TheShadySail *Commission Open 3/3*
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theshadysail.bsky.social
TheShadySail *Commission Open 3/3*
@theshadysail.bsky.social
660 followers 750 following 660 posts
(She/They) We are a married couple making TTRPG and TCG 3D printed stuff and art linktr.ee/theshadysail
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theshadysail.bsky.social
I got a lil distracted
November 24, 2025 at 2:51 PM
theshadysail.bsky.social
Trying to figure out what I wanna call it
November 24, 2025 at 1:24 PM
theshadysail.bsky.social
Really thinking about what this piece means
November 24, 2025 at 12:50 PM
theshadysail.bsky.social
Plotting shadows
November 24, 2025 at 12:32 PM
theshadysail.bsky.social
Got a second opinion on color from the non-artist brother in law and feel more confident in my direction
November 24, 2025 at 12:16 PM
theshadysail.bsky.social
I forgot how quickly I paint
November 24, 2025 at 11:46 AM
theshadysail.bsky.social
Going well
November 24, 2025 at 11:26 AM
theshadysail.bsky.social
Watching 9-1-1 and painting an oil portrait
November 24, 2025 at 11:11 AM
theshadysail.bsky.social
Update to Leonaris WIP

#characterart #Sketch
Portrait of a Male Satyr with red horns and a text box that reads "Damaged Ear from Dare; He was dared to get a cattle tag pierced into his ear and rip it out without tearing up" This boy is a dumbass.
November 13, 2025 at 12:36 AM
theshadysail.bsky.social
Made up a quart of Russian tea fortified with Preacher from @fridaytea.com and a tablespoon of honey.
November 12, 2025 at 8:12 PM
theshadysail.bsky.social
Working on Leonaris, Honeys Satyr companion in my Monday Theros 5E Game
The upper body and portrait of a Male Saytr Work in Progress, he has shaggy browm hair and a GOAT-tee (haha)
November 11, 2025 at 8:55 PM
theshadysail.bsky.social
Quick portrait appreciation of some #ttrpgcharacters I have drawn in the recent past.

3 Slots still opened for sketches.
Portrait of a pale female demon with pink hair and shiny black horns. Portrait of a redheaded woman with ribbons with greek writing on them A portrait of a pale elf with slicked back black hair and a cured black eye Portrait of a brown haired blue eyed male character with a 5 o'clock shadow
November 11, 2025 at 5:11 PM
theshadysail.bsky.social
Moving in the Goth Direction here is more lovely character art

3 Slots Still Open
A female Mermaid with long black hair, a both bikini top and a balck and gold fin A Pale Female drow with a cursed eye with an inky black stain corrupting her face holding two fairy fires in her hands, wearing a fully black outfit
November 11, 2025 at 1:15 AM
theshadysail.bsky.social
Hi I am TheShadySail, I draw a lot of DnD stuff and 3D Model TTRPG supplies~

(I also currently have Sketch slots available)
November 10, 2025 at 5:52 PM
theshadysail.bsky.social
Hey #TTRPG Folks,

Opening up 3 Quick Sketches, This could be a: character, Item, A character detail or just a cute lil silly guy.

With the holidays coming up this could be a fun present for a friend or your DM to show appriciation and help add some zest to games~

#DnDcharacterArt #sketches
A gray full body sketch of a joyful looking female character with a shroud over her face and a staff in her hand A stylized sketch of a little goblin/kobold guy who is red and ornge with floppy red ears wearing blue pants and brown boots. A lizard wizard, a red dragonfolk in a joyous pose wearing purple and gold robes with a cool wizard hat. A sketch of one hand holding an open beige book and another hand pointing to a line on the page.
November 10, 2025 at 5:45 PM
theshadysail.bsky.social
Opening Halloween headshots to hopefully help catch up on debt
A blue women with an earring in the left ear with white bone like markings A white woman with red hair and a bookmark in greek hanging off her hair A white man with blue eyes and brown hair Three people from right to left: Black man in a pink argyle sweater, Asian woman in a gold and red shirt, and a non-binary person wear a fur trimmed cloak with braids
October 30, 2025 at 10:50 AM
theshadysail.bsky.social
Hey #ttrpg Folks~

I am opening up 5 Discounted Portrait Slots to help out my DM, she is an amazing DM and school teacher and she is really swimming in debt right now. So for a combined total of $50 you too can have a cool drawing of your character~

Details below~

Please repost/share
A portrait of a pale female demon with vibrant pink hair and black eyes Portrait of a pale human female with brownish red short hair and a paper with greek writing on it hanging from a braid A pale female human with blond hair and blue eyes, wearing a blue cloak with white fur trim three portraits of humans, a non-binary character with long black braided hair wearing a red cape with fur trim, a pale woman with short black hair wearing a red and gold shirt, and a black male character wearing a pink argyle sweater vest.
October 13, 2025 at 5:45 PM
theshadysail.bsky.social
Some more Portraits~
A human woman with long brown braided hair wearing a white top and deep blue corset A pale female Elf with slicked back black hair, one eye has a black mark coming off of it A blond human woman wearing a blue cloak with a white fur trim. A young human woman with a brown shirt and a large cursed section of her face
October 6, 2025 at 6:13 AM
theshadysail.bsky.social
Some quicker art, sketches and WIPs
Sketch of a womans back holding a rod of sorts. Black and grey A Kobold Lizard wearing a purple and gold outfit in a playful jumping pose. Portrait of a white male human, pale with blue eyes and brown hair. "Think twink" A pale book held open by a hand with another hand pointing to a page
October 4, 2025 at 2:18 PM
theshadysail.bsky.social
Giving a lil love to some portraits/tokens
Portrait of a blue skinned character with white markings and a single long earring in their left ear. A female orc with red eyes, green skin, afro style hari with tight braids along one side, wearing a red and gold cropped military sytle top and a scale mail poldrun with a chainshirt sleeve on the right arm. A token portrait of a Pale female human with OOrange/Red hair with a paper decoration in her hair, surrounded by a green laurel border A token Portrait of a pale white elf with black hair and a cursed mark around one eye, the eye glowing a bright purple. Surrounded by a worn purple stone border
October 4, 2025 at 12:34 AM
theshadysail.bsky.social
Hey Folks,

I am behind on rent and hoping to pick up some work here to make up for it!

Please consider helping out by having me draw your character/item or reposting this/tagging people who maybe interested~

ko-fi.com/theshadysail...
#ttrpg #dnd #pathfinder #characterart
A light purple female orc wearing white and gold holding a glaive, she is missing one leg replaced by a red shadow of her leg. Yuli, a female black and red kenku holding a censor being lit by violet light Three portraits, from left to right a non-binary character with long dark hair braided with ribbon wearing a cape. A asain female wearing a gold and red shirt, A black male wearing a pink argyle sweater vest over a white button up A female Arcane trickster wielding fairy fire with a blackened curse mark surrounding her left eye wearing all black.
October 2, 2025 at 3:11 PM
theshadysail.bsky.social
Looking at the full image he is drawn with the same tones as every other white person depicted by this artist on this day.

Courtroom sketch artists have crazy deadlines and limited supplies so although this isn't a super accurate depiction I don't think there was an agenda on the artists part.
September 30, 2025 at 11:12 AM
theshadysail.bsky.social
Made a lil GIF for a friends wonderous item in our Monday night Theros 5E Game~
September 24, 2025 at 4:53 AM
theshadysail.bsky.social
Man I don't do a lot of chest up drawings but when I do~
A green femal orc wearing deep red and gold clothes with scale mail pauldrons. A white woman with long braided hair in a deep blue corset and white chemise. A red haired elf with maple leaf earrings holding a coat over his shoulder. A variety of individual portraits line up, a native american with braids, asian woman and black man.
September 1, 2025 at 10:48 AM
theshadysail.bsky.social
I'l be opening commission soon for TTRPG folks, So here is some of my work.
A bird folk that is black and orange flying named yuli a black and white sketch of a female character with a staff a ratfolk with mismatched coloration in their garb A young purple orc staring then on her knees wearing black, with text saying " Sszon? Are you Ok?" and "I'm fine..." and " Young Dillisnya, you'll do just fine"
August 30, 2025 at 6:06 AM