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1930s

1930s 1girls 2012 2boys all_the_way_through anal_penetration anal_sex bisexual bisexual_sandwich bottomless erection fondling_balls hand_on_ass holding_penis large_penis legs_apart legs_up long_penis looking_at_penis nude_female nude_male olive_oyl pants_down pipe popeye popeye_(series) question_mark sex small_breasts tagme tattoo tijuana_bible vaginal_penetration vaginal_sex vintage wimpy
1930s 1girls 2012 2boys all_the_way_through anal_penetration anal_sex bisexual bisexual_sandwich bottomless erection fondling_balls hand_on_ass holding_penis large_penis legs_apart legs_up long_penis looking_at_penis nude_female nude_male olive_oyl pants_down pipe popeye popeye_(series) question_mark sex small_breasts tagme tattoo tijuana_bible vaginal_penetration vaginal_sex vintage wimpy
1930s 1938 1boy 20th_century 2girls animal animal_genitalia animal_penis ass bedroom blonde blonde_female bottomless canid canine canine_genitalia canine_penis canis clothed clothing dog_leash doggy_style domestic_dog dominant_female dominant_feral dominant_male female female_focus female_on_feral femdom feral feral_on_female feral_on_human feral_penetrating from_behind_position group human human_on_feral interspecies julie_delcourt kneeling leash leash_and_collar leash_pull legwear looking_at_another looking_at_partner looking_back looking_down male mammal mounting painting_(artwork) penis pet pink restrained restrained_legs sex smiling smiling_at_partner stockings straight submissive_female submissive_human thigh_high_socks thigh_highs thighhighs threesome traditional_art traditional_media_(artwork) watercolor_(artwork) zoophilia
1930s 1938 1boy 20th_century 2girls animal animal_genitalia animal_penis ass bedroom blonde blonde_female bottomless canid canine canine_genitalia canine_penis canis clothed clothing dog_leash doggy_style domestic_dog dominant_female dominant_feral dominant_male female female_focus female_on_feral femdom feral feral_on_female feral_on_human feral_penetrating from_behind_position group human human_on_feral interspecies julie_delcourt kneeling leash leash_and_collar leash_pull legwear looking_at_another looking_at_partner looking_back looking_down male mammal mounting painting_(artwork) penis pet pink restrained restrained_legs sex smiling smiling_at_partner stockings straight submissive_female submissive_human thigh_high_socks thigh_highs thighhighs threesome traditional_art traditional_media_(artwork) watercolor_(artwork) zoophilia
1930s betty_boop popeye popeye_(series) tagme tijuana_bible vintage
1930s betty_boop popeye popeye_(series) tagme tijuana_bible vintage
1930s anal avian balls bird blackjack_(artist) bottomless canine clothed clothing comic disney donald_duck duck duo english_text half-dressed male mammal older_than_internet oral penis pimp prostitution rhyme text tijuana_bible vintage yaoi
1930s anal avian balls bird blackjack_(artist) bottomless canine clothed clothing comic disney donald_duck duck duo english_text half-dressed male mammal older_than_internet oral penis pimp prostitution rhyme text tijuana_bible vintage yaoi
1930s 1938 1boy 1girls 20th_century all_fours animal_genitalia animal_penis arched_back ass back_arch barely_visible_genitalia bent_over bent_over_chair bottomless canid canine canine_penis canis clothed clothing doggy_style doggy_style_position doggystyle domestic_dog dubious_consent duo enema enema_bulb female feral feral_on_female feral_on_human feral_penetrating feral_penetrating_human footwear from_behind from_behind_position garter garter_straps garters great_dane hands_crossed high_heels human human_on_feral human_penetrated implied_penetration implied_rape interspecies julie_delcourt legwear looking_away looking_away_from_viewer male mammal mounting neutral_expression painting_(artwork) part_of_a_set partially_clothed partially_undressed penetration penis presenting presenting_hindquarters questionable_consent sex shoes spotted_fur stocking_garters stockings straight traditional_art traditional_media_(artwork) vaginal_penetration watercolor_(artwork) zoophilia
1930s 1938 1boy 1girls 20th_century all_fours animal_genitalia animal_penis arched_back ass back_arch barely_visible_genitalia bent_over bent_over_chair bottomless canid canine canine_penis canis clothed clothing doggy_style doggy_style_position doggystyle domestic_dog dubious_consent duo enema enema_bulb female feral feral_on_female feral_on_human feral_penetrating feral_penetrating_human footwear from_behind from_behind_position garter garter_straps garters great_dane hands_crossed high_heels human human_on_feral human_penetrated implied_penetration implied_rape interspecies julie_delcourt legwear looking_away looking_away_from_viewer male mammal mounting neutral_expression painting_(artwork) part_of_a_set partially_clothed partially_undressed penetration penis presenting presenting_hindquarters questionable_consent sex shoes spotted_fur stocking_garters stockings straight traditional_art traditional_media_(artwork) vaginal_penetration watercolor_(artwork) zoophilia
1930s 1938 1boy 1girls 20th_century ass bestiality bottomless canid canine canis caught_off_guard clothed clothing dog domestic_dog duo enema enema_bulb female female_human feral feral_on_female feral_on_human footwear garter_straps garters great_dane heels high_heels human human_female imminent_sex indoors julie_delcourt legwear looking_at_partner looking_away looking_away_from_partner looking_away_from_viewer male male_canine male_dog male_feral mammal no_panties open_mouth panting part_of_a_set pointy_ears shoes stocking_garters stockings surprised thigh_high_socks thigh_highs thigh_stockings thighhighs tongue_out traditional_art traditional_media traditional_media_(artwork) watercolor watercolor_(artwork)
1930s 1938 1boy 1girls 20th_century ass bestiality bottomless canid canine canis caught_off_guard clothed clothing dog domestic_dog duo enema enema_bulb female female_human feral feral_on_female feral_on_human footwear garter_straps garters great_dane heels high_heels human human_female imminent_sex indoors julie_delcourt legwear looking_at_partner looking_away looking_away_from_partner looking_away_from_viewer male male_canine male_dog male_feral mammal no_panties open_mouth panting part_of_a_set pointy_ears shoes stocking_garters stockings surprised thigh_high_socks thigh_highs thigh_stockings thighhighs tongue_out traditional_art traditional_media traditional_media_(artwork) watercolor watercolor_(artwork)
1930s 1938 1boy 1girls 20th_century animal_genitalia animal_penis balls bottomless canid canine canine_penis canis clothed clothing domestic_dog dubious_consent duo enema enema_bulb erect_penis female feral feral_on_female feral_penetrating footwear great_dane heterosexual high_heels human human_on_feral imminent_rape imminent_sex interspecies julie_delcourt legwear male mammal mounting painting_(artwork) part_of_a_set penis questionable_consent red_penis shoes spotted spotted_fur stockings straight surprised tackle tail tapered_cock tapering_penis tongue_out torn_clothes traditional_art traditional_media traditional_media_(artwork) watercolor watercolor_(artwork) zoophilia
1930s 1938 1boy 1girls 20th_century animal_genitalia animal_penis balls bottomless canid canine canine_penis canis clothed clothing domestic_dog dubious_consent duo enema enema_bulb erect_penis female feral feral_on_female feral_penetrating footwear great_dane heterosexual high_heels human human_on_feral imminent_rape imminent_sex interspecies julie_delcourt legwear male mammal mounting painting_(artwork) part_of_a_set penis questionable_consent red_penis shoes spotted spotted_fur stockings straight surprised tackle tail tapered_cock tapering_penis tongue_out torn_clothes traditional_art traditional_media traditional_media_(artwork) watercolor watercolor_(artwork) zoophilia
1930s 1939 1animal 1girls 5_fingers arm_over_eyes avian bird blush bracelet breasts bush closed_eyes covering_eyes covering_face deity duo european_mythology feathered_wings feathers female female_on_feral female_pubic_hair feral feral_on_female feral_on_human feral_penetrating fine_art ginger ginger_hair ginger_pubic_hair greek_mythology gripping_sheets hair hidden_penetration human human_on_feral implied_penetration implied_sex implied_transformation interspecies jewelry jewelry_only laying laying_down laying_on_back laying_on_bed leda leda_and_the_swan long_hair long_neck lying male_feral mammal mostly_nude mythology necklace nipples nude obscured_genitals obscured_penetration on_back orange_hair orange_pubic_hair painting_(artwork) pale pale_skin paul_mathias_padua pearl_necklace pink_nipples pubic_hair public_domain rapist rapist_real reclining red_hair redhead sex small_areola small_areolae swan traditional_art traditional_media traditional_media_(artwork) watermark wings zeus zoophilia
1930s 1939 1animal 1girls 5_fingers arm_over_eyes avian bird blush bracelet breasts bush closed_eyes covering_eyes covering_face deity duo european_mythology feathered_wings feathers female female_on_feral female_pubic_hair feral feral_on_female feral_on_human feral_penetrating fine_art ginger ginger_hair ginger_pubic_hair greek_mythology gripping_sheets hair hidden_penetration human human_on_feral implied_penetration implied_sex implied_transformation interspecies jewelry jewelry_only laying laying_down laying_on_back laying_on_bed leda leda_and_the_swan long_hair long_neck lying male_feral mammal mostly_nude mythology necklace nipples nude obscured_genitals obscured_penetration on_back orange_hair orange_pubic_hair painting_(artwork) pale pale_skin paul_mathias_padua pearl_necklace pink_nipples pubic_hair public_domain rapist rapist_real reclining red_hair redhead sex small_areola small_areolae swan traditional_art traditional_media traditional_media_(artwork) watermark wings zeus zoophilia