#you can't shame me miss jess. jessica even.

[aemondtargeryen]

now why were you looking at his ass? what kind of intellectual interest is this?? are you perhaps sexualizing this man?!

most ardently. most diligently. most constantly. always. next question.

[deans-baby-momma]

Never Have I Ever-Chapter ONE

Summary: When the Winchester family gets together to commemorate a milestone, the celebration takes a turn no one expected. How will they continue to be a family afterwards? CAN they?!

Or did they cross a line of no return?

Takes place in 2005. Dean is 26, Sam is 22 and Y/N is 19. An AU of sorts as there are no monsters, no talk of the Supernatural.  John and Mary are both alive and had another kid after Sam. Y/N is the baby of the family and their only daughter. 

A/N: This is an Alternate Universe where Mary didn’t die on the ceiling of Sam’s nursery; John didn’t go out seeking revenge on the monster that killed in wife, thus raising his sons like soldiers. No Mary and John is a married couple who have had their bumps and through their 30 years of marriage. 

This first chapter is just an introduction, if you will, of the characters in my story. 

Also a huge thank you to @firefly-graphics​ for providing me with the awesome divider!! 

California, 2005

"Yes Dean," Sam says into the phone, annoyed.  "My flight gets in on the 17th at 4. It'll give me plenty of time to get to the house and settle in before the party."

Not only has his older brother called to confirm he was going to make it home for their parents' anniversary party, but so had Mary and his younger sister, Y/N.

His girlfriend, Jessica-Jess for short- giggles beside him in the bed. He glances down at her and rolls his eyes. 

When Jess' hand makes its way under the sheet and her fingers wrap around his limp cock, Sam hurriedly gets off the phone with his brother.

Rolling to hover her equally naked body, Sam quirks an eyebrow. "Did you have to do that while I was talking to Dean?"

"I want you Sam," Jess says. "Make love to me."

Grabbing his now engorged member,  Sam threads it through her slick folds and pushes in, groaning at the snug fit. "Fuck Jess, you're so damn tight."

Hours later, while sitting through another lecture on the basics of criminal justice, Sam can't take his mind off the fact that he is going to be flying home to his family while his girlfriend stays back in their apartment. 

He had wished to take her home to meet his parents and siblings but she had a big test to study for in one of her classes and couldn't get away. He just hoped he didn't miss her too much. 

Little did he know, missing Jessica would be the least of his worries while he was home.

Meanwhile in Kansas 

Dean hangs up the phone in his office at the garage and sits back. It's all coming together.  In a couple of weeks, his parents, Mary and John Winchester, will be celebrating their 30th wedding anniversary with a huge party at their house.

At 26, even Dean knows in this day and age a marriage lasting that long was uncommon and a feat worth celebrating. 

Sure, Mary and John hadn't had bliss the whole 30 years but they worked through it and came out barely scathed. 

One bump in the road that Dean could remember was when Mary had become pregnant with Y/N, his baby sister. After she had given birth to Sam, the doctors advised Mary not to have any more children due to a blood disorder they had found during her second pregnancy.

For almost 3 years it had been just Sam and Dean then suddenly, Mary had gotten pregnant and in 8 months brought home the cutest little girl either boy had ever laid eyes on. They vowed to be her protectors, her guardians. No one would mess with Y/N without feeling the wrath of the Winchester brothers. 

Her early teens years had been difficult as Y/N went through a rebellious stage but once again, after some time it had all worked out and now the three siblings were best friends and confidants. 

Dean would soon discover just how close the three of them could be.

Across town, Y/N bounced down the stairs of her childhood home; her y/h/c hair flowing down her back.

Nineteen years old and still living at home, but she didn't mind one bit. Y/N had yet to figure out what she wanted to do since graduating high school earlier in the year. She was free from books and studying and boring old teachers who droned on all day.

"Mornin' Mom," she says as she makes her way into the kitchen and to the fridge to grab the orange juice. "You look lovely today."

"Thanks sweetie," Mary smiles at her daughter. "Your dad and I are meeting the party planner this afternoon to put the finishing touches on the party."

"Ok. I called Sam. He promises he'll be here. I warned him if he misses it, I will come to Cali and kick his ass."

Mary laughs. "I called him too. He told me the same thing."

"Oops!" Y/N giggles as she sips her juice. "Ok, well I got to meet up with Katie and Bekka so I will see you later. Love you," she says, kissing her mom on the cheek.

"Love you too. Don't misbehave."

Y/N turns as she goes to walk out of the room. "Who me? Pssh!" 

Her smile matches the one on her mother's face. Y/N heads out the door and off to her 'date' with her friends.

Y/N had no idea that soon she'd not be able to look her friends in the face without feeling shame and humiliation.

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