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anthro avian bird bound cape clothing duo formal_clothing formal_wear grey_background hair helluva_boss hi_res imp looking_up lying male on_back on_top owl owl_demon short_hair simple_background stolas_(helluva_boss) striker_(helluva_boss) tail tail_motion teathekook wounded 2023 abs anal anal_penetration artist_name athletic athletic_male bar biceps big_butt big_penis black_pupils bodily_fluids bottom_heavy bow_tie bubble_butt butt butt_grab butt_squish clothing cowboy_hat demon demon_humanoid detailed_background duo eyes_closed facial_hair feet fingerless_gloves fingers genitals girly gloves hair hand_on_butt handwear hat headgear headwear helluva_boss hi_res horn horned_humanoid huge_butt humanoid imp inside long_tail male male/male muscular muscular_male mustache nude open_mouth parasitedeath pecs penetration penis pupils red_body red_skin sex sharp_teeth short_hair spade_tail spikes spikes_(anatomy) squish striker_(helluva_boss) sweat tail tan_body tan_skin teeth thick_thighs toes tongue tongue_out top_hat traditional_media_(artwork) wally_wackford watermark white_hair wide_hips 2022 4_fingers alligator alligatorid animatronic anthro artist_name axe black_clothing black_hair blush blush_lines bottomwear claws clothed clothing colored cowboy_hat crocodilian deltarune demon digital_media_(artwork) digital_painting_(artwork) dinosaur disney dragon eyebrows eyewear female fingerless_gloves fingers five_nights_at_freddy's five_nights_at_freddy's:_security_breach gloves green_body green_scales grey_body group hair hand_on_hip handwear hat headgear headwear helluva_boss hi_res holding_object horn human humanoid imp jacket lidded_eyes lizard long_hair long_neck long_tail looking_at_viewer machine male mammal melee_weapon monster montgomery_gator_(fnaf) multicolored_body multicolored_skin neckerchief necktie pants portrait purple_body purple_skin red_hair reptile robot rtootb scales scalie scottgames sharp_teeth shirt shoulder_pads simple_background simple_coloring sketch smile standing star_sunglasses star_vs._the_forces_of_evil steel_wool_studios striker_(helluva_boss) suit sunglasses susie_(deltarune) tail tall teeth toffee_(svtfoe) topless topless_anthro topless_male topwear torn_bottomwear torn_clothing two_tone_body two_tone_skin undertale_(series) weapon weapon_on_shoulder white_clothing white_topwear yellow_body yellow_eyes yellow_sclera yellow_skin <3 absurd_res angel big_penis blush bovid canid canid_demon canine canis caprine chart clothing collin_(helluva_boss) crotch_tuft demon english_text fluffy flustered foreskin genitals grin group halo hat headgear headwear hellhound helluva_boss hi_res humanoid_genitalia humanoid_penis imp knot leponsart long_penis male mammal penis penis_lineup penis_size_chart penis_size_difference pubes retracted_foreskin sheep simple_background small_penis smile striker_(helluva_boss) text thick_penis tongue tongue_out tuft vein veiny_penis vortex_(helluva_boss) wally_wackford wolf absurd_res andrealphus_(helluva_boss) anthro armpit_fetish armpit_play asmodeus_(helluva_boss) beanie blitzo_(helluva_boss) breasts cash_buckzo chaz_(helluva_boss) clothing crimson_(helluva_boss) fellatio female fizzarolli_(helluva_boss) gangbang group group_sex handjob hat headgear headwear helluva_boss hi_res incest_(lore) male male/female moxxie_(helluva_boss) octavia_(helluva_boss) oral paimon_(helluva_boss) penetration penile sebasdono sex stolas_(helluva_boss) striker_(helluva_boss) vortex_(helluva_boss) 3_fingers anthro bandanna clothed clothing fingers genitals helluva_boss hi_res horn humanoid imp kerchief male penis solo spiked_tail spikes spikes_(anatomy) striker_(helluva_boss) tail unknown_artist western anal anal_penetration anthro asphyxiation avian bedroom_eyes bird black_text choking clothing crown dialogue dominant dominant_female duo ejaculation eyelashes female grey_clothing grey_leggings grey_legwear grey_text hair handjob headgear helluva_boss horn imp leggings legwear long_eyelashes long_hair male male/female male_penetrated narrowed_eyes object_in_ass owl owl_demon pegging penetration penile potatonebula seductive sex sex_toy sex_toy_in_ass sex_toy_insertion sex_toy_penetration short_hair simple_background smile stella_(helluva_boss) striker_(helluva_boss) submissive submissive_male text tongue tongue_out toying_partner white_background anal anal_penetration anthro avian bedroom_eyes begging big_penis bird black_text breasts butt clothing collar dominant dominant_female duo eyelashes female genitals hair helluva_boss hi_res horn imp lingerie long_eyelashes long_hair male male/female male_penetrated moan narrowed_eyes nude object_in_ass owl owl_demon pegging penetration penis potatonebula seductive sex sex_toy sex_toy_in_ass sex_toy_insertion sex_toy_penetration short_hair smile stella_(helluva_boss) striker_(helluva_boss) submissive submissive_male text toying_partner 2023 anthro blazemizu boots bottomwear clothing cowboy_hat demon digital_media_(artwork) fingerless_gloves footwear gloves gun handwear hat headgear headwear helluva_boss imp lidded_eyes male neckerchief pants ranged_weapon sharp_teeth signature sitting solo striker_(helluva_boss) teeth torn_clothing weapon yellow_eyes abuse anal animal_humanoid anthro anus arms_tied bed bedroom bodily_fluids boots bound claws close-up clothing cowboy cuff_(restraint) cum cum_drip cum_in_ass cum_inside cum_on_penis demon demon_humanoid dominant dripping drooling duo ejaculation facial_hair fingerless_gloves footwear forced forced_anal forked_tongue freckles furniture genital_fluids genitals gloves handcuffs hands_behind_back hands_tied handwear hell helluva_boss helpless hi_res hoof_fetish hooves horn humanoid humiliation hybrid imp intimacy kidnapping male male/male metal_cuffs moxxie_(helluva_boss) mustache penis peril punishment red_body red_skin reptile reptile_humanoid restrained restraints revenge rosewhite saliva scalie scalie_humanoid scar sharp_claws sharp_teeth size_difference snake_humanoid spade_tail striker_(helluva_boss) striped_body stripes struggling submissive sunrise sweat sweatdrop tail tears teasing teeth tongue trapped undressed yellow_eyes anthro avian bird bodily_fluids demon duo female helluva_boss hi_res imp male male/female octavia_(helluva_boss) omegamax on_bottom on_top owl penetration reverse_cowgirl_position sex striker_(helluva_boss) sweat 2022 abs artist_name athletic athletic_humanoid athletic_male biceps boots bottomwear bulge claws clothed clothing cowboy cowboy_boots cowboy_hat crunkerton demon demon_humanoid detailed_background digital_drawing_(artwork) digital_media_(artwork) fence fingers footwear gesture gloves gold_(metal) gold_tooth hair handwear hat headgear headwear helluva_boss hi_res horn horned_humanoid humanoid imp long_tail looking_at_viewer low-angle_view male middle_finger muscular muscular_humanoid muscular_male nipples not_furry outside pants pecs scarf sharp_teeth signature smile solo spade_tail spikes spikes_(anatomy) straw straw_in_mouth striker_(helluva_boss) tail tan_body tan_skin teeth topless topless_humanoid topless_male torn_bottomwear torn_clothing torn_pants white_hair worm's-eye_view yellow_eyes yellow_sclera andrealphus_(helluva_boss) annoyed annoyed_expression anthro avian bird black_text blue_eyes clothing crown dress eyes_closed facepalm female formal_clothing formal_wear fur grey_text group growling hair headgear helluva_boss hi_res holding_tail imp lizsketches long_hair male orange_body orange_skin owl owl_demon short_hair simple_background stella_(helluva_boss) striker_(helluva_boss) tail text trio white_background white_body white_fur white_hair yellow_eyes yellow_teeth animated anthro avian big_breasts bird breasts duo elelite female genitals helluva_boss humanoid male nipples penetration penis pussy simpl stella_(helluva_boss) striker_(helluva_boss) vaginal vaginal_penetration bandolier big_butt blush bottomwear breath butt butt_cleavage butt_squish clothing cowboy_hat cutaway detailed_background duo english_text female fence grey_clothing grey_shirt grey_topwear hat headgear headwear helluva_boss hi_res huge_butt humanoid hyper hyper_butt imp male motion_lines necrofeline pants sallie_may_(helluva_boss) shirt speedo squish stretched_clothing stretched_pants striker_(helluva_boss) swimwear tan_jeans teasing text topwear torn_bottomwear torn_clothing torn_pants trans_(lore) wheat <3 aipeco18 balls blitzo_(helluva_boss) blush boots claws clothed clothing demon digital_media_(artwork) duo erection footwear genitals hair headgear headwear helluva_boss hi_res horn imp looking_at_viewer male male/male penis red_body reptile scalie simple_background snake striker_(helluva_boss) white_hair 2023 absurd_res anthro black_horn circusb0nes clothed clothing cloud crescent_moon demon digital_drawing_(artwork) digital_media_(artwork) hat headgear headwear helluva_boss hi_res horn imp jacket male moon multicolored_horn night reptile scalie snake solo striker_(helluva_boss) teeth topwear white_horn yellow_eyes anthro avian bandanna bird blitzo_(helluva_boss) blood blood_on_face blood_on_ground blood_on_weapon blood_splatter bodily_fluids boots bottomwear clothing corpse cowboy_boots cowboy_hat death defeated dialogue double_barrel_shotgun english_text engraving fatal fingerless_gloves footwear gloves gore group gun gun_smoke handwear hat headgear headwear helluva_boss holding_gun holding_object holding_shotgun holding_weapon horn humanoid imp keno9988 kerchief male missing_head morbid owl owl_demon pants ranged_weapon reptile rope scalie sharp_teeth shocked snake stolas_(helluva_boss) striker_(helluva_boss) tail teeth text tongue tongue_out torn_bottomwear torn_clothing torn_pants trio weapon absurd_res anthro avian bodily_fluids bound buzya chastity_device clothing cum cum_in_mouth cum_inside deep_throat dominant dominant_male duo forced genital_fluids genitals helluva_boss hi_res imp livestream male male/male male_penetrated male_penetrating male_penetrating_male oral owl_demon penetration penis rape recording running_makeup sex stolas_(helluva_boss) striker_(helluva_boss) torn_clothing absurd_res anthro avian bodily_fluids bound broken_rape_victim buzya chat clothing cum cum_in_mouth cum_inside cum_on_face dialogue dominant dominant_male duo finger_in_mouth forced genital_fluids genitals helluva_boss hi_res imp livestream male male/male oral owl_demon penetration penis presenting_mouth rape recording running_makeup sex stolas_(helluva_boss) striker_(helluva_boss) torn_clothing absurd_res alley anthro avian bodily_fluids bound bukkake buzya clothing cum cum_everywhere cum_from_ass cum_in_ass cum_in_mouth cum_inside cum_on_face dialogue dominant dominant_male duo forced genital_fluids genitals helluva_boss hi_res imp livestream male male/male messy owl_demon penis public_use rape recording sex solo stolas_(helluva_boss) striker_(helluva_boss) torn_clothing absurd_res anthro balcony beak blush body_blush breasts crown eyelashes feathers female fogata genitals headgear helluva_boss hi_res night pussy pussy_blush solo spanish_text star stella_(helluva_boss) striker_(helluva_boss) text white_body white_feathers arms_tied blush bodily_fluids boots bound claws close-up clothing cowboy cuff_(restraint) curtains demon dominant drooling duo evil_grin facial_hair fingerless_gloves footwear forced freckles gloves hair handcuffs hands_behind_back hands_tied handwear hell helluva_boss helpless hi_res hooves horn humanoid hybrid imminent_rape imp implied_rape kidnapping legwear male male/male metal_cuffs moxxie_(helluva_boss) mustache on_lap peril punishment red_body red_skin reptile restrained restraints revenge rosewhite saliva scalie scar sharp_claws sharp_teeth sitting_on_lap size_difference smile snake striker_(helluva_boss) striped_body stripes struggling sunset sweat sweatdrop tail tears teasing teeth thigh_highs trapped underwear undressing white_hair window wrist_cuffs yellow_eyes arms_tied blush bodily_fluids boots bound claws close-up clothing cowboy cuff_(restraint) curtains demon dominant drooling duo evil_grin facial_hair fingerless_gloves footwear forced freckles gloves hair handcuffs hands_behind_back hands_tied handwear hell helluva_boss helpless hi_res hooves horn humanoid hybrid imminent_rape imp implied_rape intimate kidnapping legwear male male/male metal_cuffs moxxie_(helluva_boss) mustache on_lap panties peril punishment red_body red_skin reptile restrained restraints revenge rosewhite saliva scalie scar sharp_claws sharp_teeth sitting_on_lap size_difference smile snake striker_(helluva_boss) striped_body stripes struggling sunset sweat sweatdrop tail tears teasing teeth thigh_highs trapped underwear undressing white_hair window wrist_cuffs yellow_eyes arms_tied blush bodily_fluids boots bound claws close-up clothing cowboy cuff_(restraint) curtains demon dominant drooling duo evil_grin facial_hair fingerless_gloves footwear forced freckles gloves hair handcuffs hands_behind_back hands_tied handwear hell helluva_boss helpless hi_res hooves horn humanoid hybrid imminent_rape imp implied_rape intimate kidnapping legwear male male/male metal_cuffs moxxie_(helluva_boss) mustache on_lap panties peril punishment red_body red_skin reptile restrained restraints revenge rosewhite saliva scalie scar sharp_claws sharp_teeth sitting_on_lap size_difference smile snake striker_(helluva_boss) striped_body stripes struggling struggling_prey submissive submissive_male sunset sweat sweatdrop tail tears teasing teeth thigh_highs trapped underwear undressing white_hair window wrist_cuffs yellow_eyes arms_tied blush bodily_fluids boots bound claws close-up clothing cowboy cuff_(restraint) curtains demon dominant drooling duo evil_grin facial_hair fingerless_gloves footwear forced freckles gloves hair handcuffs hands_behind_back hands_tied handwear hell helluva_boss helpless hi_res hooves horn humanoid hybrid imminent_rape imp implied_rape intimate kidnapping legwear male male/male metal_cuffs moxxie_(helluva_boss) mustache on_lap panties peril punishment red_body red_skin reptile restrained restraints revenge rosewhite saliva scalie scar sharp_claws sharp_teeth sitting_on_lap size_difference smile snake striker_(helluva_boss) striped_body stripes struggling sunset sweat sweatdrop tail tears teasing teeth thigh_highs trapped underwear undressing white_hair window wrist_cuffs yellow_eyes arms_tied blush bodily_fluids boots bound claws close-up clothing cowboy cuff_(restraint) curtains demon dominant drooling duo evil_grin facial_hair fingerless_gloves footwear forced freckles gloves hair handcuffs hands_behind_back hands_tied handwear hell helluva_boss helpless hi_res hooves horn humanoid hybrid imminent_rape imp implied_rape intimate kidnapping legwear male male/male metal_cuffs moxxie_(helluva_boss) mustache on_lap panties peril punishment red_body red_skin reptile restrained restraints revenge rosewhite saliva scalie scar sharp_claws sharp_teeth sitting_on_lap size_difference smile snake striker_(helluva_boss) striped_body stripes struggling sunset sweat sweatdrop tail tears teasing teeth thigh_highs trapped underwear undressing white_hair window wrist_cuffs yellow_eyes 2023 2:3 4_fingers black_hair camel_toe carliabot clothed clothing crossgender demon dialogue duo english_text erection erection_under_clothing female fingers hair hat headgear headwear helluva_boss hi_res horn imp male male/female moxxie_(helluva_boss) open_mouth striker_(helluva_boss) text tongue white_hair <3 2023 2:3 4_fingers areola black_hair breasts breath camel_toe carliabot clothed clothing crossgender demon dialogue duo english_text erection erection_under_clothing female fingers genitals hair hat headgear headwear helluva_boss hi_res horn imp male male/female moxxie_(helluva_boss) navel nipples onomatopoeia open_mouth penetration penile penile_penetration penis penis_in_pussy plap pussy red_penis sex sharp_teeth sound_effects striker_(helluva_boss) teeth text tongue tongue_out vaginal vaginal_penetration white_hair 2022 absurd_res black_bottomwear black_clothing black_pants bottomwear chair cigarette clothing demon digital_drawing_(artwork) digital_media_(artwork) distracting_watermark duo footwear furniture green_eyes hair helluva_boss hi_res horn humanoid imp larger_male male mammon_(helluva_boss) pants reptile scalie shoes sinnamon-bun sitting size_difference smaller_male snake striker_(helluva_boss) teeth torn_clothing watermark white_bottomwear white_clothing white_hair white_pants yellow_eyes bodily_fluids clothing cum cum_in_ass cum_inside ejaculation genital_fluids hat hat_only headgear headgear_only headwear headwear_only helluva_boss hi_res hooves horn imp male mostly_nude ns4w_negative penetration scarf scarf_only sharp_teeth solo striker_(helluva_boss) submissive submissive_male tail teeth 2022 anthro bottomwear circusb0nes clothing demon digital_drawing_(artwork) digital_media_(artwork) gun hair handgun helluva_boss hi_res holding_gun holding_handgun holding_object holding_pistol holding_weapon horn imp male multicolored_horn pants pistol ranged_weapon red_body red_skin reptile scalie snake solo striker_(helluva_boss) teeth torn_bottomwear torn_clothing torn_pants weapon white_hair yellow_eyes 2021 anthro boots bulge butt clothing cowboy demon digital_drawing_(artwork) digital_media_(artwork) footwear fur hair hat headgear headwear helluva_boss hi_res imp lasso looking_at_viewer looking_back male monster neckerchief pink_body pink_skin rickityrabbit shaded sharp_teeth simple_background slim small_butt smile smug solo spade_tail striker_(helluva_boss) teeth underwear white_body white_fur white_hair anthro book casual_conversation cellphone chaz_(helluva_boss) demon dialogue duo english_text fish helluva_boss horn imp line_art lying male marine phone pissabelle reptile scalie shark sitting snake striker_(helluva_boss) text angry anthro avian beach bird clothing dialogue eye_contact eyes_closed female fight group hair helluva_boss hi_res horn imp long_hair looking_at_another male one-piece_swimsuit owl owl_demon pink_background sallie_may_(helluva_boss) seaside simple_background sitting smile stella_(helluva_boss) striker_(helluva_boss) sun_hat swimwear teathekook text trio white_text chaz_(helluva_boss) fish green_body green_hair group hair helluva_boss horn imp licking male male/male marine mhaelt moxxie_(helluva_boss) red_body reptile scalie scar shark shirtless shirtless_male snake striker_(helluva_boss) teeth tongue tongue_out trio white_hair albablue777 blitzo_(helluva_boss) body_hair chaz_(helluva_boss) demon fish group hair helluva_boss horn imp male male/male marine moxxie_(helluva_boss) muscular muscular_male pose reptile scalie scar shark shirtless shirtless_male slim smile snake striker_(helluva_boss) tongue angry bow_tie chaz_(helluva_boss) clothing cowboy cowboy_hat demon dvdf_1005 fish flirting formal_wear group hair hat headgear headwear helluva_boss horn imp male marine moxxie_(helluva_boss) reptile scalie shark size_difference smile snake striker_(helluva_boss) teeth trio white_hair absurd_res akirerosales angel_dust anthro avian beak bird black_body black_boots black_boxer_briefs black_clothing black_footwear black_fur black_hair black_legwear black_lipstick black_nose black_speedo black_stockings black_swimwear black_thigh_highs black_underwear blush boots bottomwear boxer_briefs bra breasts butt canid canid_demon canine canis cigar claws clothed clothing demon eye_scar eyelashes facial_hair facial_scar fangs feathers female fluffy fluffy_tail footwear freckles fur grey_body grey_fur grey_hair group hair hands_in_lap hands_on_shoulders harem hazbin_hotel hellhound helluva_boss hi_res hooves horn humanoid imp larger_female larger_male legwear lipstick loona_(helluva_boss) lying makeup male male/female male/male mammal millie_(helluva_boss) moxxie_(helluva_boss) multi_arm multi_limb muscular muscular_male mustache nipples on_side open_mouth open_smile owl owl_demon panties pants partially_clothed pawpads paws piercing pink_body pink_fur pink_hair purple_bra purple_clothing purple_panties purple_underwear red_body red_eyes red_sclera red_skin scar screen screen_face simple_background sitting_in_lap size_difference smaller_male smile smoking spade_tail speedo stella_(helluva_boss) stockings striker_(helluva_boss) swimwear tan_body teeth television thigh_highs toe_claws tongue tongue_out tooth_gap topless topless_male topwear torn_bottomwear torn_clothing torn_pants underwear verosika_mayday_(helluva_boss) vortex_(helluva_boss) vox_(hazbin_hotel) white_body white_feathers white_fur white_hair wings wolf yellow_sclera andrealphus_(helluva_boss) anthro avian bird black_text brother brother_and_sister clothing crossed_arms crown dialogue dress eyelashes eyes_closed female frown grey_background group hair helluva_boss hi_res horn imp long_eyelashes long_hair male owl owl_demon scarf sibling simple_background sister speech_bubble stella_(helluva_boss) striker_(helluva_boss) teathekook text trio abdominal_bulge absurd_res anthro belly belly_expansion belly_inflation digital_drawing_(artwork) digital_media_(artwork) egg egg_bulge egg_inflation expansion feeding force_feeding forced forced_vore hell helluva_boss hi_res imp inflation male oviposition reptile salh scalie snake solo striker_(helluva_boss) unwilling_pred unwilling_vore vore <3 anthro balls black_hair blush bodily_fluids breasts butt claws clothing cum cum_in_pussy cum_inside demon demon_humanoid detailed_background duo fangs female female_penetrated french_kissing from_behind_position genital_fluids genitals gloves group hair handwear helluva_boss hi_res horn humanoid imp infidelity intraspecies kissing kojot looking_pleasured male male/female male_penetrating male_penetrating_female millie_(helluva_boss) nipples on_bottom on_top open_mouth open_smile orange_body penetration penile penile_penetration penis_in_pussy pillow pussy red_body saliva sex smile spoon_position spooning striker_(helluva_boss) text tongue tongue_out vaginal vaginal_penetration white_hair yellow_eyes