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shadowthedemon
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2019 5_fingers ambiguous_gender animal_genitalia animal_penis anthro ass ballbusting balls balls_fondling balls_grab balls_tugging big_balls big_penis bodily_fluids canid canine canine_genitalia canine_penis canis claws closed_eyes cock_and_ball_torture cock_and_balls_torture dated disembodied_hand duo enro_the_mutt erection fingers fondling fur genital_fluids genital_torture genitals knot knot_root legs_up looking_pleasured male male/ambiguous mammal muscular muscular_anthro muscular_male muscular_thighs nude open_mouth pawpads paws penis precum presenting presenting_balls presenting_penis saliva saliva_string shadowthedemon sharp_teeth sheath signature spreading squeezing tail teeth toe_claws tongue tongue_out vein veiny_knot veiny_penis wolf
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2019 5_fingers ambiguous_gender animal_genitalia animal_penis anthro ass ballbusting balls balls_fondling balls_grab balls_tugging big_balls big_penis bodily_fluids canid canine canine_genitalia canine_penis canis claws closed_eyes cock_and_ball_torture cock_and_balls_torture dated disembodied_hand duo enro_the_mutt erection fingers fondling fur genital_fluids genital_torture genitals knot knot_root legs_up looking_pleasured male male/ambiguous mammal muscular muscular_anthro muscular_male muscular_thighs nude open_mouth pawpads paws penis precum presenting presenting_balls presenting_penis saliva saliva_string shadowthedemon sharp_teeth sheath signature spreading squeezing tail teeth toe_claws tongue tongue_out vein veiny_knot veiny_penis wolf
13
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animal_genitalia animal_penis anthro anus ass balls big_balls big_penis black_body black_fur blue_body blue_fur blush canid canine canine_genitalia canine_penis canis dildo english_text forest fur gaping gaping_anus genitals group hi_res ill_dingo imminent_sex knot knotted_dildo male mammal muscular muscular_anthro mythological_canine mythological_creature mythology penis plant presenting presenting_hindquarters red_body red_fur sex_toy shadowthedemon solo solo_focus speech_bubble tail text tongue tongue_out tree were werecanid werecanine werewolf white_body white_fur wolf
22
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27
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absurd_res after_sex animal_genitalia animal_penis anthro anus ass ass_up balls black_body black_fur blue_markings bodily_fluids canid canine canine_genitalia canine_penis canis duo emanata fur genital_fluids genitals hi_res joonkorner looking_back male male/male mammal markings nude penis presenting presenting_hindquarters question_mark red_markings shadowthedemon spread_anus spread_ass spread_butt spreading white_body white_fur wolf
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absurd_res after_sex animal_genitalia animal_penis anthro anus ass ass_up balls black_body black_fur blue_markings bodily_fluids canid canine canine_genitalia canine_penis canis duo emanata fur genital_fluids genitals hi_res joonkorner looking_back male male/male mammal markings nude penis presenting presenting_hindquarters question_mark red_markings shadowthedemon spread_anus spread_ass spread_butt spreading white_body white_fur wolf
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animal_genitalia animal_penis anthro anus ass ass_focus athletic backsack balls ballsack big_ass big_butt bodily_fluids butt_focus canid canine canine_penis canis demonhybrid dripping gaping gaping_anus genital_fluids genitals hand_on hi_res knot licking looking_at_viewer looking_back male male_only mammal mgangalion open_anus open_mouth pawpads paws penis penis_backwards playful precum raised_tail shadowthedemon solo spread_anus spread_ass spread_butt spreading tongue tongue_out wolf
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animal_genitalia animal_penis anthro anus ass ass_focus athletic backsack balls ballsack big_ass big_butt bodily_fluids butt_focus canid canine canine_penis canis demonhybrid dripping gaping gaping_anus genital_fluids genitals hand_on hi_res knot licking looking_at_viewer looking_back male male_only mammal mgangalion open_anus open_mouth pawpads paws penis penis_backwards playful precum raised_tail shadowthedemon solo spread_anus spread_ass spread_butt spreading tongue tongue_out wolf
40
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absurd_res after_kiss alister_(sangreroja) animal_genitalia animal_penis anthro ass bite_mark black_body black_fur black_hair black_nose blue_markings bodily_fluids breast_squish breasts canid canine canis deaddomovec demon fangs female fox fur fur_tuft genitals grey_body grey_nipples group hair hand_on_ass hand_on_butt hand_on_shoulder hi_res highlights_(coloring) holo_(argorrath) hybrid inverted_nipples male male/female mammal markings muscular muscular_anthro muscular_male nipples nude open_mouth pecs penis pussy red_markings saliva saliva_string sex shadowthedemon sharp_teeth snout squish teeth thigh_sex trio tuft were werecanid werecanine werewolf white_body white_fur wolf yellow_eyes
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absurd_res after_kiss alister_(sangreroja) animal_genitalia animal_penis anthro ass bite_mark black_body black_fur black_hair black_nose blue_markings bodily_fluids breast_squish breasts canid canine canis deaddomovec demon fangs female fox fur fur_tuft genitals grey_body grey_nipples group hair hand_on_ass hand_on_butt hand_on_shoulder hi_res highlights_(coloring) holo_(argorrath) hybrid inverted_nipples male male/female mammal markings muscular muscular_anthro muscular_male nipples nude open_mouth pecs penis pussy red_markings saliva saliva_string sex shadowthedemon sharp_teeth snout squish teeth thigh_sex trio tuft were werecanid werecanine werewolf white_body white_fur wolf yellow_eyes
22
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animal_genitalia animal_penis anthro anus ass ass_focus athletic backsack balls ballsack big_ass big_butt bodily_fluids butt_focus canid canine canine_penis canis cum cum_drip cum_inside cum_on_ass cum_on_balls cum_on_butt cum_on_penis demon dripping gaping gaping_anus genital_fluids genitals hand_on_ass hand_on_butt hi_res hybrid knot licking looking_at_viewer looking_back male mammal mgangalion open_mouth pawpads paws penis playful precum raised_tail shadowthedemon solo spread_anus spread_ass spread_butt spreading tongue tongue_out wolf
24
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18
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animal_genitalia animal_penis anthro anus ass ass_focus athletic balls big_ass big_butt bodily_fluids butt_focus canid canine canine_penis canis cum cum_drip cum_on_ass cum_on_balls cum_on_butt cum_on_penis demon dripping gaping gaping_anus genital_fluids genitals hand_on_ass hand_on_butt hi_res hybrid male mammal mgangalion open_mouth pawpads penis playful precum shadowthedemon solo spread_ass spread_butt spreading tail tongue tongue_out wolf
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animal_genitalia animal_penis anthro anus ass ass_focus athletic balls big_ass big_butt bodily_fluids butt_focus canid canine canine_penis canis cum cum_drip cum_on_ass cum_on_balls cum_on_butt cum_on_penis demon dripping gaping gaping_anus genital_fluids genitals hand_on_ass hand_on_butt hi_res hybrid male mammal mgangalion open_mouth pawpads penis playful precum shadowthedemon solo spread_ass spread_butt spreading tail tongue tongue_out wolf
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16:10 alna_fratcher animal_genitalia animal_penis anthro balls bodily_fluids canid canine canine_penis canis ceejay duo fox genital_fluids genitals glowing glowing_eyes hand_behind_head hi_res hindpaw hot_dogging imminent_sex knot leaking_precum male male/male mammal moon paws penis precum shadowthedemon spread_legs spreading standing teeth text url vein veiny_penis were werecanid werecanine werewolf widescreen wolf
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16:10 alna_fratcher animal_genitalia animal_penis anthro balls bodily_fluids canid canine canine_penis canis ceejay duo fox genital_fluids genitals glowing glowing_eyes hand_behind_head hi_res hindpaw hot_dogging imminent_sex knot leaking_precum male male/male mammal moon paws penis precum shadowthedemon spread_legs spreading standing teeth text url vein veiny_penis were werecanid werecanine werewolf widescreen wolf
16
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3:4 against_surface anal anal_sex anthro canid canine canis casparr duo furry gay glowing glowing_eyes hyaenid hyena imminent_knotting knot leash leash_and_collar leash_pull looking_back looking_pleasured male male/male male_only mammal muscular muscular_male original original_character original_characters penetration shadowthedemon tail tongue tongue_out trixtheyeen were werecanid werecanine werewolf wolf yaoi
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3:4 against_surface anal anal_sex anthro canid canine canis casparr duo furry gay glowing glowing_eyes hyaenid hyena imminent_knotting knot leash leash_and_collar leash_pull looking_back looking_pleasured male male/male male_only mammal muscular muscular_male original original_character original_characters penetration shadowthedemon tail tongue tongue_out trixtheyeen were werecanid werecanine werewolf wolf yaoi
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9:16 anal anal_penetration anal_sex animated anthro anthro_only ass balls bouncing_ass bouncing_balls bouncing_butt canid canine canine_penis canis duo fox fuzzamorous gay genitals hi_res homosexual knot knot_fucking looking_pleasured male male/male male_only mammal muscular muscular_male no_humans original original_character original_characters penetration penis raised_tail riding shadowthedemon short_playtime spread_legs spreading wolf
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9:16 anal anal_penetration anal_sex animated anthro anthro_only ass balls bouncing_ass bouncing_balls bouncing_butt canid canine canine_penis canis duo fox fuzzamorous gay genitals hi_res homosexual knot knot_fucking looking_pleasured male male/male male_only mammal muscular muscular_male no_humans original original_character original_characters penetration penis raised_tail riding shadowthedemon short_playtime spread_legs spreading wolf
13
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abs absurd_res anal animal_genitalia animal_penis anthro anus ass balls barbell_piercing biceps black_body black_fur blue_markings bodily_fluids canid canine canine_penis canis duo ear_piercing facial_piercing frohti fur genitals heterochromia hi_res male male/male mammal markings muscular muscular_anthro muscular_male nose_piercing nose_ring nude oral penis piercing red_markings rimming ring_piercing sex shadowthedemon tongue tongue_out white_body white_fur wolf
40
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2022 4_toes absurd_res animal_genitalia animal_penis anthro ass ass_up balls black_body black_fur blush bodily_fluids canid canine canine_penis canis collar cum cum_in_ass cum_inside digitigrade duo feet fucked_silly fur genital_fluids genitals hi_res knot lying male male/male male_only male_penetrated male_penetrating male_penetrating_male mammal muscular muscular_male nude on_front onomatopoeia overflowing_cum pawpads paws penetration penis seibear sex shadowthedemon sound_effects text toes tongue tongue_out wolf yellow_pawpads
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2022 4_toes absurd_res animal_genitalia animal_penis anthro ass ass_up balls black_body black_fur blush bodily_fluids canid canine canine_penis canis collar cum cum_in_ass cum_inside digitigrade duo feet fucked_silly fur genital_fluids genitals hi_res knot lying male male/male male_only male_penetrated male_penetrating male_penetrating_male mammal muscular muscular_male nude on_front onomatopoeia overflowing_cum pawpads paws penetration penis seibear sex shadowthedemon sound_effects text toes tongue tongue_out wolf yellow_pawpads
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2022 4_toes absurd_res animal_genitalia animal_penis anthro ass ass_up balls black_body black_fur blush canid canine canine_penis canis collar digitigrade duo feet fur genitals hi_res knot lying male male/male male_only male_penetrated male_penetrating male_penetrating_male mammal muscular muscular_male nude on_front onomatopoeia pawpads paws penetration penis seibear sex shadowthedemon sound_effects text toes tongue tongue_out wolf yellow_pawpads
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2022 4_toes absurd_res animal_genitalia animal_penis anthro ass ass_up balls black_body black_fur blush canid canine canine_penis canis collar digitigrade duo feet fur genitals hi_res knot lying male male/male male_only male_penetrated male_penetrating male_penetrating_male mammal muscular muscular_male nude on_front onomatopoeia pawpads paws penetration penis seibear sex shadowthedemon sound_effects text toes tongue tongue_out wolf yellow_pawpads
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absurd_res anal anthro bodily_fluids canid canine canis deaddomovec domestic_dog double_penetration fellatio genital_fluids german_shepherd group herding_dog hi_res knot legs_up lube male male/male mammal masturbation oral oral_penetration pastoral_dog penetration penile penis precum rough_sex saliva sex shadowthedemon spitroast spreading tongue trio wolf
20
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anthro audience backsack balls ballsack bodily_fluids canid canine canis clockhands clothing genitals glowstick group jockstrap looking_at_viewer looking_back male mammal muscular presenting raised_tail shadowthedemon solo stage sweat tongue underwear wolf
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43
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absurd_res after_sex ailurid ambiguous_gender anthro ass balls bodily_fluids canid canine canis closed_eyes cum cum_inside duo free_use genital_fluids genitals glory_wall hi_res knot leaking_cum mako_rivers male male_only mammal pawpads raised_tail rear_view red_panda seibear shadowthedemon tally_marks through_wall towel wolf
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absurd_res after_sex ailurid ambiguous_gender anthro ass balls bodily_fluids canid canine canis closed_eyes cum cum_inside duo free_use genital_fluids genitals glory_wall hi_res knot leaking_cum mako_rivers male male_only mammal pawpads raised_tail rear_view red_panda seibear shadowthedemon tally_marks through_wall towel wolf
14
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animal_genitalia animal_penis anthro anus ass backsack balls ballsack bodily_fluids canid canine canine_penis canis dripping genital_fluids genitals hi_res knot light looking_at_viewer looking_pleasured male male_only mammal moon moonlight muscular penis precum precum_drip presenting presenting_hindquarters raised_tail shadowthedemon solo tongue vallhund vein veiny_penis were werecanid werecanine werewolf wolf
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animal_genitalia animal_penis anthro anus ass backsack balls ballsack bodily_fluids canid canine canine_penis canis dripping genital_fluids genitals hi_res knot light looking_at_viewer looking_pleasured male male_only mammal moon moonlight muscular penis precum precum_drip presenting presenting_hindquarters raised_tail shadowthedemon solo tongue vallhund vein veiny_penis were werecanid werecanine werewolf wolf
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5:4 amazinggwen animal_genitalia animal_penis anthro anus ass backsack balls ballsack black_body black_fur blue_body blue_fur blush canid canine canine_penis canis cuckold dialogue digital_media_(artwork) duo english_text erection frostbone_(character) fur genitals green_body green_fur infidelity knot looking_at_viewer looking_back male male/male male_only mammal multicolored_body multicolored_fur muscular penis perineum presenting presenting_hindquarters presenting_partner purple_eyes raised_tail red_eyes shadowthedemon spread_anus spreading swingers text vein veiny_penis white_body white_fur wolf yaoi
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5:4 amazinggwen animal_genitalia animal_penis anthro anus ass backsack balls ballsack black_body black_fur blue_body blue_fur blush canid canine canine_penis canis cuckold dialogue digital_media_(artwork) duo english_text erection frostbone_(character) fur genitals green_body green_fur infidelity knot looking_at_viewer looking_back male male/male male_only mammal multicolored_body multicolored_fur muscular penis perineum presenting presenting_hindquarters presenting_partner purple_eyes raised_tail red_eyes shadowthedemon spread_anus spreading swingers text vein veiny_penis white_body white_fur wolf yaoi
52
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13
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absurd_res against_surface animal_genitalia animal_penis anthro anus ass backsack balls ballsack canid canine canine_penis canis frohti frosty-art genitals hi_res knot looking_at_viewer looking_back male mammal musk on_glass penis raised_tail rear_view shadowthedemon solo spread_legs spreading steam wolf
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11
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achaiwolf anal anthro anus ass bodily_fluids canid canine canis closed_eyes deep_rimming duo facesitting frosty-art hi_res looking_pleasured male male/male mammal muscular musk muzzle_(disambiguation) oral rimming saliva saliva_string sex shadowthedemon spreading tail wolf
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2021 5_fingers animal_genitalia animal_penis animated anthro anus avian balls biped bird bouncing_balls brown_body brown_eyes brown_fur canid canine canine_penis canis diegodadingo dingo duo erection eyewear fingers forced forced_oral foursome fur genitals glasses group group_sex hand_holding irrumatio kissing knot lying male male/male mammal on_back oral pawpads paws penile penis peyotethehyena purple_eyes sex shadowthedemon short_playtime simple_background throat_swabbing wolf
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2021 5_fingers animal_genitalia animal_penis animated anthro anus avian balls biped bird bouncing_balls brown_body brown_eyes brown_fur canid canine canine_penis canis diegodadingo dingo duo erection eyewear fingers forced forced_oral foursome fur genitals glasses group group_sex hand_holding irrumatio kissing knot lying male male/male mammal on_back oral pawpads paws penile penis peyotethehyena purple_eyes sex shadowthedemon short_playtime simple_background throat_swabbing wolf
20
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19
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5:4 amazinggwen animal_genitalia animal_penis anthro anus ass backsack balls ballsack blush canid canine canine_penis canis cuckold dialogue duo frostbone_(character) genitals infidelity knot looking_at_viewer looking_back male male/male mammal muscular penis presenting presenting_hindquarters raised_tail shadowthedemon spread_anus spreading vein veiny_penis wolf
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5:4 amazinggwen animal_genitalia animal_penis anthro anus ass backsack balls ballsack blush canid canine canine_penis canis cuckold dialogue duo frostbone_(character) genitals infidelity knot looking_at_viewer looking_back male male/male mammal muscular penis presenting presenting_hindquarters raised_tail shadowthedemon spread_anus spreading vein veiny_penis wolf
23
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4:5 amazinggwen animal_genitalia animal_penis anthro anus ass backsack balls ballsack bodily_fluids canid canine canine_penis canis cuckold cum cum_in_ass cum_inside cum_leaking dialogue duo ejaculation english_text genital_fluids genitals hi_res infidelity knot looking_at_viewer looking_back male male/male mammal muscular penis presenting presenting_anus presenting_hindquarters raised_tail shadowthedemon spread_anus spreading text tongue vein veiny_penis wolf
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4:5 amazinggwen animal_genitalia animal_penis anthro anus ass backsack balls ballsack bodily_fluids canid canine canine_penis canis cuckold cum cum_in_ass cum_inside cum_leaking dialogue duo ejaculation english_text genital_fluids genitals hi_res infidelity knot looking_at_viewer looking_back male male/male mammal muscular penis presenting presenting_anus presenting_hindquarters raised_tail shadowthedemon spread_anus spreading text tongue vein veiny_penis wolf
18
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18
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4_toes animal_genitalia animal_penis anthro balls bodily_fluids breast_sucking breasts canid canine canine_penis canis claws clitoris duo feet felid feline female female_penetrated genital_fluids genitals hi_res knot legs_up lynx male male/female male_penetrating male_penetrating_female mammal marsccts muscular nipple_fetish nipple_play nipple_suck nipples orgasm_face pawpads paws penetration penile penile_penetration penis penis_in_pussy pussy pussy_juice sex shadowthedemon spread_legs spreading sucking sweat toe_claws toes vaginal_penetration wolf
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4_toes animal_genitalia animal_penis anthro balls bodily_fluids breast_sucking breasts canid canine canine_penis canis claws clitoris duo feet felid feline female female_penetrated genital_fluids genitals hi_res knot legs_up lynx male male/female male_penetrating male_penetrating_female mammal marsccts muscular nipple_fetish nipple_play nipple_suck nipples orgasm_face pawpads paws penetration penile penile_penetration penis penis_in_pussy pussy pussy_juice sex shadowthedemon spread_legs spreading sucking sweat toe_claws toes vaginal_penetration wolf
11
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absurd_res anthro anus ass backsack balls ballsack bodily_fluids canid canine canis frostbone genitals hi_res male mammal muscular muscular_male presenting presenting_hindquarters raised_tail shadowthedemon solo spreading sweat wolf
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absurd_res amazinggwen anal anal_fingering anal_masturbation anal_sex animal_genitalia animal_penis anthro bedroom bodily_fluids bulge canid canine canine_penis canis clothing comic cum_tube dildo dildo_in_ass dildo_penetration dildo_sitting ejaculation fingering genital_fluids genitals hi_res jockstrap knot knotting lube lube_bottle lube_in_ass lube_on_dildo male male_focus male_only male_penetrated mammal masturbation muscular penetration penis penis_tip precum presenting sex sex_toy sex_toy_in_ass sex_toy_penetration shadowthedemon sheath sleeping solo sound_effects spreading text underwear wolf
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absurd_res amazinggwen anal anal_fingering anal_masturbation anal_sex animal_genitalia animal_penis anthro bedroom bodily_fluids bulge canid canine canine_penis canis clothing comic cum_tube dildo dildo_in_ass dildo_penetration dildo_sitting ejaculation fingering genital_fluids genitals hi_res jockstrap knot knotting lube lube_bottle lube_in_ass lube_on_dildo male male_focus male_only male_penetrated mammal masturbation muscular penetration penis penis_tip precum presenting sex sex_toy sex_toy_in_ass sex_toy_penetration shadowthedemon sheath sleeping solo sound_effects spreading text underwear wolf
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1boy animal_genitalia animal_penis anthro balls beach bedroom_eyes bodily_fluids canid canine canine_penis canis furry genital_fluids genitals jonas-puppeh knot looking_at_viewer male male_only mammal muscular muscular_anthro muscular_male narrowed_eyes penis precum presenting raised_leg seaside seductive shadowthedemon solo spreading testicles wolf
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1boy animal_genitalia animal_penis anthro balls beach bedroom_eyes bodily_fluids canid canine canine_penis canis furry genital_fluids genitals jonas-puppeh knot looking_at_viewer male male_only mammal muscular muscular_anthro muscular_male narrowed_eyes penis precum presenting raised_leg seaside seductive shadowthedemon solo spreading testicles wolf
11
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1boy animal_genitalia animal_penis anthro balls beach bedroom_eyes canid canine canine_penis canis furry genitals half-erect jonas-puppeh looking_at_viewer male male_only mammal muscular muscular_anthro muscular_male narrowed_eyes penis penis_tip presenting raised_leg seaside seductive shadowthedemon sheath solo spreading testicles wolf
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1boy animal_genitalia animal_penis anthro balls beach bedroom_eyes canid canine canine_penis canis furry genitals half-erect jonas-puppeh looking_at_viewer male male_only mammal muscular muscular_anthro muscular_male narrowed_eyes penis penis_tip presenting raised_leg seaside seductive shadowthedemon sheath solo spreading testicles wolf