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For the first little while, it was easy. Well, that wasn’t entirely accurate. It was incredibly difficult, day to day, living with the fact that he’d given Sam over to this angel, knowing for a fact that Sam would never have agreed if Dean hadn’t tricked him into it. The more time it took for Ezekiel to heal Sam, the worse it was going to be when Dean had to tell him the truth (or when Sam found out for himself, which would be even more horrific). But those first few weeks, when Sam was still really sick and exhausted, Dean could get away with just lying in bed until Sam fell asleep or limiting their physical contact to hugs and resting his head on Sam’s shoulder. Those things could all be left in the category of comforting gestures, theoretically.
As time passed, though, and Sam started improving physically, he grew increasingly frustrated with Dean’s reluctance to go any further than that. Of course, because he was Sam, he saw it as rejection. He’d accused Dean of treating him like an injured kid when he felt just fine, of being ridiculously over-cautious, and worst of all, one day in tears he’d confessed to not understanding why Dean didn’t want him anymore, and shut himself in his room for a whole day.
During his limited interactions with Ezekiel, Dean had been told that the angel didn’t see or hear much of what was going on while he was hidden away healing himself and his brother. Of course, Dean wasn’t able to get really specific with his questions; he couldn’t come right out and ask how much he knew about his intimate relationship with Sam. Honestly, he kind of figured there was no way he didn’t know about it, considering he was all up in Sam’s soul or whatever. It hadn’t ever come up explicitly, but Dean was fairly certain that Cas had always known about him and Sam, for basically the same reason. Cas had access to everything in Dean’s mind once upon a time, so he must have known. It just wasn’t something they talked about. So the problem wasn’t so much that Dean was afraid of the angel finding out about him and Sam. It was the idea that Ezekiel might be…watching? Like, figuratively have a chair pulled up next to the bed while they were fooling around, kind of. And that – well, it was a bit much for Dean. Even when he could manage to put it out of his mind long enough for them to start making out, as soon as hands started to wander, Dean had to come up with an excuse to shut it down.
For the entire day after Sam had lost it, ending their argument over whether or not Sam was physically well enough to just lay in the bed and let Dean suck him off by breaking down, crying those big ugly tears and slamming the door because Dean obviously thought he was “defective”, Dean sat in the lounge sipping bourbon and trying so damn hard to figure the whole thing out. It wasn’t true, of course, his feelings and attraction toward Sam hadn’t changed a bit. Hell, if anything he was so fucking grateful his brother was still alive that he would have gladly kept him in bed for days if that was what Sam wanted. But he couldn’t get past the sense of being observed, the idea that someone else was in there during his and Sam’s most intimate moments, watching it all, maybe even feeling it all. And wasn’t that just a complete and total boner-killer right there? That added another complication – Dean was truly concerned that if he could let himself go there with Sam, knowing Ezekiel was on board, he might not be able to go through with it physically. And if Dean tried and couldn’t, that was just another reason for Sam to feel rejected and unwanted. God, it was just this big ugly circle that kept coming back around to the fact that if he went to bed with Sam, he wasn’t only going to bed with Sam. He kept going back to the time years ago when Sam had been possessed by Meg, and thinking how awful it would have been for them both if they’d fooled around while Meg was controlling Sam. Dean couldn’t be sure that was a completely fair comparison, but then again, he couldn’t be sure Ezekiel was as hidden away as he claimed to be, either.
Was it worth the risk? Was Dean only making things worse? Or would it be worse to give in and go to bed with Sam? Hell, Sam was already going to be pissed enough when the time came for Dean to tell him the truth about how he’d been healed after the trials. Would he be even more angry that Dean had slept with him when he knew Ezekiel was in there? Or was he doing more damage by continuing to refuse Sam’s advances now, making him think Dean didn’t want him?
Not for the first time, Dean was staring down a situation where he honestly felt like he couldn’t win no matter what he did. He didn’t have another choice, right? Letting Sam die when there was a way to save him wasn’t an option. So the way to save him wasn’t ideal, but it was better than that crossroads deal he’d made when they were so much younger.
Or was it? Their relationship had been screwed six ways to Sunday when Dean had come back from Hell, and it took forever to repair it, to get things back to anywhere even remotely close to normal between them. What if he was doing the same thing all over again? What if by the time Ezekiel decided it was time to leave, Dean had already hurt Sam so much that Sam would stop trying, would just give up on that part of their relationship?
Once again, damned if he did and damned if he didn’t. Dean was starting to think no matter how hard he tried, he never made the right call.