After that night the next few months were hell for Samantha. Whenever her father was there, which thankfully was even less than normal, they fought just as horribly, but twice as much. He thought she was confused and rebelling, yelling at her to forget about the 'girl' nonsense and fall back in line. He refused to accept that it wasn't a new thing or a way of rebelling against him no matter how many times she told him or in how many different ways.
Dean took her side through it all, unwilling to go against Samantha and her need to be who she was. His refusal to help their father convince her she was confused made the time when their father was there tense and uncomfortable for all of them.
Never one to back down, Samantha took to wearing her 'girl' clothes in the house full time. Most of the time he'd look at her and tell her to change back into her real clothes, other times he'd give her a sad and confused look that once or twice made her even plead with him to understand and try to accept it. Long after the fights had ended, one or both of them storming off, doors slamming in their wake, Dean would hold her in his arms while she cried herself to sleep, asking why he couldn't accept her like she was. He would murmur to her and tell her it would be alright, both of them ignoring the sliver of doubt in his voice every time he said the words.
Finally one night, their dad came home after being gone for a three week hunt and sat them all down in the kitchen.
"I stopped by Missouri's on my way to the hunt for help with the ritual," her father said quietly as he fiddled with the beer bottle in his hand. "She told me she knew what was going on and to get my head out of my ass and make it right."
Dean moved his hand under the table and gripped hers tightly, giving her support and strength.
"Missouri said she'd seen what your future is and that 'if you can't accept Samantha Winchester and all she entails you'll lose them both forever.' She told me I was a fool if I didn't listen to her."
Samantha felt Dean stiffen at his words as her body did the same. Did she know about them? Did she tell their father? He wasn't ready to hear about that change in their relationship as well as Samantha's gender issues and they weren't ready to tell him for risk of the fallout. She knew that whatever the future held for her, Dean would be right beside her as her brother and as the man she loved, but they were still young and she knew the world wouldn't see their love as anything but wrong and disgusting.
After a moment he looked Samantha in the eye and then Dean, his eyes glistening with unshed tears. "You're my boys… well, my children, and I love you. I don't understand it, probably never will, but I can accept it if that means you two are still with me."
"Before you go any farther I want to say that you don't know everything…" Samantha softly interrupted him, squeezing Dean's hand tight as she spoke. "… and that before you say you can accept me for me, I need to tell you that I want to start living as Samantha Winchester full time, in public the next time we move and that I want to start taking hormones to begin the change from male to female."
Her father sucked in a deep breath and closed his eyes for a moment. He gripped the bottle in his hand so tight that his knuckles turned white with the strain and then he blew the breath back out.
"I can still accept that, but I want to make a few rules with this new change." He waited until she nodded and then spoke again. "You changing your body will make people see you different and that means men will see you differently. I need to make sure you know how to protect yourself when Dean and I aren't with you. I've been thinking for a while that you needed to learn the family business and start training… now's as good a time as any I'm thinking."
Worrying her bottom lip, Samantha said, "Okay."
Training to be a hunter was brutal. Dean and their father spent hours upon hours making Samantha spar with them, learning how to take a hit, how to hit back, how to duck and dive and all that other stuff. She would go to bed at the end of each night feeling like her body was nothing but one big bruise and wishing that the soreness and the ache would go away. She grew skilled with every weapon in the family's arsenal, but was very adept at knives and her father made her always keep a couple on her body after she proved skillful with them.
She started gaining muscles that at first were a good thing. She liked the toned firmness of her abs and the slight curve to her biceps instead of spaghetti arms she'd had previously, but the more she trained the more her male body moved farther away from the way she wanted it to be.
"God, look at that, I'm starting to look like one of those bodybuilders. Not even my loosest clothing is hiding these anymore…" Samantha sighed as she looked at her body in the mirror.
She was wearing a pairing of pink boy-cut panties with little hearts on them and a matching bra. Before she started training if she didn't looking too closely at her body she could convince herself that it was female; the thin slight frame had made it easier to believe. But now with all the muscles she'd gained from training she just looked like a teenage boy in girls clothes… she hated it.
"Sammy, you don't look like a body builder," Dean laughed as he stepped behind her and wrapped his arms around her waist. "You look beautiful, baby."
"No I don't, I look like a boy in drag."
"Well, technically, you are a boy in drag."
Huffing, she slipped out of his arms and walked back into their bedroom and started dressing for school. "Yeah, but at least before I was so slim that it wasn't so noticeable. Now I can't hide the fact that I'm a male wearing girl clothes. I need to start taking hormones soon or I won't be able to look like a girl, no matter what I wear."
"Okay, then let's find a doctor to start you on hormones then."
Whirling around with a nervous smile, Samantha blurted out, "Really?"
"Yeah, it was gonna happen sooner or later, and now that Dad is somewhat okay with you being a girl… why wait? Unless you're not ready?"
"No, I'm ready; I've been ready for years now!" Giggling, she launched herself into Dean's arms, wrapping her legs around his waist and kissing him all over his face. "Thank you, thank you, thank you!"
Dean laughed and kissed her back. "Love you, baby." He murmured against her lips.
"Love you too," Samantha sighed, her breath mingling with his as she licked his bottom lip; nibbling the plump flesh with a soft moan. "Love you so much, Dean."
As it turns out, a lot of doctors had a problem with her desire to start the process from male to female. Six doctors wouldn't even consider treating her, they recommended psychologists to treat her "mental illness" as one put it, the others thought she was just confused and needed a listening ear to work out her issues. Three were too uncomfortable to begin the process before she was 18, even with her father's consent. Four were willing to proceed, but required two years, or more, of counseling before starting the treatment.
Samantha was frustrated by the fact that so many people believed that she was confused or 'mentally ill.' One doctor had implied that if she just waited long enough she would be alright with the body she was born in… that she was a "young boy on the verge of manhood with a world of possibilities ahead of you; don't let insecurity lead you astray."
She knew who she was and what she wanted, thank you very much! She'd known since she was eight years old that she was born in the wrong body. It made her mad that other people thought they knew what was best for her, despite her vehement assertion that she had been contemplating this for years since she realized what was wrong. They wouldn't change her mind. She may be young, but she still knew what was right for her.
After that last appointment she had even begun looking for alternate ways to begin hormone treatment on her own. She'd read online that many transsexuals have problems getting the initial process started, just like her, and had begun the hormone treatments themselves through less than reputable means. Dean had flat out refused after hearing that, saying that he didn't want to take a chance that something would go wrong and hurt Samantha.
Finally after a month of refusals or stipulations that would take years to complete before she began hormone replacement therapy, or HRT as it was known as, Dean stumbled upon a doctor who specialized in treating the LGBT community specifically and had experience with transgendered patients. The doctor required counseling sessions before and throughout the process, but was willing to proceed within the year.
So seven weeks after Dean and Samantha's conversation, she began HRT.
The first month or two Samantha didn't notice much of a change, maybe her nipples being a bit sore and itchy or a little less hair here or there, but nothing much. Then it seemed over night that she started noticing changes in her body. Her nipples grew larger and her chest began to grow minutely as she slowly filled out the training bras she had always worn without true need of them. The fat on her body began to shift as it redistributed to other places like her hips and thighs. Her face thinned out and she began taking on more of the delicate feminine features that she had envied on other girls for years now.
What made her giddy and excited though were the changes in her genitals. In the last four or five months she had begun entering into puberty. Her testes had begun to drop and heavy coarse public hair had begun to form around them and on her legs, arms and armpits. Samantha's unusually high voice had started to lower and she had irrationally feared that she had waited too long before beginning HRT. But when the changes from the hormones began, her testes stopped growing and even grew a little smaller. The hair that had begun to sprout in unsightly places thinned out or stopped growing all together, and her voice got a smooth feminine quality to it that had Dean's eyes glazing over in lust whenever she teased him with it.
Besides the fact that she was slowly making her way from a male to female body like she had longed for for so long, there were a few other perks to the HRT. Dean seemed to find the changes in her body beautiful and he spent hours in the bed at night cataloging the changes to it. His hands and lips, the weight of his body on top of hers; every look made her feel cherished and loved for who she was and what she'd be one day. It was something Samantha looked forward to each night, though sadly things never went past a certain point.
It had been a year since they had gotten together and though they had graduated to mutual orgasms, they hadn't gone all the way yet. Samantha had just turned fifteen the week before and, while she felt she was ready to go further, Dean held steadfast to the fact that he wanted to wait until she was sixteen. But just because they hadn't gone all the way yet, which Samantha looked forward to with bated breath, didn't mean that they didn't make up for it in other ways…
"Please, Dean?" Samantha pleaded, giving him the biggest puppy dog eyes she could, her bottom lip jutted out as she looked up at her brother who was laid out on top of her.
"I thought we decided to wait until you're sixteen?" Dean hedged, as if she had played any part in 'their' decision.
"Yeah, to go all the way, but I've been thinking about you fingering me," she breathed into his ear, her warm breath ghosting over him, making him shiver and give an involuntary thrust against her.
She would have smirked at the glazed look that fell over his eyes if she wasn't worried he would say no just to spite her. "Remember last week when you and Dad went on that hunt in Witchita overnight?"
"Yeah," he groaned as he nuzzled her neck, licking the fine sheen of sweat that had gathered in the unusually warm spring night.
"I fingered myself in our bed, thinking about you doing it… your thick fingers inside me, thrusting in and out as you sucked my nipples... they're so sensitive since I started HRT, can't stop thinking about how it will feel with you sucking them inside your mouth." A mewl slipped past her lips as Dean thrust down against her again, this time slamming into her body as his hands slipped underneath her body and gripped her ass.
Their groins slid against each other's, the sweat and pre-come giving just enough lubrication to allow their flesh to glide back and forth, the friction setting her body on fire. She tightened her legs around his waist, holding on as he pounded into her, wishing he was inside of her, filling her up and stretching her wide. "Please… please, please, PLEASE!"
Dean groaned and then scrambled over her body to reach the nightstand and grab the half used bottle of lube they kept on hand. He squirted a drop of lube on his fingers and threw the tube on the bed as Samantha wantonly spread her legs as wide she could. She glided a hand down her chest until the fingers brushed past a sensitive nipple, her moan filling the quiet room.
One of her brother's fingers lightly circled the furled muscle guarding her entrance, letting the lube slick the edges before he pressed the finger into the first knuckle. It wasn't large, but it was bigger than her own fingers and she sighed in bliss at the feeling of a part of Dean inside her for the first time.
"I can take another, Dean, give me another!"
She thrust her fingers through his short spiky blonde hair and gripped his scalp as he pushed another finger in along with the first, pushing them both in as far as he could go. Samantha gasped and rocked her hips upwards as he pressed against her prostate, a burst of pleasure unfolding within her.
She could feel Dean's warm breath against her hipbone, his lips kissing the flesh every time she thrust down onto his fingers. All she wanted was that hot wet mouth making its way up her body, licking and sucking and biting as it moved until those lips wrapped around her aching nipples and pulled the building orgasm from her body. She knew it would be explosive, his lips suckling her nipples, his fingers thrusting inside her… his dirty words taking her higher and higher.
Dean pulled his fingers out of her and then added a third, pressing repeatedly against her prostate as he thrust them in and out, in and out, in and out; her breath coming out shallow pants as he worked her over.
"God, so beautiful, baby girl," Dean groaned against her hip, "knew your pussy would be tight and wet for me. Just waiting for me to shove my fingers and dick in there and slam home. Can't wait 'til I can get in there and mark you as mine inside and out. Fill you full of my cum."
Samantha choked on a sob, Dean's voice and words sending spikes on painful pleasure coursing from her groin outwards. Just that husky growl of his, the way vowels rolled off his tongue like molasses, made her want to cream her panties on most days… now, with those filthy words and those skillful fingers working her body over, she was on the edge of oblivion and a second away from falling.
Dean slowly worked his way up her body, filthy dirty words spilling from his lips and staining her sweat slicked skin as he went. His tongue slid out from between his lips to flick around the curve of her belly button making her cry out in shock as it felt like the small little square inch bit of flesh was directly linked to her groin; sending pulse after pulse of pleasure spiking towards her core.
Her body tightened up as she felt the edge coming closer and closer. Samantha began babbling uncontrollably as his wet mouth finally covered one of her nipples, teeth scraping against the sensitive flesh before pulling the nub inside with a powerful suction that brought a scream from her lips as she exploded into tiny little pieces of pure sensation.
When she came to, Dean was slowly thrusting against her hip, his cock slick with pre-come as he grunted around her aching nipple. His eyes were on her face, filled with love and wonder and trust, as he came closer to orgasm. Samantha slipped a hand in between their bodies and wrapped it around his cock, his groan making her grin as she began sliding her hand up and down the length, gripping him tight as she brought him off.
"Love you, baby girl… look so perfect under me," Dean groaned as he flicked the tip of his tongue around her areola, smirking when she gasped at the pleasure/pain it elicited. "Can't wait to be inside you for real; your tight pussy wrapped around my cock as I pound inside you. Fuck!"
Pressing his face into her breasts, Dean gave a deep groan as he came, his cum spilling over her hand and onto her stomach, the warm wet semen a balm to her aching body. He slumped down onto her with another groan and then slid off a bit to make sure he wasn't squishing her. Dean was always looking out for her that way, even in a moment like this when he brain was short circuited on overwhelming pleasure.
Leaning over her again, Dean threaded a hand through her hair before cupping her cheek. He pressed his lips against hers, their breaths mingling before he coaxed her lips open and slid his tongue inside. Lifting her arms up, Samantha wrapped them around his neck and kissed him back with all the emotion she had inside her before sleep finally pulled her under.
Four months after she began taking hormones, they moved again. Using a contact he had through hunting, their father had Samantha's records hacked, including her birth certificate, and altered them so that she was now listed as Samantha Winchester, female.
She'd hugged her daddy so hard when he'd told her, with a blush on his face. That night she had made a big dinner with all the fixings. They spent hours at the kitchen table laughing and joking, a true family for what felt like the first time in a very long time. Just the memory of it made her all warm and happy inside.
"Sammy, you ready yet?" Dean yelled from the living room of their new apartment.
Samantha could hear him grumbling about being late for work if she didn't hurry her pretty ass up. Her eyes bouncing back and forth between the two outfits laid out on the bed, Samantha bit her lip as she tried to choose which one to wear.
It was her first day at the high school and her first day ever as Samantha Winchester in public. Up until then she had been nervous about being herself out in public. There was no doubt that she was comfortable with herself and her choices, but she worried that people would find out and judge her… make fun of her. She was a girl in her heart and mind but to everyone else, besides her brother and father, she would be just some weirdo boy who liked to dress up in girls' clothes and who'd started to grow breasts.
This was a big step and, though she was sure it was the right one, taking that step was the hardest thing she'd done since she'd confessed to Dean and then their father about her transsexualism. She was doing this, she'd made up her mind, but she had to look perfect… like a proper lady; a real lady.
Blowing out a puff of air to get a strand of hair out of her eyes she closed her eyes and said a quick 'eeny meeny miny moe' and then hurriedly to pulled on the winning outfit. Running to the bathroom she made sure her hair and makeup were still in place and then walked into the living room.
Dean stared at her for a full minute, his eyes roaming lustfully over the pink knitted sleeveless sundress that showed a hint of her every growing breasts and the white cardigan over it. She had on a pair of strappy white sandals and a few multi-colored bangles on her wrists. Samantha's hair was in long loose wavy curls that had grown quite a bit over the last few months and brushed just passed her shoulder blades.
She felt like a million dollars through Dean's eyes and she couldn't help but giggle in glee. "So what do you think? Do I look like a lady?"
"Baby, you look perfect." Dean said softly as he walked up to her and wrapped his arms around her tiny waist and pulled her close. "I'm gonna have to beat all the boys at your school off you, you look so good."
Laughing, Samantha grabbed her messenger bag from the couch and then said quietly, "Okay, I'm ready."
Dean looked at her a moment. "You sure? We can wait a while, screw the school."
Lifting up her chin in and giving him a determined look she nodded. "No… I'm as ready as I'll ever be."
"That's my girl."
Ten minutes later, walking up the steps of the high school, Samantha took one last look at Dean for courage. He stood leaning against the driver's side door grinning at her, shooing her forward like a mother hen. Smiling back at him, she walked through the entrance and made her way to the school's front office.
A woman that looked like she had a pound of makeup on her face, artfully applied with a paint brush, stood behind the counter at the office. As Samantha stepped up to the counter, one of the woman's painted eyebrows rose, "Can I help you, missy?"
"Um… I'm a new student. It's my first day."
"You must be Samantha." She grabbed a sheet of paper from a file and handed to her.
"Here's your schedule with a map of the school, as well as school policies to abide by. If you have any questions please feel free to come back and we can answer them for you."
Nodding, Samantha noticed the time on the clock over the woman's head and then said thank you before hurrying to her first class. She made it just as the bell rang and she took the last open desk in the very back.
The teacher read from a sheet on the table, calling out student names, making a checkmark as each student answered. After a minute he called out, "Samantha Winchester?"
Raising her hand, Samantha looked said, "Present."
"Hey, you must be new! I'm Marnie." She heard a chipper voice from beside her.
Turning her head, Samantha smiled at the girl in the desk next to her. Marnie was dressed in a black ruffled skirt with purple leggings and a striped black and white shirt. Her hair was black streaked with gray and red and just from the first look Samantha could see at least six piercings and a layer of dark heavy makeup on the girl's eyes and lips. She wasn't normally the kind of person Samantha made friends with, Marnie was obviously an extrovert, something worlds away from Samantha. Of course, it wasn't like she made a lot of friends anyways. Usually she kept to herself, but occasionally she formed a friendship with a fellow geek. However, Marnie had a welcoming smile and a curious interest on her face that made Samantha feel like she could be a good friend, for however long they were in the town at least.
"Hey, I'm Samantha. Nice to meet you."
Introducing herself to Marnie as 'Samantha' felt like the first truly genuine thing she'd ever said to anyone besides her brother and father, and it felt wonderful.
