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1girl armor artist_request asymmetrical_clothes asymmetrical_legwear blonde_hair blue_eyes dungeons_&_dragons freckles full_body hat hat_feather highres history horse landsknecht mismatched_legwear pantyhose puffy_sleeves renaissance_clothes solo sword weapon white_background
1girl armor artist_request asymmetrical_clothes asymmetrical_legwear blonde_hair blue_eyes dungeons_&_dragons freckles full_body hat hat_feather highres history horse landsknecht mismatched_legwear pantyhose puffy_sleeves renaissance_clothes solo sword weapon white_background
ass bandaged_arm bandaged_foot bandages barefoot black_hair breath cloak hidden_eyes history hood ichiren_takushou katana kunoichi lips muscular muscular_female ninja sweat sword tea tea_kettle underwear weapon
ass bandaged_arm bandaged_foot bandages barefoot black_hair breath cloak hidden_eyes history hood ichiren_takushou katana kunoichi lips muscular muscular_female ninja sweat sword tea tea_kettle underwear weapon
1boy 1girl amazon_warrior androgynous anger_vein angry animated anime_screenshot anus armor artifacts ass audible_speech begging black_thighhighs blonde_hair blush bottomless breasts broken_armor buddhism bulging_veins canines censored clitoral_stimulation clitoris_expansion clitoris_piercing clitoris_ring clitoris_torture clitoris_tweak clitoris_vibrator coercion cum cum_in_pussy desert erect_clitoris fellatio forced_masturbation forced_orgasm gokuu_(secret_journey) grabbing_another's_breast groping hairband hetero history huge_ass huge_clitoris large_breasts large_penis long_nipples missionary monkey monster_girl mosaic_censoring nipple_expansion nipple_stimulation nipple_tweak nipples object_insertion oral orgasm orgasm_control orgasm_denial pain penis pervert piercing po-ju pointy_ears precum purple_eyes pussy pussy_juice pussy_piercing red_armor red_hair revealing_clothes saliva sanzoo_(secret_journey) secret_journey seductive_smile shiny_skin shota smile sound tagme tears thighhighs tomboy torn_clothes unbuckled unbuckling unbuttoned unbuttoned_pants vaginal vaginal_jewelry vaginal_object_insertion veins video wide_hips wrist_guards yellow_eyes
1boy 1girl amazon_warrior androgynous anger_vein angry animated anime_screenshot anus armor artifacts ass audible_speech begging black_thighhighs blonde_hair blush bottomless breasts broken_armor buddhism bulging_veins canines censored clitoral_stimulation clitoris_expansion clitoris_piercing clitoris_ring clitoris_torture clitoris_tweak clitoris_vibrator coercion cum cum_in_pussy desert erect_clitoris fellatio forced_masturbation forced_orgasm gokuu_(secret_journey) grabbing_another's_breast groping hairband hetero history huge_ass huge_clitoris large_breasts large_penis long_nipples missionary monkey monster_girl mosaic_censoring nipple_expansion nipple_stimulation nipple_tweak nipples object_insertion oral orgasm orgasm_control orgasm_denial pain penis pervert piercing po-ju pointy_ears precum purple_eyes pussy pussy_juice pussy_piercing red_armor red_hair revealing_clothes saliva sanzoo_(secret_journey) secret_journey seductive_smile shiny_skin shota smile sound tagme tears thighhighs tomboy torn_clothes unbuckled unbuckling unbuttoned unbuttoned_pants vaginal vaginal_jewelry vaginal_object_insertion veins video wide_hips wrist_guards yellow_eyes
aircraft airplane antenna_mast battleship cannon fire firing highres historical_event history military military_vehicle mo_yu_de_jiaozi muzzle_flash ocean original ship turret united_states_navy uss_massachusetts_(bb-59) uss_south_dakota_(bb-57) vehicle_focus warship watercraft waves world_war_ii
aircraft airplane antenna_mast battleship cannon fire firing highres historical_event history military military_vehicle mo_yu_de_jiaozi muzzle_flash ocean original ship turret united_states_navy uss_massachusetts_(bb-59) uss_south_dakota_(bb-57) vehicle_focus warship watercraft waves world_war_ii
1boy absurdres arms_up astolfo_(fate) ballet ballet_boots blush bow circle crossdressing english_text fashion fate_(series) flat_chest footwear_bow footwear_ribbon hadaparuka heart highres history leaning_forward leg_up long_hair long_sleeves looking_away one_eye_closed pink_eyes pink_hair pink_skirt pleated_skirt ponytail skirt smile solo thighs trap white_legwear yellow_background
1boy absurdres arms_up astolfo_(fate) ballet ballet_boots blush bow circle crossdressing english_text fashion fate_(series) flat_chest footwear_bow footwear_ribbon hadaparuka heart highres history leaning_forward leg_up long_hair long_sleeves looking_away one_eye_closed pink_eyes pink_hair pink_skirt pleated_skirt ponytail skirt smile solo thighs trap white_legwear yellow_background
2boys abs battle bead_necklace beads black_pants blood blood_on_clothes blood_on_face blood_splatter blue_jacket broken broken_sword broken_weapon evil_smile eyepatch glowing glowing_eyes highres history jacket japanese_clothes jewelry jiao_mao katana looking_at_viewer majima_goro male_focus manly moon moonlight multiple_boys necklace night night_sky okita_souji_(ishin) open_clothes open_jacket pants red_eyes ryuu_ga_gotoku_(series) ryuu_ga_gotoku_ishin! samurai sky smile splatter sword weapon
2boys abs battle bead_necklace beads black_pants blood blood_on_clothes blood_on_face blood_splatter blue_jacket broken broken_sword broken_weapon evil_smile eyepatch glowing glowing_eyes highres history jacket japanese_clothes jewelry jiao_mao katana looking_at_viewer majima_goro male_focus manly moon moonlight multiple_boys necklace night night_sky okita_souji_(ishin) open_clothes open_jacket pants red_eyes ryuu_ga_gotoku_(series) ryuu_ga_gotoku_ishin! samurai sky smile splatter sword weapon
barbarian celt celtic celtic_tattoos historical historical_porn history tagme tribal tribal_clothing tribal_tattoo
barbarian celt celtic celtic_tattoos historical historical_porn history tagme tribal tribal_clothing tribal_tattoo
bikini bikini_bottom bikini_top french_flag history napoleon napoleon_bonaparte shitpost
bikini bikini_bottom bikini_top french_flag history napoleon napoleon_bonaparte shitpost
1futa 1girl black_hair blonde_hair breasts colonial colonialism english_text futa_with_female historical historical_porn history interracial map national_personification native_american nipples nude pulling_another's_hair racism sex speech_bubble tagme united_states_of_america
1futa 1girl black_hair blonde_hair breasts colonial colonialism english_text futa_with_female historical historical_porn history interracial map national_personification native_american nipples nude pulling_another's_hair racism sex speech_bubble tagme united_states_of_america
2boys abs battle bead_necklace beads black_pants blood blood_on_clothes blood_on_face blood_splatter blue_jacket broken broken_sword broken_weapon evil_smile eyepatch glowing glowing_eyes highres history jacket japanese_clothes jewelry jiao_mao katana looking_at_viewer majima_goro male_focus manly moon moonlight multiple_boys necklace night night_sky okita_souji_(ishin) open_clothes open_jacket pants red_eyes ryuu_ga_gotoku_(series) ryuu_ga_gotoku_ishin! samurai sky smile splatter sword weapon
2boys abs battle bead_necklace beads black_pants blood blood_on_clothes blood_on_face blood_splatter blue_jacket broken broken_sword broken_weapon evil_smile eyepatch glowing glowing_eyes highres history jacket japanese_clothes jewelry jiao_mao katana looking_at_viewer majima_goro male_focus manly moon moonlight multiple_boys necklace night night_sky okita_souji_(ishin) open_clothes open_jacket pants red_eyes ryuu_ga_gotoku_(series) ryuu_ga_gotoku_ishin! samurai sky smile splatter sword weapon
1girls countryhumans countryhumans_girl female german_empire german_empire_(countryhumans) history lkaisersieg56_(artist) only_female towel towel_only
1girls countryhumans countryhumans_girl female german_empire german_empire_(countryhumans) history lkaisersieg56_(artist) only_female towel towel_only
1girl beads black_hair boots coat eskimo female female_focus from_below fur greenland highres historical historical_porn historically_accurate_costume history hood hoodie inuit looking_at_viewer mossacannibalis native_american navel smile solo thighs thong underwear
1girl beads black_hair boots coat eskimo female female_focus from_below fur greenland highres historical historical_porn historically_accurate_costume history hood hoodie inuit looking_at_viewer mossacannibalis native_american navel smile solo thighs thong underwear
1boy absurdres alternate_language arms_up astolfo_(fate) ballet ballet_boots blush bow circle codpiece crossdressing english_text fashion fate/grand_order fate_(series) flat_chest footwear_bow footwear_ribbon hadaparuka heart highres history leaning_forward leg_up long_hair long_sleeves looking_away pink_eyes pink_hair pink_skirt pleated_skirt ponytail skirt smile solo thighs trap white_legwear yellow_background
1boy absurdres alternate_language arms_up astolfo_(fate) ballet ballet_boots blush bow circle codpiece crossdressing english_text fashion fate/grand_order fate_(series) flat_chest footwear_bow footwear_ribbon hadaparuka heart highres history leaning_forward leg_up long_hair long_sleeves looking_away pink_eyes pink_hair pink_skirt pleated_skirt ponytail skirt smile solo thighs trap white_legwear yellow_background
animated austria black_hair catherine_the_great elizabeth_of_russia historical_event history joseph_ii king louis_xvi madame_de_pompadour madame_du_barry maria_theresa marie_antoinette multiple_boys multiple_girls niconico parody poland princess princess_bride prussia pyotr_iii queen russia stanisław_august_poniatowski subtitled tagme video
animated austria black_hair catherine_the_great elizabeth_of_russia historical_event history joseph_ii king louis_xvi madame_de_pompadour madame_du_barry maria_theresa marie_antoinette multiple_boys multiple_girls niconico parody poland princess princess_bride prussia pyotr_iii queen russia stanisław_august_poniatowski subtitled tagme video
! 18th_century 1dickgirl 1futa 1futanari 1girl1futa 1girls :0 accidental_paizuri big_breasts big_penis blush bouncing_breasts breasts_out brown_hair brown_hair_female catherine_the_great clothed_female_nude_futanari colored colorful cyclone123 dark-skinned_futanari dubious_consent extra_credits extra_history futa_on_female hi_res highres historical historical_figure historical_porn history huge_cock light-skinned_female looking_at_penis mature_female mob_face motion_blur motion_lines open_eyes open_mouth paizuri paizuri_on_lap porn_of_real_person public_domain purple_background queen real_person ripped_clothing royal royalty russia shocked shocked_expression shocked_look surprised surprised_expression tahiti text_bubble unseen_futa_face white_body yellow_outfit youtube
! 18th_century 1dickgirl 1futa 1futanari 1girl1futa 1girls :0 accidental_paizuri big_breasts big_penis blush bouncing_breasts breasts_out brown_hair brown_hair_female catherine_the_great clothed_female_nude_futanari colored colorful cyclone123 dark-skinned_futanari dubious_consent extra_credits extra_history futa_on_female hi_res highres historical historical_figure historical_porn history huge_cock light-skinned_female looking_at_penis mature_female mob_face motion_blur motion_lines open_eyes open_mouth paizuri paizuri_on_lap porn_of_real_person public_domain purple_background queen real_person ripped_clothing royal royalty russia shocked shocked_expression shocked_look surprised surprised_expression tahiti text_bubble unseen_futa_face white_body yellow_outfit youtube
2boys 2girls animal black_eyes black_hair black_headwear bridle closed_mouth commentary_request donkey geumsu hair_ornament hair_stick hat_feather highres history horse horseback_riding korean_clothes korean_commentary multiple_boys multiple_girls original riding saddle sash simple_background standing stirrups_(riding) tassel white_background
2boys 2girls animal black_eyes black_hair black_headwear bridle closed_mouth commentary_request donkey geumsu hair_ornament hair_stick hat_feather highres history horse horseback_riding korean_clothes korean_commentary multiple_boys multiple_girls original riding saddle sash simple_background standing stirrups_(riding) tassel white_background
1girl blue_eyes brown_hair full_body grin hat hat_feather highres history holding holding_sword holding_weapon landsknecht long_sleeves medium_hair open_mouth original ostwindprojekt red_hat scabbard shadow sheath simple_background smile solo standing sword teeth weapon white_background zweihander
1girl blue_eyes brown_hair full_body grin hat hat_feather highres history holding holding_sword holding_weapon landsknecht long_sleeves medium_hair open_mouth original ostwindprojekt red_hat scabbard shadow sheath simple_background smile solo standing sword teeth weapon white_background zweihander
britannia british british_female british_flag history national_personification
britannia british british_female british_flag history national_personification
azur_lane battleship blonde_hair blush dark_blonde_hair german_empire german_female german_flag history lützow_(azur_lane) ocean red_eyes tagme tim_heyderich underwear ww1
azur_lane battleship blonde_hair blush dark_blonde_hair german_empire german_female german_flag history lützow_(azur_lane) ocean red_eyes tagme tim_heyderich underwear ww1
ancient ancient_history ancient_rome bikini blonde_hair harem historical historical_porn history midriff multiple_girls roman_empire rome
ancient ancient_history ancient_rome bikini blonde_hair harem historical historical_porn history midriff multiple_girls roman_empire rome
1girl barefoot capelin_s dress flower full_body grey_eyes hands_up highres history long_sleeves looking_at_viewer original parted_lips print_dress red_background red_dress red_flower smile solo standing traditional_clothes wide_sleeves
1girl barefoot capelin_s dress flower full_body grey_eyes hands_up highres history long_sleeves looking_at_viewer original parted_lips print_dress red_background red_dress red_flower smile solo standing traditional_clothes wide_sleeves
1boy 1futa :) ;) after_sex aftermath anal anal_rape anal_sex anne_boleyn arm_behind_back bed bedroom bent_over_bed brown_hair cocky cocky_smile cum_in_ass cum_inside decapitated decapitated_head dress england fat fat_man french_hood futa_on_male futadom futanari ghost ghost_girl gown grey_background hand_on_penis heavy_balls henry_viii historical historical_porn history historylover huge_balls huge_cock karma leaking_ass leaking_asshole leaking_cum leaking_penis light-skinned_female light-skinned_futanari light-skinned_male long_hair looking_away male maroon_clothing medieval medieval_england mob_face motion_lines non_con non_consensual nude_male_clothed_female partial_male public_domain queen rape red_ass revenge ripped_clothing ripped_dress rough_sex simple_background simple_face simple_shading smirk smirking source_request trembling trembling_pleasure tudor_era unseen_male_face veiny_penis
1boy 1futa :) ;) after_sex aftermath anal anal_rape anal_sex anne_boleyn arm_behind_back bed bedroom bent_over_bed brown_hair cocky cocky_smile cum_in_ass cum_inside decapitated decapitated_head dress england fat fat_man french_hood futa_on_male futadom futanari ghost ghost_girl gown grey_background hand_on_penis heavy_balls henry_viii historical historical_porn history historylover huge_balls huge_cock karma leaking_ass leaking_asshole leaking_cum leaking_penis light-skinned_female light-skinned_futanari light-skinned_male long_hair looking_away male maroon_clothing medieval medieval_england mob_face motion_lines non_con non_consensual nude_male_clothed_female partial_male public_domain queen rape red_ass revenge ripped_clothing ripped_dress rough_sex simple_background simple_face simple_shading smirk smirking source_request trembling trembling_pleasure tudor_era unseen_male_face veiny_penis
>:/ ... 14th_century 2boys anger_vein angry angry_expression annoyed annoyed_expression assjob back_view black_hat brown_hair clothed clothed_male_nude_male clothed_sex comic cousins cyclone123 dat_ass death_glare disembodied_arm disembodied_arms disembodied_hands disgust disgusted dubious_consent extra_credits extra_history fat_ass france frown frowning frowning_at_partner frowning_at_viewer furious gay glare glaring glaring_at_partner glaring_at_viewer gradient_background gradient_shading grey_background groping groping_ass historical_porn history hotdogging hotdogging_ass imminent_anal imminent_penetration imminent_sex incest john_the_fearless light-skinned_male louis_i_duke_of_orléans mad male_focus male_only male_pov medieval medieval_europe medieval_france medieval_history mob_face motion_lines public_domain red_outfit robe simple_background simple_coloring simple_shading squeezing squeezing_ass squeezing_butt text_bubble thick_ass thick_thighs throbbing_penis tight_clothing uncut uncut_penis youtube
>:/ ... 14th_century 2boys anger_vein angry angry_expression annoyed annoyed_expression assjob back_view black_hat brown_hair clothed clothed_male_nude_male clothed_sex comic cousins cyclone123 dat_ass death_glare disembodied_arm disembodied_arms disembodied_hands disgust disgusted dubious_consent extra_credits extra_history fat_ass france frown frowning frowning_at_partner frowning_at_viewer furious gay glare glaring glaring_at_partner glaring_at_viewer gradient_background gradient_shading grey_background groping groping_ass historical_porn history hotdogging hotdogging_ass imminent_anal imminent_penetration imminent_sex incest john_the_fearless light-skinned_male louis_i_duke_of_orléans mad male_focus male_only male_pov medieval medieval_europe medieval_france medieval_history mob_face motion_lines public_domain red_outfit robe simple_background simple_coloring simple_shading squeezing squeezing_ass squeezing_butt text_bubble thick_ass thick_thighs throbbing_penis tight_clothing uncut uncut_penis youtube
1girl absurdres ancient_greek_clothes black_hair blush border bracelet braid braided_ponytail breasts cleavage dizuke gradient_background greco-roman_clothes greyscale hand_up highres history jewelry medium_breasts minoan_clothes monochrome navel nipples original parted_lips solo traditional_clothes upper_body white_border
1girl absurdres ancient_greek_clothes black_hair blush border bracelet braid braided_ponytail breasts cleavage dizuke gradient_background greco-roman_clothes greyscale hand_up highres history jewelry medium_breasts minoan_clothes monochrome navel nipples original parted_lips solo traditional_clothes upper_body white_border
aircraft aircraft_carrier airplane bomb dive_bomber explosion explosive fire gun highres historical_event history imperial_japanese_navy machine_gun military military_vehicle mo_yu_de_jiaozi ocean original pilot propeller roundel sbd_dauntless ship shouhou_(aircraft_carrier) sky smoke star_(symbol) united_states_navy vehicle_focus warship watercraft waves weapon world_war_ii
aircraft aircraft_carrier airplane bomb dive_bomber explosion explosive fire gun highres historical_event history imperial_japanese_navy machine_gun military military_vehicle mo_yu_de_jiaozi ocean original pilot propeller roundel sbd_dauntless ship shouhou_(aircraft_carrier) sky smoke star_(symbol) united_states_navy vehicle_focus warship watercraft waves weapon world_war_ii
5boys absurdres animal arrow_(projectile) beard black_hair black_headwear blood bow bullet_hole clenched_teeth commentary_request day death closed_eyes facial_hair geumsu grass grey_hair gun hat highres history holding holding_gun holding_sword holding_weapon korean_clothes korean_commentary long_sleeves multiple_boys musket mustache old old_man open_mouth original outdoors ruler sash sword tassel teeth tiger tree weapon
5boys absurdres animal arrow_(projectile) beard black_hair black_headwear blood bow bullet_hole clenched_teeth commentary_request day death closed_eyes facial_hair geumsu grass grey_hair gun hat highres history holding holding_gun holding_sword holding_weapon korean_clothes korean_commentary long_sleeves multiple_boys musket mustache old old_man open_mouth original outdoors ruler sash sword tassel teeth tiger tree weapon
blowjob blushing clothed concerned disembodied_hands extra_credits extra_history femboy first_porn_of_character frederick_the_great history kattesbobcxt old_fritz older_male powdered_wig public_domain royalty submissive_male yaoi youtube
blowjob blushing clothed concerned disembodied_hands extra_credits extra_history femboy first_porn_of_character frederick_the_great history kattesbobcxt old_fritz older_male powdered_wig public_domain royalty submissive_male yaoi youtube
>:/ ... 14th_century 2boys annoyed annoyed_expression big_ass black_hat brown_hair bubble_ass bubble_butt cousins cyclone123 dat_ass dat_butt disembodied_arm disembodied_hand dubious_consent extra_credits extra_history fat_ass first_porn_of_character france frown frowning frowning_at_partner gay grabbing grabbing_ass grabbing_from_behind gradient gradient_background gradient_shading grey_background groping groping_ass groping_from_behind historical historical_porn history imminent_sex incest interrupted interuption john_the_fearless light-skinned_male looking_at_another looking_at_partner looking_back louis_i_duke_of_orleans mature_male medieval medieval_europe medieval_france mob_face public_domain real_person red_outfit red_robe robe royalty simple_background simple_eyes simple_shading squeezing_ass squeezing_butt text_bubble thick_ass thick_thighs tight_clothing unseen_male_face voluptuous_male white_body younger_male youtube
>:/ ... 14th_century 2boys annoyed annoyed_expression big_ass black_hat brown_hair bubble_ass bubble_butt cousins cyclone123 dat_ass dat_butt disembodied_arm disembodied_hand dubious_consent extra_credits extra_history fat_ass first_porn_of_character france frown frowning frowning_at_partner gay grabbing grabbing_ass grabbing_from_behind gradient gradient_background gradient_shading grey_background groping groping_ass groping_from_behind historical historical_porn history imminent_sex incest interrupted interuption john_the_fearless light-skinned_male looking_at_another looking_at_partner looking_back louis_i_duke_of_orleans mature_male medieval medieval_europe medieval_france mob_face public_domain real_person red_outfit red_robe robe royalty simple_background simple_eyes simple_shading squeezing_ass squeezing_butt text_bubble thick_ass thick_thighs tight_clothing unseen_male_face voluptuous_male white_body younger_male youtube
1girls 4boys black_hair clothed_sex cum cum_in_mouth cum_in_pussy cum_inside cum_on_face dark-skinned_female dark-skinned_male dark_skin erect_nipples erect_nipples_under_clothes erect_penis female gangbang handjob history interracial latina latina_female light-skinned_male maria_ramirez oral_penetration oral_sex original our_friend_martin pigtail_braids smile sparrow_(artist) speech twintails
1girls 4boys black_hair clothed_sex cum cum_in_mouth cum_in_pussy cum_inside cum_on_face dark-skinned_female dark-skinned_male dark_skin erect_nipples erect_nipples_under_clothes erect_penis female gangbang handjob history interracial latina latina_female light-skinned_male maria_ramirez oral_penetration oral_sex original our_friend_martin pigtail_braids smile sparrow_(artist) speech twintails
armbinder bad_end big_breasts black_hair blush breasts captured captured_heroine chel chel_(the_road_to_el_dorado) collar colonialism crossover dark-skinned_female dark_skin defeat defeated defeated_heroine disney dreamworks enslaved exposed_breasts female femsub gag gagged historical history latina moana moana_waialiki multiple_girls multiple_subs native native_american native_american_clothing native_american_female native_latina nipple_piercing nipple_rings peytell raceplay racism ring ring_gag ring_piercing slave slave_auction slave_collar slavegirl the_road_to_el_dorado
armbinder bad_end big_breasts black_hair blush breasts captured captured_heroine chel chel_(the_road_to_el_dorado) collar colonialism crossover dark-skinned_female dark_skin defeat defeated defeated_heroine disney dreamworks enslaved exposed_breasts female femsub gag gagged historical history latina moana moana_waialiki multiple_girls multiple_subs native native_american native_american_clothing native_american_female native_latina nipple_piercing nipple_rings peytell raceplay racism ring ring_gag ring_piercing slave slave_auction slave_collar slavegirl the_road_to_el_dorado