iiinova — where your digital self keeps evolving

Freak 🔞 [Comms Open] @sinfuljessie.com · 29/08/2026

I got excited lmao. Raggie beach day, but bottomless. Also gave her extra doll features...and a zipper pussy. Doesn't affect much other than her clit. [ #genitalcircus #boobs #dollgirl #sex #cum #porn #nsfw #nsfwart ]

A series of doodles where Ragatha (TADC) shows off her pussy, gets her breasts fondled, gets picked up and fucked, laid down and fucks, and a shot of her dripping with excess cum. There are small pop-ups, one asking to go again, a "fill meter", and a success status "filled 100%". Otherwise a little dialogue, especially for moans. Everything is in Ragatha's swimsuit, but bottomless.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 22/08/2026

Fucking machine perhaps? Could combine with another dildo suggested since it's kinda just dildo attached to a motor.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 13/08/2026

Trying to pace myself better on art but still post, so: yesterday's drawing but with the jerking animated. I'll probably expand on it slowly unless I get sick of it lmao. [ #shadowvanilla #pureshadow #puremilk #cookiecum #coochierun #nsfc #nsfw #nsfwanimation #nsfwart #animation #digitalart ]

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Freak 🔞 [Comms Open] @sinfuljessie.com · 11/08/2026

Got Milk Cookie in the new CR Crumble game and holy shit he's so fine. Did not initially clock he's a pediatrician specifically. Hilarious that the costume that makes me like Milk Cookie is this of all things! [ #sketch #doodle #milkcookie #abdl (implied) ]

Milk Cookie (pediatrician costume) holding a milk bottle with a smile.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 04/08/2026

I want to torture PV! Brain is fried so not 100% satified with this as is, but I like the overall vibe. Might explore it more later? [ #crk #purevanilla #bodyhorror #fanart #doodle #sketch #fantasyart #horrorart ]

WIP of an illustration of a corrupted Pure Vanilla. Meant to be a fusion with the Ultimate Dough, but I don't quite feel satisfied with it yet. I think I'd like to skew it closer to Shadow Milk's Ulti design, if I do more with it.

Very long explanation of the design as is: His upper body is covered in a viscous black fluid, visually playing on the chocolate syrup in his normal costumes. The actual substance would be closer to polluted syrup and oil. Psilocybin mushrooms (or magic mushrooms) are growing out of him and emitting spores. His chest is severely cracked. His hair drapes over his shoulders and loops around his wrists. The latter is because this PV's hair is meant to double as thread to puppet and move other things. His eye is barely visible through his hair, the iris dripping down like a tear. A feral grin also peaks through his hair.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 03/08/2026

VGen Commissions - vgen.co/sketchyjessie If you like my style or wanna support me, feel free to grab a commission! I draw horny and kinky stuff, and I can draw YOUR horny and kinky stuff for a bit of cash. [ #nsfwart #nsfwcomms #vgen ]

Screenshot of my VGen commissions: Sketch / Doodle, [Spicy] Sketch / Doodle, [Spicy] Rough Greyscale Illustration

Shadow Milk and Pure Vanilla NSFW greyscale illustration with dialogue.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 03/08/2026

BurningNella for your viewing pleasure!! They make me sick (positive) Samonella Cookie - @radiostarmaniac.bsky.social [ #cookiecum #coochierun #nsfc #nsfw #yaoi #ocxcanon #burningnella ]

[ Burning Spice x Nella ] Three major doodles: one of Burning Spice giving Nella oral, one of Burning Spice holding Nella up and fucking him from behind, one of Burning Spice cumming in Nella in the same situation as last. There's also a tiny doodle of Nella steaming (basically overwhelmed/sweating) labelled 'fried egg'.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 28/07/2026

Discord got on a chat / doodle sesh about collars. Kink as a form of trauma processing is very special to me! Also collars are hot. (,,♡‿♡,,) [ #cookiecum #coochierun #nsfc #nsfw #kink #nonsexualkink #suggestive #collar #bdsm #yumeship #ocxcanon ]

Sketch. Mocha Cream (sona) holding a leash attached to a collar on Mold Dough, the latter of which is fidgeting nervously with part of the leash. Mocha Cream checks in on Mold Dough: "Doing ok?" Mold Dough just hums in response.

Details I like that feel worth mentioning:
- Mocha Cream's right knee is hyperextended. I have some level of hypermobility, so just slapped it onto the sona for my own personal enrichment.
- Mold Dough's expression is relatively soft, even if he's nervous. Dude could absolutely wreck house if he didn't want the leash on, so he's giving a level of trust even if it's difficult to do so.
- Mold Dough's collar is decorated with a flower, and the leash in attached with a small bow. Basically trying to decorate and reclaim a collar originally representing entrapment, using BDSM as a vector to process trauma and rewrite the response to triggers? Since the dough trio seem to keep their chains, cuffs, and collars even after escaping, I headcanon that those are necessary to keep their body intact.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 25/07/2026

Gay sex! Also some very light bondage. Left: Aksa, he/him, @antumbrae.bsky.social Right: Arte, they/them, mine [ #ocsky #ocship #gaysex #queersex #bondage #sketch #doodle #illustration #nsfw #nsfwart ]

[Rendered sketch / rough illustration] Aksa and Arte having standing sex, Aksa thrusting in Arte, a little cum dripping down the shaft of his penis. Both are kissing. Arte is wearing a dress and ripped tights. Aksa is wearing a cropped tank top, tights, and pants, the latter of which has been unbuttoned and unzipped, hanging around his thighs. Aksa's hands are bound by ribbons controlled by Arte, tied behind their back. Arte's legs are wrapped around Aksa.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 18/07/2026

Got back into reading Berserk! Guts is very special to me for a few reasons, so I've been wanting to draw him for a little bit. Enjoy the emo bitchboy. [ #doodle #sketch #art #fanart #berserk #guts ]

Doodle of Guts from Berserk, focused on his face.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 16/07/2026

Don't you just love hugging your partner? Aka passionate gay sex ft Fwuki (mine) and Anti (@antumbrae.bsky.social) [ #gaysex #sketch #doodle #nsfwart #analsex #ocship #ocsky #yaoi #bl ]

Anti and Fwuki embracing, chest to chest. They're lying on a bed, Fwuki on top, Anti beneath. Anti has his pants down, thrusting into Fwuki, who's nervous system is glowing as a result.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 13/07/2026

Got a chance to sit for a while and animate today, my sona (basically) getting railed by an anon girl with a penis. [ #matingpress #nsfw #nsfwart #nsfwanimation #cum #creampie #anal #t4t #transsex #girldick #analsex #anal ]

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Freak 🔞 [Comms Open] @sinfuljessie.com · 09/07/2026

𝕋𝕙𝕖 𝔸𝕟𝕘𝕖𝕝 𝕤𝕠𝕦𝕟𝕕𝕖𝕕 𝕥𝕙𝕖𝕚𝕣 𝕔𝕝𝕒𝕣𝕚𝕠𝕟, 𝕤𝕙𝕒𝕜𝕚𝕟𝕘 𝕥𝕙𝕖 𝕙𝕖𝕒𝕧𝕖𝕟𝕤 𝕒𝕟𝕕 𝕖𝕒𝕣𝕥𝕙𝕓𝕣𝕖𝕒𝕕 𝕒𝕝𝕚𝕜𝕖. Keep overthinking what to draw so made myself just draw some shit and stick to a single prompt. Shamimi with Lucifer imagery! [ #shadowmilkcookie #crk #art ]

Shadow Milk with angelic features. Only one eye is visible, and it's dripping / melting like a tear. His scar is warped, and the other half of his face is glitching out. He has a white halo with a very faint image of his milkcrown in it. His wings are milky white, and his hair is relatively flatter, flowing into a lake of milk like a waterfall. He has a very small toga wrapped around his midsection, baring his chest with his soul jam embedded unevenly into it. The painting is mostly black and white, but there's a faint overlay of a blue gradient on top over Shadow Milk's body and yellow gradient on the lake of milk.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 05/07/2026

This is the thing I was drawing while figuring out those Krita settings btw. I love these freaks. [ #shadowvanilla #pureshadow #puremilk #cookiecum #coochierun #nsfc #nsfw #nsfwart #yaoi #bl #gaysex #transsex ]

Pure Vanilla topping Shadow Milk. Important details: Shadow Milk is pretty much incoherent and practically vibrating. Also his hair is filled with hearts. Both have major scars, each with a chest scar and SM with the dismemberment scars + doll features I recently decided on. They each have their soul jams dangling on a necklace, and the soul jams are resonating together.

Dialogue:
PV: "Good boy <3"
SM moans
PV: "Your voice is so sweet."
SM: "N-nilla-a~" moans

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Freak 🔞 [Comms Open] @sinfuljessie.com · 05/07/2026

Screenshots to clarify a bit. By default, Ten Brushes lets you use Ctrl+Alt+[number] to access each slot. In the keyboard shortcut settings, you can change the shortcut to each slot, which is how I setup my eraser / brush swap.

Screenshot of the Krita Ten Brushes script window. Shows 4 brush presets set with a custom keyboard shortcut, and blank presets with the default Ctrl+Alt+[number] keyboard shortcut.

Krita Keyboard Shortcut settings for Ten Brushes with brush presets 1-4 given custom shortcuts.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 30/06/2026

Watching some Mashle right now and wanted to doodle the ace king Mash. He's so cool and stupid. [ #mashle #asexual #fanart #doodle ]

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Freak 🔞 [Comms Open] @sinfuljessie.com · 24/06/2026

I forgot to post this here (drew it before the public episode release), but AU where Bubble gets a body like Caine and starts unabstracting folks to spite him. They're a shitty little guy! #tadc #tadcspoilers #tadcau #doodle

Concepts related to the AU:
text: "AU where Bubble / blue AI gets a body. Bubble un-abstracts people to spite Caine, relatively better at reading emotions. Mean. Scratch back! Jax back! and trans!"
The most important images are: Jax in a feminine outfit that takes some aspects from Caine, including his bowtie on her head. Bubble with a body, similar to Caine with the floating head, but more designed around clown imagery. Scratch looking nervous. There's a small doodle to the side of Bubble telling Caine "KYS."
Jax and Scratch also have visual errors on their body, meant to represent "scars" from their abstraction. Tried to mimic the glitchy effect Pomni and Ragatha got when touching an abstraction with that.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 23/06/2026

VGen commission for vgen.co/panstel. Doodle of her characters - Astraeus fantasizing about Amais getting some attention from tentacles! #vgen #commission #nsfwcommisions #nsfwart #tentaclesex

Astraeus fantasizes about the following scene: Amias is held by multiple tentacles. The tentacles are taking his clothes off, jerking him off, and entering his mouth.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 23/06/2026

Age regression doodle time! Baby Shamimi on a walk with Mama Nilla. #shadowvanilla #pureshadow #puremilk #agere

Shadow Milk as an extremely young child, holding Pure Vanilla's hand. Shadow Milk has a pacifier in his mouth, a flower in his hair, a small dress, and a bunny plush. Pure Vanilla is wearing a simple robe and holding a basket in his other hand.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 21/06/2026

Late reply but- Fwukipap (he/him), shapeshifter twink who has been through some shit. He can't die in most cases, at least not permanently. I have built up so much worldbuilding and lore around this freak, including a fictional language. I'm very normal.

Doodle of Fwuki regrowing his arms sith the caption: "haters will see you regenerate limbs, and be like he can't afford healthcare"

Comic panel of Fwukipap (Kem) as a child, regenerating his head and arm in a vat. Dialogue saying: "But... at least Kem is recovering quickly. His healing's gotten faster."

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Freak 🔞 [Comms Open] @sinfuljessie.com · 19/06/2026

Drew gore of my comfort character <3 Shamimi decapitated head cradled in PV's arms, going off the idea he was dismembered and thrown in the Lake of Truth. Added some notes in the alt-text about how I drew SM. #crk #shadowvanilla #gore #bodyhorror

Pure Vanilla holding Shadow Milk (Fount of Knowledge)'s decapitated head. Pure Vanilla's face is out of frame. Shadow Milk's face is somewhat melted and cracked, like the colors were smudged, and jam is dripping out of his mouth and neck.

Notes: Tried to think about what a decaying cookie would look like instead of making him look like a dead human. Rigid face, some of his expression moments before dying kept instead of completely relaxed muscles. Cracks, like he's actively crumbling. Smudged icing and milk, partially from the Lake of Truth, but also with the concept that a decaying cookie's icing might bleed and smear over time.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 19/06/2026

Hello ArtShare folks! I'm Jessie (they/he), I draw a lot of NSFW about whatever I'm hyperfixated on at the moment - CRK rn. I make a lot of very kinky, queer, sex-positive art and make an effort to include diverse bodies, including disability. 🔗: vgen.co/sketchyjessie

Shadow Milk and Pure Vanilla cuddling. Shadow Milk has a pacifier in his mouth.

Croissant doodles: one fully dressed, one of her lifting her tanktop to wipe sweat off her forehead (revealing her entire chest).

Mold Dough crying, sweating, drooling, and shaking. He thinks: "It hurts so much. Can't think. Can't sleep. Can't breathe- Hurts! It- hurts!"

Drawing of Shadow Milk in trans colors. He's covered in scars, including top scars, and has ball jointed arms with doll-like segmented hands. He's flushed and smirking. There's an overlay of hearts, a snake draped over his torso, and a star in his hand.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 19/06/2026

idk if I remembered to share this, but I have an ongoing Pride Month sale on my sketch comms for the month of June! vgen.co/sketchyjessie I'm fairly open to a lot: yumeships, various kinks, horror, etc. Anything I make here is free game! [ #commissions #nsfwcommsopen ]

Screenshot of my VGen services on sale (30% off) for pride month. Both are sketch / doodle services, one SFW and one NSFW.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 19/06/2026

he's totally cool and sane and just doing what is right folks, trust!

text: "This show will not fail." SMC, trying not to sob.
doodle: Shadow Milk crying and smiling in extreme rage.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 18/06/2026

Ok grandpa let's get you to bed cookie run kingdom update spoilers ofc

Doodle tracing the "ok grandma" meme, Shadow Milk is the grandma because he is Unwell.

Shadow Milk: "The Ultimate Dough corrupts from within, worming into the depths of your mind and whispering to you."
Black Sapphire: "Oh! That's... very powerfl, Master Shadow Milk Cookie! Are you sure you're ok??" (internally screaming FUCK)

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Freak 🔞 [Comms Open] @sinfuljessie.com · 15/06/2026

Feel weird directly submitting to the event this is for, but I wanted to write to the creature with the format regardless so I did! Thanks Shamimi for making me ill.

Using the 17th CookieRun Day Letter template, modified to be themed around Shadow Milk.

"To: Shadow Milk, From: Mocha Cream.

Master Shadow Milk Cookie,

Thank you for letting me witness your great story. Fate has been unkind to you and many others, but fate is nothing to a playwright such as yourself. Who cares what the witches want? What those fools think?

Your story is yours to write, your dough is yours to mould. You are an inspiration and muse to me. May we take the future we want by our own hands.

Your loyal servant, Mocha Cream Cookie"

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Freak 🔞 [Comms Open] @sinfuljessie.com · 12/06/2026

Reposting the pregnancy comic I did a while back now that I can put it all in one post. Might go through other past comics to repost for the same reason. #pregnancy #shadowvanilla #pureshadow #puremilk #smpv

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Freak 🔞 [Comms Open] @sinfuljessie.com · 12/06/2026

Walking back to apartment, saw a brown blob I thought was like, dog poop or trash. It was dark so couldn't tell, I could only see the big rabbit. To my surprise the brown blob is two itty bitty baby rabbits and one bolted when I got close. The other huddled to the ground. Artist rendition:

Doodle of the situation described in post. I see a brown blob and a rabbit, don't connect the two. I walk forward, closer to the brown blob, thinking "weird." Then the brown blob reveals itself to be two baby rabbits, one bolting away and the other still.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 07/06/2026

Happy Pride!!! Finally got to a piece. Despite everything this little shit has done and suffered, I think his story of transformation is beautiful. May he find love and acceptance, to shed himself of the shame and duty so he can be Shadow Milk, no more and no less. #crk #nsfc #nsfw

Shadow Milk, nude, with an overlay of the trans pride colors. He's scarred in several places (including top scars), has ball-jointed arms, and a penis. He holds a light in his fingers, and has images of a snake coiling around his chest and hearts around him. He smirks, looking down at someone.

Little explanation of my headcanons for the details: I view Shadow Milk as fully a shapeshifter, choosing the top scars deliberately. Maybe pre-corruption he was straight up trans, but the choice to keep the top scars when he can just make his body whatever means something to him. Other scars are implied dismemberment and the scars from being Ultimilk in the most recent updates. The snake and light are kinda just visual flairs, but I think add to the whole vibe of self acceptance even with the more rough-around-the-edges features.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 04/06/2026

Headcanons about Dough Trio and thoughts on Mocha Cream and how they fit into canon. If any of this contradicts canon uhhhh oops

Since I'm a little obsessed, headcanons related to Dough Trio and Mocha Cream. I don't think it counts as headcanons for an OC but yknow.

- Since Mocha Cream is a sona, slapping on my irl traits: they're a transmasc enby, disabled, and chronically ill. So they relate in certain ways to Dough Trio because of their own experiences with persistent pain and exhaustion.
- Mocha Cream learned rudimentary healing from Cream Ferret and general magic from the academy in the Vanilla Kingdom. They heal themself and sometimes help the Dough Trio when they can.
- The Dough Trio all have very weird bodies. DEC didn't exactly make them well, they're already canonically falling apart at the seams and in constant pain. But beyond that, I think some of their body systems just malfunction out of nowhere. Maybe they lose vision out of nowhere, an organ ruptures, something grows somewhere it shouldn't, a chemical in the body is over- or under-produced.

- Mold Dough enjoys taking orders to an extent, almost missing the simplicity of life under DEC, even if he hates the thought of going back.
- When Mocha Cream agrees to give Mold Dough orders, most of these orders are self-care tasks. For information, they check in with "status report," ask direct questions, and generally try to minimize how much Mold Dough has to think to respond.
- Venom and Pom-Pom hate taking orders completely. Both are hostile even to more neutral orders, or really just being told what to do, but Venom is at least willing to play along when the situation suits. Pom-Pom is just feral. All the time. She bites people.
- Mold Dough vibes as the oldest sibling, Venom next and close in vibe, Pom-Pom vibes most as a little sister. This isn't really reflected in their literal ages, counting from date of creation.

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Freak 🔞 [Comms Open] @sinfuljessie.com · 04/06/2026

(3/3) If you ask enough people to command you, you'll find a dom eventually, probably. Capping it here just to avoid overworking myself from sheer hyperfixation.

Mocha Cream blushes and tries to explain / backtrack offering to command Mold Dough. Meanwhile Mold Dough is shivering and kinda just staring at Mocha Cream stumble over themself.

Mold Dough (thoughts): Hm. Didn't expect them to offer... Should I trust it? Orders...

Mold Dough makes his decision: "Command me."
Mocha Cream: "Huh?!"
Mold Dough: "You offered."

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Freak 🔞 [Comms Open] @sinfuljessie.com · 04/06/2026

(2/3) Assuming Mold Dough and Mocha Cream (sona) have met at least once because I don't feel like drawing their introductions.

Mold Dough: "Command me."

Mocha cream is blushing and caught off gaurd, sputtering and confused.

Mocha Cream, still blushing and a bit nervous, looks up at Mold Dough.

Mold Dough: "Sorry. Habit." He looks sheepish and tired.
Mocha Cream: "Oh." thinking: Holy shit he's tall.

Mocha Cream recovers from their shock, still looking a birt confused.

Mocha Cream: "Do you...normally take orders?"
Mold Dough: "...Yes."
Mocha Cream: "Oh Uh. I mean- I could?"

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Freak 🔞 [Comms Open] @sinfuljessie.com · 04/06/2026

"Command Me" (1/3) Brain blast from Mold Dough first chat message lmao. He's in hell! #crk #molddoughcookie #doughtrio

Dough Trio hanging out. Venom and Pom-Pom argue loudly while Mold sits and watches them.

Mold Dough Cookie (thoughts): It's strange. No orders. No war. Just...peace. Futile fights. We lived.

Mold dough in pain, head in hands.

Mold Dough (thoughts): Out of habit, I still ask for orders. "Command me." "You don't have to!" "Do what you want!" Want? What do _I want? I don't want. I hurt.

Mold Dough in severe pain, breathing heavily with drool and snot dripping down his face. He's sweating and shaky, eyes unfocused.

Mold Dough (thoughts): It hurts so much. Can't think. Can't sleep. Can't breath- Hurts! It- hurts!

Mold Dough in severe pain, groaning and shaking. He holds the side of his head with his hands, curled into himself a bit.

Mold Dough (thoughts): Can't think! I miss- I _hate it! Need an order- Need- Pain. Stop! Hate- I hate her. Shouldn't have been made- Augh-

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