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126

1femboy 2boys anal_fingering ass ass_focus badlybeatenaguacate balls bare_ass barefoos bent_over big_ass big_butt black_stripes blonde_hair blush bunk_bed cavity_search cell dyed_hair edit edited femboy feminine_male fingering gay gay_male genitals guard inmate inmates_clothing jail jail_cell kneeling ladder male male_only medium_hair moaning no_shoes pants_down penis pink_hair prison prison_cell prison_clothes prison_guard prison_guard_uniform prison_uniform prisoner recolor strip_search striped_clothing stripes submissive submissive_male tears tears_of_pleasure testicles toilet white_stripes yaoi

318

ai_generated ai_generated_video animated audio blindfold bondage bondage_harness chainsaw_man chastity_cage clothed_female_nude_male cock_ring denji_(chainsaw_man) dildo dominant dungeon female female_domination femdom gagged handcuffed handcuffs jail leash leash_pull makima_(chainsaw_man) male pegging penis phantom_draft prison prostate_stimulation reverse_rape sound submissive_male tagme torture_chamber video

100

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ai_generated big_breasts breasts celica_(fire_emblem) female fire_emblem fire_emblem_echoes:_shadows_of_valentia jail mugshot red_eyes red_hair

242

1boy 1girls 3d batman_(series) blowjob dc dc_comics fellatio female glory_hole guard harley_quinn harley_quinn_(arkham) harley_quinn_(suicide_squad_game) jail light-skinned_female light-skinned_male light_skin male oral oral_penetration oral_sex part_4 part_of_a_set penis prison prison_cell prisoner quick_e suicide_squad suicide_squad:_kill_the_justice_league villain

182

1boy 1girls 3d batman_(series) dc dc_comics female glory_hole guard harley_quinn harley_quinn_(arkham) harley_quinn_(suicide_squad_game) jail licking_penis light-skinned_female light-skinned_male light_skin male oral oral_sex part_3 part_of_a_set penis prison prison_cell prisoner quick_e suicide_squad suicide_squad:_kill_the_justice_league villain

150

1boy 1boy1girl 1girls ai_generated anal anus big_ass big_breasts bondage breasts cum cum_drip cumming domina dominant dominant_female dominated domination dominatrix doskoinpo_art_style female female_dominating_male female_on femdom femdomfantasyai fingering forced forced_orgasm gear jail male male_sub pegging prostate_massage prostate_milking prostate_orgasm top_femboy

2boys 2d 2d_(artwork) blushing_profusely cmnm douglas_reed gay gay_sex jail jail_cell light-skinned_male light_skin male male_only male_penetrated male_penetrating male_penetrating_male wererdraws

#mrgalahad 3boys blood blood_drip blood_in_mouth blood_on_face blowjob blowjob_face blowjob_gesture blowjob_while_penetrated brown_hair crying crying_with_eyes_open cum cum_drip cum_in_ass cum_in_mouth cum_in_pussy cum_inside cum_on_body cum_on_face dick dominant dominant_male domination female forced forced_anal forced_exposure forced_oral forced_orgasm forced_sex forced_yaoi grey_hair guard jail kneeling knife male male/male male_focus male_only male_penetrated male_penetrating male_penetrating_male male_pov naked naked_male officer oral oral_penetration oral_sex orange_hair penetration penis penis_out pillow pink_eyes pokemon police police_officer police_uniform policeman prison prison_cell prison_clothes prison_uniform prisoner pussy raped raped_into_submission restrained restrained_arms restrained_legs restrained_male shadow submissive submissive_human submissive_male tears tied tied_arms tied_hands trio trio_focus trio_male trio_oc yaoi yaoi_orgy young younger_male younger_penetrated

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ai_generated bara bara_tits breasts gay glass jail male male_only muscular muscular_male pecs phone pressed_against pressed_against_glass pressed_on_glass snake_jailbird the_simpsons yaoi

ai_generated bara bara_tits breasts cumming gay holding_bars jail jail_cell male male_only muscular muscular_male shirt_lift shirt_up snake_jailbird snake_jailbird, solo solo_male tattoo the_simpsons underwear underwear_down yaoi

289

ai_generated anal_fingering anal_insertion animated audio balls bondage clothed_female_nude_male cum dominant dungeon ejaculation female female_domination femdom fingering genshin_impact gloved_handjob handjob interrogation_room jail large_penis large_testicles male milking_handjob penis phantom_draft prison prostate_massage prostate_milking prostate_stimulation restrained rope_bondage sadistic sound sound_effects submissive_male tagme testicles torture_chamber video yelan_(genshin_impact)

114

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105

1femboy 2boys ai_generated bedroom black_hair blonde_hair blonde_male boy_rape boyrape brown_skin cat_ears catboy cellmates clothed_sex collar completely_nude cum cumming curvy curvy_body curvy_figure dark-skinned_male dark_skin dominant_male ejaculation enjoying enjoying_rape enjoying_sex enjoyment fat_bastard fat_male femboy feminine feminine_body feminine_male flat_chest forced forced_orgasm gay grabbing grabbing_penis gripping_cock groping handjob handjob_from_behind hands-free hug hugging hugging_from_behind inmate jail light-skinned_male light_skin makeup male male_focus male_only medium_hair molestation molesting mtf_transformation muscular nonconsensual orange_clothing orange_pants penis penis_grab prison prison_bitch prison_cell prison_clothes prison_uniform prisoner sleeves submissive submissive_male tagme thick_thighs transformation uncomfortable underwear uniform

3d 3girls anus ass black_hair breasts bubble_butt cd_projekt_red ciri completely_nude female freckles green_eyes high_heel_boots jail jintsuriki light-skinned_female looking_at_viewer mascara necklace nipples nude panties purple_eyes pussy red_hair scar stockings the_witcher_(series) the_witcher_3:_wild_hunt tongue_out triss_merigold white_hair witcher_medallion yennefer

157

1boy 1girls 3d batman_(series) dc dc_comics female glory_hole guard harley_quinn harley_quinn_(arkham) harley_quinn_(suicide_squad_game) jail light-skinned_female light-skinned_male light_skin male part_2 part_of_a_set penis prison prison_cell prison_guard_position prisoner quick_e suicide_squad suicide_squad:_kill_the_justice_league

1boy 1girls 3d animated artist_request big_ass big_breasts big_penis black_cat_(marvel) bodysuit breasts cunnilingus demon demon_horns doggy_style felicia_hardy female fingering horns jail longer_than_10_minutes longer_than_2_minutes longer_than_5_minutes longer_than_one_minute male marvel marvel_comics moaning nude penis police_uniform sex sex_from_behind sound spider-man_(series) standing standing_doggy_style standing_sex tagme video white_hair

1boy 1girls ai_generated anal anal_sex anal_sex anal_slut asking_for_it blue_eyes brown_hair confident dark-skinned_male eager faceless_male female full_nelson full_nelson_(legs_held) full_nelson_anal gloves gold_jewelry grabbing_ass grabbing_own_ass gyakuten_saiban interracial jail jail_cell jewelry male naked nude nude_female nude_male scarf smug top_hat trucy_wright wanting_sex

466

2d ai_generated aifurryposter69 animal_crossing animal_pussy animated anthro ball_gag blindfold bondage bound breasts canid canine canine_pussy canis chains cum cum_in_pussy cumming domestic_dog dominant_male dungeon ejaculation feet_up female forced furry gag isabelle_(animal_crossing) jail legs_up lying_on_back male missionary_position moaning on_back on_table petite pussy rape size_difference small_breasts spread_legs submissive_female tagme tears video

1futa ai_generated ass bed bedroom big_breasts black_hair black_legwear breasts curvy dialogue dick english english_text erect_penis erection fishnets floating_heart futa_only futa_sans_pussy futadom futanari goth goth_futa gothic horny horny_futa intersex jail jail_cell kinkyra light-skinned_futa light_skin lingerie looking_at_viewer partially_clothed penis skinny_futa solo_futa standing taker_pov veins_on_dick veiny_penis

149

10_seconds 10s ai_generated animated audio bondage defeated defeated_hero dildo dildo_in_ass dominant dominatrix dungeon facesitting fatal_fury female female_domination femdom footjob footjob_with_legwear handcuffed handcuffs humiliation jail joe_higashi mai_shiranui male phantom_draft prison rope_bondage sitting_on_dildo sound sound_effects submissive_male tagme torture torture_chamber torture_device trample trampling video

1futa 3d 3d_model abs animal_genitalia_on_humanoid animal_penis athletic athletic_futa blonde_hair blue_eyes boots breasts equine_penis fendravr fingers fit fit_futa functionally_nude futa_focus futa_only futanari goth goth_futa gothic horns horsecock horsecock_futa horsecock_on_humanoid huge_breasts huge_cock humanoid indoor indoor_nudity indoors inside intersex jail jail_bars jail_cell knees large_breasts large_penis legs light light-skinned_futa light_skin looking_at_viewer mature_futa messy messy_hair minotaur minotaur_futa mostly_nude naked naked_futa no_panties no_pants no_underwear nude pale_skin penis solo solo_futa standing tall_futa thick_thighs thigh_boots thighs undressed virtual_reality virtual_youtuber vrchat vrchat_avatar vrchat_media vrchat_model vrchat_penis white_sclera

1futa ai_generated ass bed bedroom big_breasts black_hair black_legwear breasts curvy dick erect_penis erection fishnets floating_heart futa_only futa_sans_pussy futadom futanari goth goth_futa gothic green_eyes horny horny_futa intersex jail jail_cell kinkyra light-skinned_futa light_skin lingerie looking_at_viewer partially_clothed penis skinny_futa solo_futa standing taker_pov veins_on_dick veiny_penis

2girls1boy ai_generated dominant dungeon female female_domination femdom final_fantasy final_fantasy_vii final_fantasy_vii_remake from_side gloved_handjob handjob jail male phantom_draft prison rimjob rimming rimming_male submissive_male tifa_lockhart tongue tongue_out x-ray xray yuffie_kisaragi

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1futa ai_generated balls batman_(series) big_ass big_balls big_breasts big_penis breasts dc dc_comics dripping_cum futa_only futanari harley_quinn heavy_balls huge_balls huge_cock intersex jail justice_league long_penis looking_at_viewer no_panties no_pants penis poney solo standing sydlorem thick_penis

after_rimming ai_generated cammy_white dominant dominatrix drool_string drooling dungeon female female_domination femdom gloved_handjob handjob jail lipstick_mark male phantom_draft prison rimming street_fighter street_fighter_6 street_fighter_v submissive_male

146

3boys ai_generated anal anal_sex bars bent_over bentover07 blowjob breasts cellmates cock-tail crying femboy freckles_on_ass gangbang glistening_body handjob inmate jail male male_only male_penetrated male_penetrating penetration penis police prison prison_clothes prison_guard prison_uniform prisoner raped red_hair self_upload sissy small_breasts small_penis spitroast threesome yaoi

1femboy 3boys ai_generated balls bentover07 blowjob cellmates cock crying cum_in_ass cum_in_mouth cum_on_body cumshot dick femboy feminine_male gangbang gangrape genitals handjob handprint inmate jail leaking_cum male male_focus male_only oral oral_sex orange_clothing penis penis_in_hand penis_in_mouth prison prison_clothes prison_uniform prisoner raped red_hair self_upload sucking testicles thick_thighs uniform yaoi

1boy 1femboy anal anal_insertion anal_masturbation anal_penetration balls black_shoes blue_hair braid braided_hair brown_eyes chains cuffs dick dildo dildo_in_ass erection femboy femboy_focus femboy_only feminine_male glasses handcuffs hands_on_ground inmate jail large_penis legcuffs long_dick long_hair long_hair_male long_penis male male_focus male_only male_penetrated masturbation open_mouth open_mouth_smile orange_clothing orange_eyes orange_stripes penis prison prison_clothes prisoner restrained restraints riding riding_dildo shackles shoes smile solo solo_male striped_clothes striped_clothing stripes testicles weirdo_dork white_male white_skin

1boy 1femboy anal anal_insertion balls black_and_white_stripes black_shoes black_stripes blue_hair braid braided_hair brown_eyes chains cuffs dick dildo dildo_in_ass erection femboy femboy_focus femboy_only feminine_male glasses handcuffs hands_on_ground inmate jail large_penis legcuffs long_dick long_hair long_hair_male long_penis male male_focus male_only male_penetrated open_mouth open_mouth_smile orange_eyes penis prison prison_clothes prisoner restrained restraints riding riding_dildo shackles shoes smile solo solo_male striped_clothes striped_clothing stripes testicles weirdo_dork white_male white_skin white_stripes

after_rimming ai_generated dead_or_alive dead_or_alive_5 dominant dominatrix drool_string drooling dungeon female female_domination femdom gloved_handjob handjob jail lipstick_mark male marie_rose phantom_draft prison rimming submissive_male

240

10s ai_generated anal_beads anal_beads_in_ass animated audio blindfold bondage chain_leash chained_up chained_wrists chainsaw_man cum denji_(chainsaw_man) dominant dominant_female dominatrix dungeon female female_domination femdom gagged gloved_handjob handjob interrogation interrogation_room jail jerking_off jerking_off_another jerkingoff makima_(chainsaw_man) male nipple_play nipple_stimulation nipple_suck nipple_tweak phantom_draft prison sound spread_legs submissive_male sucking_nipples tagme torture torture_chamber torture_device tweaking_nipple video

451

2d ai_generated animated anthro blowjob bodily_fluids breasts couple cum cum_in_mouth cum_in_pussy cum_on_body cum_on_face deepthroat drinking_cum dungeon ejaculation featureless_breasts fellatio female flat_chest flat_chested french_kiss genital_fluids handjob human human_on_anthro interspecies jail kissing kobold long_tongue male male/female no_nipples nude on_bottom on_top oral passionate penis pixelpawai prison_cell pussy reverse_cowgirl_position romantic romantic_couple scales scalie sex sound tagme tail throat_swabbing tongue_around_penis tongue_kiss video

250

1boy 1girls arm_support arms_up bars big_breasts boruto:_naruto_next_generations breasts carrying carrying_partner cheating cheating_female cheating_wife dark-skinned_male dark_skin detached_collar female footwear footwear_only heels high_heels interracial jail looking_pleasured male milf naked_footwear naked_with_shoes_on naruto penis platform_heels pleasure_face prisoner pussy raikage raikage_art sakura_haruno sex spread_legs stand_and_carry_position straight tagme uncensored vaginal_penetration

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