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1990s

1990s 1990s_(style) 1992 1boy 1girls 2d 2d_(artwork) 720p 90s animated arthropod_girl assassin audible_speech bar bar_fight black_hair blowjob breasts breathing_heavily brown_eyes buju_(urotsukidouji) censored central_park_media china_dress chinese_clothes cowgirl_position dress dubbed_version english_audio english_dialogue english_dub english_voice english_voice_acting fangs fellatio female fingering fingering_partner green_hair half-demon hentai high_heels indoors interior jewelry licking_breasts licking_nipple lipstick long_black_hair long_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes lowres makeup male male_moaning mantis_woman_(urotsukidouji) medium_breasts monster mp4 muscular muscular_male neon_lights neon_sign nipple_stimulation nipples nude oral oral_sex over_480p penis prostitution pubic_hair pussy pussy_fingering red_lips red_lipstick retro retro_artstyle riding_penis scar sex sound spread_legs straddling straight tagme tail tentacle uncensored urotsukidouji vaginal_penetration video voice_acted wanting_sex warrior

1990s 1990s_(style) 1992 1boy 1girls 2d 2d_(artwork) 720p 90s animated arthropod_girl assassin audible_speech bar bar_fight black_hair blowjob breasts breathing_heavily brown_eyes buju_(urotsukidouji) censored central_park_media china_dress chinese_clothes cowgirl_position dress dubbed_version english_audio english_dialogue english_dub english_voice english_voice_acting fangs fellatio female fingering fingering_partner green_hair half-demon hentai high_heels indoors interior jewelry licking_breasts licking_nipple lipstick long_black_hair long_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes lowres makeup male male_moaning mantis_woman_(urotsukidouji) medium_breasts monster mp4 muscular muscular_male neon_lights neon_sign nipple_stimulation nipples nude oral oral_sex over_480p penis prostitution pubic_hair pussy pussy_fingering red_lips red_lipstick retro retro_artstyle riding_penis scar sex sound spread_legs straddling straight tagme tail tentacle uncensored urotsukidouji vaginal_penetration video voice_acted wanting_sex warrior

animatedarthropod_girl

1990s 1994 1995 1boy 1girls 20th_century 2d 2d_animation 90s animated bed bedroom bondage_queen_kate character_request close-up dark-skinned_male dark_skin drill_hair dubbed_version english_dub english_voice_acting female female_protagonist kate_(bondage_queen_kate) light-skinned_female light_skin longer_than_4_minutes male nessa_no_wakusei nude nude_female pussy red_hair retro_artstyle sex sex_in_bed shorter_than_five_minutes straight vaginal_penetration video voice_acted whentai

1990s 1994 1995 1boy 1girls 20th_century 2d 2d_animation 90s animated bed bedroom bondage_queen_kate character_request close-up dark-skinned_male dark_skin drill_hair dubbed_version english_dub english_voice_acting female female_protagonist kate_(bondage_queen_kate) light-skinned_female light_skin longer_than_4_minutes male nessa_no_wakusei nude nude_female pussy red_hair retro_artstyle sex sex_in_bed shorter_than_five_minutes straight vaginal_penetration video voice_acted whentai

00s 1990s 1990s_(style) 1999 1boy 1girls 2000 2d 2d_animation 90s all_fours animal_ears animated arched_back arms_(studio) astral_(words_worth) back bell bent_over blush breasts canonical_impregnation canonical_sex cat_ears cat_girl cat_tail catgirl cave closed_eyes clothed_female_nude_male clothed_sex collar cum cum_in_pussy cum_inside deep_penetration doggy_style female female_penetrated fingering fingering_partner grabbing_another's_breast groping hentai hentai_series jingle_bell kissing leaning_forward long_hair longer_than_2_minutes longer_than_3_minutes longer_than_one_minute lowres male male/female medium_breasts moaning moaning_in_pleasure naked navel neck_bell nina_(words_worth) nipples nude on_hands_and_knees open_mouth passionate_kiss pink_hair pumping pussy restrained retro_artstyle sex sex_from_behind sound straight tagme tail tongue_kiss top-down_bottom-up uncensored vaginal_penetration vaginal_sex video words_worth

00s 1990s 1990s_(style) 1999 1boy 1girls 2000 2d 2d_animation 90s all_fours animal_ears animated arched_back arms_(studio) astral_(words_worth) back bell bent_over blush breasts canonical_impregnation canonical_sex cat_ears cat_girl cat_tail catgirl cave closed_eyes clothed_female_nude_male clothed_sex collar cum cum_in_pussy cum_inside deep_penetration doggy_style female female_penetrated fingering fingering_partner grabbing_another's_breast groping hentai hentai_series jingle_bell kissing leaning_forward long_hair longer_than_2_minutes longer_than_3_minutes longer_than_one_minute lowres male male/female medium_breasts moaning moaning_in_pleasure naked navel neck_bell nina_(words_worth) nipples nude on_hands_and_knees open_mouth passionate_kiss pink_hair pumping pussy restrained retro_artstyle sex sex_from_behind sound straight tagme tail tongue_kiss top-down_bottom-up uncensored vaginal_penetration vaginal_sex video words_worth

all_foursanimal_ears

1990s 1990s_(style) 1999 1boy 2d 90s animal_ears animated arms_(studio) astral_(words_worth) back bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar cum doggy_style female fingering grabbing_another's_breast groping hentai hentai_series jingle_bell leaning_forward long_hair longer_than_one_minute lowres male medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping pussy restrained retro_artstyle sex sex_from_behind sound straight tagme tail top-down_bottom-up uncensored vaginal_penetration video words_worth

1990s 1990s_(style) 1999 1boy 2d 90s animal_ears animated arms_(studio) astral_(words_worth) back bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar cum doggy_style female fingering grabbing_another's_breast groping hentai hentai_series jingle_bell leaning_forward long_hair longer_than_one_minute lowres male medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping pussy restrained retro_artstyle sex sex_from_behind sound straight tagme tail top-down_bottom-up uncensored vaginal_penetration video words_worth

animal_earsanimated

1990s 1990s_(style) 1999 1boy 2d 90s animal_ears animated arms_(studio) astral_(words_worth) bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar female fingering grabbing_another's_breast groping hentai hentai_series jingle_bell long_hair longer_than_one_minute lowres male medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping retro_artstyle sound straight tagme tail uncensored video words_worth

1990s 1990s_(style) 1999 1boy 2d 90s animal_ears animated arms_(studio) astral_(words_worth) bell bent_over blush breasts cat_ears cat_tail cave closed_eyes clothed_female_nude_male clothed_sex collar female fingering grabbing_another's_breast groping hentai hentai_series jingle_bell long_hair longer_than_one_minute lowres male medium_breasts moaning navel neck_bell nina_(words_worth) nipples nude open_mouth pink_hair pumping retro_artstyle sound straight tagme tail uncensored video words_worth

animal_earsanimated

1990s 1990s_(style) 1999 2d 90s animated arms_(studio) bathroom blonde_hair blue_eyes breasts censored female hentai hentai_series indoors interior long_hair longer_than_one_minute lowres navel nipples nude pubic_hair retro_artstyle sharon_(words_worth) solo sound standing tagme video washing_hair words_worth

1990s 1990s_(style) 1999 2d 90s animated arms_(studio) bathroom blonde_hair blue_eyes breasts censored female hentai hentai_series indoors interior long_hair longer_than_one_minute lowres navel nipples nude pubic_hair retro_artstyle sharon_(words_worth) solo sound standing tagme video washing_hair words_worth

animatedarms_(studio)

1990s 1990s_(style) 1999 2d 90s animated arms_(studio) bathroom blonde_hair blue_eyes breasts censored female hentai hentai_series indoors interior long_hair lowres navel nipples nude retro_artstyle sharon_(words_worth) shorter_than_10_seconds solo sound standing tagme video washing_hair words_worth

1990s 1990s_(style) 1999 2d 90s animated arms_(studio) bathroom blonde_hair blue_eyes breasts censored female hentai hentai_series indoors interior long_hair lowres navel nipples nude retro_artstyle sharon_(words_worth) shorter_than_10_seconds solo sound standing tagme video washing_hair words_worth

animatedarms_(studio)

1990s 1boy 1girls artist_request blue_eyes blue_hair breasts female fucked_from_behind grabbing_ass grabbing_from_behind holding_object kaoru_kamiya large_breasts light-skinned_female light_skin long_hair male pussy rurouni_kenshin stripper_pole sweat tongue tongue_out uncensored unknown_artist vaginal_penetration

1990s 1boy 1girls artist_request blue_eyes blue_hair breasts female fucked_from_behind grabbing_ass grabbing_from_behind holding_object kaoru_kamiya large_breasts light-skinned_female light_skin long_hair male pussy rurouni_kenshin stripper_pole sweat tongue tongue_out uncensored unknown_artist vaginal_penetration

artist_requestblue_eyes

1990s 1girls 3boys artist_request ass beach blue_eyes blue_hair breasts cum cum_in_mouth cum_in_pussy cum_inside cum_on_hair ejaculation fat_male female fingering_ass gangbang hairjob kaoru_kamiya large_breasts large_penis licking_penis light-skinned_female light_skin long_hair male outdoors penis penis_in_pussy pleasure_face pussy rurouni_kenshin sex sitting_on_person thick_thighs threesome uncensored unknown_artist vaginal_penetration

1990s 1girls 3boys artist_request ass beach blue_eyes blue_hair breasts cum cum_in_mouth cum_in_pussy cum_inside cum_on_hair ejaculation fat_male female fingering_ass gangbang hairjob kaoru_kamiya large_breasts large_penis licking_penis light-skinned_female light_skin long_hair male outdoors penis penis_in_pussy pleasure_face pussy rurouni_kenshin sex sitting_on_person thick_thighs threesome uncensored unknown_artist vaginal_penetration

artist_requestass

1990s 1girls artist_request beach blue_eyes blue_hair breasts female fully_nude kaoru_kamiya large_breasts light-skinned_female light_skin long_hair naked_female outdoors ponytail rurouni_kenshin thighs uncensored unknown_artist

1990s 1girls artist_request beach blue_eyes blue_hair breasts female fully_nude kaoru_kamiya large_breasts light-skinned_female light_skin long_hair naked_female outdoors ponytail rurouni_kenshin thighs uncensored unknown_artist

artist_requestbeach

1990s 1boy 1girls anal_sex ass blue_eyes blue_hair breasts cheating female humping kaoru_kamiya large_breasts light-skinned_female light_skin long_hair looking_at_viewer looking_back male penis pussy rurouni_kenshin sideboob thighs uncensored

1990s 1boy 1girls anal_sex ass blue_eyes blue_hair breasts cheating female humping kaoru_kamiya large_breasts light-skinned_female light_skin long_hair looking_at_viewer looking_back male penis pussy rurouni_kenshin sideboob thighs uncensored

1990s 2d 2d_animation 2girls 90s age_difference animated areolae ass barefoot big_ass big_breasts blonde_hair bouncing_breasts breast_press breast_to_breast breasts brown_hair completely_nude female female/female female_on_female female_on_top female_only floor floor_sex gedou_gakuen girl_on_girl grinding hentai japanese_voice_acting kiss kiss_on_lips kissing lesbian lesbian_kiss lesbian_sex lesbians longer_than_10_seconds mature mature_female medium_hair missionary_position missionary_tribadism moaning moaning_in_pleasure nipples nipples_touching nude nude_female older_female older_female_and_younger_female on_top ova pussy pussy_grinding pussy_to_pussy scissoring sex short_hair shorter_than_10_seconds sound tagme tribadism uncensored vagina very_short_hair video voice_acted yuri

1990s 2d 2d_animation 2girls 90s age_difference animated areolae ass barefoot big_ass big_breasts blonde_hair bouncing_breasts breast_press breast_to_breast breasts brown_hair completely_nude female female/female female_on_female female_on_top female_only floor floor_sex gedou_gakuen girl_on_girl grinding hentai japanese_voice_acting kiss kiss_on_lips kissing lesbian lesbian_kiss lesbian_sex lesbians longer_than_10_seconds mature mature_female medium_hair missionary_position missionary_tribadism moaning moaning_in_pleasure nipples nipples_touching nude nude_female older_female older_female_and_younger_female on_top ova pussy pussy_grinding pussy_to_pussy scissoring sex short_hair shorter_than_10_seconds sound tagme tribadism uncensored vagina very_short_hair video voice_acted yuri

age_differenceanimated

1990s 2d 2d_animation 2girls 90s animated animated_gif areolae big_breasts bouncing_breasts breasts completely_nude eyebrows_visible_through_hair female female/female female_focus female_only gif hentai hentai_series injuu_gakuen_la_blue_girl kai_fubuki la_blue_girl large_breasts lesbian lesbian_sex light-skinned_female light_skin long_hair nipples nude nude_female ova pubes pubic_hair pussy pussy_to_pussy rubbing_pussies_together scissoring sex short_hair shoulder_length_hair sitting sitting_on_ground small_breasts thick thick_thighs tribadism uncensored vagina yaku yuri

1990s 2d 2d_animation 2girls 90s animated animated_gif areolae big_breasts bouncing_breasts breasts completely_nude eyebrows_visible_through_hair female female/female female_focus female_only gif hentai hentai_series injuu_gakuen_la_blue_girl kai_fubuki la_blue_girl large_breasts lesbian lesbian_sex light-skinned_female light_skin long_hair nipples nude nude_female ova pubes pubic_hair pussy pussy_to_pussy rubbing_pussies_together scissoring sex short_hair shoulder_length_hair sitting sitting_on_ground small_breasts thick thick_thighs tribadism uncensored vagina yaku yuri

animatedanimated_gif

1990s 1girls 3boys anal_sex artist_request ass blowjob blue_eyes blue_hair breasts cheating cum cum_in_ass cum_in_pussy cum_inside dark-skinned_male dark_skin double_penetration ejaculation fellatio female foursome gangbang kaoru_kamiya large_breasts large_penis light-skinned_female light_skin long_hair looking_at_partner looking_up male penis penis_in_ass penis_in_mouth penis_in_pussy ponytail pussy reverse_cowgirl_double_penetration reverse_cowgirl_position rurouni_kenshin sex sitting_on_person spread_legs sweat uncensored unknown_artist vaginal_penetration

1990s 1girls 3boys anal_sex artist_request ass blowjob blue_eyes blue_hair breasts cheating cum cum_in_ass cum_in_pussy cum_inside dark-skinned_male dark_skin double_penetration ejaculation fellatio female foursome gangbang kaoru_kamiya large_breasts large_penis light-skinned_female light_skin long_hair looking_at_partner looking_up male penis penis_in_ass penis_in_mouth penis_in_pussy ponytail pussy reverse_cowgirl_double_penetration reverse_cowgirl_position rurouni_kenshin sex sitting_on_person spread_legs sweat uncensored unknown_artist vaginal_penetration

anal_sexartist_request

1990s 1boy 1girls artist_request blue_eyes blue_hair breasts cheating condom cum cum_in_pussy cum_inside fan female half_naked holding_object holding_thigh kaoru_kamiya kimono large_breasts light-skinned_female light_skin long_hair looking_at_partner male penis penis_in_pussy ponytail pussy rurouni_kenshin sex spread_legs sweat uncensored unknown_artist vaginal_penetration

1990s 1boy 1girls artist_request blue_eyes blue_hair breasts cheating condom cum cum_in_pussy cum_inside fan female half_naked holding_object holding_thigh kaoru_kamiya kimono large_breasts light-skinned_female light_skin long_hair looking_at_partner male penis penis_in_pussy ponytail pussy rurouni_kenshin sex spread_legs sweat uncensored unknown_artist vaginal_penetration

artist_requestblue_eyes

1990s 1girls 3boys anal_sex artist_request ass black_hair breasts cheating closed_eyes double_penetration female foursome gangbang kaoru_kamiya large_penis light-skinned_female light_skin long_hair male medium_breasts open_mouth penis penis_in_ass penis_in_pussy pussy rurouni_kenshin sandwiched sex uncensored unknown_artist vaginal_penetration

1990s 1girls 3boys anal_sex artist_request ass black_hair breasts cheating closed_eyes double_penetration female foursome gangbang kaoru_kamiya large_penis light-skinned_female light_skin long_hair male medium_breasts open_mouth penis penis_in_ass penis_in_pussy pussy rurouni_kenshin sandwiched sex uncensored unknown_artist vaginal_penetration

anal_sexartist_request

1990s 1990s_(style) 1993 1girls 1monster 2d amano_megumi_(urotsukidouji) animated audible_speech bare_shoulders black_hair breasts breasts_out central_park_media chojin_(urotsukidouji) closed_eyes dark-skinned_female dark_skin doggy_style english_audio english_dialogue female green_hair hentai interspecies longer_than_30_seconds lowers lowres lying medium_breasts megumi_amano missionary monster nipples on_back open_mouth rape restrained retro_artstyle sex sex_from_behind short_hair size_difference sound tagme undead urotsukidouji video

1990s 1990s_(style) 1993 1girls 1monster 2d amano_megumi_(urotsukidouji) animated audible_speech bare_shoulders black_hair breasts breasts_out central_park_media chojin_(urotsukidouji) closed_eyes dark-skinned_female dark_skin doggy_style english_audio english_dialogue female green_hair hentai interspecies longer_than_30_seconds lowers lowres lying medium_breasts megumi_amano missionary monster nipples on_back open_mouth rape restrained retro_artstyle sex sex_from_behind short_hair size_difference sound tagme undead urotsukidouji video

amano_megumi_(urotsukidouji)animated

1990s 1990s_(style) 1993 1girls 2d 2d_(artwork) 2d_animation 90s amano_megumi_(urotsukidouji) animated audible_speech bare_shoulders black_hair bouncing_breasts breasts breasts_out central_park_media chojin_(urotsukidouji) closed_eyes dark-skinned_female dark_skin doggy_style earrings english_audio english_dialogue female green_hair hentai jewelry longer_than_30_seconds lowres medium_breasts monster nipples rape restrained retro_artstyle sex sex_from_behind short_hair sound tagme transformation undead upside-down urotsukidouji video

1990s 1990s_(style) 1993 1girls 2d 2d_(artwork) 2d_animation 90s amano_megumi_(urotsukidouji) animated audible_speech bare_shoulders black_hair bouncing_breasts breasts breasts_out central_park_media chojin_(urotsukidouji) closed_eyes dark-skinned_female dark_skin doggy_style earrings english_audio english_dialogue female green_hair hentai jewelry longer_than_30_seconds lowres medium_breasts monster nipples rape restrained retro_artstyle sex sex_from_behind short_hair sound tagme transformation undead upside-down urotsukidouji video

amano_megumi_(urotsukidouji)animated

1990s 1990s_(style) 1992 1boy 1girls 2d 2d_(artwork) animated arthropod_girl assassin audible_speech black_hair breasts brown_eyes buju_(urotsukidouji) censored central_park_media china_dress chinese_clothes cowgirl_position dress english_audio english_dialogue fangs female green_hair half-demon hentai indoors interior jewelry lipstick long_black_hair long_hair longer_than_30_seconds lowres makeup male mantis_woman_(urotsukidouji) medium_breasts monster muscular muscular_male nipples nude penis prostitution pubic_hair pussy retro retro_artstyle riding_penis scar sex shorter_than_3_minutes shorter_than_four_minutes shorter_than_one_minute shorter_than_two_minutes sound spread_legs straddling straight tagme tail tentacle tits urotsukidouji vaginal_penetration video warrior

1990s 1990s_(style) 1992 1boy 1girls 2d 2d_(artwork) animated arthropod_girl assassin audible_speech black_hair breasts brown_eyes buju_(urotsukidouji) censored central_park_media china_dress chinese_clothes cowgirl_position dress english_audio english_dialogue fangs female green_hair half-demon hentai indoors interior jewelry lipstick long_black_hair long_hair longer_than_30_seconds lowres makeup male mantis_woman_(urotsukidouji) medium_breasts monster muscular muscular_male nipples nude penis prostitution pubic_hair pussy retro retro_artstyle riding_penis scar sex shorter_than_3_minutes shorter_than_four_minutes shorter_than_one_minute shorter_than_two_minutes sound spread_legs straddling straight tagme tail tentacle tits urotsukidouji vaginal_penetration video warrior

animatedarthropod_girl

1990s 1990s_(style) 1991 1boy 1girls 2d animated blonde_female blonde_hair blonde_hair_female breast_sucking breasts breasts_squeezed_together clothed_sex clothing_aside demon faust_münchhausen_ii female hentai indoors licking_nipple longer_than_one_minute lowres magic_circle male medium_breasts monster nipple_stimulation nipples rape retro_artstyle ritual sound subtitled subtitles sucking_nipple summon summoning tagme tentacle tentacle_sex tentacles_under_clothes urotsukidouji video

1990s 1990s_(style) 1991 1boy 1girls 2d animated blonde_female blonde_hair blonde_hair_female breast_sucking breasts breasts_squeezed_together clothed_sex clothing_aside demon faust_münchhausen_ii female hentai indoors licking_nipple longer_than_one_minute lowres magic_circle male medium_breasts monster nipple_stimulation nipples rape retro_artstyle ritual sound subtitled subtitles sucking_nipple summon summoning tagme tentacle tentacle_sex tentacles_under_clothes urotsukidouji video

animatedblonde_female

1990s 1girls anime berserk black_eyes black_hair broken_sword candlelight casca contemplating dark-skinned_female dark_skin embrace female fit fit_female full_lips hugging_object lonely medieval_clothing pink_clothing sad screencap short_hair solo solo_female sword two-handed_sword

1990s 1girls anime berserk black_eyes black_hair broken_sword candlelight casca contemplating dark-skinned_female dark_skin embrace female fit fit_female full_lips hugging_object lonely medieval_clothing pink_clothing sad screencap short_hair solo solo_female sword two-handed_sword

1990s 1990s_(style) 1girls abs ai_generated blush breasts brown_hair completely_naked completely_nude embarrassed_female embarrassed_nude_female fake_screenshot female female_only humiliated humiliation looking_at_viewer muscular muscular_female naked naked_female nipples nude nude_female original original_character ponytail sweat tan_body tan_skin tanline tomboy

1990s 1990s_(style) 1girls abs ai_generated blush breasts brown_hair completely_naked completely_nude embarrassed_female embarrassed_nude_female fake_screenshot female female_only humiliated humiliation looking_at_viewer muscular muscular_female naked naked_female nipples nude nude_female original original_character ponytail sweat tan_body tan_skin tanline tomboy

absai_generated

1990s 1990s_(style) 1girls abs ai_generated blush breasts brown_hair completely_naked completely_nude embarrassed_female embarrassed_nude_female fake_screenshot female female_only humiliated humiliation looking_at_viewer muscular muscular_female naked naked_female nipples nude nude_female original original_character ponytail sweat tan_body tan_skin tanline tomboy

1990s 1990s_(style) 1girls abs ai_generated blush breasts brown_hair completely_naked completely_nude embarrassed_female embarrassed_nude_female fake_screenshot female female_only humiliated humiliation looking_at_viewer muscular muscular_female naked naked_female nipples nude nude_female original original_character ponytail sweat tan_body tan_skin tanline tomboy

absai_generated

1990s 1boy 1girls ai_art ai_assisted ai_generated ai_hands anus ass autismmix_pony(model) balls blue_eyes blush breasts cartoon classroom couple creampie crying desk female holding holding_legs legs_up lum male menda69 missionary_position nipples nude nude_female nude_male older older_male older_male_and_younger_female older_penetrating_younger open_legs penetration penis perfect_body perfect_legs pony_diffusion_(model) pony_diffusion_xl pussy rape raped school schoolgirl sex silly slim_waist squirting stable_diffusion tiger_print tits urusei_yatsura vaginal_penetration young younger_female younger_penetrating_older

1990s 1boy 1girls ai_art ai_assisted ai_generated ai_hands anus ass autismmix_pony(model) balls blue_eyes blush breasts cartoon classroom couple creampie crying desk female holding holding_legs legs_up lum male menda69 missionary_position nipples nude nude_female nude_male older older_male older_male_and_younger_female older_penetrating_younger open_legs penetration penis perfect_body perfect_legs pony_diffusion_(model) pony_diffusion_xl pussy rape raped school schoolgirl sex silly slim_waist squirting stable_diffusion tiger_print tits urusei_yatsura vaginal_penetration young younger_female younger_penetrating_older

ai_artai_assisted

1990s 1girls big_breasts blue_hair breasts brown_eyes busty censored female female_only hair_ribbon hi_res large_breasts legs long_hair looking_at_viewer navel nipples nude parted_lips pose posing pubic_hair pussy red_bow retro_artstyle sakura_shinguji sakura_wars sega sensual sexy_armpits spread_legs squatting thick_thighs thighs

1990s 1girls big_breasts blue_hair breasts brown_eyes busty censored female female_only hair_ribbon hi_res large_breasts legs long_hair looking_at_viewer navel nipples nude parted_lips pose posing pubic_hair pussy red_bow retro_artstyle sakura_shinguji sakura_wars sega sensual sexy_armpits spread_legs squatting thick_thighs thighs

big_breastsblue_hair

1990s 1990s_(style) 1996 2d 90s animated demon demon_beast_invasion female hentai longer_than_30_seconds longer_than_one_minute naked_female nude nude_female ocean skinny_dipping sound swimming tagme tentacle_sex underwater underwater_sex video youjuu_kyoushitsu

1990s 1990s_(style) 1996 2d 90s animated demon demon_beast_invasion female hentai longer_than_30_seconds longer_than_one_minute naked_female nude nude_female ocean skinny_dipping sound swimming tagme tentacle_sex underwater underwater_sex video youjuu_kyoushitsu

1990s 1990s_(style) 1996 2d 90s animated bed bedroom bedsheets demon_beast_invasion demons female hentai kayo_asakura longer_than_30_seconds music naked_female night nightmare sleeping_naked sleeping_nude sound sound_effects tagme video voice_acted youjuu_kyoushitsu

1990s 1990s_(style) 1996 2d 90s animated bed bedroom bedsheets demon_beast_invasion demons female hentai kayo_asakura longer_than_30_seconds music naked_female night nightmare sleeping_naked sleeping_nude sound sound_effects tagme video voice_acted youjuu_kyoushitsu

1990s 1998 anthro aroma_skunk bear black_nose blonde_hair blue_body blue_fur blue_hair bodily_fluids breasts brown_bear brown_body brown_fur clitoral_hood clitoris closed_eyes clothing dialogue drooling english_text female female/female finger_fuck fingering fisting fluffy fluffy_tail fragrance_skunk fur genital_fluids genitals gif grizzly_bear group hair kthanid_(artist) mammal mephitid nipple_fetish nipple_pinch nipple_play nipple_suck nipples nude outside penetration pinch pink_nose pussy rutwell_forest saliva shirt skunk static_gif sucking tail tank_top text tongue tongue_out toony topwear trio ursine ursula_bruin vaginal_fisting vaginal_fluids vaginal_penetration

1990s 1998 anthro aroma_skunk bear black_nose blonde_hair blue_body blue_fur blue_hair bodily_fluids breasts brown_bear brown_body brown_fur clitoral_hood clitoris closed_eyes clothing dialogue drooling english_text female female/female finger_fuck fingering fisting fluffy fluffy_tail fragrance_skunk fur genital_fluids genitals gif grizzly_bear group hair kthanid_(artist) mammal mephitid nipple_fetish nipple_pinch nipple_play nipple_suck nipples nude outside penetration pinch pink_nose pussy rutwell_forest saliva shirt skunk static_gif sucking tail tank_top text tongue tongue_out toony topwear trio ursine ursula_bruin vaginal_fisting vaginal_fluids vaginal_penetration

anthroaroma_skunk

1990s 1girls alternate_hairstyle big_breasts bikini blonde_hair breasts busty cleavage cross cross_necklace female female_only green_eyes highres janne_d'arc jewelry large_breasts legs medium_hair navel necklace open_mouth pink_bikini retro_artstyle smile snk solo swimsuit thighs tongue traditional_media traditional_media_(artwork) twintails voluptuous world_heroes

1990s 1girls alternate_hairstyle big_breasts bikini blonde_hair breasts busty cleavage cross cross_necklace female female_only green_eyes highres janne_d'arc jewelry large_breasts legs medium_hair navel necklace open_mouth pink_bikini retro_artstyle smile snk solo swimsuit thighs tongue traditional_media traditional_media_(artwork) twintails voluptuous world_heroes

alternate_hairstylebig_breasts

1990s 1997 1girls armpits arms_behind_head asuka_langley_sohryu b_village big_breasts breasts busty confident female female_only highres large_breasts long_hair looking_at_viewer monochrome neon_genesis_evangelion nipples nude pose posing seductive_look seductive_smile sensual sexy_armpits smile solo traditional_media traditional_media_(artwork) twintails voluptuous

1990s 1997 1girls armpits arms_behind_head asuka_langley_sohryu b_village big_breasts breasts busty confident female female_only highres large_breasts long_hair looking_at_viewer monochrome neon_genesis_evangelion nipples nude pose posing seductive_look seductive_smile sensual sexy_armpits smile solo traditional_media traditional_media_(artwork) twintails voluptuous

armpitsarms_behind_head

1990s 1girls 90s angry angry_face closed_eyes cum cum_on_face facial female pc98 pocket_dream purple_eyes purple_hair vision_soft

1990s 1girls 90s angry angry_face closed_eyes cum cum_on_face facial female pc98 pocket_dream purple_eyes purple_hair vision_soft

angryangry_face

1990s 1girls 90s d.o. dildo dildo_in_ass female hoshi_no_suna_monogatari hoshi_no_suna_monogatari_3 pc98 strap-on

1990s 1girls 90s d.o. dildo dildo_in_ass female hoshi_no_suna_monogatari hoshi_no_suna_monogatari_3 pc98 strap-on

1990s 1girls 90s cum cum_on_face female glasses green_hair jast_(company) pc98 tenshi-tachi_no_hohoemi

1990s 1girls 90s cum cum_on_face female glasses green_hair jast_(company) pc98 tenshi-tachi_no_hohoemi

1990s 1girls 90s cum cum_on_body d.o. female glasses nerd pc98 solo_female youjuu_senki_a.d._2048

1990s 1girls 90s cum cum_on_body d.o. female glasses nerd pc98 solo_female youjuu_senki_a.d._2048

1990s 1girls 90s brown_hair cum cum_on_face d.o. female hoshi_no_suna_monogatari hoshi_no_suna_monogatari_3 open_mouth pc98

1990s 1girls 90s brown_hair cum cum_on_face d.o. female hoshi_no_suna_monogatari hoshi_no_suna_monogatari_3 open_mouth pc98

1990s 1girls 90s blue_hair cry_sweeper d.o. female glasses open_mouth pc98 school_uniform

1990s 1girls 90s blue_hair cry_sweeper d.o. female glasses open_mouth pc98 school_uniform

blue_haircry_sweeper

1990s 1girls 90s cum cum_on_face d.o. facial female head_grab pc98 toriko_(d.o.) unwanted_cumshot

1990s 1girls 90s cum cum_on_face d.o. facial female head_grab pc98 toriko_(d.o.) unwanted_cumshot

1990s 1girls 90s female horikawa_nanase houkago_ren-ai_club libido_(company) orange_hair pc98 smile solo_female

1990s 1girls 90s female horikawa_nanase houkago_ren-ai_club libido_(company) orange_hair pc98 smile solo_female

femalehorikawa_nanase

1990s 1girls 90s abs bishoujo_dorei_club blush breasts brown_hair closed_eyes cowgirl_position female guilty_(company) pc98 penetration pubic_hair school_uniform

1990s 1girls 90s abs bishoujo_dorei_club blush breasts brown_hair closed_eyes cowgirl_position female guilty_(company) pc98 penetration pubic_hair school_uniform

absbishoujo_dorei_club

1990s big_breasts breasts comm commission cum_on_breasts cum_on_face dark_skin dialogue dirtyero_(artist) english_text eye_contact female male milf monica_(xenoblade) monica_vandham paizuri partial_male xenoblade_(series) xenoblade_chronicles_3

1990s big_breasts breasts comm commission cum_on_breasts cum_on_face dark_skin dialogue dirtyero_(artist) english_text eye_contact female male milf monica_(xenoblade) monica_vandham paizuri partial_male xenoblade_(series) xenoblade_chronicles_3

big_breastsbreasts

1990s 1992 1girls 20th_century animated ass black_hair bra breasts cleavage dancer dancing download:_devil's_circuit female female_focus female_only fingerless_gloves garter hoop_earrings hourglass_figure long_hair madhouse medium_breasts navel neon_lights nightclub solo solo_female suzie_wong thighs very_long_hair

1990s 1992 1girls 20th_century animated ass black_hair bra breasts cleavage dancer dancing download:_devil's_circuit female female_focus female_only fingerless_gloves garter hoop_earrings hourglass_figure long_hair madhouse medium_breasts navel neon_lights nightclub solo solo_female suzie_wong thighs very_long_hair

1990s 1990s_(style) 1996 20th_century 2d 2d_(artwork) 2d_animation 3animals 3dogs 3girls 480p 6+boys 720x480 90s animated assisted_exposure bdsm begging_to_stop being_watched blonde_female blonde_hair blonde_hair_female bondage brown_hair brown_hair_female cool_devices crowd crowd_watching cunnilingus_from_canine dilated_pupils dogs dominant_feral drool dubbed_version electric_shock electricity electrodes electrostimulation english_audio english_dub english_voice english_voice_acting evil_smile female flashback haruka haruka_uciumi hi_res high_resolution highres indoors licking_pussy lipstick long_brown_hair male male_canine marino_okura masks multiple_boys multiple_females multiple_girls multiple_males muscular muscular_male nose_hook nutech_digital pee peeing peeing_self pink_pineapple pussy red_eyes_female red_lips red_lipstick retro retro_artstyle ripped_clothing sadist sadistic_female sadistic_smile sadomasochism saki_(cool_devices) saki_yazawa saliva scream screaming_in_pain seek_~chikashitsu_no_mesu_dorei-tachi~ sexually_aggressive_animal shock shocked shocking sniffing_panties tagme tears tears_of_desperation torn_bra torn_skirt trained video voice_acted watching watching_rape watching_through_window waterboarding whip whip_marks whipping wooden_wheel

1990s 1990s_(style) 1996 20th_century 2d 2d_(artwork) 2d_animation 3animals 3dogs 3girls 480p 6+boys 720x480 90s animated assisted_exposure bdsm begging_to_stop being_watched blonde_female blonde_hair blonde_hair_female bondage brown_hair brown_hair_female cool_devices crowd crowd_watching cunnilingus_from_canine dilated_pupils dogs dominant_feral drool dubbed_version electric_shock electricity electrodes electrostimulation english_audio english_dub english_voice english_voice_acting evil_smile female flashback haruka haruka_uciumi hi_res high_resolution highres indoors licking_pussy lipstick long_brown_hair male male_canine marino_okura masks multiple_boys multiple_females multiple_girls multiple_males muscular muscular_male nose_hook nutech_digital pee peeing peeing_self pink_pineapple pussy red_eyes_female red_lips red_lipstick retro retro_artstyle ripped_clothing sadist sadistic_female sadistic_smile sadomasochism saki_(cool_devices) saki_yazawa saliva scream screaming_in_pain seek_~chikashitsu_no_mesu_dorei-tachi~ sexually_aggressive_animal shock shocked shocking sniffing_panties tagme tears tears_of_desperation torn_bra torn_skirt trained video voice_acted watching watching_rape watching_through_window waterboarding whip whip_marks whipping wooden_wheel

animatedassisted_exposure

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