(Narrator POV)
A young blonde woman in her early twenties stepped out of her light blue Impala, which she had parked next to its classic black counterpart in the driveway.
She grabbed a terrarium out of the backseat and rested it on her hip as she went up the path to the house. With her free hand she opened the door to her childhood home.
"Hey, everybody!" Clarity "Claire" Bobby Gabriel Winchester-Singer greeted her family members as she shut the door behind herself.
The house was virtually the same, but the residences had changed over the years.
Claire's long wavy blonde hair fell to her mid-back, her blue eyes sparkled under dark eyebrows, and the pale skin of her face was slightly stretched by a smile.
She was 22 years old and had just graduated from the police academy while being a hunter on the side. Her girlfriend was a brave woman named Kaia who she'd one day end up marrying.
"Hey, Claire!" A chorus of voices said at once. Her siblings and parents were apparently all downstairs waiting for her.
The quadruplets were on the couch, Jack and Cas were at the dining table, and Dean was in the kitchen making dinner.
Claire moved through the living room to put her terrarium and the snake it contained on the dinner table.
"Where's Kaia?" Samantha "Mandy" Jessica Megan Winchester-Singer asked as she stood from the couch to join them in the dining area.
Her wavy hair was dark brown and to her shoulders. The hazel of her eyes almost shimmered gold in the light as her slightly tan skin caught the sun's rays from the window. She wore a navy blue tank top, a purple flannel, dark blue jeans, and some brown ankle boots.
Mandy was 16 years old, and would one day become a marine biologist and veterinarian. She would also meet a sweet blonde by the name of Freddie who she would eventually marry. Diana and Reagan would be the names of their twin daughters.
Claire gave a small grin at the mention of her girlfriend. She took off her black leather jacket to leave her in an olive green t-shirt, black boots, and black leggings.
"I dropped her off at the airport early. She's a bit of a nervous flyer, so she wanted to interrogate and demon-test our pilot before we take off." She explained.
Dean seemed to get a contemplative look on his face from where he was making hamburger paddies at the counter. "That's not a bad idea."
"Wait, Kaia is afraid of flying? Kaia!?" Benjamin "Ben" Grace Crowley Winchester-Singer asked in disbelief. His dark brown eyes brightened with a prank idea as he eagerly leaned against the back of the couch.
He was wearing a black t-shirt, green flannel, blue jeans, and green sneakers. His short dark brown hair and pale skin contrasted against each other nicely.
Ben was 16, and would soon meet a fierce girl named Krissy who he would marry much later in life. They would have one son named Rowen.
The career he would choose was the same as his dad's, and one day he'd inherit the garage for himself.
(Dean's bar was going to be a gift to Benny and Meg's daughter Ashly Singer Jessie Lafitte, in the far future.)
"Shut up, Ben." Claire answered him.
"Your father is afraid of flying." Cas commented absentmindedly while all of the kids whipped their heads to face him and Dean made 'please don't' gestures from the kitchen.
"Dad is afraid to fly?" Mary "MJ" Jody Ellen Winchester-Singer asked as she stood up to head into the kitchen. "Dude, you killed a demon and you're scared of an airplane?"
Her reddish brown hair was slightly wavy and flipped to one side as it went down to her mid-back. The color of her eyes was a vibrant green and her skin was pale.
She wore a red long-sleeves shirt to compliment her red painted nails, her shoes were black knee-high boots, and she had on black skinny jeans too.
MJ was 16 years old and would become a pro baseball player, hunter, PI, and bounty hunter. She didn't end up with anyone and was perfectly happy by herself.
"I'm not scared of the airplane!" Dean said indignantly. When she just tilted her head with a raised eyebrow, he went on. "I'm scared of airplanes crashing."
"I can't believe that you're going to Norway for two weeks. I'm so jealous." Mandy changed the subject as she spoke to Claire.
"Yeah, why can't you bring us?" Jack Rowen Pamela Winchester-Singer questioned his older sister.
His hair was straight and brown, and his eyes were still blue with golden flecks in them. His outfit consisted of a red flannel, cream colored shirt, black sneakers, and black jeans.
He was 20 years old and going to college for an archaeology degree, using his soccer scholarship to his advantage. His real dream was to take over the flower shop and market from his Papa.
Alex and Jack had just started dating and (although they didn't know it) they'd be married in a few years time. There only daughter would be named Lilly.
"I'm not taking my siblings with me to Norway because it's supposed to be a romantic trip." Claire answered Jack like it was the most obvious thing in the world.
To be fair, it kind of was.
Charlie "CJ" Asher Joanna Winchester-Singer had remained quiet the entire conversation, just happy to listen to his family for now.
He was 16 years old and would soon become an astrologist and engineer. Later on in life he would even get to be an astronaut.
Little Star was gonna go to space.
He would also meet a charming man named Andy who he would end up marrying, and having a daughter named Lyra (after the constellation).
His short (but longer than Ben's) hair was a light brown and curly, his eyes were insanely bright blue, and he wore an outfit that consisted of a blue sweater, black jeans, and grey converse.
The door was suddenly opened and a boy with fair skin, dark brown (straight, pushed back, and longish) hair, and blue-green eyes entered.
He was wearing a jean jacket, tie-dye t-shirt, dark jeans, and brown boots. His age was 18, and he would soon become a hunter and weapon maker (specializing in weapons against the supernatural). He had a girlfriend named Lexie and would have one son named James.
It was none other than Dean "DB" Bobby Jody Winchester-Singer.
"Hey, I kinda need a bit of help from the mechanically inclined." He said with a big grin.
"Your piece of junk pickup break down again?" CJ asked quietly.
"No!" DB denied as he moved to get a drink from the fridge. "...Okay, maybe." Everyone groaned. "Hey! In my defense, they sold it to me like that."
"That doesn't make it better." Mandy told him, but couldn't stop herself from laughing a bit at her cousin.
"Fine, whatever. You all are being extra hostile today, what's up?" He asked as he shut the fridge with a soda in hand.
"I'm just going to the airport." Claire explained and he huffed slightly.
"That doesn't seem like a reason to be crabby." DB responded and made an excited noise when Miracle (a blond Doodle mix that saved Dean's life when a werewolf had come into town.) came around the corner to get some petting.
"We're not crabby." Ben defended while watching his cousin crouch down to pet the dog.
"If you say so." The man said in slight disbelief. DB pushed his hair back a bit as he kept petting Miracle.
"What's up with the hair, Princess?" MJ questioned him. "If you're trying to grow out a mullet like Uncle Ash, I'll sneak into your house and cut your hair while you sleep." She threatened.
"Geez, MJ. I'm not trying to grow a mullet, but why can't I if Uncle Ash can?"
"Because Uncle Ash, is Uncle Ash. Rules don't apply to him." CJ reasoned simply while he casually flipped through a book. DB couldn't argue with that so he just went back to petting Miracle.
The door opened without warning again to reveal a 12 year old girl with curly blonde hair to her waist, fair skin, and brown-hazel eyes.
She wore a teal unzipped hoodie, teal converse, grey skinny jeans, and a white t-shirt. On her back was a black and white backpack.
In the future, she would be an excellent nurse who wasn't married or dating, but had a daughter named Gabrielle.
Cassandra "Sandra" Mary Megan Winchester-Singer walked in with a glare toward her brother.
"Sandra, I told you to wait in the car." He whined at her while she huffed and made her way inside after closing the door.
"Why? So you wouldn't have to tell them that I need a ride again?" She saw right through him and marched toward him to take his soda.
He made a disgruntled noise at the theft, but she went on before he could speak. "Because every time you offer to drive me somewhere, your stupid truck decides to break down."
"It's you!" DB exclaimed and stood from his crouch to steal back his drink, then made a grossed out face when he realized that her saliva had already contaminated it. "You're a bad luck charm, and keep breaking my sweet darling! You're bad hoodoo, or somethin'."
Sandra just stared at him for a moment before speaking again. "Are you seriously blaming your car troubles on your little sister, instead of just admitting that you picked a crappy truck?"
"...Yes?"
She rolled her eyes and went to sit by CJ on the couch. "Whatever. You should really just have Grandpa scrap it."
DB gave a scandalized gasp and put his hand on his heart. "Don't talk about her like that, Sandy! Peggy has feelings too."
MJ watched the entire scene along with everyone else and then leaned over the island counter dividing her and her dad. "If DB is actually our brother, you can tell us."
"Hush, Little Lioness." Dean answered with a bit of a laugh. He did have to admit that his nephew was scarily like him sometimes.
"Where are you going, Sandra? Maybe I can drop you off on my way to the airport." Claire offered.
"The Roadhouse. I'm hanging out with Deanna today." Sandra answered, referring to Jo and Charlie's daughter (Deanna Samantha Ellen Bradbury-Harvelle).
Claire gave a nod. "I'll drive you then." She agreed and earned an excited 'thank you' from her cousin.
"You having burgers?" DB asked suddenly as he saw his uncle finishing with the meat for the meal. Dean gave a nod as he went to wash his hands. "Can I stay?"
"Don't you have parents who feed you?" MJ asked him sarcastically.
"They're having sushi for dinner." DB explained with a wrinkle of his nose. Everybody knew that the boy didn't share his parents taste in food very often.
"Yes, you can stay." Castiel said once he heard that. Dean always made extra, and never minded when more family members trickled in for a meal at the house.
"Thank you, Uncle Cas!"
"Alright, I gotta go or I'm gonna miss the plane. Thank you for taking care of Salazar." Claire said and Dean gave the snake she was referring to a shifty look.
"I'm not going anywhere near it." He said and Claire just rolled her eyes as she went around hugging everyone goodbye.
She and Sandra both hurried out the door as Ben went to take the terrarium, up to his room since he'd be the one actually taking care of Salazar the most.
(Salazar was a relatively small black snake that Claire had had for quite awhile, Ben had a bearded dragon named Avocado, Jack had a cream colored hamster named Nougat, CJ had a turtle named Timothy, MJ had a colorful parrot named Pirate, Mandy had a brown chinchilla named Chewbacca, and the whole family shared the other animals).
Over the years the family had grown in people and animals, Gabe and Pam had moved into a house, and new relationships developed.
Adam had ended up with a woman named Talia and gotten married a few years afterwards. They had a son named Caspian Dean Winchester and a daughter named Katherine "Katie" Samuel Winchester.
Kate (now Milligan again) had ended up with Crowley after a few years of John being gone.
Gabe and Pam had had a daughter named Cassiopeia Diana Bow Barnes (they took her last name and moved his to the middle of his name so he could get farther away from his family, and Bow was a combination of Benny and Rowena.)
Ash was still single, but only because he wanted to be.
All the companies/businesses/shops were thriving just like they had been for years, and the only change in them was growth and improvement.
The whole family got together often to bond and just be with one another. Each couple also took time to love and appreciate each other and their own little segment of the family.
Cas and Dean were just as in love as they had always been, if not more so.
Everyone in the family was happy and prosperous, and there wasn't much they would change despite the fight they had to go through to get to this point.
Truthfully, the fight had made the reward all that much sweeter.
All of them had been on slightly different roads in the beginning which led them to their lives and to each other, but they could all agree on one thing.
Those roads were the Trails To Happiness.
A/N Hey! You made it to the end and so did I! A miracle, honestly.
I'm so happy to be done and I'm actually pretty pleased with this story so I hope you are too!
Check out my farewell chapter, or I'll hopefully meet you again in my next story!
~Taboojinx <3