almost_crying best from all time -animated

Time frame

Tags

almost crying

1boy 2girls ? absurd_res adopted adopted_son adoptive_mother after_rape almost_crying ambiguous_penetration anthro anthro_penetrated ashamed ass big_breasts blush bodily_fluids bottomless bovid breasts brown_hair caprine car clothed clothed_rape clothing deltarune dripping duo enigi09 female female_penetrated from_behind_position genital_fluids goat group hair heart hi_res huge_breasts human human_on_anthro human_penetrating human_penetrating_anthro incest interspecies kris_(deltarune) male male/female male_human/female_anthro male_human/female_monster male_penetrating male_penetrating_female mammal milf monster penetration pussy_juice pussy_juice_drip rape reptile scalie sex susie_(deltarune) technical_incest toriel undertale undertale_(series) vehicle video_games
1boy 2girls ? absurd_res adopted adopted_son adoptive_mother after_rape almost_crying ambiguous_penetration anthro anthro_penetrated ashamed ass big_breasts blush bodily_fluids bottomless bovid breasts brown_hair caprine car clothed clothed_rape clothing deltarune dripping duo enigi09 female female_penetrated from_behind_position genital_fluids goat group hair heart hi_res huge_breasts human human_on_anthro human_penetrating human_penetrating_anthro incest interspecies kris_(deltarune) male male/female male_human/female_anthro male_human/female_monster male_penetrating male_penetrating_female mammal milf monster penetration pussy_juice pussy_juice_drip rape reptile scalie sex susie_(deltarune) technical_incest toriel undertale undertale_(series) vehicle video_games
1girls 2boys absurd_res ai_generated almost_crying animal_ears big_ass blowjob blush blush_lines blushing_at_viewer brown_hair dog_ears doggy_style double_penetration eye_contact eyebrows eyebrows_visible_through_hair fellatio female female_focus full_mouth half-dressed half_naked hands_on_ass hands_on_penis hi_res highres light-skinned_female light-skinned_male light_skin long_hair male nemus_waifu_generator no_panties no_skirt on_all_fours orange_eyes penetration penis pubic_hair rape raped_girl saliva saliva_on_penis saliva_trail school_uniform schoolgirl simple_background socks thighs vaginal_penetration white_socks
1girls 2boys absurd_res ai_generated almost_crying animal_ears big_ass blowjob blush blush_lines blushing_at_viewer brown_hair dog_ears doggy_style double_penetration eye_contact eyebrows eyebrows_visible_through_hair fellatio female female_focus full_mouth half-dressed half_naked hands_on_ass hands_on_penis hi_res highres light-skinned_female light-skinned_male light_skin long_hair male nemus_waifu_generator no_panties no_skirt on_all_fours orange_eyes penetration penis pubic_hair rape raped_girl saliva saliva_on_penis saliva_trail school_uniform schoolgirl simple_background socks thighs vaginal_penetration white_socks
almost_crying belly_button big_breasts blush cowgirl_position cum_in_pussy cum_inside fertilization grabbing_own_breast hayashi_custom impregnation looking_at_viewer looking_down maid maid_headdress naked naked_female navel pov pubic_hair red_eyes ribbons sakuya_izayoi thighs touhou white_hair
almost_crying belly_button big_breasts blush cowgirl_position cum_in_pussy cum_inside fertilization grabbing_own_breast hayashi_custom impregnation looking_at_viewer looking_down maid maid_headdress naked naked_female navel pov pubic_hair red_eyes ribbons sakuya_izayoi thighs touhou white_hair
1boy 1girls 3d 3d_(artwork) about_to_cum almost_crying anal anal_insertion anal_sex asshole_opened_wide bedroom big_balls big_penis boots brown_hair capcom carlos_oliveira erection_under_clothes female_orgasm female_penetrated fucked_senseless fucked_silly giant_cock giant_penis hairless_balls hand_on_ass huge_balls huge_cock jill_valentine jill_valentine_(sasha_zotova) long_penis looking_pleasured masculine monster_cock muscular_legs muscular_male nude_male orgasm pants_down pants_pulled_down pleasure_face pounding resident_evil resident_evil_3 resident_evil_3_remake reverse_cowgirl_position rough_sex sfmlover22 short_hair stretched_anus stretching thick_penis
1boy 1girls 3d 3d_(artwork) about_to_cum almost_crying anal anal_insertion anal_sex asshole_opened_wide bedroom big_balls big_penis boots brown_hair capcom carlos_oliveira erection_under_clothes female_orgasm female_penetrated fucked_senseless fucked_silly giant_cock giant_penis hairless_balls hand_on_ass huge_balls huge_cock jill_valentine jill_valentine_(sasha_zotova) long_penis looking_pleasured masculine monster_cock muscular_legs muscular_male nude_male orgasm pants_down pants_pulled_down pleasure_face pounding resident_evil resident_evil_3 resident_evil_3_remake reverse_cowgirl_position rough_sex sfmlover22 short_hair stretched_anus stretching thick_penis
almost_crying almost_naked ardouuu asphyxiation breath_play bungo_stray_dogs domination fyodor_dostoevsky gay gay_sex male male_only monochrome nikolai_gogol outline rough_sketch strangling yaoi
almost_crying almost_naked ardouuu asphyxiation breath_play bungo_stray_dogs domination fyodor_dostoevsky gay gay_sex male male_only monochrome nikolai_gogol outline rough_sketch strangling yaoi
1boy 1boy1girl 2d 2girls almost_crying ambiguous_consent anal anal_sex angry aphrodos beast beast_boy big_ass big_balls big_breasts big_butt big_dick big_penis bubble_butt bulge camera comic comic_page console cum cum_in_ass cum_inside dc dc_comics exclamation_point eyepatch finger_in_mouth fish_hooking forehead_jewel functionally_nude furious gamecube gamecube_controller garfield_logan grey-skinned_female grey_skin hand_on_ass hand_on_butt instant_loss koriand'r legs_behind_head legs_over_head mario_(series) mario_party nipples nude open_mouth phone photo_(object) pretzel_position purple_hair pussy question_mark rachel_roth rape raven_(dc) revenge revenge_sex reverse_suspended_congress sad scared scared_expression size_difference smiling smug smug_face spit_bubble spread_legs spying starfire stomach_bulge story sweat teen_titans teeth_showing text text_bubble transformation veiny_testicles
1boy 1boy1girl 2d 2girls almost_crying ambiguous_consent anal anal_sex angry aphrodos beast beast_boy big_ass big_balls big_breasts big_butt big_dick big_penis bubble_butt bulge camera comic comic_page console cum cum_in_ass cum_inside dc dc_comics exclamation_point eyepatch finger_in_mouth fish_hooking forehead_jewel functionally_nude furious gamecube gamecube_controller garfield_logan grey-skinned_female grey_skin hand_on_ass hand_on_butt instant_loss koriand'r legs_behind_head legs_over_head mario_(series) mario_party nipples nude open_mouth phone photo_(object) pretzel_position purple_hair pussy question_mark rachel_roth rape raven_(dc) revenge revenge_sex reverse_suspended_congress sad scared scared_expression size_difference smiling smug smug_face spit_bubble spread_legs spying starfire stomach_bulge story sweat teen_titans teeth_showing text text_bubble transformation veiny_testicles
2boys almost_crying anal_sex bungo_stray_dogs cum cum_on_body gay gay_sex golemc long_hair nikolai_gogol pleasure_face saliva saliva_string sigma_(bungo_stray_dogs) two_tone_hair yaoi
2boys almost_crying anal_sex bungo_stray_dogs cum cum_on_body gay gay_sex golemc long_hair nikolai_gogol pleasure_face saliva saliva_string sigma_(bungo_stray_dogs) two_tone_hair yaoi
almost_crying come_on gay gay_sex m/m male/male male_only no_visible_genitalia penetrated south_park stephen_stotch sweat sweating tied_up what yaoi
almost_crying come_on gay gay_sex m/m male/male male_only no_visible_genitalia penetrated south_park stephen_stotch sweat sweating tied_up what yaoi
1girls almost_crying areola areolae artist_request bed bedding_background bedroom bedroom_setting bedroom_sex belly_button big_areola big_areolae big_areolas big_breasts boob_drop breasts brown_hair caucasian_female closed_mouth collarbone coloured completely_nude completely_nude_female cowgirl_position disheveled_hair english_text female grey_background harry_potter harry_potter:_hogwarts_mystery hogwarts_student impregnation_attempt impregnation_request large_breasts light-skinned light-skinned_female light_blush merula_snyde messy_hair nude nude_female orange_hair purple_eyes slight_blush solo tagme talking talking_to_partner tears text topless_female wanted_impregnation wholesome wholesome_sex
1girls almost_crying areola areolae artist_request bed bedding_background bedroom bedroom_setting bedroom_sex belly_button big_areola big_areolae big_areolas big_breasts boob_drop breasts brown_hair caucasian_female closed_mouth collarbone coloured completely_nude completely_nude_female cowgirl_position disheveled_hair english_text female grey_background harry_potter harry_potter:_hogwarts_mystery hogwarts_student impregnation_attempt impregnation_request large_breasts light-skinned light-skinned_female light_blush merula_snyde messy_hair nude nude_female orange_hair purple_eyes slight_blush solo tagme talking talking_to_partner tears text topless_female wanted_impregnation wholesome wholesome_sex
abs absurd_res against_wall ai_generated almost_crying almost_naked almost_nude arms_behind_back ass balls big_breasts black_legwear blue_hoodie blue_shirt blush blush breasts brown_eyes cat_ears catgirl collar cum cum_drip cum_in_pussy cum_inside cumshot dog_collar erection eyebrows_visible_through_hair futa_only futanari hi_res huge_breasts huge_cock huge_nipples light-skinned_futanari light_skin long_penis neko nekomimi nemus_waifu_generator open_mouth panties penetration penis penis_out pleasure_face pleasured precum purple_hair pussy saliva saliva_string saliva_trail spread_legs street teeth testicles thick_thighs thighs upshirt veiny_penis visible_nipples wall wall_(structure)
abs absurd_res against_wall ai_generated almost_crying almost_naked almost_nude arms_behind_back ass balls big_breasts black_legwear blue_hoodie blue_shirt blush blush breasts brown_eyes cat_ears catgirl collar cum cum_drip cum_in_pussy cum_inside cumshot dog_collar erection eyebrows_visible_through_hair futa_only futanari hi_res huge_breasts huge_cock huge_nipples light-skinned_futanari light_skin long_penis neko nekomimi nemus_waifu_generator open_mouth panties penetration penis penis_out pleasure_face pleasured precum purple_hair pussy saliva saliva_string saliva_trail spread_legs street teeth testicles thick_thighs thighs upshirt veiny_penis visible_nipples wall wall_(structure)
1boy about_to_cry almost_crying ass_expansion balls ballsack bdsm_room begging begging_for_mercy begging_pose begging_to_stop black_hair blur_censor bondage brown_body brown_skin censored censored_penis clenched_hand clenched_hands clenched_teeth completely_naked completely_nude completely_nude_male confused confused_look cum cum_between_legs cum_between_thighs dark_elf dark_skin ejaculation embarrassed embarrassed_nude_exposure embarrassed_nude_male gay imminent_anal imminent_penetration imminent_rape imminent_sex male_only male_rape_victim malesub muscular muscular_male muscular_sub nude_male raraja77 restrain restrained restrained_arms restrained_legs restraints semen yellow_eyes
1boy about_to_cry almost_crying ass_expansion balls ballsack bdsm_room begging begging_for_mercy begging_pose begging_to_stop black_hair blur_censor bondage brown_body brown_skin censored censored_penis clenched_hand clenched_hands clenched_teeth completely_naked completely_nude completely_nude_male confused confused_look cum cum_between_legs cum_between_thighs dark_elf dark_skin ejaculation embarrassed embarrassed_nude_exposure embarrassed_nude_male gay imminent_anal imminent_penetration imminent_rape imminent_sex male_only male_rape_victim malesub muscular muscular_male muscular_sub nude_male raraja77 restrain restrained restrained_arms restrained_legs restraints semen yellow_eyes
3d 3d_animation 3d_model 40s 50s abs african_american african_male age_difference aggressive akiyama_shun almost_crying anal anal_sex ass_fucking ass_out beard bedroom bedroom_sex big_forearms black_male blonde_hair chest_hair cock cock_hungry cumming cumming_from_masturbation cumshot cumshot_in_mouth cumshot_on_face dominant_male domination dragon_tattoo exhausted exhausted_male eyes_half_closed flat_ass forearms forehead_kiss fucked_from_behind fucked_silly gang_bang gangbang gangster gay gay_anal gay_sex getting_fucked goda_ryuji groping_ass group group_sex hand_on_back hand_on_butt handjob head_on_lap head_on_thighs holding_penis holding_waist homosexual homosexual_sex hotel hotel_room interracial interracial_sex jerking_off kiryu_kazuma kissing_forehead large_penis larger_male laying_on_back legs_together licking_chest licking_partner like_a_dragon_(series) long_penis loving_look man_ass man_boobs man_tits medium_hair medium_penis men_kissing midriff milking moaning moaning_in_pleasure mullet_(hairstyle) muscular_male nervous no_pubic_hair old_man old_man_yaoi on_knees open_mouth orgy pinned_down pinned_to_bed rubbing_back ryu_ga_gotoku ryuu_ga_gotoku self_fondle self_fuck self_grope self_groping silver_fox skinny_male slapping_butt slippery small_pecs smirking_at_partner stroking_cock stroking_penis tattoo_on_ass thick_cum thighs_together thin_male touching_ass unhappy unhappy_male unspecified wet_cock white_hair whore_eyes yakuza_(series) yakuza_boss yakuza_tattoo yaoi yaoi_orgy
3d 3d_animation 3d_model 40s 50s abs african_american african_male age_difference aggressive akiyama_shun almost_crying anal anal_sex ass_fucking ass_out beard bedroom bedroom_sex big_forearms black_male blonde_hair chest_hair cock cock_hungry cumming cumming_from_masturbation cumshot cumshot_in_mouth cumshot_on_face dominant_male domination dragon_tattoo exhausted exhausted_male eyes_half_closed flat_ass forearms forehead_kiss fucked_from_behind fucked_silly gang_bang gangbang gangster gay gay_anal gay_sex getting_fucked goda_ryuji groping_ass group group_sex hand_on_back hand_on_butt handjob head_on_lap head_on_thighs holding_penis holding_waist homosexual homosexual_sex hotel hotel_room interracial interracial_sex jerking_off kiryu_kazuma kissing_forehead large_penis larger_male laying_on_back legs_together licking_chest licking_partner like_a_dragon_(series) long_penis loving_look man_ass man_boobs man_tits medium_hair medium_penis men_kissing midriff milking moaning moaning_in_pleasure mullet_(hairstyle) muscular_male nervous no_pubic_hair old_man old_man_yaoi on_knees open_mouth orgy pinned_down pinned_to_bed rubbing_back ryu_ga_gotoku ryuu_ga_gotoku self_fondle self_fuck self_grope self_groping silver_fox skinny_male slapping_butt slippery small_pecs smirking_at_partner stroking_cock stroking_penis tattoo_on_ass thick_cum thighs_together thin_male touching_ass unhappy unhappy_male unspecified wet_cock white_hair whore_eyes yakuza_(series) yakuza_boss yakuza_tattoo yaoi yaoi_orgy
4st_injection almost_crying capcom censored clenched_teeth defeated drooling female highres human male penetration pussy pussy_juice rape sakura_kasugano school_uniform sex straight street_fighter sweat
4st_injection almost_crying capcom censored clenched_teeth defeated drooling female highres human male penetration pussy pussy_juice rape sakura_kasugano school_uniform sex straight street_fighter sweat
! 1boy 1girls ? abs almost_crying alternate_breast_size anal anal_sex anal_through_clothes anythinggoes areolae ass ass_grab balls bangs barefoot big_balls big_breasts black_hair breasts capcom cleavage clenched_teeth clitoris comic defeated dialogue domination drill_hair duo feet female female_on_top femsub forced forced_in_fabric fucked_silly hairless_pussy highres holding_ass huge_ass huge_breasts huge_cock human instant_loss instant_loss_2koma interracial juri_han large_breasts larger_male leg_grab legs_held_open male maledom monochrome nail_polish navel nipples nude on_one_leg penetration_through_clothes penis profanity puffy_nipples pussy rape raped reverse_suspended_congress rolling_eyes sidelocks size_difference skimpy smaller_female smirk soles solo_focus spread_legs straight street_fighter sweat tears text thick_thighs thong through_clothes toenail_polish toes toned topless towel towel_around_neck twin_drills underwear urien voluptuous wide_hips
! 1boy 1girls ? abs almost_crying alternate_breast_size anal anal_sex anal_through_clothes anythinggoes areolae ass ass_grab balls bangs barefoot big_balls big_breasts black_hair breasts capcom cleavage clenched_teeth clitoris comic defeated dialogue domination drill_hair duo feet female female_on_top femsub forced forced_in_fabric fucked_silly hairless_pussy highres holding_ass huge_ass huge_breasts huge_cock human instant_loss instant_loss_2koma interracial juri_han large_breasts larger_male leg_grab legs_held_open male maledom monochrome nail_polish navel nipples nude on_one_leg penetration_through_clothes penis profanity puffy_nipples pussy rape raped reverse_suspended_congress rolling_eyes sidelocks size_difference skimpy smaller_female smirk soles solo_focus spread_legs straight street_fighter sweat tears text thick_thighs thong through_clothes toenail_polish toes toned topless towel towel_around_neck twin_drills underwear urien voluptuous wide_hips
1girls almost_crying archway_of_venus bangs black_hair blush blushing breasts completely_naked completely_nude completely_nude_female cowboy_shot embarrassed embarrassed_nude_female erect_nipples exposing_self female female_focus female_only flashing flashing_breasts flashing_pussy forehead gluteal_fold gradient_hair high_resolution hips innie irohakaede kaguya-sama_wa_kokurasetai_~tensai-tachi_no_renai_zunousen~ looking_at_viewer navel nipples nude nude_female nude_filter parted_bangs pettanko puffy_vulva pussy red_background revealing shaved_crotch shaved_pussy shinomiya_kaguya simple_background small_breasts solo solo_female solo_focus stomach tagme thigh_gap third-party_edit uncensored vagina very_high_resolution
1girls almost_crying archway_of_venus bangs black_hair blush blushing breasts completely_naked completely_nude completely_nude_female cowboy_shot embarrassed embarrassed_nude_female erect_nipples exposing_self female female_focus female_only flashing flashing_breasts flashing_pussy forehead gluteal_fold gradient_hair high_resolution hips innie irohakaede kaguya-sama_wa_kokurasetai_~tensai-tachi_no_renai_zunousen~ looking_at_viewer navel nipples nude nude_female nude_filter parted_bangs pettanko puffy_vulva pussy red_background revealing shaved_crotch shaved_pussy shinomiya_kaguya simple_background small_breasts solo solo_female solo_focus stomach tagme thigh_gap third-party_edit uncensored vagina very_high_resolution
1boy 1boy1girl 1girls 2d ai_generated almost_crying angry anus areolae ass bed big_ass big_balls big_breasts big_butt big_nipples big_penis black_body blush bubble_ass bubble_butt clenched_teeth completely_naked completely_nude completely_nude_female completely_nude_male crying curvy curvy_body curvy_female curvy_figure curvy_hips cute cute_expression cute_face dark-skinned_male dark_skin dat_ass female female_focus female_penetrated female_protagonist from_behind from_behind_position grabbing grabbing_from_behind grabbing_sheets grabbing_thigh grabbing_thighs green_eyes green_hair horny horny_female huge_ass huge_balls huge_belly huge_breasts huge_butt huge_cock huge_nipples huge_testicles interracial large_ass large_balls large_breasts large_penis large_testicles light-skinned light-skinned_female light_skin male male/female male_penetrating_female medium_breasts medium_penis naked naked_female navel nude nude_female on_bed one-punch_man open_legs pale-skinned_female pale_skin penetration pounding pussy rekonai rough rough_sex seductive seductive_body seductive_pose sex short_hair smaller_female surprise surprise_buttsex surprised surprised_expression surprised_face tagme tatsumaki thick thick_ass thick_hips thick_legs thick_lips thick_penis thick_thighs thin thin_female thin_waist thrusting thrusting_hard thrusting_into_ass tight_fit uncensored vagina wide_hips wide_spread_legs wide_thighs
1boy 1boy1girl 1girls 2d ai_generated almost_crying angry anus areolae ass bed big_ass big_balls big_breasts big_butt big_nipples big_penis black_body blush bubble_ass bubble_butt clenched_teeth completely_naked completely_nude completely_nude_female completely_nude_male crying curvy curvy_body curvy_female curvy_figure curvy_hips cute cute_expression cute_face dark-skinned_male dark_skin dat_ass female female_focus female_penetrated female_protagonist from_behind from_behind_position grabbing grabbing_from_behind grabbing_sheets grabbing_thigh grabbing_thighs green_eyes green_hair horny horny_female huge_ass huge_balls huge_belly huge_breasts huge_butt huge_cock huge_nipples huge_testicles interracial large_ass large_balls large_breasts large_penis large_testicles light-skinned light-skinned_female light_skin male male/female male_penetrating_female medium_breasts medium_penis naked naked_female navel nude nude_female on_bed one-punch_man open_legs pale-skinned_female pale_skin penetration pounding pussy rekonai rough rough_sex seductive seductive_body seductive_pose sex short_hair smaller_female surprise surprise_buttsex surprised surprised_expression surprised_face tagme tatsumaki thick thick_ass thick_hips thick_legs thick_lips thick_penis thick_thighs thin thin_female thin_waist thrusting thrusting_hard thrusting_into_ass tight_fit uncensored vagina wide_hips wide_spread_legs wide_thighs
1girls 2020 4:5 almost_crying angry angry_nude_female big_breasts blush blushing breast_squeeze breasts breasts_together cloud_strife completely_naked completely_nude completely_nude_female cute embarrassed embarrassed_nude_female exposed eyebrows_visible_through_hair female female_focus final_fantasy final_fantasy_vii full_body gloves hands_between_legs head_pat highres holding_person inksgirls kneeling looking_at_viewer medium_breasts minigirl monochrome navel nipples nude only_one_naked patting_head pouting pov pushing_breasts_together pussy short_hair simple_background sitting size_difference tearing_up tears thighs v_arms wariza white_background wholesome yuffie_kisaragi
1girls 2020 4:5 almost_crying angry angry_nude_female big_breasts blush blushing breast_squeeze breasts breasts_together cloud_strife completely_naked completely_nude completely_nude_female cute embarrassed embarrassed_nude_female exposed eyebrows_visible_through_hair female female_focus final_fantasy final_fantasy_vii full_body gloves hands_between_legs head_pat highres holding_person inksgirls kneeling looking_at_viewer medium_breasts minigirl monochrome navel nipples nude only_one_naked patting_head pouting pov pushing_breasts_together pussy short_hair simple_background sitting size_difference tearing_up tears thighs v_arms wariza white_background wholesome yuffie_kisaragi
2boys about_to_cry about_to_cum almost_crying anal anal_insertion anal_sex anus ass blind blue_(rainbow_friends) blush bombbf bubble_ass bubble_butt digital_media_(artwork) dripping_cum dripping_precum dripping_wet duo fast_thrusts frown gay green_(rainbow_friends) heavy_breathing huge_balls looking_at_genitalia looking_back male male/male male_only multiple_boys penis pounding rainbow_friends roblox roblox_game sex size_difference smaller_penetrating source_request stomach_bulge struggling struggling_to_fit sweat sweatdrop sweating_profusely thrusting thrusting_hard thrusting_into_ass tongue_out wet wet_genitalia
2boys about_to_cry about_to_cum almost_crying anal anal_insertion anal_sex anus ass blind blue_(rainbow_friends) blush bombbf bubble_ass bubble_butt digital_media_(artwork) dripping_cum dripping_precum dripping_wet duo fast_thrusts frown gay green_(rainbow_friends) heavy_breathing huge_balls looking_at_genitalia looking_back male male/male male_only multiple_boys penis pounding rainbow_friends roblox roblox_game sex size_difference smaller_penetrating source_request stomach_bulge struggling struggling_to_fit sweat sweatdrop sweating_profusely thrusting thrusting_hard thrusting_into_ass tongue_out wet wet_genitalia