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jesterwing

2024 absurd_res anthro arm_support arm_tuft backward_arm_support bikini biped bite biting_lip black_bikini black_clothing black_fingernails black_nails black_nose black_swimwear breasts canid canid_demon canine cheek_tuft choker cleavage clothed clothing colored_nails demon facial_tuft female fingernails fur grey_body grey_fur hair hellhound helluva_boss hi_res inner_ear_fluff jesterwing jewelry looking_at_viewer loona_(helluva_boss) lying mammal medium_breasts mythological_canine mythological_creature mythology nails navel necklace presenting red_sclera shaded shoulder_tuft solo spread_legs spreading swimwear tuft two-piece_swimsuit under_boob white_body white_eyes white_fur white_hair
2024 absurd_res anthro arm_support arm_tuft backward_arm_support bikini biped bite biting_lip black_bikini black_clothing black_fingernails black_nails black_nose black_swimwear breasts canid canid_demon canine cheek_tuft choker cleavage clothed clothing colored_nails demon facial_tuft female fingernails fur grey_body grey_fur hair hellhound helluva_boss hi_res inner_ear_fluff jesterwing jewelry looking_at_viewer loona_(helluva_boss) lying mammal medium_breasts mythological_canine mythological_creature mythology nails navel necklace presenting red_sclera shaded shoulder_tuft solo spread_legs spreading swimwear tuft two-piece_swimsuit under_boob white_body white_eyes white_fur white_hair
absurd_res angry anthro arm_tuft avian bikini bird bird_demon breasts choker clothing demon female glowing_eyes grey_body hair hand_on_hair helluva_boss hi_res jesterwing jewelry looking_at_viewer medium_breasts necklace octavia_(helluva_boss) open_mouth owl owl_demon shoulder_tuft solo swimsuit tuft two-piece_swimsuit wet
absurd_res angry anthro arm_tuft avian bikini bird bird_demon breasts choker clothing demon female glowing_eyes grey_body hair hand_on_hair helluva_boss hi_res jesterwing jewelry looking_at_viewer medium_breasts necklace octavia_(helluva_boss) open_mouth owl owl_demon shoulder_tuft solo swimsuit tuft two-piece_swimsuit wet
absurd_res anthro arm_tuft ass back bare_butt blush bodily_fluids breasts bubble canid canid_demon canine canis cheek clothing demon ear_piercing ear_ring facial_tuft female fur hellhound helluva_boss hi_res inner_ear_fluff jesterwing leg_tuft legwear looking looking_at_viewer loona_(helluva_boss) mammal marks multicolored_body multicolored_fur mythological_canine mythological_creature mythology piercing ring_piercing shoulder solo spank stockings sweat sweaty tail tuft wolf
absurd_res anthro arm_tuft ass back bare_butt blush bodily_fluids breasts bubble canid canid_demon canine canis cheek clothing demon ear_piercing ear_ring facial_tuft female fur hellhound helluva_boss hi_res inner_ear_fluff jesterwing leg_tuft legwear looking looking_at_viewer loona_(helluva_boss) mammal marks multicolored_body multicolored_fur mythological_canine mythological_creature mythology piercing ring_piercing shoulder solo spank stockings sweat sweaty tail tuft wolf
1girls angel angel_girl angel_wings armwear black_heels black_lipstick blue_eyes bow choker female female_only freckles freckles_on_face halo heels jesterwing lingerie lipstick long_stockings looking_at_viewer ribbon thigh_high_stockings thigh_highs thigh_stockings thighhigh_stockings thighhighs white_armwear white_bow white_choker white_female white_girl white_hair white_lingerie white_ribbon white_skin white_skinned_female white_stockings winged_humanoid wings wingsspreading
1girls angel angel_girl angel_wings armwear black_heels black_lipstick blue_eyes bow choker female female_only freckles freckles_on_face halo heels jesterwing lingerie lipstick long_stockings looking_at_viewer ribbon thigh_high_stockings thigh_highs thigh_stockings thighhigh_stockings thighhighs white_armwear white_bow white_choker white_female white_girl white_hair white_lingerie white_ribbon white_skin white_skinned_female white_stockings winged_humanoid wings wingsspreading
1girls angry angry_expression angry_face bow bracelet breasts dress female female_only helluva_boss jesterwing laying_down laying_on_ground legs_together long_hair pink_eyes pissed_off purple_bracelet ribbon short_dress stella_(helluva_boss) sunhat teeth_clenched teeth_showing teeth_visible thighs_together
1girls angry angry_expression angry_face bow bracelet breasts dress female female_only helluva_boss jesterwing laying_down laying_on_ground legs_together long_hair pink_eyes pissed_off purple_bracelet ribbon short_dress stella_(helluva_boss) sunhat teeth_clenched teeth_showing teeth_visible thighs_together
2024 absurd_res anthro arm_tuft avian beak bird bird_demon bra breasts cleavage clothed clothing demon digital_media_(artwork) female fingers hair helluva_boss hi_res jesterwing lingerie long_hair looking_at_viewer navel octavia_(helluva_boss) owl owl_demon panties selfie shoulder_tuft solo standing tuft underwear young
2024 absurd_res anthro arm_tuft avian beak bird bird_demon bra breasts cleavage clothed clothing demon digital_media_(artwork) female fingers hair helluva_boss hi_res jesterwing lingerie long_hair looking_at_viewer navel octavia_(helluva_boss) owl owl_demon panties selfie shoulder_tuft solo standing tuft underwear young
bra female hi_res jesterwing looking_at_viewer red_body reposted solo underwear
bra female hi_res jesterwing looking_at_viewer red_body reposted solo underwear
bra emily_(hazbin_hotel) female hazbin_hotel hi_res jesterwing looking_at_viewer red_body selfie solo underwear
bra emily_(hazbin_hotel) female hazbin_hotel hi_res jesterwing looking_at_viewer red_body selfie solo underwear
absurd_res canid canid_demon canine clothed clothing demon hellhound helluva_boss hi_res jesterwing looking_at_viewer loona_(helluva_boss) mammal mythological_canine mythological_creature mythology red_background red_eyes simple_background smile solo standing tongue
absurd_res canid canid_demon canine clothed clothing demon hellhound helluva_boss hi_res jesterwing looking_at_viewer loona_(helluva_boss) mammal mythological_canine mythological_creature mythology red_background red_eyes simple_background smile solo standing tongue
black_bra black_panties blush bra canon_couple charlie_morningstar_(hazbin_hotel) fingering hazbin_hotel heart-shaped_pupils jesterwing lingerie panties vaggie_(hazbin_hotel) wholesome yuri
black_bra black_panties blush bra canon_couple charlie_morningstar_(hazbin_hotel) fingering hazbin_hotel heart-shaped_pupils jesterwing lingerie panties vaggie_(hazbin_hotel) wholesome yuri
absurd_res angry anthro arm_tuft arm_under_breasts avian bird breasts clothing crossed_legs crown demon female goth hair headgear helluva_boss hi_res jesterwing jewelry legwear long_hair medium_breasts necklace octavia_(helluva_boss) owl owl_demon shoulder_tuft solo stockings tiara tuft
absurd_res angry anthro arm_tuft arm_under_breasts avian bird breasts clothing crossed_legs crown demon female goth hair headgear helluva_boss hi_res jesterwing jewelry legwear long_hair medium_breasts necklace octavia_(helluva_boss) owl owl_demon shoulder_tuft solo stockings tiara tuft
5:6 absurd_res anthro breasts canid canid_demon canine clothed clothing convenient_censorship demon duo fan_character feet female hellhound helluva_boss hi_res jesterwing knee_tuft leg_tuft loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology nude nude_male panties pawpads paws sex side_boob topless topless_female tuft underwear
5:6 absurd_res anthro breasts canid canid_demon canine clothed clothing convenient_censorship demon duo fan_character feet female hellhound helluva_boss hi_res jesterwing knee_tuft leg_tuft loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology nude nude_male panties pawpads paws sex side_boob topless topless_female tuft underwear
2024 absurd_res anthro arm_tuft black_bra black_clothing black_panties black_underwear body_hair bra breasts canid canid_demon canine canis cheek_piercing cheek_tuft chest_hair choker clothing cute_expression demon digital_media_(artwork) eyebrow_piercing eyebrow_ring eyebrow_through_hair eyebrows facial_piercing facial_tuft female fur grey_body grey_fur grey_hair hair heart_eyes heart_symbol hellhound helluva_boss hi_res jacket jesterwing jewelry leg_tuft lingerie long_hair looking_at_viewer looking_back loona_(helluva_boss) mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology navel necklace notched_ear panties piercing red_clothing red_jacket red_sclera red_topwear ring_piercing shoulder_tuft smile solo topwear translucent translucent_hair tuft underwear white_body white_eyes white_fur wolf
2024 absurd_res anthro arm_tuft black_bra black_clothing black_panties black_underwear body_hair bra breasts canid canid_demon canine canis cheek_piercing cheek_tuft chest_hair choker clothing cute_expression demon digital_media_(artwork) eyebrow_piercing eyebrow_ring eyebrow_through_hair eyebrows facial_piercing facial_tuft female fur grey_body grey_fur grey_hair hair heart_eyes heart_symbol hellhound helluva_boss hi_res jacket jesterwing jewelry leg_tuft lingerie long_hair looking_at_viewer looking_back loona_(helluva_boss) mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology navel necklace notched_ear panties piercing red_clothing red_jacket red_sclera red_topwear ring_piercing shoulder_tuft smile solo topwear translucent translucent_hair tuft underwear white_body white_eyes white_fur wolf
ambiguous_penetration black_socks black_stockings cum cum_dripping female fucked_from_behind fucking jesterwing long_socks nails penetration penetration_from_behind purple_hair semen semen_dripping sex socks stockings teeth_showing thigh_high_socks thigh_highs thighhigh_socks thighhighs unknown_character
ambiguous_penetration black_socks black_stockings cum cum_dripping female fucked_from_behind fucking jesterwing long_socks nails penetration penetration_from_behind purple_hair semen semen_dripping sex socks stockings teeth_showing thigh_high_socks thigh_highs thighhigh_socks thighhighs unknown_character
1boy 1boy1girl 1girls alastor_(hazbin_hotel) ambiguous_consent betrayal black_lipstick blonde_hair blonde_hair_female chained chained_collar chained_wrists chains charlie_morningstar_(hazbin_hotel) crying crying_with_eyes_open enslaved female gold_chains grin hazbin_hotel imminent_rape jesterwing lipstick makeup male no_consent questionable_consent red_eyes slave slave_collar slavegirl slavery smile teeth teeth_clenched teeth_showing teeth_visible worried worried_expression worried_face worried_look
1boy 1boy1girl 1girls alastor_(hazbin_hotel) ambiguous_consent betrayal black_lipstick blonde_hair blonde_hair_female chained chained_collar chained_wrists chains charlie_morningstar_(hazbin_hotel) crying crying_with_eyes_open enslaved female gold_chains grin hazbin_hotel imminent_rape jesterwing lipstick makeup male no_consent questionable_consent red_eyes slave slave_collar slavegirl slavery smile teeth teeth_clenched teeth_showing teeth_visible worried worried_expression worried_face worried_look
1girl 1girls angry angry_face black_hair black_socks choker female fingerless_gloves flustered garter_straps girl gloved gloves helluva_boss jesterwing long_socks octavia_(helluva_boss) red_choker red_tie school_skirt schoolgirl schoolgirl_clothes schoolgirl_uniform short_skirt skirt socks thigh_high_socks thigh_highs thighhigh_socks thighhighs tie
1girl 1girls angry angry_face black_hair black_socks choker female fingerless_gloves flustered garter_straps girl gloved gloves helluva_boss jesterwing long_socks octavia_(helluva_boss) red_choker red_tie school_skirt schoolgirl schoolgirl_clothes schoolgirl_uniform short_skirt skirt socks thigh_high_socks thigh_highs thighhigh_socks thighhighs tie
anthro_only belt belt_buckle black_hair blouse blush blushing_at_viewer blushing_female business_attire business_woman highres intern jesterwing leather_belt office_lady office_worker pencil_skirt red_eyes skirt tie tipsy wine wine_glass wolf wolf_girl
anthro_only belt belt_buckle black_hair blouse blush blushing_at_viewer blushing_female business_attire business_woman highres intern jesterwing leather_belt office_lady office_worker pencil_skirt red_eyes skirt tie tipsy wine wine_glass wolf wolf_girl
ambiguous_penetration anthro_only breasts breasts_out collar fucked_from_behind helluva_boss jesterwing kneeling kneeling_down kneeling_female kneeling_position leash leash_and_collar leash_pull leashed leashed_collar loona_(helluva_boss) questionable_consent white_fur white_hair
ambiguous_penetration anthro_only breasts breasts_out collar fucked_from_behind helluva_boss jesterwing kneeling kneeling_down kneeling_female kneeling_position leash leash_and_collar leash_pull leashed leashed_collar loona_(helluva_boss) questionable_consent white_fur white_hair
blonde_hair bra breasts charlie_morningstar_(hazbin_hotel) female hazbin_hotel jesterwing lingerie panties partially_clothed red_eyes side_view solo standing thighs twitter
blonde_hair bra breasts charlie_morningstar_(hazbin_hotel) female hazbin_hotel jesterwing lingerie panties partially_clothed red_eyes side_view solo standing thighs twitter
anthro bra breasts canid canid_demon clothing collar demon eyebrow_piercing eyebrow_ring facial_piercing female fur grey_hair hair hair_over_eye hellhound helluva_boss hi_res inside jesterwing lingerie looking_at_viewer loona_(helluva_boss) lying mammal on_back one_eye_obstructed piercing rain_on_window raining red_eyes ring_piercing solo spiked_collar spikes underwear white_body white_fur window
anthro bra breasts canid canid_demon clothing collar demon eyebrow_piercing eyebrow_ring facial_piercing female fur grey_hair hair hair_over_eye hellhound helluva_boss hi_res inside jesterwing lingerie looking_at_viewer loona_(helluva_boss) lying mammal on_back one_eye_obstructed piercing rain_on_window raining red_eyes ring_piercing solo spiked_collar spikes underwear white_body white_fur window
absurd_res anthro black_clothing black_panties black_underwear bottomless breasts canid canid_demon choker clothed clothing demon dress ear_piercing ear_ring female fur grey_body grey_fur grey_hair grin hair hellhound helluva_boss hi_res holding_clothing holding_object holding_panties holding_underwear inner_ear_fluff jesterwing jewelry looking_at_viewer looking_back looking_back_at_viewer loona_(helluva_boss) mammal necklace no_underwear panties piercing rear_view red_eyes ring_piercing side_boob sign smile solo standing tuft underwear white_body white_fur
absurd_res anthro black_clothing black_panties black_underwear bottomless breasts canid canid_demon choker clothed clothing demon dress ear_piercing ear_ring female fur grey_body grey_fur grey_hair grin hair hellhound helluva_boss hi_res holding_clothing holding_object holding_panties holding_underwear inner_ear_fluff jesterwing jewelry looking_at_viewer looking_back looking_back_at_viewer loona_(helluva_boss) mammal necklace no_underwear panties piercing rear_view red_eyes ring_piercing side_boob sign smile solo standing tuft underwear white_body white_fur
absurd_res anthro avian beak bird bra breasts cheek_tuft chest_tuft clothing crown demon eyelashes female female_only fur glowing glowing_eyes hair helluva_boss hi_res jesterwing mature_anthro mature_female milf owl owl_demon panties pink_sclera solo stella_(helluva_boss) tuft underwear white_eyes white_feathers white_fur
absurd_res anthro avian beak bird bra breasts cheek_tuft chest_tuft clothing crown demon eyelashes female female_only fur glowing glowing_eyes hair helluva_boss hi_res jesterwing mature_anthro mature_female milf owl owl_demon panties pink_sclera solo stella_(helluva_boss) tuft underwear white_eyes white_feathers white_fur
5:6 absurd_res anthro bra canid canid_demon chest_tuft choker clothing demon devil_horns_(gesture) female fur gesture grey_body grey_fur grey_hair hair hellhound helluva_boss hi_res jesterwing jewelry loona_(helluva_boss) mammal necklace red_eyes simple_background smile solo tuft underwear white_body white_fur
5:6 absurd_res anthro bra canid canid_demon chest_tuft choker clothing demon devil_horns_(gesture) female fur gesture grey_body grey_fur grey_hair hair hellhound helluva_boss hi_res jesterwing jewelry loona_(helluva_boss) mammal necklace red_eyes simple_background smile solo tuft underwear white_body white_fur
2023 5_fingers absurd_res anthro avian beak belt bird black_body bottomwear breasts brown_hair clothed clothing demon digital_media_(artwork) eyebrows eyelashes eyeshadow feathered_wings feathers female fingers fishnet_clothing front_view hair headgear headwear helluva_boss hi_res jesterwing long_eyelashes long_hair makeup octavia_(helluva_boss) owl owl_demon red_sclera shorts simple_background solo sparkles standing torn_clothing wings
2023 5_fingers absurd_res anthro avian beak belt bird black_body bottomwear breasts brown_hair clothed clothing demon digital_media_(artwork) eyebrows eyelashes eyeshadow feathered_wings feathers female fingers fishnet_clothing front_view hair headgear headwear helluva_boss hi_res jesterwing long_eyelashes long_hair makeup octavia_(helluva_boss) owl owl_demon red_sclera shorts simple_background solo sparkles standing torn_clothing wings
2022 absurd_res anthro biped black_collar bomb bottomwear breasts canid canid_demon cleavage clothed clothing collar crop_top demon ear_piercing ear_ring english_text explosives eyebrow_piercing eyebrow_ring facial_piercing female flare_(object) fur grey_background hair hellhound helluva_boss hi_res holding_bomb holding_object jesterwing looking_at_viewer loona_(helluva_boss) mammal midriff navel pentagram piercing ring_piercing shirt shorts simple_background solo spiked_collar spikes text topwear underwear white_body white_fur white_hair
2022 absurd_res anthro biped black_collar bomb bottomwear breasts canid canid_demon cleavage clothed clothing collar crop_top demon ear_piercing ear_ring english_text explosives eyebrow_piercing eyebrow_ring facial_piercing female flare_(object) fur grey_background hair hellhound helluva_boss hi_res holding_bomb holding_object jesterwing looking_at_viewer loona_(helluva_boss) mammal midriff navel pentagram piercing ring_piercing shirt shorts simple_background solo spiked_collar spikes text topwear underwear white_body white_fur white_hair
<3_eyes 2023 anthro arm_warmers armwear bedroom_eyes belt black_claws black_clothing black_nose black_topwear bottomwear breasts canid canid_demon chest_tuft choker claws cleavage clothed clothing collarbone countershade_fur countershading crop_top demon denim denim_bottomwear denim_clothing digital_media_(artwork) eyebrow_piercing eyebrow_ring eyelashes eyeshadow facial_piercing female fur grey_body grey_countershading grey_hair hair head_on_hand heart hellhound helluva_boss hi_res inner_ear_fluff jeans jesterwing jewelry looking_at_viewer loona_(helluva_boss) lying makeup mammal midriff narrowed_eyes navel necklace on_side outline panties pants piercing pupils red_outline red_pupils red_sclera ring_piercing seductive shaded shirt simple_background smile solo tail tank_top thigh_gap thong thong_above_pants thong_straps tongue tongue_out topwear torn_bottomwear torn_clothing torn_jeans torn_pants tuft underwear white_body white_eyes white_fur
<3_eyes 2023 anthro arm_warmers armwear bedroom_eyes belt black_claws black_clothing black_nose black_topwear bottomwear breasts canid canid_demon chest_tuft choker claws cleavage clothed clothing collarbone countershade_fur countershading crop_top demon denim denim_bottomwear denim_clothing digital_media_(artwork) eyebrow_piercing eyebrow_ring eyelashes eyeshadow facial_piercing female fur grey_body grey_countershading grey_hair hair head_on_hand heart hellhound helluva_boss hi_res inner_ear_fluff jeans jesterwing jewelry looking_at_viewer loona_(helluva_boss) lying makeup mammal midriff narrowed_eyes navel necklace on_side outline panties pants piercing pupils red_outline red_pupils red_sclera ring_piercing seductive shaded shirt simple_background smile solo tail tank_top thigh_gap thong thong_above_pants thong_straps tongue tongue_out topwear torn_bottomwear torn_clothing torn_jeans torn_pants tuft underwear white_body white_eyes white_fur
2023 absurd_res anthro avian bed bird blush breasts canid canid_demon clothing demon duo eye_contact female female/female furniture hand_on_breast hellhound helluva_boss hi_res jesterwing lesbian looking_at_another loona_(helluva_boss) mammal octavia_(helluva_boss) owl romantic romantic_ambiance smile undressing
2023 absurd_res anthro avian bed bird blush breasts canid canid_demon clothing demon duo eye_contact female female/female furniture hand_on_breast hellhound helluva_boss hi_res jesterwing lesbian looking_at_another loona_(helluva_boss) mammal octavia_(helluva_boss) owl romantic romantic_ambiance smile undressing
2023 absurd_res anthro avian bird bra_strap chest_tuft clothed clothing digital_media_(artwork) female helluva_boss hi_res jesterwing kneeling no_underwear octavia_(helluva_boss) owl owl_demon pantsless shirt shoulder_tuft smile solo topwear tuft
2023 absurd_res anthro avian bird bra_strap chest_tuft clothed clothing digital_media_(artwork) female helluva_boss hi_res jesterwing kneeling no_underwear octavia_(helluva_boss) owl owl_demon pantsless shirt shoulder_tuft smile solo topwear tuft
2024 absurd_res avian bikini bird breasts choker clothing demon digital_media_(artwork) female hair helluva_boss hi_res holding_hair inflatable_ride jesterwing jewelry knee_tuft leg_tuft looking_at_viewer navel necklace octavia_(helluva_boss) owl owl_demon seductive shoulder_tuft solo swimsuit swimwear touching_hair tuft
2024 absurd_res avian bikini bird breasts choker clothing demon digital_media_(artwork) female hair helluva_boss hi_res holding_hair inflatable_ride jesterwing jewelry knee_tuft leg_tuft looking_at_viewer navel necklace octavia_(helluva_boss) owl owl_demon seductive shoulder_tuft solo swimsuit swimwear touching_hair tuft
absurd_res aged_up anthro avian beak bird black_clothing black_hair black_panties black_underwear breasts clothing cosmic_hair dress ethereal_hair eyeshadow feathers female grey_body grey_feathers hair hair_over_eye helluva_boss hi_res jesterwing legwear makeup octavia_(helluva_boss) one_eye_obstructed open_beak open_mouth owl owl_demon panties pole purple_eyeshadow red_clothing red_dress solo stockings tail tail_feathers thigh_highs thong underwear
absurd_res aged_up anthro avian beak bird black_clothing black_hair black_panties black_underwear breasts clothing cosmic_hair dress ethereal_hair eyeshadow feathers female grey_body grey_feathers hair hair_over_eye helluva_boss hi_res jesterwing legwear makeup octavia_(helluva_boss) one_eye_obstructed open_beak open_mouth owl owl_demon panties pole purple_eyeshadow red_clothing red_dress solo stockings tail tail_feathers thigh_highs thong underwear
absurd_res avian beak big_breasts bikini bird bird_demon bodily_fluids breasts cheek_tuft cleavage clothed clothing demon facial_tuft female galliform glowing glowing_eyes helluva_boss hi_res jesterwing looking_at_viewer looking_down looking_down_at_viewer peafowl phasianid smile solo stella_(helluva_boss) sweat swimwear tuft
absurd_res avian beak big_breasts bikini bird bird_demon bodily_fluids breasts cheek_tuft cleavage clothed clothing demon facial_tuft female galliform glowing glowing_eyes helluva_boss hi_res jesterwing looking_at_viewer looking_down looking_down_at_viewer peafowl phasianid smile solo stella_(helluva_boss) sweat swimwear tuft
2022 absurd_res alcohol anthro beach beverage black_nose canid canid_demon canine claws clothing cocktail cocktail_glass container cup demon detailed_background digital_media_(artwork) drinking_glass ear_piercing ear_ring eyebrows eyelashes eyeshadow female finger_claws fur glass glass_container glass_cup grey_body grey_fur hair hellhound helluva_boss hi_res holding_cocktail inner_ear_fluff jesterwing long_hair looking_at_viewer loona_(helluva_boss) makeup mammal multicolored_body multicolored_fur navel night open_mouth outside piercing red_sclera ring_piercing seaside sitting sky solo swimwear tuft two_tone_body two_tone_fur white_body white_fur white_hair
2022 absurd_res alcohol anthro beach beverage black_nose canid canid_demon canine claws clothing cocktail cocktail_glass container cup demon detailed_background digital_media_(artwork) drinking_glass ear_piercing ear_ring eyebrows eyelashes eyeshadow female finger_claws fur glass glass_container glass_cup grey_body grey_fur hair hellhound helluva_boss hi_res holding_cocktail inner_ear_fluff jesterwing long_hair looking_at_viewer loona_(helluva_boss) makeup mammal multicolored_body multicolored_fur navel night open_mouth outside piercing red_sclera ring_piercing seaside sitting sky solo swimwear tuft two_tone_body two_tone_fur white_body white_fur white_hair
2022 accessory anthro black_nose bra breasts canid canid_demon canine cheek_tuft clothed clothing demon digital_media_(artwork) eyebrows eyelashes eyeshadow facial_tuft female flower flower_in_hair fluffy fluffy_tail fur grey_body grey_fur grey_hair hair hair_accessory hellhound helluva_boss hi_res holding_clothing holding_object jesterwing long_hair looking_at_viewer loona_(helluva_boss) makeup mammal multicolored_body multicolored_fur notched_ear panties partially_clothed plant pupils purple_theme red_clothing red_sclera red_underwear side_view simple_background slit_pupils solo standing tail tuft two_tone_body two_tone_fur underwear white_body white_fur
2022 accessory anthro black_nose bra breasts canid canid_demon canine cheek_tuft clothed clothing demon digital_media_(artwork) eyebrows eyelashes eyeshadow facial_tuft female flower flower_in_hair fluffy fluffy_tail fur grey_body grey_fur grey_hair hair hair_accessory hellhound helluva_boss hi_res holding_clothing holding_object jesterwing long_hair looking_at_viewer loona_(helluva_boss) makeup mammal multicolored_body multicolored_fur notched_ear panties partially_clothed plant pupils purple_theme red_clothing red_sclera red_underwear side_view simple_background slit_pupils solo standing tail tuft two_tone_body two_tone_fur underwear white_body white_fur
absurd_res ankle_tuft anthro bedroom_eyes big_breasts black_choker black_claws black_jewelry black_necklace black_pupils bra breasts canid canid_demon canine canis cheek_tuft chest_tuft choker clawed_fingers claws clothed clothing condom countershading demon ear_piercing ear_ring eyelashes facial_tuft female fur garter_belt garter_straps grey_body grey_fur hair heart hellhound helluva_boss hi_res jesterwing jewelry kneeling leg_tuft legwear lingerie long_hair loona_(helluva_boss) mammal narrowed_eyes necklace off_shoulder panties piercing pupils red_sclera ring_piercing seductive sexual_barrier_device shoulder_tuft solo stockings toe_claws tuft underwear unused_condom white_body white_countershading white_eyes white_fur wolf wrapped_condom
absurd_res ankle_tuft anthro bedroom_eyes big_breasts black_choker black_claws black_jewelry black_necklace black_pupils bra breasts canid canid_demon canine canis cheek_tuft chest_tuft choker clawed_fingers claws clothed clothing condom countershading demon ear_piercing ear_ring eyelashes facial_tuft female fur garter_belt garter_straps grey_body grey_fur hair heart hellhound helluva_boss hi_res jesterwing jewelry kneeling leg_tuft legwear lingerie long_hair loona_(helluva_boss) mammal narrowed_eyes necklace off_shoulder panties piercing pupils red_sclera ring_piercing seductive sexual_barrier_device shoulder_tuft solo stockings toe_claws tuft underwear unused_condom white_body white_countershading white_eyes white_fur wolf wrapped_condom
1:1 2021 anthro avian black_hair blep canid canid_demon clothed clothing collar demon duo eye_contact female female/female freckles fur hair hellhound helluva_boss hi_res inside jesterwing looking_at_another loona_(helluva_boss) lying mammal octavia_(helluva_boss) off_shoulder on_back red_sclera spiked_collar spikes tongue tongue_out white_body white_eyes white_fur
1:1 2021 anthro avian black_hair blep canid canid_demon clothed clothing collar demon duo eye_contact female female/female freckles fur hair hellhound helluva_boss hi_res inside jesterwing looking_at_another loona_(helluva_boss) lying mammal octavia_(helluva_boss) off_shoulder on_back red_sclera spiked_collar spikes tongue tongue_out white_body white_eyes white_fur
2023 absurd_res anthro avian beak bikini bird black_body breasts clothed clothing demon digital_media_(artwork) eyebrows eyelashes eyeshadow feathered_wings feathers female hair helluva_boss hi_res jesterwing long_eyelashes long_hair looking_at_viewer looking_back makeup octavia_(helluva_boss) open_beak open_mouth owl owl_demon partially_clothed pink_sclera purple_theme rear_view simple_background solo string_bikini swimwear wings
2023 absurd_res anthro avian beak bikini bird black_body breasts clothed clothing demon digital_media_(artwork) eyebrows eyelashes eyeshadow feathered_wings feathers female hair helluva_boss hi_res jesterwing long_eyelashes long_hair looking_at_viewer looking_back makeup octavia_(helluva_boss) open_beak open_mouth owl owl_demon partially_clothed pink_sclera purple_theme rear_view simple_background solo string_bikini swimwear wings