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2boys anal anal_juice anal_sex anal_through_clothes annoyed annoyed_expression annoyed_face ass_focus ass_juice bed bedsheets black_hat brown_hair bubble_ass bubble_butt clothed clothed_male_nude_male clothed_sex corkscrew_position crossover crossover_pairing crossover_shipping cyclone123 dark-skinned_male extra_credits extra_history france french fully_clothed fully_clothed_male furrowed_eyebrows gay gay_anal gay_sex gradient_background history john_the_fearless light-skinned_male lil_nas_x medieval medieval_europe medieval_france medieval_history mob_face motion_blur nude_male plain_background plap plap_(sound) plump_butt plump_thighs public_domain red_outfit red_robe robe simple_background text thick_ass thick_thighs unseen_male_face weird_crossover yaoi youtube
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>:/ ... 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
2girls ai_generated bare_shoulders bare_thighs blonde_hair_female brown_hair_female burning_building captured_girl dall-e3 defeated dress_pulled_down enslaved_royal femsub historical history imminent_rape jewelry kneeling_on_ground medieval_clothing medieval_history multiple_boys night outdoors rain raining sad scared soldiers spoils_of_war tagme torn_dress treasure wet_clothes wet_clothing white_dress white_skinned_female
2girls ai_generated bare_shoulders bare_thighs blonde_hair_female brown_hair_female burning_building captured_girl dall-e3 defeated dress_pulled_down enslaved_royal femsub historical history imminent_rape jewelry kneeling_on_ground medieval_clothing medieval_history multiple_boys night outdoors rain raining sad scared soldiers spoils_of_war tagme torn_dress treasure wet_clothes wet_clothing white_dress white_skinned_female
5girls ai_generated breasts_out brown_hair_female crowd crowd_watching crown dall-e3 embarrassed_female enslaved_royal femsub historical historical_porn history humiliated humiliation jewelry medieval_clothing medieval_history mother_and_daughter multiple_girls multiple_subs outside parade princess public_exposure public_humiliation queen rain raining see-through_dress sisters spoils_of_war tagme walk_of_shame walking wet_clothes wet_hair
5girls ai_generated breasts_out brown_hair_female crowd crowd_watching crown dall-e3 embarrassed_female enslaved_royal femsub historical historical_porn history humiliated humiliation jewelry medieval_clothing medieval_history mother_and_daughter multiple_girls multiple_subs outside parade princess public_exposure public_humiliation queen rain raining see-through_dress sisters spoils_of_war tagme walk_of_shame walking wet_clothes wet_hair
4girls ai_generated back back_view black_dress brown_hair_female crowd crowd_watching crown dall-e3 embarrassed_female enslaved_royal femsub golden_dress historical historical_porn history humiliated humiliation medieval_armour medieval_clothing medieval_history mother_and_daughter multiple_girls multiple_subs outside parade pink_dress princess public_humiliation queen rain raining sisters spoils_of_war tagme walk_of_shame walking wet_clothes wet_hair
4girls ai_generated back back_view black_dress brown_hair_female crowd crowd_watching crown dall-e3 embarrassed_female enslaved_royal femsub golden_dress historical historical_porn history humiliated humiliation medieval_armour medieval_clothing medieval_history mother_and_daughter multiple_girls multiple_subs outside parade pink_dress princess public_humiliation queen rain raining sisters spoils_of_war tagme walk_of_shame walking wet_clothes wet_hair
1boy 1girls ai_failure ai_generated ancient_history breasts creedfen87 eleanor_of_aquitaine female history male medieval_history nipples nude queen royal royalty sex
1boy 1girls ai_failure ai_generated ancient_history breasts creedfen87 eleanor_of_aquitaine female history male medieval_history nipples nude queen royal royalty sex
ai_failure ai_generated breasts creedfen87 doggy_style eleanor_of_aquitaine female history male medieval_history nude queen royal royalty sex
ai_failure ai_generated breasts creedfen87 doggy_style eleanor_of_aquitaine female history male medieval_history nude queen royal royalty sex
ai_generated ancient_history breasts creedfen87 early_pregnancy eleanor_of_aquitaine female history male medieval_history nipples nude pregnant pregnant_sex queen royal royalty sex
ai_generated ancient_history breasts creedfen87 early_pregnancy eleanor_of_aquitaine female history male medieval_history nipples nude pregnant pregnant_sex queen royal royalty sex
ai_generated ancient_history breasts creedfen87 eleanor_of_aquitaine female female_only history medieval_history nipples nude queen royal royalty
ai_generated ancient_history breasts creedfen87 eleanor_of_aquitaine female female_only history medieval_history nipples nude queen royal royalty
1930 1930s 1girls 20th_century breasts clothed_male_nude_female edmond_malassis human_furniture kneeling louis_xi medieval medieval_clothing medieval_history nude_female public_domain reading_book traditional_media_(artwork) vintage
1930 1930s 1girls 20th_century breasts clothed_male_nude_female edmond_malassis human_furniture kneeling louis_xi medieval medieval_clothing medieval_history nude_female public_domain reading_book traditional_media_(artwork) vintage
after_anal after_rape after_sex after_vaginal amanitore ancient_history ancient_middle_east artist_request ba-trieu catherine_de_medici civilization civilization_(series) civilization_vi cleopatra cleopatra_(civilization_vi) clothes_on_floor clothes_removed clothing_aside collage cum_in_ass cum_in_mouth cum_in_pussy cum_inside cum_on_body cum_on_breasts cum_on_face dido_of_carthage dyah_gytarja eleanor_of_aquitaine eleanor_of_aquitaine_(civilization_vi) european excessive_cum female female_only gorgo harem history human human_only jadwiga kristina lady_six_sky medieval_history middle_eastern middle_eastern_female multiple_girls public_domain queen_victoria queen_wilhelmina rape scythia seondeok straight tamar_of_georgia tomyris
after_anal after_rape after_sex after_vaginal amanitore ancient_history ancient_middle_east artist_request ba-trieu catherine_de_medici civilization civilization_(series) civilization_vi cleopatra cleopatra_(civilization_vi) clothes_on_floor clothes_removed clothing_aside collage cum_in_ass cum_in_mouth cum_in_pussy cum_inside cum_on_body cum_on_breasts cum_on_face dido_of_carthage dyah_gytarja eleanor_of_aquitaine eleanor_of_aquitaine_(civilization_vi) european excessive_cum female female_only gorgo harem history human human_only jadwiga kristina lady_six_sky medieval_history middle_eastern middle_eastern_female multiple_girls public_domain queen_victoria queen_wilhelmina rape scythia seondeok straight tamar_of_georgia tomyris
2boys army army_uniform big_balls big_penis breasts cum cumming ejaculation gabrielrd gay history human human_only king light-skinned_male light_skin male male_only male_penetrated masturbation medieval_history monarch philip_ii_of_spain public_domain royal royalty spain spanish uniform vein veiny_penis yaoi
2boys army army_uniform big_balls big_penis breasts cum cumming ejaculation gabrielrd gay history human human_only king light-skinned_male light_skin male male_only male_penetrated masturbation medieval_history monarch philip_ii_of_spain public_domain royal royalty spain spanish uniform vein veiny_penis yaoi
2019 2d athletic athletic_female big_ass bodybuilding brown_hair civilization civilization_vi crown eastern_european female female_only human human_only jadwiga janrock light-skinned_female light_skin mature mature_female medieval medieval_history milf muscular muscular_ass muscular_back muscular_female muscular_thighs poland polish public_domain queen rear_view royalty slavic smooth_skin solo solo_female thick_ass undressing
2019 2d athletic athletic_female big_ass bodybuilding brown_hair civilization civilization_vi crown eastern_european female female_only human human_only jadwiga janrock light-skinned_female light_skin mature mature_female medieval medieval_history milf muscular muscular_ass muscular_back muscular_female muscular_thighs poland polish public_domain queen rear_view royalty slavic smooth_skin solo solo_female thick_ass undressing
1boy armor balls ballsack beard big_balls big_penis boots civilization civilization_vi cum ejaculation erection facial_hair gabrielrd handjob history human human_only king light-skinned_male light_skin male male_only manly masturbating mature_male medieval medieval_history military military_uniform monochrome mustache necklace open_clothes penis penis_out philip_ii_of_spain portugal portuguese public_domain royal royalty scabbard scrotum smooth_skin solo spain spanish sword testicles uniform vein veins veiny_penis
1boy armor balls ballsack beard big_balls big_penis boots civilization civilization_vi cum ejaculation erection facial_hair gabrielrd handjob history human human_only king light-skinned_male light_skin male male_only manly masturbating mature_male medieval medieval_history military military_uniform monochrome mustache necklace open_clothes penis penis_out philip_ii_of_spain portugal portuguese public_domain royal royalty scabbard scrotum smooth_skin solo spain spanish sword testicles uniform vein veins veiny_penis
1girls breasts crown crown_only crusader_kings duchess duchess_matilda_(crusader_kings_3) european european_female female female_only game_screenshot history human human_only light-skinned_female light_skin matilda_of_tuscany medieval medieval_history medium_breasts nude nude_female public_domain royalty screenshot small_breasts solo solo_female
1girls breasts crown crown_only crusader_kings duchess duchess_matilda_(crusader_kings_3) european european_female female female_only game_screenshot history human human_only light-skinned_female light_skin matilda_of_tuscany medieval medieval_history medium_breasts nude nude_female public_domain royalty screenshot small_breasts solo solo_female
6girls ancient_history ancient_korea ass barefoot barely_clothed breasts byzantine byzantine_empire cathedral catherine_ii_of_russia civilization civilization_(series) civilization_v civilization_vi civpinups cross crown elizabeth_i_of_england empress england english female female_only hagia_sophia_cathedral history hourglass_figure human human_only isabella_i_of_castile legs_together light-skinned_female light_skin lit_candle mature mature_female medieval medieval_history mediterranean milf multiple_girls national_personification pinup pinup_pose public_domain queen revealing_clothes royalty russia seondeok skimpy smooth_skin spain tamar_of_georgia theodora_of_byzantium voluptuous voluptuous_female
6girls ancient_history ancient_korea ass barefoot barely_clothed breasts byzantine byzantine_empire cathedral catherine_ii_of_russia civilization civilization_(series) civilization_v civilization_vi civpinups cross crown elizabeth_i_of_england empress england english female female_only hagia_sophia_cathedral history hourglass_figure human human_only isabella_i_of_castile legs_together light-skinned_female light_skin lit_candle mature mature_female medieval medieval_history mediterranean milf multiple_girls national_personification pinup pinup_pose public_domain queen revealing_clothes royalty russia seondeok skimpy smooth_skin spain tamar_of_georgia theodora_of_byzantium voluptuous voluptuous_female
1girls breasts cape civilization civpinups covering_breasts dress female female_only fit fit_female history human human_only light-skinned_female light_skin maria_i mature mature_female medieval_history milf pinup pinup_pose portugal queen royalty sensual skirt smooth_skin solo solo_female topless topless_female voluptuous voluptuous_female
1girls breasts cape civilization civpinups covering_breasts dress female female_only fit fit_female history human human_only light-skinned_female light_skin maria_i mature mature_female medieval_history milf pinup pinup_pose portugal queen royalty sensual skirt smooth_skin solo solo_female topless topless_female voluptuous voluptuous_female
1girls abs anklewear areola biceps big_areola big_breasts big_nipples breasts breasts_apart brown_hair byzantine byzantine_empire casual civilization cleft_of_venus empress facing_viewer feet female female_only fresco full_lips functionally_nude headwear hips history human human_only janrock light-skinned_female light_skin looking_at_viewer mature mature_female medieval medieval_history mediterranean middle_ages muscular muscular_female neckwear nipples orthodox perky_breasts plump_labia pose pubic_hair puffy_areola pussy queen roman roman_empire royal royalty sitting sitting_on_throne smooth_skin solo solo_female source_request southern_european straight-on theodora_of_byzantium thick_thighs thighs throne toes uncensored voluptuous voluptuous_female wide_hips wristwear
1girls abs anklewear areola biceps big_areola big_breasts big_nipples breasts breasts_apart brown_hair byzantine byzantine_empire casual civilization cleft_of_venus empress facing_viewer feet female female_only fresco full_lips functionally_nude headwear hips history human human_only janrock light-skinned_female light_skin looking_at_viewer mature mature_female medieval medieval_history mediterranean middle_ages muscular muscular_female neckwear nipples orthodox perky_breasts plump_labia pose pubic_hair puffy_areola pussy queen roman roman_empire royal royalty sitting sitting_on_throne smooth_skin solo solo_female source_request southern_european straight-on theodora_of_byzantium thick_thighs thighs throne toes uncensored voluptuous voluptuous_female wide_hips wristwear
1girls arabian_clothes arabic_text armor big_belly blonde_hair brown-skinned_male brown_skin collar commission cross crusader dark-skinned_male dark_skin double_penetration female female_knight gangbang group group_sex helmet history holding_breast interracial jiragora knight lactation light-skinned_female light_skin male mask medieval medieval_armour medieval_history middle_eastern_clothing multiple_boys pale-skinned_female pale_skin partial_male penetration persian_text pregnant pregnant_sex pubic_hair raceplay reverse_cowgirl_double_penetration reverse_cowgirl_position slave turkish_clothing urdu_text warrior
1girls arabian_clothes arabic_text armor big_belly blonde_hair brown-skinned_male brown_skin collar commission cross crusader dark-skinned_male dark_skin double_penetration female female_knight gangbang group group_sex helmet history holding_breast interracial jiragora knight lactation light-skinned_female light_skin male mask medieval medieval_armour medieval_history middle_eastern_clothing multiple_boys pale-skinned_female pale_skin partial_male penetration persian_text pregnant pregnant_sex pubic_hair raceplay reverse_cowgirl_double_penetration reverse_cowgirl_position slave turkish_clothing urdu_text warrior
1boy 1girls aztec aztec_headgear blonde_hair blue_eyes civilization civilization_v coppered dark-skinned_male dark_skin defeated eleanor_of_aquitaine european female femsub france french history human human_only interracial light-skinned_female light_skin male maledom medieval medieval_history mesoamerican mexican_male montezuma native_american native_american_male popthesnowman public_domain queen rape royalty smooth_skin spit spoils_of_war straight submissive
1boy 1girls aztec aztec_headgear blonde_hair blue_eyes civilization civilization_v coppered dark-skinned_male dark_skin defeated eleanor_of_aquitaine european female femsub france french history human human_only interracial light-skinned_female light_skin male maledom medieval medieval_history mesoamerican mexican_male montezuma native_american native_american_male popthesnowman public_domain queen rape royalty smooth_skin spit spoils_of_war straight submissive
abs anthro_only biceps bodybuilder civilization hyper hyper_balls hyper_genitalia hyper_muscles hyper_penis hyper_testicles male male_focus male_only medieval_history muscle muscles muscular muscular_anthro muscular_arms muscular_ass muscular_back muscular_legs muscular_male muscular_thighs nipples pecs philip_ii_of_spain regnar solo veins veiny_penis
abs anthro_only biceps bodybuilder civilization hyper hyper_balls hyper_genitalia hyper_muscles hyper_penis hyper_testicles male male_focus male_only medieval_history muscle muscles muscular muscular_anthro muscular_arms muscular_ass muscular_back muscular_legs muscular_male muscular_thighs nipples pecs philip_ii_of_spain regnar solo veins veiny_penis
1boy 1girls 3d anal anal_penetration anal_sex animated arcadnsfw areolae bouncing_breasts breasts byzantine byzantine_empire cathedral civilization civilization_v cleft_of_venus day daytime empress european european_female eyeliner female from_behind greek green_eyes hagia_sophia_cathedral hetero history human human_only indoors jewelry light-skinned_female light-skinned_male light_skin male medieval medieval_history medium_breasts nipples no_sound nude_male_clothed_female penile_penetration penis_in_anus penis_in_ass pubic_hair public_domain pussy reverse_cowgirl_position royal royalty smooth_skin spread_legs straight tan-skinned_female theodora_of_byzantium uncensored unseen_male_face video
1boy 1girls 3d anal anal_penetration anal_sex animated arcadnsfw areolae bouncing_breasts breasts byzantine byzantine_empire cathedral civilization civilization_v cleft_of_venus day daytime empress european european_female eyeliner female from_behind greek green_eyes hagia_sophia_cathedral hetero history human human_only indoors jewelry light-skinned_female light-skinned_male light_skin male medieval medieval_history medium_breasts nipples no_sound nude_male_clothed_female penile_penetration penis_in_anus penis_in_ass pubic_hair public_domain pussy reverse_cowgirl_position royal royalty smooth_skin spread_legs straight tan-skinned_female theodora_of_byzantium uncensored unseen_male_face video
1boy anal_fingering big_ass big_balls big_penis blue civilization civilization_vi cum ejaculation fingering fingering_self history human human_only king light-skinned_male light_skin male male_only medieval_history penis philip_ii_of_spain royal royalty smooth_skin solo_male uniform
1boy anal_fingering big_ass big_balls big_penis blue civilization civilization_vi cum ejaculation fingering fingering_self history human human_only king light-skinned_male light_skin male male_only medieval_history penis philip_ii_of_spain royal royalty smooth_skin solo_male uniform
1girls ancient ancient_history ancient_rome areola arm_support bed big_areola big_belly big_breasts big_nipples breasts breasts_apart brown_eyes brown_hair bunintheoven byzantine byzantine_empire cathedral civilization civilization_v cleft_of_venus curtains day empress english_text europe facing_viewer feet female female_only full_body full_lips gold_jewelry hagia_sophia_cathedral headwear_only hips history human_only indoors jewelry_only large_areolae large_breasts legs_together linea_nigra looking_at_viewer lying lying_on_side medieval medieval_history medium_breasts naked naked_female naked_jewelry navel necklace nipples nude nude_female on_bed on_side outie_navel pale-skinned_female pale_skin perky_breasts plump_labia pose pregnant pregnant_belly pregnant_female public_domain puffy_areola pussy ready_to_pop roman roman_empire solo speech_bubble talking_to_viewer text text_box theodora_of_byzantium thick_thighs thighs toes uncensored wide_hips
1girls ancient ancient_history ancient_rome areola arm_support bed big_areola big_belly big_breasts big_nipples breasts breasts_apart brown_eyes brown_hair bunintheoven byzantine byzantine_empire cathedral civilization civilization_v cleft_of_venus curtains day empress english_text europe facing_viewer feet female female_only full_body full_lips gold_jewelry hagia_sophia_cathedral headwear_only hips history human_only indoors jewelry_only large_areolae large_breasts legs_together linea_nigra looking_at_viewer lying lying_on_side medieval medieval_history medium_breasts naked naked_female naked_jewelry navel necklace nipples nude nude_female on_bed on_side outie_navel pale-skinned_female pale_skin perky_breasts plump_labia pose pregnant pregnant_belly pregnant_female public_domain puffy_areola pussy ready_to_pop roman roman_empire solo speech_bubble talking_to_viewer text text_box theodora_of_byzantium thick_thighs thighs toes uncensored wide_hips
1girls 3boys ancient ancient_china china chinese_clothes chinese_history clothing cum cum_in_pussy cum_inside defeated duo east_asian_clothing enslaved_royal far_eastern_history female firolian game_over history long_hair male medieval medieval_china medieval_history multiple_boys national_personification partial_male penetration penis princess public_domain pussy rape royalty sex sex_slave slave slave_girl slavegirl spoils_of_war straight sun_ren total_war total_war:_three_kingdoms vaginal_penetration
1girls 3boys ancient ancient_china china chinese_clothes chinese_history clothing cum cum_in_pussy cum_inside defeated duo east_asian_clothing enslaved_royal far_eastern_history female firolian game_over history long_hair male medieval medieval_china medieval_history multiple_boys national_personification partial_male penetration penis princess public_domain pussy rape royalty sex sex_slave slave slave_girl slavegirl spoils_of_war straight sun_ren total_war total_war:_three_kingdoms vaginal_penetration
1girls amazon biceps bodybuilding breasts brown_hair cape crown eastern_european extreme_muscles female female_only flag history human human_only jadwiga janrock light-skinned_female light_skin long_hair medieval medieval_history muscles muscular muscular_arms muscular_female muscular_legs navel nipples poland polish pubic_hair public_domain queen royalty slavic solo solo_female sword thick_thighs weapon
1girls amazon biceps bodybuilding breasts brown_hair cape crown eastern_european extreme_muscles female female_only flag history human human_only jadwiga janrock light-skinned_female light_skin long_hair medieval medieval_history muscles muscular muscular_arms muscular_female muscular_legs navel nipples poland polish pubic_hair public_domain queen royalty slavic solo solo_female sword thick_thighs weapon
after_rape areolae blasphemy breasts civilization civilization_v cum cum_on_face defeated enslaved_royal europe european female female_only history isabella_i_of_castile latina latina_female looking_at_viewer medieval medieval_history natthelich nipples partial_male public_domain queen rape royal royalty slave_girl slavegirl smooth_skin solo spain spanish spanish_history spoils_of_war
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angry_face areolae blasphemy breasts civilization civilization_v crown defeated enslaved_royal europe european female female_only history imminent_rape isabella_i_of_castile latina latina_female looking_at_viewer medieval medieval_history natthelich nipples partial_male public_domain royal royalty slave_girl slavegirl smooth_skin solo spain spanish spanish_history spoils_of_war
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1boy 3d 4girls ancient ancient_china ancient_history animated boudica boudica_(boadicea) british catherine_ii_of_russia celt celtic civilization civilization_v collaborative_fellatio diversity east_asian eastern_european elizabeth_i_of_england empress england english fellatio female fivesome from_above hand_on_head history human human_only interracial light-skinned_female light_skin male male_pov medieval medieval_history multiple_girls partial_male penis pov public_domain quadruple_fellatio queen quick_e royalty russia russian source_filmmaker straight teamwork wu_zetian
1boy 3d 4girls ancient ancient_china ancient_history animated boudica boudica_(boadicea) british catherine_ii_of_russia celt celtic civilization civilization_v collaborative_fellatio diversity east_asian eastern_european elizabeth_i_of_england empress england english fellatio female fivesome from_above hand_on_head history human human_only interracial light-skinned_female light_skin male male_pov medieval medieval_history multiple_girls partial_male penis pov public_domain quadruple_fellatio queen quick_e royalty russia russian source_filmmaker straight teamwork wu_zetian
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