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male masochism

1boy 1girls bare_legs bare_thighs black_hair blazer bleach breasts canonical_scene close-up clothed clothed_female enjoying female full_body going_commando kon kuchiki_rukia legwear light-skinned_female light_skin long_hair male male/female male_masochism masochism masochist no_panties no_shoes no_underwear nopan petite purple_eyes pussy ribbon ribbon_choker rozuberry school_uniform schoolgirl short_black_hair skirt small_breasts smaller_female socks spoken_heart stomping stuffed_animal stuffed_toy upskirt wide_hips
1boy 1girls bare_legs bare_thighs black_hair blazer bleach breasts canonical_scene close-up clothed clothed_female enjoying female full_body going_commando kon kuchiki_rukia legwear light-skinned_female light_skin long_hair male male/female male_masochism masochism masochist no_panties no_shoes no_underwear nopan petite purple_eyes pussy ribbon ribbon_choker rozuberry school_uniform schoolgirl short_black_hair skirt small_breasts smaller_female socks spoken_heart stomping stuffed_animal stuffed_toy upskirt wide_hips
1boy 1girls anal anal_bleeding anal_juice anal_sex arms_behind_back ball_gag bar_censor big_dildo black_hair blonde_hair blood blue_background blush bondage bottomless butterfly_hair_ornament closed_eyes deep_penetration demon_slayer douma drooling duct_tape erection fake_penis female femdom from_behind gag gakuran garter_straps happy_sub heart-shaped_pupils kimetsu_no_yaiba kochou_shinobu lace lace-trimmed_thighhighs large_insertion leash leash_pull long_hair_male male male_masochism male_penetrated male_pubic_hair male_urethral_insertion malesub masochism masochist nipple_piercing pegging penis piercing_pull smile sounding spiky_hair stockings strap-on studded_dildo tape tape_bondage tears thighhighs two_tone_hair uniform urethral_beads urethral_insertion wisteria x-ray
1boy 1girls anal anal_bleeding anal_juice anal_sex arms_behind_back ball_gag bar_censor big_dildo black_hair blonde_hair blood blue_background blush bondage bottomless butterfly_hair_ornament closed_eyes deep_penetration demon_slayer douma drooling duct_tape erection fake_penis female femdom from_behind gag gakuran garter_straps happy_sub heart-shaped_pupils kimetsu_no_yaiba kochou_shinobu lace lace-trimmed_thighhighs large_insertion leash leash_pull long_hair_male male male_masochism male_penetrated male_pubic_hair male_urethral_insertion malesub masochism masochist nipple_piercing pegging penis piercing_pull smile sounding spiky_hair stockings strap-on studded_dildo tape tape_bondage tears thighhighs two_tone_hair uniform urethral_beads urethral_insertion wisteria x-ray
1boy black_corset black_garter_straps black_high_heels black_latex black_latex_corset black_latex_garter_straps black_latex_thighhighs black_latex_thong black_thighhighs black_thong bondage bound bustier cleavage clothed_female_nude_male commentary_request commission corset dominatrix dungeon elbow_gloves female femdom fetish fetish_wear garter_straps gloves high_heels highres indoors kantai_collection katsuten latex latex_corset latex_garter_straps latex_lingerie latex_thighhighs latex_thong male male_masochism malesub masochism nude penis red_whip sadism sendai_(kantai_collection) textless thighhighs thong whip
1boy black_corset black_garter_straps black_high_heels black_latex black_latex_corset black_latex_garter_straps black_latex_thighhighs black_latex_thong black_thighhighs black_thong bondage bound bustier cleavage clothed_female_nude_male commentary_request commission corset dominatrix dungeon elbow_gloves female femdom fetish fetish_wear garter_straps gloves high_heels highres indoors kantai_collection katsuten latex latex_corset latex_garter_straps latex_lingerie latex_thighhighs latex_thong male male_masochism malesub masochism nude penis red_whip sadism sendai_(kantai_collection) textless thighhighs thong whip
1boy 1girls anal anal_penetration androgynous animal_ears areolae arms_up aroused ass ass_focus ass_grab ball_gag bed bed_sheet bedroom black_hair blush bondage bondage_outfit bound breasts brown_eyes brown_hair bunny_ears bunny_tail bunnysuit canon_crossdressing casino celestia_ludenberg clenched_hand clenched_hands collar crossdressing crying danganronpa danganronpa_1 dildo domination dominatrix drooling dutch_angle elbow_gloves english_text eudetenis female femboy femdom feminization fishnet_legwear fishnets frills fujisaki_chihiro functionally_nude gag gagged girly gloves gothic_lolita handjob harness harness_ball_gag harness_gag head_harness high_heels humiliation lolita_fashion male male_masochism male_penetrated malesub masochism medium_breasts nipples one_eye_closed pegging penetration precum precum_drip precum_trail reach_around red_eyes sadism sex sex_toy size_difference small_nipples small_penis smooth_skin speech_bubble stockings strap-on tail tears text wanderer2691
1boy 1girls anal anal_penetration androgynous animal_ears areolae arms_up aroused ass ass_focus ass_grab ball_gag bed bed_sheet bedroom black_hair blush bondage bondage_outfit bound breasts brown_eyes brown_hair bunny_ears bunny_tail bunnysuit canon_crossdressing casino celestia_ludenberg clenched_hand clenched_hands collar crossdressing crying danganronpa danganronpa_1 dildo domination dominatrix drooling dutch_angle elbow_gloves english_text eudetenis female femboy femdom feminization fishnet_legwear fishnets frills fujisaki_chihiro functionally_nude gag gagged girly gloves gothic_lolita handjob harness harness_ball_gag harness_gag head_harness high_heels humiliation lolita_fashion male male_masochism male_penetrated malesub masochism medium_breasts nipples one_eye_closed pegging penetration precum precum_drip precum_trail reach_around red_eyes sadism sex sex_toy size_difference small_nipples small_penis smooth_skin speech_bubble stockings strap-on tail tears text wanderer2691
abuse always-under-feet barefoot bent_over black_hair boxers closed_eyes clothed_female_nude_male collar dominant dominant_female domination feet_on_face female foot_fetish foot_focus foot_worship kurenai_yuhi lipstick makeup male male_masochism malesub masochism masochist milf naruto naruto_(series) naruto_shippuden red_eyes sadism sex_slave short_hair smile spiked_collar standing stepped_on stomping submissive submissive_male underwear yuuhi_kurenai
abuse always-under-feet barefoot bent_over black_hair boxers closed_eyes clothed_female_nude_male collar dominant dominant_female domination feet_on_face female foot_fetish foot_focus foot_worship kurenai_yuhi lipstick makeup male male_masochism malesub masochism masochist milf naruto naruto_(series) naruto_shippuden red_eyes sadism sex_slave short_hair smile spiked_collar standing stepped_on stomping submissive submissive_male underwear yuuhi_kurenai
1boy 1girls barefoot blonde_hair blue_eyes body_writing bondage brown_hair censored chains clothed_female_nude_male completely_nude completely_nude_male couch cum erection feet female femboy femdom glasses highres locker long_hair male_masochism malesub masochism nipple_piercing nude open_mouth original pantyhose penis piercing sadism school_uniform shoes short_hair smile standing tears testicles torture translation_request violence whip whip_marks whipping wokada
1boy 1girls barefoot blonde_hair blue_eyes body_writing bondage brown_hair censored chains clothed_female_nude_male completely_nude completely_nude_male couch cum erection feet female femboy femdom glasses highres locker long_hair male_masochism malesub masochism nipple_piercing nude open_mouth original pantyhose penis piercing sadism school_uniform shoes short_hair smile standing tears testicles torture translation_request violence whip whip_marks whipping wokada
1boy 1girls anger_vein blush butterfly_hair_ornament demon_boy demon_slayer dominant_female domination douma female femdom fully_clothed haori happy_sub heart i katana kimetsu_no_yaiba kochou_shinobu lean! love male male_masochism malesub masochism masochist nikkiyan pantsuyan size_difference small_dom_big_sub smile stepped_on stepping_on_penis sword uniform weapon wholesome zouri
1boy 1girls anger_vein blush butterfly_hair_ornament demon_boy demon_slayer dominant_female domination douma female femdom fully_clothed haori happy_sub heart i katana kimetsu_no_yaiba kochou_shinobu lean! love male male_masochism malesub masochism masochist nikkiyan pantsuyan size_difference small_dom_big_sub smile stepped_on stepping_on_penis sword uniform weapon wholesome zouri
1boy 1girls 69 abuse abused akame_ga_kill! asphyxiation ass ass_sniffing ass_worship big_ass big_breasts blue_eyes blue_hair blush breasts broken_nose bruise bruise_on_face bruised bruises butt_sniffing cry crying cunnilingus domination dominatrix esdeath_(akame_ga_kill!) face_in_ass facesitting female femdom fetish green_eyes green_hair humiliation licking licking_pussy looking_down lubbock_(akame_ga_kill!) male male_masochism malesub masochism masochist nose_in_anus nose_to_anus punishment sadism sadistic sadistic_girl sitting sitting_on_face sitting_on_person slave smell smelling smile smiling smirk smirking smothering sniff sniffing spreading_ass tears torture x-ray
1boy 1girls 69 abuse abused akame_ga_kill! asphyxiation ass ass_sniffing ass_worship big_ass big_breasts blue_eyes blue_hair blush breasts broken_nose bruise bruise_on_face bruised bruises butt_sniffing cry crying cunnilingus domination dominatrix esdeath_(akame_ga_kill!) face_in_ass facesitting female femdom fetish green_eyes green_hair humiliation licking licking_pussy looking_down lubbock_(akame_ga_kill!) male male_masochism malesub masochism masochist nose_in_anus nose_to_anus punishment sadism sadistic sadistic_girl sitting sitting_on_face sitting_on_person slave smell smelling smile smiling smirk smirking smothering sniff sniffing spreading_ass tears torture x-ray
1boy 1boy1girl 1girls ahoge atalanta_(fate) bed bedroom bedroom_setting bedroom_sex big_ass big_butt big_thighs bigger_dom black_hair black_lingerie black_thighhighs blonde_hair blush cat_ears cat_tail catgirl curvy curvy_body curvy_female curvy_figure detailed_background faceless_male facesitting fate/apocrypha fate/grand_order fate_(series) female femdom fujimaru_ritsuka_(male) glistening_skin green_eyes green_hair gudao hands_on_thighs happy height_difference huge_ass huge_butt japanese_text larger_female lingerie long_hair looking_back looking_down male_masochism malesub masochism masochist motion_lines open_mouth pink_background pink_text pleasure_face red_text round_ass short_hair shorter_male sitting sitting_on_penis sitting_on_person size_difference size_play smaller_male smaller_sub smiling steamy steamy_ass steamy_breath steamy_pussy sweat sweaty taller_female taller_girl text_box thick_thighs thigh_highs thighhighs visible_breath voluptuous
1boy 1boy1girl 1girls ahoge atalanta_(fate) bed bedroom bedroom_setting bedroom_sex big_ass big_butt big_thighs bigger_dom black_hair black_lingerie black_thighhighs blonde_hair blush cat_ears cat_tail catgirl curvy curvy_body curvy_female curvy_figure detailed_background faceless_male facesitting fate/apocrypha fate/grand_order fate_(series) female femdom fujimaru_ritsuka_(male) glistening_skin green_eyes green_hair gudao hands_on_thighs happy height_difference huge_ass huge_butt japanese_text larger_female lingerie long_hair looking_back looking_down male_masochism malesub masochism masochist motion_lines open_mouth pink_background pink_text pleasure_face red_text round_ass short_hair shorter_male sitting sitting_on_penis sitting_on_person size_difference size_play smaller_male smaller_sub smiling steamy steamy_ass steamy_breath steamy_pussy sweat sweaty taller_female taller_girl text_box thick_thighs thigh_highs thighhighs visible_breath voluptuous
always-under-feet barefoot black_hair clothed_female_nude_male feet female femdom foot_fetish foot_focus foot_lick foot_worship from_below kurenai_yuhi long_hair male male_masochism masochism masochist mature mature_female milf naruto naruto_(series) naruto_shippuden oral sex_slave slave step_pose toes tongue tongue_out viewed_from_below voluptuous wide_hips yuuhi_kurenai
always-under-feet barefoot black_hair clothed_female_nude_male feet female femdom foot_fetish foot_focus foot_lick foot_worship from_below kurenai_yuhi long_hair male male_masochism masochism masochist mature mature_female milf naruto naruto_(series) naruto_shippuden oral sex_slave slave step_pose toes tongue tongue_out viewed_from_below voluptuous wide_hips yuuhi_kurenai
1boy 1boy1girl 1girls armbinder arms_tied black_corset black_text black_thigh_highs black_thighhighs bodysuit bondage bondage_chair bondage_gear bondage_outfit breasts brown_background corset dark-skinned_male dildo_in_ass dominant_female dominatrix fate/extra fate/grand_order fate_(series) female femdom gradient_background heart japanese_text latex latex_gloves latex_legwear light-skinned_female long_hair male_masochism malesub masochism masochist medium_breasts pegging pink_heart pink_lips pink_lipstick purple_bodysuit purple_eyes purple_hair sadistic scathach_(fate) scathach_(swimsuit_assassin) smiling strap-on submissive_male sweating thighhighs
1boy 1boy1girl 1girls armbinder arms_tied black_corset black_text black_thigh_highs black_thighhighs bodysuit bondage bondage_chair bondage_gear bondage_outfit breasts brown_background corset dark-skinned_male dildo_in_ass dominant_female dominatrix fate/extra fate/grand_order fate_(series) female femdom gradient_background heart japanese_text latex latex_gloves latex_legwear light-skinned_female long_hair male_masochism malesub masochism masochist medium_breasts pegging pink_heart pink_lips pink_lipstick purple_bodysuit purple_eyes purple_hair sadistic scathach_(fate) scathach_(swimsuit_assassin) smiling strap-on submissive_male sweating thighhighs
1boy 1boy1girl 1girls ahoge angry angry_expression angry_face angry_sex atalanta_(fate) bed bedroom bedroom_setting bedroom_sex big_ass big_butt big_thighs bigger_dom black_hair black_lingerie black_text black_thighhighs blonde_hair blush cat_ears cat_tail catgirl curvy curvy_body curvy_female curvy_figure detailed_background exclamation faceless_male facesitting fangs fate/apocrypha fate/grand_order fate_(series) female femdom fujimaru_ritsuka_(male) glistening_skin green_eyes green_hair gudao hands_on_thighs height_difference huge_ass huge_butt japanese_text larger_female lingerie long_hair looking_back looking_down male_masochism malesub masochism masochist open_mouth pink_background pink_text round_ass short_hair shorter_male shouting sitting sitting_on_penis sitting_on_person size_difference size_play smaller_male smaller_sub sound_effects speech_bubble sweat sweaty talking_to_partner taller_female taller_girl thick_thighs thigh_highs thighhighs voluptuous white_text yelling
1boy 1boy1girl 1girls ahoge angry angry_expression angry_face angry_sex atalanta_(fate) bed bedroom bedroom_setting bedroom_sex big_ass big_butt big_thighs bigger_dom black_hair black_lingerie black_text black_thighhighs blonde_hair blush cat_ears cat_tail catgirl curvy curvy_body curvy_female curvy_figure detailed_background exclamation faceless_male facesitting fangs fate/apocrypha fate/grand_order fate_(series) female femdom fujimaru_ritsuka_(male) glistening_skin green_eyes green_hair gudao hands_on_thighs height_difference huge_ass huge_butt japanese_text larger_female lingerie long_hair looking_back looking_down male_masochism malesub masochism masochist open_mouth pink_background pink_text round_ass short_hair shorter_male shouting sitting sitting_on_penis sitting_on_person size_difference size_play smaller_male smaller_sub sound_effects speech_bubble sweat sweaty talking_to_partner taller_female taller_girl thick_thighs thigh_highs thighhighs voluptuous white_text yelling
1boy 1girls black_hair blue_eyes blush canon_genderswap collar demon_boy demon_slayer demoness doenmu enmu facial_markings female femdom fully_clothed genderswap_(mtf) hair_bun hair_ornament kimetsu_no_yaiba kimono leash leash_pull lipstick looking_at_another looking_pleasured male male_masochism malesub masochism multicolored_hair muzan_kibutsuji nail_polish obi pale-skinned_female pale-skinned_male pale_skin red_eyes red_lipstick rule_63 sharp_nails sidelocks smile upper_body veins wavy_hair
1boy 1girls black_hair blue_eyes blush canon_genderswap collar demon_boy demon_slayer demoness doenmu enmu facial_markings female femdom fully_clothed genderswap_(mtf) hair_bun hair_ornament kimetsu_no_yaiba kimono leash leash_pull lipstick looking_at_another looking_pleasured male male_masochism malesub masochism multicolored_hair muzan_kibutsuji nail_polish obi pale-skinned_female pale-skinned_male pale_skin red_eyes red_lipstick rule_63 sharp_nails sidelocks smile upper_body veins wavy_hair
1girls 3boys bb_(baalbuddy) belly black_hair comedy coomer female funny garter_belt highschool_of_the_dead katana large_breasts long_black_hair long_hair male_masochism masochism masochist meme monochrome navel ripped_clothing saeko_busujima school_uniform skirt zombies
1girls 3boys bb_(baalbuddy) belly black_hair comedy coomer female funny garter_belt highschool_of_the_dead katana large_breasts long_black_hair long_hair male_masochism masochism masochist meme monochrome navel ripped_clothing saeko_busujima school_uniform skirt zombies
... 1boy 1girls between_thighs braided_hair breasts canon_couple cleavage couple cowgirl_position deep_skin demon_slayer female gradient_hair green_eyes green_legwear grey_background haori headlock headscissor highres huge_breasts iguro_obanai japanese_clothes kaburamaru kanroji_mitsuri kimetsu_no_yaiba long_hair lying male_masochism masochism mole mole_under_eye multicolored_hair on_back open_clothes pink_hair pleated_skirt ribbed_legwear sadism scissorhold shounen_jump simple_background sitting skirt spoken_ellipsis straight text thick_thighs thigh_grab thighhighs thighs thumbs_up thunder_thighs tingtongten twin_braids very_long_hair
... 1boy 1girls between_thighs braided_hair breasts canon_couple cleavage couple cowgirl_position deep_skin demon_slayer female gradient_hair green_eyes green_legwear grey_background haori headlock headscissor highres huge_breasts iguro_obanai japanese_clothes kaburamaru kanroji_mitsuri kimetsu_no_yaiba long_hair lying male_masochism masochism mole mole_under_eye multicolored_hair on_back open_clothes pink_hair pleated_skirt ribbed_legwear sadism scissorhold shounen_jump simple_background sitting skirt spoken_ellipsis straight text thick_thighs thigh_grab thighhighs thighs thumbs_up thunder_thighs tingtongten twin_braids very_long_hair