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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 absurd_res 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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 beak big_breasts bird bodily_fluids breast_size_difference breasts choker crossgender demon duo elz_(elzzombie) eyes_closed feathers female female/female goolee grey_body grey_feathers hair helluva_boss hooves horn horn_jewelry humanoid humanoid_on_anthro imp jewelry kissing mtf_crossgender multi_eye necklace nude owl owl_demon red_body red_eyes red_skin skinny small_breasts smile spade_tail stolas_(helluva_boss) sweat tail white_hair 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 3d_(artwork) anthro avian balls big_balls big_penis bird blender_(artwork) blue_body bodily_fluids charleskirbyiii chest_tuft clothed clothing coffee_mug container cum cup demon digital_media_(artwork) feathers genital_fluids genitals hair hand_on_hip helluva_boss hi_res huge_balls huge_penis hyper hyper_balls hyper_genitalia hyper_penis leaking_cum male multi_eye owl owl_demon pantsless penis red_eyes shirt solo stolas_(helluva_boss) topwear tuft unimpressed 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 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