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1930s

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 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
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 betty_boop popeye popeye_(series) tagme tijuana_bible vintage
1930s betty_boop popeye popeye_(series) tagme tijuana_bible vintage
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 1boy 1girls artist_request ass black_border black_fur comic compression_artifacts disney erect_penis erection female french_text from_behind fur furry furry_only high_heels imminent_sex looking_back male mickey_mouse minnie_mouse monochrome mouse panties penis penis_out pointing shirtless shorts sofa source_request straight tail text tijuana_bible topless undressing vintage what
1930s 1boy 1girls artist_request ass black_border black_fur comic compression_artifacts disney erect_penis erection female french_text from_behind fur furry furry_only high_heels imminent_sex looking_back male mickey_mouse minnie_mouse monochrome mouse panties penis penis_out pointing shirtless shorts sofa source_request straight tail text tijuana_bible topless undressing vintage what