canid_demon -animated best from all time

Time frame

canid demon

16:9 2_girls 2boys 2d_animation 2girls ahegao animated anus arm_tattoo ass ball_slap balls balls_deep bed bedroom bedroom_eyes being_watched big_ass billboard bite biting_lip black_hair black_lips blitzo_(helluva_boss) blush bodily_fluids body_part_in_mouth bouncing_ass bouncing_balls breasts broken_window bubble_butt camera canid canid_demon canon_couple cartoonsaur cellphone chair choker clitoris clothing cuddling cum cum_in_pussy cum_inside curtains deepthroat demon dildo drooling duo ejaculation entwined_tails erection eyelashes eyelids fellatio female female_on_bottom female_penetrated fingerless_gloves foreskin from_behind_position from_front_position furniture genital_fluids genitals gesture gloves hair handwear heart_shaped_butt hellhound helluva_boss hi_res horn huge_filesize humanoid humanoid_genitalia humanoid_on_humanoid humanoid_on_top humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid humanoid_penis humanoid_pov imminent_anal imminent_pegging imminent_sex imp intraspecies irrumatio jewelry kissing knife knife_wound laugh legs_up legwear lips long_playtime looking_at_another looking_pleasured loona_(helluva_boss) male male/female male_on_top male_penetrating male_penetrating_female male_pov mammal marker married_couple mating_press middle_finger millie_(helluva_boss) moan moxxie_(helluva_boss) multiple_positions music narrowed_eyes necklace nipples office office_chair on_bottom on_top oral oral_penetration orgasm penetrating_pov penetration penile penile_penetration penis penis_in_mouth penis_in_pussy phone phone_view pose pov precum profanity pussy pussy_juice raised_leg record record_player red_body red_skin retracted_foreskin romantic romantic_ambiance romantic_couple romantic_sex saliva seductive self_bite sex sex_toy shaking_ass slap smartphone sound spade_tail strap-on sweat table tail tail_coil tail_motion tailwag tattoo tears teeth television texting throbbing throbbing_penis tooth_gap vaginal vaginal_penetration video vivzmind voice_acted wall_(structure) wallpaper_(decoration) webm white_hair widescreen window writing_utensil yellow_eyes
16:9 2_girls 2boys 2d_animation 2girls ahegao animated anus arm_tattoo ass ball_slap balls balls_deep bed bedroom bedroom_eyes being_watched big_ass billboard bite biting_lip black_hair black_lips blitzo_(helluva_boss) blush bodily_fluids body_part_in_mouth bouncing_ass bouncing_balls breasts broken_window bubble_butt camera canid canid_demon canon_couple cartoonsaur cellphone chair choker clitoris clothing cuddling cum cum_in_pussy cum_inside curtains deepthroat demon dildo drooling duo ejaculation entwined_tails erection eyelashes eyelids fellatio female female_on_bottom female_penetrated fingerless_gloves foreskin from_behind_position from_front_position furniture genital_fluids genitals gesture gloves hair handwear heart_shaped_butt hellhound helluva_boss hi_res horn huge_filesize humanoid humanoid_genitalia humanoid_on_humanoid humanoid_on_top humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid humanoid_penis humanoid_pov imminent_anal imminent_pegging imminent_sex imp intraspecies irrumatio jewelry kissing knife knife_wound laugh legs_up legwear lips long_playtime looking_at_another looking_pleasured loona_(helluva_boss) male male/female male_on_top male_penetrating male_penetrating_female male_pov mammal marker married_couple mating_press middle_finger millie_(helluva_boss) moan moxxie_(helluva_boss) multiple_positions music narrowed_eyes necklace nipples office office_chair on_bottom on_top oral oral_penetration orgasm penetrating_pov penetration penile penile_penetration penis penis_in_mouth penis_in_pussy phone phone_view pose pov precum profanity pussy pussy_juice raised_leg record record_player red_body red_skin retracted_foreskin romantic romantic_ambiance romantic_couple romantic_sex saliva seductive self_bite sex sex_toy shaking_ass slap smartphone sound spade_tail strap-on sweat table tail tail_coil tail_motion tailwag tattoo tears teeth television texting throbbing throbbing_penis tooth_gap vaginal vaginal_penetration video vivzmind voice_acted wall_(structure) wallpaper_(decoration) webm white_hair widescreen window writing_utensil yellow_eyes
1boy 1boy2girls 2_girls 2girls ambiguous_penetration angry animated arm_pull armwear ass balls big_penis bisexual black_body black_eye_(injury) black_fur black_tail blank_thumbnail blue_hair blush bodily_fluids bordeaux_black breast_fondling breast_play breasts breath bruised canid canid_demon canine canis cartoonsaur clothing collar cowgirl_position cum cum_in_mouth cum_inside demon dialogue dream drinking drinking_cum ear_piercing earring elbow_gloves female female/female female_penetrated ffm_threesome fingerless_gloves fondling fondling_self forced forced_oral from_behind_position from_front_position fucked_silly fur genital_fluids genitals gloves grey_body grey_fur group group_sex growling hair hand_on_breast handwear hellhound helluva_boss hi_res horn huge_filesize imp irrumatio kissing larger_female legwear longer_than_3_minutes looking_pleasured loona_(helluva_boss) lying makeup male male/female male_penetrating male_penetrating_female mammal mascara medium_breasts millie_(helluva_boss) missionary missionary_position moan mostly_nude moxxie_(helluva_boss) music navel nipples on_back on_bottom on_top oral oral_penetration orgasm panting penetration penile penile_penetration penis penis_in_mouth penis_in_pussy perching_position piercing pink_nipples prison_guard_position punch pussy pussy_juice pussylicking red_body red_sclera red_skin ring_piercing sex shorter_than_five_minutes size_difference small_breasts smaller_female smaller_male smile snowballing sound spade_tail spiked_collar spikes stockings straddling sweat tail thigh_high_stockings threesome toeless_legwear toeless_stockings trio two_tone_tail vaginal vaginal_penetration video violence vivzmind voice_acted webm wet_dream white_body white_fur white_hair white_tail wolf yellow_sclera
1boy 1boy2girls 2_girls 2girls ambiguous_penetration angry animated arm_pull armwear ass balls big_penis bisexual black_body black_eye_(injury) black_fur black_tail blank_thumbnail blue_hair blush bodily_fluids bordeaux_black breast_fondling breast_play breasts breath bruised canid canid_demon canine canis cartoonsaur clothing collar cowgirl_position cum cum_in_mouth cum_inside demon dialogue dream drinking drinking_cum ear_piercing earring elbow_gloves female female/female female_penetrated ffm_threesome fingerless_gloves fondling fondling_self forced forced_oral from_behind_position from_front_position fucked_silly fur genital_fluids genitals gloves grey_body grey_fur group group_sex growling hair hand_on_breast handwear hellhound helluva_boss hi_res horn huge_filesize imp irrumatio kissing larger_female legwear longer_than_3_minutes looking_pleasured loona_(helluva_boss) lying makeup male male/female male_penetrating male_penetrating_female mammal mascara medium_breasts millie_(helluva_boss) missionary missionary_position moan mostly_nude moxxie_(helluva_boss) music navel nipples on_back on_bottom on_top oral oral_penetration orgasm panting penetration penile penile_penetration penis penis_in_mouth penis_in_pussy perching_position piercing pink_nipples prison_guard_position punch pussy pussy_juice pussylicking red_body red_sclera red_skin ring_piercing sex shorter_than_five_minutes size_difference small_breasts smaller_female smaller_male smile snowballing sound spade_tail spiked_collar spikes stockings straddling sweat tail thigh_high_stockings threesome toeless_legwear toeless_stockings trio two_tone_tail vaginal vaginal_penetration video violence vivzmind voice_acted webm wet_dream white_body white_fur white_hair white_tail wolf yellow_sclera
1girl anthro bbmbbf blush breasts canid canid_demon canine demon female female_only fur34 fur34* furry gold_level hellhound helluva_boss loona_(helluva_boss) loona_(vivzmind) mammal nude palcomix pietro's_secret_club pietros_secret_club pussy shower solo vivienne_medrano vivzmind youtube
1girl anthro bbmbbf blush breasts canid canid_demon canine demon female female_only fur34 fur34* furry gold_level hellhound helluva_boss loona_(helluva_boss) loona_(vivzmind) mammal nude palcomix pietro's_secret_club pietros_secret_club pussy shower solo vivienne_medrano vivzmind youtube
<3 136 16:9 1girl 3_toes 4_fingers 6boys animal_dildo animal_sex_toy animated announcing_orgasm anthro anthro_on_anthro anthro_on_bottom anthro_on_top anthro_penetrated anthro_penetrating anthro_penetrating_anthro areola armwear ass assertive_female balls bandage bandaged_arm bed big_dom_small_sub bite biting_lip blitzo_(helluva_boss) blush bodily_fluids bouncing_balls bouncing_breasts bouncing_butt box breasts canid canid_demon canine canine_dildo canis cartoonsaur cervical_contact claws clitoris clothing collar container cowgirl_position demon dildo dirty_talk doggy_position dominant elbow_gloves english_text erection fangs fantasizing feet female female_on_top female_penetrated finger_claws fingerless_gloves fingers from_behind_position from_front_position fucked_silly furniture gangbang genital_fluids genitals gloves group group_sex half-closed_eyes handjob handwear hellhound helluva_boss hi_res holding_leg human human_on_anthro human_penetrating human_penetrating_anthro imp interspecies knot knot_fucking knotted_dildo knotting larger_male leg_grab legwear long_playtime looking_pleasured loona_(helluva_boss) lying male male/female male_on_bottom male_penetrating male_penetrating_female mammal masturbation millie_(helluva_boss) missionary missionary_position moan moxxie_(helluva_boss) multiple_positions muscular muscular_male narrowed_eyes o_o on_back on_bottom on_model on_top orgasm orgasm_face pawpads penetration penile penile_penetration penis penis_everywhere penis_in_pussy pink_areola profanity pussy pussy_juice red_sclera sex sex_toy size_difference small_dom_big_sub smaller_female solo_focus sound stockings submissive submissive_anthro submissive_female teeth text toe_claws toes tongue tongue_out vaginal vaginal_knotting vaginal_masturbation vaginal_penetration vivzmind voice_acted vortex_(helluva_boss) webm widescreen wolf
<3 136 16:9 1girl 3_toes 4_fingers 6boys animal_dildo animal_sex_toy animated announcing_orgasm anthro anthro_on_anthro anthro_on_bottom anthro_on_top anthro_penetrated anthro_penetrating anthro_penetrating_anthro areola armwear ass assertive_female balls bandage bandaged_arm bed big_dom_small_sub bite biting_lip blitzo_(helluva_boss) blush bodily_fluids bouncing_balls bouncing_breasts bouncing_butt box breasts canid canid_demon canine canine_dildo canis cartoonsaur cervical_contact claws clitoris clothing collar container cowgirl_position demon dildo dirty_talk doggy_position dominant elbow_gloves english_text erection fangs fantasizing feet female female_on_top female_penetrated finger_claws fingerless_gloves fingers from_behind_position from_front_position fucked_silly furniture gangbang genital_fluids genitals gloves group group_sex half-closed_eyes handjob handwear hellhound helluva_boss hi_res holding_leg human human_on_anthro human_penetrating human_penetrating_anthro imp interspecies knot knot_fucking knotted_dildo knotting larger_male leg_grab legwear long_playtime looking_pleasured loona_(helluva_boss) lying male male/female male_on_bottom male_penetrating male_penetrating_female mammal masturbation millie_(helluva_boss) missionary missionary_position moan moxxie_(helluva_boss) multiple_positions muscular muscular_male narrowed_eyes o_o on_back on_bottom on_model on_top orgasm orgasm_face pawpads penetration penile penile_penetration penis penis_everywhere penis_in_pussy pink_areola profanity pussy pussy_juice red_sclera sex sex_toy size_difference small_dom_big_sub smaller_female solo_focus sound stockings submissive submissive_anthro submissive_female teeth text toe_claws toes tongue tongue_out vaginal vaginal_knotting vaginal_masturbation vaginal_penetration vivzmind voice_acted vortex_(helluva_boss) webm widescreen wolf
1girl 2019 anthro bodily_fluids breasts canid canid_demon canine canis clothing collar demon digital_media_(artwork) fur furry hair hellhound helluva_boss high_res legwear lonelycross loona_(helluva_boss) mammal nipple_slip simple_background spiked_collar spikes stockings sweat under_boob vivienne_medrano vivziepop white_body white_fur wolf
1girl 2019 anthro bodily_fluids breasts canid canid_demon canine canis clothing collar demon digital_media_(artwork) fur furry hair hellhound helluva_boss high_res legwear lonelycross loona_(helluva_boss) mammal nipple_slip simple_background spiked_collar spikes stockings sweat under_boob vivienne_medrano vivziepop white_body white_fur wolf
1girl 2020 against_glass anthro areola big_breasts breasts breasts_on_glass canid canid_demon collar darkhazard demon digital_media_(artwork) eyebrows eyelashes fangs featureless_crotch front_view furry hair hellhound helluva_boss high_res inner_ear_fluff long_hair looking_at_viewer loona_(helluva_boss) mammal nipples on_glass open_mouth piercing spiked_collar spikes tongue tongue_out tongue_piercing tuft vivienne_medrano vivzmind
1girl 2020 against_glass anthro areola big_breasts breasts breasts_on_glass canid canid_demon collar darkhazard demon digital_media_(artwork) eyebrows eyelashes fangs featureless_crotch front_view furry hair hellhound helluva_boss high_res inner_ear_fluff long_hair looking_at_viewer loona_(helluva_boss) mammal nipples on_glass open_mouth piercing spiked_collar spikes tongue tongue_out tongue_piercing tuft vivienne_medrano vivzmind
2021 2:1 abdominal_bulge anal anal_penetration animated anus big_breasts bodily_fluids breasts canid canid_demon canine cum cumshot dalwart demon dildo dildo_in_ass dildo_penetration dildo_sitting ejaculation furaffinity furry genital_fluids genitals gynomorph hellhound helluva_boss hi_res intersex lactating loona_(vivzmind) mammal patreon penetration penis red_sclera sex_toy sex_toy_in_ass sex_toy_penetration solo sound sweat tagme text twitter url watermark webm
2021 2:1 abdominal_bulge anal anal_penetration animated anus big_breasts bodily_fluids breasts canid canid_demon canine cum cumshot dalwart demon dildo dildo_in_ass dildo_penetration dildo_sitting ejaculation furaffinity furry genital_fluids genitals gynomorph hellhound helluva_boss hi_res intersex lactating loona_(vivzmind) mammal patreon penetration penis red_sclera sex_toy sex_toy_in_ass sex_toy_penetration solo sound sweat tagme text twitter url watermark webm
1girl 2020 anthro areola big_breasts blush breasts cameltoe canid canid_demon clothed clothing demon ear_piercing earring furry hair hellhound helluva_boss high_res huge_breasts looking_at_viewer loona_(helluva_boss) mammal navel notched_ear piercing red_sclera simple_background tailzkim translucent translucent_hair vivienne_medrano vivzmind white_background white_hair
1girl 2020 anthro areola big_breasts blush breasts cameltoe canid canid_demon clothed clothing demon ear_piercing earring furry hair hellhound helluva_boss high_res huge_breasts looking_at_viewer loona_(helluva_boss) mammal navel notched_ear piercing red_sclera simple_background tailzkim translucent translucent_hair vivienne_medrano vivzmind white_background white_hair
2_girls anthro areola arms_crossed artist_name big_breasts black_fur black_nose breasts canid canid_demon canine canis choker clothed clothing countershade_face countershade_torso countershading crossed_arms crossover cubedcoconut duo fang female_only five_nights_at_freddy's five_nights_at_freddy's:_security_breach fur furry green_hair grey_body grey_fur grey_hair grey_skin hair half-closed_eyes halloween hellhound helluva_boss long_hair looking_at_viewer loona_(helluva_boss) loona_(vivzmind) mammal medium_breasts mostly_clothed multicolored_body multicolored_face multicolored_fur multicolored_hair multicolored_skin multicolored_tail multiple_girls narrowed_eyes naughty_face navel nipples portrait red_sclera roxanne_wolf_(fnaf) sexy sexy_body sexy_breasts shiny shiny_skin smile smiling_at_viewer standing thick_thighs thighs three-quarter_portrait two_tone_body two_tone_face two_tone_fur two_tone_hair two_tone_skin two_tone_tail white_body white_countershading white_skin wide_hips wolf
2_girls anthro areola arms_crossed artist_name big_breasts black_fur black_nose breasts canid canid_demon canine canis choker clothed clothing countershade_face countershade_torso countershading crossed_arms crossover cubedcoconut duo fang female_only five_nights_at_freddy's five_nights_at_freddy's:_security_breach fur furry green_hair grey_body grey_fur grey_hair grey_skin hair half-closed_eyes halloween hellhound helluva_boss long_hair looking_at_viewer loona_(helluva_boss) loona_(vivzmind) mammal medium_breasts mostly_clothed multicolored_body multicolored_face multicolored_fur multicolored_hair multicolored_skin multicolored_tail multiple_girls narrowed_eyes naughty_face navel nipples portrait red_sclera roxanne_wolf_(fnaf) sexy sexy_body sexy_breasts shiny shiny_skin smile smiling_at_viewer standing thick_thighs thighs three-quarter_portrait two_tone_body two_tone_face two_tone_fur two_tone_hair two_tone_skin two_tone_tail white_body white_countershading white_skin wide_hips wolf
1girl 2020 angry annoyed anthro anus areola big_tail black_nose blush breaking_the_fourth_wall breasts canid canid_demon canine canis choker clitoral_hood clitoris demon dialogue digital_media_(artwork) ear_piercing english english_text eyebrows eyelashes eyeshadow female_only female_solo frown fur furry genitals glistening glistening_body glistening_genitalia grey_body grey_fur grey_hair hair half-closed_eyes hellhound helluva_boss high_resolution jewelry large_filesize long_hair loona_(helluva_boss) makeup mammal medium_breasts multicolored_body multicolored_fur narrowed_eyes necklace nipples notched_ear nude piercing pussy pussy_focus pussy_towards_viewer raised_tail red_sclera signature simple_background spread_legs spread_vagina spreading teeth text thick_thighs thighs very_high_resolution vivienne_medrano vivziepop vksuika white_background white_body white_fur
1girl 2020 angry annoyed anthro anus areola big_tail black_nose blush breaking_the_fourth_wall breasts canid canid_demon canine canis choker clitoral_hood clitoris demon dialogue digital_media_(artwork) ear_piercing english english_text eyebrows eyelashes eyeshadow female_only female_solo frown fur furry genitals glistening glistening_body glistening_genitalia grey_body grey_fur grey_hair hair half-closed_eyes hellhound helluva_boss high_resolution jewelry large_filesize long_hair loona_(helluva_boss) makeup mammal medium_breasts multicolored_body multicolored_fur narrowed_eyes necklace nipples notched_ear nude piercing pussy pussy_focus pussy_towards_viewer raised_tail red_sclera signature simple_background spread_legs spread_vagina spreading teeth text thick_thighs thighs very_high_resolution vivienne_medrano vivziepop vksuika white_background white_body white_fur
1girl 2019 anthro big_breasts breasts canid canid_demon canine canis cellphone clothing demon fur furry grey_hair hair helluva_boss high_res kaviki looking_at_viewer loona_(helluva_boss) mammal nipples phone pussy red_eyes smile tongue tongue_out vivienne_medrano vivziepop white_body white_fur wolf
1girl 2019 anthro big_breasts breasts canid canid_demon canine canis cellphone clothing demon fur furry grey_hair hair helluva_boss high_res kaviki looking_at_viewer loona_(helluva_boss) mammal nipples phone pussy red_eyes smile tongue tongue_out vivienne_medrano vivziepop white_body white_fur wolf
1girl anthro big_breasts bodily_fluids breasts canid canid_demon canine demon faeki furry genital_fluids genitals hellhound helluva_boss loona_(vivzmind) mammal pussy pussy_floss pussy_juice tongue tongue_out
1girl anthro big_breasts bodily_fluids breasts canid canid_demon canine demon faeki furry genital_fluids genitals hellhound helluva_boss loona_(vivzmind) mammal pussy pussy_floss pussy_juice tongue tongue_out
1girl 2020 4_fingers anthro areola big_breasts bikini breasts canid canid_demon clothing collar demon fingerless_gloves fingers fur furry gloves grey_body grey_fur grey_hair hair handwear hellhound helluva_boss holding_object holding_phone legwear loona_(helluva_boss) mammal phone red_sclera skygracer sling_bikini spiked_collar spikes stockings swimwear vivienne_medrano vivzmind white_body white_eyes white_fur
1girl 2020 4_fingers anthro areola big_breasts bikini breasts canid canid_demon clothing collar demon fingerless_gloves fingers fur furry gloves grey_body grey_fur grey_hair hair handwear hellhound helluva_boss holding_object holding_phone legwear loona_(helluva_boss) mammal phone red_sclera skygracer sling_bikini spiked_collar spikes stockings swimwear vivienne_medrano vivzmind white_body white_eyes white_fur
<3 1girl 1girl 2021 3_toes 4_fingers anthro areola bed_sheet bedding big_tail black_nose blush bodily_fluids breasts canid canid_demon canine canis clothing demon english_text eyebrow_piercing facial_piercing facial_tuft feet fingering fingerless_gloves fingers fur furry genital_fluids genitals gloves grey_body grey_fur grey_hair hair hand_on_breast handwear hellhound helluva_boss high_res legwear long_hair looking_pleasured loona_(vivzmind) lying mammal masturbation moan nipples notched_ear on_back piercing plump_labia portrait pussy pussy_blush pussy_juice raised_tail red_sclera simple_background spread_legs spreading stockings submissive text toes translucent translucent_hair tuft vaginal vksuika watermark white_body white_fur
<3 1girl 1girl 2021 3_toes 4_fingers anthro areola bed_sheet bedding big_tail black_nose blush bodily_fluids breasts canid canid_demon canine canis clothing demon english_text eyebrow_piercing facial_piercing facial_tuft feet fingering fingerless_gloves fingers fur furry genital_fluids genitals gloves grey_body grey_fur grey_hair hair hand_on_breast handwear hellhound helluva_boss high_res legwear long_hair looking_pleasured loona_(vivzmind) lying mammal masturbation moan nipples notched_ear on_back piercing plump_labia portrait pussy pussy_blush pussy_juice raised_tail red_sclera simple_background spread_legs spreading stockings submissive text toes translucent translucent_hair tuft vaginal vksuika watermark white_body white_fur
1girl 1girl 1girl anthro breasts canid canid_demon canine canis clothing collar demon digital_media_(artwork) ear_piercing earrings female_only female_solo fingerless_gloves fur furry genitals gloves hair handwear hellhound helluva_boss high_resolution jewelry legwear looking_at_viewer loona_(vivzmind) mammal nipples nude piercing pkuai pussy red_sclera simple_background smile stockings white_body white_fur wolf
1girl 1girl 1girl anthro breasts canid canid_demon canine canis clothing collar demon digital_media_(artwork) ear_piercing earrings female_only female_solo fingerless_gloves fur furry genitals gloves hair handwear hellhound helluva_boss high_resolution jewelry legwear looking_at_viewer loona_(vivzmind) mammal nipples nude piercing pkuai pussy red_sclera simple_background smile stockings white_body white_fur wolf
1girl 2020 accessory anthro anus areola ass blue_hair breasts canid canid_demon canine crossover demon digital_media_(artwork) duo eyelashes female/female fingers fox front_view furry genitals green_eyes grey_hair hair hair_accessory hairband hand_behind_back hand_on_breast hellhound helluva_boss high_res inner_ear_fluff krystal long_hair looking_at_viewer looking_back loona_(vivzmind) mammal markings navel nintendo nipples notched_ear nude pussy rear_view red_sclera short_hair shoulder_tuft smile star_fox text tribal_markings tuft twistedscarlett60 url video_games
1girl 2020 accessory anthro anus areola ass blue_hair breasts canid canid_demon canine crossover demon digital_media_(artwork) duo eyelashes female/female fingers fox front_view furry genitals green_eyes grey_hair hair hair_accessory hairband hand_behind_back hand_on_breast hellhound helluva_boss high_res inner_ear_fluff krystal long_hair looking_at_viewer looking_back loona_(vivzmind) mammal markings navel nintendo nipples notched_ear nude pussy rear_view red_sclera short_hair shoulder_tuft smile star_fox text tribal_markings tuft twistedscarlett60 url video_games
1girl 2019 animal_genitalia animal_penis anonymous anthro balls big_breasts black_penis bodily_fluids breasts canid canid_demon canine canine_penis clothing collar demon demonic fluffy_fur fluffy_hair fur furry genital_fluids grey_body grey_fur group hair hazbin_hotel helluva_boss high_res humanoid_penis johnithanial knot legwear long_hair loona_(helluva_boss) male mammal nipples penis piercing precum red_eyes undressing vivienne_medrano vivziepop
1girl 2019 animal_genitalia animal_penis anonymous anthro balls big_breasts black_penis bodily_fluids breasts canid canid_demon canine canine_penis clothing collar demon demonic fluffy_fur fluffy_hair fur furry genital_fluids grey_body grey_fur group hair hazbin_hotel helluva_boss high_res humanoid_penis johnithanial knot legwear long_hair loona_(helluva_boss) male mammal nipples penis piercing precum red_eyes undressing vivienne_medrano vivziepop
1boy 1girl anthro areola ass_visible_through_thighs big_breasts black_body black_fur black_legwear black_skin black_thighhighs blush breast_grab breasts canid canid_demon collar demon eye_contact faceless_male female_anthro female_focus first_person_view fondling fondling_breasts fur furry grabbing_breasts grey_body grey_eyes grey_fur grey_hair grey_skin groping hair_over_one_eye helluva_boss huge_breasts human human/anthro human_on_anthro human_pov inner_ear_fluff interspecies kironzen legwear long_hair looking_at_viewer loona_(helluva_boss) male_human male_human/female_anthro male_pov mammal mostly_nude multicolored_body multicolored_fur multicolored_skin navel nipples nude pov pov_eye_contact pov_hands pussy red_sclera sexy sexy_body sexy_breasts smile smiling_at_viewer stockings thick thick_thighs thighs two_tone_body unseen_male_face white_body white_skin
1boy 1girl anthro areola ass_visible_through_thighs big_breasts black_body black_fur black_legwear black_skin black_thighhighs blush breast_grab breasts canid canid_demon collar demon eye_contact faceless_male female_anthro female_focus first_person_view fondling fondling_breasts fur furry grabbing_breasts grey_body grey_eyes grey_fur grey_hair grey_skin groping hair_over_one_eye helluva_boss huge_breasts human human/anthro human_on_anthro human_pov inner_ear_fluff interspecies kironzen legwear long_hair looking_at_viewer loona_(helluva_boss) male_human male_human/female_anthro male_pov mammal mostly_nude multicolored_body multicolored_fur multicolored_skin navel nipples nude pov pov_eye_contact pov_hands pussy red_sclera sexy sexy_body sexy_breasts smile smiling_at_viewer stockings thick thick_thighs thighs two_tone_body unseen_male_face white_body white_skin
1girl 2021 4_fingers anthro anus areola ass black_nose blush breasts canid canid_demon canine canis chest_tuft clitoral_hood clitoris clothing collar demon digital_media_(artwork) english_text fingers fluffy_tail fur furry genitals grey_body grey_fur grey_hair hair hellhound helluva_boss high_res legs_up legwear licking licking_lips long_hair looking_at_genitalia looking_down loona_(vivzmind) mammal mostly_nude multicolored_body multicolored_fur nipples piercing portrait presenting presenting_anus presenting_pussy pussy red_sclera smile spiked_collar spikes spread_legs spread_pussy spreading stockings text thick_thighs tongue tongue_out tuft two_tone_body two_tone_fur vksuika watermark white_body white_fur
1girl 2021 4_fingers anthro anus areola ass black_nose blush breasts canid canid_demon canine canis chest_tuft clitoral_hood clitoris clothing collar demon digital_media_(artwork) english_text fingers fluffy_tail fur furry genitals grey_body grey_fur grey_hair hair hellhound helluva_boss high_res legs_up legwear licking licking_lips long_hair looking_at_genitalia looking_down loona_(vivzmind) mammal mostly_nude multicolored_body multicolored_fur nipples piercing portrait presenting presenting_anus presenting_pussy pussy red_sclera smile spiked_collar spikes spread_legs spread_pussy spreading stockings text thick_thighs tongue tongue_out tuft two_tone_body two_tone_fur vksuika watermark white_body white_fur
1girl 2021 3:4 anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro black_body black_fur black_nose bodily_fluids breasts canid canid_demon capaoculta collar cowgirl_position cum cum_in_pussy cum_inside demon duo erection female_penetrated first_person_view fur furry genital_fluids genitals grey_body grey_fur hellhound helluva_boss high_res licking licking_lips licking_own_lips loona_(vivzmind) male male/female male_penetrating male_penetrating_female mammal navel nipples nude on_bottom on_top penetration penile penile_penetration penis penis_in_pussy pink_nipples pink_penis red_background red_sclera self_lick sex simple_background spiked_collar spikes tongue tongue_out vaginal vaginal_penetration white_body white_fur
1girl 2021 3:4 anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro black_body black_fur black_nose bodily_fluids breasts canid canid_demon capaoculta collar cowgirl_position cum cum_in_pussy cum_inside demon duo erection female_penetrated first_person_view fur furry genital_fluids genitals grey_body grey_fur hellhound helluva_boss high_res licking licking_lips licking_own_lips loona_(vivzmind) male male/female male_penetrating male_penetrating_female mammal navel nipples nude on_bottom on_top penetration penile penile_penetration penis penis_in_pussy pink_nipples pink_penis red_background red_sclera self_lick sex simple_background spiked_collar spikes tongue tongue_out vaginal vaginal_penetration white_body white_fur
1girl anthro black_nose breasts canid canid_demon canine closed_eyes clothing collar crossover demon dialogue duo facesitting female/female fox furry glistening glistening_body hellhound helluva_boss high_res krystal legwear loona_(helluva_boss) mammal nintendo nipple_fetish nipple_play nipples series star_fox stockings twiren video_games vivienne_medrano vivziepop
1girl anthro black_nose breasts canid canid_demon canine closed_eyes clothing collar crossover demon dialogue duo facesitting female/female fox furry glistening glistening_body hellhound helluva_boss high_res krystal legwear loona_(helluva_boss) mammal nintendo nipple_fetish nipple_play nipples series star_fox stockings twiren video_games vivienne_medrano vivziepop
1girl anthro anus ass bodily_fluids book breasts canid canid_demon canine closed_eyes clothing collar demon dialogue english_text erect_nipples furry genital_fluids genitals hellhound helluva_boss high_res improvised_sex_toy legwear looking_pleasured loona_(helluva_boss) mammal masturbation millie_(helluva_boss) nipples profanity pussy pussy_juice stockings text twiren url vivienne_medrano vivzmind
1girl anthro anus ass bodily_fluids book breasts canid canid_demon canine closed_eyes clothing collar demon dialogue english_text erect_nipples furry genital_fluids genitals hellhound helluva_boss high_res improvised_sex_toy legwear looking_pleasured loona_(helluva_boss) mammal masturbation millie_(helluva_boss) nipples profanity pussy pussy_juice stockings text twiren url vivienne_medrano vivzmind
1girl anthro black_eyebrows black_nose canid canid_demon canine canis cherryhaze choker collar demon ear_piercing earring eyebrow_piercing eyebrows facial_piercing furry grey_body hellhound helluva_boss jewelry loona_(helluva_boss) mammal monster necklace piercing red_eyes red_tongue teeth tongue vivienne_medrano vivzmind were werecanid white_body wolf
1girl anthro black_eyebrows black_nose canid canid_demon canine canis cherryhaze choker collar demon ear_piercing earring eyebrow_piercing eyebrows facial_piercing furry grey_body hellhound helluva_boss jewelry loona_(helluva_boss) mammal monster necklace piercing red_eyes red_tongue teeth tongue vivienne_medrano vivzmind were werecanid white_body wolf
1girl 2019 absurd_res anthro areola big_areolae big_breasts breasts canid canid_demon canine cervina7_(artist) clothing collar curvy_figure demon fingerless_gloves fur furry genitals gloves grey_body grey_fur grey_hair hair half-closed_eyes handwear hazbin_hotel hellhound helluva_boss high_res huge_breasts looking_at_viewer loona_(helluva_boss) mammal multicolored_body multicolored_fur narrowed_eyes navel nipples nude open_mouth pink_nipples pussy red_background red_eyes red_sclera simple_background thick_thighs vivienne_medrano vivzmind voluptuous white_body white_eyes white_fur wide_hips
1girl 2019 absurd_res anthro areola big_areolae big_breasts breasts canid canid_demon canine cervina7_(artist) clothing collar curvy_figure demon fingerless_gloves fur furry genitals gloves grey_body grey_fur grey_hair hair half-closed_eyes handwear hazbin_hotel hellhound helluva_boss high_res huge_breasts looking_at_viewer loona_(helluva_boss) mammal multicolored_body multicolored_fur narrowed_eyes navel nipples nude open_mouth pink_nipples pussy red_background red_eyes red_sclera simple_background thick_thighs vivienne_medrano vivzmind voluptuous white_body white_eyes white_fur wide_hips
1girl 2019 anthro anus ass black_penis breasts canid canid_demon canine canis cellphone claws clothed clothing collar demon digital_media_(artwork) dildo dildo_sitting fingers fur furry hair hellhound helluva_boss high_res holding_object loona_(helluva_boss) mammal nude ownychan penetration penis phone pussy red_sclera sex_toy simple_background text topwear vaginal vaginal_penetration vivienne_medrano vivziepop white_body white_fur wolf
1girl 2019 anthro anus ass black_penis breasts canid canid_demon canine canis cellphone claws clothed clothing collar demon digital_media_(artwork) dildo dildo_sitting fingers fur furry hair hellhound helluva_boss high_res holding_object loona_(helluva_boss) mammal nude ownychan penetration penis phone pussy red_sclera sex_toy simple_background text topwear vaginal vaginal_penetration vivienne_medrano vivziepop white_body white_fur wolf
1girl 2019 absurd_res angry anthro breasts canid canid_demon canine canis claws demon digital_media_(artwork) fingers fur furry goth hair helluva_boss high_res looking_at_viewer loona_(helluva_boss) mammal nipples nude piercing pussy red_eyes ruetteroulette simple_background teeth text vivienne_medrano vivziepop white_body white_fur wolf
1girl 2019 absurd_res angry anthro breasts canid canid_demon canine canis claws demon digital_media_(artwork) fingers fur furry goth hair helluva_boss high_res looking_at_viewer loona_(helluva_boss) mammal nipples nude piercing pussy red_eyes ruetteroulette simple_background teeth text vivienne_medrano vivziepop white_body white_fur wolf
1girl 1girl 2021 anthro ass big_ass big_breasts bodily_fluids breasts canid canid_demon clothed clothing collar crouching demon drooling faeki feet footwear fur furry genital_fluids genitals grey_hair hair hellhound helluva_boss legwear loona_(vivzmind) mammal nipples pink_nipples pussy pussy_floss pussy_juice rear_view red_eyes saliva simple_background socks spiked_collar spikes stockings thong toeless_footwear toeless_socks toes tongue tongue_out topless underwear white_background white_body white_fur
1girl 1girl 2021 anthro ass big_ass big_breasts bodily_fluids breasts canid canid_demon clothed clothing collar crouching demon drooling faeki feet footwear fur furry genital_fluids genitals grey_hair hair hellhound helluva_boss legwear loona_(vivzmind) mammal nipples pink_nipples pussy pussy_floss pussy_juice rear_view red_eyes saliva simple_background socks spiked_collar spikes stockings thong toeless_footwear toeless_socks toes tongue tongue_out topless underwear white_background white_body white_fur
1girl 1girl 1girl anthro anus ass big_ass bottomwear breasts canid canid_demon clothing demon ear_piercing fox fur furry genitals grey_body grey_hair hair hellhound helluva_boss high_res looking_at_viewer loona_(vivzmind) mammal medium_breasts nude panties pattern_bottomwear pattern_clothing pattern_panties pattern_underwear piercing presenting presenting_anus presenting_pussy pussy shvarno smile smiling_at_viewer striped_bottomwear striped_clothing striped_panties striped_underwear stripes tail thick_thighs underwear undressing vivzmind white_body white_eyes wide_hips
1girl 1girl 1girl anthro anus ass big_ass bottomwear breasts canid canid_demon clothing demon ear_piercing fox fur furry genitals grey_body grey_hair hair hellhound helluva_boss high_res looking_at_viewer loona_(vivzmind) mammal medium_breasts nude panties pattern_bottomwear pattern_clothing pattern_panties pattern_underwear piercing presenting presenting_anus presenting_pussy pussy shvarno smile smiling_at_viewer striped_bottomwear striped_clothing striped_panties striped_underwear stripes tail thick_thighs underwear undressing vivzmind white_body white_eyes wide_hips
2023 activision anal anal_only anal_sex animal_crossing animated ankha_(animal_crossing) anthro anus areola ass balls bare_back big_ass big_breasts big_penis bodily_fluids breasts brothel cameltoe canid canid_demon canine canis clothing crossover cum cum_in_ass cum_inside cumshot dalwart dat_ass demon detailed_background diane_foxington digital_drawing_(artwork) digital_media_(artwork) disney domestic_cat dreamworks duo ear_piercing earring ejaculation elora english_text eyebrow_piercing eyebrow_ring faceless_character faceless_male facial_piercing feet felid feline felis female female_penetrated fingers front_view fur fur_markings gardevoir gen_3_pokemon gen_4_pokemon genital_fluids genitals hellhound helluva_boss hi_res hindpaw huge_filesize human human_penetrating humanoid_genitalia humanoid_penis illumination_entertainment judy_hopps lagomorph legwear leporid lola_bunny long_playtime looking_up loona_(vivzmind) looney_tunes lucario male male/female male_penetrating male_penetrating_female mammal markings multicolored_body multicolored_fur navel nintendo nipple_piercing nipples oatmealpecheneg orgasm paws penetration penile penile_penetration penis penis_in_ass piercing pink_areola pink_nipples pokemon pokemon_(species) porsha_crystal presenting presenting_anus presenting_pussy puffy_anus pussy pussy_juice pussy_tape rabbit red_sclera ring_piercing saliva saliva_on_tongue saliva_string sex sing_(movie) sound spyro_the_dragon sticker tagme text the_bad_guys thick_thighs tongue tongue_out two_tone_body two_tone_fur url video vivzmind warner_brothers watermark white_body white_fur wolf zootopia
2023 activision anal anal_only anal_sex animal_crossing animated ankha_(animal_crossing) anthro anus areola ass balls bare_back big_ass big_breasts big_penis bodily_fluids breasts brothel cameltoe canid canid_demon canine canis clothing crossover cum cum_in_ass cum_inside cumshot dalwart dat_ass demon detailed_background diane_foxington digital_drawing_(artwork) digital_media_(artwork) disney domestic_cat dreamworks duo ear_piercing earring ejaculation elora english_text eyebrow_piercing eyebrow_ring faceless_character faceless_male facial_piercing feet felid feline felis female female_penetrated fingers front_view fur fur_markings gardevoir gen_3_pokemon gen_4_pokemon genital_fluids genitals hellhound helluva_boss hi_res hindpaw huge_filesize human human_penetrating humanoid_genitalia humanoid_penis illumination_entertainment judy_hopps lagomorph legwear leporid lola_bunny long_playtime looking_up loona_(vivzmind) looney_tunes lucario male male/female male_penetrating male_penetrating_female mammal markings multicolored_body multicolored_fur navel nintendo nipple_piercing nipples oatmealpecheneg orgasm paws penetration penile penile_penetration penis penis_in_ass piercing pink_areola pink_nipples pokemon pokemon_(species) porsha_crystal presenting presenting_anus presenting_pussy puffy_anus pussy pussy_juice pussy_tape rabbit red_sclera ring_piercing saliva saliva_on_tongue saliva_string sex sing_(movie) sound spyro_the_dragon sticker tagme text the_bad_guys thick_thighs tongue tongue_out two_tone_body two_tone_fur url video vivzmind warner_brothers watermark white_body white_fur wolf zootopia
1girl 5_fingers anthro ass black_body black_hair black_nose blue_fur blue_hair canid canid_demon curved_horn demon duo fan_character fingers furry gloves grey_body grey_fur grey_hair hair helluva_boss horn looking_at_another loona_(vivzmind) markings multicolored_body multicolored_fur purple_claws red_sclera signature snout sora_(sorafoxyteils) sorafoxyteils water white_body white_fur
1girl 5_fingers anthro ass black_body black_hair black_nose blue_fur blue_hair canid canid_demon curved_horn demon duo fan_character fingers furry gloves grey_body grey_fur grey_hair hair helluva_boss horn looking_at_another loona_(vivzmind) markings multicolored_body multicolored_fur purple_claws red_sclera signature snout sora_(sorafoxyteils) sorafoxyteils water white_body white_fur
1girl anthro big_breasts breasts canid canid_demon canine demon furry hellhound helluva_boss high_res loona_(helluva_boss) mammal slightly_chubby viejillox vivienne_medrano vivzmind
1girl anthro big_breasts breasts canid canid_demon canine demon furry hellhound helluva_boss high_res loona_(helluva_boss) mammal slightly_chubby viejillox vivienne_medrano vivzmind
1girl 2019 anthro areola areola_slip bedroom_eyes big_breasts bodily_fluids breasts cameltoe canid canid_demon canine canis clothing collar demon digital_media_(artwork) fur furry glistening glistening_body hair hellhound helluva_boss high_res legwear loona_(helluva_boss) mammal narrowed_eyes pentagram red_sclera seductive simple_background spiked_collar spikes stockings sweat topwear under_boob vivienne_medrano vivzmind whisperingfornothing white_body white_fur wolf
1girl 2019 anthro areola areola_slip bedroom_eyes big_breasts bodily_fluids breasts cameltoe canid canid_demon canine canis clothing collar demon digital_media_(artwork) fur furry glistening glistening_body hair hellhound helluva_boss high_res legwear loona_(helluva_boss) mammal narrowed_eyes pentagram red_sclera seductive simple_background spiked_collar spikes stockings sweat topwear under_boob vivienne_medrano vivzmind whisperingfornothing white_body white_fur wolf
1girl 2019 5_fingers anthro areola bdsm big_breasts bondage bound breasts canid canid_demon canine canis cellphone christmas clothing collar demon digital_media_(artwork) fingers fur furry gloves grimace hair handwear hazelmere hellhound helluva_boss high_res holidays kneel legwear looking_at_viewer loona_(helluva_boss) mammal nipples pentagram phone red_sclera ribbons stockings teeth vivienne_medrano vivzmind white_body white_fur wolf
1girl 2019 5_fingers anthro areola bdsm big_breasts bondage bound breasts canid canid_demon canine canis cellphone christmas clothing collar demon digital_media_(artwork) fingers fur furry gloves grimace hair handwear hazelmere hellhound helluva_boss high_res holidays kneel legwear looking_at_viewer loona_(helluva_boss) mammal nipples pentagram phone red_sclera ribbons stockings teeth vivienne_medrano vivzmind white_body white_fur wolf
1girl 2019 anthro blush breasts canid canid_demon canine canis clothed clothing clothing_lift collar demon fangs furry hellhound helluva_boss looking_at_viewer loona_(helluva_boss) mammal nipple_piercing nipples nude piercing pussy red_eyes red_sclera shirt shirt_lift stargazer text topwear underwear vivienne_medrano vivziepop wolf
1girl 2019 anthro blush breasts canid canid_demon canine canis clothed clothing clothing_lift collar demon fangs furry hellhound helluva_boss looking_at_viewer loona_(helluva_boss) mammal nipple_piercing nipples nude piercing pussy red_eyes red_sclera shirt shirt_lift stargazer text topwear underwear vivienne_medrano vivziepop wolf
<3 1girl 2021 anthro areola balls blush bodily_fluids breasts canid canid_demon chest_tuft clothing collar collar_only conditional_dnp demon dialogue digital_media_(artwork) duo english_text eyebrows faceless_character faceless_male fingers furry genital_fluids genitals hair hellhound helluva_boss high_res imminent_fellatio imminent_sex imminent_vaginal legwear long_hair looking_at_genitalia looking_at_penis loona_(vivzmind) male male/female mammal navel nipples open_mouth penis penis_awe penis_worship pussy red_sclera sitting solo_focus text tuft vivzmind vortex_(vivzmind) whisperfoot
<3 1girl 2021 anthro areola balls blush bodily_fluids breasts canid canid_demon chest_tuft clothing collar collar_only conditional_dnp demon dialogue digital_media_(artwork) duo english_text eyebrows faceless_character faceless_male fingers furry genital_fluids genitals hair hellhound helluva_boss high_res imminent_fellatio imminent_sex imminent_vaginal legwear long_hair looking_at_genitalia looking_at_penis loona_(vivzmind) male male/female mammal navel nipples open_mouth penis penis_awe penis_worship pussy red_sclera sitting solo_focus text tuft vivzmind vortex_(vivzmind) whisperfoot
<3 1girl 2021 after_fellatio after_sex anthro areola blush bodily_fluids breasts canid canid_demon chest_tuft collar collar_only conditional_dnp cum cum_in_hair cum_on_face cum_on_tongue demon dialogue digital_media_(artwork) english_text eyebrows eyelashes fingers furry genital_fluids genitals hair half-closed_eyes hellhound helluva_boss high_res long_hair loona_(vivzmind) mammal narrowed_eyes navel nipples pussy red_sclera satisfied sitting text tongue tongue_out tuft whisperfoot
<3 1girl 2021 after_fellatio after_sex anthro areola blush bodily_fluids breasts canid canid_demon chest_tuft collar collar_only conditional_dnp cum cum_in_hair cum_on_face cum_on_tongue demon dialogue digital_media_(artwork) english_text eyebrows eyelashes fingers furry genital_fluids genitals hair half-closed_eyes hellhound helluva_boss high_res long_hair loona_(vivzmind) mammal narrowed_eyes navel nipples pussy red_sclera satisfied sitting text tongue tongue_out tuft whisperfoot