prison_rape best from all time

Time frame

Tags

prison rape

2024 against_surface against_wall ahe_gao anthro armor belgian_tervuren bodily_fluids bound canid canine chain_leash chains claws clenched_teeth clothed clothed/nude clothing corruption cuff_(restraint) cum cum_in_mouth cum_inside dungeon duo duo_focus english_text eyeshadow female fennec_fox forced fox genital_fluids glowing glowing_eyes green_eyes group handcuffed handcuffs hi_res hyena imminent_pain inside ky_(malamute) leash leona_the_depraved_(-ky-) lingerie looking_pleasured makeup male male/female mammal metal_cuffs nude oblivious open_mouth penetration pink_sclera prison prison_rape pushing_object rape restraints sex simple_background size_difference struggling teeth text thought_bubble tongue tongue_out true_fox unconvincing_armor
2024 against_surface against_wall ahe_gao anthro armor belgian_tervuren bodily_fluids bound canid canine chain_leash chains claws clenched_teeth clothed clothed/nude clothing corruption cuff_(restraint) cum cum_in_mouth cum_inside dungeon duo duo_focus english_text eyeshadow female fennec_fox forced fox genital_fluids glowing glowing_eyes green_eyes group handcuffed handcuffs hi_res hyena imminent_pain inside ky_(malamute) leash leona_the_depraved_(-ky-) lingerie looking_pleasured makeup male male/female mammal metal_cuffs nude oblivious open_mouth penetration pink_sclera prison prison_rape pushing_object rape restraints sex simple_background size_difference struggling teeth text thought_bubble tongue tongue_out true_fox unconvincing_armor
absurd_res anthro anus ass balls big_breasts bodily_fluids breasts canid canine cellmates cum digital_media_(artwork) female forced fur genital_fluids genitals gimpis grouo_rape group group_sex hair hi_res male male/female mammal muscular nipples nude penis prison prison_cell prison_rape prisoner pussy rape sex threesome trio vaginal_penetration
absurd_res anthro anus ass balls big_breasts bodily_fluids breasts canid canine cellmates cum digital_media_(artwork) female forced fur genital_fluids genitals gimpis grouo_rape group group_sex hair hi_res male male/female mammal muscular nipples nude penis prison prison_cell prison_rape prisoner pussy rape sex threesome trio vaginal_penetration
6ix9ine ahe_gao anal anal_sex arm_grab balls_deep big_penis celebrity comic dialogue femboy gay gay_sex imminent_rape imminent_sex instant_loss_2koma murgosworld prison_rape pulling_arm rape rough_sex silhouette sketch sweat tattoo tattoos x-ray
6ix9ine ahe_gao anal anal_sex arm_grab balls_deep big_penis celebrity comic dialogue femboy gay gay_sex imminent_rape imminent_sex instant_loss_2koma murgosworld prison_rape pulling_arm rape rough_sex silhouette sketch sweat tattoo tattoos x-ray
1boy 1girls avatar_legends avatar_the_last_airbender black_and_white clothing earth_kingdom english_text erect_nipples erect_nipples_under_clothes female fire_nation male male/female medium_breasts nonbender oral_sex prison_rape pubic_hair rape samson_00 sex speech_bubble straight_hair suki text
1boy 1girls avatar_legends avatar_the_last_airbender black_and_white clothing earth_kingdom english_text erect_nipples erect_nipples_under_clothes female fire_nation male male/female medium_breasts nonbender oral_sex prison_rape pubic_hair rape samson_00 sex speech_bubble straight_hair suki text
2_penises 4:3 absurd_res all_three_filled anal anal_sex animal_genitalia animal_penis armor arms_tied blue_penis bodily_fluids bondage bound bound_together closed_eyes cum cum_drip cum_in_ass cum_in_mouth cum_in_pussy cum_in_uterus cum_inside cum_on_self cum_splatter cumshot cutaway deep_throat diphallia diphallism dragon dreyk-daro dripping eastern_dragon ejaculation female feral feral_on_feral forced fur furred_dragon furred_scalie genital_fluids genital_markings genitals green_body green_fur green_penis group hemipenes hi_res horn internal internal_anal internal_oral internal_vaginal kerchief knot knot_in_mouth knotted_penis legs_tied male male/female male/male markings multi_genitalia multi_penis multiple_penetration mythological_creature mythological_scalie mythology neckerchief neckwear oral oral_penetration penetration penis penis_markings prison prison_rape prisoner pyrope_(genericdef) rape red_body red_penis red_scales restraints rope rope_bondage rope_harness scales scalie scar sex skywing_(wof) sycamore_(wanishi) uterus vaginal_penetration wings_of_fire wings_tied
2_penises 4:3 absurd_res all_three_filled anal anal_sex animal_genitalia animal_penis armor arms_tied blue_penis bodily_fluids bondage bound bound_together closed_eyes cum cum_drip cum_in_ass cum_in_mouth cum_in_pussy cum_in_uterus cum_inside cum_on_self cum_splatter cumshot cutaway deep_throat diphallia diphallism dragon dreyk-daro dripping eastern_dragon ejaculation female feral feral_on_feral forced fur furred_dragon furred_scalie genital_fluids genital_markings genitals green_body green_fur green_penis group hemipenes hi_res horn internal internal_anal internal_oral internal_vaginal kerchief knot knot_in_mouth knotted_penis legs_tied male male/female male/male markings multi_genitalia multi_penis multiple_penetration mythological_creature mythological_scalie mythology neckerchief neckwear oral oral_penetration penetration penis penis_markings prison prison_rape prisoner pyrope_(genericdef) rape red_body red_penis red_scales restraints rope rope_bondage rope_harness scales scalie scar sex skywing_(wof) sycamore_(wanishi) uterus vaginal_penetration wings_of_fire wings_tied
anthro asphyxiation blizzard_entertainment bodily_fluids bucket canid canine collar container cum cum_drip doggy_style dominant dragon dripping duo fan_character forced from_behind_position genital_fluids hi_res hybrid leash male male/male mammal penis_on_butt prison prison_bars prison_cell prison_rape prisoner questionable_consent rape sex seyrmo warcraft were werecanid werecanine werewolf worgen
anthro asphyxiation blizzard_entertainment bodily_fluids bucket canid canine collar container cum cum_drip doggy_style dominant dragon dripping duo fan_character forced from_behind_position genital_fluids hi_res hybrid leash male male/male mammal penis_on_butt prison prison_bars prison_cell prison_rape prisoner questionable_consent rape sex seyrmo warcraft were werecanid werecanine werewolf worgen
2_penises 4:3 absurd_res all_three_filled anal anal_sex animal_genitalia animal_penis armor arms_tied blue_penis bodily_fluids bondage bound bound_together diphallia diphallism dragon dreyk-daro eastern_dragon female feral feral_on_feral forced fur furred_dragon furred_scalie genital_fluids genital_markings genitals green_body green_fur green_penis hemipenes hi_res horn internal internal_anal internal_oral internal_vaginal kerchief knot knot_in_mouth knotted_penis legs_tied male male/female male/male markings multi_genitalia multi_penis multiple_penetration mythological_creature mythological_scalie mythology neckerchief neckwear oral oral_penetration penetration penis penis_markings precum prison prison_rape prisoner pyrope_(genericdef) rape red_body red_penis red_scales restraints rope rope_bondage rope_harness scales scalie scar sex skywing_(wof) sycamore_(wanishi) vaginal_penetration wings_of_fire wings_tied
2_penises 4:3 absurd_res all_three_filled anal anal_sex animal_genitalia animal_penis armor arms_tied blue_penis bodily_fluids bondage bound bound_together diphallia diphallism dragon dreyk-daro eastern_dragon female feral feral_on_feral forced fur furred_dragon furred_scalie genital_fluids genital_markings genitals green_body green_fur green_penis hemipenes hi_res horn internal internal_anal internal_oral internal_vaginal kerchief knot knot_in_mouth knotted_penis legs_tied male male/female male/male markings multi_genitalia multi_penis multiple_penetration mythological_creature mythological_scalie mythology neckerchief neckwear oral oral_penetration penetration penis penis_markings precum prison prison_rape prisoner pyrope_(genericdef) rape red_body red_penis red_scales restraints rope rope_bondage rope_harness scales scalie scar sex skywing_(wof) sycamore_(wanishi) vaginal_penetration wings_of_fire wings_tied
anal anal_sex anthro arc_rose arms_tied bodily_fluids bondage bondage bound digital_drawing_(artwork) digital_media_(artwork) domestic_cat double_penetration dungeon eye_scar facial_scar felid feline felis female female_penetrated forced furniture genital_fluids genitals guards hybrid inside knot legs_tied male male/female mammal nude pantherine penetration prison prison_bars prison_rape pussy pussy_juice rape rape_face restraints rope rope_bondage scar sex spread_eagle spread_legs spreading table table_sex tears tears_of_desperation tears_of_pain tiger vaginal_penetration vaginal_penetration
anal anal_sex anthro arc_rose arms_tied bodily_fluids bondage bondage bound digital_drawing_(artwork) digital_media_(artwork) domestic_cat double_penetration dungeon eye_scar facial_scar felid feline felis female female_penetrated forced furniture genital_fluids genitals guards hybrid inside knot legs_tied male male/female mammal nude pantherine penetration prison prison_bars prison_rape pussy pussy_juice rape rape_face restraints rope rope_bondage scar sex spread_eagle spread_legs spreading table table_sex tears tears_of_desperation tears_of_pain tiger vaginal_penetration vaginal_penetration
abs anal ape balls_deep big_muscles big_pecs bite biting_another bodily_fluids brown_hair domination/submission feet foot_fetish foot_on_face foot_play forced forced_anal fur genitals gorilla grey_body grey_fur hair haplorhine hi_res huge_muscles hyper hyper_genitalia hyper_muscles khrunkisillegal male male/male mammal murid murine muscular nipples obese overly_muscular overweight pecs penetration penis pink_body primate prison prison_rape rape rat rodent roque_(khrunkisillegal) rough_sex sex shoulder_bite sweat vein veiny_muscles veiny_penis
abs anal ape balls_deep big_muscles big_pecs bite biting_another bodily_fluids brown_hair domination/submission feet foot_fetish foot_on_face foot_play forced forced_anal fur genitals gorilla grey_body grey_fur hair haplorhine hi_res huge_muscles hyper hyper_genitalia hyper_muscles khrunkisillegal male male/male mammal murid murine muscular nipples obese overly_muscular overweight pecs penetration penis pink_body primate prison prison_rape rape rat rodent roque_(khrunkisillegal) rough_sex sex shoulder_bite sweat vein veiny_muscles veiny_penis
2_penises 4:3 absurd_res all_three_filled anal anal_sex animal_genitalia animal_penis armor arms_tied blue_penis bodily_fluids bondage bound bound_together cum cum_drip cum_in_ass cum_in_mouth cum_in_pussy cum_in_uterus cum_inside cum_on_self cum_on_tongue cum_splatter cumshot cutaway diphallia diphallism disembodied_penis dragon dreyk-daro dripping eastern_dragon ejaculation female feral feral_on_feral forced fur furred_dragon furred_scalie genital_fluids genital_markings genitals green_body green_fur green_penis group hemipenes hi_res horn internal internal_anal internal_oral internal_vaginal kerchief knot knot_in_mouth knotted_penis legs_tied male male/female male/male markings multi_genitalia multi_penis multiple_penetration mythological_creature mythological_scalie mythology neckerchief neckwear oral oral_penetration penetration penis penis_markings penis_on_tongue prison prison_rape prisoner pyrope_(genericdef) rape red_body red_penis red_scales restraints rope rope_bondage rope_harness scales scalie scar sex skywing_(wof) sycamore_(wanishi) tongue uterus vaginal_penetration wings_of_fire wings_tied
2_penises 4:3 absurd_res all_three_filled anal anal_sex animal_genitalia animal_penis armor arms_tied blue_penis bodily_fluids bondage bound bound_together cum cum_drip cum_in_ass cum_in_mouth cum_in_pussy cum_in_uterus cum_inside cum_on_self cum_on_tongue cum_splatter cumshot cutaway diphallia diphallism disembodied_penis dragon dreyk-daro dripping eastern_dragon ejaculation female feral feral_on_feral forced fur furred_dragon furred_scalie genital_fluids genital_markings genitals green_body green_fur green_penis group hemipenes hi_res horn internal internal_anal internal_oral internal_vaginal kerchief knot knot_in_mouth knotted_penis legs_tied male male/female male/male markings multi_genitalia multi_penis multiple_penetration mythological_creature mythological_scalie mythology neckerchief neckwear oral oral_penetration penetration penis penis_markings penis_on_tongue prison prison_rape prisoner pyrope_(genericdef) rape red_body red_penis red_scales restraints rope rope_bondage rope_harness scales scalie scar sex skywing_(wof) sycamore_(wanishi) tongue uterus vaginal_penetration wings_of_fire wings_tied
anthro blue_body blue_feathers bodily_fluids cum cum_on_ground don't_drop_the_soap duo feathers feet forced genital_fluids hi_res human kalsim_(the_nature_of_predators) krakotl_(the_nature_of_predators) lobotomiskii male mammal nude prison prison_rape rape soap_bar talons the_nature_of_predators toes
anthro blue_body blue_feathers bodily_fluids cum cum_on_ground don't_drop_the_soap duo feathers feet forced genital_fluids hi_res human kalsim_(the_nature_of_predators) krakotl_(the_nature_of_predators) lobotomiskii male mammal nude prison prison_rape rape soap_bar talons the_nature_of_predators toes
3boys anthro armor balls bars big_dom_small_sub bodily_fluids bound breath clothed clothing cum cum_in_ass cum_inside cum_on_face cum_on_penis cum_on_tongue disney domination dragon dungeon erection forced foreskin gay genital_fluids genitals green_body green_scales grey_body grey_skin group group_sex guards headgear helmet horn humanoid_genitalia jususama_(artist) male male/male male_only mammal masturbation medieval_armour open_mouth overweight penile penile_masturbation penis prison prison_rape rape rhino_guard rhinocerotoid robin_hood_(disney) rope scales scalie sex signature size_difference stripes threesome tongue tongue_out wingless_dragon wooden_horse_(device) yaoi
3boys anthro armor balls bars big_dom_small_sub bodily_fluids bound breath clothed clothing cum cum_in_ass cum_inside cum_on_face cum_on_penis cum_on_tongue disney domination dragon dungeon erection forced foreskin gay genital_fluids genitals green_body green_scales grey_body grey_skin group group_sex guards headgear helmet horn humanoid_genitalia jususama_(artist) male male/male male_only mammal masturbation medieval_armour open_mouth overweight penile penile_masturbation penis prison prison_rape rape rhino_guard rhinocerotoid robin_hood_(disney) rope scales scalie sex signature size_difference stripes threesome tongue tongue_out wingless_dragon wooden_horse_(device) yaoi
alligator alligatorid anal anal_sex anthro anus balls bandanna_on_arm bandits bear boots bound clothing cowboy_boots cowboy_hat criminal criminal_scum crocodilian degradation doggy_style domination/submission duo eyewear footwear forced from_behind_position genitals giant_panda glasses hand_on_head hand_on_shoulder hands_tied hat headgear headwear hi_res humiliation leg_spreader lying male male/male mammal markwulfgar mask on_front one_eye_closed penetration prison prison_bars prison_cell prison_rape rape reptile restraints scalie sex shoes slightly_chubby smile snaggle_teeth spread_legs spreader_bar spreading spurs trigger_(wordcaster)
alligator alligatorid anal anal_sex anthro anus balls bandanna_on_arm bandits bear boots bound clothing cowboy_boots cowboy_hat criminal criminal_scum crocodilian degradation doggy_style domination/submission duo eyewear footwear forced from_behind_position genitals giant_panda glasses hand_on_head hand_on_shoulder hands_tied hat headgear headwear hi_res humiliation leg_spreader lying male male/male mammal markwulfgar mask on_front one_eye_closed penetration prison prison_bars prison_cell prison_rape rape reptile restraints scalie sex shoes slightly_chubby smile snaggle_teeth spread_legs spreader_bar spreading spurs trigger_(wordcaster)