depressing best from all time

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depressing

1boy 2girls areolae assisted_masturbation big_breasts blue_eyes blush breasts brown_hair collecting_cum condom_on_penis cum cum_in_condom depressing dialogue erection female gloves hand_holding handjob holding_hands large_breasts long_hair looking_at_viewer male mare_ten milking_handjob missionary_position nipples nude nurse nurse_uniform open_mouth original original_character penetration penis penis_milking pleasured pov pussy pussy_juice sad_sex sex shaved_pussy smile speech_bubble spread_legs straight text trembling vaginal_penetration veiny_penis virtual_reality visor vr vr_headset wearing_condom
1boy 2girls areolae assisted_masturbation big_breasts blue_eyes blush breasts brown_hair collecting_cum condom_on_penis cum cum_in_condom depressing dialogue erection female gloves hand_holding handjob holding_hands large_breasts long_hair looking_at_viewer male mare_ten milking_handjob missionary_position nipples nude nurse nurse_uniform open_mouth original original_character penetration penis penis_milking pleasured pov pussy pussy_juice sad_sex sex shaved_pussy smile speech_bubble spread_legs straight text trembling vaginal_penetration veiny_penis virtual_reality visor vr vr_headset wearing_condom
1girls animated blue_eyes bouncing_breasts breasts brown_hair brown_hair_female casual chicken chicken_(minecraft) depressing diamond_helmet english_subtitles english_text female human jenny_belle_(slipperyt) jenny_odd_adventure lizzlewaffle longer_than_one_minute minecraft minecraft_mob nonsexual_nudity nude nude_female oddly_wholesome pale_skin preview sad slipperyt sound tagme thick thick_ass video wholesome
1girls animated blue_eyes bouncing_breasts breasts brown_hair brown_hair_female casual chicken chicken_(minecraft) depressing diamond_helmet english_subtitles english_text female human jenny_belle_(slipperyt) jenny_odd_adventure lizzlewaffle longer_than_one_minute minecraft minecraft_mob nonsexual_nudity nude nude_female oddly_wholesome pale_skin preview sad slipperyt sound tagme thick thick_ass video wholesome
1girls abuse ahe_gao ahegao beaten black_eye black_eye_(injury) blonde_hair blush blushing_at_viewer breasts breasts_on_sign breasts_out bruise bruise_on_face bruised bruised_eye bruised_face bruises crown cruelty crying crying_with_eyes_open cursed_image degradation depressing disgusting do_whatever_you_want_to_me drooling earrings edit edited ereshkigal_(fate) exposed fate/grand_order fate_(series) feels goddess gross happy_sub heart-shaped_pupils holding_object holding_sign humiliation long_hair looking_at_viewer masochism misogyny nagelen naked nightmare_fuel nipple_piercing nude queen queen_of_the_underworld red_eyes red_ribbon ribbons ruler ruler_of_the_underworld ryona shaking sign smile smiling smiling_at_viewer suffering tearing_up tears tongue_out twintails what why
1girls abuse ahe_gao ahegao beaten black_eye black_eye_(injury) blonde_hair blush blushing_at_viewer breasts breasts_on_sign breasts_out bruise bruise_on_face bruised bruised_eye bruised_face bruises crown cruelty crying crying_with_eyes_open cursed_image degradation depressing disgusting do_whatever_you_want_to_me drooling earrings edit edited ereshkigal_(fate) exposed fate/grand_order fate_(series) feels goddess gross happy_sub heart-shaped_pupils holding_object holding_sign humiliation long_hair looking_at_viewer masochism misogyny nagelen naked nightmare_fuel nipple_piercing nude queen queen_of_the_underworld red_eyes red_ribbon ribbons ruler ruler_of_the_underworld ryona shaking sign smile smiling smiling_at_viewer suffering tearing_up tears tongue_out twintails what why
1boy 1femboy animated bird bird_girl black_clothing blush_lines blushing clothes_on_floor coffee coffee_cup coffee_mug comic comic_dub comic_page comic_panel concerned depressed depressing depression doggy_style english_voice_acting female femboy furry gay hearts kissing male manipulation manipulative moaning mouse mouse_boy mouse_ears mouse_tail mp4 rat rat_boy rat_ears reggie_(whygena) resting resting_on_arms resting_on_partner sad sex_on_bed sleeping sound sound_effects tagme tentacle tentacles texting thighhighs toxic toxic_relationship toxic_yaoi video voice_acted whygena yandere zombibatz
1boy 1femboy animated bird bird_girl black_clothing blush_lines blushing clothes_on_floor coffee coffee_cup coffee_mug comic comic_dub comic_page comic_panel concerned depressed depressing depression doggy_style english_voice_acting female femboy furry gay hearts kissing male manipulation manipulative moaning mouse mouse_boy mouse_ears mouse_tail mp4 rat rat_boy rat_ears reggie_(whygena) resting resting_on_arms resting_on_partner sad sex_on_bed sleeping sound sound_effects tagme tentacle tentacles texting thighhighs toxic toxic_relationship toxic_yaoi video voice_acted whygena yandere zombibatz
1boy 1girls 2020 alternate_breast_size barely_clothed belly_chain belly_dancer belly_dancer_outfit big_breasts blush blushing chain_collar chained_collar collar crying depressed depressing english_text eyebrows_visible_through_hair female female_focus flower_in_hair furry_ears holding_head huge_belly league_of_legends mostly_nude naked naked_female neeko netorare nude nude_female ponytail practically_nude pregnant pregnant_belly pregnant_female pubic_tattoo purple_hair rakan ratatatat74 ready_to_pop red_hair riot_games sad shaved_crotch shaved_pussy simple_background small_breasts source_request speech_bubble text transformation transparent_clothing tunic vastaya veil white_background white_hair xayah
1boy 1girls 2020 alternate_breast_size barely_clothed belly_chain belly_dancer belly_dancer_outfit big_breasts blush blushing chain_collar chained_collar collar crying depressed depressing english_text eyebrows_visible_through_hair female female_focus flower_in_hair furry_ears holding_head huge_belly league_of_legends mostly_nude naked naked_female neeko netorare nude nude_female ponytail practically_nude pregnant pregnant_belly pregnant_female pubic_tattoo purple_hair rakan ratatatat74 ready_to_pop red_hair riot_games sad shaved_crotch shaved_pussy simple_background small_breasts source_request speech_bubble text transformation transparent_clothing tunic vastaya veil white_background white_hair xayah
1boy 1girls areola areolae blue_panties blush boku_no_hero_academia brown_eyes brown_hair camera color depressing dialogue double_v exposed_breasts humor izuku_midoriya kneeling looking_at_viewer medium_breasts meme my_hero_academia nipples ochako_uraraka on_bed on_knees onlyfans open_mouth panties partially_colored peace_sign prostitution sad shadow speech_bubble suoiresnu text underwear v white_background white_skin
1boy 1girls areola areolae blue_panties blush boku_no_hero_academia brown_eyes brown_hair camera color depressing dialogue double_v exposed_breasts humor izuku_midoriya kneeling looking_at_viewer medium_breasts meme my_hero_academia nipples ochako_uraraka on_bed on_knees onlyfans open_mouth panties partially_colored peace_sign prostitution sad shadow speech_bubble suoiresnu text underwear v white_background white_skin
1girls alternate_breast_size big_breasts blonde_hair breasts busty censored_age censored_text closed_eyes curvaceous curvy curvy_body curvy_female curvy_figure depressing english english_text eyes_closed female game_freak huge_breasts implied_rape lactating lactation large_breasts lillie_(pokemon) nintendo pokemon pokemon_(game) pokemon_sm ponytail pubic_hair pubic_hair_on_face rape skirt stray_pubic_hair text thick_thighs thighs voluptuous what woohyoot
1girls alternate_breast_size big_breasts blonde_hair breasts busty censored_age censored_text closed_eyes curvaceous curvy curvy_body curvy_female curvy_figure depressing english english_text eyes_closed female game_freak huge_breasts implied_rape lactating lactation large_breasts lillie_(pokemon) nintendo pokemon pokemon_(game) pokemon_sm ponytail pubic_hair pubic_hair_on_face rape skirt stray_pubic_hair text thick_thighs thighs voluptuous what woohyoot
1girls 3boys abigail_walker ahe_gao alcohol anal anal_sex bad_end breasts broken_rape_victim chris3000 clothed_sex cum cum_in_ass cum_on_body cum_on_breasts defeated defeated_heroine depressing dialogue double_peace_sign drugged drugged_sex drugs earrings english english_text enjoying erection female female_focus fetch_(character) foreskin foreskin_folds fuck_meat game_over gangbang group_sex humiliation infamous:_first_light infamous:_second_son infamous_(series) intact mind_break nipples partial_male peace_sign penis purple_hair retracted_foreskin shaved_crotch straight tongue tongue_out torn_clothes uncut used_condom veiny_penis
1girls 3boys abigail_walker ahe_gao alcohol anal anal_sex bad_end breasts broken_rape_victim chris3000 clothed_sex cum cum_in_ass cum_on_body cum_on_breasts defeated defeated_heroine depressing dialogue double_peace_sign drugged drugged_sex drugs earrings english english_text enjoying erection female female_focus fetch_(character) foreskin foreskin_folds fuck_meat game_over gangbang group_sex humiliation infamous:_first_light infamous:_second_son infamous_(series) intact mind_break nipples partial_male peace_sign penis purple_hair retracted_foreskin shaved_crotch straight tongue tongue_out torn_clothes uncut used_condom veiny_penis
1girls ass carton_of_milk clothes dark depressing dildo female female_only filth fingering fingering_self i_dont_want_to_be_horny_anymore idolmaster idolmaster_cinderella_girls legs_together looking_at_phone masturbation messy_room napkin panties peeing peeing_into_container phone pillow pussy_juice relatable short_hair solo sunaba_suzume tissue tissue_box trash trash_bag trash_can underwear urination urine urine_in_container vibrator watching_porn white_panties yumemi_riamu
1girls ass carton_of_milk clothes dark depressing dildo female female_only filth fingering fingering_self i_dont_want_to_be_horny_anymore idolmaster idolmaster_cinderella_girls legs_together looking_at_phone masturbation messy_room napkin panties peeing peeing_into_container phone pillow pussy_juice relatable short_hair solo sunaba_suzume tissue tissue_box trash trash_bag trash_can underwear urination urine urine_in_container vibrator watching_porn white_panties yumemi_riamu
abuse anthro areola arm_tuft armpits bad_end balls bangs big_areola big_breasts big_dom_small_sub big_nipples big_penis black_nose blue_eyes blue_fur blue_hair blue_tail blush bodily_fluids bound breasts breeding_slave broken_rape_victim canid canine captured cleft_of_venus clenched_teeth clitoris comic crotch_tuft cum cum_in_nipples cum_in_pussy cum_inflated_breasts cum_inflation cum_inside cum_on_breasts curvaceous curvy curvy_figure depressing dialogue dipstick_tail english_text erection eyebrows eyelashes faceless_male female female_focus fluffy fluffy_tail forced foreskin fox frenulum front_view frown fur fur_markings gang gangbang genital_fluids glans glistening glistening_breasts glistening_eyes glistening_hair glistening_nose gold_(metal) gold_jewelry green_balls green_eyes green_glans green_penis green_scales grey_background group group_sex hair hair_over_eyes hakiahki half-closed_eyes hard_translated hi_res huge_ass huge_breasts huge_cock huge_thighs humanoid_penis humanoid_pussy inflation inner_ear_fluff jewelry krystal larger_male lizardman long_tail male mammal markings mind_break multicolored_fur multicolored_tail musclegut muscular muscular_male navel never_back_down never_give_up nintendo nipple_penetration nipples nude objectification pecs penetration penis pink_areola pink_clitoris pink_nipples pink_pussy pregnant pregnant_sex pregnant_sex_penis_bulge prick_ears pubic_mound public_sex_slave public_use pussy raised_arm rape reptile retracted_foreskin scales scalie sex sex_slave sharpclaw short_hair simple_background size_difference slave small_waist smaller_female smile snout solo_focus star_fox stomach_bulge straight sweat tag_panic tail_jewelry tailband teeth text thick_penis thick_thighs translated tribal tribal_markings two_tone_tail ugly_man uncut urethra vaginal_penetration vein veiny_penis video_games voluptuous white_belly white_fur white_markings white_tail wide_hips
abuse anthro areola arm_tuft armpits bad_end balls bangs big_areola big_breasts big_dom_small_sub big_nipples big_penis black_nose blue_eyes blue_fur blue_hair blue_tail blush bodily_fluids bound breasts breeding_slave broken_rape_victim canid canine captured cleft_of_venus clenched_teeth clitoris comic crotch_tuft cum cum_in_nipples cum_in_pussy cum_inflated_breasts cum_inflation cum_inside cum_on_breasts curvaceous curvy curvy_figure depressing dialogue dipstick_tail english_text erection eyebrows eyelashes faceless_male female female_focus fluffy fluffy_tail forced foreskin fox frenulum front_view frown fur fur_markings gang gangbang genital_fluids glans glistening glistening_breasts glistening_eyes glistening_hair glistening_nose gold_(metal) gold_jewelry green_balls green_eyes green_glans green_penis green_scales grey_background group group_sex hair hair_over_eyes hakiahki half-closed_eyes hard_translated hi_res huge_ass huge_breasts huge_cock huge_thighs humanoid_penis humanoid_pussy inflation inner_ear_fluff jewelry krystal larger_male lizardman long_tail male mammal markings mind_break multicolored_fur multicolored_tail musclegut muscular muscular_male navel never_back_down never_give_up nintendo nipple_penetration nipples nude objectification pecs penetration penis pink_areola pink_clitoris pink_nipples pink_pussy pregnant pregnant_sex pregnant_sex_penis_bulge prick_ears pubic_mound public_sex_slave public_use pussy raised_arm rape reptile retracted_foreskin scales scalie sex sex_slave sharpclaw short_hair simple_background size_difference slave small_waist smaller_female smile snout solo_focus star_fox stomach_bulge straight sweat tag_panic tail_jewelry tailband teeth text thick_penis thick_thighs translated tribal tribal_markings two_tone_tail ugly_man uncut urethra vaginal_penetration vein veiny_penis video_games voluptuous white_belly white_fur white_markings white_tail wide_hips
1boy 1girls :>= barbara_millicent_roberts barbenheimer barbie_(2023) barbie_(franchise) barbie_(margot_robbie) blonde_hair blowjob blue_eyes color_contrast deepthroat depressing eye_contact fellatio female human human_only humor implied_deepthroat implied_fellatio implied_oral julius_robert_oppenheimer kneeling long_hair male mammal margot_robbie meme monochrome monochrome_background nuke oppenheimer oppenheimer_(film) oral petite pink_background pink_eyeshadow pink_lipstick pov rerorero seductive_eyes seductive_look seductive_mouth suit suit_and_tie text tie traumatized what_she_sees
1boy 1girls :>= barbara_millicent_roberts barbenheimer barbie_(2023) barbie_(franchise) barbie_(margot_robbie) blonde_hair blowjob blue_eyes color_contrast deepthroat depressing eye_contact fellatio female human human_only humor implied_deepthroat implied_fellatio implied_oral julius_robert_oppenheimer kneeling long_hair male mammal margot_robbie meme monochrome monochrome_background nuke oppenheimer oppenheimer_(film) oral petite pink_background pink_eyeshadow pink_lipstick pov rerorero seductive_eyes seductive_look seductive_mouth suit suit_and_tie text tie traumatized what_she_sees
1futa 2girls being_watched blackmail caught caught_in_the_act cheating cheating_girlfriend comic cuck cucked_by_futa cuckold cuckquean depressed depressing english_text female futa_on_female futanari netorare ntr on_top penis penny_polendina robot ruby_rose rwby sex sinccubi testicles text weiss_schnee
1futa 2girls being_watched blackmail caught caught_in_the_act cheating cheating_girlfriend comic cuck cucked_by_futa cuckold cuckquean depressed depressing english_text female futa_on_female futanari netorare ntr on_top penis penny_polendina robot ruby_rose rwby sex sinccubi testicles text weiss_schnee
3d 3d_(artwork) after_anal after_sex amputated_arms amputated_legs amputation amputee astolfo_(fate) big_ass big_balls big_breasts big_butt big_penis blood bullying chastity_cage cock_ring crossover cruelty cum depressing dick dickgirl evil fate_(series) futa_on_femboy futa_on_male futanari glowing_eyes guro horror huge_cock hung_futanari little_penis male nightmare_fuel penis_to_the_knees pink_hair pubic_hair red_eyes red_hair ring saiko-chan saiko_no_sutoka sfm simon_sklar snuff source source_filmmaker sperm steam steaming_body tears trap what yandere
3d 3d_(artwork) after_anal after_sex amputated_arms amputated_legs amputation amputee astolfo_(fate) big_ass big_balls big_breasts big_butt big_penis blood bullying chastity_cage cock_ring crossover cruelty cum depressing dick dickgirl evil fate_(series) futa_on_femboy futa_on_male futanari glowing_eyes guro horror huge_cock hung_futanari little_penis male nightmare_fuel penis_to_the_knees pink_hair pubic_hair red_eyes red_hair ring saiko-chan saiko_no_sutoka sfm simon_sklar snuff source source_filmmaker sperm steam steaming_body tears trap what yandere
1girls 2d 6_panel_comic 6boys after_sex big_breasts blush comic crossdressing cum cum_in_mouth cum_in_pussy cum_inside cum_on_body cum_on_breasts depressing femboy femboy_on_female handjob leaking_cum nipples nude seductivesquid sex smile standing sweat tagme tears thewill toby_fox toriel tutori_(under(her)tail) under(her)tail undertail undertale undertale_(series) white_fur
1girls 2d 6_panel_comic 6boys after_sex big_breasts blush comic crossdressing cum cum_in_mouth cum_in_pussy cum_inside cum_on_body cum_on_breasts depressing femboy femboy_on_female handjob leaking_cum nipples nude seductivesquid sex smile standing sweat tagme tears thewill toby_fox toriel tutori_(under(her)tail) under(her)tail undertail undertale undertale_(series) white_fur
1futa 6+girls akiza_izinski being_watched cheating cheating_girlfriend cinder_fall crossover crying cuck cucked_by_futa cuckold cuckquean cum cum_on_body cum_on_breasts depressed depressing english_text female futa_on_female futanari glynda_goodwitch human implied_futanari jinn_(rwby) long_hair netorare ntr relic_of_knowledge ruby_rose rwby sad sinccubi teenage_girl teenager text velvet_scarlatina weiss_schnee yu-gi-oh! yu-gi-oh!_5d's
1futa 6+girls akiza_izinski being_watched cheating cheating_girlfriend cinder_fall crossover crying cuck cucked_by_futa cuckold cuckquean cum cum_on_body cum_on_breasts depressed depressing english_text female futa_on_female futanari glynda_goodwitch human implied_futanari jinn_(rwby) long_hair netorare ntr relic_of_knowledge ruby_rose rwby sad sinccubi teenage_girl teenager text velvet_scarlatina weiss_schnee yu-gi-oh! yu-gi-oh!_5d's
2020 animal_crossing anthro beverage blush bodily_fluids breasts canid canine canis clothed clothing depressing domestic_dog english_text female food fur genitals hair head_down isabelle_(animal_crossing) mammal masturbation muffin nintendo panken pussy relatable relaxing sad sex_toy shih_tzu solo speech_bubble tears text toy_dog vibrator video_games yellow_body yellow_fur
2020 animal_crossing anthro beverage blush bodily_fluids breasts canid canine canis clothed clothing depressing domestic_dog english_text female food fur genitals hair head_down isabelle_(animal_crossing) mammal masturbation muffin nintendo panken pussy relatable relaxing sad sex_toy shih_tzu solo speech_bubble tears text toy_dog vibrator video_games yellow_body yellow_fur
1boy 1girls abs adam_smasher bad_end bathsalts1 beer_bottle big_breasts cd_projekt_red clutching_chest comic crying crying_with_eyes_open cuddling cyberpunk:_edgerunners cyberpunk_2077 david_martinez_(edgerunners) depressing digital_clock earth empty_bottle english_text female female_focus full_moon handgun happy heart_broken holding_self hologram impending_doom jacket jacket_only latino laughing light-skinned_female light_skin lucyna_kushinada memories moon muscular muscular_male netflix night_sky nightmare nude nude_female outer_space pill_bottle sad satellite shocked shocked_expression short_hair sitting_on_bed sleeping sobbing space_station spoilers star stars studio_trigger tagme text thick_thighs urn
1boy 1girls abs adam_smasher bad_end bathsalts1 beer_bottle big_breasts cd_projekt_red clutching_chest comic crying crying_with_eyes_open cuddling cyberpunk:_edgerunners cyberpunk_2077 david_martinez_(edgerunners) depressing digital_clock earth empty_bottle english_text female female_focus full_moon handgun happy heart_broken holding_self hologram impending_doom jacket jacket_only latino laughing light-skinned_female light_skin lucyna_kushinada memories moon muscular muscular_male netflix night_sky nightmare nude nude_female outer_space pill_bottle sad satellite shocked shocked_expression short_hair sitting_on_bed sleeping sobbing space_station spoilers star stars studio_trigger tagme text thick_thighs urn
2girls beverly_(nortuet) big_breasts blonde_hair blue_eyes breasts casual cleavage comedy depressing english_text f_in_chat female_focus female_only funny green_eyes happy hi_res human humor live_snail_reaction long_hair muscular muscular_female nortuet nortuet_universe nude original petite pink_phone red_hair sad sad_snail sad_snail_hours sdnail small_breasts snail speech_bubble tan tan_skin tanned tara_(nortuet) text why_would_you_say_that_snails_are_great_partners yuri
2girls beverly_(nortuet) big_breasts blonde_hair blue_eyes breasts casual cleavage comedy depressing english_text f_in_chat female_focus female_only funny green_eyes happy hi_res human humor live_snail_reaction long_hair muscular muscular_female nortuet nortuet_universe nude original petite pink_phone red_hair sad sad_snail sad_snail_hours sdnail small_breasts snail speech_bubble tan tan_skin tanned tara_(nortuet) text why_would_you_say_that_snails_are_great_partners yuri
1girls after_rape after_sex after_vaginal ai-created ai_generated anus arms_around_knees ass bangs barefoot bathing bathroom black_hair blue_hair blush bodily_fluids breasts clitoris clorinde_(genshin_impact) closed_mouth completely_nude crying crying_with_eyes_open cum cum_drip cum_in_pussy cum_inside cum_pool depressing dripping_semen english english_text feet female female_only full_body genital_fluids genshin_impact hair_between_eyes high_resolution hugging_own_legs indoors jenneth_blackray knees_to_chest knees_together knees_up large_breasts legs legs_together light-skinned_female long_hair looking_down medium_breasts multicolored_hair nail_polish nipples nude on_floor parted_lips purple_eyes rape sad semen shower showering sitting soles solo stable_diffusion streaked_hair tears thighs tile_wall tiles toenail_polish toenails toes trembling uncensored vagina vaginal_juices very_high_resolution very_long_hair water wet
1girls after_rape after_sex after_vaginal ai-created ai_generated anus arms_around_knees ass bangs barefoot bathing bathroom black_hair blue_hair blush bodily_fluids breasts clitoris clorinde_(genshin_impact) closed_mouth completely_nude crying crying_with_eyes_open cum cum_drip cum_in_pussy cum_inside cum_pool depressing dripping_semen english english_text feet female female_only full_body genital_fluids genshin_impact hair_between_eyes high_resolution hugging_own_legs indoors jenneth_blackray knees_to_chest knees_together knees_up large_breasts legs legs_together light-skinned_female long_hair looking_down medium_breasts multicolored_hair nail_polish nipples nude on_floor parted_lips purple_eyes rape sad semen shower showering sitting soles solo stable_diffusion streaked_hair tears thighs tile_wall tiles toenail_polish toenails toes trembling uncensored vagina vaginal_juices very_high_resolution very_long_hair water wet
2012 2girls addiction big_breasts blonde_hair breasts brown_hair comic cooking_mama crying depressing drug_abuse drug_addict drugs female female_only heroine high_heels hooker mama_(cooking_mama) multiple_girls piercing prostitution ptsd sad shadman slut tears text toilet upset
2012 2girls addiction big_breasts blonde_hair breasts brown_hair comic cooking_mama crying depressing drug_abuse drug_addict drugs female female_only heroine high_heels hooker mama_(cooking_mama) multiple_girls piercing prostitution ptsd sad shadman slut tears text toilet upset
after_sex after_vaginal ai-created ai_generated anus arms_around_knees ass bangs barefoot bathing bathroom black_hair blue_hair blush bodily_fluids breasts clitoris clorinde_(genshin_impact) closed_mouth completely_nude crying crying_with_eyes_open cum cum_drip cum_in_pussy cum_inside cum_pool depressing dripping_semen feet female female_only full_body genital_fluids genshin_impact hair_between_eyes high_resolution hugging_own_legs indoors jenneth_blackray knees_to_chest knees_together knees_up large_breasts legs legs_together light-skinned_female long_hair looking_down medium_breasts multicolored_hair nail_polish nipples nude on_floor parted_lips purple_eyes sad semen shower showering sitting soles solo stable_diffusion streaked_hair tears thighs tile_wall tiles toenail_polish toenails toes trembling uncensored vagina vaginal_juices very_high_resolution very_long_hair water wet
after_sex after_vaginal ai-created ai_generated anus arms_around_knees ass bangs barefoot bathing bathroom black_hair blue_hair blush bodily_fluids breasts clitoris clorinde_(genshin_impact) closed_mouth completely_nude crying crying_with_eyes_open cum cum_drip cum_in_pussy cum_inside cum_pool depressing dripping_semen feet female female_only full_body genital_fluids genshin_impact hair_between_eyes high_resolution hugging_own_legs indoors jenneth_blackray knees_to_chest knees_together knees_up large_breasts legs legs_together light-skinned_female long_hair looking_down medium_breasts multicolored_hair nail_polish nipples nude on_floor parted_lips purple_eyes sad semen shower showering sitting soles solo stable_diffusion streaked_hair tears thighs tile_wall tiles toenail_polish toenails toes trembling uncensored vagina vaginal_juices very_high_resolution very_long_hair water wet
2023 5girls barefoot_on_grass breasts clenched_teeth death depressing disney disney_fairies e254e execution fawn_(disney_fairies) female female_only femsub guillotine imminent_death kneeling multiple_girls naked periwinkle_(disney_fairies) pussy restrained rosetta_(disney_fairies) sad scared straight_hair tinker_bell what
2023 5girls barefoot_on_grass breasts clenched_teeth death depressing disney disney_fairies e254e execution fawn_(disney_fairies) female female_only femsub guillotine imminent_death kneeling multiple_girls naked periwinkle_(disney_fairies) pussy restrained rosetta_(disney_fairies) sad scared straight_hair tinker_bell what
1boy anthro depressed depressing dog_boy fat_ass futa_is_bigger futa_on_male futanari inuki_(character) inuki_zu inuzu master_and_pet penis_size_difference rika_rose_(inuzu) small_penis tagme vent_art
1boy anthro depressed depressing dog_boy fat_ass futa_is_bigger futa_on_male futanari inuki_(character) inuki_zu inuzu master_and_pet penis_size_difference rika_rose_(inuzu) small_penis tagme vent_art
1girls 2boys animated areolae bb_(baalbuddy) big_breasts birthday birthday_cake birthday_hat birthday_party breasts_out breasts_outside comedy comic depressing elf elf_ears elf_female female female_focus funny happy_birthday neon_genesis_evangelion nipples one_breast_out original original_character pointy_ears rei_ayanami skeleton solus_astorias sound tagme video voice_acted voice_acted_comic
1girls 2boys animated areolae bb_(baalbuddy) big_breasts birthday birthday_cake birthday_hat birthday_party breasts_out breasts_outside comedy comic depressing elf elf_ears elf_female female female_focus funny happy_birthday neon_genesis_evangelion nipples one_breast_out original original_character pointy_ears rei_ayanami skeleton solus_astorias sound tagme video voice_acted voice_acted_comic
1boy 1girls animated arms_held_back arms_tied ass ass_visible_through_thighs bad_end bb_(baalbuddy) big_ass big_breasts breasts comedy comic computer depressing depression female funny husband_and_wife midriff miko nipple_bulge original original_character sad shrine_maiden social_commentary solus_astorias sound tagme tentacle tentacle_sex video voice_acted voice_acted_comic
1boy 1girls animated arms_held_back arms_tied ass ass_visible_through_thighs bad_end bb_(baalbuddy) big_ass big_breasts breasts comedy comic computer depressing depression female funny husband_and_wife midriff miko nipple_bulge original original_character sad shrine_maiden social_commentary solus_astorias sound tagme tentacle tentacle_sex video voice_acted voice_acted_comic
big_ass big_thighs canine crying crying_with_eyes_open depressed depressing dog_boy furry inuki_zu inuzu page_1 rika_rose_(inuzu) self_harm tagme tears tears_of_pain vent_art
big_ass big_thighs canine crying crying_with_eyes_open depressed depressing dog_boy furry inuki_zu inuzu page_1 rika_rose_(inuzu) self_harm tagme tears tears_of_pain vent_art
1girls abby_(w0m1) breasts chubby chubby_female depressed depressing existential_crisis female pouting sad tagme thighs w0m1
1girls abby_(w0m1) breasts chubby chubby_female depressed depressing existential_crisis female pouting sad tagme thighs w0m1
1girls big_ass big_breasts breasts cd_projekt_red convenient_censoring crying crying_with_eyes_open cybernetics cyberpunk:_edgerunners cyberpunk_2077 depressing earth eyelashes feet female female_only glass kino_(artist) light-skinned_female light_skin lips looking_up lucyna_kushinada moon multicolored_hair netflix nude sad solo solo_female solo_focus space spoilers studio_trigger tear thighs wholesome
1girls big_ass big_breasts breasts cd_projekt_red convenient_censoring crying crying_with_eyes_open cybernetics cyberpunk:_edgerunners cyberpunk_2077 depressing earth eyelashes feet female female_only glass kino_(artist) light-skinned_female light_skin lips looking_up lucyna_kushinada moon multicolored_hair netflix nude sad solo solo_female solo_focus space spoilers studio_trigger tear thighs wholesome
1boy 1girls anal anal_insertion anal_masturbation crying depressing depression english_text female hero_(omori) male male_focus mari_(omori) masturbation mob_face monochrome not_worth_jacking omori sad sammycj11 sex_toy solo_focus text
1boy 1girls anal anal_insertion anal_masturbation crying depressing depression english_text female hero_(omori) male male_focus mari_(omori) masturbation mob_face monochrome not_worth_jacking omori sad sammycj11 sex_toy solo_focus text
1girls 2021 2koma allison_eckhart alternate_version_available artist_logo before_and_after begging blue_bra blue_panties blush bra bra_lift breasts brown_eyes cleavage clothing crying cuknite32 depressing dialogue english_text female female_only freckles fully_clothed grey_panties legs_together lifting_own_shirt matching_underwear midriff nipples open_mouth orange_eyes pleading red_hair red_skirt redhead sad scp-2565 scp_foundation shirt shirt_lift short_hair skirt small_breasts solo solo_female solo_focus standing sweatpants talking_to_viewer tears text text_bubble time_skip white_shirt worried worried_expression
1girls 2021 2koma allison_eckhart alternate_version_available artist_logo before_and_after begging blue_bra blue_panties blush bra bra_lift breasts brown_eyes cleavage clothing crying cuknite32 depressing dialogue english_text female female_only freckles fully_clothed grey_panties legs_together lifting_own_shirt matching_underwear midriff nipples open_mouth orange_eyes pleading red_hair red_skirt redhead sad scp-2565 scp_foundation shirt shirt_lift short_hair skirt small_breasts solo solo_female solo_focus standing sweatpants talking_to_viewer tears text text_bubble time_skip white_shirt worried worried_expression
1boy animated anthro anus ass backsack balls bed blue_eyes blush canaryprimary canid canine canis clothing dalmatian depressing dialogue digital_drawing_(artwork) digital_media_(artwork) domestic_dog edit english_text english_voice_acting fur furniture furry furry_only genitals girly heart hi_res male male_only mammal mp4 nervous on_bed one_eye_closed open_mouth open_smile oriole_(canaryprimary) smile solo solo_male sound sound_edit speech_bubble spots tagme tail text under_covers video voice_acted white_body white_fur
1boy animated anthro anus ass backsack balls bed blue_eyes blush canaryprimary canid canine canis clothing dalmatian depressing dialogue digital_drawing_(artwork) digital_media_(artwork) domestic_dog edit english_text english_voice_acting fur furniture furry furry_only genitals girly heart hi_res male male_only mammal mp4 nervous on_bed one_eye_closed open_mouth open_smile oriole_(canaryprimary) smile solo solo_male sound sound_edit speech_bubble spots tagme tail text under_covers video voice_acted white_body white_fur
ball_sucking bed bedroom blowjob blowjob_face bottomless bottomless_male bruno_carrelli cock_milking collaborative_fellatio comic comic_page cuck cucked cucked_by_friend cucked_by_rival cuckold cum_hungry depressed depressed_face depressing discord_(marvel) earrings english english_dialogue english_text exhausted_male female hijab hijabi joshua_richardson kamala_khan light-skinned_female light-skinned_male light_skin male marvel marvel_comics milking ms._marvel ms._marvel_(kamala_khan) naked nakia_bahadir nude nude_female pain penis_milking rough_sex sad sad_face saliva smartphone speech_bubble sucking sucking_balls sucking_off sucking_penis sucking_testicles sucking_too_hard thirsty too_rough upset wall wall_(structure) zoe_zimmer
ball_sucking bed bedroom blowjob blowjob_face bottomless bottomless_male bruno_carrelli cock_milking collaborative_fellatio comic comic_page cuck cucked cucked_by_friend cucked_by_rival cuckold cum_hungry depressed depressed_face depressing discord_(marvel) earrings english english_dialogue english_text exhausted_male female hijab hijabi joshua_richardson kamala_khan light-skinned_female light-skinned_male light_skin male marvel marvel_comics milking ms._marvel ms._marvel_(kamala_khan) naked nakia_bahadir nude nude_female pain penis_milking rough_sex sad sad_face saliva smartphone speech_bubble sucking sucking_balls sucking_off sucking_penis sucking_testicles sucking_too_hard thirsty too_rough upset wall wall_(structure) zoe_zimmer
2017 age_difference alcohol anthro beverage bojack_horseman bottomless chromosomefarm clothed clothed_sex clothing comic cunnilingus depressing dress feline female giraffe giraffid glory_hole hi_res interspecies jewelry looking_pleasured lying majike male mammal mature_female monochrome necklace night office older_female on_table oral orgasm princess_carolyn pussy pussy_juice raised_dress regret sad sex shame smile solo stranger table tears through_wall tongue tongue_out unprofessional_behavior vaginal_penetration
2017 age_difference alcohol anthro beverage bojack_horseman bottomless chromosomefarm clothed clothed_sex clothing comic cunnilingus depressing dress feline female giraffe giraffid glory_hole hi_res interspecies jewelry looking_pleasured lying majike male mammal mature_female monochrome necklace night office older_female on_table oral orgasm princess_carolyn pussy pussy_juice raised_dress regret sad sex shame smile solo stranger table tears through_wall tongue tongue_out unprofessional_behavior vaginal_penetration
after_rape bathroom blood brown_hair covering_crotch covering_face crying cuntboy cuntboy_only dark_room depressing friday_night_funkin friday_night_funkin_lullaby hypnos_lullaby intersex long_hair masturbation naked night not_porn shower steven_(strangled_red) water
after_rape bathroom blood brown_hair covering_crotch covering_face crying cuntboy cuntboy_only dark_room depressing friday_night_funkin friday_night_funkin_lullaby hypnos_lullaby intersex long_hair masturbation naked night not_porn shower steven_(strangled_red) water
1futa blush breasts censored depressing dickgirl erection futa_only futanari hair huge_cock human hyuuga_hinata intersex naruto nipples nude open_mouth penis short_hair solo solo_futa testicles text transplanted_penis uzumaki_naruto veins veiny_penis what white_background
1futa blush breasts censored depressing dickgirl erection futa_only futanari hair huge_cock human hyuuga_hinata intersex naruto nipples nude open_mouth penis short_hair solo solo_futa testicles text transplanted_penis uzumaki_naruto veins veiny_penis what white_background
areolae breasts bullying comic depressing envy erection female long_hair male masturbation nipples nude nude_female original original_character penis sad speech_bubble straight text tongue_out wjs07
areolae breasts bullying comic depressing envy erection female long_hair male masturbation nipples nude nude_female original original_character penis sad speech_bubble straight text tongue_out wjs07