\m/ I like the devil's music (and his beard). Hide your daughters etc. I mostly write Discord stuff, because nobody parties like a trickster god.
Everytime someone tells me Discord should never be portrayed as someone with a sexual history or bisexual or pansexual I picture him singing this complete with dance moves. Probably lewd ones.
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Possibly ones impossible to any normal creature.
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"I treat a man like he treats me. The difference between a hooker and a ho' ain't nothin' but a fee" *TURNS IN AN UNDULATING MOBIUS STRIP*
I mostly picture Discord as Discordantly sexual. This is a condition exclusive to our favorite god of chaos that means his interests tend to vary and change often. One day you might find him trying to romance Fluttershy and the next you might find him proposing to a small body of water that was once used to drown a duke.
3812469
In one of my stories he had a relationship with a comet that lasted years and his fur looked like he had rubbed up an epic plasma ball when it was over.
3812471 I know. I think I've read it already. The question is though, what other inanimate objects can we ship him with?
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A bottle of hot sauce. A single plum floating in perfume served in a man's hat. A persian rug. Keanu Reeves.
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Pretty much, yes.
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I think he has preferences, though. "Strange attractors" if you will. Behaviors to which he is drawn, and which he mostly performs. That's why it's possible to meaningfully have him as a friend or a foe.
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I think one of the reasons he's drawn to ponies like Twilight and Fluttershy is they give as much lip as they get. If they just nodded and went along with everything he wanted he would likely lose interest. It would be no different than all the ponies he had as "yes men" when he was ruler, and he very likely got sick of them quickly. Also the fact that he finds them both smart and beautiful mares who actually seem to want him around without an ulterior motive.
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They're also fun to play with, whether as opponents, allies, or somewhere in between. The fact that they're smart means that they come up with ideas he can't always predict. Discord is a hedonist and he enjoys watching smart Ponies to see what they'll do next when he presents them with an unexpected stimulus.
This is, ironically, something he has in common with Celestia as well. The main difference is that Celestia has much stronger moral self-restraint. But, come on, you know she invited Discord to the Gala because she wanted to see what crazy silly thing he would do that would surprise her.