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ai ai_generated angry angry_expression angry_eyes angry_face beautiful before_rape before_sex big_breasts bitch brocolizz brown_eyes bun_hair cells curvy disgust disgusted disgusted_expression disgusted_face disgusted_look female glasses large_breasts lipstick long_breasts mature_female neckline open_shirt prison prison_bitch prison_cell prison_clothes prison_school prison_uniform prisoner sagging_breasts shaded_face shiraki_meiko silver_hair striped_clothes striped_shirt tall_female taller_female taller_girl tape teeth_clenched thick_thighs thin_eyebrow thin_eyebrows tied tied_arms tied_hair white_skin

1boy alien alien_boy big_ass big_balls big_penis biting black_and_white bondage bound bound_wrists captive dialogue english_text femboy huge_cock hung hung_femboy hung_trap inquisition inquisition_(warhammer_40k) inquisitor kneeling large_balls large_penis leaking leaking_cum leaking_precum looking_at_viewer male male_focus offscreen_character prisoner prisoner_of_war qt0ri red_eyes short_hair skin_tight skin_tight_outfit skin_tight_suit solo struggling sweating tau text thick_thighs tight_shirt warhammer_(franchise) warhammer_40k wip work_in_progress xenophilia

1girls angry angry_expression angry_eyes angry_face armpits arms_above_head arms_up belly big_breasts breasts crying crying_with_eyes_open female female_human fit_female green_eyes hands_above_head hands_tied hourglass_figure human large_breasts light-skinned_female lingerie lingerie_only long_hair mature_female navel oc on_back original original_character pissed_off prisoner pubic_hair red_lingerie red_ribbon restrained restraints ribbon rororo slim_waist spread_legs thick_thighs thighs thighs_spread tied_up wide_hips

angryangry_expression

anthro bear butt_slap domestic_cat duo felid feline felis generation_3_pokemon generation_6_pokemon giant_panda hi_res male male/male male_only mammal nintendo paddle pangoro pokemon pokemon_(species) police police_badge police_officer prisoner slap spanking zangoose

ai_generated anal cum_in_ass cum_in_pussy feet feet_up female foot_fetish prisoner shackles soles soles_female

ai_generatedanal

1girls big_breasts blue_eyes female genderswap green_eyes heterochromia huge_breasts long_hair mokushiroku_no_yonkishi nanatsu_no_taizai prisoner tagme tristan_liones white_hair

big_breastsblue_eyes

abs ai_generated big_breasts big_penis black_hair blue_eyes cellmates dickgirl dickgirl_only futa_focus futa_only futadom futanari huge_cock intersex looking_at_viewer muscular muscular_arms muscular_futanari nayvenn pants_down prison prison_bars prison_cell prison_clothes prisoner self_upload stable_diffusion stern_expression tattoo tattoo_on_arm tattoo_on_belly tattoo_on_chest tattooed_arm tattoos

absai_generated

ai_generated anus ass asshole attack_on_titan balls big_ass big_balls big_butt big_penis createai_art dilated_anus focus_on_ass focus_on_butt gapping gay jean_kirstein male_only penis prison prisoner shingeki_no_kyojin solo yaoi

ai_generatedanus

ai_generated blowjob blush chains cuffs cum cum_in_mouth cum_on_breasts cum_on_face irelia_xan kneeling league_of_legends looking_at_viewer male penis pov_eye_contact prison_cell prisoner rokc123 scars

ai_generatedblowjob

ai_generated blowjob blush chains cuffs irelia_xan kneeling league_of_legends looking_at_viewer pov_eye_contact prison_cell prisoner rokc123

ai_generatedblowjob

ai_generated blowjob blush chains cuffs irelia_xan kneeling league_of_legends looking_at_viewer pov_eye_contact prison_cell prisoner rokc123

ai_generatedblowjob

anal_juice anal_orgasm anal_sex anus anus_focus bumhole_destruction bumrape dungeon exposed_anus female_penetrated juicy_ass monster_cock muscular_female muscular_male prison_bitch prison_cell prisoner rape woahsasaur

anal_juiceanal_orgasm

1girls accidental_circumstance adventurer anal anal_orgasm anal_sex anus ass ass_exposed asshole bad_end baggy_pants blonde_hair blush boots boppin butthole captured captured_girl captured_heroine chibi clothing commission crotchless crotchless_clothes cum cum_drip cum_dripping cum_dripping_from_ass cum_dripping_out_of_pussy cum_in_ass cum_in_pussy cum_inside cum_on_boots cum_on_clothes cum_on_lower_body cum_on_shoes cum_puddle cum_running_down_leg cute cute_girl dangling_legs defeat defeated defeated_female defeated_hero defeated_heroine defenseless dominant_male dominated dominated_female domination dripping dripping_cum dumb dumb_girl dungeon dungeons_and_dragons duty_failed embarrassed embarrassed_female embarrassed_nude_exposure exposed_anus exposed_ass exposed_pussy failed_attempt failure female filled_ass filled_belly filled_to_the_brim fox_ears fox_girl fox_spirit fox_tail free_use from_behind front_and_back functionally_nude functionally_nude_female gushing gushing_cum heavenly_ass heavy_breathing helpless helpless_female helpless_girl humiliated humiliating humiliation imminent_anal imminent_penetration imminent_rape imminent_sex immobile immobilization immobilized in_heat japanese_clothes kitsune legs_together living_sex_toy long_hair nervous nervous_smile nervous_sweat open_mouth orgasm orgasm_from_anal panting pink_anus prisoner public_use pussy pussy_ejaculation pussy_exposed pussy_juice pussy_juice_drip rape raped raped_by_enemy raped_girl red_anus restrained round_ass round_butt sarayah scared sex_from_behind small_breasts squirting squirting_from_anal squirting_orgasm stuck stuck_in_wall submission submissive submissive_female sweat sweating sweaty sweaty_body tail_aside thick_thighs thigh_gap trapped trembling tricked tricked_into_exposure tricked_into_sex used_as_an_object used_like_a_toy vagina vaginal vulnerable vulnerable_expression weak wet_pussy wide_eyed

accidental_circumstanceadventurer

2d areolae big_breasts breasts busty comic female female_focus female_only hourglass_figure lara_and_the_golden_idol_(comic) lara_croft lara_croft_(classic) large_breasts monochrome monster nipples nude nude_female nudity prisoner rope sabudenego tagme tied_up tomb_raider wide_hips

areolaebig_breasts

1boy alien alien_boy big_ass big_balls big_penis biting bondage bound bound_wrists captive dialogue english_text femboy hung hung_femboy inquisition inquisition_(warhammer_40k) inquisitor kneeling large_balls large_penis leaking leaking_cum leaking_precum looking_at_viewer male male_focus offscreen_character prisoner prisoner_of_war qt0ri red_eyes red_hair short_hair skin_tight skin_tight_outfit skin_tight_suit solo struggling sweating tau text thick_thighs tight_shirt warhammer_(franchise) warhammer_40k xenophilia

activision bodily_fluids bound captured corrupt_cynder cum cum_in_mouth cum_inside cynder dragon dreyk-daro female feral genital_fluids genitals hi_res ignitus male male/female mythological_creature mythological_scalie mythology oral penis prisoner scalie spyro_the_dragon

activisionbodily_fluids

absurd_res ambiguous_gender belly body_writing breasts cuff_(restraint) demidoggo demon demon_humanoid dialogue disembodied_hand english_text eye_roll female female/ambiguous female_focus genitals hair handcuffed handcuffs heart_symbol hi_res horn human_is_better humanoid humanoid_focus imp intelligence_loss jewelry membrane_(anatomy) membranous_wings metal_cuffs mind_break necklace pink_body pink_skin poking_stomach prisoner pussy restraints short_stack small_wings solo_focus spade_tail speech_bubble tail text white_hair wide_hips wings

absurd_resambiguous_gender

1girls absurd_res ambiguous_gender arms_up belly breasts cuff_(restraint) cuffs demidoggo demon demon_humanoid dialogue disembodied_hand english_text female female/ambiguous female_focus genitals hair handcuffed handcuffs heart_symbol hi_res horn humanoid humanoid_focus imp jewelry legs_together membrane_(anatomy) membranous_wings metal_cuffs necklace open_mouth pink_body pink_skin poking_stomach prisoner pussy restrained restraints short_stack small_wings solo_focus spade_tail speech_bubble tail text white_hair wide_hips wings

absurd_resambiguous_gender

1girls 2d ai_generated annie_leonhardt areolae armbinder athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female female_only fit fit_female focus hair harness high_quality leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup mascara medium_breasts naked nero100 nipples nude nude_female o-ring on_the_floor pale-skinned_female pale_skin perky_breasts posing prison prisoner pussy seductive seductive_look sex_slave shingeki_no_kyojin spread_legs stable_diffusion tagme thighs thin_waist vagina

ai_generatedannie_leonhardt

1boy 1boy1girl 1girls 2d ai_generated annie_leonhardt areolae athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female fit fit_female floor_sex focus hair handcuffs harness high_quality leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup male mascara medium_breasts missionary missionary_position naked nero100 nipples nude nude_female o-ring on_the_floor pale-skinned_female pale_skin penis perky_breasts posing prison prisoner pussy rape rough_sex seductive seductive_look sex sex_slave shingeki_no_kyojin spread_legs stable_diffusion tagme thighs thin_waist tied_hands tied_up vagina vaginal_insertion vaginal_penetration vaginal_sex wild_sex

ai_generatedannie_leonhardt

1boy 1boy1girl 1girls 2d ai_generated annie_leonhardt areolae armbinder athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar cowgirl_position curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female fit fit_female focus gag gagged hair harness high_quality latex latex_legwear leaning_back leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup male mascara medium_breasts naked nero100 nipples nude nude_female o-ring pale-skinned_female pale_skin penis perky_breasts posing prison prisoner pussy rape rough_sex seductive seductive_look sex sex_slave shingeki_no_kyojin spread_legs stable_diffusion tagme thighs thin_waist vagina vaginal_insertion vaginal_penetration vaginal_sex wild_sex

ai_generatedannie_leonhardt

1boy 1boy1girl 1girls 2d ai_generated annie_leonhardt areolae athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female fit fit_female floor_sex focus hair handcuffs harness high_quality leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup male mascara medium_breasts missionary missionary_position naked nero100 nipples nude nude_female o-ring on_the_floor pale-skinned_female pale_skin penis perky_breasts posing prison prisoner pussy rape rough_sex seductive seductive_look sex sex_slave shingeki_no_kyojin spread_legs stable_diffusion tagme thighs thin_waist tied_hands tied_up vagina vaginal_insertion vaginal_penetration vaginal_sex wild_sex

ai_generatedannie_leonhardt

2d ai_generated annie_leonhardt areolae athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage chain_leash chained chains chest collar completely_naked completely_nude completely_nude_female curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female female female_only fit fit_female focus hair high_quality leash leash_and_collar leashed_collar legs legs_up light-skinned_female light_skin lips lipstick long_hair makeup mascara medium_breasts naked nero100 nipples nude nude_female pale-skinned_female pale_skin perky_breasts pillory posing prison prisoner pussy restrained seductive seductive_look sex_slave shingeki_no_kyojin slave spread_legs stable_diffusion tagme thighs thin_waist vagina

ai_generatedannie_leonhardt

1girls 2d after_rape after_sex after_vaginal ai_generated annie_leonhardt areolae athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage chest completely_naked completely_nude completely_nude_female cum cum_drip cum_in_pussy cum_inside curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female female_only fit fit_female focus hair high_quality legs light-skinned_female light_skin lips lipstick long_hair makeup mascara medium_breasts naked nero100 nipples nude nude_female pale-skinned_female pale_skin perky_breasts pillory posing prison prisoner pussy restrained seductive seductive_look sex_slave shingeki_no_kyojin slave stable_diffusion tagme thighs thin_waist vagina

after_rapeafter_sex

1boy 1boy1girl 1girls 2d ai_generated annie_leonhardt areolae athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female fit fit_female floor_sex focus hair handcuffs harness high_quality leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup male mascara medium_breasts missionary missionary_position naked nero100 nipples nude nude_female o-ring on_the_floor pale-skinned_female pale_skin penis perky_breasts posing prison prisoner pussy rape rough_sex seductive seductive_look sex sex_slave shingeki_no_kyojin spread_legs stable_diffusion tagme thighs thin_waist tied_hands tied_up vagina vaginal_insertion vaginal_penetration vaginal_sex wild_sex

ai_generatedannie_leonhardt

1boy 1boy1girl 1girls 2d ai_generated annie_leonhardt areolae armbinder athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blowjob blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar curvy curvy_figure cute cute_face detailed eyelashes eyeshadow fellatio female fit fit_female focus hair harness high_quality leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup male mascara medium_breasts naked nero100 nipples nude nude_female o-ring oral oral_penetration oral_sex pale-skinned_female pale_skin penis penis_in_mouth perky_breasts posing prison prisoner pussy seductive seductive_look sex sex_slave shingeki_no_kyojin stable_diffusion tagme thighs thin_waist

ai_generatedannie_leonhardt

2d ai_generated annie_leonhardt areolae arms_at_sides athletic athletic_female attack_on_titan big_breasts blonde_female blonde_hair blonde_hair_female blue_eyes_female bondage bondage_gear bondage_harness bondage_outfit chain_leash chained chains chest collar curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female female female_only fit fit_female focus gag gagged hair harness high_quality leash leash_and_collar leashed_collar legs light-skinned_female light_skin lips lipstick long_hair makeup mascara medium_breasts naked nero100 nipples nude nude_female o-ring pale-skinned_female pale_skin perky_breasts posing prison prisoner pussy seductive seductive_look sex_slave shackles shingeki_no_kyojin stable_diffusion standing tagme thighs thin_waist vagina

ai_generatedannie_leonhardt

absurd_res anal anal_sex anthro ass big_penis bodily_fluids canid character_request clothing cum dog_man_(character) dog_man_(series) dogman_(character) dogman_(series) duo erection felid feline genital_fluids genitals gregory_bailey gregory_knight hi_res hotdogging hotdogging_legs looking_for_someone male male/male mammal penetration penile penile_penetration penis penis_in_ass petey_the_cat police police_uniform prisoner reverse_hotdogging ryru thigh_sex uniform

ai_art ai_assisted ai_generated big_breasts big_breasts bondage bondage_gear bound bound_wrists breasts breasts chained chains excella_gionne giant_breasts huge_breasts prisoner resident_evil shackled shackles tits_bigger_than_head tits_out

ai_artai_assisted

1girls 2boys 2boys1girl ai_generated ass ass_up big_ass big_breasts big_butt big_nipples doggy_style double_penetration face_down_ass_up fat_ass female from_behind from_behind_position grabbing grabbing_from_behind green_hair holding_arm huge_ass jail jojo's_bizarre_adventure jolyne_kujo male prisoner prone_bone serious serious_look sex shounen_jump stone_ocean sweaty_breasts threesome vaginal_penetration

ai_generatedass

1boy 1boy1girl 1girls against_wall ai_generated ass ass_up big_ass big_breasts big_butt doggy_style excited face_down_ass_up fat_ass female from_behind from_behind_position grabbing grabbing_ass grabbing_from_behind green_hair huge_ass jail jojo's_bizarre_adventure jolyne_kujo male prisoner prone_bone sex shiny shiny_ass shiny_skin shounen_jump smile stone_ocean sweat sweatdrop sweating sweaty sweaty_breasts sweaty_butt vaginal_penetration

against_wallai_generated

1boy1girl ai_generated breasts cock hiiragi_yuzu huge_breasts pink_hair prisoner purple_hair pussy pussy_penetration tied_hands touching_breast yu-gi-oh! yu-gi-oh!_arc-v yuri_(yu-gi-oh!) zuzu_boyle

ai_generatedbreasts

1boy 1girls 3d baldur's_gate_3 balls big_penis black_sclera blowjob cage domination drooling duo excessive_saliva eye_contact fellatio female femsub forced forced_oral foreskin goblin goblin_female green_eyes green_skin hair head_up human human_on_humanoid humanoid in_cage interspecies jail leeterr long_ears male maledom open_eyes oral oral_penetration oral_sex pale-skinned_male pale_skin penis penis_out pointy_ears prison prison_bars prisoner rape red_hair saliva saliva_string sazza side_view sidecut straight submissive unseen_male_face upper_body veiny_penis yellow_eyes

baldur's_gate_3balls

ai_generated angry_face black_sclera breasts captured castlevania castlevania_nocturne chained_up chained_wrists dark-skinned_female dark_sclera demon_wings drolta_tzuentes dungeon earrings elbow_gloves fangs female female_only fiery_hair fiery_tail fur_reaper head_jewel horns jewelry looking_at_viewer medium_breasts naked navel nude open_mouth pink_eyes pink_hair pointy_ears prisoner pussy stable_diffusion standing tail thigh_highs thighhighs vagina vampire wings

ai_generatedangry_face

1girls ass_expansion bimbofication bondage bottomless brainwashing breast_expansion breasts_bigger_than_head bursting_breasts dark-skinned_female dark_skin dialogue drooling dubious_consent earrings enemy_conversion english english_text eyes_open female female_focus forced_orgasm freckles green_eyes held_down huge_ass huge_breasts huge_nipples hypnosis large_ass large_breasts long_hair magic marvel marvel_comics marvel_rivals on_back open_mouth pleasure_face plump_lips prisoner red_hair restrained scarlet_witch scarlet_witch_(marvel_rivals) skinny_waist stockholm_syndrome tearing_clothes text text_bubble vibrator wand_vibrator wanda_maximoff zephyrgales

ass_expansionbimbofication

1boy 2d ahe_gao ai_generated animal_genitalia balls big_balls big_penis bikini blue-skinned_female breeding canid canine canine_penis cock_worship cow_print face_covered female giant_cock goth heart heart-shaped_pupils huge_cock hugoroman hyper_penis imminent_sex kiss_mark kissing_penis league_of_legends male massive_penis mating_press monster_cock penetration penis petite poppy prison prisoner shortstack size_difference spiked_penis straight_sex vaginal_penetration vaginal_sex veiny_penis werewolf wet wet_body wet_pussy wolf yordle

ahe_gaoai_generated

1boy 2d ai_generated animal_genitalia bikini canine_penis cock_worship cow_print face_covered female giant_cock huge_cock hugoroman hyper_penis imminent_sex kiss_mark kissing_penis league_of_legends massive_penis missionary_position monster_cock penetration petite poppy prison prisoner shortstack size_difference spiked_penis straight_sex vaginal_penetration vaginal_sex werewolf wet wet_body wet_pussy yordle

ai_generatedanimal_genitalia

1boy 2d ai_generated animal_genitalia bikini blowjob blowjob_face canine_penis cock_worship cow_print face_covered female giant_cock goth huge_cock hugoroman hyper_penis imminent_sex kiss_mark kissing_penis league_of_legends massive_penis monster_cock petite poppy prison prisoner shortstack size_difference spiked_penis straight_sex werewolf wet wet_body wet_pussy yordle

ai_generatedanimal_genitalia

1boy 2d ai_generated animal_genitalia bikini canine_penis cock_worship cow_print face_covered female giant_cock goth huge_cock hugoroman hyper_penis imminent_sex kiss_mark kissing_penis league_of_legends massive_penis monster_cock petite poppy prison prisoner shortstack size_difference spiked_penis straight_sex werewolf wet wet_body wet_pussy yordle

ai_generatedanimal_genitalia

1boy 2d ai_generated animal_genitalia big_balls big_penis bikini canine canine_penis cock_worship cow_print face_covered female giant_cock goth huge_cock hugoroman hyper_penis imminent_sex kiss_mark kissing_penis league_of_legends massive_penis monster_cock petite poppy prison prisoner shortstack size_difference spiked_penis straight_sex werewolf wet wet_body wet_pussy wolf yordle

ai_generatedanimal_genitalia

1boy 2girls ai_generated arms_behind_back bangs big_breasts blonde_hair blowjob blowjob_sandwich blush breast_press breasts brown_eyes clothing collaborative_fellatio double_blowjob fellatio female glasses hair_bun indoors large_breasts licking licking_penis looking_at_viewer midorikawa_hana multiple_girls open_mouth oral_sex patreon_username penguih penis pov prison_school prisoner saliva shiraki_meiko short_hair silver_hair striped striped_clothing sucking_penis threesome tongue white_hair

ai_generatedarms_behind_back

absurd_res anonymous_artist anthro apogee_(tinygaypirate) armbinder ball_gag binder_(restraint) bondage bondage_gear bound boxbinder brown_body brown_eyes brown_fur brown_hair canid canine canis chest_tattoo clothing collar digital_drawing_(artwork) digital_media_(artwork) digital_painting_(artwork) domestic_dog ear_piercing female fur gag gagged hair hi_res laika leg_tattoo legwear mammal nipples painting_(artwork) piercing prisoner restraints sex_toy simple_background solo stockings tattoo vibrator

absurd_resanonymous_artist

2boys androgynous aqua_hair aqua_nails arm_tattoo asymmetrical_gloves barbie_(franchise) barbie_(live_action) barbie_mugshot_(meme) bard bead_necklace beads beret black_gloves black_hair blush braid cape cecilia_flower_(genshin_impact) character_name collared_cape collared_shirt diamond-shaped_pupils diamond_(shape) eyeshadow facial_mark flower forehead_mark frilled_sleeves frills genshin_impact gloves gradient_hair green_cape green_eyes green_gloves green_hair green_headwear hat hat_flower heart height_chart height_mark highres holding holding_sign jewelry juliet_sleeves koi_kuze long_sleeves looking_at_viewer makeup male_focus meme mugshot multicolored_hair multiple_boys necklace one_eye_closed open_mouth prison prisoner puffy_sleeves red_eyeshadow shirt short_hair_with_long_locks shoulder_spikes side_braids sign smile spikes symbol-shaped_pupils tassel tattoo twin_braids upper_body venti_(genshin_impact) white_flower white_shirt xiao_(genshin_impact) yaoi yellow_eyes

androgynousaqua_hair

2boys barbie_mugshot_(meme) black_hair character_name chest_tattoo collared_shirt earrings facial_hair finger_tattoo fur_hat grin hat height_chart height_mark highres holding holding_sign jewelry lightacrobat long_sideburns long_sleeves looking_at_another looking_at_viewer male_focus meme monkey_d._luffy mugshot multiple_boys one_eye_closed one_piece open_mouth prison prisoner red-tinted_eyewear shirt short_hair sideburns sign smile straw_hat sunglasses tattoo tinted_eyewear trafalgar_law upper_body white_headwear white_shirt

barbie_mugshot_(meme)black_hair

1girl barbie_mugshot_(meme) blonde_hair blue_eyes bob_cut brown_capelet brown_headwear capelet collared_shirt deerstalker detective hat height_chart height_mark highres holding holding_sign hololive hololive_english long_sleeves looking_at_viewer meme mugshot necktie onionyaa open_mouth prison prisoner red_necktie shirt short_hair short_necktie sign upper_body virtual_youtuber watson_amelia watson_amelia_(1st_costume) white_shirt

barbie_mugshot_(meme)blonde_hair

1girl barbie_mugshot_(meme) blonde_hair bob_cut character_name collared_shirt detective height_chart height_mark highres holding holding_sign hololive hololive_english long_sleeves looking_at_viewer meme mugshot necktie onionyaa prison prisoner red_necktie shirt short_hair short_necktie sign smol_ame upper_body virtual_youtuber watson_amelia white_shirt

barbie_mugshot_(meme)blonde_hair

1boy barbie_mugshot_(meme) blue_eyes blue_hair dark_blue_hair height_chart height_mark highres holding holding_sign looking_at_viewer male_focus meme mugshot parted_lips plave prisoner short_hair short_sleeves sign upper_body white-framed_eyewear yejun_(plave) yoonmiumi

barbie_mugshot_(meme)blue_eyes

1boy barbie_mugshot_(meme) blonde_hair blue_eyes height_chart height_mark highres holding holding_sign long_sleeves looking_at_viewer male_focus meme mugshot noah_(plave) one_eye_closed parted_lips pink_sweater plave prisoner short_hair sign smile sweater upper_body yellow-framed_eyewear yoonmiumi

barbie_mugshot_(meme)blonde_hair

1boy barbie_mugshot_(meme) blonde_hair bombyoon brown_eyes haikyuu!! height_chart height_mark highres holding holding_sign light_brown_hair long_sleeves looking_at_viewer male_focus meme miya_atsumu mugshot multicolored_hair open_mouth prisoner short_hair sign smile two-tone_hair upper_body

barbie_mugshot_(meme)blonde_hair

1girl barbie_mugshot_(meme) beret blue_eyes brown_hair bug butterfly hat height_chart height_mark holding holding_sign insect juliet_sleeves kimleepark1129 long_sleeves looking_at_viewer maid meme mugshot prison prisoner puffy_sleeves shannon_(umineko) short_hair sign umineko_no_naku_koro_ni upper_body white_hat yellow_butterfly

barbie_mugshot_(meme)beret

1other androgynous barbie_mugshot_(meme) brown_dress brown_hair dress flower grey_eyes hair_flower hair_ornament height_chart height_mark holding holding_sign juliet_sleeves kimleepark1129 long_sleeves looking_at_viewer meme mugshot open_mouth prison prisoner puffy_sleeves red_flower red_rose rose short_hair sign spoilers umineko_no_naku_koro_ni upper_body yasu_(umineko)

androgynousbarbie_mugshot_(meme)

1boy barbie_mugshot_(meme) black_eyes black_hair black_shirt bombyoon closed_mouth haikyuu!! height_chart height_mark highres holding holding_sign long_sleeves looking_at_viewer male_focus meme mole mole_above_eye mugshot multiple_moles prisoner sakusa_kiyoomi shirt short_hair sign simple_background upper_body wavy_hair

barbie_mugshot_(meme)black_eyes

1girl 2others abs angry areola_slip armor armpits arms_up blonde_hair blue_eyes bound breasts chained_wrists chainmail closed_mouth clothed_male_nude_female collar commentary_request grabbing_another's_hair greaves hand_on_another's_head helmet highres holding holding_weapon huge_breasts ichiren_takushou indoors loincloth long_hair looking_at_viewer metal_collar multiple_others muscular muscular_female navel no_panties nude obliques original pelvic_curtain plate_armor prisoner pubic_hair pubic_hair_peek restrained scar scar_on_leg solo_focus standing steam sweat thighhighs toned topless torn_clothes underboob very_long_hair weapon whip_marks window

1girl audrey_(perfect_gold) barbie_(franchise) barbie_(live_action) barbie_mugshot_(meme) card character_name english_text hairband height_chart height_mark holding holding_card holding_sign medium_hair meme mole mole_under_eye mugshot official_art perfect_gold pink_eyes prisoner purple_hair school_uniform sign solo

audrey_(perfect_gold)barbie_(franchise)

2girls :o absurdres belt black_belt black_necktie black_pants blue_eyes blush bocchi_the_rock! breasts buttons cleavage closed_mouth collared_shirt cube_hair_ornament double-breasted gotoh_hitori green_eyes grey_background hair_between_eyes hair_ornament highres kita_ikuyo large_breasts long_hair long_sleeves meijio3 multiple_girls necktie pants pink_hair police police_uniform policewoman prison_clothes prisoner red_hair shirt speech_bubble standing sweatdrop tearing_up translation_request

1girl barbie_(franchise) barbie_(live_action) barbie_mugshot_(meme) blue_eyes creatures_(company) deitycyla game_freak happy highres jessie_(pokemon) meme nintendo open_mouth pokemon pokemon_(anime) prison prisoner red_hair smile team_rocket

barbie_(franchise)barbie_(live_action)

1boy barbie_(franchise) barbie_(live_action) barbie_mugshot_(meme) blue_hair creatures_(company) crying deitycyla game_freak green_eyes highres james_(pokemon) meme nintendo pokemon pokemon_(anime) prison prisoner sad team_rocket tears

barbie_(franchise)barbie_(live_action)

1girl 3boys abs absurdres anal ass back bare_back barefoot black_hair blonde_hair boruto:_naruto_next_generations breasts censored cheating_(relationship) cowgirl_position doctor doggystyle double_penetration facial_mark forehead_jewel forehead_mark green_eyes group_sex hair_pulled hair_pulled_back hand_on_another's_ass handjob haruno_sakura highres jiji kumostudios large_breasts mature_female medium_breasts multiple_boys muscular muscular_arms muscular_legs muscular_male naruto_(series) netorare nurse open_mouth pectorals penis penis_grab pink_hair prisoner sex sex_from_behind sideboob straddling thick_thighs thighs vaginal

1girl 6+boys absurdres boruto:_naruto_next_generations doctor fellatio group_sex haruno_sakura highres jiji_(boruto) kumostudios lab_coat mature_female multiple_boys naruto naruto_(series) netorare oral penis prisoner sakura

absurdresboruto:_naruto_next_generations

3girls all_fours american_flag ass braid breasts dorkbum english_text green_eyes green_hair green_lips highres huge_ass jojo_no_kimyou_na_bouken kuujou_jolyne long_hair looking_back medium_breasts multicolored_hair multiple_girls nipples nude prison prison_guard prisoner solo_focus stone_ocean thick_thighs thighs two-tone_hair wide_hips

all_foursamerican_flag

1boy 1girl after_vaginal aftersex barefoot bdsm blush bondage bound breasts chain collar cuffs cum cum_in_pussy cumdrip feet finger_to_another's_mouth gluteal_fold heart heart-shaped_pupils hetero heterochromia highres hololive houshou_marine large_breasts long_hair looking_at_viewer moral_cacoethes nipples open_mouth prison_clothes prisoner pussy red_eyes red_hair restrained saliva slave symbol-shaped_pupils virtual_youtuber yellow_eyes

after_vaginalaftersex

1boy 1girl after_vaginal aftersex barefoot bdsm blush bondage bound breasts chain collar cuffs cum cum_in_pussy cumdrip feet female_pubic_hair finger_to_another's_mouth gluteal_fold heart heart-shaped_pupils hetero heterochromia highres hololive houshou_marine large_breasts long_hair looking_at_viewer moral_cacoethes nipples open_mouth prison_clothes prisoner pubic_hair pussy red_eyes red_hair restrained saliva slave symbol-shaped_pupils virtual_youtuber yellow_eyes

after_vaginalaftersex

1boy 1girl absurdres arm_tattoo baton_(weapon) belt black_belt black_dress black_gloves black_hair black_headwear black_mask black_necktie black_shirt blonde_hair chain chained chained_wrists collar collared_dress cuffs dress fingerless_gloves full_body gloves hair_between_eyes hat high_heels highres holding holding_megaphone iv_4t long_hair megaphone metal_collar necktie nijisanji o-ring o-ring_thigh_strap police police_hat police_uniform policewoman prison_clothes prisoner red_eyes red_footwear red_nails shackles shirt short_hair short_sleeves sleeveless sleeveless_shirt standing striped_clothes striped_shirt sweatdrop takamiya_rion tattoo thigh_strap torn_clothes torn_shirt virtual_youtuber weapon white_shirt yumeoi_kakeru

absurdresarm_tattoo

1girl 2boys artist_request baton blue_dress chain cosplay dress fallenshadow handwraps hat helmet highres multiple_boys one_eye_closed persona persona_5 prison prisoner purple_eyes purple_hair ribbon smirk thighhighs velvet_room virtual_youtuber wink

artist_requestbaton

2girls age_difference animal_ears armpits arms_behind_back bat_ears bat_girl bat_wings black_background black_leotard blush breasts captured chain chained clothed_female_nude_female colored_skin defeat elbow_gloves embarrassed euf-dreamer eyelashes eyeshadow female_focus furry furry_female gloves highres humiliation large_breasts legs leotard looking_at_another looking_to_the_side makeup mature_female multicolored_skin multiple_girls navel nipples nude open_mouth panties prisoner rabbit_ears rabbit_girl rabbit_tail restrained rouge_the_bat shiny_skin simple_background skin_tight sonic_(series) source_request standing tail tears thighs topless_female two-tone_skin underwear underwear_only unworn_clothes vanilla_the_rabbit white_panties wings yellow_eyes

age_differenceanimal_ears

artist_namebelt

1boy 1futa altered_history anal bible_black breasts brown_hair futa_with_male futanari green_eyes highres imari_kurumi large_breasts lying male_penetrated minase_taki nipples nude on_back pegging possessed prisoner sex standing torture witch

altered_historyanal

1boy 1futa anal bible_black breasts brown_hair futa_with_male futanari green_eyes highres huge_breasts imari_kurumi large_breasts lying male_penetrated minase_taki nipples nude on_back pegging possessed prisoner sex standing torture witch

analbible_black

1boy bed brown_hair depressed hand_on_own_head highres konami male_focus murphy_pendleton official_art prison prison_clothes prisoner promotional_art purple_theme shadow silent_hill silent_hill:_downpour silent_hill_(series) sitting solo writing_on_wall

1boy abs ankle_cuffs arm_hair armpit_hair bara body_hair borrowed_character boxers chest_hair come_hither commission crack cracked_wall cuffs dark-skinned_male dark_skin dragmire full_body green_male_underwear grin hairy handcuffs highres large_pectorals leg_hair long_sideburns male_focus male_underwear mature_male muscular muscular_male navel_hair nipples oc_(sharlin) orc original pectorals prisoner seductive_smile short_hair sideburns smile solo standing stomach thick_thighs thighs topless_male tusks underwear

1boy 1girl absurdres angry armor bad_end black_hair bodysuit breasts captured captured_heroin commission dark_skin defeat english_text halo_(game) halo_(series) highres imminent_penetration imminent_rape interspecies medium_breasts mia-b013 nipples non-web_source original prisoner pussy rammionn restrained sex_slave spartan_(halo) spoils spoils_of_war

1boy 1girl absurdres armor bad_end black_hair bodysuit breasts captured captured_heroin commission dark_skin defeat english_text halo_(game) halo_(series) highres imminent_penetration imminent_rape interspecies large_penis medium_breasts mia-b013 nipples non-web_source original partially_undressed penis penis_awe prisoner rammionn restrained sex_slave spartan_(halo) spoils spoils_of_war

1boy 1girl absurdres angry armor bad_end bdsm black_hair blush bodysuit bondage bound breasts captured captured_heroin clenched_teeth clitoris clothed_sex commission dark-skinned_female dark_skin defeat english_text female_focus girl_on_top halo_(game) halo_(series) hetero highres indoors interspecies large_penis lips looking_at_viewer mia-b013 motion_lines muscular muscular_female nipples no_bra no_panties non-web_source open_clothes original partially_undressed penis pov pov_crotch pov_hands prisoner pussy rammionn rape restrained sex sex_slave short_hair solo_focus spartan_(halo) spoils spoils_of_war spread_legs stationary_restraints teeth uncensored vaginal yellow_eyes

1boy 1girl absurdres ahegao angry armor bad_end black_hair bodysuit breasts captured captured_heroin commission cum cum_in_pussy dark_skin defeat english_text halo_(game) halo_(series) hetero highres interspecies large_insertion large_penis medium_breasts mia-b013 nipples non-web_source original partially_undressed penis prisoner pussy rammionn rape restrained sex_slave spartan_(halo) spoils spoils_of_war vaginal

absurdresahegao

1boy 1girl absurdres angry armor bad_end black_hair bodysuit breasts captured captured_heroin commission cum cum_in_container cum_in_headwear cum_in_pussy dark_skin defeat english_text halo_(game) halo_(series) hetero highres interspecies large_penis medium_breasts mia-b013 nipples non-web_source original partially_undressed penis prisoner pussy rammionn rape restrained sex_slave spartan_(halo) spoils spoils_of_war vaginal

1boy 1girl absurdres after_rape angry armor bad_end black_hair bodysuit breasts captured captured_heroin commission cum cum_in_container cum_in_headwear cum_in_pussy dark_skin defeat english_text female_orgasm halo_(game) halo_(series) hetero highres interspecies large_penis medium_breasts mia-b013 nipples non-web_source orgasm original partially_undressed penis prisoner pussy rammionn rape restrained sex_slave spartan_(halo) spoils spoils_of_war vaginal

absurdresafter_rape

1boy age_progression ass bara blush bodysuit bulge bulge_lift chain character_request copyright_request cuffs denim dressing facial_hair feet_out_of_frame from_side goatee handcuffs highres i've_never_seen_a_guy_recreate_this_successfully_tbh_(meme) jeans large_pectorals male_focus mature_male meme muscular muscular_male open_pants pants pants_lift pectorals prison_clothes prisoner short_hair sideburns striped_clothes striped_pants stubble undersized_clothes vest zonknuckle

age_progressionass

1boy blue_hair buggy_the_clown clown_nose highres impel_down mature_male one_piece pants pirate ponytail prison prison_cell prison_clothes prisoner red_nose shirt signature sitting smile striped_clothes striped_pants striped_shirt topless_male umikochannart

blue_hairbuggy_the_clown

1girl ;o arms_behind_back arms_up azur_lane blush bound bound_arms breasts brown_hair chain chained chained_wrists commentary_request commission dress fang feathers from_below groin hair_between_eyes hat highres kneeling large_breasts long_hair long_sleeves looking_at_viewer looking_down manjuu_(azur_lane) medium_breasts no_bra no_panties one_eye_closed pamiat_merkuria_(azur_lane) pamiat_merkuria_(caged_minx)_(azur_lane) pink_eyes prison_clothes prisoner restrained side-tie_dress side_slit sitting skeb_commission solo striped_clothes striped_dress striped_headwear tears thighs tickling tickling_armpits tickling_legs tickling_sides torn_clothes torn_dress translation_request twitter_username underboob very_long_hair waa!_okami

;oarms_behind_back

1boy absurdres animal_ears arknights bara beard blue_eyes eyebrow_cut facial_hair frown furry furry_male highres looking_at_viewer male_focus mature_male mountain_(arknights) official_alternate_costume pluto_(pu94_d1de4c) prisoner short_hair solo tiger_boy tiger_ears upper_body white_fur

absurdresanimal_ears

1boy 1girl 69 amazon_position anilingus animated asian ass assertive_female bandages boots bouncing bouncing_ass brown_hair censored cjod-267 cowgirl_position cum cum_in_pussy cunnilingus cunnilingus_through_clothes ejaculation erection fellatio femdom girl_on_top glansjob gloves handjob hasumi_kurea hat hetero high_heels jacket japanese_(nationality) jav kiss latex leather leather_jacket licking licking_nipple long_hair male_squirt milk mosaic_censoring nipple_stimulation nipples on_floor on_ground oral paddle penis photo_(medium) police police_hat police_uniform policewoman post_orgasm_torture pouring prison prison_cell prison_clothes prisoner pulling real_life reverse_cowgirl_position rubbing rusty_trombone sex sitting sitting_on_person skirt slapping sound spanked spanking standing standing_on_one_leg stepped_on stepping straddling tagme thighs undressing undressing_another vaginal video

amazon_positionanilingus

ahoge blood braid close-up collar comic commentary faceless faceless_male greyscale highres kantai_collection looking_outside masukuza_j monochrome prisoner rain shigure_(kancolle) torn_clothes translation_request

4girls ahoge alternate_hairstyle braid close-up collar comic commentary flashlight greyscale highres kantai_collection long_hair masukuza_j medium_hair monochrome multiple_girls murasame_(kancolle) prisoner shigure_(kancolle) shiratsuyu_(kancolle) slave torn_clothes twintails two-page_spread yuudachi_(kancolle)

ahogealternate_hairstyle

2girls abyssal_ship ahoge blood cannon close-up collar comic dismemberment greyscale highres kantai_collection long_hair masukuza_j medium_hair missing_limb monochrome multiple_girls potato prisoner regeneration repair_bucket screaming shigure_(kancolle) torn_clothes torpedo_tubes

abyssal_shipahoge

1girl akatsuki_blitzkampf akatsuki_denko_senki anal anilingus anus_licking ass clothed_female_nude_male cum dark-skinned_male dark_penis ejaculation femdom gloves hair hair_over_one_eye horny interracial jerking_off kanae kisuu licking muscle odd_(pixiv159317) oral penis prison prisoner purple_hair rimjob slut solo_focus sweat testicles tongue uncensored uniform upside-down

akatsuki_blitzkampfakatsuki_denko_senki

akatsuki_blitzkampf breasts cum hair horny kanae nipple penis prison prisoner sideboob single_breast

akatsuki_blitzkampfbreasts

dr._ivo_'eggman'_robotnik dr_eggman dr_robotnik egg_mobile endured_face erect_nipples fat furry glasses machine moustache nancher penetration plump prisoner rape rouge_the_bat sega simple_background sonic_*(series) sonic_the_hedgehog_(series) tongue wink

dr._ivo_'eggman'_robotnikdr_eggman

1girl armor bdsm blonde_hair bondage bound breasts cameltoe curvy duel_monster hair_over_one_eye hips huge_breasts long_hair mole nipple_slip nipples prisoner restrained senbei senbei_(avocadochaya) solo thick_thighs thighs wide_hips x-saber_anapelera x-saber_anu_piranha you_gonna_get_raped yu-gi-oh! yuu-gi-ou yuu-gi-ou_duel_monsters

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