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anthro ball_gag bodily_fluids bondage 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
anthro ball_gag bodily_fluids bondage 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
2021 angry anthro bodily_fluids bondage canid canid_demon canine collar crying cum cum_in_mouth cum_inside demon digital_media_(artwork) duo erection fellatio female forced forced_oral fur gag gagged genital_fluids genitals hellhound helluva_boss hi_res loona_(helluva_boss) male male/female mammal oral partial_male penetration penile penis rape red_sclera ring_gag sadtoasterr sex simple_background spiked_collar spikes tears tongue tongue_out
2021 angry anthro bodily_fluids bondage canid canid_demon canine collar crying cum cum_in_mouth cum_inside demon digital_media_(artwork) duo erection fellatio female forced forced_oral fur gag gagged genital_fluids genitals hellhound helluva_boss hi_res loona_(helluva_boss) male male/female mammal oral partial_male penetration penile penis rape red_sclera ring_gag sadtoasterr sex simple_background spiked_collar spikes tears tongue tongue_out
1boy 1girls bodily_fluids bondage bound breasts clothing duo eyebrow_piercing face_lick female forced gag gagged genitals gwen_stacy helpless hi_res human humanoid licking male male/female mammal marvel muscular muscular_male nipples penetration penis pinned pinned_to_wall pussy rape restrained restrained_arms sadtoasterr saliva sex shaved_side size_difference spider-gwen superhero superhero_costume superheroine symbiote tears tongue torn_clothing vaginal_penetration venom venom_(marvel)
1boy 1girls bodily_fluids bondage bound breasts clothing duo eyebrow_piercing face_lick female forced gag gagged genitals gwen_stacy helpless hi_res human humanoid licking male male/female mammal marvel muscular muscular_male nipples penetration penis pinned pinned_to_wall pussy rape restrained restrained_arms sadtoasterr saliva sex shaved_side size_difference spider-gwen superhero superhero_costume superheroine symbiote tears tongue torn_clothing vaginal_penetration venom venom_(marvel)
1girls 2021 3_toes 5_fingers angry anthro arms_above_head arms_tied bared_teeth 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 furry 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_(helluva_boss) mammal muffled multicolored_body multicolored_fur navel nipples paws red_sclera sadtoasterr scowl shorts signature snout solo speech_bubble stockings teeth toe_claws toeless_legwear toeless_stockings toes topless topless_female torn_bottomwear torn_clothing torn_shorts two_tone_body two_tone_fur vivienne_medrano white_body white_eyes white_fur
1girls 2021 3_toes 5_fingers angry anthro arms_above_head arms_tied bared_teeth 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 furry 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_(helluva_boss) mammal muffled multicolored_body multicolored_fur navel nipples paws red_sclera sadtoasterr scowl shorts signature snout solo speech_bubble stockings teeth toe_claws toeless_legwear toeless_stockings toes topless topless_female torn_bottomwear torn_clothing torn_shorts two_tone_body two_tone_fur vivienne_medrano white_body white_eyes white_fur
anal anal_sex anthro anthro_on_anthro anthro_penetrated arms_above_head arms_tied ass avian ball_gag bodily_fluids bondage bound breasts butt_grab canid canine captured crying dominant dominant_male duo eyeless_male 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
anal anal_sex anthro anthro_on_anthro anthro_penetrated arms_above_head arms_tied ass avian ball_gag bodily_fluids bondage bound breasts butt_grab canid canine captured crying dominant dominant_male duo eyeless_male 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 bodily_fluids bondage bound canid canid_demon canine captured demon drooling faceless_male 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
anthro bodily_fluids bondage bound canid canid_demon canine captured demon drooling faceless_male 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
anthro arms_above_head avian ball_gag bird bodily_fluids bondage bound bound_wrists breast_grab breasts captured clothed clothing drooling female forced gag gagged grope hand_on_breast hands_under_clothes helluva_boss helpless hi_res imminent_rape kidnapping male male/female octavia_(helluva_boss) owl owl_demon panties partial_male sadtoasterr saliva scared slave tears underwear
anthro arms_above_head avian ball_gag bird bodily_fluids bondage bound bound_wrists breast_grab breasts captured clothed clothing drooling female forced gag gagged grope hand_on_breast hands_under_clothes helluva_boss helpless hi_res imminent_rape kidnapping male male/female octavia_(helluva_boss) owl owl_demon panties partial_male sadtoasterr saliva scared slave tears underwear
angry anthro avian ball_gag bed bondage 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
angry anthro avian ball_gag bed bondage 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
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
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
1girls angry anthro bondage bound breasts canid_demon demon grey_hair hair hellhound helluva_boss leggings legwear loona_(helluva_boss) nipples red_sclera sadtoasterr teeth tied tied_up toe_claws topless vivienne_medrano white_eyes
1girls angry anthro bondage bound breasts canid_demon demon grey_hair hair hellhound helluva_boss leggings legwear loona_(helluva_boss) nipples red_sclera sadtoasterr teeth tied tied_up toe_claws topless vivienne_medrano white_eyes
anthro arms_tied ball_gag bodily_fluids bondage bondage bound breasts canid canid_demon canine captured clothing crying demon erection fellatio female forced gag gagged hellhound helluva_boss helpless hi_res kneeling loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology nipples nude octavia_(helluva_boss) oral penile rape sadtoasterr saliva sex shirt slave tank_top tears topwear
anthro arms_tied ball_gag bodily_fluids bondage bondage bound breasts canid canid_demon canine captured clothing crying demon erection fellatio female forced gag gagged hellhound helluva_boss helpless hi_res kneeling loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology nipples nude octavia_(helluva_boss) oral penile rape sadtoasterr saliva sex shirt slave tank_top tears topwear
anal anal_fingering anal_sex anthro anus arms_tied ass ball_gag balls bed bodily_fluids bondage bondage bound breast_grab breasts canid canid_demon canine demon digital_media_(artwork) dildo duo erection feet female female_penetrated fingering fingering_partner fingers forced fox fur furniture gag gagged genitals hair hand_on_breast hellhound helluva_boss hi_res loona_(helluva_boss) lying male male/female male_penetrating male_penetrating_female mammal mythological_canine mythological_creature mythology nude on_bed on_side open_mouth pawpads penetration penis pussy rape red_sclera rope sadtoasterr sex sex_toy tail tears toes white_body white_fur
anal anal_fingering anal_sex anthro anus arms_tied ass ball_gag balls bed bodily_fluids bondage bondage bound breast_grab breasts canid canid_demon canine demon digital_media_(artwork) dildo duo erection feet female female_penetrated fingering fingering_partner fingers forced fox fur furniture gag gagged genitals hair hand_on_breast hellhound helluva_boss hi_res loona_(helluva_boss) lying male male/female male_penetrating male_penetrating_female mammal mythological_canine mythological_creature mythology nude on_bed on_side open_mouth pawpads penetration penis pussy rape red_sclera rope sadtoasterr sex sex_toy tail tears toes white_body white_fur
2021 absurd_res anthro 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_(helluva_boss) mammal nipples notched_ear orgasm paws pussy pussy_juice sadtoasterr sex_toy solo vibrator white_body white_fur
2021 absurd_res anthro 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_(helluva_boss) mammal nipples notched_ear orgasm paws pussy pussy_juice sadtoasterr sex_toy solo vibrator white_body white_fur