The Captain, The Hunter, The Con-Artist

Meeting by chance was so rare that they didn't even think it was possible. They only met when they needed something from the other, or had something to offer. Of course they were good friends, lovers –some would call them, but they were all busy with different things. And recently, with Neal's new limitation after his time in jail, they could only meet up if they went to him (but of course that was better of being cock blocked by police, though Jack might have just called it kinky and tried it anyway).

Anyways, Dean and Jack would help each other when one of them was out of their depth – whether it be aliens or classic monsters. Neal would forge documents for the Winchesters – and sometimes other hunters – and he'd give Jack advice on how to get over a lover's death. Jack had a lot of back channels that were useful to Neal. After all, he'd been around a long time. And Dean was good for silent nights, sitting in the dark, thinking. Maybe Neal would paint, or Dean would watch Dr. Sexy on silent. Dean would have a beer and Neal would smirk at him in a way that he'd learned was meant to be offensive long ago as he poured himself a glass of wine.

But when they got together, things were different. They wouldn't just sit in silence, because Jack's thoughts turned dark faster than either of the others'. One time, Neal had painted Jack and Dean together – naked, of course. After that first time, they decided never to do that again. Jack couldn't sit still for a second, and the more he moved, the more Dean would be tempted to do the same. They couldn't blast rock music, because Neal wouldn't scrunch his nose up – partly at the song itself and partly at the off-tune singing of the other two. They couldn't go out to drink, either, because Dean honestly had no idea to stop, and it wasn't fair to Jack – who couldn't get drunk at all.

Sure, they could think of something. And sometimes they did.

But, when they all got together, it usually just meant sex.

Dean's on top. Dean's always on top, even if he's bottom at the same time. Neal and Jack know that his hunter instincts don't exactly shut off, and that he doesn't really like being underneath another steady weight. No one mentions it, of course, but everyone knows and everyone can tell that Dean is silently grateful.

Jack's top as well, even though he's on the bottom. As in, beneath. It's the only way things like this work. Well, maybe not the only way… Jack's a switch. He'll try anything and he'll love anything. Both Dean and Neal call him a slut jokingly, but they both know that Jack loves a bit of dirty talk and that it's pretty much accurate.

Neal's bottom, as is what happens most of the time. He can be plenty dominant when he wants to, of course, but he sees no reason to fight this when it feels so good. They've tried many positions before, of course – being Jack's lover kind of implies that – but this is the one they've found that works out the best.

Jack's below Neal, and Dean's on top of them both. Neal's laying on his back, against Jack's chest, with his knees over Dean's shoulders. Dean leans forward and places one hand just over Jack's shoulder to steady himself on the bed. The lubed finger Dean's circling Neal's hole with pauses and Jack turns his head to the side and starts nibbling and licking the inside of Dean's wrist. Dean thinks it shouldn't be as hot as it is, but he soon throws that thought out the window when Neal makes an annoyed noise in the back of his throat and thrusts down a little.

Dean smirks down at the con-artist and pushes his finger in, earning a whine from Neal and a chuckle from Jack. Dean quickly inserts a second finger, knowing by now that Neal likes it a little rough. The man groans and throws his head back over Jack's other shoulder. Of course, the Captain turns his head to the other side and starts sucking at a special spot just behind Neal's ear. Dean takes Neal's loud moan as a good time to push another finger into him.

Just as Dean curls his fingers, Neal thrusts down on them and pushes them into his prostate hard. His back arches and his mouth opens in a silent scream. Dean pauses for a moment, staring at his mouth and remembering just how talented it is. As he glances at Jack, he can tell the Captain is thinking the same thing. Dean removes his fingers and thrusts into Neal quickly, having already lubed his cock up. Neal and Dean both moan as Dean slides in to the hilt. Jack throws his head back but keeps his eyes wide open and thrusts uselessly against Neal's back. He knows he has to wait, but that doesn't make it any easier.

Dean thrusts a few times, barely keep control. Neal curls one hand into the bedspread and one around Jack's arm. With his free arm, Jack begins to trace patterns over Neal's chest, and the con-artist's head thrashes back and forth. Dean take the hint and re-lubes his fingers. He pulls back a little and curls his hand around his cock, two fingers straight against it and thrusts in again. Neal clenches around him briefly before relaxing again with a groan. Dean looks up and grins at his wanton lover. He pulls back out and shifts his knees slightly. Dean adds another finger and positions them so that they'll make a much wider stretch.

Dean thrusts in with agonizing slowness this time, and Neal lets out one long moan as he does so. Maybe they've been calling the wrong man a slut. Neal's much more vocal this time than most of the others. Maybe he has a bit more stress to work off this time. Dean thrusts in and out a couple more times before he thinks Neal's stretched enough, and about a second away from Jack finally ordering him do pay the Captain some attention. Dean must read that on his face, though, as he smirks at Jack and pulls out of Neal once more.

He lubes up Jack and presses their cocks together. Jack moans loudly, eyes nearly rolling back in his head at the pleasure of finally having someone touch him after waiting for so long. Dean aligns them both and thrusts in quickly, sitting up slightly and wrapping his other hand around Neal's cock at the same time. Neal shouts at all the stimulation at once – two cocks in his ass, both hitting his prostate and Dean's hand doing his favorite things to his own cock.

Jack starts thrusting slowly, and Dean sets his rhythm opposite of the Captain's. They each his Neal's prostate on each thrust, and the con-artist gets no relief from the nearly unbearable pleasure. There's so much more pressure when they get together and do it like this. Neal feels so much more full, so much more… complete. Dean and Jack get the perfect friction and even when they pull out, the other's cock is still brushing against their cocks. The heat is more intense, with how close they are. None would ever admit it, but they all last a bit shorter than they normally would when they do it like this.

Dean's pace falters first, but he holds back his orgasm with an impressive show of will. Jack's thrusts stutter after a few moments and Dean starts thrusting in harder, faster, and Jack follows. Jack's hand joins Dean's on Neal's cock and bright blue eyes fly open from where they'd been clenched shut. Neal screams as his orgasm rips through him. As he clenches around Dean and Jack, the other two are pulled over the edge with him, coming together. Their muscles tense. Dean groans and Jack shouts.

Dean slumps onto Neal, who honestly doesn't care because he hasn't come down from his rush yet. Jack certainly doesn't care, being in the same state as the other two. They normally fall asleep like this, although normally, Dean and Jack pull out of Neal so that he isn't overly sore in the morning.

But sometimes he likes to be.

And tomorrow morning would be made even better with a vague, throbbing ache in his ass and a hickey behind his left ear.