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absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face 2024 after_sex anthro avian_demon bed black_nose blitzo_(helluva_boss) blush bodily_fluids breasts canid canid_demon canine claws clothed clothing collar comic cubedcoconut cum cum_from_pussy cum_in_pussy cum_inside demon dialogue english_text female fingers fur furniture genital_fluids genitals grey_body grey_fur grey_hair group hair heart_symbol hellhound helluva_boss hi_res holding_knife holding_object imp knife legwear loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nipples open_mouth overprotective owl_demon pillow portal profanity protective pussy raised_clothing raised_topwear red_sclera spiked_collar spikes spread_legs spreading stolas_(helluva_boss) teeth text thigh_highs toe_claws tongue topwear url vortex_(helluva_boss) white_body white_fur 2024 adopted_(lore) adopted_daughter_(lore) adoptive_father_(lore) angry anthro avian_demon black_clothing black_legwear black_nose black_thigh_highs blitzo_(helluva_boss) breasts canid canid_demon canine clothing collar comic cubedcoconut demon dialogue english_text female fingers fur grey_body grey_eyes grey_fur grey_hair group hair hellhound helluva_boss hi_res imp legwear loona_(helluva_boss) mammal mythological_canine mythological_creature mythology open_mouth owl_demon pillow portal profanity red_sclera speech_bubble spiked_collar spikes stolas_(helluva_boss) teeth text thigh_highs tongue url vortex_(helluva_boss) white_body white_fur yellow_sclera 2024 anthro avian_demon black_nose blitzo_(helluva_boss) breasts canid canid_demon canine clothing collar comic cubedcoconut demon dialogue english_text female fingers fur grey_body grey_fur grey_hair group hair heart_symbol hellhound helluva_boss hi_res holding_knife holding_object imp knife legwear loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nipples open_mouth owl_demon pillow portal red_sclera spiked_collar spikes stolas_(helluva_boss) teeth text thigh_highs tongue url vortex_(helluva_boss) white_body white_fur absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face 2024 after_sex anthro avian_demon bed black_nose blitzo_(helluva_boss) blush bodily_fluids breasts canid canid_demon canine claws clothed clothing collar comic cubedcoconut cum cum_from_pussy cum_in_pussy cum_inside demon dialogue english_text female fingers fur furniture genital_fluids genitals grey_body grey_fur grey_hair group hair heart_symbol hellhound helluva_boss hi_res holding_knife holding_object imp knife legwear loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nipples open_mouth overprotective owl_demon pillow portal profanity protective pussy raised_clothing raised_topwear red_sclera spiked_collar spikes spread_legs spreading stolas_(helluva_boss) teeth text thigh_highs toe_claws tongue topwear url vortex_(helluva_boss) white_body white_fur 2024 adopted_(lore) adopted_daughter_(lore) adoptive_father_(lore) angry anthro avian_demon black_clothing black_legwear black_nose black_thigh_highs blitzo_(helluva_boss) breasts canid canid_demon canine clothing collar comic cubedcoconut demon dialogue english_text female fingers fur grey_body grey_eyes grey_fur grey_hair group hair hellhound helluva_boss hi_res imp legwear loona_(helluva_boss) mammal mythological_canine mythological_creature mythology open_mouth owl_demon pillow portal profanity red_sclera speech_bubble spiked_collar spikes stolas_(helluva_boss) teeth text thigh_highs tongue url vortex_(helluva_boss) white_body white_fur yellow_sclera 2024 anthro avian_demon black_nose blitzo_(helluva_boss) breasts canid canid_demon canine clothing collar comic cubedcoconut demon dialogue english_text female fingers fur grey_body grey_fur grey_hair group hair heart_symbol hellhound helluva_boss hi_res holding_knife holding_object imp knife legwear loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nipples open_mouth owl_demon pillow portal red_sclera spiked_collar spikes stolas_(helluva_boss) teeth text thigh_highs tongue url vortex_(helluva_boss) white_body white_fur absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face blitzo_(helluva_boss) chain chained clothed clothing collar covered_eyes demon dream facial_scar feathers fully_clothed glowing gouache_(artwork) hallucination helluva_boss hi_res horn horror_(theme) hottmutton humanoid imp leash male nightmare open_mouth painting_(artwork) restrained restraints scar screaming simple_background solo spikes spikes_(anatomy) teeth traditional_media_(artwork) yellow_body yellow_feathers absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res angry angry_sex anthro areola arm_around_neck balls biped blitzo_(helluva_boss) bodily_fluids bottomless breasts canid canid_demon canine clothed clothing demon eyelashes female from_behind_position fur genitals group heart_symbol hellhound helluva_boss hi_res humanoid imp jizoku lactating loona_(helluva_boss) male male/female mammal milk moxxie_(helluva_boss) mythological_canine mythological_creature mythology nipples oblivious penetration penile penile_penetration red_body red_sclera red_tail saliva sex tail tongue tongue_out trio white_body white_eyes white_fur absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face 2023 3sdice absurd_res animal_genitalia animal_penis anthro avian_feet balls beak big_balls big_flare big_penis biped black_body black_feathers blitzo_(helluva_boss) blue_penis blue_tongue claws condom demon demon_humanoid digital_media_(artwork) duo equine_genitalia equine_penis erection feathers finger_claws flared_penis genitals grey_body grey_feathers hand_on_hip hand_on_own_hip helluva_boss hi_res holding_condom holding_object huge_balls huge_penis humanoid hyper hyper_genitalia hyper_penis imp knot knotted_penis knotted_tapering_penis male male_anthro male_humanoid medial_ring owl_demon penis pink_penis red_body red_skin sexual_barrier_device smile smiling_at_viewer spade_tail stolas_(helluva_boss) tail tail_feathers tapering_penis tongue tongue_out unused_condom unusual_anatomy unusual_genitalia unusual_penis white_body white_feathers white_skin absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face anthro blitzo_(helluva_boss) boots bow_tie carmilla_carmine choker clothing comic demon dialogue ear_piercing ear_ring elcee_rod english_text female footwear group hazbin_hotel helluva_boss hi_res horn imp jewelry makeup male monochrome moxxie_(helluva_boss) necklace piercing ring_piercing shoes signature sinner_demon sketch text trio absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face anthro blitzo_(helluva_boss) boots bow_tie carmilla_carmine choker clothing comic demon dialogue ear_piercing ear_ring elcee_rod english_text female footwear group hazbin_hotel helluva_boss hi_res horn imp jewelry makeup male monochrome moxxie_(helluva_boss) necklace piercing ring_piercing shoes signature sinner_demon sketch text trio absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face anthro blitzo_(helluva_boss) boots bow_tie carmilla_carmine choker clothing comic demon dialogue ear_piercing ear_ring elcee_rod english_text female footwear group hazbin_hotel helluva_boss hi_res horn imp jewelry makeup male monochrome moxxie_(helluva_boss) necklace piercing ring_piercing shoes signature sinner_demon sketch text trio absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face anthro blitzo_(helluva_boss) boots bow_tie carmilla_carmine choker clothing comic demon dialogue ear_piercing ear_ring elcee_rod english_text female footwear group hazbin_hotel helluva_boss hi_res horn imp jewelry makeup male monochrome moxxie_(helluva_boss) necklace piercing ring_piercing shoes signature sinner_demon sketch text trio absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face