semi-grimdark best from all time

Time frame

Tags

semi grimdark

1girls 4:3 after_sex animated anus ass bad_end bat_pony belly_inflation big_belly bitassembly bodily_fluids bondage bound clenched_teeth closed_eyes cum cum_in_pussy cum_inside cum_leaking cumflation defeated digital_media_(artwork) dripping dungeon equine female feral forced game_over gameplay_mechanics genital_fluids genitals gif green_eyes horse inflation long_hair low_res lowres mammal mimic monster my_little_pony naked nightglider nude one_eye_closed open_mouth penetration pixel_art pony pussy rape restrained semi-grimdark sex spread_legs spreading tentacle tentacle_bondage tentacle_bulge tentacles_on_female treasure_chest vaginal_penetration wide_eyed
1girls 4:3 after_sex animated anus ass bad_end bat_pony belly_inflation big_belly bitassembly bodily_fluids bondage bound clenched_teeth closed_eyes cum cum_in_pussy cum_inside cum_leaking cumflation defeated digital_media_(artwork) dripping dungeon equine female feral forced game_over gameplay_mechanics genital_fluids genitals gif green_eyes horse inflation long_hair low_res lowres mammal mimic monster my_little_pony naked nightglider nude one_eye_closed open_mouth penetration pixel_art pony pussy rape restrained semi-grimdark sex spread_legs spreading tentacle tentacle_bondage tentacle_bulge tentacles_on_female treasure_chest vaginal_penetration wide_eyed
<3_eyes 2021 alexis_(oc) anthro balls big_breasts bikini bimbo bimbofication blush bodily_fluids brain_drain breasts cleavage clothed clothing cum cum_in_ear cum_inside cum_through derp_eyes ear_penetration english_text equid equine eyewear fan_character fuzzy_balls genital_fluids genitals glasses hasbro heart hi_res horn huge_breasts jay_(oc) jrvanesbroek lips mammal medial_ring mindfuck my_little_pony nipple_outline orientation_play penetration penis pubes semi-grimdark sex silly skull_fucking swimwear text thick_lips unicorn wingding_eyes
<3_eyes 2021 alexis_(oc) anthro balls big_breasts bikini bimbo bimbofication blush bodily_fluids brain_drain breasts cleavage clothed clothing cum cum_in_ear cum_inside cum_through derp_eyes ear_penetration english_text equid equine eyewear fan_character fuzzy_balls genital_fluids genitals glasses hasbro heart hi_res horn huge_breasts jay_(oc) jrvanesbroek lips mammal medial_ring mindfuck my_little_pony nipple_outline orientation_play penetration penis pubes semi-grimdark sex silly skull_fucking swimwear text thick_lips unicorn wingding_eyes
4girls adagio_dazzle aria_blaze arms_behind_back asphyxiation bad_end belly_button bikini bondage bound_and_gagged breasts bubble busty cliff cloth_gag clothes comic commission crotch_rope dialogue drowning equestria_girls erect_nipples evil execution female females_only fetish friendship_is_magic gag gaggeddude32 hasbro human looking_down muffled_words my_little_pony navel night nipple_outline peril questionable red_eyes rope rope_bondage screaming semi-grimdark shackles silhouette sonata_dusk speech_bubble sunset_shimmer swimsuit the_dazzlings tied_ankles tied_up underwater weight
4girls adagio_dazzle aria_blaze arms_behind_back asphyxiation bad_end belly_button bikini bondage bound_and_gagged breasts bubble busty cliff cloth_gag clothes comic commission crotch_rope dialogue drowning equestria_girls erect_nipples evil execution female females_only fetish friendship_is_magic gag gaggeddude32 hasbro human looking_down muffled_words my_little_pony navel night nipple_outline peril questionable red_eyes rope rope_bondage screaming semi-grimdark shackles silhouette sonata_dusk speech_bubble sunset_shimmer swimsuit the_dazzlings tied_ankles tied_up underwater weight
1boy 3d 6girls abs air_bubble anthro applejack_(mlp) aquaphilia armpits asphyxiation barefoot big_breasts breasts bubble busty cave chubby comforting daemont92 dragon drowning explicit feet female fetish flat_chest fluttershy_(mlp) freediving friendship_is_magic hasbro huge_breasts mane_six_(mlp) muscles my_little_pony nipples nude pegasus peril piggyback pinkie_pie_(mlp) plantigrade_anthro pony puffy_cheeks rainbow_dash_(mlp) rarity_(mlp) semi-grimdark skinny_dipping smooth_skin source_filmmaker spike_(mlp) swimming trapped twilight_sparkle_(mlp) underwater unicorn
1boy 3d 6girls abs air_bubble anthro applejack_(mlp) aquaphilia armpits asphyxiation barefoot big_breasts breasts bubble busty cave chubby comforting daemont92 dragon drowning explicit feet female fetish flat_chest fluttershy_(mlp) freediving friendship_is_magic hasbro huge_breasts mane_six_(mlp) muscles my_little_pony nipples nude pegasus peril piggyback pinkie_pie_(mlp) plantigrade_anthro pony puffy_cheeks rainbow_dash_(mlp) rarity_(mlp) semi-grimdark skinny_dipping smooth_skin source_filmmaker spike_(mlp) swimming trapped twilight_sparkle_(mlp) underwater unicorn
1girls absurd_res accessory anal anal_sex bad_end being_sold bodily_fluids book buttplug buttplug_in_ass buttplug_insertion chains cleric container cursed cut_horn dock docked_tail equid equine fan_character fearful_expression female feral furgonomics genitals gloriajdrawing glowing glowing_eyes hasbro hi_res horn horn_accessory horn_cap horse jar ladypot mammal my_little_pony object_in_ass objectification objectified open_mouth penetrable_sex_toy penetration plug_(sex_toy) plug_insertion pony price_tag pussy scared semi-grimdark sex_toy sex_toy_in_ass sex_toy_insertion short_tail solo speech_bubble story story_in_description stump_horn tail tears unicorn what
1girls absurd_res accessory anal anal_sex bad_end being_sold bodily_fluids book buttplug buttplug_in_ass buttplug_insertion chains cleric container cursed cut_horn dock docked_tail equid equine fan_character fearful_expression female feral furgonomics genitals gloriajdrawing glowing glowing_eyes hasbro hi_res horn horn_accessory horn_cap horse jar ladypot mammal my_little_pony object_in_ass objectification objectified open_mouth penetrable_sex_toy penetration plug_(sex_toy) plug_insertion pony price_tag pussy scared semi-grimdark sex_toy sex_toy_in_ass sex_toy_insertion short_tail solo speech_bubble story story_in_description stump_horn tail tears unicorn what
1girls 3d air_bubble anthro aquaphilia armpits asphyxiation barefoot belly_button big_breasts breasts cave daemont92 death drowned drowning explicit feet female_death fetish friendship_is_magic hasbro my_little_pony nipples nude nudity open_mouth plantigrade_anthro semi-grimdark skinny_dipping source_filmmaker twilight_sparkle_(mlp) underwater unicorn vulva water wide_eyes
1girls 3d air_bubble anthro aquaphilia armpits asphyxiation barefoot belly_button big_breasts breasts cave daemont92 death drowned drowning explicit feet female_death fetish friendship_is_magic hasbro my_little_pony nipples nude nudity open_mouth plantigrade_anthro semi-grimdark skinny_dipping source_filmmaker twilight_sparkle_(mlp) underwater unicorn vulva water wide_eyes
1boy 1girls air_bubble anthro asphyxiation barefoot big_breasts breast_fondling breast_grab breasts bubble busty byondrage drowning erection explicit feet female fetish friendship_is_magic grope hasbro imminent_death male my_little_pony nipples nudity penis peril piggyback_ride plantigrade_anthro semi-grimdark smooth_skin snuff spike_(mlp) straight twilight_sparkle_(mlp) underwater vulva water
1boy 1girls air_bubble anthro asphyxiation barefoot big_breasts breast_fondling breast_grab breasts bubble busty byondrage drowning erection explicit feet female fetish friendship_is_magic grope hasbro imminent_death male my_little_pony nipples nudity penis peril piggyback_ride plantigrade_anthro semi-grimdark smooth_skin snuff spike_(mlp) straight twilight_sparkle_(mlp) underwater vulva water
1boy 1girls air_bubble angry anthro aquaphilia asphyxiation barefoot belly_button big_breasts big_nipples breast_fondling breast_grab breasts bubble busty byondrage determined drowning erection explicit feet female fetish freediving friendship_is_magic grope hasbro holding_breath huge_breasts imminent_death male my_little_pony nipples nudity penis peril piggyback_ride pillar plantigrade_anthro puffy_cheeks semi-grimdark skinny_dipping smooth_skin spear spike_(mlp) straight swimming temple thighs thunder_thighs tongue_out twilight_sparkle_(mlp) underwater water weapon
1boy 1girls air_bubble angry anthro aquaphilia asphyxiation barefoot belly_button big_breasts big_nipples breast_fondling breast_grab breasts bubble busty byondrage determined drowning erection explicit feet female fetish freediving friendship_is_magic grope hasbro holding_breath huge_breasts imminent_death male my_little_pony nipples nudity penis peril piggyback_ride pillar plantigrade_anthro puffy_cheeks semi-grimdark skinny_dipping smooth_skin spear spike_(mlp) straight swimming temple thighs thunder_thighs tongue_out twilight_sparkle_(mlp) underwater water weapon
1boy 1girls air_bubble anthro aquaphilia areola armpits asphyxiation barefoot belly_button big_areola big_breasts big_nipples breast_fondling breast_grab breasts bubble busty byondrage daemont92 diving dragon drowning explicit feet female fetish friendship_is_magic grope hasbro hug imminent_death male my_little_pony nipples nudity ocean penis peril piggyback_ride plantigrade_anthro puffy_nipples semi-grimdark shipwreck skinny_dipping smooth_skin spike_(mlp) straight swimming thighs thunder_thighs twilight_sparkle_(mlp) underwater vulva water wide_hips
1boy 1girls air_bubble anthro aquaphilia areola armpits asphyxiation barefoot belly_button big_areola big_breasts big_nipples breast_fondling breast_grab breasts bubble busty byondrage daemont92 diving dragon drowning explicit feet female fetish friendship_is_magic grope hasbro hug imminent_death male my_little_pony nipples nudity ocean penis peril piggyback_ride plantigrade_anthro puffy_nipples semi-grimdark shipwreck skinny_dipping smooth_skin spike_(mlp) straight swimming thighs thunder_thighs twilight_sparkle_(mlp) underwater vulva water wide_hips
after_rape bleeding canine canine_pussy chained crying cub cum_in_pussy domestic_dog female feral gore open_pussy pajamas paw_patrol purple_eye restrained semi-grimdark skye_(paw_patrol)
after_rape bleeding canine canine_pussy chained crying cub cum_in_pussy domestic_dog female feral gore open_pussy pajamas paw_patrol purple_eye restrained semi-grimdark skye_(paw_patrol)
<3_eyes anal clothed clothing cowgirl_position crossdressing eyewear food from_front_position fruit girly glasses halloween_costume hasbro heart hi_res husdur knife male male/male my_little_pony nurse_clothing nurse_uniform on_bottom on_top plant pumpkin semi-anthro semi-grimdark sex tinker_doo uniform
<3_eyes anal clothed clothing cowgirl_position crossdressing eyewear food from_front_position fruit girly glasses halloween_costume hasbro heart hi_res husdur knife male male/male my_little_pony nurse_clothing nurse_uniform on_bottom on_top plant pumpkin semi-anthro semi-grimdark sex tinker_doo uniform
1:1 absurd_res alternate_species anthro anthrofied blush breasts dominant equid equine female friendship_is_magic genitals greyscale hasbro hi_res horn hybrid imminent_sex interspecies interspecies_domination larger_male male mammal mind_break mind_control monochrome muscular muscular_male my_little_pony nipples nude pussy race_swap rarity_(mlp) semi-grimdark sex_slave size_difference slashysmiley slave smaller_female smile story story_in_description story_included straight_hair striped_body stripes submissive submissive_female tentacle unicorn zebra
1:1 absurd_res alternate_species anthro anthrofied blush breasts dominant equid equine female friendship_is_magic genitals greyscale hasbro hi_res horn hybrid imminent_sex interspecies interspecies_domination larger_male male mammal mind_break mind_control monochrome muscular muscular_male my_little_pony nipples nude pussy race_swap rarity_(mlp) semi-grimdark sex_slave size_difference slashysmiley slave smaller_female smile story story_in_description story_included straight_hair striped_body stripes submissive submissive_female tentacle unicorn zebra
<3_eyes anal clothed clothing cowgirl_position crossdressing cum_edit eyewear food from_front_position fruit girly glasses halloween_costume hasbro heart hi_res husdur knife male male/male my_little_pony nurse_clothing nurse_uniform on_bottom on_top plant pumpkin semi-anthro semi-grimdark sex tinker_doo uniform
<3_eyes anal clothed clothing cowgirl_position crossdressing cum_edit eyewear food from_front_position fruit girly glasses halloween_costume hasbro heart hi_res husdur knife male male/male my_little_pony nurse_clothing nurse_uniform on_bottom on_top plant pumpkin semi-anthro semi-grimdark sex tinker_doo uniform
10s 2014 4chan anthro anus ass clitoris dialogue ebola-chan equine looking_behind mashed_sushi mashedsushi my_little_pony original_character presenting pussy pussy_juice semi-grimdark tentacle uncensored upside-down
10s 2014 4chan anthro anus ass clitoris dialogue ebola-chan equine looking_behind mashed_sushi mashedsushi my_little_pony original_character presenting pussy pussy_juice semi-grimdark tentacle uncensored upside-down
3d animated anthro blood breasts epickitty54 friendship_is_magic gainaxing jiggle kicking my_little_pony rainbow_dash_(mlp) semi-grimdark source_filmmaker straight_hair
3d animated anthro blood breasts epickitty54 friendship_is_magic gainaxing jiggle kicking my_little_pony rainbow_dash_(mlp) semi-grimdark source_filmmaker straight_hair