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1990s

1990s 1990s_(style) 1997 20th_century 2d 2d_(artwork) 2d_animation 2girls 3boys 540p 90s 960x540 abandoned_building age_difference animated ankles_tied areola arms_above_head arms_tied_above_head asian asian_female assisted_rape begging_to_stop big_breasts black_hair black_heels blue_skirt bra_lift breast_fondle breast_grab breast_sucking breasts breasts_out brown_eyes_male brown_hair clothed_male coercion crickets_chirping dirty_talk earrings elf_(company) english_audio english_dialogue english_dub english_voice english_voice_acting exposed_breasts feet_tied female fingering fingering_another floor forced glasses green_eyes green_eyes_female green_panties groping_breasts groping_from_behind group hair_pull hair_ribbon hands_tied haunted_house hentai hentai_series hi_res high_heel_boots highres hosome_eyes isaku itou_isaku large_ass large_breasts long_brown_hair long_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_5_minutes longer_than_one_minute maledom medium_breasts mikihara_akemi mp4 nipple_licking nipples older_male older_man_and_teenage_girl older_woman_and_younger_boy orange_hair panties_down pantyhose penetration pink_pineapple pink_skirt purple_panties pussy rape restrained retro retro_artstyle sex shimada_jinpachi shirt_up shocked_female skirt_lift skirt_up socks soga_munemitsu sound takashima_kumi teacher tennis_uniform uncensored uniform unwanted_sex vaginal_penetration vaginal_rape video videotape voice_acted watching_rape what_did_he_say wooden_floor younger_female
1990s 1990s_(style) 1997 20th_century 2d 2d_(artwork) 2d_animation 2girls 3boys 540p 90s 960x540 abandoned_building age_difference animated ankles_tied areola arms_above_head arms_tied_above_head asian asian_female assisted_rape begging_to_stop big_breasts black_hair black_heels blue_skirt bra_lift breast_fondle breast_grab breast_sucking breasts breasts_out brown_eyes_male brown_hair clothed_male coercion crickets_chirping dirty_talk earrings elf_(company) english_audio english_dialogue english_dub english_voice english_voice_acting exposed_breasts feet_tied female fingering fingering_another floor forced glasses green_eyes green_eyes_female green_panties groping_breasts groping_from_behind group hair_pull hair_ribbon hands_tied haunted_house hentai hentai_series hi_res high_heel_boots highres hosome_eyes isaku itou_isaku large_ass large_breasts long_brown_hair long_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_5_minutes longer_than_one_minute maledom medium_breasts mikihara_akemi mp4 nipple_licking nipples older_male older_man_and_teenage_girl older_woman_and_younger_boy orange_hair panties_down pantyhose penetration pink_pineapple pink_skirt purple_panties pussy rape restrained retro retro_artstyle sex shimada_jinpachi shirt_up shocked_female skirt_lift skirt_up socks soga_munemitsu sound takashima_kumi teacher tennis_uniform uncensored uniform unwanted_sex vaginal_penetration vaginal_rape video videotape voice_acted watching_rape what_did_he_say wooden_floor younger_female
1990s 1996 animated asian deadly_sex death desiccated desiccation energy_drain extreme_content female female_death hentai human injuu_kateikyoushi lesson_of_darkness male/female moaning monster murder offscreen_death outdoors pale_skin pink_pineapple pubic_hair public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1990s 1996 animated asian deadly_sex death desiccated desiccation energy_drain extreme_content female female_death hentai human injuu_kateikyoushi lesson_of_darkness male/female moaning monster murder offscreen_death outdoors pale_skin pink_pineapple pubic_hair public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1990s 1990s_(style) 1boy 1girls 2d 2d_(artwork) 2d_animation 360p 90s adult_and_teenager age_difference all_fours animated breasts completely_nude desert doggy_style female imma_youjo long_hair night night_sky nipples no_clothes nude nude_female nude_female_nude_male nude_male nude_male_nude_female outdoor_sex outdoors outside outside_sex pink_pineapple rape raped retro retro_artstyle sex sex_from_behind swaying_breasts taken_from_behind teenager thrusting white_hair young younger_female
1990s 1990s_(style) 1boy 1girls 2d 2d_(artwork) 2d_animation 360p 90s adult_and_teenager age_difference all_fours animated breasts completely_nude desert doggy_style female imma_youjo long_hair night night_sky nipples no_clothes nude nude_female nude_female_nude_male nude_male nude_male_nude_female outdoor_sex outdoors outside outside_sex pink_pineapple rape raped retro retro_artstyle sex sex_from_behind swaying_breasts taken_from_behind teenager thrusting white_hair young younger_female
1080p 1440x1080 1990s 1990s_(style) 1996 1boy 1boy1girl 1girls 20th_century 2boys 2d 2d_(artwork) 2d_animation 90s abuse_of_power acquiescent_female animated ass_grab begging_to_stop blackmail blowjob blush bouncing_breasts breasts coercion crying cunnilingus_through_clothes disabled drool elf_(company) english english_dialogue english_dub english_voice english_voice_acting fellatio female female_moaning fondling hands_on_head hd hi_res highres holding_flowers hospital indoors leggings listening listening_to_sex long_hair long_pink_hair long_twintails male mp4 nipples nonomura_byouin_no_hitobito nurse nurse_cap nurse_uniform oral oral_sex over_480p peeping pink_eyes pink_eyes_female pink_hair pink_pineapple police_officer pussy_fingering rape retro retro_artstyle saliva sex sex_from_behind socks sound spying straight tears thigh_socks thighhighs tied_hair tile tile_floor tiles twintails uncensored video voice_acted wheelchair white_socks
1080p 1440x1080 1990s 1990s_(style) 1996 1boy 1boy1girl 1girls 20th_century 2boys 2d 2d_(artwork) 2d_animation 90s abuse_of_power acquiescent_female animated ass_grab begging_to_stop blackmail blowjob blush bouncing_breasts breasts coercion crying cunnilingus_through_clothes disabled drool elf_(company) english english_dialogue english_dub english_voice english_voice_acting fellatio female female_moaning fondling hands_on_head hd hi_res highres holding_flowers hospital indoors leggings listening listening_to_sex long_hair long_pink_hair long_twintails male mp4 nipples nonomura_byouin_no_hitobito nurse nurse_cap nurse_uniform oral oral_sex over_480p peeping pink_eyes pink_eyes_female pink_hair pink_pineapple police_officer pussy_fingering rape retro retro_artstyle saliva sex sex_from_behind socks sound spying straight tears thigh_socks thighhighs tied_hair tile tile_floor tiles twintails uncensored video voice_acted wheelchair white_socks
1990s 1999 20th_century anal anal_sex animated anthro anthro_on_anthro ass big_breasts bodily_fluids bouncing_breasts breasts classic_animations closed_eyes cum cum_in_ass cum_inside do_not_distribute doggy_style duo erection eric_schwartz female female_penetrated from_behind_position genital_fluids genitals low_res male male/female male_penetrating male_penetrating_female mammal mephitid nude penetration penile penile_penetration penis pussy sex side_boob simple_background skunk stacey_(ews) stacey_skunk striped_skunk tongue
1990s 1999 20th_century anal anal_sex animated anthro anthro_on_anthro ass big_breasts bodily_fluids bouncing_breasts breasts classic_animations closed_eyes cum cum_in_ass cum_inside do_not_distribute doggy_style duo erection eric_schwartz female female_penetrated from_behind_position genital_fluids genitals low_res male male/female male_penetrating male_penetrating_female mammal mephitid nude penetration penile penile_penetration penis pussy sex side_boob simple_background skunk stacey_(ews) stacey_skunk striped_skunk tongue
1990s 1998 1girls 20th_century animated anthro ass_bigger_than_head black_screen_roulette blonde_hair blue_pony bouncing_breasts breasts_bigger_than_head fat fat_woman female female_only fuusenroba gif horse inflated_belly running solo tagme
1990s 1998 1girls 20th_century animated anthro ass_bigger_than_head black_screen_roulette blonde_hair blue_pony bouncing_breasts breasts_bigger_than_head fat fat_woman female female_only fuusenroba gif horse inflated_belly running solo tagme
1990s 1990s_(style) 1girls 90s animated animated_gif areola areolae atlus bangs big_breasts blue_eyes blue_hair blush bouncing_breasts breasts defeat defeated defeated_heroine door embarrassed embarrassed_female embarrassed_nude_exposure embarrassing embarrassment female female_focus female_only female_solo frown game_cg gif glowing hair_between_eyes human human_only humiliated humiliating humiliation japanese_language japanese_text jiggle jiggling jiggling_breasts large_breasts light-skinned_female light_skin long_hair looking_at_own_breasts looking_at_viewer looking_down lost_bet lowres matching_hair/eyes miko nipples non-web_source nude opening opening_door psikyo punishment punishment_game retro_artstyle sengoku_ace sengoku_blade shrine shrine_maiden solo solo_focus standing taisen_hot_gimmick taisen_hot_gimmick_kairakuten text togashi_koyori topless topless_female tsukasa_jun uncensored upper_body
1990s 1990s_(style) 1girls 90s animated animated_gif areola areolae atlus bangs big_breasts blue_eyes blue_hair blush bouncing_breasts breasts defeat defeated defeated_heroine door embarrassed embarrassed_female embarrassed_nude_exposure embarrassing embarrassment female female_focus female_only female_solo frown game_cg gif glowing hair_between_eyes human human_only humiliated humiliating humiliation japanese_language japanese_text jiggle jiggling jiggling_breasts large_breasts light-skinned_female light_skin long_hair looking_at_own_breasts looking_at_viewer looking_down lost_bet lowres matching_hair/eyes miko nipples non-web_source nude opening opening_door psikyo punishment punishment_game retro_artstyle sengoku_ace sengoku_blade shrine shrine_maiden solo solo_focus standing taisen_hot_gimmick taisen_hot_gimmick_kairakuten text togashi_koyori topless topless_female tsukasa_jun uncensored upper_body
1990s 1996 20th_century animated asian deadly_sex death desiccated desiccation energy_drain extreme_content female female_death final_orgasm human injuu_kateikyoushi lesson_of_darkness male/female moaning monster murder outdoors pale_skin pink_pineapple public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1990s 1996 20th_century animated asian deadly_sex death desiccated desiccation energy_drain extreme_content female female_death final_orgasm human injuu_kateikyoushi lesson_of_darkness male/female moaning monster murder outdoors pale_skin pink_pineapple public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1990 1990s 1girls animated ass character_request kounai_shasei panties red_background removing_clothing removing_panties stripping studio_fantasia studio_signal
1990 1990s 1girls animated ass character_request kounai_shasei panties red_background removing_clothing removing_panties stripping studio_fantasia studio_signal
1990s 1997 20th_century animated anime_style blonde_hair breasts brown_hair dna_productions first_porn_of_franchise glasses lost_media nanna nanna_and_lil'_puss_puss nipples no_sound orange_hair panties tagme video
1990s 1997 20th_century animated anime_style blonde_hair breasts brown_hair dna_productions first_porn_of_franchise glasses lost_media nanna nanna_and_lil'_puss_puss nipples no_sound orange_hair panties tagme video
1990s 1996 20th_century animated asian deadly_sex death desiccated desiccation energy_drain extreme_content female female_death final_orgasm human injuu_kateikyoushi lesson_of_darkness male/female moaning monster murder outdoors pale_skin pink_pineapple public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
1990s 1996 20th_century animated asian deadly_sex death desiccated desiccation energy_drain extreme_content female female_death final_orgasm human injuu_kateikyoushi lesson_of_darkness male/female moaning monster murder outdoors pale_skin pink_pineapple public rape sex snuff sound straight tagme tentacle vaginal vaginal_penetration video
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
1990s 1995 1girls animated bouncing_breasts bra character_request cleavage female female_focus female_only gif idol_project legwear skirt stripping studio_ox thighhighs
1990s 1995 1girls animated bouncing_breasts bra character_request cleavage female female_focus female_only gif idol_project legwear skirt stripping studio_ox thighhighs
1080p 1440x1080 1990s 1997 20th_century 2boys 2d 2girls 90s animated asakawa_kotomi ass_fondling ass_grab beard_stubble bed black_hair breaking_in captured captured_heroine coercion cunnilingus drool dubbed_version elf_(company) enema enema_syringe english_dialogue english_dub english_voice english_voice_acting female fingering fingering_another forced hands_tied hi_res hiding hiding_under_bed highres hosome_eyes humiliation indoors isaku itou_isaku knocking_on_door kogure_kenta long_black_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_5_minutes longer_than_one_minute male mp4 older_male older_male_younger_female over_480p pee peeing peeing_female peeing_self pink_hair pink_pineapple retro retro_artstyle sakaki_miyuki saliva socks sound tear tear_streaks tears tongue tongue_kiss tongue_kissing trying_to_escape ugly_man upskirt urinating_female urination urine urine_pool video voice_acted wooden_floor wooden_wall yellow_hair_ribbon yellow_panties younger_female
1080p 1440x1080 1990s 1997 20th_century 2boys 2d 2girls 90s animated asakawa_kotomi ass_fondling ass_grab beard_stubble bed black_hair breaking_in captured captured_heroine coercion cunnilingus drool dubbed_version elf_(company) enema enema_syringe english_dialogue english_dub english_voice english_voice_acting female fingering fingering_another forced hands_tied hi_res hiding hiding_under_bed highres hosome_eyes humiliation indoors isaku itou_isaku knocking_on_door kogure_kenta long_black_hair long_video longer_than_30_seconds longer_than_3_minutes longer_than_5_minutes longer_than_one_minute male mp4 older_male older_male_younger_female over_480p pee peeing peeing_female peeing_self pink_hair pink_pineapple retro retro_artstyle sakaki_miyuki saliva socks sound tear tear_streaks tears tongue tongue_kiss tongue_kissing trying_to_escape ugly_man upskirt urinating_female urination urine urine_pool video voice_acted wooden_floor wooden_wall yellow_hair_ribbon yellow_panties younger_female
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 gif hoop_earrings hourglass_figure jiggling_breasts long_hair madhouse_(studio) medium_breasts navel neon_lights nightclub solo solo_female 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 gif hoop_earrings hourglass_figure jiggling_breasts long_hair madhouse_(studio) medium_breasts navel neon_lights nightclub solo solo_female thighs very_long_hair
1990s 1990s_(style) 1boy 2girls 720p 90s 960x720 animated anime background_music bed bedroom big_penis bisexual_(female) black_hair blonde_hair blowjob blue_eyes blush breasts brown_hair collaborative_fellatio compilation cousins double_blowjob fellatio gloria_kindan_no_ketsuzoku green_eyes hd hd_(traditional) hentai holding_penis incest japanese_dialogue kissing kissing_penis lesbian_kiss licking_penis light-skinned_female light-skinned_male light_skin longer_than_30_seconds longer_than_one_minute maid multiple_girls night passionate pink_pineapple red_hair retro saliva_trail short_hair sound subtitled tagme teamwork undressing video voice_acted
1990s 1990s_(style) 1boy 2girls 720p 90s 960x720 animated anime background_music bed bedroom big_penis bisexual_(female) black_hair blonde_hair blowjob blue_eyes blush breasts brown_hair collaborative_fellatio compilation cousins double_blowjob fellatio gloria_kindan_no_ketsuzoku green_eyes hd hd_(traditional) hentai holding_penis incest japanese_dialogue kissing kissing_penis lesbian_kiss licking_penis light-skinned_female light-skinned_male light_skin longer_than_30_seconds longer_than_one_minute maid multiple_girls night passionate pink_pineapple red_hair retro saliva_trail short_hair sound subtitled tagme teamwork undressing video voice_acted
1990s 1990s_(style) 1girls 90s animated animated_gif areola areolae armpits arms_up atlus bangs big_breasts blue_eyes blue_hair blush bouncing_breasts breasts defeat defeated defeated_heroine dutch_angle embarrassed embarrassed_female embarrassed_nude_exposure embarrassing embarrassment eye_twitch female female_focus female_only female_solo forced game_cg gif hair_between_eyes hakama human human_only humiliated humiliating humiliation japanese_clothes jewelry jiggle jiggling jiggling_breasts kosode large_breasts light-skinned_female light_skin long_hair looking_at_viewer lost_bet lying matching_hair/eyes miko navel necklace nipples non-web_source nude ofuda ofuda_on_nipples on_back on_floor open_mouth pasties pasties_removed peeling psikyo punishment punishment_game retro_artstyle sengoku_ace sengoku_blade shrine_maiden solo solo_focus surprised surprised_expression surprised_face surprised_look taisen_hot_gimmick taisen_hot_gimmick_kairakuten talisman tape taped_nipples togashi_koyori topless topless_female tsukasa_jun twitching uncensored unworn_clothes upper_body wince wooden_floor
1990s 1990s_(style) 1girls 90s animated animated_gif areola areolae armpits arms_up atlus bangs big_breasts blue_eyes blue_hair blush bouncing_breasts breasts defeat defeated defeated_heroine dutch_angle embarrassed embarrassed_female embarrassed_nude_exposure embarrassing embarrassment eye_twitch female female_focus female_only female_solo forced game_cg gif hair_between_eyes hakama human human_only humiliated humiliating humiliation japanese_clothes jewelry jiggle jiggling jiggling_breasts kosode large_breasts light-skinned_female light_skin long_hair looking_at_viewer lost_bet lying matching_hair/eyes miko navel necklace nipples non-web_source nude ofuda ofuda_on_nipples on_back on_floor open_mouth pasties pasties_removed peeling psikyo punishment punishment_game retro_artstyle sengoku_ace sengoku_blade shrine_maiden solo solo_focus surprised surprised_expression surprised_face surprised_look taisen_hot_gimmick taisen_hot_gimmick_kairakuten talisman tape taped_nipples togashi_koyori topless topless_female tsukasa_jun twitching uncensored unworn_clothes upper_body wince wooden_floor
1990s 1990s_(style) 1998 1girls 20th_century 2boys 2d 2d_(artwork) 2d_animation 90s ambiguous_penetration animated arm_grab arm_pull asakawa_kotomi bouncing_breasts breasts clothed_female clothed_male_nude_female elf_(company) face_fucking female from_behind gif group group_rape group_sex hands_on_head isaku itou_isaku light-skinned_female low_res lowres mmf_threesome naked_female nipples pink_hair pink_pineapple rape ribbons sex_from_behind shimada_jinpachi spitroast standing_spitroast threesome twintails
1990s 1990s_(style) 1998 1girls 20th_century 2boys 2d 2d_(artwork) 2d_animation 90s ambiguous_penetration animated arm_grab arm_pull asakawa_kotomi bouncing_breasts breasts clothed_female clothed_male_nude_female elf_(company) face_fucking female from_behind gif group group_rape group_sex hands_on_head isaku itou_isaku light-skinned_female low_res lowres mmf_threesome naked_female nipples pink_hair pink_pineapple rape ribbons sex_from_behind shimada_jinpachi spitroast standing_spitroast threesome twintails