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1990 -3d best from all time

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1990 1990s_(style) 1995 1boy 1boy1girl 1girls 2d amano_jyaku animated anus areola_slip ass audible_speech blue_hair bouncing_breasts bouncing_on_penis boy_rape breast_sucking breasts censored central_park_media clothed_male cowgirl_position demon demon_girl distortion english_audio english_dialogue fellatio female female_moaning female_on_top female_penetrated female_rapist femdom glowing glowing_eyes hentai hikimayu inside_view japanese_clothes kimono leather_belt licking_another's_face lipstick long_hair longer_than_2_minutes lowres makeup male male_rape_victim medium_breasts nipples on_ground oral outdoors paralysis penis princess rape red_eyes red_hair retro_artstyle reverse_forced_oral reverse_rape riding riding_cock riding_dick riding_penis self_breast_sucking sex shoes smile sound spiked_hair spread_legs statue straddling straight sucking_own_breasts supernatural sweat tagme time_stop tongue transparent unable_to_move undressing urotsukidouji vaginal_sex very_long_hair vest video wristband yellow_vest yoenhime_(urotsukidouji) yoenki_(urotsukidouji)

amano_jyakuanimated

1990 1990s_(style) 2d amano_megumi_(urotsukidouji) anal anatomy animated ass blue_eyes breasts demon female green_hair hentai kohoki lowres monster multiple_insertions nipples penis rape retro_artstyle sex sound tagme tentacle tentacle_sex thighhighs torn_clothes triple_penetration undressing urotsukidouji vaginal_penetration video window zettai_ryouiki

amano_megumi_(urotsukidouji)anal

1990 1990s 1girls 20th_century blush breasts clitoris clothed_masturbation clothing female female_only genderswap_(mtf) masturbation pubic_hair pussy ranma-chan ranma_1/2 ranma_saotome red_hair rule_63 signature small_breasts solo straight_hair sweat takashi_taya uncensored

1990 1990s_(style) 1995 1boy 1girls 2d amano_jyaku animated anus ass blue_hair bouncing_breasts breast_sucking breasts bridal_gauntlets censored cowgirl_position demon demon_girl facial_mark fellatio female femdom hentai hikimayu inside_view japanese_clothes kimono leather_belt licking_another's_face lipstick long_hair longer_than_one_minute lowres makeup male male_rape_victim medium_breasts music nipples on_ground oral outdoors paralysis princess rape red_eyes red_hair retro_artstyle reverse_forced_oral reverse_rape sex shoes short_hair smile sound spiked_hair spread_legs statue straddling straight tagme time_stop tongue urotsukidouji very_long_hair vest video wristband yellow_vest yoenhime_(urotsukidouji) yoenki_(urotsukidouji)

amano_jyakuanimated

1990 1990s 1girls animated ass character_request female kounai_shasei panties red_background removing_clothing removing_panties stripping studio_fantasia studio_signal

1990 1990s_(style) 1996 1boy 2d amano_megumi_(urotsukidouji) androgynous animated ass belt black_hair black_thighhighs blue_eyes blush bracelet breasts breasts_out doggy_style fellatio female floating glowing glowing_eyes green_hair hentai heterochromatic_eyewear holding_legs jewelry levitation licking licking_nipple licking_penis longer_than_3_minutes lowres magic male medium_breasts mind_control miniskirt mizuchi_(urotsukidouji) nipple_stimulation nipples open_mouth oral penis penis_tip retro_artstyle sex sex_from_behind shapeshifting short_hair sidelocks skirt sleeves_pushed_up sound sweater tagme teasing thighhighs tinted_eyewear tongue torn_clothes torn_thighhighs urotsukidouji video zettai_ryouiki

amano_megumi_(urotsukidouji)androgynous

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 female full_body grin hand_on_hip happy hat hoe hoe_(tool) larry_welz looking_at_viewer male monochrome naked_overalls nipples 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_(style) 1995 1boy amano_jyaku animated anus ass blue_hair bouncing_breasts breast_sucking breasts bridal_gauntlets censored collarbone cowgirl_position demon demon_girl facial_mark fellatio female femdom glowing glowing_eyes hikimayu inside_view japanese_clothes kimono leather_belt licking_another's_face lipstick long_hair lowres makeup male medium_breasts nails nipples on_ground oral outdoors paralysis princess purple_lips rape red_eyes red_hair retro_artstyle sex shoes smile sound spiked_hair spread_legs statue straddling straight tagme thick_eyebrows time_stop tongue undressing urotsukidouji vaginal_penetration very_long_hair vest video wristband yellow_vest yoenhime_(urotsukidouji) yoenki_(urotsukidouji)

amano_jyakuanimated

1990 1990s_(style) 2d amano_megumi_(urotsukidouji) anal animated closed_eyes female green_hair hentai kohoki lowres monster multiple_insertions rape retro_artstyle sex sound tagme tentacle tentacle_sex thighhighs torn_clothes urotsukidouji vaginal_penetration video zettai_ryouiki

amano_megumi_(urotsukidouji)anal

1990 1animal 1girls bear black_and_white black_fur blush bow breast_grab breasts clothed_sex clothing eyes_closed female genma_saotome human japanese_text kasumi_tendo legs_held_apart male panda pubic_hair pussy_juice ranma_1/2 reverse_cowgirl_position sex shirt shirt_lift sitting sitting_on_lap small_breasts speech_bubble takashi_taya tongue_out translation_request uncensored ursid white_fur zoophilia

bearblack_and_white

1990 1990s_(style) 2d animated blonde_hair breasts closed_eyes demon doggy_style drill_hair drill_sidelocks female ferris_wheel glowing glowing_eyes grabbing_another's_breast groping groping_breast held_up hentai implied_sex interspecies lingerie longer_than_30_seconds lowres monster night nipples nude rape red_eyes retro_artstyle sex sex_from_behind sidelocks sound straight tagme thighhighs underwear urotsukidouji vaginal_penetration video

animatedblonde_hair

1990 2girls akane_tendo ass bottomless breasts clothing female incest multiple_girls nabiki_tendo nipples nude pussy pussy_juice ranma_1/2 siblings sister sisters small_breasts sweat takashi_taya yuri

1990s 1girls 9/11 911 1990 anthro black_and_white blonde_hair breasts female footwear furry high_heels leg_warmers long_hair milestone_post monochrome never_forget nipples no_color pussy removing_clothing shoes shoes_only side_boob skunk terrie_smith they_hit_the_pentagon

anthroblack_and_white

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 male no_panties no_pants pantsless partly_clothed partly_nude pillows shirt_only straight_hair tagme top_only

1990 1990s_(style) 2d animated breast_sucking breasts demon double_bun female hair_bun hentai japanese_clothes kimono kuroko_(urotsukidouji) longer_than_10_seconds lowres monster nagumo_tatsuo nipples prostitution retro_artstyle shorter_than_30_seconds slap_mark slap_mark_on_face small_breasts sound sucking_nipple tagme urotsukidouji video window yukata

animatedbreast_sucking

1990 1990s 20th_century 3girls amagi_kei aqua_eyes 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 female 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

amagi_keiaqua_eyes

1990 1girls bow breasts clothed_sex clothing doujinshi female genma_saotome giant_panda kasumi_tendo monochrome panda ranma_1/2 sex small_breasts takashi_taya translation_request uncensored vaginal_penetration zoophilia

1990 1990s 1girls 20th_century adam_hughes beatriz_da_costa breasts dc dc_comics female fire_(dc) jla justice_league justice_league_international latina straight_hair year

adam_hughesbeatriz_da_costa

1990 1990s 20th_century 2girls alien alien_girl arisia_rrab artist_name blonde blonde_hair blue_hair breasts cleavage clothed clothed_sex clothing color colored costume dark_hair dated dc dc_comics dress female gloves green_lantern green_lantern_(series) green_lantern_corps grey_background hair hand_on_hip hands_on_hips humanoid katma_tui long_hair martin multiple_females multiple_girls nipple_bulge panties pantyshot red_skin signature skirt standing straight_hair superheroine tight_clothing uncensored underwear white_gloves year yellow_hair

alienalien_girl

1990 1990s_(style) 1995 animated breast_sucking breasts breasts_sucking closed_eyes demon demon_girl female femdom japanese_clothes kimono licking_nipple lipstick long_hair lowres makeup medium_breasts nipple_stimulation nipples princess red_hair retro_artstyle self_breast_sucking sucking_nipple sucking_own_breasts tagme urotsukidouji very_long_hair yoenki_(urotsukidouji)

animatedbreast_sucking

1990 1boy 1girls akane_tendo clothed_sex clothing crying doggy_style dress faceless_male female fred_kelly from_behind hand_on_head male monochrome panties panties_down ranma_1/2 rape tagme tears

akane_tendoclothed_sex

1990 1990s_(style) amano_megumi_(urotsukidouji) animated belt black_thighhighs blowing_kiss blue_eyes bracelet earrings female female_focus green_hair jewelry love_hearts lowres miniskirt one_eye_closed retro_artstyle short_hair skirt sleeves_pushed_up smile solo sweater tagme thighhighs urotsukidouji wink zettai_ryouiki

amano_megumi_(urotsukidouji)animated

1990 1990s_(style) 1995 1boy amano_jyaku animated ass blue_hair bouncing_breasts breasts cowgirl_position demon demon_girl earth_(planet) female femdom hikimayu japanese_clothes kimono lipstick long_hair lowres makeup male medium_breasts nipples on_ground open_clothes outdoors paralysis planet princess red_eyes red_hair retro_artstyle sex smile sound spiked_hair spread_legs straddling straight tagme time_stop urotsukidouji very_long_hair vest video wristband yellow_vest yoenki_(urotsukidouji)

amano_jyakuanimated

1990 1990s_(style) 1996 1boy amano_megumi_(urotsukidouji) androgynous animated ass black_hair doggy_style female floating green_hair holding_legs levitation lowres male mind_control mizuchi_(urotsukidouji) retro_artstyle sex sex_from_behind short_hair sidelocks tagme takeaki_kiryu thighhighs tongue torn_clothes torn_thighhighs urotsukidouji zettai_ryouiki

amano_megumi_(urotsukidouji)androgynous

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

all_foursambiguous_penetration

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 male nipple_bulge pink_bikini purple_bikini red_bikini skinny skinny_girl straight_hair text_bubble tiara word_bubble year

beauty_contestbig_hair

1990 1990s 1girls 20th_century armpits arms_behind_head bikini boots breasts bustier cleavage cry_for_dawn dawn_(comics) elbow_gloves facial_mark female female_only garter_belt garter_straps gloves hair_over_one_eyes joseph_michael_linsner knee_boots leg_lift lingerie lipstick long_hair makeup medium_breasts midriff monochrome panties red_eyes red_hair red_lipstick runny_makeup skull_print solo spot_color straight_hair swimsuit thighhighs underwear year

armpitsarms_behind_head

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 breasts comic cum cum_on_face female female_on_top girl_on_top human long_hair male medium_breasts one_eye_closed open_mouth paizuri penetration penis pubic_hair pussy ranma_1/2 rumoi_jun ryoga_hibiki sex shampoo_(ranma_1/2) spread_legs straight straight_hair titfuck uncensored vaginal_penetration

1990 1girls breasts clitoris clothed_masturbation clothing female female_only greyscale masturbation monochrome pubic_hair ranma-chan ranma_1/2 ranma_saotome small_breasts solo takashi_taya uncensored

breastsclitoris

1990 1990s_(style) 1995 1boy amano_jyaku animated ass blue_hair cowgirl_position demon demon_girl female femdom hikimayu japanese_clothes kimono long_hair lowres male on_ground outdoors paralysis princess red_hair retro_artstyle sex spiked_hair spread_legs straddling straight tagme time_stop urotsukidouji very_long_hair vest wristband yellow_vest yoenki_(urotsukidouji)

amano_jyakuanimated

1990 1girls bath breasts colored edit female human male nude ranma-kun ranma_1/2 ranma_saotome shampoo_(ranma_1/2) small_breasts straight takahashi_rumiko water

1990 1990s 20th_century braid breasts dated female human long_hair male naoki_koichi navel nipples penis pubic_hair pussy ranma-kun ranma_1/2 ranma_saotome sex shampoo_(ranma_1/2) small_breasts straight straight_hair uncensored unshaved_pussy vaginal_penetration

1990 1990s_(style) animated blonde_hair breasts closed_eyes demon doggy_style drill_hair drill_sidelocks female glowing glowing_eyes held_up interspecies lingerie lowres monster night nipples nude rape red_eyes retro_artstyle sex sex_from_behind sidelocks tagme thighhighs underwear urotsukidouji

animatedblonde_hair

1990 2girls blue_hair blue_hair_female blush breasts comic crossover doujin_cover duo female female/female female_only green_hair green_hair_female hand_on_breast hand_on_shoulder horns human humanoid large_breasts light-skinned_female light_skin long_hair looking_at_viewer lum multiple_girls nipples nude nude_female oni pointy_ears price_tag princess ranma_1/2 shampoo_(ranma_1/2) small_breasts tokimiran urusei_yatsura yuri

blue_hairblue_hair_female

1990 1990s_(style) animated animated blonde_hair blue_eyes breasts choker demon female leather_belt lipstick lowres makeup medium_breasts medium_hair mimi_(urotsukidouji) one_eye_closed pointy_ears princess retro_artstyle short_hair sidelocks smile tagme urotsukidouji wink

animatedanimated

1990 1990s_(style) amano_megumi_(urotsukidouji) anal animated animated female kohoki lowres monster multiple_insertions rape retro_artstyle sex tagme tentacle tentacle_sex thighhighs torn_clothes urotsukidouji vaginal_penetration zettai_ryouiki

amano_megumi_(urotsukidouji)anal

1990 1990s 1girls 90s black_background blonde_hair breasts cleavage clothed clothing custom_(company) cyberblock_metal_orange female female_only game_cg light-skinned_female light_skin pc88 pc98 pixel_art ponytail screenshot simple_background solo solo_female thighs tomo_(cyberblock_metal_orange) twintails yellow_eyes

black_backgroundblonde_hair

1990 1girls blue_hair blush breasts female female_only highres human long_hair nipples nude pubic_hair ranma_1/2 red_eyes shampoo_(ranma_1/2) small_breasts solo unshaved_pussy water yada_masaka

1990 1990s 20th_century 5boys arm_tattoo artist_signature balls 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 foreskin gay giving_head going_down_on group holding_penis large_penis male 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 uncircumcised uncut veiny_penis yaoi

arm_tattooartist_signature

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 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

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