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1990s

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
1280x720 1990s 1990s_(style) 1997 1boy 1boy1girl 1girls 1min_video 20th_century 720p 90s anal animated areola beard bed bedroom big_breasts bouncing_breasts breast_grab breasts castle count_pickingel_(imma_youjo) dark-skinned_male dark_penis dark_skin doggy_style dubbed_version english english_dialogue english_dub erection female female_moaning grunting hd hi_res highres huge_breasts human imma_youjo intense_sex isabel_(imma_youjo) large_breasts licking_wound light-skinned_female light_skin lipstick long_hair longer_than_30_seconds longer_than_one_minute male male_moaning mature_woman mistress moaning moaning_in_pleasure mp4 nail_polish night nipples no_clothes nude nude_female nude_male penis pink_pineapple pleased_expression purple_lips purple_lipstick purple_nail_polish purple_nails pussy_juice red_hair retro retro_artstyle rough_sex satisfied screencap sex sound straight suprise_anal sweat thick_thighs thrusting uncensored vaginal_penetration video voice_acted webm wound
1280x720 1990s 1990s_(style) 1997 1boy 1boy1girl 1girls 1min_video 20th_century 720p 90s anal animated areola beard bed bedroom big_breasts bouncing_breasts breast_grab breasts castle count_pickingel_(imma_youjo) dark-skinned_male dark_penis dark_skin doggy_style dubbed_version english english_dialogue english_dub erection female female_moaning grunting hd hi_res highres huge_breasts human imma_youjo intense_sex isabel_(imma_youjo) large_breasts licking_wound light-skinned_female light_skin lipstick long_hair longer_than_30_seconds longer_than_one_minute male male_moaning mature_woman mistress moaning moaning_in_pleasure mp4 nail_polish night nipples no_clothes nude nude_female nude_male penis pink_pineapple pleased_expression purple_lips purple_lipstick purple_nail_polish purple_nails pussy_juice red_hair retro retro_artstyle rough_sex satisfied screencap sex sound straight suprise_anal sweat thick_thighs thrusting uncensored vaginal_penetration video voice_acted webm wound
1990s 1990s_(style) 1boy 1girls 2d 2d_(artwork) 90s a_kite age_difference akai_(kite) animated arms_behind_back bdsm bed being_watched blue_eyes bob_cut bondage bouncing_breasts bound bound_wrists breasts brown_hair bulldog_position casual clothing crying cum cum_in_pussy cum_inside dark_skin deleted_scene doggy_style drooling english_text fat_man female firearm from_behind gag gagged gun handgun human improvised_gag kite_(anime) longer_than_30_seconds male medium_breasts monster_rape muffled_moaning muffled_squeal nipples nude on_side pale_skin penis petite pussy pussy_juice rape red_hair reverse_cowgirl_position sex short_hair shorter_than_one_minute side_position size_difference sound straight surprised sweat tape tape_bondage tape_gag tears text_focus top-down_bottom-up ugly_bastard ugly_man umetsu_yasuomi uncensored vaginal vaginal_penetration video voice_acted weapon
1990s 1990s_(style) 1boy 1girls 2d 2d_(artwork) 90s a_kite age_difference akai_(kite) animated arms_behind_back bdsm bed being_watched blue_eyes bob_cut bondage bouncing_breasts bound bound_wrists breasts brown_hair bulldog_position casual clothing crying cum cum_in_pussy cum_inside dark_skin deleted_scene doggy_style drooling english_text fat_man female firearm from_behind gag gagged gun handgun human improvised_gag kite_(anime) longer_than_30_seconds male medium_breasts monster_rape muffled_moaning muffled_squeal nipples nude on_side pale_skin penis petite pussy pussy_juice rape red_hair reverse_cowgirl_position sex short_hair shorter_than_one_minute side_position size_difference sound straight surprised sweat tape tape_bondage tape_gag tears text_focus top-down_bottom-up ugly_bastard ugly_man umetsu_yasuomi uncensored vaginal vaginal_penetration video voice_acted weapon
1990s 1996 20th_century 2d 2d_(artwork) 3boys 3girls 480p 90s advancer_tina animated breasts city clothing criminal dialogue female forced longer_than_30_seconds longer_than_one_minute nipples nun nun's_habit nun_outfit oral public_sex punk rape sound tagme text vagina video
1990s 1996 20th_century 2d 2d_(artwork) 3boys 3girls 480p 90s advancer_tina animated breasts city clothing criminal dialogue female forced longer_than_30_seconds longer_than_one_minute nipples nun nun's_habit nun_outfit oral public_sex punk rape sound tagme text vagina video
1990s 1990s_(style) 1996 1girls 2d 2d_(artwork) 480p 90s advancer_tina animated ass bathroom black_screen_roulette breasts female female_focus female_masturbation female_only hi_res highres longer_than_30_seconds masturbation medium_breasts medium_hair mp4 nipples nude pussy retro retro_artstyle screencap short_playtime shorter_than_one_minute shower sole_female solo solo_female solo_focus sound uncensored vagina video water yellow_hair
1990s 1990s_(style) 1996 1girls 2d 2d_(artwork) 480p 90s advancer_tina animated ass bathroom black_screen_roulette breasts female female_focus female_masturbation female_only hi_res highres longer_than_30_seconds masturbation medium_breasts medium_hair mp4 nipples nude pussy retro retro_artstyle screencap short_playtime shorter_than_one_minute shower sole_female solo solo_female solo_focus sound uncensored vagina video water yellow_hair
1990s 1998 1boy 1girls 20th_century 90s animated animated_gif arched_back areolae asakawa_kotomi ass blush breasts clothed_male_nude_female elf_(company) female gif hair_ornament hair_ribbon hanging_breasts isaku male naked nipples nude nude_female over_480p pink_pineapple prison_guard_position rape red_hair sex small_breasts tears
1990s 1998 1boy 1girls 20th_century 90s animated animated_gif arched_back areolae asakawa_kotomi ass blush breasts clothed_male_nude_female elf_(company) female gif hair_ornament hair_ribbon hanging_breasts isaku male naked nipples nude nude_female over_480p pink_pineapple prison_guard_position rape red_hair sex small_breasts tears
1990s 1990s_(style) 1998 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 2d_animation 90s abandoned_building age_difference animated ankle_socks anklehighs ankles_tied arms_above_head arms_tied_above_head black_hair breast_grab breasts brown_hair clothed_male elf_(company) exposed_breasts feet_tied female gif glasses groping_breasts groping_from_behind hair_ribbon hands_tied hi_res highres isaku itou_isaku long_hair male medium_breasts mikihara_akemi over_480p panties_down penetration pink_pineapple pink_socks pussy rape restrained retro_artstyle rope_around_ankle sex shirt_up skirt_up socks tennis_uniform uncensored vaginal_rape
1990s 1990s_(style) 1998 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 2d_animation 90s abandoned_building age_difference animated ankle_socks anklehighs ankles_tied arms_above_head arms_tied_above_head black_hair breast_grab breasts brown_hair clothed_male elf_(company) exposed_breasts feet_tied female gif glasses groping_breasts groping_from_behind hair_ribbon hands_tied hi_res highres isaku itou_isaku long_hair male medium_breasts mikihara_akemi over_480p panties_down penetration pink_pineapple pink_socks pussy rape restrained retro_artstyle rope_around_ankle sex shirt_up skirt_up socks tennis_uniform uncensored vaginal_rape
1990s 1990s_(style) 1998 1boy 20th_century 2d 2d_(artwork) 2girls 720p 90s 960x720 abandoned_building animated brown_hair collaborative_fellatio dark-skinned_male double_fellatio elf_(company) faceless_male fellatio female female_only ffm_threesome gif hi_res highres human isaku licking_penis mikihara_akemi multiple_fellatio multiple_girls oral oral_sex penis pink_pineapple serizawa_mio sex sweat teamwork threesome tongue tongue_on_penis tongue_out uncensored
1990s 1990s_(style) 1998 1boy 20th_century 2d 2d_(artwork) 2girls 720p 90s 960x720 abandoned_building animated brown_hair collaborative_fellatio dark-skinned_male double_fellatio elf_(company) faceless_male fellatio female female_only ffm_threesome gif hi_res highres human isaku licking_penis mikihara_akemi multiple_fellatio multiple_girls oral oral_sex penis pink_pineapple serizawa_mio sex sweat teamwork threesome tongue tongue_on_penis tongue_out uncensored
1990s 1990s_(style) 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 90s animated blush boobs bouncing_breasts breasts brown_hair clothed_male clothed_male_nude_female elf_(company) faceless_male female female_focus hands_behind_back hands_on_legs hands_tied haunted_house holding_legs indoors isaku itou_isaku lying_on_back lying_on_floor male moaning nude_female over_480p piledriver_position pink_pineapple rape sakaki_miyuki sex spread_legs stitched tits upper_teeth wooden_floor
1990s 1990s_(style) 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 90s animated blush boobs bouncing_breasts breasts brown_hair clothed_male clothed_male_nude_female elf_(company) faceless_male female female_focus hands_behind_back hands_on_legs hands_tied haunted_house holding_legs indoors isaku itou_isaku lying_on_back lying_on_floor male moaning nude_female over_480p piledriver_position pink_pineapple rape sakaki_miyuki sex spread_legs stitched tits upper_teeth wooden_floor
1990s 1girls 20th_century 2d 2d_(artwork) 3boys 90s akagawa_rika animated big_breasts blush bondage boobs bound_feet elf_(company) female female_focus filming glasses haunted_house hi_res highres isaku itou_isaku long_hair lying_on_back lying_on_table male no_panties over_480p pink_hair pink_pineapple rape rope_bondage schoolgirl sex shimada_jinpachi skirt_lift soga_munemitsu table tits twintails uncensored unseen_male_face vaginal_sex watching watching_sex wooden_table
1990s 1girls 20th_century 2d 2d_(artwork) 3boys 90s akagawa_rika animated big_breasts blush bondage boobs bound_feet elf_(company) female female_focus filming glasses haunted_house hi_res highres isaku itou_isaku long_hair lying_on_back lying_on_table male no_panties over_480p pink_hair pink_pineapple rape rope_bondage schoolgirl sex shimada_jinpachi skirt_lift soga_munemitsu table tits twintails uncensored unseen_male_face vaginal_sex watching watching_sex wooden_table
1990s 1boy 1girls 20th_century 2d 2d_(artwork) 90s akagawa_rika animated big_breasts blush bondage boobs bound_feet elf_(company) female film_set filming gif glasses hair_ribbon haunted_house hi_res highres isaku long_twintails lying_on_back lying_on_table male moaning no_panties over_480p penis pink_hair pink_pineapple rape rope_bondage schoolgirl sex table tits twintails uncensored unseen_male_face vaginal_penetration vaginal_sex wooden_table yellow_hair_ribbon
1990s 1boy 1girls 20th_century 2d 2d_(artwork) 90s akagawa_rika animated big_breasts blush bondage boobs bound_feet elf_(company) female film_set filming gif glasses hair_ribbon haunted_house hi_res highres isaku long_twintails lying_on_back lying_on_table male moaning no_panties over_480p penis pink_hair pink_pineapple rape rope_bondage schoolgirl sex table tits twintails uncensored unseen_male_face vaginal_penetration vaginal_sex wooden_table yellow_hair_ribbon
1990s 1boy 1girls 20th_century 90s akagawa_rika animated blush bondage bound_feet brown_hair elf_(company) female film_set filming glasses hair_ribbon haunted_house hi_res highres isaku long_twintails looking_at_another looking_back lying_on_back lying_on_table male no_panties over_480p pink_hair pink_pineapple rape rope_bondage schoolgirl sex soga_munemitsu table twintails uncensored unseen_male_face vaginal_sex wooden_table yellow_hair_ribbon
1990s 1boy 1girls 20th_century 90s akagawa_rika animated blush bondage bound_feet brown_hair elf_(company) female film_set filming glasses hair_ribbon haunted_house hi_res highres isaku long_twintails looking_at_another looking_back lying_on_back lying_on_table male no_panties over_480p pink_hair pink_pineapple rape rope_bondage schoolgirl sex soga_munemitsu table twintails uncensored unseen_male_face vaginal_sex wooden_table yellow_hair_ribbon
1990s 1girls 20th_century 2d 2d_(artwork) 90s akagawa_rika animated breast_grab breasts elf_(company) enjoying female female_focus female_masturbation female_only fingering_self gif glasses hair_ribbon haunted_house hi_res highres isaku masturbation nude pink_hair pink_pineapple pussy_juice_trail ribbons screencap screenshot smile solo solo_female solo_focus twintails uncensored wooden_wall
1990s 1girls 20th_century 2d 2d_(artwork) 90s akagawa_rika animated breast_grab breasts elf_(company) enjoying female female_focus female_masturbation female_only fingering_self gif glasses hair_ribbon haunted_house hi_res highres isaku masturbation nude pink_hair pink_pineapple pussy_juice_trail ribbons screencap screenshot smile solo solo_female solo_focus twintails uncensored wooden_wall
1990s 1990s_(style) 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 2d_animation 720p 90s 960x720 animated big_breasts boobs brown_eyes brown_hair earring earrings elf_(company) face_focus faceless_male female female_focus haunted_house hi_res highres indoors isaku licking_penis long_hair loop looping_animation male nude nude_female outercourse paizuri penis_between_breasts pink_pineapple takashima_kumi teacher tits tongue uncensored
1990s 1990s_(style) 1boy 1boy1girl 1girls 20th_century 2d 2d_(artwork) 2d_animation 720p 90s 960x720 animated big_breasts boobs brown_eyes brown_hair earring earrings elf_(company) face_focus faceless_male female female_focus haunted_house hi_res highres indoors isaku licking_penis long_hair loop looping_animation male nude nude_female outercourse paizuri penis_between_breasts pink_pineapple takashima_kumi teacher tits tongue uncensored
1990s 1995 1boy 1girls 20th_century animated bio_hunter black_hair breast_fondling breasts fujihiko_hosono hi_res long_hair nipples oldschool
1990s 1995 1boy 1girls 20th_century animated bio_hunter black_hair breast_fondling breasts fujihiko_hosono hi_res long_hair nipples oldschool
1990s animated big_breasts big_penis bishoujo_senshi_sailor_moon blonde_hair brutal crossover deep_penetration dragon_ball goku hair_ribbon holding long_hair medium_breasts minako_aino mmg necklace rape retro_artstyle sailor_and_the_7_ballz sailor_venus son_goku tiara uncensored
1990s animated big_breasts big_penis bishoujo_senshi_sailor_moon blonde_hair brutal crossover deep_penetration dragon_ball goku hair_ribbon holding long_hair medium_breasts minako_aino mmg necklace rape retro_artstyle sailor_and_the_7_ballz sailor_venus son_goku tiara uncensored
1990s 1996 20th_century 2girls animated breasts brown_hair katana kotetsu_no_daibouken long_hair multiple_girls nude oldschool ponytail red_hair sword
1990s 1996 20th_century 2girls animated breasts brown_hair katana kotetsu_no_daibouken long_hair multiple_girls nude oldschool ponytail red_hair sword
1990s 1997 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_the_idiot_adventures purple_hair
1990s 1997 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century animated female fight keyne_aqua naked nude oldschool photon_earth photon_the_idiot_adventures purple_hair
1990s 1997 1boy 1girls 20th_century 90s ahoge angry animated antenna_hair armpits ass back barefoot bed_sheet black_eyes blush blushing body_writing bouncing_breasts bracelet breasts brown_hair clenched_teeth close-up clothed clothed_male clothed_male_nude_female clothing completely_naked completely_nude completely_nude_female covering covering_breasts covering_crotch covering_pussy covering_self defeat dive dizzy dodging earrings embarrassed embarrassed_nude_female energy energy_ball facial_mark feet female fighting fighting_stance flying full_body humor indoors jewelry jumping keyne_aqua kicking large_breasts levitating levitation long_hair looking_at_another male navel nipples no_sound nude nude_cover nude_female only_one_naked open_mouth pale_skin photon_earth photon_the_idiot_adventures pillow pointy_ears punching purple_hair red_eyes ring running running_away shaved_crotch shaved_pussy single_earring size_difference smaller_male smile soles sudden_realization takahashi_shinya teeth text toes tongue video
1990s 1997 1boy 1girls 20th_century 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 1994 1girls 20th_century animated arms_above_head bed bondage bottomless close-up f3:_frantic_frustrated_&_female female female_only hentai hiroe_ogawa_(f3) nageki_no_kenkou_yuuryouji nude ogawa_hiroe panties restrained socks socks_only solo spreader_bar struggling teenage_girl
1990s 1994 1girls 20th_century animated arms_above_head bed bondage bottomless close-up f3:_frantic_frustrated_&_female female female_only hentai hiroe_ogawa_(f3) nageki_no_kenkou_yuuryouji nude ogawa_hiroe panties restrained socks socks_only solo spreader_bar struggling teenage_girl
1990s 1994 20th_century 2girls animated assisted_exposure blonde_hair blue_eyes bra_lift breasts brown_hair ellyse_aldomordish embarrassed embarrassed_nude_female enf female long_hair multiple_girls nipples open_mouth plastic_little retro retro_artstyle shirt_up stripping tita_mu_koshigaya undressing undressing_another urushihara_satoshi
1990s 1994 20th_century 2girls animated assisted_exposure blonde_hair blue_eyes bra_lift breasts brown_hair ellyse_aldomordish embarrassed embarrassed_nude_female enf female long_hair multiple_girls nipples open_mouth plastic_little retro retro_artstyle shirt_up stripping tita_mu_koshigaya undressing undressing_another urushihara_satoshi
1990s 1996 1girl 20th_century animated breasts burn_up!_w cleavage clothing downblouse female_only fingerless_gloves gif gun heavy_breathing lying_on_back maya_jinguu_(burn_up!) microphone no_bra on_stomach solo sweat tank_top
1990s 1996 1girl 20th_century animated breasts burn_up!_w cleavage clothing downblouse female_only fingerless_gloves gif gun heavy_breathing lying_on_back maya_jinguu_(burn_up!) microphone no_bra on_stomach solo sweat tank_top
1990s 1999 1futa 20th_century animated anthro balls balls_clenching black_background breasts brown_hair canid canine canis clothing collar domestic_dog doug_winger english_text fully_sheathed futanari genitals getting_erect gif green_eyes gynomorph hair intersex low_res mammal nipples original pandora_(doug_winger) penis sheath short_hair short_playtime simple_background solo text throbbing_penis underwear
1990s 1999 1futa 20th_century animated anthro balls balls_clenching black_background breasts brown_hair canid canine canis clothing collar domestic_dog doug_winger english_text fully_sheathed futanari genitals getting_erect gif green_eyes gynomorph hair intersex low_res mammal nipples original pandora_(doug_winger) penis sheath short_hair short_playtime simple_background solo text throbbing_penis underwear
1990s 1999 1futa 20th_century animated anthro balls balls_clenching black_background breasts brown_hair canid canine canis clothing collar domestic_dog doug_winger english_text fully_sheathed futa_only futanari genitals getting_erect gif green_eyes gynomorph hair intersex low_res mammal nipples original pandora_(doug_winger) penis sheath short_hair short_playtime simple_background solo solo_futa text throbbing_penis underwear
1990s 1999 1futa 20th_century animated anthro balls balls_clenching black_background breasts brown_hair canid canine canis clothing collar domestic_dog doug_winger english_text fully_sheathed futa_only futanari genitals getting_erect gif green_eyes gynomorph hair intersex low_res mammal nipples original pandora_(doug_winger) penis sheath short_hair short_playtime simple_background solo solo_futa text throbbing_penis underwear
1990s 1999 1:1 1futa 20th_century all_fours animated anthro black_background blonde_hair bodily_fluids breasts canid canine canis collar cum domestic_dog doug_winger ejaculation_bulge english_text eyelashes futanari genital_fluids genitals green_eyes gynomorph hair humanoid_genitalia humanoid_penis intersex low_res mammal nipples open_mouth pandora_(doug_winger) penis short_playtime simple_background solo solo_futa tailwag text what
1990s 1999 1:1 1futa 20th_century all_fours animated anthro black_background blonde_hair bodily_fluids breasts canid canine canis collar cum domestic_dog doug_winger ejaculation_bulge english_text eyelashes futanari genital_fluids genitals green_eyes gynomorph hair humanoid_genitalia humanoid_penis intersex low_res mammal nipples open_mouth pandora_(doug_winger) penis short_playtime simple_background solo solo_futa tailwag text what
1990s 1998 1futa 20th_century animal_genitalia animal_penis animated anthro balls big_penis blinking breasts brown_eyes brown_hair canid canine canis collar domestic_dog doug_winger english_text equine_penis erection futanari genitals grin gynomorph hair horsecock intersex knot knotted_horsecock looking_at_viewer low_res mammal nipples nude original penis pup_(doug_winger) red_penis short_hair short_playtime smile solo solo_futa text
1990s 1998 1futa 20th_century animal_genitalia animal_penis animated anthro balls big_penis blinking breasts brown_eyes brown_hair canid canine canis collar domestic_dog doug_winger english_text equine_penis erection futanari genitals grin gynomorph hair horsecock intersex knot knotted_horsecock looking_at_viewer low_res mammal nipples nude original penis pup_(doug_winger) red_penis short_hair short_playtime smile solo solo_futa text
1990s 1995 1boy 1boy1girl 1girls 2d 2d_(artwork) 2d_animation 480p 640x480 90s alcohol_bottles alcoholic_beverage alcoholic_drink animated animated_gif bartender being_watched blue_hair bouncing_breasts breasts cool_devices elbow_gloves exhibitionism female gif human male nipple_piercing nipples nutech_digital oldschool pink_pineapple public retro see-through see-through_clothing short_hair staring surprised transparent_clothing walking watching
1990s 1995 1boy 1boy1girl 1girls 2d 2d_(artwork) 2d_animation 480p 640x480 90s alcohol_bottles alcoholic_beverage alcoholic_drink animated animated_gif bartender being_watched blue_hair bouncing_breasts breasts cool_devices elbow_gloves exhibitionism female gif human male nipple_piercing nipples nutech_digital oldschool pink_pineapple public retro see-through see-through_clothing short_hair staring surprised transparent_clothing walking watching
1990s 1994 2girls 90s animated ass bed begging_for_more blonde_hair blue_eyes blue_hair blush breasts dildo doggy_style dubbed_version english_dialogue english_dub english_voice english_voice_acting eyes_closed f3:_frantic_frustrated_&_female female female_only hentai hiroe_ogawa_(f3) long_hair longer_than_30_seconds longer_than_one_minute mayaka_(f3) mayaka_(nageki_no_kenkou_yuuryouji) medium_breasts medium_hair moaning mp4 multiple_girls nageki_no_kenkou_yuuryouji nipples nude ogawa_hiroe orgasm orgasm_denial screencap sex sex_toy softcel(dub) sound strap-on tagme thick_thighs topless underwear vaginal_penetration video voice_acted webm yuri
1990s 1994 2girls 90s animated ass bed begging_for_more blonde_hair blue_eyes blue_hair blush breasts dildo doggy_style dubbed_version english_dialogue english_dub english_voice english_voice_acting eyes_closed f3:_frantic_frustrated_&_female female female_only hentai hiroe_ogawa_(f3) long_hair longer_than_30_seconds longer_than_one_minute mayaka_(f3) mayaka_(nageki_no_kenkou_yuuryouji) medium_breasts medium_hair moaning mp4 multiple_girls nageki_no_kenkou_yuuryouji nipples nude ogawa_hiroe orgasm orgasm_denial screencap sex sex_toy softcel(dub) sound strap-on tagme thick_thighs topless underwear vaginal_penetration video voice_acted webm yuri
1990s 2d 2d_(artwork) 2girls 90s animated ass butt_crack couch cunnilingus desert_island_story_x female female_focus female_only hi_res highres indoors mujintou_monogatari_x multiple_girls natsuno_(mujintou_monogatari_x) oral panties_around_leg panties_down pink_pineapple red_hair red_skirt retro retro_artstyle screencap skirt_lift touko_(mujintou_monogatari_x) uncensored yuri
1990s 2d 2d_(artwork) 2girls 90s animated ass butt_crack couch cunnilingus desert_island_story_x female female_focus female_only hi_res highres indoors mujintou_monogatari_x multiple_girls natsuno_(mujintou_monogatari_x) oral panties_around_leg panties_down pink_pineapple red_hair red_skirt retro retro_artstyle screencap skirt_lift touko_(mujintou_monogatari_x) uncensored yuri
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
1990s 1995 1boy 20th_century 2girls animated bdsm bdsm_gear blue_hair breasts breasts_out censored chains collar cool_devices cum_in_mouth cum_on_breasts cum_on_face fetish_wear fingering hentai human_furniture multiple_girls nipple_piercing oral pink_hair purple_hair retro rubbing_pussy sex_club sound tagme video whip
1990s 1995 1boy 20th_century 2girls animated bdsm bdsm_gear blue_hair breasts breasts_out censored chains collar cool_devices cum_in_mouth cum_on_breasts cum_on_face fetish_wear fingering hentai human_furniture multiple_girls nipple_piercing oral pink_hair purple_hair retro rubbing_pussy sex_club sound tagme video whip
1990s 1990s_(style) 1girls 2d 2d_(artwork) 2d_animation 90s akagawa_rika animated animated_gif brown_eyes cum_from_mouth cum_in_mouth cum_leak cum_leaking elf_(company) english_subtitles female female_focus female_only gif glasses hair_ribbon haunted_house hi_res highres indoors isaku looking_at_viewer looking_back low_twintails lying_on_floor lying_on_side nude nude_female pink_hair pink_pineapple resting ribbons smile solo solo_female solo_focus twintails uncensored wooden_floor yellow_bowtie
1990s 1990s_(style) 1girls 2d 2d_(artwork) 2d_animation 90s akagawa_rika animated animated_gif brown_eyes cum_from_mouth cum_in_mouth cum_leak cum_leaking elf_(company) english_subtitles female female_focus female_only gif glasses hair_ribbon haunted_house hi_res highres indoors isaku looking_at_viewer looking_back low_twintails lying_on_floor lying_on_side nude nude_female pink_hair pink_pineapple resting ribbons smile solo solo_female solo_focus twintails uncensored wooden_floor yellow_bowtie