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monochrome sketch spade_tail tail text accessory anthro blush bow_ribbon clothed clothing duo english_text female hair hair_accessory hair_bow hair_ribbon helluva_boss hi_res horn imp lewdchuu_(artist) male mitzy_(lewdchuu) monochrome ribbons sitting sketch spade_tail striker_(helluva_boss) tail text accessory anthro bow_ribbon breasts clothing crimson_(helluva_boss) duo english_text female hair_accessory hair_bow hair_ribbon helluva_boss hi_res horn imp lewdchuu_(artist) maid_uniform male mitzy_(lewdchuu) monochrome ribbons shirt simple_background sketch spade_tail tail text thought_bubble topwear uniform white_background anthro big_breasts breasts clothing duo english_text female hat headgear headwear helluva_boss hi_res horn huge_breasts imp lewdchuu_(artist) male mitzy_(lewdchuu) monochrome scarf sketch spade_tail striker_(helluva_boss) tail text uniform anthro big_breasts big_butt blush bottomwear breasts butt clothing duo english_text female helluva_boss hi_res horn huge_breasts huge_butt imp lewdchuu_(artist) male mitzy_(lewdchuu) monochrome shirt shorts sketch spade_tail striker_(helluva_boss) tail text topwear anthro clothing food hair helluva_boss hi_res horn imp lewdchuu_(artist) male pink_body pizza red_clothing scarf shirt solo spade_tail striker_(helluva_boss) tail topwear white_hair yellow_eyes accessory anthro big_breasts black_hair bottomwear bow_ribbon breasts clothing english_text female hair hair_accessory hair_bow hair_ribbon hi_res horn imp lewdchuu_(artist) mitzy_(lewdchuu) necktie red_body red_eyes ribbons shirt skirt solo spade_tail tail text topwear balls black_hair crossgender demon ftm_crossgender genitals hair hands_behind_back helluva_boss hi_res horn humanoid imp kneeling male millie_(helluva_boss) nipples penis pillow poraka7 red_body red_skin solo thick_thighs anthro big_breasts breasts dialogue english_text female hair helluva_boss hi_res horn huge_breasts imp lewdchuu_(artist) male monochrome sketch solo striker_(helluva_boss) text 5_fingers 5_toes absurd_res blitzo_(helluva_boss) butt claws duo feet fingers fizzarolli_(helluva_boss) helluva_boss hi_res horn humanoid imp male male/male nude sparksstars toes 5_fingers 5_toes absurd_res blitzo_(helluva_boss) burns butt claws duo feet fingers fizzarolli_(helluva_boss) helluva_boss hi_res horn humanoid humanoid_feet imp male male/male nude plantigrade robotic_arm robotic_leg sparksstars toes animated anthro big_breasts bikini black_hair bouncing_breasts breasts canid canid_demon canine cleavage clothed clothing collar creatiffy demon digital_media_(artwork) duo english_text female fur gloves hair handwear hellhound helluva_boss hi_res horn humanoid imp legwear looking_at_viewer loona_(helluva_boss) mammal millie_(helluva_boss) mythological_canine mythological_creature mythology outside poolside red_body red_sclera short_playtime simple_background smile stockings swimwear tail teeth text thick_thighs topwear under_boob white_body white_fur yellow_sclera anthro avian ball_gag bdsm bird blitzo_(helluva_boss) bodily_fluids bondage bondage_gear bound chest_tuft cuddling demon duo emoji gag head_on_chest heart_eyes heart_symbol helluva_boss helluvaboss hi_res horn horn_grab humanoid imp male male/male meme muscular muscular_male owl owl_demon reachahighernoon restraints romantic romantic_couple stolas_(helluva_boss) straitjacket tears tears_of_pleasure tuft black_blood blood bodily_fluids chimeracocks clothed clothing colored_blood demon duo erection erection_under_clothing female female/female helluva_boss hi_res holding_head humanoid imp incest_(lore) knife_play millie_(helluva_boss) sallie_may_(helluva_boss) tail tail_around_leg tail_around_neck trans_(lore) trans_woman_(lore) unusual_blood unusual_bodily_fluids abstract_background anthro avian bird bodily_fluids bovid caprine caprine_demon clothing cluster_fuck confusion demon dragon ducktape_lizard_inc enfer_belial erection european_mythology forced_perspective girly goat_demon greek_mythology gremile_'hotshot' group imp magician mal_leviathan male male/male mammal muscular mythological_avian mythological_bird mythological_creature mythological_firebird mythological_scalie mythology phenex_(kings_of_hell) phoenix scalie speech_bubble speedo sweat sweatdrop swimwear text animated bestiality biggcuties canid canine canis duo female female_on_feral feral forced humanoid imp link_(wolf_form) male male/female mammal midna morpskorp nintendo rape the_legend_of_zelda twilight_princess wolf 2024 5_fingers anthro asphyxiation bed bedroom black_hair black_nose blush bodily_fluids breasts canid canid_demon canine choking clothing comic demon drooling english_text female fingering fingerless_gloves fingers fur furniture gloves grey_body grey_fur group hair handwear hellhound helluva_boss hi_res horn humanoid humanoid_hands humanoid_on_humanoid husband_and_wife imp loona_(helluva_boss) male male/female mammal married_couple millie_(helluva_boss) moxxie_(helluva_boss) multicolored_body multicolored_fur mythological_canine mythological_creature mythology nipples nude on_bed orgasm red_body red_sclera red_skin saliva sex silver_hair star_eyes swain_(artist) sweat teeth text tongue tongue_out trio two_tone_body two_tone_fur url vaginal vaginal_fingering white_body white_eyes white_fur white_hair animal_genitalia animal_penis bestiality biggcuties canid canine canine_genitalia canine_penis canis duo female female_on_feral feral forced genitals hi_res human imp link_(wolf_form) male male/female mammal midna morpskorp nintendo penis rape short_stack text the_legend_of_zelda twilight_princess wolf animal_genitalia anthro avian bird bird_demon breast_grab breast_squeeze breasts censored cloaca danidrawsandstuff demon duo feathers female galliform genitals grey_body grey_feathers hair hand_on_breast helluva_boss hi_res humanoid imp kiss_on_lips male male/female masturbation peafowl peafowl_demon penetration penis phasianid squish stella_(helluva_boss) striker_(helluva_boss) 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imp_(doom) knife larger_female looking_at_another looking_at_partner looking_down looking_down_at_another looking_down_at_partner looking_up looking_up_at_another looking_up_at_partner male male/female mammal mtf_crossgender multicolored_body multicolored_skin muscular muscular_female one_eye_obstructed open_mouth orange_body orange_skin orgasm pants partially_clothed penetration penile penile_penetration penis penis_in_pussy portrait power_tool questionable_consent red_eyes saladbearer scared sex shell_(projectile) shotgun_shell size_difference smaller_male submissive submissive_male teeth text tight_clothing tools torn_bottomwear torn_clothing torn_pants two_tone_body two_tone_skin vaginal vaginal_penetration visor weapon alongmouf anthro big_butt bulge butt clothing cowboy_hat demon gremile_'hotshot' gun handgun hat headgear headwear holster imp kings_of_hell leotard male pistol ranged_weapon short_stack solo thick_thighs weapon areola bracelet bracelet_only breasts cowlick eclair_(spicymancer) eyewear eyewear_only female freckles full-length_portrait genitals glasses glasses_only gold_(metal) gold_bracelet gold_jewelry hair hi_res horn horned_humanoid huffslove humanoid humanoid_pointy_ears imp jewelry nipples notebook nude pencil_(object) portrait pubes purple_areola purple_body purple_hair purple_nipples purple_skin pussy short_hair short_stack simple_background small_waist smile solo standing tome_imp unguligrade_legs wearing_glasses wide_hips 2022 2_horns abstract_background beauty_mark big_butt black_eyes black_hair buckteeth butt demon eyebrows eyelashes female genitals hair helluva_boss hi_res horn humanoid imp juggertuul looking_at_viewer millie_(helluva_boss) not_furry pussy red_body red_skin short_hair smile solo spade_tail tail teeth thick_thighs wide_hips yellow_sclera absurd_res anal anal_penetration big_butt butt clothing deltarune duo faceless_character faceless_male fauxtellno1 fool's_hat hat headgear headwear hi_res humanoid imp jester jevil_(deltarune) looking_back male male/male not_furry penetration short_stack tail undertale_(series) 2024 absurd_res black_hair clothing demon demon_humanoid female fishnet fishnet_legwear hair helluva_boss hi_res horn humanoid imp jizoku legwear looking_at_viewer millie_(helluva_boss) not_furry red_body solo striptease 2024 anonymous_artist barefoot black_eyes black_hair bodily_fluids bow_tie breasts clothing demon embarrassed feet female flat_colors fool's_hat genitals hair hat headgear headwear helluva_boss hi_res humanoid imp impni jester looking_away lying medium_breasts mostly_nude nervous nipples noseless not_furry on_back parody_character pubes pussy red_body red_skin short_hair simple_background solo space_king spade_tail sweat tail tailed_humanoid white_background yellow_sclera 2024 anonymous_artist arm_support barefoot beach black_eyes border breasts brown_hair cleavage clothed clothing cute_fangs day demon dreadlocks eating eating_food feet female flat_colors food food_in_mouth fool's_hat full-length_portrait furrowed_brow hair hat headgear headwear hi_res holding_food holding_object humanoid imp impni jester leaning_on_elbow looking_at_viewer lying medium_breasts noseless not_furry on_back one-piece_swimsuit parody_character popsicle portrait question_mark reclining red_body red_skin sand short_hair sky solo space_king spade_tail swimwear tail tailed_humanoid water white_border white_clothing white_swimwear yellow_sclera 2024 anthro ass_up biped black_hair black_horn blue_background blue_bottomwear blue_clothing blue_jeans blue_pants blush bottomwear breasts clothed clothing demon denim denim_bottomwear denim_clothing female fingers hair helluva_boss hi_res horn humanoid imp jeans lips long_tail looking_at_viewer lying millie_(helluva_boss) pants red_body red_breasts red_lips red_skin red_tail short_hair simple_background solo squaresville tail yellow_eyes 2024 2_horns anal anal_masturbation anal_penetration anthro anus areola biped black_hair black_horn black_lips blue_background blush breasts demon dildo female fingers genitals hair helluva_boss horn humanoid humanoid_genitalia humanoid_pussy imp lips long_tail masturbation millie_(helluva_boss) nipples nude on_ground one_eye_closed open_mouth penetration pink_areola pink_nipples pussy red_body red_breasts red_pussy red_skin red_tail sex_toy short_hair simple_background sitting solo squaresville tail toying_self yellow_eyes absurd_res anthro balls demon genitals hair helluva_boss hi_res horn humiliation imp looking_at_viewer male moxxie_(helluva_boss) penis penis_humiliation red_body rotten_owl simple_background small_penis small_penis_humiliation solo tail text traditional_media_(artwork) white_background white_hair absurd_res anal bodily_fluids cum cum_on_face demon doggystyle double_penetration excessive_cum excessive_genital_fluids female from_behind_position genital_fluids genitals goopyarts group group_sex hi_res imp male orgasm orgy penetration penis sex threesome vaginal absurd_res anthro anthro_on_anthro areola bandai_namco bent_over big_breasts bodily_fluids breasts canid canine coyotek cum cum_drip cum_in_pussy cum_inside digimon digimon_(species) dripping female fox genital_fluids genitals group group_sex hair hair_down hand_on_butt hand_on_hip hi_res hot_spring human human_on_anthro humanoid imp impmon interspecies leaking_cum male male/female mammal nipples nude one_eye_closed penetration penile penile_penetration penis penis_in_pussy red_hair renamon rika_nonaka sex threesome trio vaginal vaginal_penetration water anal anal_penetration anthro anus backsack balls blep blue_eyes bodily_fluids book bookshelf bottomless bottomless_anthro bottomless_male bottomless_sex butt casual_sex claws clothed clothing clothing_on_floor collar cum cum_in_ass cum_inside curtains curtains_open digital_media_(artwork) dipstick_ears dipstick_fingers dipstick_tail disptick_toes domestic_cat domestic_ferret dresser dresser_drawer duo ejaculation erection eyewear felid feline felis fur furniture geary genital_fluids genitals glasses grey_body hair head_down_ass_up hi_res hybrid imp inside magic_user male male/male male_penetrated male_penetrating male_penetrating_male mammal markings multicolored_ears multitasking mustelid musteline nixuelle otter paws_on_butt penetration penile penile_penetration penis penis_in_ass pink_nose poncho raised_tail reading reading_book red_eyes sash scroll semi_public sex smile smirk spots spotted_markings tail tail_markings teeth tongue tongue_out topwear true_musteline vampirika wand weasel white_body window window_light animal_humanoid anthro avian avian_feet avian_humanoid bird blitzo_(helluva_boss) bone cape cigarette clothing demon demon_humanoid demonic duo feathers height helluva_boss hi_res hooves horn humanoid imp male male/male mintwo owl owl_demon red_body red_eyes royalty size_difference skull smoking smoking_cigarette spade_tail stolas_(helluva_boss) tail tail_feathers 2024 2:3 5_fingers anthro black_body black_fur breasts canid canid_demon canine carliabot cellphone clothing collar comic demon dialogue duo electronics english_text erection female fingerless_gloves fingers fur furniture gloves grey_hair hair handwear heart_eyes heart_symbol hellhound helluva_boss hi_res holding_cellphone holding_object holding_phone holding_smartphone imp legwear loona_(helluva_boss) male mammal midriff moxxie_(helluva_boss) mythological_canine mythological_creature mythology on_sofa open_mouth phone potion potion_bottle red_body red_sclera red_skin sitting sitting_on_sofa smartphone sofa speech_bubble spiked_collar spikes text tongue url white_body white_fur white_hair yellow_sclera anal anal_penetration animal_genitalia animal_penis anthro big_macintosh_(mlp) cutie_mark demon duo earth_pony equid equine equine_genitalia equine_penis friendship_is_magic genitals hasbro helluva_boss hi_res horn horse humanoid imp male male/male mammal melthoras_den moxxie_(helluva_boss) 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