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formal_wear group headgear helluva_boss hi_res imp male owl owl_demon paimon_(helluva_boss) parent parent_and_child sad scared simple_background son standing stolas_(helluva_boss) tears teathekook trio wounded anthro avian bird black_background bodily_fluids crown crying dialogue duo father father_and_child father_and_son formal_clothing formal_wear headgear helluva_boss hi_res looking_at_viewer male owl owl_demon paimon_(helluva_boss) parent parent_and_child red_text sad scared simple_background son standing stern stern_look stolas_(helluva_boss) tears teathekook text anthro avian bird book chair child clothed clothing container cup dialogue duo father father_and_child father_and_son furniture grey_background helluva_boss hi_res looking_away looking_up male owl owl_demon paimon_(helluva_boss) parent parent_and_child simple_background sitting son stolas_(helluva_boss) table teathekook text white_text young anthro avian bird cape clothing dialogue duo eye_contact father father_and_child father_and_son formal_clothing formal_wear frown grey_background helluva_boss hi_res looking_at_another looking_down looking_up male owl owl_demon paimon_(helluva_boss) parent parent_and_child scared simple_background son stolas_(helluva_boss) teathekook text threat threatening white_text anthro avian bird child clothing crossed_arms dialogue dress father father_and_child father_and_son female formal_clothing formal_wear grey_background group hair helluva_boss hi_res husband husband_and_wife long_hair looking_away male married_couple mother mother_and_child mother_and_son owl owl_demon paimon_(helluva_boss) parent parent_and_child queen_octavia_(teathekook) short_hair simple_background sleeping son speech_bubble standing stolas_(helluva_boss) teathekook text trio white_text wife worried young absurd_res anthro helluva_boss hi_res male rolling_beast solo stolas_(helluva_boss) angry anthro avian bird bodily_fluids crossed_arms crown crying father father_and_child father_and_son female formal_clothing formal_wear grey_background group hair headgear helluva_boss hi_res holding_another holding_child hurt_expression husband husband_and_wife long_hair male married_couple owl owl_demon paimon_(helluva_boss) parent parent_and_child queen_octavia_(teathekook) sad scared short_hair simple_background son stolas_(helluva_boss) tears teathekook trio wife anthro avian bird child dialogue duo facial_hair formal_clothing formal_wear grey_background hair helluva_boss hi_res hiding imp looking_down male mustache owl owl_demon plushie sad short_hair simple_background sitting stolas_(helluva_boss) teathekook text white_text young anthro avian beak bed big_butt bird blue_body blue_feathers butt clothed clothing demon digital_media_(artwork) feathers footwear furniture gwizzly helluva_boss hi_res hoodie huge_butt legwear looking_at_viewer looking_back male on_ground owl owl_demon red_eyes smile solo stolas_(helluva_boss) thick_thighs thigh_highs topwear 2023 4_eyes after_anal after_sex anthro anus avian beak big_butt bird blitzo_(helluva_boss) bodily_fluids butt clothing cum cum_in_ass cum_inside demon demon_humanoid duo english_text feathers gaping gaping_anus genital_fluids helluva_boss hi_res horn humanoid humanoid_on_anthro humor imp legs_up legwear looking_at_viewer lying male male/male meme multi_eye nude on_back owl owl_demon pun reaction_image red_background salamikii shitpost silly_face simple_background smile stolas_(helluva_boss) text thick_thighs thigh_highs 2023 ambiguous_gender anthro avian beak biped blush demon dialogue english_text helluva_boss hi_res looking_at_viewer open_mouth oro97 profanity red_sclera simple_background solo stolas_(helluva_boss) text texting <3 3_toes alcohol anthro avian belly beverage big_feet bird black_lips boots bottle bulge chubby_male claws clothing collar container demon digital_media_(artwork) duo feet foot_fetish footwear furniture girly gloves glowing hair handwear hell helluva_boss hi_res huge_feet humanoid inside jacket kangaroo lamp latex leash leg_cuff legwear licking lips looking_down looking_down_at_partner lying macropod male male/male mammal marsupial mesh_shirt on_back open_mouth rubber rubber_clothing rubber_suit rug sitting sofa stolas_(helluva_boss) teeth thigh_highs toe_claws toes tongue tongue_out topwear veyen wine xdarkspace abdominal_bulge absurd_res anal anal_orgasm anal_penetration anthro anthro_penetrated arms_bent arms_tied armwear avian balls balls_deep balls_touching bdsm belly_riding belt bent_legs big_butt bird black_sclera blush bodily_fluids bondage bottomwear bound butt canid canid_demon canine chair clothed clothing cum cum_drip cum_in_ass cum_in_mouth cum_inflation cum_inside cum_on_balls cum_on_face cum_on_penis cum_on_self cum_on_tongue cum_while_penetrated demon desk digital_media_(artwork) drinking drinking_cum dripping duo ejaculation elbow_gloves erection fannypacking feathered_wings feathers feet feet_on_balls fellatio fluffy fluffy_tail foot_fetish foot_play footwear forced forced_oral forced_orgasm foreskin fucked_silly fur furniture genital_fluids genitals girly gloves grin hair hair_over_eye hair_over_eyes half-closed_eyes hands-free handwear hellhound helluva_boss hi_res humanoid_genitalia humanoid_penis inflation knotting leather leather_clothing leather_legwear leather_stockings leather_straps legs_tied legwear long_tongue looking_at_viewer looking_pleasured loona_(helluva_boss) male male/male male_penetrated male_penetrating male_penetrating_male mammal mostly_nude multi_eye muscular muscular_male musk narrowed_eyes nude office office_chair office_sex one_eye_obstructed open_mouth oral oral_penetration orgasm oro97 owl owl_demon penetration penile penile_penetration penis precum red_eyes red_sclera rough_sex sex shaking shirt shuddering simple_background size_difference sloppy_seconds smile smoke stockings stolas_(helluva_boss) submissive swallowing swallowing_sound_effect sweat sweaty_balls sweaty_genitalia sweaty_legs sweaty_penis sweaty_thighs table tail tentacle_penetration tentacle_sex tentacles text text_message text_messaging thick_thighs thigh_highs time_lapse tongue tongue_out topwear torn_fabric trembling uncut_dick wallpaper_(decoration) white_body white_fur wide_hips wings zerva_von_zadok_(capesir) anthro avian bird blitzo_(helluva_boss) crown dialogue eyes_closed father father_and_child father_and_son formal_clothing formal_wear frown globe group hair headgear helluva_boss hi_res imp looking_away male owl owl_demon paimon_(helluva_boss) parent parent_and_child purple_background short_hair simple_background sitting smile son speech_bubble standing stolas_(helluva_boss) teathekook text trio white_text anthro anthro_on_anthro avian bird black_body black_feathers blitzo_(helluva_boss) blush breasts claws crossgender demon dialogue duo english_text feathers female female/female fluffy fluffy_tail fur helluva_boss hi_res horn imp interspecies mature_female multicolored_body multicolored_fur owl red_body red_eyes romantic simple_background skeleslay smile stolas_(helluva_boss) tail text thick_thighs two_tone_body white_background white_body anthro anthro_on_anthro avian bed bird blitzo_(helluva_boss) blush breasts claws crossgender demon duo feathers female female/female fluffy fluffy_tail fur furniture grey_body grey_feathers hand_on_breast helluva_boss hi_res horn imp interspecies mature_female multicolored_body multicolored_fur on_bed owl owl_demon red_body red_eyes romantic simple_background skeleslay smile stolas_(helluva_boss) tail thick_thighs traditional_media_(artwork) two_tone_body white_background white_body anthro anthro_on_anthro avian bed bird blitzo_(helluva_boss) blush breasts claws crossgender demon duo feathers female female/female fluffy fluffy_tail fur furniture genitals grey_body grey_feathers helluva_boss hi_res horn imp interspecies mature_female multicolored_body multicolored_fur nipples on_bed open_mouth open_smile owl owl_demon pussy red_body red_eyes romantic simple_background skeleslay smile stolas_(helluva_boss) tail thick_thighs traditional_media_(artwork) two_tone_body white_background white_body anthro avian big_butt bird blush breasts butt claws clothed clothing crossgender demon eyewear fangs feathers female fur glasses grey_body grey_feathers helluva_boss multi_eye open_mouth owl owl_demon panties partially_clothed red_eyes simple_background skeleslay solo stolas_(helluva_boss) teeth thick_thighs traditional_media_(artwork) underwear andrealphus_(helluva_boss) anthro avian bird book brother brother_and_sister bully bullying clothing crown dress evil_grin female formal_clothing formal_wear frown grey_background group hair headgear helluva_boss hi_res laugh long_hair looking_down looking_up male owl owl_demon plushie ponytail reaching reaching_out short_hair sibling simple_background sister smile stella_(helluva_boss) stolas_(helluva_boss) teathekook trio anthro avian bird clothing dialogue ellipsis frown grey_background helluva_boss hi_res magic magic_user male on_phone owl owl_demon phone pillow robe simple_background sitting solo speech_bubble stolas_(helluva_boss) teathekook text towel towel_on_head white_text andrealphus_(helluva_boss) anthro avian bird brother brother_and_sister cape clothing crossed_arms crown dress eye_contact female formal_clothing formal_wear frown grey_background group hat headgear headwear helluva_boss hi_res looking_at_another male owl owl_demon sibling simple_background sister smile standing stella_(helluva_boss) stolas_(helluva_boss) teathekook top_hat trio andrealphus_(helluva_boss) anthro avian bird cape clothing dialogue eye_contact female formal_clothing formal_wear frown grey_background group hair hat headgear headwear helluva_boss hi_res insult long_hair looking_at_another male owl owl_demon short_hair simple_background standing stella_(helluva_boss) stolas_(helluva_boss) teathekook text top_hat trio white_text andrealphus_(helluva_boss) anthro avian bird bound cape clothing crown dialogue duo evil_grin formal_clothing formal_wear frown grey_background hair headgear helluva_boss hi_res holding_another male owl owl_demon rope short_hair simple_background smile speech_bubble stolas_(helluva_boss) teathekook text white_text anthro anthro_on_anthro anus avian bird black_body black_feathers blitzo_(helluva_boss) blue_body blue_feathers blush bodily_fluids breast_grab breast_play breast_suck breasts claws crossgender demon dominant dominant_female duo feathers female female/female fluffy fluffy_tail fur genital_fluids genitals hand_on_breast helluva_boss hi_res horn imp interspecies looking_pleasured masturbation mature_female multicolored_body multicolored_fur nipples open_mouth open_smile owl pussy pussy_juice red_body red_eyes romantic saliva simple_background skeleslay smile stolas_(helluva_boss) submissive submissive_female sucking tail tongue two_tone_body vaginal vaginal_masturbation white_background white_body anthro avian bird cape clothing detailed_background formal_clothing formal_wear fur grey_body grey_fur grey_hair group hair hat headgear headwear helluva_boss hi_res lanveril looking_at_viewer male neutral_expression owl owl_demon red_eyes short_hair standing stolas_(helluva_boss) top_hat white_face window wings anthro avian bird black_hair cape clothing formal_clothing formal_wear frown goth hair helluva_boss hi_res lanveril looking_at_viewer male owl owl_demon red_background red_eyes red_sky short_hair simple_background sky solo standing stolas_(helluva_boss) white_face 3:4 anthro avian bird cape chair clothing crown curtains curtains_open duo father father_and_child father_and_son formal_clothing formal_wear fur furniture grey_body grey_fur grey_hair hair headgear helluva_boss hi_res holding_another holding_child lanveril looking_down looking_up male night on_lap owl owl_demon paimon_(helluva_boss) parent parent_and_child pink_eyes short_hair simple_background sitting sky son star starry_sky stolas_(helluva_boss) throne white_face 3:4 absurd_res anthro avian bedding beverage bird blanket brown_body brown_fur brown_hair chair container crescent_moon cup duo eyes_closed father father_and_child father_and_son fur furniture grey_body grey_fur grey_hair hair helluva_boss hi_res lanveril male moon owl owl_demon paimon_(helluva_boss) parent parent_and_child plushie short_hair simple_background sitting sleeping smile son star stolas_(helluva_boss) tea throne toy white_face anthro avian bird bodily_fluids camel camelid crown crying dialogue eyes_closed facial_hair father father_and_child father_and_son fire formal_clothing formal_wear group hair headgear helluva_boss hi_res holding_another holding_child horn imp long_hair male mammal mustache owl owl_demon paimon_(helluva_boss) parent parent_and_child purple_background simple_background son speech_bubble standing stolas_(helluva_boss) tears teathekook text trio white_text anthro avian bird black_hair clothed clothing crossdressing dress ear_piercing ear_ring fur girly gloves grey_background grey_body grey_fur hair handwear helluva_boss hi_res holding_microphone holding_object long_hair looking_at_viewer male microphone musical_note owl owl_demon piercing red_eyes ring_piercing simple_background solo standing stolas_(helluva_boss) teathekook text white_clothing white_face white_gloves white_handwear white_text wig 1:1 2023 ambiguous_gender animal_humanoid anthro avian avian_humanoid bdsm bdsm_collar beak bird bird_humanoid black_body black_feathers black_hair blush blush_lines bodily_fluids bondage bound collar colored digital_drawing_(artwork) digital_media_(artwork) feathers hair helluva_boss hi_res humanoid icon looking_at_another looking_at_partner looking_at_viewer looking_back looking_back_at_viewer male male/ambiguous open_mouth owl owl_demon owl_humanoid pleased pleased_expression portrait red_eyes rtootb saliva saliva_string shaded signature simple_background sketch solo stolas_(helluva_boss) anthro avian beanie beverage bird cape clothing container crown cup daughter detailed_background father female formal_clothing formal_wear fur furniture grandchild granddaughter grandfather grandfather_and_grandchild grandparent grandparent_and_grandchild grey_body grey_fur grey_hair group hair hat headgear headwear helluva_boss hi_res long_hair looking_down male nixxxy9 octavia_(helluva_boss) owl owl_demon paimon_(helluva_boss) parent pink_eyes potrait red_eyes short_hair sitting sofa standing stolas_(helluva_boss) tea top_hat trio white_face anthro avian bird child clothing daughter diabloku duo eyes_closed father father_and_child father_and_daughter female formal_clothing formal_wear fur grey_body grey_fur grey_hair hair helluva_boss hi_res holding_another holding_child long_hair male octavia_(helluva_boss) owl owl_demon pajamas parent parent_and_child red_eyes short_hair simple_background smile stolas_(helluva_boss) white_background white_face young absurd_res anthro avian bird brown_background chiizz crown duo father father_and_child father_and_son formal_clothing formal_wear fur grey_body grey_fur grey_hair hair headgear helluva_boss hi_res holding_another holding_child looking_at_viewer looking_down male owl owl_demon paimon_(helluva_boss) parent parent_and_child short_hair simple_background son stolas_(helluva_boss) white_face anthro apology avian beverage bird blitzo_(helluva_boss) clothing container crossed_arms cup dialogue drinking duo eye_contact eyewear glasses grey_background hair helluva_boss hi_res horn imp looking_at_another male owl owl_demon shirt short_hair simple_background sitting smile speech_bubble standing stolas_(helluva_boss) teathekook text topwear white_text worried worried_face worried_look anthro avian bedding bird blanket blitzo_(helluva_boss) bored bored_expression clothing collared_shirt dialogue duo food grey_background hair helluva_boss hi_res horn lying male necktie on_front owl owl_demon popcorn profanity shirt short_hair simple_background speech_bubble stolas_(helluva_boss) teathekook text topwear white_text anthro avian bed bird black_clothing black_shirt black_topwear clothing daughter duo embrace father father_and_child father_and_daughter female fur furniture good_parenting grey_body grey_fur grey_hair hair helluva_boss hidekirider07 hug long_hair looking_down male octavia_(helluva_boss) owl owl_demon pajama_shirt pajamas parent parent_and_child pink_eyes red_eyes robe shirt short_hair simple_background sitting smile star stolas_(helluva_boss) topwear white_face anthro anthro_on_anthro avian balls beak big_balls big_breasts big_butt big_penis bird black_body black_feathers blue_body blue_feathers blush bovid breasts butt caprine claws crossover duo eyelashes eyes_closed feathers female fluffy fluffy_tail fur genitals goat hair helluva_boss hi_res interspecies male male/female mammal mature_female mature_male multi_eye owl owl_demon penis pussy red_body red_eyes red_sclera simple_background stolas_(helluva_boss) tail thick_thighs toriel undertale_(series) vein veiny_penis white_body white_fur xdscoutacrisdx anthro avian avislio bird black_background blitzo_(helluva_boss) bodily_fluids cape clothing crying depression duo embrace formal_clothing formal_wear frown grey_hair hair helluva_boss holding_object holding_phone horn hug imp male owl owl_demon phone red_body red_eyes red_skin sad short_hair simple_background sitting stolas_(helluva_boss) tears white_face yellow_eyes anthro avian bird blitzo_(helluva_boss) bodily_fluids crown crying depression detailed_background duo eyes_closed formal_clothing formal_wear frown fur grey_body grey_fur grey_hair hair headgear helluva_boss horn imp looking_down male owl owl_demon red_body red_eyes red_skin sad short_hair sitting smile someredfox standing stolas_(helluva_boss) tears white_face yellow_eyes