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painful penetration

ai_generated anal anal_insertion anal_pain anal_penetration anal_sex armor artist_name ass bed black_hair cock deep_anal deep_anal_penetration dialog dialogue dick doggy doggy_style english_dialogue hands_on_bed hurt kai'sa league_of_legends league_of_legends:_wild_rift legends_of_runeterra looking_side male nude open_mouth painful painful_anal painful_penetration penis penis_in_ass pussy sex soulmantm video_games white_body white_skin

ai_generatedanal

ai ai_art ai_assisted ai_generated bent_over cum cum_in_pussy cum_inside doggy_style doggy_style painful painful_anal painful_penetration scooby-doo shocked_expression velma_dinkley

1boy 1girls absurdly_large_cock ai_generated anthro anthro_penetrating anthro_penetrating_human belly_bulge belly_expansion big_balls big_penis bigger_male bovine bovine_humanoid cow_girl cowgirl_position crown crying deep_penetration drolling drooling enormous_penis esd esdai extreme_size_difference female garter_belt garter_straps giant_penis grabing green_skin holding_legs huge_balls huge_cock impossible_fit kitty_pride legs_up lingerie male male/female nintendo one_punch_man open_legs open_mouth orgasm painful painful_penetration perky_nipples petite petite_body petite_breasts petite_female princess rape saliva screaming sheet_grab sheets straight tatsumaki vaginal_penetration white_body white_legwear young young_woman

absurdly_large_cockai_generated

1boy 1girls 2020s 2023 20s 2d 2d_animation 2koma after_fellatio after_oral after_rape after_sex after_vaginal animated animated_image anus areolae ass balls_deep before_and_after belly_bulge big_ass big_breasts big_butt big_cock big_penis blonde_female blonde_hair blonde_hair_female blush bouncing_breasts breasts broken_rape_victim captured censored censored_genitalia censored_penis censored_pussy clenched_teeth close-up clothed clothed_female clothed_sex clothing cock cock_hungry crying crying_with_eyes_open cum_drip cum_dripping cum_explosion cum_in_mouth cum_in_pussy cum_in_uterus cum_inside cum_leaking cum_overflow cum_trail cumming cumming_while_penetrating cumshot deep_blowjob deep_penetration deepthroat dripping dripping_cum ejaculation erect_penis erection excessive_cum eyebrows eyelashes eyes_rolling_back face_fucking female female_penetrated forced forced_oral from_behind from_behind_position from_side front_view genitals gif grin hard_on huge_breasts huge_cock imminent_fellatio imminent_oral imminent_penetration imminent_rape imminent_sex insertion instant_loss instant_loss_2koma large_insertion large_penis leaking_cum legs_apart legs_spread legwear light-skinned_female light_skin long_hair looking_at_viewer looking_up male male/female male_penetrating male_penetrating_female monster monster_cock monster_rape mosaic_censoring nipples no_panties no_sound open_mouth oral oral_insertion oral_penetration oral_sex pain painful_insertion painful_penetration pale-skinned_female pale_skin penetration penis penis_in_mouth penis_out pounding pussy_juice pussy_juice_trail rakuen_shinshoku_island_of_the_dead rape restrained restrained_by_tentacles rolling_eyes rough_sex saliva saliva_drip saliva_trail semen sex showten side_view skirt skirt_up spitroast split_screen spread_legs stand_and_carry_position standing standing_sex stomach_bulge sweat sweatdrop sweating sweaty_body tears tentacle tentacle_in_mouth tentacle_in_pussy tentacle_monster tentacle_penetration tentacle_rape tentacle_sex testicles thighhighs thighs thrusting tongue tongue_out vaginal_insertion vaginal_penetration vaginal_sex voluptuous voluptuous_female wet wet_pussy white_legwear white_thighhighs x-ray

after_fellatioafter_oral

1boy 1girls absurdly_large_cock ai_generated anthro anthro_penetrating anthro_penetrating_human belly_bulge belly_expansion big_balls big_penis bigger_male bovine bovine_humanoid cow_girl cowgirl_position crown crying deep_penetration drolling drooling enormous_penis esd esdai extreme_size_difference female garter_belt garter_straps giant_penis grabing green_skin holding_legs huge_balls huge_cock impossible_fit kitty_pryde legs_up lingerie male male/female marvel nintendo open_legs open_mouth orgasm painful painful_penetration perky_nipples petite petite_body petite_breasts petite_female princess rape saliva screaming shadowcat sheet_grab sheets straight vaginal_penetration white_body white_legwear x-men x-men_evolution young young_woman

absurdly_large_cockai_generated

1boy 1boy1girl 1girl1boy 1girls animated begging_to_slow_down begging_to_stop blue_eyes blue_hair carrying_position clothed_rape clothed_sex cowgirl_position cum_in_pussy cum_inside cumming cumming_in_pussy cumming_while_penetrating deep_penetration defeated defeated_heroine defeated_with_sex doggy_style doggystyle dripping_cum ejaculating ejaculating_cum ejaculating_in_vagina ejaculating_while_penetrating ejaculation_while_penetrating endured_face enjoying enjoying_rape fast_thrusts fatal_fury fatal_fury:_city_of_the_wolves female female_ejaculation female_penetrated forced forced_ejaculation forced_exposure forced_in_by_cock forced_orgasm forced_pleasure forced_rape forced_sex forced_submission forced_vaginal fully_clothed fully_clothed_female garou:_mark_of_the_wolves girl_raped heart heart_symbol hotaru_futaba human_penetrated impregnation interspecies k.o. king_of_fighters kof large_insertion larger_male leaking_cum legs_held_open lotus lotus_position m.u.g.e.n male male/female male_penetrating male_penetrating_female mating_press minotaur minotaur_(mugen) missionary missionary_position moaning moaning_in_pleasure monster monster_on_female monster_on_human monster_rape mp4 multiple_poses muscular muscular_male no_escape open_mouth orgasm orgasm_face overwhelming_orgasm overwhelming_pleasure painful_penetration pale-skinned_female pale_skin panties panties_aside panties_down penis penis_in_pussy pleasure_face pussy pussy_ejaculation pussy_juice pussy_juice_drip pussy_juice_leaking pussy_juice_puddle pussy_juice_splatter rape raped_by_monster raped_female raped_girl resisting_orgasm resisting_pleasure riding_penis rough_sex scared scared_expression screaming sitting_on_penis size_difference skinny_girl skinny_legs slow_penetration smaller_female snk sound spread_legs sprite striped striped_panties sudden_insertion tagme twintails vaginal_penetration vaginal_sex video voice_acted x-ray

animatedbegging_to_slow_down

1man ai_generated anal anal_insertion anal_pain anal_sex anus artist_name asian asian_female ass ass_grab bed big_ass blush cock dialog dialogue dick doggy doggy_style english_dialogue english_text female grabbing_ass hurt juno_(overwatch) nude on_bed orange_jacket overwatch overwatch_2 pain pain_anal painful painful_anal painful_penetration penis_in_ass purple_hair pussy sex soulmantm space space_background talking teo_minh white_body white_skin

ai_generatedanal

1boy 1girls absurdly_large_cock ai_generated anthro anthro_penetrating anthro_penetrating_human belly_bulge belly_expansion big_balls big_penis bigger_male bovine bovine_humanoid cow_girl cowgirl_position crown crying deep_penetration drolling drooling enormous_penis esd esdai extreme_size_difference female garter_belt garter_straps giant_penis grabing green_skin holding_legs huge_balls huge_cock impossible_fit legs_up lingerie male male/female nintendo open_legs open_mouth orgasm painful painful_penetration partial_male perky_nipples petite petite_body petite_breasts petite_female princess princess_zelda saliva screaming sheet_grab sheets straight the_legend_of_zelda vaginal_penetration white_body white_legwear young young_woman zelda_(breath_of_the_wild)

absurdly_large_cockai_generated

age_differenceall_fours

anal anal_rape anal_sex animal_genitalia anthro anus balls belly big_balls big_dom_small_sub big_penis bound brown_body brown_fur dominant duo equid equine erection feet forced fur genitals hanging_from_rope hi_res horse huge_cock licking licking_lips low-angle_view male male/male mammal membrane_(anatomy) mustelid nude open_mouth otter overweight painal painful_penetration pandottermon penetration penis pink_anus pink_penis rape rape_face ridiculous_fit rope sheath size_difference teeth toes tongue tongue_out vein veiny_penis webbed_feet white_body white_fur

ai_generated anal anal_sex artist_request ass beaten broly broly_(dragon_ball_super) bruised clothing crossover defeated defeated_with_sex dragon_ball dragon_ball_super female forced large_penis larger_male male nico_robin one_piece open_mouth painful painful_penetration rape raped rough_sex size_difference struggling thick_penis torn_clothes torn_clothing veiny_penis

ai_generatedanal

1boy 1boy1girl 1girls ai_generated akemi_homura anal anal_sex ass_grab beaten black_hair broly broly_(dragon_ball_super) bruised crossover defeated defeated_heroine destroyed_anus dragon_ball dragon_ball_super female forced grabbing_ass huge_ass huge_cock in_pain large_penis mahou_shoujo_madoka_magica male male/female open_mouth painful painful_penetration rape rough_sex size_difference struggling thick_penis torn_clothes torn_clothing veiny_penis woman

ai_generatedakemi_homura

ai_generated anal anal_sex ass beaten broly broly_(dragon_ball_super) bruised clapping_cheeks defeated defeated_heroine destruction dragon_ball dragon_ball_heroes dragon_ball_super forced fucked_from_behind huge_cock large_penis note_(dragon_ball) open_mouth painful painful_penetration petite pinned_down rough_sex size_difference struggling thick_penis torn_clothes torn_clothing veiny_penis

ai_generatedanal

1futa ai_assisted anal anal_insertion anal_sex angry anthro anus_juice bedroom big_anus big_balls big_penis blush boner boobjob cameo claws closed_eyes comic_page covered_in_cum cum cum_in_face cum_in_mouth cum_in_own_mouth dialogue digital_media_(artwork) eating_cum excessive_cum feet first_anal fluids furry futa_only futa_sans_pussy futanari grabbing_own_leg infinite_cum kiara kiara_(the_lion_king) lion_ears lion_girl lion_tail lioness massive_penis medium_ass medium_breasts mentioned_character moaning moaning_in_pleasure nala nala_(the_lion_king) orgasm painful painful_penetration penis_between_breasts pink_anus pink_nipples punishment puvlodoran rani_(the_lion_guard) stuck stuck_in_object text text_bubble the_lion_guard the_lion_king the_lion_king_ii:_simba's_pride vibrator vibrator_in_ass

ai_assistedanal

all_fours anal anal_sex anthro ass bed completely_nude disney doggy_style female female_anthro goof_troop nipple_piercing nipples nude pain painal pained_expression painful_penetration peg_pete penis peter_pete_sr. pussy red_hair sudden_insertion surprised thehumancopier variant_set

1girl 1girls artist_request ass ayano_aishi bad_idea big_breasts black_hair blade breasts crazy crazy_girl grey_eyes grey_hair knife knife_in_pussy nude nude_female ouch painful painful_penetration ponytail psychotic pussy riding sharp_object_insertion teen teenager thats_gotta_hurt vagina vaginal_insertion vaginal_penetration white_hair yandere yandere-chan yandere_simulator young

artist_requestass

ai_art ai_assisted ai_generated big_breasts bondage bound bound_wrists breasts chains cum cum_in_pussy cum_inside cumshot dominated_female dungeon final_fantasy gigantic_breasts male painful painful_penetration penis screaming shackles tied_up tifa_lockhart tits_bigger_than_head tits_out

ai_artai_assisted

1boy 1girls absurdly_large_cock ai_generated anal anal_insertion anal_orgasm anal_sex anthro anthro_penetrating anthro_penetrating_human ass_up belly_bulge belly_expansion big_balls big_penis bigger_male bovine bovine_humanoid cow_girl cowgirl_position crown crying deep_penetration drolling drooling enormous_penis esd esdai extreme_size_difference female garter_belt garter_straps giant_penis grabing green_skin huge_balls huge_cock impossible_fit lingerie male male/female nintendo open_mouth orgasm painful painful_penetration partial_male perky_nipples petite petite_body petite_breasts petite_female princess princess_zelda saliva screaming sheet_grab sheets straight the_legend_of_zelda white_body white_legwear x-ray young young_female young_woman zelda_(breath_of_the_wild)

absurdly_large_cockai_generated

ai_generated anal anal_sex ass beaten broly broly_(dragon_ball_super) bruised cinderella_(disney) crossover defeated disney dragon_ball dragon_ball_super forced huge_cock large_penis open_mouth painful painful_penetration partial_male princess rape rough_sex size_difference struggling thick_penis tight_fit torn_clothes torn_clothing veiny_penis

ai_generatedanal

2d ai_generated alice_(disney) alice_in_wonderland alice_nude anthro big_insertion bigger_male blonde_hair bumhole_destruction esd esdai esdaiart esdart extreme_size_difference eyes_rolling_back female female_orgasm giant_penis gigantic_insertion human_female hyper_penetration impossible_fit landscape large_insertion long_hair looking_up male minotaur monster nude_female orgasm painful painful_penetration public ridiculous_fit sand side_view sitting sitting_on_lap sitting_on_penis smaller_female spread_anus spread_ass stretched_anus suffering tan_body tan_skin thick thick_ass thick_legs thick_penis uncensored vaginal_insertion vaginal_penetration vaginal_sex

ai_generatedalice_(disney)

ai_generated anal anal_sex beaten broly bruised crossover defeated dragon_ball dragon_ball_super forced hatsune_miku huge_cock large_penis open_mouth painful painful_penetration pinned_down pinned_to_floor rape rough_sex size_difference thick_penis tight_fit torn_clothes torn_clothing vocaloid

ai_generatedanal

abuse anal bite bite_mark blood bruise duc_de_puce duc_volpe gay gay_rape hairy hairy_back hairy_male male_on_male male_rape male_rape_victim medieval nonconsensual painful_anal painful_penetration rape rote_haare scars stronghold_(game)

ai_generated anal anal_sex broly broly_(dragon_ball_super) chronoa destruction dragon_ball dragon_ball_super dragon_ball_xenoverse hair_grab hair_pull hair_pulling huge_cock large_penis larger_male larger_male_smaller_female legendary_super_saiyan muscular muscular_male painful painful_penetration petite pink_skin pulling_hair shortstack size_difference super_saiyan tight_fit

ai_generatedanal

ai_generated anal anal_sex broly crossover defeated dragon_ball dragon_ball_super forced in_pain large_penis open_mouth painful painful_penetration pinned pinned_down rape raped rough_sex size_difference struggling suzumiya_haruhi suzumiya_haruhi_no_yuuutsu thick_penis tight_fit torn_clothes torn_clothing upside-down veiny_penis

ai_generatedanal

ai_generated beaten broly bruised clapping_cheeks crossover defeated destruction doggy_style doki_doki_literature_club dragon_ball fucked_from_behind huge_cock large_penis larger_male larger_male_smaller_female monika_(doki_doki_literature_club) muscular_male pain painful painful_penetration rape raped rough_sex school_uniform schoolgirl size_difference tears thick_penis thighhighs vaginal_penetration

ai_generatedbeaten

ai_generated anal anal_sex backshots blue_hair broly broly_(dragon_ball_super) clapping_cheeks crossover dragon_ball dragon_ball_super femboy forced gay gay_anal gay_domination gay_male gay_sex large_penis open_mouth painful painful_penetration rimuru_tempest rough_sex size_difference tensei_shitara_slime_datta_ken thick_penis torn_clothes torn_clothing yaoi

ai_generatedanal

2boys 2male 2males anal anal_sex blush blushing_profusely dubcon dubious_consent gay gay_sex gray_glans grey_glans hands_on_hips incredibox looking_at_partner male/male male_focus male_only painful_anal painful_penetration penis_size_difference pink_nipples pink_tongue polo_(incredibox) poorly_drawn so_far_so_good sweat sweating sweaty thrusting thrusting_into_ass thrusting_up traced traced_art tremble_lines what_the_fuck_is_this white_body white_skin

anal anal_sex anthro arm_grab arm_hair armpit_hair balls bathroom beard being_watched belly belly_hair body_hair bottomwear canid canine canis chest_hair chokehold clothed clothing clothing_around_legs dialogue domestic_dog dominant duo_focus facial_hair foreskin from_behind_position genitals glory_hole group hairy hairy_balls heart_symbol hi_res homophobic_slur javier_(tracho) larger_male looking_at_another male male/male mammal masturbation murid murine nipples open_bottomwear open_clothing open_pants open_shirt open_topwear overweight pain painful_penetration pants partially_clothed penetration penis pubes public_restroom rat rodent samuel_(tracho) sex shirt size_difference slightly_chubby slim speech_bubble suid suine sus_(pig) text toilet topless topwear tracho trio underwear underwear_around_legs voyeur wild_boar

ai_generated ass ass ass_focus broly broly_(dragon_ball_super) bulma_briefs dragon_ball dragon_ball_super forced in_pain outdoors painful painful_penetration rape raped screaming size_difference torn_clothes torn_clothing vaginal_penetration

ai_generatedass

ai_generated anal anal_sex beaten broly broly_(dragon_ball_super) bruised bulma defeated dragon_ball dragon_ball_super face_down_ass_up forced fucked_from_behind fucked_into_submission huge_balls huge_cock large_penis larger_male larger_male_smaller_female pain painful painful_penetration pinned_down rough_sex size_difference tears thick_penis thick_thighs torn_clothes torn_clothing

ai_generatedanal

ai_generated beaten broken_weapon broly broly_(dragon_ball_super) bruise bruised defeated defeated_heroine doggy_style dragon_ball dragon_ball_super forced grabbing_ass hair_grab hair_pull hair_pulling huge_ass huge_cock in_pain open_mouth painful painful_penetration ponytail ponytail_hold pov rape raped screaming size_difference torn_clothes torn_clothing vados vaginal_penetration

ai_generatedbeaten

after_battle ai_generated breasts breasts_out breasts_out_of_clothes broly broly_(dragon_ball_super) clapping_cheeks crying crying_with_eyes_open defeated defeated_heroine destruction doggy_style dragon_ball dragon_ball_super eyes_wide_open forced from_behind fucked_from_behind goddess hair_grab hair_pull hair_pulling huge_cock large_penis larger_male larger_male_smaller_female madoka_kaname mahou_shoujo_madoka_magica muscular_male painful painful_penetration pulling_hair size_difference tears thick_penis torn_clothes torn_clothing ultimate_madoka

after_battleai_generated

ai_generated anal anal_sex anal_sex beaten broly broly_(dragon_ball_super) bruised crossover defeated defeated_heroine dragon_ball dragon_ball_super forced hatsune_miku huge_cock large_penis larger_male larger_male_smaller_female open_mouth pain painful painful_penetration pinned pinned_down rough_sex size_difference struggling tears thick_penis torn_clothes torn_clothing veiny_penis vocaloid

ai_generatedanal

1920x1080 1boy 1girls after_hours after_school all_the_way_to_the_base alternate_version_at_source anal anal_fuck anal_only anal_pounding anal_rape anal_sex angry angry_expression angry_face animated anus apollosixty9 apollyon9 asian asian_female asian_male ass ass_exposed ass_fuck ass_rape ayano_aishi backshots bare_ass bareback bathroom bathroom_sex bathroom_stall bent_over big_penis blindfold blindfolded breast_exposed breasts breasts_out chest_exposed clothed clothed_female clothed_male confusion covered_eyes crazy crazy_girl defeat defeat_rape defeated defeated_female depth_of_field female forced_anal forcing from_behind from_behind_position front_view fucked fucked_from_behind fucked_in_the_ass hate hate_fuck hate_sex hi_res high_resolution highres in_pain japanese_female japanese_male long_penis longer_than_2_minutes longer_than_one_minute loop looping_animation male/female male_penetrating male_penetrating_female male_pov nice_ass night pain painal painful painful_anal painful_penetration painful_sex penis_in_ass pov questionable_consent rape raped school school_uniform schoolgirl senpai senpai_(yandere_simulator) shirtless skirt skirt_lift sound stall stretched_anus stretching stuck stuck_in_door stuck_in_object tagme taking_it_all taro_yamada tight_anus tight_fit tits_out uncensored video widescreen wrong_hole yandere yandere-chan yandere_simulator

after_hoursafter_school

2025 3_fingers 4_fingers anal anal_sex anon anthro anthro_penetrated ass ass_up bare_shoulders bent_legs big_breasts big_butt big_eyes big_penis biped black_and_white black_text blush bodily_fluids breast_rest breasts butt_grab cheek_tuft clothed clothed/nude clothed_sex clothing crossed_arms cutaway dbaru dialogue digital_drawing_(artwork) digital_media_(artwork) domestic_cat dress duo emanata english_text extended_arms eyebrows eyelashes faceless_character faceless_human faceless_male facial_tuft felid feline felis female female_on_human female_penetrated fingers flash_emanata from_behind_position frown fur fur_tuft genitals grabbing_from_behind half-closed_eyes hand_on_another's_butt hand_on_arm hand_on_butt hand_on_own_arm head_turned heavy_blush hi_res human human_on_anthro human_penetrating human_penetrating_anthro human_penetrating_female humanoid_genitalia humanoid_hands humanoid_penis interspecies long_eyelashes looking_at_viewer looking_pleasured lying male male/female male_on_anthro male_penetrating male_penetrating_anthro male_penetrating_female mammal monochrome motion_lines narrowed_eyes navel nipples no_bra no_underwear nude nude_human nude_male on_front open_frown open_mouth painful_penetration partially_clothed partially_clothed_anthro partially_clothed_female penetration penile penile_penetration penis penis_in_ass pointy_ears prick_ears raised_clothing raised_dress raised_tail rear_admiral_position sex shima_luan speech_bubble super_planet_dolan sweat sweaty_face tail talking_to_viewer text thick_eyebrows thick_penis thick_thighs three-quarter_view tuft

ai_generated anal anal_sex broly broly_(dragon_ball_super) cheelai clapping_cheeks defeated doggy_style dragon_ball dragon_ball_super forced huge_cock hyper_penis in_pain large_penis larger_male larger_male_smaller_female pain painful painful_anal painful_penetration pinned pinned_down pinned_to_floor rough_sex size_difference tears thick_penis tight_fit torn_clothes torn_clothing

ai_generatedanal

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