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1999

1999 anthro ass backsack balls black_nose blue_sky brown_body brown_fur canid canine dark_natasha day detailed_background full-length_portrait fur genitals grass grey_pawpads hand_on_leg hand_on_own_leg hand_on_own_thigh hand_on_thigh hindpaw humanoid_hands male mammal mountain nude outside pawpads paws plant portrait rear_view rock shaded sky snout solo tail traditional_media_(artwork)
1999 anthro ass backsack balls black_nose blue_sky brown_body brown_fur canid canine dark_natasha day detailed_background full-length_portrait fur genitals grass grey_pawpads hand_on_leg hand_on_own_leg hand_on_own_thigh hand_on_thigh hindpaw humanoid_hands male mammal mountain nude outside pawpads paws plant portrait rear_view rock shaded sky snout solo tail traditional_media_(artwork)
1999 anthro b_(artist) balls black_claws buckteeth claws condom crossed_legs full-length_portrait fur genitals hair hindpaw holding_condom holding_object lagomorph leporid licking licking_lips licking_own_lips looking_at_viewer male male_only mammal navel nude paws pen_(artwork) penis penis_tip pink_inner_ear pink_nose portrait rabbit red_tongue seducing_viewer sexual_barrier_device shaded simple_background sitting solo teeth toe_claws tongue traditional_media_(artwork) unused_condom white_background white_body white_fur white_hair wrapped_condom
1999 anthro b_(artist) balls black_claws buckteeth claws condom crossed_legs full-length_portrait fur genitals hair hindpaw holding_condom holding_object lagomorph leporid licking licking_lips licking_own_lips looking_at_viewer male male_only mammal navel nude paws pen_(artwork) penis penis_tip pink_inner_ear pink_nose portrait rabbit red_tongue seducing_viewer sexual_barrier_device shaded simple_background sitting solo teeth toe_claws tongue traditional_media_(artwork) unused_condom white_background white_body white_fur white_hair wrapped_condom
1999 1girls artistic_nude closed_eyes featureless_breasts female game_freak kasumi_(pokemon) ken_sugimori nintendo nonsexual_nudity nude nude_female official_art orange_hair pokemon pokemon_rgby pokemon_trading_card_game sideboob small_breasts solo solo_female staryu tears water
1999 1girls artistic_nude closed_eyes featureless_breasts female game_freak kasumi_(pokemon) ken_sugimori nintendo nonsexual_nudity nude nude_female official_art orange_hair pokemon pokemon_rgby pokemon_trading_card_game sideboob small_breasts solo solo_female staryu tears water
1999 athletic athletic_female big_breasts blackfell blue_eyes breasts busty female female_focus female_only hourglass_figure lara_croft lara_croft_(classic) large_breasts lipstick looking_over_eyewear looking_over_sunglasses makeup navel nude nude_female nudity slim_waist sunglasses tagme tinted_eyewear tomb_raider water wide_hips
1999 athletic athletic_female big_breasts blackfell blue_eyes breasts busty female female_focus female_only hourglass_figure lara_croft lara_croft_(classic) large_breasts lipstick looking_over_eyewear looking_over_sunglasses makeup navel nude nude_female nudity slim_waist sunglasses tagme tinted_eyewear tomb_raider water wide_hips
1999 2_penises 2_tails ambiguous_penetration american_tails anthro archie_comics black_nose bodily_fluids boots bottomless breasts brown_body brown_fur canid canine classic_tails clothed clothing dialogue diphallia diphallism dipstick_tail duo english_text female footwear fox fur genital_fluids genitals gloves ground_squirrel hair handwear kthanid_(artist) looking_at_another looking_at_partner looking_back looking_back_at_another looking_back_at_partner male male/female mammal markings multi_genitalia multi_penis multi_tail nipples nude open_clothing open_topwear open_vest penetration penis red_hair rodent sally_acorn sciurid scut_tail sega shoes short_tail small_breasts sonic_(series) sonic_satam sonic_the_hedgehog_(archie) sonic_the_hedgehog_(comics) sonic_the_hedgehog_(series) tail tail_markings tails text topwear vaginal_fluids vest wildbrain
1999 2_penises 2_tails ambiguous_penetration american_tails anthro archie_comics black_nose bodily_fluids boots bottomless breasts brown_body brown_fur canid canine classic_tails clothed clothing dialogue diphallia diphallism dipstick_tail duo english_text female footwear fox fur genital_fluids genitals gloves ground_squirrel hair handwear kthanid_(artist) looking_at_another looking_at_partner looking_back looking_back_at_another looking_back_at_partner male male/female mammal markings multi_genitalia multi_penis multi_tail nipples nude open_clothing open_topwear open_vest penetration penis red_hair rodent sally_acorn sciurid scut_tail sega shoes short_tail small_breasts sonic_(series) sonic_satam sonic_the_hedgehog_(archie) sonic_the_hedgehog_(comics) sonic_the_hedgehog_(series) tail tail_markings tails text topwear vaginal_fluids vest wildbrain
1999 3_toes 4_fingers accessory anthro ass bedroom_eyes black_body black_fur bodily_fluids bottomwear braided_hair breasts butt_focus camera chest_tuft cleavage clitoral_hood clitoris close-up closed_eyes clothed clothing cum cum_on_anus cum_on_butt cum_on_penis cum_on_tail cum_string dialogue digital_media_(artwork) disembodied_penis duo erection eric_schwartz facial_markings feet felid fellatio female fingers fur genital_close-up genital_fluids genitals hair hair_accessory hair_ribbon hatching_(art) head_markings hi_res holding_camera holding_object holding_photo humanoid_genitalia humanoid_penis hybrid licking licking_lips long_hair male male/female mammal markings multiple_images narrowed_eyes nipple_outline open_mouth oral pantherine pants penetration penile penis plantigrade pussy pussy_close-up question raised_tail ribbons saliva saliva_on_tongue seductive sex shaded shirt shorts signature simple_background speech_bubble standing striped_body striped_fur striped_markings striped_tail stripes t-shirt tail tail_markings tamar toes tongue topwear tuft vaginal_fluids vaginal_penetration vein veiny_penis white_background white_body white_fur white_hair zig_zag
1999 3_toes 4_fingers accessory anthro ass bedroom_eyes black_body black_fur bodily_fluids bottomwear braided_hair breasts butt_focus camera chest_tuft cleavage clitoral_hood clitoris close-up closed_eyes clothed clothing cum cum_on_anus cum_on_butt cum_on_penis cum_on_tail cum_string dialogue digital_media_(artwork) disembodied_penis duo erection eric_schwartz facial_markings feet felid fellatio female fingers fur genital_close-up genital_fluids genitals hair hair_accessory hair_ribbon hatching_(art) head_markings hi_res holding_camera holding_object holding_photo humanoid_genitalia humanoid_penis hybrid licking licking_lips long_hair male male/female mammal markings multiple_images narrowed_eyes nipple_outline open_mouth oral pantherine pants penetration penile penis plantigrade pussy pussy_close-up question raised_tail ribbons saliva saliva_on_tongue seductive sex shaded shirt shorts signature simple_background speech_bubble standing striped_body striped_fur striped_markings striped_tail stripes t-shirt tail tail_markings tamar toes tongue topwear tuft vaginal_fluids vaginal_penetration vein veiny_penis white_background white_body white_fur white_hair zig_zag
1999 4_fingers anthro black_and_white breasts cleavage closed_eyes clothed clothing digital_drawing_(artwork) digital_media_(artwork) duo english_text eric_schwartz eyewear eyewear_on_head facial_markings fantasizing female fingers fur glasses glasses_on_head hair hand_on_own_breast head_markings head_on_hand heart_symbol hybrid lidded_eyes long_hair looking_pleasured mammal markings medium_hair mephitid monochrome nipple_outline open_mouth sabrina_(sabrina_online) sabrina_online signature simple_background skunk striped_body striped_fur stripes text thought_bubble translucent translucent_hair white_background white_hair zig_zag
1999 4_fingers anthro black_and_white breasts cleavage closed_eyes clothed clothing digital_drawing_(artwork) digital_media_(artwork) duo english_text eric_schwartz eyewear eyewear_on_head facial_markings fantasizing female fingers fur glasses glasses_on_head hair hand_on_own_breast head_markings head_on_hand heart_symbol hybrid lidded_eyes long_hair looking_pleasured mammal markings medium_hair mephitid monochrome nipple_outline open_mouth sabrina_(sabrina_online) sabrina_online signature simple_background skunk striped_body striped_fur stripes text thought_bubble translucent translucent_hair white_background white_hair zig_zag
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 2girls 90s 960x720 almost_caught animated 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_dialogue english_dub english_voice english_voice_acting female forest fujima_moeko glasses green_eyes green_eyes_female 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 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 2girls 90s 960x720 almost_caught animated 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_dialogue english_dub english_voice english_voice_acting female forest fujima_moeko glasses green_eyes green_eyes_female 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 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_request artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty edit female female_focus female_only grobulus hourglass_figure parasite_eve pinup pinup_pose short_hair tagme wide_hips
1999 artist_name artist_request artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty edit female female_focus female_only grobulus hourglass_figure parasite_eve pinup pinup_pose short_hair tagme wide_hips
1999 artist_name artist_request artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty female female_focus female_only hourglass_figure parasite_eve pinup pinup_pose short_hair tagme wide_hips
1999 artist_name artist_request artist_signature athletic athletic_female aya_brea blonde_hair blue_eyes busty female female_focus female_only hourglass_figure parasite_eve pinup pinup_pose short_hair tagme 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_only female_solo metal_collar naked_female nude_female render restrained thrallord wooden_wall
1999 3d blonde_hair bondage chained_to_pole chained_to_post covering_breast covering_pussy female_only female_solo metal_collar naked_female nude_female render restrained thrallord wooden_wall
1999 3d blonde_hair bondage female_only female_solo render see-through_clothing shackled shackles thrallord tree
1999 3d blonde_hair bondage female_only female_solo render see-through_clothing shackled shackles 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 comic defeated female 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 comic defeated female 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 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 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 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 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 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 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 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 comic dialogue fuusenroba glasses horse inflation multiple_girls narration nude tagme tail text
1990s 1999 anthro belly_expansion boxers bra breast_expansion christmas fuusenroba horse hug inflation inflation_fetish panties soft_belly tagme
1990s 1999 anthro belly_expansion boxers bra breast_expansion christmas fuusenroba horse hug inflation inflation_fetish 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 3some 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 3some 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