I get the call in the middle of the afternoon: “Casey, it’s Jack. I’m in trouble; I need you to go to Nate’s, get him and come down to bail me out.”
He tells me where he is, I ask no questions and I’m out the door. I arrive at Nate’s not 10 minutes later and am half way through “Jack needs our help he’s—”, before he stops me with his keys already in his hands, “Alright, where to?”
We’ve been on the highway for an hour now and all I can think about – when I’m not worrying about Jack – is how long it’s been since I’ve been this close to Nate. I’d always considered him as my big “what-if”, but figured my chance was gone forever because he’d recently gotten a girlfriend who was oh-so-wonderful.
We’d only been together as young teenagers, barely 17, all sweaty palms and rough kisses. We never got to sex but the nights I had stayed up imagining how amazing it would be between us were suddenly flashing behind my eyes.
Jack being thrown in jail for public drunkenness three states away wasn’t looking so bad. My view of Nate’s bulging arm on the steering wheel, 6-foot plus body barely fitting in this old truck, was making this so much easier.
We get to the police station at around nine that night and request to see Jack. On the phone he hadn’t told me what he’d gotten in trouble for so I had no idea what to expect but I figured it couldn’t have been too bad.
When we get there we can’t even bail him out. Something about disorderly conduct regulation being letting the person spend at least a full 24 hours in jail.
“Jackson Heathridge was brought in at 3 am this morning, so you’ll only be able to get him out after 3 tomorrow. And even then, we don’t even allow releases until 9 am.”
Nate has to hold me back before I can lunge at this oversized beanbag chair telling me her stupid regulations.
“So we came all this way and drove like 6 hours for nothing!” I scream, as I’m being lead out of the tiny department against my will. “This is so fucking ridiculous. I am going to kill Jack. Kill him! He couldn’t have mentioned these details over the phone?!”
“He was probably too out of it to even remember any details of his arrest. It’ll be fine. We’ll crash at a motel we passed on the way here and just get him tomorrow morning.”
I stop putting up all resemblances of a fight once we get to the motel and it hits me that neither of us anticipated we’d be staying the night: therefore, no clothes.
"It doesn't really matter. I sleep in my bra and panties anyways; you’ll just sleep in your boxers. Nothing we haven’t seen each other in before.” It’s true too; those nights we spent together as kids, we never went all the way, but the places we did go were always good enough.
I undo my bun and start to peel off my layers as I walk to the shower, "I'll be out soon,” I mention.
I shower quickly. I was upset about Jack but I decide to just put it behind me; everything should be fixed in the morning. I washed my underwear so that I could dry it and just wear it again. I come out in my towel and wet hair, Nate’s sitting on the bed.
"Shower's free," I say lowly. I sit down on a chair near the radiator and put my panties and bra to dry while I watch TV for a bit. Nate’s still in the shower when I decide to put on my underwear, they feel dry enough so I start to put on my bra. Right as I start to slip my panties around my thighs I hear the door open. I slip them up as fast as I can and start to blush when I see Nate come out of the bathroom in his boxers, blushing just as hard.
"Oh, sorry. My bad. I should've warned you."
"No, no. It's cool don't worry about it, it's nothing really."
I head over to the bed, trying to calm down. He comes up to the foot of the bed staring down at me, looking unsure of himself, "Uh, okay, so I'll just sleep on the couch and...."
"Oh, shut up. Just sleep here with me, you idiot. It's not a big deal." I open the sheets for him on his side of the bed. He still looks unsure, but very relieved at the idea of getting to sleep in a bed and lies down next to me.
I haven’t been this close to him since we were 17, so it’s been a few years. We grew apart, then we were just friends, now it’s been four years and here we were. It’s like we’re nervous teenagers again… for me at least.
I keep looking at him. My eyes graze down his stomach, over his tan skin and tight stomach. He’s lying on his back staring up at the ceiling. I’m on my side facing him and suddenly realize how little clothing we’re both wearing, and how this could be my last chance. I reach over and put my hand on his shoulder, "Hey, are you okay?" He looks at me like he's just remembered I was next to him.
"Huh? ... Oh yeah. Just thinking about Jack, and how we’ve made this trip in vain."
I sigh, “Don't remind me, sometimes I wonder why we put up with this kid." I put my hands on my face. “And then I remember that he’s not so bad…”
He laughs a bit and turns onto his side to face me, “Yeah, only when he’s not being reckless.”
“Yeah, like that’ll ever happen,” I put my hands down and look up into his eyes, staring right through me.
"Everything will turn out just fine. We'll get him out tomorrow. Everything will be back to normal."
I search his eyes and move closer. He's significantly taller than me so even though we're lying down I'm still titling my head to look at him. My head is at his shoulders and I lean in right under his chin. I feel him tense up as our bodies inch closer.
"I know. I'm just worried is all."
"Just try to sleep,” he says finally after a long pause and puts his hand on my shoulder, grazing it slowly down my arm.
I shift and turn around so that my back is to him. He keeps his hand on my arm for a while. I move myself closer to him so that now my practically bare ass is sitting right in front of his cock. I didn’t think I’d be able to go through with it, but just the feeling of him being so close to me has made me want to feel like more of him around me. If I got anything from that look in his eyes he wants this too.
I feel his hand squeeze my arm a little as my ass brushes up against him. I take my other hand and place it over his and pull it down to my hips, then around my waist and to just below my belly button where the hem of my panties sits. I still have my hand over his and I leave it there for a bit, basking in the moment of having him so close to where I want him to be. I decide I could live with this moment, even if he doesn’t make another move, and I pull my hand away.
The seconds before his next move seemed to take so long but thankfully I haven't misread what he wants to happen and I quickly realize he wants this too.
He starts to rim his finger right under the elastic, just barely. I stay in position as he moves his hand lower into my underwear. He’s got his whole hand inside and I feel the first tentative graze of his fingers over my clit. I take a deep breath and quickly turn around so that now I'm facing him again; his hand didn’t travel with me and has now moved to my lower back, slowly inching down my ass. I stare up at him as I start to tangle our legs together. He's now moved his whole hand into my panties again and has clasped a whole cheek and with a squeeze he pulls me closer.
I put my hands on his chest and wrap my legs around him. He then moves his hand to the front of my panties where he goes lower until I feel one long cold finger skim the folds of my wet pussy just once. I bite my lip and continue to keep eye contact with him as we lie on our sides in this straddled position. One of my hands has traveled down his chest and is now reaching into his boxers: reaching my fingers lower. This doesn't seem to distract him from his task because in the next second I feel one finger slide inside of me so tantalizingly slow I can't help but let out a long soft "fuuuccckkk" till he's all the way in.
He pumps it in and out slowly, his palm pushing against my clit with each push. In and out, in and out, by the third time he goes back in with a second finger and this is where I need to break eye contact as I shut my eyes tight trying to savor the moment.
I let out a long moan this time and my breathing has begun to get shallower. I move my hand down into his boxers and get my first feel cock; it’s hard and think in the grasp of my hand. I travel along the length of it lightly all the way to the tip, this time it's his turn to close his eyes as I continue this motion twice more. But my time with him is cut short as he moves his free hand to unclasp my bra and I have to finish taking it off and throwing it across the room. After that he moves his head to my neck and starts sucking on it all the while still pumping in two of his fingers into my pussy.
His fingers feel so good going inside of me. Over and over again they pump into me and I give a little shudder as I feel myself pull him in, every time getting a little bit wetter as he pulls out. By this time I'm moaning and twisting under his touch so much the bed is shaking.
Suddenly he moves his free hand to cup the nape of my neck and I open my eyes again, knowing something’s coming. All in one motion he slips in the third finger just as he leans in for a hard kiss.
The feel of his lips against mine, his fingers inside me, are all enough to almost make me cum right on them. Our kiss gets more intense as I start gasping for breath from the sensation of his thick fingers fucking me at the same time.
I pull away from our kiss for a second just so I can whisper into his ear "I want you to fuck me. Get. Inside me. Now... fuck…” He’s quickened the pace of his hand inside of me, “uhh... fuckkkk" I'm barely able to get the words out with every push into me he makes, “fuck me, please, just fuuu…” He's moved his lips back to my neck again and makes a slight "mmm" sound into it. I follow that by moving my hands to his boxers and quickly pushing them down. I want him inside me so badly I know I'll explode by just the thought of it if he doesn't do it soon.
Luckily he knows this and in one swift motion he pushes down my underwear as he takes his fingers out of me, and pushes his hard cock inside of me. "Ahhhhhh" I sigh and moan at the same time with relief. I can’t even imagine the sight of us. Still on our sides, my legs wrapped around him, he’s pushed his entire length into me, but he's not moving.
He's got his cock buried inside of me and the feel of him filling me up is pushing me closer and closer to my edge, any wrong move and it could end. He knows this and puts his hands on my ass, squeezes it, looks at me and kisses me just as he pulls out slowly, only to pound right back into me so hard he's fucked the breath right out of me.
I've got my arms around his neck and bury my face into it as I moan out the motions of him fucking me. I’m gasping so loudly I'm getting dizzy, but I'm so fucking close all I can concentrate on is how his fucking cock feels so fucking good inside of me right now. I don't even have time to think before he's pulled out again. I almost gasp at the mere feeling of not having him filling me up that I don’t have time to think before he's pushed himself into me so hard I know this is the one.
I'm writhing in his arms so much I don't know how he's still holding me so close as I feel my climax brim open. The spasms hit my body and it allows his cock to move into me in small movements. I feel my cum pouring out of me and spilling out around his cock, still inside me. My hands are on his chest practically pushing against him in the way my body is thrashing. He holds me tight and I feel him tense so I know pretty soon he’ll be ready.
I’m coming down from my high and have stopped squirming so much but I’m still breathing heavily. I feel him grasp my ass and push himself deep into me one last time before he’s pulled out, cumming right between us. It’s his turn to breath hard now. I wrap myself around him again so that this time his cock is right beneath my pussy and I kiss him one last time with a sigh.
He tangles his fingers in my hair tightly at first then loosens up. We pull away and look at each other again.
“Maybe this trip didn’t turn out so bad,” he laughs pulling me back into his arms.
“I’ve decided I can’t stay mad at him.” I smile back. We laugh a bit and drift off to sleep still in each others arms.
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