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ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair male sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res hug humanoid long_hair sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) winged_humanoid wings acky05 angel ankle_cuffs anthro blep bottomwear chest_tuft clothing cuff_(restraint) feathered_wings feathers fluffy fluffy_tail green_eyes hair hair_over_eye hands_behind_head heart_symbol hi_res horn inner_ear_fluff kneeling kobold loincloth looking_at_viewer male metal_cuffs neck_cuff one_eye_obstructed pubes restraints solo tail tongue tongue_out tuft wings yayuri 2000s_theme 2021 2_horns ambiguous_feral ambiguous_gender angel black_body black_fur blue_collar blue_eyes brother_(lore) brothers_(lore) cel_shading claws collar compression_artifacts cute_fangs demon digital_drawing_(artwork) digital_media_(artwork) domestic_cat duo eyebrows eyelashes facial_tuft feathered_wings feathers feet felid feline felis feral firestar_(warriors) fur glistening glistening_eyes gloves_(marking) green_eyes half-brothers halo head_tuft horn kemono leg_markings looking_at_viewer male_(lore) mammal markings membrane_(anatomy) membranous_wings meow286 multicolored_body open_mouth open_smile orange_body orange_fur paws red_background red_horn red_sclera scar scourge_(warriors) semi-anthro shaded sibling_(lore) simple_background smile spiked_collar spikes striped_body striped_fur stripes tabby_cat toes tongue tuft warm_colors warriors_(book_series) whiskers white_body white_fur white_markings white_wings wings yellow_sclera ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear absurd_res anal anal_fingering anal_orgasm angel anthro arms_tied assisted_exposure avian barbie_(helluva_boss) barbie_wire bird bodily_fluids bound clothing ejaculation exorcist_(hazbin_hotel) female fingering fingering_partner forced forced_ejaculation forced_exposure forced_orgasm genital_fluids ghostgallora gremlin hazbin_hotel helluva_boss hi_res humanoid humiliation imp lute_(hazbin_hotel) masked_female orgasm penetration public public_exposure public_humiliation pussy_ejaculation rape recording resisting resisting_orgasm sex sex_toy sex_toy_in_pussy sex_toy_insertion shaking size_difference small_dom_big_sub stella_(helluva_boss) sweat sweating_profusely tears torn_clothing trembling vaginal vaginal_fluids vaginal_penetration vibrator ally_kat angel angel_humanoid begging begging_for_mercy begging_pose bodily_fluids comic crying dialogue duo emily_(hazbin_hotel) female frown hair hazbin_hotel hi_res humanoid long_hair pose sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair male sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res hug humanoid long_hair sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) winged_humanoid wings acky05 angel ankle_cuffs anthro blep bottomwear chest_tuft clothing cuff_(restraint) feathered_wings feathers fluffy fluffy_tail green_eyes hair hair_over_eye hands_behind_head heart_symbol hi_res horn inner_ear_fluff kneeling kobold loincloth looking_at_viewer male metal_cuffs neck_cuff one_eye_obstructed pubes restraints solo tail tongue tongue_out tuft wings yayuri 2000s_theme 2021 2_horns ambiguous_feral ambiguous_gender angel black_body black_fur blue_collar blue_eyes brother_(lore) brothers_(lore) cel_shading claws collar compression_artifacts cute_fangs demon digital_drawing_(artwork) digital_media_(artwork) domestic_cat duo eyebrows eyelashes facial_tuft feathered_wings feathers feet felid feline felis feral firestar_(warriors) fur glistening glistening_eyes gloves_(marking) green_eyes half-brothers halo head_tuft horn kemono leg_markings looking_at_viewer male_(lore) mammal markings membrane_(anatomy) membranous_wings meow286 multicolored_body open_mouth open_smile orange_body orange_fur paws red_background red_horn red_sclera scar scourge_(warriors) semi-anthro shaded sibling_(lore) simple_background smile spiked_collar spikes striped_body striped_fur stripes tabby_cat toes tongue tuft warm_colors warriors_(book_series) whiskers white_body white_fur white_markings white_wings wings yellow_sclera ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear 3d_(artwork) angel angel_humanoid balls big_balls big_breasts big_penis breasts clothed clothing demon demon_humanoid detailed_background digital_media_(artwork) dominant dominant_female duo erection female genitals hair hazbin_hotel helluva_boss hi_res horn humanoid imp light-skinned_female lute_(hazbin_hotel) male male/female moxxie_(helluva_boss) nipples partially_clothed penis red_body silver2299nsfw submissive submissive_male thick_thighs white_hair wings yellow_eyes ally_kat angel angel_humanoid begging begging_for_mercy begging_pose bodily_fluids comic crying dialogue duo emily_(hazbin_hotel) female frown hair hazbin_hotel hi_res humanoid long_hair pose sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair male sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res hug humanoid long_hair sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) winged_humanoid wings acky05 angel ankle_cuffs anthro blep bottomwear chest_tuft clothing cuff_(restraint) feathered_wings feathers fluffy fluffy_tail green_eyes hair hair_over_eye hands_behind_head heart_symbol hi_res horn inner_ear_fluff kneeling kobold loincloth looking_at_viewer male metal_cuffs neck_cuff one_eye_obstructed pubes restraints solo tail tongue tongue_out tuft wings yayuri 2000s_theme 2021 2_horns ambiguous_feral ambiguous_gender angel black_body black_fur blue_collar blue_eyes brother_(lore) brothers_(lore) cel_shading claws collar compression_artifacts cute_fangs demon digital_drawing_(artwork) digital_media_(artwork) domestic_cat duo eyebrows eyelashes facial_tuft feathered_wings feathers feet felid feline felis feral firestar_(warriors) fur glistening glistening_eyes gloves_(marking) green_eyes half-brothers halo head_tuft horn kemono leg_markings looking_at_viewer male_(lore) mammal markings membrane_(anatomy) membranous_wings meow286 multicolored_body open_mouth open_smile orange_body orange_fur paws red_background red_horn red_sclera scar scourge_(warriors) semi-anthro shaded sibling_(lore) simple_background smile spiked_collar spikes striped_body striped_fur stripes tabby_cat toes tongue tuft warm_colors warriors_(book_series) whiskers white_body white_fur white_markings white_wings wings yellow_sclera ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear ally_kat angel angel_humanoid begging begging_for_mercy begging_pose bodily_fluids comic crying dialogue duo emily_(hazbin_hotel) female frown hair hazbin_hotel hi_res humanoid long_hair pose sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair male sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res hug humanoid long_hair sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) winged_humanoid wings acky05 angel ankle_cuffs anthro blep bottomwear chest_tuft clothing cuff_(restraint) feathered_wings feathers fluffy fluffy_tail green_eyes hair hair_over_eye hands_behind_head heart_symbol hi_res horn inner_ear_fluff kneeling kobold loincloth looking_at_viewer male metal_cuffs neck_cuff one_eye_obstructed pubes restraints solo tail tongue tongue_out tuft wings yayuri 2000s_theme 2021 2_horns ambiguous_feral ambiguous_gender angel black_body black_fur blue_collar blue_eyes brother_(lore) brothers_(lore) cel_shading claws collar compression_artifacts cute_fangs demon digital_drawing_(artwork) digital_media_(artwork) domestic_cat duo eyebrows eyelashes facial_tuft feathered_wings feathers feet felid feline felis feral firestar_(warriors) fur glistening glistening_eyes gloves_(marking) green_eyes half-brothers halo head_tuft horn kemono leg_markings looking_at_viewer male_(lore) mammal markings membrane_(anatomy) membranous_wings meow286 multicolored_body open_mouth open_smile orange_body orange_fur paws red_background red_horn red_sclera scar scourge_(warriors) semi-anthro shaded sibling_(lore) simple_background smile spiked_collar spikes striped_body striped_fur stripes tabby_cat toes tongue tuft warm_colors warriors_(book_series) whiskers white_body white_fur white_markings white_wings wings yellow_sclera ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear ally_kat angel angel_humanoid begging begging_for_mercy begging_pose bodily_fluids comic crying dialogue duo emily_(hazbin_hotel) female frown hair hazbin_hotel hi_res humanoid long_hair pose sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair male sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res hug humanoid long_hair sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) winged_humanoid wings acky05 angel ankle_cuffs anthro blep bottomwear chest_tuft clothing cuff_(restraint) feathered_wings feathers fluffy fluffy_tail green_eyes hair hair_over_eye hands_behind_head heart_symbol hi_res horn inner_ear_fluff kneeling kobold loincloth looking_at_viewer male metal_cuffs neck_cuff one_eye_obstructed pubes restraints solo tail tongue tongue_out tuft wings yayuri 2000s_theme 2021 2_horns ambiguous_feral ambiguous_gender angel black_body black_fur blue_collar blue_eyes brother_(lore) brothers_(lore) cel_shading claws collar compression_artifacts cute_fangs demon digital_drawing_(artwork) digital_media_(artwork) domestic_cat duo eyebrows eyelashes facial_tuft feathered_wings feathers feet felid feline felis feral firestar_(warriors) fur glistening glistening_eyes gloves_(marking) green_eyes half-brothers halo head_tuft horn kemono leg_markings looking_at_viewer male_(lore) mammal markings membrane_(anatomy) membranous_wings meow286 multicolored_body open_mouth open_smile orange_body orange_fur paws red_background red_horn red_sclera scar scourge_(warriors) semi-anthro shaded sibling_(lore) simple_background smile spiked_collar spikes striped_body striped_fur stripes tabby_cat toes tongue tuft warm_colors warriors_(book_series) whiskers white_body white_fur white_markings white_wings wings yellow_sclera ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear 2017 2_horns absurd_res angel angel_humanoid anthro back_wings bent_over biped black_clothing black_hair black_hooves black_jacket black_topwear blue_eyes bottomwear bovid brown_body brown_fur brown_hair brown_tail bullying caprine caprine_demon character_name clothing cloven_hooves colored deisel_(toxicsoul77) demon duo english_honorific facial_piercing female flash_(toxicsoul77) footwear fur goat_demon hair halo hi_res hooves horn humanoid jacket larger_anthro larger_humanoid larger_male male mammal nipples nose_piercing nose_ring piercing pigtails pistol_(toxicsoul77) red_body red_ear red_horn red_nipples red_skin ring_piercing sharp_teeth shoes simple_background size_difference skirt sleeveless smaller_anthro smaller_female smiley_face split_form tail teeth topwear toxicsoul77 unguligrade unguligrade_anthro white_bottomwear white_clothing white_dress_shirt white_skirt winged_humanoid wings ally_kat angel angel_humanoid begging begging_for_mercy begging_pose bodily_fluids comic crying dialogue duo emily_(hazbin_hotel) female frown hair hazbin_hotel hi_res humanoid long_hair pose sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair sad sera_(hazbin_hotel) seraph_(angel) short_hair simple_background speech_bubble tears text vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res humanoid long_hair male sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) white_text winged_humanoid wings ally_kat angel angel_humanoid black_text bodily_fluids charlie_morningstar comic crying demon dialogue emily_(hazbin_hotel) female frown group hair hazbin_hotel hi_res hug humanoid long_hair sad seraph_(angel) short_hair simple_background speech_bubble tears text trio vaggie_(hazbin_hotel) winged_humanoid wings acky05 angel ankle_cuffs anthro blep bottomwear chest_tuft clothing cuff_(restraint) feathered_wings feathers fluffy fluffy_tail green_eyes hair hair_over_eye hands_behind_head heart_symbol hi_res horn inner_ear_fluff kneeling kobold loincloth looking_at_viewer male metal_cuffs neck_cuff one_eye_obstructed pubes restraints solo tail tongue tongue_out tuft wings yayuri