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16th century

16th_century absurd_res albrecht_durer ambiguous_gender ancient_art animal_genitalia animal_penis armor black_and_tan black_line_art bone cc0 claws clothed clothing creative_commons crown dragon equid equine equine_genitalia equine_penis european_mythology feet feral fingers fully_clothed genitals group headgear helmet hi_res holding_melee_weapon holding_object holding_polearm holding_spear holding_weapon hooves horse human imminent_death killing knight long_neck male mammal melee_weapon membrane_(anatomy) membranous_wings mythological_creature mythological_scalie mythology open_mouth outside penis polearm rib_cage riding rock saddle saint_george scalie sharp_teeth side_view simple_background skull snout spear tail tan_background teeth toe_claws toes trio_focus warrior weapon western_dragon wings woodcut
16th_century absurd_res albrecht_durer ambiguous_gender ancient_art animal_genitalia animal_penis armor black_and_tan black_line_art bone cc0 claws clothed clothing creative_commons crown dragon equid equine equine_genitalia equine_penis european_mythology feet feral fingers fully_clothed genitals group headgear helmet hi_res holding_melee_weapon holding_object holding_polearm holding_spear holding_weapon hooves horse human imminent_death killing knight long_neck male mammal melee_weapon membrane_(anatomy) membranous_wings mythological_creature mythological_scalie mythology open_mouth outside penis polearm rib_cage riding rock saddle saint_george scalie sharp_teeth side_view simple_background skull snout spear tail tan_background teeth toe_claws toes trio_focus warrior weapon western_dragon wings woodcut
16th_century 1girls ai_generated alley anthro breasts breasts_focus casual_nudity female female_only fish gloves_(marking) green_eyes green_hair hair_over_one_eye hands_covering_crotch hands_covering_pussy hands_together japan japanese looking_at_viewer marine mint_eyes mint_hair non-mammal_breasts non-mammal_ears non-mammal_nipples nude nude_female public public_nudity red_body shark shark_girl shark_teeth short_hair shy small_nipples smile white_body
16th_century 1girls ai_generated alley anthro breasts breasts_focus casual_nudity female female_only fish gloves_(marking) green_eyes green_hair hair_over_one_eye hands_covering_crotch hands_covering_pussy hands_together japan japanese looking_at_viewer marine mint_eyes mint_hair non-mammal_breasts non-mammal_ears non-mammal_nipples nude nude_female public public_nudity red_body shark shark_girl shark_teeth short_hair shy small_nipples smile white_body
1549 16th_century anatomically_correct anatomically_correct_genitalia ancient_art animal_genitalia canid canine canine_sheath canis claws collar collar_only curled_tail dated digitigrade domestic_dog feral fully_sheathed fur genitals graphite_(artwork) grass greyhound hi_res hunting_dog male mammal monochrome nude paws plant public_domain quadruped sheath side_view sighthound simple_background snout solo tail tan_background traditional_media_(artwork) virgil_solis
1549 16th_century anatomically_correct anatomically_correct_genitalia ancient_art animal_genitalia canid canine canine_sheath canis claws collar collar_only curled_tail dated digitigrade domestic_dog feral fully_sheathed fur genitals graphite_(artwork) grass greyhound hi_res hunting_dog male mammal monochrome nude paws plant public_domain quadruped sheath side_view sighthound simple_background snout solo tail tan_background traditional_media_(artwork) virgil_solis
16th_century after_birth anatid ancient_art anseriform anserinae areola avian baby balls beak bird birth breasts brown_hair building_destruction cesare_da_sesto duo_focus egg embrace european_mythology feathered_wings feathers feet female feral formal_art genitals grass greek_mythology group hair happy hatched human humanoid_feet humanoid_hands interspecies leda leda_and_the_swan male mammal medium_breasts membrane_(anatomy) micropenis mythology narrowed_eyes navel nipples nude oil_painting_(artwork) outside painting_(artwork) penis plant plantigrade public_domain rapist rapist_real romantic romantic_couple small_penis smile swan tan_body tan_skin toes traditional_media_(artwork) tree webbed_feet wings young zeus zoophilia
16th_century after_birth anatid ancient_art anseriform anserinae areola avian baby balls beak bird birth breasts brown_hair building_destruction cesare_da_sesto duo_focus egg embrace european_mythology feathered_wings feathers feet female feral formal_art genitals grass greek_mythology group hair happy hatched human humanoid_feet humanoid_hands interspecies leda leda_and_the_swan male mammal medium_breasts membrane_(anatomy) micropenis mythology narrowed_eyes navel nipples nude oil_painting_(artwork) outside painting_(artwork) penis plant plantigrade public_domain rapist rapist_real romantic romantic_couple small_penis smile swan tan_body tan_skin toes traditional_media_(artwork) tree webbed_feet wings young zeus zoophilia
16th_century artist_request blowjob catherine_de_medici civilization civilization_(series) civilization_vi cum cum_in_mouth cum_on_face defeated facial game_over history monarch partial_male public_domain queen video_game_character
16th_century artist_request blowjob catherine_de_medici civilization civilization_(series) civilization_vi cum cum_in_mouth cum_on_face defeated facial game_over history monarch partial_male public_domain queen video_game_character
16th_century aldegrever beard centaur female fine_art greek_mythology heinrich_aldegrever human kidnapping male male_focus muscles non-human penis public_domain
16th_century aldegrever beard centaur female fine_art greek_mythology heinrich_aldegrever human kidnapping male male_focus muscles non-human penis public_domain
16th_century 5_fingers 5_toes ass baboon balls biped crouching erection feet feral fine_art fingers full-length_portrait fur genitals glans grey_balls grey_body grey_fur haplorhine humanoid_genitalia humanoid_penis male mammal monkey nude old_world_monkey penis portrait primate public_domain red_butt side_view simple_background solo toes traditional_media_(artwork) unknown_artist
16th_century 5_fingers 5_toes ass baboon balls biped crouching erection feet feral fine_art fingers full-length_portrait fur genitals glans grey_balls grey_body grey_fur haplorhine humanoid_genitalia humanoid_penis male mammal monkey nude old_world_monkey penis portrait primate public_domain red_butt side_view simple_background solo toes traditional_media_(artwork) unknown_artist
16th_century aldegrever beard centaur cropped fine_art greek_mythology heinrich_aldegrever human kidnapping male male_focus muscles penis small_image
16th_century aldegrever beard centaur cropped fine_art greek_mythology heinrich_aldegrever human kidnapping male male_focus muscles penis small_image
16th_century aurochs balls bovid bovine feral fine_art hi_res horn male male_only mammal presenting presenting_balls solo teodoro_ghisi traditional_media_(artwork)
16th_century aurochs balls bovid bovine feral fine_art hi_res horn male male_only mammal presenting presenting_balls solo teodoro_ghisi traditional_media_(artwork)
1528 16th_century avian balls beard bed bird blinding breasts deity eagle erection facial_hair feathered_wings feathers female feral fine_art fresco giulio_romano group hair human humanoid_penis hybrid jupiter lightning lightning_bolt lying male mammal missionary_position navel nipples nude olympias_of_epirus on_back penis philip_ii_of_macedon public_domain rapist rapist_real renaissance reptile scalie sex side_view snake spread_wings straight thick_foreskin traditional_media_(artwork) uncut unusual_anatomy wings zeus
1528 16th_century avian balls beard bed bird blinding breasts deity eagle erection facial_hair feathered_wings feathers female feral fine_art fresco giulio_romano group hair human humanoid_penis hybrid jupiter lightning lightning_bolt lying male mammal missionary_position navel nipples nude olympias_of_epirus on_back penis philip_ii_of_macedon public_domain rapist rapist_real renaissance reptile scalie sex side_view snake spread_wings straight thick_foreskin traditional_media_(artwork) uncut unusual_anatomy wings zeus
16th_century ass breasts dahr eastern_european harem harem_girl harem_girls human human_only ivan_the_terrible light-skinned_female light-skinned_male light_skin medieval multiple_girls northern_european political politician politics prime_minister public_domain slave slave_market slave_sale slavegirl slaves tagme ukraine ukrainian vladimir_putin yuliya_timoshenko
16th_century ass breasts dahr eastern_european harem harem_girl harem_girls human human_only ivan_the_terrible light-skinned_female light-skinned_male light_skin medieval multiple_girls northern_european political politician politics prime_minister public_domain slave slave_market slave_sale slavegirl slaves tagme ukraine ukrainian vladimir_putin yuliya_timoshenko
16th_century 2010 2boys 3girls 6+futas ankh areolae balls bottomless_skirt breasts cavewoman cleavage cock_ribbon cowboy curvy dickgirl egyptian erect_nipples erection erection_under_clothes erection_under_loincloth erection_under_skirt female female_with_female futa_on_female futa_on_male futa_with_female futa_with_futa futa_with_male futadom futanari future gideon gigantic_penis gladiator hippie history huge_cock human humor hyper hyper_balls hyper_breasts hyper_penis ineffective_clothing ineffective_loincloth intersex knight large_nipples larger_futanari loincloth loincloth_lift male male_with_female male_with_male malesub monochrome muscular_futanari nipples no_panties nun penis penis_out penis_ribbon penis_under_clothes penis_under_loincloth penis_under_skirt pun roman sketch skirt skirt_lift space sword timelapse trident ufo wide_hips
16th_century 2010 2boys 3girls 6+futas ankh areolae balls bottomless_skirt breasts cavewoman cleavage cock_ribbon cowboy curvy dickgirl egyptian erect_nipples erection erection_under_clothes erection_under_loincloth erection_under_skirt female female_with_female futa_on_female futa_on_male futa_with_female futa_with_futa futa_with_male futadom futanari future gideon gigantic_penis gladiator hippie history huge_cock human humor hyper hyper_balls hyper_breasts hyper_penis ineffective_clothing ineffective_loincloth intersex knight large_nipples larger_futanari loincloth loincloth_lift male male_with_female male_with_male malesub monochrome muscular_futanari nipples no_panties nun penis penis_out penis_ribbon penis_under_clothes penis_under_loincloth penis_under_skirt pun roman sketch skirt skirt_lift space sword timelapse trident ufo wide_hips