Jack x Reader One-Shots/Trilogies

First Time

Omg I'm so sorry I haven't posted in a few days. Thanksgiving was a disaster and then I had to go to the ER but I'm ok now :))
(Got this idea from a lovely follower of mine)

I was laying down, next to Jack just looking at the television. We've been dating for a few weeks now, behind Sam and Dean's back.
"I'm hella bored." I groaned, surfing through channels.

"You shouldn't cuss, Y/N." Jack said, playing with my hair. I shot him a bitch face and just laughed while shaking my head.

When we stopped at a channel the movie was pretty good until it got awkward... and what I mean by awkward was a sex scene. (Oh boy another one.)

I turned the television off and snuggled into Jack's chest, drowsing off.
"Y/N... could you help me understand sex?" Jack said, continuing playing with my hair. I became flushed and looked up at him.

"... p-pardon?" I stuttered, looking red as a cherry.

"I just don't understand the pleasuring and the sexual intercourse." He added.

"Well Jack... I wouldn't really know because I'm a... virgin. But! I would ask Dean because he knows all that kind of stuff."

"Okay, thank you Y/N."

I blushed and planted my face into the pillow, dying because of the awkward silence.

~

I was walking out of the kitchen back into the bedroom when Dean came up to me.
"Hey Y/N, could I ask you something?" He said, leaning against the entryway.

"Uh... yeah sure. What's up?"

"Jack just asked me how to have sex. Does that sound... odd to you?" Dean asked.

I pinched the bridge of my nose and began to blush.
"He asked me about it and since I have no clue.. I told him to ask you about it." I replied, nervously.

Dean nodded his head and laughed.
"Well damn. He wanted to know everything."

"D-did you tell him everything?" I stuttered.

"Only the good stuff." Dean winked and headed to the kitchen.

I headed towards the bed and sat on it, searching for the remote. Jack later came in with a smile planted on his face.
"Sam and Dean are going to be gone for a few hours."

"Alright."

Jack sat down next to me and I noticed he was studying me while I was flipping channels. I became flustered and turned to him.

"Is everything alrigh-"

Jack pulled me into a kiss and I did nothing but kiss him back. He snaked his arm around my waist and laid me down on the bed to where he was over me.

I pulled away from his soft lips and blushed.
"Are we actually doing this?"

Jack nodded his head and planted his lips on mine again. Dean wasn't lying when he told me he taught him the good stuff.

Jack picked me up and slammed my back into the wall, exploring my mouth with his tongue. I jumped and he wrapped my legs around his waist and pinned my arms against my head, aggressively.

Jack tore off our clothes and studied my body, looking at it in awe.

"God you're beautiful." He groaned, kissing my neck roughly. I moaned when he found the sweet spot which turned him on.

It's like Jack couldn't maintain himself anymore and so he quickly slid his member into me. I winced in the pain and groaned as he paced back and forth. For having no experience, Jack was amazing.

We were both very rough with each other as we slammed each other into walls and he bruised my wrists from squeezing so tight.

He pumped in and out unbelievable fast and didn't stop. I groaned out his name and he smirked, planting his lips back onto mine.

~

Our hearts were racing and I collapsed onto him, panting. My body ached of pain once my adrenaline slowed down and I groaned.

Jack noticed this and kissed my lips, healing my aching, bruised body.

Sorry for shortish chapter I've been soooo busy 😅