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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
2022 5:4 butt demon digital_drawing_(artwork) digital_media_(artwork) ellipsis heart_symbol hellaverse helluva_boss humanoid male mammon_(helluva_boss) monochrome saucymist simple_background solo teeth white_background wings
2022 cigar clothed clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) grey_background heart_symbol hellaverse helluva_boss humanoid long_tongue male mammon_(helluva_boss) monochrome saucymist simple_background solo teeth tongue tongue_out wings
2022 6:5 animal_print asmodeus_(helluva_boss) clothing cow_print demon digital_drawing_(artwork) digital_media_(artwork) duo heart_symbol hellaverse helluva_boss humanoid male mammon_(helluva_boss) monochrome saucymist simple_background white_background wings
1:1 2022 clothing demon digital_drawing_(artwork) digital_media_(artwork) food hellaverse helluva_boss holding_food holding_object holding_popsicle humanoid male mammon_(helluva_boss) monochrome not_furry popsicle print_clothing saucymist shirt simple_background solo tongue tongue_out topwear white_background wings
1:1 2022 asmodeus_(helluva_boss) black_clothing breasts cigar clothed clothing crossgender demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes female gesture green_eyes hand_gesture hand_on_another's_hip hand_on_hip hat headgear headwear heart_symbol hellaverse helluva_boss humanoid mammon_(helluva_boss) middle_finger mtf_crossgender red_clothing saucymist simple_background teeth tongue tongue_out top_hat white_background wings
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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
2023 asmodeus_(helluva_boss) blush clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text heart_symbol hellaverse helluva_boss humanoid jester larger_male leg_grab legwear male male/male mammon_(helluva_boss) multi_arm multi_limb saucymist simple_background size_difference smaller_male teeth text thigh_highs waist_grab white_background
2023 anal anal_penetration asmodeus_(helluva_boss) blush clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes english_text footwear genitals green_eyes grey_background handjob handjob_while_penetrating hellaverse helluva_boss hi_res humanoid kirkland897 male male/male male_penetrated male_penetrating male_penetrating_male mammon_(helluva_boss) penetration penile penile_penetration penis penis_in_ass profanity sex simple_background socks teeth text
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
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2023 4_arms absurd_res anal anal_penetration antennae_(anatomy) anthro anthro_penetrated arthropod balls bee black_clothing black_legwear black_thigh_highs bow_ribbon breasts clothing collar demon demongirl_demoness digital_drawing_(artwork) digital_media_(artwork) duo genitals gynomorph gynomorph/male gynomorph_penetrated hair hand_on_leg hand_on_thigh hellaverse helluva_boss hi_res humanoid humanoid_on_anthro humanoid_penetrating humanoid_penetrating_anthro hymenopteran insect intersex intersex/male intersex_penetrated leash legwear male male_penetrating male_penetrating_gynomorph male_penetrating_intersex mammon_(helluva_boss) masturbating_while_penetrated masturbation multi_arm multi_limb nipples penetration penis ribbons sex simple_background spiked_collar spikes teeth thigh_highs white_eyes
2023 cigar clothed clothing demon digital_drawing_(artwork) digital_media_(artwork) duo empty_eyes green_eyes hellaverse helluva_boss humanoid male male/male mammon_(helluva_boss) saucymist teeth
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2023 4_arms black_clothing black_legwear black_thigh_highs cigar clothing controller demon digital_drawing_(artwork) digital_media_(artwork) hellaverse helluva_boss hi_res holding_cigar holding_controller holding_leash holding_object holding_remote_control humanoid kirkland897 leash legwear male mammon_(helluva_boss) multi_arm multi_limb remote_control simple_background solo teeth thigh_highs white_background
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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
1:1 2022 armwear black_wings breasts clothing criss09944084 crossgender demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes female green_hair hair hellaverse helluva_boss humanoid looking_at_viewer mammon_(helluva_boss) mtf_crossgender panties purple_clothing simple_background solo underwear white_background wings yellow_eyes
2023 4_arms clothing demon dialogue digital_drawing_(artwork) digital_media_(artwork) duo english_text feet genitals grey_background headgear headwear hellaverse helluva_boss hi_res holding_object holding_towel humanoid kirkland897 machine male mammon_(helluva_boss) mostly_nude multi_arm multi_limb penis robo_fizzarolli robot simple_background text towel
1:1 2022 black_wings breasts clothing criss09944084 crossgender demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes female green_hair hair hellaverse helluva_boss humanoid looking_at_viewer mammon_(helluva_boss) mtf_crossgender open_mouth purple_clothing solo white_body white_skin wings yellow_eyes
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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 4_arms black_clothing black_gloves black_handwear black_legwear black_thigh_highs boots cigar clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes footwear gesture gloves grey_background hand_gesture handwear hellaverse helluva_boss high_heeled_boots high_heels holding_cigar holding_object humanoid legwear male mammon_(helluva_boss) middle_finger multi_arm multi_limb overweight overweight_male pasties shoes simple_background sleepybud smoke solo thigh_boots thigh_highs yellow_eyes
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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
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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
2023 3:4 clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes exposed_back green_clothing green_eyes hellaverse helluva_boss hi_res humanoid looking_at_viewer lucifervalenti7 male mammon_(helluva_boss) ring_(jewelry) simple_background solo white_body white_skin
2022 4_arms black_clothing black_footwear black_gloves black_handwear black_shoes clothing demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes footwear gloves green_clothing green_eyes grey_background handwear hellaverse helluva_boss hi_res humanoid male mammon_(helluva_boss) multi_arm multi_limb shoes simple_background solo tan_clothing teeth wkydiamond51243
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