_next popular

Tags

male masochism

1boy 1girls animated bootjob boots city cityscape cleavage clothed_female cum dominant_female domination dominatrix dress fate/grand_order fate_(series) femdom foot_focus footjob helmet high_heel_boots inin4531 jeanne_alter jeanne_d'arc_(fate) leather_boots light-skinned_female light-skinned_male light_skin low_cut_dress low_framerate male_masochism male_pov malesub masochism night nighttime nude_male outdoors penis pov pov_ass receiving_on_back receiving_pov ruined_orgasm stepped_on stepping_on_penis white_hair
1boy 1girls animated bootjob boots city cityscape cleavage clothed_female cum dominant_female domination dominatrix dress fate/grand_order fate_(series) femdom foot_focus footjob helmet high_heel_boots inin4531 jeanne_alter jeanne_d'arc_(fate) leather_boots light-skinned_female light-skinned_male light_skin low_cut_dress low_framerate male_masochism male_pov malesub masochism night nighttime nude_male outdoors penis pov pov_ass receiving_on_back receiving_pov ruined_orgasm stepped_on stepping_on_penis white_hair
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 1girls alternate_costume ass_up black_gloves black_thong blood breasts_out bruised bustier canon_genderswap clothed clothed_dom_nude_sub clothed_female clothed_female_nude_male corset dokayuki dominatrix elbow_gloves face_down_ass_up female femdom full_body garter_straps genderswap_(ftm) genderswap_(mtf) ginko_sakata gintama gintoki_sakata glasses gloves high_heels lingerie looking_at_viewer looking_back male male_masochism malesub masochism masochist masochistic_male medium_breasts naked_glasses neck_ribbon nude nude_male nylons purple_hair red_eyes restrained riding_crop rope rule_63 sarutobi_ayame sarutobi_ayao sheer_legwear short_hair sideboob sitting_on_person spreader_bar stockings thong very_short_hair whip_marks white_hair wrists_to_ankles
1boy 1girls alternate_costume ass_up black_gloves black_thong blood breasts_out bruised bustier canon_genderswap clothed clothed_dom_nude_sub clothed_female clothed_female_nude_male corset dokayuki dominatrix elbow_gloves face_down_ass_up female femdom full_body garter_straps genderswap_(ftm) genderswap_(mtf) ginko_sakata gintama gintoki_sakata glasses gloves high_heels lingerie looking_at_viewer looking_back male male_masochism malesub masochism masochist masochistic_male medium_breasts naked_glasses neck_ribbon nude nude_male nylons purple_hair red_eyes restrained riding_crop rope rule_63 sarutobi_ayame sarutobi_ayao sheer_legwear short_hair sideboob sitting_on_person spreader_bar stockings thong very_short_hair whip_marks white_hair wrists_to_ankles
2022 2boys absurd_res alcohol anthro antlers arthur_(furfragged) bathroom beverage biped bottomless breasts canid canine cervid chubby_anthro chubby_male clothed clothing cloven_hooves colored countershading critical_hit digitigrade door duo end_table english_text eyewear female foreplay furfragged furniture gameplay_mechanics glasses gui health_bar heart hi_res hooves horn hud intraspecies life_(gaming) male male/male male_masochism male_only mammal masochism mug on_sofa potbelly public public_sex sadism scut_tail sex short_tail sigh sino_(furfragged) slightly_chubby smile sofa spanking sperm_cell stat_bars status_effect text tongue tongue_out voyeur
2022 2boys absurd_res alcohol anthro antlers arthur_(furfragged) bathroom beverage biped bottomless breasts canid canine cervid chubby_anthro chubby_male clothed clothing cloven_hooves colored countershading critical_hit digitigrade door duo end_table english_text eyewear female foreplay furfragged furniture gameplay_mechanics glasses gui health_bar heart hi_res hooves horn hud intraspecies life_(gaming) male male/male male_masochism male_only mammal masochism mug on_sofa potbelly public public_sex sadism scut_tail sex short_tail sigh sino_(furfragged) slightly_chubby smile sofa spanking sperm_cell stat_bars status_effect text tongue tongue_out voyeur
1boy 1boy1girl 1girls angry annoyed bare_legs bare_thighs barefoot black_hair blazer bleach bunny_panties bunny_print cameltoe canonical_scene clothed clothed_female ecchisage feet female female_focus irritated kon kuchiki_rukia long_hair male_masochism masochism masochist no_shoes panties pantsu petite petite_body pout pouting purple_eyes school_uniform shirt skirt smaller_female socks stomp stomping stuffed_animal stuffed_toy toes under_skirt underwear white_panties
1boy 1boy1girl 1girls angry annoyed bare_legs bare_thighs barefoot black_hair blazer bleach bunny_panties bunny_print cameltoe canonical_scene clothed clothed_female ecchisage feet female female_focus irritated kon kuchiki_rukia long_hair male_masochism masochism masochist no_shoes panties pantsu petite petite_body pout pouting purple_eyes school_uniform shirt skirt smaller_female socks stomp stomping stuffed_animal stuffed_toy toes under_skirt underwear white_panties
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
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 abs awesamdude balls bite_marks blood claw_marks dialogue diphallia diphallism dream_smp foolish foolish_gamers gay male male_masochism masochism minecraft_youtubers multi_penis muscular muscular_male nude nude_male penis solo speech_bubble szensizzle
1boy abs awesamdude balls bite_marks blood claw_marks dialogue diphallia diphallism dream_smp foolish foolish_gamers gay male male_masochism masochism minecraft_youtubers multi_penis muscular muscular_male nude nude_male penis solo speech_bubble szensizzle
1boy 1femboy 1girls 3d bellatrix_(tsob) bite_gag bondage darktoz dominant_female domination dominatrix female female_domination femboy femboy_masochism femboysub femdom gag gagged hotel_room human human_only light-skinned_femboy light-skinned_male light_skin male male_masochism malesub masochism mc_(tsob) nipple_play nipples pale-skinned_female pale_skin restrained sadism spikes straight taller_girl the_shadow_over_blackmore tied_up vampire vampirism
1boy 1femboy 1girls 3d bellatrix_(tsob) bite_gag bondage darktoz dominant_female domination dominatrix female female_domination femboy femboy_masochism femboysub femdom gag gagged hotel_room human human_only light-skinned_femboy light-skinned_male light_skin male male_masochism malesub masochism mc_(tsob) nipple_play nipples pale-skinned_female pale_skin restrained sadism spikes straight taller_girl the_shadow_over_blackmore tied_up vampire vampirism
1boy 1boy1girl 1girls age_difference akame_ga_kill! ass big_ass big_butt black_and_white black_pants black_shirt blush blush_lines breasts bubble_butt choker closed_eyes dominant dominant_female domination english english_commentary english_text eyepatch facesitting female femdom funny gutsbro14 hair_between_eyes hair_over_one_eye height_difference hetero heterosexual large_ass large_breasts large_butt looking_at_another lubbock_(akame_ga_kill!) male male_masochism malesub mature mature_female mature_woman mechanical mechanical_arm najenda_(akame_ga_kill!) prosthetic prosthetic_arm short_hair simple_background sitting sitting_on_person sketch smile smiling smug smug_face smug_smile straps teeth thick_thighs thighs thumbs_up tomboy white_background white_hair
1boy 1boy1girl 1girls age_difference akame_ga_kill! ass big_ass big_butt black_and_white black_pants black_shirt blush blush_lines breasts bubble_butt choker closed_eyes dominant dominant_female domination english english_commentary english_text eyepatch facesitting female femdom funny gutsbro14 hair_between_eyes hair_over_one_eye height_difference hetero heterosexual large_ass large_breasts large_butt looking_at_another lubbock_(akame_ga_kill!) male male_masochism malesub mature mature_female mature_woman mechanical mechanical_arm najenda_(akame_ga_kill!) prosthetic prosthetic_arm short_hair simple_background sitting sitting_on_person sketch smile smiling smug smug_face smug_smile straps teeth thick_thighs thighs thumbs_up tomboy white_background white_hair
1boy 1boy1girl 2012 =_= all_fours artist_name big_breasts bleach blue_eyes braid brand_name_imitation breasts bust busty character_name cleavage copyright_name dominant dominant_female domination duo duo_focus female femdom gairon hanataro_yamada height_difference highres katana large_breasts leash lips long_hair male/female male_masochism male_with_female malesub masochism masochist mature mature_female mature_woman milf mop older_female older_woman_and_younger_boy oppai shoes short_shorts shorts single_braid size_difference smile sneakers stepped_on submissive submissive_male sword tank_top unohana_retsu wavy_mouth weapon younger_male
1boy 1boy1girl 2012 =_= all_fours artist_name big_breasts bleach blue_eyes braid brand_name_imitation breasts bust busty character_name cleavage copyright_name dominant dominant_female domination duo duo_focus female femdom gairon hanataro_yamada height_difference highres katana large_breasts leash lips long_hair male/female male_masochism male_with_female malesub masochism masochist mature mature_female mature_woman milf mop older_female older_woman_and_younger_boy oppai shoes short_shorts shorts single_braid size_difference smile sneakers stepped_on submissive submissive_male sword tank_top unohana_retsu wavy_mouth weapon younger_male
1boy 1girls anger_vein blush butterfly_hair_ornament demon_boy demon_slayer dominant_female domination douma female femdom fully_clothed haori happy_sub heart katana kimetsu_no_yaiba kochou_shinobu 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 katana kimetsu_no_yaiba kochou_shinobu 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 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 1boy1girl 1girls big_ass big_breasts bigger_female bike_shorts breast_smother buttjob character_request cling cum femdom holding_hands humiliation interlocked_fingers large_breasts light-skinned_female light_skin looking_at_viewer male_masochism malesub masochism medium_hair pink_eyes pink_hair reverse_ryona smiling smiling_at_viewer smothering source_request thigh_job thigh_sex topless twintails wrestling wrestling_ring wrestlingryona
1boy 1boy1girl 1girls big_ass big_breasts bigger_female bike_shorts breast_smother buttjob character_request cling cum femdom holding_hands humiliation interlocked_fingers large_breasts light-skinned_female light_skin looking_at_viewer male_masochism malesub masochism medium_hair pink_eyes pink_hair reverse_ryona smiling smiling_at_viewer smothering source_request thigh_job thigh_sex topless twintails wrestling wrestling_ring wrestlingryona
1boy 1girls big_ass big_breasts blush butterfly_hair_ornament butterfly_wings choke_hold choking demon_boy demon_slayer dialogue douma english_text fangs female femdom fully_clothed green_eyes hanging_breasts happy_sub heart_eyes huge_breasts kimetsu_no_yaiba kimono long_hair looking_at_viewer looking_back male male_masochism malesub masochism masochist neck_grab nipple_bulge original_character pointy_ears speech_bubble the80scryptid white_hair
1boy 1girls big_ass big_breasts blush butterfly_hair_ornament butterfly_wings choke_hold choking demon_boy demon_slayer dialogue douma english_text fangs female femdom fully_clothed green_eyes hanging_breasts happy_sub heart_eyes huge_breasts kimetsu_no_yaiba kimono long_hair looking_at_viewer looking_back male male_masochism malesub masochism masochist neck_grab nipple_bulge original_character pointy_ears speech_bubble the80scryptid white_hair
1boy 1male 2022 ahe_gao ahegao ball_gag blank_eyes cartoon_network collar digital_media_(artwork) drool drool_on_face drooling excessive_drooling gagged gay hi_res latex looking_up male male_focus male_masochism male_only male_solo malesub masochism naked naked_male nipple_chain nipple_piercing nipples solo solo_focus solo_male steven_quartz_universe steven_universe steven_universe_future submissive submissive_male tears tears_of_pain tears_of_pleasure toofygoru twitter_username
1boy 1male 2022 ahe_gao ahegao ball_gag blank_eyes cartoon_network collar digital_media_(artwork) drool drool_on_face drooling excessive_drooling gagged gay hi_res latex looking_up male male_focus male_masochism male_only male_solo malesub masochism naked naked_male nipple_chain nipple_piercing nipples solo solo_focus solo_male steven_quartz_universe steven_universe steven_universe_future submissive submissive_male tears tears_of_pain tears_of_pleasure toofygoru twitter_username
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
2022 absurd_res alcohol anthro antlers arthur_(furfragged) bathroom beverage biped bottomless breasts canid canine cervid chubby_anthro chubby_male clothed clothing cloven_hooves critical_hit daddy digitigrade door duo end_table english_text eyewear female foreplay furfragged furniture gameplay_mechanics glasses gui health_bar heart hi_res hooves horn hud intraspecies life_(gaming) male male/male male_masochism male_only mammal masochism monochrome mug on_sofa potbelly public public_sex sadism scut_tail sex short_tail sigh sino_(furfragged) slightly_chubby smile sofa spanking stat_bars status_effect text tongue tongue_out traditional_media_(artwork) voyeur
2022 absurd_res alcohol anthro antlers arthur_(furfragged) bathroom beverage biped bottomless breasts canid canine cervid chubby_anthro chubby_male clothed clothing cloven_hooves critical_hit daddy digitigrade door duo end_table english_text eyewear female foreplay furfragged furniture gameplay_mechanics glasses gui health_bar heart hi_res hooves horn hud intraspecies life_(gaming) male male/male male_masochism male_only mammal masochism monochrome mug on_sofa potbelly public public_sex sadism scut_tail sex short_tail sigh sino_(furfragged) slightly_chubby smile sofa spanking stat_bars status_effect text tongue tongue_out traditional_media_(artwork) voyeur