demon_on_angel best from all time

Time frame

Tags

demon on angel

angel angel_humanoid anus ass balls big_breasts big_butt bitterbunz bitterrbunz black_body black_feathers blush bodily_fluids breasts cowgirl_position cum demon demon_humanoid demon_on_angel dialogue erection faceless_character faceless_male feathers female female_penetrated foursome from_front_position gangbang genital_fluids genitals group group_sex hair halo handjob hazbin_hotel hi_res humanoid interspecies looking_pleasured lute_(hazbin_hotel) male male/female male_penetrating male_penetrating_female masturbation nipples on_bottom on_top open_mouth open_smile penetration penile penile_masturbation penile_penetration penis penis_in_pussy precum pussy red_body saliva sex smile speech_bubble sweat thick_thighs tongue tongue_out vaginal_fluids vaginal_penetration vein veiny_penis vivienne_medrano white_body white_feathers white_hair wings yellow_eyes
angel angel_humanoid anus ass balls big_breasts big_butt bitterbunz bitterrbunz black_body black_feathers blush bodily_fluids breasts cowgirl_position cum demon demon_humanoid demon_on_angel dialogue erection faceless_character faceless_male feathers female female_penetrated foursome from_front_position gangbang genital_fluids genitals group group_sex hair halo handjob hazbin_hotel hi_res humanoid interspecies looking_pleasured lute_(hazbin_hotel) male male/female male_penetrating male_penetrating_female masturbation nipples on_bottom on_top open_mouth open_smile penetration penile penile_masturbation penile_penetration penis penis_in_pussy precum pussy red_body saliva sex smile speech_bubble sweat thick_thighs tongue tongue_out vaginal_fluids vaginal_penetration vein veiny_penis vivienne_medrano white_body white_feathers white_hair wings yellow_eyes
after_sex angel anus ass bad_ending bed breasts cum cum_in_ass cum_in_pussy cum_inside demon demon_on_angel duo female grey_body hair hazbin_hotel helmet horns interspecies kyh_hkun male male/female money nude open_mouth partial_male picture pleasure_face pussy red_body short_hair smile tears teeth vaggie_(hazbin_hotel) white_hair
after_sex angel anus ass bad_ending bed breasts cum cum_in_ass cum_in_pussy cum_inside demon demon_on_angel duo female grey_body hair hazbin_hotel helmet horns interspecies kyh_hkun male male/female money nude open_mouth partial_male picture pleasure_face pussy red_body short_hair smile tears teeth vaggie_(hazbin_hotel) white_hair
1_eye 2angels angel angel_humanoid anus ass big_breasts big_butt bitterbunz bitterrbunz blonde_hair blue_eyes blue_hair bodily_fluids breasts charlie_morningstar charlie_morningstar_(hazbin_hotel) clothed clothing demon demon_humanoid demon_on_angel detailed_background emily_(hazbin_hotel) eye_patch eyewear female female/female genital_fluids genitals grey_body group hair halo hazbin_hotel hi_res humanoid nipples open_mouth open_smile partially_clothed pussy red_eyes seraph_(angel) smile thick_thighs trio vaggie_(hazbin_hotel) vaginal_fluids vivienne_medrano
1_eye 2angels angel angel_humanoid anus ass big_breasts big_butt bitterbunz bitterrbunz blonde_hair blue_eyes blue_hair bodily_fluids breasts charlie_morningstar charlie_morningstar_(hazbin_hotel) clothed clothing demon demon_humanoid demon_on_angel detailed_background emily_(hazbin_hotel) eye_patch eyewear female female/female genital_fluids genitals grey_body group hair halo hazbin_hotel hi_res humanoid nipples open_mouth open_smile partially_clothed pussy red_eyes seraph_(angel) smile thick_thighs trio vaggie_(hazbin_hotel) vaginal_fluids vivienne_medrano
absurd_res angel anthro balls black_hair bodily_fluids bovid breasts caprine cheating cheating_wife cherub closed_eyes collin_(helluva_boss) demon demon_humanoid demon_on_angel duo female female_penetrated fluffy fluffy_tail fur gatojack3 genital_fluids genitals hair helluva_boss hi_res humanoid imp interspecies looking_pleasured male male/female male_penetrating male_penetrating_female mammal millie_(helluva_boss) nipples penetration penile penile_penetration penis_in_pussy purple_body purple_fur pussy pussy_juice sex sheep tail teeth thick_thighs vaginal_penetration wings
absurd_res angel anthro balls black_hair bodily_fluids bovid breasts caprine cheating cheating_wife cherub closed_eyes collin_(helluva_boss) demon demon_humanoid demon_on_angel duo female female_penetrated fluffy fluffy_tail fur gatojack3 genital_fluids genitals hair helluva_boss hi_res humanoid imp interspecies looking_pleasured male male/female male_penetrating male_penetrating_female mammal millie_(helluva_boss) nipples penetration penile penile_penetration penis_in_pussy purple_body purple_fur pussy pussy_juice sex sheep tail teeth thick_thighs vaginal_penetration wings
2024 4_arms adam_(hazbin_hotel) angel balls belly boner clothed clothing demon demon_on_angel digital_drawing_(artwork) digital_media_(artwork) duo erection genitals green_clothing hazbin_hotel helluva_boss hi_res humanoid kirkland897 larger_male licking long_tongue male male/male male_only mammon_(helluva_boss) multi_arm multi_limb open_mouth oral overweight overweight_male penile penis penis_lick sex simple_background size_difference smaller_male spread_wings striped_tongue teeth tongue white_background wings yellow_wings
2024 4_arms adam_(hazbin_hotel) angel balls belly boner clothed clothing demon demon_on_angel digital_drawing_(artwork) digital_media_(artwork) duo erection genitals green_clothing hazbin_hotel helluva_boss hi_res humanoid kirkland897 larger_male licking long_tongue male male/male male_only mammon_(helluva_boss) multi_arm multi_limb open_mouth oral overweight overweight_male penile penis penis_lick sex simple_background size_difference smaller_male spread_wings striped_tongue teeth tongue white_background wings yellow_wings
2girls abdominal_bulge angel anus ass big_ass big_breasts bitterbunz blonde_hair blush breasts canon_couple charlie_morningstar_(hazbin_hotel) choker demon demon_form demon_on_angel doggy_style domination female female/female female_penetrated female_penetrating female_penetrating_female femdom femsub girlfriend girlfriends grey-skinned_female hazbin_hotel horns long_hair multiple_girls nipples nude open_mouth open_smile penetration pleasure_face pussy pussy_juice red_eyes rough_sex saliva smile strap-on strap-on_sex submissive submissive_female tail thighhighs vaggie_(hazbin_hotel) vivienne_medrano white-skinned_female white_hair wings yuri
2girls abdominal_bulge angel anus ass big_ass big_breasts bitterbunz blonde_hair blush breasts canon_couple charlie_morningstar_(hazbin_hotel) choker demon demon_form demon_on_angel doggy_style domination female female/female female_penetrated female_penetrating female_penetrating_female femdom femsub girlfriend girlfriends grey-skinned_female hazbin_hotel horns long_hair multiple_girls nipples nude open_mouth open_smile penetration pleasure_face pussy pussy_juice red_eyes rough_sex saliva smile strap-on strap-on_sex submissive submissive_female tail thighhighs vaggie_(hazbin_hotel) vivienne_medrano white-skinned_female white_hair wings yuri
angel angel_humanoid anthro big_breasts blue_hair blush breasts dark_body dark_skin demon demon_on_angel derocrossh duo female female_on_anthro female_penetrated from_behind_position fur hair halo hazbin_hotel hi_res humanoid interspecies lagomorph leporid looking_pleasured male male/female male_penetrating male_penetrating_female mammal mature_female mythology nipples nude open_mouth open_smile penetration rabbit red_eyes sera_(hazbin_hotel) seraph_(angel) sex smile standing standing_doggystyle standing_sex tail teeth thick_thighs white_body white_fur white_hair
angel angel_humanoid anthro big_breasts blue_hair blush breasts dark_body dark_skin demon demon_on_angel derocrossh duo female female_on_anthro female_penetrated from_behind_position fur hair halo hazbin_hotel hi_res humanoid interspecies lagomorph leporid looking_pleasured male male/female male_penetrating male_penetrating_female mammal mature_female mythology nipples nude open_mouth open_smile penetration rabbit red_eyes sera_(hazbin_hotel) seraph_(angel) sex smile standing standing_doggystyle standing_sex tail teeth thick_thighs white_body white_fur white_hair
1girls angel angel_humanoid big_breasts big_butt big_penis bitterbunz bitterrbunz black_body black_feathers blush bodily_fluids breasts butt cum demon demon_humanoid demon_on_angel dominant english_text erection faceless_character faceless_male feathers female genital_fluids genitals hair halo hazbin_hotel hi_res humanoid interspecies interspecies_domination looking_pleasured lute_(hazbin_hotel) male male/female nipples nude penis red_body short_hair text thighs tongue tongue_out vein veiny_penis vivienne_medrano white_body white_feathers wings yellow_eyes
1girls angel angel_humanoid big_breasts big_butt big_penis bitterbunz bitterrbunz black_body black_feathers blush bodily_fluids breasts butt cum demon demon_humanoid demon_on_angel dominant english_text erection faceless_character faceless_male feathers female genital_fluids genitals hair halo hazbin_hotel hi_res humanoid interspecies interspecies_domination looking_pleasured lute_(hazbin_hotel) male male/female nipples nude penis red_body short_hair text thighs tongue tongue_out vein veiny_penis vivienne_medrano white_body white_feathers wings yellow_eyes
adam_(hazbin_hotel) almohady_nsfw angel angel_humanoid black_body blush bodily_fluids breasts demon demon_humanoid demon_on_angel erection exorcist_(hazbin_hotel) faceless_character faceless_male female genital_fluids genitals green_hair group group_sex hair halo hazbin_hotel helluva_boss horn humanoid light-skinned_female lute_(hazbin_hotel) male male/female mammon_(helluva_boss) mature_male nipples nude open_mouth overweight overweight_male penis piyama_(artist) precum pubes sex simple_background slightly_chubby slightly_chubby_male sweat teeth thick_thighs threesome trio white_hair wings yellow_eyes
adam_(hazbin_hotel) almohady_nsfw angel angel_humanoid black_body blush bodily_fluids breasts demon demon_humanoid demon_on_angel erection exorcist_(hazbin_hotel) faceless_character faceless_male female genital_fluids genitals green_hair group group_sex hair halo hazbin_hotel helluva_boss horn humanoid light-skinned_female lute_(hazbin_hotel) male male/female mammon_(helluva_boss) mature_male nipples nude open_mouth overweight overweight_male penis piyama_(artist) precum pubes sex simple_background slightly_chubby slightly_chubby_male sweat teeth thick_thighs threesome trio white_hair wings yellow_eyes
angel angel_humanoid balls big_breasts big_penis bitterbunz bitterrbunz blush bodily_fluids breast_milking breast_play breast_sucking breasts cheating_husband clothed clothing dark_body dark_skin demon demon_humanoid demon_on_angel dialogue duo female genital_fluids genitals hair halo hazbin_hotel helluva_boss hi_res hooves horn humanoid imp infidelity interspecies lactating lactation male male/female masturbation mature_female moxxie_(helluva_boss) open_mouth partially_clothed penile penile_masturbation penis precum red_body sera_(hazbin_hotel) seraph_(angel) speech_bubble sucking tail teeth thick_thighs vivienne_medrano white_hair wings
angel angel_humanoid balls big_breasts big_penis bitterbunz bitterrbunz blush bodily_fluids breast_milking breast_play breast_sucking breasts cheating_husband clothed clothing dark_body dark_skin demon demon_humanoid demon_on_angel dialogue duo female genital_fluids genitals hair halo hazbin_hotel helluva_boss hi_res hooves horn humanoid imp infidelity interspecies lactating lactation male male/female masturbation mature_female moxxie_(helluva_boss) open_mouth partially_clothed penile penile_masturbation penis precum red_body sera_(hazbin_hotel) seraph_(angel) speech_bubble sucking tail teeth thick_thighs vivienne_medrano white_hair wings
1boy 1girls 3d angel angel_and_devil angel_wings angry animated areolae arms_behind_back arms_tied arms_tied_behind_back bad_end barefoot beaten big_breasts bondage bouncing_breasts breasts busty captured captured_heroine cowgirl_position dark-skinned_female darksiders darksiders_2 defeated defeated_heroine demon demon_boy demon_horns demon_on_angel embarrassed erect_nipples female female_on_top fit_female golden_eyes interspecies long_hair male mature_female mature_male monster_rape mp4 nipples no_sound non-human penetration penis pinned_down rape red_body red_skin restrained restraints rexxcraft riding_penis sex sex_slave slim_waist straddling straight straight_hair straight_sex tagme thrusting uriel_(darksiders) vagina vaginal vaginal_penetration vaginal_sex video voluptuous white_hair wide_hips
1boy 1girls 3d angel angel_and_devil angel_wings angry animated areolae arms_behind_back arms_tied arms_tied_behind_back bad_end barefoot beaten big_breasts bondage bouncing_breasts breasts busty captured captured_heroine cowgirl_position dark-skinned_female darksiders darksiders_2 defeated defeated_heroine demon demon_boy demon_horns demon_on_angel embarrassed erect_nipples female female_on_top fit_female golden_eyes interspecies long_hair male mature_female mature_male monster_rape mp4 nipples no_sound non-human penetration penis pinned_down rape red_body red_skin restrained restraints rexxcraft riding_penis sex sex_slave slim_waist straddling straight straight_hair straight_sex tagme thrusting uriel_(darksiders) vagina vaginal vaginal_penetration vaginal_sex video voluptuous white_hair wide_hips
4:3 absurd_res angel anonymous_artist anthro anthro_on_anthro bovid breasts canid canid_demon caprine cherub claws collin_(helluva_boss) demon demon_on_angel doggy_style duo ear_piercing ear_ring edit fangs female female_penetrated fluffy fluffy_tail from_behind_position fur grey_body grey_fur grey_hair hair halo hellhound helluva_boss hi_res interspecies looking_pleasured loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal multicolored_body multicolored_fur nipples open_mouth orgasm orgasm_face penetration penile penile_penetration penis_in_pussy piercing purple_body purple_fur red_sclera ring_piercing sex sheep simple_background tail teeth tongue tongue_out two_tone_body two_tone_fur vaginal_penetration vaginal_penetration white_body white_fur wings
4:3 absurd_res angel anonymous_artist anthro anthro_on_anthro bovid breasts canid canid_demon caprine cherub claws collin_(helluva_boss) demon demon_on_angel doggy_style duo ear_piercing ear_ring edit fangs female female_penetrated fluffy fluffy_tail from_behind_position fur grey_body grey_fur grey_hair hair halo hellhound helluva_boss hi_res interspecies looking_pleasured loona_(helluva_boss) male male/female male_penetrating male_penetrating_female mammal multicolored_body multicolored_fur nipples open_mouth orgasm orgasm_face penetration penile penile_penetration penis_in_pussy piercing purple_body purple_fur red_sclera ring_piercing sex sheep simple_background tail teeth tongue tongue_out two_tone_body two_tone_fur vaginal_penetration vaginal_penetration white_body white_fur wings
absurd_res angel anthro anthro_on_anthro anus ass balls big_balls big_butt blush bodily_fluids bovid canid canid_demon canine caprine cherub collin_(helluva_boss) cum cum_in_pussy cum_inside demon demon_on_angel doggy_style duo excessive_cum excessive_genital_fluids female fluffy fluffy_tail foxylovescoke from_behind_position fur genital_fluids genitals grey_hair hair hellhound helluva_boss hi_res interspecies looking_pleasured loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology nude penis pubes purple_body purple_fur pussy sex sheep sweat tail thick_thighs vaginal_penetration
absurd_res angel anthro anthro_on_anthro anus ass balls big_balls big_butt blush bodily_fluids bovid canid canid_demon canine caprine cherub collin_(helluva_boss) cum cum_in_pussy cum_inside demon demon_on_angel doggy_style duo excessive_cum excessive_genital_fluids female fluffy fluffy_tail foxylovescoke from_behind_position fur genital_fluids genitals grey_hair hair hellhound helluva_boss hi_res interspecies looking_pleasured loona_(helluva_boss) male male/female mammal mythological_canine mythological_creature mythology nude penis pubes purple_body purple_fur pussy sex sheep sweat tail thick_thighs vaginal_penetration
aggressivedog angel angry blush breasts claws damaged_clothes demon demon_on_angel dialogue duo feathers female female_penetrated forced gag glasses hair halo hat hazbin_hotel interspecies lute_(hazbin_hotel) male male/female male_penetrating male_penetrating_female moth nude partially_clothed penetration penis penis_in_pussy purple_body pussy pussy_juice rape red_eyes saliva sex speech_bubble straight teeth tongue tongue_out vaginal_penetration valentino_(hazbin_hotel) vein veiny_penis white_hair wings yellow_eyes
aggressivedog angel angry blush breasts claws damaged_clothes demon demon_on_angel dialogue duo feathers female female_penetrated forced gag glasses hair halo hat hazbin_hotel interspecies lute_(hazbin_hotel) male male/female male_penetrating male_penetrating_female moth nude partially_clothed penetration penis penis_in_pussy purple_body pussy pussy_juice rape red_eyes saliva sex speech_bubble straight teeth tongue tongue_out vaginal_penetration valentino_(hazbin_hotel) vein veiny_penis white_hair wings yellow_eyes
1boy 1boy1girl 1girls angel angel_girl angel_wings angry animated areolae arms_behind_back arms_tied arms_tied_behind_back bad_end barefoot beaten big_breasts bondage breasts busty captured captured_heroine cleft_of_venus clitoris completely_naked completely_nude completely_nude_female completely_nude_male dark-skinned_female darksiders darksiders_2 defeated defeated_heroine demon demon_boy demon_horns demon_on_angel embarrassed erect_nipples female female/male female_penetrated fit_female golden_eyes large_breasts long_hair male male_penetrating male_penetrating_female markings mature_female monster_rape naked nipples nude nude_female nude_male nudity pussy rape red_body red_skin restrained restraints reverse_suspended_congress rexxcraft sex sex_slave slim_waist spread_legs standing_sex straight straight_hair straight_sex tagme tattoo thrusting uriel_(darksiders) vagina vaginal vaginal_penetration vaginal_sex video white_hair wide_hips
1boy 1boy1girl 1girls angel angel_girl angel_wings angry animated areolae arms_behind_back arms_tied arms_tied_behind_back bad_end barefoot beaten big_breasts bondage breasts busty captured captured_heroine cleft_of_venus clitoris completely_naked completely_nude completely_nude_female completely_nude_male dark-skinned_female darksiders darksiders_2 defeated defeated_heroine demon demon_boy demon_horns demon_on_angel embarrassed erect_nipples female female/male female_penetrated fit_female golden_eyes large_breasts long_hair male male_penetrating male_penetrating_female markings mature_female monster_rape naked nipples nude nude_female nude_male nudity pussy rape red_body red_skin restrained restraints reverse_suspended_congress rexxcraft sex sex_slave slim_waist spread_legs standing_sex straight straight_hair straight_sex tagme tattoo thrusting uriel_(darksiders) vagina vaginal vaginal_penetration vaginal_sex video white_hair wide_hips
angel angel_humanoid anus ass big_breasts big_butt bitterbunz bitterrbunz black_body black_feathers blush bodily_fluids breasts butt_grab cum cum_in_pussy cum_inside demon demon_humanoid demon_on_angel dialogue duo erection faceless_character faceless_male feathers female female_penetrated genital_fluids genitals hair halo hand_on_butt hazbin_hotel hi_res humanoid interspecies looking_pleasured lute_(hazbin_hotel) male male/female male_penetrating male_penetrating_female nipples open_mouth open_smile overweight overweight_male penetration penile penile_penetration penis_in_pussy pussy red_body sex smile speech_bubble sweat thick_thighs tongue tongue_out vaginal_fluids vaginal_penetration vivienne_medrano white_body white_feathers white_hair wings yellow_eyes
angel angel_humanoid anus ass big_breasts big_butt bitterbunz bitterrbunz black_body black_feathers blush bodily_fluids breasts butt_grab cum cum_in_pussy cum_inside demon demon_humanoid demon_on_angel dialogue duo erection faceless_character faceless_male feathers female female_penetrated genital_fluids genitals hair halo hand_on_butt hazbin_hotel hi_res humanoid interspecies looking_pleasured lute_(hazbin_hotel) male male/female male_penetrating male_penetrating_female nipples open_mouth open_smile overweight overweight_male penetration penile penile_penetration penis_in_pussy pussy red_body sex smile speech_bubble sweat thick_thighs tongue tongue_out vaginal_fluids vaginal_penetration vivienne_medrano white_body white_feathers white_hair wings yellow_eyes
adam_(hazbin_hotel) angel angel_humanoid ass balls blush bodily_fluids breasts clothed clothing cum cum_in_pussy cum_inside demon demon_humanoid demon_on_angel dialogue duo empty_eyes english_text faceless_character faceless_female faekeout fangs female female_penetrated genital_fluids genitals hair halo hazbin_hotel hi_res horn humanoid looking_pleasured male male/female male_penetrating male_penetrating_female nude open_mouth partially_clothed penetration penile penile_penetration penis penis_in_pussy profanity sex speech_bubble stand_and_carry_position standing standing_sex tail teeth text thick_thighs vaginal_penetration vaginal_penetration wings yellow_eyes
adam_(hazbin_hotel) angel angel_humanoid ass balls blush bodily_fluids breasts clothed clothing cum cum_in_pussy cum_inside demon demon_humanoid demon_on_angel dialogue duo empty_eyes english_text faceless_character faceless_female faekeout fangs female female_penetrated genital_fluids genitals hair halo hazbin_hotel hi_res horn humanoid looking_pleasured male male/female male_penetrating male_penetrating_female nude open_mouth partially_clothed penetration penile penile_penetration penis penis_in_pussy profanity sex speech_bubble stand_and_carry_position standing standing_sex tail teeth text thick_thighs vaginal_penetration vaginal_penetration wings yellow_eyes
angel bad_ending big_penis breasts choking cum cum_in_mouth cum_in_pussy cum_inside demon demon_on_angel duo erection female female_penetrated grey_body hair hazbin_hotel interspecies kyh_hkun male male/female male_penetrating male_penetrating_female male_pov missionary_position muscular muscular_male nipples nude open_mouth open_smile orgasm orgasm_face partial_male penetration penis_in_pussy pleasure_face prostitution pussy pussy_juice red_body rough_sex saliva sex short_hair smile stomach_bulge straight tears teeth vaggie_(hazbin_hotel) vaginal_penetration vein veiny_penis white_hair
angel bad_ending big_penis breasts choking cum cum_in_mouth cum_in_pussy cum_inside demon demon_on_angel duo erection female female_penetrated grey_body hair hazbin_hotel interspecies kyh_hkun male male/female male_penetrating male_penetrating_female male_pov missionary_position muscular muscular_male nipples nude open_mouth open_smile orgasm orgasm_face partial_male penetration penis_in_pussy pleasure_face prostitution pussy pussy_juice red_body rough_sex saliva sex short_hair smile stomach_bulge straight tears teeth vaggie_(hazbin_hotel) vaginal_penetration vein veiny_penis white_hair