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arcane arcane_vi ball_gag big_breasts bondage bondage_gear bondage_outfit breasts gag gagged inmate league_of_legends prison prisoner punished riot_games straitjacket uberis vi visor

arcanearcane_vi

1girls bars blanket blue_hair blush bunk_bed buttons cell en17 female female_only fingering fingering_self inmate jail jail_cell laugh magenta_eyes masturbation medium_hair orange_clothing prison prison_bars prison_cell prison_clothes prison_uniform prisoner shadow toilet unbuttoned uniform

1girls anklehighs black_hair breasts cell en17 execution exposed_breasts female female_only inmate jail jail_cell jumpsuit medium_hair peeing ponytail prison prison_cell prison_jumpsuit prisoner red_eyes sad shadow sink socks tabi toilet toilet_use uniform white_socks yellow_clothing

anklehighsblack_hair

1girls 3d arrest arrested batesz batman_(series) big_breasts blonde_hair blue_eyes blue_hair breasts breasts_out cleavage crazy_eyes crazy_smile dc dc_comics female female_only fully_clothed glass harley_quinn harley_quinn_(injustice) hips huge_breasts injustice_2 inmate large_breasts light-skinned_female light_skin looking_at_viewer netherrealm_studios open_clothes open_mouth pink_hair prison prison_clothes prison_uniform prisoner smile solo teeth twintails wide_hips

1girls black_hair breasts buttons en17 female female_only glasses inmate jail jumpsuit medium_hair orange_clothing patreon ponytail prison prison_clothes prison_jumpsuit prison_uniform prisoner purple_eyes sad showing_breasts showing_off solo_female tattoo uniform

black_hairbreasts

2boys 5_fingers 5_toes african african_male anal anal_insertion anal_sex bara barefoot cellmates crying crying_with_eyes_open dark-skinned_male dark_skin domination feet forced gay gay_domination gay_sex greenzbamboo human human_only inmate inmates jail male male/male male_focus male_only melanin prison prison_rape prisoner questionable_consent rape self_upload yaoi

africanafrican_male

anthro anthro_only anus ball_blush balls butt_crack crew_cut cum cum_on_self cumshot fangs felid feline felis hand_behind_head humanoid_genitalia humanoid_penis inmate lenny_ringtail male male_only muscular muscular_anthro muscular_male on_bed orange_fur pecs penile_masturbation prison_cell tail tongue_out wink

anthroanthro_only

1girls 3boys bald big_ass bottom_heavy cake cell cheating choker comic doggy_style fellatio female fishnets hand_on_head happy_birthday high_heels inmate jucika jucika's_husband kyde lingerie male male/female medium_breasts netorare no_dialogue old_man older_male oral prison prison_cell prison_uniform prisoner questionable_consent rape sex shocked suprised sweat sweatdrop thick_thighs underwear wide_hips wristband younger_female

6+boys 6+girls doggy_style erenisch fucktoy fully_clothed group group_sex inmate japanese mass_rape multiple_boys multiple_girls older_male orgy prison prisoner public_use rape sailor_uniform schoolgirl_uniform sex sex_slave

doggy_styleerenisch

6+boys 6+girls bondage clothed_male_nude_female doggy_style erenisch fucktoy gag group group_sex inmate mass_rape multiple_girls older_male orgy prison prisoner rape sex sex_slave shackles tape_gag

bondageclothed_male_nude_female

anthro bondage caroo english_text feet feet_focus femsub idw_comics idw_publishing inmate lemur lock_symbol long_duration_bondage long_term_bondage mammal mobian_(species) primate prison prisoner punishment restrained sega sonic_(series) sonic_the_hedgehog_(comics) sonic_the_hedgehog_(idw) sonic_the_hedgehog_(series) tail tail_bondage tangle_the_lemur text tickle_torture tickling tickling_feet tickling_machine

1futa aronhilistix big_breasts breasts brick_wall cell_bars futa_only futanari inmate intersex jail peanut_butter_(theycallhimcake) prison prison_bars prison_cell prisoner tagme thick_thighs

aronhilistixbig_breasts

2boys 2girls 3d animated ass behind_bars big_ass big_breasts big_butt bottomless breasts butt character_request copyright_request fellatio female ffmm_foursome foursome fuck_the_police gigantic_breasts gloves hooker huge_breasts hyper_breasts inmate large_breasts longer_than_30_seconds male mp4 ozisan police police_girl police_hat police_uniform police_woman policewoman prison prison_break prisoner rape sound video

2boys 2girls 3d all_fours animated ass balls big_ass big_breasts big_butt blonde_hair boots breasts breasts_out brown_hair bulldog_position butt dark-skinned_male dark_skin doggy_style fuck_the_police gigantic_breasts gloves huge_breasts hyper_breasts inmate large_breasts light-skinned_female light_skin longer_than_30_seconds mp4 ozisan police police_girl police_hat police_uniform police_woman policewoman prison prison_break prisoner rape sex sound thick_thighs vaginal_penetration video

all_foursanimated

2boys absorption anal bike_shorts comic domination femboy gay helpless inmate interspecies lewderthanblue monster oc original prison ran(ltb) restrained simple_background size_difference slime torn_bike_shorts

1girls ass big_ass big_breasts big_butt big_penis braided_hair breasts brown_hair chains cock dialogue dick ear_piercing earring edit english_text female_focus handcuffed handcuffs huge_ass imminent_rape imminent_sex inmate large_ass large_butt looking_back male muscles muscular muscular_back muscular_female naked offscreen_male original original_character pants_down penis plump_ass prisoner red_hair scars_on_face shadman sideboob sweat tattooed_arm tattoos thick_ass topless_female

1boy 1girls alt_cor altcor arkham_asylum ass asylum batman:_arkham_city batman_(series) blonde_hair cell clayface clenched_teeth closed_eyes crying crying_with_eyes_closed dc_comics female forced inmate long_hair male milf mother panties panties_down pants_down prison prisoner red_ass rocksteady_studios spanked spanking talia_al_ghul talia_al_ghul_(arkham_city) tears

1boy 1girls alt_cor altcor anne_hathaway arkham_asylum ass asylum batman_(series) brown_hair catwoman catwoman_(the_dark_knight_rises) cell clayface clenched_teeth closed_eyes comic crying dc dc_comics dialogue female heels inmate lipstick long_hair male over_the_knee_spanking paddle panties panties_down prison red_ass spanked spanking spanking_paddle speech_bubble tears text the_dark_knight_rises

1boy 1girls alt_cor altcor arkham_asylum ass asylum batman_(series) batman_and_robin cell clayface clenched_teeth comic dc dc_comics dialogue female green_skin inmate lipstick long_hair male maledom panties poison_ivy prison red_hair spanked spanking speech_bubble text

1boy 1girls alt_cor altcor arkham_asylum ass asylum bare_ass batman_(series) blonde_hair blue_eyes cell clayface comic dc dc_comics dc_extended_universe dialogue english_text female fingerless_gloves handstand harley_quinn inmate jacket legs lipstick makeup male maledom necklace over_the_knee_spanking paddle pigtails prison red_ass shorts_down spanked spanking speech_bubble suicide_squad text thighs twintails

3d hairy_armpits hairy_legs hairy_pussy inmate prison_guard prisoner

hairy_armpitshairy_legs

2022 2boys 4k amuzoreh amuzoreh_(artist) bird blue_fur blue_hair bow bowtie chained_ankles chandgrit chastity chastity_cage cuffed gay half-closed_eyes hd hi_res high_resolution highres inmate jail_sex male male/male prison prison_guard_position prison_sex prisoner red_fur red_hair sex sonic_(series) sonic_the_hedgehog sonic_the_hedgehog_(series) yaoi

amuzorehamuzoreh_(artist)

blonde_hair bondage bound breasts breasts_out brown_eyes cell chained chains dungeon ferres inmate straitjacket thighhighs

blonde_hairbondage

asylum bondage coax coaxdreams crazy_eyes inmate insane magazine_cover narrow_pupils padded_cell padded_room padded_walls panties patient red_hair straitjacket text

2018 2girls asylum black_and_white black_hair blonde_hair bondage coax coaxdreams drugs female force_feeding gag hospital inmate nurse patient pills wheelchair

asylumblack_and_white

1girls 2d arkham_asylum asylum batman:_arkham_asylum batman_(series) belly breasts casual_nudity cell convenient_censoring dc dc_comics feet female female_only flower flower_bikini flowers flytrap green-skinned_female green_skin inmate jago_dibuja large_breasts leaf leaf_clothing leaf_on_breast leaves legs long_hair looking_at_viewer pamela_isley patient plant plants poison_ivy red_hair solo thighs venus_flytrap vines wet yellow_eyes

arkham_asylumasylum

2girls asylum bondage bondage coax coaxdreams escape female inmate outdoors outside panties patient runaway smile smiling straitjacket

asylum ball_gag black_hair bondage coax coaxdreams escape female guards gun heels hiding hospital inmate pale_skin patient runaway straitjacket tights wet

1boy 2girls baton big_ass big_balls big_breasts big_penis bimbo bimbo_lips black_body black_nails black_penis black_skin blonde_hair caroline_(persona_5) chair cock criminal cuffs cum dark-skinned_male dark_skin ear_ring eye_patch female gloves guard hair_grab hand_cuffs handcuffs high_heels hoop_earrings hoop_earrings_oversized huge_ass huge_breasts huge_cock inmate interracial jail jail_cell justine_(persona_5) long_hair male male/female mascara mascara_tears night nightstick penetration penis persona persona_5 pink_lipstick platinum_blonde_hair prison prison_clothes prison_guard pubic_hair pussy pussy_grip pussy_juice saliva saliva_trail skirt stiletto_heels teen temogam tongue_out tongue_piercing twins ugly vagina vaginal_juices vaginal_penetration vaginal_sex very_high_heels white_body white_skin yellow_eyes

1boy anthro ball belt bindings binds bondage bound cage canid canine canis cell chastity_(disambiguation) chastity_cage chastity_device discipline eldingo eldingo_(artist) frustration gag gay genitals hi_res inmate male malesub mammal muzzle_(disambiguation) paws perineum prison punishment restraints solo submissive submissive_male wolf ych_(character)

1boy absurd_res animal_ears animal_genitalia animal_nose animal_only animal_tail anthro anthro_focus anthro_only anthro_solo ball belt bindings binds bondage bound cage canid canine canis cell chastity chastity_(disambiguation) chastity_cage chastity_device discipline eldingo_(artist) frustration furry furry_ears furry_focus furry_only furry_solo furry_tail gag gay genitals hi_res inmate male mammal muzzle_(disambiguation) no_humans paws perineum prison punishment restraints solo solo_anthro solo_furry submissive wolf yaoi ych_(character)

absurd_resanimal_ears

1boy 1boy1girl 1girls against_wall barefoot black_hair deep_penetration demon demon's_souls demon_girl demon_humanoid demon_sex demoness feet female_penetrated fromsoftware guard inmate knight maiden_in_black male_penetrating male_penetrating_female medieval_armour mindless pigutao prison_cell prisoner risky_sex rough_sex security_guard seduced seductive sex slayer_of_demons succubus temptation third-party_edit tricked tricked_into_sex unprotected_sex unsafe_sex vaginal_penetration vaginal_sex

against_wallbarefoot

1boy absurd_res anthro ball belt bindings binds bondage bound canid canine canis cell chastity chastity_cage chastity_device discipline eldingo_(artist) frustration gag gay genitals hi_res inmate male malesub mammal muzzle_(object) muzzled paws perineum prison punishment restraints solo submissive_male wolf ych_(character)

absurd_resanthro

1boy absurd_res anthro belt bindings binds blush bondage bound chastity_cage chastity_device discipline eldingo_(artist) felid feline frustration gag gay harness hi_res inmate male malesub mammal pantherine pet punishment restraints solo submissive_male tiger

absurd_resanthro

1boy anthro ball_gag belt bindings binds bodily_fluids bondage bound cell chastity_cage chastity_device cum dildo discipline eldingo_(artist) gag gagged gay genital_fluids genitals harness hi_res inmate male malesub penis prison punishment restraints sex_toy solo submissive_male

1boy absurd_res anthro ball belt bindings binds bondage bound cage canid canine cell chastity_(disambiguation) chastity_cage chastity_device discipline eldingo eldingo_(artist) fox frustration gag gay genitals hi_res inmate male male/male malesub mammal muzzle_(disambiguation) pawpads prison punishment restraints solo submissive_male

absurd_resanthro

cum_machine horny horny_jail inmate jail jumpsuit laser lockedup male_only malesub mesomorph milking milking_machine penis_milking prison prison_cell prisoner

cum_machinehorny

1boy anthro ball_gag belt bindings binds bodily_fluids bondage bound cell cum cum_in_ass cum_inside cum_leaking dildo discipline eldingo_(artist) gag gay genital_fluids genitals harness hi_res inmate lying male male_only malesub muzzle_(object) muzzled on_back penis prison punishment restraints sex_toy solo submissive_male

2boys anal anal_sex armpitslayer balls completely_nude dialogue diamond_is_unbreakable english_text fingers_in_mouth genitals hand_on_hip handcuffs hip_grab inmate jojo's_bizarre_adventure josuke_higashikata male/male male_penetrated male_penetrating male_penetrating_male nude nude_male penetration penis prison prison_cell pubes pubic_hair rimmybone speech_bubble testicles tongue tongue_out unknown_male

2boys anal anal_sex balls belt clothing dialogue diamond_is_unbreakable english_text fingers_in_mouth gay genitals hand_on_hip handcuffs hip_grab inmate jojo's_bizarre_adventure josuke_higashikata male/male male_penetrated male_penetrating male_penetrating_male pants_pull penetration penis police_uniform prison prison_cell prison_uniform prisoner pubes pubic_hair rimmybone speech_bubble testicles tongue tongue_out unbuckled_belt unknown_male yaoi

bondage bound chains cuffed cuffs en17 female female_only femsub fully_clothed high_heel_boots high_heels inmate jail jumpsuit neo_(rwby) orange_stripes prison prison_clothes prison_jumpsuit prison_uniform prisoner restrained restraints rwby striped striped_clothing striped_jumpsuit uniform

2boys anal anal_sex armpits balls blush cum cum_in_ass diamond_is_unbreakable dubious_consent ejaculation ejaculation_while_penetrated faceless_male finger_in_mouth fingers_in_mouth fucked_silly gay genitals hand_on_hip handcuffs hip_grab inmate jojo's_bizarre_adventure josuke_higashikata male/male male_only male_penetrated male_penetrating male_penetrating_male muscular orgasm pants_pull penetration penis prison prison_cell prison_uniform prisoner pubes pubic_hair rimmybone testicles tongue tongue_out unknown_male

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