Five time Sam almost came out...
and one time Castiel messed up and she had to come out.
Warnings: Sam is MtF and John is an ass in this.
Mentions of Jess, but only minor.
(1)
The first time Sam was ten years old, he had been hanging out with a friend and she had put her moms make up on him and she made him wear one of her dresses. Sam had liked it allot and he loved pretending to be a girl.
"Sammie you are so pretty." His friend gushed.
"T-thank you Abby." Sam mumered. She smiled at him and held his hand as she led them to the kitchen.
"Mama, can we go to the park?" She asked. Abby's mom nodded and Abby led Sam out the door and they started walking to the park. Sam loved walking around in the dress, he felt so much more at ease in it.
Once it was at noon Abby led Sam back to her house so they could eat lunch.
"So Abigail, Samantha how was your day?" Abby's mom asked. Sam was about to correct her but Abby started bouncing in her seat.
"It was so much fun, Sammie looked so pretty in the dress and allot of the boys couldn't keep their eyes off of her." Abbie said excitedly. Abbys mom smiled and the two of them walked back to Abby's room after they finished.
"I have to change, Dean will be here soon." Sam whispered. Abby nodded and helped Sam out of the dress and cleaned off his makeup. She then handed Sam the dress after he got changed into his jeans and shirt.
"Keep it, doesn't fit me anymore anyways." She said. Sam smiled and put it in his bag. He then heard the door bell and they walked back down the stairs.
"By Samatha." Abby's mom said.
"By Sammie." Abby called. Sam smiled and left the house and was met by Dean.
"Hey Sammy." Dean said. Sam smiled and Dean pulled his arm slightly so they could walk to the motel.
"So how was your day?" Dean asked. Sam looked up and smiled brightly.
"Awesome." He said.
"So what did you do?" He asked. Sam was about to tell him all about what they did but he didn't know how to explaine why he did it.
"Got dressed up a bit and went to the park." He finally desited.
"Cool." Dean said. They then walked passed the park Sam and Abby went to and one of the kids who had been there earlier pointed at Sam.
"Mama look it's Samantha!" She yelled.
"Why is that kid calling you Samantha?" Dean asked.
'Becuase I went by Samantha when we came, and I liked it allot.' Sam thought but he shrugged his shoulders.
"Maybe I looked like a girl from her angel." Sam said. Dean nodded and they walked the rest of the way. Sam sighed quietly one they were there.
'Why did I want to tell Dean?' He thought to himself.
(2)
The second time Sam was thirteen and just starting puberty. Sam had been weirded out when he woke up with a hard on and even more weirded out when he saw hair in his private area. When Dean saw his little problem though he laughed.
"You're becoming a man Sammy." He said. Sam would give him a week smile though.
"I will go get you some stuff Sammy. I will be back." Dean said and once Dean left Sam would cry and cry because his body wasn't listening to him. Once Dean got back to the motel with the stuff Sam saw it was porn magazines and lube.
"You are going to need this." Dean said. Sam looked at the things and sighed.
'I don't want this. I just want my body to be different' Sam thought as he grabbed it.
"I um..." Sam started.
"What's wrong Sam?" Dean asked.
"Um... I- nothing. Just thanks Dean." Sam mumbled. Dean sighed and laid down on one of the beds and Sam went to the bathroom and closed the door. Sam felt the tears run down his face and he sighed.
"Why couldn't you have just been late." Sam mumbled.
(3)
The third time Sam was seventeen and just found the term that described him in a medical dictionary. He had been at the public library, trying to avoide his dad at all cost, and he found the book and looked through it. He had been so excited bpwhen he found the word.
"Transgender. I'm not a freak, this happens to other people." Sam whispered. Sam felt the tears run down and honestly he didn't care. He then put the book away and he checked the time. Once he saw it was nearly five he got up and started to head back home. He then picked up a newspaper and read the headline.
'three men found dead...'
Sam continued reading and found out that they were found dead in the next town over so he decided to let his dad home when he got back.
Once Sam got home he handed John the newspaper and turned on the t.v.
"We aren't doing it." John said. Sam looked up and gave him a confused look.
"What?" Sam asked in surprise.
"We aren't doing the hunt. Damn faggots deserve what they got." John grumbled. Sam was about to blow his top when Dean showed up.
"Dad, found a hunt?" Dean asked, eyeing the newspaper.
"Nope, I'm going to the local library and find something." John said. Once he left Sam sighed and he looked at his big brother.
"Dean, why doesn't dad like gay people?" Sam asked. Deans eyes got wide and he pulled Sam into a hug.
"Sammy, there isn't anything wrong with that. Wait were you trying to come out?" Dean asked.
"Wait what?" Sam squeaked, had he been to obvious?
"You know, that you like guys as well?" Dean asked. Sam sighed and shook his head.
"No. And I'm not gay." Sam said.
"Oh, well if you were it would be okay.. Dad is just a little old fashioned." Dean said. Sam smiled and she shook her head fondly.
"It's okay Dean. I know." She whispered.
(4)
The fourth time Sam was nineteen and she was beguning her transition. She was given hormone suppressants and she was making some minor progress already. Jess, her girlfriend had been nothing but supported. She had helped Sam start dressing more girly, helped with her make up, her hair, she even taught her how to shave her legs. Sam had been blessed when she met Jess.
"So, when are you going to tell your family?" Jess asked.
"I don't know, my dad is a homophobe and I-I don't want Dean to hate me more than he probably does." Sam whispered. Jess nodded and rubbed her shoulders.
"I'm going to make us tea." She whispers. Sam smiled and Jess walked into the kitchen. Sam then pulled out her phone and started dialing Deans number. She then stopped herself and sighed.
"Dean, I'm not your brother, I'm your sister." She whispers. She then sighed again and stood up.
"Jess, why don't we just go out?" Sam asked. Jess smiled and walked out of the kitchen.
"As long as you dress in that skirt I got you." Jess said. Sam nodded and they headed to the bedroom so Sam could get ready.
(5)
The fifth time Sam was twenty two and was going to get her operation the next week. Sam already had slightly larger hips and she was starting to develope breast. Jess had been excited for Sam and Sam couldn't believe she was finally going to be Samantha. Though Dean then broke into her house, Jess nearly told, Sam got her not to, Dean talked her into a hunt and they went on a hunt. Now Sam was standing in front of her burning building and she was softly crying.
"It's okay Sammy." Dean said. Sam nodded and closed the trunk of the car.
"We have work to do." Sam mumbled. She then realized that she didn't grab her pills from the house and she sighed.
"Dean..." She mumbled.
"Hmm?" He asked.
"Never mind." Sam said.
(1)
Cas was staring at Sam as she walked around the bunker with her arms wrapped around herself. She seemed sad and no one noticed. Dean had been out and Kevin had been in the library so Sam was left to her own demise.
"Samantha." Castiel said. Sam looked up in shock and Cas smiled.
"H-how did you.." Sam started but Cas smiled again.
"Your soul is female." Castiel explained.
"Oh." She whispered.
"What's wrong?" Cas asked.
"It's the aniversary of my moms death, and my girlfriends." Sam explained softly.
"Oh, I understand." Castiel said.
"I can't help but think if she was still alive, I would be in the right body." Sam continued. Castiel looked at her in shock and Sam smiled.
"I was going to have the surgery the next week." Sam explained.
"Can't you still have the surgery?" Castiel asked.
"Not enough money and Dean doesn't know." Sam whispered.
"I think he would understand." Cas said. Dean chose that moment to walk in and he looked at them confused.
"Understand what?" Dean asked.
"That Samantha wishes to have the right body for her gender." Cas said. Sam paled and Dean looked confused for a second before he smiled.
"Wait a minute, Kay?" He asked. Sam gave him a confused look and Dean left the room. Once Dean was back he handed Sam a number.
"I um have a friend. Her name is Rhonda Hurley and well she was born Ron... She had a great doctor to who would do your surgery." Dean explained. Sam looked up, tears forming in her eyes.
"So you..." She started.
"I've know sense you were two and wanted the princess dress." Dean explained. Sam smiled and hugged Dean.
"I- thank you Dean." She whispers.
"Anything for my baby sister." Dean replied.
For the first time in a while Sam finally felt right.
Alright so I have no clue about the whole transition stage and how long it tends to take. I am going off of some other fics I read.