Theo Winterwood
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theo-winterwood.bsky.social
Theo Winterwood
@theo-winterwood.bsky.social
160 followers 280 following 200 posts
They/Them
Thirtysomething, queer, does some art and writing (sporadically and without an audience), not sure what else to say here right now.
(Could potentially occasionally repost 18+ art)
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theo-winterwood.bsky.social
Quote your art with glasses on! 🕶⭐✨
A digital drawing of a faerie with light green skin, sitting on a chest freezer, smoking a cigarette, and soldering a homemade gadget while referencing a journal of handwritten notes. He has four arms and the lower right arm is amputated below the elbow. One wing is brown and orange and the other is dark blue and black; the hands on each respective side have skin slightly tinted to match that wing. One eye is also dark blue and the other is dark brown. He wears glasses with unfashionable aviator frames made of translucent beige plastic and a pair of brown overalls with one strap undone and both thighs patched. He does not wear a shirt and his body is heavily tattooed in blue-black stick-and-poke art. His dark hair is buzzed short in an undercut around the sides and back, with the rest pulled up in a messy bun. There are four small insert images: 1. A philips head screwdriver tip and carpenter pencil. 2. A handmade bottlecap pin with the words "know-it-all smartass" painted on it. 3. A closeup on his eyes. 4. Honeysuckle flowers in pale yellow and white. #queerart #queercharacter #oc #ocsky #faerie #fairy #scifi #fantasyart #daggerheart #ttrpg #fae #originalcharacter #oc
November 26, 2025 at 3:21 PM
theo-winterwood.bsky.social
The art vs the artist's hand 🌈
A crop of a larger piece: A fat elf with warm tan skin and dark brown eyes, who wears his long black hair (with a dark green undertone) in a braid filled with colorful wildflowers. He sits naked on the side of his bed, and in front of him kneels a tall slender fae (Archfey). The elf cups the fae's chin with one hand, and the fae's tongue brushes the elf's thumb. The fae's skin is a cool near-white color, turning gradually black as it goes down his forearm to the hand that grasps his lover's side. He has loose black waves of hair and white antlers that turn black at the prongs, and wears a simple silver circlet over his forehead with a small oval white stone in it. The room is comfortable and opulent, with bold florals on the wall, and warm low lighting coming from two lanterns above their heads. A hand, warmish peachish skintone, somewhat grown out black nail polish, dark hair on arm and some on the hand/knuckles.
November 7, 2025 at 3:47 PM
theo-winterwood.bsky.social
Post your best elf #art!

(Crop of a bigger piece)
A crop of a larger piece: A fat elf with warm tan skin and dark brown eyes, who wears his long black hair (with a dark green undertone) in a braid filled with colorful wildflowers. He sits naked on the side of his bed, and in front of him kneels a tall slender fae (Archfey). The elf cups the fae's chin with one hand, and the fae's tongue brushes the elf's thumb. The fae's skin is a cool near-white color, turning gradually black as it goes down his forearm to the hand that grasps his lover's side. He has loose black waves of hair and white antlers that turn black at the prongs, and wears a simple silver circlet over his forehead with a small oval white stone in it. The room is comfortable and opulent, with bold florals on the wall, and warm low lighting coming from two lanterns above their heads.
November 6, 2025 at 8:15 PM
theo-winterwood.bsky.social
2005 - 2025

Fuck 🖕 AI
I have genuinely no context for this. Pulled it from the place I originally posted it, where I said it was apparently an illustration of a friend's short story? A thin person, no shirt, necktie, bloody(?) feather boa, 00s era accurate low rise tight pants, platform boots, large confusing hair in purple, blue, and black, with a tiara, and face in white greasepaint. There are song lyrics in the background; I have no idea what song this is. A figure with pale greenish skin and shoulder-length white hair, with two black horns. They are holding a large book, and are dressed in mismatched layers of dark muted reds and grays, with a necklace of bones and teeth around their neck. The left hazel eye is normal, the other has a cluster of several smaller irises and pupils that match the one on the left. They have a pear-shaped figure with broad hips and thighs and dark circles under their eyes.
November 6, 2025 at 5:47 PM
theo-winterwood.bsky.social
Quote with your pink art!! 🌸
A person in a pink floral dress with short puffed sleeves and a pale green petticoat is sitting on a small couch covered in blankets and pillows. They also wear a ruffled white pinafore apron, strawberry earrings, and white stocking patterned with pink rosebudes. They have short pink hair, multicolored stars on their cheeks and forehead, and a few prominent facial scars on their cheeks. They are working on an embroidery piece in a hoop and have one foot resting on the coffee table, which also has a teapot, sandwich, and partially eaten cherry pie on it. Behind them, a window filled with hanging plants looks out into an evening sky.
October 21, 2025 at 8:27 PM
theo-winterwood.bsky.social
My favorite page
October 19, 2025 at 5:27 AM
theo-winterwood.bsky.social
I can be trusted to make a normal lowkey character sheet (just a few of the pages....) #dnd #Journaling (ish) #crookedmoon
October 19, 2025 at 3:06 AM
theo-winterwood.bsky.social
QRB w/ your pumpkin art ;3
A fat scarecrow? Or something. tbh, I've just think of them as "a pumpkin." They have a jack-o-lantern head and are running terrified from a vague silhouette of a monster behind them. The pumpkin is wearing loafers, plaid slacks, an argyle sweater vest, and a necktie and button-up shirt. Their sweater vest has two small gold pins on it, one shaped like a planchette and the other with an eye.
October 10, 2025 at 3:55 PM
theo-winterwood.bsky.social
Did this very fast little doodle thinking about how our DM mentioned Over the Garden Wall as one of the touchpoints for this game. #originalcharacter #dnd #crookedmoon #oc #ocart
A flat cartoon-style drawing of a character with greenish gray skin, black horns, shoulder-length white hair, and vaguely goth(ish) red and gray clothing. One eye has multiple irises and even in simplified cartoon form, they have dark circles under their eyes.
October 8, 2025 at 9:09 PM
theo-winterwood.bsky.social
Just a close-up because I really like their eyes. #dnd #warlock #oc #originalcharacter #dndcharacter #crookedmoon #fantasyart #horrorart #queercharacter #queerart
Closeup of a face with pale greenish skin. The left hazel eye is normal, the other has a cluster of several smaller irises and pupils that match the one on the left. They have shoulder-length white hair, black horns, and dark circles under their eyes.
October 4, 2025 at 11:16 PM
theo-winterwood.bsky.social
Adipocere (he/they), my warlock for an upcoming game in the Crooked Moon campaign setting by @avantris.bsky.social - Horned King Patron, Scholar of the Forbidden background, built out of Hexblood. #dnd #warlock #oc #originalcharacter #dndcharacter #crookedmoon #spookyart #queercharacter #queerart
A figure with pale greenish skin and shoulder-length white hair, with two black horns. They are holding a large book, and are dressed in mismatched layers of dark muted reds and grays, with a necklace of bones and teeth around their neck. The left hazel eye is normal, the other has a cluster of several smaller irises and pupils that match the one on the left. They have a pear-shaped figure with broad hips and thighs and dark circles under their eyes.
October 3, 2025 at 7:54 PM
theo-winterwood.bsky.social
Post something random or have an awful October
September 29, 2025 at 2:56 AM
theo-winterwood.bsky.social
Artists, how do you draw hair? Show your art! ✨
September 28, 2025 at 1:16 PM
theo-winterwood.bsky.social
Welcoming any ideas/thoughts/headcanons for this character, just 'cause I'm curious what y'all would do ❤️
#oc #artistonbsky #originalcharacter #wip #fantasyart #queerart
September 25, 2025 at 2:38 AM
theo-winterwood.bsky.social
The last month sure has been a long year (and the next month looks like it'll be the same), but at least I'm making something new finally.
September 25, 2025 at 2:09 AM
theo-winterwood.bsky.social
Spooky season is here!
🧡🎃QRP your Pumpkin Art!🎃🧡
A charming fat scarecrow (or something like it, tbh I've always just thought of them as a pumpkin) with a jack-o-lantern head is running terrified from a vague silhouette of a monster behind them. The pumpkin is wearing loafers, plaid slacks, an argyle sweater vest, and a necktie and button-up shirt. Their sweater vest has two small gold pins on it, one shaped like a planchette and the other with an eye.
September 15, 2025 at 10:49 PM
theo-winterwood.bsky.social
If you see this, post a witch!
A 1990s swamp witch is using a pay phone and lighting a cigarette. His long hair is bleached and dyed green, the green dye fading and dark roots heavily grown out. His red witch hat is heavily festooned with greenery, namely Queen Anne's lace, green hellebore, and green pitcher plants. He has a lot of tattoos, and his knuckles are bloody and bandaged. The overall dominant color and quality of light suggests a swampy acid green. It's implied the pay phone is in a rundown police station, and so he may have been arrested.
September 2, 2025 at 4:15 AM
theo-winterwood.bsky.social
A digital drawing of a faerie with light green skin, sitting on a chest freezer, smoking a cigarette, and soldering a homemade gadget while referencing a journal of handwritten notes. He has four arms and the lower right arm is amputated below the elbow. One wing is brown and orange and the other is dark blue and black; the hands on each respective side have skin slightly tinted to match that wing. One eye is also dark blue and the other is dark brown. He wears glasses with unfashionable aviator frames made of translucent beige plastic and a pair of brown overalls with one strap undone and both thighs patched. He does not wear a shirt and his body is heavily tattooed in blue-black stick-and-poke art. His dark hair is buzzed short in an undercut around the sides and back, with the rest pulled up in a messy bun. There are four small insert images: 1. A philips head screwdriver tip and carpenter pencil. 2. A handmade bottlecap pin with the words "know-it-all smartass" painted on it. 3. A closeup on his eyes. 4. Honeysuckle flowers in pale yellow and white. A crop of a larger piece: A fat elf with warm tan skin and dark brown eyes, who wears his long black hair (with a dark green undertone) in a braid filled with colorful wildflowers. He sits naked on the side of his bed, and in front of him kneels a tall slender fae (Archfey). The elf cups the fae's chin with one hand, and the fae's tongue brushes the elf's thumb. The fae's skin is a cool near-white color, turning gradually black as it goes down his forearm to the hand that grasps his lover's side. He has loose black waves of hair and white antlers that turn black at the prongs, and wears a simple silver circlet over his forehead with a small oval white stone in it. The room is comfortable and opulent, with bold florals on the wall, and warm low lighting coming from two lanterns above their heads. Two figures walk down a narrow alley together; the alley is dim and grimy, lit by neon signs, with graffiti on the walls and cracked pavement underfoot. The character on the right is an oni with glasses, a beard, and long dark salt-and-pepper hair pulled back. He is fat with very thick muscular arms, wearing a sleeveless undershirt, work boots, and coveralls knotted around his waist. He has a large forearm tattoo of a dragon. The figure on the left is a human with vivid red hair in an undercut and facial piercings. He is trans, has not had top surgery, and is fat, with and thick thighs and a soft belly with visible stretch marks. He wears a cropped hoodie, short red athletic shorts, and shiny red combat boots. A tiefling with light green skin and gold eyes. His dark blue hair is shaved on the sides and messily braided on top of his head. His horns are like short antlers, dark green shot through with streaks of gold. He wears an old silver oval locket and an open sheer white shirt that shows off a variety of dark blue stick-and-poke tattoos scattered over his body. He has multiple gold piercings in his face and ears, plus one pierced nipple
August 30, 2025 at 1:25 PM
theo-winterwood.bsky.social
"I don't care what anyone says, I like that movie"
Jesse from A Nightmare on Elm Street 2, shirtless and screaming at his own right hand, now wearing Freddy Krueger's knife glove.
August 25, 2025 at 2:30 PM
theo-winterwood.bsky.social
QRT Your oldest art vs Newest!
✨️2005 vs 2025✨️

(I probably could find older, but this is the oldest I can easily find. Also I kind of like the way these parallel each other.)
Pen and colored pencil drawing of two people kind of cuddling on a very very large green couch. One of them has long black hair, white facepaint, and black lipstick, and wear black flared jeans and a plain black t-shirt. The other person has 2000s era layered shirts and chin-length brown hair. The picture is decorated with Bee Gees lyrics in part of the background. The rest of the background is wallpaper and a door. A fat elf with warm tan skin and dark brown eyes, who wears his long black hair (with a dark green undertone) in a braid filled with colorful wildflowers. He sits naked on the side of his bed, and in front of him kneels a tall slender fae (Archfey). The elf cups the fae's chin with one hand, and the fae's tongue brushes the elf's thumb. The fae's skin is a cool near-white color, turning gradually black as it goes down his forearm to the hand that grasps his lover's side. He has loose black waves of hair and white antlers that turn black at the prongs, and wears a simple silver circlet over his forehead with a small oval white stone in it. The room is comfortable and opulent, with bold florals on the wall, and warm low lighting coming from two lanterns above their heads.
August 17, 2025 at 6:58 PM
theo-winterwood.bsky.social
Qrp with your 10 or 20 year old art!

2015 vs 2025

(And this is with multiple years in the last decade that I regretfully made little to no art.)
A person in tattered vaguely punk clothes sits on their bed (in the middle of their bed still wearing combat boots??). They have a bright pink Mohawk and are putting on eyeliner. In the background, there is the neon green case for an upright bass. The lineart is inexplicably neon pink. A digital drawing of a faerie with light green skin, sitting on a chest freezer, smoking a cigarette, and soldering a homemade gadget while referencing a journal of handwritten notes. He has four arms and the lower right arm is amputated below the elbow. One wing is brown and orange and the other is dark blue and black; the hands on each respective side have skin slightly tinted to match that wing. One eye is also dark blue and the other is dark brown. He wears glasses with unfashionable aviator frames made of translucent beige plastic and a pair of brown overalls with one strap undone and both thighs patched. He does not wear a shirt and his body is heavily tattooed in blue-black stick-and-poke art. His dark hair is buzzed short in an undercut around the sides and back, with the rest pulled up in a messy bun. There are four small insert images: 1. A philips head screwdriver tip and carpenter pencil. 2. A handmade bottlecap pin with the words "know-it-all smartass" painted on it. 3. A closeup on his eyes. 4. Honeysuckle flowers in pale yellow and white.
August 17, 2025 at 6:48 PM
theo-winterwood.bsky.social
Post a witch, if you wish.
A 1990s swamp witch is using a pay phone and lighting a cigarette. His long hair is bleached and dyed green, the green dye fading and dark roots heavily grown out. His red witch hat is heavily festooned with greenery, namely Queen Anne's lace, green hellebore, and green pitcher plants. He has a lot of tattoos, and his knuckles are bloody and bandaged. The overall dominant color and quality of light suggests a swampy acid green. It's implied the pay phone is in a rundown police station, and so he may have been arrested.
August 17, 2025 at 2:50 AM
theo-winterwood.bsky.social
A crop of the image below: Sir Criseyde is a knight in the Court of Wildflowers, whose lover is the Pale King, the Archfey of Moonlight. (If Criseyde was a DnD character, he'd be a battlemaster fighter/archfey patron warlock.)
#oc #fantasyart #elves #fae #queerart #dndart #artistonbsky
August 12, 2025 at 12:00 AM
theo-winterwood.bsky.social
Finished piece off that half-finished rough sketch from 2022 I rediscovered: queer elf/fae romance, loosely adapted out of a DnD character concept I'd had in passing at the time. #fantasyart #queerart #oc #dndoc #fae #elves #queercharacter #fatcharacter #originalcharacter #artistonbsky
A fat elf with warm tan skin and dark brown eyes, who wears his long black hair (with a dark green undertone) in a braid filled with colorful wildflowers. He sits naked on the side of his bed, and in front of him kneels a tall slender fae (Archfey). The elf cups the fae's chin with one hand, and the fae's tongue brushes the elf's thumb. The fae's skin is a cool near-white color, turning gradually black as it goes down his forearm to the hand that grasps his lover's side. He has loose black waves of hair and white antlers that turn black at the prongs, and wears a simple silver circlet over his forehead with a small oval white stone in it. The room is comfortable and opulent, with bold florals on the wall, and warm low lighting coming from two lanterns above their heads.
August 11, 2025 at 11:46 PM
theo-winterwood.bsky.social
the violent jump from 2019 vs 2025

(This is the only art from 2019 I can even find. It's a drow for someone's very very short-lived game, done in Sharpie and pen--but there's kind a nice parallel to the 2025 drawing)
Black Sharpie drawing of a drow with solid red eyes, gold piercings, no shirt, and witchy tattoos in white. His hair is buzzed short in an undercut around the sides and back, with the rest pulled up in a messy bun. A bat is perched on one shoulder. A digital drawing of a faerie with light green skin, sitting on a chest freezer, smoking a cigarette, and soldering a homemade gadget while referencing a journal of handwritten notes. He has four arms and the lower right arm is amputated below the elbow. One wing is brown and orange and the other is dark blue and black; the hands on each respective side have skin slightly tinted to match that wing. One eye is also dark blue and the other is dark brown. He wears glasses with unfashionable aviator frames made of translucent beige plastic and a pair of brown overalls with one strap undone and both thighs patched. He does not wear a shirt and his body is heavily tattooed in blue-black stick-and-poke art. His dark hair is buzzed short in an undercut around the sides and back, with the rest pulled up in a messy bun. There are four small insert images: 1. A philips head screwdriver tip and carpenter pencil. 2. A handmade bottlecap pin with the words "know-it-all smartass" painted on it. 3. A closeup on his eyes. 4. Honeysuckle flowers in pale yellow and white. #queerart #queercharacter #oc #ocsky #faerie #fairy #scifi #fantasyart #daggerheart #ttrpg #fae #originalcharacter #oc
August 7, 2025 at 4:01 PM