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1990s

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1990s 1girls ai_generated ass_visible_through_thighs breasts brown_eyes brown_hair duch_angle female iria iria:_zeiram_the_animation looking_at_viewer panties retro_artstyle solo thick_thighs thighs underboob underwear

ai_generatedass_visible_through_thighs

1990s ai_generated all_fours anus ass breasts brown_eyes brown_hair female female_only futuristic_background iria iria:_zeiram_the_animation looking_at_viewer multiple_views nipples nude nude_female on_back pussy retro_artstyle spread_legs thighs

ai_generatedall_fours

1990s ai_generated anus ass ass_focus bedroom brown_eyes brown_hair iria iria:_zeiram_the_animation looking_at_viewer looking_back mole_under_eye nude nude_female pussy retro_artstyle

ai_generatedanus

1990s ai_generated anus ass breasts brown_fur female female_only iria iria:_zeiram_the_animation legs_up mole_under_eye nipples nude nude_female pale-skinned_female pale_skin pussy retro_artstyle short_hair

ai_generatedanus

1990s 1990s_(style) 1futa ai_generated blush brown_hair cum_on_food fingerless_gloves futanari intersex large_breasts large_penis leaking_cum lifting_skirt meta: no_panties ova pixai ponytail public public_exposure public_indecency retro retro_artstyle self_upload semi-erect tagme uncensored uncut uncut_futa uncut_penis variable_geo very_long_hair waitress waitress_uniform yuka_takeuchi

ai_generatedblush

1990s 1futa ai_generated areola areolae balls_on_table brown_hair cum cum_on_food cum_on_table cumming_on_food diner fingerless_gloves futanari intersex large_breasts meta: naked ova pixai ponytail public public_exposure public_indecency public_nudity restaurant retro retro_artstyle self_upload solo solo_futa tagme uncensored uncut uncut_futa uncut_penis variable_geo very_long_hair yuka_takeuchi

ai_generatedareola

1990s ai_generated bed bedroom brown_eyes brown_hair female female_only iria iria:_zeiram_the_animation mole_under_eye on_bed open_bra pale-skinned_female pale_skin short_hair smile underwear white_underwear

ai_generatedbed

1990s 1990s_(style) 1boy 1girls accurate_art_style ai_generated areola areolae ayako_yuuki big_penis closed_eyes cum cum_on_face earrings hand_on_penis imminent_oral jewelry large_breasts medium_breasts meta: naked naked_female open_mouth ova pixai purple_hair retro retro_artstyle self_upload tagme tongue tongue_out uncensored unseen_male variable_geo very_long_hair

accurate_art_styleai_generated

1990s 1990s_(style) 1boy 1girls ai_generated areola areolae brown_hair cowgirl_position female fingerless_gloves hands_on_chest huge_breasts male_penetrating male_penetrating_female male_pubic_hair meta: ova pink_nipples ponytail retro retro_artstyle self_upload tagme underbust variable_geo very_long_hair yuka_takeuchi

ai_generatedareola

1990s 1994 1boy 1girls 20th_century censored censored_pussy cum cum_on_body cum_on_breasts drill_hair erect_nipples feet_out_of_frame feet_up female game_cg giga_(company) large_breasts mature mature_female meta: mosaic_censoring naked_female nipples open_mouth pc98 peeing peeing_in_mouth peeing_self pissing_in_mouth pixel_art reimi_jahana retro retro_artstyle silver_eyes silver_hair tagme unseen_male urination urine urine_stream variable_geo

censoredcensored_pussy

1990s 1990s_(style) 1girls ai_generated angry areola areolae arms_tied big_breasts blush blush blush_lines bondage bondage breasts brown_eyes brown_hair choker clenched_teeth completely_nude completely_nude_female female hands_tied_above_head headgear kunoichi legs_tied masuda_chiho meta: ninja ninja_girl no_blood no_bra no_panties potential_ryona questionable_consent retro retro_artstyle satoshi_donald scar scar_on_face scars scars_all_over short_hair solo solo_female solo_focus tagme upset variable_geo whip_marks

ai_generatedangry

1990s 1990s_(style) 1boy 1girls ai_generated bedroom bedroom_setting bedroom_sex big_penis blowjob blowjob_face cum_on_face dark-skinned_male drill_hair female hand_on_head large_breasts light-skinned_female long_hair mature mature_female meta: naked on_bed open_mouth penis_on_tongue pillow reimi_jahana retro retro_artstyle saliva saliva_drip satoshi_donald silver_hair tagme tongue tongue_out_blowjob variable_geo

ai_generatedbedroom

1990s 1990s_(style) 1boy 1girls ai_generated ass breasts_out choking cum cum_in_pussy cum_inside cum_on_ass exposed_breasts female leaking_cum male_penetrating male_pubic_hair mature mature_female milf miranda_jahana mother mother_(lore) no_bra no_panties retro_artstyle satoshi_donald tagme thick_ass tight_pussy unseen_male_face vaginal_penetration variable_geo

ai_generatedass

1990s 1990s_(style) 1boy 1girls ai_generated big_penis braid brown_eyes brown_hair cum cum_in_pussy cum_on_breasts cum_on_face cum_on_pantyhose female large_breasts long_hair meta: mitsurugi_tamao on_bed pantyhose penis_in_pussy pussy retro retro_artstyle satoshi_donald sex tagme teen teenage_girl teenager tight_pussy unseen_male_face vaginal_penetration variable_geo

ai_generatedbig_penis

1990s 2d 2girls ai_generated black_and_white cute lesbian_sex long_hair sex shower yuri

ai_generatedblack_and_white

1990s 1girls 2boys ai_generated anal_sex bishoujo_senshi_sailor_moon blue_eyes blue_hair bracelet breasts double_penetration gangbang large_breasts light-skinned_female light_skin lipstick long_hair looking_at_viewer looking_back looking_pleasured penis pink_lipstick pov pussy_juice pussy_juice_drip retro_ai_ecchi_dude sailor_aluminum_siren sideboob sitting_on_person stockings tagme thighhighs thighs threesome uncensored unseen_male_face vaginal_penetration

ai_generatedanal_sex

1990s 1boy 1girls ai_generated blue_hair blush braided_hair breasts cum cum_drip cum_in_pussy cum_inside cumshot dna^2 green_eyes heavy_breathing karin_aoi large_breasts large_penis light-skinned_female light_skin looking_at_viewer medium_hair penis penis_in_pussy pleasure_face pov retro_ai_ecchi_dude shounen_jump spread_legs spread_pussy spreading sweat sweaty_body tagme thighhighs tongue_out uncensored vaginal_penetration

ai_generatedblue_hair

1990s 1boy 1girls ai_generated blue_hair blush braided_hair breasts cum cum_drip cum_on_penis dna^2 green_eyes heavy_breathing horny_female karin_aoi large_breasts large_penis light-skinned_female light_skin looking_at_viewer looking_pleasured medium_hair penis penis_on_face pov retro_ai_ecchi_dude shounen_jump sweat sweaty_body tagme tongue_out uncensored

ai_generatedblue_hair

1990s 1990s_(style) 1girls ai_generated black_bra female hands_behind_back kubota_jun long_hair meta: ova pixai retro retro_artstyle solo solo_female solo_focus tagme variable_geo

ai_generatedblack_bra

1990s 1990s_(style) 1boy 1girls ai_generated balls ballsack blowjob boobs_out brown_hair deepthroat exposed_breasts fellatio female hand_on_head irrumatio long_hair male_pubic_hair meta: pink_nipples pixai ponytail retro retro_artstyle self_upload tagme variable_geo waitress yuka_takeuchi

ai_generatedballs

1990s 1990s_(style) 1boy 1girls ai_generated balls ballsack blowjob boobs_out deepthroat exposed_breasts fellatio female hand_on_head irrumatio large_breasts meta: ova penis pink_nipples pixai ponytail retro_artstyle self_upload tagme variable_geo very_long_hair yuka_takeuchi

ai_generatedballs

1990s 1990s_(style) 1boy 1girls ai_generated areola areolae blowjob breasts_out brown_hair clothed_female clothed_female_nude_male deepthroat deepthroat_hug fellatio female hand_on_head irrumatio large_breasts meta: orange_dress ova pink_nipples pixai ponytail retro retro_artstyle self_upload tagme variable_geo very_long_hair waitress waitress_uniform yuka_takeuchi

ai_generatedareola

1990s 1girls arm_under_breasts ass big_ass big_breasts black_hair blue_eyes blush bodysuit breasts busty cosplay fat_ass female female_only hair_ribbon half-closed_eyes hi_res highres huge_ass king_of_fighters large_breasts legs long_hair looking_at_viewer looking_back nakoruru neon_genesis_evangelion pose posing rei_ayanami retro_artstyle ribbon samurai_shodown sitting snk solo thighs unamused

arm_under_breastsass

1990s 1990s_(style) 4girls 720p 90s anal_insertion black_hair_female blonde_female bondage breasts brown_hair_female brown_hair_male candle_wax candles cool_devices cum cum_on_back dominatrix dubbed_version english_audio english_dub english_voice english_voice_acting eye_mask female_masturbation group_sex halloween halloween_costume haruka haruka_uciumi hi_res high_resolution highres indoors inner_thoughts karma licking_nipples lipstick long_blonde_hair long_hair long_hair_female longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_one_minute male_master mansion marino_okura mask masks moaning moaning_in_pleasure momomi_okazaki monoglove mp4 multiple_boys multiple_girls non-virgin nutech_digital offering over_480p party penis pink_pineapple red_rose retro retro_artstyle roses sadistic_smile saki_(cool_devices) saki_yazawa seek_~chikashitsu_no_mesu_dorei-tachi~ sex sex_party shorter_than_five_minutes sound thinking_about_another thinking_of_someone_else thorn uh_oh uncensored vaginal_penetration vibrator vibrator_in_ass video voice_acted watching watching_sex wax wax_on_body wet_pussy whip whipping_butt witch witch_hat

anal_insertionblack_hair_female

1990s 1990s_(style) 1995 1996 1girls 2025 2d 2d_(artwork) 90s after_orgasm after_sex ass athletic athletic_female back back_dimples back_view big_ass big_butt brown_hair bubble_butt closed_eyes completely_naked completely_naked_female completely_nude completely_nude_female curvy_ass curvy_body curvy_female curvy_figure cute cute_face dimples_of_venus female_focus female_protagonist fushigi_yuugi head_tilt high_quality high_resolution highres large_ass large_butt light-skinned_female light_skin medium_hair miaka_yuki naked naked_female no_sex not_ai_generated nude nude_female official_art perfect_body realistic_proportions retro_artstyle shower showering slim_girl slim_waist solo_female teen teen_girl teenage_girl teenager thin_female water waterfall wet young young_female young_woman younger_female

after_orgasmafter_sex

1990s 1993 90s blonde_female blonde_hair canonical_scene clothes_disappearing comic comic_page comic_panel covering_breasts covering_crotch dark-skinned_male embarrassed_female embarrassed_naked_female embarrassed_nude_female embarrassed_nude_male enf english english_dialogue english_text enm euf female glasses humiliation invisible_clothes invisible_woman marvel marvel_comics mass_embarrassment naked official_art old_man public public_humiliation suddenly_naked sue_storm

blonde_femaleblonde_hair

1990s 1990s_(style) 1996 1boy 1boy2girls 2d 2d_(artwork) 2girls 720p 90s 960x720 anal anal_creampie anal_insertion anal_juice anal_leakage anal_pump anal_sex animated anulingus anus assisted_masturbation barefoot big_breasts black_hair_female bondage bondage_harness breasts brown_hair brown_hair_female cell chains collar cool_devices cuffs cum cum_in_ass cum_inside demanding doggy_style dominatrix dubbed_version enema enema_punishment english_audio english_dialogue english_dub english_voice english_voice_acting exhausted fart farting female female_masturbation female_moaning femdom femsub fingering fingering_pussy forced_cunnilingus gloves harness indoors inflatable_sex_toy latex_armwear leash licking_anus licking_neck long_hair long_hair_female long_video longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes male male_master maledom marino_okura masturbation moaning monoglove mp4 nude_female nutech_digital object_insertion oppai over_480p penis_in_ass pet pink_pineapple prisoner red_thighhighs retro retro_artstyle saki_(cool_devices) saki_yazawa seek_~chikashitsu_no_mesu_dorei-tachi~ sex sex_slave sound spreading_ass stomach_noises straight tagme thighhighs tongue uncensored video voice_acted whip whipping worried_expression worried_face yuri

analanal_creampie

1990s 1990s_(style) 1996 1boy 1boy2girls 20th_century 2d 2d_(artwork) 2d_animation 2girls 720p 90s 960x720 animated aphrodisiac begging_to_stop big_breasts black_corset black_hair_female bondage bound_arms bound_legs candles cervix collar cool_devices dominatrix dubbed_version enduring_face english_audio english_dialogue english_dub english_voice english_voice_acting female female_moaning female_slave femsub fingerless_gloves fondling fondling_breasts fondling_pussy gloves gynecological_chair hands_tied hi_res high_resolution highres indoors insertion latex_legwear long_brown_hair long_hair long_hair_female longer_than_30_seconds longer_than_one_minute male male_master maledom marino_okura master_and_slave mp4 nipples no_bra no_panties nutech_digital over_480p pink_pineapple pussy red_eyes_female red_latex_legwear retro retro_artstyle saki_(cool_devices) saki_yazawa seek_~chikashitsu_no_mesu_dorei-tachi~ sex_slave shorter_than_3_minutes shorter_than_five_minutes shorter_than_four_minutes shorter_than_two_minutes smile sound spread_eagle spread_legs spreading_pussy tagme tile tile_floor tiles tits uncensored vaginal_insertion video

animatedaphrodisiac

1990s 1990s_(style) 1girls ai_generated belt blush bob_cut breasts breasts_out brown_eyes brown_hair goonedoutp3rv huge_breasts jacket jujutsu_kaisen kugisaki_nobara looking_away nipples open_clothes open_jacket open_shirt pout school_uniform shirt shirt_pull skirt solo

ai_generatedbelt

1990s 1990s_(style) 1992 1boy 1boy1girl 1girls 2d 2d_(artwork) 720p 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 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 prostitution pubic_hair 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 1girls 3boys artist_request ass beach blue_eyes blue_hair breasts cum cum_in_mouth cum_on_hair fat_man fingering_ass gangbang hairjob kaoru_kamiya large_breasts large_penis licking_penis light-skinned_female light_skin long_hair outdoors penis penis_in_pussy pleasure_face rurouni_kenshin sitting_on_person thick_thighs threesome uncensored unknown_artist vaginal_penetration

artist_requestass

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

1990s 1girls 3boys anal_sex artist_request blowjob blue_eyes blue_hair breasts cheating cum cum_in_ass cum_in_pussy cum_inside dark-skinned_male dark_skin double_penetration foursome gangbang kaoru_kamiya large_breasts large_penis light-skinned_female light_skin long_hair looking_at_partner looking_up penis penis_in_ass penis_in_mouth penis_in_pussy ponytail reverse_cowgirl_double_penetration reverse_cowgirl_position rurouni_kenshin 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_in_pussy cum_inside fan half_naked holding_object holding_thigh kaoru_kamiya kimono large_breasts light-skinned_female light_skin long_hair looking_at_partner penis penis_in_pussy ponytail rurouni_kenshin spread_legs sweat uncensored unknown_artist vaginal_penetration

artist_requestblue_eyes

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

anal_sexartist_request

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 jewelry 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 1boy1girl 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 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 prostitution pubic_hair 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 animated blonde_female blonde_hair blonde_hair_female breast_sucking breasts breasts_squeezed_together clothed_sex clothing_aside demon faust_münchhausen_ii indoors licking_nipple lowres magic_circle 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 embrace 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_naked_female completely_nude completely_nude_female 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_naked_female completely_nude completely_nude_female 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 1boy1girl 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_man_and_teenage_girl 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

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