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helluva boss

after_sex after_vaginal ahe_gao anus arm_up bare_shoulders black_gloves black_hair black_horns breasts colored_sclera colored_skin completely_nude cum cum_in_pussy demon_girl demon_horns demon_tail fangs female fingerless_gloves gloves grass gun helluva_boss highres holding holding_gun holding_weapon horns large_breasts looking_at_viewer lying meesh_(mushymeesh) millie_(helluva_boss) navel nipple_piercing nude on_back piercing pussy red_skin short_hair solo spread_legs striped_horns tail teeth watermark weapon web_address yellow_sclera
after_sex after_vaginal ahe_gao anus arm_up bare_shoulders black_gloves black_hair black_horns breasts colored_sclera colored_skin completely_nude cum cum_in_pussy demon_girl demon_horns demon_tail fangs female fingerless_gloves gloves grass gun helluva_boss highres holding holding_gun holding_weapon horns large_breasts looking_at_viewer lying meesh_(mushymeesh) millie_(helluva_boss) navel nipple_piercing nude on_back piercing pussy red_skin short_hair solo spread_legs striped_horns tail teeth watermark weapon web_address yellow_sclera
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anus arm_up bare_shoulders biting_own_lip black_gloves black_hair black_horns breasts colored_sclera colored_skin completely_nude demon_girl demon_horns demon_tail female fingerless_gloves gloves grass gun helluva_boss highres holding holding_gun holding_weapon horns large_breasts looking_at_viewer lying meesh_(mushymeesh) millie_(helluva_boss) navel nipple_piercing nude oerba_yun_fang on_back piercing pussy red_skin short_hair solo spread_legs striped_horns tail teeth watermark weapon web_address yellow_sclera
arm_up bare_shoulders biting_own_lip black_gloves black_hair black_horns black_panties breasts colored_sclera colored_skin demon_girl demon_horns demon_tail female fingerless_gloves gloves grass gun heart heart_print helluva_boss highres holding holding_gun holding_weapon horns large_breasts looking_at_viewer lying meesh_(mushymeesh) millie_(helluva_boss) navel nipple_piercing nipples oerba_yun_fang on_back panties piercing red_skin short_hair solo spread_legs striped_horns tail teeth topless torn_clothes torn_panties underwear watermark weapon web_address yellow_sclera
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ai_generated beach duo fingering_partner french_kiss french_kissing furry furry_only headletzer helluva_boss lola_bunny loona_(helluva_boss) nude tagme
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ai_generated beach duo fingering_partner furry furry_only headletzer helluva_boss kissing lola_bunny loona_(helluva_boss) swimsuit tagme
2girls absurd_res anthro anthrofied ass bent_over black_body black_fur breast_press breast_squeeze breast_to_breast breasts busty canid canid_demon canine choker collar cum cum_in_pussy cum_inside curvaceous curvy curvy_figure dialogue digital_media_(artwork) duo elzorrogomita english_text eyebrows eyelashes female female/female female_focus female_only foxgumie fur furry glistening glistening_body helluva_boss hi_res hourglass_figure looking_at_another loona_(helluva_boss) magma_cube mammal mature_female minecraft mojang motion_lines penetration penis penis_in_pussy queen_bee-lzebub_(helluva_boss) red_eyes tagme tentacle tentacle_sex text thick_thighs video_games voluptuous voluptuous_female white_body white_fur wide_hips wolf xbox_game_studios yellow_eyes yuri
2girls absurd_res anthro anthrofied ass bent_over black_body black_fur breast_press breast_squeeze breast_to_breast breasts busty canid canid_demon canine choker collar cum cum_in_pussy cum_inside curvaceous curvy curvy_figure dialogue digital_media_(artwork) duo elzorrogomita english_text eyebrows eyelashes female female/female female_focus female_only foxgumie fur furry glistening glistening_body helluva_boss hi_res hourglass_figure looking_at_another loona_(helluva_boss) magma_cube mammal mature_female minecraft mojang motion_lines penetration penis penis_in_pussy queen_bee-lzebub_(helluva_boss) red_eyes tagme tentacle tentacle_sex text thick_thighs video_games voluptuous voluptuous_female white_body white_fur wide_hips wolf xbox_game_studios yellow_eyes yuri
animal_genitalia animal_penis anthro balls big_balls big_breasts big_penis blonde_hair blush bodily_fluids breasts cheating_wife claws demon dialogue dragon equine_genitalia equine_penis erection faceless_character faceless_male fat_man female female_on_anthro genital_fluids genital_piercing genitals gothstoat green_body green_hair group hair hazbin_hotel helluva_boss hi_res horsecock humanoid imminent_sex infidelity interspecies kiss_mark knot licking lilith_morningstar_(hazbin_hotel) looking_pleasured makeup male male/female mammon_(helluva_boss) mascara mascara_tears mature_female multicolored_body muscular muscular_male mythological_creature mythological_scalie mythology nipple_piercing nipples nude open_mouth oral overweight overweight_male penile penis penis_lick penis_piercing piercing precum pubes pussy red_body saliva satan_(helluva_boss) scalie sex speech_bubble tail teeth thick_thighs tongue tongue_out trio two_tone_body ugly_bastard ugly_man vaginal_fluids vein veiny_penis yellow_body
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2024 4_eyes 9:16 abs anthro biceps demon dragon genitals helluva_boss hi_res horn humanoid_genitalia humanoid_penis looking_at_viewer male morinetsu multi_eye muscular muscular_anthro muscular_male muscular_thighs mythological_creature mythological_scalie mythology nipples nude pecs penis red_body satan_(helluva_boss) scalie simple_background solo speech_bubble tail triceps vein veiny_penis wings
anal anal_sex angel_dust animal_humanoid arachnid arachnid_humanoid arthropod arthropod_humanoid bodily_fluids dialogue dracreloaded duo english_text erection exclamation_point fur genitals hazbin_hotel helluva_boss hi_res humanoid humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid imp male male/male male_penetrated male_penetrating male_penetrating_male moxxie_(helluva_boss) open_mouth penetration penile penile_penetration penile_spines penis pink_body pink_eyes pink_fur red_body sex simple_background spider_humanoid sweat teeth text url
anal anal_sex angel_dust animal_humanoid arachnid arachnid_humanoid arthropod arthropod_humanoid bodily_fluids dialogue dracreloaded duo english_text erection exclamation_point fur genitals hazbin_hotel helluva_boss hi_res humanoid humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid imp male male/male male_penetrated male_penetrating male_penetrating_male moxxie_(helluva_boss) open_mouth penetration penile penile_penetration penile_spines penis pink_body pink_eyes pink_fur red_body sex simple_background spider_humanoid sweat teeth text url
animal_genitalia animal_pussy anthro canid canid_demon canine canine_genitalia canine_pussy demon female genitals hellhound helluva_boss hi_res loona_(helluva_boss) mammal msc_cat mythological_canine mythological_creature mythology pussy solo
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2024 2boys 3d 3d_animation 4k anal anal_orgasm anal_sex animated anus ass ass_up balls bdanimare bed bedroom bent_over big_ass big_balls big_penis bodily_fluids bouncing_balls bouncing_penis clothing collaboration cum cum_in_ass cum_inside cum_while_penetrated dark_anus digital_media_(artwork) digitigrade disembodied_penis duo ejaculation fist freckles from_behind_position functionally_nude furniture gay genital_fluids genitals hair hands-free head_tuft helluva_boss hi_res high_framerate horn horns huge_balls huge_cock huge_filesize human humanoid imp latex latex_clothing latex_legwear latex_thighhighs latex_topwear legwear long_playtime looking_pleasured lying male male/male male_focus male_only male_penetrated mammal moxxie_(helluva_boss) moxxie_(valorlynz) on_bed on_front open_mouth penetration penis platform_standing_doggystyle pupils red_body red_skin running_makeup running_mascara setrixart sex shaking sharp_teeth shivering skimpy slit_pupils spade_tail standing_doggystyle striped_horn stripes sweat sweaty_ass sweaty_balls sweaty_genitalia tagme tail tail_motion teeth thighhighs tongue tongue_out tophat_turtle topwear tuft video voice_acted white_hair yaoi yellow_eyes
aged_down big_ass black_markings blitzo_(helluva_boss) blush body_fluids crown cumming_from_rimjob dark_blue_body demon_boy demon_horns desperate dirty_talk fat_ass feet_up gay hand_on_butt hands_behind_head helluva_boss holding_ass imp_horns japansadface legs_apart male male_cub male_only red_eyes red_skin rimjob rimming_male royalty spit_string steaming_body stolas_(helluva_boss) sweaty_body sweaty_butt tears_in_eyes text tongue_out two_males wet_anus wet_tongue yellow_eyes yellow_teeth younger_male
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anthro black_body black_ears black_fur black_lips black_nose black_tail breasts canid canid_demon canine demon ear_piercing ear_ring eyebrows female fur grey_body grey_fur grey_hair hair hands_behind_head hellhound helluva_boss hi_res light_hair lips loona_(helluva_boss) mammal multicolored_body multicolored_fur multicolored_tail mythological_canine mythological_creature mythology piercing pose red_sclera ring_piercing solo tail teeth two_tone_body two_tone_fur white_body white_fur white_tail zodiacsc
anthro black_body black_ears black_fur black_lips black_nose black_tail breasts canid canid_demon canine demon ear_piercing ear_ring eyebrows female fur grey_body grey_fur grey_hair hair hands_behind_head hellhound helluva_boss hi_res light_hair lips loona_(helluva_boss) mammal multicolored_body multicolored_fur multicolored_tail mythological_canine mythological_creature mythology piercing pose red_sclera ring_piercing solo tail teeth two_tone_body two_tone_fur white_body white_fur white_tail zodiacsc
2023 absurd_res anthro big_breasts breasts canid canid_demon canine crossover crossover_ship demon digital_drawing_(artwork) digital_media_(artwork) duo female female/female five_nights_at_freddy's five_nights_at_freddy's:_security_breach hellhound helluva_boss hi_res looking_at_viewer loona_(helluva_boss) mammal marcsello mythological_canine mythological_creature mythology nude patreon roxanne_wolf_(fnaf) scottgames simple_background steel_wool_studios subscribestar
2023 absurd_res anthro big_breasts breasts canid canid_demon canine crossover crossover_ship demon digital_drawing_(artwork) digital_media_(artwork) duo female female/female five_nights_at_freddy's five_nights_at_freddy's:_security_breach hellhound helluva_boss hi_res looking_at_viewer loona_(helluva_boss) mammal marcsello mythological_canine mythological_creature mythology nude patreon roxanne_wolf_(fnaf) scottgames simple_background steel_wool_studios subscribestar
absurd_res ass blood bodily_fluids buckteeth choker clothed clothing demon demon_humanoid english_text female grey_background grin helluva_boss hi_res humanoid imp jewelry knife legwear looking_at_viewer millie_(helluva_boss) necklace nipple_piercing nipples piercing rear_view simple_background smile solo spade_tail tail teeth text thigh_highs thong topless underwear zr_furious
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2023 2:3 alcohol anthro beer beer_mug beverage big_breasts black_lipstick blush breasts canid canid_demon canine cleavage clothed clothing collar demon dress ear_piercing ear_ring eyebrow_piercing eyebrow_ring facial_piercing female fur grey_body grey_fur hellhound helluva_boss hi_res lipstick loona_(helluva_boss) makeup mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology panties piercing ring_piercing smoking solo spiked_collar spikes turtlessoul underwear white_body white_fur
2023 2:3 alcohol anthro beer beer_mug beverage big_breasts black_lipstick blush breasts canid canid_demon canine cleavage clothed clothing collar demon dress ear_piercing ear_ring eyebrow_piercing eyebrow_ring facial_piercing female fur grey_body grey_fur hellhound helluva_boss hi_res lipstick loona_(helluva_boss) makeup mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology panties piercing ring_piercing smoking solo spiked_collar spikes turtlessoul underwear white_body white_fur
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absurd_res anthro arthropod bee belly big_belly big_breasts black_body black_fur black_nipples black_nose blue_hair bottomwear breast_grab breasts canid canid_demon canine claws clothed clothing colored demon detailed_background eyebrows eyelashes eyeliner eyeshadow female fishnet_clothing food food_fetish food_play fur hair half_clothed hand_on_breast hellhound helluva_boss hi_res honey_(food) honeycomb huge_breasts hybrid hymenopteran insect_wings insects licking licking_lips lionberrymochi lips looking_at_viewer makeup mammal mythological_canine mythological_creature mythology narrowed_eyes nipples obese obese_anthro obese_female overweight overweight_anthro overweight_female partially_clothed public public_exposure public_nudity queen_bee-lzebub_(helluva_boss) red_hair sharp_teeth smile solo teeth thick_lips thick_thighs tongue tongue_out topwear white_body white_fur wide_hips wings yellow_body yellow_fur
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2022 anthro ass bakufu canid canid_demon canine clothing demon digital_media_(artwork) ear_piercing ear_ring eyebrows female fingers hair hellhound helluva_boss hi_res holding_object kneeling legwear long_hair loona_(helluva_boss) mammal mythological_canine mythological_creature mythology piercing red_sclera ring_piercing simple_background solo
2022 anthro ass bakufu canid canid_demon canine clothing demon digital_media_(artwork) ear_piercing ear_ring eyebrows female fingers hair hellhound helluva_boss hi_res holding_object kneeling legwear long_hair loona_(helluva_boss) mammal mythological_canine mythological_creature mythology piercing red_sclera ring_piercing simple_background solo
2022 anthro ass bakufu breasts canid canid_demon canine demon digital_media_(artwork) ear_piercing ear_ring eyebrows female fingers hair hellhound helluva_boss hi_res holding_object kneeling long_hair loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nude piercing red_sclera ring_piercing simple_background solo
2022 anthro ass bakufu breasts canid canid_demon canine demon digital_media_(artwork) ear_piercing ear_ring eyebrows female fingers hair hellhound helluva_boss hi_res holding_object kneeling long_hair loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nude piercing red_sclera ring_piercing simple_background solo
1boy 1girls age_difference animated anthro balls big_penis blitzo_(helluva_boss) cub cum cum_in_pussy cum_inside delete_this delete_this_shit demon duo female fleshlight_position fucktoy furry hellhound helluva_boss horn loona_(helluva_boss) male older_male penetration penis sex sound stepfather_and_stepdaughter t.f.a.n.c.s. uncensored vaginal_penetration video young younger_anthro younger_female
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2025 2d_animation all_fours animal_dildo animal_sex_toy animated anthro anus ass black_body black_fur blush bodily_fluids canid canid_demon canine canine_dildo dakkomako demon dildo dildo_in_pussy dildo_insertion female fur genital_fluids genitals grey_body grey_fur hellhound helluva_boss knotted_dildo looking_back loona_(helluva_boss) mammal masturbation multicolored_body multicolored_fur mythological_canine mythological_creature mythology nude penetration pussy sex_toy sex_toy_in_pussy sex_toy_insertion short_playtime solo tongue tongue_out vaginal_fluids vaginal_masturbation vaginal_penetration white_body white_fur
2025 2d_animation all_fours animal_dildo animal_sex_toy animated anthro anus ass black_body black_fur blush bodily_fluids canid canid_demon canine canine_dildo dakkomako demon dildo dildo_in_pussy dildo_insertion female fur genital_fluids genitals grey_body grey_fur hellhound helluva_boss knotted_dildo looking_back loona_(helluva_boss) mammal masturbation multicolored_body multicolored_fur mythological_canine mythological_creature mythology nude penetration pussy sex_toy sex_toy_in_pussy sex_toy_insertion short_playtime solo tongue tongue_out vaginal_fluids vaginal_masturbation vaginal_penetration white_body white_fur
1:1 animated anthro anuminati canid canid_demon canine demon feet female foot_fetish foot_play footjob hellhound helluva_boss loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology sex short_playtime unfinished
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2_heads anthro big_breasts blue_body blue_hair boss) breasts claws conjoined demon demon_humanoid green_eyes helluva_boss leviathan_(helluva multi_head multicolored_body prostochel40 prostochel40_(artist) smug_face two_tone_body
big_dick black_clothing black_hair clothed helluva_boss horned_humanoid long_eyelashes male/female millie_(helluva_boss) prostochel40 prostochel40_(artist) red_body tattoo veins veiny_penis yellow_eyes
big_dick black_clothing black_hair clothed helluva_boss horned_humanoid long_eyelashes male/female millie_(helluva_boss) prostochel40 prostochel40_(artist) red_body tattoo veins veiny_penis yellow_eyes
1boy 1girls big_ass big_butt big_penis bird butler cheating cheating_wife comcic comic demon dominant dominant_female feather_hair feather_pubes feathers femdom fluffy_rob helluva_boss imp long_eyelashes red_skin robe robe_only shorter_male spiralart stella_(helluva_boss) striped_horn submissive submissive_male tagme taller_girl white_hair
1boy 1girls big_ass big_butt big_penis bird butler cheating cheating_wife comcic comic demon dominant dominant_female feather_hair feather_pubes feathers femdom fluffy_rob helluva_boss imp long_eyelashes red_skin robe robe_only shorter_male spiralart stella_(helluva_boss) striped_horn submissive submissive_male tagme taller_girl white_hair
16:9 3d anal anal_sex anthro balls bandai_namco being_watched big_breasts big_penis breasts canid canid_demon canine crossover demon dialogue digimon digimon_(species) digital_media_(artwork) dildo dildo_in_pussy dildo_insertion english_text female ftg_crossgender fti_crossgender genitals group gynomorph gynomorph/male gynomorph_penetrating gynomorph_penetrating_male handjob hellhound helluva_boss hi_res humanoid_genitalia humanoid_penis intersex intersex/male intersex_penetrating intersex_penetrating_male looking_at_another loona_(helluva_boss) male male_penetrated mammal masturbation mythological_canine mythological_creature mythology nintendo nipples nude penetration penile penile_penetration penis penis_in_ass pokemon pussy recording renamon sex sex_toy sex_toy_in_pussy sex_toy_insertion sourcebumbiscuit stomach_bulge text trio vaginal_masturbation vaginal_penetration voyeur warfare_renamon widescreen
16:9 3d anal anal_sex anthro balls bandai_namco being_watched big_breasts big_penis breasts canid canid_demon canine crossover demon dialogue digimon digimon_(species) digital_media_(artwork) dildo dildo_in_pussy dildo_insertion english_text female ftg_crossgender fti_crossgender genitals group gynomorph gynomorph/male gynomorph_penetrating gynomorph_penetrating_male handjob hellhound helluva_boss hi_res humanoid_genitalia humanoid_penis intersex intersex/male intersex_penetrating intersex_penetrating_male looking_at_another loona_(helluva_boss) male male_penetrated mammal masturbation mythological_canine mythological_creature mythology nintendo nipples nude penetration penile penile_penetration penis penis_in_ass pokemon pussy recording renamon sex sex_toy sex_toy_in_pussy sex_toy_insertion sourcebumbiscuit stomach_bulge text trio vaginal_masturbation vaginal_penetration voyeur warfare_renamon widescreen
asmodeus'_assistant ass bed bedroom big_butt bodily_fluids bra cafe-grimful clothing demon eyewear female freckles furniture giddy_(helluva_boss) glasses hair hell helluva_boss hi_res horn huge_butt humanoid membrane_(anatomy) membranous_wings panties pink_body pink_hair pointy_ears solo steam steamy_butt sweat sweatdrop sweaty_butt tail thick_thighs underwear wide_hips wings yellow_eyes
asmodeus'_assistant ass bed bedroom big_butt bodily_fluids bra cafe-grimful clothing demon eyewear female freckles furniture giddy_(helluva_boss) glasses hair hell helluva_boss hi_res horn huge_butt humanoid membrane_(anatomy) membranous_wings panties pink_body pink_hair pointy_ears solo steam steamy_butt sweat sweatdrop sweaty_butt tail thick_thighs underwear wide_hips wings yellow_eyes
aquamarine_(steven_universe) blue-skinned_female cartoon_network cum_in_pussy futa_on_female futanari helluva_boss large_ass large_breasts large_penis lifting_person millie_(helluva_boss) shortstack standing_sex steven_universe theslashfive vivienne_medrano vivziepop
aquamarine_(steven_universe) blue-skinned_female cartoon_network cum_in_pussy futa_on_female futanari helluva_boss large_ass large_breasts large_penis lifting_person millie_(helluva_boss) shortstack standing_sex steven_universe theslashfive vivienne_medrano vivziepop
ahe_gao cropped_image drooling helluva_boss japansadface needs_tags stolas_(helluva_boss) tagme young
ahe_gao cropped_image drooling helluva_boss japansadface needs_tags stolas_(helluva_boss) tagme young
absurd_res anthro big_breasts bondage breasts clothing collar darkadibuja female genitals grey_hair hair helluva_boss hi_res huge_breasts legwear loona_(helluva_boss) petplay pussy red_eyes roleplay solo stockings white_body ych_(character)
absurd_res anthro big_breasts bondage breasts clothing collar darkadibuja female genitals grey_hair hair helluva_boss hi_res huge_breasts legwear loona_(helluva_boss) petplay pussy red_eyes roleplay solo stockings white_body ych_(character)
anthro anus aroused ass bed belphegor_(helluva_boss) bodily_fluids bovid candle caprine clitoris cum cum_on_butt female furniture genital_fluids genitals goat helluva_boss hi_res hooves humanoid lying mammal on_bed on_side pilosan pussy pussy_juice_string seven_deadly_sins sloth solo tired toxis vaginal_fluids xenarthran
anthro anus aroused ass bed belphegor_(helluva_boss) bodily_fluids bovid candle caprine clitoris cum cum_on_butt female furniture genital_fluids genitals goat helluva_boss hi_res hooves humanoid lying mammal on_bed on_side pilosan pussy pussy_juice_string seven_deadly_sins sloth solo tired toxis vaginal_fluids xenarthran
5_fingers areola breasts demon deskmaniac digital_media_(artwork) fellatio female female_penetrated fingers genitals hair helluva_boss hi_res horn humanoid imp mammal milky_(helluva_boss) nipples not_furry nude oral oral_penetration penetration penile pussy restrained restrained_by_tentacles sex simple_background solo spade_tail spread_legs spreading tail tentacle tentacle_in_mouth tentacle_penetration tentacle_sex vaginal_penetration vaginal_penetration
5_fingers areola breasts demon deskmaniac digital_media_(artwork) fellatio female female_penetrated fingers genitals hair helluva_boss hi_res horn humanoid imp mammal milky_(helluva_boss) nipples not_furry nude oral oral_penetration penetration penile pussy restrained restrained_by_tentacles sex simple_background solo spade_tail spread_legs spreading tail tentacle tentacle_in_mouth tentacle_penetration tentacle_sex vaginal_penetration vaginal_penetration