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2019 anal anal_penetration anthro anthro_on_anthro barn bodily_fluids bovid bovine butt canid canine canis cattle chaps clothing cowboy cowboy_hat cowgirl_position digital_media_(artwork) dobermann domestic_dog duo erection farm from_front_position genitals hat headgear headwear highpups interspecies jake_the_cowboy kissing male male/male male_on_bottom male_on_top male_penetrated male_penetrating male_penetrating_male mammal manny_the_cowboy muscular muscular_male on_bottom on_top penetration penis pinscher saliva sex slightly_chubby thick_thighs underwear
2019 aggressive anal anal_penetration animal_genitalia animal_penis anthro anthro_on_anthro arterian_(character) balls big_butt bodily_fluids butt canid canine canis cum digital_media_(artwork) dirty dobermann domestic_dog duo erection genital_fluids genitals hi_res kitafune_matsuki knot male male/male male_penetrated male_penetrating male_penetrating_male mammal manny_the_cowboy messy mud mud_covered mud_sex muddy mudwuff muscular muscular_male mythological_canine mythological_creature mythology nude penetration penis pinscher sex simple_background smile teeth thick_thighs wam werecanid werecanine werecreature werewolf wolf
2020 absurd_res anal anal_knotting anal_penetration animal_genitalia animal_penis anthro anthro_dominating_human anthro_dominating_male anthro_penetrating anthro_penetrating_human anthro_penetrating_male anus arterian_(character) big_butt blush bodily_fluids butt canid canine canine_genitalia canine_penis canis chaps clothing cowboy cowboy_hat cowboy_outfit cum cum_in_ass cum_inside dialogue dobermann domestic_dog dominant dominant_anthro dominant_male duo english_text facesitting french_kissing from_front_position genital_fluids genitals hat headgear headwear hi_res human human_on_anthro human_penetrated humanoid_genitalia interspecies kerchief kissing knot knotting lying male male/male male_anthro male_human male_on_anthro male_on_bottom male_on_human male_on_top male_penetrated male_penetrating male_penetrating_human male_penetrating_male mammal manny_the_cowboy mating_press muscular muscular_male nipples nude on_back on_bottom on_top oral penetration penile penile_penetration penis pinscher rimming severeni sex simple_background sitting sitting_on_another submissive submissive_human submissive_male tattoo text tribal tribal_tattoo
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animal_genitalia animal_penis anthro balls bedroom_eyes belly big_butt bodily_fluids butt canid canine canine_genitalia canine_penis canis chaps clothing cowboy dobermann domestic_dog erection fence genital_fluids genitals hat headgear headwear hi_res kerchief knot leaking_precum leaning leaning_backward leather leather_clothing looking_at_viewer male mammal manny_the_cowboy musclegut muscular muscular_male narrowed_eyes nipples penis pinscher precum seductive simple_background slightly_chubby smile snail3n solo thick_thighs
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anal anal_penetration animal_genitalia animal_penis animated anthro anus balls bastion_(red_winds) big_butt bovid bovine butt canid canine canis cattle chaps cowboy dobermann domestic_dog duo equine_genitalia equine_penis erection gaping gaping_anus genitals hi_res highland_cattle horn kerchief male male/male male_penetrated male_penetrating male_penetrating_male mammal manny_the_cowboy muscular muscular_anthro muscular_male neckerchief neckwear no_sound penetration penis pinscher power_bottom puffy_anus retracted_balls sergevna sex short_playtime simple_background smile throbbing throbbing_balls throbbing_penis video
2019 after_anal after_orgasm after_sex anal anthro anus balls barn bodily_fluids bovid bovine butt canid canine canis cattle chaps clothing cowbell cowboy cowboy_hat cowgirl_position cum cum_in_ass cum_inside digital_media_(artwork) dobermann domestic_dog duo erection facial_piercing from_front_position gaping gaping_anus genital_fluids genitals half-closed_eyes hat headgear headwear hi_res highpups humanoid_genitalia humanoid_penis interspecies jake_the_cowboy kissing light light_beam looking_back lying male male/male male_on_bottom male_on_top mammal manny_the_cowboy muscular muscular_male narrowed_eyes nose_piercing nose_ring on_back on_bottom on_top open_mouth penis piercing pinscher pubes ring_piercing saliva sex slightly_chubby sweat thick_thighs
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absurd_res anthro anus back_muscles balls big_butt butt canid canine canis chaps clothing cowboy cowboy_hat dobermann domestic_dog fence genitals hat headgear headwear hi_res kerchief looking_at_viewer male mammal manny_the_cowboy muscular muscular_anthro muscular_male paw_shoes paxemerson pinscher presenting presenting_hindquarters simple_background smile solo traditional_media_(artwork)
2023 anthro big_butt bubble butt canid canine canis chaps chest_harness clothing cowboy cowboy_hat digital_media_(artwork) dobermann domestic_dog falling feet harness hat headgear headwear hi_res hindpaw male mammal manny_the_cowboy messy mud mudwuff muscular muscular_male partially_submerged pawpads paws peril pinscher plant quicksand sinking solo stuck swamp thick_thighs
9:16 absurd_res animal_genitalia animal_penis anthro anus balls big_butt butt canid canine canine_genitalia canine_penis canis clothing cowboy cowboy_hat dobermann domestic_dog genitals hat headgear headwear hi_res jackaloqe kerchief kerchief_only looking_at_viewer male mammal manny_the_cowboy muscular muscular_anthro muscular_male nude penis penis_backwards pinscher presenting presenting_anus presenting_hindquarters smile solo tongue tongue_out
absurd_res anthro anus arterian_(character) balls big_butt butt canid canine canis chaps clothing cowboy dazed digital_media_(artwork) dobermann domestic_dog duo facesitting genitals hair hi_res human male male/male male_on_anthro male_on_human mammal manny_the_cowboy markings musclegut muscular muscular_anthro muscular_male nipples nub_tail nude paws pecs pinscher severeni simple_background sitting sitting_on_another smile smothering text tongue tongue_out tribal tribal_markings
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