22 they/she———coming to terms with my gender…one Miles drawing at a time———feel free to use my art for recreational purposes :D
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Hello fellow Outlasters, I plan to make an Outlast Secret Santa event this year. I did this back in 2019 and I'd like to hold the event again this year as Outlast Trials has released.
The deadline would be approximately a month and all the gifts will be posted in the new year (as in Christmas Week I wouldn't be on my laptop sadly). You would create and receive either art or fanfiction, so please let me know if you are interested in the event.
Reblogs and shares are encouraged !
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DO *NOT* ATTEMPT THE MOUNT MASSIVE 3:AM CHALLENGE ‼‼ (TOTALLY REAL) (NOT FAKE) (I DIED????)
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all i want to say is ur likr the main reason i got into outlast and seeing u rb my outlast fanart gen had me crying☹️☹️😢😢😢🙏🏼🙏🏼UR SO COOL
AAAA YOU’RE SO KIND💜💜💜 I loved your outlast fanart!!!!! It was so cute🥹 thank you for sending me this!!!! (And sorry for responding so late, I’ve been so busy lately—thank you for your patience!!!)🫶🏽🫶🏽🫶🏽
A little Outlast doodle in response: this is how I imagine Waylon & Miles rescuing Blake from Murkoff (BUT the message also applies to you—I’m happy you’re here and thank you for the kind words!!)

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I love that it's commonly accepted that Miles is a disaster gay who lives on his lonesome. Like his outfit and way of writing says it all.
LOVE that also.
I love seeing him as a mess—seeing him as someone with values and a lifestyle that don’t fit into western society’s expectations. Also he has a great fashion sense. And his writing…so beautiful… I get a really good idea of his mental state lmaodjdgsjfh
THANK YOU FOR THE SUBMISSIONS, I always enjoy responding to them :) <3
Some silly doodles hehe:
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Miles Upshur Headcanon:
My personal headcanon for his firing from his old company was that he posted about U.S atrocities in Afghanistan, leading me to believe he's anti war, anti capitalist, punk and probably watched a lot of LiveLeak.
YEEEEEAAAAAA I share many many similarities in my headcanons also :)
I wonder what kind of life he grew up in, along with when/how he came to embrace his values…👀
Thank you for sharing your headcanon!!!!!! <3
(Miles Upshur… *shakes fist* …you don’t know how much you MEAN TO ME)
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Honesty really curious if u have any Lisa Park headcanons? :3
(Some fanart for how I imagine her :) — inspired by fellow fanartists!)
Thank you for asking! :D I have a couple—inspired by any info on her provided by Waylon’s notes:
Both Lisa and Waylon seem to share many values and interests, or at least partake in each others’ values and interests.
I like the detail of Lisa calling Waylon “too literal-minded”—it feels like a common sentiment made towards tech people by folks outside of the tech community. It also makes me believe she’s a very reasonable/down-to-earth person—maybe even more compassionate about human rights/ethics/law/poli sci compared to Waylon. I like to think that Lisa was the reason Waylon became so passionate about Murkoff’s shady business. Maybe she was the one who introduced Miles’ journals to Waylon👀👀👀
It’d be really cool if Lisa and Waylon met at Berkeley! :)
I think Lisa would be able to finish Waylon’s whistleblowing business if he ever died at Mount Massive.
I don’t have too many headcanons of her, but she seems like an overall caring and compassionate person with a sense of doing the right thing—similar to Waylon. It’d be great to get more info on her in the future! Would love to see how she adapts to the new lifestyle of constantly hiding from Murkoff.
Thank you for the ask!!! I’ve been so busy lately so thank you for being patient with my response :’) <3
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Outlastober 2023 - Day 28, Fired
Outlastober by prettyboychainsaw
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things got out of hand
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miles upshur should have been at the club.
#and he should’ve been bottoms up when I first met him#(HDHSHDH I’m trying to reference that one boyboy west coast song)#I agree tho
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An Upshur I commissioned from @jihadmilk !! thank you again Jericho ugh I love her art so much give her some love❤️❤️❤️💥
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Outlastober 2023 - Day 13, Trager Juice
TRAGER JUICE! UPSHUR APPROVED! (Disclaimer: fingers not included)
Outlastober by prettyboychainsaw
#UPSHUR APPROVED#HAHAHSGSJDHS YES#miles just needs a nice cold refreshing beverage to keep him going
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First post camerashipping cringe ughhhh
The..the sillies..I love them..
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Outlastober 2023 - Day 15, Trinity
Outlastober by prettyboychainsaw
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Pretty Boy's Outlastober 2023,
Day 13.) Trager Juice
Prompt list here!
#LETS GO BEAR MILES#op I love your art and style so much#I’m having so much fun seeing all the art being made with your prompts
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dude wheres my jeep
no this iwas not an excuse to draw miles and waylon i swea.r...
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