sad animated best from all time

Time frame

Tags

sad

1boy angry animal_ears animated animated_gif brown_hair craft_lawrence crying holo red_eyes sad screencap spice_and_wolf surprised tail tears upset wolf_ears wolf_tail yandere
1boy angry animal_ears animated animated_gif brown_hair craft_lawrence crying holo red_eyes sad screencap spice_and_wolf surprised tail tears upset wolf_ears wolf_tail yandere
:>= altered_common_sense animated animated_gif black_eyes black_hair blue_socks blush brown_eyes brown_hair common_sense_change crying crying_with_eyes_open cum_in_mouth emotionless emotionless_sex ero-note:_ore_ga_nani_shite_mo_mondai_ni_naranai_kyoushitsu fat_man first_time gif hands_on_head hypnosis indifferent kneeling leo_shishioka licking_penis looking_at_viewer mind_break mind_control no_skirt nyuu_(manekin-eko) oral oral_sex pink_eyes pink_hair ribbon_matsumoto sachi_(ero-note) sad school_uniform schoolgirl sex shoes skirt_removed unhappy virginity_loss wet_clothes
:>= altered_common_sense animated animated_gif black_eyes black_hair blue_socks blush brown_eyes brown_hair common_sense_change crying crying_with_eyes_open cum_in_mouth emotionless emotionless_sex ero-note:_ore_ga_nani_shite_mo_mondai_ni_naranai_kyoushitsu fat_man first_time gif hands_on_head hypnosis indifferent kneeling leo_shishioka licking_penis looking_at_viewer mind_break mind_control no_skirt nyuu_(manekin-eko) oral oral_sex pink_eyes pink_hair ribbon_matsumoto sachi_(ero-note) sad school_uniform schoolgirl sex shoes skirt_removed unhappy virginity_loss wet_clothes
1boy 1girls anal animated blowjob brother_and_sister cowgirl_position creampie cum cum_in_mouth cum_in_pussy cum_inside cumshot cunnilingus depression dialogue doggy_style dream dreaming eating_pussy fellatio handjob horror i_love_you impregnation incest kissing mari_(omori) missionary_position music nightmare nighttime older_female older_sister omori on_table oral oral_creampie oral_sex pixel_animation pixel_art sad siblings sound sound_warning sprite sprites subliminal sunny_(omori) tagme text_box theevilfallenone vaginal_penetration video younger_brother younger_male
1boy 1girls anal animated blowjob brother_and_sister cowgirl_position creampie cum cum_in_mouth cum_in_pussy cum_inside cumshot cunnilingus depression dialogue doggy_style dream dreaming eating_pussy fellatio handjob horror i_love_you impregnation incest kissing mari_(omori) missionary_position music nightmare nighttime older_female older_sister omori on_table oral oral_creampie oral_sex pixel_animation pixel_art sad siblings sound sound_warning sprite sprites subliminal sunny_(omori) tagme text_box theevilfallenone vaginal_penetration video younger_brother younger_male
2boys 3d 3girls animated animated_gif black_hair blake_belladonna blue_eyes bowl fish grin lowres multiple_boys multiple_girls rwby sad smile weiss_schnee white_hair yellow_eyes
2boys 3d 3girls animated animated_gif black_hair blake_belladonna blue_eyes bowl fish grin lowres multiple_boys multiple_girls rwby sad smile weiss_schnee white_hair yellow_eyes
1boy 1girls animated anime areola arms_up athletic_female beard big_breasts blonde_hair bondage bound brown_eyes brown_hair captive captured captured_heroine curvy damsel_in_distress danger defeated defeated_heroine dialogue domination dubbed_version dungeon embarrassed embarrassed_nude_exposure embarrassed_nude_female english english_dialogue english_voice enslaved fairy_tail fairy_tail:_dragon_cry female female_focus femsub forced forced_exposure forced_submission helpless hostage huge_breasts humiliation hypnosis kidnapped large_breasts light_skin lucy_heartfilia maledom mind_control multiple_females multiple_girls nipples nude nude_filter official_animation prison_bitch prisoner pussy resisting restrained s10collage sad sad_sub screenshot_edit sex_slave slave slavegirl slaver sound submissive submissive_female surprised sword sехual tagme thick_thighs torture uncomfortable unhappy unhappy_female video voice_acted wide_hips worried zash_caine
1boy 1girls animated anime areola arms_up athletic_female beard big_breasts blonde_hair bondage bound brown_eyes brown_hair captive captured captured_heroine curvy damsel_in_distress danger defeated defeated_heroine dialogue domination dubbed_version dungeon embarrassed embarrassed_nude_exposure embarrassed_nude_female english english_dialogue english_voice enslaved fairy_tail fairy_tail:_dragon_cry female female_focus femsub forced forced_exposure forced_submission helpless hostage huge_breasts humiliation hypnosis kidnapped large_breasts light_skin lucy_heartfilia maledom mind_control multiple_females multiple_girls nipples nude nude_filter official_animation prison_bitch prisoner pussy resisting restrained s10collage sad sad_sub screenshot_edit sex_slave slave slavegirl slaver sound submissive submissive_female surprised sword sехual tagme thick_thighs torture uncomfortable unhappy unhappy_female video voice_acted wide_hips worried zash_caine
animated big_ass bouncing_ass bouncing_breasts bubble_butt butt_crack capdocks clothed clothing dialogue dressing huge_ass huge_butt humanoid medium_breasts no_humans panties pants pants_down pants_pull red_skin sad shaking_butt tammy_(averyshadydolphin) tight_clothing twerking white_background
animated big_ass bouncing_ass bouncing_breasts bubble_butt butt_crack capdocks clothed clothing dialogue dressing huge_ass huge_butt humanoid medium_breasts no_humans panties pants pants_down pants_pull red_skin sad shaking_butt tammy_(averyshadydolphin) tight_clothing twerking white_background
1girl animated anime_screenshot black_hair blood breasts cleavage crying crying_with_eyes_open en'en_no_shouboutai injury long_hair looking_at_viewer sad solo tamaki_kotatsu tears trembling twintails upper_body video yellow_eyes
1girl animated anime_screenshot black_hair blood breasts cleavage crying crying_with_eyes_open en'en_no_shouboutai injury long_hair looking_at_viewer sad solo tamaki_kotatsu tears trembling twintails upper_body video yellow_eyes
1girl animated animated_gif breasts brown_eyes brown_hair cleavage cleavage_cutout clothing_cutout crop_top female_focus front-tie_top halterneck midriff open_mouth sad solo tears twintails viper_(series) viper_rsr
1girl animated animated_gif breasts brown_eyes brown_hair cleavage cleavage_cutout clothing_cutout crop_top female_focus front-tie_top halterneck midriff open_mouth sad solo tears twintails viper_(series) viper_rsr
3d 6+girls alicia_arcturus animated armor athletic_female bad_end big_ass big_breasts big_butt big_penis blender bondage bound broken_rape_victim captured captured_heroine captured_villainess celestine_lucross claudia_levantine cloe_(kuroinu) cowgirl_position damsel_in_distress dark_elf dark_elf_female defeated defeated_heroine defeated_villainess domination elf elf_female enslaved fellatio female femsub forced forced_exposure forced_submission gangbang gangrape group group_rape group_sex helpless humiliation kaguya_(kuroinu) kidnapped kidnapping kuroinu_~kedakaki_seijo_wa_hakudaku_ni_somaru~ longer_than_2_minutes maia_(kuroinu) maledom missionary_position mp4 multiple_boys multiple_females multiple_girls olga_discordia opiumud orgy penis preview prim_fiorire prisoner rape restrained ruu_ruu sad sad_sub sex_slave slave slavegirl slaver sound spitroast splits spoils_of_war submissive submissive_female unhappy unhappy_female video villainess
3d 6+girls alicia_arcturus animated armor athletic_female bad_end big_ass big_breasts big_butt big_penis blender bondage bound broken_rape_victim captured captured_heroine captured_villainess celestine_lucross claudia_levantine cloe_(kuroinu) cowgirl_position damsel_in_distress dark_elf dark_elf_female defeated defeated_heroine defeated_villainess domination elf elf_female enslaved fellatio female femsub forced forced_exposure forced_submission gangbang gangrape group group_rape group_sex helpless humiliation kaguya_(kuroinu) kidnapped kidnapping kuroinu_~kedakaki_seijo_wa_hakudaku_ni_somaru~ longer_than_2_minutes maia_(kuroinu) maledom missionary_position mp4 multiple_boys multiple_females multiple_girls olga_discordia opiumud orgy penis preview prim_fiorire prisoner rape restrained ruu_ruu sad sad_sub sex_slave slave slavegirl slaver sound spitroast splits spoils_of_war submissive submissive_female unhappy unhappy_female video villainess
2girls 4boys ahe_gao animated big_ass black_hair blonde_hair blowjob blue_eyes breast_grab clothed_male clothed_male_nude_female defeated defeated_heroine demon dominant_male ejaculation female_knight gangbang grabbing_breasts grabbing_own_breast handjob happy happy_sex hime_cut holding_penis huge_breasts large_breasts luvirias male_penetrating maledom mind_break mindbreak multiple_boys multiple_handjob nude_female nude_female_clothed_male nun ochi_mono_rpg_seikishi_luvilias on_knees orgy outercourse paizuri purple_eyes rape sad smile smiling sound spitroast straight submission tongue_out twintails video virgin virginity_loss
2girls 4boys ahe_gao animated big_ass black_hair blonde_hair blowjob blue_eyes breast_grab clothed_male clothed_male_nude_female defeated defeated_heroine demon dominant_male ejaculation female_knight gangbang grabbing_breasts grabbing_own_breast handjob happy happy_sex hime_cut holding_penis huge_breasts large_breasts luvirias male_penetrating maledom mind_break mindbreak multiple_boys multiple_handjob nude_female nude_female_clothed_male nun ochi_mono_rpg_seikishi_luvilias on_knees orgy outercourse paizuri purple_eyes rape sad smile smiling sound spitroast straight submission tongue_out twintails video virgin virginity_loss
1boy 1boy1girl 1girl 1girls 3d 3d_animation 69 69_position abuse abused_female after_fellatio after_oral after_sex all_the_way_to_the_base alley alleyway angry angry_expression angry_face animated animation ashamed asian balls_deep big_balls big_dick big_lips big_penis bimbo_lips black_body black_cock black_hair black_lingerie black_male black_man black_penis blowjob blowjob_face blue_eyeshadow broken brown_eyes brown_skin choking_on_cock choking_on_penis chun-li close-up cock cock_in_mouth cock_sucking cum cum_covered cum_in_mouth cum_on_face cum_on_tongue cumshot cumstargames dark-skinned_male dark_hair dark_skin dark_skinned_penis deepthroat deepthroat_no_hands defeated defeated_heroine degradation degraded dick dirt dirty dirty_penis disgusted double_bun dubious_consent ejaculate ejaculating ejaculating_cum ejaculation ejaculation_in_mouth face_fucking female floor floor_sex forced forced_oral gag gagged gagged_female gagging gagging_noise gagging_on_penis game game_cg gameplay gameplay_mechanics ground hair hair_in_bun hand_on_head huge_balls huge_breasts huge_cock huge_penis humiliated humiliating humiliation humiliation_fetish interracial interracial_sex kneeling large_balls large_lips large_penis light_skin light_skinned_female lingerie lingerie_only lips lipstick long_penis looking_at_viewer loud_sex moan moaning moaning_in_pleasure monster_cock mouth_full_of_cock naked naked_female naked_male nasty nastyfarm naughty_face night no_gag_reflex nude nude_female nude_male old_man older_male older_man_and_teenage_girl older_penetrating_younger on_floor oral oral_creampie oral_penetration oral_rape orgasm pale-skinned_female pavement penis penis_in_mouth public public_humiliation public_indecency public_sex questionable_consent red_eyeliner red_eyeshadow red_lips red_lipstick restrained ribbon ribbons rough_sex sad sad_expression sad_eyes saliva saliva_drip saliva_on_penis saliva_string saliva_trail seductive_eyes seductive_mouth sex_on_floor shame shiny_skin slave slavegirl sloppy sloppy_blowjob sloppy_deepthroat sloppy_fellatio soaked sound sound_effect sound_effects spit_bubble spit_on_face stepfather_and_stepdaughter stranger street street_fighter street_fighter_6 sucked_dry sucked_off sucked_silly sucking sucking_off sucking_penis surprise surprise_deepthroat surprise_sex surprised surprised_expression surprised_look tagme testicles throat_abuse throat_barrier throat_fuck throat_noise tight_throat tongue tongue_out trash used veiny_balls veiny_penis video video_game video_game_character video_game_franchise video_games wet wet_body wet_mouth wet_penis wet_skin younger_female zoomed_view
1boy 1boy1girl 1girl 1girls 3d 3d_animation 69 69_position abuse abused_female after_fellatio after_oral after_sex all_the_way_to_the_base alley alleyway angry angry_expression angry_face animated animation ashamed asian balls_deep big_balls big_dick big_lips big_penis bimbo_lips black_body black_cock black_hair black_lingerie black_male black_man black_penis blowjob blowjob_face blue_eyeshadow broken brown_eyes brown_skin choking_on_cock choking_on_penis chun-li close-up cock cock_in_mouth cock_sucking cum cum_covered cum_in_mouth cum_on_face cum_on_tongue cumshot cumstargames dark-skinned_male dark_hair dark_skin dark_skinned_penis deepthroat deepthroat_no_hands defeated defeated_heroine degradation degraded dick dirt dirty dirty_penis disgusted double_bun dubious_consent ejaculate ejaculating ejaculating_cum ejaculation ejaculation_in_mouth face_fucking female floor floor_sex forced forced_oral gag gagged gagged_female gagging gagging_noise gagging_on_penis game game_cg gameplay gameplay_mechanics ground hair hair_in_bun hand_on_head huge_balls huge_breasts huge_cock huge_penis humiliated humiliating humiliation humiliation_fetish interracial interracial_sex kneeling large_balls large_lips large_penis light_skin light_skinned_female lingerie lingerie_only lips lipstick long_penis looking_at_viewer loud_sex moan moaning moaning_in_pleasure monster_cock mouth_full_of_cock naked naked_female naked_male nasty nastyfarm naughty_face night no_gag_reflex nude nude_female nude_male old_man older_male older_man_and_teenage_girl older_penetrating_younger on_floor oral oral_creampie oral_penetration oral_rape orgasm pale-skinned_female pavement penis penis_in_mouth public public_humiliation public_indecency public_sex questionable_consent red_eyeliner red_eyeshadow red_lips red_lipstick restrained ribbon ribbons rough_sex sad sad_expression sad_eyes saliva saliva_drip saliva_on_penis saliva_string saliva_trail seductive_eyes seductive_mouth sex_on_floor shame shiny_skin slave slavegirl sloppy sloppy_blowjob sloppy_deepthroat sloppy_fellatio soaked sound sound_effect sound_effects spit_bubble spit_on_face stepfather_and_stepdaughter stranger street street_fighter street_fighter_6 sucked_dry sucked_off sucked_silly sucking sucking_off sucking_penis surprise surprise_deepthroat surprise_sex surprised surprised_expression surprised_look tagme testicles throat_abuse throat_barrier throat_fuck throat_noise tight_throat tongue tongue_out trash used veiny_balls veiny_penis video video_game video_game_character video_game_franchise video_games wet wet_body wet_mouth wet_penis wet_skin younger_female zoomed_view
1boy 1boy1girl 1girls :>= animated blowjob clothing dark-skinned_male dark_skin dirty dirty_penis fellatio female game game_cg hobo homeless hours_later huge_breasts huge_cock interracial longer_than_one_minute male mp4 oral oral_cock_cleaning oral_penetration oral_sex pale-skinned_female pale_skin penis prisoner sad sad_face screencap secretly_loves_it shinachiku_castella shy smegma smegma_in_mouth smell smelling smelling_penis sound text thick_thighs ugly_bastard ugly_man video video_games visual_novel
1boy 1boy1girl 1girls :>= animated blowjob clothing dark-skinned_male dark_skin dirty dirty_penis fellatio female game game_cg hobo homeless hours_later huge_breasts huge_cock interracial longer_than_one_minute male mp4 oral oral_cock_cleaning oral_penetration oral_sex pale-skinned_female pale_skin penis prisoner sad sad_face screencap secretly_loves_it shinachiku_castella shy smegma smegma_in_mouth smell smelling smelling_penis sound text thick_thighs ugly_bastard ugly_man video video_games visual_novel
1girl animated animated_gif annie_leonhart blonde_hair blood blue_eyes female_focus female_titan lowres sad shingeki_no_kyojin solo spoilers standing tears titan_(shingeki_no_kyojin)
1girl animated animated_gif annie_leonhart blonde_hair blood blue_eyes female_focus female_titan lowres sad shingeki_no_kyojin solo spoilers standing tears titan_(shingeki_no_kyojin)
10s animated animated_gif lonely lowres mukaido_manaka nagi_no_asukara sad school_uniform solo tears
10s animated animated_gif lonely lowres mukaido_manaka nagi_no_asukara sad school_uniform solo tears
1girl animated blue_eyes blue_hair blush crying heterochromia looking_at_viewer rain red_eyes sad short_hair simple_background stain tatara_kogasa teardrop tears tongue touhou umbrella undefined_fantastic_object video wet wet_clothes
1girl animated blue_eyes blue_hair blush crying heterochromia looking_at_viewer rain red_eyes sad short_hair simple_background stain tatara_kogasa teardrop tears tongue touhou umbrella undefined_fantastic_object video wet wet_clothes
1girl 2girls animated apron bloody_marie_(skullgirls) brooch crying disembodied_hand food grey_hair hair_ornament headpat jewelry looking_down lowres minmi_kyouto multiple_girls peacock_(skullgirls) pie pov pov_hands red_eyes sad skull_hair_ornament skullgirls solo_focus sound twintails upper_body video
1girl 2girls animated apron bloody_marie_(skullgirls) brooch crying disembodied_hand food grey_hair hair_ornament headpat jewelry looking_down lowres minmi_kyouto multiple_girls peacock_(skullgirls) pie pov pov_hands red_eyes sad skull_hair_ornament skullgirls solo_focus sound twintails upper_body video
1boy animated animated_gif bed bedroom blue_eyes blush crawling kirby kirby_(series) looking_at_viewer looking_back male_focus nintendo no_humans open_mouth pillow sad sitting solo window
1boy animated animated_gif bed bedroom blue_eyes blush crawling kirby kirby_(series) looking_at_viewer looking_back male_focus nintendo no_humans open_mouth pillow sad sitting solo window
1boy 1girls 3d :( animated ass big_breasts bouncing_breasts breasts broken broken_rape_victim butt canon_couple cheating cheating_boyfriend cheating_girlfriend cheating_husband cheating_wife cowgirl_position dead dead_body death emotional female femscout forced forced_sex heavy_weapons_guy male male_death male_on_female medic medic_(team_fortress_2) mrfestive ntr nude nude_female nude_male penis rape reverse_rape sad sex socks sound straight tagme team_fortress_2 tragedy vaginal_penetration video
1boy 1girls 3d :( animated ass big_breasts bouncing_breasts breasts broken broken_rape_victim butt canon_couple cheating cheating_boyfriend cheating_girlfriend cheating_husband cheating_wife cowgirl_position dead dead_body death emotional female femscout forced forced_sex heavy_weapons_guy male male_death male_on_female medic medic_(team_fortress_2) mrfestive ntr nude nude_female nude_male penis rape reverse_rape sad sex socks sound straight tagme team_fortress_2 tragedy vaginal_penetration video
10s 3boys 3girls animated ash_ketchum black_hair blush choker creatures_(company) dancing dress formal_clothes game_freak gen_6_pokemon klefki light_brown_hair looking_at_another mightyena_girl multiple_boys multiple_girls nintendo o_o official_alternate_costume pokemon pokemon_(anime) pokemon_(creature) pokemon_xy red_dress ribbon sad serena_(pokemon) short_hair smile sound standing strapless strapless_dress talking video
10s 3boys 3girls animated ash_ketchum black_hair blush choker creatures_(company) dancing dress formal_clothes game_freak gen_6_pokemon klefki light_brown_hair looking_at_another mightyena_girl multiple_boys multiple_girls nintendo o_o official_alternate_costume pokemon pokemon_(anime) pokemon_(creature) pokemon_xy red_dress ribbon sad serena_(pokemon) short_hair smile sound standing strapless strapless_dress talking video
10s 1girl animated animated_gif ass bare_shoulders breasts bruise censored_nipples cleavage clenched_teeth convenient_arm convenient_censoring crying crying_with_eyes_open dark-skinned_female dark_skin defeat dress embarrassed eyebrows eyeshadow fairy_tail female_focus gloves humiliation injury large_breasts lips lipstick long_hair lying makeup minerva_orlando navel no_bra on_side open_mouth panties pantyshot sad scared screencap solo squinting striped_clothes striped_panties tears teeth thick_eyebrows thick_lips thick_thighs thighs torn_clothes torn_dress trembling underwear
10s 1girl animated animated_gif ass bare_shoulders breasts bruise censored_nipples cleavage clenched_teeth convenient_arm convenient_censoring crying crying_with_eyes_open dark-skinned_female dark_skin defeat dress embarrassed eyebrows eyeshadow fairy_tail female_focus gloves humiliation injury large_breasts lips lipstick long_hair lying makeup minerva_orlando navel no_bra on_side open_mouth panties pantyshot sad scared screencap solo squinting striped_clothes striped_panties tears teeth thick_eyebrows thick_lips thick_thighs thighs torn_clothes torn_dress trembling underwear
1970s_(style) 1girl 70s animated breasts completely_nude falling gradient_hair jeanne_(kanashimi_no_belladonna) kanashimi_no_belladonna lips long_hair looking_at_viewer lowres multicolored_hair nipples no_pussy nude oldschool painting_(medium) psychedelic retro_artstyle sad simple_background solo studio_mushi surreal traditional_media very_long_hair video watercolor_(medium) white_background wide_hips
1970s_(style) 1girl 70s animated breasts completely_nude falling gradient_hair jeanne_(kanashimi_no_belladonna) kanashimi_no_belladonna lips long_hair looking_at_viewer lowres multicolored_hair nipples no_pussy nude oldschool painting_(medium) psychedelic retro_artstyle sad simple_background solo studio_mushi surreal traditional_media very_long_hair video watercolor_(medium) white_background wide_hips
1boy 1girl animated animated_gif black_shirt blue_eyes bow crying doki_doki_literature_club closed_eyes hair_bow hair_ornament half-closed_eyes hug indoors long_sleeves open_mouth pink_hair pink_shirt protagonist_(doki_doki_literature_club) red_bow sad sayori_(doki_doki_literature_club) shirt short_hair slothitice standing tears upper_body
1boy 1girl animated animated_gif black_shirt blue_eyes bow crying doki_doki_literature_club closed_eyes hair_bow hair_ornament half-closed_eyes hug indoors long_sleeves open_mouth pink_hair pink_shirt protagonist_(doki_doki_literature_club) red_bow sad sayori_(doki_doki_literature_club) shirt short_hair slothitice standing tears upper_body
1girls 3d absurdly_large_cock animal_genitalia animated anus areola areolae ass backless_gloves backpussy balls bare_shoulders big_breasts black_balls black_gloves blunt_penis breaking_the_fourth_wall breasts breasts_out brown_eyes brown_hair bucket busty buzzer chains cleavage cleavage_cutout cloth clothing door equine erection eyelashes female female_focus female_masturbation fingering fingerless_gloves flaccid footwear getting_erect glory_hole gloves half-mast hand_on_penis handjob handwear hanging_penis horse horse_penis horseballs horsecock hourglass_figure huge_cock human jewelry kneeling lara_croft lara_croft_(survivor) large_breasts leg_tattoo leotard loincloth long_balls long_hair long_penis long_video longer_than_30_seconds longer_than_one_minute looking_at_penis looking_at_viewer makeup male masturbation metal_bucket nail_polish necklace nipples no_sound penis penis_awe penis_expansion penis_under_clothes piercing pink_penis pussy ringing_bell rubbing_pussy rugged_penis sad semi-erect shaking_head size_difference smooth_balls soft_penis staring_at_penis stroking swinging_penis tagme tattoo thigh_strap thigh_tattoo throbbing throbbing_penis thrusting tied_hair tomb_raider top_heavy_penis vagina veiny_penis video vulva wet_penis wet_pussy white_nail_polish wide_hips wildeerstudio wooden_door
1girls 3d absurdly_large_cock animal_genitalia animated anus areola areolae ass backless_gloves backpussy balls bare_shoulders big_breasts black_balls black_gloves blunt_penis breaking_the_fourth_wall breasts breasts_out brown_eyes brown_hair bucket busty buzzer chains cleavage cleavage_cutout cloth clothing door equine erection eyelashes female female_focus female_masturbation fingering fingerless_gloves flaccid footwear getting_erect glory_hole gloves half-mast hand_on_penis handjob handwear hanging_penis horse horse_penis horseballs horsecock hourglass_figure huge_cock human jewelry kneeling lara_croft lara_croft_(survivor) large_breasts leg_tattoo leotard loincloth long_balls long_hair long_penis long_video longer_than_30_seconds longer_than_one_minute looking_at_penis looking_at_viewer makeup male masturbation metal_bucket nail_polish necklace nipples no_sound penis penis_awe penis_expansion penis_under_clothes piercing pink_penis pussy ringing_bell rubbing_pussy rugged_penis sad semi-erect shaking_head size_difference smooth_balls soft_penis staring_at_penis stroking swinging_penis tagme tattoo thigh_strap thigh_tattoo throbbing throbbing_penis thrusting tied_hair tomb_raider top_heavy_penis vagina veiny_penis video vulva wet_penis wet_pussy white_nail_polish wide_hips wildeerstudio wooden_door
animated animated_gif blush commentary_request creatures_(company) dripping food game_freak gen_1_pokemon hitotubosi holding ketchup ketchup_bottle looking_up nintendo no_humans nose_blush open_mouth pikachu pokemon pokemon_(anime) pokemon_(classic_anime) pokemon_(creature) pokemon_ep042 sad solo standing tearing_up tears tongue ugoira wooden_floor
animated animated_gif blush commentary_request creatures_(company) dripping food game_freak gen_1_pokemon hitotubosi holding ketchup ketchup_bottle looking_up nintendo no_humans nose_blush open_mouth pikachu pokemon pokemon_(anime) pokemon_(classic_anime) pokemon_(creature) pokemon_ep042 sad solo standing tearing_up tears tongue ugoira wooden_floor
1futa 3d anal_insertion animated areolae ass big_penis blue_penis blue_skin bottle bouncing_penis breasts cowgirl_position crotch_cutout cum cum_explosion cumshot cutout dickgirl dildo dominothecat drinking drunk ejaculation erection fellatio fluids full-package_futanari futa_on_female futa_only futanari herm innuendo intersex large_insertion long_video masturbation medium_breasts nipples object_insertion oral overwatch penis purple_skin pussy sad sfm sitting_on_dildo solo sound source_filmmaker swinging_penis tracer video visor widowmaker
1futa 3d anal_insertion animated areolae ass big_penis blue_penis blue_skin bottle bouncing_penis breasts cowgirl_position crotch_cutout cum cum_explosion cumshot cutout dickgirl dildo dominothecat drinking drunk ejaculation erection fellatio fluids full-package_futanari futa_on_female futa_only futanari herm innuendo intersex large_insertion long_video masturbation medium_breasts nipples object_insertion oral overwatch penis purple_skin pussy sad sfm sitting_on_dildo solo sound source_filmmaker swinging_penis tracer video visor widowmaker
abused adeptussteve after_sex animated anthro becoming_erect bestiality black_hair blowjob crying cum cum_all_over cum_blast cum_dump cum_everywhere cum_explosion cum_in_mouth cum_on_ass cum_on_belly cum_on_body cum_on_breasts cum_on_face cum_on_vagina cummed_on deepthroat dubious_consent excessive_cum face_fucking face_humping face_mounting face_rape fellatio furious_masturbation gagging getting_erect interspecies irrumatio jacket jacket_open jerking jerking_off jerkingoff on_back on_knees oral oral_sex rat red_lipstick ruined ruined_makeup running_makeup running_mascara sad scared smaller_male sound sucking_penis tagme tears throat_fuck throatfuck too_much_cum video wildlife_(video_game)
abused adeptussteve after_sex animated anthro becoming_erect bestiality black_hair blowjob crying cum cum_all_over cum_blast cum_dump cum_everywhere cum_explosion cum_in_mouth cum_on_ass cum_on_belly cum_on_body cum_on_breasts cum_on_face cum_on_vagina cummed_on deepthroat dubious_consent excessive_cum face_fucking face_humping face_mounting face_rape fellatio furious_masturbation gagging getting_erect interspecies irrumatio jacket jacket_open jerking jerking_off jerkingoff on_back on_knees oral oral_sex rat red_lipstick ruined ruined_makeup running_makeup running_mascara sad scared smaller_male sound sucking_penis tagme tears throat_fuck throatfuck too_much_cum video wildlife_(video_game)
1girl 2girls akemi_homura akemi_homura_(magical_girl) animated black_hair black_pantyhose bow braid closed_eyes constricted_pupils crying dress glasses hair_bow hair_down hair_ribbon happy high_collar kaname_madoka kaname_madoka_(magical_girl) long_hair magical_girl mahou_shoujo_madoka_magica mahou_shoujo_madoka_magica_(anime) multiple_girls open_mouth pantyhose pink_hair ribbon rok0813 sad screaming side-by-side simple_background skirt smile surprised thighhighs twin_braids twintails very_long_hair video white_background white_thighhighs
1girl 2girls akemi_homura akemi_homura_(magical_girl) animated black_hair black_pantyhose bow braid closed_eyes constricted_pupils crying dress glasses hair_bow hair_down hair_ribbon happy high_collar kaname_madoka kaname_madoka_(magical_girl) long_hair magical_girl mahou_shoujo_madoka_magica mahou_shoujo_madoka_magica_(anime) multiple_girls open_mouth pantyhose pink_hair ribbon rok0813 sad screaming side-by-side simple_background skirt smile surprised thighhighs twin_braids twintails very_long_hair video white_background white_thighhighs
1boy 1girls 1monster 3d 3d_(artwork) angry animated breaking camera camera_view capcom carlos_oliveira cockblock compilation computer device device_bondage edit electronics experiment facility fanboy_sound female firearm giant_cock giant_penis gun horse_penis horsecock hospital human jill_valentine jill_valentine_(sasha_zotova) laboratory legs_apart legs_spread legs_up long_video longer_than_30_seconds longer_than_one_minute male moaning monster monster_cock monster_on_female nemesis_(resident_evil) pc piledriver_position punch raccoon_city resident_evil resident_evil_3 resident_evil_3_remake rifle sad soles sound study stuffed umbrella umbrella_corporation upset video weapon zmsfm
1boy 1girls 1monster 3d 3d_(artwork) angry animated breaking camera camera_view capcom carlos_oliveira cockblock compilation computer device device_bondage edit electronics experiment facility fanboy_sound female firearm giant_cock giant_penis gun horse_penis horsecock hospital human jill_valentine jill_valentine_(sasha_zotova) laboratory legs_apart legs_spread legs_up long_video longer_than_30_seconds longer_than_one_minute male moaning monster monster_cock monster_on_female nemesis_(resident_evil) pc piledriver_position punch raccoon_city resident_evil resident_evil_3 resident_evil_3_remake rifle sad soles sound study stuffed umbrella umbrella_corporation upset video weapon zmsfm
1girls 2d animated bad_end blonde_hair captive captured captured_heroine closed_eyes clothed damsel_in_distress defeated defeated_heroine domination dungeon earrings embarrassed embarrassed_nude_exposure embarrassed_nude_female eyelashes falsealias female femsub forced forced_exposure forced_nudity forced_submission forced_undressing frustrated game_over game_over_screen game_ui jail jail_cell kidnapped koopa lip mario_(series) nintendo nude nude_female one_eye_closed princess princess_rosalina prisoner sad scared sex_slave sound source_request struggling super_mario_galaxy tied_up underwear undressing video worried
1girls 2d animated bad_end blonde_hair captive captured captured_heroine closed_eyes clothed damsel_in_distress defeated defeated_heroine domination dungeon earrings embarrassed embarrassed_nude_exposure embarrassed_nude_female eyelashes falsealias female femsub forced forced_exposure forced_nudity forced_submission forced_undressing frustrated game_over game_over_screen game_ui jail jail_cell kidnapped koopa lip mario_(series) nintendo nude nude_female one_eye_closed princess princess_rosalina prisoner sad scared sex_slave sound source_request struggling super_mario_galaxy tied_up underwear undressing video worried
00s 1girl animated animated_gif bare_shoulders barefoot bed black_hair blue_eyes breasts cleavage female_focus fujimura_shizuru gloves large_breasts long_hair nude sad screencap shinkon_gattai_godannar!! towel
00s 1girl animated animated_gif bare_shoulders barefoot bed black_hair blue_eyes breasts cleavage female_focus fujimura_shizuru gloves large_breasts long_hair nude sad screencap shinkon_gattai_godannar!! towel
1boy 2girls 3d :i animated back_pain blackmalou blue_archive carrying carrying_person chibi closed_eyes crying doodle_sensei_(blue_archive) fleeing halo happy heavy indoors interior koyuki_(blue_archive) lifting_person mechanical_halo multiple_girls sad school_uniform sensei_(blue_archive) speech_bubble struggling t-pose teacher_and_student third-party_edit third-party_source thought_bubble video weight_conscious weights yuuka_(blue_archive)
1boy 2girls 3d :i animated back_pain blackmalou blue_archive carrying carrying_person chibi closed_eyes crying doodle_sensei_(blue_archive) fleeing halo happy heavy indoors interior koyuki_(blue_archive) lifting_person mechanical_halo multiple_girls sad school_uniform sensei_(blue_archive) speech_bubble struggling t-pose teacher_and_student third-party_edit third-party_source thought_bubble video weight_conscious weights yuuka_(blue_archive)
1boy 1girls 3d alien animated background bad_end belly_button bikini blonde_hair bondage collar crossover defeated defeated_heroine disgusted domination duo eastern_and_western_character female femsub flying forced front_view garryswood gold_(metal) hair hand_on_shoulder holding holding_leash holding_object hutt indoors jabba_the_hutt larger_male leash light-skinned_female light_skin long_hair long_tongue male maledom metal_bikini metroid monster mp4 neckwear patreon sad sail_barge saliva samus_aran sarah_bryant_(model) signature sitting size_difference slave slave_bikini slave_leia_(cosplay) slave_outfit slug smaller_female sound source_filmmaker star_wars straight submissive tail tatooine tied_hair tomboy tongue tongue_out trophy_wife twitter_username ugly_bastard ugly_man vehicle video
1boy 1girls 3d alien animated background bad_end belly_button bikini blonde_hair bondage collar crossover defeated defeated_heroine disgusted domination duo eastern_and_western_character female femsub flying forced front_view garryswood gold_(metal) hair hand_on_shoulder holding holding_leash holding_object hutt indoors jabba_the_hutt larger_male leash light-skinned_female light_skin long_hair long_tongue male maledom metal_bikini metroid monster mp4 neckwear patreon sad sail_barge saliva samus_aran sarah_bryant_(model) signature sitting size_difference slave slave_bikini slave_leia_(cosplay) slave_outfit slug smaller_female sound source_filmmaker star_wars straight submissive tail tatooine tied_hair tomboy tongue tongue_out trophy_wife twitter_username ugly_bastard ugly_man vehicle video
1girls 3d accurate_art_style airship animated areolae arms_behind_back bad_end ball_gag banzai_bill belly_button blonde_hair blue_eyes bondage bound breasts bullet_bill bullet_bill_launcher cannon captured captured_heroine clouds crying damsel_in_distress decoration defeated defeated_heroine domination embarrassed embarrassed_nude_exposure embarrassed_nude_female enf enslaved enslaved_royal erect_nipples eye_contact female female_focus female_only femsub figurehead forced forced_exposure forced_submission frustrated functionally_nude gag gagged game_over gloves helpless heroine_in_trouble high_heels human_figurehead human_furniture humiliation kidnapped maledom mario_(series) medium_breasts new_super_mario_bros. nintendo nipples nude objectification onmodel3d peril ponytail princess princess_peach punishment pussy red_ball_gag resisting restrained rope rope_bondage royalty sad sad_sub scared self_upload sex_slave shorter_than_30_seconds shorter_than_3_minutes shorter_than_five_minutes shorter_than_four_minutes shorter_than_one_minute shorter_than_two_minutes slave slave_outfit slavegirl sole_female solo sound submissive submissive_female super_mario_bros. surprised tagme tears thighhighs tied_up torture trapped trophy uncomfortable unhappy unhappy_female video worried
1girls 3d accurate_art_style airship animated areolae arms_behind_back bad_end ball_gag banzai_bill belly_button blonde_hair blue_eyes bondage bound breasts bullet_bill bullet_bill_launcher cannon captured captured_heroine clouds crying damsel_in_distress decoration defeated defeated_heroine domination embarrassed embarrassed_nude_exposure embarrassed_nude_female enf enslaved enslaved_royal erect_nipples eye_contact female female_focus female_only femsub figurehead forced forced_exposure forced_submission frustrated functionally_nude gag gagged game_over gloves helpless heroine_in_trouble high_heels human_figurehead human_furniture humiliation kidnapped maledom mario_(series) medium_breasts new_super_mario_bros. nintendo nipples nude objectification onmodel3d peril ponytail princess princess_peach punishment pussy red_ball_gag resisting restrained rope rope_bondage royalty sad sad_sub scared self_upload sex_slave shorter_than_30_seconds shorter_than_3_minutes shorter_than_five_minutes shorter_than_four_minutes shorter_than_one_minute shorter_than_two_minutes slave slave_outfit slavegirl sole_female solo sound submissive submissive_female super_mario_bros. surprised tagme tears thighhighs tied_up torture trapped trophy uncomfortable unhappy unhappy_female video worried
10s 2boys 2girls animated animated_gif anime_screenshot computer glasses koizumi_itsuki kyon lowres multiple_boys multiple_girls nagato_yuki paper purple_hair sad school_uniform spoilers suzumiya_haruhi suzumiya_haruhi_no_shoushitsu suzumiya_haruhi_no_yuuutsu tears
10s 2boys 2girls animated animated_gif anime_screenshot computer glasses koizumi_itsuki kyon lowres multiple_boys multiple_girls nagato_yuki paper purple_hair sad school_uniform spoilers suzumiya_haruhi suzumiya_haruhi_no_shoushitsu suzumiya_haruhi_no_yuuutsu tears
1boy 1girls alternate_version_at_source animated areolae big_breasts blush blush_lines breasts ceyamart_(artist) cum doki_doki_literature_club female frottage happy heart-shaped_pupils long_hair male naked naked_female nipples nude nude_female outercourse paizuri penis purple_eyes purple_hair sad sound tagme titjob video yuri_(doki_doki_literature_club)
1boy 1girls alternate_version_at_source animated areolae big_breasts blush blush_lines breasts ceyamart_(artist) cum doki_doki_literature_club female frottage happy heart-shaped_pupils long_hair male naked naked_female nipples nude nude_female outercourse paizuri penis purple_eyes purple_hair sad sound tagme titjob video yuri_(doki_doki_literature_club)
3d 3girls animated ass black_hair blonde_hair bondage bouncing_breasts bound bound_ankles bound_wrists breasts captured captured_heroine cloth_gag damsel_in_distress defeated defeated_heroine domination english_voice_acting enslaved female female_only femsub forced forced_exposure forced_submission gag gagged heart-shaped_pupils helpless highres humiliation improvised_gag kidnapped kurenai_yuhi longer_than_2_minutes mitarashi_anko mp4 multiple_girls multiple_subs naked naruto naruto_(series) navel nipples nude over_the_nose_gag prisoner punishment rape restrained sad sad_sub scared sex_slave sex_toy shepirotcloud shorter_than_3_minutes slave slavegirl slaver sound struggling submissive submissive_female tagme trapped tsunade uncomfortable unhappy unhappy_female vibrator video voice_acted worried yuuhi_kurenai
3d 3girls animated ass black_hair blonde_hair bondage bouncing_breasts bound bound_ankles bound_wrists breasts captured captured_heroine cloth_gag damsel_in_distress defeated defeated_heroine domination english_voice_acting enslaved female female_only femsub forced forced_exposure forced_submission gag gagged heart-shaped_pupils helpless highres humiliation improvised_gag kidnapped kurenai_yuhi longer_than_2_minutes mitarashi_anko mp4 multiple_girls multiple_subs naked naruto naruto_(series) navel nipples nude over_the_nose_gag prisoner punishment rape restrained sad sad_sub scared sex_slave sex_toy shepirotcloud shorter_than_3_minutes slave slavegirl slaver sound struggling submissive submissive_female tagme trapped tsunade uncomfortable unhappy unhappy_female vibrator video voice_acted worried yuuhi_kurenai