Supernatural Imagines

Gangster (Dean x Reader)

Warning- long, and smut at the end
Summary: AU World where Dean and Sam run gangs and run into some trouble when Dean marries Y/N. Her family's enemies are now after Y/N and her lover.

The Winchesters were known to be the wealthiest family in the state. Sam and Dean inherited the business when their father turned 50 recently. No one dared to mess with them. They lived up to the family name from what their father taught them. Sam and Dean were ruthless. They tortured a lot of people when they knew they were lying about information. They were really intimidating and attractive. All the girls wanted them. But, traditionally, you have to marry within the gang community.

Dean was determined to take the lead in finding a wife first. Sam had a few years under his belt before he would be able to find a wife. John and Mary looked at their candidates for who would be the perfect match for their oldest son. They agreed on one specific family: Anderson. Their daughter, Y/N, was the exact age as Dean and they had good relations with the family already. Y/N would be a good reliable choice for them.

What the Winchesters didn't know about Y/N's family was that they were a bit more complicated. They had a past history of violent crimes and anger issues with other gangs. This all came from her father and now there was the downfall.

Y/N didn't necessarily like being part of the gang. Her father expected her to take over the business when he was old enough and it disappointed him how she treated the gang. The job scared her and made her worry about people she loved all the time. Her father wasn't the most reliable person either. He always needed help getting out of something and he'd ask for Y/N to help him. He claimed it was to prepare her for the future. It just made her more of a target than he was.

She wanted nothing to do the gang if her father was just going to use her. She was a quiet person. She liked keeping to herself and being a normal citizen. Her family had a big reputation but didn't justify their past history of violence. Y/N thought they could do better but never got the chance to speak up.

John received word shortly back from Y/N's father that he had accepted the marriage request. "Perfect." He told himself.

John announced that night at the dinner table that Dean was getting married to Y/N. He watched his son's reaction to the news. Dean didn't have an ounce of emotion. He was good at hiding them. "Well, what do you think?" John asked, then sipping his wine.

"If you think she's a good fit. I trust you. I should have no reason to doubt your expertise." Dean responded with.

"Very good." John says and looked to his side to see Mary smiling too.

Meanwhile, Y/N's father announced it at their dinner table. Y/N stopped eating immediately and stared at her father in shock. She didn't want to get married into another gang but this life wasn't easy for any of them. Y/N was more so shocked that she was getting married to Dean. They had met a few times. Those few times, Y/N stayed in the car while her father dealt with the business.

"It will be a small and short wedding." Her father told her. "You should go dress shopping tomorrow with your mother. I'll send my bodyguards with you." He told Y/N. Y/N picked at her food.

"Um, alright." She says. Not like she had a choice.

-time skip-

Y/N got fitted into her dress and did her own makeup and hair. She took photos with her mother and father before arriving at the church.

She could feel herself getting sweaty from the nervousness. She rubbed her hands on her dress.

"It's normal wedding jitters it'll be okay." Her mother promised with a small smile. Y/N returned the smile.