20th_century best from all time

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20th century

1940 1940s 1girls 20th_century 2d 4:3 ancient_furry_art animated anthro anthrofied bad_metadata breaking_the_fourth_wall breasts butt canonical_scene cartoon censor_bar censored clothing cross_country_detours dancing desert female female_focus female_only feral feral_to_anthro fourth_wall fourth_wall_broken frame_by_frame johnny_johnsen lizard long_playtime looking_at_viewer looney_tunes low_res morphing mp4 music narration non-mammal_breasts official_art performance performing public_domain reptile rita_skopt rotoscoping scalie scalie_female scalie_only skinsuit softcore solo solo_female song sound striptease tex_avery throwing_clothing tight_clothing traditional_media_(artwork) transformation undressing video voice_acted warner_brothers
1940 1940s 1girls 20th_century 2d 4:3 ancient_furry_art animated anthro anthrofied bad_metadata breaking_the_fourth_wall breasts butt canonical_scene cartoon censor_bar censored clothing cross_country_detours dancing desert female female_focus female_only feral feral_to_anthro fourth_wall fourth_wall_broken frame_by_frame johnny_johnsen lizard long_playtime looking_at_viewer looney_tunes low_res morphing mp4 music narration non-mammal_breasts official_art performance performing public_domain reptile rita_skopt rotoscoping scalie scalie_female scalie_only skinsuit softcore solo solo_female song sound striptease tex_avery throwing_clothing tight_clothing traditional_media_(artwork) transformation undressing video voice_acted warner_brothers
1990s 1998 1futa 1girl1futa 1girls 20th_century blush bra breasts closed_eyes dated female from_behind futa_on_female futanari g-taste glasses intersex large_breasts lingerie necktie older_futanari older_penetrating_younger open_mouth panties panty_pull pink_panties school_uniform short_hair skirt sweat teacher teacher_and_student underwear younger_female
1990s 1998 1futa 1girl1futa 1girls 20th_century blush bra breasts closed_eyes dated female from_behind futa_on_female futanari g-taste glasses intersex large_breasts lingerie necktie older_futanari older_penetrating_younger open_mouth panties panty_pull pink_panties school_uniform short_hair skirt sweat teacher teacher_and_student underwear younger_female
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 90s animated breast_grab breasts brown-tinted_eyewear censored chikan cool_devices denim denim_shorts embarrassed exhibitionism female fingering fingering_pussy fondling forced gif glasses groping groping_breasts groping_from_behind human low_res lowres midriff molestation nutech_digital pink_hair pussy rape resisting rina_yuki_(cool_devices) shirt_lift short_hair shorts standing sunglasses tinted_eyewear train train_interior uncensored
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 90s animated breast_grab breasts brown-tinted_eyewear censored chikan cool_devices denim denim_shorts embarrassed exhibitionism female fingering fingering_pussy fondling forced gif glasses groping groping_breasts groping_from_behind human low_res lowres midriff molestation nutech_digital pink_hair pussy rape resisting rina_yuki_(cool_devices) shirt_lift short_hair shorts standing sunglasses tinted_eyewear train train_interior uncensored
1990s 1999 20th_century alien alien_girl arica armpits arms_behind_head arms_up back background bald barefoot blanket bodily_fluids bottomless bottomless_female breasts breasts_outside brown_hair closed_eyes clothing clothing_aside collar completely_nude curtains dancers'_pit enslaved_royal eyes feet female female_only forced front_view gloves hair hairy_pussy hands_behind_head harem horn human humanoid indoors jabba's_palace kneeling light-skinned_female light_skin loincloth long_gloves long_hair lyn_me mara_jade mara_jade_skywalker miravi multiple_girls nipples nude on_floor open_eyes partially_clothed pillow princess princess_leia_organa pubic_hair pussy_juice pussy_juice_drip rear_view red_hair red_light return_of_the_jedi return_of_the_jedi_(radio) rystall_sant sad see-through sex_slave signature sitting slave slave_leia slavegirl small_breasts standing star_wars tatooine theelin thin_waist tiptoes topless topless_female towel twi'lek wraps
1990s 1999 20th_century alien alien_girl arica armpits arms_behind_head arms_up back background bald barefoot blanket bodily_fluids bottomless bottomless_female breasts breasts_outside brown_hair closed_eyes clothing clothing_aside collar completely_nude curtains dancers'_pit enslaved_royal eyes feet female female_only forced front_view gloves hair hairy_pussy hands_behind_head harem horn human humanoid indoors jabba's_palace kneeling light-skinned_female light_skin loincloth long_gloves long_hair lyn_me mara_jade mara_jade_skywalker miravi multiple_girls nipples nude on_floor open_eyes partially_clothed pillow princess princess_leia_organa pubic_hair pussy_juice pussy_juice_drip rear_view red_hair red_light return_of_the_jedi return_of_the_jedi_(radio) rystall_sant sad see-through sex_slave signature sitting slave slave_leia slavegirl small_breasts standing star_wars tatooine theelin thin_waist tiptoes topless topless_female towel twi'lek wraps
1990s 1990s_(style) 1998 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 2d_animation 90s abandoned_building age_difference animated ankle_socks anklehighs ankles_tied arms_above_head arms_tied_above_head black_hair breast_grab breasts brown_hair clothed_male elf_(company) exposed_breasts feet_tied female gif glasses groping_breasts groping_from_behind hair_ribbon hands_tied hi_res highres isaku itou_isaku long_hair male medium_breasts mikihara_akemi over_480p panties_down penetration pink_pineapple pink_socks pussy rape restrained retro_artstyle rope_around_ankle sex shirt_up skirt_up socks tennis_uniform uncensored vaginal_rape
1990s 1990s_(style) 1998 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 2d_animation 90s abandoned_building age_difference animated ankle_socks anklehighs ankles_tied arms_above_head arms_tied_above_head black_hair breast_grab breasts brown_hair clothed_male elf_(company) exposed_breasts feet_tied female gif glasses groping_breasts groping_from_behind hair_ribbon hands_tied hi_res highres isaku itou_isaku long_hair male medium_breasts mikihara_akemi over_480p panties_down penetration pink_pineapple pink_socks pussy rape restrained retro_artstyle rope_around_ankle sex shirt_up skirt_up socks tennis_uniform uncensored vaginal_rape
1girls 20th_century areolae art_frahm bed blonde_hair blush breasts female female_only high_heels lipstick looking_at_viewer negligee nightgown nipples original painting_(artwork) pinup pinup_girl see-through smile solo straight_hair traditional_media_(artwork) vintage
1girls 20th_century areolae art_frahm bed blonde_hair blush breasts female female_only high_heels lipstick looking_at_viewer negligee nightgown nipples original painting_(artwork) pinup pinup_girl see-through smile solo straight_hair traditional_media_(artwork) vintage
1950s 1953 1girls 20th_century 50s areolae blonde_hair breasts choker female female_only gil_elvgren holding_object lipstick looking_at_viewer nipples nude original painting_(artwork) pinup pinup_girl smile solo straight_hair text traditional_media_(artwork) vintage
1950s 1953 1girls 20th_century 50s areolae blonde_hair breasts choker female female_only gil_elvgren holding_object lipstick looking_at_viewer nipples nude original painting_(artwork) pinup pinup_girl smile solo straight_hair text traditional_media_(artwork) vintage
1boy 1girls 20th_century after_sex aged_up annie_leonhardt armin_arlert attack_on_titan bedroom blonde_female blonde_female/blonde_male blonde_hair covering female hair_down hand_on_back hand_on_waist looking_at_partner male male/female nude on_bed resting sheets shingeki_no_kyojin short_hair_female sleeping sleeping_on_bed smiling_at_partner straight suggestive time_skip under_sheets wholesome
1boy 1girls 20th_century after_sex aged_up annie_leonhardt armin_arlert attack_on_titan bedroom blonde_female blonde_female/blonde_male blonde_hair covering female hair_down hand_on_back hand_on_waist looking_at_partner male male/female nude on_bed resting sheets shingeki_no_kyojin short_hair_female sleeping sleeping_on_bed smiling_at_partner straight suggestive time_skip under_sheets wholesome
1990s 1999 1girls 20th_century animal_penis bent_over bestiality blush bondage boots bound_arms breasts brown_eyes brown_hair clothed_sex clothing doggy_style dress dress_lift drooling female female_on_feral feral feral_on_female feral_on_human from_behind fur gundam horse horse_penis horsecock human human_on_feral interspecies light-skinned_female light_skin nipples no_bra open_mouth penis rape rope saliva sex shadow short_hair size_difference sochie_heim solo sweat turn_a_gundam youkai_ankake zoophilia
1990s 1999 1girls 20th_century animal_penis bent_over bestiality blush bondage boots bound_arms breasts brown_eyes brown_hair clothed_sex clothing doggy_style dress dress_lift drooling female female_on_feral feral feral_on_female feral_on_human from_behind fur gundam horse horse_penis horsecock human human_on_feral interspecies light-skinned_female light_skin nipples no_bra open_mouth penis rape rope saliva sex shadow short_hair size_difference sochie_heim solo sweat turn_a_gundam youkai_ankake zoophilia
1990s 1996 1boy 1girls 20th_century anna_marie female gambit headband male marvel marvel_comics rogue_(x-men) senseixxx sex straight_hair x-men
1990s 1996 1boy 1girls 20th_century anna_marie female gambit headband male marvel marvel_comics rogue_(x-men) senseixxx sex straight_hair x-men
1990s 1990s_(style) 1998 1boy 1girls 20th_century 2d 2d_(artwork) 2d_animation 3boys 90s animated areola areolae ass ass_fondling ass_grab black_hair blowjob blush boobs breast_fondle breast_fondling_under_clothes breasts bushes clothed clothed_male cum cum_on_face dark_blue_hair deceit desert_island_story_x doggy_style dubbed_version english_dialogue english_voice evil_laugh facial fellatio female forced gangbang gangrape glasses group hairband hands_on_ass hands_on_head hentai hi_res highres island large_breasts long_blue_hair long_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male meganekko moaning mp4 mujintou_monogatari_x night nipples oral oral_sex outdoors palm_tree pink_pineapple privacy rape retro retro_artstyle sex shocked sound spread_legs surprise_gangbang tied_arms tits touko_(mujintou_monogatari_x) tricked video voice_acted yuka_(mujintou_monogatari_x)
1990s 1990s_(style) 1998 1boy 1girls 20th_century 2d 2d_(artwork) 2d_animation 3boys 90s animated areola areolae ass ass_fondling ass_grab black_hair blowjob blush boobs breast_fondle breast_fondling_under_clothes breasts bushes clothed clothed_male cum cum_on_face dark_blue_hair deceit desert_island_story_x doggy_style dubbed_version english_dialogue english_voice evil_laugh facial fellatio female forced gangbang gangrape glasses group hairband hands_on_ass hands_on_head hentai hi_res highres island large_breasts long_blue_hair long_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male meganekko moaning mp4 mujintou_monogatari_x night nipples oral oral_sex outdoors palm_tree pink_pineapple privacy rape retro retro_artstyle sex shocked sound spread_legs surprise_gangbang tied_arms tits touko_(mujintou_monogatari_x) tricked video voice_acted yuka_(mujintou_monogatari_x)
1990s 1996 20th_century animated asian construction_site corpse deadly_sex death desiccated desiccation energy_drain extreme_content female female_death human injuu_kateikyoushi lesson_of_darkness male/female mass_death mass_rape moaning monster multiple_deaths multiple_girls murder outdoors pale_skin party_wipe pink_pineapple public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1990s 1996 20th_century animated asian construction_site corpse deadly_sex death desiccated desiccation energy_drain extreme_content female female_death human injuu_kateikyoushi lesson_of_darkness male/female mass_death mass_rape moaning monster multiple_deaths multiple_girls murder outdoors pale_skin party_wipe pink_pineapple public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1080p 1440x1080 1990s 1997 20th_century 2boys 2d 2girls 90s animated asakawa_kotomi ass_fondling ass_grab beard_stubble bed begging_to_stop black_hair breaking_in captured captured_heroine coercion cunnilingus drool dubbed_version elf_(company) enema enema_syringe english_dialogue english_dub english_voice english_voice_acting female fingering fingering_another forced hands_tied hi_res hiding hiding_under_bed highres hosome_eyes humiliation indoors insult isaku itou_isaku knocking_on_door kogure_kenta long_black_hair long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male male_pervert mp4 older_male older_male_younger_female over_480p pee peeing peeing_female peeing_self pink_hair pink_pineapple retro retro_artstyle sakaki_miyuki saliva socks sound tear tear_streaks tears tongue tongue_kiss tongue_kissing trying_to_escape ugly_man upskirt urinating_female urination urine urine_pool video voice_acted wooden_floor wooden_wall yellow_hair_ribbon yellow_panties younger_female
1080p 1440x1080 1990s 1997 20th_century 2boys 2d 2girls 90s animated asakawa_kotomi ass_fondling ass_grab beard_stubble bed begging_to_stop black_hair breaking_in captured captured_heroine coercion cunnilingus drool dubbed_version elf_(company) enema enema_syringe english_dialogue english_dub english_voice english_voice_acting female fingering fingering_another forced hands_tied hi_res hiding hiding_under_bed highres hosome_eyes humiliation indoors insult isaku itou_isaku knocking_on_door kogure_kenta long_black_hair long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male male_pervert mp4 older_male older_male_younger_female over_480p pee peeing peeing_female peeing_self pink_hair pink_pineapple retro retro_artstyle sakaki_miyuki saliva socks sound tear tear_streaks tears tongue tongue_kiss tongue_kissing trying_to_escape ugly_man upskirt urinating_female urination urine urine_pool video voice_acted wooden_floor wooden_wall yellow_hair_ribbon yellow_panties younger_female
2023 2023s 20th_century alien alien_girl anthro artist_name ass big_ass_(female) big_breasts big_butt black_nose blue_body blue_fur blue_sky_studios blush bodysuit border camel_toe cameltoe clothing curvy_figure digital_media_(artwork) dumptruck_ass dumptruck_butt eyebrows eyelashes female fingers hi_res ice_age_(series) ice_age_collision_course light_blue_body light_blue_fur looking_back mammal nexcoyotlgt purple_bodysuit purple_border purple_eyes purple_eyeshadow rear_view rodent sciurid scrat_spaced_out scratazon scratazon_leader sharp_teeth simple_background skin_tight_suit solo solo_female squirrel_ears squirrel_girl squirrel_tail tail teeth voluptuous wide_hips
2023 2023s 20th_century alien alien_girl anthro artist_name ass big_ass_(female) big_breasts big_butt black_nose blue_body blue_fur blue_sky_studios blush bodysuit border camel_toe cameltoe clothing curvy_figure digital_media_(artwork) dumptruck_ass dumptruck_butt eyebrows eyelashes female fingers hi_res ice_age_(series) ice_age_collision_course light_blue_body light_blue_fur looking_back mammal nexcoyotlgt purple_bodysuit purple_border purple_eyes purple_eyeshadow rear_view rodent sciurid scrat_spaced_out scratazon scratazon_leader sharp_teeth simple_background skin_tight_suit solo solo_female squirrel_ears squirrel_girl squirrel_tail tail teeth voluptuous wide_hips
1941 1girls 20th_century 40s ass ass_focus ass_out bathroom blonde_female blonde_hair blush blushing breasts covering covering_breasts covering_crotch covering_self covering_with_object female female_only footwear gil_elvgren high_heels lipstick looking_at_viewer minimalist_background mirror mirror_reflection naked_footwear nude nude_female original painting_(artwork) pinup pinup1940s pinup_girl pursed_lips realistic red_lips red_lipstick reflection slippers slippers_only solo solo_female straight_hair surprise surprised surprised_expression surprised_face surprised_look towel traditional_art traditional_media traditional_media_(artwork) vintage
1941 1girls 20th_century 40s ass ass_focus ass_out bathroom blonde_female blonde_hair blush blushing breasts covering covering_breasts covering_crotch covering_self covering_with_object female female_only footwear gil_elvgren high_heels lipstick looking_at_viewer minimalist_background mirror mirror_reflection naked_footwear nude nude_female original painting_(artwork) pinup pinup1940s pinup_girl pursed_lips realistic red_lips red_lipstick reflection slippers slippers_only solo solo_female straight_hair surprise surprised surprised_expression surprised_face surprised_look towel traditional_art traditional_media traditional_media_(artwork) vintage
1080p 1990s 1992 1girls 20th_century 4:3 90s animated anime ass big_ass big_breasts black_hair black_underwear bra breasts cleavage club crowd dancer dancing download:_devil's_circuit earrings female female_focus fingerless_gloves garter hoop_earrings hourglass_figure human indoors jiggle jiggling_breasts long_hair madhouse_(studio) medium_breasts mp4 music navel neon_lights nightclub on_stage pale-skinned_female red_lipstick red_nails rose_(flower) screencap solo solo_female sound stage thigh_strap thighs thong very_long_hair video
1080p 1990s 1992 1girls 20th_century 4:3 90s animated anime ass big_ass big_breasts black_hair black_underwear bra breasts cleavage club crowd dancer dancing download:_devil's_circuit earrings female female_focus fingerless_gloves garter hoop_earrings hourglass_figure human indoors jiggle jiggling_breasts long_hair madhouse_(studio) medium_breasts mp4 music navel neon_lights nightclub on_stage pale-skinned_female red_lipstick red_nails rose_(flower) screencap solo solo_female sound stage thigh_strap thighs thong very_long_hair video
1990s 1998 1girls 20th_century arabian big_breasts black_hair breasts dark-skinned_female dark_skin female female_only kevin_j_taylor nipples solo
1990s 1998 1girls 20th_century arabian big_breasts black_hair breasts dark-skinned_female dark_skin female female_only kevin_j_taylor nipples solo
1990s 1999 1girls 20th_century bat breasts breasts_out cape clothes color disney disney_villains elf_(artist) fairy female female_only horns human maleficent nipple_chain nipple_piercing nipples partially_clothed pencil_(artwork) piercing sleeping_beauty_(1959_film) solo villain villainess witch yellow_sclera
1990s 1999 1girls 20th_century bat breasts breasts_out cape clothes color disney disney_villains elf_(artist) fairy female female_only horns human maleficent nipple_chain nipple_piercing nipples partially_clothed pencil_(artwork) piercing sleeping_beauty_(1959_film) solo villain villainess witch yellow_sclera