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English
Series:
Part 107 of May Tropes Mayhem , Part 1 of Marriage as a Solution to Problems
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May Trope Mayhem 2026
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Published:
2026-05-05
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842
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1/1
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2
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7
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61

Questionable Descent

Summary:

Castiel doesn't hesitate one bit when he realizes who he's reaching out to, other than a reasonable skepticism of how on Earth he's supposed to convince an enemy to help him.

Notes:

Written for May Trope Mayhem 2026
Day 4: Road Trip

Work Text:

He’d heard all about Sam Winchester. The Boy with the Demon Blood. Castiel had always considered the nickname somewhat cruel; it was hardly Sam’s fault that John was supposed to have been rendered infertile in the time between his elder son’s birth and younger son’s conception. Mary swore up and down – including successfully on a holy relic – that her child was John’s son and no other’s, but when she died six months to the day after Sam’s birth, John had taken it as proof that his younger son was tainted and somehow demonic. Castiel could sympathize with being born of uncertain parentage; although Lucifer had claimed him as his son, his mother told him she was only taking his claims seriously because it meant Castiel’s future would be assured. His true father was, according to her, some tax collector who had agreed to an alternative form of payment when she couldn’t raise the coin for her yearly taxes one year. Given that he looked almost nothing like Lucifer, he was inclined to believe her – as, unfortunately, was Lucifer’s elder brother Michael. When Lucifer disappeared and reappeared at the head of an invading army, Michael had found many ways to make his displeasure at his so-called nephew’s presence clear.

That was why, when Castiel caught Thaddeus “interrogating” Dean Winchester, he’d gone to Anna. When Anna confirmed that it was on Michael’s orders, and Castiel would likely be sent in next, he told Anna he planned to leave and find Sam. “I don’t know if bringing Sam here is the best idea, but it’s certainly Dean’s best hope for escape.”

“You’re not wrong there,” Anna said. “Go. I’ll cover for you here. You’re on a special undercover mission for me and out of contact until you return.”

He’d heard the rumors – Anna’s special assignment had him going in the opposite direction of his true destination. Perfect. He could hide out as Steve, a messenger from the castle, seeking Winchester lands to deliver a ransom demand. That got him good enough directions that he could easily find his way, and promised safe passage. No one would harm a messenger, not unless directly ordered to by their lord.

 

Sam was instantly recognizable – part of the evidence used for his alleged demonic blood was his height, significantly more than his father or brother, and his hair, which was rumored to be supernaturally soft in addition to its beauty. Looking at the man in front of him, Castiel could almost believe that there was something supernatural in his heritage.

“Steve, right?” Castiel blinked. He hadn’t been prepared for Sam to be the one to approach him. He tried to respond, but found himself lost in the eyes gazing curiously at him. He hadn’t heard of their supernatural beauty, and it made him wonder why not. Such colors were not found in any natural eyes he’d ever seen. “Hi. I’m told that there’s a messenger from Himmel looking for a Winchester. Will I do, or do you specifically need to deliver your message to my father?”

“Actually, I was specifically looking for you,” Castiel managed to say on the second try. “I set out three weeks ago, and I hope we can make the return trip equally fast, but it’s unlikely. I also must admit to meeting you under somewhat false pretenses.”

Sam’s eyebrows shot up, and he reached for the dagger strapped to his hip. “Convince me not to use this. You’re clearly actually from Himmel, so if you’re not here to deliver a message, what are you here for?”

“My true name is Castiel.” This was going to be the most difficult part of Castiel’s mission, if not the most dangerous. “My uncle, Michael, has your brother. I’m here because I’ll need your help to get him out.”

“Or you’re hoping to earn your uncle’s forgiveness for existing by bringing him the missing brother, and really putting my dad in a bind,” Sam said, though there was no accusation in his voice. “It’s what I might do, if the situations were reversed.”

Castiel shrugged. “I will never have Michael’s forgiveness for existing, and I’ve accepted that. I’ve done what I can to work within his constraints, but the time has come where I cannot. He is violating all bounds of decency in the way he’s allowing your brother to be treated.”

“Get me there. If you’re leading me into betrayal, you’ll be the first one to die. Probably not the last.” Sam got to his feet. “How much rest do you need before we set out?”

“Not much, but shouldn’t we make a plan for how to get you in safely? Protect you in case of capture?” Castiel had some ideas, but none he thought might be useful. His favorite was perhaps the most impractical.

Sam shook his head. “Give me an hour to grab my bag and lay a false trail for where Dad’s going to think I went, and then we head for the border. We can figure out the actual plan on the road.”