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1femoby 2boys ai_generated anal anal_sex anus aroused aroused_face ass ass_focus asshole balls blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus femboy_only feminine_male gay gay_male gay_sex genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only open_mouth orange_clothing penis ponytail prison prison_cell prison_clothes prison_uniform prisoner redcherryart testicles

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1boy 1femoby ai ai-created ai_art ai_assisted ai_generated anus ass ass_focus asshole balls blonde_hair blonde_male blush cock dick femboy femboy_focus femboy_only feminine_male gay gay_male genitals inmate inmates_clothing jail long_hair_male looking_at_viewer looking_back male male_focus male_only orange_clothing penis prison prison_clothes prison_uniform prisoner redcherryart shoes spread_ass spreading_anus spreading_ass stretched_anus testicles thin thin_male

1boy 1femoby ai_generated ass ass_focus balls bars blonde_hair blonde_male blush femboy femboy_focus femboy_only feminine_male gay gay_male inmate inmates_clothing jail long_hair_male male male_focus male_only orange_clothing prison prison_clothes prison_uniform prisoner redcherryart testicles

1boy 1femboy ai_generated ass asshole balls blonde_hair blush cellmates femboy femboy_focus feminine_male freckles inmate inmates_clothing jail long_hair male male_focus male_only no_panties otoko_no_ko prison prison_clothes prisoner redcherryart sissy spread_ass t-shirt testicles trap

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1boy 1futa 1futa2girls 2girls 2girls1futa after_paizuri ahe_gao ahegao ai:_the_somnium_files ai:_the_somnium_files_-_nirvana_initiative aiba_(ai:_the_somnium_files) ass balls barcode_tattoo big_balls big_breasts big_penis blue_penis blush blushing_at_viewer blushing_female bondage boss_[shizue_kuranushi] breast_grab breastfeeding breastfeeding_during_sex breasts brown_hair bukkake chain_leash chained chains chocolate_and_vanilla collaborative_paizuri color comic comic_strip cum cum_eating cum_in_mouth cum_in_pussy cum_in_uterus cum_in_vagina cum_in_womb cum_inside cum_kiss cum_leaking cum_leaking_out_of_pussy cum_on_breasts cum_on_face cum_on_hair cum_on_tongue cum_pool cum_shot cum_string cum_swallow cum_swap cum_trail cumming cumshot curvaceous curvy curvy_female curvy_figure dark-skinned_bottom dark-skinned_female dark_skin disembodied_penis domination double_paizuri drained egg_cell ejaculation embarrassed embarrassed_female erect_penis erection facial feet female femdom fertilization ffm_threesome french_kiss french_kissing full_color futa_on_female futanari giant_breasts giant_penis gigantic_breasts grabbing_breasts gui handcuffed handcuffed_to_bed handcuffs heart-shaped_pupils hi_res high_resolution highres horny horny_female hud huge_breasts huge_cock imminent_rape impregnation intersex jail kissing kuruto_ryuki lactating lactation large_breasts large_penis leash leg_tattoo lesbian_kiss lezdom light-skinned_bottom light-skinned_female light-skinned_male light-skinned_top light_skin long_hair long_penis looking_at_penis male massive_breasts muscular muscular_female nipple_piercing nipples nude_female nude_male on_bed on_knees paizuri partially_clothed partially_clothed_female penetration penis pierced_nipples piercing police police_hat police_uniform police_woman policewoman prison prison_guard prison_uniform prisoner pupils pussy rape red_eyes red_eyes_female semen sex shamashiel sharing_cum shirt_up sperm_cell spread_legs spread_pussy squeezing_breast squishing_breasts stomach_bulge straight_sex tagme tagme_(character) tama_(ai:_the_somnium_files) tattoo tattoos thick_ass thick_penis thick_thighs thighs_together threesome tied tied_hands tied_up titjob toned_female vaginal vaginal_penetration vaginal_sex veiny_penis white_hair white_hair_female wide_hips x-ray yellow_eyes yellow_eyes_female yuri

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1femboy 2boys ai_generated anal anal_insertion anal_sex blonde_hair blonde_male blue_eyes blush cell cellmates cock dick femboy femboy_focus feminine feminine_body feminine_male feminine_pose freckles gay gay_male gay_sex inmate jail jail_cell laying_down laying_on_back long_hair long_hair_male male orange_clothing penis penis_in_ass pov prison prison_cell prisoner redcherryart sex sissy

ai_generated anal anal_insertion anal_sex blonde_hair blonde_male blue_eyes blush cell cellmates femboy femboy_focus feminine feminine_body feminine_male feminine_pose freckles gay gay_male gay_sex inmate jail jail_cell long_hair long_hair_male male orange_clothing prison prison_cell prisoner redcherryart sex sissy

2boys ai_generated ass balls bars big_butt blonde_hair blue_eyes blush buttcheeks cell cellmates cock femboy femboy_focus feminine_male freckles freckles_on_face gay gay_male homosexual inmate jail key male male_focus male_on_femboy male_only orange_clothing orange_shirt penis penis_in_ass prison prison_cell prison_clothes prison_uniform prisoner redcherryart sissy testicles

ai_generated ass balls blonde_hair dick femboy from_below inmate jail male no_panties orange_clothes orange_clothing otoko_no_ko penis prison prison_uniform prisoner redcherryart sissy spread_ass t-shirt testicles trap

193

2boys aass ai_generated aiser0 anal anal_sex ass balls black_hair blush dark-skinned_male dark_skin femboy feminine_male gay gay_sex grey_eyes inmate inmates_clothing interracial jail male male_only nude one-punch_man otoko_no_ko penis prison prison_stripes prison_uniform prisoner sex short_hair sissy speed-o'-sound_sonic stripes sweat testicles trap uncensored yaoi

158

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1boy 1girls after_sex after_vaginal animated areolae ass big_breasts blue_eyes blush breasts chained_wrists cum cum_in_pussy cum_inside disembodied_penis faceless_male female game_cg jail large_breasts looking_back male nipples open_mouth penis pink_hair project_qt pussy sex sideboob slap_mark striped_thighhighs sweaty_ass sweaty_butt thighhighs tongue tongue_out twintails uncensored vaginal_penetration vaginal_sex vivian_(project_qt) watermark

1boy 1girls animated areolae ass big_breasts blue_eyes blush breasts chained_wrists disembodied_hand disembodied_penis faceless_male female game_cg jail large_breasts looking_back male nipples open_mouth penis pink_hair project_qt pussy sex sideboob slap_mark slapping_ass slapping_butt striped_thighhighs sweaty_ass sweaty_butt thighhighs tongue tongue_out twintails uncensored vaginal_penetration vaginal_sex vivian_(project_qt) watermark

angry angry_expression angry_eyes angry_face boots breasts breasts_out cage cameltoe cameltoe_pants female female glasses grey_hair hentadraw imprisoned jacket jacket_open jail kinktober kinktober_2025 large_breasts naked_breasts nipples open_clothes panty prison_school ribbon_choker school_uniform shiraki_meiko sketch skirt thigh_highs thighhighs tits_out

205

1boy 1girls 3d after_fellatio batman_(series) cum cum_on_face dc dc_comics english_text 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 part_of_a_set penis prison prison_cell prisoner quick_e speech_bubble suicide_squad suicide_squad:_kill_the_justice_league text villain

150

1boy 1girls 3d batman_(series) dc dc_comics english_text 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_of_a_set penis prison prison_cell prisoner quick_e speech_bubble suicide_squad suicide_squad:_kill_the_justice_league text villain

192

1080p 10_seconds 10s ai_generated animated audio blindfold bondage cock_ring dead_or_alive dead_or_alive_5 dominant dominatrix dungeon female female_domination femdom gagged gloved_handjob handjob interrogation_room jail legs_up licking_ear lifting_leg male marie_rose penis phantom_draft pixel_animation pixel_art prison rope_bondage sound submissive_male tagme torture_chamber video

1girls 3d 4boys age_difference arms_behind_back being_watched blue_eyes bondage breast_grab breasts breasts_out dark-skinned_male dark_skin female finger_in_mouth freckles ginger ginger_female ginger_hair handcuffs hi_res human human_only imminent_gangbang imminent_sex jail jail_cell light-skinned_female light-skinned_male light_skin male multiple_boys multiple_males nipples no_bra old_male older_male open_clothes open_mouth open_shirt orange_hair original_character panties petite petite_body petite_female police police_officer police_uniform prison prison_cell prisoner questionable_consent red_hair redhead rori_collins_(troxvi) self_upload sheriff sheriff_coleman_(troxvi) skirt small_breasts teenage_female teenager troxvi upskirt watching younger_female

106

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

ai_generated anal anal_sex bara big_ass big_butt big_muscles black_hair bottomless chain_leash chain_necklace chained chained_collar chained_cuffs chained_wrists chains completely_naked completely_naked_male completely_nude completely_nude_male dat_ass dat_butt defeated_hero defeated_male gay gay_sex glistening_ass glistening_body glistening_butt glistening_skin handsome hunk imprisoned jail jail_cell juicy_ass knight large_ass large_butt large_muscles long_hair looking_at_viewer male male_only male_penetrating_male masculine_male muscles muscular muscular_arms muscular_ass muscular_back muscular_legs muscular_male naked naked_male nude nude_male original_character ponytail prison prisoner provocative round_ass round_butt seductive_body seductive_look seductive_pose shiny_ass shiny_butt shiny_skin showing_ass showing_off_ass smooth_ass sweat sweaty sweaty_ass sweaty_body thick_ass thick_butt thrusting_into_ass tight_ass veiny_muscles warrior yaoi zodoai

ai_generated bara big_ass big_butt big_muscles black_hair bottomless chain_leash chain_necklace chained chained_collar chained_cuffs chained_wrists chains completely_naked completely_naked_male completely_nude completely_nude_male covered_in_cum cumming dat_ass dat_butt defeated_hero defeated_male gay glistening_ass glistening_body glistening_butt glistening_skin handsome hunk imprisoned jail jail_cell juicy_ass knight large_ass large_butt large_muscles long_hair looking_at_viewer male male_only masculine_male muscles muscular muscular_arms muscular_ass muscular_back muscular_legs muscular_male naked naked_male nude nude_male original_character ponytail prison prisoner provocative round_ass round_butt seductive_body seductive_look seductive_pose shiny_ass shiny_butt shiny_skin showing_ass showing_off_ass smooth_ass sweat sweaty sweaty_ass sweaty_body thick_ass thick_butt tight_ass veiny_muscles warrior yaoi zodoai

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