2023 5:4 accessory asmodeus_(helluva_boss) clothing demon digital_drawing_(artwork) digital_media_(artwork) group hellaverse helluva_boss humanoid legwear male male/male male_penetrated male_penetrating male_penetrating_male mammon_(helluva_boss) necktie penetration saucymist sex simple_background teeth thigh_highs tongue tongue_out trio white_background white_eyes wings
2023 asmodeus_(helluva_boss) black_horn blitzo_(helluva_boss) blue_body bodily_fluids cum demon digital_drawing_(artwork) digital_media_(artwork) fizzarolli_(helluva_boss) french_kissing genital_fluids genitals green_tongue group hellaverse helluva_boss hi_res horn humanoid imp kissing larger_male male male/male multicolored_horn penis prosthetic red_body red_skin sblitos simple_background size_difference smaller_male tongue trio urethral white_horn
2022 asmodeus_(helluva_boss) clothed clothing demon duo fizzarolli_(helluva_boss) headgear headwear heart_symbol hellaverse helluva_boss humanoid imp jester male pink_clothing simple_background skeleslay traditional_media_(artwork) white_background yellow_eyes
2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear blue_clothing clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) dontbeazombie english_text eyes_closed fizzarolli_(helluva_boss) green_eyes grey_background group hat hat_feather headgear headwear hellaverse helluva_boss hi_res humanoid imp jester loose_feather male red_clothing simple_background text top_hat trio tuft
2023 asmodeus_(helluva_boss) black_clothing black_hat black_headwear clothed clothing demon detailed_background digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes eyes_closed fizzarolli_(helluva_boss) garland hat headgear headwear hellaverse helluva_boss hi_res holding_object humanoid imp male open_mouth plant red_clothing tree tuft wizzlydraws yellow_eyes
2023 4_arms asmodeus_(helluva_boss) black_clothing black_hat black_headwear blue_clothing clothed clothing crimson_(helluva_boss) demon digital_drawing_(artwork) digital_media_(artwork) fizzarolli_(helluva_boss) green_clothing green_eyes group hair hat headgear headwear hellaverse helluva_boss hi_res holding_money holding_object humanoid imp lying machine male mammon_(helluva_boss) money multi_arm multi_limb pink_clothing rivet_theproto robo_fizzarolli robot teeth white_hair yellow_clothing yellow_eyes
2023 asmodeus_(helluva_boss) black_clothing black_hat black_headwear chest_tuft clothing demon digital_drawing_(artwork) digital_media_(artwork) dress duo female hair hand_on_hip hand_on_leg hand_on_thigh hat headgear headwear hellaverse helluva_boss hi_res humanoid humanoid_pointy_ears kirkland897 long_hair male pointy_ears simple_background succubus top_hat tuft white_background white_eyes
2023 asmodeus_(helluva_boss) avian chef_hat clothed clothing clown demon demon_humanoid dialogue digital_drawing_(artwork) digital_media_(artwork) english_text fizzarolli_(helluva_boss) food grey_background group harlequin hat headgear headwear hellaverse helluva_boss hi_res holding_object humanoid imp male mammon_(helluva_boss) pizza samcubuss simple_background sketch text trio
2023 4_arms asmodeus_(helluva_boss) carton chair clothed clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text furniture gesture gloves hand_gesture hand_on_table handwear hat headgear headwear hellaverse helluva_boss hi_res humanoid kirkland897 male mammon_(helluva_boss) middle_finger multi_arm multi_limb simple_background sitting table teeth text top_hat white_background
2023 asmodeus_(helluva_boss) clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) hand_on_head happy headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid imp jester kirkland897 male simple_background tuft white_background
2023 asmodeus_(helluva_boss) black_clothing black_dress black_hair black_hat black_headwear black_top_hat blue_clothing box clothed clothing container demon digital_drawing_(artwork) digital_media_(artwork) dress duo female hair hat hat_feather headgear headwear hellaverse helluva_boss hi_res holding_box holding_container holding_object humanoid humanoid_pointy_ears long_hair loose_feather male pink_body pink_skin pointy_ears red_clothing succubus theroseinvasion top_hat yellow_eyes
2023 asmodeus_(helluva_boss) black_clothing black_legwear black_leotard black_thigh_highs butt clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) english_text hellaverse helluva_boss hi_res kirkland897 legwear leotard male pink_background simple_background solo text thigh_highs white_eyes
1:1 2023 asmodeus_(helluva_boss) black_bars black_clothing black_hat black_headwear clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) duo hat hat_feather headgear headwear heart_symbol hellaverse helluva_boss larger_male letterbox loose_feather male mammon_(helluva_boss) pattern_clothing purple_clothing saucymist size_difference smaller_male
1:1 2022 asmodeus_(helluva_boss) black_clothing black_legwear black_thigh_highs black_wings clothing collar demon digital_drawing_(artwork) digital_media_(artwork) duo grey_background heart_symbol hellaverse helluva_boss humanoid larger_male legwear male male/male mammon_(helluva_boss) saucymist simple_background size_difference smaller_male thigh_highs wings
2022 asmodeus_(helluva_boss) black_clothing black_gloves black_handwear black_legwear black_thigh_highs butt clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) gloves green_eyes handwear heart_symbol hellaverse helluva_boss humanoid imp larger_male legwear male male/male prosthetic saucymist simple_background size_difference smaller_male thick_thighs thigh_highs white_background white_clothing
2023 absurd_res anal asmodeus_(helluva_boss) demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes fellatio fizzarolli_(helluva_boss) grey_background group group_sex hand_on_leg hand_on_thigh hellaverse helluva_boss hi_res humanoid imp kirkland897 kissing larger_male male male/male male_penetrated male_penetrating male_penetrating_male mammon_(helluva_boss) monochrome multi_arm multi_limb oral penetration penile sex simple_background size_difference smaller_male smaller_penetrated solo_focus spitroast spitroast_kiss threesome tongue tongue_out tongue_out_fellatio white_eyes
2021 3:4 anthro asmodeus_(helluva_boss) blue_body blue_clothing blue_fur blue_nose canid canine canis citrinehypno clothing demon digital_drawing_(artwork) digital_media_(artwork) domestic_dog duo fur green_eyes hand_behind_head hellaverse helluva_boss hi_res horn male mammal mastectomy_scar multicolored_body multicolored_fur red_clothing scar trans_(lore) trans_man_(lore) white_body white_fur
2023 asmodeus_(helluva_boss) black_clothing black_hair black_hat black_headwear blue_clothing clothed clothing crossed_arms demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo ellipsis english_text female green_eyes hair hat headgear headwear hellaverse helluva_boss hi_res humanoid imp larger_male male red_body red_clothing red_skin simple_background size_difference smaller_female text top_hat tuft witcheryz
2023 anthro asmodeus_(helluva_boss) black_clothing black_hat black_headwear clothed clothing darkmythiccat demon detailed_background digital_drawing_(artwork) digital_media_(artwork) domestic_cat duo empty_eyes felid feline felis female hat headgear headwear hellaverse helluva_boss hi_res larger_male male mammal size_difference smaller_anthro smaller_female top_hat tuft yellow_eyes
2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_top_hat blue_clothing clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes glowing glowing_eyes hat hat_feather headgear headwear hellaverse helluva_boss hi_res humanoid looking_at_viewer loose_feather male pink_clothing pl_trip solo top_hat yellow_eyes
2022 asmodeus_(helluva_boss) blue_clothing clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes flower gloves green_eyes handwear hat hat_flower headgear headwear hellaverse helluva_boss hi_res humanoid looking_at_viewer male plant solo soylamhoony tuft white_clothing white_hat white_headwear
2022 absurd_res art_of_iris asmodeus_(helluva_boss) black_boots black_clothing black_footwear boots clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes footwear hellaverse helluva_boss hi_res high_heeled_boots high_heels hoodie humanoid legwear looking_at_viewer male multicolored_clothing shoes simple_background solo thigh_boots thigh_highs topwear white_clothing yellow_eyes
1:1 2022 asmodeus_(helluva_boss) blue_clothing clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid looking_at_viewer maathedino male open_mouth pink_clothing solo yellow_eyes
2022 asmodeus_(helluva_boss) black_clothing black_hat black_headwear blue_body clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes hat hat_feather headgear headwear hellaverse helluva_boss hi_res humanoid looking_at_viewer loose_feather male solo soylamhoony yellow_eyes
1:1 2021 asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_top_hat clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes fkimnsfw hat headgear headwear hellaverse helluva_boss hi_res humanoid looking_at_viewer male red_clothing solo top_hat tuft yellow_eyes
2023 absurd_res asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_top_hat blue_clothing clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) green_eyes hat headgear headwear hellaverse helluva_boss hi_res humanoid male pattern_clothing penny-wren pink_clothing solo striped_clothing stripes top_hat
1:1 2023 absurd_res armwear asmodeus_(helluva_boss) balls blue_body clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes genitals green_eyes hand_on_chest hand_on_leg hand_on_thigh hellaverse helluva_boss hi_res humanoid legwear looking_at_viewer male navel not_furry penis simple_background solo thigh_highs white_armwear white_clothing white_legwear white_thigh_highs
2023 alpha_channel asmodeus_(helluva_boss) bathrobe blue_body clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) green_eyes hellaverse helluva_boss hi_res humanoid imp inkscape_(artwork) jenna-lynx larger_male male pink_clothing prosthetic red_clothing red_eyes red_robe robe size_difference smaller_male
2023 absurd_res asmodeus_(helluva_boss) blush bodily_fluids clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) english_text fizzarolli_(helluva_boss) foreskin genital_fluids genitals group hand_on_chest handjob headgear headwear hellaverse helluva_boss hi_res humanoid imp kirkland897 male male/male mammon_(helluva_boss) multi_arm multi_limb penile penis precum sex simple_background teeth text trio white_background white_eyes
2022 asmodeus_(helluva_boss) balls bite black_boots black_clothing black_footwear black_legwear black_thigh_highs blue_body blush boots butt butt_slap clothing demon duo fizzarolli_(helluva_boss) footwear genitals hellaverse helluva_boss humanoid imp legwear male male/male open_mouth pillow pillow_bite pink_clothing shoes simple_background skeleslay slap spank_marks spanking thigh_boots thigh_highs traditional_media_(artwork) white_background yellow_eyes
2023 anal asmodeus_(helluva_boss) bite_mark blue_body blue_clothing clothing demon duo empty_eyes eyes_closed fizzarolli_(helluva_boss) genitals hand_on_leg hand_on_thigh hellaverse helluva_boss humanoid imp male male/male oral penis red_clothing rimming sex simple_background skeleslay tail tail_around_penis tail_fetish tail_play tail_sex tailjob traditional_media_(artwork) white_background yellow_eyes
anus asmodeus_(helluva_boss) big_butt big_penis blush breasts butt butt_grab demon demon_humanoid duo faceless_character faceless_male female genitals gothstoat grey_hair hair hand_on_butt heart_symbol hellaverse helluva_boss hi_res humanoid lin_(helluva_boss) male male/female mature_female nipples one_eye_closed penis pubes red_body solo_focus tail vein veiny_penis
anus asmodeus_(helluva_boss) big_butt big_penis blush bodily_fluids breasts butt butt_grab cum cum_in_vagina cum_inside demon demon_humanoid dialogue duo english_text explicitly_stated_consent faceless_character faceless_male female genital_fluids genitals gothstoat grey_hair hair hand_on_butt heart_symbol hellaverse helluva_boss hi_res humanoid impregnation_request lin_(helluva_boss) looking_pleasured male male/female mature_female nipples one_eye_closed open_mouth open_smile penis pubes red_body smile solo_focus tail teeth text vein veiny_penis
6:5 abdominal_bulge asmodeus_(helluva_boss) balls big_balls big_butt big_penis black_hair blush bodily_fluids breasts butt demon demon_humanoid dialogue duo english_text faceless_character faceless_male female female_penetrated genitals gothstoat hair heart_symbol hellaverse helluva_boss hi_res humanoid male male/female male_penetrating male_penetrating_female mature_female moxxie's_mother nipples penetration penile penile_penetration penis penis_in_vagina pubes red_body sex solo_focus sweat tail text vaginal vaginal_penetration vein veiny_penis
6:5 abdominal_bulge asmodeus_(helluva_boss) balls big_balls big_butt big_penis black_hair blush bodily_fluids breasts butt cum cum_in_vagina cum_inside demon demon_humanoid dialogue duo english_text faceless_character faceless_male female female_penetrated genital_fluids genitals gothstoat hair heart_symbol hellaverse helluva_boss hi_res humanoid male male/female male_penetrating male_penetrating_female mature_female moxxie's_mother nipples orgasm orgasm_face penetration penile penile_penetration penis penis_in_vagina pubes red_body sex solo_focus sweat tail teeth text tongue tongue_out vaginal vaginal_penetration vein veiny_penis
anthro asmodeus_(helluva_boss) avian bird black_background demon dialogue duo hair hellaverse helluva_boss hi_res holding_arm male monochrome owl owl_demon short_hair simple_background stolas_(helluva_boss) teathekook text white_text
angry anthro asmodeus_(helluva_boss) avian bird black_background clothing crown demon dialogue duo hair hat headgear headwear hellaverse helluva_boss hi_res holding_arm male owl owl_demon paimon_(helluva_boss) red_text short_hair simple_background smile teathekook text top_hat white_text
2023 absurd_res asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_top_hat blep cellphone clothing demon digital_drawing_(artwork) digital_media_(artwork) electronics fizzarolli_(helluva_boss) green_eyes group hat headgear headwear hellaverse helluva_boss hi_res holding_object holding_phone humanoid kirkland897 male mammon_(helluva_boss) phone prosthetic red_clothing smartphone tongue tongue_out top_hat trio
1:1 2023 absurd_res asmodeus_(helluva_boss) blue_body bulge chest_tuft demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes feet green_eyes hellaverse helluva_boss hi_res looking_at_viewer male navel not_furry one_eye_closed simple_background solo tuft
2023 asmodeus_(helluva_boss) black_clothing black_legwear black_thigh_highs blue_body clothing collar demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text genitals green_eyes hand_on_leg heart_symbol hellaverse helluva_boss humanoid legwear male male/male mammon_(helluva_boss) penis saucymist simple_background spiked_collar spikes teeth text thigh_highs white_background
16:10 absurd_res anthro anus asmodeus_(helluva_boss) big_penis bodily_fluids confusion duo_focus female female_anthro female_focus genital_fluids genitals group hazbin_hotel hellaverse helluva_boss hi_res male male/female male_anthro niffty_(hazbin_hotel) nude octavia_(helluva_boss) penis plump_labia precum pubic_mound puffy_anus rubbing rubbing_penis rubbing_vulva size_difference spiralart thick_thighs trio vulva widescreen
16:10 absurd_res anal anal_penetration anthro anthro_penetrated anus asmodeus_(helluva_boss) bedroom_eyes big_penis bodily_fluids cum cum_drip cum_from_ass cum_from_mouth cum_in_ass cum_in_mouth cum_inside cum_through dripping female fucked_silly genital_fluids genitals group hazbin_hotel heart_symbol hellaverse helluva_boss hi_res holding_another's_penis holding_penis leaking_cum looking_pleasured male male/female male_penetrating_anthro narrowed_eyes niffty_(hazbin_hotel) octavia_(helluva_boss) orgasm penetration penile penile_penetration penis penis_in_ass seductive size_difference spiralart spread_anus spreading trio vaginal_fluids vulva widescreen
absurd_res andrealphus_(helluva_boss) asmodeus_(helluva_boss) avian balls bedroom_eyes big_penis black_glans black_penis blitzo_(helluva_boss) blush chart chest_tuft demon erection fizzarolli_(helluva_boss) fluffy foreskin genitals glans green_glans grin group hair heart_eyes heart_symbol hellaverse helluva_boss hi_res huge_penis humanoid_genitalia humanoid_penis imp laugh leponsart long_hair long_penis male moxxie_(helluva_boss) narrowed_eyes owl_demon penis penis_chart penis_lineup penis_size_difference pubes red_balls red_body red_glans red_penis red_skin retracted_foreskin seductive sharp_teeth simple_background smile stolas_(helluva_boss) teeth thick_penis tuft vein veiny_penis
2023 4_arms absurd_res asmodeus_(helluva_boss) clothing demon dialogue digital_media_(artwork) digital_painting_(artwork) dirty_talk dominant dominant_male duo english_text fellatio footwear genitals grey_background hair hellaverse helluva_boss hi_res humanoid kirkland897 male male/male mammon_(helluva_boss) masturbation multi_arm multi_limb oral painting_(artwork) penile penis pulling_hair sex simple_background socks submissive submissive_male text touching_hair
2023 4:3 asmodeus_(helluva_boss) blush boxers_(clothing) clothing condom demon digital_drawing_(artwork) digital_media_(artwork) discarded_clothing duo empty_eyes eyes_closed fizzarolli_(helluva_boss) hat headgear headwear hellaverse helluva_boss hi_res holding_clothing holding_hat holding_headgear holding_headwear holding_object humanoid imp kissing larger_male lying male male/male on_back prosthetic rillunax sexual_barrier_device size_difference smaller_male tail tail_around_leg top_hat underwear yellow_eyes
2023 absurd_res asmodeus_(helluva_boss) dancing demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes eyes_closed fizzarolli_(helluva_boss) green_eyes hand_on_belly hellaverse helluva_boss hi_res humanoid imp male nigirioff pole pole_dancing red_body red_skin tail teeth
1_eye 3:5 absurd_res anthro asmodeus_(helluva_boss) ass_to_mouth avian beanie big_butt big_penis bird bodily_fluids butt clothing comic crown cum cum_in_ass cum_in_vagina cum_inside demon dialogue english_text female fizzarolli_(helluva_boss) foursome genital_fluids genitals group group_sex hat hazbin_hotel headgear headwear hellaverse helluva_boss hi_res kiss_on_penis kissing licking male male/female musical_note musical_symbol niffty_(hazbin_hotel) nude octavia_(helluva_boss) oral owl penile penis penis_lick sex size_difference spiralart stroking_penis symbol text tired tongue tongue_out
1:1 2023 alyachan13 asmodeus_(helluva_boss) clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes hat headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid looking_at_viewer male not_furry solo yellow_eyes
2023 asmodeus_(helluva_boss) black_clothing black_hat black_headwear black_top_hat blue_body clothing demon digital_drawing_(artwork) digital_media_(artwork) duo fizzarolli_(helluva_boss) green_eyes hat hat_feather headgear headwear hellaverse helluva_boss humanoid loose_feather male not_furry open_mouth purple_background simple_background top_hat volticglitch
2023 4_arms absurd_res angry asmodeus_(helluva_boss) clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text hand_on_shoulder hellaverse helluva_boss hi_res humanoid kirkland897 male mammon_(helluva_boss) multi_arm multi_limb simple_background sweater teeth text topwear white_background
Next