19th_century best from all time -animated

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19th century

19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only muscle older_male rd_(artist) solo solo_male
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only muscle older_male rd_(artist) solo solo_male
19th_century 1boy bestiality covered_wagon english_text fake_screenshot gay gay_sex human male outdoors ox rape river som starry_sky tagme the_oregon_trail yaoi zoophilia
19th_century 1boy bestiality covered_wagon english_text fake_screenshot gay gay_sex human male outdoors ox rape river som starry_sky tagme the_oregon_trail yaoi zoophilia
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century ancient_art animal_genitalia animal_pussy black_hair blue_clothing blue_robe bodily_fluids bowl brown_body brown_fur canid canine canis closed_eyes clothing container doggy_style domestic_dog duo female female_penetrated feral feral_penetrated from_behind_position fur genital_fluids genitals hair hairy_arms hairy_legs hand_on_back human human_on_feral human_penetrating human_penetrating_feral humanoid_genitalia humanoid_penis interspecies japanese_text kneeling looking_pleasured male male/female male_penetrating male_penetrating_female mammal multi_nipple multicolored_body multicolored_fur nipples open_mouth penetration penis pink_pussy prick_ears pubes public_domain pussy red_nipples robe sex shunga simple_background text tongue tongue_out traditional_media_(artwork) translation_request tsukioka_yoshitoshi two_tone_body two_tone_fur white_background white_body white_fur woodblock_print zoophilia
19th_century ancient_art animal_genitalia animal_pussy black_hair blue_clothing blue_robe bodily_fluids bowl brown_body brown_fur canid canine canis closed_eyes clothing container doggy_style domestic_dog duo female female_penetrated feral feral_penetrated from_behind_position fur genital_fluids genitals hair hairy_arms hairy_legs hand_on_back human human_on_feral human_penetrating human_penetrating_feral humanoid_genitalia humanoid_penis interspecies japanese_text kneeling looking_pleasured male male/female male_penetrating male_penetrating_female mammal multi_nipple multicolored_body multicolored_fur nipples open_mouth penetration penis pink_pussy prick_ears pubes public_domain pussy red_nipples robe sex shunga simple_background text tongue tongue_out traditional_media_(artwork) translation_request tsukioka_yoshitoshi two_tone_body two_tone_fur white_background white_body white_fur woodblock_print zoophilia
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only muscle older_male rd_(artist) solo solo_male
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only muscle older_male rd_(artist) solo solo_male
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century ambiguous_gender ambiguous_penetrated ancient_art black_clothing black_robe black_spots brown_spots canid canine canis clothing doggy_style domestic_dog duo feral feral_penetrated footwear from_behind_position fur grass grey_hair hair human human_on_feral human_penetrating human_penetrating_feral interspecies japanese_text looking_at_another male male/ambiguous male_penetrating male_penetrating_ambiguous mammal melee_weapon multicolored_body multicolored_fur outside peeping penetration plant public_domain robe sandals scabbard sex shunga spots standing sword tail tail_grab text tongue tongue_out translation_request ukiyo-e unknown_artist voyeur weapon white_body white_fur window zoophilia
19th_century ambiguous_gender ambiguous_penetrated ancient_art black_clothing black_robe black_spots brown_spots canid canine canis clothing doggy_style domestic_dog duo feral feral_penetrated footwear from_behind_position fur grass grey_hair hair human human_on_feral human_penetrating human_penetrating_feral interspecies japanese_text looking_at_another male male/ambiguous male_penetrating male_penetrating_ambiguous mammal melee_weapon multicolored_body multicolored_fur outside peeping penetration plant public_domain robe sandals scabbard sex shunga spots standing sword tail tail_grab text tongue tongue_out translation_request ukiyo-e unknown_artist voyeur weapon white_body white_fur window zoophilia
19th_century ancient_art bent_over black_hair blue_clothing blue_robe broom bucket cleaning_tool closed_eyes clothing container doggy_style duo face_lick female female_penetrated feral feral_penetrated footwear from_behind_position fur green_clothing green_robe hair happy happy_sex human human_on_feral human_penetrating human_penetrating_feral inside interspecies japanese_text kneeling licking looking_at_another looking_back looking_back_at_another male male/female male_penetrating male_penetrating_female mammal monotone_body monotone_fur penetration pubes public_domain robe sandals sex shunga smile text tongue tongue_out translation_request ukiyo-e utagawa_kuniyoshi wall_(structure) yellow_body yellow_fur zoophilia
19th_century ancient_art bent_over black_hair blue_clothing blue_robe broom bucket cleaning_tool closed_eyes clothing container doggy_style duo face_lick female female_penetrated feral feral_penetrated footwear from_behind_position fur green_clothing green_robe hair happy happy_sex human human_on_feral human_penetrating human_penetrating_feral inside interspecies japanese_text kneeling licking looking_at_another looking_back looking_back_at_another male male/female male_penetrating male_penetrating_female mammal monotone_body monotone_fur penetration pubes public_domain robe sandals sex shunga smile text tongue tongue_out translation_request ukiyo-e utagawa_kuniyoshi wall_(structure) yellow_body yellow_fur zoophilia
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
1871 19th_century ancient_art anus bovid bovine cattle detailed_background feral hi_res male mammal open_mouth outside painting_(artwork) raised_tail realistic_feral rudolph_koller solo standing tail traditional_media_(artwork)
1871 19th_century ancient_art anus bovid bovine cattle detailed_background feral hi_res male mammal open_mouth outside painting_(artwork) raised_tail realistic_feral rudolph_koller solo standing tail traditional_media_(artwork)
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male/male male_only muscle older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male/male male_only muscle older_male rd_(artist) solo solo_male suit yaoi
1890 19th_century ancient_art balls bible briton_riviere christianity clothed clothing felid female feral genitals group human lion male mammal mane oil_painting_(artwork) older_male pantherine pawpads paws public_domain quadruped religion tail tail_tuft tuft
1890 19th_century ancient_art balls bible briton_riviere christianity clothed clothing felid female feral genitals group human lion male mammal mane oil_painting_(artwork) older_male pantherine pawpads paws public_domain quadruped religion tail tail_tuft tuft
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
1898 19th_century 2_horns absurd_res ancient_art balls barely_visible_balls barely_visible_genitalia black_body black_fur black_nose bovid branch brown_body brown_fur caprine curved_horn duo_focus eating fur genitals goat grass group hi_res hooves horizontal_pupils horn ibex joseph_wolf mammal multicolored_body multicolored_fur nature nature_background plant public_domain pupils pyrenean_ibex quadruped scut_tail short_tail snout snow standing tail traditional_media_(artwork) tree walking white_body white_fur yellow_sclera
1898 19th_century 2_horns absurd_res ancient_art balls barely_visible_balls barely_visible_genitalia black_body black_fur black_nose bovid branch brown_body brown_fur caprine curved_horn duo_focus eating fur genitals goat grass group hi_res hooves horizontal_pupils horn ibex joseph_wolf mammal multicolored_body multicolored_fur nature nature_background plant public_domain pupils pyrenean_ibex quadruped scut_tail short_tail snout snow standing tail traditional_media_(artwork) tree walking white_body white_fur yellow_sclera
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy gay ia male male_only military military_uniform muscle older_male rd_(artist) soldier solo solo_male uniform
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male/male male_only older_male rd_(artist) solo solo_male suit yaoi
1845 19th_century ambiguous_gender ancient_art animal_genitalia black_body black_fur brown_body brown_fur detailed_background duo_focus equid equine feral fight fur genitals group horse lying male mammal on_side open_mouth outside painting_(artwork) rudolph_koller sheath traditional_media_(artwork) white_body white_fur
1845 19th_century ambiguous_gender ancient_art animal_genitalia black_body black_fur brown_body brown_fur detailed_background duo_focus equid equine feral fight fur genitals group horse lying male mammal on_side open_mouth outside painting_(artwork) rudolph_koller sheath traditional_media_(artwork) white_body white_fur
1885 19th_century absurd_res ancient_art anus biological_illustration english_text female feral hi_res holding_object legless mammal manatee marine monochrome multiple_images perineum philibert_charles_berjeau plant public_domain sirenian solo tail technical_illustration text traditional_media_(artwork)
1885 19th_century absurd_res ancient_art anus biological_illustration english_text female feral hi_res holding_object legless mammal manatee marine monochrome multiple_images perineum philibert_charles_berjeau plant public_domain sirenian solo tail technical_illustration text traditional_media_(artwork)
1821 19th_century ancient_art asian_clothing black_hair body_horror clothing duo east_asian_clothing female genitals hair head_penis head_pussy hi_res humanoid japanese_clothing japanese_text katsushika_hokusai kimono male male/female monophalia monophallia nightmare_fuel outside penis penis_head purple_clothing pussy pussy_head red_clothing text traditional_media_(artwork) ukiyo-e unusual_anatomy unusual_genitalia_placement unusual_penis_placement unusual_pussy_placement what
1821 19th_century ancient_art asian_clothing black_hair body_horror clothing duo east_asian_clothing female genitals hair head_penis head_pussy hi_res humanoid japanese_clothing japanese_text katsushika_hokusai kimono male male/female monophalia monophallia nightmare_fuel outside penis penis_head purple_clothing pussy pussy_head red_clothing text traditional_media_(artwork) ukiyo-e unusual_anatomy unusual_genitalia_placement unusual_penis_placement unusual_pussy_placement what
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi
19th_century 1boy ai_generated big_balls big_penis daddy ia male male_only older_male rd_(artist) solo solo_male suit yaoi