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3:2 6+boys 7boys affinity_(bayonetta) angel anthro ass ass_bigger_than_head back_muscles background_text backsack balls bandana bayonetta bayonetta_(series) big_ass big_butt big_penis black_fur blue_eyes blush blush_lines bodily_fluids chains clothing crossover detailed_background dialogue domestic_cat dripping eastern_and_western_character enochian felid feline felis femboy genital_fluids genitals glistening glistening_body gold_(metal) gold_band gold_chain gold_jewelry group gun handgun heart_reaction heart_symbol hearts_around_body hearts_around_head heaven helluva_boss hi_res holding_gun holding_object holding_weapon huge_ass imminent_sex imp inviting_to_sex jewelry kerchief large_ass large_penis latex latex_clothing latex_skinsuit longhair love love_is_blue_(bayonetta) male male/male male_only mammal megami_tensei monana-yo1 morgana_(persona) moxxie_(helluva_boss) multiple_boys nature nature_background penis persona persona_(series) persona_5 pistol pistol_holster pistol_out pistols precum precum_drip ranged_weapon red_skin scarborough_fair_(bayonetta) shocked skinsuit sky smile smiling_at_viewer smirk smirking_at_partner smirking_at_viewer sparkles surrounded surrounded_by_penis surrounded_by_penises tight_clothing weapon wobbly yaoi yellow_sclera
3:2 6+boys 7boys affinity_(bayonetta) angel anthro ass ass_bigger_than_head back_muscles background_text backsack balls bandana bayonetta bayonetta_(series) big_ass big_butt big_penis black_fur blue_eyes blush blush_lines bodily_fluids chains clothing crossover detailed_background dialogue domestic_cat dripping eastern_and_western_character enochian felid feline felis femboy genital_fluids genitals glistening glistening_body gold_(metal) gold_band gold_chain gold_jewelry group gun handgun heart_reaction heart_symbol hearts_around_body hearts_around_head heaven helluva_boss hi_res holding_gun holding_object holding_weapon huge_ass imminent_sex imp inviting_to_sex jewelry kerchief large_ass large_penis latex latex_clothing latex_skinsuit longhair love love_is_blue_(bayonetta) male male/male male_only mammal megami_tensei monana-yo1 morgana_(persona) moxxie_(helluva_boss) multiple_boys nature nature_background penis persona persona_(series) persona_5 pistol pistol_holster pistol_out pistols precum precum_drip ranged_weapon red_skin scarborough_fair_(bayonetta) shocked skinsuit sky smile smiling_at_viewer smirk smirking_at_partner smirking_at_viewer sparkles surrounded surrounded_by_penis surrounded_by_penises tight_clothing weapon wobbly yaoi yellow_sclera
2boys actor anal anal_sex angel armpit_hair artist_name artist_signature ass bara bed biceps big_penis black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes completely_nude cum cumshot dark_hair dean_winchester depairt dialogue duo ejaculation enochian enochian_tattoo enochian_text erect_penis erection gay gay_anal gay_sex green_eyes human in_character jensen_ackles light-skinned_male light_skin looking_at_partner looking_pleasured male male/male male_only male_penetrated male_penetrating male_penetrating_male male_pubic_hair misha_collins muscles muscular muscular_male naked naked_male nipples nude nude_male occult_symbol on_bed on_top orgasm orgasm_face pecs penetration penile_penetration penis penis_in_ass pentagram pubic_hair reverse_cowgirl_position sex speech supernatural_(series) tattoo text yaoi
2boys actor anal anal_sex angel armpit_hair artist_name artist_signature ass bara bed biceps big_penis black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes completely_nude cum cumshot dark_hair dean_winchester depairt dialogue duo ejaculation enochian enochian_tattoo enochian_text erect_penis erection gay gay_anal gay_sex green_eyes human in_character jensen_ackles light-skinned_male light_skin looking_at_partner looking_pleasured male male/male male_only male_penetrated male_penetrating male_penetrating_male male_pubic_hair misha_collins muscles muscular muscular_male naked naked_male nipples nude nude_male occult_symbol on_bed on_top orgasm orgasm_face pecs penetration penile_penetration penis penis_in_ass pentagram pubic_hair reverse_cowgirl_position sex speech supernatural_(series) tattoo text yaoi
3:2 6+boys 7boys affinity_(bayonetta) angel anthro ass ass_bigger_than_head back_muscles background_text backsack balls bandana bayonetta bayonetta_(cosplay) bayonetta_(series) big_ass big_penis black_fur blue_eyes blush blush_lines chains clothing cosplay crossover detailed_background domestic_cat eastern_and_western_character enochian felid feline felis femboy genitals glistening glistening_body gold_(metal) gold_chain gold_jewelry group gun heart_reaction heart_symbol hearts_around_body heaven helluva_boss hi_res holding_gun holding_object holding_weapon huge_ass imminent_sex imp jewelry kerchief large_ass large_penis latex latex_clothing latex_skinsuit longhair love love_is_blue_(bayonetta) male male/male male_only mammal megami_tensei monana-yo1 morgana_(persona) moxxie_(helluva_boss) multiple_boys nature nature_background penis persona persona_(series) persona_5 pistol pistol_out pistols ranged_weapon red_skin scarborough_fair_(bayonetta) shocked skinsuit sky tight_clothing weapon wobbly yaoi yellow_sclera
3:2 6+boys 7boys affinity_(bayonetta) angel anthro ass ass_bigger_than_head back_muscles background_text backsack balls bandana bayonetta bayonetta_(cosplay) bayonetta_(series) big_ass big_penis black_fur blue_eyes blush blush_lines chains clothing cosplay crossover detailed_background domestic_cat eastern_and_western_character enochian felid feline felis femboy genitals glistening glistening_body gold_(metal) gold_chain gold_jewelry group gun heart_reaction heart_symbol hearts_around_body heaven helluva_boss hi_res holding_gun holding_object holding_weapon huge_ass imminent_sex imp jewelry kerchief large_ass large_penis latex latex_clothing latex_skinsuit longhair love love_is_blue_(bayonetta) male male/male male_only mammal megami_tensei monana-yo1 morgana_(persona) moxxie_(helluva_boss) multiple_boys nature nature_background penis persona persona_(series) persona_5 pistol pistol_out pistols ranged_weapon red_skin scarborough_fair_(bayonetta) shocked skinsuit sky tight_clothing weapon wobbly yaoi yellow_sclera
2boys actor anal anal_sex angel animated animated animation armpit_hair artist_name artist_signature ass bara bed biceps big_penis black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes completely_nude cum cumshot dark_hair dean_winchester depairt dialogue duo ejaculation enochian enochian_tattoo enochian_text erect_penis erection gay gay_anal gay_sex green_eyes human in_character jensen_ackles light-skinned_male light_skin looking_at_partner looking_pleasured male male/male male_only male_penetrated male_penetrating male_penetrating_male male_pubic_hair misha_collins muscles muscular muscular_male naked naked_male nipples nude nude_male occult_symbol on_bed on_top orgasm orgasm_face pecs penetration penile_penetration penis penis_in_ass pentagram pubic_hair reverse_cowgirl_position sex speech supernatural_(series) tagme tattoo text video yaoi
2boys actor anal anal_sex angel animated animated animation armpit_hair artist_name artist_signature ass bara bed biceps big_penis black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes completely_nude cum cumshot dark_hair dean_winchester depairt dialogue duo ejaculation enochian enochian_tattoo enochian_text erect_penis erection gay gay_anal gay_sex green_eyes human in_character jensen_ackles light-skinned_male light_skin looking_at_partner looking_pleasured male male/male male_only male_penetrated male_penetrating male_penetrating_male male_pubic_hair misha_collins muscles muscular muscular_male naked naked_male nipples nude nude_male occult_symbol on_bed on_top orgasm orgasm_face pecs penetration penile_penetration penis penis_in_ass pentagram pubic_hair reverse_cowgirl_position sex speech supernatural_(series) tagme tattoo text video yaoi
2boys actor almost_kissing angel armpit_hair artist_signature ass bara black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes cuddling dark_hair dean_winchester duo enochian enochian_tattoo enochian_text freckles gay half-dressed half_naked human in_character jensen_ackles kneeling licieoic light-skinned_male light_skin looking_pleasured male male/male male_only misha_collins nipples occult_symbol pants pants_down pentagram realistic supernatural_(series) tattoo yaoi
2boys actor almost_kissing angel armpit_hair artist_signature ass bara black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes cuddling dark_hair dean_winchester duo enochian enochian_tattoo enochian_text freckles gay half-dressed half_naked human in_character jensen_ackles kneeling licieoic light-skinned_male light_skin looking_pleasured male male/male male_only misha_collins nipples occult_symbol pants pants_down pentagram realistic supernatural_(series) tattoo yaoi
2boys abs actor angel artist_signature balls ballsack bara beard_stubble biceps big_penis biting_lip biting_own_lip black_hair blowjob brown_hair castiel castiel_(supernatural) celebrity chest_hair chest_tattoo closed_eyes cum cum_in_mouth dark_hair dean_winchester duo enochian enochian_tattoo enochian_text erect_penis erection facial_hair fellatio freckles gay gay_sex hairy_chest half-dressed half_naked hand_around_neck holding_hands human in_character jensen_ackles kneeling light-skinned_male light_skin looking_pleasured male male/male male_only male_penetrated male_penetrating male_penetrating_male misha_collins muscles muscular muscular_male nipple_play nipples occult_symbol open open_pants oral oral_penetration oral_sex orgasm orgasm_face pants pants_down pecs penis penis_in_mouth pentagram pubic_hair saliva saliva_on_penis sex shirt shirtless sircatherineafterdark standing standing_position stubble supernatural_(series) tattoo yaoi
2boys abs actor angel artist_signature balls ballsack bara beard_stubble biceps big_penis biting_lip biting_own_lip black_hair blowjob brown_hair castiel castiel_(supernatural) celebrity chest_hair chest_tattoo closed_eyes cum cum_in_mouth dark_hair dean_winchester duo enochian enochian_tattoo enochian_text erect_penis erection facial_hair fellatio freckles gay gay_sex hairy_chest half-dressed half_naked hand_around_neck holding_hands human in_character jensen_ackles kneeling light-skinned_male light_skin looking_pleasured male male/male male_only male_penetrated male_penetrating male_penetrating_male misha_collins muscles muscular muscular_male nipple_play nipples occult_symbol open open_pants oral oral_penetration oral_sex orgasm orgasm_face pants pants_down pecs penis penis_in_mouth pentagram pubic_hair saliva saliva_on_penis sex shirt shirtless sircatherineafterdark standing standing_position stubble supernatural_(series) tattoo yaoi
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1boy angel armpit_hair asleep bara bed biceps black_hair blanket castiel castiel_(supernatural) closed_eyes dark_hair enochian enochian_tattoo enochian_text in_bed licieoic light-skinned_male light_skin lying lying_down lying_on_back male male_only male_pubic_hair misha_collins muscles muscular muscular_male naked naked_male nipples nude nude_male pecs pillow pubic_hair realistic sleep sleeping solo solo_male supernatural_(series) tattoo
1boy abs actor angel artist_signature bara beard_stubble belt biceps black_hair blue_eyes castiel castiel_(supernatural) celebrity dark_hair enochian enochian_tattoo enochian_text facial_hair half-dressed in_character licieoic light-skinned_male light_skin looking_at_viewer male male_only misha_collins muscles muscular muscular_male necktie nipples open_shirt pants realistic shirt solo solo_male standing standing_position stubble supernatural_(series) tattoo undressing
1boy abs actor angel artist_signature bara beard_stubble belt biceps black_hair blue_eyes castiel castiel_(supernatural) celebrity dark_hair enochian enochian_tattoo enochian_text facial_hair half-dressed in_character licieoic light-skinned_male light_skin looking_at_viewer male male_only misha_collins muscles muscular muscular_male necktie nipples open_shirt pants realistic shirt solo solo_male standing standing_position stubble supernatural_(series) tattoo undressing
2boys actor anal anal_sex anal_sex angel artist_signature ass bara beard black_hair brown_hair castiel castiel_(supernatural) celebrity completely_nude dark_hair dean_winchester duo enochian enochian_tattoo enochian_text facial_hair gay gay_anal gay_sex holding_hands human in_character jensen_ackles licieoic light-skinned_male light_skin lying lying_down lying_on_partner lying_on_person male male/male male_only male_penetrated male_penetrating male_penetrating_male misha_collins naked naked_male nude nude_male penetration penile_penetration penis_in_ass realistic sex supernatural_(series) tattoo yaoi
2boys actor anal anal_sex anal_sex angel artist_signature ass bara beard black_hair brown_hair castiel castiel_(supernatural) celebrity completely_nude dark_hair dean_winchester duo enochian enochian_tattoo enochian_text facial_hair gay gay_anal gay_sex holding_hands human in_character jensen_ackles licieoic light-skinned_male light_skin lying lying_down lying_on_partner lying_on_person male male/male male_only male_penetrated male_penetrating male_penetrating_male misha_collins naked naked_male nude nude_male penetration penile_penetration penis_in_ass realistic sex supernatural_(series) tattoo yaoi
2boys actor anal anal_sex anal_sex angel artist_signature ass bara black_hair brown_hair castiel castiel_(supernatural) celebrity closed_eyes dark_hair dean_winchester duo enochian enochian_tattoo enochian_text freckles gay gay_anal gay_sex holding_partner human in_character jensen_ackles licieoic light-skinned_male light_skin looking_at_partner lying lying_down lying_on_stomach male male/male male_only male_penetrated male_penetrating male_penetrating_male misha_collins nipples penetration penile_penetration penis_in_ass realistic sex standing supernatural_(series) tattoo yaoi
2boys actor anal anal_sex anal_sex angel artist_signature ass bara black_hair brown_hair castiel castiel_(supernatural) celebrity closed_eyes dark_hair dean_winchester duo enochian enochian_tattoo enochian_text freckles gay gay_anal gay_sex holding_partner human in_character jensen_ackles licieoic light-skinned_male light_skin looking_at_partner lying lying_down lying_on_stomach male male/male male_only male_penetrated male_penetrating male_penetrating_male misha_collins nipples penetration penile_penetration penis_in_ass realistic sex standing supernatural_(series) tattoo yaoi
2boys actor angel artist_signature ass_grab bara beard black_hair brown_hair bulge castiel castiel_(supernatural) celebrity closed_eyes cuddling dark_hair dean_winchester duo enochian enochian_tattoo enochian_text facial_hair freckles gay grabbing_ass half-dressed half_naked head_on_chest holding_partner human in_character jensen_ackles kneeling licieoic light-skinned_male light_skin looking_happy male male/male male_only misha_collins nipples romantic sitting supernatural_(series) tattoo underwear yaoi
2boys actor angel artist_signature ass_grab bara beard black_hair brown_hair bulge castiel castiel_(supernatural) celebrity closed_eyes cuddling dark_hair dean_winchester duo enochian enochian_tattoo enochian_text facial_hair freckles gay grabbing_ass half-dressed half_naked head_on_chest holding_partner human in_character jensen_ackles kneeling licieoic light-skinned_male light_skin looking_happy male male/male male_only misha_collins nipples romantic sitting supernatural_(series) tattoo underwear yaoi
1boy actor angel artist_signature bara biceps black_hair bulge bulge_through_clothing castiel castiel_(supernatural) celebrity dark_hair enochian enochian_tattoo enochian_text half-dressed half_naked human human_only in_character licieoic light-skinned_male light_skin male male_only misha_collins muscles muscular muscular_male nipples outdoors outside pecs realistic standing standing_position supernatural_(series) tattoo underwear
1boy actor angel artist_signature bara biceps black_hair bulge bulge_through_clothing castiel castiel_(supernatural) celebrity dark_hair enochian enochian_tattoo enochian_text half-dressed half_naked human human_only in_character licieoic light-skinned_male light_skin male male_only misha_collins muscles muscular muscular_male nipples outdoors outside pecs realistic standing standing_position supernatural_(series) tattoo underwear
2boys abs actor angel armchair artist_signature bara beard_stubble biceps black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes dark_hair dean_winchester duo enochian enochian_tattoo enochian_text facial_hair freckles gay hand_around_waist human human_only in_character jensen_ackles licieoic light_skin light_skinned_male looking_pleasured male male/male male_only misha_collins muscles muscular muscular_male nipples occult_symbol pants pecs pentagram realistic shirtless sitting sitting_in_chair smile smiling stubble supernatural_(series) tattoo tattoos tight_clothing tight_pants wings_tattoo
2boys abs actor angel armchair artist_signature bara beard_stubble biceps black_hair brown_hair castiel castiel_(supernatural) celebrity chest_tattoo closed_eyes dark_hair dean_winchester duo enochian enochian_tattoo enochian_text facial_hair freckles gay hand_around_waist human human_only in_character jensen_ackles licieoic light_skin light_skinned_male looking_pleasured male male/male male_only misha_collins muscles muscular muscular_male nipples occult_symbol pants pecs pentagram realistic shirtless sitting sitting_in_chair smile smiling stubble supernatural_(series) tattoo tattoos tight_clothing tight_pants wings_tattoo
2boys abs actor angel artist_signature balls ballsack bara beard_stubble biceps big_penis black_hair blowjob brown_hair castiel castiel_(supernatural) celebrity chest_hair closed_eyes cum cum_in_mouth dark_hair dean_winchester duo enochian enochian_tattoo enochian_text erect_penis erection facial_hair fellatio freckles gay gay_sex grabbing_penis green_eyes hairy_chest hand_on_head human in_character jensen_ackles kneeling licking licking_penis light-skinned_male light_skin looking_at_partner looking_pleasured male_only male_pubic_hair misha_collins muscles muscular muscular_male necktie nipples open_shirt oral oral_penetration oral_sex orgasm orgasm_face pants pants_down pants_open pecs penis penis_grab precum pubic_hair shirtless sircatherineafterdark speech speech_bubble standing standing_position stubble supernatural_(series) tattoo text text_bubble underwear yaoi
2boys abs actor angel artist_signature balls ballsack bara beard_stubble biceps big_penis black_hair blowjob brown_hair castiel castiel_(supernatural) celebrity chest_hair closed_eyes cum cum_in_mouth dark_hair dean_winchester duo enochian enochian_tattoo enochian_text erect_penis erection facial_hair fellatio freckles gay gay_sex grabbing_penis green_eyes hairy_chest hand_on_head human in_character jensen_ackles kneeling licking licking_penis light-skinned_male light_skin looking_at_partner looking_pleasured male_only male_pubic_hair misha_collins muscles muscular muscular_male necktie nipples open_shirt oral oral_penetration oral_sex orgasm orgasm_face pants pants_down pants_open pecs penis penis_grab precum pubic_hair shirtless sircatherineafterdark speech speech_bubble standing standing_position stubble supernatural_(series) tattoo text text_bubble underwear yaoi
1boy abs actor angel artist_signature bara biceps black_hair castiel castiel_(supernatural) celebrity dark_hair enochian enochian_tattoo enochian_text in_character licieoic light-skinned_male light_skin looking_down male male_only misha_collins muscles muscular muscular_male nipples pants pecs pulling_shirt realistic shirt shirt_pull smile smiling solo solo_male standing standing_position supernatural_(series) tattoo undressing undressing_self
1boy abs actor angel artist_signature bara biceps black_hair castiel castiel_(supernatural) celebrity dark_hair enochian enochian_tattoo enochian_text in_character licieoic light-skinned_male light_skin looking_down male male_only misha_collins muscles muscular muscular_male nipples pants pecs pulling_shirt realistic shirt shirt_pull smile smiling solo solo_male standing standing_position supernatural_(series) tattoo undressing undressing_self