Maestro Psychopomp
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maestropsychopomp.bsky.social
Maestro Psychopomp
@maestropsychopomp.bsky.social
160 followers 34 following 360 posts
36 | Artist + Writer | You'll mostly see Crimson and Alessio when I get the nerve to post
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maestropsychopomp.bsky.social
It turns out, you can draw the same idea as many times as you want. 😌❤️

#HelluvaBossCriminAle
#HelluvaBossCrimson
#HelluvaBossAlessio
Many sketched ideas of the same pose: Alessio leaned back on the ground, braced up on his elbows. And Crimson leaning over him, moving towards him on hands and knees. Crimson is looking up at Alessio while saying, "Yer a smart guy. I don't gotta say what this is." Alessio in under Crimson. Alessio says, "Say it anyway." He has a slight blush.
October 30, 2025 at 11:10 PM
maestropsychopomp.bsky.social
Oops! You woke a grumpy Crimson. 💖🤭

#HelluvaBossCrimson
Crimson is lying on his side, his arms and legs are wrapped around a stuffed shark. There's drool on his shark. Crimson looks annoyed and groggy.
October 30, 2025 at 2:48 AM
maestropsychopomp.bsky.social
A smoking break can be relaxing. But Crimson is suspicious of the nice feelings he's getting.

#HelluvaBossCriminAle
#HelluvaBossCrimson
#HelluvaBossAlessio
Alessio and Crimson are relaxing on a couch together. Alessio is talking while holding a cigarette. Crimson is smiling with a cigar in one hand and a drink in the other. Alessio laughs. Crimson looks a bit surprised. There's a small heart above his head. Crimson squints suspiciously while smoking his cigar. There's a little heart with a question mark. "Hmm..." is written beside him.
September 20, 2025 at 5:40 AM
maestropsychopomp.bsky.social
I was having a rough time when I drew this, but I'm already starting to feel better.
I hope everyone is doing okay! 🫂

#HelluvaBossAlessio
Alessio is sitting on the floor with his hands folded over his face. His tail curved around him.
August 17, 2025 at 10:04 PM
maestropsychopomp.bsky.social
A thank you to @ghostyhaunts.bsky.social for letting me draw their character, Domino! ✨️ They're a snake/imp-sona (a snimp) and they're so fun to draw! 🐍

Ghostyhaunts has wonderful of art of them and makes a lot of great posts. 😌 You should check them out! 💖

#HelluvabossOC
#HelluvabossImpsona
August 5, 2025 at 1:41 PM
maestropsychopomp.bsky.social
I needed some serotonin, so I drew a CriminAle kiss. ❤️
I think it helped. 😌

#HelluvaBossCrimson
#HelluvaBossAlessio
#HelluvaBossCriminale
Crimson is seated. Alessio is on his knees in front of him. The two are kissing. Alessio is caressing Crimson's cheek and hair, while Crimson holds Alessio's waist with both hands.
July 18, 2025 at 6:03 AM
maestropsychopomp.bsky.social
Here's some Magma sketches I forgot to post!
😌 @chex-psychopomp.bsky.social and I drew sad CriminAle, but then we made them happy together. 💕I adore the way they inked it!
And we did some fun Andrealphus for our buddy @impassociate.bsky.social !🤭

#HelluvaBossCriminale
#HelluvaBossAndrealphus
At the top, Crimson is sitting aside in black and white. He's got a gay-pride broken heart by him. Alessio is in his gay-pride colors, looking over at him with concern. At the bottom, Alessio embraces Crimson from behind, nuzzling against him and making him laugh. Crimson says "Ale, dat tickles." They're fingers are laced while holding each other's hands. Also, there's pan-colored dildo on the right (different artist) and a cute Andre in the bottom right, but I don't know who drew them! Two Andrealphus drawings. The top one is sticking his butt out and shaking it. It says "Makin dreams come true" and "twerk twerk." A drawing of Vassago (by impassociate) stares in awe! The bottom text reads And so I said, "I don't get hungry, I get fun-gry." --It's a quote from Bob's Burgers.
July 10, 2025 at 9:12 PM
maestropsychopomp.bsky.social
The new playmat is so vibrant! ✨️ I love how grumpy Crimson looks, surrounded by all the bright glitter and rainbows.

Now that he's arriving to people's homes, it feels like he's keeping Pride going, congratulating us all (in his own, unique way) for being “a gay.” 🌈🎊

😌 It's an honor, sir.
Our set-up at home! Chex's pink laptop and accessories are on the left with a pink Blitz playmat. My black and greens are on the right with the green Crimson playmat. The screens on our mats are drawing tablets. And the new Crimson playmat is front and center! He's bold and sparkling and beautiful! 💖
July 6, 2025 at 1:26 AM
maestropsychopomp.bsky.social
POV: You got one good punch in. But you might regret it.

#HelluvaBossAlessio
Alessio is kneeling on the ground. He's wiping blood off his mouth while glaring at the viewer.
June 26, 2025 at 12:30 AM
maestropsychopomp.bsky.social
"Can you see the man with the evil eyes?"

This is a gift for my good buddy, ✨Dean Draws! @deandraws.bsky.social
You rock, man! 😌 I hope you had a great birthday! 🎉

#Ganondorf
This is Ganondorf from the Zelda video games. He kneels for the king in Tears of the Kingdom (2023), echoing his first appearance in Ocarina of Time (1998). He has a dark expression, clearly showing his insincerity when pledging his allegiance.
June 18, 2025 at 2:16 AM
maestropsychopomp.bsky.social
YES. What an amazing moment! 😩🙏✨️
I can't believe I forgot how to speak. At least I mustered up a polite thank you! 😅
June 17, 2025 at 12:04 AM
maestropsychopomp.bsky.social
Too Proud

#HelluvaBossCrimson
Crimson grips a Straight-Pride black and white flag tightly. He's facing it, pointed towards the dark. His other hand barely holds onto an MLM-Pride flag that's slipping out of his fingers.
June 15, 2025 at 9:26 PM
maestropsychopomp.bsky.social
Alessio lighting Crimson's cigar just delights me. 😌
But I'd love more suggestions for how to show Alessio's servitude, because it has my heart. ❤️

#HelluvaBossCrimson
#HelluvaBossAlessio
#HelluvaBossCriminAle
Alessio bends forward to light Crimson's cigar. Crimson smirks at him, pleased to receive his service.
June 8, 2025 at 7:41 PM
maestropsychopomp.bsky.social
Alessio's inner thoughts are fun to imagine. 😌

Thank you @chex-psychopomp.bsky.social for this cute idea!

#HelluvaBossCriminAle
#HelluvaBossCrimson
#HelluvaBossAlessio
Crimson shows off a board covered in papers and pictures. He talks as if he's just explained an elaborate and costly scheme. Crimson asks for Alessio's opinion. Alessio's many thoughts are depicted. He thinks Crimson is cute and passionate. He also thinks Crimson's plan won't work, but it makes him oddly happy to have an opportunity to support Crimson if failure happens. Alessio then changes his thoughts again, arguing with himself that he shouldn't let a bad plan happen at all. In the last frame, Alessio gives a simple "Mm" as his answer with a neutral face. Crimson responds as if he understands Alessio clearly. Crimson even suggests that he can "see it in Ale's eyes" that Alessio likes the idea, despite "saying" he doesn't.
May 23, 2025 at 3:36 AM
maestropsychopomp.bsky.social
Day 7: Wedding

I really enjoyed fussing over these. I'm a softie for romance, so you know I had to make them look extra lovey-dovey and proud to have each other. 😌❤️

#CriminAleWeek2025
#HelluvaBossCrimson
#HelluvaBossAlessio
#HelluvaBossCriminAle
Alessio looks fondly at Crimson as Crimson walks up the isle. Alessio is wearing a suit that has a mesh back to show his back markings. There's lace detailing around the edges of the mesh, as well as lace on his cuffs and the tail of his suit. Crimson is wearing a white suit with gold details. Instead of a dress, he has a long, sheer cape. He's also carrying a bouquet in a pageant style, like he's just won an award. Crimson smiles as Alessio proudly reaches out to him. The front of Alessio's suit shows more lace and hints of silver. He has a flower on his chest that matches Crimson's bouquet.
May 16, 2025 at 4:31 AM
maestropsychopomp.bsky.social
Day 6: Injury

I added a bit of color for this one, but I'm sharing the plain black and white version, too.

#CriminAleWeek2025
#HelluvaBossCrimson
#HelluvaBossAlessio
Alessio is unconscious in a hospital bed. Crimson stands at a large window in the room, looking out at the Sloth ring with hands folded behind his back. There are signs that Crimson has been waiting in this room for a long time. There's a pillow and blanket on a chair, a suitcase, a stack of books, and a coffee cup over multiple coffee-ring stains. A bouquet of flowers is on the table beside Alessio. An ottoman sits at the end of the bed to give Alessio more room for his feet and tail. It matches the look of Crimson's personal decor, suggesting Crimson has brought this piece from his house. An electric fireplace is also glowing at the end of the hospital bed, possibly to keep the shark warm, or to make him feel more at home. Alessio is unconscious in a hospital bed. Crimson stands at a large window in the room, looking out at the Sloth ring with hands folded behind his back. There are signs that Crimson has been waiting in this room for a long time. There's a pillow and blanket on a chair, a suitcase, a stack of books, and a coffee cup over multiple coffee-ring stains. A bouquet of flowers is on the table beside Alessio. An ottoman sits at the end of the bed to give Alessio more room for his feet and tail. It matches the look of Crimson's personal decor, suggesting Crimson has brought this piece from his house. An electric fireplace is also glowing at the end of the hospital bed, possibly to keep the shark warm, or to make him feel more at home.
May 11, 2025 at 4:02 AM
maestropsychopomp.bsky.social
Day 4: Possessiveness part 2

The last page of the little comic! Good things can come from stubbornness. 😌

#CriminAleWeek2025
#HelluvaBossCrimson
#HeluuvaBossAlessio
Crimson and Alessio stand in a fancy couple's hotel room. It comes with a heart shaped bed, a mirror above the bed, and complimentary champaign for two. Crimson sees the trouble he's gotten them in, but says they can make it work. He clearly would rather deal with this situation over admitting he's done anything wrong. Alessio looks more nervous than before. He's shaking and blushing.
May 9, 2025 at 5:04 AM
maestropsychopomp.bsky.social
Day 4: Possessiveness

The idea of a jealous Crimson was too fun! I made too many pages, though! So here's 1 through 4 out of 5.

Also, a thank you to my partner Chex @chex-psychopomp.bsky.social who inked this comic for me! ❤️✨

#CriminAleWeek2025
#HelluvaBossCrimson
#HelluvaBossAlessio
Alessio rings a bell to get the attention of a girl working at the front desk of a hotel. The front desk gal is surprised, then flirts with the tall shark, offering to guide him to his hotel room. Crimson is quick to interrupt the interaction. A grumpy Crimson tells the hotel clerk that Alessio is here with him. The clerk figures he's upset over being (short) ignored. She gives him professional attention by requesting the name on his reservation. Crimson motions for Alessio to come close to him. Alessio kneels. They are out of ear-shot from the clerk as Crimson tells Alessio to not leave his side. Alessio accepts the request, but suggests that the hotel might treat them like a couple. He looks nervous. Crimson smiles and waves off Alessio's concerns, saying there's no way someone would assume the pair are gay. He looks playful and relaxed. The hotel clerk perks up at finding the reservation in her system. As she notes that the gentlemen have two separate rooms, she winks and motions for Alessio to call her. Crimson snaps his head to her, yelling that they have one room. Alessio looks surprised to see Crimson's sudden anger, and to hear Crimson yell something that will -absolutely- make it look like they're in a relationship.
May 9, 2025 at 4:49 AM
maestropsychopomp.bsky.social
Day 2: Gay Mischief at Work

I imagined a busy day that has Crimson feeling frustrated at work. He can't wait to get rid of his company so he can spend time with his man. ❤️

#CriminAleWeek2025
#HelluvaBossCrimson
#HelluvaBossAlessio
May 7, 2025 at 3:33 AM
maestropsychopomp.bsky.social
Day 1: Scars

It's ointment for men: so even the most masculine men can try out healing. 😌✨

#CriminAleWeek2025
#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle
May 6, 2025 at 4:25 AM
maestropsychopomp.bsky.social
Please enjoy a few extra sharks while I'm working on CriminAle week. We've got pre-boyfriends Stu and DB. And in the background is Nickel, Tazer, and Jelly Sharko. (Sharks are so fun to draw!)
#HelluvaBossSharks
#HelluvaBossCrimsonsMafia
DB stares nervously at Stu while Stu lights a cigarette. Nickel laughs. Tazer kicks his feet. Jelly Sharko shivers while waiting for a command from his two-way radio.
April 14, 2025 at 5:24 AM
maestropsychopomp.bsky.social
Yeeesss!! I'm SO excited!!
March 12, 2025 at 1:33 AM
maestropsychopomp.bsky.social
In my mind, sharks love to dance. It's a way for them to swim on land. Sense Alessio is a dedicated man at work, I think he'd be a dedicated dancer, too. #HelluvabossAlessio
March 4, 2025 at 6:18 PM
maestropsychopomp.bsky.social
I always keep an eye out for Crimson when there's new merch. Since we didn't get him this time, I drew a couple of pin ideas for him and Alessio! I liked making them go together, like fire and smoke. ❤️
#HelluvaBossCrimson #HelluvaBossAlessio #Criminale
February 13, 2025 at 11:57 PM
maestropsychopomp.bsky.social
Here's some of the sketches I did on Magma in a birthday drawing party for @impassociate.bsky.social ! It was a lot of fun to see so many people draw their HB favs together! And I met so many awesome people! Thanks for inviting me, Ia!

#HelluvaBossCrimson
#HelluvaBossAlessio
#CriminAle
November 3, 2024 at 1:30 AM