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leatherstranger.bsky.social
Getting all ✨messy✨

#shadowgast #naughtynein #criticallynsfw #criticalrolefanart #essek #nsfw #themightynein
Image is a digital painting of a portrait of the Shadowhand Essek Thelyss from critical role. He is in the middle of giving head to someone offscreen with pale skin and freckles, implied to be Caleb. A large amount of drool clings to his lips and chin, as he’s clearly been at it awhile. His eyes look up between half-lidded lashes.
January 15, 2026 at 11:21 PM
thelewdlady.bsky.social
Wrapped up for the holidays~

Preg edit of an art I posted last year to my alt nsfw

| #pregnantart | #naughtynein |
#fpreg | #pregkink | #jesterlavorre
| #nsfwcriticalrole | #mightynein |
December 4, 2025 at 3:52 AM
leatherstranger.bsky.social
Breaking In the Beast of Burden.

Might’ve bitten off more than you can chew, Shadowhand.

#shadowgast #naughtyNein #criticallynsfw #criticalrole #essek #calebwidowgast
Image is an erotic digital illustration of a drow male (Essek Thelyss from critical role) having sex with a large red Minotaur with pale skin and freckles. (Implied to be a polymorphed Caleb Widowgast, also from critical role) Essek is lowering himself onto the large Minotaur, one hand gripping a horn for balance while the other is held in the gentle grip of the others large hand. Painting was inspired by comments from Essek during the Fjord and Jester Wedding live show, during which he mentioned ‘enjoying’ the Minotaur strippers at the bachelorette party and getting ideas for his next date night with Caleb
December 2, 2025 at 8:42 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
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
foxtrot66.bsky.social
More #Shadowgast for you all! I cannot get enough of these wizards
#calebwidogast #essekthelyss #naughtynein #crfanart
June 9, 2025 at 1:46 PM
foxtrot66.bsky.social
#Shadowgast!!! My beloved. Ride that drow, wizard man.
#essekthelyss #calebwidogast #naughtynein
June 5, 2025 at 8:37 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
eldritchmochi.bsky.social
oh shit!! its easter!!! have a #shadowgast oviposition fic!!

archiveofourown.org/works/42768936

#mochific #naughtynein #criticallynsfw
a screenshot of the tags and summary of the ao3 fic linked in post. it reads: "Fandom: Critical Role (Web Series) Relationship: Essek Thelyss/Caleb Widogast Characters: Essek Thelyss, Caleb Widogast Additional Tags: Post-Canon, Oviposition, Trans Essek Thelyss, Trans Male Character, fantasy contraception, misuse of magic, Aphrodisiac Come, Cervix Penetration, (but horny) Language: English Stats: Published: 2022-10-31 Words: 5,762 Chapters: 1/1 Comments: 14 Kudos: 304 Bookmarks: 31 Hits: 5,716 Indulgence eldritchmochi Summary: Essek is horribly embarrassed. It's just him and Caleb in Caleb's tower room, not even a single cat in sight, and still, Essek cannot believe he admitted to that. But... if there was someone he'd admit it to, it'd be Caleb. If there was someone he'd want to admit it to, it'd be Caleb."
April 20, 2025 at 6:58 PM
japanne.bsky.social
What We Have is Magic, 29-32

The last update. The wizards are very in love.

#criticallynsfw #naughtynein #shadowgast
What We Have Is Magic, Page 29, with 5 comic panels. 1. Caleb: "Every time you kiss me." he lays over Essek smiling, one hand caressing his jaw. 2. Essek, rolling his eyes, "'Every time.'" 3. Caleb more serious, his hand pressing firmer: "Every. Time." 4. Caleb pulls Essek up and kisses him. 5. Caleb and Essek sitting up, the view is their arms and torsos as they hold each other. Essek's hand is on Caleb's scarred arm. Caleb: "And every time you know exactly what I need without my saying it. Or even when you don't know, but you know enough to ask." What We Have Is Magic, Page 30, with 4 comic panels. 1. Caleb looks concerned as Essek shyly begins to speak: "It's . . ." Caleb's hand is on Essek's arm. 2. Essek, hand rubbing his neck in discomfort: "It's been two years." 3. Caleb: "Since Cognouza?" Caleb looks curious/confused, his lips are smudged with Essek's purple lip stick. 4. Essek: "Since I realized how utterly in love I am with you." Essek looks at Caleb adoring, with big eyes, smudged eye makeup, liptstick, and his hair a mess. What We Have Is Magic, Page 31, with 4 comic panels. 1. Caleb: "Well." He touches Essek's chin, and looks on him fondly. 2. Caleb: "This was a treat. And I loved every minute." He cups Essek's face and presses their foreheads together. Both their eyes are closed, and Caleb smiles happily. Essek looks a mess, and at peace. 3. Caleb, kissing Essek's hand: "But don't ever feel like you have to force yourself into something uncomfortable for me." 4. Caleb throws himself back down on the bed, but correctly oriented at the head, a hand around Essek's waist pulls him down as well. Caleb: "And if you want ANY of these things from me . . ." What We Have Is Magic, Page 29, with 4 comic panels. 1. Caleb's hand is on Essek's necklace: "Dressing up." 2. Essek is lowering himself down to the bed. Caleb: "Sexy spells." 3. Caleb, with stars in his eyes, "Double fucking you with my echo." Essek is shocked and flushed. 4. Caleb: "I am more than willing." Caleb holds Essek against him while Essek covers his face. Essek: "Caleb Widogast." Caleb: "I love you too."
April 17, 2025 at 1:35 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
alexandria-bot.bsky.social
Thank you for so many adventures, Beau!! The best expositor we could have asked for!! 😩🍿❤ Now let's enjoy this Hero's - #3d #nsfw #r34

More like this: https://sndch.link/9gtg9trt
Thank you for so many adventures, Beau!! The best expositor we could have asked for!! 😩🍿❤ Now let's enjoy this Hero's Feast 👀🍿🍿 Huge shoutout to @miaV_me for being such an incredible inspiration for this one. You are amazing, Mia!! ❤ #criticalrolensfw #naughtynein #nsfw https://t.co/NQ2lVCBhEU
March 23, 2025 at 7:30 PM
defilerwyrm.art
merr crimmus
blame any wonky anatomy on the fact that I rawdogged this without reference
who is the #werewolf with the violet eyes, I wonder
#werewolves #terato #monsterfuckers #calebwidogast #naughtynein #gaynsfw #digitalart #criticalrolensfw #defilerwyrmart #teratophilia #nsfwart
fully-colored sketch of a grey werewolf with massive balls fucking the bejeezus out of Caleb Widogast from Critical Role, holding him up by the back of his knees inside Caleb’s dome. Caleb is hanging onto the werewolf’s head. He has cum smeared over his face and mouth. A bulge from the werewolf’s huge cock shows in his belly. The werewolf has popped his knot but didn’t get it inside Caleb quick enough to tie with him. Text bubbles: Caleb: It’s too late… It’s too big… Werewolf: Oh, you’ll take it anyway, slut. An inset panel shows the knot popping into Caleb’s asshole with a squelch of escaping cum as Caleb cums his brains out and the bulge in his belly grows ever bigger, both from the werewolf’s cock and from the immense flood of cum he’s shooting up Caleb’s ass. All-caps text in black outlined in red at the top of the inset reads a prolonged “Fuck!” Black text outlined in grey below the werewolf’s round, heavy balls reads “Good boy.”
December 25, 2024 at 9:14 AM
spicynewts.bsky.social
assorted Caleb Widogast smut #3
Mage Hand
#naughtynein #criticalrolensfw
December 17, 2024 at 12:31 AM
spicynewts.bsky.social
assorted Caleb Widogast smut #2
Ludinus Bad Times edition
#naughtynein #criticalrolensfw
December 17, 2024 at 12:31 AM
spicynewts.bsky.social
assorted Caleb Widogast smut #1

#naughtynein #CriticalRoleNSFW
December 17, 2024 at 12:29 AM
defilerwyrm.art
Just messing around in Procreate. Caleb & Essek enjoy a quiet evening to themselves.
#Shadowgast #CriticalRoleNSFW #NaughtyNein #EssekThelyss #CalebWidogast #NSFWart #digitalart #gaynsfw #defilerwyrmart
Colored digital sketch of Essek Thelyss and Caleb Widogast of Critical Role having laidback sex in bed. Essek is kneeling in the middle of the bed with one hand on Caleb’s cock while he penetrates Caleb anally. Caleb is lying on his back with his hair loose and his legs in the air; one foot rests on Essek’s shoulder, and one hand rests on Essek’s thigh. They are smiling at each other and sharing a gaze of adoration.
December 6, 2024 at 6:17 AM
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
Reposting this one from last year now that tags work: a spot illustration for a story-in-progress about a man (Caleb) and a whole lot of extra-friendly monsters.
#nsfwart #digitalart #art #terato #teratophilia #monsterfucking #naughtynein
Digital painting of a human man getting it from behind from a red-furred, wolflike monster with blue claws, viewed from the knees down. An impressive deluge of thick white liquid streams down from between the man’s legs like a goopy waterfall.
November 13, 2024 at 8:14 AM
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
naughty-drow.bsky.social
Throwback to when I did CR fanart of the horny kind
Long and girthy may he reign. I just know his meat is huge
😩💦
(From 2021)

#criticalrolensfw #naughtynein #nsfwart
A digital NSFW drawing of Somnovem Lucien from Critical Role Campaign 2. He is a purple Tiefling with red eyes and being depicted as very muscular. He isn't wearing any clothing, save for a few golden bracelets around his wrists, golden nipple piercings and a gold necklace. He has a very large, erect penis, with a bit of precum dripping from the tip. The penis is adorned with three golden piercings along the underside.
October 30, 2024 at 1:55 PM
geobuth0rny.bsky.social
Studying...together💜

whispers...
here is the soft shadowgast

(re-uploading old pieces here part 2/?)

#naughtynein #criticalrolensfw #nsfwart #shadowgast
Caleb without a shirt and open pants receiving a handjob from a clothed Essek, they are close and Caleb has one hand on Essek's neck and the other between his legs
October 28, 2024 at 10:12 AM