1:1 2021 asmodeus_(helluva_boss) clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie empty_eyes eyes_closed fizzarolli_(helluva_boss) group happy hat headgear headwear hellaverse helluva_boss hi_res humanoid imp larger_male male mammon_(helluva_boss) open_mouth prosthetic red_body red_skin simple_background size_difference smaller_male teeth top_hat trio
2021 asmodeus_(helluva_boss) backless_clothing backless_dress balls blue_bottomwear blue_clothing blue_dress blue_pants bottomwear clothed clothing crossdressing demon dialogue digital_drawing_(artwork) digital_media_(artwork) dontbeazombie dress duo english_text fizzarolli_(helluva_boss) footwear genitals green_eyes green_penis hand_on_hip hellaverse helluva_boss high_heels humanoid imp larger_male male pants penis pink_clothing pink_dress purple_background shoes sideless_clothing sideless_dress simple_background size_difference smaller_male strapless_clothing strapless_dress text
2022 asmodeus_(helluva_boss) blue_body demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) hand_on_face heart_symbol hellaverse helluva_boss hi_res humanoid imp jester kiss_on_lips kissing male male/male prosthetic red_body red_skin simple_background sweetpupperoo tail tail_motion
2022 asmodeus_(helluva_boss) blue_body chest_tuft demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text fizzarolli_(helluva_boss) hand_on_chest heart_symbol hellaverse helluva_boss male nipples sweetpupperoo text tuft
2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear boots boxers_(clothing) clothing demon digital_media_(artwork) duo emburne fizzarolli_(helluva_boss) footwear green_eyes hat headgear headwear hellaverse helluva_boss humanoid imp jester larger_male male mirror red_body red_skin shoes simple_background size_difference sketch smaller_male top_hat underwear
2021 arm_around_neck asmodeus_(helluva_boss) black_clothing black_hat black_headwear clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) hat headgear headwear hellaverse helluva_boss hi_res humanoid jester karmindey male simple_background smile teeth top_hat yellow_eyes
2022 black_bottomwear black_clothing black_pants bottomwear clothing collar demon digital_drawing_(artwork) digital_media_(artwork) eggplant fizzarolli_(helluva_boss) food fruit hellaverse helluva_boss hi_res humanoid imp jester looking_at_viewer male midriff pants pink_clothing plant red_background red_body red_skin simple_background solo sweetpupperoo teeth
2022 3:4 asmodeus_(helluva_boss) clothing demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie duo fizzarolli_(helluva_boss) food fruit green_eyes hand_on_belly hellaverse helluva_boss hi_res humanoid imp male open_mouth pillow plant pregnant pregnant_male robe simple_background strawberry translucent translucent_clothing translucent_robe
2022 asmodeus_(helluva_boss) blue_body bodily_fluids demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie duo female fizzarolli_(helluva_boss) green_tongue grey_background hellaverse helluva_boss humanoid imp lactating male male/female male_lactation moobs nipples pregnant pregnant_male prosthetic simple_background tongue white_body
4_missing_limbs absurd_res amputee asmodeus_(helluva_boss) balls bound butt censored chain chained demon disability duo erection femboy fizzarolli_(helluva_boss) flaccid genitals hellaverse helluva_boss hi_res humanoid imp male male/male mosaic_censorship penis quadruple_amputee size_difference size_play stump_cap stump_socket sugata1616 suspension
butt currency_symbol demon dollar_sign duo electronics ellipsis english_text erection fizzarolli_(helluva_boss) genitals hellaverse helluva_boss hi_res humanoid imp looking_at_object looking_at_phone machine male penetrable_sex_toy penis phone robo_fizzarolli robot sex_toy sugata1616 symbol text
asmodeus_(helluva_boss) censored demon erection fellatio fizzarolli_(helluva_boss) genitals handjob hellaverse helluva_boss hi_res humanoid humanoid_genitalia humanoid_penis imp japanese_text larger_male male male/male mosaic_censorship oral penile penis sex size_difference size_play smaller_male sugata1616 text translation_request
asmodeus_(helluva_boss) dancing demon duo fizzarolli_(helluva_boss) hellaverse helluva_boss hi_res imp instagram male muscular muscular_male nipples pecs pole pole_dancing size_difference sugata1616
2021 asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_top_hat clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fauzer fizzarolli_(helluva_boss) hat hat_feather headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid imp loose_feather male open_mouth teeth top_hat yellow_eyes
anthro blitzo_(helluva_boss) cariaguilar98 demon duo fizzarolli_(helluva_boss) hell hellaverse helluva_boss hi_res imp male male/male scared
5:6 5_fingers absurd_res anthro avian balls beanie bird black_nipples bodily_fluids breast_grab breasts clothing crying duo erection female fingers fizzarolli_(helluva_boss) forced genitals grey_body grin hand_on_breast hat headgear headwear hellaverse helluva_boss hi_res imp male male/female nipples octavia_(helluva_boss) on_model on_style owl owl_demon penetration penis pink_eyes pink_sclera rape red_balls red_penis sex smile spiralart tears torn_clothing vaginal vaginal_penetration white_eyes yellow_sclera
5:6 5_fingers absurd_res anthro avian balls bird black_nipples bodily_fluids breast_grab breasts clothed clothed/nude clothed_male clothing crying duo entangled erection female fingers fizzarolli_(helluva_boss) forced genitals grey_body hand_on_breast hellaverse helluva_boss hi_res imp male male/female nipples nude octavia_(helluva_boss) on_model on_style owl owl_demon penetration penis pink_eyes pink_sclera rape red_balls red_penis sex spiralart tears vaginal vaginal_penetration white_eyes yellow_sclera
1:1 absurd_res big_butt blush bubble_butt butt clothing demon fizzarolli_(helluva_boss) headgear headwear hellaverse helluva_boss hi_res huge_butt hyper hyper_butt imp jester looking_at_viewer looking_back male multicolored_body nude open_mouth schplingnops sharp_teeth simple_background smile solo teeth thick_thighs wide_hips
anthro avian balloon balloon_animal bird blitzo_(helluva_boss) book brown_body brown_fur cash_buckzo child clothing crown curtains detailed_background dress eyelashes female fizzarolli_(helluva_boss) formal_clothing formal_wear frown fur grey_body grey_fur group hair hat headgear headwear hellaverse helluva_boss hi_res holding_balloon holding_object horn imp inflatable lamp long_eyelashes long_hair looking_back magic magic_user makeup male mascara modelling_balloon offscreen_character owl owl_demon paimon_(helluva_boss) pink_eyes powers ramonyyytv red_eyes running_makeup running_mascara sad shaped_balloon short_hair smile stella_(helluva_boss) stolas_(helluva_boss) top_hat white_body white_fur window yellow_eyes young
4_fingers anthro arm_tuft avian beak bird blue_body blue_feathers chest_tuft clothing crossgender crunkerton demon detailed_background feather_tuft feathers female fingers fizzarolli_(helluva_boss) genitals hellaverse helluva_boss hi_res imp male mature_female multi_eye nipples open_mouth open_smile owl owl_demon shoulder_tuft smile solo spread_vulva spreading stolas_(helluva_boss) thick_thighs tongue tuft vulva
16:9 adopted_(lore) adopted_daughter_(lore) adoptive_father_(lore) animated animation_meme anthro bathtub blitzo_(helluva_boss) candle canid canid_demon canine cemetery chair clothed clothing dancing daughter_(lore) demon english_audio father_(lore) father_and_child_(lore) father_and_daughter_(lore) female fizzarolli_(helluva_boss) funeral furniture hell hellaverse hellhound helluva_boss hi_res holding_object holding_weapon imp knife long_playtime loona_(helluva_boss) magazine male mammal meme millie_(helluva_boss) moxxie_(helluva_boss) music music_video mythological_canine mythological_creature mythology neoni_(musician) occult_symbol octavia_(helluva_boss) office parent_(lore) parent_and_child_(lore) parent_and_daughter_(lore) pentagram rocky_rakoon satanic sega singing sofa solo sonic_the_hedgehog sonic_the_hedgehog_(series) sound sound_warning stepdaughter_(lore) stepfather_(lore) stepfather_and_stepchild_(lore) stepfather_and_stepdaughter_(lore) stepparent_(lore) stepparent_and_stepchild_(lore) stepparent_and_stepdaughter_(lore) stolas_(helluva_boss) striker_(helluva_boss) symbol throne throne_room tombstone verosika_mayday video vortex_(helluva_boss) weapon widescreen
2023 asmodeus_(helluva_boss) black_clothing black_hat black_headwear chest_tuft clothing demon digital_media_(artwork) duo fizzarolli_(helluva_boss) hat headgear headwear hellaverse helluva_boss hoodie humanoid male purple_body teeth top_hat topwear traditional_media_(artwork) tuft white_eyes zjealy
2023 3:4 angry anthro asmodeus_(helluva_boss) avian bird black_clothing black_hat black_headwear blitzo_(helluva_boss) blue_body blue_clothing blue_feathers chest_tuft cloak clothing demon digital_drawing_(artwork) digital_media_(artwork) feathers fizzarolli_(helluva_boss) green_eyes green_sclera group hat headgear headwear hellaverse helluva_boss hi_res horn humanoid imp jester larger_male male open_mouth owl owl_demon red_body red_clothing red_eyes red_skin size_difference smaller_male stolas_(helluva_boss) stuffoflegend96 teeth top_hat tuft white_body white_skin yellow_sclera
1:1 2023 asmodeus_(helluva_boss) cake cherry clothed clothing crossdressing demon dessert detailed_background digital_drawing_(artwork) digital_media_(artwork) dress duo fizzarolli_(helluva_boss) flower food fruit furniture green_eyes hat hat_feather headgear headwear hellaverse helluva_boss humanoid imp loose_feather lucifervalenti7 lying male on_side plant red_clothing rose_(flower) yellow_sclera
2023 absurd_res asmodeus_(helluva_boss) bathing bubble clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) headgear headwear hellaverse helluva_boss hi_res humanoid imp male restricted_palette signature steam tuft white_eyes zjealy
5:6 5_fingers absurd_res anthro avian balls bird black_nipples bodily_fluids breast_grab breasts clothed clothed/nude clothed_male clothing duo entangled erection female fingers fizzarolli_(helluva_boss) genitals grey_body hand_on_breast hellaverse helluva_boss hi_res imp looking_pleasured male male/female nipples nude octavia_(helluva_boss) on_model on_style open_mouth open_smile owl owl_demon penetration penis pink_eyes pink_sclera red_balls red_penis sex smile spiralart third-party_edit vaginal vaginal_penetration vulva white_eyes yellow_sclera
absurd_res anal anal_penetration anthro anus avian backsack balls beanie bird cellphone clothing double_penetration duo electronics english_text female first_person_view fizzarolli_(helluva_boss) forced genitals glowing glowing_eyes group group_sex hat headgear headwear hellaverse helluva_boss hi_res imp landline_phone male male/female mmf_threesome octavia_(helluva_boss) owl penetration penile penile_penetration penis_in_ass penis_in_vagina phone phone_call profanity rape sex smartphone spiralart stella_(helluva_boss) text threesome vaginal vaginal_penetration
2023 4_arms balls blush clothing demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie duo fizzarolli_(helluva_boss) footwear genitals green_nipples green_sclera grey_background headgear headwear hellaverse helluva_boss hi_res humanoid imp larger_male male male/male mammon_(helluva_boss) money multi_arm multi_limb nipple_piercing nipples penis piercing prosthetic red_body red_eyes red_skin shoes simple_background size_difference smaller_male teeth
16:9 anal anal_penetration animated anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro anus aroused asmodeus_(helluva_boss) ass_up balls bed bedroom_eyes bedroom_sex big_balls big_penis blue_body blue_fur blue_hair blue_skin butt butt_from_the_front closed_smile demon doggystyle duo erection eyelashes fizzarolli_(helluva_boss) from_behind_position fur furniture genitals hair heart_symbol hellaverse helluva_boss horn humanoid imp legs_up looking_pleasured looking_up loop lying male male/male mammal mouth_closed multicolored_body multicolored_skin narrowed_eyes no_sound on_front open_mouth open_smile penetration penile penile_penetration penis penis_in_ass penis_size_difference pillow pupils red_body red_pupils red_skin saucymist seductive sex short_playtime size_difference smile spread_legs spreading tongue two_tone_body two_tone_skin video white_body white_skin widescreen yellow_sclera
2023 4_arms asmodeus_(helluva_boss) boots cellphone clothed clothing crossdressing demon digital_drawing_(artwork) digital_media_(artwork) dress electronics eyewear fizzarolli_(helluva_boss) footwear group hand_holding headgear headwear hellaverse helluva_boss hi_res holding_glass holding_object holding_phone humanoid imp kirkland897 male mammon_(helluva_boss) multi_arm multi_limb phone purse robo_fizzarolli shoes simple_background smartphone sunglasses teeth
2023 4:3 anal asmodeus_(helluva_boss) balls blue_body bodily_fluids clothing cum demon dialogue digital_drawing_(artwork) digital_media_(artwork) digitigrade dontbeazombie duo english_text fizzarolli_(helluva_boss) genital_fluids genitals green_eyes green_sclera grey_background hand_on_shoulder headgear headgear_only headwear headwear_only hellaverse helluva_boss hi_res humanoid imp jester larger_male male male/male male_penetrated male_penetrating male_penetrating_male moan mostly_nude nipples open_mouth penetration penis prosthetic red_body red_eyes red_skin sex simple_background size_difference smaller_male standing standing_sex text
2023 asmodeus_(helluva_boss) belly big_belly demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie duo fizzarolli_(helluva_boss) green_eyes green_sclera hand_on_belly hellaverse helluva_boss hi_res humanoid imp male pregnant pregnant_male red_body red_eyes red_skin simple_background
anal asmodeus_(helluva_boss) bodily_fluids cum cum_in_ass cum_inside curling_tail cybernetic_limb demon demon_humanoid drooling duo fizzarolli_(helluva_boss) genital_fluids genitals hellaverse helluva_boss humanoid imp jester male male/male male_penetrated male_penetrating male_penetrating_male ockiller101 penetration penis saliva scared sex tail tears tears_of_pleasure
anal anal_penetration asmodeus_(helluva_boss) bodily_fluids cum cum_in_ass cum_inside curling_tail cybernetic_limb demon demon_humanoid dildo drooling duo fizzarolli_(helluva_boss) genital_fluids hellaverse helluva_boss humanoid imp jester male male/male object_in_ass obscured_penetration ockiller101 penetration rough_sex saliva scared sex sex_toy sex_toy_in_ass sex_toy_insertion strapon strapon_in_ass strapon_insertion strapon_sex tail tears tears_of_pleasure toying_partner wearing_strapon
anal anal_fingering anal_penetration asmodeus_(helluva_boss) bodily_fluids cybernetic_limb demon demon_humanoid drooling duo fingering fizzarolli_(helluva_boss) genital_fluids hellaverse helluva_boss humanoid imp jester male male/male ockiller101 penetration saliva sex sex_toy size_difference teasing toying_partner
asmodeus_(helluva_boss) blush blush_lines cybernetic_limb demon demon_humanoid duo fizzarolli_(helluva_boss) genitals heart_symbol hellaverse helluva_boss humanoid imp male male/male ockiller101 penis size_difference uwu
absurd_res anthro areola asmodeus_(helluva_boss) avian beanie bird blue_eyes blush breasts butt butt_grab choker clothing demon female fizzarolli_(helluva_boss) forced glowing glowing_eyes group hand_on_butt hat head_grab headgear headwear hellaverse helluva_boss hi_res imp jewelry male male/female necklace nipples octavia_(helluva_boss) owl penetration rape sex spiralart trio
absurd_res anthro asmodeus_(helluva_boss) avian beanie big_penis bird blush bodily_fluids butt butt_grab choker clothing demon faceless_character female fizzarolli_(helluva_boss) forced genital_fluids genitals glowing glowing_eyes group group_sex hand_on_butt hat head_grab headgear headwear hellaverse helluva_boss hi_res humanoid_genitalia humanoid_penis imp jewelry male male/female mmf_threesome mostly_offscreen_character necklace octavia_(helluva_boss) owl penetration penile penis precum rape sex spiralart threesome trio
absurd_res anthro asmodeus_(helluva_boss) avian beanie big_penis bird blush butt butt_grab choker clothing demon double_penetration fellatio female fizzarolli_(helluva_boss) forced forced_oral genitals glowing glowing_eyes group group_sex hand_on_butt hat head_grab headgear headwear hellaverse helluva_boss hi_res imp jewelry male male/female mmf_threesome necklace octavia_(helluva_boss) oral owl penetration penile penis rape sex spiralart spitroast threesome torn_clothing trio
2022 absurd_res asmodeus_(helluva_boss) black_background black_clothing black_hat black_headwear bottomwear carrying_another clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) hat hat_feather headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid imp loose_feather male pants pink_eyes sebasdono simple_background top_hat yellow_eyes yellow_sclera
1:1 2022 abs anthro asmodeus_(helluva_boss) beverage black_body black_clothing black_fur black_hat black_headwear black_horn black_nose blitzo_(helluva_boss) blue_clothing canid canid_demon canine canis clothing collar demon dialogue digital_drawing_(artwork) digital_media_(artwork) english_text female fizzarolli_(helluva_boss) fur green_eyes grey_hair group hair hat headgear headwear heart_symbol hellaverse hellhound helluva_boss hi_res horn humanoid imp loona_(helluva_boss) male mammal millie_(helluva_boss) moxxie_(helluva_boss) multicolored_body multicolored_fur multicolored_horn mythological_canine mythological_creature mythology paulette_cort red_body red_clothing red_eyes red_sclera red_skin simple_background smoothie spiked_collar spikes text top_hat tuft white_body white_fur white_hair white_horn wolf yellow_sclera
1:1 2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) green_eyes green_sclera hat headgear headwear hellaverse helluva_boss hug humanoid imp male red_eyes simple_background top_hat white_background wyspur
2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear blue_clothing bottomwear clothing demon digital_drawing_(artwork) digital_media_(artwork) duo eyewear fizzarolli_(helluva_boss) gohanaddiction420 green_eyes hat headgear headwear hellaverse helluva_boss hi_res humanoid imp kiss_on_hand kissing male pants red_clothing sitting sunglasses top_hat
2022 bottomwear clothing demon digital_drawing_(artwork) digital_media_(artwork) eyewear fizzarolli_(helluva_boss) green_clothing headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid imp male multicolored_clothing pants prosthetic solo sunglasses sweetpupperoo teeth white_clothing
absurd_res anal anal_penetration anthro asmodeus_(helluva_boss) avian beanie big_penis bird black_body black_feathers blue_body blue_feathers bodily_fluids clothing cum cum_in_mouth cum_inside cum_on_face demon double_penetration feathers female fizzarolli_(helluva_boss) forced forced_kiss genital_fluids genitals glowing glowing_eyes group group_sex hat headgear headwear heart_eyes heart_symbol hellaverse helluva_boss hi_res kissing makeup male male/female mascara mind_break mmf_threesome octavia_(helluva_boss) owl penetration penile penile_penetration penis penis_in_ass penis_in_vagina rape ruined_makeup running_makeup running_mascara sex spiralart threesome tongue tongue_out trio vaginal vaginal_penetration
2022 3:4 absurd_res asmodeus_(helluva_boss) black_clothing blitzo_(helluva_boss) clothing demon digital_drawing_(artwork) digital_media_(artwork) fizzarolli_(helluva_boss) gesture green_eyes green_sclera group hand_gesture headgear headwear hellaverse helluva_boss hi_res humanoid imp male middle_finger multicolored_clothing open_mouth red_body red_eyes red_skin teeth thelisforluis trio yellow_sclera
2023 asmodeus_(helluva_boss) bdsm bondage bound chain demon digital_drawing_(artwork) digital_media_(artwork) dominant dominant_male dontbeazombie duo fizzarolli_(helluva_boss) genitals green_eyes green_nipples green_sclera hands_tied hellaverse helluva_boss hi_res humanoid imp larger_male male male/male nipples penis red_eyes simple_background size_difference smaller_male submissive submissive_male
2023 andromorph andromorph/male asmodeus_(helluva_boss) balls demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie duo fizzarolli_(helluva_boss) genitals green_eyes hellaverse helluva_boss hi_res humanoid imp intersex intersex/male larger_male male open_mouth penetration penis sex simple_background size_difference smaller_andromorph smaller_intersex teeth vaginal vaginal_penetration
2023 after_anal after_anal_penetration after_vaginal after_vaginal_penetration andromorph anus bodily_fluids cum cum_from_ass cum_from_vagina cum_in_ass cum_in_vagina cum_inside cum_on_ground cum_on_tail demon digital_drawing_(artwork) digital_media_(artwork) dontbeazombie excessive_cum excessive_genital_fluids fizzarolli_(helluva_boss) genital_fluids genitals green_sclera hellaverse helluva_boss hi_res humanoid imp impregnation intersex leaking_cum lying on_front ovum presenting presenting_cum_inside presenting_vulva prosthetic purple_anus purple_vulva red_body red_eyes red_skin simple_background solo sperm_cell tail vulva
2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_legwear black_thigh_highs blue_body blue_clothing blush clothing demon duo empty_eyes eyes_closed fizzarolli_(helluva_boss) hat hat_feather headgear headwear hellaverse helluva_boss hi_res humanoid imp legwear loose_feather male red_clothing simple_background skeleslay teeth thigh_highs top_hat traditional_media_(artwork) tuft white_background yellow_eyes
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