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@twocoffeedraws.bsky.socialSep 19, 2026, 12:29 AM

CriminAle Week Afterparty!

Day 3 - Body Worship

I'll be slowly working my way through the rest of the prompts, wishing I was a faster artist the whole time 😭

#CriminAleWeek2026

#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle #HelluvaBossFanart

Crimson has Alessio's chin grasped in one hand, and is examining one of his long, sharp teeth with a finger. Alessio's confused as to what's going on, while Crimson is just enamored.
@foxwot.bsky.socialSep 13, 2026, 1:29 PM

Better late than never! Thanks again for the commission to @norrynator.bsky.social for date night in #criminaleweek2026! The pasta may not be ready but Crimson's bakery is! 🤌🇮🇹

#HelluvabossCrimson
#HelluvabossAlessio
#criminaleweek2026

Crimson and Alessio having a date night but Crimson craving the pasta in his mouth than his own man! 😂
@twocoffeedraws.bsky.socialSep 13, 2026, 7:30 AM

Day 2 - First Date

It's still CriminAle Week somewhere ;p

This is the prompt I wanted to do the most! I've had this image in my head for well over a year

#CriminAleWeek2026

#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle #HelluvaBossFanart

Alessio and Crimson having a sushi dinner date. Alessio is hand feeding Crimson a piece of sushi with a tentacle in it. Alessio's sushi rolls have tentacles, Crimson's have eyeballs. The view is from behind the sushi bar.
@chinheitsang2.bsky.socialSep 13, 2026, 5:18 AM

☺️👍CriminAle Week 2026 Day 3 Body Worship (SFW)😈🦈💕
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026 #CriminAleWeek

Alessio removed Crimson's hat with his right hand, then transferred the hat from his right hand to his left; with his right hand, he gently stroked Crimson's left horn. Alessio said earnestly: Crim, your horns are very sturdy. Crimson blushed with shyness upon seeing Alessio, and his tail wagged incessantly—a sign that he was in high spirits yet feeling somewhat bashful. Crimson said, looking a bit bashful: Yes, you're right, Ale. CriminAle Week 2026 Day 3 Body Worship (Helluva Boss) (SFW version) 13-09-2026
@astarvingfarbeagle.bsky.socialSep 10, 2026, 10:47 AM

#criminaleweek2026 Day 5: Sick/Injury

stupid clingy shark got sick🦈🤧😈

#CrimsonHelluvaBoss
#AlessioHelluvaBoss

Alessio is laying sick in a bed. Tissues are strewn around and and there's a hot tea on the nightstand. Crimson is sitting on the bed next to him, scolding him but also petting his snout. Text: Crimson: I told ya to keep your distance, but ya just HAD to play Mother Hen. Ya know how much that big drippy ass nose is gonna cost me in tissues? Alessio: Sorry, Boss... Crimson: Just get better. I can’t afford havin’ my number one laid up with the sniffles for a month.
@twocoffeedraws.bsky.socialSep 9, 2026, 8:02 PM

Day 4 - Possessiveness

Crimson, you aren't gonna lose your man to his masseuse :p

#CriminAleWeek2026

#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle #HelluvaBossFanart

Crimson and Alessio are getting a couple's massage. Crimson is fuming in the background, jealous of the shark/imp hybrid giving Alessio a massage. Crimson's masseuse: You're very tense... Alessio's masseuse is saying something indistinguishable, to which Alessio chuckles.
@vaudevilfair.bsky.socialSep 7, 2026, 4:18 PM

#criminaleweek2026
Day 2🦈👍 Some POV action after a business gig perhaps
#helluvabossfanart
#helluvabosscrimson

Crim and Alessio sitting in a car
@lovelypurple.bsky.socialSep 6, 2026, 10:59 PM

I TOTALLY DIDNT FORGET

First kiss!

#CriminAleWeek2026

#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle #HelluvaBossFanart

@chinheitsang2.bsky.socialSep 6, 2026, 5:17 PM

☺️😈🦈CriminAle Week 2026 Day 2 Date Night (Modified)🌃🍷🕯️💚💕
#HelluvaBoss #HelluvaBossFanart #HelluvaBossCrimson #Crimson #CrimsonHelluvaBoss #CrimsonxAlessio #HelluvaBossAlessio #Alessio #AlessioHelluvaBoss #HelluvaBossCriminAle #CriminAle #Vivziepop #Hellaverse #Spindlehorse #CriminAleWeek2026

Around 7 p.m., Crimson and Alessio were enjoying an outdoor candlelight dinner at a restaurant near the beach in Greed Ring. A candelabra with three long white French candles sat on the table, along with two mini scented white candles. Two plates of dinner were on the table: cooked salmon, mashed potatoes, and green beans. Cutlery and napkins were placed next to the plates; a knife was on the right of each plate, with a napkin underneath, and a fork and spoon on the left. Crimson and Alessio were seated, each holding a glass of red wine in their right hand, their eyes meeting and smiling at each other. Crimson smiled broadly, while Alessio smiled with his mouth closed. Furthermore, their tails were curled forward in a heart shape, symbolizing warmth and a deep emotional connection. CriminAle Week 2026 Day 2 Date Night (Helluva Boss) (Modified) 10-08-2026
@twocoffeedraws.bsky.socialSep 6, 2026, 5:10 PM

CriminAle Week 2026 begins!

Day 1 - First Kiss

A fun little sequel to the prompt list :3

#CriminAleWeek2026

#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle #HelluvaBossFanart

A black and white digital pencil sketch of Crimson and Alessio laying on their backs in the grass. Their bodies are parallel, but pointing in opposite directions. Their heads are tilted towards each other, lips met in a tentative kiss, Crimson cupping the back of Alessio's head with a hand.