Castiel knew, as soon as he entered Jimmy Novak's body, what the man had been trying to hide, why he had fought so much against Castiel taking his body as vessel. Because even though he had a daughter, and a wife, and a family, there was a tight binding around his chest, shaping them into pectorals beneath his shirt, and his mind shifted away at Castiel's touch.
'So this is why you denied me,' he murmured, reaching more firmly for Jimmy's memories, brushing over them. And there, there beneath the bindings, beneath the way his wife never looked at him quite the way she looked at her brother, the way he never feels quite right without his shoes with soles that raise him above her height. Castiel frowned, brushing his grace against the pain that filled Jimmy at having his secrets revealed to an angel- because at the base of it all, the thing that caused Jimmy to flinch away from Castiel, was the percieved truth that God thought him evil for denying his own body.
'No!' Jimmy tore out of his grasp, seeking a corner of his mind where Castiel could not find him. Castiel followed, and lifted him up, forced Jimmy to acknowledge him. He showed him how, through heaven's eyes, he was Claire's father, how he was Amelia's husband in every sense.
'This was your cross to bear,' Castiel explained softly. 'To know yourself, even against the uncertainty and rejection from those around you.' Jimmy flushed, pulling away from Castiel's grasp, and this time the angel let him go. For now, he had other things to attend to.
When Castiel left Jimmy for the first time, and he went limping back to the Winchesters, hungry and exhausted, the first thing he asked for was a shower. He was concerned, because as far as he knew, Castiel had never cleaned his body with anything other than his grace, and by extension, had never undressed. So if he estimated correctly, he'd been wearing his binder for almost a year. It was time to take it off.
However, when he had tossed his worn and dirty suit onto the bathroom floor and stood there in his boxers and binder, he had to take a minute to breathe. For a year, even if only as an angel, he had been himself, solely and completely. No one had doubted Castiel's voice in his throat, the way that in his body, Castiel was totally masculine. But it was time to take it off.
In a motion that he hated for it's familiarity, he shoved the tight straps of the binder off his shoulders, tugged his arms out, and took a deep breath before letting it out as he shoved the tightly woven material down until it reached his hips. Only then did he straighten to examine the damage... and froze.
He was whole. Where he had expected difficulty breathing, bruising, broken ribs and numb skin, he found instead smooth, flat chest, healthy skin, slightly furred, and unscarred, as it would be if he had had top surgery. In a daze, he lifted his hands, ran them down over the alien shape there, before laughing quietly, tears blurring his vision, because he most certainly had not done this.
And when he pushed his binder off his hips, pulled off his boxers, he found that not only that, but his packer was gone, and- he had testicles, and a cock that was anything but fake, and- the other thing, the shape he had hated- it was gone. His body was right.
Jimmy barely managed to pull his trench coat over himself as he collapsed against the bathroom door, laughing hysterically, almost sobbing. Castiel had taken his life, had taken his body and his mind and his free will, had torn him from his family and endangered all that he loved. But this- his body, the thing that drove him to distraction and extreme piousness and detachment- this, Castiel had gotten right. Castiel had healed him.
When Castiel wore Claire, when he told Jimmy that he was free to die, to move on because his job was done, Jimmy's heart nearly stopped. Not his Claire, not his little girl, never her. But at the same time- and this was something he would never admit, not to anyone who asked- he wasn't ready to stop being Jimmy. He wasn't ready to be done being a man, having a man's shape and not needing his shoes to make him an inch taller and his binder to make him flatter and a packer to feel whole. And Castiel knew all of that, would never acknowledge it.
He didn't expect the sensation as Castiel filled him again, took his mind, but this time, he let it happen. His family was safe, and he could live with Castiel inside of him as long as he needed.