the_hellhound_kid best from all time

Time frame

the hellhound kid

1:1 1boy 1girls absurd_res adult_on_cub age_difference animal_genitalia animal_penis anthro anus ass background_character balls bite_mark blush bodily_fluids breasts canid canid_demon canine canine_genitalia canine_penis canis child claws clothing color comic cub cub_and_adult cum cum_in_pussy cum_inside cum_on_breasts cum_on_face demon dialogue dirty_talk dominant dominant_young duo english_text erection fangs female female_focus female_penetrated femsub forced from_behind_position fur genital_fluids genitals hair hellhound helluva_boss hi_res impregnation knot larger_female legwear licking licking_lips loona_(helluva_boss) male male/female male_cub male_dominating_female male_penetrating male_penetrating_female mammal mind_break mythological_canine mythological_creature mythology nipple_piercing nipples older_female older_woman_and_younger_boy open_mouth pawpads penetration penile penis piercing pussy quality rape red_body red_sclera sex simple_background size_difference small_dom_big_sub smaller_male smile sound_effects stockings tail teeth text tfzn the_hellhound_kid tongue tongue_out topwear torn_clothing torn_legwear torn_stockings uncensored until_they_like_it vaginal_penetration white_body white_fur yellow_body yellow_fur young_anthro younger_dom_older_sub younger_male
1:1 1boy 1girls absurd_res adult_on_cub age_difference animal_genitalia animal_penis anthro anus ass background_character balls bite_mark blush bodily_fluids breasts canid canid_demon canine canine_genitalia canine_penis canis child claws clothing color comic cub cub_and_adult cum cum_in_pussy cum_inside cum_on_breasts cum_on_face demon dialogue dirty_talk dominant dominant_young duo english_text erection fangs female female_focus female_penetrated femsub forced from_behind_position fur genital_fluids genitals hair hellhound helluva_boss hi_res impregnation knot larger_female legwear licking licking_lips loona_(helluva_boss) male male/female male_cub male_dominating_female male_penetrating male_penetrating_female mammal mind_break mythological_canine mythological_creature mythology nipple_piercing nipples older_female older_woman_and_younger_boy open_mouth pawpads penetration penile penis piercing pussy quality rape red_body red_sclera sex simple_background size_difference small_dom_big_sub smaller_male smile sound_effects stockings tail teeth text tfzn the_hellhound_kid tongue tongue_out topwear torn_clothing torn_legwear torn_stockings uncensored until_they_like_it vaginal_penetration white_body white_fur yellow_body yellow_fur young_anthro younger_dom_older_sub younger_male
breed bulge callmewritefag cock_hungry cub female fur furry helluva_boss horny horny_thoughts loona_(helluva_boss) mind_break musk smell smelling smelling_penis the_hellhound_kid
breed bulge callmewritefag cock_hungry cub female fur furry helluva_boss horny horny_thoughts loona_(helluva_boss) mind_break musk smell smelling smelling_penis the_hellhound_kid
1boy 1girls 2d angry anthro ass background_character bare_shoulders big_penis breasts canid canid_demon cock cum cum_in_pussy cum_inside demon dick dominant_male duo enigi09 feet feet_up female from_front_position fucked_silly furry genitals heart hellhound helluva_boss hi_res large_ass larger_female laying_on_back long_hair loona_(helluva_boss) male male/female mammal mating_press multicolored_body penis quality questionable_consent ripped_clothing sex silver_hair sitting size_difference small_dom_big_sub smaller_male spread_legs steamy_breath straight submissive_female taller_female the_hellhound_kid thick_thighs torn_legwear vaginal_penetration white_body
1boy 1girls 2d angry anthro ass background_character bare_shoulders big_penis breasts canid canid_demon cock cum cum_in_pussy cum_inside demon dick dominant_male duo enigi09 feet feet_up female from_front_position fucked_silly furry genitals heart hellhound helluva_boss hi_res large_ass larger_female laying_on_back long_hair loona_(helluva_boss) male male/female mammal mating_press multicolored_body penis quality questionable_consent ripped_clothing sex silver_hair sitting size_difference small_dom_big_sub smaller_male spread_legs steamy_breath straight submissive_female taller_female the_hellhound_kid thick_thighs torn_legwear vaginal_penetration white_body
1boy 1boy1girl 1girls after_sex after_vaginal age_difference anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro anus balls bite_mark canid canid_demon canine canine_genitalia canine_penis cub cum cum_in_pussy cum_inside cum_on_breasts cum_on_face dialogue dog dog_boy dog_girl doggy_style domestic_dog dominant dominant_young duo english english_text eyelashes eyeshadow female female_penetrated femsub from_behind fur furry furry_female furry_male furry_only genitals hat hellhound helluva_boss impregnation knot larger_female larger_penetrated loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female maledom older_female older_woman_and_younger_boy pawpads penis pierced_nipples piercing rape sex size_difference small_dom_big_sub smaller_male smaller_penetrating smaller_penetrating_bigger stockings text the_hellhound_kid thighhighs torn_clothes torn_legwear trufzn until_they_like_it vagina vaginal_penetration vaginal_sex vivienne_medrano young young_anthro young_male younger_male younger_penetrating younger_penetrating_older
1boy 1boy1girl 1girls after_sex after_vaginal age_difference anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro anus balls bite_mark canid canid_demon canine canine_genitalia canine_penis cub cum cum_in_pussy cum_inside cum_on_breasts cum_on_face dialogue dog dog_boy dog_girl doggy_style domestic_dog dominant dominant_young duo english english_text eyelashes eyeshadow female female_penetrated femsub from_behind fur furry furry_female furry_male furry_only genitals hat hellhound helluva_boss impregnation knot larger_female larger_penetrated loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female maledom older_female older_woman_and_younger_boy pawpads penis pierced_nipples piercing rape sex size_difference small_dom_big_sub smaller_male smaller_penetrating smaller_penetrating_bigger stockings text the_hellhound_kid thighhighs torn_clothes torn_legwear trufzn until_they_like_it vagina vaginal_penetration vaginal_sex vivienne_medrano young young_anthro young_male younger_male younger_penetrating younger_penetrating_older
anthro cub cum cum_in_pussy cum_inside edit enigi09 furry helluva_boss impregnation instant_loss loona_(helluva_boss) mating_press quality sex the_hellhound_kid
anthro cub cum cum_in_pussy cum_inside edit enigi09 furry helluva_boss impregnation instant_loss loona_(helluva_boss) mating_press quality sex the_hellhound_kid
absurd_res age_difference animal_genitalia animal_penis anthro anus assertive_female balls blush blush_lines bodily_fluids canid canid_demon canine canine_genitalia canine_penis clothing collar comic cum cum_from_mouth cum_in_mouth cum_inside cum_on_face cum_on_penis deepthroat demon dominant dominant_female dominant_young duo excessive_cum excessive_genital_fluids face_fucking fellatio female fingerless_gloves genital_fluids genitals glowing_eyes gray_hair hat headgear headwear heart_eyes heart_symbol hellhound helluva_boss hi_res intraspecies irrumatio knot leaking_cum long_hair loona_(helluva_boss) male male/female mammal multicolored_body mythological_canine mythological_creature mythology older_female on_back open_mouth oral oral_invitation oral_penetration orgasm pencil_bolt penetration penile penis pointing_at_self ponytail pulling_down_pants red_eyes ripped_pants saliva serious sex shoulderless_shirt snout spiked_collar straight taller_female tally_marks text the_hellhound_kid throat_swabbing tongue younger_male
absurd_res age_difference animal_genitalia animal_penis anthro anus assertive_female balls blush blush_lines bodily_fluids canid canid_demon canine canine_genitalia canine_penis clothing collar comic cum cum_from_mouth cum_in_mouth cum_inside cum_on_face cum_on_penis deepthroat demon dominant dominant_female dominant_young duo excessive_cum excessive_genital_fluids face_fucking fellatio female fingerless_gloves genital_fluids genitals glowing_eyes gray_hair hat headgear headwear heart_eyes heart_symbol hellhound helluva_boss hi_res intraspecies irrumatio knot leaking_cum long_hair loona_(helluva_boss) male male/female mammal multicolored_body mythological_canine mythological_creature mythology older_female on_back open_mouth oral oral_invitation oral_penetration orgasm pencil_bolt penetration penile penis pointing_at_self ponytail pulling_down_pants red_eyes ripped_pants saliva serious sex shoulderless_shirt snout spiked_collar straight taller_female tally_marks text the_hellhound_kid throat_swabbing tongue younger_male
1boy 1boy1girl 1girls age_difference animal_genitalia animal_penis anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass ass_grab balls bed bedroom big_ass big_breasts blush breasts breasts_out collar collarbone creampie cub cum cum_in_pussy cum_in_uterus cum_inside cumshot dialogue dirty_talk english english_text female female_penetrated fur furry furry_female furry_male furry_only greenstar hellhound helluva_boss high_resolution huge_ass huge_breasts inverted_nipples knot larger_female loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female nipples penis rape sex size_difference small_dom_big_sub smaller_male speech_bubble sweat sweatdrop text the_hellhound_kid thick_thighs thighhighs thighs torn_clothes vaginal_penetration vivienne_medrano wolf wolf_ears wolf_girl wolf_tail x-ray young younger_male
1boy 1boy1girl 1girls age_difference animal_genitalia animal_penis anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass ass_grab balls bed bedroom big_ass big_breasts blush breasts breasts_out collar collarbone creampie cub cum cum_in_pussy cum_in_uterus cum_inside cumshot dialogue dirty_talk english english_text female female_penetrated fur furry furry_female furry_male furry_only greenstar hellhound helluva_boss high_resolution huge_ass huge_breasts inverted_nipples knot larger_female loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female nipples penis rape sex size_difference small_dom_big_sub smaller_male speech_bubble sweat sweatdrop text the_hellhound_kid thick_thighs thighhighs thighs torn_clothes vaginal_penetration vivienne_medrano wolf wolf_ears wolf_girl wolf_tail x-ray young younger_male
1boy 1boy1girl 1girls age_difference angry angry_sex anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls big_breasts canid canid_demon canine cub digital_drawing digital_media dog dog_boy dog_girl domestic_dog dominant dominant_male dominant_young duo eyelashes eyeshadow female female_penetrated femsub fur furry furry_female furry_male furry_only genitals hat hat_only hellhound helluva_boss larger_female larger_penetrated loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female male_penetrating_male maledom older_female older_woman_and_younger_boy penis rape size_difference small_dom_big_sub smaller_male smaller_penetrating smaller_penetrating_bigger stockings the_hellhound_kid thighhighs torn_clothes torn_legwear torn_thighhighs trufzn vagina vaginal_penetration vaginal_sex vivienne_medrano young young_anthro young_male younger_male younger_penetrating younger_penetrating_older
1boy 1boy1girl 1girls age_difference angry angry_sex anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls big_breasts canid canid_demon canine cub digital_drawing digital_media dog dog_boy dog_girl domestic_dog dominant dominant_male dominant_young duo eyelashes eyeshadow female female_penetrated femsub fur furry furry_female furry_male furry_only genitals hat hat_only hellhound helluva_boss larger_female larger_penetrated loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female male_penetrating_male maledom older_female older_woman_and_younger_boy penis rape size_difference small_dom_big_sub smaller_male smaller_penetrating smaller_penetrating_bigger stockings the_hellhound_kid thighhighs torn_clothes torn_legwear torn_thighhighs trufzn vagina vaginal_penetration vaginal_sex vivienne_medrano young young_anthro young_male younger_male younger_penetrating younger_penetrating_older
1boy 1boy1girl 1girls 2023 age_difference anthro anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass background_character balls bent_over bent_over_table breasts callmewritefag canid canid_demon canine canis colored cub demon digital_drawing_(artwork) digital_media_(artwork) domestic_dog duo ear_piercing erection female female_penetrated fur furniture furry furry_female furry_male furry_only genitals hair hellhound helluva_boss hi_res larger_female loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female mammal nipples nude open_mouth penetration penile penis piercing red_sclera sex simple_background size_difference smaller_male standing standing_sex straight table tail taller_female the_hellhound_kid white_body white_fur young younger_male
1boy 1boy1girl 1girls 2023 age_difference anthro anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass background_character balls bent_over bent_over_table breasts callmewritefag canid canid_demon canine canis colored cub demon digital_drawing_(artwork) digital_media_(artwork) domestic_dog duo ear_piercing erection female female_penetrated fur furniture furry furry_female furry_male furry_only genitals hair hellhound helluva_boss hi_res larger_female loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female mammal nipples nude open_mouth penetration penile penis piercing red_sclera sex simple_background size_difference smaller_male standing standing_sex straight table tail taller_female the_hellhound_kid white_body white_fur young younger_male
1boy 1girls age_difference anthro anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass big_ass big_breasts big_butt blush bodily_fluids breasts canid canid_demon canine canis cellmates clothing creampie cub cum cum_in_pussy cum_in_uterus cum_inside demon dog_pound doggy_style domestic_dog duo female female_penetrated fire_conejo from_behind_position fur furry furry_female furry_male furry_only genital_fluids genitals grey_body grey_fur grey_hair hair hat headgear headwear hellhound helluva_boss hi_res knot knotting larger_female loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology nipples older_female open_mouth open_smile orgasm orgasm_face penetration penile penile_penetration penis penis_in_pussy red_eyes roommate saliva sex size_difference smile the_hellhound_kid tongue tongue_out two_tone_body two_tone_fur uterus vaginal_penetration vein veiny_penis white_body white_fur xray_view young younger_male
1boy 1girls age_difference anthro anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass big_ass big_breasts big_butt blush bodily_fluids breasts canid canid_demon canine canis cellmates clothing creampie cub cum cum_in_pussy cum_in_uterus cum_inside demon dog_pound doggy_style domestic_dog duo female female_penetrated fire_conejo from_behind_position fur furry furry_female furry_male furry_only genital_fluids genitals grey_body grey_fur grey_hair hair hat headgear headwear hellhound helluva_boss hi_res knot knotting larger_female loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology nipples older_female open_mouth open_smile orgasm orgasm_face penetration penile penile_penetration penis penis_in_pussy red_eyes roommate saliva sex size_difference smile the_hellhound_kid tongue tongue_out two_tone_body two_tone_fur uterus vaginal_penetration vein veiny_penis white_body white_fur xray_view young younger_male
1boy 1girl age_difference callmewritefag cub domination female fur helluva_boss leash loona_(helluva_boss) male pregnant size_difference slave small_dom_big_sub the_hellhound_kid younger_dom_older_sub
1boy 1girl age_difference callmewritefag cub domination female fur helluva_boss leash loona_(helluva_boss) male pregnant size_difference slave small_dom_big_sub the_hellhound_kid younger_dom_older_sub
1boy 1girls age_difference all_fours animal_genitalia anthro anus ass ass_focus background_character balls ballsack barefoot big_ass big_penis black_fur blush bodily_fluids bottomless_female bottomwear breasts breasts_out canid canine canine_penis cell clitoris clothing cub cum cum_drip cum_in_pussy cum_inside cumshot demon doggy_style dominant dominant_male excessive_cum excessive_genital_fluids excessive_pussy_juice female fluffy fluffy_tail forced from_behind_position fur furry genitals grey_fur headgear headwear hellhound helluva_boss high_resolution huge_ass kitsune_youkai knot knotting long_hair long_tail loona_(helluva_boss) male mammal mammal_humanoid older_female open_mouth pants partially_clothed partially_nude penis pussy pussy_juice rape raped_girl red_sclera rough_sex saliva sex shorts shorts_down silver_eyes sweat sweatdrop tagme tail tail_aside tearing_up tears the_hellhound_kid thick_thighs thighhighs thighs tongue tongue_out torn_clothes vaginal_fluids vaginal_knotting vaginal_penetration white_fur white_hair younger_male
1boy 1girls age_difference all_fours animal_genitalia anthro anus ass ass_focus background_character balls ballsack barefoot big_ass big_penis black_fur blush bodily_fluids bottomless_female bottomwear breasts breasts_out canid canine canine_penis cell clitoris clothing cub cum cum_drip cum_in_pussy cum_inside cumshot demon doggy_style dominant dominant_male excessive_cum excessive_genital_fluids excessive_pussy_juice female fluffy fluffy_tail forced from_behind_position fur furry genitals grey_fur headgear headwear hellhound helluva_boss high_resolution huge_ass kitsune_youkai knot knotting long_hair long_tail loona_(helluva_boss) male mammal mammal_humanoid older_female open_mouth pants partially_clothed partially_nude penis pussy pussy_juice rape raped_girl red_sclera rough_sex saliva sex shorts shorts_down silver_eyes sweat sweatdrop tagme tail tail_aside tearing_up tears the_hellhound_kid thick_thighs thighhighs thighs tongue tongue_out torn_clothes vaginal_fluids vaginal_knotting vaginal_penetration white_fur white_hair younger_male
2022 absurd_res aged_up anthro anthro_on_anthro background_character bent_over bodily_fluids breasts brown_body brown_fur butt canid canid_demon canine clothed clothing collar cum cum_from_mouth cum_in_mouth cum_inside demon digital_drawing_(artwork) digital_media_(artwork) duo erection eye_contact faceless_character faceless_male fellatio female fur genital_fluids genitals hair hellhound helluva_boss hi_res leaking_cum looking_at_another looking_up loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology oral oral_penetration orgasm partially_clothed penetration penile penis red_sclera sex silviaxrk simple_background spank_marks the_hellhound_kid white_body white_fur
2022 absurd_res aged_up anthro anthro_on_anthro background_character bent_over bodily_fluids breasts brown_body brown_fur butt canid canid_demon canine clothed clothing collar cum cum_from_mouth cum_in_mouth cum_inside demon digital_drawing_(artwork) digital_media_(artwork) duo erection eye_contact faceless_character faceless_male fellatio female fur genital_fluids genitals hair hellhound helluva_boss hi_res leaking_cum looking_at_another looking_up loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology oral oral_penetration orgasm partially_clothed penetration penile penis red_sclera sex silviaxrk simple_background spank_marks the_hellhound_kid white_body white_fur
1boy 1girls age_difference all_fours animal_genitalia anthro anus ass ass_focus background_character balls ballsack barefoot big_ass big_penis black_fur blush bodily_fluids bottomless_female bottomwear breasts breasts_out canid canine canine_penis cell clitoris clothing cub demon doggy_style dominant dominant_male excessive_genital_fluids excessive_pussy_juice female fluffy fluffy_tail forced from_behind_position fur furry genitals grey_fur headgear headwear hellhound helluva_boss high_resolution huge_ass kitsune_youkai knot long_hair long_tail loona_(helluva_boss) male mammal mammal_humanoid older_female open_mouth pants partially_clothed partially_nude penis pussy pussy_juice rape raped_girl red_sclera rough_sex sex shorts shorts_down silver_eyes sweat sweatdrop tagme tail tail_aside tearing_up tears the_hellhound_kid thick_thighs thighhighs thighs tongue tongue_out torn_clothes vaginal_fluids vaginal_penetration white_fur white_hair younger_male
1boy 1girls age_difference all_fours animal_genitalia anthro anus ass ass_focus background_character balls ballsack barefoot big_ass big_penis black_fur blush bodily_fluids bottomless_female bottomwear breasts breasts_out canid canine canine_penis cell clitoris clothing cub demon doggy_style dominant dominant_male excessive_genital_fluids excessive_pussy_juice female fluffy fluffy_tail forced from_behind_position fur furry genitals grey_fur headgear headwear hellhound helluva_boss high_resolution huge_ass kitsune_youkai knot long_hair long_tail loona_(helluva_boss) male mammal mammal_humanoid older_female open_mouth pants partially_clothed partially_nude penis pussy pussy_juice rape raped_girl red_sclera rough_sex sex shorts shorts_down silver_eyes sweat sweatdrop tagme tail tail_aside tearing_up tears the_hellhound_kid thick_thighs thighhighs thighs tongue tongue_out torn_clothes vaginal_fluids vaginal_penetration white_fur white_hair younger_male
1boy 1boy1girl 1girls age_difference animal_genitalia animal_penis anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass ass_grab balls bed bedroom big_ass big_breasts blush breasts breasts_out collar collarbone completely_nude creampie cub cum cum_in_pussy cum_in_uterus cum_inside cumshot dialogue dirty_talk english english_text female female_penetrated fur furry furry_female furry_male furry_only greenstar hellhound helluva_boss high_resolution huge_ass huge_breasts inverted_nipples larger_female long_hair loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female nipples nude penis pussy pussy_juice rape sex size_difference small_dom_big_sub smaller_male speech_bubble sweat sweatdrop tears text the_hellhound_kid thick_thighs thighs vaginal_penetration vivienne_medrano white_hair wolf wolf_ears wolf_girl wolf_tail x-ray young younger_male
1boy 1boy1girl 1girls age_difference animal_genitalia animal_penis anthro anthro_female anthro_male anthro_on_anthro anthro_only anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass ass_grab balls bed bedroom big_ass big_breasts blush breasts breasts_out collar collarbone completely_nude creampie cub cum cum_in_pussy cum_in_uterus cum_inside cumshot dialogue dirty_talk english english_text female female_penetrated fur furry furry_female furry_male furry_only greenstar hellhound helluva_boss high_resolution huge_ass huge_breasts inverted_nipples larger_female long_hair loona_(helluva_boss) male male/female male_cub male_penetrating male_penetrating_female nipples nude penis pussy pussy_juice rape sex size_difference small_dom_big_sub smaller_male speech_bubble sweat sweatdrop tears text the_hellhound_kid thick_thighs thighs vaginal_penetration vivienne_medrano white_hair wolf wolf_ears wolf_girl wolf_tail x-ray young younger_male
1boy 1girls age_difference anthro anthro_on_anthro ass background_character bed big_butt bodily_fluids canid canid_demon clothed clothing cub demon doggy_style duo fangs female female_penetrated fluffy fluffy_tail from_behind_position fur furniture genital_fluids genitals hat headgear headwear hellhound helluva_boss larger_female looking_pleasured loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal older_female on_bed open_mouth open_smile partially_clothed penetration penile penile_penetration penis penis_in_pussy pussy_juice rape sex sheepsinfull size_difference sleep_molestation sleeping small_dom_big_sub smaller_male smile somnophilia tagme teeth the_hellhound_kid thick_thighs tongue tongue_out vaginal_penetration white_body white_fur young younger_male
1boy 1girls age_difference anthro anthro_on_anthro ass background_character bed big_butt bodily_fluids canid canid_demon clothed clothing cub demon doggy_style duo fangs female female_penetrated fluffy fluffy_tail from_behind_position fur furniture genital_fluids genitals hat headgear headwear hellhound helluva_boss larger_female looking_pleasured loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal older_female on_bed open_mouth open_smile partially_clothed penetration penile penile_penetration penis penis_in_pussy pussy_juice rape sex sheepsinfull size_difference sleep_molestation sleeping small_dom_big_sub smaller_male smile somnophilia tagme teeth the_hellhound_kid thick_thighs tongue tongue_out vaginal_penetration white_body white_fur young younger_male
anthro anthro_on_anthro ass background_character bed big_butt bodily_fluids canid canid_demon clothed clothing demon doggy_style duo fangs female female_penetrated fluffy fluffy_tail from_behind_position fur furniture genital_fluids genitals hat headgear headwear hellhound helluva_boss larger_female looking_pleasured loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal on_bed open_mouth open_smile partially_clothed penetration penile penile_penetration penis penis_in_pussy pussy_juice sex sheepsinfull size_difference small_dom_big_sub smaller_male smile teeth the_hellhound_kid thick_thighs tongue tongue_out vaginal_penetration white_body white_fur
anthro anthro_on_anthro ass background_character bed big_butt bodily_fluids canid canid_demon clothed clothing demon doggy_style duo fangs female female_penetrated fluffy fluffy_tail from_behind_position fur furniture genital_fluids genitals hat headgear headwear hellhound helluva_boss larger_female looking_pleasured loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal on_bed open_mouth open_smile partially_clothed penetration penile penile_penetration penis penis_in_pussy pussy_juice sex sheepsinfull size_difference small_dom_big_sub smaller_male smile teeth the_hellhound_kid thick_thighs tongue tongue_out vaginal_penetration white_body white_fur
age_difference callmewritefag cub domination fur helluva_boss loona_(helluva_boss) male mindbreak penetration sex size_difference submissive_female the_hellhound_kid younger_dom_older_sub younger_male
age_difference callmewritefag cub domination fur helluva_boss loona_(helluva_boss) male mindbreak penetration sex size_difference submissive_female the_hellhound_kid younger_dom_older_sub younger_male
age_difference animal_genitalia animal_penis anthro big_penis canid canid_demon canine canine_genitalia canine_penis canis cub demon dog_pound domestic_dog dominant dominant_male duo female fire_conejo fur genitals grey_body grey_fur hellhound helluva_boss loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology older_female oozing oral penis prisoner red_eyes red_penis submissive submissive_female the_hellhound_kid young younger_male
age_difference animal_genitalia animal_penis anthro big_penis canid canid_demon canine canine_genitalia canine_penis canis cub demon dog_pound domestic_dog dominant dominant_male duo female fire_conejo fur genitals grey_body grey_fur hellhound helluva_boss loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology older_female oozing oral penis prisoner red_eyes red_penis submissive submissive_female the_hellhound_kid young younger_male
age_difference callmewritefag cub fur helluva_boss loona_(helluva_boss) maledom size_difference small_dom_big_sub spanking submissive_female the_hellhound_kid younger_dom_older_sub
age_difference callmewritefag cub fur helluva_boss loona_(helluva_boss) maledom size_difference small_dom_big_sub spanking submissive_female the_hellhound_kid younger_dom_older_sub
2024 alternate_version_at_source angry animal_genitalia animal_penis anthro anthro_on_anthro balls bat_(object) big_breasts bodily_fluids bottomwear bottomwear_down breasts breath canid canid_demon canine_genitalia canine_penis clothed clothing crying cum cum_inside demon dipstick_tail duo eye_roll female genital_fluids genitals hellhound helluva_boss hi_res hoodie humanoid_genitalia humanoid_pussy impregnation internal jackrabbit_(artist) kneeling larger_anthro larger_female larger_submissive legwear loona_(helluva_boss) male male/female mammal markings panting pants pants_down pantsless_anthro pantsless_female partially_clothed paws penetration penis puffed_tail pussy questionable_consent rape sheath shirt signature size_difference smaller_anthro smaller_domination smaller_male spiked_bat stomach_bulge t-shirt tail tail_markings tail_motion tailwag tears the_hellhound_kid thigh_highs tongue tongue_out topwear unwanted_creampie unwanted_cum_inside unwanted_cumshot unwanted_ejaculation unwanted_impregnation unwanted_knotting vaginal_penetration
2024 alternate_version_at_source angry animal_genitalia animal_penis anthro anthro_on_anthro balls bat_(object) big_breasts bodily_fluids bottomwear bottomwear_down breasts breath canid canid_demon canine_genitalia canine_penis clothed clothing crying cum cum_inside demon dipstick_tail duo eye_roll female genital_fluids genitals hellhound helluva_boss hi_res hoodie humanoid_genitalia humanoid_pussy impregnation internal jackrabbit_(artist) kneeling larger_anthro larger_female larger_submissive legwear loona_(helluva_boss) male male/female mammal markings panting pants pants_down pantsless_anthro pantsless_female partially_clothed paws penetration penis puffed_tail pussy questionable_consent rape sheath shirt signature size_difference smaller_anthro smaller_domination smaller_male spiked_bat stomach_bulge t-shirt tail tail_markings tail_motion tailwag tears the_hellhound_kid thigh_highs tongue tongue_out topwear unwanted_creampie unwanted_cum_inside unwanted_cumshot unwanted_ejaculation unwanted_impregnation unwanted_knotting vaginal_penetration
anthro baseball_bat bat_(object) bodily_fluids canid canid_demon canine confusion cum darkness demon dottfeet duo ejaculation feet foot_fetish foot_play footjob forced forced_orgasm genital_fluids hellhound hi_res horror_(theme) male mammal mythological_canine mythological_creature mythology orgasm sex soles the_hellhound_kid
anthro baseball_bat bat_(object) bodily_fluids canid canid_demon canine confusion cum darkness demon dottfeet duo ejaculation feet foot_fetish foot_play footjob forced forced_orgasm genital_fluids hellhound hi_res horror_(theme) male mammal mythological_canine mythological_creature mythology orgasm sex soles the_hellhound_kid
adopted_(lore) angry anthro baseball_bat bat_(object) canid canid_demon canine confusion demon dottfeet duo feet foot_fetish foot_play footjob hellhound helluva_boss hi_res male male/male mammal mythological_canine mythological_creature mythology orphan sex smile smug_face the_hellhound_kid young
adopted_(lore) angry anthro baseball_bat bat_(object) canid canid_demon canine confusion demon dottfeet duo feet foot_fetish foot_play footjob hellhound helluva_boss hi_res male male/male mammal mythological_canine mythological_creature mythology orphan sex smile smug_face the_hellhound_kid young
2024 alternate_version_at_source angry animal_genitalia animal_penis anthro anthro_on_anthro balls bat_(object) big_breasts bottomwear bottomwear_down breasts breath canid canid_demon canine_genitalia canine_penis clothed clothing demon dipstick_tail duo female genitals hair hellhound helluva_boss hi_res hoodie humanoid_genitalia humanoid_pussy jackrabbit_(artist) kneeling larger_anthro larger_female larger_submissive legwear loona_(helluva_boss) male male/female mammal markings nails panting pants pants_down pantsless_anthro pantsless_female partially_clothed paws penetration penis puffed_tail pussy questionable_consent shirt signature size_difference smaller_anthro smaller_domination smaller_male spiked_bat t-shirt tagme tail tail_markings tail_motion tailwag the_hellhound_kid thigh_highs tongue tongue_out topwear vaginal_penetration
2024 alternate_version_at_source angry animal_genitalia animal_penis anthro anthro_on_anthro balls bat_(object) big_breasts bottomwear bottomwear_down breasts breath canid canid_demon canine_genitalia canine_penis clothed clothing demon dipstick_tail duo female genitals hair hellhound helluva_boss hi_res hoodie humanoid_genitalia humanoid_pussy jackrabbit_(artist) kneeling larger_anthro larger_female larger_submissive legwear loona_(helluva_boss) male male/female mammal markings nails panting pants pants_down pantsless_anthro pantsless_female partially_clothed paws penetration penis puffed_tail pussy questionable_consent shirt signature size_difference smaller_anthro smaller_domination smaller_male spiked_bat t-shirt tagme tail tail_markings tail_motion tailwag the_hellhound_kid thigh_highs tongue tongue_out topwear vaginal_penetration