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1990s 1997 20th_century anthro building canid canine canis crush crushed_underfoot crushed_vehicle female hair kolt licking licking_lips long_hair macro mammal monochrome muscular muscular_anthro muscular_female solo tongue tongue_out vehicle what wolf

1990s 1997 1boy 1girls 20th_century asuka_(viper) blush bottomless bra bra_lift breasts captain_(viper) clothing cowgirl_position defloration eyebrows_visible_through_hair female girl_on_top greyscale katsura_ken'ichirou large_breasts leg_grab long_hair male medium_breasts moaning monochrome navel night nipples novel_illustration official_art one_eye_closed open_clothes open_mouth outdoors penis pubic_hair pussy scan sogna sweat teeth thick_thighs thighs tongue tree underwear viper_(series) viper_ctr viper_ctr_(novel) virgin virginal_blood

asuka_(viper)blush

1990s 1997 1boy 1girls 20th_century arm_grab armpits asuka_(viper) blush bow bow_panties breasts captain_(viper) cleavage clothing covering covering_breasts embarrassed eyebrows_visible_through_hair feet female greyscale hakama indoors katsura_ken'ichirou kendo kneeling large_breasts long_hair looking_at_another male medium_breasts monochrome navel novel_illustration official_art open_mouth panties scan sitting sogna soles standing teeth thick_thighs thighs toes topless underwear viper_(series) viper_ctr viper_ctr_(novel) yokozuwari

arm_grabarmpits

1990s 1997 1boy 1girls 20th_century blush bow bow_bra bra bra_lift breasts closed_eyes clothed clothing eyebrows_visible_through_hair female greyscale katsura_ken'ichirou leg_grab long_hair lying male medium_breasts missionary_position monochrome nipples novel_illustration official_art on_back on_ground open_clothes open_mouth outdoors rape scan screaming sex shadow shiori_(viper) short_hair skirt socks sogna spread_legs sweat tears teeth thighs tongue underwear unseen_male_face vaginal_penetration viper_(series) viper_ctr viper_ctr_(novel)

1990s 1997 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_the_idiot_adventures purple_hair

1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair

1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair

1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair

1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair

1990s 1997 1boy 1girls 20th_century 90s ahoge angry animated antenna_hair armpits ass back barefoot bed_sheet black_eyes blush blushing body_writing bouncing_breasts bracelet breasts brown_hair clenched_teeth close-up clothed clothed_male clothed_male_nude_female clothing completely_naked completely_nude completely_nude_female covering covering_breasts covering_crotch covering_pussy covering_self defeat dive dizzy dodging earrings embarrassed embarrassed_nude_female energy energy_ball facial_mark feet female fighting fighting_stance flying full_body humor indoors jewelry jumping keyne_aqua kicking large_breasts levitating levitation long_hair looking_at_another male navel nipples no_sound nude nude_cover nude_female only_one_naked open_mouth pale_skin photon_earth photon_the_idiot_adventures pillow pointy_ears punching purple_hair red_eyes ring running running_away shaved_crotch shaved_pussy single_earring size_difference smaller_male smile soles sudden_realization takahashi_shinya teeth text toes tongue video

1990s 1997 1boy 1girls 20th_century after_sex all_fours anus aoki_reimu armpits asuka_(viper) bed_sheet black_hair blush bouncing_ass bouncing_breasts breasts brown_eyes brown_hair censored closed_eyes comic cum cum_in_pussy cum_inside cum_on_face cum_on_tongue cumshot doggy_style doujinshi ear_licking ejaculation eyebrows_visible_through_hair faceless_male facial feet female glans hand_on_hip heart highres japanese_text large_breasts leg_grab licking long_hair lying male matching_hair/eyes moaning navel nipples on_back open_mouth penis pubic_hair pussy pussy_ejaculation pussy_juice pussy_juice_drip pussy_juice_trail reverse_suspended_congress saliva saliva_drip saliva_string saliva_trail scan sex sogna soles sound_effects speech_bubble spoken_heart spread_legs squirting sweat tears teeth text thick_thighs thighs toes tongue tongue_out translation_request vaginal_penetration viper_(series) viper_anthology viper_ctr

after_sexall_fours

1990s 1997 1boy 1girls 20th_century all_fours aoki_reimu armpits ass asuka_(viper) bed_sheet black_hair blush bouncing_breasts bow bow_panties bra breast_grab breast_sucking breasts brown_eyes brown_hair cheek_bulge cleavage closed_eyes comic doggy_style doujinshi erect_nipples erect_nipples_under_clothes eye_contact eyebrows_visible_through_hair faceless_male fellatio female fingering hand_in_panties hand_on_hip hand_on_penis hand_on_shoulder highres japanese_text kissing large_breasts lingerie long_hair looking_at_each_other lying male matching_hair/eyes moaning navel nipples on_back one_breast_out open_mouth oral panties penis purple_bra purple_panties pussy_juice pussy_juice_drip pussy_juice_trail saliva saliva_drip saliva_on_penis saliva_string saliva_trail scan sex sogna sound_effects speech_bubble sweat tears teeth text thick_thighs thighs tongue tongue_out topless translation_request trembling underwear vaginal_penetration viper_(series) viper_anthology viper_ctr waist_grab

all_foursaoki_reimu

1997 1girls 4:3 akira_asagi anal anal_masturbation anal_sex animal_humanoid buttplug buttplug_tail capcom cat_humanoid clothing clothing_aside darkstalkers fake_tail felicia_(darkstalkers) felid felid_humanoid feline feline_humanoid female humanoid mammal mammal_humanoid masturbation nude orgasm_face panties penetration solo tail tail_masturbation underwear underwear_aside video_games

akira_asagianal

1990s 1997 20th_century 2boys anal_penetration anal_sex black_and_white bottomless cum cum_drip cum_in_ass douglas eyes_closed gay legs_held_open long_johns male male_only miner moustache neckerchief pick pleasure_face ripped_clothing traditional_media_(artwork) yaoi

anal_penetrationanal_sex

1990s 1997 20th_century absurdres anthro anus areola ass big_anus blue_eyes breasts female fur furry half-closed_eyes highres hindpaw james_m_hardiman looking_at_viewer mammal mephitid missing_sample natasha_(jmh) nipples nude open_mouth paws presenting presenting_anus presenting_hindquarters presenting_pussy pussy seductive skunk smile solo spread_butt spreading

absurdresanthro

1990s 1997 20th_century absurdres anthro black_fur black_nose breasts clitoris female fur furry green_eyes highres james_m_hardiman looking_down lori_(jmh) low-angle_view mammal mephitid nipples presenting pussy pussy_juice skunk solo spread_pussy spreading urethra white_fur white_hair

absurdresanthro

1990s 1997 20th_century absurdres anthro anus ass breasts clitoris close-up ear_piercing female furry highres james_m_hardiman long_labia looking_at_viewer looking_through_legs mammal mephitid nipple_piercing nipples nude onyx_(jmh) piercing presenting pussy pussy_close-up skunk solo spread_legs spread_pussy spreading upside-down

absurdresanthro

1990s 1997 20th_century absurdres anal anal_sex anthro anthro_on_anthro anus ass balls breasts clitoral_hood clitoris closed_eyes compression_artifacts cum cum_in_ass cum_inside curled_up duo erection fangs female female_penetrated furry highres james_m_hardiman lori_(jmh) lying male mammal mephitid nipples nude on_back open_mouth partial_male penis pussy sex skunk smile spread_legs spreading straight testicles white_hair

1990s 1997 20th_century absurdres anthro anus ass breasts chair female furry highres hindpaw james_m_hardiman mammal mephitid natasha_(jmh) nipples nude paws pussy sitting skunk solo

absurdresanthro

1990s 1997 20th_century absurdres anthro black_fur black_nose breasts claws female fur furry green_eyes highres james_m_hardiman lori_(jmh) mammal mephitid nipples nude pussy simple_background skunk solo white_background white_fur white_hair

absurdresanthro

1990s 1997 20th_century absurd_res anthro anus black_fur breasts brown_eyes ear_piercing female fur hair hi_res james_m_hardiman mammal mephitid nipple_piercing nipples nude onyx_(jmh) piercing pink_nose pussy raised_tail skunk solo spread_pussy spreading white_fur white_hair

absurd_resanthro

1990s 1997 20th_century all_fours anthro cum disney doggy_style domination drooling ek_goya felid female from_behind_position fucked_silly furry grin hyaenid hyena interspecies lion male mammal mane nude pantherine penis pussy saliva scar scar_(the_lion_king) sex shenzi smile spots straight the_lion_king

all_foursanthro

1990s 1997 20th_century 2boys black_hair boner brown_hair duo erect_nipples erection gay grapes horns imminent_sex looking_at_partner male male_only mouth_open penis pointy_ears retracted_foreskin satyr scottysdrawings smile tail_raised veiny_penis yaoi

black_hairboner

1990s 1997 20th_century final_fantasy final_fantasy_vii kanitama nipples red_eyes tifa_lockhart

final_fantasyfinal_fantasy_vii

1990s 1997 20th_century anthro bear blue_eyes brown_hair clothing eyelashes female fingerless_gloves gloves greg_panovich hair jynx_(greg_panovich) mammal nipples raised_eyebrow smile smirk unzipping

1990s 1997 1girls 20th_century 2d 2d_(artwork) 2d_animation 480p 640x480 90s anal_fingering animated ass ass_grab ass_grope assault breasts brown-tinted_eyewear chikan cool_devices crop_top crying denim_shorts dirty_talk english_subtitles female fingering_ass groped_from_behind groping groping_breasts hi_res high_heels highres humiliation longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_one_minute male medium_hair midriff molestation multiple_boys navel nipples orgasm penis pink_hair pussy pussy_juice red_high_heels retro retro_artstyle rina_yuki_(cool_devices) sexual_assault sexual_harassment short_shorts skimpy skimpy_clothes sound straight sunglasses tinted_eyewear train train_interior underboob video voyeurism

anal_fingeringanimated

1990s 1997 20th_century anatomically_correct anatomically_correct_anus anatomically_correct_genitalia anatomically_correct_penis anatomically_correct_pussy animal_anus animal_genitalia animal_penis animal_pussy antlers anus balls cervine cervine_anus cervine_genitalia cervine_penis cervine_pussy crouching erection female feral feral_on_feral fur genitals horn in_heat male mammal mule_deer peeing penis pussy sheath surprise tim_o'rourke urine year

anatomically_correctanatomically_correct_anus

1990s 1997 20th_century animal_genitalia anthro breasts doug_winger herm intersex mammal mouse multi_breast nude pussy rodent sheath solo

animal_genitaliaanthro

1990s 1997 20th_century 2futas anthro breasts canine cum dialogue dickgirl doug_winger duo edging erection furry futa_on_futa futa_only futanari intersex mammal pandora_(doug_winger) penis raised_tail skunk text

1990s 1997 20th_century anal cervine deer doug_winger duo male mammal nipples nude penis yaoi

1990s 1997 20th_century after_sex anal anal_sex anthro anus ass claws cum cum_drip cum_in_ass cum_inside cum_on_ass dripping duo female humanoid_penis james_m_hardiman lori_(jmh) male mammal nude penetration penis pussy raised_tail skunk spread_anus spreading straight

1990s 1997 20th_century anthro anus black_and_white breasts claws female james_m_hardiman looking_at_viewer mammal monochrome nipples nude onyx_(jmh) pussy skunk solo traditional_media_(artwork)

1990s 1997 20th_century anthro black_fur black_nose breasts clitoris female fur green_eyes hair james_m_hardiman looking_down lori_(jmh) mammal nipples pussy pussy_juice skunk solo spread_pussy spreading urethra white_fur white_hair

anthroblack_fur

1990s 1997 20th_century anthro black_fur breasts closed_eyes cum cum_in_mouth cum_inside duo female fur hair james_m_hardiman male mammal natasha_(jmh) nipples nude open_mouth penis skunk straight white_fur white_hair

anthroblack_fur

1990s 1997 20th_century anthro black_fur breasts claws female fur hair james_m_hardiman lori_(jmh) mammal nipples nude pussy skunk solo white_fur white_hair

anthroblack_fur

1990s 1997 20th_century 4_fingers anthro blue_body breasts desiree_(jmh) female green_hair hair james_m_hardiman lizard nipples nude pussy reptile scalie shampoo shower solo

anthroblue_body

1990s 1997 20th_century anus big_anus claws close-up feline female gaping gaping_pussy james_m_hardiman mammal nude piercing pussy pussy_close-up pussy_juice solo spread_pussy spreading urethra yellow_eyes

1990s 1997 20th_century anal anal_fingering anal_masturbation anthro anus big_anus claws close-up feline female finger_fuck fingering fingering_self gaping gaping_anus james_m_hardiman looking_back mammal masturbation messy pussy pussy_juice raised_tail solo spread_anus spreading vaginal_masturbation vaginal_penetration

analanal_fingering

1990s 1997 20th_century anal anal_sex anthro bat blue_eyes breasts brown_eyes canine claws duo female food_in_ass fox funnel james_m_hardiman mammal membranous_wings messy milk oral penetration piercing pussy simple_background straw tongue valerie_(jmh) white_background wings yuri yvonne_(jmh)

1997 1girls ami_mizuno anus areolae bishoujo_senshi_sailor_moon blue_eyes blue_hair blush breasts dithering eyeliner female female_only nipples nude pussy sad small_breasts solo tsukiyo_no_ribbon uncensored

1990s 1997 20th_century anthro bed blue_eyes bondage bound bound_to_bed buckteeth buttplug canine dildo domination duo english_text female femdom flat_chested fox fur furry genitals gloves_(marking) grey_eyes grey_fur half-closed_eyes imminent_sex interspecies kneeling lagomorph lube lying mammal markings multicolored_fur nude on_back orange_fur pillow predator/prey pussy rabbit rope rope_bondage sex_toy shocked simple_background smile spread_eagle spread_legs spreading strap-on teeth text tim_o'rourke two_tone_fur white_background white_fur year yuri

1990s 1997 1girls 20th_century 2boys after_sex anatomically_correct anatomically_correct_anus anatomically_correct_genitalia anatomically_correct_penis animal_anus animal_genitalia animal_penis antlers anus backsack balls bars bi_domination bisexual bit_gag black_fur blindfold bondage bound bridle centaur closed_eyes cloven_hooves cum cum_drip cum_in_ass cum_in_pussy cum_inside cum_pool cumshot domination dripping dungeon ejaculation equine equine_anus equine_genitalia equine_penis equine_taur erection female femsub feral feral_on_taur forced from_behind_position fur gag gagged genital_piercing genitals group group_sex hobbled hooves horn horsecock indoors interspecies jar larger_male lightning lube male male_and_female_subs male_domination male_on_feral malesub mammal markings mask mounting multiple_subs one_leg_up orgasm paintbrush penetration penis penis_piercing pentagram petplay piercing ponyplay raised_tail rape reins roleplay sex size_difference skull smaller_female smaller_male spread_legs spreader_bar spreading straight tail_bondage taur teats tim_o'rourke tongue tongue_out uncensored unicorn vaginal_penetration white_fur window yaoi year zoophilia

after_sexanatomically_correct

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