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1990

1990 1990s 1girls animated ass character_request kounai_shasei panties red_background removing_clothing removing_panties stripping studio_fantasia studio_signal
1990 1990s 1girls animated ass character_request kounai_shasei panties red_background removing_clothing removing_panties stripping studio_fantasia studio_signal
1990 1990s 1girls anthro black_and_white blonde_hair breasts female footwear furry high_heels long_hair monochrome never_forget nipples no_color pussy removing_clothing shoes shoes_only side_boob skunk terrie_smith
1990 1990s 1girls anthro black_and_white blonde_hair breasts female footwear furry high_heels long_hair monochrome never_forget nipples no_color pussy removing_clothing shoes shoes_only side_boob skunk terrie_smith
1990 1990s 1boy 1girls 20th_century anthro anthro_on_female anthro_on_human anthro_penetrating_female anthro_penetrating_human female groping_crotch handjob holding_penis human human_on_anthro interspecies light-skinned_female light_skin male male/female male_werewolf naked nude nude_female penis the_werewolf vagina vaginal_fingering vaginal_penetration werewolf
1990 1990s 1boy 1girls 20th_century anthro anthro_on_female anthro_on_human anthro_penetrating_female anthro_penetrating_human female groping_crotch handjob holding_penis human human_on_anthro interspecies light-skinned_female light_skin male male/female male_werewolf naked nude nude_female penis the_werewolf vagina vaginal_fingering vaginal_penetration werewolf
1990 1990s animal_humanoid big_breasts breasts clothing felid feline female hair humanoid looking_at_viewer mammal mammal_humanoid nipples not_furry olivia_de_berardinis painting_(artwork) smile solo tail traditional_media_(artwork)
1990 1990s animal_humanoid big_breasts breasts clothing felid feline female hair humanoid looking_at_viewer mammal mammal_humanoid nipples not_furry olivia_de_berardinis painting_(artwork) smile solo tail traditional_media_(artwork)
1990 1990s all_fours ambiguous_penetration anthro anthro_penetrating anthro_penetrating_human artist_name balls biped bodily_fluids bottomless claws clothed clothing colored_pencil_(artwork) cum cum_in_mouth cum_inside dialogue doggy_style drinking drinking_cum english_text erection fellatio female female_penetrated from_behind_position genital_fluids genitals group gulp_(sound_effect) hat headgear headwear human human_on_anthro human_penetrated interspecies male male/female male_penetrating male_penetrating_female mammal mostly_nude motion_outline mustelid nude onomatopoeia open_mouth oral oral_penetration otter penetration penile penile_penetration penis sex simple_background sound_effects speech_bubble strega tail text thrusting toe_claws tongue tongue_out traditional_media_(artwork) trio whiskers white_background year
1990 1990s all_fours ambiguous_penetration anthro anthro_penetrating anthro_penetrating_human artist_name balls biped bodily_fluids bottomless claws clothed clothing colored_pencil_(artwork) cum cum_in_mouth cum_inside dialogue doggy_style drinking drinking_cum english_text erection fellatio female female_penetrated from_behind_position genital_fluids genitals group gulp_(sound_effect) hat headgear headwear human human_on_anthro human_penetrated interspecies male male/female male_penetrating male_penetrating_female mammal mostly_nude motion_outline mustelid nude onomatopoeia open_mouth oral oral_penetration otter penetration penile penile_penetration penis sex simple_background sound_effects speech_bubble strega tail text thrusting toe_claws tongue tongue_out traditional_media_(artwork) trio whiskers white_background year
1990 1990s 1animal 1boy 1girls 20th_century barn barn_house border breast_out breast_outside breasts briefcase character_name cherry_poptart cherry_poptart_(comic) cloud clouds day daytime facing_viewer farm farm_girl farmer farmgirl full_body grin hand_on_hip happy hat hoe hoe_(tool) larry_welz looking_at_viewer monochrome naked_overalls nipple one_breast_out one_breast_out_of_clothes outdoors overall_shorts overalls pig pinup salesman shit-eating_grin small_breasts standing straight_hair sunflower sunflowers tool tractor trees twintails wooden_fence year
1990 1990s 1animal 1boy 1girls 20th_century barn barn_house border breast_out breast_outside breasts briefcase character_name cherry_poptart cherry_poptart_(comic) cloud clouds day daytime facing_viewer farm farm_girl farmer farmgirl full_body grin hand_on_hip happy hat hoe hoe_(tool) larry_welz looking_at_viewer monochrome naked_overalls nipple one_breast_out one_breast_out_of_clothes outdoors overall_shorts overalls pig pinup salesman shit-eating_grin small_breasts standing straight_hair sunflower sunflowers tool tractor trees twintails wooden_fence year
1990 1990s 20th_century anus barely_visible_genitalia barely_visible_pussy black_pawpads breasts brown_hair canid_taur canine canine_taur dipstick_tail female fox fox_taur furry genitals gloves_(marking) leg_markings looking_back mammal mammal_taur markings multicolored_tail nipples nude open_mouth pawpads pussy rear_view roy_d._pounds_ii socks_(marking) solo straight_hair taur year yellow_fur
1990 1990s 20th_century anus barely_visible_genitalia barely_visible_pussy black_pawpads breasts brown_hair canid_taur canine canine_taur dipstick_tail female fox fox_taur furry genitals gloves_(marking) leg_markings looking_back mammal mammal_taur markings multicolored_tail nipples nude open_mouth pawpads pussy rear_view roy_d._pounds_ii socks_(marking) solo straight_hair taur year yellow_fur
1990 1990s 1boy 1girls 20th_century ass blonde blonde_hair butt cherry_poptart cherry_poptart_(comic) comic comic_cover couch female gerbil house larry_welz no_panties no_pants pantsless partly_clothed partly_nude pillows shirt_only straight_hair tagme top_only
1990 1990s 1boy 1girls 20th_century ass blonde blonde_hair butt cherry_poptart cherry_poptart_(comic) comic comic_cover couch female gerbil house larry_welz no_panties no_pants pantsless partly_clothed partly_nude pillows shirt_only straight_hair tagme top_only
1990 1990s 1girls 20th_century 3d_glasses blonde blonde_hair bodysuit cherry_pop cherry_poptart_(comic) comic comic_cover computer english_text futuristic futuristic_clothing goggles green-tinted_eyewear larry_welz metal_skin nipple_pinch nipples red-tinted_eyewear skinsuit speech_bubble straight_hair tinted_eyewear visor
1990 1990s 1girls 20th_century 3d_glasses blonde blonde_hair bodysuit cherry_pop cherry_poptart_(comic) comic comic_cover computer english_text futuristic futuristic_clothing goggles green-tinted_eyewear larry_welz metal_skin nipple_pinch nipples red-tinted_eyewear skinsuit speech_bubble straight_hair tinted_eyewear visor
1990 1990s 1boy 20th_century 3girls beauty_contest big_hair bikini bikini_competition black_hair blonde blonde_hair blue_bikini breasts brown_hair cape cherry_poptart cherry_poptart_(comic) comic comic_cover competition competition_swimsuit contest cover_page crying curly_hair female flowers host larry_welz lola_palooza nipple_bulge pink_bikini purple_bikini red_bikini skinny skinny_girl straight_hair text_bubble tiara word_bubble year
1990 1990s 1boy 20th_century 3girls beauty_contest big_hair bikini bikini_competition black_hair blonde blonde_hair blue_bikini breasts brown_hair cape cherry_poptart cherry_poptart_(comic) comic comic_cover competition competition_swimsuit contest cover_page crying curly_hair female flowers host larry_welz lola_palooza nipple_bulge pink_bikini purple_bikini red_bikini skinny skinny_girl straight_hair text_bubble tiara word_bubble year
1990 1990s 1996 20th_century abs anthro building building_destruction building_penetration city destruction felid genitals giant_male hands_behind_head kaiju kencougr looking_at_object macro macro_male male mammal micro_on_macro monochrome muscular muscular_anthro muscular_male open_mouth pantherine penis solo tiger traditional_media_(artwork)
1990 1990s 1996 20th_century abs anthro building building_destruction building_penetration city destruction felid genitals giant_male hands_behind_head kaiju kencougr looking_at_object macro macro_male male mammal micro_on_macro monochrome muscular muscular_anthro muscular_male open_mouth pantherine penis solo tiger traditional_media_(artwork)
1990 1990s 1996 20th_century abs anthro bodily_fluids crush crushed_vehicle cum destruction duo english_text felid genital_fluids hair handjob head_grab improvised_sex_toy kencougr licking licking_lips macro male male/male mammal monochrome muscular muscular_male orgasm pantherine penile sex short_hair text tiger tongue tongue_out traditional_media_(artwork) vehicle
1990 1990s 1996 20th_century abs anthro bodily_fluids crush crushed_vehicle cum destruction duo english_text felid genital_fluids hair handjob head_grab improvised_sex_toy kencougr licking licking_lips macro male male/male mammal monochrome muscular muscular_male orgasm pantherine penile sex short_hair text tiger tongue tongue_out traditional_media_(artwork) vehicle
1990 1990s 20th_century anthro breasts female fur furry lagomorph mammal mauvette pussy rabbit solo space steve_martin straight_hair year
1990 1990s 20th_century anthro breasts female fur furry lagomorph mammal mauvette pussy rabbit solo space steve_martin straight_hair year
1990 1990s 20th_century 3girls amagi_kei aqua_eyes arm arms art ass back bare_arms bare_back bare_legs bare_shoulders barefoot beach blonde_hair blue_eyes blush bow breasts character_request closed_mouth collarbone hairbow idol_densetsu_eriko legs looking_at_another looking_at_viewer looking_back lying medium_breasts multiple_girls neck nipples nude on_back on_side on_stomach orange_hair outdoors parted_lips pink_bow public_nudity sand short_hair smile straight_hair tamura_eriko twintails water wet
1990 1990s 20th_century 3girls amagi_kei aqua_eyes arm arms art ass back bare_arms bare_back bare_legs bare_shoulders barefoot beach blonde_hair blue_eyes blush bow breasts character_request closed_mouth collarbone hairbow idol_densetsu_eriko legs looking_at_another looking_at_viewer looking_back lying medium_breasts multiple_girls neck nipples nude on_back on_side on_stomach orange_hair outdoors parted_lips pink_bow public_nudity sand short_hair smile straight_hair tamura_eriko twintails water wet
1990 1990s 20th_century ambiguous_gender balls black_and_white caprine chasing cliff comic fairy female feral forced grass human human_on_feral humanoid_penis humor interspecies magic male mammal monochrome mountain nipples nude open_mouth outside penis pubes rape running sheep traditional_media traditional_media_(artwork) transformation zoophilia
1990 1990s 20th_century ambiguous_gender balls black_and_white caprine chasing cliff comic fairy female feral forced grass human human_on_feral humanoid_penis humor interspecies magic male mammal monochrome mountain nipples nude open_mouth outside penis pubes rape running sheep traditional_media traditional_media_(artwork) transformation zoophilia
1990 1990s 20th_century ambiguous_gender balls black_and_white caprine chasing cliff comic feral forced grass human human_on_feral humanoid_penis humor imminent_rape interspecies male mammal monochrome mountain nude open_mouth outside penis rape running sheep zoophilia
1990 1990s 20th_century ambiguous_gender balls black_and_white caprine chasing cliff comic feral forced grass human human_on_feral humanoid_penis humor imminent_rape interspecies male mammal monochrome mountain nude open_mouth outside penis rape running sheep zoophilia
! 1990 1990s 20th_century balls big_breasts bovine bow breasts chode cum cumshot elephant english_text equine eyewear female flaccid glans glasses karno long_penis male midget monochrome mouse muscles nipples orgasm paizuri penis pussy rodent straight_hair text wet
! 1990 1990s 20th_century balls big_breasts bovine bow breasts chode cum cumshot elephant english_text equine eyewear female flaccid glans glasses karno long_penis male midget monochrome mouse muscles nipples orgasm paizuri penis pussy rodent straight_hair text wet
1990 1990s 20th_century anthro balls big_breasts breasts chode cum cum_inside elephant end_page english_text equine eyewear female flaccid fur furry glans glasses karno long_penis male midget monochrome mouse muscles nipples penis pussy rodent straight_hair text wet
1990 1990s 20th_century anthro balls big_breasts breasts chode cum cum_inside elephant end_page english_text equine eyewear female flaccid fur furry glans glasses karno long_penis male midget monochrome mouse muscles nipples penis pussy rodent straight_hair text wet
1990 1990s 20th_century balls big_breasts bovine breasts cape chode elephant english_text female flaccid furry horn huge_cock karno male midget monochrome mouse muscles nipples oils penis rodent straight_hair text
1990 1990s 20th_century balls big_breasts bovine breasts cape chode elephant english_text female flaccid furry horn huge_cock karno male midget monochrome mouse muscles nipples oils penis rodent straight_hair text
1990 1990s 20th_century 5boys arm_tattoo artist_signature balls_on_chin blonde_hair blowjob blowjob_face closed_eyes cock_gobble cock_hungry cum cum_hungry cum_in_mouth cum_on_face cumshot_into_mouth dark-skinned_male dark_penis ed_cervone erection fellatio gay giving_head going_down_on group holding_penis large_penis montage moustache mouth_open mouthful multiple_males multiple_penises nude oral oral_sex orgy pale-skinned_male penis penis_in_mouth penis_on_face penis_size_difference pubic_hair retracted_foreskin sketch straight_hair stroking_cock sucking sucking_off testicles tongue_out uncut veiny_penis yaoi
1990 1990s 20th_century 5boys arm_tattoo artist_signature balls_on_chin blonde_hair blowjob blowjob_face closed_eyes cock_gobble cock_hungry cum cum_hungry cum_in_mouth cum_on_face cumshot_into_mouth dark-skinned_male dark_penis ed_cervone erection fellatio gay giving_head going_down_on group holding_penis large_penis montage moustache mouth_open mouthful multiple_males multiple_penises nude oral oral_sex orgy pale-skinned_male penis penis_in_mouth penis_on_face penis_size_difference pubic_hair retracted_foreskin sketch straight_hair stroking_cock sucking sucking_off testicles tongue_out uncut veiny_penis yaoi
1990 1990s 1girls 20th_century blush breasts female female_only masturbation pussy ranma-chan ranma_1/2 ranma_saotome red_hair signature solo straight_hair sweat takashi_taya uncensored
1990 1990s 1girls 20th_century blush breasts female female_only masturbation pussy ranma-chan ranma_1/2 ranma_saotome red_hair signature solo straight_hair sweat takashi_taya uncensored
1990 1990s 1boy 1girls 20th_century akane_tendo artist_request bed doggy_style female male monochrome ranma-kun ranma_1/2 ranma_saotome sex straight straight_hair year
1990 1990s 1boy 1girls 20th_century akane_tendo artist_request bed doggy_style female male monochrome ranma-kun ranma_1/2 ranma_saotome sex straight straight_hair year
1990 1990s 20th_century anal anal_sex anus balls bear big_penis black_fur bovine breasts bull cape chapter_1 curled_hair double_penetration end_page equine erection female hooves horse karno male muscles penetration penis pussy straight_hair vaginal_penetration
1990 1990s 20th_century anal anal_sex anus balls bear big_penis black_fur bovine breasts bull cape chapter_1 curled_hair double_penetration end_page equine erection female hooves horse karno male muscles penetration penis pussy straight_hair vaginal_penetration
1990 1990s 20th_century anus balls bear big_penis black_fur bovine bow breasts bull cape curled_hair english_text equine erection eyeswear female furry giraffe glasses hooves horse karno male muscles original original_character penetration penis pussy pussy_juice straight_hair sword_fight vaginal_penetration victory
1990 1990s 20th_century anus balls bear big_penis black_fur bovine bow breasts bull cape curled_hair english_text equine erection eyeswear female furry giraffe glasses hooves horse karno male muscles original original_character penetration penis pussy pussy_juice straight_hair sword_fight vaginal_penetration victory
1990 1990s 20th_century 2boys 90s ass balls big_penis black_fur bovine bull cape comic english_text equine erection furry furry_only hooves horse karno male male_only monochrome muscles muscular muscular_male penis speech_bubble straight_hair sword_fight text veiny_penis
1990 1990s 20th_century 2boys 90s ass balls big_penis black_fur bovine bull cape comic english_text equine erection furry furry_only hooves horse karno male male_only monochrome muscles muscular muscular_male penis speech_bubble straight_hair sword_fight text veiny_penis
1990 1990s 20th_century balls bear big_breasts big_penis black_fur bovine breasts bull cape curled_hair elephant equine erection flaccid giraffe hooves horse karno muscles penis pussy straight_hair sword_fight
1990 1990s 20th_century balls bear big_breasts big_penis black_fur bovine breasts bull cape curled_hair elephant equine erection flaccid giraffe hooves horse karno muscles penis pussy straight_hair sword_fight
1990 1990s 20th_century angry balls bear big_hair big_penis black_fur bovine breasts bull cape curled_hair elephant equine flaccid fur giraffe hair hooves horse karno muscles penis pussy straight_hair
1990 1990s 20th_century angry balls bear big_hair big_penis black_fur bovine breasts bull cape curled_hair elephant equine flaccid fur giraffe hair hooves horse karno muscles penis pussy straight_hair
1990 1990s 20th_century angry bear big_hair big_penis black_fur bovine breasts bull cape curled_hair elephant equine fur giraffe hair hooves horse karno kicking monochrome muscles oral penis pussy straight_hair testicles text
1990 1990s 20th_century angry bear big_hair big_penis black_fur bovine breasts bull cape curled_hair elephant equine fur giraffe hair hooves horse karno kicking monochrome muscles oral penis pussy straight_hair testicles text
1990 1990s 20th_century 2boys 90s balls black_fur boing bored bovine bull cape comic dated english_text equine furry furry_only hooves horse karno male male_only monochrome muscles nude page_1 penis sitting speech_bubble straight_hair text
1990 1990s 20th_century 2boys 90s balls black_fur boing bored bovine bull cape comic dated english_text equine furry furry_only hooves horse karno male male_only monochrome muscles nude page_1 penis sitting speech_bubble straight_hair text
1990 1990s 20th_century breasts censored female long_hair mihoshi_kuramitsu monochrome tagme tenchi_masaki tenchi_muyo! year
1990 1990s 20th_century breasts censored female long_hair mihoshi_kuramitsu monochrome tagme tenchi_masaki tenchi_muyo! year
1990 1990s 1girls 20th_century anal_insertion bondage boots breasts curvaceous dirty_pair female greyscale human large_breasts long_hair monochrome nipples nude pussy straight_hair tagme wingbird year yuri_(dirty_pair)
1990 1990s 1girls 20th_century anal_insertion bondage boots breasts curvaceous dirty_pair female greyscale human large_breasts long_hair monochrome nipples nude pussy straight_hair tagme wingbird year yuri_(dirty_pair)
1990 1990s 1girls 20th_century adam_hughes beatriz_da_costa breasts dc female fire_(dc) jla justice_league justice_league_international latina straight_hair year
1990 1990s 1girls 20th_century adam_hughes beatriz_da_costa breasts dc female fire_(dc) jla justice_league justice_league_international latina straight_hair year
1990 1990s anthro bed breasts canine chest_tuft cougar couple crimson_rose cunnilingus feline female force fox fur furry kencougr male oral oral_sex orgasm ouch puma sex size_difference straight straight_hair
1990 1990s anthro bed breasts canine chest_tuft cougar couple crimson_rose cunnilingus feline female force fox fur furry kencougr male oral oral_sex orgasm ouch puma sex size_difference straight straight_hair
1990 1990s 20th_century anthro bed breasts brian_o'connell canine female fox fur furry greyscale hair looking_at_viewer monochrome on_side pussy signature solo straight_hair tail year
1990 1990s 20th_century anthro bed breasts brian_o'connell canine female fox fur furry greyscale hair looking_at_viewer monochrome on_side pussy signature solo straight_hair tail year
1990 1990s 20th_century amy_fox anthro breasts brian_sutton briano canine female fox fur furry jewelry pottery pussy straight_hair year
1990 1990s 20th_century amy_fox anthro breasts brian_sutton briano canine female fox fur furry jewelry pottery pussy straight_hair year
1990 1990s 20th_century anniversary anthro bed bovine breasts bull candle female furry green_eyes hooves horns karno male nude on_side orange_hair penis straight_hair year
1990 1990s 20th_century anniversary anthro bed bovine breasts bull candle female furry green_eyes hooves horns karno male nude on_side orange_hair penis straight_hair year