cowboy_outfit -animated best from all time

Time frame

Tags

cowboy outfit

animal_humanoid areola areolae beard big_breasts black_hair blonde_hair bodily_fluids bovid bovid_humanoid bovine bovine_humanoid breast_milking breasts breeding_slave breeding_stand cattle_humanoid closed_eyes clothing completely_naked completely_naked_female completely_nude completely_nude_female cowboy cowboy_hat cowboy_outfit curled_hair doggy_style dominant_human facial_hair female female_penetrated forced freckles from_behind_position group hair half-closed_eyes hat headgear headwear horn huge_breasts human human_is_better human_on_humanoid human_penetrating human_penetrating_humanoid human_supremacy humaned humanoid humanoid_penetrated interspecies lactating machine male male/female male_penetrating male_penetrating_female mammal mammal_humanoid milking_machine moustache narrowed_eyes penetration rape red_hair sabudenego sex standing standing_sex straw_in_mouth suspenders vaginal_penetration women_livestock
animal_humanoid areola areolae beard big_breasts black_hair blonde_hair bodily_fluids bovid bovid_humanoid bovine bovine_humanoid breast_milking breasts breeding_slave breeding_stand cattle_humanoid closed_eyes clothing completely_naked completely_naked_female completely_nude completely_nude_female cowboy cowboy_hat cowboy_outfit curled_hair doggy_style dominant_human facial_hair female female_penetrated forced freckles from_behind_position group hair half-closed_eyes hat headgear headwear horn huge_breasts human human_is_better human_on_humanoid human_penetrating human_penetrating_humanoid human_supremacy humaned humanoid humanoid_penetrated interspecies lactating machine male male/female male_penetrating male_penetrating_female mammal mammal_humanoid milking_machine moustache narrowed_eyes penetration rape red_hair sabudenego sex standing standing_sex straw_in_mouth suspenders vaginal_penetration women_livestock
1girls 4boys animal_genitalia anus ass belt bent_forward bent_over big_ass big_balls big_breasts big_butt big_penis blue_nails blunt_penis breasts brown_fur brown_skin chaps cock_sleeve cowboy_outfit crotchless_pants dark-skinned_female dark_skin dialogue egyptian erection farah female flared_penis gangbang gigantic_breasts going_commando grass green_eyes hazel_eyes headband heels height_difference high_heels holster horny horsecock huge_ass huge_balls huge_breasts huge_cock huge_penis hyper_breasts imminent_penetration imminent_sex indian_(cosplay) invitation inviting jeans larger_male legend_of_queen_opala long_penis looking_back male male_out_of_frame milf miniskirt multiple_boys multiple_males multiple_penises native_american no_panties one_eye_closed penis penis_holster penis_out penis_through_fly pink_anus pink_pussy pocahontas_(cosplay) precum presenting_hindquarters pussy secretly_loves_it size_difference skimpy_clothes smaller_female sparrow_(artist) speech_bubble stiletto_heels teasing text text_box text_bubble thigh_strap throbbing two_tone_penis upskirt very_high_heels wink winking
1girls 4boys animal_genitalia anus ass belt bent_forward bent_over big_ass big_balls big_breasts big_butt big_penis blue_nails blunt_penis breasts brown_fur brown_skin chaps cock_sleeve cowboy_outfit crotchless_pants dark-skinned_female dark_skin dialogue egyptian erection farah female flared_penis gangbang gigantic_breasts going_commando grass green_eyes hazel_eyes headband heels height_difference high_heels holster horny horsecock huge_ass huge_balls huge_breasts huge_cock huge_penis hyper_breasts imminent_penetration imminent_sex indian_(cosplay) invitation inviting jeans larger_male legend_of_queen_opala long_penis looking_back male male_out_of_frame milf miniskirt multiple_boys multiple_males multiple_penises native_american no_panties one_eye_closed penis penis_holster penis_out penis_through_fly pink_anus pink_pussy pocahontas_(cosplay) precum presenting_hindquarters pussy secretly_loves_it size_difference skimpy_clothes smaller_female sparrow_(artist) speech_bubble stiletto_heels teasing text text_box text_bubble thigh_strap throbbing two_tone_penis upskirt very_high_heels wink winking
1girls 3d abs apone3d belly_button belt belt_buckle blue_scarf breasts cowboy_boots cowboy_gloves cowboy_hat cowboy_outfit cowgirl cowgirl_boots cowgirl_hat cowgirl_outfit female female_only freckles freckles_on_face gloves hat high_resolution large_breasts light-skinned_female light_skin lips looking_at_viewer muscle muscles nipples pussy red_dead_redemption_(series) red_dead_redemption_2 sadie_adler scarf shotgun shotgun_shell solo thick thick_thighs thighhigh_boots thighs vagina very_high_resolution wide_hips
1girls 3d abs apone3d belly_button belt belt_buckle blue_scarf breasts cowboy_boots cowboy_gloves cowboy_hat cowboy_outfit cowgirl cowgirl_boots cowgirl_hat cowgirl_outfit female female_only freckles freckles_on_face gloves hat high_resolution large_breasts light-skinned_female light_skin lips looking_at_viewer muscle muscles nipples pussy red_dead_redemption_(series) red_dead_redemption_2 sadie_adler scarf shotgun shotgun_shell solo thick thick_thighs thighhigh_boots thighs vagina very_high_resolution wide_hips
1girl ass ass_focus bare_back bare_hips bare_shoulders bashou_(senran_kagura) boots bouncing_breasts breasts bull cowboy cowboy_boots cowboy_hat cowboy_outfit cowboy_western green_hair hat highres huge_ass huge_breasts large_breasts leather leather_boots leather_pants legs looking_to_the_side pants purple_eyes revealing_clothes riding senran_kagura short_hair sweat nervous_sweating thick_thighs thighs western yaegashi_nan
1girl ass ass_focus bare_back bare_hips bare_shoulders bashou_(senran_kagura) boots bouncing_breasts breasts bull cowboy cowboy_boots cowboy_hat cowboy_outfit cowboy_western green_hair hat highres huge_ass huge_breasts large_breasts leather leather_boots leather_pants legs looking_to_the_side pants purple_eyes revealing_clothes riding senran_kagura short_hair sweat nervous_sweating thick_thighs thighs western yaegashi_nan
1boy 1boy1girl 1girls anal anal_penetration anal_sex android_18 ass big_breasts blonde_hair blue_eyes breasts cowboy_outfit cum cum_in_ass cum_inside dragon_ball dragon_ball_z equine equine_penis horse horse_penis horsecock human humanoid nipples ruru-raida zoophilia
1boy 1boy1girl 1girls anal anal_penetration anal_sex android_18 ass big_breasts blonde_hair blue_eyes breasts cowboy_outfit cum cum_in_ass cum_inside dragon_ball dragon_ball_z equine equine_penis horse horse_penis horsecock human humanoid nipples ruru-raida zoophilia
1girl :o ahoge alternate_costume armpits arms_up bare_arms bare_legs bare_shoulders bed_sheet belt black_footwear blonde_hair blue_skirt blush boots breast_hold breasts brown_footwear christmas cleavage collarbone cowboy_boots cowboy_clothes cowboy_hat cowboy_outfit dakimakura_(medium) dress dual_persona envelope female_focus from_above full_body fur-trimmed_boots fur_trim hat unworn_hat unworn_headwear heart highres holly jewelry knees_together_feet_apart large_breasts legs letter long_hair lying miniskirt multiple_views neck necklace on_back panties pantyshot pink_panties purple_eyes red_dress red_ribbon ribbon rwby sample_watermark santa_boots santa_costume santa_hat seirei911 shirt short_dress skirt sleeveless sleeveless_dress smile strapless strapless_dress tank_top underwear vest watermark wavy_hair white_shirt yang_xiao_long
1girl :o ahoge alternate_costume armpits arms_up bare_arms bare_legs bare_shoulders bed_sheet belt black_footwear blonde_hair blue_skirt blush boots breast_hold breasts brown_footwear christmas cleavage collarbone cowboy_boots cowboy_clothes cowboy_hat cowboy_outfit dakimakura_(medium) dress dual_persona envelope female_focus from_above full_body fur-trimmed_boots fur_trim hat unworn_hat unworn_headwear heart highres holly jewelry knees_together_feet_apart large_breasts legs letter long_hair lying miniskirt multiple_views neck necklace on_back panties pantyshot pink_panties purple_eyes red_dress red_ribbon ribbon rwby sample_watermark santa_boots santa_costume santa_hat seirei911 shirt short_dress skirt sleeveless sleeveless_dress smile strapless strapless_dress tank_top underwear vest watermark wavy_hair white_shirt yang_xiao_long
1boy 2024 absurd_res belly_button blonde_hair blush blushing commission cowboy_hat cowboy_outfit crop_top cum cumming cumshot ejaculating_cum ejaculation femboy flannel flannel_shirt girly jackrockhardt jean_shorts leaning_on_rail long_hair looking_at_own_penis male male_masturbation male_only masturbating masturbation minishorts open_mouth penile_masturbation penis penis_grab penis_out public public_masturbation sleeves_rolled_up smiling solo stroking_penis unbuttoned_pants
1boy 2024 absurd_res belly_button blonde_hair blush blushing commission cowboy_hat cowboy_outfit crop_top cum cumming cumshot ejaculating_cum ejaculation femboy flannel flannel_shirt girly jackrockhardt jean_shorts leaning_on_rail long_hair looking_at_own_penis male male_masturbation male_only masturbating masturbation minishorts open_mouth penile_masturbation penis penis_grab penis_out public public_masturbation sleeves_rolled_up smiling solo stroking_penis unbuttoned_pants
ameizing_lewds angel_dust_(hazbin_hotel) big_ass big_breasts big_penis blowjob boob_window breasts_bigger_than_head breasts_out charlie_morningstar_(hazbin_hotel) cheating cheating_girlfriend clothed cock_shadow costume cowboy_hat cowboy_outfit demon demon_girl dialogue excessive_precum fellatio female giant_penis hazbin_hotel huge_ass huge_breasts huge_cock hyper_penis instant_loss_2koma massive_breasts no_bra non-con oral oral_sex paizufella paizuri penis penis_shadow questionable_consent rape shadow straight tagme text text_bubble throat_fuck
ameizing_lewds angel_dust_(hazbin_hotel) big_ass big_breasts big_penis blowjob boob_window breasts_bigger_than_head breasts_out charlie_morningstar_(hazbin_hotel) cheating cheating_girlfriend clothed cock_shadow costume cowboy_hat cowboy_outfit demon demon_girl dialogue excessive_precum fellatio female giant_penis hazbin_hotel huge_ass huge_breasts huge_cock hyper_penis instant_loss_2koma massive_breasts no_bra non-con oral oral_sex paizufella paizuri penis penis_shadow questionable_consent rape shadow straight tagme text text_bubble throat_fuck
1girls alabasta alternate_breast_size arabasta_saga belt black_hair breasts_bigger_than_head breasts_bigger_than_torso cleavage coat corset cowboy_hat cowboy_outfit enormous_breasts female female_only female_solo gigantic_breasts green_eyes hyper hyper_breasts licking long_hair mangrowing massive_breasts midriff miss_all_sunday navel nico_robin one_piece pre-timeskip river shorts solo solo_female tagme top_heavy watermark
1girls alabasta alternate_breast_size arabasta_saga belt black_hair breasts_bigger_than_head breasts_bigger_than_torso cleavage coat corset cowboy_hat cowboy_outfit enormous_breasts female female_only female_solo gigantic_breasts green_eyes hyper hyper_breasts licking long_hair mangrowing massive_breasts midriff miss_all_sunday navel nico_robin one_piece pre-timeskip river shorts solo solo_female tagme top_heavy watermark
2boys andy_von_de_oniyate cowboy_bebop cowboy_hat cowboy_outfit green_hair hat multiple_boys spike_spiegel tagme yaoi
2boys andy_von_de_oniyate cowboy_bebop cowboy_hat cowboy_outfit green_hair hat multiple_boys spike_spiegel tagme yaoi
5boys abs aka6 ambush_(trap) ass balls balls_in_panties belt big_ass big_penis bimbo cowboy_hat cowboy_outfit crossdressing eyewear femboy firearm footwear girly gun handwear headwear human imminent_anal imminent_rape imminent_sex male male_only maledom malesub neckwear pale_skin penis ram_ranch rifle shotgun testicles trap weapon yaoi
5boys abs aka6 ambush_(trap) ass balls balls_in_panties belt big_ass big_penis bimbo cowboy_hat cowboy_outfit crossdressing eyewear femboy firearm footwear girly gun handwear headwear human imminent_anal imminent_rape imminent_sex male male_only maledom malesub neckwear pale_skin penis ram_ranch rifle shotgun testicles trap weapon yaoi
1boy 1boy1girl 1girls anonviscom bliss blonde_hair bottomless_female bottomless_female_nude_male braid braided_ponytail closed_eyes clothed_female_nude_male cowboy_hat cowboy_outfit cum_in_mouth cum_in_pussy cum_on_breasts cum_on_face day english_text grass hairy_male hetero hetero_sex highres light_skinned_female lying missionary_position mostly_offscreen_character mostly_offscreen_male no_bra nude_male on_grass outdoor_sex outdoors outside partial_male penile_penetration penis_in_pussy realistic red_dead_redemption_2 sadie_adler sex speech_bubble spread_legs straight straight_sex suspenders text_bubble uncensored vaginal vaginal_penetration vaginal_sex
1boy 1boy1girl 1girls anonviscom bliss blonde_hair bottomless_female bottomless_female_nude_male braid braided_ponytail closed_eyes clothed_female_nude_male cowboy_hat cowboy_outfit cum_in_mouth cum_in_pussy cum_on_breasts cum_on_face day english_text grass hairy_male hetero hetero_sex highres light_skinned_female lying missionary_position mostly_offscreen_character mostly_offscreen_male no_bra nude_male on_grass outdoor_sex outdoors outside partial_male penile_penetration penis_in_pussy realistic red_dead_redemption_2 sadie_adler sex speech_bubble spread_legs straight straight_sex suspenders text_bubble uncensored vaginal vaginal_penetration vaginal_sex
2018 2girls alternate_breast_size american animal_tail areolae arm_gloves bangs bent_over big_ass big_breasts big_hair bigdad bimbo blonde_hair bolo_tie boots bottomless breast_milk breast_sucking breasts brown_hair clothed_female_nude_female cow_accoutrements cow_ears cow_girl cow_print cow_print_lingerie cowboy_boots cowboy_gloves cowboy_hat cowboy_outfit cowgirl dazed disney disney_channel doggy_style doggystyle domination duo female female_only femdom femsub footwear from_behind from_behind_position garter_belt garter_straps gravity_falls hand_behind_head handwear hanging_breasts happy_sex hat headwear horns hucow huge_breasts huge_nipples human implied_penetration lactation lesbian mabel_pines milk milking_machine moaning moo_bitch multiple_girls nipples no_bra one_eye_closed pacifica_northwest pale_skin sex_toy shiny_skin simple_background smug standing_doggy_style standing_sex stockings strap-on strapon submissive submissive_female tail_grab tanlines thighhighs thin_waist topless very_long_hair vest white_background yuri
2018 2girls alternate_breast_size american animal_tail areolae arm_gloves bangs bent_over big_ass big_breasts big_hair bigdad bimbo blonde_hair bolo_tie boots bottomless breast_milk breast_sucking breasts brown_hair clothed_female_nude_female cow_accoutrements cow_ears cow_girl cow_print cow_print_lingerie cowboy_boots cowboy_gloves cowboy_hat cowboy_outfit cowgirl dazed disney disney_channel doggy_style doggystyle domination duo female female_only femdom femsub footwear from_behind from_behind_position garter_belt garter_straps gravity_falls hand_behind_head handwear hanging_breasts happy_sex hat headwear horns hucow huge_breasts huge_nipples human implied_penetration lactation lesbian mabel_pines milk milking_machine moaning moo_bitch multiple_girls nipples no_bra one_eye_closed pacifica_northwest pale_skin sex_toy shiny_skin simple_background smug standing_doggy_style standing_sex stockings strap-on strapon submissive submissive_female tail_grab tanlines thighhighs thin_waist topless very_long_hair vest white_background yuri
2boys ass bromeo_(lacryboy) bulge cowboy_outfit gay girly kneeling lacryboy male/male male_only melanpsycholia miles_(melanpsycholia) multiple_views presenting sex sketch yaoi
2boys ass bromeo_(lacryboy) bulge cowboy_outfit gay girly kneeling lacryboy male/male male_only melanpsycholia miles_(melanpsycholia) multiple_views presenting sex sketch yaoi
1futa 2012 abs androgynous areola arm_tattoo balls bare_shoulders barn beauty_mark bedroom_eyes biceps big_breasts big_penis blonde_hair blue_eyes blush braided_hair breasts chaps cowboy_outfit cowgirl cowgirl_outfit dickgirl erect_nipples flaccid futa_only futanari gloves green_eyes hair horsecock horsegirl huge_cock human humanoid incase intersex long_hair looking_at_viewer mole_under_mouth muscles muscular muscular_futanari navel nipples outside penis penis_to_the_knees pointy_ears sheath skimpy smile solo solo_futa tattoo testicles twintails veins veiny_penis
1futa 2012 abs androgynous areola arm_tattoo balls bare_shoulders barn beauty_mark bedroom_eyes biceps big_breasts big_penis blonde_hair blue_eyes blush braided_hair breasts chaps cowboy_outfit cowgirl cowgirl_outfit dickgirl erect_nipples flaccid futa_only futanari gloves green_eyes hair horsecock horsegirl huge_cock human humanoid incase intersex long_hair looking_at_viewer mole_under_mouth muscles muscular muscular_futanari navel nipples outside penis penis_to_the_knees pointy_ears sheath skimpy smile solo solo_futa tattoo testicles twintails veins veiny_penis
2animals 2girls blue_eyes blue_hair blush bunny_and_fox_world cheeks_broadchester closed_eyes cowboy_boots cowboy_hat cowboy_outfit cum cum_in_mouth darkartskai ejaculation freckles green_eyes group handjob horse horsecock long_hair oral shephira short_hair stable tagme tied_hair vaginal_penetration white_hair zoophilia
2animals 2girls blue_eyes blue_hair blush bunny_and_fox_world cheeks_broadchester closed_eyes cowboy_boots cowboy_hat cowboy_outfit cum cum_in_mouth darkartskai ejaculation freckles green_eyes group handjob horse horsecock long_hair oral shephira short_hair stable tagme tied_hair vaginal_penetration white_hair zoophilia
1girls 2011 5_fingers all_fours anal anal_insertion anal_object_insertion anal_penetration animal_print animate_inanimate arm_support ass battery bent_over blue_bottomwear blue_clothing blue_pants blush boots bottomwear braid braided_hair braided_ponytail brown_boots butt chaps clothed clothed_masturbation clothing cloud cloudscape cow_print cowboy cowboy_boots cowboy_hat cowboy_outfit cowgirl disney doll enjoying fabio_paulino female female_focus female_masturbation female_only female_penetrated female_solo fingers footwear full-length_portrait full_body genitals glistening glistening_body glistening_skin green_eyes hair hand_on_wall happy hat headgear headwear human humanoid humanoid_genitalia humanoid_pussy inside jessie_(toy_story) large_insertion light-skinned_female light_skin linno lips long_hair long_sleeves looking_pleasured looking_up masturbation medium_breasts no_underwear object_insertion open_mouth open_smile pants pants_down partially_clothed penetration pixar pleasure_face ponytail portrait pussy rear_view red_hair red_lips round_ass shiny shiny_skin sky slit smile solo solo_female solo_focus teeth thighs tied_hair topwear toy toy_story uncensored upper_teeth vagina wall wall_(disambiguation)
1girls 2011 5_fingers all_fours anal anal_insertion anal_object_insertion anal_penetration animal_print animate_inanimate arm_support ass battery bent_over blue_bottomwear blue_clothing blue_pants blush boots bottomwear braid braided_hair braided_ponytail brown_boots butt chaps clothed clothed_masturbation clothing cloud cloudscape cow_print cowboy cowboy_boots cowboy_hat cowboy_outfit cowgirl disney doll enjoying fabio_paulino female female_focus female_masturbation female_only female_penetrated female_solo fingers footwear full-length_portrait full_body genitals glistening glistening_body glistening_skin green_eyes hair hand_on_wall happy hat headgear headwear human humanoid humanoid_genitalia humanoid_pussy inside jessie_(toy_story) large_insertion light-skinned_female light_skin linno lips long_hair long_sleeves looking_pleasured looking_up masturbation medium_breasts no_underwear object_insertion open_mouth open_smile pants pants_down partially_clothed penetration pixar pleasure_face ponytail portrait pussy rear_view red_hair red_lips round_ass shiny shiny_skin sky slit smile solo solo_female solo_focus teeth thighs tied_hair topwear toy toy_story uncensored upper_teeth vagina wall wall_(disambiguation)
beelzebub_(helltaker) big_breasts choker cleavage cowboy_hat cowboy_outfit demon_girl demon_horns demon_tail dialogue farmer farmgirl gloves grey_background helltaker horns huge_breasts krekk0v naughty_face plain_background red_eyes seductive seductive_smile short_hair smile smug thick_thighs tied_shirt wheat
beelzebub_(helltaker) big_breasts choker cleavage cowboy_hat cowboy_outfit demon_girl demon_horns demon_tail dialogue farmer farmgirl gloves grey_background helltaker horns huge_breasts krekk0v naughty_face plain_background red_eyes seductive seductive_smile short_hair smile smug thick_thighs tied_shirt wheat
1girls beelzebub_(helltaker) big_breasts choker cleavage colorized cowboy_hat cowboy_outfit ddl demon_girl demon_horns demon_tail dialogue edit farmer farmgirl gloves grey_background helltaker horns huge_breasts krekk0v naughty_face plain_background red_eyes seductive seductive_smile short_hair smile smug the_void thick_thighs third-party_edit tied_shirt wheat
1girls beelzebub_(helltaker) big_breasts choker cleavage colorized cowboy_hat cowboy_outfit ddl demon_girl demon_horns demon_tail dialogue edit farmer farmgirl gloves grey_background helltaker horns huge_breasts krekk0v naughty_face plain_background red_eyes seductive seductive_smile short_hair smile smug the_void thick_thighs third-party_edit tied_shirt wheat
1futa abs animal_genitalia areolae balls blonde_hair boots breasts casual coat cowboy_hat cowboy_outfit cowgirl cowgirl_outfit cybernetics dickgirl fingerless_gloves flaccid flexing footwear futa_only futanari hand_on_hip handwear headwear horsecock huge_cock human intersex itchyears looking_at_viewer muscular muscular_futanari neckwear nipples one_hand_on_hip outerwear pale_skin penis prosthetic_arm purple_eyes rwby sheath smile solo solo_futa testicles yang_xiao_long
1futa abs animal_genitalia areolae balls blonde_hair boots breasts casual coat cowboy_hat cowboy_outfit cowgirl cowgirl_outfit cybernetics dickgirl fingerless_gloves flaccid flexing footwear futa_only futanari hand_on_hip handwear headwear horsecock huge_cock human intersex itchyears looking_at_viewer muscular muscular_futanari neckwear nipples one_hand_on_hip outerwear pale_skin penis prosthetic_arm purple_eyes rwby sheath smile solo solo_futa testicles yang_xiao_long
2boys arm_restraints ball_gag bitchsuit blindfold blonde_hair bondage chastity chastity_cage chastity_device cock_cage contraption_concept cow_print cowboy_hat cowboy_outfit design_sheet dildo dildo_riding electricity femboy gag horse horsecock latex latex_suit pet pet_play petplay pony saddle sissy stallion tagme text trap yazva zoophilia
2boys arm_restraints ball_gag bitchsuit blindfold blonde_hair bondage chastity chastity_cage chastity_device cock_cage contraption_concept cow_print cowboy_hat cowboy_outfit design_sheet dildo dildo_riding electricity femboy gag horse horsecock latex latex_suit pet pet_play petplay pony saddle sissy stallion tagme text trap yazva zoophilia