320x240 best from all time

Time frame

320x240

1boy 1boy1girl 1girls 2004 2d 2d_(artwork) 2d_animation 320x240 absurdly_large_cock animated anus apple_butt ass big_ass breasts female gif hair huge_cock ikusa_otome_valkyrie interspecies long_hair long_twintails low_res low_resolution lowres male monster nude orc penis pussy rape red_hair red_twintails ride_of_the_valkyrie scar sex sexual_assault size_difference skuld_(ikusa_otome_valkyrie) small_breasts tied_hair twintails under_480p vaginal_penetration vaginal_rape
1boy 1boy1girl 1girls 2004 2d 2d_(artwork) 2d_animation 320x240 absurdly_large_cock animated anus apple_butt ass big_ass breasts female gif hair huge_cock ikusa_otome_valkyrie interspecies long_hair long_twintails low_res low_resolution lowres male monster nude orc penis pussy rape red_hair red_twintails ride_of_the_valkyrie scar sex sexual_assault size_difference skuld_(ikusa_otome_valkyrie) small_breasts tied_hair twintails under_480p vaginal_penetration vaginal_rape
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_(artwork) 2d_animation 320x240 animated ass female flossing gif itou_kisaku kisaku kisaku_spirit low_res lowres male panties panty_pull pink_panties pink_pineapple skirt skirt_lift straight sugimoto_shouko_(kisaku) wedgie
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_(artwork) 2d_animation 320x240 animated ass female flossing gif itou_kisaku kisaku kisaku_spirit low_res lowres male panties panty_pull pink_panties pink_pineapple skirt skirt_lift straight sugimoto_shouko_(kisaku) wedgie
00s 1girls 2000s 2000s_(style) 2000s_and_2010s_style 2d 2d_(artwork) 320x240 abs animated animation big_breasts bondage breasts convulsing convulsions delivery_man electric electric_shock electricity electro electrodes electrostimulation erect_nipples female_only femsub interrogation kay_yuzuiri living_sex_toy_delivery low_res low_resolution lowres muscle muscles muscular muscular_female muscular_sub nude nude_female pubic_hair restrained restraints shock shocked shocking short_hair spasm spasming spasms tagme tied_down twitching under_480p video wires
00s 1girls 2000s 2000s_(style) 2000s_and_2010s_style 2d 2d_(artwork) 320x240 abs animated animation big_breasts bondage breasts convulsing convulsions delivery_man electric electric_shock electricity electro electrodes electrostimulation erect_nipples female_only femsub interrogation kay_yuzuiri living_sex_toy_delivery low_res low_resolution lowres muscle muscles muscular muscular_female muscular_sub nude nude_female pubic_hair restrained restraints shock shocked shocking short_hair spasm spasming spasms tagme tied_down twitching under_480p video wires
00s 1boy 2000s 2000s_(style) 2000s_and_2010s_style 2002 2d 2d_(artwork) 2d_animation 2girls 320x240 animated animated_gif anna_kurashiki areolae behind_closed_doors blue_hair bondage breasts corset dominatrix female gif kenichi_sakaki kurashiki_anna lezdom low_res lowres male mask milky_animation_label multiple_girls shiny_skin skirt under_480p waver whip yuri
00s 1boy 2000s 2000s_(style) 2000s_and_2010s_style 2002 2d 2d_(artwork) 2d_animation 2girls 320x240 animated animated_gif anna_kurashiki areolae behind_closed_doors blue_hair bondage breasts corset dominatrix female gif kenichi_sakaki kurashiki_anna lezdom low_res lowres male mask milky_animation_label multiple_girls shiny_skin skirt under_480p waver whip yuri
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_animation 320x240 animated bishoujo_senshi_sailor_moon blush bouncing_breasts clothed_sex clothing cosplay crying crying_with_eyes_open dead_eyes drool drooling egg_vibrator faceless_male female female_focus gif green_eyes looking_at_viewer low_res lowres male medium_breasts murakami_teruaki nipple_tweak on_back oppai orange_hair pink_pineapple pov ribbon sailor_moon_(cosplay) school_uniform screen_capture seifuku_shoujo serafuku sex shirt shirt_lift tear tears tied_hair twintails vibrator
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_animation 320x240 animated bishoujo_senshi_sailor_moon blush bouncing_breasts clothed_sex clothing cosplay crying crying_with_eyes_open dead_eyes drool drooling egg_vibrator faceless_male female female_focus gif green_eyes looking_at_viewer low_res lowres male medium_breasts murakami_teruaki nipple_tweak on_back oppai orange_hair pink_pineapple pov ribbon sailor_moon_(cosplay) school_uniform screen_capture seifuku_shoujo serafuku sex shirt shirt_lift tear tears tied_hair twintails vibrator
00s 1boy 1boy1girl 1girls 2000s 2002 2d 2d_(artwork) 2d_animation 320x240 akimoto_aoi animated bouncing_breasts breasts elf_(company) female female_focus gif glasses green_hair kisaku large_breasts long_hair low_res lowres male megane meganekko nurse nurse_cap pink_pineapple qvga screencap under_480p
00s 1boy 1boy1girl 1girls 2000s 2002 2d 2d_(artwork) 2d_animation 320x240 akimoto_aoi animated bouncing_breasts breasts elf_(company) female female_focus gif glasses green_hair kisaku large_breasts long_hair low_res lowres male megane meganekko nurse nurse_cap pink_pineapple qvga screencap under_480p
320x240 animated balls big_ass dsi femboy flipnote fuzz_the_cat pixel_art the_june_archive_and_restoration_project twerking
320x240 animated balls big_ass dsi femboy flipnote fuzz_the_cat pixel_art the_june_archive_and_restoration_project twerking
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_animation 320x240 animated bishoujo_senshi_sailor_moon blush bouncing_breasts censored closed_eyes clothed_sex clothing cosplay drooling egg_vibrator faceless_male female female_focus gif large_breasts long_hair low_res lowres male murakami_teruaki nipple_tweak oppai orange_hair pink_pineapple ribbon sailor_moon_(cosplay) school_uniform screen_capture seifuku_shoujo serafuku sex shirt shirt_lift vibrator
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_animation 320x240 animated bishoujo_senshi_sailor_moon blush bouncing_breasts censored closed_eyes clothed_sex clothing cosplay drooling egg_vibrator faceless_male female female_focus gif large_breasts long_hair low_res lowres male murakami_teruaki nipple_tweak oppai orange_hair pink_pineapple ribbon sailor_moon_(cosplay) school_uniform screen_capture seifuku_shoujo serafuku sex shirt shirt_lift vibrator
1girls 2000 2000s 2000s_(style) 2000s_and_2010s_style 2d 2d_(artwork) 2d_animation 320x240 after_sex ail_soft animated blackmail blood breasts cum cum_in_pussy cum_inside cum_leaking cum_leaking_out_of_pussy female female_focus glasses kyouhaku long_red_hair low_res lowres meganekko nipples pink_pineapple pubes pubic_hair pussy qvga red_hair redhead uncensored under_480p virgin virginal_blood virginity_loss yuuki_aya
1girls 2000 2000s 2000s_(style) 2000s_and_2010s_style 2d 2d_(artwork) 2d_animation 320x240 after_sex ail_soft animated blackmail blood breasts cum cum_in_pussy cum_inside cum_leaking cum_leaking_out_of_pussy female female_focus glasses kyouhaku long_red_hair low_res lowres meganekko nipples pink_pineapple pubes pubic_hair pussy qvga red_hair redhead uncensored under_480p virgin virginal_blood virginity_loss yuuki_aya
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_animation 320x240 animated bishoujo_senshi_sailor_moon blush bouncing_breasts censored closed_eyes clothed_sex clothing cosplay egg_vibrator faceless_male female female_focus gif long_hair low_res lowres male medium_breasts murakami_teruaki nipple_tweak on_back open_mouth oppai orange_hair pink_pineapple sailor_moon_(cosplay) school_uniform screen_capture seifuku_shoujo serafuku sex shirt shirt_lift skirt vibrator
00s 1boy 1boy1girl 1girls 2000s 2004 2d 2d_animation 320x240 animated bishoujo_senshi_sailor_moon blush bouncing_breasts censored closed_eyes clothed_sex clothing cosplay egg_vibrator faceless_male female female_focus gif long_hair low_res lowres male medium_breasts murakami_teruaki nipple_tweak on_back open_mouth oppai orange_hair pink_pineapple sailor_moon_(cosplay) school_uniform screen_capture seifuku_shoujo serafuku sex shirt shirt_lift skirt vibrator
1990s 1990s_(style) 1boy 1girls 320x240 69 1997 90s animated female low_res lowres male nonomura_byouin_no_hitobito pink_pineapple retro retro_artstyle sex uncensored
1990s 1990s_(style) 1boy 1girls 320x240 69 1997 90s animated female low_res lowres male nonomura_byouin_no_hitobito pink_pineapple retro retro_artstyle sex uncensored