headware best from all time

Time frame

Tags

headware

1girls alternate_breast_size arched_back ass bare_ass bare_back beach beach_towel beanie big_ass big_breasts big_butt big_thighs breasts_bigger_than_head brown_hair bubble_butt cleavage curvaceous curvy dat_ass erect_nipples exposed_ass exposed_breasts family_guy female female_only glasses green_eyes hat headware headwear hourglass_figure huge_areolae huge_ass huge_breasts ladycandy2011 large_breasts looking_at_viewer meg_griffin nipple nude nude_female pink_beanie pink_hat pink_headwear puffy_nipples short_hair sideboob solo solo_female tan_lines tanlines teenager thick_lips voluptuous wide_hips
1girls alternate_breast_size arched_back ass bare_ass bare_back beach beach_towel beanie big_ass big_breasts big_butt big_thighs breasts_bigger_than_head brown_hair bubble_butt cleavage curvaceous curvy dat_ass erect_nipples exposed_ass exposed_breasts family_guy female female_only glasses green_eyes hat headware headwear hourglass_figure huge_areolae huge_ass huge_breasts ladycandy2011 large_breasts looking_at_viewer meg_griffin nipple nude nude_female pink_beanie pink_hat pink_headwear puffy_nipples short_hair sideboob solo solo_female tan_lines tanlines teenager thick_lips voluptuous wide_hips
2boys a_hat_in_time anthro ass avian bedroom_eyes big_butt blush bottomless clothed clothing crossover duo femboy girly grey_body hat headgear headware headwear heart honkai:_star_rail honkai_(series) horny huge_butt inuzu lagomorph leporid mammal massive_ass mihoyo narrowed_eyes onomatopoeia open_mouth pom-pom_(honkai:_star_rail) quality question_mark rabbit seductive shirt sound_effects speech_bubble take_your_pick text the_conductor tongue tongue_out yellow_body
2boys a_hat_in_time anthro ass avian bedroom_eyes big_butt blush bottomless clothed clothing crossover duo femboy girly grey_body hat headgear headware headwear heart honkai:_star_rail honkai_(series) horny huge_butt inuzu lagomorph leporid mammal massive_ass mihoyo narrowed_eyes onomatopoeia open_mouth pom-pom_(honkai:_star_rail) quality question_mark rabbit seductive shirt sound_effects speech_bubble take_your_pick text the_conductor tongue tongue_out yellow_body
1girls ai_generated arms_behind_back big_breasts black_hair civitai female female_only hat headware hyuuga_hinata large_boobs large_breasts light-skinned_female light_skin military military_uniform naruto naruto_(series) naruto_shippuden nazi necktie nipple_slip nipples no_pupils open_clothes pale_skin purple_eyes solo warden
1girls ai_generated arms_behind_back big_breasts black_hair civitai female female_only hat headware hyuuga_hinata large_boobs large_breasts light-skinned_female light_skin military military_uniform naruto naruto_(series) naruto_shippuden nazi necktie nipple_slip nipples no_pupils open_clothes pale_skin purple_eyes solo warden
ass ball_gag big_dildo bondage bound bound_ankles bound_tail bound_wrists breasts canine clothing collar dildo disney female femdom fox fur furniture furry gag gagged grey_fur headware imminent_rape judy_hopps lagomorph male malesub mammal nick_wilde nipple_tassels orange_fur ottoghetto_(artist) pegging pink_ball_gag rabbit sex_toy skirt small_breasts submissive_male tape tied_up top-down_bottom-up zootopia
ass ball_gag big_dildo bondage bound bound_ankles bound_tail bound_wrists breasts canine clothing collar dildo disney female femdom fox fur furniture furry gag gagged grey_fur headware imminent_rape judy_hopps lagomorph male malesub mammal nick_wilde nipple_tassels orange_fur ottoghetto_(artist) pegging pink_ball_gag rabbit sex_toy skirt small_breasts submissive_male tape tied_up top-down_bottom-up zootopia
alien anthro ass ass_to_ass baseball_cap belly big_ass big_butt bodily_fluids bottom_heavy clothing crossed_arms curvy_figure duo erection eyewear eyewear_on_head femboy genital_fluids genitals girly glasses glasses_on_head glistening glistening_butt grin grinning_at_viewer hat headgear headware headwear hi_res huge_ass huge_butt humanoid hyper hyper_ass hyper_butt jubee_(sqoon) looking_at_viewer male male/male penis precum puwa red_(sethkeidashi) smile sqoon tail thick_thighs
alien anthro ass ass_to_ass baseball_cap belly big_ass big_butt bodily_fluids bottom_heavy clothing crossed_arms curvy_figure duo erection eyewear eyewear_on_head femboy genital_fluids genitals girly glasses glasses_on_head glistening glistening_butt grin grinning_at_viewer hat headgear headware headwear hi_res huge_ass huge_butt humanoid hyper hyper_ass hyper_butt jubee_(sqoon) looking_at_viewer male male/male penis precum puwa red_(sethkeidashi) smile sqoon tail thick_thighs
anthro big_breasts black_body black_fur bottomwear breasts canid canid_demon clothed clothing cross demon female fur gesture gloves hair hand_on_leg hand_on_thigh handwear headware hellhound helluva_boss hi_res huge_breasts hyper hyper_breasts legwear loona_(helluva_boss) mammal midriff nipple_piercing nipples nun nun_outfit piercing pointing pointing_up princedragonsfw red_sclera ripped_thigh_highs skirt solo solo_focus tail thick_thighs thigh_highs thighhighs torn_clothes visible_areola white_body white_fur white_hair
anthro big_breasts black_body black_fur bottomwear breasts canid canid_demon clothed clothing cross demon female fur gesture gloves hair hand_on_leg hand_on_thigh handwear headware hellhound helluva_boss hi_res huge_breasts hyper hyper_breasts legwear loona_(helluva_boss) mammal midriff nipple_piercing nipples nun nun_outfit piercing pointing pointing_up princedragonsfw red_sclera ripped_thigh_highs skirt solo solo_focus tail thick_thighs thigh_highs thighhighs torn_clothes visible_areola white_body white_fur white_hair
3d allaynsfw aubrey_(fortnite) blender blush breasts breasts_out brunnette fortnite fortnite:_battle_royale hands_behind_head headgear headware light-skinned_female light_skin money money_under_clothes pov pov_eye_contact skinny skinny_girl toned_female topless topless_female
3d allaynsfw aubrey_(fortnite) blender blush breasts breasts_out brunnette fortnite fortnite:_battle_royale hands_behind_head headgear headware light-skinned_female light_skin money money_under_clothes pov pov_eye_contact skinny skinny_girl toned_female topless topless_female
anal anal_sex anal_tugging anthro ass avian balls bandage bandaged_arm bandaged_leg big_butt blin_(tloz) bodily_fluids breath_of_the_wild bubble_butt claws coercion dripping duo english_text erection foreskin furry genital_fluids genitals half-closed_eyes headware heart_(marking) hi_res humanoid_genitalia humanoid_penis larger_male looking_pleasured male male/male male_only moblin moblin_(breath_of_the_wild) muscular muscular_male narrowed_eyes nintendo nipples open_mouth pecs penetration penis power_bottom precum precum_drip precum_in_ass public public_sex questionable_consent rito sex size_difference small_dom_big_sub smaller_male stomach_bulge text the_legend_of_zelda tongue tongue_out v3rg3
anal anal_sex anal_tugging anthro ass avian balls bandage bandaged_arm bandaged_leg big_butt blin_(tloz) bodily_fluids breath_of_the_wild bubble_butt claws coercion dripping duo english_text erection foreskin furry genital_fluids genitals half-closed_eyes headware heart_(marking) hi_res humanoid_genitalia humanoid_penis larger_male looking_pleasured male male/male male_only moblin moblin_(breath_of_the_wild) muscular muscular_male narrowed_eyes nintendo nipples open_mouth pecs penetration penis power_bottom precum precum_drip precum_in_ass public public_sex questionable_consent rito sex size_difference small_dom_big_sub smaller_male stomach_bulge text the_legend_of_zelda tongue tongue_out v3rg3
abs absurd_res anal anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bar bar_stool barefoot biceps biped black_body black_penis claws clothing digital_media_(artwork) duo erection feet fingers fur furniture genitals hair hait hand_on_penis hat headgear headware headwear hi_res inside male male/male male_penetrated male_penetrating male_penetrating_male muscular muscular_anthro muscular_male muscular_thighs nude pawpads pecs penetration penile penile_penetration penis reach_around sex sitting sitting_on_bar_counter solard0gg0 stomach_bulge stool tagg taggz_(character) tail teeth toe_claws toes triceps tuft white_body white_fur white_hair
abs absurd_res anal anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bar bar_stool barefoot biceps biped black_body black_penis claws clothing digital_media_(artwork) duo erection feet fingers fur furniture genitals hair hait hand_on_penis hat headgear headware headwear hi_res inside male male/male male_penetrated male_penetrating male_penetrating_male muscular muscular_anthro muscular_male muscular_thighs nude pawpads pecs penetration penile penile_penetration penis reach_around sex sitting sitting_on_bar_counter solard0gg0 stomach_bulge stool tagg taggz_(character) tail teeth toe_claws toes triceps tuft white_body white_fur white_hair
abs anal anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bar bar_stool barefoot biceps biped black_body black_penis blush bodily_fluids claws clothing cum cumshot duo ejaculation erection feet fingers fur furniture genital_fluids genitals hair hait hand_on_penis hat headgear headware headwear hi_res inside male male/male male_penetrated male_penetrating male_penetrating_male muscular muscular_anthro muscular_male muscular_thighs navel nude orgasm pawpads pecs penetration penile penile_penetration penis reach_around sex sitting sitting_on_bar_counter solard0gg0 stool taggz_(character) tail teeth toe_claws toes triceps tuft white_body white_fur white_hair
abs anal anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bar bar_stool barefoot biceps biped black_body black_penis blush bodily_fluids claws clothing cum cumshot duo ejaculation erection feet fingers fur furniture genital_fluids genitals hair hait hand_on_penis hat headgear headware headwear hi_res inside male male/male male_penetrated male_penetrating male_penetrating_male muscular muscular_anthro muscular_male muscular_thighs navel nude orgasm pawpads pecs penetration penile penile_penetration penis reach_around sex sitting sitting_on_bar_counter solard0gg0 stool taggz_(character) tail teeth toe_claws toes triceps tuft white_body white_fur white_hair
2019 4_toes absurd_res anatomically_correct animal_genitalia anus ass_up avian beak bird brick cloaca clothing crane_(bird) defeated detailed_background digital_media_(artwork) dreamworks feathered_wings feathers feet feral fireproof galliform gruiform hat headgear headware headwear hi_res imminent_rape kung_fu_panda light lord_shen male male_only master_crane monochrome nude open_mouth peafowl phasianid presenting smile smirk sunlight talons toes white_body white_feathers wings
2019 4_toes absurd_res anatomically_correct animal_genitalia anus ass_up avian beak bird brick cloaca clothing crane_(bird) defeated detailed_background digital_media_(artwork) dreamworks feathered_wings feathers feet feral fireproof galliform gruiform hat headgear headware headwear hi_res imminent_rape kung_fu_panda light lord_shen male male_only master_crane monochrome nude open_mouth peafowl phasianid presenting smile smirk sunlight talons toes white_body white_feathers wings
abs anal anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bar bar_stool barefoot belly_inflation biceps biped black_body black_penis blush bodily_fluids claws clothing cum cum_inside cum_string duo erection feet fingers fur furniture genital_fluids genitals hair hait hand_on_penis hat headgear headware headwear hi_res inflation inflation inside male male/male male_penetrated male_penetrating male_penetrating_male muscular muscular_anthro muscular_male muscular_thighs navel nude pawpads pecs penetration penile penile_penetration penis reach_around sex sitting sitting_on_bar_counter solard0gg0 stool taggz_(character) tail teeth toe_claws toes triceps tuft white_body white_fur white_hair
abs anal anal_sex anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro balls bar bar_stool barefoot belly_inflation biceps biped black_body black_penis blush bodily_fluids claws clothing cum cum_inside cum_string duo erection feet fingers fur furniture genital_fluids genitals hair hait hand_on_penis hat headgear headware headwear hi_res inflation inflation inside male male/male male_penetrated male_penetrating male_penetrating_male muscular muscular_anthro muscular_male muscular_thighs navel nude pawpads pecs penetration penile penile_penetration penis reach_around sex sitting sitting_on_bar_counter solard0gg0 stool taggz_(character) tail teeth toe_claws toes triceps tuft white_body white_fur white_hair
absurd_res anthro backwards_baseball_cap backwards_hat baseball_cap big_breasts breasts clothing colored_nails feet female fish genitals hair hat headgear headware headwear hi_res hybrid marine nails nipple_piercing nipples piercing purple_hair pussy shark skidd solo
absurd_res anthro backwards_baseball_cap backwards_hat baseball_cap big_breasts breasts clothing colored_nails feet female fish genitals hair hat headgear headware headwear hi_res hybrid marine nails nipple_piercing nipples piercing purple_hair pussy shark skidd solo
ai_generated arms_behind_back big_breasts black_hair cap civitai cosplay hat headware hyuuga_hinata hyuuga_hinata large_boobs large_breasts mario_(series) naruto naruto_(series) naruto_shippuden no_pupils purple_eyes red_hat
ai_generated arms_behind_back big_breasts black_hair cap civitai cosplay hat headware hyuuga_hinata hyuuga_hinata large_boobs large_breasts mario_(series) naruto naruto_(series) naruto_shippuden no_pupils purple_eyes red_hat
amira azaleesh bodily_fluids bondage bound breasts canid canine drooling female female/female fox headware invalid_tag mammal nipples pussy rope saliva samira yuri
amira azaleesh bodily_fluids bondage bound breasts canid canine drooling female female/female fox headware invalid_tag mammal nipples pussy rope saliva samira yuri
aubrey_(fortnite) blush brown_hair dr34ms_3d fortnite headgear headware light-skinned_female naked shy solo_female
aubrey_(fortnite) blush brown_hair dr34ms_3d fortnite headgear headware light-skinned_female naked shy solo_female
absurd_res argon_vile blush burt clothing dreamworks elephant elephantid foot_play foreskin gay genitals hat headgear headware headwear hi_res king_julien lemur madagascar_(series) mammal nickelodeon penetration penis primate proboscidean strepsirrhine the_penguins_of_madagascar toe_in_penis toe_in_urethra toe_insertion urethral urethral_penetration urethral_toeing
absurd_res argon_vile blush burt clothing dreamworks elephant elephantid foot_play foreskin gay genitals hat headgear headware headwear hi_res king_julien lemur madagascar_(series) mammal nickelodeon penetration penis primate proboscidean strepsirrhine the_penguins_of_madagascar toe_in_penis toe_in_urethra toe_insertion urethral urethral_penetration urethral_toeing
ahe_gao alien alien_genitalia alien_humanoid barefoot bikini bikini_top blue_tongue bra breasts claytonh clothing colored_nails cowboy_clayton cowboyclayton digital_drawing_(artwork) digital_media_(artwork) digital_painting_(artwork) feet female foot_focus genitals goo_creature green_goo green_slime hair hands_on_legs hands_on_thighs headgear headphones headset headware hi_res humanoid ibispaintx looking_down looking_pleasured mostly_nude nails nude nude_female orgasm_face pale pale_skin penetrating_slime penetration purple_eyes purple_hair pussy red_bikini red_bikini_top red_bra red_clothing red_swimwear red_underwear science_fiction slime slime_(blob) small_breasts small_waist space spread_legs spread_pussy spreading swimwear tizzat tizzat1894 toenail_gunk tongue tongue_out underwear vaginal_penetration vaginal_penetration white_body white_skin zoe(cowboyclayton) zoe_(cowboyclayton)
ahe_gao alien alien_genitalia alien_humanoid barefoot bikini bikini_top blue_tongue bra breasts claytonh clothing colored_nails cowboy_clayton cowboyclayton digital_drawing_(artwork) digital_media_(artwork) digital_painting_(artwork) feet female foot_focus genitals goo_creature green_goo green_slime hair hands_on_legs hands_on_thighs headgear headphones headset headware hi_res humanoid ibispaintx looking_down looking_pleasured mostly_nude nails nude nude_female orgasm_face pale pale_skin penetrating_slime penetration purple_eyes purple_hair pussy red_bikini red_bikini_top red_bra red_clothing red_swimwear red_underwear science_fiction slime slime_(blob) small_breasts small_waist space spread_legs spread_pussy spreading swimwear tizzat tizzat1894 toenail_gunk tongue tongue_out underwear vaginal_penetration vaginal_penetration white_body white_skin zoe(cowboyclayton) zoe_(cowboyclayton)
absurd_res alpha_channel anthro chubby_anthro chubby_belly chubby_male clothing domestic_cat felid feline felis flaccid genitals headgear headware hi_res male mammal mostly_nude penis salamikii simple_background slightly_chubby solo squire_(salamikii) transparent_background yellow_eyes
absurd_res alpha_channel anthro chubby_anthro chubby_belly chubby_male clothing domestic_cat felid feline felis flaccid genitals headgear headware hi_res male mammal mostly_nude penis salamikii simple_background slightly_chubby solo squire_(salamikii) transparent_background yellow_eyes