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1920s

1920s 2024 anthro areola armwear biped black_body black_clothing black_hair black_legwear black_markings black_nose black_stockings blush bodily_fluids bottle bottomwear breasts canid canine clothed clothed_sex clothing container countershade_face countershade_torso countershading dipstick_tail domestic_cat dress dress_shirt drunk duo elbow_gloves eye_roll eyebrows facial_hair facial_markings felid feline felis female female_penetrated fluffy fluffy_tail footwear fox genital_fluids genitals gloves hair hait handwear head_markings heart_symbol hi_res holding_bottle holding_container holding_glass holding_object humanoid_genitalia humanoid_penis hybrid ivy_pepper kandlin lackadaisy legwear looking_pleasured male male/female male_penetrating male_penetrating_female mammal markings mask_(marking) moustache multicolored_body nipples no_bra open_mouth pants partially_clothed penetration penile penile_penetration penis penis_in_pussy pink_nose plantigrade procyonid pussy pussy_juice_on_penis raccoon raised_leg rick2tails ring_(marking) ringed_tail sex shirt short_hair simple_background stockings striped_markings striped_tail stripes substance_intoxication suit sweat tail tail_markings teeth thigh_highs tongue topwear two_tone_body vaginal_fluids vaginal_penetration white_background white_body white_clothing white_countershading white_gloves white_handwear white_markings yellow_body yellow_clothing yellow_dress
1920s 2024 anthro areola armwear biped black_body black_clothing black_hair black_legwear black_markings black_nose black_stockings blush bodily_fluids bottle bottomwear breasts canid canine clothed clothed_sex clothing container countershade_face countershade_torso countershading dipstick_tail domestic_cat dress dress_shirt drunk duo elbow_gloves eye_roll eyebrows facial_hair facial_markings felid feline felis female female_penetrated fluffy fluffy_tail footwear fox genital_fluids genitals gloves hair hait handwear head_markings heart_symbol hi_res holding_bottle holding_container holding_glass holding_object humanoid_genitalia humanoid_penis hybrid ivy_pepper kandlin lackadaisy legwear looking_pleasured male male/female male_penetrating male_penetrating_female mammal markings mask_(marking) moustache multicolored_body nipples no_bra open_mouth pants partially_clothed penetration penile penile_penetration penis penis_in_pussy pink_nose plantigrade procyonid pussy pussy_juice_on_penis raccoon raised_leg rick2tails ring_(marking) ringed_tail sex shirt short_hair simple_background stockings striped_markings striped_tail stripes substance_intoxication suit sweat tail tail_markings teeth thigh_highs tongue topwear two_tone_body vaginal_fluids vaginal_penetration white_background white_body white_clothing white_countershading white_gloves white_handwear white_markings yellow_body yellow_clothing yellow_dress
1920s 3/4_view anthro anthro_cat anthro_only anthropomorphic black_and_white_fur black_fur black_nose black_pupils blank_expression blush_lines blushing boner cat_tail catboy character_name clawed_fingers domestic_cat erect_penis erection exposing_self felid feline full_color furry furry_only gentleman glans glasses goatene green_eyes green_sclera half_dressed half_naked hi_res high_socks humanoid_genitalia humanoid_hands humanoid_penis kneeling lackadaisy male_only mordecai_heller naughtybassard no_visible_balls no_visible_nipples pants_pull partially_retracted_foreskin partially_visible_genitals partially_visible_penis penis penis_peek penis_through_leghole pink_penis pinup practically_nude round_glasses simple_background sitting_on_knees sock_garters socks solo_male tagme tail thick_penis torquewintress tuxedo_cat two_tone_fur uncensored uncensored_penis uncircumcised uncircumcised_penis underwear underwear_aside underwear_pull veiny_penis webcomic webcomic_character white_fur white_underwear
1920s 3/4_view anthro anthro_cat anthro_only anthropomorphic black_and_white_fur black_fur black_nose black_pupils blank_expression blush_lines blushing boner cat_tail catboy character_name clawed_fingers domestic_cat erect_penis erection exposing_self felid feline full_color furry furry_only gentleman glans glasses goatene green_eyes green_sclera half_dressed half_naked hi_res high_socks humanoid_genitalia humanoid_hands humanoid_penis kneeling lackadaisy male_only mordecai_heller naughtybassard no_visible_balls no_visible_nipples pants_pull partially_retracted_foreskin partially_visible_genitals partially_visible_penis penis penis_peek penis_through_leghole pink_penis pinup practically_nude round_glasses simple_background sitting_on_knees sock_garters socks solo_male tagme tail thick_penis torquewintress tuxedo_cat two_tone_fur uncensored uncensored_penis uncircumcised uncircumcised_penis underwear underwear_aside underwear_pull veiny_penis webcomic webcomic_character white_fur white_underwear
1920s 2024 angry_face animal_humanoid anthro artist_name artist_signature big_breasts big_hat big_thighs black_background black_hat bouncing_breasts breasts canid canine cigar cigar_in_mouth cigarette cigarette_in_mouth clothed clothing comic_style commission countershade_face countershade_torso countershading digital_media_(artwork) finger_on_trigger firing_weapon fishnet_clothing fishnet_legwear fox fox_ears fox_girl gangster grainy hat hi_res holding_object holding_weapon legwear long_ears machine_gun mad mafia mammal mammal_humanoid motion_lines multicolored_body multicolored_fur onomatopoeia orange_body orange_fur ranged_weapon recoil red_eyes shooting shooting_gun showing_teeth signature smoking smug_face sound_effects tansau thick_thighs thighs thunder_thighs tommy_gun two_tone_fur weapon white_body white_fur wide_brim_hat
1920s 2024 angry_face animal_humanoid anthro artist_name artist_signature big_breasts big_hat big_thighs black_background black_hat bouncing_breasts breasts canid canine cigar cigar_in_mouth cigarette cigarette_in_mouth clothed clothing comic_style commission countershade_face countershade_torso countershading digital_media_(artwork) finger_on_trigger firing_weapon fishnet_clothing fishnet_legwear fox fox_ears fox_girl gangster grainy hat hi_res holding_object holding_weapon legwear long_ears machine_gun mad mafia mammal mammal_humanoid motion_lines multicolored_body multicolored_fur onomatopoeia orange_body orange_fur ranged_weapon recoil red_eyes shooting shooting_gun showing_teeth signature smoking smug_face sound_effects tansau thick_thighs thighs thunder_thighs tommy_gun two_tone_fur weapon white_body white_fur wide_brim_hat
1920s 2024 black_and_white brown_eyes brown_hair chesshire cleavage clothed flapper fully_clothed gender_transformation glasses headband high_heels microphone mtf_transformation necklace new_year plaid reality_change reality_warping short_hair short_hair_female smartphone solo solo_focus surprised surprised_expression tagme time_travel transformation transformation_through_technology
1920s 2024 black_and_white brown_eyes brown_hair chesshire cleavage clothed flapper fully_clothed gender_transformation glasses headband high_heels microphone mtf_transformation necklace new_year plaid reality_change reality_warping short_hair short_hair_female smartphone solo solo_focus surprised surprised_expression tagme time_travel transformation transformation_through_technology
1920s 2girls ass bondage bottomless femdom patrick_rocca torture_chamber traditional_media_(artwork) vintage wooden_horse yuri
1920s 2girls ass bondage bottomless femdom patrick_rocca torture_chamber traditional_media_(artwork) vintage wooden_horse yuri
1920s 1boy 1girls aether_(genshin_impact) alternate_timeline blonde_hair blue_eyes blue_hair comic couple couple_(romantic) crossdressing_female dialogue fedora female genshin_impact history jacket_vest kinkymation text yelan_(genshin_impact)
1920s 1boy 1girls aether_(genshin_impact) alternate_timeline blonde_hair blue_eyes blue_hair comic couple couple_(romantic) crossdressing_female dialogue fedora female genshin_impact history jacket_vest kinkymation text yelan_(genshin_impact)
1920s 1boy1girl 2021 ashily_(trevorsgaming) ass big_balls big_breasts big_penis black black_and_white breasts bubble cartoony daniel_(trevorsgaming) digital_art digital_media digital_media_(artwork) dress eyes fat female gloves grayscale greyscale hair handwear heavy hips human hyper_balls hyper_penis legs monochrome nipples onyx_twilight onyxtwilight_(artist) pale-skinned_female retro_artstyle rubber_hose rubberhose signed skin thick thighs thunder title_card toony top vein veiny veiny_penis vintage wide_hips wife_and_husband
1920s 1boy1girl 2021 ashily_(trevorsgaming) ass big_balls big_breasts big_penis black black_and_white breasts bubble cartoony daniel_(trevorsgaming) digital_art digital_media digital_media_(artwork) dress eyes fat female gloves grayscale greyscale hair handwear heavy hips human hyper_balls hyper_penis legs monochrome nipples onyx_twilight onyxtwilight_(artist) pale-skinned_female retro_artstyle rubber_hose rubberhose signed skin thick thighs thunder title_card toony top vein veiny veiny_penis vintage wide_hips wife_and_husband
<3 1920s 1928 1929 20s 20th_century 2_horns 2d 4:3 5_fingers ? accidentally_gay age_difference alarm_clock ambiguous_gender anal anal_penetration ancient_art animated annoyed anonymous_artist areola arm_support aroused arthropod asinus avian balls beach beckoning becoming_erect becoming_flaccid bestiality better_version_at_source big_balls big_penis binoculars bird black_and_white black_background black_bars black_border black_screen_roulette blank_thumbnail blinking blowing_kiss bodily_fluids border bottomwear bovid bovid_horn bovine bovine_horn bracelet breast_lick breast_milking breast_play breast_squeeze breast_sucking breasts butt cactus canid canine canis cattle circumcised clock clothed clothing cloud cock_and_ball_torture collaboration crab crustacean decapoda detachable detachable_penis dialogue digitigrade dildo dildo_in_ass dildo_in_pussy dildo_insertion dipteran doggy_style domestic_dog donkey drinking_milk duo_focus english_text entwined_tails equid equine erect_nipples erection eveready_harton eveready_harton_in_buried_treasure exclamation_point eye_roll eyebrows eyes_closed facial_hair fellatio female female_on_human female_penetrated fence feral feral_on_feral feral_penetrated feral_penetrating feral_penetrating_feral fingers fisting flaccid fleischer_style_toon flexible_penis footwear forced from_behind_position from_front_position frottage furrowed_eyebrows genital_torture genitals gesture glans glory_hole grainy group gun hair hand_on_breast hand_on_own_breasts happy hat headgear headwear high_heels holding_breast hooves horn huge_penis human human_focus human_on_feral human_on_human human_penetrated human_penetrating human_penetrating_female human_penetrating_feral human_penetrating_human humanoid_genitalia humanoid_penis humanoid_pussy humor insect interspecies intraspecies island jewelry jumping kissing lactating lactation larger_penetrated laugh leaning leaning_back leggings legwear licking line_art living_penis long_playtime long_tongue longer_than_30_seconds longer_than_3_minutes longer_than_5_minutes longer_than_one_minute looking_pleasured lost_my_keys low_res lying malacostracan male male/ambiguous male/female male/male male_focus male_on_bottom male_on_feral male_on_top male_penetrated male_penetrating male_penetrating_female male_penetrating_feral male_penetrating_male mammal marine masturbation max_fleischer missionary_position monochrome mostly_clothed mostly_nude mountain_range mp4 mustache nipple_fetish nipple_lick nipple_play nipple_suck nipples no_sound non-mammal_balls not_furry_focus nude object_in_pussy old_toon older_penetrated on_back on_bottom on_top open_mouth oral outside outside_masturbation outside_sex pain pants penetration penile penile_penetration penis penis_bite penis_in_ass penis_in_pussy penis_kissing penis_lick penis_slap penis_through_fly perching_position pile pivoted_ears plant plantigrade poking_out prehensile_penis prehensile_tongue pubes pubic_hair public public_domain public_sex pussy raised_tail ranged_weapon rape reptile rock running sand scalie scanlines seaside sentient_penis serpentine sex sex_toy sex_toy_in_ass sex_toy_in_pussy sex_toy_insertion shadow shirt shoes shorts simple_background sitting size_difference slap small_breasts smoke snake solo solo_focus sombrero spot_shadow spread_legs spreading standing stretched_penis stuck_penis sucking surprise_buttsex swordfight tail_coil tank_top text title_card tongue tongue_on_breast tongue_out too_many_tags toony topwear toying_self traditional_media_(artwork) tree umbrella unicycle unknown_artist urethra vaginal vaginal_fisting vaginal_masturbation vaginal_penetration video voyeur wagging_finger walking weapon webm white_text wide_eyed yaoi yawn younger_dom_older_sub zoophilia
<3 1920s 1928 1929 20s 20th_century 2_horns 2d 4:3 5_fingers ? accidentally_gay age_difference alarm_clock ambiguous_gender anal anal_penetration ancient_art animated annoyed anonymous_artist areola arm_support aroused arthropod asinus avian balls beach beckoning becoming_erect becoming_flaccid bestiality better_version_at_source big_balls big_penis binoculars bird black_and_white black_background black_bars black_border black_screen_roulette blank_thumbnail blinking blowing_kiss bodily_fluids border bottomwear bovid bovid_horn bovine bovine_horn bracelet breast_lick breast_milking breast_play breast_squeeze breast_sucking breasts butt cactus canid canine canis cattle circumcised clock clothed clothing cloud cock_and_ball_torture collaboration crab crustacean decapoda detachable detachable_penis dialogue digitigrade dildo dildo_in_ass dildo_in_pussy dildo_insertion dipteran doggy_style domestic_dog donkey drinking_milk duo_focus english_text entwined_tails equid equine erect_nipples erection eveready_harton eveready_harton_in_buried_treasure exclamation_point eye_roll eyebrows eyes_closed facial_hair fellatio female female_on_human female_penetrated fence feral feral_on_feral feral_penetrated feral_penetrating feral_penetrating_feral fingers fisting flaccid fleischer_style_toon flexible_penis footwear forced from_behind_position from_front_position frottage furrowed_eyebrows genital_torture genitals gesture glans glory_hole grainy group gun hair hand_on_breast hand_on_own_breasts happy hat headgear headwear high_heels holding_breast hooves horn huge_penis human human_focus human_on_feral human_on_human human_penetrated human_penetrating human_penetrating_female human_penetrating_feral human_penetrating_human humanoid_genitalia humanoid_penis humanoid_pussy humor insect interspecies intraspecies island jewelry jumping kissing lactating lactation larger_penetrated laugh leaning leaning_back leggings legwear licking line_art living_penis long_playtime long_tongue longer_than_30_seconds longer_than_3_minutes longer_than_5_minutes longer_than_one_minute looking_pleasured lost_my_keys low_res lying malacostracan male male/ambiguous male/female male/male male_focus male_on_bottom male_on_feral male_on_top male_penetrated male_penetrating male_penetrating_female male_penetrating_feral male_penetrating_male mammal marine masturbation max_fleischer missionary_position monochrome mostly_clothed mostly_nude mountain_range mp4 mustache nipple_fetish nipple_lick nipple_play nipple_suck nipples no_sound non-mammal_balls not_furry_focus nude object_in_pussy old_toon older_penetrated on_back on_bottom on_top open_mouth oral outside outside_masturbation outside_sex pain pants penetration penile penile_penetration penis penis_bite penis_in_ass penis_in_pussy penis_kissing penis_lick penis_slap penis_through_fly perching_position pile pivoted_ears plant plantigrade poking_out prehensile_penis prehensile_tongue pubes pubic_hair public public_domain public_sex pussy raised_tail ranged_weapon rape reptile rock running sand scalie scanlines seaside sentient_penis serpentine sex sex_toy sex_toy_in_ass sex_toy_in_pussy sex_toy_insertion shadow shirt shoes shorts simple_background sitting size_difference slap small_breasts smoke snake solo solo_focus sombrero spot_shadow spread_legs spreading standing stretched_penis stuck_penis sucking surprise_buttsex swordfight tail_coil tank_top text title_card tongue tongue_on_breast tongue_out too_many_tags toony topwear toying_self traditional_media_(artwork) tree umbrella unicycle unknown_artist urethra vaginal vaginal_fisting vaginal_masturbation vaginal_penetration video voyeur wagging_finger walking weapon webm white_text wide_eyed yaoi yawn younger_dom_older_sub zoophilia
1920s 1girls black_dress blonde blonde_hair breasts breasts_out bush daisy_buchanan eyelashes female female_only hackman hairy_pussy headband pubic_hair retro short_hair smoking solo the_great_gatsby
1920s 1girls black_dress blonde blonde_hair breasts breasts_out bush daisy_buchanan eyelashes female female_only hackman hairy_pussy headband pubic_hair retro short_hair smoking solo the_great_gatsby
1920s 1921 20th_century armand_rassenfosse black_and_white bookplate duo female fictional_interracial fine_art hooves human latin_text low_res male mammal mastery_position monochrome monster obscured_penetration public_domain riding riding_penis satyr sex simple_background sitting straight straight_hair tagme text
1920s 1921 20th_century armand_rassenfosse black_and_white bookplate duo female fictional_interracial fine_art hooves human latin_text low_res male mammal mastery_position monochrome monster obscured_penetration public_domain riding riding_penis satyr sex simple_background sitting straight straight_hair tagme text
1920s 1928 1929 1boy 1boy1girl 1girls 20th_century 2d animated cloaca eveready_harton_in_buried_treasure female feral feral_on_feral feral_only kissing kissing_while_penetrated loop lowres male monochrome penetration public_domain reptile shaky_screen snake straight tail traditional_media_(artwork) vintage wrapped_around_another wrapped_tail zoophilia
1920s 1928 1929 1boy 1boy1girl 1girls 20th_century 2d animated cloaca eveready_harton_in_buried_treasure female feral feral_on_feral feral_only kissing kissing_while_penetrated loop lowres male monochrome penetration public_domain reptile shaky_screen snake straight tail traditional_media_(artwork) vintage wrapped_around_another wrapped_tail zoophilia
1920s 1928 1929 1boy1girl 20th_century 2d animated bush dicksucking_creature eveready_harton_in_buried_treasure loop lowres penis penis_on_pussy pubic_hair public_domain pussy pussy_with_mouth pussyjob shaky_screen traditional_media_(artwork) unusual_anatomy unusual_genitalia unusual_pussy vagina vintage
1920s 1928 1929 1boy1girl 20th_century 2d animated bush dicksucking_creature eveready_harton_in_buried_treasure loop lowres penis penis_on_pussy pubic_hair public_domain pussy pussy_with_mouth pussyjob shaky_screen traditional_media_(artwork) unusual_anatomy unusual_genitalia unusual_pussy vagina vintage
1920s 1928 1929 20th_century 2boys 2d animated balls duo eveready_harton_in_buried_treasure humor lowres male male_focus male_only monochrome monophallia penis penis_body penis_creature penis_head public_domain traditional_media_(artwork) vintage
1920s 1928 1929 20th_century 2boys 2d animated balls duo eveready_harton_in_buried_treasure humor lowres male male_focus male_only monochrome monophallia penis penis_body penis_creature penis_head public_domain traditional_media_(artwork) vintage