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ancient_rome asexualhub assassins bimbo black_serpent cherry_mouse_street comic cult dominance gaius_julius_caesar historical historical_event jove jovilius julius_caesar kennycomix penny_burfine pink_lotus porn_star the_black_serpent
ancient_rome asexualhub assassins bimbo black_serpent cherry_mouse_street comic cult dominance gaius_julius_caesar historical historical_event jove jovilius julius_caesar kennycomix penny_burfine pink_lotus porn_star the_black_serpent
2girls arms_behind_back ass ballet_boots black_one-piece_swimsuit bondage bound bound_arms breast_bondage breasts breasts_out competition_swimsuit covered_navel cowgirl_position dorachan_r face_in_ass female_ejaculation femdom gloves grey_hair hair_ribbon highleg highleg_one-piece_swimsuit highres historical_event i-168_(kantai_collection) kantai_collection kinbaku large_breasts long_hair more_at_source multiple_girls nipples one-piece_swimsuit ponytail pussy_juice red_hair ribbon rope rope_bondage scamp_(kantai_collection) shiba*ri shibari shibari_over_clothes short_shorts shorts side_ponytail sitting_on_face stepped_on swimsuit thighs_together translation_request two-tone_one-piece_swimsuit white_gloves white_one-piece_swimsuit white_shorts yuri
2girls arms_behind_back ass ballet_boots black_one-piece_swimsuit bondage bound bound_arms breast_bondage breasts breasts_out competition_swimsuit covered_navel cowgirl_position dorachan_r face_in_ass female_ejaculation femdom gloves grey_hair hair_ribbon highleg highleg_one-piece_swimsuit highres historical_event i-168_(kantai_collection) kantai_collection kinbaku large_breasts long_hair more_at_source multiple_girls nipples one-piece_swimsuit ponytail pussy_juice red_hair ribbon rope rope_bondage scamp_(kantai_collection) shiba*ri shibari shibari_over_clothes short_shorts shorts side_ponytail sitting_on_face stepped_on swimsuit thighs_together translation_request two-tone_one-piece_swimsuit white_gloves white_one-piece_swimsuit white_shorts yuri
1futa 1girls all_fours areolae arms_behind_back arms_tied artist_name ass ass_grab ass_up azur_lane bangs bed bedroom big_breasts bismarck_(azur_lane) blonde_hair blue_eyes blue_fingernails blue_ribbon blush cum defeat defeat_sex defeated dialogue doggy_style door duo english_text eyes_rolling_back female futa_on_female futadom futanari hair_between_eyes historical_event historical_porn human indoors king_george_v_(azur_lane) light-skinned_female light-skinned_futanari light_skin long_hair looking_at_partner looking_down nipples nude rape red_eyes red_fingernails rolling_eyes sideboob sirceasar squeezing squeezing_butt standing sweat sweating tears text tongue tongue_out top-down_bottom-up twitter_username voluptuous voluptuous_female
1futa 1girls all_fours areolae arms_behind_back arms_tied artist_name ass ass_grab ass_up azur_lane bangs bed bedroom big_breasts bismarck_(azur_lane) blonde_hair blue_eyes blue_fingernails blue_ribbon blush cum defeat defeat_sex defeated dialogue doggy_style door duo english_text eyes_rolling_back female futa_on_female futadom futanari hair_between_eyes historical_event historical_porn human indoors king_george_v_(azur_lane) light-skinned_female light-skinned_futanari light_skin long_hair looking_at_partner looking_down nipples nude rape red_eyes red_fingernails rolling_eyes sideboob sirceasar squeezing squeezing_butt standing sweat sweating tears text tongue tongue_out top-down_bottom-up twitter_username voluptuous voluptuous_female
1boy 1girls adult against_wall ai_generated america anal anal_sex barefoot bent_over big_breasts biting_lip blush boots braid braided_hair brown_hair brown_hair_female buttons clothed_sex clothes_grab doggy_style eighteenth_century eighteenth_century_clothing epaulettes fancy_clothing female focused fourth_of_july frilly from_behind_position general george_washington grabbing_from_behind gray_hair hair_tie hair_tied hair_tied_back hat hazel_eyes headwear high_effort_ai_art high_res high_resolution historical_event historical_porn holidays horny_female indoors jacket lapel large_anal_insertion large_breasts large_penis large_testicles leaning_against_wall leaning_against_window leaning_forward legwear looking_back male mature_female military military_hat military_jacket military_uniform national_holiday navel no_panties no_shoes partially_clothed partially_clothed_female partially_clothed_male president probably_controversial public_domain redcoat revolutionary_war soldier stable_diffusion standing standing_position standing_sex straight thick_thighs thigh_highs thin_waist tiptoes toes tricorne tricorne_hat tricorner_hat trimmed_pubic_hair washington window
1boy 1girls adult against_wall ai_generated america anal anal_sex barefoot bent_over big_breasts biting_lip blush boots braid braided_hair brown_hair brown_hair_female buttons clothed_sex clothes_grab doggy_style eighteenth_century eighteenth_century_clothing epaulettes fancy_clothing female focused fourth_of_july frilly from_behind_position general george_washington grabbing_from_behind gray_hair hair_tie hair_tied hair_tied_back hat hazel_eyes headwear high_effort_ai_art high_res high_resolution historical_event historical_porn holidays horny_female indoors jacket lapel large_anal_insertion large_breasts large_penis large_testicles leaning_against_wall leaning_against_window leaning_forward legwear looking_back male mature_female military military_hat military_jacket military_uniform national_holiday navel no_panties no_shoes partially_clothed partially_clothed_female partially_clothed_male president probably_controversial public_domain redcoat revolutionary_war soldier stable_diffusion standing standing_position standing_sex straight thick_thighs thigh_highs thin_waist tiptoes toes tricorne tricorne_hat tricorner_hat trimmed_pubic_hair washington window
1boy 1girls 2022 2023s 5_fingers achaemenid ancient_greece ancient_history ancient_middle_east ancient_persia anthro anthro_on_anthro anthro_penetrated anthro_penetrating anus ass balls big_breasts big_penis black_hair black_nose bodily_fluids bottomwear bottomwear_down bracelet braided_hair breasts breasts_bigger_than_head bronze_(metal) bronze_mirror canid canine canis cheetah clothed clothed/nude clothed_male clothed_male_nude_female clothing crown cum cum_in_pussy cum_inside digital_media_(artwork) domestic_dog dress duo ear_piercing ear_ring feet felid feline female female_penetrated fingers footwear from_behind_position fur genital_fluids genitals green_eyes hat headgear headwear hi_res historical_event history holding_mirror holding_object humanoid_feet humanoid_hands hunting_dog jewelry looking_pleasured male male/female male_penetrating male_penetrating_female mammal mirror naked nipples nude nude_female ohs688 open_mouth open_smile pants pants_down partially_clothed penetration penile penile_penetration penis penis_in_pussy persian_clothing piercing pussy saluki sex shoes sighthound smile spots spotted_body spotted_fur standing standing_doggystyle standing_sex straight toes tongue traditional_clothes tunic vaginal_penetration voluptuous white_body white_fur yellow_body yellow_fur
1boy 1girls 2022 2023s 5_fingers achaemenid ancient_greece ancient_history ancient_middle_east ancient_persia anthro anthro_on_anthro anthro_penetrated anthro_penetrating anus ass balls big_breasts big_penis black_hair black_nose bodily_fluids bottomwear bottomwear_down bracelet braided_hair breasts breasts_bigger_than_head bronze_(metal) bronze_mirror canid canine canis cheetah clothed clothed/nude clothed_male clothed_male_nude_female clothing crown cum cum_in_pussy cum_inside digital_media_(artwork) domestic_dog dress duo ear_piercing ear_ring feet felid feline female female_penetrated fingers footwear from_behind_position fur genital_fluids genitals green_eyes hat headgear headwear hi_res historical_event history holding_mirror holding_object humanoid_feet humanoid_hands hunting_dog jewelry looking_pleasured male male/female male_penetrating male_penetrating_female mammal mirror naked nipples nude nude_female ohs688 open_mouth open_smile pants pants_down partially_clothed penetration penile penile_penetration penis penis_in_pussy persian_clothing piercing pussy saluki sex shoes sighthound smile spots spotted_body spotted_fur standing standing_doggystyle standing_sex straight toes tongue traditional_clothes tunic vaginal_penetration voluptuous white_body white_fur yellow_body yellow_fur
2futas achaemenid anal anal_sex ancient ancient_greece ancient_history ancient_middle_east ancient_persia angry angry_face angry_sex annoyed annoyed_expression ass ass_grab assertive athena battle big_breasts big_penis black_hair blue_eyes catfight countryhumans crown curly_hair defeated deity destruction doggy_style domination erect_while_penetrated european_mythology faravahar fight from_behind futa_on_futa futa_only futadom futanari futanari_penetrated futasub goddess greece greece_(countryhumans) greek_mythology gritted_teeth hands_on_hips hate_sex hill historical historical_event history iran light-skinned_futanari light_skin middle_eastern_clothing mythology national_personification necklace night on_all_fours persia persian_clothing personification power_symbol public_domain queen rape rape_face royalty screaming sexfight shiny_skin simple_background smug speech_bubble stars straight_hair stretched_anus stretching submissive tight_anal tongue tongue_out virgin virginity_loss war xerxes_the_great yellow_eyes
2futas achaemenid anal anal_sex ancient ancient_greece ancient_history ancient_middle_east ancient_persia angry angry_face angry_sex annoyed annoyed_expression ass ass_grab assertive athena battle big_breasts big_penis black_hair blue_eyes catfight countryhumans crown curly_hair defeated deity destruction doggy_style domination erect_while_penetrated european_mythology faravahar fight from_behind futa_on_futa futa_only futadom futanari futanari_penetrated futasub goddess greece greece_(countryhumans) greek_mythology gritted_teeth hands_on_hips hate_sex hill historical historical_event history iran light-skinned_futanari light_skin middle_eastern_clothing mythology national_personification necklace night on_all_fours persia persian_clothing personification power_symbol public_domain queen rape rape_face royalty screaming sexfight shiny_skin simple_background smug speech_bubble stars straight_hair stretched_anus stretching submissive tight_anal tongue tongue_out virgin virginity_loss war xerxes_the_great yellow_eyes
3girls ahoge anal anal_object_insertion black_eyes black_hair blue_eyes blue_hair blush breasts breath carrying carrying_partner collarbone commission detached_sleeves dildo double_penetration enjaku_izuku eyebrows_visible_through_hair female female_penetrated female_penetrating fff_threesome girl_sandwich glasses green-framed_eyewear grey_eyes grey_hair group_sex hair_ornament hairband headgear highres historical_event kantai_collection kirishima_(kantai_collection) long_hair looking_at_another lower_teeth medium_breasts multicolored_hair multiple_girls necktie nipple_piercing nipples nontraditional_miko object_insertion open_mouth piercing red_hair sandwiched sex_toy short_hair simple_background skeb_commission south_dakota_(kantai_collection) standing standing_sex star_(symbol) star_hair_ornament strap-on suspended_double_penetration sweat teeth thighhighs threesome tongue tongue_out vaginal_object_insertion vaginal_penetration washington_(kantai_collection) yuri
3girls ahoge anal anal_object_insertion black_eyes black_hair blue_eyes blue_hair blush breasts breath carrying carrying_partner collarbone commission detached_sleeves dildo double_penetration enjaku_izuku eyebrows_visible_through_hair female female_penetrated female_penetrating fff_threesome girl_sandwich glasses green-framed_eyewear grey_eyes grey_hair group_sex hair_ornament hairband headgear highres historical_event kantai_collection kirishima_(kantai_collection) long_hair looking_at_another lower_teeth medium_breasts multicolored_hair multiple_girls necktie nipple_piercing nipples nontraditional_miko object_insertion open_mouth piercing red_hair sandwiched sex_toy short_hair simple_background skeb_commission south_dakota_(kantai_collection) standing standing_sex star_(symbol) star_hair_ornament strap-on suspended_double_penetration sweat teeth thighhighs threesome tongue tongue_out vaginal_object_insertion vaginal_penetration washington_(kantai_collection) yuri
4girls 6+boys angry arms_tied_behind_back asphyxiation barbarian bondage breasts breasts_apart cigarette cigarette_holder clothed clothed_male clothed_male_nude_female completely_nude_female covering_crotch dark-skinned_male dark_skin female femsub fez fine_art goatee gottfried_sieben groping group hanged historical historical_event history house human human_only imminent_rape interracial kneeling laughing light-skinned_female light_skin male maledom mass_rape military_uniform moustache multiple_boys multiple_girls multiple_subs naked nipples nude nude_female ottoman_empire outdoors party_wipe public_domain public_nudity restrained scared slave slave_market small_breasts smoking soldier spoils_of_war straight straight_hair turban turkey turkish_clothing turkish_hat uncensored warcrime
4girls 6+boys angry arms_tied_behind_back asphyxiation barbarian bondage breasts breasts_apart cigarette cigarette_holder clothed clothed_male clothed_male_nude_female completely_nude_female covering_crotch dark-skinned_male dark_skin female femsub fez fine_art goatee gottfried_sieben groping group hanged historical historical_event history house human human_only imminent_rape interracial kneeling laughing light-skinned_female light_skin male maledom mass_rape military_uniform moustache multiple_boys multiple_girls multiple_subs naked nipples nude nude_female ottoman_empire outdoors party_wipe public_domain public_nudity restrained scared slave slave_market small_breasts smoking soldier spoils_of_war straight straight_hair turban turkey turkish_clothing turkish_hat uncensored warcrime
4girls 5boys balkan_states bondage church clothed clothed_male clothed_male_nude_female completely_nude_female exposed_breasts female femsub fine_art gottfried_sieben historical historical_event history indoors male maledom mass_rape multiple_boys multiple_girls multiple_subs naked nipples nude nude_female older_male older_man older_man_and_younger_girl ottoman_empire party_wipe priest public_domain rape screaming soldier spoils_of_war straight_hair tagme the_ottoman_empire turkish_clothing turkish_hat
4girls 5boys balkan_states bondage church clothed clothed_male clothed_male_nude_female completely_nude_female exposed_breasts female femsub fine_art gottfried_sieben historical historical_event history indoors male maledom mass_rape multiple_boys multiple_girls multiple_subs naked nipples nude nude_female older_male older_man older_man_and_younger_girl ottoman_empire party_wipe priest public_domain rape screaming soldier spoils_of_war straight_hair tagme the_ottoman_empire turkish_clothing turkish_hat
abuse barefoot being_watched bite bite_mark bite_marks biting blood caramel_deus clothed clothes countryhumans crying defeated doggy_style forced gay hentai historical_event historically_accurate history japanese_empire_(countryhumans) japanese_text military_uniform nude rape republic_of_china_(countryhumans) saliva saliva_string scars tears uniform violence yaoi
abuse barefoot being_watched bite bite_mark bite_marks biting blood caramel_deus clothed clothes countryhumans crying defeated doggy_style forced gay hentai historical_event historically_accurate history japanese_empire_(countryhumans) japanese_text military_uniform nude rape republic_of_china_(countryhumans) saliva saliva_string scars tears uniform violence yaoi
1boy 1girls anthropomorphization balls cruise_ship female frozen historical_event iceberg looking_at_viewer male mast nature night no_humans ocean outside penis personification smokestack testicles titanic uncensored water what
1boy 1girls anthropomorphization balls cruise_ship female frozen historical_event iceberg looking_at_viewer male mast nature night no_humans ocean outside penis personification smokestack testicles titanic uncensored water what
10s 2girls :t absurdres after_rape ashtray bad_id barack_obama book cigar comic crying english fume glasses greyscale grin highres historical_event instant_loss_2koma iowa_(kantai_collection) kantai_collection katori_(kantai_collection) lying monochrome multiple_girls nude on_side pout revision riding_crop ruined_for_marriage smile smoking tears trembling wangphing yes_we_can yuri
10s 2girls :t absurdres after_rape ashtray bad_id barack_obama book cigar comic crying english fume glasses greyscale grin highres historical_event instant_loss_2koma iowa_(kantai_collection) kantai_collection katori_(kantai_collection) lying monochrome multiple_girls nude on_side pout revision riding_crop ruined_for_marriage smile smoking tears trembling wangphing yes_we_can yuri
2girls :t after_rape ashtray barack_obama book cigar comic english female fume glasses greyscale grin high_resolution historical_event instant_loss_2koma iowa_(kantai_collection) kantai_collection katori_(kantai_collection) lying megane monochrome multiple_girls nude on_side pouting riding_crop ruined_for_marriage smile smoking tears trembling very_high_resolution wangphing yes_we_can yuri
2girls :t after_rape ashtray barack_obama book cigar comic english female fume glasses greyscale grin high_resolution historical_event instant_loss_2koma iowa_(kantai_collection) kantai_collection katori_(kantai_collection) lying megane monochrome multiple_girls nude on_side pouting riding_crop ruined_for_marriage smile smoking tears trembling very_high_resolution wangphing yes_we_can yuri
1boy :t after_sex annoyed armor armored_boots arthur_kirkland axis_powers_hetalia black_gloves blue_eyes blush boots brown_hair cum cum_in_pussy embarrassed england_(hetalia) english female flower gloves green_eyes hat hat_flower hat_removed headwear_removed historical_event kantai_collection melisaongmiqin object_namesake oc original_character panties panties_aside pout pun seaport_hime seaport_summer_hime shinkaisei-kan singapore_(hetalia) spread_legs sweatdrop thigh_boots thighhighs too_literal underwear white_hair white_panties
1boy :t after_sex annoyed armor armored_boots arthur_kirkland axis_powers_hetalia black_gloves blue_eyes blush boots brown_hair cum cum_in_pussy embarrassed england_(hetalia) english female flower gloves green_eyes hat hat_flower hat_removed headwear_removed historical_event kantai_collection melisaongmiqin object_namesake oc original_character panties panties_aside pout pun seaport_hime seaport_summer_hime shinkaisei-kan singapore_(hetalia) spread_legs sweatdrop thigh_boots thighhighs too_literal underwear white_hair white_panties
1boy 4_fingers 5girls blood body_horror cactus cloud colonialism copyright_name custer's_revenge desert devil_wings ejaculation enneaphallia eye_penetration female full_body general_custer gigantic_penis goatee gore guro height_difference historical_event historical_people historical_porn historical_revisionist historically_inaccurate male monster multi_eye multi_genitalia multi_mouth multi_penis mustache mutant native native_american nude_female orange_sky paul_robertson penis pixel pixel_art real_person sharp_teeth snuff tagme uncensored vore
1boy 4_fingers 5girls blood body_horror cactus cloud colonialism copyright_name custer's_revenge desert devil_wings ejaculation enneaphallia eye_penetration female full_body general_custer gigantic_penis goatee gore guro height_difference historical_event historical_people historical_porn historical_revisionist historically_inaccurate male monster multi_eye multi_genitalia multi_mouth multi_penis mustache mutant native native_american nude_female orange_sky paul_robertson penis pixel pixel_art real_person sharp_teeth snuff tagme uncensored vore
2boys affront_to_nature blood bullfighter clothed_male dark-skinned_male death gore guro historical_event historical_revisionist historically_inaccurate interracial julio_aparicio male_death male_only matador necrophilia nude_male penis real_person reverse_blowjob seelacanth signature slit_throat snuff spain straight_hair tears throat_fuck throat_penetration toreador torero uncensored wound wound_fucking yaoi
2boys affront_to_nature blood bullfighter clothed_male dark-skinned_male death gore guro historical_event historical_revisionist historically_inaccurate interracial julio_aparicio male_death male_only matador necrophilia nude_male penis real_person reverse_blowjob seelacanth signature slit_throat snuff spain straight_hair tears throat_fuck throat_penetration toreador torero uncensored wound wound_fucking yaoi
1boy 1girls anthropomorphization balls cruise_ship female first_porn_of_franchise frozen historical_event iceberg inanimate looking_at_viewer male mast nature night no_humans ocean outside parody penis personification rape ship smokestack tear testicles titanic uncensored water what
1boy 1girls anthropomorphization balls cruise_ship female first_porn_of_franchise frozen historical_event iceberg inanimate looking_at_viewer male mast nature night no_humans ocean outside parody penis personification rape ship smokestack tear testicles titanic uncensored water what
2boys anal arm_support artist_request bent_over bulldog_position character_request doggy_style_position domination facial_hair fine_art forced forced_yaoi from_behind gay gun hat historical_event history human human_only humiliation male male/male male_on_male male_only male_pubic_hair male_rape_victim military military_uniform mustache nihonga old parody peaked_cap penis personification police print public_domain rape rifle sex shunga soldier spoils_of_war straight_hair sword traditional translated ukiyo-e uncensored uniform war weapon yaoi
2boys anal arm_support artist_request bent_over bulldog_position character_request doggy_style_position domination facial_hair fine_art forced forced_yaoi from_behind gay gun hat historical_event history human human_only humiliation male male/male male_on_male male_only male_pubic_hair male_rape_victim military military_uniform mustache nihonga old parody peaked_cap penis personification police print public_domain rape rifle sex shunga soldier spoils_of_war straight_hair sword traditional translated ukiyo-e uncensored uniform war weapon yaoi