from the bed to stand in front of the mirror on the back of the door.

Stephanie-Anne's eyes got as big as saucers. She had a boy's haircut. It was short and parted on the side. Then she looked at what she was wearing. The nightshirt she had worn to bed was replaced with a t-shirt that said "PS 51 Boy's Phys Ed". Peeking out from below the hem of her t-shirt, Stephanie-Anne could see that was still wearing her boy's underwear.

She shook her head again. "What the heck was going on?" she thought. "Wait. Am I a boy now? Or am I still a girl?"

Stephanie-Anne pulled down her boy's underwear. She was still a girl to be sure, she still had a vagina. She pulled up the t-shirt. She still had the two little budding breasts that she had when she went to bed. Yet other wise she looked like a boy.

Just then Joseph pushed open the door and entered her room. Stephanie-Anne stood there petrified, her boy's underwear around her ankles.

"Hey little brother, what're you doin'. How's it hangin'?" Joseph asked.

Stephanie-Anne looked at him. She blinked her eyes.

"Hey. What were you doin' Stephanie-Anne? Beatin' your meat? Don't let mum find out that you playing with your cock or she'll have a fit."

"My cock?" Stephanie-Anne asked. "Huh?"

"Your penis little brother! Geez, Stephanie-Anne what's up with you?"

"My penis?" she asked.

Joseph lifted the front of his t-shirt. He was wearing a pair of white Jockey Y-Fronts. Unlike Stephanie-Anne's they did have a bulge in the front.

"Yeah -- what d'ya think we have, pussies like girls do?" he said as he grabbed his basket.

Stephanie-Anne looked at the bulge in her brother's Jockey Y-Fronts and then down at her pussy. Why did Joseph think that it was penis.

"Joseph, do I look different to you?" Stephanie-Anne asked.

"No, Stephanie-Anne, not at all."

"You mean I don't look like a girl to you?"

"A girl?" Joseph laughed. "Why would you say that?"

"Well, its," Stephanie-Anne started to stammer.

"C'mon Stephanie-Anne, you're a boy and maybe you should start to learn some boy's things, like shaving. Grab a clean pair of briefs and meet me in the bathroom."

Joseph left the room and Stephanie-Anne sat on her bed. She looked around her room and noticed that it was now decidedly un-girly. No ballerinas or stuffed animals, apart from the teddy bear that she had hidden the stolen pair of boy's underwear in.

The clothes the she had taken off then night before lay in pile on the floor. She picked them set them on the bed. They were different. Instead of being powder blue and white with a kitten on the front, the t-shirt was dark blue and white and said "Cougars Boy's Midget Football - Stephanie-Anne '06"

The jeans looked about the same, but the embroidered flowers were gone. Stephanie-Anne's sneakers know looked like boy's trainers and there were a pair of white athletic socks. As for the pair of panties she had tossed in the corner the night before, they were now a pair of boy's white Fruit of the Loom briefs.

Joseph called out from the bathroom, "Stephanie-Anne? You coming for your shaving lesson, little brother?"

Glancing over at her closet she saw that it was filled with shirts and pants. The Girls Scout uniform that had hung on the doorknob the night before was replaced with a Boy Scout uniform. Looking closely at it she noticed that a label was sewn in the collar of the shirt. It neat letters it said "PROPERTY OF STEPHANIE-ANNE HUNTER".

Stephanie-Anne went to the dresser drawer where her panties were and pulled it open. Just as she thought. No panties. It was full of all neatly folded boy's underwear.

Stephanie-Anne sorted through them and pulled out a pair of Jockey Y-Fronts like her brother Joseph had on. She grabbed the white athletic socks and then walked across the hallway to the bathroom just as Joseph was pulling on a clean pair of Jockey Y-Fronts. Yep, he had a penis. She looked at it in awe.

He noticed this and said to her "Envious little brother? Don't worry Stephanie-Anne; soon as those hormones for puberty start kicking in, your penis will grow too. Go ahead and toss your dirty undies in laundry basket and take off your t-shirt. I'll get the stuff ready to teach you to shave."

Stephanie-Anne pulled off her boy's underwear and t-shirt. She stood before her brother and looked down at her vagina again. Joseph handed her the pair of boy's Jockey Y-Fronts that she had brought into the bathroom. After she put them on, sat on the toilet to put on her socks. She pulled them on and stood next to him at the sink.

Joseph lathered up his face and then instructed her to wash her face.

"Hold out your hand," Joseph said as he shook the can of shaving cream. He then squirted a glob of the white soapy goo into her palm.

"Now smear it onto your cheeks like I did," Joseph instructed.

Stephanie-Anne did as he instructed and when she had finished Joseph handed her a razor.

"Now, make careful long strokes like this, little brother," Joseph said as he ran the razor over his cheeks.

Stephanie-Anne took a stroke at her cheek with razor and looked over at Joseph.

"Good boy, Stephanie-Anne," Joseph observed.

Stephanie-Anne smiled. She looked in the mirror at the image of her and her brother, both in their Jockey Y-Fronts, shaving and felt very happy inside.

After they had finished, Joseph instructed her to wash off her face and then go get dressed.

"Mum has breakfast for us. You wanna go play some hoops? We can go down to the junior high gym?" Joseph asked.

"Sure Joseph, I'd like that," Stephanie-Anne replied.

"Then go get dressed and meet me downstairs," her brother instructed.

Stephanie-Anne returned to her bedroom. She pulled on the boy's jeans and boy's t-shirt that had somehow replaced her girl's clothes and then she slipped on her trainers. Looking at herself in the mirror she ran her fingers through her short boy's haircut.

"Way cool!" Stephanie-Anne said. "I really do look like a boy."

She bounced downs the stairs to the kitchen and joined her brother. Mum turned around from the fridge and looked at her. Stephanie-Anne gulped.

"How's my two strong boys today?" Stephanie-Anne's mum asked. "Joseph tells me that you two boys are going to go play basketball together, Stephanie-Anne. I understand he has a surprise for you."

Stephanie-Anne looked at her brother. Joseph smiled. "Yep, just a little present for my little brother. But you'll get it when we get to the gym."

Stephanie-Anne's eyes lit up at the mystery of the present that her brother had for her. As she dug into her bowl of Wheaties her mind was awash in wonder at the way her life had suddenly turned. Even though she was physically a 13-year-old girl, everyone treated her like a 13-year-old boy and she was dressed like a boy. She smiled, cause it felt good every time someone referred to her as a boy.

Breakfast wrapped up and Joseph was smiling a big grin at Stephanie-Anne. "Let's head out to play some hoops. We'll hop on our bikes and head down to the junior high. Old man Duffy the janitor said that could use the gym anytime we wanted."

Stephanie-Anne followed her brother out to the garage. In the place where her pink girl's bike with the basket adorned with flowers normally sat she found a blue boy's bike.

Stephanie-Anne hopped on her boy's bike and headed down the driveway shouting, "Last one to the gym is a girl!" The cool air felt good rushing through her boy's haircut.

After locking their bikes in the stand outside the entrance to the school, Stephanie-Anne and Joseph entered the building and walked down the hallway. Stephanie-Anne was in such a dream state that when they got to door marked "GIRL'S LOCKER ROOM" she grabbed the handle to open it.

"Whoa, Stephanie-Anne! That's the girl's locker room. Hey, you are really out of it today. We don't go in there, bro!"

Stephanie-Anne smiled. "Dun! Oh yeah right, the boy's locker room is just up the hall."

They walked down the hall and Stephanie-Anne followed her brother into the boy's locker room. Joseph flipped on the lights and Stephanie-Anne stood in awe. She had always wanted to go into the boy's locker room and now she was there.

"C'mon little brother." Joseph said to her. "I'll go to the equipment room and get you some shorts and a basketball jersey to wear. Go grab a locker and I'll be right back."

"Okay Joseph. Er, ah, I have to pee," Stephanie-Anne observed.

"There's a boy's restroom right next the equipment room, Stephanie-Anne. You pop in there while I get your uniform. Hope everything comes out okay," Joseph told his sister.

Stephanie-Anne entered the boy's restroom. She examined the urinals and walked up to one of them, She stood there for a moment and imagined that she had pulled out her penis to pee. Stephanie-Anne glanced in the mirror at the reflection of herself standing in front of the urinal.

"This looks so cool," she thought.

But, because she really did have to pee, she went into one of the stall and had a seat on the toilet. As she sat there, Stephanie-Anne looked down at the site of her Jockey boy's Y-Fronts around her ankles. She couldn't believe it, those were really her boy's underwear!

When she had finished pee-ing, Stephanie-Anne redid her jeans and went back out to the boy's locker room went her brother was waiting for her. He had a silky basketball uniform waiting for her. A small package sat on top of the pile of clothes.

"I got a uniform for you," Joseph said, picked up the package and continued proudly. "This is your jockstrap!"

"My jockstrap?" Stephanie-Anne asked. She had never seen anything like this before.

"Sure, little brother," Joseph said to Stephanie-Anne. "All us boys wear one when we play sports. It will protect your penis and testicles, Stephanie-Anne."

Joseph opened the package and handed the jock to his sister. She stretched the straps and examined the pouch.

"But I've never worn a jockstrap before, Joseph," she said. "How's it go?"

"I'll show you little brother. Get undressed and watch me."

Stephanie-Anne stripped down and then stood in front of Joseph wearing just her Jockey Y-Fronts as her brother pulled the jockstrap up his legs.

Joseph adjusted the straps around his rear. "Just pull it up your legs and then adjust the straps around your butt."

Stephanie-Anne pulled off her boy's underwear and then slid the jockstrap up her legs. As she did Joseph continued his instruction.

"Then just adjust your dick in the pouch, Stephanie-Anne."

Stephanie-Anne adjusted the pouch of the jockstrap in front. She looked over and could see that while Joseph had a nice cock bulge in his jockstrap, her jockstrap was quite flat as it nestled against her pussy.

"Good boy, Stephanie-Anne. That's support your penis and testicles!" Joseph told her.

Stephanie-Anne looked at him. "Huh?"

"It'll hold your cock and balls in place while you run, little bro. Get used to it! You're a boy, Stephanie-Anne, and just like girls wear bras, us boys get to wear jockstraps. A heck of a lot cooler than wearing a silly bra!" he told her.

Stephanie-Anne grabbed the pouch of her jockstrap. "Yeah, wearing a jockstrap really IS cool!"

With that Stephanie-Anne and her brother headed out to the gym floor. As they played a mean game of hoops, Stephanie-Anne noted that it really did feel good wearing a jockstrap.

They got all sweaty playing the game and when they were all done Joseph said, "We better hit the showers and head home for lunch, c'mon little bro!"

Stephanie-Anne gulped. She'd be taking a shower, fully nude with her brother. What if he finally noticed that she wasn't a boy?

Nervously Stephanie-Anne followed her brother back to the boy's locker room. They stripped down and Joseph handed her a towel.

"Off to the showers," Joseph said.

Stephanie-Anne followed her brother into the shower and soon the room filled with steam. Joseph was totally oblivious to the fact that she was girl. For all intents and purpose he was treating her exactly like a boy. She smiled as she lathered up, following her brother's every move, right down to washing her vagina in the same way as Joseph cupped his cock and balls as he washed them.

When they had finished showering Stephanie-Anne stood before her brother and dressed. Pausing for a moment she held up her boy's Jockey Y-Fronts and looked at them before putting them on. These were now her underwear, she was now a boy, and life was good.

  

  

  

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