Title: You Never Forget Your First Time
Synopsis: Stories describing the Winchester brothers' first sexual experiences with women and how both of them lost their virginity.
Author: lovepass77
Rating: M for pervasive sexuality, nudity and some violence.
Genre: Supernatural Romance
Based On: Supernatural the television series created by Eric Kripke
Main Characters: Sam Winchester, Dean Winchester, John Winchester, Liz Silverstone, Janie Tyler, Rachel Nave, Dirty Diana and Azazel.
Pairings: Dean, Liz Silverstone and Janie Tyler; Sam, Rachel Nave and Dirty Diana,
Songs: I like to incorporated songs and lyrics into my stories because music is such a wonderful inspiration for me, but especially because of Supernatural and the songs I choose help me to tell the story and it helps if you listen to theses songs as you read along to better understand my stories and the vibe I'm trying to create.
Disclaimer: I have absolutely no rights to Supernatural, it belongs to Eric Kripke aka T-Bear. I just like to write stories about this great show.
Author's note: I will also be writing stories about Mary and John's first time, Bobby and Karen's first time and Castiel's first time losing his virginity an all of these stories including these on Sam and Dean are in honor of the upcoming episode Like a Virgin. These are just my personal interpretations of these events so I don't mean to offend anyone who may have different ideas, but I do appreciate positive feedback that can help me to write my stories. Thank you for taking the time to read this.
Story 1: Dean's Crazy Amazing First Time
Location: White Pine, Nevada
Time: The Summer of 1994
Scene: Mojave High School
Introduction:
Dean Winchester pokes his head out of one of the boys' bathroom windows to check to see if the coast is clear.
The school security guards on campus are real douche bags and if Dean gets caught ditching again he knows they'll try to make him spend another whole week after school in detention with mean old vice princpal Mr. Finch.
Dean is determined to make a stealthy get away. Its way too hot today to stay in summer school Dean decides. He would much rather be hanging out with his buddy Pedro in the backyards of White Pine Hills homes making a little money.
White Pine Hills is the only ritzy neighborhood in White Pines located down the main highway about two exits from his high school. Pedro will soon be coming to pick him up. Its not that Dean can't walk there on foot his dad has him use to hiking long distances by now, but it's a 110 degrees outside and Dean can already feel the sweat starting to form on his brow as he crawls out the bathroom window so he is glad to have a ride to take him there.
Pedro Gonzales runs a pool cleaning business in White Pines and Dean met him when he was cleaning the pool at the Blue Canon motel where the Winchesters have been staying for the last few months. Pedro offered to let Dean work with him cleaning pools in exchange for some extra cash so Dean can blow it at the video arcade and occasionally have some left over to go to movies with Sam.
Cleaning pools gives Dean a chance to check out the sexy housewives who strut about their homes in White Pines Hills half naked. For a fifteen year old boy as far as Dean is concerned it's pretty much a dream summer job. He especially loves it when some of the nicer housewives always offer them cold lemonade while they work and invite Dean inside to move furniture around instead which gets him out of the hot sun for awhile.
Dean knows that anytime now his dad, John Winchester will be finished working the area for leads on the demon that killed their mother and they'll be moving on again to another city soon. Dean can't wait to leave White Pines. He hates the summertime in Nevada which he thinks is way too damn hot.
Dean also hates being cooped up in the motel all the time while his dad is out on hunting trips, but mostly he hates sitting in class during his summer vacation because it's so boring. The guy who sits behind him Todd Linkenheimer always falls asleep and his hot breath blows on Dean's neck making him even more uncomfortable sitting in Social Studies.
He escapes the bathroom and quickly heads towards the front of the school making sure to stay in the shade and to watch out for any security guards.
Dean makes it to the front of the school and checks his watch. It's already 12:59 and Pedro usually picks him up on the corner of the parking lot at 1:00pm.
He sits in his usual spot behind the school garbage bins so he can look out for Pedro's truck without being seen. He takes his army green jacket off and lays his jacket against a bin as he leans back on it to cushion his back a little.
Dean is wearing a black t-shirt which he is thankful hides sweat stains pretty well and his faded light colored jeans have holes at the knees to give his legs a little more air in the summertime because he refuses to wear shorts.
Dean knows his dad wouldn't really approve of him ditching school like this, but then again it's not like he plans on becoming a doctor or lawyer some day like his little brother Sammy dreams of.
He knows exactly what he'll be doing; working the family business just like John so a high school diploma isn't really on his top list of priorities since hunting down supernatural creatures involves a whole different type of education that he can't get at Mojave.
Information that helps him to become a hunter Dean finds a lot more useful and interesting to learn about, especially because it gives him a chance to impress his father who seems to only have time for him when he's training Dean about hunting.
Dean thinks about their previous summer together when his dad put him through rigorous boot camp training exercises to prepare him for the future. He learned a lot of fighting skills and his dad finally gave Dean his own gun.
He smiles to himself when he remembers how for first time during one particular exercise in late August he was able to knock his dad to ground in the middle of combat. As far as he's concerned his father is the best of the best when it comes to hunting and Dean wants to make him proud and help John kill all the evil sons of bitches that are out there.
Dean's mind drifts to his little brother Sammy Winchester who is completely the opposite when it comes to his schooling. He knows Sam is still sitting in his own summer school class probably enjoying it. I can't understand what's wrong with that boy's head. He'd rather spend all day at school or at the library reading Charles Dickens, Shakespeare or whatever boring book he can find. But, dad and I tried to teach Sammy how to shoot a ghost and he acts like it's the most depressing thing ever. What ten year old red blooded American boy doesn't want to play with guns? I mean come on! Dad has the coolest job ever!
This summer he says he's going to teach Sammy and me how to use a sniper gun. I can't wait, but I just wish Sam wouldn't be such a stick in the mud. Learning how to kill those monsters in the dark is real life hero work! None of that apple pie Leave it to Beaver nonsense that world doesn't matter it's all just an illusion. We know what's really out there and we've got to protect the other poor bastards that don't have a clue.
Dad always says to me about Sammy "I swear that kid's going to be death of me," and that's because dad babies him too much. He gives Sam whatever he wants. I ask for some money to get some new cooler clothes because I've outgrown most of mine or money to buy more food because I'm a growing boy who likes to eat and he tells me to go get a job if I want more money.
But, Sammy just has to bat those little puppy dog eyes of his when he asks dad for cash to buy comic books or trick cards or some gay looking top hat so he can learn how to do magic tricks and dad just forks over the money. Un-freaking-believable!
Dean frowns as he thinks about it and wipes the sweat from his face with his hand.
That kid gets whatever he wants it's a damn shame! If I try to be helpful and teach him a new fighting move Sammy always screws it up at first then when he gets a bump or a bruise he goes off whining to dad about it. So I'm the one who gets chewed out for not protecting him and forced to wax the Impala down while Sammy shows dad one of his lame little card tricks. It's a nightmare sometimes living with that kid really I'd like to stuff him in a closet somewhere and leave him, but Sam's already learned too well how to pick locks so he'd just escape or run away again.
Dean sighs to himself.
The worst of it is sharing a room with him. I can barely get any privacy at all. I'm fifteen for Christ sake I need some alone time, but Sammy is always there asking questions or just breathing it's the most annoying thing he does! I can't even go out after it gets dark to party like everyone else because he gets scared alone by himself what a baby!
Still I know I have to protect him. There's a lot of bad shit out there just waiting to strike and even though Sammy knows how to fight the kid is still as green as they come. He couldn't take down a werewolf or a banshee by himself yet. Nope, I've got to look out for him and keep his butt out of trouble because one day dad is going to get that son of bitch that got mom. One day he will and I'm going to help him. Then Sammy will be glad he had us looking out for him all these years. I'm going to be his hero a regular Batman.
Dean fondles the necklace Sammy gave him last Christmas that hangs around his neck every day now.
The golden head glistens as it catches the sunlight. The sides of Dean's lips start to creep up almost into a smile as he touches it, but his thoughts are suddenly interrupted by the sound of two people arguing outside.
Dean peaks around the corner of the main auditorium at his high school and sees them.
Liz Silverstone is a sixteen year old with very long straight blond hair. She shoots dirty looks at an irritating jock named Paul Foster who keeps trying to get her to date him.
Paul: "Babe, you don't know what ya missing?"
Liz: "I know that you're missing a few too many brain cells and can't take a hint."
Paul frowns and stands in front of her to block off her exit.
Paul: "You're not being very friendly. Give me a chance. I'll make it worth your while."
Liz: "And you don't seem to be getting the message dude. I've got shit to do today that doesn't involve you so back off!"
Liz moves to get around Paul.
Paul grabs her arm to hold her back.
Paul: "Don't be such a bitch! I'm offering you the greatest opportunity to be with me."
She glares back at him almost ready to punch him for grabbing her like this.
Liz: "You'd better let go of my arm now unless you want to have to learn to masturbate with your left hand only."
Paul smirks at her and refuses to let her go.
Dean has seen enough of this idjit.
Dean: "Hey dipshit! Let her go!"
Dean marches up to them ready for a fight if Paul doesn't cooperate, but Liz puts her other arm out and her hand up to stop Dean in his tracks.
Dean stares into her sexy greenish hazel eyes. Liz is wearing faded cut-off blue denim shorts, an army green camisole that barely covers up the silver hoop in her belly button, green Nikes and a silver and black friendship bracelet on her right wrist.
Liz: "Get back to class, kid. I can handle this myself."
Dean frowns at her for calling him a kid even though he's still about a half foot shorter than both of these seniors he doesn't care.
Dean: "Hey, I'm not just some kid!"
Liz rolls her eyes at Dean.
Paul: "Look you better listen to her before I lay you out right here freshman!"
Dean steps closer
Dean: "I'd like to see you try dumbass!"
Dean throws his jacket down on the ground.
Paul: "Oh you think you're a tough guy huh?"
A loud honking noise comes from the parking lot and Dean hears a classic rock tune blasting on the radio in Spanish. Dean realizes immediately it sounds like Pedro pulling up in his truck.
Dean turns his head towards the parking lot to see and Paul takes the opportunity to hit him.
Paul releases Liz's arm steps up to Dean while he's face is turned and punches Dean in the side of face.
Dean falls to the ground on top of his jacket.
Liz angrily screams at Paul.
Liz: "Stop it asshole!"
Paul ignores her and stares down at Dean with a cruel smile.
Paul: "Who's that in the car you're boyfriend? You should have run off with him when you had the chance. Now I'm going have to teach you a lesson kid.'
Paul laughs and prepares to kick Dean in the chest.
Dean uses his quick reflexes to stop Paul's kick mid air by grabbing on to his shoe with both hands. Then with a fast twisting motion knocks Paul of his feet while twisting Paul's ankle at the same time.
Paul hits the ground and cries out in pain.
Paul: "Ahhhhhh…..my ankle!"
Dean quickly jumps up to his feet and balls his fist ready to strike Paul again.
Liz grabs Dean's fist with both hands to stop him.
Liz: "No, let me!"
Liz then turns towards Paul and punches him out with one quick shot to the nose.
Paul's head falls back against the grass with a thud as blood begins to drip from his broken nose.
Dean looks at Paul then back at Liz.
Dean smiles at her.
Dean: "Not bad for a girl."
Liz: "I told you I could handle it. This really was none of your business."
Dean: "Maybe not, but I'm not one of those guys whose sees someone in trouble and just doesn't nothing."
Liz looks Dean up and down for a minute thinking he's a cocky little thing, but then finally she cracks a smile.
Liz: "You're alright kid. So where ya off too?"
Dean: "Why do you need a lift?'
Liz smirks at him a bit then picks up his jacket off the ground dusts it off then hands it to him.
Liz: "Maybe. I was going to take the bus."
Dean: "Nah, keep your money. We'll take you wherever you want to go."
Liz: "Oh really? That's a pretty big commitment to make to someone you just met. You don't even know my name yet."
Dean smiles and holds out his hand to shake hers.
Dean: "Well, I'm Dean Winchester."
Liz shakes Dean's hand as she thinks of what name to give him.
Liz: "You can call me Cleopatra."
Dean raises his eyebrows at her for a moment.
Dean: "You're not going to tell me your real name are you?"
Liz laughs at him.
Liz: "Nah, that be too big of a commitment, but I'll take a ride from you and your friend over there."
Dean smiles at her realizing this chick has a lot of spunk.
Dean: "Alright, let's go!"
Dean and Liz walk over to Pedro's truck. Dean opens the door for her and Liz sits down in between Dean and Pedro.
Pedro Gonzales is a young man of 23, but a life of hard labor makes him look quite a bit older than he actually is. Pedro smiles at them then offers Liz a piece of chewing tobacco speaking to her in Spanish though he can speak English very well.
Liz: "Sure, thanks."
Liz takes a piece and begins to chew it.
Pedro winks at Dean indicating to him that he approves of her which makes Dean smile back at him. Then Pedro takes off out of the school parking lot just as two security guards rush around the corner towards them to try to stop them from leaving.
After they are down the street a ways Pedro turns his music down so they can talk.
Pedro: "So where to?"
Liz: "There is a truck stop out on 93 right pass Elmer's gas station. Do you know where that is?"
Pedro nods as he heads for the ramp on to the highway.
Liz leans back against the seat and stares out the window.
Dean graciously angles the vent blowing cool air at them towards her.
Dean: "So what's at this truck stop?"
Sarcastically, she replies back to him.
Liz: "Truckers."
Dean looks at her suspiciously.
Dean: "You're going to meet up with a bunch of truckers?"
Liz: "Maybe. What's it to ya?"
Dean: "Hey, look that sounds like fun and all getting raped and killed at a truck stop by truckers, but how about instead you come and hang out with us at the pool?"
Liz smiles at Dean, then she smacks the tobacco in her mouth at him and pinches one of his cheek.
Liz: "You're such a cute kid, but I'll be fine."
Pedro bites his tongue to keep from busting out laughing.
Dean rolls his eyes at the both of them.
Dean: "Fine then I'll just hang out at the truck stop too."
She frowns at him.
Liz: "I don't need you looking out from me Dean."
Dean: "Oh I'm not going for that. I heard somewhere there are a lot of silly young high school babes that like to hang out at these truck stops so I'm sure I'll find one there that will actually interest me.
Liz: "Oh you heard that somewhere did ya?"
Dean nods then turns his head away from her to look out the window. He frowns as he stares out at the homes they pass by, but he tries his best to hide it from her.
Liz smiles at the back of Dean's head enjoying his obvious attempt to pretend like he's not that into her.
Pedro turns his rock music back up and the three of them ride the rest of the way in silence as Led Zeppelin plays on the radio.
'Your Time is Gonna Come' Lyrics by Led Zeppelin
"Lyin', cheatin', hurtin, that's all you seem to do
Messin' around, every guy in town
Puttin' me down for thinkin' of someone new
Always the same, playin' your game
Drive me insane, trouble's gonna come to you
One of these days, and it won't be long
You'll look for me, but, baby, I'll be gone
This is all I gotta say to ya, woman
Your time is gonna come, your time is gonna come
Your time is gonna come, your time is gonna come
Made up my mind, break you this time
Won't be so kind, it's my turn to cry
Do what you want, I won't take the brunt
It's fadin' away, can't feel you anymore
Don't care what you say 'cause I'm goin' away to stay
Gonna make you pay for that great big hole in my heart
People talkin' all around
Watch out, woman, no longer is the joke gonna be on my heart
You been bad to me, woman, but it's comin' back home to you
Your time is gonna come, your time is gonna come
Your time is gonna come, your time is gonna come
Your time is gonna come, 'bye, 'bye-'bye, baby
Your time is gonna come, right now, right now
Your time is gonna come, believe me, my girl
Your time is gonna come, oh, oh, oh, oh-oh
Your time is gonna come, nah-nah, nah-nah, nah-nah
Your time is gonna come, I'm not likely to wait for ya
Your time is gonna come, goodbye, baby
Your time is gonna come."