2023 4_arms black_clothing blush bracelet bulge clothing corset demon dialogue digital_drawing_(artwork) digital_media_(artwork) empty_eyes english_text hellaverse helluva_boss hi_res humanoid jewelry kirkland897 lingerie male mammon_(helluva_boss) multi_arm multi_limb simple_background solo spiked_bracelet spikes teeth text topwear white_background white_eyes
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
2023 4_arms absurd_res asphyxiation black_clothing choking cigar clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes english_text gloves grey_background handwear hellaverse helluva_boss hi_res humanoid kirkland897 larger_male male mammon_(helluva_boss) multi_arm multi_limb simple_background size_difference teeth text white_eyes
2023 4_arms clothed clothing crossed_arms demon digital_drawing_(artwork) digital_media_(artwork) fully_clothed green_clothing green_eyes grey_background hand_in_pocket hellaverse helluva_boss humanoid male mammon_(helluva_boss) multi_arm multi_limb pinapler pockets simple_background solo
1:1 2023 4_arms absurd_res belly black_clothing bulge clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes grey_background hellaverse helluva_boss hi_res humanoid latex latex_clothing latex_skinsuit looking_at_viewer male mammon_(helluva_boss) multi_arm multi_limb navel nipples overweight overweight_male simple_background skinsuit solo teeth tight_clothing white_eyes
1:1 2023 absurd_res belly black_clothing black_legwear black_thigh_highs bulge clothed clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes gloves handwear hellaverse helluva_boss hi_res humanoid legwear male mammon_(helluva_boss) multi_arm multi_limb navel overweight overweight_male partially_clothed simple_background solo teeth thigh_highs white_eyes
2023 4_arms adam_(hazbin_hotel) angel clothing crossed_arms demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text halo hazbin_hotel hellaverse helluva_boss hi_res holding_object humanoid kirkland897 male mammon_(helluva_boss) monochrome multi_arm multi_limb open_mouth shirt simple_background sketch t-shirt teeth text topwear white_background
2023 absurd_res bed black_bottomwear black_clothing black_footwear black_hair black_pants black_shoes bottomwear clothing demon detailed_background digital_drawing_(artwork) digital_media_(artwork) duo eyes_closed female footwear furniture green_clothing hair hellaverse helluva_boss hi_res high_heels humanoid humanoid_pointy_ears kissing lying male male/female mammon_(helluva_boss) on_back pants pink_body pink_skin pointy_ears shoes skellatin succubus
2023 4_arms absurd_res armwear balls black_armwear black_clothing black_legwear black_thigh_highs clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) dominant empty_eyes genitals hellaverse helluva_boss hi_res holding_object holding_whip humanoid leash legwear male mammon_(helluva_boss) moobs multi_arm multi_limb overweight overweight_male penis simple_background solo teeth thigh_highs whip white_eyes
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
2023 absurd_res animal_print armwear belly boots clothing cow_print demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes footwear hand_behind_head hellaverse helluva_boss hi_res high_heeled_boots high_heels humanoid legwear male mammon_(helluva_boss) multi_arm multi_limb navel overweight overweight_male shoes simple_background solo teeth thigh_highs white_eyes
2023 4_arms absurd_res black_clothing black_underwear clothing crossed_arms demon dialogue digital_drawing_(artwork) digital_media_(artwork) gesture hand_gesture hellaverse helluva_boss hi_res humanoid kirkland897 male mammon_(helluva_boss) middle_finger multi_arm multi_limb simple_background solo underwear white_background
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 4_arms absurd_res armwear belly black_armwear black_boots black_clothing black_footwear black_legwear black_thigh_highs boots bulge clothing dancing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes footwear hellaverse helluva_boss hi_res high_heeled_boots high_heels humanoid legwear male mammon_(helluva_boss) moobs multi_arm multi_limb navel overweight overweight_male pole pole_dancing shoes simple_background solo teeth thigh_boots thigh_highs white_eyes
2023 4_arms absurd_res belly bottomwear clothed clothing crossdressing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes garter_straps hellaverse helluva_boss hi_res holding_object humanoid legwear maid_uniform male mammon_(helluva_boss) multi_arm multi_limb navel overweight overweight_male simple_background skirt solo teeth thigh_highs uniform white_eyes
2023 4_arms absurd_res black_hair black_wings bodily_fluids demon detailed_background dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text female green_eyes hair hellaverse helluva_boss hi_res humanoid kirkland897 larger_humanoid larger_male male mammon_(helluva_boss) multi_arm multi_limb pillow pink_body pink_skin size_difference smaller_female smaller_humanoid succubus tail tail_around_leg tears text wings
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
2023 4_arms absurd_res bottomwear chair clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) duo electric_guitar electronics furniture guitar hat hazbin_hotel headgear headwear hellaverse helluva_boss hi_res holding_guitar holding_musical_instrument holding_object humanoid kirkland897 male mammon_(helluva_boss) microphone multi_arm multi_limb musical_instrument one_eye_closed pants plucked_string_instrument seviathan_von_eldritch sitting string_instrument table teeth
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 absurd_res anal_beads armwear balls black_clothing black_legwear black_thigh_highs clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes genitals hand_on_leg hand_on_thigh hellaverse helluva_boss hi_res humanoid legwear male mammon_(helluva_boss) moobs multi_arm multi_limb navel overweight overweight_male penis sex_toy simple_background solo teeth thigh_highs white_eyes
2023 absurd_res anal anal_masturbation anal_penetration animal_dildo animal_sex_toy balls_in_underwear big_dildo black_clothing black_legwear black_thigh_highs canine_dildo clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) dildo dildo_in_ass dildo_insertion dildo_sitting empty_eyes equine_dildo genitals hellaverse helluva_boss hi_res humanoid legwear looking_pleasured male mammon_(helluva_boss) masturbation medial_ring nipple_fetish nipple_play object_in_ass penetration penis sex_toy sex_toy_in_ass sex_toy_insertion simple_background solo teeth thigh_highs tongue white_eyes
2023 4_arms black_horn cellphone cigar clothed clothing demon detailed_background dialogue digital_drawing_(artwork) digital_media_(artwork) duo electronics english_text erection erection_under_clothing green_clothing green_eyes green_swimming_trunks green_swimwear hellaverse helluva_boss holding_cigar holding_object holding_phone horn humanoid imp kirkland897 male mammon_(helluva_boss) multi_arm multi_limb multicolored_horn phone phone_call red_body red_skin smartphone swimming_pool swimming_trunks swimwear text water white_horn yellow_sclera
2023 4_arms absurd_res black_clothing black_underwear clothing demon digital_drawing_(artwork) digital_media_(artwork) gesture hand_gesture hellaverse helluva_boss hi_res humanoid kirkland897 male mammon_(helluva_boss) middle_finger money multi_arm multi_limb print_clothing simple_background slightly_chubby solo teeth underwear white_background
2023 4_arms absurd_res black_clothing black_collar black_footwear black_high_heels black_thong black_underwear cigarette cigarette_in_mouth clothing collar demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes fishnet_clothing footwear gloves handwear hellaverse helluva_boss hi_res high_heels humanoid male mammon_(helluva_boss) multi_arm multi_limb object_in_mouth overweight overweight_male shoes simple_background smoke solo spiked_collar spikes thong underwear white_eyes
2023 4_arms absurd_res anal anal_masturbation anal_penetration big_dildo clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) dildo dildo_in_ass dildo_insertion empty_eyes exercise footwear hand_on_butt hand_on_own_butt hellaverse helluva_boss hi_res humanoid male mammon_(helluva_boss) masturbation multi_arm multi_limb object_in_ass overweight overweight_male penetration sex_toy sex_toy_in_ass sex_toy_insertion sexercise shoes simple_background sneakers solo teeth topwear weightlifting white_eyes workout
2023 4_arms absurd_res demon digital_drawing_(artwork) digital_media_(artwork) duo eyes_closed french_kissing green_eyes hellaverse helluva_boss hi_res humanoid imp kirkland897 kissing machine male male/male mammon_(helluva_boss) multi_arm multi_limb overweight overweight_male robo_fizzarolli robot simple_background teeth tongue white_background
2023 absurd_res anthro aquatic demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo fish hellaverse helluva_boss hi_res humanoid kirkland897 larger_humanoid larger_male lying male mammon_(helluva_boss) monochrome multi_arm multi_limb overweight overweight_male pillow shark simple_background size_difference sketch smaller_anthro smaller_male teeth white_background
2023 4_arms absurd_res belly bendy_straw beverage bikini clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) drinking_straw empty_eyes fingerless_gloves gloves hand_on_leg hand_on_thigh handwear hellaverse helluva_boss hi_res holding_glass holding_object humanoid looking_at_viewer male mammon_(helluva_boss) multi_arm multi_limb navel navel_piercing overweight overweight_male piercing simple_background solo swimwear teeth two-piece_swimsuit white_eyes
2023 4_arms absurd_res anus armwear back_rolls backsack balls black_armwear black_clothing black_legwear black_thigh_highs boots butt clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) empty_eyes footwear genitals hand_on_butt hellaverse helluva_boss hi_res high_heeled_boots high_heels humanoid legwear looking_at_viewer male mammon_(helluva_boss) multi_arm multi_limb perineum shoes simple_background solo teeth thigh_boots thigh_highs white_eyes
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
1:1 2023 4_arms absurd_res anthro anthro_penetrated balls big_breasts bodily_fluids breasts canid canid_demon canine clasped_hands clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) duo female female_penetrated fox fucked_silly genital_fluids genitals hair hand_on_breast hand_on_leg happy happy_sex hellaverse hellhound helluva_boss hi_res humanoid humanoid_on_anthro humanoid_penetrating humanoid_penetrating_anthro large_penetration legwear looking_pleasured male male/female male_penetrating male_penetrating_anthro male_penetrating_female mammal mammon_(helluva_boss) multi_arm multi_limb mythological_canine mythological_creature mythology narrowed_eyes nipples nude nude_female one_eye_closed open_mouth penetration penile penile_penetration penis penis_in_vagina queen_bee-lzebub_(helluva_boss) sex simple_background spread_legs spreading teeth thigh_highs tongue vaginal vaginal_fluids vaginal_penetration vulva
2023 4_arms absurd_res anthro arthropod black_clothing bottle bottomwear canid canid_demon canine clothing container demon digital_drawing_(artwork) digital_media_(artwork) duo female fox gloves handwear hellaverse hellhound helluva_boss hi_res holding_bottle holding_container holding_object humanoid hybrid insect kirkland897 larger_humanoid larger_male male mammal mammon_(helluva_boss) monochrome multi_arm multi_limb mythological_canine mythological_creature mythology queen_bee-lzebub_(helluva_boss) shorts simple_background size_difference smaller_anthro smaller_female teeth white_background
2023 absurd_res bottomwear clothing demon digital_drawing_(artwork) digital_media_(artwork) duo headgear headwear hellaverse helluva_boss hi_res humanoid imp kirkland897 larger_male machine male mammon_(helluva_boss) monochrome multi_arm multi_limb pants robo_fizzarolli robot shirt simple_background sitting size_difference smaller_male t-shirt teeth topwear white_background
2023 4_arms arm_support beverage blush clothed clothing coffee container cup demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes gloves handwear headgear headwear hellaverse helluva_boss holding_container holding_cup holding_mug holding_object humanoid imp kirkland897 machine male mammon_(helluva_boss) mug multi_arm multi_limb robo_fizzarolli robot spitting_drink
2023 4_arms arinfrankanon asmodeus_(helluva_boss) bed_sheet bedding cigar demon digital_drawing_(artwork) digital_media_(artwork) duo hand_on_back heart_symbol hellaverse helluva_boss holding_cigar holding_object hug humanoid male male/male mammon_(helluva_boss) multi_arm multi_limb pasties sketch
2023 absurd_res anal anal_penetration anthro anthro_penetrating anthro_penetrating_humanoid armwear back_rolls balls breasts butt_slap canid canid_demon canine clothing collar demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) dildo dominant dominant_anthro dominant_female duo female female_penetrating female_penetrating_male fox genitals hair heart_symbol hellaverse hellhound helluva_boss hi_res holding_paddle humanoid humanoid_on_anthro humanoid_penetrated leash leashed_collar leashed_male legwear licking licking_lips licking_own_lips male male/female male_penetrated mammal mammon_(helluva_boss) mythological_canine mythological_creature mythology nipples object_in_ass paddle pegging penetration queen_bee-lzebub_(helluva_boss) sex sex_toy sex_toy_in_ass sex_toy_insertion slap spanking strapon strapon_sex submissive submissive_humanoid submissive_male teeth thigh_highs tongue tongue_out toying_partner
2023 absurd_res anthro balls belly breasts canid canid_demon canine chastity_cage chastity_device clothing collar demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) duo female fishnet_clothing fishnet_legwear fox genitals gesture hair hand_gesture hellaverse hellhound helluva_boss hi_res humanoid key leash legwear male male/female mammal mammon_(helluva_boss) mythological_canine mythological_creature mythology navel nipples one_eye_closed overweight overweight_male queen_bee-lzebub_(helluva_boss) tongue tongue_out v_sign
2023 absurd_res asmodeus_(helluva_boss) bed_sheet bedding blue_body clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes eyes_closed fizzarolli_(helluva_boss) green_eyes group headgear headwear heart_symbol hellaverse helluva_boss hi_res humanoid imp male mammon_(helluva_boss) open_mouth red_body red_skin rosy_fun teeth trio
2023 absurd_res asmodeus_(helluva_boss) blush demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes hand_on_belly hellaverse helluva_boss hi_res humanoid kirkland897 licking licking_lips male mammon_(helluva_boss) simple_background teeth tongue tongue_out white_background
1:1 2023 absurd_res anal anal_penetration anthro anthro_penetrating anthro_penetrating_humanoid anus balls canid canid_demon canine canis clothing demon demongirl_demoness dialogue digital_drawing_(artwork) digital_media_(artwork) double_anal double_penetration english_text fox genitals group group_sex gynomorph gynomorph/male gynomorph_penetrating gynomorph_penetrating_male hair hellaverse hellhound helluva_boss hi_res humanoid humanoid_on_anthro humanoid_penetrated intersex intersex/male intersex_penetrating intersex_penetrating_male legwear loona_(helluva_boss) male male_penetrated mammal mammon_(helluva_boss) moan mythological_canine mythological_creature mythology nipples penetration penile penile_penetration penis penis_in_ass profanity queen_bee-lzebub_(helluva_boss) sex teeth text thigh_highs threesome tongue tongue_out trio twisted_sandwich_position wolf
2023 4_arms bottomwear cellphone clothing demon digital_drawing_(artwork) digital_media_(artwork) duo electronics empty_eyes hellaverse helluva_boss hi_res holding_object holding_phone humanoid imp kirkland897 larger_male machine male mammon_(helluva_boss) multi_arm multi_limb phone robo_fizzarolli robot simple_background size_difference smaller_male white_eyes
11:8 2023 andromorph andromorph/male andromorph_penetrated asmodeus_(helluva_boss) demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes genitals hellaverse helluva_boss humanoid intersex intersex/male intersex_penetrated kissing male male/male male_penetrating male_penetrating_andromorph male_penetrating_intersex mammon_(helluva_boss) moan penetration penile penile_penetration penis penis_in_vagina saucymist sex vaginal vaginal_penetration white_eyes
11:8 2023 anal anal_penetration asmodeus_(helluva_boss) balls black_clothing black_legwear black_thigh_highs butt clothing demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes genitals hellaverse helluva_boss legwear male male/male male_penetrated male_penetrating male_penetrating_male mammon_(helluva_boss) penetration penile penile_penetration penis penis_in_ass saucymist sex thigh_highs tongue tongue_out white_eyes
11:8 2023 asmodeus_(helluva_boss) balls big_penis clothing demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes eyes_closed genitals heart_symbol hellaverse helluva_boss humanoid larger_male legwear male male/male mammon_(helluva_boss) one_eye_closed penis pink_background saucymist simple_background size_difference smaller_male teeth thigh_highs white_eyes
1:1 2023 absurd_res anal anal_penetration anthro anthro_on_bottom anthro_penetrating anthro_penetrating_humanoid anthro_penetrating_male balls breasts canid canid_demon canine clothing demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) duo fox genitals gynomorph gynomorph/male gynomorph_anthro gynomorph_on_bottom gynomorph_penetrating gynomorph_penetrating_humanoid gynomorph_penetrating_male hair hellaverse hellhound helluva_boss hi_res humanoid humanoid_genitalia humanoid_on_anthro humanoid_penetrated humanoid_penis intersex intersex/male intersex_anthro intersex_on_bottom intersex_on_humanoid intersex_penetrating intersex_penetrating_humanoid intersex_penetrating_male interspecies large_penetration larger_anthro larger_gynomorph larger_intersex legwear male male_on_top male_penetrated mammal mammon_(helluva_boss) moobs mythological_canine mythological_creature mythology nipples on_bottom on_top penetration penile penile_penetration penis penis_in_ass queen_bee-lzebub_(helluva_boss) sex size_difference slightly_chubby slightly_chubby_humanoid slightly_chubby_male smaller_humanoid smaller_male smaller_penetrated thigh_highs
2023 asmodeus_(helluva_boss) cigar clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) fizzarolli_(helluva_boss) furniture green_clothing green_eyes group hellaverse helluva_boss hi_res humanoid imp male mammon_(helluva_boss) sitting sofa teeth vanillabrwnsugr
2023 4_arms animal_print belly clothing cow_print demon dialogue digital_drawing_(artwork) digital_media_(artwork) empty_eyes english_text gesture hand_behind_head hand_gesture hellaverse helluva_boss hi_res humanoid kirkland897 legwear male mammon_(helluva_boss) middle_finger moobs multi_arm multi_limb overweight overweight_male simple_background solo teeth text thigh_highs white_background
2023 absurd_res black_clothing black_underwear bulge clothing demon digital_drawing_(artwork) digital_media_(artwork) duo glowing glowing_eyes green_eyes hair hand_on_knee hand_on_leg hellaverse helluva_boss hi_res humanoid imp kirkland897 larger_male machine male mammon_(helluva_boss) multi_arm multi_limb not_furry pillow robo_fizzarolli robot size_difference smaller_male underwear yellow_eyes
2023 cauldronmixing clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) duo eyes_closed fizzarolli_(helluva_boss) footwear hellaverse helluva_boss hi_res humanoid imp kissing male male/male mammon_(helluva_boss) monochrome multi_arm multi_limb ruff_(clothing) shoes tail
2023 absurd_res anthro anthro_penetrating anthro_penetrating_humanoid armwear canid canid_demon canine clothing crymini_(hazbin_hotel) demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) duo english_text gynomorph gynomorph/male gynomorph_penetrating gynomorph_penetrating_male hair hand_on_back hazbin_hotel hellaverse hellhound helluva_boss hi_res humanoid humanoid_on_anthro humanoid_penetrated intersex intersex/male intersex_penetrating intersex_penetrating_male larger_humanoid larger_male larger_penetrated larger_sub legwear male male_penetrated mammal mammon_(helluva_boss) mythological_canine mythological_creature mythology overweight overweight_male penetration pillow profanity sex size_difference smaller_anthro smaller_gynomorph smaller_intersex submissive text thigh_highs
Next