I'm @'ing @j-h-cubedman for this after a lil back and forth we had about our respective takes on Dess. So here's mine! ID is beneath the pictures :>
Fair warning, this is me playing with toys at the end of the day. I am taking elements of a hardly revealed character from a popular franchise I have only played 3 out of 5 chapters of so far, along with whatever content I have socially osmosized (thats not a word before but it is now!). Anything illustrated here is, at the end of the day, my preference. That just happens to be making incredibly flawed and unlikable characters bc that intrigues me, for whatever reason. Hashtag my torment.
To start, Dess would be a young trans man who essentially carved his own life out from Carol's shadow. He would often head out to the edge of Hometown, where a military surplus store, that he works under the table at, lies. He very much makes a point to be as counterculture to the Holiday household as he possibly can, including everything from his rugged clothes being unbuttoned and self-trimmed bangs (with strands intentionally left uncut), to buying his own diesel motorcycle, a USMC Kawasaki KLR 650/m1030m1.
Rudy was the one to get him fixated on military gear, starting with the old Jeep YJ he used to own and take Dess on offroading trips with as a kid.
He is very much a jaded man who tries to be the first one to move on pushing others away so he doesnt get hurt any more than he already does. Asriel is about the only peer his age who gets through to him, really just so Carol doesn't call a search party on him whenever he rides off into the woods for a couple days of unannounced camping. About the only other person he cleans up for is Noelle, seeing as she'd be young enough in this interpretation to not really understand the tension between him and Carol.
Oh, and as a little bonus doodle for a real cool person with a real cool AU...
[ Image Description: In the first picture are multiple grayscale sketches of a headcanon of Dess Holiday. Hes transmasc in these pieces.
Top left: a bust of him staring at the viewer w/ a tired but neutral expression. Hes wearing a binder & a military surplus shirt.
Top mid: Him posing w/ a diesel motorcycle. Hes posed w/ his hips sticking back while balancing on his heels. His left hand is in his left pocket while his right hand is laid on his right thigh. Theres two arrows pointing to his bike & shirt respectively. Text below each arrow reads "USMCm1030m1" referring to the model of milsurp motorcycle. Oher text reads "Netherland Marines Jungle Camo Field Shift" referring to the long sleeve shirt. Underneath both lines of text read "His ass in NOT in the military!!!"
Beneath both sketches are three headshot sketches, leftmost one: Dess looking down at the viewer, head tilted up at a 3/4 angle. He looks angry, Text under reads "…did you touch my guitar".
Middle sketch: Dess looking up, slouched, w/ a scowl on his face. He has water drop marks on his face & in his hair. Text underneath reads "I just wanted to swim. Alone".
Rightmost sketch: Side profile of Dess. His eyes are wide w/ fear, face in a shouting position w/ a silhouette of the Roaring Knight. Text below reads "ELLY!" in all caps.
Rightmost sketch of all sketches: Dess is lit by flashlight held by Asriel. He is holding a bottle of alcohol. Dialogue between the two reads;
D: Quit blinding me, will you?! Yes Officer, I've been drinking. No, I didn't drive out h-
D: The f- Az-hole? Fuck're you doing out here! Are you just flashbanging monsters for fun? I coulda broke this over your horns, dickhead!
A: Sorry, sorry… I just, you weren't answering any of Carol's calls so she wigged out, called the cops…"
D: Fucking bitch, she knows I can care for myself…yeah? She knows I come back home, too. I clean up, I always do.
D: Maybe if she stopped addressing me after a month, treat me like my own person…
The second picture is a higher res screenshot of Dess' aforementioned headshot sketches. The third picture is another closeup of Dess getting blinded by the flashlight with the dialogue between him and Asriel. The fourth picture is the same as the third, without the dialogue.
In the fifth picture, Dess is painted over Winslow from the movie The Lighthouse, who is making a scrunched up, irritated face. December is wearing a binder and long sleeved shirt. There are subtitles below that read "Ugh, don't be such an old bitch!", addressed to Carol."
The sixth picture is a colored headshot sketch of both OP's and j-h-cubedman's interpretations of Dess. OP's dess is looking up at cubedman's December with an frustrated appearance, nose scrunched and eyes narrowed. There is a textbox with an arrow pointing to him that reads "(Is jealous that she's taller/how is her hair doing THAT)". Cubedman's December is looking down and to the side towards OP's Dess with an uneasy, concerned look. She is leaning away slightly. There is text to the right of her that reads "...dude what is your problem". There is also a picture of a white dog pressing its face aggressively against a gold colored dog between the two.
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