Story 1: Dean's Crazy Amazing First Time continued
Scene: Inside Janie's Guest House.
Dean sits back down on the couch and looks up at his Aphrodite and his Cleopatra. He grins excitedly.
Dean: "So how do ya'll want to do…uh this?"
Janie: "Well there is a bed upstairs in the loft. My parents won't be home for at least a few more hours and my brother usually stays over at his girlfriend's place until really late."
Dean nods and immediately stands up.
Liz: "But, I think we should take turns it'll be easier that way.
Janie nods at her then giggles. Dean loves her giggling.
Liz: "Which of us do you want first Dean?"
Dean can't even fathom choosing at this point. He is totally in love with them both at the moment.
Dean tries to get his mind to calm down enough so he can actual think, but already most of the blood in his body is currently being driven elsewhere. His brain finally manages to recall a game he often plays with his brother Sam to settle disputes when they are deciding who has to do what chores.
Dean: "How about we play Rock Paper Scissors to decide? I play it with my little brother all the time!"
Liz and Janie look at him for a moment then they both crack up laughing.
Dean cheeks turn bright pink with embarrassment. He can't believe he just brought up his little brother at time like this and playing some silly kids game.
Great now they are going to think I'm completely geek loser and change their mind all together Dean thinks to himself.
Liz: "That is so adorable, I never would have thought of that."
Janie giggles again then she holds out her hand.
Janie: "So how does this game work again? I haven't played since I was like in first grade."
Liz: "First ball up your hand into a fist, then I think it goes rock beats scissor, scissor cuts paper and paper covers rock or something like that right?"
Dean nods at her in agreement.
Liz: "Okay, Dean why don't you and I play first just to show Janie here how it's done."
Liz holds out her hand in a fist and begins to shake it up and down.
Dean holds out his hand as well
Liz: "Rock! Paper! Scissors! Shoot!"
Dean does what he always does and chooses scissors and Liz picks Rock.
Liz grins when she sees their hands.
Liz: "I won!"
Liz laughs happily.
Janie: "Now is it my turn?"
Liz nods at her.
Liz: "If you beat him too then I guess he'll just have to watch us get it on."
Janie giggles back at her.
Dean grins.
Janie: "Oh okay."
Dean: "Man, is it bad I hope I lose now?"
Liz laughs at his remark then pushes Dean slightly on the shoulder.
Dean holds out his hand in a fist and shakes it so does Janie.
He again picks scissors, but Janie picks paper.
Janie pretends to pout a bit.
Janie: "Oh well. I guess you two will have to have all the fun without me."
Liz frowns as Janie picks up her dress preparing to walk back to the main house alone.
Liz: "No wait! This is your house Jan and you gave us a ride, food even let us hang here you deserve something."
Liz looks at Dean with a sexy smirk. He can tell already she has an idea.
Liz: "Dean, would you mind before you and I do this uh why don't you give Janie some head?"
Janie grins when she hears Liz's idea for a compromise, but Dean just looks surprised and a bit nervous to complete the task.
I've only ever done gone down on a girl once before in backseat of my dad's car he recalls. It was pretty hard to breath down there with her clamping my face so hard with her legs. I almost lost all consciousness so it was way more awkward than it was sexy and I couldn't even last long. But, I can't disappoint these girls now, not when I'm so close to paradise.
Dean finally takes a gulp then nods his head "yes" at them. He walks over to Janie and kisses her on the lips softly. Janie enjoys the taste of them right away. She turns to look back at Liz.
Janie: "Oh this is gonna be fun!"
Liz wraps her beach towel back around her body as she plops down on the couch and turns the television off so there are no distractions. Janie removes her dress again.
Dean takes Janie by the shoulders and positions her up against one arm of the couch so she can lean back against it while he goes down on her.
He kisses Janie gently on the neck then looks at Liz.
Dean: "Are you really going to just sit there and watch us?"
Liz: "Don't be nervous dude. I won't interrupt I swear. I just want a little preview before it's my turn."
Janie: "She'll be cool just go for it."
Dean smiles then kisses Janie again this time he doesn't stop kissing her. He kisses her neck, shoulders, chest, and stomach slowly working his way down her body until he is on his knees in front of her.
Janie spreads her legs a bit and leans backs.
Dean finally kisses her sweet spot and Janie can't help, but giggle at first. The more he kisses and touches and tastes her soon her giggles turn into moans.
He can't help, but grin at the sound of it feeling extremely proud and excited all at the same time. He immediately enjoys the way her soft short pubes tickle his chin as he continues to pleasure her.
Dean thinks to himself, her moans are even sexier than the giggling, damn this is amazing. I can really do this.
Dean prods Janie's opening with his index finger creating even more moans from her so he continues and she guides his finger even deeper inside. He smiles up at her for a moment then starts using his tongue again.
Janie can't help waiting anymore she is getting so turned on. She grabs Dean's hand and positions it over her clit.
Dean rubs it while tenderly kissing Janie's vagina and within a few minutes Janie comes with a huge moan her hands entangled in his brown hair.
Janie breathes heavily as she throws her arms back against the couch to brace herself to keep from totally collapsing on top of him as her orgasm sends delicious shock waves through her entire body.
Dean moves his hands to the sides of her hips to steady her until she calms down from the sweet pleasure of it all.
Janie smiles as she looks down at Dean.. He stands up and she throws her arms around him to give him a big hug.
Dean buries his face in her hair for a moment and takes in the sexy scent of it. He is so glad she enjoyed it so much that his erection grows even more.
Liz finally sits up after spending most of the time touching herself on the couch while watching Dean go at it.
Liz: "Well all I can anyone can say about that is…wow!"
Janie starts to giggle again still breathing heavily. She turns to look at her then nods.
Janie finally picks her dress up off the floor.
Then she kisses Dean's cheek and smiles at him.
Janie: "You go get her Tiger!"
Janie smacks Dean on the butt which puts an even bigger grin on his face.
Then she kisses Liz goodbye.
Dean frowns when he sees Janie put her dress on preparing to leave.
Dean: "Wait, you're not going to watch us too?"
Janie: "I would, but I have my dad's fundraiser to get ready for tonight so I need to get ready. Liz will tell me all about later I'm sure. I rather hear her whisper it to me at the fundraiser while all those boring politicians are droning on giving speeches it'll keep us entertained."
Liz smiles at her and nods in agreement.
Janie: "Oh and my brother keeps his condoms upstairs in his dresser top drawer so you two be safe."
Dean waves goodbye at Janie feeling sad to see her go.
Janie exits the guest house and heads back inside the main house to get ready for the party.
Liz stands up and takes Dean's hand. She slowly leads him up the stairs to the loft. The thought of what they're about to do and what Liz will tell Janie about it later makes Dean extremely hard. His heart begins beating so loudly in his chest it actually hurts.
Dean: "I don't know how much more of this I can take!"
Liz laughs at him.
Liz: "We're almost there just hold on there."
Liz pushes Dean back against the bed.
She goes over to the dresser and opens all the top drawers until she finds a box of condoms.
Liz checks the size on the box then looks at Dean's cock afraid they won't even fit at this point.
Liz: "Um…Dean, you need to try and relax a bit so I can get this on you okay. Try thinking of something that turns you off I've read it helps you guys."
Dean shyly nods at her. He begins to picture all the horrible hideous monsters that his dad fights and kills. It takes a few minutes, but soon he begins to feel softer as his body relaxes that is until Liz puts the condom on him.
She smiles as she rolls it on. Her touch quickly makes him hard again and this time he can't wait any longer to have her.
Dean pulls Liz on to his lap quickly and grabs her hair.
Liz positions herself on top of him and tosses her towel to the side. She leans down to kiss him and he captures her mouth with his harder than ever.
Liz moans against his mouth just as Dean feels himself slipping into her body.
Liz stays still for a few more torturous seconds then she finally begins to grind her hips on top of him.
Dean almost screams out loud, but he bites his own lip really hard to keep from coming right away.
Liz sits up more and rides him extremely smoothly at her own slow leisurely pace. Dean actually wonders how it is she has never done this before when she is so good at it.
She takes Dean's hand and places it on her breasts as the both start to move together in unison.
Dean pinches her nipples and when she moans out "Oh I like that." His has had enough!
Dean comes hard filling up the condom quickly. He feels as though he is about to pass out and falls back against the bed from the amazing pleasure.
Liz leans down and kisses his forehead which is the last thing Dean remembers before completely falling asleep.
An hour later, Liz gently wakes him up.
Dean bats his eyelashes at her as he wakes up smiles then he reaches over to hug her.
Liz whispers in his ear.
Liz: "You never forget your first time."
Dean just quietly nods feeling so satisfied and happy he wishes they could never get out bed again.
Dean: "That is for sure! I'll never forget you or Janie."
Liz: "Good. I'm glad. But, Dean there is just one more thing I want you to do for me before I go to Janie's room and get ready for the party tonight."
Dean sighs and brushes a few strands of hair from Liz's sweaty face.
Dean: "Anything for you babe?"
Liz: "I want you to go down on me like you did for Janie."
Dean sits up right away and grins at her. He jumps out of bed and removes the condom still surrounding his penis. Dean tosses it in the trash by the dresser then walks over to edge of the bed and kneels down.
He reaches out and pulls Liz by her leg which makes her laugh.
Dean realizes now that Liz didn't come earlier when he did and he doesn't want to leave her unsatisfied so he becomes determined to give it all he has.
Within minutes Liz is moaning even louder than Janie was and Dean uses two fingers this time along with his tongue to really drive her crazy.
Liz: "Oh Dean, I'm almost there. Don't stop!"
Dean decides to make it extra special. He quickly runs over and grabs another condom, puts it on and before Liz even knows what is really happening Dean is on top of her.
He pushes his dick into her from behind unknowingly hitting her sweet G-spot. She buries her face in a pillow to muffle her scream as she comes shaking frantically.
Dean grins then pulls out of her and sits up beside her as he pulls her closer to him again.
Liz takes deep loud breaths as she looks up at him happily.
Dean: "So am I really your first?"
Liz: "Yes, you're the only man."
Dean smiles at her for finally calling him a man and not a kid like she use to. He figures Liz will probably go back to being strictly lesbian with Janie after this, but he is glad to know he could be part of their little experiment.
After a few more minutes of making out Liz tells Dean to get dressed and meet them out by the pool in an hour so they can drive him home before heading off to Janie's dad's big fundraiser.
Scene: The Mojave Motel
Time: 9pm that night.
Dean waves goodbye as the two beautiful girls dressed to the nines smile and blow kisses as they pull out of the parking lot in Janie's Mustang blasting more classic rock.
He puts the key in the lock and goes inside his hotel room.
Sam immediately looks up from his spot in front of the television as Dean enters the room. Sam turns off the television and stands up.
Sam: "Dean, you missed dinner so I had to cook it myself. I left you some on the stove though. Were you really out cleaning pools with Pedro all this time? You must be starving."
Dean smiles as he takes his jacket off.
Dean: "Don't trip Sammy boy, I already ate twice in fact."
Dean laughs, but Sam has no idea why that was supposed to be funny.
Sam: "Yeah, well while you were out dad call. He is coming back to get us tomorrow. He says we're heading to South Dakota next. Bobby called too and he agreed to take us to see Searching for Bobby Fischer."
Dean rolls his eyes at his brother for wanting to see such a nerdy movie.
Sam smiles happily glad that they will be leaving Nevada during the hot summer and going to Bobby's house in Sioux Falls where it's much cooler.
Sammy loves going to Bobby's because there are plenty of books to read at the Sioux Fall Library. Bobby's cooking is a lot better than Dean's and he knows that won't have to share a room with Dean while he is there either.
Dean stares at Sammy sadly for a moment then flops down on the edge of his bed.
Dean: "Oh, okay I'll get our stuff packed up."
Sam: "What's the matter Dean? Am I missing something here? I thought you couldn't wait to get out White Pines?"
Dean: "I'm fine. I know it's really hot here Sam, but that isn't always a bad thing you know."
Sam looks at Dean confused for a moment by his expression and his comment. Sam knows how much Dean hates very hot summer weather.
Sam: "You'll miss hanging with Pedro is that it?"
Dean rolls his eyes at Sam.
Dean: "Uh yeah sure that is it."
Sam studies Dean's face and can tell right away there is something more going on.
Sam: "No, that isn't it! What are you hiding Dean?"
Dean: "Look Sam, I promise I'll tell you all about it someday when you're older just not right now okay. I'm beat its been a long hot day"
Sam rolls his eyes and sighs at Dean.
Sam: "Yeah, okay whatever dude."
Sam turns the television back on and starts washing the dishes in the sink.
Amazing by Aerosmith video comes on the T.V.
Dean kicks his shoes off then moves back further onto his bed to lean back against the head board. He closes his eyes for a moment picturing his Aphrodite and Cleopatra singing and dancing for him in the guest house to this Aerosmith song.
"I kept the right ones out
And let the wrong ones in
Had an angel of mercy to see me through all my sins
There were times in my life
When I was goin' insane
Tryin' to walk through
The pain
When I lost my grip
And I hit the floor
Yeah, I thought I could leave but couldn't get out the door
I was so sick and tired
Of a livin' a lie
I was wishin' that I
Would die
It's Amazing
With the blink of an eye you finally see the light
It's Amazing
When the moment arrives that you know you'll be alright
It's Amazing
And I'm sayin' a prayer for the desperate hearts tonight
That one last shot's a Permanent Vacation
And how high can you fly with broken wings?
Life's a journey not a destination
And I just can't tell just what tomorrow brings
You have to learn to crawl
Before you learn to walk
But I just couldn't listen to all that righteous talk
I was out on the street,
Just a tryin' to survive"
The End of Story 1
*Author's Note: Thanks for reading and please feel free to leave comments or reviews on Story 1. I'll be putting up Story 2 shortly starting with Chapter 6 and it will feature Sam's first sexual experience then Story 3 will be all about Castiel's upcoming first time.