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female prisoner

1girl anal animated animated_gif arms_behind_back bdsm bondage bouncing_breasts bound bound_wrists breasts censored chain collar distressed double_penetration female_focus female_prisoner group_sex indoors mosaic_censoring multiple_penetration nipples pink_hair prison prisoner raika_grace rape restrained screaming sex slave third-party_edit vaginal viper_(series) viper_ctr viper_f40
1girl anal animated animated_gif arms_behind_back bdsm bondage bouncing_breasts bound bound_wrists breasts censored chain collar distressed double_penetration female_focus female_prisoner group_sex indoors mosaic_censoring multiple_penetration nipples pink_hair prison prisoner raika_grace rape restrained screaming sex slave third-party_edit vaginal viper_(series) viper_ctr viper_f40
1girl ankle_cuffs arms_up ass barefoot bdsm bikini blonde_hair blue_eyes blush bondage bound bound_ankles bound_wrists breasts chain chained chained_ankles chained_cuffs chained_wrists character_request cuffs dungeon feet female_focus female_prisoner huge_breasts indoors large_breasts lento_(glamour_works) long_hair nipples one_eye_closed open_mouth original prisoner restrained sitting solo source_request spread_legs swimsuit toes wink wrist_cuffs
1girl ankle_cuffs arms_up ass barefoot bdsm bikini blonde_hair blue_eyes blush bondage bound bound_ankles bound_wrists breasts chain chained chained_ankles chained_cuffs chained_wrists character_request cuffs dungeon feet female_focus female_prisoner huge_breasts indoors large_breasts lento_(glamour_works) long_hair nipples one_eye_closed open_mouth original prisoner restrained sitting solo source_request spread_legs swimsuit toes wink wrist_cuffs
1girl arms_behind_back bar_censor barefoot bdsm black_eyes black_hair blush bondage bound bound_arms breasts censored clenched_teeth collar completely_nude feet female_focus female_prisoner female_pubic_hair full_body indoors kneeling large_breasts long_hair navel nipples nude original ponytail prison prisoner pubic_hair pussy sitting solo sweat tears teeth zutsu
1girl arms_behind_back bar_censor barefoot bdsm black_eyes black_hair blush bondage bound bound_arms breasts censored clenched_teeth collar completely_nude feet female_focus female_prisoner female_pubic_hair full_body indoors kneeling large_breasts long_hair navel nipples nude original ponytail prison prisoner pubic_hair pussy sitting solo sweat tears teeth zutsu
1girls big_breasts blush bottomless breasts faceless_male favorite female female_focus female_prisoner green_hair green_lipstick human jojo's_bizarre_adventure jolyne_kujo jumbogumbo large_breasts light-skinned_female light_skin long_hair penis prison prisoner rape sex shounen_jump stone_ocean straight thick_lips
1girls big_breasts blush bottomless breasts faceless_male favorite female female_focus female_prisoner green_hair green_lipstick human jojo's_bizarre_adventure jolyne_kujo jumbogumbo large_breasts light-skinned_female light_skin long_hair penis prison prisoner rape sex shounen_jump stone_ocean straight thick_lips
1girl armbinder arms_behind_back bars bdsm bondage bound bound_arms bowl breasts brown_hair bucket chain chain_leash collar coma_(artist) female_focus female_prisoner game_cg harness indoors leash long_hair medium_breasts nipples nude pc-98_(style) pet_bowl pet_play pil_(company) prison prison_bars prisoner seek_~chikashitsu_no_mesu_dorei-tachi~ sitting slave solo very_long_hair vinyl
1girl armbinder arms_behind_back bars bdsm bondage bound bound_arms bowl breasts brown_hair bucket chain chain_leash collar coma_(artist) female_focus female_prisoner game_cg harness indoors leash long_hair medium_breasts nipples nude pc-98_(style) pet_bowl pet_play pil_(company) prison prison_bars prisoner seek_~chikashitsu_no_mesu_dorei-tachi~ sitting slave solo very_long_hair vinyl
1girls after_rape artoria_pendragon birth birthing bondage broken_rape_victim censored chained chains childbirth crowning crying_with_eyes_open cum despair dungeon fate_(series) female female_focus female_prisoner huge_breasts koboshi_no_niwa lactation nipples nude pregnant prisoner raped royalty saber slave tears thick_thighs
1girls after_rape artoria_pendragon birth birthing bondage broken_rape_victim censored chained chains childbirth crowning crying_with_eyes_open cum despair dungeon fate_(series) female female_focus female_prisoner huge_breasts koboshi_no_niwa lactation nipples nude pregnant prisoner raped royalty saber slave tears thick_thighs
1boy 1girls arena arms_behind_back audience baggy_shirt beheaded beheading belt bent_over black_vest blonde_hair blood blood_splatter blood_spray blood_spurt blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block clenched_fists closed_eyes clothed_male_nude_female cut_neck death decapitated decapitated_head decapitation execution exhibitionism fate/grand_order fate_(series) female female_death female_prisoner fire2water flag french french_girl gloves gore hair_ribbon hands_behind_back hands_tied hands_tied_behind_back jeanne_d'arc_(fate) kneeling kneeling_on_flag kneeling_on_floor knight long_hair male medium_breasts neck_bound nipples nude nude_female nude_female_clothed_male original presenting_ass princess_knight prisoner severed_head snuff tongue tongue_out unseen_male_face white_woman wooden_platform
1boy 1girls arena arms_behind_back audience baggy_shirt beheaded beheading belt bent_over black_vest blonde_hair blood blood_splatter blood_spray blood_spurt blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block clenched_fists closed_eyes clothed_male_nude_female cut_neck death decapitated decapitated_head decapitation execution exhibitionism fate/grand_order fate_(series) female female_death female_prisoner fire2water flag french french_girl gloves gore hair_ribbon hands_behind_back hands_tied hands_tied_behind_back jeanne_d'arc_(fate) kneeling kneeling_on_flag kneeling_on_floor knight long_hair male medium_breasts neck_bound nipples nude nude_female nude_female_clothed_male original presenting_ass princess_knight prisoner severed_head snuff tongue tongue_out unseen_male_face white_woman wooden_platform
1boy 1girl arms_behind_back azuki_kurenai bdsm blush bondage bound breast_bondage breasts brown_eyes brown_hair censored collar female_prisoner game_cg guilty_(company) hetero ingoku_no_gakuen large_breasts long_hair looking_at_viewer mosaic_censoring navel nipples nude open_mouth prisoner pubic_hair pussy rope saliva sex shibari slave spread_legs sweat vaginal
1boy 1girl arms_behind_back azuki_kurenai bdsm blush bondage bound breast_bondage breasts brown_eyes brown_hair censored collar female_prisoner game_cg guilty_(company) hetero ingoku_no_gakuen large_breasts long_hair looking_at_viewer mosaic_censoring navel nipples nude open_mouth prisoner pubic_hair pussy rope saliva sex shibari slave spread_legs sweat vaginal
1girl ankle_cuffs artist_cg bad_tag barefoot bdsm blush bondage bottomless bound breasts brown_hair censored chain chained chained_ankles chained_cuffs character_request clenched_teeth copyright_request cuffs dungeon feet female_prisoner hair_ornament hair_ribbon indoors large_breasts mosaic_censoring navel nipples no_bra no_panties no_underwear prisoner purple_eyes pussy ribbon short_hair slave soba_udon spread_legs squatting teeth toes torn_clothes
1girl ankle_cuffs artist_cg bad_tag barefoot bdsm blush bondage bottomless bound breasts brown_hair censored chain chained chained_ankles chained_cuffs character_request clenched_teeth copyright_request cuffs dungeon feet female_prisoner hair_ornament hair_ribbon indoors large_breasts mosaic_censoring navel nipples no_bra no_panties no_underwear prisoner purple_eyes pussy ribbon short_hair slave soba_udon spread_legs squatting teeth toes torn_clothes
1girl all_fours angry ass ass_grab bdsm black_hair blush bondage bound bound_arms breasts closed_mouth female_focus female_prisoner grabbing_another's_breast groping hanging_breasts headband lipstick long_hair looking_at_viewer makeup maku_(l-u) naruto naruto_(series) nipples nude pillory prison prisoner pussy_juice red_eyes stocks swea sweat yuuhi_kurenai
1girl all_fours angry ass ass_grab bdsm black_hair blush bondage bound bound_arms breasts closed_mouth female_focus female_prisoner grabbing_another's_breast groping hanging_breasts headband lipstick long_hair looking_at_viewer makeup maku_(l-u) naruto naruto_(series) nipples nude pillory prison prisoner pussy_juice red_eyes stocks swea sweat yuuhi_kurenai
1boy 1girls after_oral after_rape after_sex arena arms_behind_back audience baggy_shirt belt bent_over black_vest blonde_hair blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block closed_eyes clothed_male_nude_female cum cum_drip cum_in_mouth cum_on_ass cum_on_thighs cum_outside execution exhibitionism fate/grand_order fate_(series) female female_prisoner fire2water flag french french_girl gloves hair_ribbon hands_behind_back hands_tied hands_tied_behind_back imminent_death imminent_decapitation jeanne_d'arc_(fate) kneeling kneeling_on_flag kneeling_on_floor knight long_hair male medium_breasts neck_bound nipples nude nude_female nude_female_clothed_male original presenting_ass princess_knight prisoner white_woman wooden_platform
1boy 1girls after_oral after_rape after_sex arena arms_behind_back audience baggy_shirt belt bent_over black_vest blonde_hair blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block closed_eyes clothed_male_nude_female cum cum_drip cum_in_mouth cum_on_ass cum_on_thighs cum_outside execution exhibitionism fate/grand_order fate_(series) female female_prisoner fire2water flag french french_girl gloves hair_ribbon hands_behind_back hands_tied hands_tied_behind_back imminent_death imminent_decapitation jeanne_d'arc_(fate) kneeling kneeling_on_flag kneeling_on_floor knight long_hair male medium_breasts neck_bound nipples nude nude_female nude_female_clothed_male original presenting_ass princess_knight prisoner white_woman wooden_platform
1girls armpit blue_eyes blue_hair braid breasts brown_coat chained_wrists chains cleft_of_venus coat coat_on_shoulders coat_only cuffs curvaceous dead_or_alive dead_or_alive_xtreme_venus_vacation earrings enormous_breasts erect_nipples exhibitionism exposed_areolae exposed_breasts exposed_nipples exposed_pussy female_focus female_prisoner hairless_pussy handcuffed handcuffs hi_res high_resolution highres hourglass_figure huge_areolae huge_breasts huge_nipples legs_apart lobelia_(dead_or_alive) long_hair looking_at_viewer makeup mascara massive_breasts matching_hair/eyes matching_hair_and_eyes nipples no_pubic_hair nude nude_female open_mouth parted_lips partially_nude partially_undressed piercing pinkseito prison prison_bars prison_cell prisoner public_exposure public_indecency pussy shaved_pussy shiny_body shiny_breasts shiny_hair shiny_skin side_braid skindentation smile smiling_at_viewer solo solo_female standing thin_eyebrows uncensored voluptuous
1girls armpit blue_eyes blue_hair braid breasts brown_coat chained_wrists chains cleft_of_venus coat coat_on_shoulders coat_only cuffs curvaceous dead_or_alive dead_or_alive_xtreme_venus_vacation earrings enormous_breasts erect_nipples exhibitionism exposed_areolae exposed_breasts exposed_nipples exposed_pussy female_focus female_prisoner hairless_pussy handcuffed handcuffs hi_res high_resolution highres hourglass_figure huge_areolae huge_breasts huge_nipples legs_apart lobelia_(dead_or_alive) long_hair looking_at_viewer makeup mascara massive_breasts matching_hair/eyes matching_hair_and_eyes nipples no_pubic_hair nude nude_female open_mouth parted_lips partially_nude partially_undressed piercing pinkseito prison prison_bars prison_cell prisoner public_exposure public_indecency pussy shaved_pussy shiny_body shiny_breasts shiny_hair shiny_skin side_braid skindentation smile smiling_at_viewer solo solo_female standing thin_eyebrows uncensored voluptuous
00s 1girl arms_behind_back bdsm black_thighhighs blush bondage bound breasts brown_hair chain chained chained_arms clitoris closed_eyes collage_(artist) collar drugged feeding female_prisoner force-feeding gag gagged hiiragi_akao huge_belly indoors inflation intravenous_drip jinki lactation long_hair milking_machine navel nipples nude pipelining plug_gag prison prisoner pussy spread_legs spread_pussy stomach_bulge tape tears thighhighs torture uncensored women_livestock
00s 1girl arms_behind_back bdsm black_thighhighs blush bondage bound breasts brown_hair chain chained chained_arms clitoris closed_eyes collage_(artist) collar drugged feeding female_prisoner force-feeding gag gagged hiiragi_akao huge_belly indoors inflation intravenous_drip jinki lactation long_hair milking_machine navel nipples nude pipelining plug_gag prison prisoner pussy spread_legs spread_pussy stomach_bulge tape tears thighhighs torture uncensored women_livestock
1boy 1girls arena arms_behind_back audience baggy_shirt belt bent_over black_vest blonde_hair blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block closed_eyes clothed_male_nude_female execution exhibitionism fate/grand_order fate_(series) female female_prisoner fire2water french french_girl gloves hair_ribbon hands_behind_back hands_tied hands_tied_behind_back imminent_death imminent_decapitation jeanne_d'arc_(fate) kneeling knight long_hair male medium_breasts neck_bound nipples nude nude_female nude_female_clothed_male original princess_knight prisoner white_woman wooden_platform
1boy 1girls arena arms_behind_back audience baggy_shirt belt bent_over black_vest blonde_hair blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block closed_eyes clothed_male_nude_female execution exhibitionism fate/grand_order fate_(series) female female_prisoner fire2water french french_girl gloves hair_ribbon hands_behind_back hands_tied hands_tied_behind_back imminent_death imminent_decapitation jeanne_d'arc_(fate) kneeling knight long_hair male medium_breasts neck_bound nipples nude nude_female nude_female_clothed_male original princess_knight prisoner white_woman wooden_platform
1girl barefoot bars bdsm blonde_hair blush bondage bound breasts cell censored chain chain_leash collar completely_nude feet female_focus female_prisoner female_pubic_hair indoors leash long_hair looking_at_viewer momo_chan navel nipples nude original prison prisoner pubic_hair pussy solo stocks toes torture
1girl barefoot bars bdsm blonde_hair blush bondage bound breasts cell censored chain chain_leash collar completely_nude feet female_focus female_prisoner female_pubic_hair indoors leash long_hair looking_at_viewer momo_chan navel nipples nude original prison prisoner pubic_hair pussy solo stocks toes torture
2girls beth_stevens_(hap) blonde_hair cfnf clothed clothed_female clothed_female_nude_female comic female female_prisoner femdom housewives housewives_at_play inmate lezdom lezsub looking_at_pussy madeline_nelson_(hap) multiple_girls nude nude_female prison psychologist rebecca_(artist) short_hair therapist whip yuri
2girls beth_stevens_(hap) blonde_hair cfnf clothed clothed_female clothed_female_nude_female comic female female_prisoner femdom housewives housewives_at_play inmate lezdom lezsub looking_at_pussy madeline_nelson_(hap) multiple_girls nude nude_female prison psychologist rebecca_(artist) short_hair therapist whip yuri
1girl armpits arms_up barefoot bdsm blue_hair blunt_bangs blush bondage bound bound_wrists breasts breasts_apart chain chained character_request clenched_teeth completely_nude creatures_(company) crying crying_with_eyes_open cuffs death_note dutch_angle female_focus female_prisoner game_freak green_eyes handcuffs indoors lizabeth_(pokemon) long_hair looking_at_viewer lowres medium_breasts navel nintendo nipples nude object_insertion peeking pokemon pokemon_(anime) pokemon_(creature) pokemon_ranger_and_the_temple_of_the_sea pokemon_rse_(anime) prison prisoner pussy_juice remote_control_vibrator running_bond ryuk sex_toy small_areolae small_nipples solo squatting stone_wall sunset tagme tears teeth twintails uncensored vaginal vaginal_object_insertion vibrator vibrator_cord wall when_you_see_it window
1girl armpits arms_up barefoot bdsm blue_hair blunt_bangs blush bondage bound bound_wrists breasts breasts_apart chain chained character_request clenched_teeth completely_nude creatures_(company) crying crying_with_eyes_open cuffs death_note dutch_angle female_focus female_prisoner game_freak green_eyes handcuffs indoors lizabeth_(pokemon) long_hair looking_at_viewer lowres medium_breasts navel nintendo nipples nude object_insertion peeking pokemon pokemon_(anime) pokemon_(creature) pokemon_ranger_and_the_temple_of_the_sea pokemon_rse_(anime) prison prisoner pussy_juice remote_control_vibrator running_bond ryuk sex_toy small_areolae small_nipples solo squatting stone_wall sunset tagme tears teeth twintails uncensored vaginal vaginal_object_insertion vibrator vibrator_cord wall when_you_see_it window
10s 1boy 1girl arms_up bdsm blush bondage bound breasts breasts_apart breasts_out brown_eyes cape censored chain clothing_aside cunnilingus dungeon bad_tag female_focus female_prisoner game_cg gladys_von_walkenheim hetero huge_breasts indoors kyonyuu_fantasy large_breasts mosaic_censoring navel nipples no_bra one_eye_closed open_mouth oral panties panties_aside prisoner pussy pussy_juice q-gaku ryuuto_henge saliva short_hair standing teeth underwear waffle_(company) white_hair
10s 1boy 1girl arms_up bdsm blush bondage bound breasts breasts_apart breasts_out brown_eyes cape censored chain clothing_aside cunnilingus dungeon bad_tag female_focus female_prisoner game_cg gladys_von_walkenheim hetero huge_breasts indoors kyonyuu_fantasy large_breasts mosaic_censoring navel nipples no_bra one_eye_closed open_mouth oral panties panties_aside prisoner pussy pussy_juice q-gaku ryuuto_henge saliva short_hair standing teeth underwear waffle_(company) white_hair
1girl 4bpp armpits arms_up bdsm bondage bondage_outfit bound bound_wrists breasts breasts_apart chain chain_leash chastity_belt collar coma_(artist) corset dutch_angle female_focus female_prisoner fetish_wear game_cg garter_belt garter_straps indoors leash looking_at_viewer nipples pc-98_(style) pil_(company) prison prison_bars prisoner rope seek_~chikashitsu_no_mesu_dorei-tachi~ sitting slave solo thighhighs
1girl 4bpp armpits arms_up bdsm bondage bondage_outfit bound bound_wrists breasts breasts_apart chain chain_leash chastity_belt collar coma_(artist) corset dutch_angle female_focus female_prisoner fetish_wear game_cg garter_belt garter_straps indoors leash looking_at_viewer nipples pc-98_(style) pil_(company) prison prison_bars prisoner rope seek_~chikashitsu_no_mesu_dorei-tachi~ sitting slave solo thighhighs
1girl armbinder arms_behind_back ass barefoot bars bdsm blush bondage bound bound_arms bowl breasts brown_eyes brown_hair bucket chain chain_leash closed_mouth collar coma_(artist) completely_nude feet female_focus female_prisoner floor game_cg harness indoors leash long_hair looking_at_viewer lying nipples nude on_floor on_side pc-98_(style) pet_bowl pil_(company) prison prison_bars prisoner seek_~chikashitsu_no_mesu_dorei-tachi~ slave solo toes vinyl
1girl armbinder arms_behind_back ass barefoot bars bdsm blush bondage bound bound_arms bowl breasts brown_eyes brown_hair bucket chain chain_leash closed_mouth collar coma_(artist) completely_nude feet female_focus female_prisoner floor game_cg harness indoors leash long_hair looking_at_viewer lying nipples nude on_floor on_side pc-98_(style) pet_bowl pil_(company) prison prison_bars prisoner seek_~chikashitsu_no_mesu_dorei-tachi~ slave solo toes vinyl
animated arms_up blush bondage chained_up chains cunnilingus damsel_in_distress dorei_ichiba dungeon female female_prisoner femsub helpless leg_up male maledom no_escape nude oral prisoner rape resisting resisting_pleasure restrained reverse_forced_oral separated_arms shaved_pussy struggling writhing
animated arms_up blush bondage chained_up chains cunnilingus damsel_in_distress dorei_ichiba dungeon female female_prisoner femsub helpless leg_up male maledom no_escape nude oral prisoner rape resisting resisting_pleasure restrained reverse_forced_oral separated_arms shaved_pussy struggling writhing
1boy 1girls arena arms_behind_back audience baggy_shirt beheaded beheading belt bent_over black_vest blonde_hair blood blood_splatter blood_spray blood_spurt blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block clenched_fists closed_eyes clothed_male_nude_female cut_neck death decapitated decapitated_head decapitation execution exhibitionism fate/grand_order fate_(series) female female_death female_prisoner fire2water flag french french_girl gloves gore hair_ribbon hands_behind_back hands_tied hands_tied_behind_back interracial jeanne_d'arc_(fate) kneeling kneeling_on_flag kneeling_on_floor knight long_hair male medium_breasts motion_lines neck_bound nipples nude nude_female nude_female_clothed_male original presenting_ass princess_knight prisoner quivering severed_head snuff tongue tongue_out trembling unseen_male_face white_woman wooden_platform
1boy 1girls arena arms_behind_back audience baggy_shirt beheaded beheading belt bent_over black_vest blonde_hair blood blood_splatter blood_spray blood_spurt blood_stain blue_pants bondage boots breasts british brown_belt brown_boots brown_gloves chopping_block clenched_fists closed_eyes clothed_male_nude_female cut_neck death decapitated decapitated_head decapitation execution exhibitionism fate/grand_order fate_(series) female female_death female_prisoner fire2water flag french french_girl gloves gore hair_ribbon hands_behind_back hands_tied hands_tied_behind_back interracial jeanne_d'arc_(fate) kneeling kneeling_on_flag kneeling_on_floor knight long_hair male medium_breasts motion_lines neck_bound nipples nude nude_female nude_female_clothed_male original presenting_ass princess_knight prisoner quivering severed_head snuff tongue tongue_out trembling unseen_male_face white_woman wooden_platform