Cat marries Billionaire!Asher
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It's not that he needs the money. Although he supposes his dad will probably disinherit him when he hears, and then he'll need some money. 

It's not that he wants to marry a billionaire, in particular. There are probably people who kink on that but Lee isn't one of them. It's just that he doesn't have a better idea for what to do with himself after college, so he figured he might as well horrify his father and stepmother by trying to find a man to marry as fast as possible.

Billionaire Marriage Brokers isn't the only agency he's signed up for, but it's the one with the most rigorous selection process. So...probably the safest?

He can tell himself that for now, anyway. 

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He gets a phone call!

"We've found someone for you!" Pauline chirps.

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"Anyone I'll have heard of?" 

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"How often do you read tabloids?"

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Oh, that's promising.

"Not...often?" Never, in fact. 

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"How about books about military hardware?"

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"...no. Is this, what, a tank designer?"

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"We don't typically share this sort of information until you've signed the non-disclosure agreement but I don't think you would have heard of him!"

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"Right, the NDA thing. Uh, I'm free...pretty much any time, if you want me to come in and sign things?" It's not like he has a job or anything, as his stepmother points out whenever she wants Lee to do something for her. 

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"How's tomorrow?"

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"Works for me." 

Lee shows up at the appropriate time and place. He definitely did not spend any of last night googling military contractors, but he thought about it. 

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Once he signs the NDA, she says, "You'll be marrying Asher Stark, heir to Stark Industries."

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"...yeah, no, doesn't ring a bell." He might have heard the name at some point, but he doesn't remember anything about the context if so. 

"So, who is this guy and why does he need a mail-order spouse." 

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"Well, his parents died when he was seventeen, and since then he's been a bit off the rails. Lots of partying, drugs, casual sex, puking on the paparazzi's shoes... Obadiah Stane, a family friend who runs Stark Industries, is at his wits' end. So he gave Asher an ultimatium-- that he had to be married for a year or he would lose access to his trust fund-- and called me for help."

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"That's...better than some reasons people end up in the tabloids, I guess." And it sounds like this guy is somewhere near Lee's age, which is better than the worst-case scenarios he was imagining. "Wait, how old is he now?" 

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"Twenty. I'll show you his file."

The first page of the file is photos. Asher Stark is, it turns out, incredibly good-looking.

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Huh. Lee wasn't really expecting to be the older one, even if it's only by two years. 

...yes. He is good-looking. That is a true statement.

Not really enough to be the basis of a decision, though. "Has he seen my file yet, or are you waiting on me saying yes?" Lee wonders as he turns to the next page. 

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"We'll get your decision before we talk to Asher."

Asher Stark! Personality test: 92nd percentile openness, 52nd percentile conscientiousness, 98th percentile extroversion, 32nd percentile agreeableness, 3rd percentile neuroticism. Daily life varies; he parties a lot, but he's also single-handedly responsible for the latest innovations Stark Industries has made in explosives and other forms of weaponry. Asher completely failed to fill out the list of expectations, instead writing a sentence on the bottom that says "lets me keep my trust fund."

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Lee wishes this was at all surprising. 

"Do you know if he's bi, or not expecting to have sex, or what?" Being married to a man will be substantially less interesting if they're not having sex, and being married to a man as attractive as Asher without having sex seems like a bit of a waste, but since he didn't check 'no sleeping with other people' it's not exactly a dealbreaker. 

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"He's bisexual. I suspect if you want to have sex with him you'll end up having sex with him. About whether you have sex with him twice I make no promises."

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"Okay."

He considers the information he has about Asher, the likely outcomes...

"I don't know if I'd tie myself down to a year-long marriage yet but I'm willing to do some kind of...trial period? I guess this is what engagement periods were originally for, or something." 

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"Obadiah Stane has set up your contract so that you won't get any of the money unless you're married for the full year, barring abuse, neglect, or unreasonable treatment."

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"Oookay then. Just checking, Asher Stark apparently doesn't care whether I sleep with other people, but does Stane have an opinion?" 

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"That brings us to a very important part of this contract! Because the person contracting isn't the husband himself, Obadiah Stane wants to make sure it's a real marriage. Here's the file of additional guidelines."

The additional guidelines are five pages long in fairly small type. Some of the guidelines are obvious (Asher and Lee can't live separately). Some are irritating (Asher and Lee are expected to attend cocktail parties and weddings together as a couple).

"To answer your question, Obadiah Stane has specified that the tabloids can't find out about your relationships with anyone else, and Asher Stark knows how to evade the tabloids and will be extremely happy to help you have sex with whomever you want to have sex with."

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He snorts. "Sure, that sounds tolerable. Assuming I don't turn out to hate the guy or vice versa. He's not gonna hate me, right? Pretty sure I'd hate someone my legal guardian was making me marry." 

Is there anything in the five fucking pages of additional guidelines that goes past "irritating" to "objectionable"? He can deal with a little bit of acting in public, might even be fun as long as Asher isn't hating it the entire time. A dealbreaker would be if he was banned from seeing his sister, or had to pretend to be a Conservative or pro-gun-lobby or something. 

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The guidelines have no opinion on him seeing his sister or on his political affiliations, although he is required to be extremely bland in interviews.

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