Eventually I'll Get There

Dean/Jimmy

Rating: M

Summary: It's been like this for so long. Dancing around each other, coming together and backing off. It's driving me absolutely insane.

There're no real spoilers, just tags from Season Four, and it's kind of...sad, this fic. Sorry.

I can feel him. He's right behind me, and he's warm and there's not enough room and it's almost too hot in this middle-of-the-spring night. And every now and again wind will blow through the window of his closet-like room but it's not enough to cool me down; I'm sweating and I know my face is red, and I can feel him warm and hard behind me. It's not doing anything to calm me down.

There's the three of us, crowded together in this tiny room of his. Me, him and his little brother. He's sandwiched between the two of us, and we're all on the floor caught between his bed and the wall, because none of us were willing to be the one on the bed to leave the others to the floor, and I kind of like the hard wood against my body – it feels good on my back and hip, much better than the too-soft mattress I'm used to sleeping in.

I'm turned on my side, my back to the both of them. It's safer this way. We've been drinking a little – playing some game watching a TV show and taking a tiny shot of whatever the hell we could find whenever something awesome happened, and since the show is quite awesome we're all sufficiently buzzed. It's enough to make Sam drowsy, and enough for Dean to let loose a little, and it's enough for me to be scared that I'll do something I'll regret. Or that Dean will regret.

It's been like this for so long. Dancing around each other, coming together and backing off. It's driving me absolutely insane.

Let me explain; Dean, Sam and I are enrolled in the same school. Dean's in my year, so of course that means I spend a lot of time with him. Over the weeks he's been here I've sort of…developed a little crush, and it's infuriating because, up until a little while ago, I thought he was 100% absolutely straight, and that I'd have no chance with him.

Until he asked me to be friends with benefits.

Well…that's not really the words he used, but it amounted to the same thing. In an all-guys' school it tends to be that some boys will grow closer than others. I can name three couples off the top of my head that met at and attended our school. So it wasn't a really big deal, right? But I liked Dean, really, really liked him and I knew that if I let him – let us – do this, then someone would get emotionally invested (ie, me) and it'd end ugly. I'd rather have an unfulfilled friendship than none at all. And Dean let it go; he said that he only asked because I was, like, his best friend at the school and he thought he could trust me with something like that…because he still had a rep to protect. It kind of made me glad I didn't say anything beyond my reasons for turning him down. Also, I really didn't want to get caught; my parents are hugely religious and if they found out I'd been doing something with another guy they'd likely exorcise me.

So I said no. And I regret it every day of my life. Especially in moments like this.

Because Dean is slightly drunk, and he's affectionate when he's drunk. I can feel him shifting behind me, getting just a little too close, and his hand resting on the floor just behind my back. We're sharing a blanket, his sasquatch brother getting one all to himself, and it's too hot and I just want to escape, but at the same time I find myself begging for his touch…just a little further.

Dean didn't just keep it to that one time, when he asked me. I guess he saw it as a challenge, now that I had refused him. He wasn't used to it – and why would he be? He's gorgeous. He's tan and muscled – but not too muscled – and his eyes are beautiful and when he smiles…

He's breathtaking. But he's not mine. He's going to move in a few days, a week at most. I couldn't allow myself to get hurt like that.

So I kept refusing, and each time it got a little harder.

"You up for it tonight?" His voice is soft; not wanting to wake up Sam, though I'm sure his little brother isn't asleep. I think Sam knows about my crush on his brother, because he keeps kicking Dean, forcing him closer to me to get out of the way of his harmful feet. Dean's right up behind me now, and I can feel his breath on my neck and I know that if I turn around, I'll be able to see his beautiful eyes, and I'll break. One of his hands runs down my flank, stopping at my hip and he doesn't go further, feeling the sudden tenseness of my body.

It's so hard, to just keep refusing like this. Because I can feel Dean's readiness in the way his hands gently take hold of my hips, and I push back to his chest, allowing him to pull me closer because I want it, and I must be a masochist because I love that even this little forbidden touch is going to make this so much harder.

I shake my head, feeling how the action causes his nose to brush through the finer strands along my nape, a place I've always been sensitive, and I shiver against him. "Maybe later." It's all I can say, because how can I possibly say 'Yes, God yes, Dean, I want you' like some whore, and I want to turn around and swallow him down, make him so crazy with lust for me that he'll dominate me, take control of our kissing, and it'll be hot and heady and we'll both be too hot, too sweaty from the heat in the room and it won't matter. I'll kiss a trail down his over-heated body and take his erection into my mouth, and I'll let him thrust up into my mouth because Dean is far more dominant than me, and every tug of his hands in my hair will make me moan around him, because I want that so badly…and…

And I want him to fuck me. Right next to his sleeping baby brother.

But I can't do that. So I just say 'Maybe later' and fall asleep.

When I wake up the next morning, Dean's arm is draped around my stomach, his head still buried in the hair at the nape of my neck. Every warm exhale of his breath makes me shiver. His hand is splayed over my stomach, underneath my shirt in such a possessive gesture, and the sneaky bastard must have waited until I fell asleep to do that, because I'm pretty sure I would have freaked out more if I'd been awake…like I was doing right now, for instance.

Sam's not in the room. That's the first thing I notice.

The second thing is that Dean's got morning wood, and it's very obviously settled in the small of my back. Any moment I make will cause friction against him and that could either be very bad or very good. I'm not sure which way I'm inclined to think.

Damn it, this is so hard. All I want to do is be with Dean, is that so bad? I want to be able to kiss him and touch him and have him touch me, but I know he's leaving soon. I'm seeing less and less of him as it is what with him always taking care of his little brother since their Dad's never home.

The third thing I notice, and I'm only really noticing because I only just tried to move, is that I'm hard as well. Dean's proximity was affecting my body in my sleep – this is just fucking unfair!

Is it later yet? How bad can it be? After all…tis better to have loved and lost, isn't that what they always say? And maybe Dean could stay…maybe…This is all wishful thinking; I know it is, but I can't help it. I don't want him to leave, and I especially don't want him to leave without knowing what he tastes like, how his skin feels when it's slick with sweat, what the painful stretch and burn of sex is like. I want to experience all these things with him, and if I keep waiting the opportunity will eventually be gone.

Of course, there's a difference between wanting it and being brave enough to take it. Carefully I ease myself away from Dean's arms, though reluctantly, the room seemingly too cold without him there, and I try to will my erection away. It fades enough for me to walk. That's something. Going downstairs, I search for Sam but he's nowhere to be found. There's a note on the kitchen table in Sam's handwriting and I pick it up and read it;

I'll be out until about one. Go for it, Jay.

Okay, Sam is officially my second favorite Winchester. I have to smile when I read the note, because it's so obvious what Sam's talking about, and it's nice that I have his blessing because not a lot of people would be okay with someone of the same gender trying to get into their big brother's pants. Sam's a good guy.

I hear Dean's footsteps heavy on the stairs and I quickly slip the note into the garbage, leaning against the kitchen countertop when Dean comes into the room, and fuck me, he's beautiful. He's still kind of sleepy, blinking away the last remnants of unconsciousness from his beautiful green eyes, his hair mussed and very obviously 'bed head', which is just hot. His cheeks are flushed from the heat of his bedroom and his smile is slightly tired when he looks over at me.

My heart is pounding. With Sam's note, I am finally ready to accept that I want this, really want it. Enough to take it. This might be my last chance ever. And I want to make love to Dean if it's the last thing I do.

But I'm still nervous. Dean's no virgin, and I've never had sex with a man before. I cross my arms over my chest, a blush creeping onto my face at the thought as I look down, one leg hooking over the other at the ankle.

"Something wrong, Jay?" Dean asks me, and I smile, looking up at him from under my slight fringe of black hair. I love the nickname he gave me, adopted by Sam, but still his. Jay. Short for James or Jimmy, of course. It's exclusively for the Winchesters to use – anyone else tries and I usually make sure they don't do it a second time.

Now or never. And I take a deep breath and uncross my legs, pushing myself up from the counter in a fluid motion so I'm standing upright. My hands are shaking, I can feel it, but that doesn't stop me stepping closer to Dean, looking up our small height difference into his grass-green eyes.

I smile at him, placing a hand on either side of his face and bring his head down. His breath hitches, eyes widening and I hesitate, just for a second. His breath his warm on my face and he smells faintly of the alcohol from the night before, and Listerine. "It's later, now," I say before I pull him down the final fractions of an inch, lips brushing together hesitantly with his.

There's a brief moment of nothing, me just kissing unresponsive lips but I keep going, because I know he wants this, wants me. He's asked for it often enough. And then he grabs for my hips, bringing the both of us flush together and I can feel his hard-on against my stomach and hip, and there's a fluttering that feels faintly like nervousness and excitement rolled into one. His answering kiss feels like an 'Are you sure?'. I give him no reason to think I'm anything but.

We've kissed before, a few times. Experimental slides of tongue and teeth in the darker times of night when it was just the two of us. I remember I used to use too much teeth; I liked to bite and by the end of our kissing I would always be able to taste blood in his mouth. Dean taught me to be gentler, using more tongue and lip and sheathing my teeth to cause less damage.

But this…this feels different. It's not just…kissing. I mean, it is, but…I don't know. There was something different. Dean tastes like mint and alcohol and everything. His hair is soft between my fingers when I comb my hands through his hair, and it might seem like romanticizing, but he fits perfectly against me, all hard muscle and strength and power. His kiss is gentle against me, knowing how nervous and skittish I've been of him in the past. Like he's afraid I'm going to bolt.

I might. My heart is pounding so badly I feel like I'm going to pass out.

But I want this. I want it so badly and I can feel in the way he responds to me that he's ready to accept what I'm giving him. He walks the both of us backwards, the cold countertop digging into my lower back and he pins me there, his hands exploring my body like it belongs to him, and it does. I'm discovering things I didn't even know about myself when Dean runs a hand down my side and I shy away, ticklish. He nips and mouths at my jaw before breathing on my skin, and the contrast of warmth and cold makes me shiver. He's bringing more sensation to me in the last five minutes than I've ever experienced in my life, and I want more.

"Dean…please…" I don't care that I'm begging, because Dean's always had a thing for getting the upper hand. He likes to hear people plead for mercy, whether it's his brother shouting 'Uncle' in the face of the world's longest noogie, or someone standing down in a fight…or a lover, begging for more, for more touch, more kissing, more sensation. "God, Dean, please…"

"Shh, Jay." His voice is soothing, rough and low against my temple and I shiver against him, even more so when his fingers tangle in my hair, teasing at my nape. It's embarrassing; the sound I let loose when he bites down on my neck, below my ear. "I'll take care of you. It's alright. I just want to enjoy this, and I want you to enjoy it too."

It's all I can do to nod, his voice helping to calm down the fire raging up my spine, and yet at the same time add fuel to it. He smiles, that beautiful smile, just for me, and places a kiss at the corner of my mouth before pulling me upstairs, back into his room, and I've never been happier to see that tiny space, or to lie upon that hard, motel-quality bed. His body is warm weight on top of mine, and it feels a little like I'm suffocating but I don't care because Dean is here, and he's solid on top of me and this isn't a dream, it can't be a fucking dream, otherwise I'll die.

He's not like my fantasies. Everything about Dean, in daylight, screams 'Power' and 'Predator', and he's a ruthless son-of-a-bitch when he's crossed. He's also fiercely loyal and incredibly doting to those he loves. I was his friend, I'd been on the receiving end of that loyalty and that love and it was the most soul-deep-warming feeling in the world, when Dean loves you. It can't be compared to anything else, really.

That's how he was now. He was staring at me like I was precious, like I would break if he handled me too roughly. Yes, he was also very clearly the dominant one, evident in the way he would kiss and bite under my jaw, forcing me to tilt me head back and bare my throat to him like a wolf, in the way his hands trailed possessively, marked my body with little digs of his nails, bruises sucked onto my neck and chest by his exploring mouth.

I'm on fire, electric. Every nerve ending feels like a livewire and Dean's touch just brings me closer and closer. I'm not sure at what point he got the two of us naked, but suddenly he's there again, all hard-packed muscle and tanned skin and beauty, and he's all mine.

"Hmm…" He chuckles against my lips, parting them with his skilled tongue and granting me another taste. He pulls away only for a second, to add; "Didn't know you were so possessive, Jay. I love that." And I flush, because I didn't realize I had been speaking aloud, and I have to wonder what else I've been saying.

"Hey, none of that now," Dean chides, forcing my gaze to lock with his through a hand on my jaw. "You're perfect, Jay. And I like knowing what you're thinking." A smirk, then, something foreign darkening those grass-green eyes and I want to think it's lust. Nothing negative.

I'm still blushing when he distracts me with his talented lips again, and there's a rustle near my head. I break the kiss, wanting to see what he's doing, just in time to glimpse the hand clutching a bottle of lube and a condom. I can't help it; I tense, my hands momentarily digging into his shoulders and pushing, wanting him off of me, away from me, because he's going too fast and I want this too much and fuck it all, I need to breathe. It's getting harder and harder to breathe.

It takes me a moment to realize he's talking to me. He stopped, the bottle and condom lying by my side so that his hand can stroke my face, the other still wound in my hair. I can feel the cold, scratchy corner of the condom wrapper against my side and it makes me shift, trying to get away from the uncomfortable sensation. Dean's eyes are serious, on mine, trying to get me to focus on him, and I do eventually, once his calloused thumb starts rubbing under my jaw, along the sensitive underside and forces me to tilt my head back, just a little. Enough to submit.

"I meant what I said, Jay," Dean murmurs, and it takes a Herculean effort to translate his words into something I understand; "I'll take care of you. You're alright, I promise. Am I going too fast?"

The answer I want to give is No, to tell him that he's not going fast enough, and I want him inside of me yesterday, but the truth is…Yes. I'm afraid. I'm terrified because this…this sex thing…it's complete surrender, to things I'm not meant to feel, giving myself to a person that's not going to be here by the end of the month. And I know it makes me sound like a virginal girl, but that's what I feel like, right now. I can't seem to calm my breathing down, and now that I've noticed it seems my panting is so loud it blocks out almost everything, except his voice.

I reach a hand up to wrap around the back of his neck, pulling his lips to mine. My words come out between soft kisses and nuzzles against his skin, letting myself just revel in the scent of him. "Just…slower. Keep talking to me, please. Your voice helps." And I blush at that admission, but it makes him smile.

"Sure thing, Jay," he promises, his tongue a reassuring slide along the roof of my mouth for a moment before he shifts, putting his weight onto one arm. The muscles of his arm bunch and stand out from the strain and I wrap a hand around the bicep, feeling his pulse along the tender inside. He smiles more widely at the action, before suddenly everything is a frenzy of sensation as his hands close around my erection.

It's sudden and there's no preamble. It's like Dean can read my mind, knows exactly what I want. He knows when to add pressure, how fast a stroke I need to get closer and closer. He knows the sensitive spot underneath the head, and he knows that running a thumb through the slit will force me to arch into his body, feeling muscle against muscle as he leans down, bringing us flush together on his bed. He reached around underneath me and grabs the lube and condom before I can lie back down on top of it. His hand leaving my cock is like a shock of cold water to my system and I gasp with it, shuddering at the loss. There's a needy whine escaping my throat before I can stop it, which he soothes away, telling me that the best is yet to come.

I know what he means by it. This must have been his plan, because I'm no longer quite so nervous.

He slicks his fingers up liberally, sitting back so he's kneeling between my spread legs, and looks down at me as though considering. I can only stare up at him, panting and trying to calm my too-heated body. I know I must make a picture; hair in disarray from sleep and Dean's coaxing fingers, cheeks and chest flushed red, sweat slicking my sides and back from the effort it's taking to hold back on my orgasm (a control which I didn't even know I had, but it was important to hold off for Dean). He didn't seem to mind, leaning back down as one of his hands gently pushes my thigh outwards, thumb rubbing teasingly against my entrance.

"I'm gonna need you on your side, Jay. Can you do that for me?" His words are gravel in my ear, making me shudder as, swiftly; he pushes one finger in, up to the first knuckle. The sensation is weird and kind of unpleasant, the burn and stretch of someone touching where no one had ever touched, but I know it can get better. After all, men don't have sex with each other if it doesn't feel good. "You're gonna have to relax, man."

I try. I really do. But it's hard; it's instinct to push out the invading force, to keep Dean away from me. But he keeps pushing in and I learn that, if I just let him in it doesn't feel so bad. Soon his first finger is in as far as it can go, thrusting in and out slowly, twisting just a little. I breathe heavily through my nose to fight back the noise of discomfort. "That's right, Jay, just relax for me, you're doing fine."

I have to smile, glad that Dean's remembering my earlier request; to just keep talking to me. He kisses me hard, then, his mouth far more aggressive than his fingers as, almost unnoticed, a second enters me. There's more burn and stretch, and he moves his hand as though searching for something. I'm not sure what, but then there's sudden white behind my eyes and I gasp heavily into his mouth, my eyes flying open for just a second. I tear my head away, body arching, unable to process what the fuck just happened, and Dean's chuckling against my temple like it's the funniest thing in the world; "Found it."

'Found it?'

…Oh.

I can't help but blush when I understand; my prostate. Which Dean is now mercilessly pushing against with his fingers, and sometimes the thrusts are hard enough I can feel them in my throat, and it's starting to feel really fucking good when Dean starts scissoring, stretching me further. There's burn and ache and fullness, and I know I'm going to be feeling this for days, but I can't bring myself to care as long as Dean keeps hitting that spot.

By the time his third finger's inside of me, I'm a babbling, wanton mess. He's making good on his promise to make it good for me, but this isn't what we're both looking for and we know it. This is foreplay; I'm ready for the real show.

"Dean…please…come on!" I growl at him, wrapping my legs around his hips and pulling, as though through sheer force of will I can make him start fucking me. His hands stop me, pushing my thighs apart again.

"Woah, hold up there." He's grinning, his eyes brighter than I've seen them in days. He looks happy, and the thought that I'm the one putting that light in his eyes makes my chest tighten. "Need you on your side, Jay."

What? "No," I say, shaking my head frantically, pulling him down and trying to force him inside of me once again. "I need to see you, Dean. Want to see you, please?" I'm begging, and I know it, and I also know what effect my 'puppy dog eyes' have on Dean, and I try and bring them out to full effect. There's no way in hell our first time's going to be looking away from each other. No way in hell.

He smiled, brushing a hand through my hair, pushing it away from my face. "You will, I promise. But it'll hurt a lot more if you're on your back. Trust me, Jay. You trust me, don't you?" And the sneaky bastard freaking nuzzles me, right underneath my jaw and uses his hands on my hips to move me before I can even reply, and I'm suddenly facing out into the room, and he's lying behind me on his side. I can feel his arm moving behind me, along with the muffled groan as he presses his forehead against the nape of my neck, and I look behind myself to see him putting the condom on, covering his erection with the rest of the lube from his fingers. Before my eyes his clean hand grabs hold of my thigh, pulls my leg up and gives him enough room to maneuver, so his cock is lined up with my entrance. The position is awkward and I'm forced to face out again.

I feel his lips on my neck, his other arm snaking around the underside of my body, and he takes a hold of my cock and jerks it once, twice, enough that the pleasure is almost bordering pain, before he pushes in, and everything melts away.

There's very little I remember about that first time. I remember details. I remember noticing that it was 10:07 in the morning when Dean actually penetrated me, his cock splitting my still-tight body in two. I remember fisting the sheets in front of me, hissing as I pressed my face into his bed. It hurt; he was so much bigger than his fingers. The stretching hadn't felt like nearly enough, and for a split second I cursed my own impatience. And when Dean had bottomed out he kissed my neck and my head, waiting until I stopped shaking and gave him permission to keep going. I trusted him with my life; I could trust him to make this good for me.

His hand was Heaven on my cock as he began to set a rhythm, the thrusts deep and jolting inside of my body. I could feel him in my throat, at my back, the pain in my ass slowly fading away as he continually hit my prostate, every other thrust, and I had to shut my eyes despite my need to see his face. The sensations were all too much, too much and I didn't last long. Neither of us did. Can't really blame us, though; we'd been building up to it for weeks, it seemed. Like running a marathon and this was the final 100 meters.

The numbers on his alarm clock were blurry by the time he pulled out of me, rolling me onto my back and his weight was on me suddenly, stealing what little breath I had managed to gain. My thighs and my stomach were sticky, we were both sweaty and gross from the sex but as I predicted, neither of us cared. We were all for each other, saliva and sweat and semen and it was perfect.

Dean moved three days later. I didn't see him for years. I moved on; I had to. Yes, it hurt, but we'd known it was coming for a long while. That morning had been the perfect farewell; we had sex one more time and had showered together, me finally getting to be on my knees for him, by the time Sam came home. I smiled at him and hugged him and thanked him, and the Winchesters disappeared from my life.

I met Amelia my first year after college. She was kind, beautiful in my eyes, and within a year of meeting her I knew that I wanted to spend the rest of my life with her. She had the most vibrant red hair I'd ever seen and hazel-blue eyes. She didn't remind me at all of him, so she was perfect. I did love her, and over time, with our daughter, Claire, I learned to keep Dean Winchester to the back of my thoughts, like a dirty fetish I could only bring out in the darkest hours before dawn.

Then…Castiel. The Angel. He spoke to me, looking inside my soul, and he knew things I had tried to keep buried and he exploited them. I wanted to keep my family safe and he guaranteed that, but he also…Damn him, he mentioned Dean. 'Together we will save Dean Winchester', he'd said. And I fell so easily, because I would have sold my very soul to see him one last time.

Giving up my body seemed like the easy option.

I wasn't surprised when he didn't recognize me. Sad, yes, because I'd always hoped…But still, Castiel was in this body, and he wore me differently. I'm sure if I'd had control over my body he would have at least recognized some of the mannerisms he used to ridicule me for. Dean…had changed. He was older, so much older than he should be, and he looked like he'd been through Hell and back.

He has. I learned that later. What those demons must have put him through…

I saw through Castiel's influence when the Angel met Sam for the first time. I saw darkness in him through my own eyes, and when Sam reached out to shake his – my – hand, he looked at me. And I mean really looked at me, and for a moment I thought he would recognize me, but he didn't. It was bittersweet, because here I was; a prisoner in my own body and I just wanted to shout to Dean that I was here and I had never forgotten him…But I couldn't.

I tried to stay silent inside my own head when Castiel went about his business, but the Angel knew. He always knew.

'I could tell him if you wanted,' he would say, and he tried to sound comforting, I think, but really it was just annoying and seemed patronizing. I pushed momentarily against his influences, hissed as I was burned on the outer reaches of his Grace and pulled back. 'It's nothing to be ashamed of. He could remember you.'

'It's not me anymore!' I yelled back, frustrated when Castiel's unfeeling Grace merely crept closer. It was too cold around him, too…pure. It was sickening. 'It's not me, and it never will be me. So just shut up and do your Goddamn job so that you can leave my body and I can get back to my family.'

Be careful what you wish for…

Dean never ended up finding out about me. Even when it was actually me, I had to go blab about my family…because I did miss them. I missed their companionship, even if it wasn't my wife I wanted. And so of course Dean, being the Hunter who always protected people, wanted to bring me back as soon as possible. I didn't want to go…but at the same time I had to, because if I didn't I would do something I would never regret but might freak Dean out just a little.

Then Cas came back. I didn't want him inside my daughter for all eternity and I have to admit…my motives were still a little selfish. I wanted to stay with Dean forever, and if Castiel took control over my body again then I could be.

I never made it to see who won. Michael or Lucifer. I didn't make it far enough to see if Dean actually said 'Yes'. I hope he didn't, really I do. I was burned out of my body when Castiel carved the banishing sigil onto my own chest, burning me out and permanently placing me in Heaven. Castiel must have my body now, be a full human or Angel or whatever without my annoying pining in the background.

He kept his promise to me; I now walk forever in the fields of the Lord. Only it isn't a field; it's a bedroom, and it's too small and it's too hot, in the middle of spring, and there's sunlight coming through the small, open window. Loving fingers coax me open, a nose and soft lips force my head back, force my submission, and then there's burn, and stretch, and fullness…

…And green eyes stay with me forever.

Author's Note: So...yeah. This has been rolling about in my mind for a while and I was feeling kind of sad so this seemed like the perfect little thing. I wanted to end up with it being Castiel/Dean with Jimmy in the background, but I think it ended better like this.

For those who are waiting for Rowan Winchester or More Than Strangers, I ask patience. I've just gotten out of school for a week so will hopefully be able to update, as well as get together with my beta for some writing but I'm not promising anything.

Much loves, though.

Please review,

HigherMagic x