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absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear absurd_res anthro avian bird daughter_(lore) digital_media_(artwork) duo duo_focus embrace father_(lore) father_and_child_(lore) father_and_daughter_(lore) female group heart_symbol helluva_boss hi_res incest_(lore) kaitosha kissing kissing_chest male male/female octavia_(helluva_boss) owl owl_demon parent_(lore) parent_and_child_(lore) parent_and_daughter_(lore) romantic romantic_couple stolas_(helluva_boss) tickling anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro arctic_wolf blush canid canine canis deep_throat dialogue duo english_text fur hand_on_head helluva_boss hi_res illegaleel looking_up male male/male mammal oral oral_penetration owl_demon penetration raaf_helder_(character) sex stolas_(helluva_boss) tagme text white_body white_fur wolf yellow_sclera anthro arctic_wolf canid canine canis dialogue duo english_text hand_on_face helluva_boss hi_res illegaleel imminent_anal imminent_sex looking_back male male/male mammal owl_demon raaf_helder_(character) stolas_(helluva_boss) tagme text wolf worried anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear 4_eyes abs anthro avian big_muscles big_pecs bird black_body black_feathers black_hair blitzo_(helluva_boss) bodily_fluids clothing crying demon duo feathers grey_body grey_feathers hair helluva_boss hi_res horn huge_muscles huge_pecs huge_thighs imp larger_male male mrmelted multi_eye multicolored_body multicolored_feathers muscular muscular_anthro muscular_arms muscular_legs muscular_male owl owl_demon pec_grab pecs red_body red_eyes size_difference smaller_male stolas_(helluva_boss) suit tears thick_thighs anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear anthro avian back_spikes beak bird blitzo_(helluva_boss) cartoon_network demon duo feathers grey_body grey_feathers helluva_boss horn humanoid imp larger_male male open_mouth owl raised_leg red_body red_eyes regular_show reillow simple_background size_difference skinny_male smaller_male spiked_tail spikes spikes_(anatomy) spots standing stolas_(helluva_boss) tail text white_background writing_text yellow_eyes absurd_res anthro avian avian_demon bdsm bird bit_gag blindfold blitzo_(helluva_boss) butt demon duo fur gag gagged grey_body grey_fur grey_hair hair helluva_boss hi_res horn looking_at_another male male/male nervous nude owl owl_demon paldobeobe59670 red_body red_eyes red_skin short_hair simple_background smile stolas_(helluva_boss) white_face ahegao alternate_costume anal anal_penetration angel anthro blush bodily_fluids bovid bukkake caprine cherub clothed clothed_sex clothing coat collin_(helluva_boss) cum cum_in_ass cum_in_mouth cum_in_own_mouth cum_in_self cum_inside cum_on_face cum_on_self dildo dildo_insertion duo enookie face_fucking fellatio foreskin genital_fluids genitals heart_eyes heart_symbol helluva_boss hi_res humanoid_genitalia irrumatio jabot looking_pleasured male male/male mammal masturbation milking_tentacles oral owl_demon penetration penile penis romantic romantic_sex sex sex_toy sex_toy_insertion sheep size_difference stolas_(helluva_boss) tentacle_in_ass tentacle_penetration tentacle_sex tentacles topwear