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2boys 4_arms ? absurd_res ahe_gao all_fours anal anal_sex angel_dust_(hazbin_hotel) animal_humanoid arachnid arms_behind_head arthropod ass ass_grab balls bed bedroom bedroom_eyes big_penis black_sclera blush bodily_fluids bow_tie breasts breath canid canine canis cheating cheek_tuft clothed_male clothed_male_nude_male clothing cowgirl_position cum cum_in_ass cum_inside doggy_style drooling ear_piercing erection excited eye_contact eyeshadow facial_hair facial_tuft fellatio fluffy_balls foaming_at_the_mouth from_behind_position fuf fur furniture furry genital_fluids genitals gloves gold_tooth green_eyes grey_body grey_fur half-closed_eyes hands_behind_head handwear hazbin_hotel heart heart-shaped_pupils heavy_breathing helluva_boss heterochromia hi_res huge_cock huge_penis large_penis leg_grab licking_penis loona_(helluva_boss) lying male multi_arm multi_limb narrowed_eyes navel on_back on_bed open_mouth oral oral_penetration paizuri panting pawpads penis penis_size_difference piercing pink_spots red_eyes red_sclera riding saliva saliva_on_penis seductive seductive_look seductive_smile sex sharp_teeth smile spider spots surprised teeth titjob tongue tongue_out tuft undressing vivienne_medrano vivienne_style white_body white_fur wolf yaoi
2boys 4_arms ? absurd_res ahe_gao all_fours anal anal_sex angel_dust_(hazbin_hotel) animal_humanoid arachnid arms_behind_head arthropod ass ass_grab balls bed bedroom bedroom_eyes big_penis black_sclera blush bodily_fluids bow_tie breasts breath canid canine canis cheating cheek_tuft clothed_male clothed_male_nude_male clothing cowgirl_position cum cum_in_ass cum_inside doggy_style drooling ear_piercing erection excited eye_contact eyeshadow facial_hair facial_tuft fellatio fluffy_balls foaming_at_the_mouth from_behind_position fuf fur furniture furry genital_fluids genitals gloves gold_tooth green_eyes grey_body grey_fur half-closed_eyes hands_behind_head handwear hazbin_hotel heart heart-shaped_pupils heavy_breathing helluva_boss heterochromia hi_res huge_cock huge_penis large_penis leg_grab licking_penis loona_(helluva_boss) lying male multi_arm multi_limb narrowed_eyes navel on_back on_bed open_mouth oral oral_penetration paizuri panting pawpads penis penis_size_difference piercing pink_spots red_eyes red_sclera riding saliva saliva_on_penis seductive seductive_look seductive_smile sex sharp_teeth smile spider spots surprised teeth titjob tongue tongue_out tuft undressing vivienne_medrano vivienne_style white_body white_fur wolf yaoi
1boy 1girls 2020 absurdres animal_genitalia animal_penis anthro blush bodily_fluids breasts canid canid_demon canine canine_penis canis capaoculta cum cum_on_breasts cum_on_face cum_on_tongue demon duo fellatio female female_focus fur furry genital_fluids giver_pov grey_body grey_fur hellhound helluva_boss highres licking looking_at_viewer loona_(helluva_boss) male mammal nipples open_mouth oral outercourse paizuri penile penis penis_lick penis_on_tongue red_eyes sex straight teeth tongue tongue_out vivienne_medrano vivienne_style white_fur wolf wolf_girl wolf_tail
1boy 1girls 2020 absurdres animal_genitalia animal_penis anthro blush bodily_fluids breasts canid canid_demon canine canine_penis canis capaoculta cum cum_on_breasts cum_on_face cum_on_tongue demon duo fellatio female female_focus fur furry genital_fluids giver_pov grey_body grey_fur hellhound helluva_boss highres licking looking_at_viewer loona_(helluva_boss) male mammal nipples open_mouth oral outercourse paizuri penile penis penis_lick penis_on_tongue red_eyes sex straight teeth tongue tongue_out vivienne_medrano vivienne_style white_fur wolf wolf_girl wolf_tail
1boy 1girls 2019 2demons ass bed black_hair black_lipstick bowtie breasts choker couple demon erect_nipples female fingerless_gloves gloves helluva_boss horns licking_pussy millie_(helluva_boss) mole moxxie_(helluva_boss) naked nipples one_eye_closed open_mouth partially_clothed penis pillow red_skin short_hair speech_bubble spoken_heart stockings straight suit sweat tail vivienne_medrano vivienne_style white_hair yellow_eyes zusurumiyansfw
1boy 1girls 2019 2demons ass bed black_hair black_lipstick bowtie breasts choker couple demon erect_nipples female fingerless_gloves gloves helluva_boss horns licking_pussy millie_(helluva_boss) mole moxxie_(helluva_boss) naked nipples one_eye_closed open_mouth partially_clothed penis pillow red_skin short_hair speech_bubble spoken_heart stockings straight suit sweat tail vivienne_medrano vivienne_style white_hair yellow_eyes zusurumiyansfw
2boys avian bird blush bodily_fluids bow_tie chest_tuft clothed clothed_sex clothing cum demon digitigrade erection feathers genital_fluids handjob heart helluva_boss horn imp larger_male male male_only malesub masturbation motion_lines moxxie_(helluva_boss) multi_eye nude on_lap owl owl_demon partially_clothed penile red_eyes sex sharp_teeth simple_background sitting sitting_on_lap size_difference smaller_male steam stolas_(helluva_boss) suspicious_spirit sweat teeth tuft vivienne_medrano vivienne_style watermark yaoi yellow_eyes
2boys avian bird blush bodily_fluids bow_tie chest_tuft clothed clothed_sex clothing cum demon digitigrade erection feathers genital_fluids handjob heart helluva_boss horn imp larger_male male male_only malesub masturbation motion_lines moxxie_(helluva_boss) multi_eye nude on_lap owl owl_demon partially_clothed penile red_eyes sex sharp_teeth simple_background sitting sitting_on_lap size_difference smaller_male steam stolas_(helluva_boss) suspicious_spirit sweat teeth tuft vivienne_medrano vivienne_style watermark yaoi yellow_eyes
1boy 1girls 2020 2020s absurd_res after_sex angel_dust_(hazbin_hotel) animal_humanoid anus black_hair black_nose blush bodily_fluids breasts breath canid canid_demon canine canis claws clothing collar comic cum cum_drip cum_in_ass cum_in_pussy cum_inside cum_leaking demon dripping drooling ear_piercing erection eyelashes fangs female finger_to_mouth foaming_at_mouth foaming_at_the_mouth fuf fur furry genital_fluids genitals green_eyes grey_body grey_fur hair hair_over_eyes hazbin_hotel heart hellhound helluva_boss hi_res humanoid_genitalia humanoid_penis long_hair looking_pleasured loona_(helluva_boss) male mammal nipples open_mouth open_smile panting penetration penis piercing pink_nipples pink_nose pussy pussy_juice red_sclera riding saliva sharp_teeth shoulder_tuft smile spiked_collar spikes spiral_eyes stomach_bulge straight sweat teeth tongue tongue_out tuft undressing vaginal_penetration vivienne_medrano vivienne_style white_body white_eyes white_fur wolf
1boy 1girls 2020 2020s absurd_res after_sex angel_dust_(hazbin_hotel) animal_humanoid anus black_hair black_nose blush bodily_fluids breasts breath canid canid_demon canine canis claws clothing collar comic cum cum_drip cum_in_ass cum_in_pussy cum_inside cum_leaking demon dripping drooling ear_piercing erection eyelashes fangs female finger_to_mouth foaming_at_mouth foaming_at_the_mouth fuf fur furry genital_fluids genitals green_eyes grey_body grey_fur hair hair_over_eyes hazbin_hotel heart hellhound helluva_boss hi_res humanoid_genitalia humanoid_penis long_hair looking_pleasured loona_(helluva_boss) male mammal nipples open_mouth open_smile panting penetration penis piercing pink_nipples pink_nose pussy pussy_juice red_sclera riding saliva sharp_teeth shoulder_tuft smile spiked_collar spikes spiral_eyes stomach_bulge straight sweat teeth tongue tongue_out tuft undressing vaginal_penetration vivienne_medrano vivienne_style white_body white_eyes white_fur wolf
2019 2boys after_sex angel_dust_(hazbin_hotel) anthro anus arachnid arthropod avian bird blush bodily_fluids chest_tuft clothed clothing crossover cum cum_in_ass cum_inside demon duo feathers furry genital_fluids hazbin_hotel helluva_boss hi_res legwear male male_only markings multi_arm multi_eye multi_limb owl owl_demon penis red_eyes sharp_teeth simple_background spider stolas_(helluva_boss) straight_hair suspicious_spirit teeth thigh_highs tuft vivienne_medrano vivienne_style watermark
2019 2boys after_sex angel_dust_(hazbin_hotel) anthro anus arachnid arthropod avian bird blush bodily_fluids chest_tuft clothed clothing crossover cum cum_in_ass cum_inside demon duo feathers furry genital_fluids hazbin_hotel helluva_boss hi_res legwear male male_only markings multi_arm multi_eye multi_limb owl owl_demon penis red_eyes sharp_teeth simple_background spider stolas_(helluva_boss) straight_hair suspicious_spirit teeth thigh_highs tuft vivienne_medrano vivienne_style watermark
1girls ass_tattoo beauty_mark bedroom_eyes big_ass black_hair bodily_fluids breasts choker curvy demon demon_girl demon_tail eye_shadow female helluva_boss hooves horn horns leg_lift leg_up lifting_leg looking_at_viewer millie_(helluva_boss) naked perilune pussy pussy_juice red_skin seductive_look seductive_smile short_hair solo tail tattoo tattoos thick_thighs two-tone_hair two_tone_body two_tone_hair two_tone_skin two_tone_tail vivienne_medrano vivienne_style wet_pussy wide_hips yellow_eyes
1girls ass_tattoo beauty_mark bedroom_eyes big_ass black_hair bodily_fluids breasts choker curvy demon demon_girl demon_tail eye_shadow female helluva_boss hooves horn horns leg_lift leg_up lifting_leg looking_at_viewer millie_(helluva_boss) naked perilune pussy pussy_juice red_skin seductive_look seductive_smile short_hair solo tail tattoo tattoos thick_thighs two-tone_hair two_tone_body two_tone_hair two_tone_skin two_tone_tail vivienne_medrano vivienne_style wet_pussy wide_hips yellow_eyes
2019 3boys angel_dust_(hazbin_hotel) avian avian_humanoid blitzo_(helluva_boss) blush boner bulge bulge_through_clothing choker clothed clothing crossed_legs demon dialogue embarrassed feathers femboy fur group hand_on_shoulder hazbin_hotel helluva_boss imminent_sex imp lipstick lipstick_mark male male_only mostly_nude naked_stockings naked_thighhighs owl_demon sandwiched seductive smile spider stockings stolas_(helluva_boss) straight_hair suspicious_spirit tailwag thighhighs vivienne_medrano vivienne_style wine wine_glass
2019 3boys angel_dust_(hazbin_hotel) avian avian_humanoid blitzo_(helluva_boss) blush boner bulge bulge_through_clothing choker clothed clothing crossed_legs demon dialogue embarrassed feathers femboy fur group hand_on_shoulder hazbin_hotel helluva_boss imminent_sex imp lipstick lipstick_mark male male_only mostly_nude naked_stockings naked_thighhighs owl_demon sandwiched seductive smile spider stockings stolas_(helluva_boss) straight_hair suspicious_spirit tailwag thighhighs vivienne_medrano vivienne_style wine wine_glass
1boy 1girls 5_fingers absurd_res ahe_gao anal anal_sex anus ass black_horn bodily_fluids butt_grab butt_slap demon demon_humanoid drooling duo enookie femdom fingers first_person_view from_behind_position grabbing_sheets hair hand_on_butt helluva_boss hi_res horn humanoid humanoid_penetrated male_focus male_penetrated malesub millie_(helluva_boss) moxxie_(helluva_boss) navel open_mouth pegging penetration pillow red_body red_butt red_skin red_tail saliva sex sharp_teeth slap spanking strap-on sweat teeth text tongue tongue_out two_tone_horn vivienne_medrano vivienne_style white_hair white_horn
1boy 1girls 5_fingers absurd_res ahe_gao anal anal_sex anus ass black_horn bodily_fluids butt_grab butt_slap demon demon_humanoid drooling duo enookie femdom fingers first_person_view from_behind_position grabbing_sheets hair hand_on_butt helluva_boss hi_res horn humanoid humanoid_penetrated male_focus male_penetrated malesub millie_(helluva_boss) moxxie_(helluva_boss) navel open_mouth pegging penetration pillow red_body red_butt red_skin red_tail saliva sex sharp_teeth slap spanking strap-on sweat teeth text tongue tongue_out two_tone_horn vivienne_medrano vivienne_style white_hair white_horn
1girls bedroom_eyes bent_over black_hair black_panties demon demon_girl demon_horns demon_tail dimples_of_venus face_down_ass_up female female_only flirting hands_on_head helluva_boss hooves horns imp looking_at_viewer millie_(helluva_boss) on_knees one_eye_covered open_mouth panties pointed_tail queencomplex red_skin ripped_stockings short_hair smiling stirrup_socks stockings tail tape taped_nipples thick thong tooth_gap vivienne_medrano vivienne_style yellow_eyes
1girls bedroom_eyes bent_over black_hair black_panties demon demon_girl demon_horns demon_tail dimples_of_venus face_down_ass_up female female_only flirting hands_on_head helluva_boss hooves horns imp looking_at_viewer millie_(helluva_boss) on_knees one_eye_covered open_mouth panties pointed_tail queencomplex red_skin ripped_stockings short_hair smiling stirrup_socks stockings tail tape taped_nipples thick thong tooth_gap vivienne_medrano vivienne_style yellow_eyes
2boys anal anal_sex anus avian balls bird blitzo_(helluva_boss) blush bodily_fluids clothed clothing cum demon detailed_background duo genital_fluids heart helluva_boss imp instant_loss_2koma larger_male male male_only mating_press motion_lines multi_eye nude owl owl_demon penetration red_eyes sex size_difference small_dom_big_sub smaller_dominant smaller_male smile sound_effects speech_bubble stolas_(helluva_boss) suspicious_spirit sweat teasing text vivienne_medrano vivienne_style yaoi
2boys anal anal_sex anus avian balls bird blitzo_(helluva_boss) blush bodily_fluids clothed clothing cum demon detailed_background duo genital_fluids heart helluva_boss imp instant_loss_2koma larger_male male male_only mating_press motion_lines multi_eye nude owl owl_demon penetration red_eyes sex size_difference small_dom_big_sub smaller_dominant smaller_male smile sound_effects speech_bubble stolas_(helluva_boss) suspicious_spirit sweat teasing text vivienne_medrano vivienne_style yaoi
2boys amazonian_mating_press animal_genitalia anus avian balls big_dom_small_sub bird blitzo_(helluva_boss) blush bodily_fluids chest_tuft cloaca clothed clothing demon digitigrade duo feathers fluffy genitals heart helluva_boss hi_res horn imp larger_male male male_only mating_press motion_lines nude owl owl_demon penetration questionable_consent sex simple_background size_difference sketch smothering sound_effects spade_tail speech_bubble steam stolas_(helluva_boss) submissive submissive_male suspicious_spirit sweat tuft vivienne_medrano vivienne_style yaoi
2boys amazonian_mating_press animal_genitalia anus avian balls big_dom_small_sub bird blitzo_(helluva_boss) blush bodily_fluids chest_tuft cloaca clothed clothing demon digitigrade duo feathers fluffy genitals heart helluva_boss hi_res horn imp larger_male male male_only mating_press motion_lines nude owl owl_demon penetration questionable_consent sex simple_background size_difference sketch smothering sound_effects spade_tail speech_bubble steam stolas_(helluva_boss) submissive submissive_male suspicious_spirit sweat tuft vivienne_medrano vivienne_style yaoi
1boy 1girls 2020 2020s 2d 2d_animation animal_genitalia animal_penis animated anthro anthro_on_anthro black_eyes black_nose butt canid canid_demon canine canine_penis canis demon dog_penis doggy_style duo faceless_male female female_focus female_penetrated from_behind from_behind_position fur furry genitals goth grey_body grey_fur hair half-closed_eyes hellhound helluva_boss its_a_mok knot looking_back loona_(helluva_boss) loop male male/female male_penetrating male_penetrating_female mammal multicolored_body narrowed_eyes nude penetration penis pussy raised_tail rear_view red_sclera sex short_playtime silver_hair straight text thin_eyebrows two_tone_body two_tone_tail url vaginal vaginal_penetration vivienne_medrano vivienne_style watermark white_body white_eyes white_fur widescreen wolf
1boy 1girls 2020 2020s 2d 2d_animation animal_genitalia animal_penis animated anthro anthro_on_anthro black_eyes black_nose butt canid canid_demon canine canine_penis canis demon dog_penis doggy_style duo faceless_male female female_focus female_penetrated from_behind from_behind_position fur furry genitals goth grey_body grey_fur hair half-closed_eyes hellhound helluva_boss its_a_mok knot looking_back loona_(helluva_boss) loop male male/female male_penetrating male_penetrating_female mammal multicolored_body narrowed_eyes nude penetration penis pussy raised_tail rear_view red_sclera sex short_playtime silver_hair straight text thin_eyebrows two_tone_body two_tone_tail url vaginal vaginal_penetration vivienne_medrano vivienne_style watermark white_body white_eyes white_fur widescreen wolf
1girls big_breasts demon demon_girl female female_focus female_only helluva_boss horns horny hyper_breasts imp looking_at_viewer millie_(helluva_boss) monster_girl red_skin shy smiling spanish_text tail text valerya5 vivienne_medrano vivienne_style
1girls big_breasts demon demon_girl female female_focus female_only helluva_boss horns horny hyper_breasts imp looking_at_viewer millie_(helluva_boss) monster_girl red_skin shy smiling spanish_text tail text valerya5 vivienne_medrano vivienne_style
1boy 1girls 2demons black_hair black_lipstick blushing canon_couple couple cute demon demon_horns demon_tail femdom fingerless_gloves flustered footwear grinding grinding_on_penis heart helluva_boss horn imp love millie_(helluva_boss) moxxie_(helluva_boss) nipple_pasties panties pasties queencomplex red_body red_skin small_breasts smile tail thighhighs vivienne_medrano vivienne_style wholesome yellow_eyes
1boy 1girls 2demons black_hair black_lipstick blushing canon_couple couple cute demon demon_horns demon_tail femdom fingerless_gloves flustered footwear grinding grinding_on_penis heart helluva_boss horn imp love millie_(helluva_boss) moxxie_(helluva_boss) nipple_pasties panties pasties queencomplex red_body red_skin small_breasts smile tail thighhighs vivienne_medrano vivienne_style wholesome yellow_eyes
1girls 2020 2boys absurd_res animal_genitalia animal_penis bodily_fluids canine canine_penis cum cum_in_mouth cum_in_pussy cum_inside demon erection fellatio female filthypally forced furry genital_fluids genitals group group_sex hellhound helluva_boss hi_res internal knot knotted knotting loona_(helluva_boss) male mammal oral penetration penile penis rape sex straight tears threesome vaginal_penetration vivienne_medrano vivienne_style
1girls 2020 2boys absurd_res animal_genitalia animal_penis bodily_fluids canine canine_penis cum cum_in_mouth cum_in_pussy cum_inside demon erection fellatio female filthypally forced furry genital_fluids genitals group group_sex hellhound helluva_boss hi_res internal knot knotted knotting loona_(helluva_boss) male mammal oral penetration penile penis rape sex straight tears threesome vaginal_penetration vivienne_medrano vivienne_style
1boy 2girls 4:5 anthro canid canid_demon canine canis cuckquean cum cum_in_pussy cum_inside demon duo english_text female hellhound helluva_boss hermitmoth hi_res humanoid humanoid_on_anthro loona_(helluva_boss) male mammal millie_(helluva_boss) monster moxxie_(helluva_boss) profanity red_sclera size_difference straight vivienne_medrano vivienne_style wolf
1boy 2girls 4:5 anthro canid canid_demon canine canis cuckquean cum cum_in_pussy cum_inside demon duo english_text female hellhound helluva_boss hermitmoth hi_res humanoid humanoid_on_anthro loona_(helluva_boss) male mammal millie_(helluva_boss) monster moxxie_(helluva_boss) profanity red_sclera size_difference straight vivienne_medrano vivienne_style wolf
1girls 2boys all_fours anal anal_sex blitzo_(helluva_boss) clothing cuckquean demon doggy_style dream erection female finger_in_mouth forced forced_yaoi from_behind_position g-h- gay ghastlygh goat_legs heart helluva_boss horn looking_pleasured male male_penetrated malesub masturbation millie_(helluva_boss) moxxie_(helluva_boss) penetration penis rape sex sketch sleeping smile spade_tail underwear vivienne_medrano vivienne_style voyeur
1girls 2boys all_fours anal anal_sex blitzo_(helluva_boss) clothing cuckquean demon doggy_style dream erection female finger_in_mouth forced forced_yaoi from_behind_position g-h- gay ghastlygh goat_legs heart helluva_boss horn looking_pleasured male male_penetrated malesub masturbation millie_(helluva_boss) moxxie_(helluva_boss) penetration penis rape sex sketch sleeping smile spade_tail underwear vivienne_medrano vivienne_style voyeur