Supernatural Imagines and Preferences

Winchesters X Reader

Gay!Reader(boy) Boy's name (Jason)
Requested by @Total_Whovian_
Imagine: Jason goes on a hunt with the Winchesters and has to flirt with with girl. The Winchesters don't know he's gay until he tells them.

Jason's POV--

"Jason! We gotta hunt!"
Dean shouted from the bunker's front door. Jason sauntered to the stairs and said
"Yeah? What's it about this time?"
"Let's just say it's gonna be great. As in strippers great. As in flirting with the strippers great."
Jason swallowed hard.
"Oh...oh yay! I've been uh waiting for one of these hunts!"
"Yeah me too dude. Be ready in five."
Jason went to pack his duffle thinking about how the hell he will make it through this hunt.

Time skip brought to you by interrupting moos- "so get this..."

They sat in the impala going a couple cities for the hunt. It seemed easy just a siren well easy for Jason and Sam. Dean not so much since he's a little hormone boy,but we still love him anyway. Once they got to the club Jason got nervous, sweaty, and dry mouth. Why is Jason so nervous you ask?

Well Jason is the one who has to flirt with the strippers for the information and well Jason is gay, but he hasn't told the Winchesters because he's scared they'll reject him or treat him different.
"Jason man you okay?"
Sam asks with a worried look on his face.
"Yeah just peachy."
They walk into the club, music blared, and a strong stench of alcohol lingered everywhere. They went to the back looking where all the off duty strippers were. They spilt up to cover more ground. Jason walks up to one of the girls, trying his best to be convincing.

"Hey there could I ask you a couple questions about the murders happening lately?"
Her eyes take down his body while smirking
"Anything for you."
"Um okay so has anyone been acting strange lately?"
"Um well one of my friends seemed a little pissed today."
"What was she doing?"
"Well she took all my shifts, so I haven't gotten much money today."
Jason nodded not wanting to be by this girl anymore since she kept looking all over him.

Dean came up behind him and said
"Come one we got what we need."
Jason nodded to the girl and walked away. They went back to the impala, but Sam stopped Jason from getting in.
"Dude what's wrong you've been acting strange today?"
"Okay fine! You wanna know what's wrong?! I'm gay!"
Dean and Sam shared shocked looks no one spoke at first until dean asked,

"Why didn't you tell us earlier?"
"I thought you guys wouldn't let me hunt with you and treat me differently."
"Dude no. It doesn't matter what you are into. Once a brother always a brother."
Jason breathed a sigh of relief.
"Thanks so much."

A/N

I'm so sorry I've been so busy with school and I felt so guilty for not updating. There was so much happening like homecoming, ten my dog got sick, and now my uncle is in the hospital. It's like I haven't even barely gotten a break, so I hope you liked this! :) But on the bright side you guys remember in my older chapters I was talking about this guy that I liked well I like him again and this time it's a really big crush. I feel like this time might be different though because we text after school and we didn't use to and he's been VERY HUGGY lately so I really hope third time is a charm!
~Baylee~