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painful insertion
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63
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21
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10_rings 1boy 3girls amiya_(arknights) animal_ears animal_girl animal_tail arknights bleeding bleeding_eyes bleeding_from_mouth bleeding_from_pussy blood blood_drip blood_everywhere blood_from_mouth blood_on_body blood_on_breasts blood_on_chest blood_on_face blood_on_fingers blood_on_hand blood_on_leg blood_on_legs blood_on_thighs blood_stain bloody_clothes blue_clothes blue_clothing blue_eyes bound breasts breasts_out brown_hair brunette cardigan_(arknights) cat_ears cat_girl cat_tail catgirl choker collar crying crying_blood crying_with_eyes_open dead death destroyed_pussy dog_ears dog_girl dog_tail dress dripping_blood ear_grab execution female female_penetrated femsub forced_penetration functionally_nude gore guangmi guerrilla_shieldguard_(arknights) guro hi_res high_resolution highres imminent_death imminent_torture impaled impalement impossible_fit infection_monitor_(arknights) jacket knee_pads knee_socks kneepads kneesocks light_brown_hair long_hair male maledom medium_breasts melantha_(arknights) neck_collar nipples one_piece_dress one_shoe one_shoe_on open_clothes open_jacket open_mouth open_vest pain painful painful_insertion painful_penetration painful_vaginal partially_clothed partially_clothed_female partially_nude partially_nude_female pink_eyes purple_eyes purple_hair pussy pussy_destruction rabbit_ears rabbit_girl ring ring_on_finger rings sadism shoes shoes_removed shoulder_grab skirt small_breasts snuff socks stockings stomach_bulge struggling thighhighs torn_clothes torn_clothing torn_dress torn_skirt torture tortured tortured_to_death vaginal_penetration vest vlad_the_impaler
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1boy 1futa 3d all_fours anal animated ass balls black_screen_roulette blank_thumbnail bottomless censored clothed clothing cock-tail cross_section crossdressing crying cum cum_in_ass cum_inside cum_while_penetrated dialogue doggy_style doggystyle ejaculation erection femboy flaccid flaccid_while_penetrated frottage futa_is_bigger futa_on_femboy futa_on_male futadom futanari hands-free handsfree_ejaculation human intersex japanese_text jaxmmd kantai_collection large_ass large_penis larger_futa light-skinned_futa light-skinned_male light_skin long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male mikumikudance mmd mosaic_censoring mp4 multiple_orgasms on_stomach orgasm otoko_no_ko otokonoko pain painful_anal painful_insertion painful_penetration partially_clothed peeing penis penis_and_balls_touching penis_on_balls penis_size_difference penis_touching_balls prone_bone prostate rape sex shimakaze_(kantai_collection) size_difference smaller_male sound takao_(kantai_collection) text thick_thighs video
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1boy 1futa 3d against_wall ahe_gao anal anal_sex animated arched_back areolae ass big_ass big_penis blush blushing_profusely bottomless breasts clothed clothing crossdressing doggy_style duo duo_focus erection femboy futa_is_bigger futa_on_femboy futa_on_male futadom futanari hand_on_another's_head hand_on_head huge_breasts human intersex jaxmmd kantai_collection large_ass large_breasts large_penis larger_futa light-skinned_femboy light-skinned_futa light-skinned_male light_skin long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male mikumikudance mmd mostly_nude mp4 nipples pain painful_anal painful_insertion painful_penetration partially_clothed penis penis_size_difference questionable_consent rape resisting rolling_eyes sex shimakaze_(kantai_collection) smaller_male sound source_request standing stomach_bulge takao_(kantai_collection) thick_ass thick_thighs thigh_sex tongue tongue_out video voluptuous wide_hips
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1futa 1girls ahe_gao amy_rose anthro areolae ass balls big_areola big_ass big_balls big_breasts big_butt big_penis blush breast_expansion breast_growth breast_growth_(enlargement) breast_inflation breasts clenched clenched_teeth cum cum_drip cum_dripping cum_from_nipples cum_in_breasts cum_inside cum_on_floor cumming cumming_while_penetrating cycilla deimion_j_shadowwolf duo female filled_to_the_brim filling forced fucked_senseless furry futa_on_female futa_penetrating futanari gaping_nipples huge_areolae huge_ass huge_balls huge_breasts huge_butt huge_cock huge_testicles hyper hyper_breasts in_pain inflation intersex large_areolae large_ass large_breasts large_insertion looking_back nipple_penetration on_knees painful painful_insertion painful_penetration pants_down penis saliva saliva_trail sega sonic_(series) sonic_the_hedgehog_(series) standing tagme talking_to_viewer teeth_clenched teeth_showing testicles too_much_cum touching_breast wagging_tail
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2dickgirls 2futas alternate_version_available anal anal_penetration anal_sex android_18 anger_vein angry angry_expression angry_eyes angry_sex areolae ass ass_jiggle balls big_areola big_ass big_balls big_breasts big_butt big_penis blonde_hair breasts crossover cum cum_drip cum_explosion cum_filled cum_in_ass cum_in_mouth cum_inside cum_on_face cum_overflow cumshot cumshot_in_anus cumshot_in_mouth dark_areola dialogue dickgirl dickgirl/dickgirl dickgirl_on_dickgirl dickgirl_only dickgirl_penetrated dickgirl_penetrating dominant_futa domination dragon_ball dragon_ball_super dragon_ball_z duo female forced forced_anal forced_oral futa_on_futa futa_only futa_penetrated futa_penetrating futa_sans_pussy futanari futasub gagged gagging gaping gaping_anus gilf gritting_teeth hips honeybread huge_areolae huge_ass huge_balls huge_breasts huge_butt huge_cock huge_testicles instant_loss_2koma insult intersex jiggling_ass large_areolae large_ass large_balls large_breasts large_insertion large_penis large_testicles larger_futa light-skinned_futa light_skin milf naruto naruto_(series) naruto_shippuden one_eye_closed open_mouth oral oral_penetration oral_sex painful painful_anal painful_insertion painful_penetration penis rape rough_sex small_dom_big_sub smaller_futa stretched_anus teeth_clenched teeth_showing testicles text thick thick_ass thick_cum thick_hips thick_legs thick_penis thick_thighs tsunade vein veiny_penis
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2girls anal arm_stockings armwear ass biting black_bow black_bow_tie black_bowtie black_eyebrows black_eyelashes black_eyeliner black_eyeshadow black_nail_polish black_nails black_tentacles blonde_hair bow_tie bowtie bowtie_only charlie_morningstar_(hazbin_hotel) cry crying crying_with_eyes_open cum cum_drip cum_dripping cum_in_ass cum_in_pussy cum_inside cum_on_lower_body cum_string drool drool_on_face drooling elbow_gloves eyebrows eyelashes eyeliner eyes eyes_rolled_up eyes_wide_open female female_focus female_only fucked_silly fully_nude gloves goatwithsauce grey_armwear grey_body grey_elbow_gloves grey_gloves grey_legwear grey_nipples grey_skin grey_socks grey_stockings grey_thighhighs hazbin_hotel high_gloves in_pain large_bow legwear long_hair long_socks looking_up mouth_open multiple_females multiple_girls naked naked_female nude nude_female pain painal painful painful_anal painful_insertion painful_penetration painful_vaginal pink_bow pink_nipples pink_striped_socks pussy rape raped raped_by_monster red_cheeks red_eyes red_nipples red_pussy sharp_teeth shaved_pussy stockings straight_hair striped_legwear striped_socks striped_stockings striped_thighhighs sweat sweatdrop sweating tagme teary_eyes teeth tentacle tentacle_in_anus tentacle_in_ass tentacle_in_pussy tentacle_rape tentacle_sex tentacles thighhigh_socks thighhighs vaggie_(hazbin_hotel) vaginal vaginal_penetration vivienne_medrano white_body white_hair white_skin wide_eyes yellow_eyes
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2girls anal arm_stockings armwear ass biting black_bow black_bow_tie black_bowtie black_eyebrows black_eyelashes black_eyeliner black_eyeshadow black_nail_polish black_nails black_tentacles blonde_hair bow_tie bowtie bowtie_only charlie_morningstar_(hazbin_hotel) cry crying crying_with_eyes_open cum cum_drip cum_dripping cum_in_ass cum_in_pussy cum_inside cum_on_lower_body cum_string drool drool_on_face drooling elbow_gloves eyebrows eyelashes eyeliner eyes eyes_rolled_up eyes_wide_open female female_focus female_only fucked_silly fully_nude gloves goatwithsauce grey_armwear grey_body grey_elbow_gloves grey_gloves grey_legwear grey_nipples grey_skin grey_socks grey_stockings grey_thighhighs hazbin_hotel high_gloves in_pain large_bow legwear long_hair long_socks looking_up mouth_open multiple_females multiple_girls naked naked_female nude nude_female pain painal painful painful_anal painful_insertion painful_penetration painful_vaginal pink_bow pink_nipples pink_striped_socks pussy rape raped raped_by_monster red_cheeks red_eyes red_nipples red_pussy sharp_teeth shaved_pussy stockings straight_hair striped_legwear striped_socks striped_stockings striped_thighhighs sweat sweatdrop sweating tagme teary_eyes teeth tentacle tentacle_in_anus tentacle_in_ass tentacle_in_pussy tentacle_rape tentacle_sex tentacles thighhigh_socks thighhighs vaggie_(hazbin_hotel) vaginal vaginal_penetration vivienne_medrano white_body white_hair white_skin wide_eyes yellow_eyes
381
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1girls anal anal_gape anal_insertion anus blue_sky cowboy_shot cum_in_pussy day elf female female_only femsub gaping gaping_anus green_hair holy_relic legs_together long_pointy_ears looking_at_viewer looking_back multiple_insertions mushoku_tensei object_insertion outdoors painful_insertion panty_pull pussy sirfy solo standing sylphiette_(mushoku_tensei) tree vaginal_insertion
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1girls anal anal_gape anal_insertion anus blue_sky cowboy_shot cum_in_pussy day elf female female_only femsub gaping gaping_anus green_hair holy_relic legs_together long_pointy_ears looking_at_viewer looking_back multiple_insertions mushoku_tensei object_insertion outdoors painful_insertion panty_pull pussy sirfy solo standing sylphiette_(mushoku_tensei) tree vaginal_insertion
401
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10_rings 1boy 3girls amiya_(arknights) animal_ears animal_girl animal_tail arknights barbed_wire bleeding bleeding_eyes bleeding_from_mouth bleeding_from_pussy blood blood_drip blood_everywhere blood_from_mouth blood_on_body blood_on_breasts blood_on_chest blood_on_face blood_on_fingers blood_on_hand blood_on_leg blood_on_legs blood_on_thighs blood_stain bloody_clothes blue_clothes blue_clothing blue_eyes bound breasts breasts_out brown_hair brunette cardigan_(arknights) cat_ears cat_girl cat_tail catgirl choker collar crying crying_blood crying_with_eyes_open dead death destroyed_pussy dog_ears dog_girl dog_tail dress dripping_blood ear_grab execution female female_penetrated femsub forced_penetration functionally_nude gore guangmi guerrilla_shieldguard_(arknights) guro hi_res high_resolution highres imminent_death imminent_torture impaled impalement impossible_fit infection_monitor_(arknights) jacket knee_pads knee_socks kneepads kneesocks light_brown_hair long_hair male maledom medium_breasts melantha_(arknights) neck_collar nipples one_piece_dress one_shoe one_shoe_on open_clothes open_jacket open_mouth open_vest pain painful painful_insertion painful_penetration painful_vaginal partially_clothed partially_clothed_female partially_nude partially_nude_female pink_eyes purple_eyes purple_hair pussy pussy_destruction rabbit_ears rabbit_girl ring ring_on_finger rings sadism shoes shoes_removed shoulder_grab skirt small_breasts snuff socks stockings stomach_bulge struggling torn_clothes torn_clothing torn_dress torn_skirt torture tortured tortured_to_death vaginal_penetration vest
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10_rings 1boy 3girls amiya_(arknights) animal_ears animal_girl animal_tail arknights barbed_wire bleeding bleeding_eyes bleeding_from_mouth bleeding_from_pussy blood blood_drip blood_everywhere blood_from_mouth blood_on_body blood_on_breasts blood_on_chest blood_on_face blood_on_fingers blood_on_hand blood_on_leg blood_on_legs blood_on_thighs blood_stain bloody_clothes blue_clothes blue_clothing blue_eyes bound breasts breasts_out brown_hair brunette cardigan_(arknights) cat_ears cat_girl cat_tail catgirl choker collar crying crying_blood crying_with_eyes_open dead death destroyed_pussy dog_ears dog_girl dog_tail dress dripping_blood ear_grab execution female female_penetrated femsub forced_penetration functionally_nude gore guangmi guerrilla_shieldguard_(arknights) guro hi_res high_resolution highres imminent_death imminent_torture impaled impalement impossible_fit infection_monitor_(arknights) jacket knee_pads knee_socks kneepads kneesocks light_brown_hair long_hair male maledom medium_breasts melantha_(arknights) neck_collar nipples one_piece_dress one_shoe one_shoe_on open_clothes open_jacket open_mouth open_vest pain painful painful_insertion painful_penetration painful_vaginal partially_clothed partially_clothed_female partially_nude partially_nude_female pink_eyes purple_eyes purple_hair pussy pussy_destruction rabbit_ears rabbit_girl ring ring_on_finger rings sadism shoes shoes_removed shoulder_grab skirt small_breasts snuff socks stockings stomach_bulge struggling torn_clothes torn_clothing torn_dress torn_skirt torture tortured tortured_to_death vaginal_penetration vest
11
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! 2017 2boys ? alolan_raticate anal anal_penetration anal_sex ass bakudanarare belly big_dom_small_sub big_penis bigger_dom bigger_male bigger_penetrating_smaller black_fur blue_eyes brown_fur bruised buckteeth coin comic cum_while_crying cum_while_forced cum_while_penetrated cumming_from_anal_sex cumming_while_penetrated deep_anal deep_anal_insertion deep_anal_penetration deep_penetration defeat_rape defeat_sex defeated drooling duo erect_while_penetrated erection feet feline forced forced_anal forced_yaoi furry gay gay_domination gay_rape hands-free handsfree_ejaculation injury interspecies japanese_text large_penetration leg_grab looking_down male male_only male_rape_victim male_rapist mammal meowth monster_rape nintendo no_humans non-con nonconsensual nude on_back one_eye_closed open_mouth pain painful painful_anal painful_insertion painful_penetration paws penetration penis penis_in_ass penis_size_difference persian_cat pokémon_(species) pokemon pokemon_(species) pokemon_rgby pokemon_sm rape rat raticate red_eyes rodent rough_sex saliva sex size_difference smaller_male smaller_penetrated smaller_sub stomach_bulge tail tears teeth text translation_request unwilling veins veiny_penis video_games violence violent_rape whiskers white_fur wince yaoi
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! 2017 2boys ? alolan_raticate anal anal_penetration anal_sex ass bakudanarare belly big_dom_small_sub big_penis bigger_dom bigger_male bigger_penetrating_smaller black_fur blue_eyes brown_fur bruised buckteeth coin comic cum_while_crying cum_while_forced cum_while_penetrated cumming_from_anal_sex cumming_while_penetrated deep_anal deep_anal_insertion deep_anal_penetration deep_penetration defeat_rape defeat_sex defeated drooling duo erect_while_penetrated erection feet feline forced forced_anal forced_yaoi furry gay gay_domination gay_rape hands-free handsfree_ejaculation injury interspecies japanese_text large_penetration leg_grab looking_down male male_only male_rape_victim male_rapist mammal meowth monster_rape nintendo no_humans non-con nonconsensual nude on_back one_eye_closed open_mouth pain painful painful_anal painful_insertion painful_penetration paws penetration penis penis_in_ass penis_size_difference persian_cat pokémon_(species) pokemon pokemon_(species) pokemon_rgby pokemon_sm rape rat raticate red_eyes rodent rough_sex saliva sex size_difference smaller_male smaller_penetrated smaller_sub stomach_bulge tail tears teeth text translation_request unwilling veins veiny_penis video_games violence violent_rape whiskers white_fur wince yaoi
234
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anal anal_insertion anal_only anal_penetration ass assembly_line blush bondage bound breasts brown_hair censored claws collar commentary_request conveyor_belt crying cuffs cum cumming feet female female_ejaculation female_orgasm forced_nudity forced_orgasm forced_presentation helpless insertion knees_together large_breasts light_skin long_hair machine mechanical mechanical_fixation nipples nude open_mouth orgasm orgasm_factory pain painful painful_anal painful_insertion painful_penetration penetration predicament_bondage pussy rape restrained screaming sex_machine shaved_pussy solo solo_focus spread_ass squirting stationary_restraints sweat tear tears top_down_bottom_up touchable trapped
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anal anal_insertion anal_only anal_penetration ass assembly_line blush bondage bound breasts brown_hair censored claws collar commentary_request conveyor_belt crying cuffs cum cumming feet female female_ejaculation female_orgasm forced_nudity forced_orgasm forced_presentation helpless insertion knees_together large_breasts light_skin long_hair machine mechanical mechanical_fixation nipples nude open_mouth orgasm orgasm_factory pain painful painful_anal painful_insertion painful_penetration penetration predicament_bondage pussy rape restrained screaming sex_machine shaved_pussy solo solo_focus spread_ass squirting stationary_restraints sweat tear tears top_down_bottom_up touchable trapped