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pear of anguish

+_+ 1girl :o animal_ears armchair bare_legs bare_shoulders black_dress blood bloody_knife blue_eyes chain chair collarbone commentary_request convenient_leg crack cracked_floor crown cuffs dress eyeball fork frilled_dress frilled_hairband frills full_body guro hair_between_eyes hairband hand_saw high_heels highres holding indoors knees knees_up knife lace_sleeves lace_trim legs light_brown_hair long_hair looking_at_viewer open_mouth original osobachan pear_of_anguish saw shackles shoes sidelocks single_shoe sitting solo tail tears torture_instruments unworn_shoes wooden_horse
+_+ 1girl :o animal_ears armchair bare_legs bare_shoulders black_dress blood bloody_knife blue_eyes chain chair collarbone commentary_request convenient_leg crack cracked_floor crown cuffs dress eyeball fork frilled_dress frilled_hairband frills full_body guro hair_between_eyes hairband hand_saw high_heels highres holding indoors knees knees_up knife lace_sleeves lace_trim legs light_brown_hair long_hair looking_at_viewer open_mouth original osobachan pear_of_anguish saw shackles shoes sidelocks single_shoe sitting solo tail tears torture_instruments unworn_shoes wooden_horse
1girl 2boys ^_^ ahoge axe balaclava black_gloves black_necktie black_shirt blood_on_axe blood_on_tool brown_jacket closed_eyes collared_shirt commentary_request crt fingerless_gloves girls'_frontline gloves grey_hair hair_between_eyes holding holding_pliers holding_power_drill holding_sign hostage jacket long_sleeves looking_at_viewer m200_(girls'_frontline) multiple_boys necktie open_mouth pear_of_anguish pliers purple_eyes saw shirt short_sleeves sign supaccha tears translation_request wavy_mouth white_shirt
1girl 2boys ^_^ ahoge axe balaclava black_gloves black_necktie black_shirt blood_on_axe blood_on_tool brown_jacket closed_eyes collared_shirt commentary_request crt fingerless_gloves girls'_frontline gloves grey_hair hair_between_eyes holding holding_pliers holding_power_drill holding_sign hostage jacket long_sleeves looking_at_viewer m200_(girls'_frontline) multiple_boys necktie open_mouth pear_of_anguish pliers purple_eyes saw shirt short_sleeves sign supaccha tears translation_request wavy_mouth white_shirt
1girl armor armpits bad_end bdsm bikini_armor bondage bound brown_hair captured clenched_teeth crying crying_with_eyes_open defeat drooling eternal_dread female_warrior from_above game_over highres horror_(theme) imminent_death imminent_penetration imminent_rape lying midriff navel on_back pear_of_anguish peeing peeing_self peril restrained ryona scalpel scared scared_expression stationary_restraints sweat tears teeth torture torture_chamber wide-eyed wide_eyes ym_(a901)
1girl armor armpits bad_end bdsm bikini_armor bondage bound brown_hair captured clenched_teeth crying crying_with_eyes_open defeat drooling eternal_dread female_warrior from_above game_over highres horror_(theme) imminent_death imminent_penetration imminent_rape lying midriff navel on_back pear_of_anguish peeing peeing_self peril restrained ryona scalpel scared scared_expression stationary_restraints sweat tears teeth torture torture_chamber wide-eyed wide_eyes ym_(a901)
1girl anger_vein blouse cardigan closed_eyes collarbone corruption false_smile fate/stay_night fate_(series) hair_ribbon highres holding long_hair matou_sakura mo_(kireinamo) open_mouth pear_of_anguish purple_hair red_ribbon ribbon shirt smile solo torture_instruments translated upper_body white_background
1girl anger_vein blouse cardigan closed_eyes collarbone corruption false_smile fate/stay_night fate_(series) hair_ribbon highres holding long_hair matou_sakura mo_(kireinamo) open_mouth pear_of_anguish purple_hair red_ribbon ribbon shirt smile solo torture_instruments translated upper_body white_background
1girl ass blue_hair bob_cut bottomless brown_eyes chain collar convenient_censoring cowboy_shot cuffs eyebrows female_focus from_behind looking_at_viewer looking_back original pear_of_anguish short_hair simple_background single_eyebrow solo standing torn_clothes ujiga_waita white_background
1girl ass blue_hair bob_cut bottomless brown_eyes chain collar convenient_censoring cowboy_shot cuffs eyebrows female_focus from_behind looking_at_viewer looking_back original pear_of_anguish short_hair simple_background single_eyebrow solo standing torn_clothes ujiga_waita white_background
1girl bat_wings blush breasts dress_shirt female_focus grappling_hook hammer_(sunset_beach) head_wings koakuma large_breasts looking_at_viewer necktie one_eye_closed pear_of_anguish red_eyes red_hair shirt simple_background smile solo tongue touhou upper_body wings
1girl bat_wings blush breasts dress_shirt female_focus grappling_hook hammer_(sunset_beach) head_wings koakuma large_breasts looking_at_viewer necktie one_eye_closed pear_of_anguish red_eyes red_hair shirt simple_background smile solo tongue touhou upper_body wings
1girl arms_behind_back ball_and_chain_restraint bdsm blood blood_from_mouth bondage bound bow bow_panties breast_pump breasts bruise chain character_request cuffs dot_nose feet female_focus forceps from_above full_body highres injury kneehighs long_hair looking_at_viewer looking_up milking_machine monochrome navel nipples panties pear_of_anguish shackles simple_background sitting sketch small_breasts socks solo topless torn_clothes traditional_media uncensored underwear underwear_only white_background zero_(miraichizu)
1girl arms_behind_back ball_and_chain_restraint bdsm blood blood_from_mouth bondage bound bow bow_panties breast_pump breasts bruise chain character_request cuffs dot_nose feet female_focus forceps from_above full_body highres injury kneehighs long_hair looking_at_viewer looking_up milking_machine monochrome navel nipples panties pear_of_anguish shackles simple_background sitting sketch small_breasts socks solo topless torn_clothes traditional_media uncensored underwear underwear_only white_background zero_(miraichizu)
1girl :d ass black_socks collarbone dot_nose empty_eyes female_focus full_body grey_hair hand_on_own_cheek hand_on_own_face highres loafers long_hair open_mouth original pear_of_anguish pleated_skirt shoes simple_background skirt smile socks solo torture_instruments white_background yellow_eyes yu-ta
1girl :d ass black_socks collarbone dot_nose empty_eyes female_focus full_body grey_hair hand_on_own_cheek hand_on_own_face highres loafers long_hair open_mouth original pear_of_anguish pleated_skirt shoes simple_background skirt smile socks solo torture_instruments white_background yellow_eyes yu-ta
1girl amputee angry bdsm bondage bound breasts elf hogtie ikelag medium_breasts nipples pear_of_anguish pointy_ears quadruple_amputee suspension
1girl amputee angry bdsm bondage bound breasts elf hogtie ikelag medium_breasts nipples pear_of_anguish pointy_ears quadruple_amputee suspension
10s 1boy 1futa 1girl after_anal aftersex anus arms_up ass ass_grab bdsm between_breasts bisexual_female bondage bottomless bound breast_press breasts breasts_out censored chronoire_schwarz_vi clothed_female_nude_male clothing_aside cum cum_in_ass cumdrip dildo dutch_angle feet ffm_threesome futa_with_female futanari group_sex hat indoors kagari_kazane kariinu large_breasts legs lolita_channel looking_at_viewer mask medium_breasts mosaic_censoring multicolored_hair navel necktie nipples no_shoes nude open_clothes orange_hair panties panties_aside pantyhose pear_of_anguish penis pussy rape sex_toy smile spiked_dildo spread_anus spread_legs standing stocks straddling strap-on tears thighs threesome torn_clothes torn_legwear underwear upright_straddle veins veiny_penis witch_craft_works
10s 1boy 1futa 1girl after_anal aftersex anus arms_up ass ass_grab bdsm between_breasts bisexual_female bondage bottomless bound breast_press breasts breasts_out censored chronoire_schwarz_vi clothed_female_nude_male clothing_aside cum cum_in_ass cumdrip dildo dutch_angle feet ffm_threesome futa_with_female futanari group_sex hat indoors kagari_kazane kariinu large_breasts legs lolita_channel looking_at_viewer mask medium_breasts mosaic_censoring multicolored_hair navel necktie nipples no_shoes nude open_clothes orange_hair panties panties_aside pantyhose pear_of_anguish penis pussy rape sex_toy smile spiked_dildo spread_anus spread_legs standing stocks straddling strap-on tears thighs threesome torn_clothes torn_legwear underwear upright_straddle veins veiny_penis witch_craft_works
1girl bare_shoulders blood chain copyright_request grey_hair hair_over_one_eye highres judas_cradle language_request mole muk_(monsieur) original oversized_object pear_of_anguish simple_background sleeveless tattoo thigh_strap translation_request yellow_eyes
1girl bare_shoulders blood chain copyright_request grey_hair hair_over_one_eye highres judas_cradle language_request mole muk_(monsieur) original oversized_object pear_of_anguish simple_background sleeveless tattoo thigh_strap translation_request yellow_eyes
1boy 3girls armpits arms_up bdsm belt_collar blindfold bondage bound branding_iron breasts breasts_apart collar dragon_quest dragon_quest_iii drooling dutch_angle gradient_background grey_background kizaki merchant_(dq3) multiple_girls nervous_sweating nipples nude open_mouth pear_of_anguish simple_background slave small_breasts snot square_enix sweat tears teeth tongue topless_frame torture volvox wet whip_marks
1boy 3girls armpits arms_up bdsm belt_collar blindfold bondage bound branding_iron breasts breasts_apart collar dragon_quest dragon_quest_iii drooling dutch_angle gradient_background grey_background kizaki merchant_(dq3) multiple_girls nervous_sweating nipples nude open_mouth pear_of_anguish simple_background slave small_breasts snot square_enix sweat tears teeth tongue topless_frame torture volvox wet whip_marks
1boy 3girls anal anal_object_insertion areola_piercing arms_behind_back bag bdsm blush bondage bookbag bound breasts brown_eyes brown_hair clitoris_piercing collar dildo egg_vibrator female_pubic_hair flute handkerchief huge_breasts huge_dildo instrument labia_piercing large_breasts large_insertion long_hair looking_at_viewer masochism mismatched_irises mouth_hold multiple_girls necktie nipple_piercing nipple_tag no_bra no_panties nude object_insertion open_mouth pants pear_of_anguish pen piercing ponytail pubic_hair public_indecency public_use pussy_piercing q_azieru recorder revealing_clothes ruler safety_pin school_uniform scissors serafuku sex_toy shirt short_hair simple_background smile socks spiked_dildo spread_legs spreader_bar surprised sweat too_many too_many_sex_toys twintails underboob vaginal vaginal_object_insertion vibrator whip white_background zenra
1boy 3girls anal anal_object_insertion areola_piercing arms_behind_back bag bdsm blush bondage bookbag bound breasts brown_eyes brown_hair clitoris_piercing collar dildo egg_vibrator female_pubic_hair flute handkerchief huge_breasts huge_dildo instrument labia_piercing large_breasts large_insertion long_hair looking_at_viewer masochism mismatched_irises mouth_hold multiple_girls necktie nipple_piercing nipple_tag no_bra no_panties nude object_insertion open_mouth pants pear_of_anguish pen piercing ponytail pubic_hair public_indecency public_use pussy_piercing q_azieru recorder revealing_clothes ruler safety_pin school_uniform scissors serafuku sex_toy shirt short_hair simple_background smile socks spiked_dildo spread_legs spreader_bar surprised sweat too_many too_many_sex_toys twintails underboob vaginal vaginal_object_insertion vibrator whip white_background zenra
1girl bdsm blonde_hair blush bondage bound breasts bubuzuke censored chichi_ninja chichi_ninja_revolution female_focus long_hair mosaic_censoring nipples nude pear_of_anguish purple_eyes pussy pussy_juice solo spreader_bar sweat tanaka_momoko vaginal
1girl bdsm blonde_hair blush bondage bound breasts bubuzuke censored chichi_ninja chichi_ninja_revolution female_focus long_hair mosaic_censoring nipples nude pear_of_anguish purple_eyes pussy pussy_juice solo spreader_bar sweat tanaka_momoko vaginal
10s 1girl 2011 anal anal_object_insertion artist_name ass ball_gag bdsm blush bodysuit chastity_belt female_focus from_behind gag gagged gloves leaning_forward long_hair looking_at_viewer looking_back object_insertion pear_of_anguish red_eyes red_hair simple_background solo uzushio_(uzusio)
10s 1girl 2011 anal anal_object_insertion artist_name ass ball_gag bdsm blush bodysuit chastity_belt female_focus from_behind gag gagged gloves leaning_forward long_hair looking_at_viewer looking_back object_insertion pear_of_anguish red_eyes red_hair simple_background solo uzushio_(uzusio)
1girl anal_beads ass backboob backpack bad_anatomy bag bdsm bent_over blush breasts brown_eyes brown_hair chair classroom cum cum_in_pussy cumdrip desk dilation_belt dildo egg_vibrator female_focus gaping happy happy_sex harness huge_breasts indoors lactation looking_at_viewer looking_back masochism milk_pool miyauchi_ushio naughty_face nekomamire nipple_tag nude object_insertion open_mouth oppai_loli pear_of_anguish puffy_nipples pussy pussy_juice randoseru school sex_toy short_hair solo spread_ass spread_pussy tiptoes underwear vaginal vaginal_object_insertion vibrator
1girl anal_beads ass backboob backpack bad_anatomy bag bdsm bent_over blush breasts brown_eyes brown_hair chair classroom cum cum_in_pussy cumdrip desk dilation_belt dildo egg_vibrator female_focus gaping happy happy_sex harness huge_breasts indoors lactation looking_at_viewer looking_back masochism milk_pool miyauchi_ushio naughty_face nekomamire nipple_tag nude object_insertion open_mouth oppai_loli pear_of_anguish puffy_nipples pussy pussy_juice randoseru school sex_toy short_hair solo spread_ass spread_pussy tiptoes underwear vaginal vaginal_object_insertion vibrator
1girl anus armpits ayane_(doa) bare_shoulders bdsm blush bondage bottomless bound breasts censored clitoris dead_or_alive detached_sleeves dilation_insertion extreme_spread faker4 gagged gaping headband keny large_insertion male_hand nipples object_insertion pear_of_anguish purple_hair purple_thighhighs pussy pussy_juice red_eyes short_hair solo_focus spread_legs spread_pussy sweat tecmo thighhighs torture torture_instruments urethra
1girl anus armpits ayane_(doa) bare_shoulders bdsm blush bondage bottomless bound breasts censored clitoris dead_or_alive detached_sleeves dilation_insertion extreme_spread faker4 gagged gaping headband keny large_insertion male_hand nipples object_insertion pear_of_anguish purple_hair purple_thighhighs pussy pussy_juice red_eyes short_hair solo_focus spread_legs spread_pussy sweat tecmo thighhighs torture torture_instruments urethra
1girl ayane_(doa) bdsm bondage bound censored dead_or_alive dilation_insertion faker4 female_focus gagged gaping keny large_insertion nipples object_insertion pear_of_anguish pussy solo spread_pussy tecmo torture torture_instruments
1girl ayane_(doa) bdsm bondage bound censored dead_or_alive dilation_insertion faker4 female_focus gagged gaping keny large_insertion nipples object_insertion pear_of_anguish pussy solo spread_pussy tecmo torture torture_instruments
1girl absurdres armpits ayane_(doa) bare_shoulders bdsm blush bondage bottomless bound breasts censored cervix clitoral_hood clitoris crying crying_with_eyes_open dead_or_alive detached_sleeves dilation_insertion extreme_spread faker4 female_focus gagged gaping grey_background highres keny large_insertion medium_breasts nipples object_insertion pear_of_anguish purple_hair purple_thighhighs pussy pussy_juice pussy_juice_puddle pussy_juice_trail red_eyes short_hair simple_background solo spread_legs spread_pussy sweat tears tecmo thighhighs torture torture_instruments
1girl absurdres armpits ayane_(doa) bare_shoulders bdsm blush bondage bottomless bound breasts censored cervix clitoral_hood clitoris crying crying_with_eyes_open dead_or_alive detached_sleeves dilation_insertion extreme_spread faker4 female_focus gagged gaping grey_background highres keny large_insertion medium_breasts nipples object_insertion pear_of_anguish purple_hair purple_thighhighs pussy pussy_juice pussy_juice_puddle pussy_juice_trail red_eyes short_hair simple_background solo spread_legs spread_pussy sweat tears tecmo thighhighs torture torture_instruments
1girl bdsm bondage bottomless bound chair clenched_teeth female_focus female_pubic_hair glasses greyscale mayonnaise_(ringo_gakuen) monochrome no_panties object_insertion original pear_of_anguish pubic_hair pussy rope short_hair simple_background solo spread_legs stomach_bulge sweat tears teeth thighhighs torn_clothes torture torture_instruments vaginal white_background
1girl bdsm bondage bottomless bound chair clenched_teeth female_focus female_pubic_hair glasses greyscale mayonnaise_(ringo_gakuen) monochrome no_panties object_insertion original pear_of_anguish pubic_hair pussy rope short_hair simple_background solo spread_legs stomach_bulge sweat tears teeth thighhighs torn_clothes torture torture_instruments vaginal white_background