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1boy 1girls 50s annie_hughes areolae big_breasts breasts brown_hair brown_hair_female cum cum_on_breasts cum_on_face dean_mccoppin diner dugg_dig facial female green_eyes lipstick male male_pov messy_hair milf nipples outercourse paizuri partial_male penis pov public public_nudity public_sex red_lipstick the_iron_giant titjob topless waitress

annie_hughesareolae

1950s 1957 1girls 20th_century 50s ass blonde_hair breasts brown_&_bigelow female female_only gil_elvgren lipstick makeup nail_polish nipples nude painting_(artwork) pinup pinup_girl see-through solo straight_hair thighs traditional_media_(artwork) vintage

1950s 1957 1girls 20th_century 50s ass bra breasts brown_&_bigelow brown_hair dress dressing female female_only gil_elvgren grass leg_up lipstick nail_polish painting_(artwork) panties parrot pinup pinup_girl side_view solo straight_hair thighs traditional_media_(artwork) vintage

1950s 1958 1girls 20th_century 50s areolae bed breasts brown_hair exposed_breasts female female_only gil_elvgren jewelry lipstick looking_down nail_polish nipples original painting_(artwork) pearl_necklace pinup pinup_girl see-through 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

areolaeblonde_hair

1950s 1girls 50s ankle_boots artist_signature black_dress cleavage crow demon_girl demon_horns disney disney_villains female female_only full_body green_skin holding_staff j_scott_campbell magic maleficent maleficent_(film) raven_(bird) red_lipstick side_slit sleeping_beauty_(1959_film) solo staff thorns villain walt_disney_animation_studios web_address

ankle_bootsartist_signature

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

blonde_hairbreasts

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 1955 1girls 20th_century 50's_theme 50s barefoot bill_randall blonde_hair breasts calendar_(medium) chasing covering_breasts crouching crouching_female english_text female female_only garter_straps looking_at_viewer naked naked_female nightgown nude nude_female nurse nurse_cap nurse_uniform original original_artwork pin_up pin_up_girl pinup pinup_art pinup_girl pinup_pose priscilla running_away see-through_clothing september_(month) side_view solo squatting straight_hair text vintage

barefootbill_randall

1950s 1957 1girls 20th_century 50s bill_randall blonde_hair breasts christmas christmas_gift christmas_present covered_crotch covered_nipples covering_breasts covering_crotch female female_only hat looking_at_viewer naked naked_female naked_footwear naked_hat naked_with_shoes_on nude nude_female original original_artwork pin_up pin_up_girl pinup pinup_girl pinup_pose solo standing straight_hair vintage

bill_randallblonde_hair

1950 1950s 1girls 20th_century 50's_theme 50s art_frahm ass blonde blonde_female blonde_hair blue_eyes blush cat dog dress female female_only high_heels leash legs_held_together legs_tied lifting_skirt original panties_down pinup pinup_girl realistic straight_hair surprised surprised_expression upskirt vintage wind wind_lift

1950 1950s 1girls 20th_century 50s bovine breasts cattle cretan_bull duo european_mythology facing_away female grass greek_mythology human implied_bestiality john_buckland-wright male mammal monochrome mythology nipples nude pasiphae plant public_domain raised_tail royalty straight_hair teats udders wooden_cow zoophilia

1950s 1954 20th_century 3girls 50s ass back_to_viewer back_view backside barefoot bill_randall black_hair blonde_hair breasts christmas christmas_decorations christmas_outfit christmas_tree crouching crouching_female decoration female female_only girl heeled_boots heels human kneeling light-skinned_female light_skin looking_at_viewer multiple_girls naked naked_female nude nude_female nudity original original_artwork pin_up_girl pinup pinup_girl pinup_pose santa_hat standing straight_hair vintage

assback_to_viewer

1950s 1952 1girls 20th_century 50s bikini bottomless breasts brown_&_bigelow female female_only fish fishing gil_elvgren goggles lipstick looking_at_viewer painting_(artwork) pinup pinup_girl small_breasts solo spear straight_hair swimsuit thighs traditional_media_(artwork) trident vintage water wet_skin

bikinibottomless

3d 3d_animation 3d_model 40s 50s abs african_american african_male age_difference aggressive akiyama_shun almost_crying anal anal_sex ass_fucking ass_out beard bedroom bedroom_sex big_forearms blonde_hair chest_hair cock cock_hungry cumming cumming_from_masturbation cumshot cumshot_in_mouth cumshot_on_face dominant_male domination dragon_tattoo exhausted exhausted_male eyes_half_closed flat_ass forearms forehead_kiss fucked_from_behind fucked_silly gang_bang gangbang gangster gay gay_anal gay_sex getting_fucked goda_ryuji groping_ass group group_sex hand_on_back hand_on_butt handjob head_on_lap head_on_thighs holding_penis holding_waist homosexual homosexual_sex hotel hotel_room interracial interracial_sex jerking_off kiryu_kazuma kissing_forehead large_penis larger_male laying_on_back legs_together licking_chest licking_partner like_a_dragon_(series) long_penis loving_look male male_breasts man_ass medium_hair medium_penis men_kissing midriff milking moaning moaning_in_pleasure mullet_(hairstyle) muscular muscular_male nervous no_pubic_hair old_male on_knees open_mouth orgy penis pinned_down pinned_to_bed rubbing_back ryu_ga_gotoku ryuu_ga_gotoku self_fondle self_fuck self_grope self_groping silver_fox skinny_male slapping_butt slippery small_pecs smirking_at_partner stroking_cock stroking_penis tattoo_on_ass thick_cum thighs_together thin_male touching_ass unhappy unhappy_male unspecified wet_cock white_hair whore_eyes yakuza_(series) yakuza_boss yakuza_tattoo yaoi yaoi_orgy

absafrican_american

50's_theme 50s artistic pinup pinup_girl zoe_mozert

1950s 1955 1girls 20th_century 50s ass bath bathroom black_hair breasts bubble cleavage female female_only joyce_ballantyne lipstick looking_at_viewer nail_polish nude original painting_(artwork) pinup pinup_girl solo straight_hair thick_thighs towel towel_on_head traditional_media_(artwork) vintage water

1950s 1958 20th_century 3boys 50s arm_restraints arms_above_head ass being_undressed bondage boots bound_ankles bound_wrists boy_rape bulge forced gay hunk leather leather_gear leather_jacket leather_pants leg_restraint leg_restraints male male_nipples male_only multiple_boys muscular nipples part_of_a_set questionable_consent restrained restrained_arms restrained_legs restraints rope straight_hair tight_pants tom_of_finland topless traditional_media traditional_media_(artwork) two_on_one undressing yaoi

arm_restraintsarms_above_head

1950s 1953 1girls 20th_century 50s alberto_vargas bewitched blonde blonde_hair blue_eyes breasts broom_riding female female_only halloween high_heels looking_back original pinup pinup_girl playing_card side_view smiling solo straight_hair tights vintage witch

alberto_vargasbewitched

1950s 1958 20th_century 3boys 50s being_undressed black_and_white boots bound_ankles bound_wrists boy_rape bulge cowboy cowboy_hat dubious_consent forced gay grayscale greyscale hunk jeans leather leather_boots leather_jacket male male_nipples male_only monochrome multiple_boys muscular muscular_male nipples part_of_a_set questionable_consent restrained rope spurs straight_hair tom_of_finland topless undressing yaoi

being_undressedblack_and_white

50's_theme 50s peter_driben pinup pinup_girl pinup_girls

peter_dribenpinup

1950s 1955 1boy 1girls 20th_century 50s belly_dancer belly_dancer_outfit book_cover breasts chains cleavage dancer dancer_outfit dancing dark-skinned_male female gong harem_girl harem_outfit jewelry large_breasts loincloth male necklace pinup rudy_nappi salambo slave straight_hair vintage

belly_dancerbelly_dancer_outfit

50s blonde_hair bodysuit comic_panel curvy helmet kit_carter lopresti raygun retro_artstyle short_hair space torn_clothes

blonde_hairbodysuit

50's_theme 50s enoch_bolles pinup pinup_girls

enoch_bollespinup

50's_theme 50s oil pinup pinup_girls vaughan_alden_bass

1950s 1960s 1boy 1boy1girl 1girls 2k 2k_games 3d 50s belly belly_button blender blue_eyes bottomless bottomless_male breasts breasts_out brown_hair car clothed clothed_male clothed_male_nude_female clothed_sex faceless faceless_character faceless_male fedora female female_soldier formal formal_wear frankiely_spicy garage grabbing grabbing_penis handjob human human_female indoor indoors indoors_sex inside legs legs_apart legs_spread looking looking_at_another looking_down looking_pleasured male military military_jacket military_uniform naked naked_female navel necktie nipples nude nude_female nude_female_clothed_male officer_chulski parking_garage parking_lot penis penis_grab penis_out short_hair smile smiling_at_partner soldier straight stroke stroking stroking_cock stroking_penis suit suit_and_tie the_bureau:_xcom_declassified tied_hair unprofessional_behavior vehicle x-com

bellybelly_button

1950s 1960s 1boy 1boy1girl 1girls 2k 2k_games 3d 50s blender blue_eyes bottomless bottomless_male brown_hair car clothed clothed_female clothed_female_clothed_male clothed_male clothed_male_clothed_female clothed_sex english_text faceless faceless_character faceless_male fedora female female_soldier formal formal_wear frankiely_spicy garage grabbing grabbing_penis handjob human human_female indoor indoors indoors_sex inside legs legs_apart legs_spread looking looking_at_another looking_down looking_pleasured male military military_jacket military_uniform name_tag necktie officer_chulski parking_garage parking_lot penis penis_grab penis_out short_hair smile smiling_at_partner soldier straight stroke stroking stroking_cock stroking_penis suit suit_and_tie text the_bureau:_xcom_declassified tied_hair unprofessional_behavior vehicle x-com

blenderblue_eyes

50s aaron_lopresti blonde_hair bodysuit comic_panel curvy helmet kit_carter kit_carter:_planet_doom raygun retro_artstyle short_hair source_request space torn_clothes

aaron_loprestiblonde_hair

1950s 1952 1boy 20th_century 50s bulge george_quaintance gold_hair horns male male_only muscular outdoors painting plump_lips pose quaintance solo_male tanned thong toned twink

bulgegeorge_quaintance

50's_theme 50s george_petty pinup pinup_girl pinup_girls swing swinging

george_pettypinup

50s black_male black_nails blonde_hair brown_eyes chin_beard chubby chubby_belly collar cum cum_drip cute_male dominican dreadlocks dreads drooling embarrassed embarrassed_nude_male extremely_hairy hairy hairy_arms hairy_balls hairy_chest hairy_legs hairy_male holding_leash leash leash_and_collar leashed_male moustache nipple_piercing nipples older_male pierced_ears pierced_nose piercing piercings septum_piercing sitting thick_hips thick_thighs very_hairy vitiligo

black_maleblack_nails

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