20th_century best from all time

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20th century

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 hentai hi_res high_heels highres humiliation longer_than_30_seconds longer_than_3_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
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 hentai hi_res high_heels highres humiliation longer_than_30_seconds longer_than_3_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
<3 1920s 1928 1929 20s 20th_century 2_horns 2d 4:3 5_fingers ? accidentally_gay age_difference alarm_clock ambiguous_gender anal anal_penetration ancient_art animated annoyed anonymous_artist areola arm_support aroused arthropod asinus avian balls beach beckoning becoming_erect becoming_flaccid bestiality better_version_at_source big_balls big_penis binoculars bird black_and_white black_background black_bars black_border black_screen_roulette blank_thumbnail blinking blowing_kiss bodily_fluids border bottomwear bovid bovid_horn bovine bovine_horn bracelet breast_lick breast_milking breast_play breast_squeeze breast_sucking breasts butt cactus canid canine canis cartoon_physics cattle circumcised classic_cartoon clock clothed clothing cloud cock_and_ball_torture collaboration crab crustacean decapoda detachable detachable_penis dialogue digitigrade dildo dildo_in_ass dildo_in_pussy dildo_insertion dipteran doggy_style domestic_dog donkey drinking_milk duo_focus english_text entwined_tails equid equine erect_nipples erection eveready_harton eveready_harton_in_buried_treasure exclamation_point eye_roll eyebrows eyes_closed facial_hair fellatio female female_on_human female_penetrated fence feral feral_on_feral feral_penetrated feral_penetrating feral_penetrating_feral fingers fisting flaccid fleischer_style_toon flexible_penis footwear forced from_behind_position from_front_position frottage funny funny_porn furrowed_eyebrows genital_torture genitals gesture glans glory_hole grainy group gun hair hand_on_breast hand_on_own_breasts happy hat headgear headwear high_heels holding_breast hooves horn huge_penis human human_focus human_on_feral human_on_human human_penetrated human_penetrating human_penetrating_female human_penetrating_feral human_penetrating_human humanoid_genitalia humanoid_penis humanoid_pussy humor humor_porn humorous insect interspecies intraspecies island jewelry jumping kissing lactating lactation larger_penetrated laugh leaning leaning_back leggings legwear licking line_art living_penis long_playtime long_tongue longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute looking_pleasured lost_my_keys low_res lying malacostracan male male/ambiguous male/female male/male male_focus male_on_bottom male_on_feral male_on_top male_penetrated male_penetrating male_penetrating_female male_penetrating_feral male_penetrating_male mammal marine masturbation max_fleischer missionary_position monochrome mostly_clothed mostly_nude mountain_range mp4 mustache nipple_fetish nipple_lick nipple_play nipple_suck nipples no_sound non-mammal_balls not_furry_focus nude object_in_pussy old_toon older_penetrated on_back on_bottom on_top open_mouth oral outside outside_masturbation outside_sex pain pants penetration penile penile_penetration penis penis_bite penis_in_ass penis_in_pussy penis_kissing penis_lick penis_slap penis_through_fly perching_position pile pivoted_ears plant plantigrade poking_out prehensile_penis prehensile_tongue pubes pubic_hair public public_domain public_sex pussy pussy_to_ass raised_tail ranged_weapon rape reptile rock running sand scalie scanlines seaside sentient_penis serpentine sex sex_toy sex_toy_in_ass sex_toy_in_pussy sex_toy_insertion shadow shirt shoes shorts simple_background sitting size_difference slap small_breasts smoke snake solo solo_focus sombrero spot_shadow spread_legs spreading standing stretched_penis stuck_penis sucking surprise_anal surprise_buttsecks surprise_buttsex swordfight tail_coil tank_top text title_card tongue tongue_on_breast tongue_out too_many_tags toony topwear toying_self traditional_media_(artwork) tree umbrella unicycle unknown_artist urethra vaginal vaginal_fisting vaginal_masturbation vaginal_penetration video voyeur wagging_finger walking weapon webm white_text wide_eyed yaoi yawn younger_dom_older_sub zoophilia
<3 1920s 1928 1929 20s 20th_century 2_horns 2d 4:3 5_fingers ? accidentally_gay age_difference alarm_clock ambiguous_gender anal anal_penetration ancient_art animated annoyed anonymous_artist areola arm_support aroused arthropod asinus avian balls beach beckoning becoming_erect becoming_flaccid bestiality better_version_at_source big_balls big_penis binoculars bird black_and_white black_background black_bars black_border black_screen_roulette blank_thumbnail blinking blowing_kiss bodily_fluids border bottomwear bovid bovid_horn bovine bovine_horn bracelet breast_lick breast_milking breast_play breast_squeeze breast_sucking breasts butt cactus canid canine canis cartoon_physics cattle circumcised classic_cartoon clock clothed clothing cloud cock_and_ball_torture collaboration crab crustacean decapoda detachable detachable_penis dialogue digitigrade dildo dildo_in_ass dildo_in_pussy dildo_insertion dipteran doggy_style domestic_dog donkey drinking_milk duo_focus english_text entwined_tails equid equine erect_nipples erection eveready_harton eveready_harton_in_buried_treasure exclamation_point eye_roll eyebrows eyes_closed facial_hair fellatio female female_on_human female_penetrated fence feral feral_on_feral feral_penetrated feral_penetrating feral_penetrating_feral fingers fisting flaccid fleischer_style_toon flexible_penis footwear forced from_behind_position from_front_position frottage funny funny_porn furrowed_eyebrows genital_torture genitals gesture glans glory_hole grainy group gun hair hand_on_breast hand_on_own_breasts happy hat headgear headwear high_heels holding_breast hooves horn huge_penis human human_focus human_on_feral human_on_human human_penetrated human_penetrating human_penetrating_female human_penetrating_feral human_penetrating_human humanoid_genitalia humanoid_penis humanoid_pussy humor humor_porn humorous insect interspecies intraspecies island jewelry jumping kissing lactating lactation larger_penetrated laugh leaning leaning_back leggings legwear licking line_art living_penis long_playtime long_tongue longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute looking_pleasured lost_my_keys low_res lying malacostracan male male/ambiguous male/female male/male male_focus male_on_bottom male_on_feral male_on_top male_penetrated male_penetrating male_penetrating_female male_penetrating_feral male_penetrating_male mammal marine masturbation max_fleischer missionary_position monochrome mostly_clothed mostly_nude mountain_range mp4 mustache nipple_fetish nipple_lick nipple_play nipple_suck nipples no_sound non-mammal_balls not_furry_focus nude object_in_pussy old_toon older_penetrated on_back on_bottom on_top open_mouth oral outside outside_masturbation outside_sex pain pants penetration penile penile_penetration penis penis_bite penis_in_ass penis_in_pussy penis_kissing penis_lick penis_slap penis_through_fly perching_position pile pivoted_ears plant plantigrade poking_out prehensile_penis prehensile_tongue pubes pubic_hair public public_domain public_sex pussy pussy_to_ass raised_tail ranged_weapon rape reptile rock running sand scalie scanlines seaside sentient_penis serpentine sex sex_toy sex_toy_in_ass sex_toy_in_pussy sex_toy_insertion shadow shirt shoes shorts simple_background sitting size_difference slap small_breasts smoke snake solo solo_focus sombrero spot_shadow spread_legs spreading standing stretched_penis stuck_penis sucking surprise_anal surprise_buttsecks surprise_buttsex swordfight tail_coil tank_top text title_card tongue tongue_on_breast tongue_out too_many_tags toony topwear toying_self traditional_media_(artwork) tree umbrella unicycle unknown_artist urethra vaginal vaginal_fisting vaginal_masturbation vaginal_penetration video voyeur wagging_finger walking weapon webm white_text wide_eyed yaoi yawn younger_dom_older_sub zoophilia
1girls 20th_century 20th_century_fox adult ai_generated alternate_version_available american_dad barefoot bed bedroom_eyes big_penis blonde_female blonde_hair bokonsfw clothed_female cum cumshot denim_shorts earrings evil_grin evil_smile feet female female_focus foot_fetish foot_focus footjob francine_smith jean_shorts large_breasts long_hair male_pov married_woman massive_cum milf patreon patreon_logo patreon_username penis pov pov_crotch pov_eye_contact red_clothing red_shirt short_sleeves shorts twitter_link
1girls 20th_century 20th_century_fox adult ai_generated alternate_version_available american_dad barefoot bed bedroom_eyes big_penis blonde_female blonde_hair bokonsfw clothed_female cum cumshot denim_shorts earrings evil_grin evil_smile feet female female_focus foot_fetish foot_focus footjob francine_smith jean_shorts large_breasts long_hair male_pov married_woman massive_cum milf patreon patreon_logo patreon_username penis pov pov_crotch pov_eye_contact red_clothing red_shirt short_sleeves shorts twitter_link
1990s 1999 20th_century 2d 2d_(artwork) 2d_animation 2girls 480p 640x480 90s age_difference animated aoi_(desert_island_story_xx) bed bedroom bouncing_breasts breast_fondling breast_frottage breast_to_breast breasts clitoris cunnilingus desert_island_story_xx dubbed_version english_audio english_dialogue english_dub english_voice english_voice_acting female female/female female_only fingering genital_fluids hand_on_breast hentai kiss kissing lesbian lesbian_sex licking_neck listening_to_sex long_playtime longer_than_2_minutes longer_than_30_seconds longer_than_one_minute low_res lowres mature_female mp4 mujintou_monogatari_xx multiple_girls night nipple_tweak nipples nipples_touching nude older_female orgasm peeping pink_pineapple pussy pussy_grinding pussy_juice pussy_to_pussy retro retro_artstyle scissoring screencap sound sweat symmetrical_docking tribadism twin_braids vagina vaginal_fingering video voice_acted younger_female yuri
1990s 1999 20th_century 2d 2d_(artwork) 2d_animation 2girls 480p 640x480 90s age_difference animated aoi_(desert_island_story_xx) bed bedroom bouncing_breasts breast_fondling breast_frottage breast_to_breast breasts clitoris cunnilingus desert_island_story_xx dubbed_version english_audio english_dialogue english_dub english_voice english_voice_acting female female/female female_only fingering genital_fluids hand_on_breast hentai kiss kissing lesbian lesbian_sex licking_neck listening_to_sex long_playtime longer_than_2_minutes longer_than_30_seconds longer_than_one_minute low_res lowres mature_female mp4 mujintou_monogatari_xx multiple_girls night nipple_tweak nipples nipples_touching nude older_female orgasm peeping pink_pineapple pussy pussy_grinding pussy_juice pussy_to_pussy retro retro_artstyle scissoring screencap sound sweat symmetrical_docking tribadism twin_braids vagina vaginal_fingering video voice_acted younger_female yuri
1930s 1938 1boy 20th_century 2girls animal animal_genitalia animal_penis ass bedroom blonde blonde_female bottomless canid canine canine_genitalia canine_penis canis clothed clothing dog_leash doggy_style domestic_dog dominant_female dominant_feral dominant_male female female_focus female_on_feral femdom feral feral_on_female feral_on_human feral_penetrating from_behind_position group human human_on_feral interspecies julie_delcourt kneeling leash leash_and_collar leash_pull legwear looking_at_another looking_at_partner looking_back looking_down male mammal mounting painting_(artwork) penis pet pink restrained restrained_legs sex smiling smiling_at_partner stockings straight submissive_female submissive_human thigh_high_socks thigh_highs thighhighs threesome traditional_art traditional_media_(artwork) watercolor_(artwork) zoophilia
1930s 1938 1boy 20th_century 2girls animal animal_genitalia animal_penis ass bedroom blonde blonde_female bottomless canid canine canine_genitalia canine_penis canis clothed clothing dog_leash doggy_style domestic_dog dominant_female dominant_feral dominant_male female female_focus female_on_feral femdom feral feral_on_female feral_on_human feral_penetrating from_behind_position group human human_on_feral interspecies julie_delcourt kneeling leash leash_and_collar leash_pull legwear looking_at_another looking_at_partner looking_back looking_down male mammal mounting painting_(artwork) penis pet pink restrained restrained_legs sex smiling smiling_at_partner stockings straight submissive_female submissive_human thigh_high_socks thigh_highs thighhighs threesome traditional_art traditional_media_(artwork) watercolor_(artwork) zoophilia
16:9 1970s 1972 1boy 20th_century 3girls 70s ancient_furry_art animated anthro anthro_female anthro_male anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass bad_metadata bath bathroom bathtub breast_fondling breast_lick breasts canid canine canis cat charlene_(fritz_the_cat) clothing dee-dee_(fritz_the_cat) dialogue dirty_talk dog domestic_cat domestic_dog eyes_closed eyewear feline female female_on_bottom female_penetrated fondling frame_by_frame fritz_the_cat fritz_the_cat_(character) gangbang glasses group hand_on_breast humor long_playtime lying male male_on_top male_penetrating mammal missionary_position moan navel nipples nude on_back ralph_bakshi robert_crumb sex slightly_chubby smile sound spread_legs spreading straight table_lotus table_lotus_position toony traditional_media_(artwork) undressing vaginal vaginal_penetration video vintage voice_acted webm widescreen winston_(fritz_the_cat)
16:9 1970s 1972 1boy 20th_century 3girls 70s ancient_furry_art animated anthro anthro_female anthro_male anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro ass bad_metadata bath bathroom bathtub breast_fondling breast_lick breasts canid canine canis cat charlene_(fritz_the_cat) clothing dee-dee_(fritz_the_cat) dialogue dirty_talk dog domestic_cat domestic_dog eyes_closed eyewear feline female female_on_bottom female_penetrated fondling frame_by_frame fritz_the_cat fritz_the_cat_(character) gangbang glasses group hand_on_breast humor long_playtime lying male male_on_top male_penetrating mammal missionary_position moan navel nipples nude on_back ralph_bakshi robert_crumb sex slightly_chubby smile sound spread_legs spreading straight table_lotus table_lotus_position toony traditional_media_(artwork) undressing vaginal vaginal_penetration video vintage voice_acted webm widescreen winston_(fritz_the_cat)
1boy 1girls 20th_century 3d alien alien/human alien_girl animated anthro_penetrated audible_creampie audible_ejaculation bathroom bbw big_ass big_butt cowgirl_position cum cum_in_pussy cum_inside disney fat_ass female_on_top female_yautja huge_ass human_on_anthro human_penetrating larger_female longer_than_30_seconds male_human/female_alien overweight overweight_female predator_(franchise) predator_hunting_grounds public smaller_male sound unseen_male_face video yautja zenith741
1boy 1girls 20th_century 3d alien alien/human alien_girl animated anthro_penetrated audible_creampie audible_ejaculation bathroom bbw big_ass big_butt cowgirl_position cum cum_in_pussy cum_inside disney fat_ass female_on_top female_yautja huge_ass human_on_anthro human_penetrating larger_female longer_than_30_seconds male_human/female_alien overweight overweight_female predator_(franchise) predator_hunting_grounds public smaller_male sound unseen_male_face video yautja zenith741
16:9 1boy 1boy1girl 1girls 2022 20th_century 3d abs after_sex afterglow against_surface against_wall alien alien/human alien_girl alien_humanoid amazon angrydraconequus animated anus areola areolae ass asshole back_muscles balls beckoning bench biceps big_areola big_areolae big_breasts big_thighs biped blender_(software) bodily_fluids bouncing_balls bouncing_breasts breasts breathing butt butt_from_the_front color cowgirl_position cuddling cum cum_in_pussy cum_inside cum_on_body cum_on_ground cum_on_penis cum_on_self cumshot cunnilingus digital_media_(artwork) disney duo ejaculating_cum ejaculation erection excessive_genital_fluids eye_contact female female_on_human female_on_top female_penetrated female_yautja femdom first_person_view from_front_position genital_fluids genitals gesture hair hand_on_knee hand_on_leg hand_on_thigh helmet holding_partner huge_filesize human human_on_bottom human_on_humanoid human_penetrating human_penetrating_humanoid human_pov humanoid humanoid_genitalia humanoid_on_top humanoid_penetrated humanoid_penis interspecies inviting kneeling kneeling_oral_position labia larger_female light-skinned_male long_playtime long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute looking_at_another looking_at_partner looking_at_viewer looking_down low-angle_view male male/female male_on_bottom male_on_humanoid male_penetrating male_penetrating_female male_pov mammal mask muscular muscular_female muscular_male nipples not_furry nude on_bench on_bottom on_top oral penetrating_pov penetration penile penile_penetration penis penis_in_pussy pinned pinned_to_wall predator_(franchise) predator_hunting_grounds pseudo_hair pussy pussy_lips rear_view sauna scar sex shiny shiny_breasts shiny_skin sitting size_difference solo_female sound spread_legs spreading steam submissive submissive_male sweat sweatdrop sweating sweaty sweaty_ass sweaty_body sweaty_breasts sweaty_butt sweaty_genitalia sweaty_legs sweaty_thighs text thick_thighs towel url vaginal vaginal_penetration video voice_acted warrior webm wholesome widescreen worm's-eye_view yautja
16:9 1boy 1boy1girl 1girls 2022 20th_century 3d abs after_sex afterglow against_surface against_wall alien alien/human alien_girl alien_humanoid amazon angrydraconequus animated anus areola areolae ass asshole back_muscles balls beckoning bench biceps big_areola big_areolae big_breasts big_thighs biped blender_(software) bodily_fluids bouncing_balls bouncing_breasts breasts breathing butt butt_from_the_front color cowgirl_position cuddling cum cum_in_pussy cum_inside cum_on_body cum_on_ground cum_on_penis cum_on_self cumshot cunnilingus digital_media_(artwork) disney duo ejaculating_cum ejaculation erection excessive_genital_fluids eye_contact female female_on_human female_on_top female_penetrated female_yautja femdom first_person_view from_front_position genital_fluids genitals gesture hair hand_on_knee hand_on_leg hand_on_thigh helmet holding_partner huge_filesize human human_on_bottom human_on_humanoid human_penetrating human_penetrating_humanoid human_pov humanoid humanoid_genitalia humanoid_on_top humanoid_penetrated humanoid_penis interspecies inviting kneeling kneeling_oral_position labia larger_female light-skinned_male long_playtime long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute looking_at_another looking_at_partner looking_at_viewer looking_down low-angle_view male male/female male_on_bottom male_on_humanoid male_penetrating male_penetrating_female male_pov mammal mask muscular muscular_female muscular_male nipples not_furry nude on_bench on_bottom on_top oral penetrating_pov penetration penile penile_penetration penis penis_in_pussy pinned pinned_to_wall predator_(franchise) predator_hunting_grounds pseudo_hair pussy pussy_lips rear_view sauna scar sex shiny shiny_breasts shiny_skin sitting size_difference solo_female sound spread_legs spreading steam submissive submissive_male sweat sweatdrop sweating sweaty sweaty_ass sweaty_body sweaty_breasts sweaty_butt sweaty_genitalia sweaty_legs sweaty_thighs text thick_thighs towel url vaginal vaginal_penetration video voice_acted warrior webm wholesome widescreen worm's-eye_view yautja
1boy 1girls 20th_century accurate_art_style affair alternate_hairstyle alternate_universe badbrains body_difference bonnie_swanson cheating cheating_wife erect_clitoris faceless_male family_guy fat_man female infidelity male married_woman necklace netorare ntr peter_griffin stockings tagme unseen_male_face vaginal_penetration
1boy 1girls 20th_century accurate_art_style affair alternate_hairstyle alternate_universe badbrains body_difference bonnie_swanson cheating cheating_wife erect_clitoris faceless_male family_guy fat_man female infidelity male married_woman necklace netorare ntr peter_griffin stockings tagme unseen_male_face vaginal_penetration
1080p 1440x1080 1990s 1990s_(style) 1998 1girls 20th_century 2boys 2boys1girl 2d 6+girls 90s abandoned_building adult_and_teenager age_difference akagawa_rika anal anal_fingering anal_penetration anal_rape anal_sex anal_virgin animated arms_behind_back asakawa_kotomi assisted_rape bad_acting bad_voice_acting beard_stubble begging_to_stop bisexual bisexual_(female) black_hair black_hair_female blowjob blue_eyes blue_hair blue_hair_female blush bondage bouncing_breasts bound bound_wrists braid breast_fondle breast_grab breast_grope breasts breasts_out broken_rape_victim brown_eyes_female brown_hair brown_hair_female carrying carrying_another clothed_male_nude_female collaborative_fellatio completely_nude completely_nude_female crying crying_with_eyes_open cum cum_on_face cumshot defloration deflowered deflowering dirty_talk double_fellatio double_penetration dubbed_version ejaculation elf_(company) english_audio english_dialogue english_dub english_voice english_voice_acting erect_nipples explicitly_stated_nonconsent exposed_breasts exposed_pussy facial fellatio female female_moaning fingering fingering_partner fingering_pussy fingering_self fondling_breast forced forced_anal forced_partners forced_to_watch grabbing_breasts grabbing_from_behind groping groping_breasts groping_from_behind guilt hairless_pussy hands_tied hd helpless hentai_series hi_res highres indoors insult isaku itou_isaku kogure_kenta larger_male larger_penetrating_smaller licking licking_penis longer_than_30_seconds longer_than_3_minutes longer_than_one_minute lying_cowgirl_position male masturbation mating_press mikihara_akemi misogyny moaning moaning_in_pain mole mole_under_eye molestation mp4 multiple_girls navel nervous_male nipple_pinch nipple_play nipple_tweak nude nude_female old_man older_male older_male_younger_female older_man_and_teenage_girl older_penetrating_younger over_480p paizuri penetration penis penis_in_pussy penis_lick perky_breasts pinching_nipples pink_hair pink_hair_female pink_pineapple pussy pussy_fingering pussy_juice pussy_juice_on_fingers rape recording restrained retro retro_artstyle sakaki_miyuki schoolgirl screaming seifuku serafuku serizawa_mio sex shimada_jinpachi size_difference small_breasts smaller_female smaller_penetrated soga_munemitsu sound spread_legs spreading sweat sweaty teamwork tear_streaks tears teen teen_girl teenage teenage_girl teenager thighs thrusting tied_wrists tight_pussy titfuck titjob tv ugly_man uncensored vaginal_penetration vaginal_sex video virgin virginity_loss voice_acted watching_porn wooden_floor young young_female younger_female younger_penetrated
1080p 1440x1080 1990s 1990s_(style) 1998 1girls 20th_century 2boys 2boys1girl 2d 6+girls 90s abandoned_building adult_and_teenager age_difference akagawa_rika anal anal_fingering anal_penetration anal_rape anal_sex anal_virgin animated arms_behind_back asakawa_kotomi assisted_rape bad_acting bad_voice_acting beard_stubble begging_to_stop bisexual bisexual_(female) black_hair black_hair_female blowjob blue_eyes blue_hair blue_hair_female blush bondage bouncing_breasts bound bound_wrists braid breast_fondle breast_grab breast_grope breasts breasts_out broken_rape_victim brown_eyes_female brown_hair brown_hair_female carrying carrying_another clothed_male_nude_female collaborative_fellatio completely_nude completely_nude_female crying crying_with_eyes_open cum cum_on_face cumshot defloration deflowered deflowering dirty_talk double_fellatio double_penetration dubbed_version ejaculation elf_(company) english_audio english_dialogue english_dub english_voice english_voice_acting erect_nipples explicitly_stated_nonconsent exposed_breasts exposed_pussy facial fellatio female female_moaning fingering fingering_partner fingering_pussy fingering_self fondling_breast forced forced_anal forced_partners forced_to_watch grabbing_breasts grabbing_from_behind groping groping_breasts groping_from_behind guilt hairless_pussy hands_tied hd helpless hentai_series hi_res highres indoors insult isaku itou_isaku kogure_kenta larger_male larger_penetrating_smaller licking licking_penis longer_than_30_seconds longer_than_3_minutes longer_than_one_minute lying_cowgirl_position male masturbation mating_press mikihara_akemi misogyny moaning moaning_in_pain mole mole_under_eye molestation mp4 multiple_girls navel nervous_male nipple_pinch nipple_play nipple_tweak nude nude_female old_man older_male older_male_younger_female older_man_and_teenage_girl older_penetrating_younger over_480p paizuri penetration penis penis_in_pussy penis_lick perky_breasts pinching_nipples pink_hair pink_hair_female pink_pineapple pussy pussy_fingering pussy_juice pussy_juice_on_fingers rape recording restrained retro retro_artstyle sakaki_miyuki schoolgirl screaming seifuku serafuku serizawa_mio sex shimada_jinpachi size_difference small_breasts smaller_female smaller_penetrated soga_munemitsu sound spread_legs spreading sweat sweaty teamwork tear_streaks tears teen teen_girl teenage teenage_girl teenager thighs thrusting tied_wrists tight_pussy titfuck titjob tv ugly_man uncensored vaginal_penetration vaginal_sex video virgin virginity_loss voice_acted watching_porn wooden_floor young young_female younger_female younger_penetrated
1970s 1972 20th_century 2d 2d_animation 70s ancient_furry_art animated anthro anthro_female anthro_male avian balls barefoot bertha_(fritz) big_bertha_(fritz) big_breasts big_butt bird black_body black_hair bottomless bottomwear breast_fondling breast_sucking breasts butt clothed clothed_sex clothing corvid corvus_(genus) crow cunnilingus dialogue duo ear_piercing english_text english_voice feet feline female flaccid fondling footwear frame_by_frame fritz_the_cat fritz_the_cat_(character) from_front_position fur genitals grey_balls grey_body grey_fur grey_penis grope hair hand_on_breast high_heels humanoid_genitalia humanoid_penis humiliation humor interspecies junkyard larger_female licking long_playtime lying male male/female male_on_female mammal missionary_position mp4 music necktie nibbling nipple_fetish nipple_lick nipple_pinch nipple_play nipple_suck nipples nude on_back on_top open_mouth oral oscine outside passerine paws penis penis_shaming piercing pillarbox pinch pink_nipples pussy racism ralph_bakshi red_nose red_tongue robert_crumb sex shirt shoes size_difference skirt small_penis small_penis_humiliation smaller_male sound spanish_text striped_body striped_fur stripes subtitled sucking tag_panic teeth text tongue tongue_out topless topwear translated undressing vaginal video vintage voice_acted webm whiskers
1970s 1972 20th_century 2d 2d_animation 70s ancient_furry_art animated anthro anthro_female anthro_male avian balls barefoot bertha_(fritz) big_bertha_(fritz) big_breasts big_butt bird black_body black_hair bottomless bottomwear breast_fondling breast_sucking breasts butt clothed clothed_sex clothing corvid corvus_(genus) crow cunnilingus dialogue duo ear_piercing english_text english_voice feet feline female flaccid fondling footwear frame_by_frame fritz_the_cat fritz_the_cat_(character) from_front_position fur genitals grey_balls grey_body grey_fur grey_penis grope hair hand_on_breast high_heels humanoid_genitalia humanoid_penis humiliation humor interspecies junkyard larger_female licking long_playtime lying male male/female male_on_female mammal missionary_position mp4 music necktie nibbling nipple_fetish nipple_lick nipple_pinch nipple_play nipple_suck nipples nude on_back on_top open_mouth oral oscine outside passerine paws penis penis_shaming piercing pillarbox pinch pink_nipples pussy racism ralph_bakshi red_nose red_tongue robert_crumb sex shirt shoes size_difference skirt small_penis small_penis_humiliation smaller_male sound spanish_text striped_body striped_fur stripes subtitled sucking tag_panic teeth text tongue tongue_out topless topwear translated undressing vaginal video vintage voice_acted webm whiskers
1girls 2020s 2022 20th_century animal_ears anthro anthro_only anthrofied anus ass blue_eyeshadow blue_sky_studios brown_nose butt completely_naked completely_naked_female completely_nude completely_nude_female conditional_dnp dat_ass digital_drawing_(artwork) digital_media_(artwork) eyebrows eyelashes eyeshadow fangs female female_focus female_only flying_squirrel fur furaffinity genitals hi_res humanoid_genitalia humanoid_hands humanoid_pussy humanoid_vagina ice_age_(series) ice_age_dawn_of_the_dinosaurs looking_at_viewer makeup mammal naked naked_female nude nude_female orionfell prehistoric presenting presenting_anus presenting_ass presenting_butt presenting_genitalia presenting_hindquarters presenting_pussy presenting_vagina pussy raised_tail rodent sciurid scratte_(ice_age) solo solo_female solo_focus spread_ass spread_butt spread_pussy spreading spreading_ass squirrel teasing vagina
1girls 2020s 2022 20th_century animal_ears anthro anthro_only anthrofied anus ass blue_eyeshadow blue_sky_studios brown_nose butt completely_naked completely_naked_female completely_nude completely_nude_female conditional_dnp dat_ass digital_drawing_(artwork) digital_media_(artwork) eyebrows eyelashes eyeshadow fangs female female_focus female_only flying_squirrel fur furaffinity genitals hi_res humanoid_genitalia humanoid_hands humanoid_pussy humanoid_vagina ice_age_(series) ice_age_dawn_of_the_dinosaurs looking_at_viewer makeup mammal naked naked_female nude nude_female orionfell prehistoric presenting presenting_anus presenting_ass presenting_butt presenting_genitalia presenting_hindquarters presenting_pussy presenting_vagina pussy raised_tail rodent sciurid scratte_(ice_age) solo solo_female solo_focus spread_ass spread_butt spread_pussy spreading spreading_ass squirrel teasing vagina
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 3girls 90s abuse ahe_gao animated anne_(imma_youjo) areola assisted_rape beard begging_to_stop big_breasts bisexual_(female) blonde_hair_female blue_eyes boobs bouncing_breasts branding breast_fondle breast_grab breasts broken_rape_victim brown_hair chains count_pickingel_(imma_youjo) cuffs cum_on_body cum_on_face dark-skinned_male dark_penis dark_skin dirty_talk doggy_style drool drooling dubbed_version dungeon english_dialogue english_dub erection facial female fivesome forced_yuri french_kiss gangrape guards hentai hi_res highres huge_breasts human imma_youjo isabel_(imma_youjo) kissing large_breasts licking_pussy light-skinned_female light_skin lipstick long_hair longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male mayatola_(imma_youjo) mistress moaning mp4 nail_polish naked night nipples nude nude_female nude_male orgy pain paizuri party_wipe penis pink_pineapple prison prisoner purple_lips purple_lipstick purple_nail_polish purple_nails pussy_juice rape red_hair retro retro_artstyle rough_sex rubbing_pussy screencap sex sex_slave sound straight sweat tears thick_thighs thrusting tits uncensored vaginal_penetration video voice_acted webm wound yuri
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 3girls 90s abuse ahe_gao animated anne_(imma_youjo) areola assisted_rape beard begging_to_stop big_breasts bisexual_(female) blonde_hair_female blue_eyes boobs bouncing_breasts branding breast_fondle breast_grab breasts broken_rape_victim brown_hair chains count_pickingel_(imma_youjo) cuffs cum_on_body cum_on_face dark-skinned_male dark_penis dark_skin dirty_talk doggy_style drool drooling dubbed_version dungeon english_dialogue english_dub erection facial female fivesome forced_yuri french_kiss gangrape guards hentai hi_res highres huge_breasts human imma_youjo isabel_(imma_youjo) kissing large_breasts licking_pussy light-skinned_female light_skin lipstick long_hair longer_than_30_seconds longer_than_3_minutes longer_than_one_minute male mayatola_(imma_youjo) mistress moaning mp4 nail_polish naked night nipples nude nude_female nude_male orgy pain paizuri party_wipe penis pink_pineapple prison prisoner purple_lips purple_lipstick purple_nail_polish purple_nails pussy_juice rape red_hair retro retro_artstyle rough_sex rubbing_pussy screencap sex sex_slave sound straight sweat tears thick_thighs thrusting tits uncensored vaginal_penetration video voice_acted webm wound yuri
2020s 2022 20s 20th_century 20th_century_fox 4_fingers animal_ears anthro anthro_only anthrofied anus ass big_ass big_butt bottomless bubble_ass bubble_butt butt canid canine claws dat_ass digital_drawing_(artwork) digital_media_(artwork) einshelm fantastic_mr._fox fat_ass fat_butt female female_focus female_only fluffy fluffy_tail fox fox_girl from_behind fur furry furry_only genitals going_commando half-dressed hi_res humanoid_genitalia humanoid_hands humanoid_pussy humanoid_vagina mammal milf mother mrs._fox multicolored_fur multicolored_tail orange_fur parent plump_ass presenting presenting_anus presenting_ass presenting_butt presenting_genitalia presenting_hindquarters presenting_pussy presenting_vagina pussy rear_view round_ass round_butt solo solo_female solo_focus spread_anus spread_legs spread_pussy spreading tail tan_fur thick thick_ass thick_thighs twitter two_tone_fur two_tone_tail vagina vixen wide_hips
2020s 2022 20s 20th_century 20th_century_fox 4_fingers animal_ears anthro anthro_only anthrofied anus ass big_ass big_butt bottomless bubble_ass bubble_butt butt canid canine claws dat_ass digital_drawing_(artwork) digital_media_(artwork) einshelm fantastic_mr._fox fat_ass fat_butt female female_focus female_only fluffy fluffy_tail fox fox_girl from_behind fur furry furry_only genitals going_commando half-dressed hi_res humanoid_genitalia humanoid_hands humanoid_pussy humanoid_vagina mammal milf mother mrs._fox multicolored_fur multicolored_tail orange_fur parent plump_ass presenting presenting_anus presenting_ass presenting_butt presenting_genitalia presenting_hindquarters presenting_pussy presenting_vagina pussy rear_view round_ass round_butt solo solo_female solo_focus spread_anus spread_legs spread_pussy spreading tail tan_fur thick thick_ass thick_thighs twitter two_tone_fur two_tone_tail vagina vixen wide_hips
1990s 1995 1girls 20th_century 90s animated breast_grab breasts gif golden_boy groping_breast groping_self implied_masturbation large_breasts lowres lying_down masturbation moaning motorcycle on_motorcycle panties reiko_terayama reupload topless underwear vehicle
1990s 1995 1girls 20th_century 90s animated breast_grab breasts gif golden_boy groping_breast groping_self implied_masturbation large_breasts lowres lying_down masturbation moaning motorcycle on_motorcycle panties reiko_terayama reupload topless underwear vehicle
1280x720 1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 3girls 720p 90s abuse angry_face angry_look animated anne_(imma_youjo) areola asking_for_it assisted_rape beard bed bedroom begging_to_stop big_breasts bleeding blonde_hair_male blood blue_dress blue_eyes boobs bouncing_breasts breast_fondle breast_grab breasts broken_rape_victim brown_hair chains count_pickingel_(imma_youjo) creampie cuffs cum cum_covered cum_in_pussy cum_inside cum_on_ass cum_on_body cum_on_face dark-skinned_male dark_penis dark_skin day desert dirty_talk disrespect doggy_style drool drooling dubbed_version dungeon ejaculation endurance_test english_dialogue english_dub english_voice_acting erection faceslap facial female fingering fingering_partner forced_yuri gangrape guards hentai hi_res highres huge_breasts human imma_youjo isabel_(imma_youjo) large_breasts licking_nipples licking_wound light-skinned_female light_skin lipstick long_hair longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male maledom mayatola_(imma_youjo) mistress moaning moaning_in_pleasure mp4 multiple_cumshots nail_polish nipples object_insertion penis pink_pineapple prison prisoner purple_lips purple_lipstick purple_nail_polish purple_nails pussy pussy_juice pussy_rub rape red_hair retro retro_artstyle ripped_clothing ripped_pants rough_sex rubbing_pussy ryona screencap sex slap slapped sound spit spitting_on_face stone_floor straight sweat sword_hilt tears thick_thighs thrusting tits torture tough_girl uncensored vaginal_object_insertion vaginal_penetration video voice_acted watching_sex webm whip whip_marks whipping whored_out wound yuri
1280x720 1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 3girls 720p 90s abuse angry_face angry_look animated anne_(imma_youjo) areola asking_for_it assisted_rape beard bed bedroom begging_to_stop big_breasts bleeding blonde_hair_male blood blue_dress blue_eyes boobs bouncing_breasts breast_fondle breast_grab breasts broken_rape_victim brown_hair chains count_pickingel_(imma_youjo) creampie cuffs cum cum_covered cum_in_pussy cum_inside cum_on_ass cum_on_body cum_on_face dark-skinned_male dark_penis dark_skin day desert dirty_talk disrespect doggy_style drool drooling dubbed_version dungeon ejaculation endurance_test english_dialogue english_dub english_voice_acting erection faceslap facial female fingering fingering_partner forced_yuri gangrape guards hentai hi_res highres huge_breasts human imma_youjo isabel_(imma_youjo) large_breasts licking_nipples licking_wound light-skinned_female light_skin lipstick long_hair longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male maledom mayatola_(imma_youjo) mistress moaning moaning_in_pleasure mp4 multiple_cumshots nail_polish nipples object_insertion penis pink_pineapple prison prisoner purple_lips purple_lipstick purple_nail_polish purple_nails pussy pussy_juice pussy_rub rape red_hair retro retro_artstyle ripped_clothing ripped_pants rough_sex rubbing_pussy ryona screencap sex slap slapped sound spit spitting_on_face stone_floor straight sweat sword_hilt tears thick_thighs thrusting tits torture tough_girl uncensored vaginal_object_insertion vaginal_penetration video voice_acted watching_sex webm whip whip_marks whipping whored_out wound yuri
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 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 20th_century 2d 2d_(artwork) 2d_animation 2girls 480p 720x480 90s animated animation anus begging_for_mercy blush bondage breasts brown_hair bustier clitoris clothing completely_nude completely_nude_female cool_devices cross_section dominatrix dubbed_version dungeon elbow_gloves english_audio english_dialogue english_dub english_voice english_voice_acting evil_face female forced forced_insertion gloves green_eyes green_eyes_female hentai hentai_series implantation large_breasts long_hair mizutani_maya multiple_girls nipples open_mouth parasite parasitic_possession penetration penis_tentacles pink_pineapple pubic_hair pussy rape red_hair restrained retro retro_artstyle slave_warrior_maya slime slime_monster sound spread_legs unbirthing uncensored vagina vaginal_insertion vaginal_penetration video voice_acted wide_eyed wtf x-ray
1990s 1997 20th_century 2d 2d_(artwork) 2d_animation 2girls 480p 720x480 90s animated animation anus begging_for_mercy blush bondage breasts brown_hair bustier clitoris clothing completely_nude completely_nude_female cool_devices cross_section dominatrix dubbed_version dungeon elbow_gloves english_audio english_dialogue english_dub english_voice english_voice_acting evil_face female forced forced_insertion gloves green_eyes green_eyes_female hentai hentai_series implantation large_breasts long_hair mizutani_maya multiple_girls nipples open_mouth parasite parasitic_possession penetration penis_tentacles pink_pineapple pubic_hair pussy rape red_hair restrained retro retro_artstyle slave_warrior_maya slime slime_monster sound spread_legs unbirthing uncensored vagina vaginal_insertion vaginal_penetration video voice_acted wide_eyed wtf x-ray