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1:1 2021 2_horns big_eyes big_horn black_and_white black_text breasts crackers_(qwerty_soda) demon dialogue digital_drawing_(artwork) digital_media_(artwork) english_text eyelashes female gesture hand_gesture handwritten_text hi_res horn monochrome open_mouth open_smile pointing qwerty_soda simple_background sketch smile solo speech_bubble text white_background 2023 2_horns bite_mark bite_mark_on_chest bite_mark_on_neck black_and_white blush blush_lines bottomwear breath bulge bulge_grab chest_lick clothed clothing curved_horn demon demon_humanoid dessert duo eyebrows eyelashes female female_humanoid fingerless_gloves floral_shirt food food_fetish food_play freckled_face freckles gloves hair handwear head_grab helluva_boss horn humanoid humanoid_on_humanoid ice_cream imp intraspecies licking long_eyelashes looking_down male male/female male_humanoid markings millie_(helluva_boss) mole_(marking) monochrome moxxie_(helluva_boss) navel not_furry open_clothing open_shirt open_topwear potatonebula shirt short_hair signature sitting sketch skirt spade_tail striped_horn stripes swimming_trunks swimwear tail teeth tongue tongue_out topwear anthro bodily_fluids breasts canid canid_demon canine clothing collar demon digital_media_(artwork) female fur genitals hair hellhound helluva_boss hi_res legwear looking_at_viewer loona_(helluva_boss) mammal mythological_canine mythological_creature mythology nipples piercing pussy red_sclera simple_background smile solo spread_legs spreading stockings sweat tail translucent translucent_clothing vina.ink white_body white_fur 2023 2_horns areola arm_around_shoulders bed bedroom black_and_pink bodily_fluids breasts cabinet cloven_hooves cowgirl_position cuff_(restraint) curved_horn demon demon_humanoid duo embrace entwined_tails eyebrows eyelashes eyes_closed female female_humanoid female_penetrated from_front_position furniture grabbing_sheets hair hand_on_head handcuffs happy happy_sex helluva_boss hooves horn humanoid humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid imp inside intraspecies kneeling laugh leaning leaning_forward long_eyelashes male male/female male_humanoid male_penetrating male_penetrating_female medium_breasts metal_cuffs millie_(helluva_boss) mirror monochrome moxxie_(helluva_boss) navel nipples not_furry on_bottom on_top open_mouth penetration penile penile_penetration penis_in_pussy pillow potatonebula reclining restraints sex short_hair signature spade_tail striped_horn stripes sweat sweaty_chest tail tail_coil teeth tongue tooth_gap vaginal vaginal_penetration window 1:1 2023 3_toes 4_fingers anthro anthro_on_anthro biped black_bra black_clothing black_text black_underwear bottomwear bra butt canid canid_demon canine clothing crouching demon digitigrade double_thumbs_up duo english_text extreme_size_difference eyebrows feet female fingers fur gesture greyscale hand_gesture hellhound helluva_boss hi_res intraspecies larger_female looking_up lying male male/female mammal meme monochrome mythological_canine mythological_creature mythology navel notched_ear on_back panties paws potatonebula queen_bee-lzebub_(helluva_boss) shorts signature size_difference sketch smaller_male snout spread_legs spreading tail tail_motion tailwag text thumbs_up toes torn_bottomwear torn_clothing torn_shorts underwear vortex_(helluva_boss) 2021 2_horns alternate_form animate_inanimate backpack black_and_white boots bottomwear clothing crackers_(qwerty_soda) demon digital_drawing_(artwork) digital_media_(artwork) doll duo eyelashes eyes_closed female fingers footwear hands_on_shoulders heart_symbol hi_res horn human kissy_face lips living_doll living_plushie male male/female mammal monochrome plushie possessed_inanimate possession puckered_lips qwerty_soda seam_(sewing) shoulder_grab simple_background size_difference skirt small_waist smile spade_tail standing_on_object stitch_(sewing) tail white_background 2023 4_fingers ambiguous_gender ambiguous_penetrating ambiguous_penetrating_male anal anal_fingering anthro anus asmodeus_(helluva_boss) balls black_and_white_and_red black_text blue_text blush blush_lines bodily_fluids carrying_another carrying_partner clothing color_coded_text cum cumshot cybernetic_arm cybernetic_leg cybernetic_limb cybernetics cyborg demon demon_humanoid drooling duo ejaculation extreme_size_difference eyebrows eyes_closed fingering fingering_partner fingers fizzarolli_(helluva_boss) genital_fluids genitals glans hands-free hat hat_only headgear headgear_only headwear headwear_only helluva_boss humanoid humanoid_genitalia humanoid_penetrated humanoid_penis imp larger_ambiguous machine male male/ambiguous male_(lore) male_humanoid male_penetrated moan mostly_nude mostly_nude_anthro mostly_nude_humanoid not_furry onomatopoeia penetration penis potatonebula profanity saliva saliva_on_face saliva_on_tongue saliva_string sex sharp_teeth signature size_difference smaller_male solo_focus sound_effects spread_legs spreading stuttering talking_to_another talking_to_partner tears teeth text tongue tongue_out torso_grab 1:1 2023 3_toes 4_fingers abstract_background anthro bite biting_lip biting_own_lip black_bottomwear black_clothing black_eyebrows black_fingerless_gloves black_gloves black_handwear black_legwear black_nose black_skirt black_tail black_thigh_highs blue_clothing blue_shirt blue_topwear border bottomwear canid canid_demon canine cheek_tuft clothing crop_top demon digitigrade ear_piercing eye_through_hair eyebrow_through_hair eyebrows eyelashes facial_tuft feet female female_anthro fingerless_gloves fingers fur gloves grey_body grey_ears grey_fur grey_hair hair handwear hellhound helluva_boss hi_res inner_ear_fluff legwear long_hair loona_(helluva_boss) mammal midriff multicolored_body multicolored_fur mythological_canine mythological_creature mythology navel notched_ear occult_symbol paws pentagram piercing potatonebula pupils purple_background red_background red_sclera shaded shirt signature simple_background skirt slit_pupils snout solo symbol tail teeth text thigh_highs toes topwear torn_clothing torn_shirt torn_skirt torn_topwear translucent translucent_hair translucent_text tuft two_tone_body two_tone_fur two_tone_tail white_body white_border white_eyes white_fur white_inner_ear white_inner_ear_fluff white_tail 2023 3_toes anal anal_penetration anthro anthro_on_anthro biped black_and_white black_text blush blush_lines bodily_fluids bottomwear breasts butt canid canid_demon canine cheek_tuft clothed clothed/nude clothed_anthro clothed_female clothing collar crop_top demon dialogue digitigrade dildo dildo_in_ass dildo_insertion dominant dominant_female duo english_text eyebrows eyelashes facial_tuft fangs feet female female/female female_anthro female_penetrated flufy_tail foot_fetish foot_play footjob genital_fluids grin hair hellhound helluva_boss holding_leash holding_object hugging_leg humiliation humping intraspecies leaning leaning_backward leaning_forward leash leash_pull leashed_collar long_hair loona_(helluva_boss) mammal medium_breasts midriff monochrome motion_lines mythological_canine mythological_creature mythology nude nude_anthro nude_female object_in_ass penetration potatonebula pussy_juice_on_butt pussy_juice_on_feet queen_bee-lzebub_(helluva_boss) sex sex_toy sex_toy_in_ass sex_toy_insertion sharp_teeth shirt shorts signature sitting sketch smile snout sound_effects speech_bubble spiked_collar spikes spread_legs spreading stuttering submissive submissive_female tail talking_to_another talking_to_partner teeth text toes topwear tuft vaginal vaginal_fluids vaginal_footjob yelling 4_eyes anthro big_breasts blush bovid breasts caprine caprine_demon cinnamoncat clothed clothing demon dress ear_piercing eldritch_being female green_eyes hi_res horn jewelry mammal multi_eye piercing rhok'zan_(sucker_for_love) solo sucker_for_love 4_eyes altered_reflection ambiguous_gender anthro big_breasts bovid breasts caprine caprine_demon clothed clothing demon dress duo eldritch_being female green_eyes hi_res hooves horn human mammal mature_female mirror multi_eye reflection rhok'zan_(sucker_for_love) robe sucker_for_love thick_thighs vernoncaolo 2023 2_horns 4_fingers apron areola background_character big_breasts breasts cleavage clothed clothing demon demon_humanoid eyebrows eyelashes eyeliner female female_humanoid fingers flashing greyscale half-closed_eyes helluva_boss horn humanoid leaning leaning_forward legwear lips looking_at_viewer makeup medium_hair monochrome narrowed_eyes no_bra not_furry notched_ear open_mouth potatonebula signature sketch solo spade_tail standing succubus tail thigh_highs 2021 2_horns 5_fingers big_breasts bodily_fluids breasts crackers_(qwerty_soda) demon drooling embroidery female fingers frown hi_res horn looking_at_mirror looking_at_object mirror motion_lines photography_(artwork) qwerty_soda red_face red_horn sad saliva seam_(sewing) sink solo stitch_(sewing) tears teeth toilet traditional_media_(artwork) 1:1 2023 2_horns 4_fingers anal anal_masturbation anal_penetration bed bite biting_lip biting_own_lip blush blush_lines bodily_fluids breasts clitoral clitoral_fingering clitoral_masturbation cloven_hooves collarbone demon demon_humanoid dildo dildo_in_ass dildo_insertion eyebrows eyelashes eyes_closed female female_humanoid fingering fingering_self fingers furniture genital_fluids genitals greyscale hair headboard helluva_boss hooves horn humanoid imp leaning leaning_backward lips long_hair masturbation medium_breasts monochrome moxxie's_mother nipples not_furry nude nude_female nude_humanoid object_in_ass on_bed penetration pillow potatonebula pussy pussy_juice_on_hand pussy_juice_on_pussy quilted_headboard sex_toy sex_toy_in_ass sex_toy_insertion signature sitting sketch solo spade_tail spread_legs spreading striped_horn stripes sweat sweaty_face tail unguligrade vaginal vaginal_fingering vaginal_fluids vaginal_masturbation 2023 2_horns 4_fingers ambiguous_penetration anal anal_penetration areola arm_tattoo bent_over black_text blush breasts building butt butt_slap chair city clothing contact_onomatopoeia cunnilingus curved_horn demon demon_humanoid dialogue duo eye_roll eye_through_hair eyebrow_through_hair eyebrows eyelashes eyes_closed fantasizing female female_humanoid female_penetrated fingerless_gloves fingers fishnet_clothing fishnet_legwear from_behind_position full_nelson_(legs_held) full_nelson_position furniture genitals gloves greyscale hair hair_grab half-closed_eyes handwear head_tilt heart_symbol heart_tattoo helluva_boss hi_res holding_leash holding_object horn humanoid humanoid_genitalia humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid humanoid_pussy imp impact_onomatopoeia inside intraspecies leash legwear lips long_eyelashes male male/female male_humanoid male_penetrating male_penetrating_female medium_breasts millie_(helluva_boss) moan monochrome motion_lines moxxie_(helluva_boss) narrowed_eyes neck_grab nipples not_furry onomatopoeia open_mouth oral penetration penile penile_penetration penis_in_ass plap potatonebula pubes pussy raised_eyebrow rough_sex running_makeup running_mascara sex sharp_teeth shirt short_hair shoulder_tattoo signature sitting skyscraper slap sound_effects spank_marks spanking speech_bubble standing_doggystyle striped_horn stripes tail tail_grab tailjob_while_penetrated talking_to_another talking_to_partner tattoo teeth term_of_endearment text tongue tongue_out tooth_gap topwear touching_hair translucent translucent_hair vaginal white_text window 1:1 2023 2_horns 4_fingers accent anal anal_penetration ass_up bed black_clothing black_fingerless_gloves black_gloves black_handwear black_horn butt clothing color_coded_text contact_onomatopoeia curved_horn demon demon_humanoid dialogue dildo dildo_in_ass dildo_insertion dominant dominant_female duo english_text female female_humanoid female_penetrating female_penetrating_male female_pov fingerless_gloves fingers first_person_view furniture gloves gloves_only hair handwear handwear_only helluva_boss hi_res horn humanoid humanoid_on_humanoid humanoid_penetrated humanoid_penetrating humanoid_penetrating_humanoid humanoid_pov imp impact_onomatopoeia intraspecies male male/female male_humanoid male_penetrated millie_(helluva_boss) moan mommy_kink mostly_nude mostly_nude_female mostly_nude_humanoid mostly_nude_male moxxie_(helluva_boss) multicolored_horn neck_grab nipples not_furry object_in_ass on_bed onomatopoeia pegging penetrating_pov penetration pillow pillow_hug plap potatonebula purple_dildo purple_sheets red_nipples red_pillow red_tail red_text sex sex_toy sex_toy_in_ass sex_toy_insertion sex_toy_penetration short_hair signature sound_effects speech_bubble striped_horn stripes stuttering submissive submissive_male tail tail_grab talking_to_another talking_to_partner text toying_partner two_tone_horn white_hair white_horn white_text 2023 2_horns accessory barefoot belt black_bottomwear black_clothing black_dress black_eyebrows black_hair black_horn black_jacket black_pants black_suit black_topwear bodypaint bottomwear bow_tie brown_belt clothing cloven_hooves curved_horn day_of_the_dead demon demon_humanoid dress eyebrows eyelashes eyes_closed face_paint feet female flower flower_in_hair ghost group hair hair_accessory hands_behind_back heart_symbol helluva_boss hi_res holidays hooves horn humanoid humanoid_on_humanoid imp jacket long_eyelashes male male/female millie_(helluva_boss) moxxie's_mother moxxie_(helluva_boss) multicolored_clothing multicolored_dress multicolored_horn not_furry orange_clothing orange_dress pants plant potatonebula red_body red_bow_tie red_clothing red_dress red_hooves red_skin red_tail ringed_horn shirt short_hair signature smile spade_tail spirit suit tail teeth tooth_gap topwear trio two_tone_horn unguligrade white_clothing white_dress white_hair white_horn white_shirt white_topwear yellow_clothing yellow_dress yellow_flower 2023 2_horns accent all_fours anal anal_beads anal_fingering ankle_cuffs anus ball_squeeze biped bite biting_lip biting_own_lip black_text butt choker clothing cloven_hooves cock_and_ball_torture crossed_legs cuff_(restraint) demon demon_humanoid dialogue dildo dominant dominant_female duo english_text eyebrows eyelashes female female_fingering_male female_humanoid fingering fingering_partner genital_torture genitals gloves good_boy greyscale hair handwear heart_symbol helluva_boss hooves horn humanoid humanoid_on_humanoid imp intraspecies jewelry long_eyelashes male male/female male_humanoid millie_(helluva_boss) moan monochrome moxxie_(helluva_boss) necklace not_furry paddle penis perineum potatonebula restraints rope sex sex_toy short_hair spade_tail spank_marks spreader_bar striped_horn stripes stuttering submissive submissive_male tail talking_to_another talking_to_partner teeth text tooth_gap underhoof unguligrade white_text wrist_cuffs 2023 2_horns 4_fingers anthro avian beak belt bite_mark bite_mark_on_breast bite_mark_on_shoulder bite_mark_on_thigh black_and_white black_text bottomwear bra breasts clothed clothing curved_horn demon demon_humanoid dialogue dressing duo english_text eyebrows eyelashes facial_hair fangs feather_hair feathers female female_anthro fingerless_gloves fingers genitals gloves hair handwear head_tilt helluva_boss holding_clothing holding_object horn humanoid humanoid_on_anthro imp interspecies lingerie long_eyelashes male male/female male_humanoid medium_breasts monochrome mouth_closed mustache navel nipples nude nude_anthro nude_female open_belt open_bottomwear open_clothing open_pants panties pants potatonebula pseudo_hair pussy raised_eyebrow ringed_eyes shirt short_hair signature sketch slim_female smile snout spade_tail spiked_tail spikes spikes_(anatomy) stella_(helluva_boss) striker_(helluva_boss) striped_horn stripes tail talking_to_another talking_to_partner teeth text topwear underwear 2023 2_horns anal anal_knotting anal_penetration animal_dildo animal_sex_toy anthro anthro_penetrating anthro_penetrating_humanoid anus arm_grab avian beak begging big_dom_small_sub black_and_white black_text blush bodily_fluids canine_dildo collar curved_horn demon demon_humanoid dialogue dildo dildo_in_ass dildo_insertion dominant dominant_anthro dominant_female dripping drooling duo english_text eyebrows eyelashes facial_hair feather_hair feathers female female_anthro female_penetrating female_penetrating_male fucked_silly hair half-closed_eyes heart_symbol helluva_boss horn humanoid humanoid_on_anthro humanoid_penetrated imp kneeling knotting larger_anthro larger_female long_eyelashes looking_back male male/female male_humanoid male_penetrated moan monochrome mustache narrowed_eyes object_in_ass open_mouth pegging penetration potatonebula profanity pseudo_hair pupils ringed_eyes saliva saliva_drip saliva_on_tongue saliva_string scar sex sex_toy sex_toy_in_ass sex_toy_insertion sex_toy_penetration sharp_teeth short_hair sitting size_difference sketch slit_pupils smaller_humanoid smaller_male smaller_penetrated snout spade_tail speech_bubble spiked_tail spikes spikes_(anatomy) stella_(helluva_boss) strapon striker_(helluva_boss) striped_horn stripes stuttering submissive submissive_humanoid submissive_male sweat sweaty_face tail tail_around_body talking_to_another talking_to_partner teeth text tongue tongue_out toying_partner 2023 2_horns 4_fingers anthro areola avian bdsm beak belt black_and_white black_text bodily_fluids bottomwear bottomwear_down breasts cellphone clit_torture clitoral clitoral_masturbation clothed clothing contact_onomatopoeia curved_horn demon demon_humanoid dialogue dirty_talk dominant dominant_humanoid dominant_male duo electronics english_text eyebrows eyelashes eyes_closed facial_hair feather_hair feathers female female_anthro fingers genital_fluids genital_torture genitals glans good_girl head_tilt helluva_boss hi_res horn humanoid humanoid_genitalia humanoid_penis imp impact_onomatopoeia jacket kerchief legwear long_eyelashes male male/female male_humanoid masturbation medium_breasts moan monochrome mostly_nude_anthro mostly_nude_female motion_lines mustache navel neckerchief nipple_clamp nipple_fetish nipple_pinch nipple_play nipple_torture nipples onomatopoeia open_belt open_mouth pants pants_down partially_clothed partially_clothed_humanoid partially_clothed_male penile penile_masturbation penis phone phone_sex pillow pinch pinching_clitoris potatonebula precum pseudo_hair pussy_spanking pussy_torture reclining running_makeup running_mascara saliva saliva_on_tongue saliva_string shaking sharp_teeth short_horn signature sketch small_horn sound_effects speech_bubble spread_legs spreading stella_(helluva_boss) striker_(helluva_boss) striped_horn stripes stuttering submissive submissive_anthro submissive_female sweat sweaty_face talking_to_another talking_to_partner teeth text thigh_highs topwear trembling underwear vein veiny_penis whining white_text 2023 4_fingers anthro avian bandage beak bird's-eye_view black_text boxer_briefs bra clothed clothing comforting cuddling demon demon_humanoid dialogue duo embrace english_text eyebrows eyelashes facial_hair feather_hair feathers female female_anthro fingerless_gloves fingers gloves greyscale hair half-closed_eyes handwear helluva_boss high-angle_view horn humanoid humanoid_on_anthro imp larger_anthro larger_female long_eyelashes looking_down male male/female male_humanoid monochrome mustache narrowed_eyes panties potatonebula pseudo_hair scar short_hair signature size_difference sketch smaller_humanoid smaller_male snout spade_tail speech_bubble spiked_tail spikes spikes_(anatomy) spooning stella_(helluva_boss) striker_(helluva_boss) tail talking_to_another talking_to_partner text topless topless_anthro topless_humanoid underwear underwear_only wounded 2girls bed black_hair breasts clothed_female_nude_female colored_skin curanto curly_hair demon demon_girl demon_horns foot_on_another's_thigh height_difference horns large_breasts monster monster_girl multiple_girls muscular muscular_female nightgown non-web_source noses_touching nude on_bed original red_skin size_difference sleepwear summoning yuri 2023 2_horns anthro armwear avian balls bdsm beak belt big_dom_small_sub black_and_white black_text blush boots breasts butt chair cleavage cleavage_cutout clothed clothed_anthro clothed_female clothing curved_horn cutout demon demon_humanoid dialogue discarded_pants dominant dominant_anthro dominant_female duo elbow_gloves english_text eyebrows eyelashes eyes_closed facial_hair feather_hair feathers female female_anthro footwear furniture genitals gloves good_boy handwear helluva_boss high_heeled_boots high_heels holding_paddle horn humanoid humanoid_on_anthro imp interspecies larger_anthro larger_female legwear leotard long_eyelashes male male/female male_humanoid medium_breasts monochrome mostly_nude mostly_nude_humanoid mostly_nude_male mustache on_lap over_knee paddle potatonebula pseudo_hair signature sitting size_difference smaller_humanoid smaller_male spade_tail spank_marks spiked_tail spikes spikes_(anatomy) spot_color stella_(helluva_boss) striker_(helluva_boss) striped_horn stripes stuttering submissive submissive_humanoid submissive_male tail tail_feathers tail_grab talking_to_another talking_to_partner text thigh_boots thigh_highs 2023 2_horns 4_fingers all_fours anal anal_masturbation anal_penetration anus arched_back balls black_and_white black_text blush blush_lines bodily_fluids clothing cloven_hooves collar cum cumshot curved_horn daddy_kink demon demon_humanoid dialogue dildo dildo_in_ass dildo_insertion disembodied_hand dripping drooling duo ejaculation english_text erection eyes_closed facial_hair fingerless_gloves fingers flaccid foreskin genital_fluids genitals gloves hair handwear helluva_boss holding_leash holding_object hooves horn humanoid humanoid_genitalia humanoid_penetrated humanoid_penis imp leash leash_pull leashed_collar looking_back lying male male/male male_humanoid male_penetrated male_penetrating male_penetrating_male masturbation moan monochrome mostly_nude mostly_nude_anthro mostly_nude_humanoid multiple_images mustache not_furry nude nude_anthro nude_male object_in_ass on_side partially_retracted_foreskin penetration penile penile_masturbation penis perineum potatonebula pupils rear_view saliva saliva_drip saliva_on_tongue scar sex sex_toy sex_toy_in_ass sex_toy_insertion short_hair sketch slit_pupils smile smirk solo solo_focus spade_tail spiked_tail spikes spikes_(anatomy) striker_(helluva_boss) striped_horn stripes sweat sweaty_face tail tail_grab tail_pull talking_to_another talking_to_partner tears text tongue tongue_out toying_self vibrator vibrator_on_penis 2023 5_fingers all_fours ambiguous_penetration anthro anthro_on_anthro anthro_penetrated anthro_penetrating anthro_penetrating_anthro areola avian barbell_piercing bdsm biped black_and_white black_text bodily_fluids breasts breath butt_slap canid cassie_(eziodude98) collar collar_only daddy_kink demon dialogue dirty_talk doggystyle dripping drooling duo ear_piercing ear_ring english_text eyebrows eyelashes feather_hair feathers female female_penetrated fingers from_behind_position genital_fluids good_girl grabbing_sheets heart_symbol helluva_boss holding_leash holding_object interspecies kneeling leash leash_pull leashed_collar long_eyelashes male male/female male_penetrating male_penetrating_female mammal medium_breasts moan monochrome motion_lines nipple_barbell nipple_piercing nipples nude open_mouth panting pecs penetration penile penile_penetration piercing potatonebula prick_ears pseudo_hair pussy_juice_drip pussy_juice_on_leg ring_piercing rough_sex saliva sex side_view signature sketch slap smile smirk snout spank_marks spanking spiral_eyes stella_(helluva_boss) tail tail_motion tailwag talking_to_another talking_to_partner tears text thrusting tongue vaginal_fluids wide_eyed 2021 2_horns 5_fingers big_breasts black_choker black_clothing black_dress black_jewelry black_necklace black_text breasts butt choker cleavage clothed clothing crackers_(qwerty_soda) cross cross-eyed cross_necklace demon dialogue digital_drawing_(artwork) digital_media_(artwork) dress english_text eyelashes female fingers front_view gesture hand_gesture heart_symbol hi_res horn jewelry long_eyelashes looking_aside looking_back multiple_poses necklace open_mouth open_smile pointing portrait pose pupils qwerty_soda rear_view red_body red_face red_horn simple_background slit_pupils smile solo speech_bubble text thick_thighs three-quarter_portrait three-quarter_view white_background 2023 2_horns accessory areola ball_gag balls bdsm black_text blindfold blush blush_lines bodily_fluids bondage bound breasts cock_ring contact_onomatopoeia curved_horn demon demon_humanoid dripping english_text erection gag gagged genital_fluids genitals glans greyscale gynomorph gynomorph_humanoid hair hands_behind_back heart_symbol helluva_boss horn humanoid humanoid_genitalia humanoid_penis imp impact_onomatopoeia intersex intersex_humanoid jewelry legs_tied long_hair medium_breasts moan monochrome nipples not_furry nude nude_female nude_humanoid onomatopoeia paddle paddling penis penis_accessory penis_jewelry potatonebula precum precum_drip restraints rope rope_bondage rope_harness sallie_may_(helluva_boss) signature solo sound_effects spade_tail spank_marks spot_color striped_horn stripes suspension suspension_bondage tail tail_tied text trans_(lore) trans_woman_(lore) white_text wrists_tied 2021 2_horns 4_fingers alternate_form big_eyes big_horn black_clothing black_dress black_text blade_arm boots breasts clothed clothing crackers_(qwerty_soda) cross cross_necklace demon dialogue digital_drawing_(artwork) digital_media_(artwork) dress english_text eyelashes female fingers footwear front_view full-length_portrait handwritten_text hat headgear headwear heart_symbol horn jewelry long_eyelashes looking_aside machine multiple_poses necklace nurse_clothing nurse_hat nurse_headwear nurse_uniform open_mouth open_smile partially_colored portrait pose profanity qwerty_soda robot simple_background sketch small_waist smile solo speech_bubble standing text uniform white_background 2023 2_horns 4_fingers anal anal_penetration animal_genitalia animal_penis anthro anthro_penetrating anthro_penetrating_humanoid arms_tied avian ball_gag balls bdsm beak big_dom_small_sub bird blitzo_(helluva_boss) blush blush_lines bodily_fluids bondage bound breath buzzing chain chair_position chastity_cage chastity_device contact_onomatopoeia cum cum_on_balls cum_on_own_balls cum_on_self cum_while_chaste cumshot curved_horn demon demon_humanoid dominant dominant_anthro dominant_male dripping drooling duo ejaculation empty_eyes english_text eyebrows eyes_closed feathers fingers from_behind_position gag gagged genital_fluids genitals greyscale hand_on_chin hands_behind_head helluva_boss hi_res hitachi_magic_wand holding_object holding_sex_toy holding_vibrator horn humanoid humanoid_on_anthro humanoid_penetrated imp impact_onomatopoeia larger_anthro legs_tied male male/male male_anthro male_humanoid male_penetrated male_penetrating male_penetrating_male moan monochrome navel nipple_clamp on_lap onomatopoeia open_mouth owl owl_demon penetration penile penile_penetration penis penis_in_ass plap potatonebula saliva saliva_drip saliva_on_face sex sex_toy signature sitting size_difference smaller_humanoid smaller_penetrated sound_effects spade_tail spot_color spread_legs spreading stolas_(helluva_boss) striped_horn stripes submissive submissive_humanoid submissive_male tail tail_around_leg tears text toying_partner vibrator vibrator_on_penis wand_vibrator white_text 2023 2_horns all_fours anal anal_penetration anthro anthro_penetrating anthro_penetrating_humanoid arms_tied ass_up avian baton bdsm bird black_text blitzo_(helluva_boss) blush blush_lines bodily_fluids bound butt caning chastity_cage chastity_device cum cum_from_ass cum_in_ass cum_inside curved_horn demon demon_humanoid dialogue doggystyle dominant dominant_anthro dominant_male drooling duo english_text from_behind_position genital_fluids greyscale helluva_boss horn humanoid humanoid_focus humanoid_on_anthro humanoid_penetrated imp male male/male male_anthro male_humanoid male_penetrated male_penetrating male_penetrating_male moan monochrome narrowed_eyes not_furry_focus owl owl_demon penetration penile penile_penetration penis_in_ass potatonebula precum profanity raised_tail saliva saliva_on_face sex sharp_teeth signature sketch solo_focus speech_bubble stolas_(helluva_boss) striped_horn stripes stuttering submissive submissive_humanoid submissive_male tail talking_to_another talking_to_partner teeth text tongue tongue_out urethral urethral_penetration wrists_tied absurd_res 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male_penetrating_male marine moan monochrome motion_lines not_furry_focus onomatopoeia partially_retracted_foreskin penetration penile penile_penetration penis penis_in_ass plap potatonebula rough_sex saliva saliva_on_face sex shark sharp_teeth signature sketch solo_focus sound_effects spade_tail stuttering tail tail_around_arm tail_grab tail_motion tailwag talking_to_another talking_to_partner tears teeth text thrusting 2023 2_horns biped black_bottomwear black_clothing black_eyebrows black_eyes black_fingerless_gloves black_gloves black_handwear black_horn black_jacket black_pants black_suit black_topwear body_hair bottomwear chest_hair cigarette clothed clothed_humanoid clothed_male clothing cloven_hooves crossed_legs curved_horn demon demon_humanoid dress_shirt eyebrows fingerless_gloves freckled_face freckles gloves hair hand_on_head handwear helluva_boss holding_cigarette holding_object hooves horn humanoid imp jacket loose_necktie male male_humanoid mouth_closed 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eyelashes femboy fingerless_gloves fingers freckled_face freckles gloves hair half-closed_eyes handwear helluva_boss hi_res horn humanoid imp legwear looking_at_viewer male male_humanoid midriff monochrome moxxie_(helluva_boss) narrowed_eyes navel not_furry pleated_skirt potatonebula shirt short_hair side_view signature sketch skirt solo spade_tail striped_horn stripes tail tail_under_skirt thigh_highs topwear unguligrade 2023 2_horns 4_fingers bdsm black_and_white breath butt butt_slap clothing cloven_hooves demon demon_humanoid dominant dominant_male duo english_text eyelashes eyeliner female female_humanoid fingerless_gloves fingers furgonomics gloves good_girl grabbing_sheets handwear helluva_boss hi_res hooves horn humanoid imp long_eyelashes looking_at_another looking_at_partner lying makeup male male/female male_humanoid millie_(helluva_boss) monochrome moxxie_(helluva_boss) not_furry on_front on_lap panties potatonebula red_text running_eyeliner signature sitting sketch slap smile smirk spank_marks spanking spot_color striped_horn stripes stuttering submissive submissive_female tail tail_grab tail_pull teeth text underwear 2023 anthro anti_material_rifle bottomwear canid canid_demon canine clothing collar demon ear_piercing english_text eye_through_hair eyebrow_through_hair eyebrows eyelashes female female_anthro fluffy fluffy_tail fur grey_text greyscale gun hair head_turned hellhound helluva_boss holding_gun holding_object holding_ranged_weapon holding_rifle holding_weapon legwear long_hair looking_at_viewer loona_(helluva_boss) mammal monochrome mythological_canine mythological_creature mythology occult_symbol pentagram piercing potatonebula prick_ears profanity pupils ranged_weapon scope shirt signature skirt slit_pupils smile smirk snout solo spiked_collar spikes standing symbol tail teeth text thigh_highs topwear torn_clothing torn_shirt torn_skirt torn_topwear translucent translucent_hair weapon 2023 2_horns 4_fingers accessory banknote black_and_white blush blush_lines bodily_fluids boots clothed clothing crossdressing cum cum_from_mouth cum_in_mouth cum_inside demon demon_humanoid duo eyebrows eyelashes facial_hair femboy fingerless_gloves fingers footwear garter garter_straps genital_fluids genitals gloves hair half-closed_eyes handwear helluva_boss horn humanoid humanoid_penetrating imp lingerie lying male male/male male_penetrated male_penetrating male_penetrating_male money monochrome mustache narrowed_eyes not_furry on_side oral oral_penetration penetration penile penile_penetration penis penis_in_mouth potatonebula prostitution pupils ringed_eyes sex short_hair signature sketch slit_pupils solo_focus spade_tail spiked_tail spikes spikes_(anatomy) striker_(helluva_boss) striped_horn stripes tail teddy_(clothing) vein veiny_penis 2023 2_horns 4_fingers barefoot black_and_white blitzo_(helluva_boss) bow_tie calvin_mcmurray clothing cloven_hooves cosplay crossover crossover_cosplay demon demon_humanoid eyebrows feet female female_humanoid fingerless_gloves fingers footwear front_view gloves group gun hair hand_on_hip handwear hat headgear headwear helluva_boss holding_gun holding_object holding_ranged_weapon holding_weapon hooves horn humanoid imp ivy_pepper jacket lackadaisy looking_at_viewer male male_humanoid millie_(helluva_boss) monochrome moxxie_(helluva_boss) necktie not_furry plant potatonebula ranged_weapon rocky_rickaby rolled_up_sleeves shoes short_hair shovel sketch smile smirk standing striped_horn stripes submachine_gun suit thompson_gun tools topwear trio unguligrade vest weapon