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vanessa (helluva boss)

2023 2girls anthro areolae avian avian_humanoid background_character big_breasts blush blush_lines blushing bodily_fluids breast_hold breasts closed_eyes demon digital_media_(artwork) duo duo_female elelite eyes_closed feathers female female/female female_only helluva_boss hi_res humanoid kissing multiple_girls nipples nude_female owl owl_demon owl_girl purple_body purple_feathers romantic stella_(helluva_boss) sweat sweatdrop sweating sweaty_body vanessa_(helluva_boss) white_body white_feathers yayap117 yellow_eyes yuri
2023 2girls anthro areolae avian avian_humanoid background_character big_breasts blush blush_lines blushing bodily_fluids breast_hold breasts closed_eyes demon digital_media_(artwork) duo duo_female elelite eyes_closed feathers female female/female female_only helluva_boss hi_res humanoid kissing multiple_girls nipples nude_female owl owl_demon owl_girl purple_body purple_feathers romantic stella_(helluva_boss) sweat sweatdrop sweating sweaty_body vanessa_(helluva_boss) white_body white_feathers yayap117 yellow_eyes yuri
2024 4_fingers abstract_background anthro anthro_on_anthro areola arm_tuft artist_name avian beak big_areola big_breasts big_nipples biped bird black_eyebrows black_markings blue_areola blue_nipples blush breasts cheek_tuft collarbone curved_eyebrows demon digital_drawing_(artwork) digital_media_(artwork) duo elbow_tuft elelite eyebrows eyelashes eyeshadow facial_tuft feather_hair feather_tuft feathers female female/female fingerless_(marking) fingers genitals glistening glistening_areola glowing glowing_eyes hair half-closed_eyes helluva_boss hi_res huge_areola innie_pussy intraspecies iris leg_markings legs_together logo long_eyelashes makeup markings mature_anthro mature_female narrowed_eyes navel nipples non-mammal_breasts nude nude_anthro nude_female one_eye_closed owl owl_demon pink_beak pink_blush pink_eyeshadow pink_sclera pseudo_hair pupils purple_body purple_breasts purple_feathers purple_hair pussy short_hair socks_(marking) standing stella_(helluva_boss) thick_eyelashes thick_thighs three-quarter_view tuft twitter twitter_logo unnamed_character vanessa_(helluva_boss) website_logo white_body white_eyes white_feathers yellow_sclera
2024 4_fingers abstract_background anthro anthro_on_anthro areola arm_tuft artist_name avian beak big_areola big_breasts big_nipples biped bird black_eyebrows black_markings blue_areola blue_nipples blush breasts cheek_tuft collarbone curved_eyebrows demon digital_drawing_(artwork) digital_media_(artwork) duo elbow_tuft elelite eyebrows eyelashes eyeshadow facial_tuft feather_hair feather_tuft feathers female female/female fingerless_(marking) fingers genitals glistening glistening_areola glowing glowing_eyes hair half-closed_eyes helluva_boss hi_res huge_areola innie_pussy intraspecies iris leg_markings legs_together logo long_eyelashes makeup markings mature_anthro mature_female narrowed_eyes navel nipples non-mammal_breasts nude nude_anthro nude_female one_eye_closed owl owl_demon pink_beak pink_blush pink_eyeshadow pink_sclera pseudo_hair pupils purple_body purple_breasts purple_feathers purple_hair pussy short_hair socks_(marking) standing stella_(helluva_boss) thick_eyelashes thick_thighs three-quarter_view tuft twitter twitter_logo unnamed_character vanessa_(helluva_boss) website_logo white_body white_eyes white_feathers yellow_sclera
1boy 2girls anthro anthro_on_anthro anus areola avian background_character bed big_ass big_breasts big_butt bird bisexual blue_body blue_feathers bodily_fluids breasts canid canine crossgender feathers female female/female female_penetrated female_stolas first_person_view fox fur furniture genderswap genderswap_(mtf) genital_fluids genitals glowing glowing_eyes group helluva_boss hi_res infidelity interspecies male male/female male_penetrating male_penetrating_female mammal mature_female milf mtf_crossgender naked nick_flynn_(bigppfox1) nipples nude owl penetration penile penile_penetration penis penis_in_pussy phone purple_body purple_feathers pussy pussy_juice red_eyes rule_63 sex stella_(helluva_boss) stolas_(helluva_boss) text thick_ass thick_thighs trio unknown_artist vaginal vaginal_penetration vanessa_(helluva_boss) vivienne_medrano wide_hips yellow_body yellow_eyes yellow_fur
1boy 2girls anthro anthro_on_anthro anus areola avian background_character bed big_ass big_breasts big_butt bird bisexual blue_body blue_feathers bodily_fluids breasts canid canine crossgender feathers female female/female female_penetrated female_stolas first_person_view fox fur furniture genderswap genderswap_(mtf) genital_fluids genitals glowing glowing_eyes group helluva_boss hi_res infidelity interspecies male male/female male_penetrating male_penetrating_female mammal mature_female milf mtf_crossgender naked nick_flynn_(bigppfox1) nipples nude owl penetration penile penile_penetration penis penis_in_pussy phone purple_body purple_feathers pussy pussy_juice red_eyes rule_63 sex stella_(helluva_boss) stolas_(helluva_boss) text thick_ass thick_thighs trio unknown_artist vaginal vaginal_penetration vanessa_(helluva_boss) vivienne_medrano wide_hips yellow_body yellow_eyes yellow_fur
absurd_res alcohol anthro avian background_character beak beverage big_breasts breasts character_request claws clothing container cup demon detailed_background drinking_glass feathers female glass glass_container glass_cup helluva_boss hi_res holding_object mature_female nipples panties purple_body purple_feathers solo theartsygirl94 thick_thighs underwear vanessa_(helluva_boss) vivienne_medrano vivziepop wine wine_glass yellow_eyes
absurd_res alcohol anthro avian background_character beak beverage big_breasts breasts character_request claws clothing container cup demon detailed_background drinking_glass feathers female glass glass_container glass_cup helluva_boss hi_res holding_object mature_female nipples panties purple_body purple_feathers solo theartsygirl94 thick_thighs underwear vanessa_(helluva_boss) vivienne_medrano vivziepop wine wine_glass yellow_eyes
anal background_characters ball_gag big_breasts bird blush bondage cum cum_inside detailed_background foursome glowing_eyes helluva_boss incest octavia_(helluva_boss) owl penetration questionable_consent sex_toy small_breasts stella_(helluva_boss) strap-on the_dark_mangaka tied_up vanessa_(helluva_boss) vivienne_style
anal background_characters ball_gag big_breasts bird blush bondage cum cum_inside detailed_background foursome glowing_eyes helluva_boss incest octavia_(helluva_boss) owl penetration questionable_consent sex_toy small_breasts stella_(helluva_boss) strap-on the_dark_mangaka tied_up vanessa_(helluva_boss) vivienne_style
ai_generated bust_portrait busty busty_female civitai crypticunmasked female_focus female_only furry helluva_boss large_breasts owl owl_demon owl_girl purple_body purple_skin vanessa_(helluva_boss)
ai_generated bust_portrait busty busty_female civitai crypticunmasked female_focus female_only furry helluva_boss large_breasts owl owl_demon owl_girl purple_body purple_skin vanessa_(helluva_boss)
absurd_res age_difference anthro aptom7747 avian background_character beak breasts collar demon dialogue duo faceless_character faceless_male female first_person_view fur genitals hair helluva_boss hi_res human human_on_anthro imminent_sex interspecies light_body light_skin male male/female male_pov mammal mature_female nipples older_anthro older_female penis purple_body purple_fur purple_hair simple_background smile tongue tongue_out vanessa_(helluva_boss) yellow_eyes younger_human younger_male
absurd_res age_difference anthro aptom7747 avian background_character beak breasts collar demon dialogue duo faceless_character faceless_male female first_person_view fur genitals hair helluva_boss hi_res human human_on_anthro imminent_sex interspecies light_body light_skin male male/female male_pov mammal mature_female nipples older_anthro older_female penis purple_body purple_fur purple_hair simple_background smile tongue tongue_out vanessa_(helluva_boss) yellow_eyes younger_human younger_male
animal_humanoid anthro avian avian_humanoid bed big_breasts bird breast_squish breasts duo elelite feathers female female/female furniture helluva_boss hi_res humanoid masturbation owl owl_demon purple_body purple_feathers red_eyes squish stella_(helluva_boss) vanessa_(helluva_boss) white_body white_feathers yellow_eyes
animal_humanoid anthro avian avian_humanoid bed big_breasts bird breast_squish breasts duo elelite feathers female female/female furniture helluva_boss hi_res humanoid masturbation owl owl_demon purple_body purple_feathers red_eyes squish stella_(helluva_boss) vanessa_(helluva_boss) white_body white_feathers yellow_eyes
1girls ass_expansion avian avian_demon avian_humanoid background_character big_breasts breast_expansion breasts cleavage demon demon_girl dress excessive_size female female_focus female_only helluva_boss jaeh non-mammal_breasts owl_demon owl_girl owl_humanoid ripped_clothing ripped_dress solo solo_female thick_thighs thighs vanessa_(helluva_boss) vivienne_medrano voluptuous wide_hips
1girls ass_expansion avian avian_demon avian_humanoid background_character big_breasts breast_expansion breasts cleavage demon demon_girl dress excessive_size female female_focus female_only helluva_boss jaeh non-mammal_breasts owl_demon owl_girl owl_humanoid ripped_clothing ripped_dress solo solo_female thick_thighs thighs vanessa_(helluva_boss) vivienne_medrano voluptuous wide_hips
1girls 2022 ambiguous_gender animated anonymous_artist anthro anthro_focus ass avian background_character bedroom_eyes big_butt bird bouncing_breasts breasts bubble_butt butt_pinch cleavage clothed clothing container cup dress duo female female_focus first_person_view gem head_turned helluva_boss hi_res holding_cup holding_object jewelry looking_at_viewer looking_back looking_back_at_viewer mature_anthro mature_female narrowed_eyes necklace owl owl_demon pearl_(gem) pearl_necklace seductive shaking_butt short_playtime sketch solo_focus surprise twerking vanessa_(helluva_boss) vivienne_medrano vivziepop wide_hips
1girls 2022 ambiguous_gender animated anonymous_artist anthro anthro_focus ass avian background_character bedroom_eyes big_butt bird bouncing_breasts breasts bubble_butt butt_pinch cleavage clothed clothing container cup dress duo female female_focus first_person_view gem head_turned helluva_boss hi_res holding_cup holding_object jewelry looking_at_viewer looking_back looking_back_at_viewer mature_anthro mature_female narrowed_eyes necklace owl owl_demon pearl_(gem) pearl_necklace seductive shaking_butt short_playtime sketch solo_focus surprise twerking vanessa_(helluva_boss) vivienne_medrano vivziepop wide_hips
2023 5:6 absurd_res ankle_strap_heels anthro areola artist_logo ass avian background_character big_areola big_breasts big_butt big_nipples biped bird black_eyebrows black_eyelashes black_fingernails black_nails black_sofa bracelet breasts carpet clothing collarbone colored_nails curved_eyebrows curvy_figure demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes eyebrows eyelashes female fingernails fingers floor footwear furniture gem hair hand_on_leg hand_on_own_leg hand_on_own_thigh hand_on_thigh helluva_boss hi_res high_heels humanoid_hands inside internal_wall jewelry logo long_eyelashes looking_at_viewer lying mature_anthro mature_female mostly_nude mostly_nude_anthro mostly_nude_female mouthless multicolored_hair nails necklace nipples on_side owl owl_demon pearl_(gem) pearl_necklace pillow pinup platform_footwear platform_heels pose purple_body ring_(jewelry) sagging_breasts short_hair sofa solo text thick_thighs two_tone_hair vanessa_(helluva_boss) vivienne_medrano vivziepop voluptuous wall_(structure) white_carpet white_clothing white_footwear white_heels white_jewelry white_necklace white_pillow white_text xartknight yellow_eyes
2023 5:6 absurd_res ankle_strap_heels anthro areola artist_logo ass avian background_character big_areola big_breasts big_butt big_nipples biped bird black_eyebrows black_eyelashes black_fingernails black_nails black_sofa bracelet breasts carpet clothing collarbone colored_nails curved_eyebrows curvy_figure demon digital_drawing_(artwork) digital_media_(artwork) empty_eyes eyebrows eyelashes female fingernails fingers floor footwear furniture gem hair hand_on_leg hand_on_own_leg hand_on_own_thigh hand_on_thigh helluva_boss hi_res high_heels humanoid_hands inside internal_wall jewelry logo long_eyelashes looking_at_viewer lying mature_anthro mature_female mostly_nude mostly_nude_anthro mostly_nude_female mouthless multicolored_hair nails necklace nipples on_side owl owl_demon pearl_(gem) pearl_necklace pillow pinup platform_footwear platform_heels pose purple_body ring_(jewelry) sagging_breasts short_hair sofa solo text thick_thighs two_tone_hair vanessa_(helluva_boss) vivienne_medrano vivziepop voluptuous wall_(structure) white_carpet white_clothing white_footwear white_heels white_jewelry white_necklace white_pillow white_text xartknight yellow_eyes
1boy 1girls 2024 absurd_res ahe_gao anthro ass avian bent_over breasts caladrius_(helluva_boss) choker demon dialogue english_text female female_focus from_behind from_behind_position glowing_eyes helluva_boss heretic_art male penetration pleasure_face public public_sex red_eyes runny_makeup speech_bubble stella_(helluva_boss) striker_(helluva_boss) thick_thighs vaginal_penetration vanessa_(helluva_boss) very_high_resolution writing_on_ass writing_on_body
1boy 1girls 2024 absurd_res ahe_gao anthro ass avian bent_over breasts caladrius_(helluva_boss) choker demon dialogue english_text female female_focus from_behind from_behind_position glowing_eyes helluva_boss heretic_art male penetration pleasure_face public public_sex red_eyes runny_makeup speech_bubble stella_(helluva_boss) striker_(helluva_boss) thick_thighs vaginal_penetration vanessa_(helluva_boss) very_high_resolution writing_on_ass writing_on_body
age_difference anal anal_sex anthro anthro_on_anthro ass avian background_character ball_gag beak big_breasts big_butt bird bisexual black_body black_feathers blush bodily_fluids bondage breasts caladrius_(helluva_boss) claws crown cum cum_in_pussy cum_inside daughter demon detailed_background dildo dildo_in_ass dildo_insertion dominant dominant_female dominant_male double_penetration erection feathers female female/female female_penetrated female_penetrating female_penetrating_female fillmore_(helluva_boss) gag gagged genital_fluids genitals group group_sex helluva_boss hi_res husband_and_wife looking_pleasured male male/female male_penetrating male_penetrating_female married_couple mature_female mature_male mother mother_and_child mother_and_daughter nipples nude octavia_(helluva_boss) open_mouth owl owl_demon parent parent_and_child penetration penile penile_penetration penis penis_in_pussy purple_body purple_feathers rape restrained saliva sex sex_toy sex_toy_in_ass sex_toy_insertion simple_background smile stella_(helluva_boss) submissive submissive_female the_dark_mangaka thick_thighs threesome trio vaginal_penetration vanessa_(helluva_boss) yellow_eyes younger_female
age_difference anal anal_sex anthro anthro_on_anthro ass avian background_character ball_gag beak big_breasts big_butt bird bisexual black_body black_feathers blush bodily_fluids bondage breasts caladrius_(helluva_boss) claws crown cum cum_in_pussy cum_inside daughter demon detailed_background dildo dildo_in_ass dildo_insertion dominant dominant_female dominant_male double_penetration erection feathers female female/female female_penetrated female_penetrating female_penetrating_female fillmore_(helluva_boss) gag gagged genital_fluids genitals group group_sex helluva_boss hi_res husband_and_wife looking_pleasured male male/female male_penetrating male_penetrating_female married_couple mature_female mature_male mother mother_and_child mother_and_daughter nipples nude octavia_(helluva_boss) open_mouth owl owl_demon parent parent_and_child penetration penile penile_penetration penis penis_in_pussy purple_body purple_feathers rape restrained saliva sex sex_toy sex_toy_in_ass sex_toy_insertion simple_background smile stella_(helluva_boss) submissive submissive_female the_dark_mangaka thick_thighs threesome trio vaginal_penetration vanessa_(helluva_boss) yellow_eyes younger_female
2022 age_difference anal anal_sex anthro anthro_on_anthro arms_tied ass avian background_character ball_gag beak big_breasts big_butt bird bisexual black_body black_feathers blush bodily_fluids bondage bound breast_bondage breasts claws crown cum cum_in_pussy cum_inside daughter demon detailed_background dildo dildo_in_ass dildo_insertion dominant dominant_female dominant_male double_penetration drooling dubious_consent erection feathers female female/female female_penetrated female_penetrating female_penetrating_female fillmore_(helluva_boss) gag gagged genital_fluids genitals glare group group_sex hand_on_leg helluva_boss husband_and_wife looking_pleasured male male/female male_penetrating male_penetrating_female married_couple mature_female mature_male mother mother_and_child mother_and_daughter nipples nude octavia_(helluva_boss) open_mouth owl owl_demon parent parent_and_child penetration penile penile_penetration penis penis_in_pussy purple_body purple_feathers rape restrained saliva sex sex_toy sex_toy_in_ass sex_toy_insertion simple_background smile stained_glass stella_(helluva_boss) submissive submissive_female the_dark_mangaka thick_thighs threesome toying_partner trio vaginal_penetration vanessa_(helluva_boss) yellow_eyes younger_female
2022 age_difference anal anal_sex anthro anthro_on_anthro arms_tied ass avian background_character ball_gag beak big_breasts big_butt bird bisexual black_body black_feathers blush bodily_fluids bondage bound breast_bondage breasts claws crown cum cum_in_pussy cum_inside daughter demon detailed_background dildo dildo_in_ass dildo_insertion dominant dominant_female dominant_male double_penetration drooling dubious_consent erection feathers female female/female female_penetrated female_penetrating female_penetrating_female fillmore_(helluva_boss) gag gagged genital_fluids genitals glare group group_sex hand_on_leg helluva_boss husband_and_wife looking_pleasured male male/female male_penetrating male_penetrating_female married_couple mature_female mature_male mother mother_and_child mother_and_daughter nipples nude octavia_(helluva_boss) open_mouth owl owl_demon parent parent_and_child penetration penile penile_penetration penis penis_in_pussy purple_body purple_feathers rape restrained saliva sex sex_toy sex_toy_in_ass sex_toy_insertion simple_background smile stained_glass stella_(helluva_boss) submissive submissive_female the_dark_mangaka thick_thighs threesome toying_partner trio vaginal_penetration vanessa_(helluva_boss) yellow_eyes younger_female
1girls absurd_res anthro ass avian avian_humanoid background_character beak big_breasts big_butt breasts demon feathers female female_only helluva_boss hi_res mature_female nude_female owl owl_demon owl_girl owl_humanoid purple_body purple_feathers simple_background solo solo_female thick_thighs vanessa_(helluva_boss) vaquerocoyote yellow_eyes
1girls absurd_res anthro ass avian avian_humanoid background_character beak big_breasts big_butt breasts demon feathers female female_only helluva_boss hi_res mature_female nude_female owl owl_demon owl_girl owl_humanoid purple_body purple_feathers simple_background solo solo_female thick_thighs vanessa_(helluva_boss) vaquerocoyote yellow_eyes