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<3 2023 anthro black_collar black_nose canid canid_demon canine canis carrying_another collar demon digital_drawing_(artwork) digital_media_(artwork) female fur grey_body grey_fur grey_hair group hair hellhound helluva_boss hi_res loona_(helluva_boss) male mammal moony0123 multicolored_body multicolored_fur one_eye_obstructed red_sclera spiked_collar spikes vortex_(helluva_boss) white_body white_eyes white_fur wolf young <3 2023 anthro big_breasts black_bottomwear black_clothing black_nipples black_nose black_shorts bottomwear breasts canid canid_demon canine canis clothing demon digital_drawing_(artwork) digital_media_(artwork) female fur grey_hair hair hellhound helluva_boss hi_res huge_breasts hyper hyper_breasts loona_(helluva_boss) mammal moony0123 nipple_piercing nipples one_eye_closed piercing red_sclera shorts solo white_body white_fur wolf <3 2023 abdominal_bulge anthro big_dildo brown_body brown_fur brown_hair brown_nose canid canine canis clothing digital_drawing_(artwork) digital_media_(artwork) dildo dildo_in_pussy dildo_insertion dildo_sitting domestic_dog eyewear female fur glasses green_clothing hair hi_res hunting_dog illumination_entertainment mammal masturbation moony0123 penetration purple_dildo saluki sex_toy sex_toy_in_pussy sex_toy_insertion sighthound simple_background sing_(movie) solo suki_lane tongue tongue_out vaginal vaginal_masturbation vaginal_penetration <3 2023 anthro belly black_body black_fur black_nose blush breasts canid canid_demon canine canis collar demon digital_drawing_(artwork) digital_media_(artwork) female fur grey_hair hair hand_on_stomach hellhound helluva_boss hi_res loona_(helluva_boss) mammal moony0123 multicolored_body multicolored_fur pregnant pregnant_female red_sclera solo spiked_collar spikes white_body white_eyes white_fur wolf 2023 3_toes anthro arm_tattoo barefoot bdsm black_nose blind_eye bondage bone bone_gag bottomwear bound breasts canid canid_demon cigarette cigarette_in_mouth claws cleavage clothed clothing collar demon dialogue digital_media_(artwork) dominant dominant_female dress duo english_text eye_scar facial_scar feet female finger_claws fingers fur gag gagged grey_body grey_fur hair hellhound helluva_boss hi_res hindpaw holding_leash holding_object humanoid_hands jacket kneeling leash leather leather_clothing leather_jacket leather_topwear leggings legwear loona_(helluva_boss) male male/female mammal moony0123 multicolored_body multicolored_fur object_in_mouth paws red_sclera scar shirt shorts silver_hair smile smoke smoking spiked_collar spikes standing submissive submissive_male tail tail_motion tailwag tattoo teeth text toe_claws toes topwear torn_bottomwear torn_clothing torn_jacket torn_shirt torn_shorts torn_topwear two_tone_body two_tone_fur vortex_(helluva_boss) white_body white_eyes white_fur