ambiguous_penetration anal anthro anthro_on_anthro anthro_penetrated arms_above_head ball_gag balls bdsm biting_hair bodily_fluids bondage bound breast_fondling breast_grab breast_play breasts cage canid canid_demon canine captured chain chained cheek_tuft chest_tuft crying cuff_(restraint) demon dildo dominant dominant_male dungeon duo ear_piercing eyes_closed facial_tuft female female_penetrated fluffy fluffy_tail fondling forced from_behind_position fur fuzzy gag gagged genitals grey_body grey_fur grin hair hair_bite hair_in_mouth hand_on_breast hellhound helluva_boss helpless hi_res humanoid_genitalia humanoid_penis loona_(helluva_boss) male male/female mammal multicolored_body multicolored_fur mythological_canine mythological_creature mythology nipples nude pain penetration penis piercing rape red_body red_fur restrained restrained_arms restraints sadtoasterr saliva sex sex_toy side_view slave slim small_breasts small_waist smile standing standing_sex tail tail_grab tail_pull tears tuft whip white_body white_fur 2023 4_arms 4_fingers 4_toes anthro arthropod bee black_clothing black_legwear black_nose blue_hair bottomwear breasts canid canid_demon canine clothed clothing collar demon digital_media_(artwork) dress erection eyebrows faceless_character faceless_male feet fellatio female female_penetrated fingerless_gloves fingers fox fur genitals gloves grey_body grey_fur grey_hair group hair hand_between_legs hand_on_breast handwear hellhound helluva_boss hi_res hybrid hymenopteran insect insect_wings kneeling kneeling_oral_position leg_markings legwear licking long_hair loona_(helluva_boss) male male/female male_penetrating male_penetrating_anthro male_penetrating_female mammal markings multi_arm multi_limb nipples oral pawpads penetration penile penis penis_in_mouth pink_eyes queen_bee-lzebub_(helluva_boss) red_clothing red_dress red_sclera sadtoasterr sex socks_(marking) spiked_collar spikes toeless_(marking) toeless_legwear toes tongue tongue_out topwear torn_clothing trio vortex_(helluva_boss) wings yellow_body yellow_fur yellow_pawpads  2022 4_toes 5_fingers against_surface against_wall ambiguous_penetration anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro arm_grab black_nose breasts brown_body brown_fur canid canid_demon clenched_teeth demon duo feet female female_penetrated fingers forced fur gag gagged grey_body grey_fur hair hands_behind_head hellhound helluva_boss hindpaw humanoid_hands loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal multicolored_body multicolored_fur nude paws penetration penile penile_penetration rape red_sclera sadtoasterr sex shower shower_sex silver_hair standing standing_sex teeth toes two_tone_body two_tone_fur wet wet_body wet_fur wet_hair white_body white_eyes white_fur  6:5 anal anthro anthro_on_anthro arms_above_head arms_tied avian ball_gag bdsm bodily_fluids bondage bound camera canid canid_demon canine captured clothed clothing crying demon dominant dominant_male female forced gag gagged group hellhound helluva_boss helpless hi_res imminent_rape kidnapping legwear loona_(helluva_boss) male male/female mammal octavia_(helluva_boss) rape recording rope sadtoasterr saliva scared sex slave submissive submissive_female tail tears trio  after_sex anal anal_penetration anthro arms_above_head arms_tied bdsm bodily_fluids bondage bound breasts canid canid_demon canine captured crying cum cum_in_mouth cum_in_pussy cum_inside cum_on_face cum_on_tail demon dildo dildo_in_ass dildo_insertion duo erection female forced gag genital_fluids genitals hair hellhound helluva_boss hi_res imminent_rape kidnapping looking_up loona_(helluva_boss) male male/female mammal nipples nude object_in_ass penetration penis pussy rape restraints ring_gag ruined_makeup sadtoasterr scared sex_toy sex_toy_in_ass sex_toy_insertion slave spread_legs spreader_bar spreading tail tears  anal anal_penetration anthro anthro_on_anthro anthro_penetrated arms_above_head arms_tied avian ball_gag bdsm bodily_fluids bondage bound breasts butt butt_grab canid canine captured crying dominant dominant_male duo female forced gag gagged genitals hand_on_butt helluva_boss helpless hi_res looking_back male male/female mammal nipples octavia_(helluva_boss) penetration penile penile_penetration penis penis_in_ass pussy rape rope sadtoasterr saliva scared sex slave submissive submissive_female tears  anthro arms_above_head avian ball_gag bdsm bird bodily_fluids bondage bound breast_grab breasts captured clothed clothing drooling female forced gag gagged grope hand_on_breast helluva_boss helpless hi_res imminent_rape kidnapping male male/female octavia_(helluva_boss) owl owl_demon panties sadtoasterr saliva scared slave tears underwear  2_toes 4_fingers alternate_species animal_genitalia animal_pussy anus anus_outline beauty_mark black_eyes black_hair black_tail blitzo_(helluva_boss) book bottomwear camel_toe clothing collar curled_horn demon demon_humanoid dock ear_piercing ear_ring equid equine equine_genitalia equine_pussy feet female feral fingers fur genital_outline genitals hair hasbro helluva_boss holding_object horn horse humanoid imp loona_(helluva_boss) male mammal millie_(helluva_boss) multicolored_body multicolored_fur my_little_pony piercing pony pussy pussy_outline raised_tail red_body red_sclera red_skin ring_piercing sadtoasterr shorts spiked_collar spikes tail toes torn_clothing transformation two_tone_body two_tone_fur two_tone_tail unicorn unicorn_horn white_body white_eyes white_fur yellow_sclera  2023 ambiguous_penetration anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro arms_tied bdsm black_nose bodily_fluids bound canid canid_demon clenched_teeth demon digital_media_(artwork) duo female female_penetrated forced fur gag gagged grey_body grey_fur grin hair hands_behind_back hellhound helluva_boss hi_res humanoid_hands loona_(helluva_boss) lying male male/female male_penetrating male_penetrating_female mammal multicolored_body multicolored_fur navel nipples nude on_back penetration penile penile_penetration rape running_mascara sadtoasterr sex silver_hair smile tape tape_gag tears teeth two_tone_body two_tone_fur white_body white_eyes white_fur  anthro bdsm bodily_fluids bondage bound canid canid_demon canine captured demon drooling female forced gag gagged genitals group hellhound helluva_boss helpless hi_res human imminent_oral imminent_rape kidnapping loona_(helluva_boss) male male/female mammal penis red_sclera ring_gag sadtoasterr saliva scared slave spread_arms spread_legs spreading  arms_above_head avian ball_gag bdsm bird bodily_fluids bondage bound captured clothed clothing drooling female forced forced_orgasm gag gagged helluva_boss helpless hi_res kidnapping octavia_(helluva_boss) orgasm owl owl_demon sadtoasterr saliva scared sex_toy slave solo tape tears vibrator  angry anthro ball_gag barefoot bdsm bondage bound canid canid_demon canine captured clothed clothing demon feet female forced gag gagged helluva_boss helpless hi_res legs_tied legwear loona_(helluva_boss) mammal red_sclera sadtoasterr slave solo submissive submissive_female  2021 anthro avian bed_sheet bedding bird black_nose blush canid canid_demon canine canis demon digital_drawing_(artwork) digital_media_(artwork) duo eyebrows feathers female female/female fur grey_body grey_fur grey_hair hair hand_on_another's_shoulder hand_on_cheek hand_on_shoulder hellhound helluva_boss hi_res loona_(helluva_boss) mammal octavia_(helluva_boss) owl owl_demon red_sclera sadtoasterr tongue white_body white_eyes white_fur wolf  angry anthro avian ball_gag bdsm bed bondage bound bra captured clothing demon female forced furniture gag gagged helluva_boss helpless hi_res panties red_sclera rope sadtoasterr stella_(helluva_boss) submissive submissive_female underwear  anthro bdsm bondage bound buttplug canid canid_demon canine demon egg_vibrator female forced gag gagged genitals hellhound helluva_boss hi_res imminent_rape loona_(helluva_boss) mammal plug_(sex_toy) pussy restraints sadtoasterr scared sex_toy straitjacket submissive submissive_anthro submissive_female vibrator  anthro bdsm bondage bound breasts canid canid_demon captured demon demon_humanoid duo female gag hellhound helluva_boss humanoid loona_(helluva_boss) mammal muzzle_gag nipple_fetish nipple_pinch nipple_play pinch sadtoasterr verosika_mayday_(helluva_boss)  anthro bdsm bondage bound bra canid canid_demon captured closet clothing demon egg_vibrator female gag hands_behind_head hellhound helluva_boss loona_(helluva_boss) mammal muzzle_gag pawpads paws raised_paw sadtoasterr sex_toy sex_toy_in_pussy sex_toy_insertion solo squirming underwear vibrator vibrator_in_pussy wet wet_clothing wet_underwear  age_difference anthro anthro_on_anthro anthro_penetrated avian bdsm bird bodily_fluids bondage bound breasts crying cum cum_in_mouth cum_inside daughter demon dominant dominant_male duo father father_and_child female forced forced_oral gag gagged genital_fluids genitals hair hair_grab helluva_boss hi_res male male/female nipples octavia_(helluva_boss) older_male oral owl owl_demon parent parent_and_child penetration penis rape ring_gag sadtoasterr sex stolas_(helluva_boss) submissive submissive_female tears teenager touching_hair young younger_female  anthro ball_gag bdsm bondage bound breasts clothed clothing demon demon_humanoid female forced gag gagged helluva_boss helpless hi_res hogtied horn humanoid millie_(helluva_boss) panties red_body sadtoasterr solo submissive submissive_female underwear yellow_sclera  all_three_filled anal anal_penetration animal_genitalia animal_pussy anthro bdsm bodily_fluids bondage bound breasts canid canid_demon canine canine_pussy clothing cum cum_in_mouth cum_inside demon double_penetration female forced genital_fluids genitals hellhound helluva_boss hi_res leg_grab legwear loona_(helluva_boss) mammal nipples oral oral_penetration pawpads paws penetration pussy rape sadtoasterr solo submissive submissive_female tail_grab tentacle_bondage tentacle_in_ass tentacle_in_mouth tentacle_in_pussy tentacle_penetration tentacle_rape tentacle_sex tentacles triple_penetration vaginal vaginal_penetration  angry anthro arms_above_head arms_tied bdsm bodily_fluids bondage bound breast_grab breasts canid canid_demon canine cum cum_in_mouth cum_inside cum_on_face demon dominant dominant_male female female_penetrated forced gag gagged genital_fluids group hand_on_breast hellhound helluva_boss helpless hi_res loona_(helluva_boss) male male/female mammal millie_(helluva_boss) nipples penetration rape sadtoasterr sex slave submissive vaginal vaginal_penetration  anthro avian bdsm bird bodily_fluids bondage bound breasts clothing demon female forced forced_orgasm gag gagged helluva_boss helpless hi_res improvised_gag nipples octavia_(helluva_boss) orgasm owl panties_in_mouth sadtoasterr sex_toy sex_toy_insertion solo submissive submissive_female tears vibrator  anthro bdsm bodily_fluids bondage bound breasts canid canid_demon canine cum cum_in_mouth cum_inside cum_on_face cum_on_tongue demon duo erection female forced fur gag gagged genital_fluids genitals hair hair_grab hellhound helluva_boss hi_res loona_(helluva_boss) male male/female mammal nipples oral penis rape ring_gag sadtoasterr slave submissive tongue tongue_out touching_hair  anal anal_penetration angry anthro bra buttplug buttplug_in_ass buttplug_insertion buttplug_tail canid canid_demon canine clothed clothing demon dialogue english_text fake_tail female fur hellhound helluva_boss hi_res looking_back loona_(helluva_boss) mammal panties panties_down partially_clothed penetration plug_(sex_toy) plug_insertion rear_view sadtoasterr sex_toy sex_toy_in_ass sex_toy_insertion solo text underwear underwear_down  angry anthro anthro_on_anthro bdsm bodily_fluids bondage bound canid canid_demon canine crying cum cum_in_mouth cum_inside demon double_penetration female female_penetrated forced gag gagged genital_fluids genitals group group_sex hellhound helluva_boss helpless hi_res loona_(helluva_boss) male male/female mammal oral penetration penis rape red_sclera ring_gag sadtoasterr sex slave submissive tail_grab tears threesome  anal anal_penetration anthro ball_gag bdsm bed bodily_fluids bondage bound breasts canid canid_demon canine crying demon duo female forced furniture gag gagged genitals hellhound helluva_boss helpless hi_res loona_(helluva_boss) male male/female mammal nipples penetration penis pussy rape red_sclera sadtoasterr scared slave tears  anthro bottomwear canid canid_demon canine clothed clothing collar demon doggystyle female from_behind_position fur hellhound helluva_boss hi_res loona_(helluva_boss) mammal paws red_sclera sadtoasterr secretary sex skirt smile solo uniform  age_difference anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro avian bdsm bird bodily_fluids bondage bound breasts crying cum cum_in_mouth cum_inside daughter demon dominant dominant_male duo father father_and_child female forced gag gagged genital_fluids genitals helluva_boss hi_res incest_(lore) male male/female nipples octavia_(helluva_boss) older_male oral owl owl_demon parent parent_and_child penetration penis rape ring_gag sadtoasterr sex stolas_(helluva_boss) submissive submissive_female tears teenager young younger_female  2021 angry anthro bdsm bodily_fluids canid canid_demon canine collar crying cum cum_in_mouth cum_inside demon digital_media_(artwork) duo erection fellatio female forced fur gag gagged genital_fluids genitals hellhound helluva_boss hi_res loona_(helluva_boss) male male/female mammal oral penetration penile penis rape red_sclera ring_gag sadtoasterr sex simple_background spiked_collar spikes tears tongue tongue_out  2021 4:5 age_difference anthro avian ball_gag bdsm bodily_fluids bondage bound breasts canid canid_demon canine clothing crying demon drooling duo female female/female forced gag gagged hair hellhound helluva_boss hi_res legwear loona_(helluva_boss) mammal nipples nude octavia_(helluva_boss) owl_demon paws red_sclera sadtoasterr saliva slim small_breasts submissive tears teenager white_body young younger_female  2021 age_difference angry anthro arms_tied avian barefoot bdsm belt bodily_fluids bondage bound bound_together breasts canid canid_demon canine clothing cock_gag collar crying demon drooling duo feet female female/female forced forced_partners fur gag gagged hair hands_behind_back hellhound helluva_boss helpless hi_res legs_tied legwear loona_(helluva_boss) mammal nipples nude octavia_(helluva_boss) owl_demon red_sclera restrained restraints sadtoasterr saliva shackles shared_gag simple_background slim small_breasts submissive submissive_female tears teenager tied_together white_body white_fur young younger_female  age_difference anthro avian ball_gag bdsm bodily_fluids bondage bound clothing demon drooling feet female forced forced_orgasm gag gagged genital_fluids helluva_boss helpless hi_res octavia_(helluva_boss) orgasm owl_demon panties pussy_juice sadtoasterr saliva sex_toy solo submissive submissive_female underwear vibrator vibrator_under_clothing wet wet_clothing young younger_female  anthro ball_gag bdsm bodily_fluids bondage bound canid canid_demon canine clothing crying demon drooling egg_vibrator female forced forced_orgasm fur gag gagged hellhound helluva_boss helpless hi_res legwear loona_(helluva_boss) mammal orgasm paws red_sclera sadtoasterr saliva sex_toy solo submissive submissive_female tears underwear vibrator vibrator_under_clothing white_body  3_toes 4_fingers age_difference anthro avian ball_gag bdsm bodily_fluids bondage bondage_gear bound crying duo feet female fingers forced gag helluva_boss hi_res hybrid imminent_rape octavia_(vivzmind) owl_demon sadtoasterr sex_toy tears toes young younger_female  anal anal_penetration anthro avian ball_gag bdsm bodily_fluids bondage bound duo female forced gag helluva_boss hi_res incest_(lore) male male/female octavia_(vivzmind) owl_demon penetration restrained sadtoasterr sex_toy sex_toy_in_ass sex_toy_in_pussy sex_toy_insertion stolas_(vivzmind) tears young  age_difference anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro avian ball_gag bdsm bodily_fluids bondage bound daughter dominant dominant_male dominant_pov duo father father_and_child father_and_daughter father_penetrating_daughter female female_penetrated first_person_view flat_chested forced gag gagged helluva_boss hi_res incest_(lore) leg_grab male male/female male_penetrating male_penetrating_female male_pov octavia_(vivzmind) older_male owl_demon parent parent_and_child parent_and_daughter penetration rape sadtoasterr sex stolas_(vivzmind) submissive submissive_female tears vaginal vaginal_penetration young younger_female younger_penetrated  2021 absurd_res anthro bdsm bodily_fluids bondage bound breasts canid canid_demon canine clothing demon female forced forced_orgasm fur gag gagged genital_fluids genitals hellhound helluva_boss hi_res legwear loona_(vivzmind) mammal nipples notched_ear orgasm paws pussy pussy_juice sadtoasterr sex_toy solo vibrator white_body white_fur  2021 agent_torque anthro apode bodily_fluids bra breasts canid canid_demon canine clothing coiling crossover demon dialogue dirty_talk dominant dominant_female draconcopode drooling duo english_text female female/female forced forked_tongue fur green_eyes grey_body grey_scales hair hand_on_breast hellhound helluva_boss hi_res interspecies legless loona_(vivzmind) mammal multicolored_body multicolored_fur multicolored_scales naga nipples non-mammal_breasts purple_background red_sclera reptile restrained sadtoasterr saliva scales scalie scared serpentine simple_background smile snake sports_bra submissive text tongue tongue_out two_tone_body two_tone_fur two_tone_scales underwear video_games viper_(x-com) voice_actor_joke white_body white_fur white_hair x-com x-com:_chimera_squad  2021 angry anthro bdsm bodily_fluids bondage bound breasts canid canid_demon canine clothing demon dialogue digital_media_(artwork) dildo dirty_talk double_penetration drooling female forced fur gag gagged genital_fluids hair hellhound helluva_boss hi_res legwear loona_(vivzmind) mammal nipples notched_ear nude paws penetration pussy_juice rape red_sclera sadtoasterr saliva sex_toy solo text white_body white_fur  2021 3_toes 5_fingers angry anthro arms_above_head arms_tied bared_teeth bdsm black_claws black_nose bondage bottomwear bound breasts canid canid_demon canine claws clenched_teeth clothed clothing demon dialogue digital_media_(artwork) digitigrade english_text eyelashes feet female fingerless_gloves fingers frown fur gag gagged gloves grey_body grey_fur grey_hair hair handwear hellhound helluva_boss hi_res hindpaw humanoid_hands kneeling legs_tied legwear long_hair looking_at_viewer looking_up loona_(vivzmind) mammal muffled multicolored_body multicolored_fur navel nipples paws red_sclera sadtoasterr scowl shorts signature snout snout_tied solo speech_bubble stockings teeth text toe_claws toeless_legwear toeless_stockings toes topless topless_female torn_bottomwear torn_clothing torn_shorts two_tone_body two_tone_fur white_body white_eyes white_fur