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1980s

1980s 1988 1girls 2boys bound bound_wrists cap censored clothed clothing crying crying_with_eyes_open deepthroat doujinshi english_text falling female gag gagging game_over gloves greyscale hand_on_leg hat highres horikawa_gorou interspecies irrumatio koopa_troopa long_hair male mario mario_(series) monochrome multiple_boys muscles muscular muscular_male musical_note nintendo note_block nude oral penis princess princess_peach running saliva saliva_drip saliva_trail scan shoes short_hair slave sound_effects super_mario_bros. super_mario_bros._(nes) tears text translated warp_pipe zip-a-tone
1980s 1988 1girls 2boys bound bound_wrists cap censored clothed clothing crying crying_with_eyes_open deepthroat doujinshi english_text falling female gag gagging game_over gloves greyscale hand_on_leg hat highres horikawa_gorou interspecies irrumatio koopa_troopa long_hair male mario mario_(series) monochrome multiple_boys muscles muscular muscular_male musical_note nintendo note_block nude oral penis princess princess_peach running saliva saliva_drip saliva_trail scan shoes short_hair slave sound_effects super_mario_bros. super_mario_bros._(nes) tears text translated warp_pipe zip-a-tone
1980s 1988 4boys anal anus ass back bound bound_wrists breast_grab breasts cap censored chains clothed clothing collar crying crying_with_eyes_open deepthroat doujinshi english_text eyebrows_visible_through_hair fat_man fire fireball flying_sweatdrops gag gagging gangbang gloves greyscale group_sex hat highres horikawa_gorou interspecies irrumatio koopa_troopa long_hair mario mario_(series) medium_breasts moaning monochrome moustache multiple_boys muscles muscular muscular_male nintendo nipples nude oral penis princess princess_peach pussy pussy_juice pussy_juice_drip restrained saliva saliva_drip scan see-through see-through_penis see-through_silhouette sex short_hair slave sound_effects spiked_collar spikes standing super_mario_bros. super_mario_bros._(nes) sweat sweatdrop tears text thighs translated triple_penetration vaginal_penetration zip-a-tone
1980s 1988 4boys anal anus ass back bound bound_wrists breast_grab breasts cap censored chains clothed clothing collar crying crying_with_eyes_open deepthroat doujinshi english_text eyebrows_visible_through_hair fat_man fire fireball flying_sweatdrops gag gagging gangbang gloves greyscale group_sex hat highres horikawa_gorou interspecies irrumatio koopa_troopa long_hair mario mario_(series) medium_breasts moaning monochrome moustache multiple_boys muscles muscular muscular_male nintendo nipples nude oral penis princess princess_peach pussy pussy_juice pussy_juice_drip restrained saliva saliva_drip scan see-through see-through_penis see-through_silhouette sex short_hair slave sound_effects spiked_collar spikes standing super_mario_bros. super_mario_bros._(nes) sweat sweatdrop tears text thighs translated triple_penetration vaginal_penetration zip-a-tone
1980s 1988 1girls 2boys anal animal_ears anus ass ass_grab back bouncing_breasts breast_grab breasts cap censored closed_eyes clothed clothing collar cowgirl_position crying doujinshi english_text eyebrows_visible_through_hair fat_man female flying_sweatdrops greyscale hat highres horikawa_gorou interspecies jumping koopa_troopa long_hair lying male mario mario_(series) medium_breasts mohawk monochrome moustache multiple_boys navel nintendo nipples nude on_back open_mouth outdoors penis piledriver_position princess princess_peach pussy pussy_juice pussy_juice_drip raccoon_ears raccoon_tail scan screaming sex shaded_face sharp_teeth shoes short_hair slave sound_effects spiked_collar spikes super_mario_bros. super_mario_bros._(nes) sweat sweatdrop tail tears text thighs tongue translated vaginal_penetration zip-a-tone
1980s 1988 1girls 2boys anal animal_ears anus ass ass_grab back bouncing_breasts breast_grab breasts cap censored closed_eyes clothed clothing collar cowgirl_position crying doujinshi english_text eyebrows_visible_through_hair fat_man female flying_sweatdrops greyscale hat highres horikawa_gorou interspecies jumping koopa_troopa long_hair lying male mario mario_(series) medium_breasts mohawk monochrome moustache multiple_boys navel nintendo nipples nude on_back open_mouth outdoors penis piledriver_position princess princess_peach pussy pussy_juice pussy_juice_drip raccoon_ears raccoon_tail scan screaming sex shaded_face sharp_teeth shoes short_hair slave sound_effects spiked_collar spikes super_mario_bros. super_mario_bros._(nes) sweat sweatdrop tail tears text thighs tongue translated vaginal_penetration zip-a-tone
1980s 1989 20th_century blonde_hair cherry_poptart cherry_poptart_(comic) comic comic_cover cover_page cowboy_hat dialogue dress_shirt farmer farmgirl female hair_ribbons hitchhiking larry_welz pink_purse ponytails purse ribbon_hair short_jeans short_shorts straight_hair tied_shirt truck twintails
1980s 1989 20th_century blonde_hair cherry_poptart cherry_poptart_(comic) comic comic_cover cover_page cowboy_hat dialogue dress_shirt farmer farmgirl female hair_ribbons hitchhiking larry_welz pink_purse ponytails purse ribbon_hair short_jeans short_shorts straight_hair tied_shirt truck twintails
1980s 1989 20th_century 3boys anthro cherry_poptart_(comic) comic comic_cover cover_page ellie_dee female fur furry glasses hair_ribbon larry_welz lion_boy lion_humanoid paperboy parody rainbow red_shoes robot robot_humanoid short_shorts straight_hair twintails
1980s 1989 20th_century 3boys anthro cherry_poptart_(comic) comic comic_cover cover_page ellie_dee female fur furry glasses hair_ribbon larry_welz lion_boy lion_humanoid paperboy parody rainbow red_shoes robot robot_humanoid short_shorts straight_hair twintails
1980s 1988 20th_century 2girls ass black_hair blonde_hair butt cherry_poptart cherry_poptart_(comic) comic comic_cover cover_page covered_breasts covering covering_breasts dialogue ellie_dee embarrassed embarrassed_nude_female enf glasses holding_blanket holding_towel larry_welz multiple_girls naked naked_female nervous nude nude_female pill_bottle pills short_shorts shortshorts shy stage stage_fright stage_lights straight_hair white_t-shirt
1980s 1988 20th_century 2girls ass black_hair blonde_hair butt cherry_poptart cherry_poptart_(comic) comic comic_cover cover_page covered_breasts covering covering_breasts dialogue ellie_dee embarrassed embarrassed_nude_female enf glasses holding_blanket holding_towel larry_welz multiple_girls naked naked_female nervous nude nude_female pill_bottle pills short_shorts shortshorts shy stage stage_fright stage_lights straight_hair white_t-shirt
1980s 1988 1boy 1girls 20th_century beach_house beachside black_hair blonde_hair car cherry_poptart cherry_poptart_(comic) clothed comic comic_cover dialogue eye_makeup female green_dress helicopter larry_welz nipples_visible_through_clothing palm_tree palm_trees straight_hair
1980s 1988 1boy 1girls 20th_century beach_house beachside black_hair blonde_hair car cherry_poptart cherry_poptart_(comic) clothed comic comic_cover dialogue eye_makeup female green_dress helicopter larry_welz nipples_visible_through_clothing palm_tree palm_trees straight_hair
1980s 1988 20th_century 2girls blonde_hair breasts brown_coat brown_jacket camera camera_flash camera_flashes cherry_poptart cherry_poptart_(comic) cleavage clothed coat comic comic_cover erect_nipples female jacket jeans larry_welz medium_breasts multiple_boys news_reporter nipple_bulge nipples_visible_through_clothing paparazzi reporter reporter_girl straight_hair wide_hips
1980s 1988 20th_century 2girls blonde_hair breasts brown_coat brown_jacket camera camera_flash camera_flashes cherry_poptart cherry_poptart_(comic) cleavage clothed coat comic comic_cover erect_nipples female jacket jeans larry_welz medium_breasts multiple_boys news_reporter nipple_bulge nipples_visible_through_clothing paparazzi reporter reporter_girl straight_hair wide_hips
1980s 1987 20th_century 2girls 3boys band bikini black_bikini black_hair blonde_hair cherry_poptart cherry_poptart_(comic) comic comic_cover concert drummer drums fog guitar guitars larry_welz lola_palooza nipples_visible_through_clothing one-piece_swimsuit revealing_clothes roadie stage stage_lights straight_hair tagme
1980s 1987 20th_century 2girls 3boys band bikini black_bikini black_hair blonde_hair cherry_poptart cherry_poptart_(comic) comic comic_cover concert drummer drums fog guitar guitars larry_welz lola_palooza nipples_visible_through_clothing one-piece_swimsuit revealing_clothes roadie stage stage_lights straight_hair tagme
1980s 1986 3boys 3girls american_flag black_hair blimp breasts brown_hair brunette cherry_pop cherry_poptart_(comic) comic comic_cover crowd dialogue ellie_dee ginger glasses helicopter larry_welz mohawk mustache nipples_visible_through_clothing patty_melt red_hair stadium straight_hair
1980s 1986 3boys 3girls american_flag black_hair blimp breasts brown_hair brunette cherry_pop cherry_poptart_(comic) comic comic_cover crowd dialogue ellie_dee ginger glasses helicopter larry_welz mohawk mustache nipples_visible_through_clothing patty_melt red_hair stadium straight_hair
1980s 1985 20th_century 2girls barefoot black_hair blonde_hair bondage breasts chained chains cherry_poptart cherry_poptart_(comic) comic comic_cover dialogue dominant_female dominated dominatrix equipment exercising_equipment female femdom femsub gym gym_clothes gym_clothing gym_uniform larry_welz leather leather_outfit monica_(cherry_poptart) multiple_girls nipples_visible_through_clothing shackles straight_hair weight_bench weights
1980s 1985 20th_century 2girls barefoot black_hair blonde_hair bondage breasts chained chains cherry_poptart cherry_poptart_(comic) comic comic_cover dialogue dominant_female dominated dominatrix equipment exercising_equipment female femdom femsub gym gym_clothes gym_clothing gym_uniform larry_welz leather leather_outfit monica_(cherry_poptart) multiple_girls nipples_visible_through_clothing shackles straight_hair weight_bench weights
1980s 1984 1boy 20th_century 2girls black_hair blonde_hair blue_sky breaking_the_fourth_wall cherry_pop cherry_poptart cherry_poptart_(comic) clothed cloud comic comic_cover cowboy_shot day daytime dialogue ellie_dee english_text fake_cover full_body ginger jean_shorts jeans jorts lamppost larry_welz midriff no_bra orange_hair parking_lot red_hair red_lips red_lipstick roller_skates round_glasses short_shorts skates skating speech_bubble standing straight_hair tank_top topwear tubetop van yellow_glasses
1980s 1984 1boy 20th_century 2girls black_hair blonde_hair blue_sky breaking_the_fourth_wall cherry_pop cherry_poptart cherry_poptart_(comic) clothed cloud comic comic_cover cowboy_shot day daytime dialogue ellie_dee english_text fake_cover full_body ginger jean_shorts jeans jorts lamppost larry_welz midriff no_bra orange_hair parking_lot red_hair red_lips red_lipstick roller_skates round_glasses short_shorts skates skating speech_bubble standing straight_hair tank_top topwear tubetop van yellow_glasses
1980s 1987 1girls 20th_century big_breasts big_hair blonde_hair breasts cherry_poptart cherry_poptart_(comic) dialogue hairy hairy_pussy hand_on_own_pussy hand_on_pussy larry_welz laying_on_bed laying_on_pillow looking_at_viewer naked naked_female no_color nude nude_female on_bed pillows pubic_hair straight_hair talking_to_viewer unshaved_pussy year
1980s 1987 1girls 20th_century big_breasts big_hair blonde_hair breasts cherry_poptart cherry_poptart_(comic) dialogue hairy hairy_pussy hand_on_own_pussy hand_on_pussy larry_welz laying_on_bed laying_on_pillow looking_at_viewer naked naked_female no_color nude nude_female on_bed pillows pubic_hair straight_hair talking_to_viewer unshaved_pussy year
1980s 1985 1girls 20th_century bible breasts cherry_poptart cherry_poptart_(comic) church coif corset female_only fishnet fishnet_legwear fishnet_stockings fishnets hairy hairy_pussy larry_welz looking_at_viewer nipples no_bra no_color no_panties nun nun's_habit nun_outfit solo_female stained_glass stained_glass_window stockings straight_hair talking_to_viewer unshaved_pussy year
1980s 1985 1girls 20th_century bible breasts cherry_poptart cherry_poptart_(comic) church coif corset female_only fishnet fishnet_legwear fishnet_stockings fishnets hairy hairy_pussy larry_welz looking_at_viewer nipples no_bra no_color no_panties nun nun's_habit nun_outfit solo_female stained_glass stained_glass_window stockings straight_hair talking_to_viewer unshaved_pussy year
1980s 1987 1girls 20th_century ass black_hair black_pubic_hair cherry_poptart_(comic) comic comic_page dialogue digital_world ellie_dee explosion female hairy hairy_pussy hairy_vagina larry_welz legs_spread maze nipples no_color normal_breasts nude nude_female pac-man pac-man_(series) skinny skinny_girl space_invaders straight_hair teleportation video_games virtual_reality
1980s 1987 1girls 20th_century ass black_hair black_pubic_hair cherry_poptart_(comic) comic comic_page dialogue digital_world ellie_dee explosion female hairy hairy_pussy hairy_vagina larry_welz legs_spread maze nipples no_color normal_breasts nude nude_female pac-man pac-man_(series) skinny skinny_girl space_invaders straight_hair teleportation video_games virtual_reality
1980s 1987 20th_century 2girls ass ass_view back_view black_hair cherry_poptart cherry_poptart_(comic) clothed_female_nude_female comic comic_page completely_nude computer conversation dialogue ellie_dee industrial larry_welz multiple_girls naked naked_female nude nude_female skinny straight_hair teleportation virtual_reality
1980s 1987 20th_century 2girls ass ass_view back_view black_hair cherry_poptart cherry_poptart_(comic) clothed_female_nude_female comic comic_page completely_nude computer conversation dialogue ellie_dee industrial larry_welz multiple_girls naked naked_female nude nude_female skinny straight_hair teleportation virtual_reality
1980s 1987 20th_century 2girls bed black_hair cherry_poptart cherry_poptart_(comic) cigarette comic comic_page computer conversation dialogue ellie_dee glasses larry_welz laying_on_bed multiple_girls no_color smoking straight_hair tagme
1980s 1987 20th_century 2girls bed black_hair cherry_poptart cherry_poptart_(comic) cigarette comic comic_page computer conversation dialogue ellie_dee glasses larry_welz laying_on_bed multiple_girls no_color smoking straight_hair tagme
1980s 1987 1girls 20th_century 6+boys 7boys actor african african_male artist_name beard beer_mug belt belt_buckle black_pants blonde_hair boots bracelet brown_belt cannon captain_hook celebrity cherry_poptart cherry_poptart_(comic) clothed copyright_name cutlass dark-skinned_male dark_skin day daytime disney_villains earrings eyepatch facing_viewer female_pirate fire full_body grin hand_on_hip headband jewelry larry_welz laurence_"mr._t"_tureaud looking_at_viewer melanin midriff mohawk mustache no_bra ocean outdoors pale-skinned_female pale_skin pants peter_pan_(disney) pirate pirate_captain pirate_costume pirate_crew pirate_hat pirate_outfit pirate_ship pirates real_person red_lips red_lipstick ring ship_deck sinking_ship small_breasts smile smoke standing straight_hair striped_shirt sword tied_shirt treasure treasure_chest white_blouse white_shirt white_skin wooden_floor wooden_ship year
1980s 1987 1girls 20th_century 6+boys 7boys actor african african_male artist_name beard beer_mug belt belt_buckle black_pants blonde_hair boots bracelet brown_belt cannon captain_hook celebrity cherry_poptart cherry_poptart_(comic) clothed copyright_name cutlass dark-skinned_male dark_skin day daytime disney_villains earrings eyepatch facing_viewer female_pirate fire full_body grin hand_on_hip headband jewelry larry_welz laurence_"mr._t"_tureaud looking_at_viewer melanin midriff mohawk mustache no_bra ocean outdoors pale-skinned_female pale_skin pants peter_pan_(disney) pirate pirate_captain pirate_costume pirate_crew pirate_hat pirate_outfit pirate_ship pirates real_person red_lips red_lipstick ring ship_deck sinking_ship small_breasts smile smoke standing straight_hair striped_shirt sword tied_shirt treasure treasure_chest white_blouse white_shirt white_skin wooden_floor wooden_ship year
1980s 1988 1girls 2boys armor bald bound_wrists censored chains clothed clothing collar crying crying_with_eyes_open dialogue doujinshi emphasis_lines english_text fat_man female fighting goomba greyscale hair_grab hammer_bros. hand_on_head hat highres horikawa_gorou interspecies licking licking_penis looking_at_another looking_up male mario mario_(series) monochrome moustache multiple_boys muscles muscular muscular_male nintendo nude open_mouth penis penis_grab princess princess_peach punch punching saliva saliva_drip saliva_trail scan serious shell smile sound_effects speech_bubble super_mario_bros. super_mario_bros._(nes) sweat tears teeth text tongue translated zip-a-tone
1980s 1988 1girls 2boys armor bald bound_wrists censored chains clothed clothing collar crying crying_with_eyes_open dialogue doujinshi emphasis_lines english_text fat_man female fighting goomba greyscale hair_grab hammer_bros. hand_on_head hat highres horikawa_gorou interspecies licking licking_penis looking_at_another looking_up male mario mario_(series) monochrome moustache multiple_boys muscles muscular muscular_male nintendo nude open_mouth penis penis_grab princess princess_peach punch punching saliva saliva_drip saliva_trail scan serious shell smile sound_effects speech_bubble super_mario_bros. super_mario_bros._(nes) sweat tears teeth text tongue translated zip-a-tone
1980s 1988 1boy 1girls 20th_century after_sex armpits ass bald big_penis bound_ankles bound_wrists breasts censored chains cheek_poke collar crying crying_with_eyes_open cuffs dialogue doujinshi english_text eyebrows_visible_through_hair female flying_sweatdrops goomba greyscale grin hair_grab highres horikawa_gorou humanoid interspecies long_hair looking_at_another looking_at_penis lying male mario_(series) medium_breasts monochrome monster muscles muscular muscular_male nintendo nipples nude on_stomach open_mouth penis princess princess_peach restrained scan slave smile smirk sound_effects speech_bubble super_mario_bros. super_mario_bros._(nes) sweat tears teeth text thighs translated zip-a-tone
1980s 1988 1boy 1girls 20th_century after_sex armpits ass bald big_penis bound_ankles bound_wrists breasts censored chains cheek_poke collar crying crying_with_eyes_open cuffs dialogue doujinshi english_text eyebrows_visible_through_hair female flying_sweatdrops goomba greyscale grin hair_grab highres horikawa_gorou humanoid interspecies long_hair looking_at_another looking_at_penis lying male mario_(series) medium_breasts monochrome monster muscles muscular muscular_male nintendo nipples nude on_stomach open_mouth penis princess princess_peach restrained scan slave smile smirk sound_effects speech_bubble super_mario_bros. super_mario_bros._(nes) sweat tears teeth text thighs translated zip-a-tone
1980s 1988 1boy 1girls 1monster 20th_century anal anus ass blooper bodily_fluids breast_grab breasts censored cheep_cheep crying crying_with_eyes_open deepthroat dialogue doujinshi english_text eyebrows_visible_through_hair facial fangs female greyscale highres horikawa_gorou humanoid irrumatio long_hair looking_at_another male mario_(series) medium_breasts mohawk monochrome navel nintendo nipples nude oral princess princess_peach pussy_juice pussy_juice_drip pussy_juice_trail rape restrained saliva saliva_drip saliva_trail scan sex smile sound_effects speech_bubble spread_legs standing suggestive_fluid sunglasses super_mario_bros. super_mario_bros._(nes) suspension sweat tears teeth tentacle tentacle_rape tentacle_sex text thighs tongue translated triple_penetration vaginal_penetration water zip-a-tone
1980s 1988 1boy 1girls 1monster 20th_century anal anus ass blooper bodily_fluids breast_grab breasts censored cheep_cheep crying crying_with_eyes_open deepthroat dialogue doujinshi english_text eyebrows_visible_through_hair facial fangs female greyscale highres horikawa_gorou humanoid irrumatio long_hair looking_at_another male mario_(series) medium_breasts mohawk monochrome navel nintendo nipples nude oral princess princess_peach pussy_juice pussy_juice_drip pussy_juice_trail rape restrained saliva saliva_drip saliva_trail scan sex smile sound_effects speech_bubble spread_legs standing suggestive_fluid sunglasses super_mario_bros. super_mario_bros._(nes) suspension sweat tears teeth tentacle tentacle_rape tentacle_sex text thighs tongue translated triple_penetration vaginal_penetration water zip-a-tone
1980s 1988 1monster blooper bodily_fluids breast_grab breasts bubble cap clothed clothing crying crying_with_eyes_open deepthroat defeated dialogue doujinshi emphasis_lines english_text eyebrows_visible_through_hair fat_man fighting greyscale half-closed_eyes hat highres horikawa_gorou interspecies irrumatio long_hair mario mario_(series) medium_breasts monochrome monster moustache muscles muscular muscular_male nintendo nipple_pinch nipples oral princess princess_peach rape restrained saliva saliva_drip saliva_trail scan serious sound_effects speech_bubble spread_legs squid suggestive_fluid super_mario_bros. super_mario_bros._(nes) suspension sweat swimming tears tentacle tentacle_in_mouth tentacle_rape text thighs translated underwater water zip-a-tone
1980s 1988 1monster blooper bodily_fluids breast_grab breasts bubble cap clothed clothing crying crying_with_eyes_open deepthroat defeated dialogue doujinshi emphasis_lines english_text eyebrows_visible_through_hair fat_man fighting greyscale half-closed_eyes hat highres horikawa_gorou interspecies irrumatio long_hair mario mario_(series) medium_breasts monochrome monster moustache muscles muscular muscular_male nintendo nipple_pinch nipples oral princess princess_peach rape restrained saliva saliva_drip saliva_trail scan serious sound_effects speech_bubble spread_legs squid suggestive_fluid super_mario_bros. super_mario_bros._(nes) suspension sweat swimming tears tentacle tentacle_in_mouth tentacle_rape text thighs translated underwater water zip-a-tone
1980s 1985 1girls 2021 areola areolae art_progression balsamique crayon_(artwork) digital_media_(artwork) drawn fins humanoid mermaid mermaid_tail nipples straight_hair voluptuous water
1980s 1985 1girls 2021 areola areolae art_progression balsamique crayon_(artwork) digital_media_(artwork) drawn fins humanoid mermaid mermaid_tail nipples straight_hair voluptuous water
1980s 1988 1girls 20th_century blonde_hair cherry_poptart cherry_poptart_(comic) corset larry_welz nightgown nipples_showing nipples_visible_through_clothing no_panties pink_background purple_corset purple_heels purple_nightgown purple_stockings signature straight_hair tagme watermark white_body white_skin year
1980s 1988 1girls 20th_century blonde_hair cherry_poptart cherry_poptart_(comic) corset larry_welz nightgown nipples_showing nipples_visible_through_clothing no_panties pink_background purple_corset purple_heels purple_nightgown purple_stockings signature straight_hair tagme watermark white_body white_skin year
1980s 1989 1996 20th_century aircraft anthro black_and_white building building_sex canid canine car chest_tuft city crush destruction female fox half_lidded_eyes helicopter hill improvised_sex_toy kencougr macro mammal monochrome open_mouth orgasm orgasm_face solo straight_hair traditional_media_(artwork) tuft vehicle year
1980s 1989 1996 20th_century aircraft anthro black_and_white building building_sex canid canine car chest_tuft city crush destruction female fox half_lidded_eyes helicopter hill improvised_sex_toy kencougr macro mammal monochrome open_mouth orgasm orgasm_face solo straight_hair traditional_media_(artwork) tuft vehicle year
1980s 1985 1996 20th_century anthro black_and_white city cityscape destruction extreme_micro female fluffy fluffy_hair giantess hair improvised_sex_toy kaiju kencougr long_hair long_tail lutrine macro macro_female mammal masturbation micro_on_macro monochrome mustelid solo tail_wiggle tongue tongue_out traditional_media_(artwork) train vagina vaginal_masturbation vaginal_penetration vehicle vehicle_destruction vehicle_sex
1980s 1985 1996 20th_century anthro black_and_white city cityscape destruction extreme_micro female fluffy fluffy_hair giantess hair improvised_sex_toy kaiju kencougr long_hair long_tail lutrine macro macro_female mammal masturbation micro_on_macro monochrome mustelid solo tail_wiggle tongue tongue_out traditional_media_(artwork) train vagina vaginal_masturbation vaginal_penetration vehicle vehicle_destruction vehicle_sex
1980s 1989 1996 20th_century abs angry anthro black_and_white car city cityscape crush crushed_vehicle destruction domestic_cat dropping dropping_object felid feline felis female hand_crush human kencougr macro mammal monochrome solo straight_hair street_lamp traditional_media_(artwork) vehicle walking year
1980s 1989 1996 20th_century abs angry anthro black_and_white car city cityscape crush crushed_vehicle destruction domestic_cat dropping dropping_object felid feline felis female hand_crush human kencougr macro mammal monochrome solo straight_hair street_lamp traditional_media_(artwork) vehicle walking year
1980s 1989 20th_century ambiguous_species anthro ass black_and_white building butt_grab crush crushed_underfoot cuddling destruction duo female female/female fingering fluffy fluffy_tail fur hair hand_on_butt house kencougr lawn lying macro mammal mephitid monochrome multicolored_body multicolored_fur neighborhood on_back orgasm orgasm_face plant sex short_hair skunk straight_hair traditional_media_(artwork) tree two_tone_body two_tone_fur year yuri
1980s 1989 20th_century ambiguous_species anthro ass black_and_white building butt_grab crush crushed_underfoot cuddling destruction duo female female/female fingering fluffy fluffy_tail fur hair hand_on_butt house kencougr lawn lying macro mammal mephitid monochrome multicolored_body multicolored_fur neighborhood on_back orgasm orgasm_face plant sex short_hair skunk straight_hair traditional_media_(artwork) tree two_tone_body two_tone_fur year yuri
1980s 1988 1boy 1girls breasts censored collar crown crying crying_with_eyes_open dialogue doujinshi english_text eyebrows_visible_through_hair feet female greyscale highres horikawa_gorou humanoid indoors interspecies koopa_troopa leg_grab legs_held_open legs_up long_hair male mario_(series) medium_breasts moaning monochrome motion_lines navel nintendo nipples nude open_mouth penis princess princess_peach pussy_juice pussy_juice_drip rape reverse_stand_and_carry_position reverse_suspended_congress scan sex soles sound_effects speech_bubble speed_lines spread_legs standing super_mario_bros. super_mario_bros._(nes) sweat sweating sweating_profusely tears text thighs translated vaginal_penetration zip-a-tone
1980s 1988 1boy 1girls breasts censored collar crown crying crying_with_eyes_open dialogue doujinshi english_text eyebrows_visible_through_hair feet female greyscale highres horikawa_gorou humanoid indoors interspecies koopa_troopa leg_grab legs_held_open legs_up long_hair male mario_(series) medium_breasts moaning monochrome motion_lines navel nintendo nipples nude open_mouth penis princess princess_peach pussy_juice pussy_juice_drip rape reverse_stand_and_carry_position reverse_suspended_congress scan sex soles sound_effects speech_bubble speed_lines spread_legs standing super_mario_bros. super_mario_bros._(nes) sweat sweating sweating_profusely tears text thighs translated vaginal_penetration zip-a-tone
1980s 1988 1girls 20th_century 2boys arms_behind_back bald blush bound_ankles breast_grab breasts clothing collar crown crying crying_with_eyes_open dialogue doujinshi dress elbow_gloves english_text eyebrows_visible_through_hair feet female forced forced_to_watch gloves greyscale highres horikawa_gorou humanoid imminent_sex indoors interspecies jewelry koopa_troopa leg_grab legs_up lifting lifting_person long_hair looking_at_another looking_down male mario_(series) medium_breasts moaning monochrome monster motion_lines nintendo nipples nude princess princess_peach rape restrained rope scan scared screaming sharp_teeth smile soles sound_effects speech_bubble speed_lines spread_legs spreading standing super_mario_bros. super_mario_bros._(nes) sweat sweating sweating_profusely tears teeth text thighs toad_(mario) tongue torn_clothes torture translated zip-a-tone
1980s 1988 1girls 20th_century 2boys arms_behind_back bald blush bound_ankles breast_grab breasts clothing collar crown crying crying_with_eyes_open dialogue doujinshi dress elbow_gloves english_text eyebrows_visible_through_hair feet female forced forced_to_watch gloves greyscale highres horikawa_gorou humanoid imminent_sex indoors interspecies jewelry koopa_troopa leg_grab legs_up lifting lifting_person long_hair looking_at_another looking_down male mario_(series) medium_breasts moaning monochrome monster motion_lines nintendo nipples nude princess princess_peach rape restrained rope scan scared screaming sharp_teeth smile soles sound_effects speech_bubble speed_lines spread_legs spreading standing super_mario_bros. super_mario_bros._(nes) sweat sweating sweating_profusely tears teeth text thighs toad_(mario) tongue torn_clothes torture translated zip-a-tone
1980s 1988 1girls 20th_century 3boys bald bound_torso breasts cap closed_eyes clothed_female_nude_male collar crown crying dialogue doujinshi dress elbow_gloves english_text eyebrows_visible_through_hair fat_man female flying_sweatdrops forced forced_to_watch frilled_dress frills gloves goomba greyscale hat highres horikawa_gorou humanoid indoors jewelry jumping koopa koopa_troopa long_hair looking_at_another male mario mario_(series) medium_breasts monochrome monster moustache multiple_boys muscles muscular muscular_male nintendo nude open_mouth outdoors princess princess_peach restrained rope scan scared screaming sharp_teeth shell smile sound_effects speech_bubble speed_lines standing super_mario_bros. super_mario_bros._(nes) sweat sweatdrop tank_top tears teeth text tight_clothing toad_(mario) tongue translated trembling zip-a-tone
1980s 1988 1girls 20th_century 3boys bald bound_torso breasts cap closed_eyes clothed_female_nude_male collar crown crying dialogue doujinshi dress elbow_gloves english_text eyebrows_visible_through_hair fat_man female flying_sweatdrops forced forced_to_watch frilled_dress frills gloves goomba greyscale hat highres horikawa_gorou humanoid indoors jewelry jumping koopa koopa_troopa long_hair looking_at_another male mario mario_(series) medium_breasts monochrome monster moustache multiple_boys muscles muscular muscular_male nintendo nude open_mouth outdoors princess princess_peach restrained rope scan scared screaming sharp_teeth shell smile sound_effects speech_bubble speed_lines standing super_mario_bros. super_mario_bros._(nes) sweat sweatdrop tank_top tears teeth text tight_clothing toad_(mario) tongue translated trembling zip-a-tone
1980s 1988 1girls 2boys arms_up bound_wrists bowser breasts cape chains clothing collar copyright_name crown crying crying_with_eyes_open dialogue doujinshi dress elbow_gloves english_text eyebrows_visible_through_hair female frilled_dress frills gloves greyscale highres horikawa_gorou humanoid indoors jewelry long_hair looking_at_another looking_away male mario mario_(series) medium_breasts monochrome monster multiple_boys nintendo open_mouth princess princess_peach restrained scan sharp_teeth size_difference smaller_female smile speech_bubble standing straight_hair super_mario_bros. super_mario_bros._(nes) sweat tears teeth text text_bubble thick_eyebrows thighs tongue torn_clothes torn_dress translated zip-a-tone
1980s 1988 1girls 2boys arms_up bound_wrists bowser breasts cape chains clothing collar copyright_name crown crying crying_with_eyes_open dialogue doujinshi dress elbow_gloves english_text eyebrows_visible_through_hair female frilled_dress frills gloves greyscale highres horikawa_gorou humanoid indoors jewelry long_hair looking_at_another looking_away male mario mario_(series) medium_breasts monochrome monster multiple_boys nintendo open_mouth princess princess_peach restrained scan sharp_teeth size_difference smaller_female smile speech_bubble standing straight_hair super_mario_bros. super_mario_bros._(nes) sweat tears teeth text text_bubble thick_eyebrows thighs tongue torn_clothes torn_dress translated zip-a-tone
1980s 1985 3girls amber_(mysteron) benten black_and_white blush bowtie breasts bunny_ears bunny_girl bunnysuit closed_eyes curvaceous detached_collar female female_only fishnets goddess greyscale japanese_text kneeling large_breasts long_hair looking_at_viewer lum monochrome oni pantyhose pointy_chin pointy_ears princess pussy ran_(urusei_yatsura) shoes tagme text tomboy trio urusei_yatsura wide_hips wrist_cuffs
1980s 1985 3girls amber_(mysteron) benten black_and_white blush bowtie breasts bunny_ears bunny_girl bunnysuit closed_eyes curvaceous detached_collar female female_only fishnets goddess greyscale japanese_text kneeling large_breasts long_hair looking_at_viewer lum monochrome oni pantyhose pointy_chin pointy_ears princess pussy ran_(urusei_yatsura) shoes tagme text tomboy trio urusei_yatsura wide_hips wrist_cuffs
1980s 1985 1girls akuma_kuma ass black_and_white breasts dildo female female_only horns humanoid large_breasts long_hair lum nipples nude oni pointy_ears princess sex_toy solo tagme urusei_yatsura
1980s 1985 1girls akuma_kuma ass black_and_white breasts dildo female female_only horns humanoid large_breasts long_hair lum nipples nude oni pointy_ears princess sex_toy solo tagme urusei_yatsura
1980s 1983 3boys audience cmnm curly_hair dark-skinned_male erect_nipples erection exposed_anus facial_hair grease holding_legs huge_cock imminent_rape legs_held_open male_only mouth_open muscular nude on_back pants_open penis_out penis_size_difference prison size_difference straight_hair tagme the_hun topless torn_pants
1980s 1983 3boys audience cmnm curly_hair dark-skinned_male erect_nipples erection exposed_anus facial_hair grease holding_legs huge_cock imminent_rape legs_held_open male_only mouth_open muscular nude on_back pants_open penis_out penis_size_difference prison size_difference straight_hair tagme the_hun topless torn_pants
1980s 1989 all_the_way_through anthro balls big_balls big_breasts bodily_fluids breasts canid canine canis centaur cum domestic_dog doug_winger furry futanari genital_fluids gynomorph gynomorph/gynomorph huge_balls huge_breasts human human_on_taur hyper hyper_penis intersex intersex/intersex interspecies mammal nude penis poodle taur
1980s 1989 all_the_way_through anthro balls big_balls big_breasts bodily_fluids breasts canid canine canis centaur cum domestic_dog doug_winger furry futanari genital_fluids gynomorph gynomorph/gynomorph huge_balls huge_breasts human human_on_taur hyper hyper_penis intersex intersex/intersex interspecies mammal nude penis poodle taur