#NaughtyNein
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defilerwyrm.art
random Caleb doodle slapped out while catching up on c4e4. No reference used so anatomical wonkiness may have occurred.
#criticallynsfw #tentacles #tentacleporn #terato #monsterfucking #calebwidogast #naughtynein #defilerwyrmart #sketches #nsfwart #teratophilia
Rough greyscale digital sketch of Caleb Widogast, nude, orgasming, suspended in the air by large, translucent tentacles which hold his legs up and penetrate his ass deep and rough in a shower of gooey liquid. Caleb’s face is turned to the side with his hand over his mouth and eyes screwed shut in ecstacy.
October 25, 2025 at 4:15 PM
defilerwyrm.art
#kinktober day 6: milking :3
In which Essek deftly displays that you can, in fact, milk a bull.
#essekthelyss #calebwidogast #minotaurs #monsterfucking #nsfwart #naughtynein #criticalrolensfw #defilerwyrmart #terato #teratophilia #nsfwfantasy
Lightly-colored digital sketch in which Caleb Widogast, in the form of a ginger minotaur, sits on a padded bench against a stone wall with his ass hanging off the end while Essek Thelyss, seen at 1/4th view from behind and to the right, pounds his ass with a very large, well-lubricated violet dildo big enough that he has to hold it in both hands (which are also lubricated, and we can easily imagine why). Caleb’s long, thin cock is fully erect and spewing cum as a violet ribbon of magic wraps around its length. Caleb wears the jade circlet that’s the material component for the shapechange spell as a cuff around his left bicep.
October 22, 2025 at 10:05 PM
defilerwyrm.art
#kinktober day 2: fingering (I’m a day behind)
I kinda overdeveloped the base sketch after the rough & went “well what if I just use this”
I think it came out well :)
#shadowgast #essekthelyss #calebwidogast #naughtynein #criticalrolensfw #gaynsfw #nsfwart #defilerwyrmart #criticalrolefanart
Greyscale digital sketch of a collared Caleb Widogast reclining on a chaise holding his legs up behind the knees while Essek Thelyss kneels in front and fingerblasts his ass with three fingers. Essek is fully dressed while Caleb is fully nude. Caleb has his right leg hoisted up over Essek’s shoulders.
October 3, 2025 at 11:14 AM
defilerwyrm.art
#kinktober day 1: threesome
Decided to make this year’s challenge a #Shadowgast one. Kicking things off with improper use of resonant echo!
#CalebWidogast #EssekThelyss #CriticalRoleNSFW #CriticalRoleFanart #NaughtyNein #NSFWart #defilerwyrmart #elfenjoyers #gayNSFW #sketches
Greyscale digital sketch of Essek Thelyss and his resonant echo double penetrating Caleb Widogast anally on a couch. They all look like they’re having a great time.
October 2, 2025 at 11:02 AM
defilerwyrm.art
A little something I drew right after Mighty Nein Reunited. I reckon the boys sometimes get a li’l hot & bothered sharing their adventures. Gotta reward cleverness! #naughtynein #criticalrolensfw #criticalrolefanart #shadowgast #calebwidogast #essekthelyss #defilerwyrmart #digitalart #gaynsfw
A two-panel digital comic of Caleb Widogast and Essek Thelyss of Critical Role. Caleb sits on a plush, berry-red sofa, naked with his legs spread wide, mouth open, blushing all the way down to his chest. Essek, also nude, kneels between Caleb’s thighs sucking his cock and fingering his ass deeply. In the top panel, Caleb says, “…And then I used shapechaaaaan—“ Essek cuts in with “Mm-hm?” Caleb continues, “—Shapechange to…gods…to turn into a…a bl— a blue, fuck, dragon—” The second panel is a close-up of Essek’s mouth grinning wide and licking Caleb’s set, uncut cock, saying, “Keep going.”
September 28, 2025 at 3:46 AM
defilerwyrm.art
Fuck yeah artshare! I specialize in the kind of artt bsky is trying to ban, and tbqh censorship and everyone who supports is can lick the seam of my balls
#nsfwart #gaynsfw #naughtynein #stucky #werewolves #tentacles #shadowgast #defilerwyrmart #teratophilia
September 21, 2025 at 5:45 PM
geobuth0rny.bsky.social
Worship

Lucien (?) x Caleb....👀🤔

(Old art repost 4/?
this one is an about uh 3 y.o doodle!)

#criticalrolensfw #nsfwart #naughtynein #criticallynsfw
#nsfwfanart
naked purple tiefling with a snake tattoo around the right arm almost gently holding the side of the head of a shirtless redhead who is busy going down on them while the head is titled a little upwards the purple tail of the tiefling is wrapped around the kneeling man's throat and they are looking down on the kneeling person with an almost fond expression red eyes are tattooed on the tiefling and sketched in the background
November 9, 2024 at 6:15 PM
foxtrot66.bsky.social
#Shadowgast!!! My beloved. Ride that drow, wizard man.
#essekthelyss #calebwidogast #naughtynein
June 5, 2025 at 8:37 PM
defilerwyrm.art
#art from last year: Caleb strikes me as a man who needs his 🍑 eaten and Essek strikes me as the kinda guy who can & will demolish a 🍑. (there are easter eggs!)
#NaughtyNein #Shadowgast #digitalart #nsfwart #criticalrolensfw #defilerwyrmart #gaynsfw #sketches
Colored digital sketch of Caleb Widogast of Critical Role from the shoulder down, naked, bent over a cluttered desk while Essek Thelyss (also nude, sweating, and flushed) eats his ass out. Caleb is scattering pages around the desk, and his erect, leaking cock is visible between the desk and his belly. Essek holds the front of Caleb’s thigh with a hand whose first three fingers are dripping with lube from having fingered Caleb. Shaky, handwritten speech-text for Caleb reads “Oh gods…” with the “Oh” drawn out with many H’es.
November 17, 2024 at 5:06 AM
defilerwyrm.art
🎃HAPPY HALLOWEEN!🎃 Looking for some spooky smut? Check out my latest #Shadowgast fic: Wie’s Tier (tear down my reason) ➡️https://archiveofourown.org/works/51248041
And here’s the little illustration I did for it, too…
#CriticalRoleNSFW #NaughtyNein #teratophilia #monsterfucking #nsfwart
Colored digital sketch of a large white werewolf fucking a man in the ass, viewed from behind. The human is on his back holding his feet up high in the air. The werewolf’s fist-sized lavender-red knot appears to have just popped free of his asshole, splashing thick white come down his ass onto the floor; or maybe it’s just about to get shoved inside. The geometric scars on the human’s forearm imply this is Caleb Widogast. The room around them lies in ruins.
October 31, 2023 at 6:11 AM
foxtrot66.bsky.social
Hello friends, Happy Monday! Full view of Caleb Widogast getting railed by Essek and his echo 🥵

This was for a fic of mine, linked further down. He just deserves a treat, you know?

#shadowgast #essekthelyss #calebwidogast #naughtynein #nsfw
March 4, 2024 at 9:33 AM
foxtrot66.bsky.social
Coming back in swinging with some #shadowgast old man yaoi shibari body worship ohhh yes. Caleb, you can't be all 'I'm too old' your 100+ year old husband my dude. He will tie you up and appreciate you no matter what.

#calebwidogast #essekthelyss #nsfw #naughtynein #criticalrolefanart #criticalrole
April 20, 2024 at 10:36 PM
foxtrot66.bsky.social
I was inspired by @petyrithoe.bsky.social to do a strip tease. Threw it out to the degenerates of aifl to choose what Essek should be wearing and what to take off, they selected this cosy Aeor Explorer theme for him.

#EssekThelyss #Shadowgast #NaughtyNein #CriticallyNSFW #criticalrolensfw
July 1, 2024 at 2:43 PM
defilerwyrm.art
Typical night in the Widogast-Thelyss household. 💜🧡🍑💦
#criticalrolensfw #shadowgast #naughtynein #digitalart #nsfwart #calebwidogast #essekthelyss #sketches #defilerwyrmart
Loose, greyscale, flat-color sketch of Essek Thelyss and Caleb Widogast in bed immediately after sex. Caleb is stretched out with his head down, ass up, and a pool of come partly visible beneath him. Heart symbols hover over the back of his head. Essek kneels between his thighs behind him with one hand on Caleb’s lower back and his still-erect, double-crowned cock drooling come onto his own fingers and Caleb’s skin. Both men have intact foreskins. The picture frame crops out both their faces. Essek has a speech bubble that simply says, “Good boy.” Blue sketch lines left visible add to the loose and casual vibe of the drawing.
May 28, 2025 at 5:33 AM
livnart.bsky.social
Spending all my time thinking about them…
#Shadowgast #EadwulfGrieve #NaughtyNein #CriticallyNSFW
A black and white illustration with four panels. In the first panel Essek slouches in an armchair with one leg stretched out. He’s wearing thigh high black leather boots, leather gloves, and a mesh-leather bodysuit. Next to his chair is a seemingly naked Caleb, subserviently kneeling, he is mostly covered by Essek. Essek looks to the right, smiling. Dialog „Ah… Caleb…“ Second panel shows Essek’s hand in Caleb‘s hair in a close up with only parts of Caleb‘s face. Caleb's eyes are closed, his face is serene. Caleb is wearing a leather collar. Dialog from Essek „Look who‘s joining us…“ Third panel, Caleb is pulled back by his hair, eyes wide open in shock, asking „Wulf?“. A golden ring on Caleb’s collar is now visible. Fourth panel shows a closeup of Wulf from the tip of his nose down to the beginning of his pectorals. He is wearing a leather collar with a silver ring and a silver leash. His face is smug with a lop-sided smile.
July 11, 2024 at 8:29 PM
foxtrot66.bsky.social
Actually, loose the cape. Now the pants. And that vest. Make a mess of the scarf.

#EssekThelyss #Shadowgast #NaughtyNein #CriticallyNSFW #criticalrolensfw
July 1, 2024 at 2:47 PM
livnart.bsky.social
what happens after studying magic... #naughtynein #shadowgast
September 9, 2023 at 9:28 AM
defilerwyrm.art
AifL #kinktober 3: edging
In which Essek introduces Caleb to a different sort of time magic.
I think I managed to do some good things here. Please full-view for details. :3
#shadowgast #nsfwart #naughtynein #criticallynsfw #gaynsfw
Greycale digital drawing of Caleb Widogast and Essek Thelyss from Critical Role. Caleb is sitting on a large desk, fully nude, with his legs spread and hands tied behind his back. He’s blushing all over his face, ears, neck, and chest, and is sweating heavily. His hair is loose. He wears a strained but enthusiastic expression, biting his lower lip. His darkly-flushed, uncut, erect penis is held in Essek’s left hand. Essek is fully clothed in multiple layers and is seated upright in a very plush chair, with his long upper sleeve draped over the armrest. Essek is not wearing jewelry, presumably for safety during sexual activity. His expression is one of Dominant attentiveness on Caleb. An ornate, half-elapsed hourglass stands precariously close to Caleb. On the desk’s shelves stand assorted books and journals, a glass box potions, a cat-shaped metal bookstop, a geode, two large crystals, a strange instrument like a sextant, a small chest, and a potted plant spilling down the side.
October 10, 2024 at 8:38 AM
foxtrot66.bsky.social
Gloves first. Okay now your booties. Then the shirt. And the trousers. Keep the cape.

#EssekThelyss #Shadowgast #NaughtyNein #CriticallyNSFW #criticalrolensfw
July 1, 2024 at 2:45 PM
defilerwyrm.art
since i’m getting a late start on #kinktober i opted to combine the first two: 1. werewolf 2. threesome
(dw, the #werewolf is a willing participant; he’s just not thrilled about the muzzle.)
#shadowgast #naughtynein #criticallynsfw #nsfwart #terato
A greyscale digital sketch depicting Caleb Widogast and Essek Thelyss having a threesome with a hybrid-form werewolf. Essek and the werewolf are double penetrating Caleb anally. Essek lies on his back on a settee with one hand on Caleb’s belly and the other holding a leash attached to a collar and muzzle on the werewolf. Caleb kneels over Essek with his back arched and hair tossing in pleasure. The werewolf kneels behind Caleb, not quite knotting him yet, baring his teeth in a recalcitrant manner as he tugs against the lead.
October 8, 2024 at 8:38 AM
japanne.bsky.social
Pages 5-8 of What We Have Is Magic. Essek settles in and gets to work.
Sometimes Caleb deserves nice things, and sometimes those things are a slutty Essek who's dtf.
#naughtynein #criticallynsfw #shadowgast
Page 5 of What We Have is Magic, with 7 comic panels 1. Caleb mirrors his cat's ire spell with his hand, causing it dump Essek onto the bed and into his lap. 2. Caleb: "I'd really like to enjoy you in this if you'd let me." He smiles at Essek and gently touches his head/ear. 3. Caleb: "Or at least le me help you out of it." Caleb reaches for Essek who is flushed and avoiding eye contact. 4. Essek: "You don't think I'm ridiculous?" He hides behind his hands. 5. Caleb: "Schatz." Caleb's totally in love with this idiot. 6. Caleb: "You're gorgeous." His hands are on Essek's upper arms. Essek: "Well." He stops hiding, sliding his hands down to his own neck. 7. Essek: "If you're interested, I had some more . . . plans." Essek moves his hands to Caleb's shoulders, grounding himself; Caleb moves his to Essek's sides. Page 6 of What We Have is Magic, with 7 comic panels 1. Caleb: "More experiments?" His face belies that this is the most exciting thing to happen to him all fucking week. Essek: "Y-yes." 2. Caleb: "I do love experiments." Caleb smooches Essek on the cheek, eyes closed. Essek is charmed and further relaxed. 3. Caleb: "Show me what you have." His hand traces up Essek's bare hip where the robe splits. 4. Essek: "If you're uncomfortable, you'll stop me." Caleb: "I am even more intrigued now, but yes. You'll know." Essek's hands rest on Caleb's chest. Caleb holds his wrists comfortingly. 5. Essek exhales, eyes closed. His right hand is horizontal and flat, his left rests perpendicular on it. 6. Essek's left hand moves upward, casting wrist pocket, retrieving two golden cuff 7. Essek latches one on Caleb's wrist with a KLCK. Essek: "For you." Page 7 of What We Have is Magic, with 6 comic panels 1. Caleb: "Enchanted?" He peers closely at one of the gold cuffs fastened on his wrists. 2. Essek: "Mmhmm. Now lay back." Essek hovers over Caleb floating, hands on his shoulders to encourage him to lay down. Caleb gazes adoringly at Essek like Winterscrest has come early. 3. Essek kisses Caleb on the mouth. 4. He bites Caleb's lip, almost off panel. The focus is on Essek's fingers laced with Caleb's has he shifts bother their hands higher across the sheets with a "sshhhff" sound. 5. Essek in undercommon: "MINE" Essek float straddles Caleb, his hands pinning Caleb's forearms in place as purple Essek magic emanates from the gold cuffs. Caleb's hands are about the same height as his head, elbows bent at right angles. Caleb is flushed. 6. Caleb: "I-immovable object bracelets?" Essek: "Yes." Caleb side-eyes one of the cuffs with a smirk. He is impressed and excited. Page 8 of What We Have is Magic, with 6 comic panels 1. Essek: "Another tower creation." A close up of his face as he, flushed, looks down on immobilized Caleb with a smile. 2. Essek: "Is this okay?" His hand is on Caleb's chest, combing through his chest hair. 3. Caleb: "Ja. Ja. Ja. Very okay. So okay." Caleb is flushed and excited as Essek's hand trails down his chest. 4. Caleb: "Have I done anything in particular to be treated to this?" He lifts his head , watching Essek kiss down his torso. 5: Caleb: "I would like to..." Essek kisses his hard dick through the blanket covering his lower half. 6. Caleb: "keep doing it." Caleb tips his head back in satisfaction, eyes closed.
April 17, 2025 at 1:17 AM
foxtrot66.bsky.social
Going back to my roots with some more Shadowgast Corp AU, can't get enough of Essek putting Caleb where he belongs. #EssekThelyss #CalebWidogast #CriticallyNSFW #NaughtyNein
November 27, 2023 at 12:02 PM
defilerwyrm.art
Caleb is a good boy who deserves a relaxing facial treatment. 😌
Or: Essek sees to Caleb’s skincare routine.
#Shadowgast #NaughtyNein #CriticalRoleNSFW #CriticalRoleFanart #EssekThelyss #CalebWidogast #NSFWArt
A colored digital drawing of Caleb Widogast, seen from the collarbones up, gazing up with an open mouth at Essek Thelyss, seen only from waist-level. Caleb’s head is tilted to one side; his face and tongue are covered in large splashes of thick semen. Essek’s fist holds the shiny, uncircumcised glans of his sizable penis (which has two coronae) against Caleb’s tongue, which is extended to curl around Essek’s cock. Caleb sports two earrings, a large gold hoop through his middle cartilage and an amber stud in his lobe.
November 5, 2023 at 5:22 AM
spicynewts.bsky.social
assorted Caleb Widogast smut #3
Mage Hand
#naughtynein #criticalrolensfw
December 17, 2024 at 12:31 AM
defilerwyrm.art
Caption this

li’l sketch based on a LOB photo :3
#Shadowgast #CriticallyNSFW #NaughtyNein #gaynsfw #nsfwart
A roughly-colored digital sketch of Essek Thelyss and Caleb Widogast from Critical Rule, both nude and erect. Essek stands facing Caleb with arms akimbo; only the right-hand edge of his face is visible, just enough to see that his cheeks are appled in a smile and his eyes are downcast onto his partner. Caleb sits on the edge of a bed with a red bedspread and a vaguely-sketched canopy frame; he is holding Essek’s cock in his right hand and his own in his left. He wears a black leather collar with a gold O-ring around his neck. He is beaming up at Essek with an adoring gaze.
September 2, 2024 at 1:29 PM