There aren't a lot of things with the potential to make a man like Tony second-guess his moral stance on things. Being a person of science, Tony constantly alters his view on things to solve problems; looking at things from this or that angle to smooth kinks in an equation, or sometimes scrapping an entire idea to build a new foundation-because being stubborn isn't compatible with being a scientist.

It's fair to say, then, that while Tony wasn't immobile when it came to inventions, the situation was different when concerning decisions of morality. When Tony Stark took a stance on things, he wasn't one to dance about it. And even then, there were certain things Tony simply never cared to change his mind about.; when it came to these things, even discussing it only got a laugh.

So, while Tony's moral compass pointed a little south of north, Tony had certain ideals he didn't intend to go against. Unfortunately, Tony circumstance didn't always allow him to abide by them. It hadn't started off as a problem Tony ever considered. It had started in that room, in Stark towers, before the end of the war Loki was waging—before the real start of it, even. It had started with that slight feeling of surprise and dread in Tony's heart when it occurred to him what he had been missing the entire time; what Loki had made no attempt to hide. It had started with the words "Son of a bitch." On the flight mechanism that had been serving as SHEILD's headquarters. But, more than anything, it had started with what the moment had meant, what all of those things had meant and what he had realized. He and Loki were the same. The only difference was that when Loki, having fucked up beyond belief, hadn't had the resources—the money, the love, the friends—to fix things the way Tony could. Loki was what Tony might have been, and Tony was what Loki never could be.
Though, honestly, this realization didn't stir much in his mind. His viewpoint changed; shifted a click or two to the left, and he had realized how to try and appeal to the God of Mischief, because suddenly he just got it. So he'd gathered everyone up and headed to Stark Tower, where he would face off, armor-less, against Loki.
"Do you want a drink?" He'd offered. Loki declined, and Tony shrugged to himself before beginning his little speech. He looked Loki in the eyes as he said the words he had planned out, had recited in his head, the words he knew would make it hardest for a man like Loki—a man like either of them—to continue with his plan. "You're missing the point! There's no throne, there is no version of this where you come out on top. Maybe your army comes and maybe it's too much for us but it's all on you." He'd said, and Loki had taken pause. The two were standing close now, though still about three feet apart. Loki looked at Tony with a sort of appraising expression in his eyes. Tony didn't know what it meant, and there was no hiding the fear in his own eyes.

"…You have doubts about my claims, of course. But I can assure you, I do have an army, and they are coming," Loki said, refusing to seem the slightest bit affected. "and while you may have reason to question my honesty, it doesn't matter. In a matter of hours you and the rest of your—your team—" he spat the word. "will be dead. And forgive me if I'm wrong, but I don't quite see you roaming the halls of Valhalla. So, Anthony Stark, if anyone were missing the point here, I'd say it was you. You have a chance, right now, to join me, and to choose to be on the winning side of this, to watch me create a world without war; simultaneously realizing the two things humans crave most." The two were, suddenly, standing closer, staring heatedly into each other's eyes.

"And what is it that humans crave the most?" Tony decided to humor him, although he wasn't entirely sure he cared to know the answer.
Loki smiled, "Surely a man as smart as yourself would know. What humans want—what they really need," Loki was dragging the tip of the spear along Tony's chest, and Tony's heart was pounding like a jackhammer against it. "is peace…" he slid the sharp point of the spear very slowly across Tony's throat, his words making slow, careful movements as they traveled between his lips. "…And subjugation." His spear tapped over Tony's arc reactor. "…They were made to be ruled, Stark; all of them…but you." He tapped again at the metal.
Tony was taken aback, to say the least; he met the eyes of the villain very steadily, trying to figure out how much of what Loki was saying was genuine. He was uncomfortable, standing this close to the god, but he didn't say it, didn't step back and let his body betray him. He just stood there, staring into unwavering pools of green, knowing that if his only chance was guessing Loki's tell—the tell of the God of Lies—that he honestly didn't stand a chance. "You want me to join your army?"
Loki rolled his eyes. "Not join my army, Stark. I wouldn't have you fighting like a common soldier." He dismissed the idea completely, both with his words and with a sweeping gesture of his staff, made to the right of them, as there was no longer enough room to gesture freely between the two.
"Oh really?" Tony said incredulously, both his right eyebrow and his mouth raised upwards in disbelieving approval.
"Really, Stark, why would I convince you to join me…only to waste your life like a pawn's, when I could so easily end you now?"
"This isn't a game of chess, Loki."

"Regardless. On my side, you would be more than the knight they seem to have elected you should play, and more than the pawn your government—and even you friend, at one point—tried to reduce you to." Loki's eyes glinted dangerously as he reference Obidiah. "On my side, your life might mean something."

"Oh yeah? Then what am I? What does the God of Mischief think I'm worth?"

"You're a rook, Stark." Loki's voice was serious. "You could do much for my side. you could have all you desire, Stark."

"A rook? Not a King? Not a queen?" He asked. "Besides, I don't know if you realize this, but I'm kind of a billionaire. Not really lacking in the want department."

Loki raised his eyebrow. "There are many things I could give you, Stark...things you would never think to ask for..." he paused, a glint in his eye. "'d have me call you a queen?" Tony's lip twitched upwards. "No, Stark. You're neither a King nor a Queen in chess. The king is powerful only in name, while the queen—"

"What makes you think you have anything I'd want, Loki? Just because you see yourself as the Queen in this game-"

"You're too presumptuous. Perhaps I am the king, Stark. The most necessary pawn in the game." Loki took a step closer to Tony, leaving the shorter man feeling painstakingly vulnerable. "And there are many, many things I could give you, Stark," Loki leaned to whisper into his ear, not brushing Tony in the slightest. There was a dark, hungry look in Loki's eyes. "if only you could open your mind..."

"…is that what this is about, Loki?" Tony was panicking; he could think of nothing to do by crack a joke. "Board games? Are you here to offer me the latest bullshit form of Monopoly? Because if you're bored, I have Scrabble in the close—"
Loki snarled, grabbing Tony by the throat. "You insolent—"

Tony was caught completely by surprise. "—well if you're still offering I'd like you to give me my life—" he choked, and Loki paused, loosening his grip on Tony's throat before dropping him back onto his feet.

"Never-mind, Stark. I was wrong about you," his eyes narrowed, and deep in them there was a trace of hurt, masked by a thick layer of disapproval.

"I'm sure you'll understand my not wanting to broadcast this to the rest of" Loki said, stepping away, suddenly casual again. "I'm afraid I'm going to have to do some significant damage in order to cover up this...offer...which still stands." As he said the words, his eyes flitted to the window.

"You're serious?" Tony asked.
"What, is the infamous Tony Stark scared of a window?"
Tony scoffed. "Try me."
And that's how Tony Stark found himself flying through the glass of his own tower.