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1990s

1990s 1girls ass big_ass black_hair blush breasts buruma female female_only from_behind hair_ribbon highres king_of_fighters legs long_hair looking_back nakoruru purple_eyes retro_artstyle ribbon samurai_shodown school_girl schoolgirl shirt sideboob small_breasts snk solo sportswear thighs
1990s 1girls ass big_ass black_hair blush breasts buruma female female_only from_behind hair_ribbon highres king_of_fighters legs long_hair looking_back nakoruru purple_eyes retro_artstyle ribbon samurai_shodown school_girl schoolgirl shirt sideboob small_breasts snk solo sportswear thighs
1990s 1girls armor artist_request big_breasts bikini_armor blonde_hair breasts busty cleavage expressionless hand_on_hip hand_on_knee hand_on_own_knee highres large_breasts leaning_forward legs long_hair looking_at_viewer navel original ponytail pose posing purple_eyes retro_artstyle thighs voluptuous
1990s 1girls armor artist_request big_breasts bikini_armor blonde_hair breasts busty cleavage expressionless hand_on_hip hand_on_knee hand_on_own_knee highres large_breasts leaning_forward legs long_hair looking_at_viewer navel original ponytail pose posing purple_eyes retro_artstyle thighs voluptuous
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 1girls after_sex after_vaginal areolae blue_eyes bluethebone blush breasts cum cum_drip cum_inside earrings english_text female female_focus female_only happy happy_female heart-shaped_pupils hi_res horny horny_female hospital indoors light-skinned_female light_skin looking_at_viewer naked naked_female nintendo nipples nude nude_female nurse nurse_cap nurse_hat nurse_joy pink_hair pokemon pubic_hair pussy pussy_juice retro_artstyle smile solo solo_female spread_legs spreading talking talking_to_viewer text thick_thighs thighs uncensored
1990s 1girls after_sex after_vaginal areolae blue_eyes bluethebone blush breasts cum cum_drip cum_inside earrings english_text female female_focus female_only happy happy_female heart-shaped_pupils hi_res horny horny_female hospital indoors light-skinned_female light_skin looking_at_viewer naked naked_female nintendo nipples nude nude_female nurse nurse_cap nurse_hat nurse_joy pink_hair pokemon pubic_hair pussy pussy_juice retro_artstyle smile solo solo_female spread_legs spreading talking talking_to_viewer text thick_thighs thighs uncensored
1990s anthro ape big_penis bovid bovine cattle comparing duo erect_nipples european_mythology genitals greek_mythology haplorhine huge_cock humiliation luxley male male/male mammal micropenis minotaur monkey musclegut muscular mythology nerd nipples penis penis_humiliation primate size_difference small_dom_big_sub small_guy_big_penis small_penis small_penis_humiliation
1990s anthro ape big_penis bovid bovine cattle comparing duo erect_nipples european_mythology genitals greek_mythology haplorhine huge_cock humiliation luxley male male/male mammal micropenis minotaur monkey musclegut muscular mythology nerd nipples penis penis_humiliation primate size_difference small_dom_big_sub small_guy_big_penis small_penis small_penis_humiliation
1990s 1996 1boy 1girls clothing comic comic_page dress female femsub fully_clothed japanese_text lily_franky lowres male maledom mario_(series) official_art oral_sex page_3 plushie png princess princess_peach satellaview shitamachi_ninjo_gekijo straight text toad_(mario)
1990s 1996 1boy 1girls clothing comic comic_page dress female femsub fully_clothed japanese_text lily_franky lowres male maledom mario_(series) official_art oral_sex page_3 plushie png princess princess_peach satellaview shitamachi_ninjo_gekijo straight text toad_(mario)
1990s 1boy 1girls after_oral areolae begging begging_for_cum begging_for_more blonde_hair bluethebone blush braid braided_twintails breasts choker collarbone cum cum_drip cum_on_body cum_on_breasts cum_on_face cum_on_hands cute dungeon_meshi elf english_text facial female female_focus french_braid green_eyes hair_ribbon handjob heart-shaped_pupils hi_res horny horny_female indoors light-skinned_female light-skinned_male light_skin long_hair male marcille_donato naked naked_female nipples nude nude_female open_mouth oral oral_sex penis pointy_ears pubic_hair pussy red_choker red_ribbon retro_artstyle ribbon straight symbol-shaped_pupils text thighs tongue_out twin_braids twintails uncensored
1990s 1boy 1girls after_oral areolae begging begging_for_cum begging_for_more blonde_hair bluethebone blush braid braided_twintails breasts choker collarbone cum cum_drip cum_on_body cum_on_breasts cum_on_face cum_on_hands cute dungeon_meshi elf english_text facial female female_focus french_braid green_eyes hair_ribbon handjob heart-shaped_pupils hi_res horny horny_female indoors light-skinned_female light-skinned_male light_skin long_hair male marcille_donato naked naked_female nipples nude nude_female open_mouth oral oral_sex penis pointy_ears pubic_hair pussy red_choker red_ribbon retro_artstyle ribbon straight symbol-shaped_pupils text thighs tongue_out twin_braids twintails uncensored
1990s 1girls :3 areolae armlet armpits big_breasts bluethebone blush breasts dark_green_hair english_text eyebrows_visible_through_hair female female_focus female_only glowing green_hair hands_behind_head happy happy_female hi_res hourglass_figure huge_breasts large_breasts lasso_of_truth looking_at_viewer naked naked_female nude nude_female olive_hair presenting purple_eyes pussy retro_artstyle skindentation slender_waist smile smirk smug smug_face smug_grin solo solo_female solo_focus sousou_no_frieren subtitled subtitles sweat sweatdrop sweating talking_to_viewer text thick_thighs thigh_strap thighs ubel_(sousou_no_frieren) voluptuous voluptuous_female whip wide_hips
1990s 1girls :3 areolae armlet armpits big_breasts bluethebone blush breasts dark_green_hair english_text eyebrows_visible_through_hair female female_focus female_only glowing green_hair hands_behind_head happy happy_female hi_res hourglass_figure huge_breasts large_breasts lasso_of_truth looking_at_viewer naked naked_female nude nude_female olive_hair presenting purple_eyes pussy retro_artstyle skindentation slender_waist smile smirk smug smug_face smug_grin solo solo_female solo_focus sousou_no_frieren subtitled subtitles sweat sweatdrop sweating talking_to_viewer text thick_thighs thigh_strap thighs ubel_(sousou_no_frieren) voluptuous voluptuous_female whip wide_hips
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 1girls areolae blue_eyes bluethebone blush breasts earrings english_text female female_focus female_only happy happy_female heart-shaped_pupils hi_res horny horny_female hospital indoors light-skinned_female light_skin looking_at_viewer naked naked_female nintendo nipples nude nude_female nurse nurse_cap nurse_hat nurse_joy pink_hair pokemon pubic_hair pussy pussy_juice retro_artstyle smile solo solo_female spread_legs spreading talking talking_to_viewer text thick_thighs thighs uncensored
1990s 1girls areolae blue_eyes bluethebone blush breasts earrings english_text female female_focus female_only happy happy_female heart-shaped_pupils hi_res horny horny_female hospital indoors light-skinned_female light_skin looking_at_viewer naked naked_female nintendo nipples nude nude_female nurse nurse_cap nurse_hat nurse_joy pink_hair pokemon pubic_hair pussy pussy_juice retro_artstyle smile solo solo_female spread_legs spreading talking talking_to_viewer text thick_thighs thighs uncensored
1990s ai_generated anus blue_hair detailed_pussy erect_nipples erect_nipples_under_clothes injuu_gakuen_la_blue_girl la_blue_girl long_hair maria_(la_blue_girl) nipples_visible_through_clothing ossangtr presenting presenting_pussy retro retro_artstyle spread_pussy spreading spreading_pussy vagina
1990s ai_generated anus blue_hair detailed_pussy erect_nipples erect_nipples_under_clothes injuu_gakuen_la_blue_girl la_blue_girl long_hair maria_(la_blue_girl) nipples_visible_through_clothing ossangtr presenting presenting_pussy retro retro_artstyle spread_pussy spreading spreading_pussy vagina
1990s 1997 1girls 90s animated big_breasts bondage bound breathing closed_eyes drawn fuchikoma ghost_in_the_shell kusanagi_motoko masamune_shirow official_art playstation playstation_1 production_ig purple_hair shirou_masamune tagme thighhighs thighs visor_(eyewear) wire wires wrapped wrapped_up
1990s 1997 1girls 90s animated big_breasts bondage bound breathing closed_eyes drawn fuchikoma ghost_in_the_shell kusanagi_motoko masamune_shirow official_art playstation playstation_1 production_ig purple_hair shirou_masamune tagme thighhighs thighs visor_(eyewear) wire wires wrapped wrapped_up
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 1girls areolae blue_eyes bluethebone blush breasts earrings english_text female female_focus female_only happy happy_female heart-shaped_pupils hi_res horny horny_female hospital indoors light-skinned_female light_skin looking_at_viewer masturbation motion_lines naked naked_female nintendo nipples nude nude_female nurse nurse_cap nurse_hat nurse_joy penetrable_sex_toy penetration pink_hair pokemon pubic_hair pussy pussy_juice retro_artstyle sex_toy smile solo solo_female spread_legs spreading talking talking_to_viewer text thick_thighs thighs uncensored vaginal_penetration vibrator vibrator_in_pussy
1990s 1girls areolae blue_eyes bluethebone blush breasts earrings english_text female female_focus female_only happy happy_female heart-shaped_pupils hi_res horny horny_female hospital indoors light-skinned_female light_skin looking_at_viewer masturbation motion_lines naked naked_female nintendo nipples nude nude_female nurse nurse_cap nurse_hat nurse_joy penetrable_sex_toy penetration pink_hair pokemon pubic_hair pussy pussy_juice retro_artstyle sex_toy smile solo solo_female spread_legs spreading talking talking_to_viewer text thick_thighs thighs uncensored vaginal_penetration vibrator vibrator_in_pussy
1990s 1990s_(style) 1cuntboy 2024 2boys 4:3 :) :d accurate_art_style andromorph andromorph/andromorph andromorph_penetrated andromorph_penetrating animal_genitalia animal_penis animal_pussy anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bed bedroom bedroom_sex bodily_fluids bodily_fluids_in_pussy canid canine chihuahua clitoris closed_eyes cock cum cum_in_pussy cum_inside cumming cumming_in_pussy cuntboy cuntboy/male cuntboy_penetrated cuntboysub digital_drawing_(artwork) digital_media_(artwork) domestic_cat domestic_dog duo ejaculation ejaculation_while_penetrated erect erect_penis erection feline feline_pussy fucked_silly gay gay_domination gay_male gay_sex genderswap genderswap_(mti) genital_fluids genitals gloves hi_res highres holding humanoid_genitalia humanoid_penis humanoid_pussy impregnation_risk intersex intersex/male intersex_penetrated lamp looking_pleasured male male/male male_penetrated male_penetrating_cuntboy male_penetrating_intersex male_penetrating_male manx manx_cat moan moaning moaning_in_pleasure nickelodeon night nizisbizzy open_mouth orgasm orgasm_face overweight overweight_andromorph overweight_anthro overweight_cuntboy overweight_intersex overweight_male penetration penile penile_penetration penis penis_in_pussy pussy red_fur redraw ren_and_stimpy ren_höek ren_hoek retro_artstyle sex smile stimpy stimpy_j._cat teeth teeth_clenched teeth_showing teeth_visible tongue tongue_out toony vagina vaginal vaginal_penetration vaginal_sex vulva white_fur yaoi
1990s 1990s_(style) 1cuntboy 2024 2boys 4:3 :) :d accurate_art_style andromorph andromorph/andromorph andromorph_penetrated andromorph_penetrating animal_genitalia animal_penis animal_pussy anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bed bedroom bedroom_sex bodily_fluids bodily_fluids_in_pussy canid canine chihuahua clitoris closed_eyes cock cum cum_in_pussy cum_inside cumming cumming_in_pussy cuntboy cuntboy/male cuntboy_penetrated cuntboysub digital_drawing_(artwork) digital_media_(artwork) domestic_cat domestic_dog duo ejaculation ejaculation_while_penetrated erect erect_penis erection feline feline_pussy fucked_silly gay gay_domination gay_male gay_sex genderswap genderswap_(mti) genital_fluids genitals gloves hi_res highres holding humanoid_genitalia humanoid_penis humanoid_pussy impregnation_risk intersex intersex/male intersex_penetrated lamp looking_pleasured male male/male male_penetrated male_penetrating_cuntboy male_penetrating_intersex male_penetrating_male manx manx_cat moan moaning moaning_in_pleasure nickelodeon night nizisbizzy open_mouth orgasm orgasm_face overweight overweight_andromorph overweight_anthro overweight_cuntboy overweight_intersex overweight_male penetration penile penile_penetration penis penis_in_pussy pussy red_fur redraw ren_and_stimpy ren_höek ren_hoek retro_artstyle sex smile stimpy stimpy_j._cat teeth teeth_clenched teeth_showing teeth_visible tongue tongue_out toony vagina vaginal vaginal_penetration vaginal_sex vulva white_fur yaoi
1990s 1boy 1girls 2d 2d_animation animated anus ass ass_focus bluesona bluethebone bluethebone_(character) blush cum cum_in_pussy cum_inside dog_ears dog_girl dog_tail doggy_style english_text female female_focus from_behind gif grabbing grabbing_ass grabbing_from_behind grass hi_res light-skinned_female light-skinned_male light_skin looking_at_viewer looking_back looking_pleasured loop looping_animation male male_pov meat naked naked_female nude nude_female original outdoors outside penetration penis petplay pov pubic_hair pussy pussy_juice retro_artstyle sex short_playtime straight stuck stuck_in_fence stuck_in_wall tail text thick_ass uncensored vaginal_penetration vaginal_sex
1990s 1boy 1girls 2d 2d_animation animated anus ass ass_focus bluesona bluethebone bluethebone_(character) blush cum cum_in_pussy cum_inside dog_ears dog_girl dog_tail doggy_style english_text female female_focus from_behind gif grabbing grabbing_ass grabbing_from_behind grass hi_res light-skinned_female light-skinned_male light_skin looking_at_viewer looking_back looking_pleasured loop looping_animation male male_pov meat naked naked_female nude nude_female original outdoors outside penetration penis petplay pov pubic_hair pussy pussy_juice retro_artstyle sex short_playtime straight stuck stuck_in_fence stuck_in_wall tail text thick_ass uncensored vaginal_penetration vaginal_sex
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 90s_clothing 90s_decade absurd_res angie_de_windt animal_humanoid anthro aroused ass big_breasts big_butt breasts canid canid_humanoid canine canine_humanoid comic comic_book digital_drawing_(artwork) digital_media_(artwork) drug_addict drug_usage drugged drugs duo female fox fox_humanoid genus_magazine gesture group hi_res humanoid junkie levi_esthersson low_life male male/female male/male mammal mammal_humanoid mustelid mustelid_humanoid nightclub nymphomania oldschool otter otter_humanoid party party_hard party_sex party_time procyonid procyonid_humanoid prostitution raccoon raccoon_dog raccoon_humanoid rave red_light_district sanya_otter sex_worker solo substance_intoxication suggestive suggestive_gesture trainspotting trio wasyl_vos wasylthefox
1990s 1girls akane_tendo barrel blue_eyes covering_self female female_focus female_only light-skinned_female light_skin looking_at_another looking_at_viewer naked naked_female nude nude_female outdoor_bath outdoor_bathing outdoor_nudity outdoors ranma_1/2 screencap screenshot short_hair solo solo_female solo_focus towel towel_covering_breasts towel_only trees
1990s 1girls akane_tendo barrel blue_eyes covering_self female female_focus female_only light-skinned_female light_skin looking_at_another looking_at_viewer naked naked_female nude nude_female outdoor_bath outdoor_bathing outdoor_nudity outdoors ranma_1/2 screencap screenshot short_hair solo solo_female solo_focus towel towel_covering_breasts towel_only trees