20th_century best from all time

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20th century

1950s 1954 1girls 20th_century 50s blonde_hair breasts dress female female_only high_heels leg_up lipstick painting_(artwork) peter_driben pinup pinup_girl smile solo stockings straight_hair thick_thighs thighhighs titter traditional_media_(artwork) vintage
1950s 1954 1girls 20th_century 50s blonde_hair breasts dress female female_only high_heels leg_up lipstick painting_(artwork) peter_driben pinup pinup_girl smile solo stockings straight_hair thick_thighs thighhighs titter traditional_media_(artwork) vintage
1girl 1girls 2024 2024s 20th_century 20th_century_fox 20th_century_studios absurd_res absurdres antennae_(anatomy) anthro arm_under_breasts ass big_ass big_butt blue_eyes blue_sky_studios breasts brown_body brown_fur butt digital_drawing_(artwork) digital_media_(artwork) eyelids fangs female female_focus female_only food fruit fur fur_markings furry furry_female heart_symbol hi_res huge_ass huge_butt ice_age_(film) ice_age_(series) ice_age_dawn_of_the_dinosaurs looking_at_viewer looking_back mammal markings milkshoba narrowed_eyes nut_(fruit) plant rear_view rodent saber-toothed_squirrel sabertooth_(anatomy) sciurid scratte_(ice_age) shaking_ass shaking_butt short_stack shortstack sitting solo solo_female solo_focus tail teeth text thick thick_ass thick_butt thick_thighs thighs
1girl 1girls 2024 2024s 20th_century 20th_century_fox 20th_century_studios absurd_res absurdres antennae_(anatomy) anthro arm_under_breasts ass big_ass big_butt blue_eyes blue_sky_studios breasts brown_body brown_fur butt digital_drawing_(artwork) digital_media_(artwork) eyelids fangs female female_focus female_only food fruit fur fur_markings furry furry_female heart_symbol hi_res huge_ass huge_butt ice_age_(film) ice_age_(series) ice_age_dawn_of_the_dinosaurs looking_at_viewer looking_back mammal markings milkshoba narrowed_eyes nut_(fruit) plant rear_view rodent saber-toothed_squirrel sabertooth_(anatomy) sciurid scratte_(ice_age) shaking_ass shaking_butt short_stack shortstack sitting solo solo_female solo_focus tail teeth text thick thick_ass thick_butt thick_thighs thighs
1990s 1999 1girls 20th_century 2d animal_ears bikini black_hair bow breasts brown_hair cat_ears cleavage collar gloves high_cut highleg inoue_takuya large_breasts long_hair nekomimi purple_eyes shiny solo striped stripes swimsuit tail thick_thighs tiger_print tiger_stripes violet_eyes
1990s 1999 1girls 20th_century 2d animal_ears bikini black_hair bow breasts brown_hair cat_ears cleavage collar gloves high_cut highleg inoue_takuya large_breasts long_hair nekomimi purple_eyes shiny solo striped stripes swimsuit tail thick_thighs tiger_print tiger_stripes violet_eyes
1990s 1993 20th_century 2girls against_wall alley alleyway amagi_kei ami_mizuno bishoujo_senshi_sailor_moon blonde_hair blue_hair blush boots bow brick_wall clothing dated dripping_pussy earrings elbow_gloves embarrassed female female_only fingering gloves heel_boots heels high_heel_boots hourglass_figure looking_at_another looking_back looking_down medium_breasts multiple_girls night open_mouth panties pussy_juice ribbon sailor_fuku sailor_mercury sailor_moon signature sitting skirt skirt_lift small_breasts standing sweat sweatdrop sweating usagi_tsukino wet_panties wet_pussy white_panties yuri
1990s 1993 20th_century 2girls against_wall alley alleyway amagi_kei ami_mizuno bishoujo_senshi_sailor_moon blonde_hair blue_hair blush boots bow brick_wall clothing dated dripping_pussy earrings elbow_gloves embarrassed female female_only fingering gloves heel_boots heels high_heel_boots hourglass_figure looking_at_another looking_back looking_down medium_breasts multiple_girls night open_mouth panties pussy_juice ribbon sailor_fuku sailor_mercury sailor_moon signature sitting skirt skirt_lift small_breasts standing sweat sweatdrop sweating usagi_tsukino wet_panties wet_pussy white_panties yuri
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 90s animated breast_grab breasts chikan cool_devices denim denim_shorts embarrassed 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 rina_yuki_(cool_devices) shirt_lift short_hair shorts standing sunglasses train train_interior uncensored
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 90s animated breast_grab breasts chikan cool_devices denim denim_shorts embarrassed 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 rina_yuki_(cool_devices) shirt_lift short_hair shorts standing sunglasses train train_interior uncensored
1990s 1998 1girls 20th_century 3girls art_of_fighting big_breasts blonde_hair blue_eyes breast_grab breasts brown_hair fatal_fury female female_only fingerless_gloves french_girl hair hands_on_breasts happy headband hourglass_figure japanese_girl king_(snk) king_of_fighters lipstick long_hair mai_shiranui medium_breasts nipples_covered partially_clothed perky_breasts ponytail pussy_peek saigado short short_hair smile snk unbuttoned_shirt unzipped_pants voluptuous yuri_sakazaki
1990s 1998 1girls 20th_century 3girls art_of_fighting big_breasts blonde_hair blue_eyes breast_grab breasts brown_hair fatal_fury female female_only fingerless_gloves french_girl hair hands_on_breasts happy headband hourglass_figure japanese_girl king_(snk) king_of_fighters lipstick long_hair mai_shiranui medium_breasts nipples_covered partially_clothed perky_breasts ponytail pussy_peek saigado short short_hair smile snk unbuttoned_shirt unzipped_pants voluptuous yuri_sakazaki
1girls 20th_century 20th_century_fox 20th_century_studios ai_generated ass athletic athletic_female big_ass big_breasts blue_sky_studios blush breasts completely_nude completely_nude_female curvy curvy_figure cute cute_face detailed dinixdream eyelashes eyeshadow female female_only fit fit_female focus hentai high_quality legs light-skinned_female light_skin linda_gunderson lips lipstick looking_at_viewer makeup mascara mature midriff naked navel nude patreon patreon_username petite pool poolside posing pussy rio_(film) rio_(series) seductive seductive_look slim stable_diffusion standing tagme teenager thick_ass thick_butt thick_thighs thighs young younger_female
1girls 20th_century 20th_century_fox 20th_century_studios ai_generated ass athletic athletic_female big_ass big_breasts blue_sky_studios blush breasts completely_nude completely_nude_female curvy curvy_figure cute cute_face detailed dinixdream eyelashes eyeshadow female female_only fit fit_female focus hentai high_quality legs light-skinned_female light_skin linda_gunderson lips lipstick looking_at_viewer makeup mascara mature midriff naked navel nude patreon patreon_username petite pool poolside posing pussy rio_(film) rio_(series) seductive seductive_look slim stable_diffusion standing tagme teenager thick_ass thick_butt thick_thighs thighs young younger_female
1990s 1999 20th_century a_new_hope astromech_droid boots cheating droid lucasfilm princess_leia_organa r2-d2 shabby_blue source_request star_wars white_boots
1990s 1999 20th_century a_new_hope astromech_droid boots cheating droid lucasfilm princess_leia_organa r2-d2 shabby_blue source_request star_wars white_boots
1990s 1999 1girls 20th_century actress areolae big_breasts bondage breasts carlos_diez celebrity collar costume erect_nipples female female_only garter headdress natalie_portman nipples padme_amidala solo star_wars stockings the_phantom_menace
1990s 1999 1girls 20th_century actress areolae big_breasts bondage breasts carlos_diez celebrity collar costume erect_nipples female female_only garter headdress natalie_portman nipples padme_amidala solo star_wars stockings the_phantom_menace
1990s 1992 1girls 20th_century bishoujo_senshi_sailor_moon clothing cunnilingus daphnia feline female female_only feral feral_on_female feral_on_human fur luna_(sailor_moon) monochrome oral_sex panties sailor_moon skirt tagme tears usagi_tsukino yuri zoophilia
1990s 1992 1girls 20th_century bishoujo_senshi_sailor_moon clothing cunnilingus daphnia feline female female_only feral feral_on_female feral_on_human fur luna_(sailor_moon) monochrome oral_sex panties sailor_moon skirt tagme tears usagi_tsukino yuri zoophilia
1girls 20th_century bikini breasts chair cleavage eyewear_removed female female_only gil_elvgren lipstick looking_at_viewer nail_polish navel original painting_(artwork) pinup pinup_girl smile solo straight_hair sun_lounger sunglasses sunglasses_removed traditional_media_(artwork) vintage wide_hips
1girls 20th_century bikini breasts chair cleavage eyewear_removed female female_only gil_elvgren lipstick looking_at_viewer nail_polish navel original painting_(artwork) pinup pinup_girl smile solo straight_hair sun_lounger sunglasses sunglasses_removed traditional_media_(artwork) vintage wide_hips
20th_century 20th_century_fox 20th_century_studios 80s_hair aliasing angleyne areolae big_areolae big_breasts big_hair big_nipples cleft_of_venus front_view futurama grey_background gynoid jaggy_lines large_areolae metallic_body original_artwork png robot robot_girl shiny_breasts shiny_thighs shoulder_pads solid_color_background solid_colors solo standing thick_thighs voluptuous voluptuous_female weird00d yellow_body yellow_hair
20th_century 20th_century_fox 20th_century_studios 80s_hair aliasing angleyne areolae big_areolae big_breasts big_hair big_nipples cleft_of_venus front_view futurama grey_background gynoid jaggy_lines large_areolae metallic_body original_artwork png robot robot_girl shiny_breasts shiny_thighs shoulder_pads solid_color_background solid_colors solo standing thick_thighs voluptuous voluptuous_female weird00d yellow_body yellow_hair
1950s 1957 1girls 20th_century 50s areolae bed big_breasts breasts canine dog domestic_dog earrings feathers female female_only gil_elvgren kneeling lipstick looking_at_viewer nightie original pillow pinup pinup_girl realistic see-through solo straight_hair thin_waist vintage
1950s 1957 1girls 20th_century 50s areolae bed big_breasts breasts canine dog domestic_dog earrings feathers female female_only gil_elvgren kneeling lipstick looking_at_viewer nightie original pillow pinup pinup_girl realistic see-through solo straight_hair thin_waist vintage
1940s 1946 1girls 20th_century 40s breasts brown_&_bigelow brown_hair cart covering covering_breasts female female_only gil_elvgren high_heels lipstick naked_footwear naked_heels nipples nude nurse painting_(artwork) pinup pinup_girl solo straight_hair traditional_art traditional_media traditional_media_(artwork) vintage
1940s 1946 1girls 20th_century 40s breasts brown_&_bigelow brown_hair cart covering covering_breasts female female_only gil_elvgren high_heels lipstick naked_footwear naked_heels nipples nude nurse painting_(artwork) pinup pinup_girl solo straight_hair traditional_art traditional_media traditional_media_(artwork) vintage
1990s 1998 1boy 20th_century 4:3_aspect_ratio 4girls artist_signature ass blonde_hair blonde_hair_female bondage ceremony chained clothed_male_nude_female cloudy_sky completely_nude_female copyright_symbol druid female grass green_grass human human_only light-skinned_female light_skin long_blonde_hair long_hair long_hair_female multicolored_sky nude nude_female offering outdoor_nudity outdoors pornotopia public_nudity pussy religious restrained ritual sagemonn spread_eagle stationary_restraints stone_circle stonehenge uncensored unseen_female_face unseen_male_face waist_length_hair web_address
1990s 1998 1boy 20th_century 4:3_aspect_ratio 4girls artist_signature ass blonde_hair blonde_hair_female bondage ceremony chained clothed_male_nude_female cloudy_sky completely_nude_female copyright_symbol druid female grass green_grass human human_only light-skinned_female light_skin long_blonde_hair long_hair long_hair_female multicolored_sky nude nude_female offering outdoor_nudity outdoors pornotopia public_nudity pussy religious restrained ritual sagemonn spread_eagle stationary_restraints stone_circle stonehenge uncensored unseen_female_face unseen_male_face waist_length_hair web_address
1990s 1999 20th_century 2girls big_breasts blush boots boots_only breasts closed_eyes comic completely_nude completely_nude_female curvaceous dirty_pair female female/female female_only greyscale headband highres human kei_(dirty_pair) large_breasts long_hair manabe_jouji manga monochrome multiple_girls nipples nude nude_female open_mouth page_43 page_number pubic_hair saliva sex short_hair sweat tomboy tribadism uncensored yuri yuri_(dirty_pair)
1990s 1999 20th_century 2girls big_breasts blush boots boots_only breasts closed_eyes comic completely_nude completely_nude_female curvaceous dirty_pair female female/female female_only greyscale headband highres human kei_(dirty_pair) large_breasts long_hair manabe_jouji manga monochrome multiple_girls nipples nude nude_female open_mouth page_43 page_number pubic_hair saliva sex short_hair sweat tomboy tribadism uncensored yuri yuri_(dirty_pair)
1990s 1995 1boy 20th_century 2girls animated bdsm bdsm_gear blue_hair breasts breasts_out censored chains collar cool_devices cum_in_mouth cum_on_breasts cum_on_face fetish_wear fingering hentai human_furniture multiple_girls nipple_piercing oral pink_hair purple_hair retro rubbing_pussy sex_club sound tagme video whip
1990s 1995 1boy 20th_century 2girls animated bdsm bdsm_gear blue_hair breasts breasts_out censored chains collar cool_devices cum_in_mouth cum_on_breasts cum_on_face fetish_wear fingering hentai human_furniture multiple_girls nipple_piercing oral pink_hair purple_hair retro rubbing_pussy sex_club sound tagme video whip
1girls 20th_century 20th_century_fox 20th_century_studios ai_generated ass athletic athletic_female big_ass big_breasts blue_sky_studios blush breasts completely_nude completely_nude_female curvy curvy_figure cute cute_face detailed dinixdream eyelashes eyeshadow female female_only fit fit_female focus hentai high_quality legs light-skinned_female light_skin linda_gunderson lips lipstick looking_at_viewer makeup mascara mature midriff naked navel nude patreon patreon_username petite pool poolside posing pussy rio_(film) rio_(series) seductive seductive_look slim stable_diffusion standing tagme teenager thick_ass thick_butt thick_thighs thighs young younger_female
1girls 20th_century 20th_century_fox 20th_century_studios ai_generated ass athletic athletic_female big_ass big_breasts blue_sky_studios blush breasts completely_nude completely_nude_female curvy curvy_figure cute cute_face detailed dinixdream eyelashes eyeshadow female female_only fit fit_female focus hentai high_quality legs light-skinned_female light_skin linda_gunderson lips lipstick looking_at_viewer makeup mascara mature midriff naked navel nude patreon patreon_username petite pool poolside posing pussy rio_(film) rio_(series) seductive seductive_look slim stable_diffusion standing tagme teenager thick_ass thick_butt thick_thighs thighs young younger_female