riddle best from all time

Time frame

Tags

riddle

2d accessory animated anus asking_a_question big_breasts bimbo bimbo_body bimbofication bimbofied black_lips bouncing_breasts brown_nipples brown_pawpads capcom claws creepy_smile dialogue dialogue_box dragon's_dogma dragon's_dogma_2 english_text erect_nipples feathered_wings female giantess gif greek_mythology huge_breasts jiggling_breasts larger_female monster_girl mythological_sphinx nervous_sweat orange_eyes pawpads pussy_juice riddle seductive shaking_ass shaking_butt size_difference smaller_male sphinx sphinx_(dragon's_dogma) sweatdrop vagina vaginal_juice wings xxxx52
2d accessory animated anus asking_a_question big_breasts bimbo bimbo_body bimbofication bimbofied black_lips bouncing_breasts brown_nipples brown_pawpads capcom claws creepy_smile dialogue dialogue_box dragon's_dogma dragon's_dogma_2 english_text erect_nipples feathered_wings female giantess gif greek_mythology huge_breasts jiggling_breasts larger_female monster_girl mythological_sphinx nervous_sweat orange_eyes pawpads pussy_juice riddle seductive shaking_ass shaking_butt size_difference smaller_male sphinx sphinx_(dragon's_dogma) sweatdrop vagina vaginal_juice wings xxxx52
1futa 1girls areolae big_areola big_nipples bog breasts clothed clothed_female clothing curved_horns dialogue dickgirl duo english english_text female female_warrior flaccid forest futanari giant giant_futanari hair_tie hanging_penis height_difference hooves horns horsecock horsecock_futanari huge_breasts huge_cock human jack_cayless katana large_penis light-skinned_female light-skinned_futanari light_skin long_hair long_horns long_penis long_sword mangrove_tree medial_ring melee_weapon monster mostly_clothed multi_arm multi_limb nipples nipples_visible_through_clothing nude_futanari partially_submerged pelvic_curtain penis ponytail rapscallion_games riddle sheathed_sword sheathed_weapon size_difference speech_bubble swamp sword sword_sheath text thighhighs thumbs_up tied_hair tree trees two_tone_penis unconvincing_armor wall_of_text water weapon wet_clothes wet_shirt
1futa 1girls areolae big_areola big_nipples bog breasts clothed clothed_female clothing curved_horns dialogue dickgirl duo english english_text female female_warrior flaccid forest futanari giant giant_futanari hair_tie hanging_penis height_difference hooves horns horsecock horsecock_futanari huge_breasts huge_cock human jack_cayless katana large_penis light-skinned_female light-skinned_futanari light_skin long_hair long_horns long_penis long_sword mangrove_tree medial_ring melee_weapon monster mostly_clothed multi_arm multi_limb nipples nipples_visible_through_clothing nude_futanari partially_submerged pelvic_curtain penis ponytail rapscallion_games riddle sheathed_sword sheathed_weapon size_difference speech_bubble swamp sword sword_sheath text thighhighs thumbs_up tied_hair tree trees two_tone_penis unconvincing_armor wall_of_text water weapon wet_clothes wet_shirt
2024 accessory anus asking_a_question big_breasts bimbo bimbo_body bimbofication bimbofied black_lips bouncing_breasts brown_nipples brown_pawpads capcom claws creepy_smile dialogue dialogue_box dragon's_dogma dragon's_dogma_2 english_text erect_nipples feathered_wings female giantess greek_mythology huge_breasts larger_female monster_girl mythological_sphinx nervous_sweat orange_eyes pawpads pussy_juice riddle seductive shaking_butt size_difference smaller_male sphinx sphinx_(dragon's_dogma) sweatdrop vagina vaginal_juices wings xxxx52
2024 accessory anus asking_a_question big_breasts bimbo bimbo_body bimbofication bimbofied black_lips bouncing_breasts brown_nipples brown_pawpads capcom claws creepy_smile dialogue dialogue_box dragon's_dogma dragon's_dogma_2 english_text erect_nipples feathered_wings female giantess greek_mythology huge_breasts larger_female monster_girl mythological_sphinx nervous_sweat orange_eyes pawpads pussy_juice riddle seductive shaking_butt size_difference smaller_male sphinx sphinx_(dragon's_dogma) sweatdrop vagina vaginal_juices wings xxxx52
all_fours ambiguous_penetration anthro anthro_on_feral anthro_penetrating anthro_penetrating_feral avoid_posting bovine breasts busty_feral doggy_style duo female feral feral_penetrated from_behind_position greyscale hooves humanoid_face male male_penetrating mammal mane minotaur monochrome morbi muscular muscular_male nipples penetration penile_penetration quadruped riddle sex sphinx straight sweat wings
all_fours ambiguous_penetration anthro anthro_on_feral anthro_penetrating anthro_penetrating_feral avoid_posting bovine breasts busty_feral doggy_style duo female feral feral_penetrated from_behind_position greyscale hooves humanoid_face male male_penetrating mammal mane minotaur monochrome morbi muscular muscular_male nipples penetration penile_penetration quadruped riddle sex sphinx straight sweat wings
abs anthro big_breasts blood bodily_fluids breasts canid canine canis castlevania container cup dialogue dialogue_box drinking_glass egyptian_mythology english_text fangs female genitals glass glass_container glass_cup hi_res huge_breasts hybrid jackal konami looking_at_viewer mammal middle_eastern_mythology mummy mythology nipples nude pussy red_eyes riddle solo talking_to_viewer teeth text thebigbadwolf01 undead vampire wine_glass
abs anthro big_breasts blood bodily_fluids breasts canid canine canis castlevania container cup dialogue dialogue_box drinking_glass egyptian_mythology english_text fangs female genitals glass glass_container glass_cup hi_res huge_breasts hybrid jackal konami looking_at_viewer mammal middle_eastern_mythology mummy mythology nipples nude pussy red_eyes riddle solo talking_to_viewer teeth text thebigbadwolf01 undead vampire wine_glass
2023 accessory anthro ball_tuft balls big_balls big_penis blush body_hair bowser bowser_jr. cock_ring describing_penis describing_size dialogue embarrassed english_text erection eyewear father_(lore) father_and_child_(lore) father_and_son_(lore) flaccid genitals glasses group hairy hairy_balls hi_res hollo_nut iggy_koopa jewelry koopa koopaling larry_koopa lemmy_koopa ludwig_von_koopa male male_only mario_(series) morton_koopa_jr. musk musk_clouds musky_cock nintendo nude parent_(lore) parent_and_child_(lore) parent_and_son_(lore) penis penis_accessory penis_jewelry penis_shot penis_size_difference pubes riddle roy_koopa scalie small_penis son_(lore) testicle_cuff text tuft
2023 accessory anthro ball_tuft balls big_balls big_penis blush body_hair bowser bowser_jr. cock_ring describing_penis describing_size dialogue embarrassed english_text erection eyewear father_(lore) father_and_child_(lore) father_and_son_(lore) flaccid genitals glasses group hairy hairy_balls hi_res hollo_nut iggy_koopa jewelry koopa koopaling larry_koopa lemmy_koopa ludwig_von_koopa male male_only mario_(series) morton_koopa_jr. musk musk_clouds musky_cock nintendo nude parent_(lore) parent_and_child_(lore) parent_and_son_(lore) penis penis_accessory penis_jewelry penis_shot penis_size_difference pubes riddle roy_koopa scalie small_penis son_(lore) testicle_cuff text tuft
bodily_fluids duo equid equine felid feral genital_fluids genitals hasbro hi_res horse magic male mammal my_little_pony mythological_sphinx mythology omorashi peeing penis pony riddle squat_toilet triple_sevens_(triplesevens) triplesevens_(artist) urinal urine urine_stream wetting wings
bodily_fluids duo equid equine felid feral genital_fluids genitals hasbro hi_res horse magic male mammal my_little_pony mythological_sphinx mythology omorashi peeing penis pony riddle squat_toilet triple_sevens_(triplesevens) triplesevens_(artist) urinal urine urine_stream wetting wings
accessory anthro balls big_balls big_penis blush bowser bowser_jr. cock_ring dialogue embarrassed erection eyewear flaccid genitals glasses group hi_res hollo_nut iggy_koopa jewelry koopa koopaling larry_koopa lemmy_koopa ludwig_von_koopa male male_only mario_(series) morton_koopa_jr. nintendo nude penis penis_accessory penis_jewelry pubes riddle roy_koopa scalie small_penis
accessory anthro balls big_balls big_penis blush bowser bowser_jr. cock_ring dialogue embarrassed erection eyewear flaccid genitals glasses group hi_res hollo_nut iggy_koopa jewelry koopa koopaling larry_koopa lemmy_koopa ludwig_von_koopa male male_only mario_(series) morton_koopa_jr. nintendo nude penis penis_accessory penis_jewelry pubes riddle roy_koopa scalie small_penis
2boys black_eyes blowjob box clown clown_boy expressive_eyes face_closeup gay genitals goatee green_beanie green_skin green_tongue herecomesthecarnival insane_clown_posse juggalo looking_at_viewer male male_only milenko multiple_boys non-human_only open_legs open_mouth oral_sex penis pink_tip purple_hair purple_nose red_pubes riddle shoulders tongue_wrapped_around_penis wet_tongue white_skin
2boys black_eyes blowjob box clown clown_boy expressive_eyes face_closeup gay genitals goatee green_beanie green_skin green_tongue herecomesthecarnival insane_clown_posse juggalo looking_at_viewer male male_only milenko multiple_boys non-human_only open_legs open_mouth oral_sex penis pink_tip purple_hair purple_nose red_pubes riddle shoulders tongue_wrapped_around_penis wet_tongue white_skin
16:10 2021 absurd_res accessory ambrose_(maxydont) anus armor ass backsack ball_stretcher balls ballsack big_balls big_butt brown_body brown_hair brown_horn brown_membrane brown_scales chair claws clothing crown curved_horn dialogue digit_ring dragon english_text feral furgonomics furniture genitals gold_(metal) gold_jewelry greaves green_horn grey_claws hi_res horn horn_jewelry horn_ring jewelry long_hair looking_at_viewer looking_back looking_back_at_viewer lying male melee_weapon membrane_(anatomy) membranous_wings multicolored_body multicolored_horn multicolored_membrane multicolored_scales on_ground on_side penis pink_anus presenting presenting_anus presenting_hindquarters presenting_penis raised_tail reclining red_membrane redishdragie reptile riddle ring ring_(jewelry) robe scales scalie scrotum signature solo sword tail_accessory tail_tuft tailband tan_balls tan_body tan_scales teeth testicles text throne toe_claws toe_ring treasure_chest tuft two_tone_body two_tone_horn two_tone_membrane two_tone_scales two_tone_wings weapon western_dragon widescreen wings
16:10 2021 absurd_res accessory ambrose_(maxydont) anus armor ass backsack ball_stretcher balls ballsack big_balls big_butt brown_body brown_hair brown_horn brown_membrane brown_scales chair claws clothing crown curved_horn dialogue digit_ring dragon english_text feral furgonomics furniture genitals gold_(metal) gold_jewelry greaves green_horn grey_claws hi_res horn horn_jewelry horn_ring jewelry long_hair looking_at_viewer looking_back looking_back_at_viewer lying male melee_weapon membrane_(anatomy) membranous_wings multicolored_body multicolored_horn multicolored_membrane multicolored_scales on_ground on_side penis pink_anus presenting presenting_anus presenting_hindquarters presenting_penis raised_tail reclining red_membrane redishdragie reptile riddle ring ring_(jewelry) robe scales scalie scrotum signature solo sword tail_accessory tail_tuft tailband tan_balls tan_body tan_scales teeth testicles text throne toe_claws toe_ring treasure_chest tuft two_tone_body two_tone_horn two_tone_membrane two_tone_scales two_tone_wings weapon western_dragon widescreen wings
anthro barbed_wire blood canine cuts dialogue fear female fur furry helpless hurt learwolf male nude pain riddle tear tied_down wolf
anthro barbed_wire blood canine cuts dialogue fear female fur furry helpless hurt learwolf male nude pain riddle tear tied_down wolf