walking_the_plank -animated best from all time

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walking the plank

1girl 1other absurdres black_hair braid crying embers fire from_side highres imminent_death korean_mythology long_hair long_sleeves looking_down mindle_(mossacannibalis) mossacannibalis profile walking_the_plank wide-eyed
1girl 1other absurdres black_hair braid crying embers fire from_side highres imminent_death korean_mythology long_hair long_sleeves looking_down mindle_(mossacannibalis) mossacannibalis profile walking_the_plank wide-eyed
2girls angry arms_behind_back arms_tied_behind_back bad_end ball_and_chain bandana betrayal blue_eyes blush blush_lines bondage bound bound_arms bound_legs bra captured choker crotch_rope dark_skin defeated defeated_heroine earrings female femsub fully_clothed gag gagged game_over genie genie_girl hair_cuff harem_outfit harem_pants headband helpless hi_res jewelry kidnapped long_hair lowleg midriff multiple_girls navel over_the_mouth_gag pants peril pirate pirate_ship pointy_ears ponytail purple_hair restrained risky_boots rope rope_bondage rope_harness shantae shantae_(character) shio-bari shoes strapless submissive surprised sword tape_gag taped_mouth tinkerbat underwater_peril_aladdin voice_actor_connection walking walking_the_plank
2girls angry arms_behind_back arms_tied_behind_back bad_end ball_and_chain bandana betrayal blue_eyes blush blush_lines bondage bound bound_arms bound_legs bra captured choker crotch_rope dark_skin defeated defeated_heroine earrings female femsub fully_clothed gag gagged game_over genie genie_girl hair_cuff harem_outfit harem_pants headband helpless hi_res jewelry kidnapped long_hair lowleg midriff multiple_girls navel over_the_mouth_gag pants peril pirate pirate_ship pointy_ears ponytail purple_hair restrained risky_boots rope rope_bondage rope_harness shantae shantae_(character) shio-bari shoes strapless submissive surprised sword tape_gag taped_mouth tinkerbat underwater_peril_aladdin voice_actor_connection walking walking_the_plank
2girls animaniacs anthro blindfold bondage bound cutlass duo female furboz genitals hi_res julie_bruin light lighting mammal melee_weapon minerva_mink mink multiple_girls mustelid musteline nipple_slip pirate plank pussy ship sword tiny_toon_adventures true_musteline uncensored ursid vehicle walking_the_plank warner_brothers watercraft weapon
2girls animaniacs anthro blindfold bondage bound cutlass duo female furboz genitals hi_res julie_bruin light lighting mammal melee_weapon minerva_mink mink multiple_girls mustelid musteline nipple_slip pirate plank pussy ship sword tiny_toon_adventures true_musteline uncensored ursid vehicle walking_the_plank warner_brothers watercraft weapon
2015 2boys anal anthro arcanine boat canine clenched_teeth cross_section cum cum_in_ass cum_inside dog-bone fox full_body hi_res internal male mammal medallion nintendo nude ocean outdoors penetration plank pokemon pokemon_(species) restrained sex teeth video_games walking_the_plank water yaoi
2015 2boys anal anthro arcanine boat canine clenched_teeth cross_section cum cum_in_ass cum_inside dog-bone fox full_body hi_res internal male mammal medallion nintendo nude ocean outdoors penetration plank pokemon pokemon_(species) restrained sex teeth video_games walking_the_plank water yaoi
1girl animal_costume bear_costume blush bound bound_arms chibi crying fang heterochromia hololive houshou_kumarine houshou_marine long_hair maposuke pirate plank red_eyes red_hair shark_fin ship signature virtual_youtuber walking_the_plank watercraft yellow_eyes
1girl animal_costume bear_costume blush bound bound_arms chibi crying fang heterochromia hololive houshou_kumarine houshou_marine long_hair maposuke pirate plank red_eyes red_hair shark_fin ship signature virtual_youtuber walking_the_plank watercraft yellow_eyes
alternate_universe apple_gag apple_in_mouth arms_behind_back b3_gf_(blazethewolf55) big_ass big_breasts boiling bondage cauldron cooking cooking_pot cooking_vore d-side_girlfriend damsel damsel_in_distress dark_skin demon_girl digital_drawing_(artwork) digital_media_(artwork) female_only fnf fnf_mods freckles freckles_on_ass freckles_on_breasts freckles_on_face freckles_on_shoulders friday_night_funkin girlfriend_(friday_night_funkin) imminent_death lemon_demon light_skin mod monster monster_(friday_night_funkin) multiple_girls multiverse naked newgrounds nsfw nude orange_hair peril poking ponytail prisoner purple_hair red_hair shaya_dearest short_girl shortstack sine420eee soup splashing stew teasing thick_ass thick_thighs three_girls tied_arms tied_up twintails vampire_girl walking_the_plank
alternate_universe apple_gag apple_in_mouth arms_behind_back b3_gf_(blazethewolf55) big_ass big_breasts boiling bondage cauldron cooking cooking_pot cooking_vore d-side_girlfriend damsel damsel_in_distress dark_skin demon_girl digital_drawing_(artwork) digital_media_(artwork) female_only fnf fnf_mods freckles freckles_on_ass freckles_on_breasts freckles_on_face freckles_on_shoulders friday_night_funkin girlfriend_(friday_night_funkin) imminent_death lemon_demon light_skin mod monster monster_(friday_night_funkin) multiple_girls multiverse naked newgrounds nsfw nude orange_hair peril poking ponytail prisoner purple_hair red_hair shaya_dearest short_girl shortstack sine420eee soup splashing stew teasing thick_ass thick_thighs three_girls tied_arms tied_up twintails vampire_girl walking_the_plank
1girl absurdres angry black_hair black_panties blue_eyes blush breasts clenched_teeth cloud creature dress eyes_visible_through_hair from_below girls_und_panzer highres jinguu_(4839ms) long_hair looking_at_viewer looking_down microskirt midriff navel ogin_(girls_und_panzer) outdoors panties pleated_skirt restrained sailor_dress skirt sky small_breasts sweat teeth underwear upskirt walking_the_plank white_skirt
1girl absurdres angry black_hair black_panties blue_eyes blush breasts clenched_teeth cloud creature dress eyes_visible_through_hair from_below girls_und_panzer highres jinguu_(4839ms) long_hair looking_at_viewer looking_down microskirt midriff navel ogin_(girls_und_panzer) outdoors panties pleated_skirt restrained sailor_dress skirt sky small_breasts sweat teeth underwear upskirt walking_the_plank white_skirt
bdsm bondage bound breasts cloth_gag execution gag gagged highres improvised_gag mukanata over_the_nose_gag princess_connect! restrained shibari walking_the_plank yui_(princess_connect!)
bdsm bondage bound breasts cloth_gag execution gag gagged highres improvised_gag mukanata over_the_nose_gag princess_connect! restrained shibari walking_the_plank yui_(princess_connect!)
1girls blue_eyes bondage damsel damsel_in_distress digital_drawing_(artwork) digital_media_(artwork) female game_over game_over_screen genie half_genie humiliating humiliation long_ponytail naked naked_female nude nude_female peril pirate pirate_ship poking_ass ponytail purple_hair risky_boots shantae shantae:_half-genie_hero shantae_(character) shantae_and_the_pirate's_curse shark sine420eee walk_the_plank walking_the_plank water
1girls blue_eyes bondage damsel damsel_in_distress digital_drawing_(artwork) digital_media_(artwork) female game_over game_over_screen genie half_genie humiliating humiliation long_ponytail naked naked_female nude nude_female peril pirate pirate_ship poking_ass ponytail purple_hair risky_boots shantae shantae:_half-genie_hero shantae_(character) shantae_and_the_pirate's_curse shark sine420eee walk_the_plank walking_the_plank water
3_toes 4_fingers ambiguous_gender anthro arms_tied asphyxiation ass big_breasts blood blood_in_water bodily_fluids bound breasts brown_hair bubble butt_from_the_front canid canine canis capelet clothed clothed/nude clothed_female clothing constricted_pupils corset cruelty curvy_figure death dismemberment dorsal_fin drowning ear_piercing eaten_alive eating evil_grin execution feeding_frenzy feet female female_dominating_female feral fin fingers fish fluffy fluffy_tail genitals gills gore grin group guro guts hair hard_vore head_tuft helpless hi_res holding_breath hourglass_figure hourglass_figured_female imminent_death intestines j.fbelen jfbelen killing leg_wound lingerie long_hair mammal marine melee_weapon nipples nude organs pain panties perineum piercing pirate pupils pussy scared shark sharp_teeth ship signature silent_screaming small_pupils smile suffering sword tail teeth toes tongue tongue_piercing topwear tuft underwater underwear vehicle villainess violence vore walking_the_plank water watercraft weapon wolf wounded
3_toes 4_fingers ambiguous_gender anthro arms_tied asphyxiation ass big_breasts blood blood_in_water bodily_fluids bound breasts brown_hair bubble butt_from_the_front canid canine canis capelet clothed clothed/nude clothed_female clothing constricted_pupils corset cruelty curvy_figure death dismemberment dorsal_fin drowning ear_piercing eaten_alive eating evil_grin execution feeding_frenzy feet female female_dominating_female feral fin fingers fish fluffy fluffy_tail genitals gills gore grin group guro guts hair hard_vore head_tuft helpless hi_res holding_breath hourglass_figure hourglass_figured_female imminent_death intestines j.fbelen jfbelen killing leg_wound lingerie long_hair mammal marine melee_weapon nipples nude organs pain panties perineum piercing pirate pupils pussy scared shark sharp_teeth ship signature silent_screaming small_pupils smile suffering sword tail teeth toes tongue tongue_piercing topwear tuft underwater underwear vehicle villainess violence vore walking_the_plank water watercraft weapon wolf wounded
10s 2girls airi_(queen's_blade) airi_(queen's_blade) airi_(the_infernal_temptress) arms_behind_back bdsm black_legwear blue_eyes blush bondage boots bound bow breasts bustier captain_liliana cleavage cleave_gag cloth_gag crotch_rope detached_collar execution frills gag gagged hat highres improvised_gag jolly_roger large_breasts legs lingerie long_hair maid maid_headdress maullarmaullar midriff miniskirt multiple_girls ocean pink_eyes pink_hair pirate pirate_hat queen's_blade queen's_blade_rebellion red_hair shark shibari shibari_over_clothes ship skirt skull_and_crossed_swords sword thighhighs twintails underwear walking_the_plank watercraft weapon
10s 2girls airi_(queen's_blade) airi_(queen's_blade) airi_(the_infernal_temptress) arms_behind_back bdsm black_legwear blue_eyes blush bondage boots bound bow breasts bustier captain_liliana cleavage cleave_gag cloth_gag crotch_rope detached_collar execution frills gag gagged hat highres improvised_gag jolly_roger large_breasts legs lingerie long_hair maid maid_headdress maullarmaullar midriff miniskirt multiple_girls ocean pink_eyes pink_hair pirate pirate_hat queen's_blade queen's_blade_rebellion red_hair shark shibari shibari_over_clothes ship skirt skull_and_crossed_swords sword thighhighs twintails underwear walking_the_plank watercraft weapon
1girl @_@ apron artist_name bandana black_bandana black_hat bowl braid cat cleaver commentary_request cooking cooking_oil deep_frying demizu_posuka dough doughnut flour flying_sweatdrops food food_focus hat hook long_hair orange_eyes orange_hair original plank scared shirt skull smile steam striped_clothes striped_shirt table twin_braids walking_the_plank wavy_mouth yellow_shirt
1girl @_@ apron artist_name bandana black_bandana black_hat bowl braid cat cleaver commentary_request cooking cooking_oil deep_frying demizu_posuka dough doughnut flour flying_sweatdrops food food_focus hat hook long_hair orange_eyes orange_hair original plank scared shirt skull smile steam striped_clothes striped_shirt table twin_braids walking_the_plank wavy_mouth yellow_shirt
2010 anthro bondage carmelita_fox female fox furry mammal nennameerkat sly_cooper_(series) smooth_fur tagme vkyrie walking_the_plank
2010 anthro bondage carmelita_fox female fox furry mammal nennameerkat sly_cooper_(series) smooth_fur tagme vkyrie walking_the_plank
2girls 4boys arms_behind_back ball_and_chain_restraint bandana bare_shoulders bdsm bikini blue_eyeshadow bondage bound bra breasts brown_hair cameltoe captain_syrup chain cleavage cloth_gag creature curvy d.d._(wario_land) evil_smile execution eyeshadow full_body gag gagged hand_on_own_hip high_heels highres imminent_death improvised_gag legs_together lingerie lipstick long_hair makeup mario_(series) medium_breasts multiple_boys multiple_girls navel nintendo no_socks outdoors pain panties pants peril pirate pirate_goom plank princess_daisy pumps purple_pants red_hair scared shaxbert ship smile spiked_koopa super_mario_land super_star_(mario) swimsuit sword tearing_up tears third-party_edit underwear underwear_only walking_the_plank wario_land wario_land:_shake_it! wario_land_ii watercraft weapon yellow_bikini yellow_bra yellow_panties
2girls 4boys arms_behind_back ball_and_chain_restraint bandana bare_shoulders bdsm bikini blue_eyeshadow bondage bound bra breasts brown_hair cameltoe captain_syrup chain cleavage cloth_gag creature curvy d.d._(wario_land) evil_smile execution eyeshadow full_body gag gagged hand_on_own_hip high_heels highres imminent_death improvised_gag legs_together lingerie lipstick long_hair makeup mario_(series) medium_breasts multiple_boys multiple_girls navel nintendo no_socks outdoors pain panties pants peril pirate pirate_goom plank princess_daisy pumps purple_pants red_hair scared shaxbert ship smile spiked_koopa super_mario_land super_star_(mario) swimsuit sword tearing_up tears third-party_edit underwear underwear_only walking_the_plank wario_land wario_land:_shake_it! wario_land_ii watercraft weapon yellow_bikini yellow_bra yellow_panties
1girls 3_toes 3d 3d_(artwork) anthro areola ass barracuda big_ass big_breasts big_butt blue_body blue_hair blue_skin blue_sky breasts claws cloud completely_nude_female day daytime earrings ed_edd_n_eddy ed_edd_n_eddy_reference eyelashes facing_viewer feet female female_focus female_only fish full_body furry genitals hair humanoid_genitalia large_breasts long_hair looking_at_viewer marine medium_breasts nipple_piercing nipples nude nude_female ocean outdoors piercing plank plank_(ed_edd_n_eddy) pointy_ears purple_eyes pussy sharp_teeth shiny_hair shiny_skin smile solo solo_focus standing teeth thick_thighs thighs uncensored very_long_hair walking_the_plank water
1girls 3_toes 3d 3d_(artwork) anthro areola ass barracuda big_ass big_breasts big_butt blue_body blue_hair blue_skin blue_sky breasts claws cloud completely_nude_female day daytime earrings ed_edd_n_eddy ed_edd_n_eddy_reference eyelashes facing_viewer feet female female_focus female_only fish full_body furry genitals hair humanoid_genitalia large_breasts long_hair looking_at_viewer marine medium_breasts nipple_piercing nipples nude nude_female ocean outdoors piercing plank plank_(ed_edd_n_eddy) pointy_ears purple_eyes pussy sharp_teeth shiny_hair shiny_skin smile solo solo_focus standing teeth thick_thighs thighs uncensored very_long_hair walking_the_plank water
1girls 3_toes 3d 3d_(artwork) anthro areola ass barracuda big_ass big_breasts big_butt blue_body blue_hair blue_skin blue_sky breasts claws cloud completely_nude_female day daytime earrings ed_edd_n_eddy ed_edd_n_eddy_reference eyelashes facing_viewer feet female female_focus female_only fish full_body furry genitals hair humanoid_genitalia large_breasts long_hair looking_at_viewer marine medium_breasts nipple_piercing nipples nude nude_female ocean outdoors piercing plank plank_(ed_edd_n_eddy) pointy_ears purple_eyes pussy shiny_hair shiny_skin smile solo solo_focus standing thick_thighs thighs uncensored very_long_hair walking_the_plank water
1girls 3_toes 3d 3d_(artwork) anthro areola ass barracuda big_ass big_breasts big_butt blue_body blue_hair blue_skin blue_sky breasts claws cloud completely_nude_female day daytime earrings ed_edd_n_eddy ed_edd_n_eddy_reference eyelashes facing_viewer feet female female_focus female_only fish full_body furry genitals hair humanoid_genitalia large_breasts long_hair looking_at_viewer marine medium_breasts nipple_piercing nipples nude nude_female ocean outdoors piercing plank plank_(ed_edd_n_eddy) pointy_ears purple_eyes pussy shiny_hair shiny_skin smile solo solo_focus standing thick_thighs thighs uncensored very_long_hair walking_the_plank water