that_must_hurt! -animated best from all time

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that must hurt!

2024 5:4 aged_up anal anal_juice anal_orgasm anal_sex animal_genitalia animal_penis anthro anthro_male anthro_penetrated ass balls bareback barefoot big_ass big_butt big_penis blush bodily_fluids bubble_butt butt_blush chastity chastity_cage chastity_cage_only chastity_device chastity_device_only claws clenched_teeth cum cum_while_penetrated cumshot curvy curvy_figure dialogue disembodied_penis double_oral dragon egg egg_in_ass egg_laying ejaculation english_text equine_genitalia equine_penis erection feet fellatio femboy flat_chastity_cage friendship_is_magic gay genital_fluids genitals gold_(metal) gold_chastity_cage gold_chastity_device group group_sex hands-free hasbro hi_res huge_cock kneeling large_breasts legs_up long_penis long_tongue lying male male/male male_penetrated male_penetrating male_penetrating_male medial_ring mtf_transformation multiple_doms_one_sub multiple_insertions multiple_penetration my_little_pony mythological_creature mythological_scalie mythology nude on_back open_mouth oral orgasm penetration penile penile_penetration penis penis_in_ass pregnant profanity ridiculous_fit scalie sex simple_background small_balls soles spike_(mlp) stomach_bulge syrios tagme teeth text that_must_hurt! thick_penis thick_thighs tongue tongue_out tophat_turtle triple_anal triple_penetration vein video voice_acted watermark wide_hips yaoi
2024 5:4 aged_up anal anal_juice anal_orgasm anal_sex animal_genitalia animal_penis anthro anthro_male anthro_penetrated ass balls bareback barefoot big_ass big_butt big_penis blush bodily_fluids bubble_butt butt_blush chastity chastity_cage chastity_cage_only chastity_device chastity_device_only claws clenched_teeth cum cum_while_penetrated cumshot curvy curvy_figure dialogue disembodied_penis double_oral dragon egg egg_in_ass egg_laying ejaculation english_text equine_genitalia equine_penis erection feet fellatio femboy flat_chastity_cage friendship_is_magic gay genital_fluids genitals gold_(metal) gold_chastity_cage gold_chastity_device group group_sex hands-free hasbro hi_res huge_cock kneeling large_breasts legs_up long_penis long_tongue lying male male/male male_penetrated male_penetrating male_penetrating_male medial_ring mtf_transformation multiple_doms_one_sub multiple_insertions multiple_penetration my_little_pony mythological_creature mythological_scalie mythology nude on_back open_mouth oral orgasm penetration penile penile_penetration penis penis_in_ass pregnant profanity ridiculous_fit scalie sex simple_background small_balls soles spike_(mlp) stomach_bulge syrios tagme teeth text that_must_hurt! thick_penis thick_thighs tongue tongue_out tophat_turtle triple_anal triple_penetration vein video voice_acted watermark wide_hips yaoi
3_eyes 4_fingers anglerfish anglerfish_humanoid anglerfish_merfolk back_arching_orgasm black_hair blue_body blue_cocks blue_eyes blue_penis blue_skin blush blushing_female cervix cervix_deep cervix_view clothed_upper_body cum cumming cumming_while_penetrated cuntboy cuntboy/male cuntboy_sans_balls diphallia diphallism ejaculating_cum ejaculating_while_penetrated ejaculation expendable_(pressure) fishtail fishtail_wagging fist_against_womb fisting fisting_pussy frowning full_pussy hand_against_womb hand_inside_pussy hand_on_tail heart_symbol herm hermaphrodite inside_pussy intersex lure_(anatomy) male maleherm merfolk merman multi_genitalia multi_penis naked_lower_body open_mouth penis pressure_(roblox) pussy scarf sebastian_solace semi_clothed semi_naked skjskxxjdkx tail_wagging tailfin tailfin_wagging that_must_hurt! tongue tongue_out womb womb_stimulation x-ray y/n
3_eyes 4_fingers anglerfish anglerfish_humanoid anglerfish_merfolk back_arching_orgasm black_hair blue_body blue_cocks blue_eyes blue_penis blue_skin blush blushing_female cervix cervix_deep cervix_view clothed_upper_body cum cumming cumming_while_penetrated cuntboy cuntboy/male cuntboy_sans_balls diphallia diphallism ejaculating_cum ejaculating_while_penetrated ejaculation expendable_(pressure) fishtail fishtail_wagging fist_against_womb fisting fisting_pussy frowning full_pussy hand_against_womb hand_inside_pussy hand_on_tail heart_symbol herm hermaphrodite inside_pussy intersex lure_(anatomy) male maleherm merfolk merman multi_genitalia multi_penis naked_lower_body open_mouth penis pressure_(roblox) pussy scarf sebastian_solace semi_clothed semi_naked skjskxxjdkx tail_wagging tailfin tailfin_wagging that_must_hurt! tongue tongue_out womb womb_stimulation x-ray y/n
1boy blush bug cum cumshot dildo dildo_in_ass imagining insect inside_view kogito lamp male_only moth moth_boy non-human non-human_only penis prostate_orgasm prostate_stimulation riding riding_dildo tagme that_must_hurt! toony_face white_background
1boy blush bug cum cumshot dildo dildo_in_ass imagining insect inside_view kogito lamp male_only moth moth_boy non-human non-human_only penis prostate_orgasm prostate_stimulation riding riding_dildo tagme that_must_hurt! toony_face white_background
1boy arched_back blush cum cumshot flapping_wings gay insects kogito lava_lamp male_only moth non-human non-human_only nude nude_male object_in_ass prostate_stimulation skinny stomach_bulge sweat sweatdrop that_must_hurt! thought_bubble thoughts toony_face wings
1boy arched_back blush cum cumshot flapping_wings gay insects kogito lava_lamp male_only moth non-human non-human_only nude nude_male object_in_ass prostate_stimulation skinny stomach_bulge sweat sweatdrop that_must_hurt! thought_bubble thoughts toony_face wings
1boy blush bottomless dildo dildo_in_ass kogito lamp male_only moth moth_boy non-human non-human_only penis riding riding_dildo tagme that_must_hurt! toony_face white_background
1boy blush bottomless dildo dildo_in_ass kogito lamp male_only moth moth_boy non-human non-human_only penis riding riding_dildo tagme that_must_hurt! toony_face white_background
3_eyes :>= alternate_version_available anglerfish anglerfish_humanoid angry angry_face balls biting_penis blood blood_on_penis blood_spray blood_spurt blowjob blowjob_face bruh cbt doodle ear_fins fellatio fellatio_face genital_torture giving_head grabbing_balls hd hi_res high_resolution highres lure_(anatomy) male male_ryona merfolk merman monochrome multi_eye ouch penis penis_bite penis_biting pressure_(roblox) roblox roblox_game sallysa20728693 sebastian_solace sharp_teeth sideways sideways_oral that_must_hurt! wavy_hair xd
3_eyes :>= alternate_version_available anglerfish anglerfish_humanoid angry angry_face balls biting_penis blood blood_on_penis blood_spray blood_spurt blowjob blowjob_face bruh cbt doodle ear_fins fellatio fellatio_face genital_torture giving_head grabbing_balls hd hi_res high_resolution highres lure_(anatomy) male male_ryona merfolk merman monochrome multi_eye ouch penis penis_bite penis_biting pressure_(roblox) roblox roblox_game sallysa20728693 sebastian_solace sharp_teeth sideways sideways_oral that_must_hurt! wavy_hair xd
1boy antennae antennae_(anatomy) biting_lip biting_own_lip blush bodily_fluids bored erection flapping_wings kogito lava_lamp looking_at_phone male_only moth non-human non-human_only object_in_ass object_insertion penis phone precum shaking_legs sweater that_must_hurt! toony_face
1boy antennae antennae_(anatomy) biting_lip biting_own_lip blush bodily_fluids bored erection flapping_wings kogito lava_lamp looking_at_phone male_only moth non-human non-human_only object_in_ass object_insertion penis phone precum shaking_legs sweater that_must_hurt! toony_face
6cinnii blood chibi cosmo_(dandy's_world) crying dandy's_world eye_fucking gore guro oh_my_god pain ryona scared skull_fucking sprout_(dandy's_world) that_must_hurt! thats_gotta_hurt unknown_source
6cinnii blood chibi cosmo_(dandy's_world) crying dandy's_world eye_fucking gore guro oh_my_god pain ryona scared skull_fucking sprout_(dandy's_world) that_must_hurt! thats_gotta_hurt unknown_source