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1999

1999 after_sex aged_down ass backsack bestiality blue_eyes bodily_fluids caught censored cum cum_in_pussy cum_inside cum_on_ground digital_media_(artwork) dripping duo felid female female_on_human feral fur genital_fluids genitals hetero hindpaw human human_on_feral ineffective_censorship interspecies japanese_text larger_female larger_feral leaking_cum long_tail looking_at_viewer looking_back lying male male_on_feral mammal momiji_yu-ga mosaic_censoring nude on_side original pantherine pawpads paws penis pussy shota simple_background size_difference smaller_human smaller_male striped striped_body striped_fur tail testicles text tiger translated yellow_eyes young_human young_male
1999 after_sex aged_down ass backsack bestiality blue_eyes bodily_fluids caught censored cum cum_in_pussy cum_inside cum_on_ground digital_media_(artwork) dripping duo felid female female_on_human feral fur genital_fluids genitals hetero hindpaw human human_on_feral ineffective_censorship interspecies japanese_text larger_female larger_feral leaking_cum long_tail looking_at_viewer looking_back lying male male_on_feral mammal momiji_yu-ga mosaic_censoring nude on_side original pantherine pawpads paws penis pussy shota simple_background size_difference smaller_human smaller_male striped striped_body striped_fur tail testicles text tiger translated yellow_eyes young_human young_male
1999 2girls age_difference aged_down alien_(franchise) alternate_species animal_humanoid brown_background brown_hair brown_nose canid canid_humanoid canine canine_humanoid carrying_character child clothed clothing coveralls curled_hair dog_humanoid duo ellen_ripley explosive female front_view fully_clothed furrification furry furry_female furry_with_furry green_clothing green_coveralls grenade grenade_belt gun hair holding holding_gun holding_object holding_ranged_weapon holding_weapon hug humanoid karabiner lifted mammal mammal_humanoid multiple_girls older_woman_and_younger_girl open_mouth protective pulse_rifle ranged_weapon rebecca_"newt"_jorden simple_background size_difference tan_clothing tan_shirt tan_topwear topwear weapon year yuri
1999 2girls age_difference aged_down alien_(franchise) alternate_species animal_humanoid brown_background brown_hair brown_nose canid canid_humanoid canine canine_humanoid carrying_character child clothed clothing coveralls curled_hair dog_humanoid duo ellen_ripley explosive female front_view fully_clothed furrification furry furry_female furry_with_furry green_clothing green_coveralls grenade grenade_belt gun hair holding holding_gun holding_object holding_ranged_weapon holding_weapon hug humanoid karabiner lifted mammal mammal_humanoid multiple_girls older_woman_and_younger_girl open_mouth protective pulse_rifle ranged_weapon rebecca_"newt"_jorden simple_background size_difference tan_clothing tan_shirt tan_topwear topwear weapon year yuri
1999 1girl 90s brown_eyes brown_hair comic_mujin cowboy_shot dress dress_lift female hairband highres hime_cut kojiki_ouji loli long_hair looking_at_viewer matching_hair/eyes nightgown non-web_source oldschool panties panty_pull pussy scan scan_artifacts signature skindentation skinny small_breasts solo striped striped_panties thighhighs underwear very_long_hair
1999 1girl 90s brown_eyes brown_hair comic_mujin cowboy_shot dress dress_lift female hairband highres hime_cut kojiki_ouji loli long_hair looking_at_viewer matching_hair/eyes nightgown non-web_source oldschool panties panty_pull pussy scan scan_artifacts signature skindentation skinny small_breasts solo striped striped_panties thighhighs underwear very_long_hair
1990s 1998 1999 animated armpits ass ass_focus back bare_ass bare_back big_ass big_buttocks black_hair blush bubble_butt chest clothed_female_nude_male comedy dokkiri_doctor embarrassed embarrassed_nude_male exposed_ass funny hongo_yukihiro huge_ass indoors knocked_out legs male non-web_source nude nude_male preteen_boy preteen_girl punching shota sound studio_pierrot underwear video weekly_shounen_sunday white_underwear
1990s 1998 1999 animated armpits ass ass_focus back bare_ass bare_back big_ass big_buttocks black_hair blush bubble_butt chest clothed_female_nude_male comedy dokkiri_doctor embarrassed embarrassed_nude_male exposed_ass funny hongo_yukihiro huge_ass indoors knocked_out legs male non-web_source nude nude_male preteen_boy preteen_girl punching shota sound studio_pierrot underwear video weekly_shounen_sunday white_underwear
1990s 1999 1boy 2000s 2009 20twenty :o animated ass ass_focus bare_ass bart_simpson big_ass big_buttocks bird blonde_hair blue_pants blue_shorts bottle bottomless brown_hair bubble_butt comedy cutting elementary_schoolboy english_audio exposed_ass fat_ass finger_pointing fox_corporation funny hiding holding_knife huge_ass kiss kissing_ass kissing_butt knife laughing little_boy male missing_tooth mooning non-web_source overalls paint pants pointing prank red_shirt screaming_out_off_camera shirt shorts shota sky sound spelling spray_bottle spray_can spray_paint spraying the_simpsons tree video yellow_skin
1990s 1999 1boy 2000s 2009 20twenty :o animated ass ass_focus bare_ass bart_simpson big_ass big_buttocks bird blonde_hair blue_pants blue_shorts bottle bottomless brown_hair bubble_butt comedy cutting elementary_schoolboy english_audio exposed_ass fat_ass finger_pointing fox_corporation funny hiding holding_knife huge_ass kiss kissing_ass kissing_butt knife laughing little_boy male missing_tooth mooning non-web_source overalls paint pants pointing prank red_shirt screaming_out_off_camera shirt shorts shota sky sound spelling spray_bottle spray_can spray_paint spraying the_simpsons tree video yellow_skin
1990s 1999 1boy 2000s 2004 20twenty :i american_flag angry_face animated armpits ass ass_focus bare_ass bart_simpson basketball_uniform big_ass big_buttocks blonde_hair bottomless bubble_butt carrot comedy covering covering_ass covering_crotch covering_nudity covering_penis destroyed_clothing donkey eating elementary_school elementary_schoolboy embarrased_male embarrassed embarrassed_nude_male english_audio exposed_ass fat_ass flag funny huge_ass indoors knees laughing legs little_boy male mooning no_pants no_underwear non-web_source photo prank public_nudity red_shirt school_gym shirt shoes shorts shota sleeveless sleeveless_shirt smile socks sound sportswear tearing_clothes tearing_up the_simpsons torn_clothes video wardrobe_malfunction white_shorts yellow_skin
1990s 1999 1boy 2000s 2004 20twenty :i american_flag angry_face animated armpits ass ass_focus bare_ass bart_simpson basketball_uniform big_ass big_buttocks blonde_hair bottomless bubble_butt carrot comedy covering covering_ass covering_crotch covering_nudity covering_penis destroyed_clothing donkey eating elementary_school elementary_schoolboy embarrased_male embarrassed embarrassed_nude_male english_audio exposed_ass fat_ass flag funny huge_ass indoors knees laughing legs little_boy male mooning no_pants no_underwear non-web_source photo prank public_nudity red_shirt school_gym shirt shoes shorts shota sleeveless sleeveless_shirt smile socks sound sportswear tearing_clothes tearing_up the_simpsons torn_clothes video wardrobe_malfunction white_shorts yellow_skin
1990s 1999 1boy 2000s 2004 20twenty accident animated ass ass_focus bare_ass barefoot bart_simpson bicycle big_ass big_buttocks blonde_hair blue_pants bottomless bubble_butt comedy elementary_schoolboy english_audio exposed_ass falling fat_ass feet fox_corporation funny green_pajamas homer_simpson huge_ass laughing little_boy male male_only medical_equipment mooning needle non-web_source outdoors pajamas pants riding running screaming shirt shoes shota smile soles sound teeth the_simpsons unicycle video white_shirt yellow_skin
1990s 1999 1boy 2000s 2004 20twenty accident animated ass ass_focus bare_ass barefoot bart_simpson bicycle big_ass big_buttocks blonde_hair blue_pants bottomless bubble_butt comedy elementary_schoolboy english_audio exposed_ass falling fat_ass feet fox_corporation funny green_pajamas homer_simpson huge_ass laughing little_boy male male_only medical_equipment mooning needle non-web_source outdoors pajamas pants riding running screaming shirt shoes shota smile soles sound teeth the_simpsons unicycle video white_shirt yellow_skin
1990s 1999 1boy 20twenty animated ass ass_focus back bare_ass bare_back barefoot bart_simpson big_ass big_buttocks blonde_hair bottomless bubble_butt coat doctor electrocution elementary_schoolboy english_audio exibitionism exposed_ass fat_ass feet hospital huge_ass indoors legs little_boy male non-web_source plaster pov robe shota sound the_simpsons toes video yellow_skin
1990s 1999 1boy 20twenty animated ass ass_focus back bare_ass bare_back barefoot bart_simpson big_ass big_buttocks blonde_hair bottomless bubble_butt coat doctor electrocution elementary_schoolboy english_audio exibitionism exposed_ass fat_ass feet hospital huge_ass indoors legs little_boy male non-web_source plaster pov robe shota sound the_simpsons toes video yellow_skin
1999 1girl 90s absurdres ass blue_eyes blue_hair blue_leotard boots english_text female full_body hairband highres hoshino_fuuta leotard loli marching_band marching_band_baton mating_press medium_hair oldschool original pinup skirt small_breasts smile solo source_request
1999 1girl 90s absurdres ass blue_eyes blue_hair blue_leotard boots english_text female full_body hairband highres hoshino_fuuta leotard loli marching_band marching_band_baton mating_press medium_hair oldschool original pinup skirt small_breasts smile solo source_request
1999 1boy 1girl 90s absurdres ahoge anus ass black_hair child_on_child closed_eyes cum cum_on_body female hetero highres hoshino_fuuta humping leg_lock loli male missionary nude oldschool original penis pleasure_face short_hair shota straight_shota
1999 1boy 1girl 90s absurdres ahoge anus ass black_hair child_on_child closed_eyes cum cum_on_body female hetero highres hoshino_fuuta humping leg_lock loli male missionary nude oldschool original penis pleasure_face short_hair shota straight_shota
1999 1girl 90s absurdres after_rape after_sex blue_eyes blue_hair blue_theme boots broken_rape_victim cum cum_in_pussy cum_inside cum_on_clothes elbow_gloves facial female gloves highres hoshino_fuuta leotard loli lying marching_band_baton matching_hair/eyes non-web_source oldschool on_back open_mouth original short_hair skirt small_breasts solo torn_clothes torn_leotard
1999 1girl 90s absurdres after_rape after_sex blue_eyes blue_hair blue_theme boots broken_rape_victim cum cum_in_pussy cum_inside cum_on_clothes elbow_gloves facial female gloves highres hoshino_fuuta leotard loli lying marching_band_baton matching_hair/eyes non-web_source oldschool on_back open_mouth original short_hair skirt small_breasts solo torn_clothes torn_leotard
1999 2girls 90s absurdres barefoot bathroom blush breasts child_on_child closed_eyes feet female female_ejaculation fingering flat_chest flat_chest_grab grabbing highres hoshino_fuuta legs loli loli_on_loli multiple_girls nipples non-web_source nude oldschool onsen open_mouth orange_hair orgasm original pee peeing pussy scan soap spread_legs toes yuri
1999 2girls 90s absurdres barefoot bathroom blush breasts child_on_child closed_eyes feet female female_ejaculation fingering flat_chest flat_chest_grab grabbing highres hoshino_fuuta legs loli loli_on_loli multiple_girls nipples non-web_source nude oldschool onsen open_mouth orange_hair orgasm original pee peeing pussy scan soap spread_legs toes yuri
1999 1girl 90s absurdres blush brown_hair cover female green_eyes hair_bobbles hair_ornament highres hoshino_fuuta japanese_text kneehighs legs looking_away medium_hair nipples non-web_source oldschool original panties panties_around_one_leg partially_visible_vulva plaid plaid_skirt pleated_skirt ponytail pussy pussy_juice red_skirt scan shirt_lift side_ponytail sitting skirt solo spread_legs tank_top tied_hair underwear white_panties
1999 1girl 90s absurdres blush brown_hair cover female green_eyes hair_bobbles hair_ornament highres hoshino_fuuta japanese_text kneehighs legs looking_away medium_hair nipples non-web_source oldschool original panties panties_around_one_leg partially_visible_vulva plaid plaid_skirt pleated_skirt ponytail pussy pussy_juice red_skirt scan shirt_lift side_ponytail sitting skirt solo spread_legs tank_top tied_hair underwear white_panties
1999 90s artist_name axe feathers female flat_chest greyscale hair_feathers hairband indigenous lips loli long_hair mihoto_kouji monochrome native_american no_bangs no_pants oldschool open_mouth original panties preteen semi-realistic straight_hair traditional_media tunic underwear upskirt weapon yawning
1999 90s artist_name axe feathers female flat_chest greyscale hair_feathers hairband indigenous lips loli long_hair mihoto_kouji monochrome native_american no_bangs no_pants oldschool open_mouth original panties preteen semi-realistic straight_hair traditional_media tunic underwear upskirt weapon yawning
1999 1girl 90s belt belt_buckle boots cowboy cowboy_boots cowboy_clothes cowboy_hat english_text female full_body greyscale gun handgun hat lips loli mihoto_kouji monochrome navel no_panties oldschool original pinup revolver semi-realistic solo weapon western
1999 1girl 90s belt belt_buckle boots cowboy cowboy_boots cowboy_clothes cowboy_hat english_text female full_body greyscale gun handgun hat lips loli mihoto_kouji monochrome navel no_panties oldschool original pinup revolver semi-realistic solo weapon western
1999 1girl 90s absurdres artist_request backpack bag blonde_hair blue_eyes copyright_request cover female freckles full_body hairband highres japanese_text light_smile loli long_hair looking_at_viewer magazine_cover non-web_source orange_backpack pantyhose randoseru school_uniform sitting smile solo strawberry_blonde_hair tech_gian traditional_media translation_request wavy_hair
1999 1girl 90s absurdres artist_request backpack bag blonde_hair blue_eyes copyright_request cover female freckles full_body hairband highres japanese_text light_smile loli long_hair looking_at_viewer magazine_cover non-web_source orange_backpack pantyhose randoseru school_uniform sitting smile solo strawberry_blonde_hair tech_gian traditional_media translation_request wavy_hair
1999 2girls 90s ass blue_eyes brown_hair christmas duo female flat_ass hat loli long_hair looking_at_another looking_at_viewer mihoto_kouji motor_vehicle motorcycle multiple_girls night original panties panty_peek pinup riding santa_costume santa_hat sitting sky star_(sky) surrealism thighhighs traditional_media underwear vehicle watermark web_address white_panties wind
1999 2girls 90s ass blue_eyes brown_hair christmas duo female flat_ass hat loli long_hair looking_at_another looking_at_viewer mihoto_kouji motor_vehicle motorcycle multiple_girls night original panties panty_peek pinup riding santa_costume santa_hat sitting sky star_(sky) surrealism thighhighs traditional_media underwear vehicle watermark web_address white_panties wind
1999 angelica_pickles female flat_chest klasky_csupo loli nickelodeon nude rugrats tentacle_sex tentacles zone
1999 angelica_pickles female flat_chest klasky_csupo loli nickelodeon nude rugrats tentacle_sex tentacles zone
1999 1boy 1girl animaniacs artist_initials brother_and_sister character_name cheek_licking cum cum_in_pussy cum_inside dot_warner english_text female furry hetero kthanid licking licking_face male offscreen_character saliva sex siblings skippy_squirrel wakko_warner warner_brothers year
1999 1boy 1girl animaniacs artist_initials brother_and_sister character_name cheek_licking cum cum_in_pussy cum_inside dot_warner english_text female furry hetero kthanid licking licking_face male offscreen_character saliva sex siblings skippy_squirrel wakko_warner warner_brothers year
1999 animaniacs dot_warner furry kthanid sex skippy_squirrel tagme warner_brothers
1999 animaniacs dot_warner furry kthanid sex skippy_squirrel tagme warner_brothers
1999 1boy 1girl bottomless brain_(inspector_gadget) brainwashed dic_entertainment duo female inspector_gadget loli male nude penny_(inspector_gadget) pussy standing
1999 1boy 1girl bottomless brain_(inspector_gadget) brainwashed dic_entertainment duo female inspector_gadget loli male nude penny_(inspector_gadget) pussy standing
1999 1boy artdecade biped blush bodily_fluids canid canine clothing cub cum cum_in_mouth cum_in_own_mouth cum_in_pussy cum_in_self cum_inside cum_on_own_face cum_on_own_tongue cum_on_self cum_on_tongue erection facial footwear fox fur furry genital_fluids genitals gloomwolfe gloves handwear japanese_text lowres male male_focus male_solo mammal miles_prower multicolored_body multicolored_fur penis sega shoes shota simple_background solo sonic_the_hedgehog_(series) testicles text tongue two_tone_body two_tone_fur white_background white_body white_fur yellow_body yellow_fur younger
1999 1boy artdecade biped blush bodily_fluids canid canine clothing cub cum cum_in_mouth cum_in_own_mouth cum_in_pussy cum_in_self cum_inside cum_on_own_face cum_on_own_tongue cum_on_self cum_on_tongue erection facial footwear fox fur furry genital_fluids genitals gloomwolfe gloves handwear japanese_text lowres male male_focus male_solo mammal miles_prower multicolored_body multicolored_fur penis sega shoes shota simple_background solo sonic_the_hedgehog_(series) testicles text tongue two_tone_body two_tone_fur white_background white_body white_fur yellow_body yellow_fur younger
1999 1girl 90s august barefoot beach blonde_hair blue_eyes blue_swimsuit blush feet female happy hoshino_fuuta innertube kneeling loli one-piece_swimsuit open_mouth ponytail sand smile soles swimsuit tied_hair toes
1999 1girl 90s august barefoot beach blonde_hair blue_eyes blue_swimsuit blush feet female happy hoshino_fuuta innertube kneeling loli one-piece_swimsuit open_mouth ponytail sand smile soles swimsuit tied_hair toes
1999 brown_hair closed_eyes erection eyebrows gloves hat kasumi_(pokemon) lowres male nintendo nude open_mouth orange_hair penis pikachu pokemon satoshi_(pokemon) shoes shota takeshi_(pokemon) testicles white_background yaoi
1999 brown_hair closed_eyes erection eyebrows gloves hat kasumi_(pokemon) lowres male nintendo nude open_mouth orange_hair penis pikachu pokemon satoshi_(pokemon) shoes shota takeshi_(pokemon) testicles white_background yaoi
1999 1girl ahoge blue_eyes blue_hair blush boots bottomless butterfly_sitting dated earrings female flat_chest gloves green_background hat hatomugisan jewelry legs loli magical_girl no_anus no_panties ojamajo_doremi open_mouth pussy senoo_aiko shoes short_hair sitting skirt solo spread_legs upskirt
1999 1girl ahoge blue_eyes blue_hair blush boots bottomless butterfly_sitting dated earrings female flat_chest gloves green_background hat hatomugisan jewelry legs loli magical_girl no_anus no_panties ojamajo_doremi open_mouth pussy senoo_aiko shoes short_hair sitting skirt solo spread_legs upskirt
1999 1boy 90s animal_ears armpits artist_name bulge bunny bunny_ears bunny_tail bunnysuit chinese_zodiac choker english_text erection erection_under_clothes kneeling male male_focus navel new_year nipples no_pants open_mouth orange_eyes original penis pet_play pink_hair po-ju red_eyes shirtless shoes shota solo tail thong
1999 1boy 90s animal_ears armpits artist_name bulge bunny bunny_ears bunny_tail bunnysuit chinese_zodiac choker english_text erection erection_under_clothes kneeling male male_focus navel new_year nipples no_pants open_mouth orange_eyes original penis pet_play pink_hair po-ju red_eyes shirtless shoes shota solo tail thong
1999 1girl 90s :3 blue_eyes cowboy_shot female flat_chest frame green_hair loli mole mole_under_eye nude solo sonnano_ari tomboy towel
1999 1girl 90s :3 blue_eyes cowboy_shot female flat_chest frame green_hair loli mole mole_under_eye nude solo sonnano_ari tomboy towel