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1999

1999 4_fingers all_the_way_through all_three_filled ambiguous_gender anal anal_sex anthro ass big_breasts black_body black_fur bodily_fluids boots breasts clothing consentacles cum cum_covered cum_in_hair cum_on_breasts cum_on_butt cum_on_face cum_on_tentacle demon demona_(joe_rosales) duo eric_schwartz female female/ambiguous fingers fishnet_clothing fishnet_legwear fur genital_fluids hair hand_on_butt hatching_(art) heart_symbol high_heeled_boots high_heels horn legwear legwear_only licking licking_lips lidded_eyes long_hair looking_at_another looking_at_partner looking_back looking_pleasured mammal mephitid messy monochrome multiple_insertions nipples oral oral_penetration penetration raised_tail restrained restrained_by_tentacles sex shaded side_boob side_view simple_shading skunk slimy_(eric_schwartz) tail tentacle tentacle_around_horn tentacle_creature tentacle_in_ass tentacle_in_mouth tentacle_in_pussy tentacle_penetration tentacle_sex tentacles_around_arms tentacles_around_legs tentacles_around_tail tongue traditional_media_(artwork) vaginal_penetration white_body white_fur
1999 4_fingers all_the_way_through all_three_filled ambiguous_gender anal anal_sex anthro ass big_breasts black_body black_fur bodily_fluids boots breasts clothing consentacles cum cum_covered cum_in_hair cum_on_breasts cum_on_butt cum_on_face cum_on_tentacle demon demona_(joe_rosales) duo eric_schwartz female female/ambiguous fingers fishnet_clothing fishnet_legwear fur genital_fluids hair hand_on_butt hatching_(art) heart_symbol high_heeled_boots high_heels horn legwear legwear_only licking licking_lips lidded_eyes long_hair looking_at_another looking_at_partner looking_back looking_pleasured mammal mephitid messy monochrome multiple_insertions nipples oral oral_penetration penetration raised_tail restrained restrained_by_tentacles sex shaded side_boob side_view simple_shading skunk slimy_(eric_schwartz) tail tentacle tentacle_around_horn tentacle_creature tentacle_in_ass tentacle_in_mouth tentacle_in_pussy tentacle_penetration tentacle_sex tentacles_around_arms tentacles_around_legs tentacles_around_tail tongue traditional_media_(artwork) vaginal_penetration white_body white_fur
1990s 1990s_(style) 1999 1boy 1girls 20th_century 2d 2d_(artwork) 2d_animation 2girls 90s 960x720 almost_caught animated animation apologizing bed being_watched blackmail blush bouncing_breasts breast_grab breasts brown_hair brown_hair_female changing_clothes clothed clothed_male coercion dubbed_version elf_(company) embarrassed_female english_audio english_dialogue english_dub english_voice english_voice_acting female forest fujima_moeko glasses green_eyes green_eyes_female hentai hentai_series hi_res high_resolution highres implied_masturbation implied_penetration indoors long_hair long_red_hair long_twintails long_video longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male meganekko minazuki_shiho mp4 night nipples older_male older_man_and_younger_girl orange_dress over_480p peeing peeing_female pink_pineapple rape recording recording_sex red_hair rubbing_ass rubbing_leg shusaku socks sound tears twintails twintails_(hairstyle) urine video video_camera video_recording virgin virginity_loss voice_acted waiting_for_sex watching yellow_towel younger_female
1990s 1990s_(style) 1999 1boy 1girls 20th_century 2d 2d_(artwork) 2d_animation 2girls 90s 960x720 almost_caught animated animation apologizing bed being_watched blackmail blush bouncing_breasts breast_grab breasts brown_hair brown_hair_female changing_clothes clothed clothed_male coercion dubbed_version elf_(company) embarrassed_female english_audio english_dialogue english_dub english_voice english_voice_acting female forest fujima_moeko glasses green_eyes green_eyes_female hentai hentai_series hi_res high_resolution highres implied_masturbation implied_penetration indoors long_hair long_red_hair long_twintails long_video longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male meganekko minazuki_shiho mp4 night nipples older_male older_man_and_younger_girl orange_dress over_480p peeing peeing_female pink_pineapple rape recording recording_sex red_hair rubbing_ass rubbing_leg shusaku socks sound tears twintails twintails_(hairstyle) urine video video_camera video_recording virgin virginity_loss voice_acted waiting_for_sex watching yellow_towel younger_female
1999 artist_name artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty don_shigeru edit female female_focus female_only grobulus hourglass_figure parasite_eve pinup pinup_pose short_hair square_enix tagme tagme_(artist) wide_hips
1999 artist_name artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty don_shigeru edit female female_focus female_only grobulus hourglass_figure parasite_eve pinup pinup_pose short_hair square_enix tagme tagme_(artist) wide_hips
1999 artist_name artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty don_shigeru female female_focus female_only hourglass_figure parasite_eve pinup pinup_pose short_hair square_enix tagme tagme_(artist) wide_hips
1999 artist_name artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty don_shigeru female female_focus female_only hourglass_figure parasite_eve pinup pinup_pose short_hair square_enix tagme tagme_(artist) wide_hips
1999 1girls anus big_ass big_breasts bread breasts canon_pregnancy cum cum_on_body female huge_belly huge_butt kiki's_delivery_service nipples nude osono pregnant pussy red_hair scat team_shuffle trump trump_(team_shuffle)
1999 1girls anus big_ass big_breasts bread breasts canon_pregnancy cum cum_on_body female huge_belly huge_butt kiki's_delivery_service nipples nude osono pregnant pussy red_hair scat team_shuffle trump trump_(team_shuffle)
1999 3d 4girls black_hair bondage brown_hair chain_collar chain_gang coffle collar desert execution exposed female female_only insects naked_female nude_female red_hair render spread_eagle thrallord
1999 3d 4girls black_hair bondage brown_hair chain_collar chain_gang coffle collar desert execution exposed female female_only insects naked_female nude_female red_hair render spread_eagle thrallord
1999 3d blonde_hair bondage chained_to_pole chained_to_post covering_breast covering_pussy female female_only metal_collar naked_female nude_female render restrained solo_female thrallord wooden_wall
1999 3d blonde_hair bondage chained_to_pole chained_to_post covering_breast covering_pussy female female_only metal_collar naked_female nude_female render restrained solo_female thrallord wooden_wall
1999 3d blonde_hair bondage female female_only render see-through_clothing shackled shackles solo_female thrallord tree
1999 3d blonde_hair bondage female female_only render see-through_clothing shackled shackles solo_female thrallord tree
1999 3d black_hair blonde_hair bondage cactus cowboy desert japanese_female pussy_exposed school_uniform schoolgirl thrallord tits_out western whip_marks wild_west
1999 3d black_hair blonde_hair bondage cactus cowboy desert japanese_female pussy_exposed school_uniform schoolgirl thrallord tits_out western whip_marks wild_west
1999 6boys abducted arms_tied_to_pole ballet bondage bound castle cmnf female forced_to_watch kidnapped kidnapping kneeling kneeling_female knight naked_female nude_female render rope_bondage swan_lake thrallord wrists_tied
1999 6boys abducted arms_tied_to_pole ballet bondage bound castle cmnf female forced_to_watch kidnapped kidnapping kneeling kneeling_female knight naked_female nude_female render rope_bondage swan_lake thrallord wrists_tied
1990s 1999 1boy balls boots camera condom dated english_text full_body furry furry_only giraffe gloves hammer karno male male_only penis solo speech_bubble standing tagme text
1990s 1999 1boy balls boots camera condom dated english_text full_body furry furry_only giraffe gloves hammer karno male male_only penis solo speech_bubble standing tagme text
1990s 1999 20th_century ambiguous_fluids ambiguous_gender ambiguous_genitalia bodily_fluids centaur claws closed_eyes cum cum_in_mouth cum_inside dragon duo equid equid_taur fellatio frill_(anatomy) genital_fluids head_crest head_frill hooves humanoid_taur male male/ambiguous mammal mammal_taur monochrome oral penile pillow scales scalie sex source_request taur unknown_artist western_dragon
1990s 1999 20th_century ambiguous_fluids ambiguous_gender ambiguous_genitalia bodily_fluids centaur claws closed_eyes cum cum_in_mouth cum_inside dragon duo equid equid_taur fellatio frill_(anatomy) genital_fluids head_crest head_frill hooves humanoid_taur male male/ambiguous mammal mammal_taur monochrome oral penile pillow scales scalie sex source_request taur unknown_artist western_dragon
1990s 1999 2girls balloon_inflation belly_expansion blonde_hair breast_expansion breasts_bigger_than_head brunette bursting colored comic death defeated female female_death fuusenroba gloves inflation kiss kiss_of_death kissing_through_mask kitana leotard mileena mortal_kombat multiple_girls popping ripping_clothing tagme thighhighs
1990s 1999 2girls balloon_inflation belly_expansion blonde_hair breast_expansion breasts_bigger_than_head brunette bursting colored comic death defeated female female_death fuusenroba gloves inflation kiss kiss_of_death kissing_through_mask kitana leotard mileena mortal_kombat multiple_girls popping ripping_clothing tagme thighhighs
1990s 1999 2girls anthro beer belly_expansion blimp blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue floating fuusenroba horse hose hose_bulge immobile inflation multiple_girls narration nude sunken_head sunken_limbs tagme tethered text
1990s 1999 2girls anthro beer belly_expansion blimp blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue floating fuusenroba horse hose hose_bulge immobile inflation multiple_girls narration nude sunken_head sunken_limbs tagme tethered text
1990s 1999 2girls anal_insertion anthro beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba horse hose hose_bulge immobile implied_penetration inflation leotard multiple_girls narration nipples nude rolling tagme text
1990s 1999 2girls anal_insertion anthro beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba horse hose hose_bulge immobile implied_penetration inflation leotard multiple_girls narration nipples nude rolling tagme text
1990s 1999 2girls anthro axe beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba horse immobile inflation multiple_girls narration nude tagme text
1990s 1999 2girls anthro axe beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba horse immobile inflation multiple_girls narration nude tagme text
1990s 1999 2girls anthro beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba glasses horse inflation multiple_girls narration nude tagme tail text
1990s 1999 2girls anthro beer belly_expansion blue_pony breast_expansion breasts breasts_bigger_than_head carrie_nation colored comic dialogue fuusenroba glasses horse inflation multiple_girls narration nude tagme tail text
1990s 1999 1boy1girl anthro belly_expansion boxers bra breast_expansion christmas colored female fuusenroba horse hug inflation inflation_fetish male panties soft_belly tagme
1990s 1999 1boy1girl anthro belly_expansion boxers bra breast_expansion christmas colored female fuusenroba horse hug inflation inflation_fetish male panties soft_belly tagme
1990s 1999 20th_century 3boys anthro antlers bushycat canid canine cervid cervine christmas claws cum ejaculate furry gay harness hooves interspecies living_plush living_plushie lupine male male_focus male_only penis plush plushie plushophilia reindeer semen stuffed_animal stuffed_toy testicles toe_claws traditional_art traditional_media traditional_media_(artwork) trio wolf yaoi
1990s 1999 20th_century 3boys anthro antlers bushycat canid canine cervid cervine christmas claws cum ejaculate furry gay harness hooves interspecies living_plush living_plushie lupine male male_focus male_only penis plush plushie plushophilia reindeer semen stuffed_animal stuffed_toy testicles toe_claws traditional_art traditional_media traditional_media_(artwork) trio wolf yaoi
1990s 1999 20th_century 2boys anal anal_penetration anal_sex anthro bow bunny bushycat claws crying cum cum_in_ass ejaculate felid feline furry gay lagomorph lapine living_plush living_plushie long_tail male male_penetrated male_penetrating male_penetrating_male penis penis_in_ass plush plushie plushophilia rabbit ribbon semen short_tail skinny_tail stuffed_animal stuffed_toy tail tears testicles toe_claws whiskers yaoi
1990s 1999 20th_century 2boys anal anal_penetration anal_sex anthro bow bunny bushycat claws crying cum cum_in_ass ejaculate felid feline furry gay lagomorph lapine living_plush living_plushie long_tail male male_penetrated male_penetrating male_penetrating_male penis penis_in_ass plush plushie plushophilia rabbit ribbon semen short_tail skinny_tail stuffed_animal stuffed_toy tail tears testicles toe_claws whiskers yaoi
1990s 1999 1girls 20th_century anthro breasts female female_focus female_only furry gloves_(marking) hands_behind_head ironbadger long_hair mephitid naked nipples nude nudity pussy skunk socks_(marking) solo solo_female tail_down vagina white_hair
1990s 1999 1girls 20th_century anthro breasts female female_focus female_only furry gloves_(marking) hands_behind_head ironbadger long_hair mephitid naked nipples nude nudity pussy skunk socks_(marking) solo solo_female tail_down vagina white_hair
1990s 1999 20th_century 2boys anthro canid canine cum_in_mouth cum_in_own_mouth dog drinking_own_cum duo erect_penis erection fox frank_gembeck furry gay genitals licking_ass malamute male/male male_focus male_only nipple penis rimjob rimming rimming_male vulpine yaoi
1990s 1999 20th_century 2boys anthro canid canine cum_in_mouth cum_in_own_mouth dog drinking_own_cum duo erect_penis erection fox frank_gembeck furry gay genitals licking_ass malamute male/male male_focus male_only nipple penis rimjob rimming rimming_male vulpine yaoi
1990s 1999 20th_century 3boys anal anal_penetration anal_sex canid canine collaboration couch couch_sex frank_gembeck furry gay guppy_(artist) male/male male_focus male_only masturbation penis_in_ass threesome yaoi
1990s 1999 20th_century 3boys anal anal_penetration anal_sex canid canine collaboration couch couch_sex frank_gembeck furry gay guppy_(artist) male/male male_focus male_only masturbation penis_in_ass threesome yaoi
1990s 1999 20th_century 2boys anal anal_penetration anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro collar duo eyes_closed felid feline frank_gembeck furry gay gay_sex leopard male/male male_focus male_only male_penetrated male_penetrating male_penetrating_male mammal nipples penis penis_in_ass ponytail sex sexual_intercourse snow_leopard testicles white_hair yaoi
1990s 1999 20th_century 2boys anal anal_penetration anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro collar duo eyes_closed felid feline frank_gembeck furry gay gay_sex leopard male/male male_focus male_only male_penetrated male_penetrating male_penetrating_male mammal nipples penis penis_in_ass ponytail sex sexual_intercourse snow_leopard testicles white_hair yaoi
1990s 1999 20th_century 2boys anthro associated_student_bodies balls bottomless color cum cum_on_tongue cumshot day daytime duo ejaculate erect_penis erection frank_gembeck full_body furry furry_only gay glasses hand_on_penis interspecies kneeling male male/male male_only masturbation meerkat outdoors outside penis raccoon richard_sebastian ringtail shirt testicles timothy_montgomery tongue tongue_out yaoi
1990s 1999 20th_century 2boys anthro associated_student_bodies balls bottomless color cum cum_on_tongue cumshot day daytime duo ejaculate erect_penis erection frank_gembeck full_body furry furry_only gay glasses hand_on_penis interspecies kneeling male male/male male_only masturbation meerkat outdoors outside penis raccoon richard_sebastian ringtail shirt testicles timothy_montgomery tongue tongue_out yaoi
1990s 1999 1boy 20th_century anthro ball black_and_white bucky_boy canine collar eyes_closed furry jump jumping male male_focus male_only mouth_open penis poodle solo solo_male testicles tongue
1990s 1999 1boy 20th_century anthro ball black_and_white bucky_boy canine collar eyes_closed furry jump jumping male male_focus male_only mouth_open penis poodle solo solo_male testicles tongue
1990s 1999 20th_century anthro bondage bound bound_arms bound_tail bound_wrists chains cuffs furry gay gay_flag nipples otter pride_flag rainbow_flag sheath tail testicles whitefire
1990s 1999 20th_century anthro bondage bound bound_arms bound_tail bound_wrists chains cuffs furry gay gay_flag nipples otter pride_flag rainbow_flag sheath tail testicles whitefire
1990s 1999 20th_century animal_genitalia anthro arms_above_head arms_up blond_hair bondage bound bound_wrists fox furry green_eyes long_hair long_hair_male male mammal naked naked_male nipples nude nude_male sheath tail testicles vulpine whitefire
1990s 1999 20th_century animal_genitalia anthro arms_above_head arms_up blond_hair bondage bound bound_wrists fox furry green_eyes long_hair long_hair_male male mammal naked naked_male nipples nude nude_male sheath tail testicles vulpine whitefire
1990s 1999 1boy 20th_century anthro bondage bound cbt erect_penis erection fox fur furry furry_only gay male male_only penis rope simple_background solo solo_male tagme testicles white_background whitefire
1990s 1999 1boy 20th_century anthro bondage bound cbt erect_penis erection fox fur furry furry_only gay male male_only penis rope simple_background solo solo_male tagme testicles white_background whitefire
1990s 1999 20th_century anthro black_and_white bondage bound bound_arms bound_legs bound_tail bound_wrists bushycat captured chain_bondage chains dildo feline furry group leash living_plush living_plushie living_toy orgy plush plushie plushophilia revenge revenge_sex sex_toy stuffed_animal stuffed_toy tail whiskers
1990s 1999 20th_century anthro black_and_white bondage bound bound_arms bound_legs bound_tail bound_wrists bushycat captured chain_bondage chains dildo feline furry group leash living_plush living_plushie living_toy orgy plush plushie plushophilia revenge revenge_sex sex_toy stuffed_animal stuffed_toy tail whiskers
1990s 1999 1boy 20th_century anthro balls black_and_white bushycat canine claws cum cumshot ejaculation eyes_closed furry lupine male penis plush plushie plushophilia solo solo_male stuffed_animal stuffed_toy tail testicles wolf
1990s 1999 1boy 20th_century anthro balls black_and_white bushycat canine claws cum cumshot ejaculation eyes_closed furry lupine male penis plush plushie plushophilia solo solo_male stuffed_animal stuffed_toy tail testicles wolf
1990s 1999 20th_century 2boys anthro artist_name artist_signature balls canine dialogue falstaff furry gay hybrid jessica_willard lupine male male/male male_only multicolored_body multicolored_fur nipple_piercing nipple_rings nipples nose_piercing nose_ring penis pierced_ears pierced_nipples piercings sheath signature testicle_grab testicles unseen_male_face wolf yaoi
1990s 1999 20th_century 2boys anthro artist_name artist_signature balls canine dialogue falstaff furry gay hybrid jessica_willard lupine male male/male male_only multicolored_body multicolored_fur nipple_piercing nipple_rings nipples nose_piercing nose_ring penis pierced_ears pierced_nipples piercings sheath signature testicle_grab testicles unseen_male_face wolf yaoi
1990s 1999 1intersex 20th_century 2girls anthro breasts cock female furry futanari intersex mouse mousey_love_girls nipples penis terrie_smith vaginal vaginal_penetration
1990s 1999 1intersex 20th_century 2girls anthro breasts cock female furry futanari intersex mouse mousey_love_girls nipples penis terrie_smith vaginal vaginal_penetration
1990s 1990s_(style) 1999 1girls 20th_century aozee bare_shoulders bewitching_thighs bikini bikini_bottom blue_eyes blush bra british british_female brown_hair clavicle cleavage closed_mouth collarbone curvaceous_female curvaceous_figure curvaceous_hips disney eyeshadow jane_porter light-skinned_female linea_alba long_hair looking_at_viewer lower_body makeup mascara medium_breasts messy_hair midriff narrow_shoulders narrow_waist obliques partially_colored pawg pushup_bra red_lipstick standing tarzan_(1999_film) thick_eyebrows thigh_gap toned_female underwear_only unfinished venus_body walt_disney_animation_studios wide_hips yellow_bikini
1990s 1990s_(style) 1999 1girls 20th_century aozee bare_shoulders bewitching_thighs bikini bikini_bottom blue_eyes blush bra british british_female brown_hair clavicle cleavage closed_mouth collarbone curvaceous_female curvaceous_figure curvaceous_hips disney eyeshadow jane_porter light-skinned_female linea_alba long_hair looking_at_viewer lower_body makeup mascara medium_breasts messy_hair midriff narrow_shoulders narrow_waist obliques partially_colored pawg pushup_bra red_lipstick standing tarzan_(1999_film) thick_eyebrows thigh_gap toned_female underwear_only unfinished venus_body walt_disney_animation_studios wide_hips yellow_bikini
1990s 1999 20th_century all_fours anal anal_sex animal_genitalia anthro anthro_on_anthro balls blitz_(road_rovers) blue_eyes bottomless breasts brown_body brown_fur canid canine canis clothed clothing colleen_(road_rovers) collie dialogue dobermann doggy_style domestic_dog duo english_text erection female female_penetrated from_behind_position fur genitals hair herding_dog kthanid_(artist) male male/female male_penetrating male_penetrating_female mammal nipples nude pastoral_dog penetration penis pinscher raised_tail red_eyes road_rovers sex sheath sheepdog side_boob side_view speech_bubble tail text
1990s 1999 20th_century all_fours anal anal_sex animal_genitalia anthro anthro_on_anthro balls blitz_(road_rovers) blue_eyes bottomless breasts brown_body brown_fur canid canine canis clothed clothing colleen_(road_rovers) collie dialogue dobermann doggy_style domestic_dog duo english_text erection female female_penetrated from_behind_position fur genitals hair herding_dog kthanid_(artist) male male/female male_penetrating male_penetrating_female mammal nipples nude pastoral_dog penetration penis pinscher raised_tail red_eyes road_rovers sex sheath sheepdog side_boob side_view speech_bubble tail text
1990s 1999 20th_century anthro anus bed bed_sheet bedding blonde_hair breasts brown_body brown_fur chip_'n_dale_rescue_rangers chip_(disney) chipmunk dialogue disney duo english_text female fur furniture gadget_hackwrench genitals ground_squirrel hair kthanid_(artist) male male/female mammal mouse murid murine navel nude page_5 page_number pillow pink_nose purple_eyes pussy rear_view rodent sciurid scut_tail short_tail spread_legs spreading tail tan_body tan_fur text
1990s 1999 20th_century anthro anus bed bed_sheet bedding blonde_hair breasts brown_body brown_fur chip_'n_dale_rescue_rangers chip_(disney) chipmunk dialogue disney duo english_text female fur furniture gadget_hackwrench genitals ground_squirrel hair kthanid_(artist) male male/female mammal mouse murid murine navel nude page_5 page_number pillow pink_nose purple_eyes pussy rear_view rodent sciurid scut_tail short_tail spread_legs spreading tail tan_body tan_fur text