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anthro avian bird black_eyes clothing crossed_arms crown dialogue duo father formal_clothing formal_wear grey_background hair helluva_boss hi_res looking_away male owl owl_demon paimon_(helluva_boss) parent robe short_hair simple_background son standing stolas_(helluva_boss) teathekook text white_text age_difference anthro avian bird child cigarette clothing crown dialogue duo female formal_clothing formal_wear frown grey_background hair helluva_boss hi_res male monochrome owl owl_demon robe short_hair simple_background smile smoking smoking_cigarette speech_bubble stolas_(helluva_boss) teathekook text white_text young younger_female anthro avian bird black_text crown dialogue duo formal_clothing formal_wear frown grey_background hair helluva_boss hi_res looking_at_another looking_away male owl owl_demon short_hair simple_background standing stolas_(helluva_boss) teathekook text 2022 animal_humanoid anthro avian avian_demon avian_humanoid bird bird_humanoid black_and_white bust_portrait cloak clothed clothing crown demon demon_humanoid formal_clothing formal_wear helluva_boss hi_res humanoid looking_forward male mask monochrome owl owl_demon owl_humanoid paimon_(helluva_boss) portrait signature simple_background solo the_real_mr._big_d_98 traditional_media_(artwork) 2022 animal_humanoid anthro avian avian_demon avian_humanoid bird bird_humanoid clothed clothing comic crown demon demon_humanoid digital_drawing_(artwork) digital_media_(artwork) eyes_closed formal_clothing formal_wear helluva_boss humanoid humor male microphone norithelord owl owl_demon owl_humanoid paimon_(helluva_boss) red_eyes simple_background solo sparkles star watermark white_background 2022 animal_humanoid anthro avian avian_demon avian_humanoid bird bird_humanoid clothed clothing comic crown demon demon_humanoid dialogue digital_drawing_(artwork) digital_media_(artwork) english_text exclamation_point formal_clothing formal_wear helluva_boss humanoid humor male microphone norithelord offscreen_character open_mouth owl owl_demon owl_humanoid paimon_(helluva_boss) question question_mark red_eyes simple_background solo speech_bubble text watermark white_background 2022 animal_humanoid anthro avian avian_demon avian_humanoid bird bird_humanoid clothed clothing comic crown demon demon_humanoid dialogue digital_drawing_(artwork) digital_media_(artwork) english_text eyes_closed formal_clothing formal_wear gesture helluva_boss humanoid humor male microphone norithelord open_mouth owl owl_demon owl_humanoid paimon_(helluva_boss) red_eyes simple_background solo speech_bubble text watermark white_background 2022 animal_humanoid anthro avian avian_demon avian_humanoid bird bird_humanoid clothed clothing comic crown demon demon_humanoid dialogue digital_drawing_(artwork) digital_media_(artwork) english_text formal_clothing formal_wear gesture glowing glowing_eyes helluva_boss humanoid humor male microphone norithelord open_mouth owl owl_demon owl_humanoid paimon_(helluva_boss) raised_finger raised_index_finger red_eyes simple_background solo speech_bubble text watermark white_background yelling anthro avian bird black_clothing cigarette clothing formal_clothing formal_wear frown goth grey_background hair helluva_boss hi_res looking_at_viewer male messy_hair owl owl_demon red_eyes simple_background smoking solo standing stolas_(helluva_boss) teathekook teenager text watermark young anthro domestic_cat emily_erdos felid feline felis formal_clothing hi_res ice_skates ice_skating male mammal solo solo_focus spotlight tagme unknown_character anthro avian bird bone duo formal_clothing formal_wear frown grey_background hair hand_on_shoulder helluva_boss hi_res male melee_weapon mostly_offscreen_character neutral_expression owl owl_demon paimon_(helluva_boss) red_eyes short_hair simple_background skull stolas_(helluva_boss) sword teathekook teenager weapon young </3 anthro avian bird bodily_fluids crying eyes_closed formal_clothing formal_wear grey_background hair helluva_boss hi_res male monochrome musical_note owl owl_demon short_hair simple_background singing smile solo stolas_(helluva_boss) tears teathekook anthro avian bird black_text bodily_fluids canid canine canis crying dialogue formal_clothing formal_wear hair helluva_boss hi_res male mammal owl owl_demon short_hair simple_background smile solo standing stolas_(helluva_boss) tears teathekook text wolf anthro avian bird black_text bodily_fluids canid canine canis crying dialogue formal_clothing formal_wear frown hair helluva_boss hi_res male mammal owl owl_demon short_hair simple_background solo standing stolas_(helluva_boss) tears teathekook text wolf anthro avian bird black_text bodily_fluids canid canine canis crying dialogue formal_clothing formal_wear frown hair helluva_boss hi_res looking_at_viewer male mammal owl owl_demon short_hair simple_background solo standing stolas_(helluva_boss) tears teathekook text wolf anthro blep blue_eyes blue_necktie bottomwear clothed clothing coy digital_media_(artwork) dipstick_ears dipstick_fingers dipstick_tail dipstick_toes domestic_cat dress_pants dress_shirt egyptian_mau eyewear felid feline felis fluffy fluffy_tail formal_clothing formal_wear glasses grey_body hi_res looking_at_viewer male mammal markings multicolored_ears multicolored_tail necktie nixuelle pants shirt simple_background smile solo suit_vest tail_markings tongue tongue_out topwear wysdrem anthro avian bird black_background crown duo father father_and_child father_and_son formal_clothing formal_wear glowing helluva_boss hi_res looking_down magic male owl owl_demon paimon_(helluva_boss) parent parent_and_child red_eyes simple_background smile son stolas_(helluva_boss) teathekook trademark worried anthro avian bird blitzo_(helluva_boss) crescent_moon curtains detailed_background duo eye_patch eyewear formal_clothing formal_wear fur grey_body grey_fur hair helluva_boss hi_res horn imp looking_at_viewer male moon owl owl_demon pirate red_curtains red_eyes short_hair smile standing stolas_(helluva_boss) teathekook text uneven_eyes white_text yellow_eyes anthro avian bird black_text confusion crescent_moon crossed_arms dialogue formal_clothing formal_wear grey_background helluva_boss hi_res looking_at_viewer male moon owl owl_demon simple_background solo standing stolas_(helluva_boss) teathekook text uneven_eyes anthro avian bird blue_background blue_text dialogue duo eyes_closed formal_clothing formal_wear frown goth helluva_boss hi_res imp looking_down male owl owl_demon sad simple_background sitting stolas_(helluva_boss) teathekook text alcohol alcoholic_drink anthro avian beverage bird blue_text drinking father father_and_child father_and_son formal_clothing formal_wear goth group helluva_boss hi_res horn imp looking_down male owl owl_demon paimon_(helluva_boss) parent parent_and_child simple_background smoking son stolas_(helluva_boss) teathekook teenager text trio worried worried_face worried_look young anthro avian bird black_clothing clothing crossed_arms formal_clothing formal_wear frown goth grey_background helluva_boss hi_res looking_down male owl owl_demon red_eyes simple_background solo standing stolas_(helluva_boss) teathekook teenager text white_text young anthro avian bird black_eyes crossed_arms crown duo formal_clothing formal_wear goth helluva_boss hi_res holding_mirror holding_object looking_away male mirror moody owl owl_demon paimon_(helluva_boss) purple_text simple_background stolas_(helluva_boss) teathekook text alcohol andrealphus_(helluva_boss) anthro avian beverage bird clothing container crown cup danidrawsandstuff dress drinking drinking_glass female formal_clothing formal_wear furniture glass glass_container glass_cup group hat headgear headwear helluva_boss hi_res male owl owl_demon simple_background stella_(helluva_boss) stolas_(helluva_boss) table top_hat trio wine wine_glass animal_humanoid anthro arachnid arachnid_humanoid arthropod arthropod_humanoid avian bird blue_text clothing duo evil_grin eye_contact eyewear formal_clothing formal_wear frown glasses hat hazbin_hotel headgear headwear helluva_boss hi_res humanoid looking_at_another looking_down male owl owl_demon simple_background smile spider spider_humanoid standing stolas_(helluva_boss) teathekook text top_hat valentino_(hazbin_hotel) anthro avian beanie bird clothing crown eye_contact eyes_popping_out female formal_clothing formal_wear group hat headgear headwear helluva_boss hi_res lesbian_pride_colors lgbt_pride looking_at_another male octavia_(helluva_boss) owl owl_demon paimon_(helluva_boss) pink_text pride_color_flag pride_colors rainbow_flag rainbow_pride_flag rainbow_symbol simple_background stolas_(helluva_boss) teathekook text trio anthro avian bodily_fluids bovid butler caprine caught clothing deltarune dialogue dropping_object embarrassed formal_clothing froggyzoid_(artist) genital_fluids goat greyscale hi_res looking_pleasured male mammal messy monochrome omorashi peeing public ralsei relaxing shocked simple_background solo swatchling sweatdrop_(iconography) undertale_(series) urine video_games watersports wet wet_clothing wetting andrealphus_(helluva_boss) annoyed anthro arrogant avian bird blue_text clothing duo formal_clothing formal_wear from_behind_position frown hair helluva_boss hi_res male owl owl_demon sex short_hair simple_background smile stolas_(helluva_boss) teathekook text andrealphus_(helluva_boss) anthro avian bird duo formal_clothing formal_wear from_behind_position frown hair helluva_boss hi_res looking_down male monochrome owl owl_demon sad sex short_hair simple_background sitting stolas_(helluva_boss) teathekook anthro big_breasts black_bottomwear black_clothing black_skirt blue_body blue_tail bottomwear breasts cleavage_cutout clothing computer eeveelution eyewear female footwear formal_clothing generation_1_pokemon glasses high_heels holding_object laptop legwear long_tail nervous nintendo pokemon pokemon_(species) sally_(vusvox) secretary skirt solo stockings vaporeon video_games vusvox white_clothing <3 anthro avian bird blood_on_face formal_clothing formal_wear frown frowning_at_viewer grey_background helluva_boss hi_res looking_at_another male owl owl_demon red_eyes simple_background solo stolas_(helluva_boss) teathekook <3 anthro avian bird blood_on_face formal_clothing formal_wear frown frowning_at_viewer grey_background helluva_boss hi_res looking_at_another male owl owl_demon red_eyes simple_background solo splatter stolas_(helluva_boss) teathekook andrealphus_(helluva_boss) anthro avian bird blitzo_(helluva_boss) blue_background blue_text clothing formal_clothing formal_wear frown frustrated group hair helluva_boss hi_res holding_clothing holding_object horn imp male owl owl_demon red_text short_hair simple_background smile smirk standing stolas_(helluva_boss) teathekook text trio anthro avian bird blitzo_(helluva_boss) blue_background blue_text clothing duo formal_clothing formal_wear frown hair helluva_boss hi_res holding_clothing holding_object horn imp lying male on_back on_top owl owl_demon short_hair simple_background stolas_(helluva_boss) surprise surprised_expression teathekook text andrealphus_(helluva_boss) annoyed anthro avian bird blitzo_(helluva_boss) blue_background blue_text book crown eye_contact formal_clothing formal_wear group hair helluva_boss hi_res horn imp looking_at_another male owl owl_demon short_hair simple_background standing stolas_(helluva_boss) teathekook text trio andrealphus_(helluva_boss) angry anthro avian bird blitzo_(helluva_boss) blue_eyes blue_hair clothing crown detailed_background dress excited eye_contact female formal_clothing formal_wear grey_hair group hair helluva_boss hi_res imp kneeling long_hair looking_at_another male owl owl_demon pink_eyes red_eyes smile standing stella_(helluva_boss) stolas_(helluva_boss) teathekook white_hair yellow_eyes anthro avian bird clothing crown dress duo exclamation_point female formal_clothing formal_wear grey_background hair hi_res long_hair looking_forward male object_throw owl owl_demon paimon_(helluva_boss) plushie potrait queen_octavia_(teathekook) red_eyes simple_background smile standing surprise surprised_eyes teathekook text throwing_object thrown white_text anthro avian bird bodily_fluids crown crying duo formal_clothing formal_wear grey_background helluva_boss hi_res looking_down looking_up male owl owl_demon paimon_(helluva_boss) red_eyes shaking simple_background standing stolas_(helluva_boss) tears teathekook text white_text anthro avian bird cape clothing dress duo female formal_clothing formal_wear grey_text hair hi_res long_hair looking_away looking_down male owl owl_demon paimon_(helluva_boss) queen_octavia_(teathekook) red_eyes sad simple_background standing teathekook text anthro avian bird blue_text clothing crown dress duo female formal_clothing formal_wear frown hair helluva_boss hi_res long_hair looking_away male owl owl_demon queen_octavia_(teathekook) simple_background standing stolas_(helluva_boss) teathekook text worried anthro avian bird black_eyes blue_text crown duo excited father father_and_child father_and_son formal_clothing formal_wear frown helluva_boss hi_res male owl owl_demon paimon_(helluva_boss) parent parent_and_child simple_background smile son standing stolas_(helluva_boss) teathekook text anthro avian beanie bird blitzo_(helluva_boss) blue_text clothing comic cynthesia_07 daughter detailed_background driving father female formal_clothing formal_wear grey_hair group hair hand_covering_face hat headgear headwear helluva_boss hi_res husband imp long_hair male mother obscured_eyes octavia_(helluva_boss) owl owl_demon parent phone red_eyes sad simple_background sitting standing stella_(helluva_boss) stolas_(helluva_boss) text three_frame_image three_frame_sequence white_hair wife