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3girls ass bruise caning female female_only georm human multiple_girls nemona_(pokemon) nessa_(pokemon) pokemon pokemon_sv punishment sonia_(pokemon) spanking whipping
3girls ass bruise caning female female_only georm human multiple_girls nemona_(pokemon) nessa_(pokemon) pokemon pokemon_sv punishment sonia_(pokemon) spanking whipping
beating cane_marks caning getting_spanked_while_standing gregor_(limbus_company) hook_arm hook_hand lashings limbus_company mostly_clothed pain pants_down partially_clothed project_moon prosthetic prosthetic_arm punishment spanking spanking_ass spanking_butt spanking_while_standing uncolored
beating cane_marks caning getting_spanked_while_standing gregor_(limbus_company) hook_arm hook_hand lashings limbus_company mostly_clothed pain pants_down partially_clothed project_moon prosthetic prosthetic_arm punishment spanking spanking_ass spanking_butt spanking_while_standing uncolored
ahoge anus ass barefoot black_shirt bottomless brown_hair cane caning closed_eyes commentary_request crying feet female frown hair_intakes highres kallo legs_up lying medium_hair on_back open_mouth original pussy shirt short_sleeves soles solo spanked spanking sweat teeth trembling uncensored upper_teeth_only variant_set
ahoge anus ass barefoot black_shirt bottomless brown_hair cane caning closed_eyes commentary_request crying feet female frown hair_intakes highres kallo legs_up lying medium_hair on_back open_mouth original pussy shirt short_sleeves soles solo spanked spanking sweat teeth trembling uncensored upper_teeth_only variant_set
ahe_gao audience caning pissing poop pooping punishment scat shit shitting tagme
ahe_gao audience caning pissing poop pooping punishment scat shit shitting tagme
artist_request caning crying peeing pissing punishment pussy_juice_drip scat spanking tagme
artist_request caning crying peeing pissing punishment pussy_juice_drip scat spanking tagme
amygdahlia_(artist) angry anthro ass big_butt black_nails bodily_fluids butt_slap caning clothing colored_nails crying deer feet hand_print hartswell_(amygdahlia) hoodie looking_back male mammal nails pain slap soles solo spank_marks spanking sweatpants tears teeth toes topwear
amygdahlia_(artist) angry anthro ass big_butt black_nails bodily_fluids butt_slap caning clothing colored_nails crying deer feet hand_print hartswell_(amygdahlia) hoodie looking_back male mammal nails pain slap soles solo spank_marks spanking sweatpants tears teeth toes topwear
2girls blonde_hair caning crying multiple_girls punishment punishment_spanking rwby spanked spanking vscarok weiss_schnee white_hair yang_xiao_long
2girls blonde_hair caning crying multiple_girls punishment punishment_spanking rwby spanked spanking vscarok weiss_schnee white_hair yang_xiao_long
1900s arms_above_head bondage caning caption dolly_morton engraving hatching_(art) literature monochrome public_domain spanking stockings the_memoirs_of_dolly_morton thighs tied_to_ladder traditional_media_(artwork) vintage
1900s arms_above_head bondage caning caption dolly_morton engraving hatching_(art) literature monochrome public_domain spanking stockings the_memoirs_of_dolly_morton thighs tied_to_ladder traditional_media_(artwork) vintage
1930s 2girls ass bondage caning carlo_(artist) clothed_female_nude_female femdom high_heels imminent_spanking kneeling lezdom multiple_girls rear_view spanking tied_to_wall traditional_media_(artwork) vintage
1930s 2girls ass bondage caning carlo_(artist) clothed_female_nude_female femdom high_heels imminent_spanking kneeling lezdom multiple_girls rear_view spanking tied_to_wall traditional_media_(artwork) vintage
18th_century 1boy 2girls arms_above_head bondage bustle caning damsel_in_distress engraving hoop_skirt louis_binet male public_domain sideboob tied_to_wall topless traditional_media_(artwork) vintage whipping
18th_century 1boy 2girls arms_above_head bondage bustle caning damsel_in_distress engraving hoop_skirt louis_binet male public_domain sideboob tied_to_wall topless traditional_media_(artwork) vintage whipping
ass bastinado caning covered_in_cum cuffed cuffed_ankles cuffed_penis cuffed_wrists dildo_in_ass feet flogging humiliation humiliation_fetish in_front_of_a_mirror ken_kaneki male_nudity mirror mirror_reflection penis sex_dungeon sex_toys strapped_to_a_chair tokyo_ghoul vibrator_in_ass
ass bastinado caning covered_in_cum cuffed cuffed_ankles cuffed_penis cuffed_wrists dildo_in_ass feet flogging humiliation humiliation_fetish in_front_of_a_mirror ken_kaneki male_nudity mirror mirror_reflection penis sex_dungeon sex_toys strapped_to_a_chair tokyo_ghoul vibrator_in_ass
9:16 anthro butt_slap canid canine caning cloe_(powerfulcrumpets) dipstick_tail female fox genitals hair hi_res looking_back mammal markings pink_hair powerfulcrumpets pussy slap solo spank_marks spanked_thighs spanking tail tail_markings
9:16 anthro butt_slap canid canine caning cloe_(powerfulcrumpets) dipstick_tail female fox genitals hair hi_res looking_back mammal markings pink_hair powerfulcrumpets pussy slap solo spank_marks spanked_thighs spanking tail tail_markings
absurd_res anthro antlers ass ballbusting balls big_breasts big_butt bovid bovine breast_smother breasts canid canine caning canis cassie_(piderverse) cock_and_ball_torture deer domestic_dog eeveelution embarrassed erection european_mythology fish fur generation_4_pokemon genital_torture genitals gesture girly glaceon greek_mythology group hair hand_heart hi_res honey_(stagshack) horn huge_breasts long_hair male mammal marine minotaur multicolored_body multicolored_fur mythology nintendo nipples nude penis pokemon pokemon_(species) ponytail presenting pussy raised_tail shark size_difference smaller_male smothering stagshack surprise tail thick_thighs two_tone_body two_tone_fur zadok_the_shark
absurd_res anthro antlers ass ballbusting balls big_breasts big_butt bovid bovine breast_smother breasts canid canine caning canis cassie_(piderverse) cock_and_ball_torture deer domestic_dog eeveelution embarrassed erection european_mythology fish fur generation_4_pokemon genital_torture genitals gesture girly glaceon greek_mythology group hair hand_heart hi_res honey_(stagshack) horn huge_breasts long_hair male mammal marine minotaur multicolored_body multicolored_fur mythology nintendo nipples nude penis pokemon pokemon_(species) ponytail presenting pussy raised_tail shark size_difference smaller_male smothering stagshack surprise tail thick_thighs two_tone_body two_tone_fur zadok_the_shark
1990s 1992 1girls 20th_century 2boys after_fellatio bald bald_man bdsm black_hair bondage caning chained color comic cover_page crop cum depuceleur dungeon erection female femsub hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male nude nude_female nude_male part_2 restrained sherrif spreader_bar straight whip_marks whipping
1990s 1992 1girls 20th_century 2boys after_fellatio bald bald_man bdsm black_hair bondage caning chained color comic cover_page crop cum depuceleur dungeon erection female femsub hairy_chest handdrawn human human_only lady_marilyn lady_marilyns_misfortune light-skinned_female light-skinned_male light_skin male maledom mature mature_male nude nude_female nude_male part_2 restrained sherrif spreader_bar straight whip_marks whipping
1girls 1male age_difference anthony_bridgerton ass ass_focus bending_forward bending_over bent_over bent_over_table bottomless_female bridgerton brother brother_and_sister brown_hair butt_focus cane caning daphne_bridgerton discipline dress dress_lift dress_up fully_clothed fully_clothed_male hitting incest jonathan_bailey no_panties no_underwear older_male older_man older_man_and_younger_woman phoebe_dynevor red_hair roissy room sibling sibling_incest siblings sister skirt_lift skirt_up smirk smirking spanking spanking_ass spanking_butt spanking_marks table
1girls 1male age_difference anthony_bridgerton ass ass_focus bending_forward bending_over bent_over bent_over_table bottomless_female bridgerton brother brother_and_sister brown_hair butt_focus cane caning daphne_bridgerton discipline dress dress_lift dress_up fully_clothed fully_clothed_male hitting incest jonathan_bailey no_panties no_underwear older_male older_man older_man_and_younger_woman phoebe_dynevor red_hair roissy room sibling sibling_incest siblings sister skirt_lift skirt_up smirk smirking spanking spanking_ass spanking_butt spanking_marks table
5_fingers absurd_res angry animal_ears annoyed anthro arms_above_head ass assisted_exposure bare_shoulders black_clothing black_footwear black_robe black_shoes blue_bottomwear blue_clothing blue_jeans blue_pants blush bodily_fluids bottomwear bottomwear_around_one_leg branch breasts brown_body brown_clothing brown_eyes brown_footwear brown_fur brown_hair brown_shoes brown_tail canid canine caning cat_ears cat_tail catgirl claw claws clothed clothing clothing_around_one_leg clothing_lift collarbone collared_shirt cum cum_drip cum_in_hair cum_on_face cum_on_hair cum_on_head dangling dark_nipples denim denim_clothing dialogue disembodied_hand disembodied_limb domestic_cat dripping duo embarrassed english_text exposed_breasts eyebrows eyelashes faceless_character faceless_male fangs fantasy felid feline felis female fingers footwear forced front_view full_body funny fur furrowed_brow furry gaping_mouth genital_fluids green_eyes grey_background grey_body grey_clothing grey_footwear grey_fur grey_socks grey_sweater grey_topwear group hair harry_potter harry_potter_and_the_prisoner_of_azkaban hermione_granger hi_res holding_ankle holding_leg hood hoodie hoodie_down human humanoid humanoid_hands humor jeans leg-up leg_grab leg_up light light-skinned_female light_body light_skin lighting lips long_claws long_fingernails long_hair long_tail looking_at_viewer looking_back looking_up male male/female mammal mary_janes medium_breasts motion_blur motion_lines mouth_closed multicolored_clothing multicolored_necktie multicolored_panties multicolored_underwear necktie nervous nipples no_bra offscreen_character offscreen_male ominous ominous_shadow open_clothes open_mouth open_shirt pale_body pale_skin panties pants pants_around_one_leg panty_shot pattern_bottomwear pattern_clothing pattern_necktie pattern_panties pattern_underwear penis_shadow penis_silhouette pink_clothing pink_hoodie pink_nipples pink_nose pink_shirt pink_tongue pink_topwear plain_background plant polyjuice_potion profanity pupils purple_clothing purple_panties purple_underwear raised_eyebrows rear_view red_clothing red_necktie red_panties red_underwear reference remus_lupin robe robe_lift ron_weasley round_eyes sac sad scared school_uniform shadow shiny_skin shirt shirt_collar shirt_down shocked shoe_soles shoes side_view signature simple_background skirt skirt_lift slit_pupils sneakers socks solo_focus spank_marks spanking speech_bubble standing_on_one_leg striped_bottomwear striped_clothing striped_necktie striped_panties striped_underwear stripes submissive_and_breedable suspended_in_midair swear sweater tail teenager teeth text three-quarter_view tongue topwear torn_clothing torn_panties torn_underwear transformation travis-t tree trio troll two_tone_clothing two_tone_necktie two_tone_panties two_tone_underwear underwear undressing_another uniform unseen_character unseen_male unzipped upper_body upside-down upskirt wavy_hair were werecanid werecanine werewolf whiskers white_clothing white_dress_shirt white_footwear white_socks whomping_willow wide_eyed wide_sleeves witch yellow_clothing yellow_necktie yellow_panties yellow_underwear young zipper zipper_down zipper_hoodie
5_fingers absurd_res angry animal_ears annoyed anthro arms_above_head ass assisted_exposure bare_shoulders black_clothing black_footwear black_robe black_shoes blue_bottomwear blue_clothing blue_jeans blue_pants blush bodily_fluids bottomwear bottomwear_around_one_leg branch breasts brown_body brown_clothing brown_eyes brown_footwear brown_fur brown_hair brown_shoes brown_tail canid canine caning cat_ears cat_tail catgirl claw claws clothed clothing clothing_around_one_leg clothing_lift collarbone collared_shirt cum cum_drip cum_in_hair cum_on_face cum_on_hair cum_on_head dangling dark_nipples denim denim_clothing dialogue disembodied_hand disembodied_limb domestic_cat dripping duo embarrassed english_text exposed_breasts eyebrows eyelashes faceless_character faceless_male fangs fantasy felid feline felis female fingers footwear forced front_view full_body funny fur furrowed_brow furry gaping_mouth genital_fluids green_eyes grey_background grey_body grey_clothing grey_footwear grey_fur grey_socks grey_sweater grey_topwear group hair harry_potter harry_potter_and_the_prisoner_of_azkaban hermione_granger hi_res holding_ankle holding_leg hood hoodie hoodie_down human humanoid humanoid_hands humor jeans leg-up leg_grab leg_up light light-skinned_female light_body light_skin lighting lips long_claws long_fingernails long_hair long_tail looking_at_viewer looking_back looking_up male male/female mammal mary_janes medium_breasts motion_blur motion_lines mouth_closed multicolored_clothing multicolored_necktie multicolored_panties multicolored_underwear necktie nervous nipples no_bra offscreen_character offscreen_male ominous ominous_shadow open_clothes open_mouth open_shirt pale_body pale_skin panties pants pants_around_one_leg panty_shot pattern_bottomwear pattern_clothing pattern_necktie pattern_panties pattern_underwear penis_shadow penis_silhouette pink_clothing pink_hoodie pink_nipples pink_nose pink_shirt pink_tongue pink_topwear plain_background plant polyjuice_potion profanity pupils purple_clothing purple_panties purple_underwear raised_eyebrows rear_view red_clothing red_necktie red_panties red_underwear reference remus_lupin robe robe_lift ron_weasley round_eyes sac sad scared school_uniform shadow shiny_skin shirt shirt_collar shirt_down shocked shoe_soles shoes side_view signature simple_background skirt skirt_lift slit_pupils sneakers socks solo_focus spank_marks spanking speech_bubble standing_on_one_leg striped_bottomwear striped_clothing striped_necktie striped_panties striped_underwear stripes submissive_and_breedable suspended_in_midair swear sweater tail teenager teeth text three-quarter_view tongue topwear torn_clothing torn_panties torn_underwear transformation travis-t tree trio troll two_tone_clothing two_tone_necktie two_tone_panties two_tone_underwear underwear undressing_another uniform unseen_character unseen_male unzipped upper_body upside-down upskirt wavy_hair were werecanid werecanine werewolf whiskers white_clothing white_dress_shirt white_footwear white_socks whomping_willow wide_eyed wide_sleeves witch yellow_clothing yellow_necktie yellow_panties yellow_underwear young zipper zipper_down zipper_hoodie
1990s 1992 1girls 20th_century 2boys bald bald_man bdsm black_and_white black_hair bondage breast_torture candle candle_wax caning comic crying depuceleur dungeon erection fellatio female femsub flogging forced_blowjob handdrawn human human_only lady_marilyn lady_marilyns_misfortune male mature mature_male nipple_pull nipple_torture nude nude_female nude_male rape restrained sherrif spanking spitroast stationary_restraints straight torture_device vaginal_penetration wax wax_torture whipping
1990s 1992 1girls 20th_century 2boys bald bald_man bdsm black_and_white black_hair bondage breast_torture candle candle_wax caning comic crying depuceleur dungeon erection fellatio female femsub flogging forced_blowjob handdrawn human human_only lady_marilyn lady_marilyns_misfortune male mature mature_male nipple_pull nipple_torture nude nude_female nude_male rape restrained sherrif spanking spitroast stationary_restraints straight torture_device vaginal_penetration wax wax_torture whipping
1girl 1girls 5boys anal anal_sex ass balls bent_over big_balls big_penis blargsnarf blowjob bondage breasts broken_rape_victim caning cum_in_ass cum_in_mouth cum_on_ass cum_on_face disney disney_villains eyes_rolling_back fellatio female forced_oral foreskin gangbang huge_balls huge_cock human human_male large_ass light-skinned_male light_skin madam_mim male male/female mind_break nipples oral penis pillory public_humiliation public_nudity public_use purple_hair purple_skin rape slap_mark spank_marks spanking spitroast stocks testicles the_sword_in_the_stone uncircumcised uncut witch
1girl 1girls 5boys anal anal_sex ass balls bent_over big_balls big_penis blargsnarf blowjob bondage breasts broken_rape_victim caning cum_in_ass cum_in_mouth cum_on_ass cum_on_face disney disney_villains eyes_rolling_back fellatio female forced_oral foreskin gangbang huge_balls huge_cock human human_male large_ass light-skinned_male light_skin madam_mim male male/female mind_break nipples oral penis pillory public_humiliation public_nudity public_use purple_hair purple_skin rape slap_mark spank_marks spanking spitroast stocks testicles the_sword_in_the_stone uncircumcised uncut witch
2girls ass blush cane caning chainsaw_man chair crying horns makima_(chainsaw_man) multiple_girls panties panties_down power_(chainsaw_man) red_ass red_butt shitsuten socks spanked spanking suit sweat tie white_socks
2girls ass blush cane caning chainsaw_man chair crying horns makima_(chainsaw_man) multiple_girls panties panties_down power_(chainsaw_man) red_ass red_butt shitsuten socks spanked spanking suit sweat tie white_socks
2023 3d alliance_(warcraft) bdsm blood_elf blood_elf_female blue_hair bondage buttplug cane caning death_knight_(warcraft) dildo dildo_in_mouth dildo_in_pussy dungeon elf elf_ears elf_female elves female femdom fucking_machine glowing_eyes knotted_dildo lezdom melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight night_elf_female nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment sex_machine sex_toy spanking vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blood_elf_female blue_hair bondage buttplug cane caning death_knight_(warcraft) dildo dildo_in_mouth dildo_in_pussy dungeon elf elf_ears elf_female elves female femdom fucking_machine glowing_eyes knotted_dildo lezdom melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight night_elf_female nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment sex_machine sex_toy spanking vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blue_hair bondage cane caning death_knight_(warcraft) dildo dildo_in_mouth dildo_in_pussy dungeon elf elf_ears female femdom fucking_machine glowing_eyes knotted_dildo melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment sex_machine sex_toy vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blue_hair bondage cane caning death_knight_(warcraft) dildo dildo_in_mouth dildo_in_pussy dungeon elf elf_ears female femdom fucking_machine glowing_eyes knotted_dildo melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment sex_machine sex_toy vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blue_hair bondage cane caning death_knight_(warcraft) dildo dildo_in_mouth dungeon elf elf_ears female femdom fucking_machine glowing_eyes green_eyes knotted_dildo melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment running_mascara sex_machine sex_toy vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blue_hair bondage cane caning death_knight_(warcraft) dildo dildo_in_mouth dungeon elf elf_ears female femdom fucking_machine glowing_eyes green_eyes knotted_dildo melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment running_mascara sex_machine sex_toy vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blue_hair bondage cane caning death_knight_(warcraft) dildo dildo_in_mouth dildo_in_pussy dungeon elf elf_ears female femdom fucking_machine glowing_eyes knotted_dildo melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment sex_machine sex_toy vell(vellektra) vellektra world_of_warcraft yellow_hair
2023 3d alliance_(warcraft) bdsm blood_elf blue_hair bondage cane caning death_knight_(warcraft) dildo dildo_in_mouth dildo_in_pussy dungeon elf elf_ears female femdom fucking_machine glowing_eyes knotted_dildo melwinne naked naked_female necklace necklace_between_breasts night_elf night_elf_death_knight nipple_piercing nipple_piercing_pull nude nude_female pointy_ears punishment sex_machine sex_toy vell(vellektra) vellektra world_of_warcraft yellow_hair
caning caption casual casual_nudity edit female game_mod human kena:_bridge_of_spirits kena_(character) mod naked naked_female nude nude_female outdoors pale_skin screencap screenshot screenshot_edit speech_bubble staff weapon
caning caption casual casual_nudity edit female game_mod human kena:_bridge_of_spirits kena_(character) mod naked naked_female nude nude_female outdoors pale_skin screencap screenshot screenshot_edit speech_bubble staff weapon
1girls asian asian_female cane cane_marks caning dress_lift female female_only legs_together lying_down lying_on_stomach mid-autumn_festival night no_panties no_shoes on_stomach socks solo spanked spanking spanking_marks starila table
1girls asian asian_female cane cane_marks caning dress_lift female female_only legs_together lying_down lying_on_stomach mid-autumn_festival night no_panties no_shoes on_stomach socks solo spanked spanking spanking_marks starila table
absurdres blush bra caning copyright_request embarrassed exhibitionism feet female highres huaca looking_at_viewer pantyhose public_indecency pussy sitting spanked spanking underwear white_bra
absurdres blush bra caning copyright_request embarrassed exhibitionism feet female highres huaca looking_at_viewer pantyhose public_indecency pussy sitting spanked spanking underwear white_bra
absurdres alley ass being_watched blushing blushing_profusely brown_hair caning copyright_request crying crying_with_eyes_open embarrassed embarrassed_nude_female enf exhibitionism female highres holding_object holding_sign huaca humiliation looking_at_viewer looking_back naked_footwear naked_shoes naked_sneakers nude only_one_naked public_indecency public_nudity red_ass school shoes sign sneakers spank_marks spanked spanking squatting tears
absurdres alley ass being_watched blushing blushing_profusely brown_hair caning copyright_request crying crying_with_eyes_open embarrassed embarrassed_nude_female enf exhibitionism female highres holding_object holding_sign huaca humiliation looking_at_viewer looking_back naked_footwear naked_shoes naked_sneakers nude only_one_naked public_indecency public_nudity red_ass school shoes sign sneakers spank_marks spanked spanking squatting tears
2girls anonymous_artist bending_over bent_over blonde_hair blue_eyes brown_hair cane caning dominant_female femdom femsub fukiko_ichinoyima light-skinned_female light_skin misonoo_nanako multiple_girls oniisama_e... spanking submissive_female unknown_artist
2girls anonymous_artist bending_over bent_over blonde_hair blue_eyes brown_hair cane caning dominant_female femdom femsub fukiko_ichinoyima light-skinned_female light_skin misonoo_nanako multiple_girls oniisama_e... spanking submissive_female unknown_artist
1girls ass back-seamed_legwear backseam black_and_white book_on_head bottomless_female cane cane_marks caning caning_marks chalkboard chalkboard_writing classroom dunce_cap english_text from_behind full_body garter_belt garter_straps high_heels holding_book indoors legs_together math monochrome punishment rear_view roger_benson schoolgirl short_hair solo spanked spanking spanking_marks stiletto_heels stockings thigh_gap thighhighs triangle trigonometry twintails viewed_from_behind wooden_floor
1girls ass back-seamed_legwear backseam black_and_white book_on_head bottomless_female cane cane_marks caning caning_marks chalkboard chalkboard_writing classroom dunce_cap english_text from_behind full_body garter_belt garter_straps high_heels holding_book indoors legs_together math monochrome punishment rear_view roger_benson schoolgirl short_hair solo spanked spanking spanking_marks stiletto_heels stockings thigh_gap thighhighs triangle trigonometry twintails viewed_from_behind wooden_floor
2girls bastinado black_hair blonde_hair blue_eyes cane caning eingyeo eyebrows_visible_through_hair feet femdom femsub lezdom light-skinned_female light_skin long_hair moaning_in_pain multiple_girls pain school_desk school_uniform schoolgirl skirt spank_marks spanked spanking white_background yellow_eyes yuri
2girls bastinado black_hair blonde_hair blue_eyes cane caning eingyeo eyebrows_visible_through_hair feet femdom femsub lezdom light-skinned_female light_skin long_hair moaning_in_pain multiple_girls pain school_desk school_uniform schoolgirl skirt spank_marks spanked spanking white_background yellow_eyes yuri
3girls absurdres artoria_pendragon_(all) artoria_pendragon_(fate) ass bent_over bent_over_furniture black_footwear blonde_hair blue_ribbon blush braid braided_bun brown_hair bruise bruise_on_ass cane caned caning chalk chalkboard classroom crying crying_with_eyes_open desk dress_raised_for_spanking eraser fate/stay_night fate_(series) female femdom femsub floor hair_bun highres humiliation injury kneepits matou_sakura multiple_girls multiple_subs no_skirt open_mouth pain pantyhose punishment purple_hair red_ribbon ribbon saber school school_uniform shadow shirt shoes skirt spanked spanked_thighs spanking teacher tears thighhighs welts white_shirt
3girls absurdres artoria_pendragon_(all) artoria_pendragon_(fate) ass bent_over bent_over_furniture black_footwear blonde_hair blue_ribbon blush braid braided_bun brown_hair bruise bruise_on_ass cane caned caning chalk chalkboard classroom crying crying_with_eyes_open desk dress_raised_for_spanking eraser fate/stay_night fate_(series) female femdom femsub floor hair_bun highres humiliation injury kneepits matou_sakura multiple_girls multiple_subs no_skirt open_mouth pain pantyhose punishment purple_hair red_ribbon ribbon saber school school_uniform shadow shirt shoes skirt spanked spanked_thighs spanking teacher tears thighhighs welts white_shirt
1boy all_fours arched_back ass bangs bare_shoulders barefoot blush bondage breasts breath brown_eyes butt_crack cabinet calendar calendar_(object) cane caning clothed_male_nude_female collar collared_shirt completely_nude_female cubicle desk exhibitionism female femsub file file_cabinet folder from_above furrowed_brow grey_necktie grey_neckwear hair_between_eyes hair_strand hands_on_floor highres huaca humiliation id_card kneeling knees_apart_feet_together korean_text lanyard light-skinned_female long_hair maledom monitor necktie note nude office office_lady on_desk open_mouth original out_of_frame paper parted_bangs public_exposure public_nudity punishment red_ass red_hair salaryman seiza shaded_face shadow shiny shiny_hair shiny_skin shirt sidelocks sitting sitting_on_desk sitting_on_object slap_mark soles spank_marks spanked spanking sweat sweatdrop toes wet wet_hair whip_marks white_shirt
1boy all_fours arched_back ass bangs bare_shoulders barefoot blush bondage breasts breath brown_eyes butt_crack cabinet calendar calendar_(object) cane caning clothed_male_nude_female collar collared_shirt completely_nude_female cubicle desk exhibitionism female femsub file file_cabinet folder from_above furrowed_brow grey_necktie grey_neckwear hair_between_eyes hair_strand hands_on_floor highres huaca humiliation id_card kneeling knees_apart_feet_together korean_text lanyard light-skinned_female long_hair maledom monitor necktie note nude office office_lady on_desk open_mouth original out_of_frame paper parted_bangs public_exposure public_nudity punishment red_ass red_hair salaryman seiza shaded_face shadow shiny shiny_hair shiny_skin shirt sidelocks sitting sitting_on_desk sitting_on_object slap_mark soles spank_marks spanked spanking sweat sweatdrop toes wet wet_hair whip_marks white_shirt
1boy 1girls cane caning dialogue female femsub male maledom oc rwby spanked_thighs spanking tagme touching_toes weiss_schnee white_hair wolff_calavera
1boy 1girls cane caning dialogue female femsub male maledom oc rwby spanked_thighs spanking tagme touching_toes weiss_schnee white_hair wolff_calavera
3boys 6+girls caning dress_raised_for_spanking female femsub fireball_666 imminent_spanking multiple_boys multiple_girls multiple_subs paperwork ppeping punishment school school_uniform schoolgirl spanking spying voyeur voyeurism waiting_for_turn waiting_in_line white_background
3boys 6+girls caning dress_raised_for_spanking female femsub fireball_666 imminent_spanking multiple_boys multiple_girls multiple_subs paperwork ppeping punishment school school_uniform schoolgirl spanking spying voyeur voyeurism waiting_for_turn waiting_in_line white_background
2girls bicycle bit_gag bondage caning chains closed_eyes crying deviantart discipline feet female forge gag grimace guaky kitsune light-skinned_female light_skin machinery multiple_girls nipple_clamps non-con non-human original_character painful predicament_bondage punishment reverse_prayer shackles spanking spanking_machine struggling tears thong tied_tail torture vehicle white_panties
2girls bicycle bit_gag bondage caning chains closed_eyes crying deviantart discipline feet female forge gag grimace guaky kitsune light-skinned_female light_skin machinery multiple_girls nipple_clamps non-con non-human original_character painful predicament_bondage punishment reverse_prayer shackles spanking spanking_machine struggling tears thong tied_tail torture vehicle white_panties
1girls 2020s 2021 3d 3d_(artwork) absurd_res absurdres against_wall big_ass big_butt black_ass braided_hair caning dark-skinned_female dark_skin discipline disgrace fat_ass female female_focus female_only fit from_behind full_body_view head_developer headdeveloper human large_ass long_hair naked nude nude_female painful presenting_hindquarters punished punished_ass punishment red_ass simple_background solo solo_female solo_focus spank_marks spankable spanked spanked_butt
1girls 2020s 2021 3d 3d_(artwork) absurd_res absurdres against_wall big_ass big_butt black_ass braided_hair caning dark-skinned_female dark_skin discipline disgrace fat_ass female female_focus female_only fit from_behind full_body_view head_developer headdeveloper human large_ass long_hair naked nude nude_female painful presenting_hindquarters punished punished_ass punishment red_ass simple_background solo solo_female solo_focus spank_marks spankable spanked spanked_butt