extreme_pain best from all time -animated

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extreme pain

1futa 1girls absurd_res ai_generated ambiguous_penetration anaslex animal_ears balls big_balls big_breasts bjurne blonde_hair blue_eyes blush breasts brown_fur brown_hair brunette_hair centaur centauress centorea_shianus collaboration constricted_pupils crying crying_with_eyes_open cum cum_inside cum_spurt extreme_pain female forced furry futa_on_female futa_taur futanari futanari_centaur hi_res horse horse_penis horsecock horsecock_futanari huge_breasts kobold large_breasts lying_on_stomach moaning monster_girl monster_musume_no_iru_nichijou nakadashi on_stomach overflow pain pale-skinned_female pale_skin penetration pleasured polt_(monster_musume) prone prone_bone rape sex smile sweat tail tears wide-eyed
1futa 1girls absurd_res ai_generated ambiguous_penetration anaslex animal_ears balls big_balls big_breasts bjurne blonde_hair blue_eyes blush breasts brown_fur brown_hair brunette_hair centaur centauress centorea_shianus collaboration constricted_pupils crying crying_with_eyes_open cum cum_inside cum_spurt extreme_pain female forced furry futa_on_female futa_taur futanari futanari_centaur hi_res horse horse_penis horsecock horsecock_futanari huge_breasts kobold large_breasts lying_on_stomach moaning monster_girl monster_musume_no_iru_nichijou nakadashi on_stomach overflow pain pale-skinned_female pale_skin penetration pleasured polt_(monster_musume) prone prone_bone rape sex smile sweat tail tears wide-eyed
1girls all_fours ambiguous_penetration anal anal_destruction anal_sex animal_penis ass bestiality bumhole_destruction destroyed_anus equine equine_penis extreme_pain extreme_penetration female_on_feral female_penetrated feral_penetrating forced forced_penetration from_behind from_behind_position genitals hard_pressed hardcore hardcore_sex horse horsecock huge_cock hyper_penis impossible_fit interspecies kaguya-sama_wa_kokurasetai_~tensai-tachi_no_renai_zunousen~ large_insertion large_penis mind_break outdoor_sex pain penetration penis penis_in_pussy penis_size_difference punished punishment questionable_consent rape ridiculous_fit screaming sex shinomiya_kaguya size_difference stallion tears the_dark_mangaka wide_eyed zoophilia
1girls all_fours ambiguous_penetration anal anal_destruction anal_sex animal_penis ass bestiality bumhole_destruction destroyed_anus equine equine_penis extreme_pain extreme_penetration female_on_feral female_penetrated feral_penetrating forced forced_penetration from_behind from_behind_position genitals hard_pressed hardcore hardcore_sex horse horsecock huge_cock hyper_penis impossible_fit interspecies kaguya-sama_wa_kokurasetai_~tensai-tachi_no_renai_zunousen~ large_insertion large_penis mind_break outdoor_sex pain penetration penis penis_in_pussy penis_size_difference punished punishment questionable_consent rape ridiculous_fit screaming sex shinomiya_kaguya size_difference stallion tears the_dark_mangaka wide_eyed zoophilia
2girls anatomically_incorrect arcane arcane_jinx arcane_vi begging blue_hair clothed comic crying_with_eyes_open cuntbusting english_text extreme_pain female guro jinx_(league_of_legends) league_of_legends monkeeman0918 multiple_girls naked nervous_sweat ovaries ovary pain pink_hair small_breasts speech_bubble stomach_punch sweating text tied_up uterus vi x-ray
2girls anatomically_incorrect arcane arcane_jinx arcane_vi begging blue_hair clothed comic crying_with_eyes_open cuntbusting english_text extreme_pain female guro jinx_(league_of_legends) league_of_legends monkeeman0918 multiple_girls naked nervous_sweat ovaries ovary pain pink_hair small_breasts speech_bubble stomach_punch sweating text tied_up uterus vi x-ray
ahe_gao balls ballsack breasts destroyed_pussy drawn endured_face extreme_pain extreme_penetration female female_focus flexible folded fucked_silly giant holding_partner huge_penis hyper_penis impossible_fit it'll_never_fit living_condom living_onahole living_sex_toy lynn_(mabinogi) mabinogi male massive_penis monochrome offscreen_male painful painful_penetration painful_vaginal penetration plasmidhentai size_difference small_breasts tiny_female vaginal vaginal_penetration vindictus
ahe_gao balls ballsack breasts destroyed_pussy drawn endured_face extreme_pain extreme_penetration female female_focus flexible folded fucked_silly giant holding_partner huge_penis hyper_penis impossible_fit it'll_never_fit living_condom living_onahole living_sex_toy lynn_(mabinogi) mabinogi male massive_penis monochrome offscreen_male painful painful_penetration painful_vaginal penetration plasmidhentai size_difference small_breasts tiny_female vaginal vaginal_penetration vindictus
1futa 1girls 3d ada_wong alcina_dimitrescu duo extreme_pain female futa_on_female futanari huge_cock large_penis larger_futanari pain penis_bigger_than_torso pleasure_face rape resident_evil resident_evil_8:_village shocked size_difference smaller_female source_request standing stomach_bulge tagme tunnofun
1futa 1girls 3d ada_wong alcina_dimitrescu duo extreme_pain female futa_on_female futanari huge_cock large_penis larger_futanari pain penis_bigger_than_torso pleasure_face rape resident_evil resident_evil_8:_village shocked size_difference smaller_female source_request standing stomach_bulge tagme tunnofun
1boy 1boy1girl 1girls belly bondage bound breasts cock_and_ball_torture extreme_pain female femdom gore imminent_pain imminent_sounding insertion male male_urethral_insertion malesub monochrome navel needle needleplay needles nude pain penis pussy rape reverse_rape sadism sadistic_girl spread_eagle straight torture urethral_insertion
1boy 1boy1girl 1girls belly bondage bound breasts cock_and_ball_torture extreme_pain female femdom gore imminent_pain imminent_sounding insertion male male_urethral_insertion malesub monochrome navel needle needleplay needles nude pain penis pussy rape reverse_rape sadism sadistic_girl spread_eagle straight torture urethral_insertion
2boys beard between_legs between_thighs big_breasts bikini black_bikini black_hair black_heels black_thong blonde_hair_male bodyscissor bodyscissorfan breasts chun-li crying crying_male crying_with_eyes_open dominant_female extreme_pain feet female female_dominating_male female_domination femdom femdom_caption giantess headband high_heels ken_masters muscular_arms muscular_calves muscular_female muscular_legs muscular_thighs overpowered overpowering pain painted_fingernails painted_toenails peeing peeing_self red_headwear ryu_(street_fighter) size_difference small_penis smaller_male street_fighter submission taller_female thick_legs thick_thighs thong weak_male
2boys beard between_legs between_thighs big_breasts bikini black_bikini black_hair black_heels black_thong blonde_hair_male bodyscissor bodyscissorfan breasts chun-li crying crying_male crying_with_eyes_open dominant_female extreme_pain feet female female_dominating_male female_domination femdom femdom_caption giantess headband high_heels ken_masters muscular_arms muscular_calves muscular_female muscular_legs muscular_thighs overpowered overpowering pain painted_fingernails painted_toenails peeing peeing_self red_headwear ryu_(street_fighter) size_difference small_penis smaller_male street_fighter submission taller_female thick_legs thick_thighs thong weak_male
2d agony angelia_avallone arcana_heart arcana_heart_2 ballbusting blush breasts censored cleavage cock_and_ball_torture crotch_stomp extreme extreme_pain female femdom glory_hole highres huge_cock kneeling light-skinned_female light_skin nipples no_underwear nsfw pain pale-skinned_female pale_skin penis pussy simple_background slashcat smile white_background
2d agony angelia_avallone arcana_heart arcana_heart_2 ballbusting blush breasts censored cleavage cock_and_ball_torture crotch_stomp extreme extreme_pain female femdom glory_hole highres huge_cock kneeling light-skinned_female light_skin nipples no_underwear nsfw pain pale-skinned_female pale_skin penis pussy simple_background slashcat smile white_background
1boy 2015 anthro balls blood bottomless clenched_teeth clothed clothing corset crying death erection extreme_pain fatality gore half-dressed humanoid_penis impalement male male_death male_only mammal meredith_(arcturus) monochrome msspixy pain pain_play penis red_panda solo spikes spix spot_color tears teeth torture trapped
1boy 2015 anthro balls blood bottomless clenched_teeth clothed clothing corset crying death erection extreme_pain fatality gore half-dressed humanoid_penis impalement male male_death male_only mammal meredith_(arcturus) monochrome msspixy pain pain_play penis red_panda solo spikes spix spot_color tears teeth torture trapped