sideshow_bob best from all time -animated

Time frame

Tags

sideshow bob

2022 against_glass ass_on_glass ass_squish big_ass big_breasts big_butt butt_squish detailed_background digital_media_(artwork) edit fat_ass female huge_ass huge_butt male masterj291 mooning selma_bouvier sideshow_bob the_simpsons
2022 against_glass ass_on_glass ass_squish big_ass big_breasts big_butt butt_squish detailed_background digital_media_(artwork) edit fat_ass female huge_ass huge_butt male masterj291 mooning selma_bouvier sideshow_bob the_simpsons
clothed clothed_male clothing cum cumshot dialogue ejaculation erect_penis erection machojuice male male_only masturbation penis robert_terwilliger sideshow_bob solo solo_focus solo_male swear the_simpsons
clothed clothed_male clothing cum cumshot dialogue ejaculation erect_penis erection machojuice male male_only masturbation penis robert_terwilliger sideshow_bob solo solo_focus solo_male swear the_simpsons
2boys anal anal_penetration anal_sex ass big_feet blanket_grab circumcised circumcision_scar clown drool_string erection gay gloves green_hair hand_on_cheek head_rest krusty_the_clown legs_held_open long_feet lying_on_side machojuice male male_only multiple_males multiple_penises on_bed penis_size_difference precum_drip precum_string red_hair robert_terwilliger sideshow_bob spread_legs sweat sweating the_simpsons tongue_out yaoi yellow_skin
2boys anal anal_penetration anal_sex ass big_feet blanket_grab circumcised circumcision_scar clown drool_string erection gay gloves green_hair hand_on_cheek head_rest krusty_the_clown legs_held_open long_feet lying_on_side machojuice male male_only multiple_males multiple_penises on_bed penis_size_difference precum_drip precum_string red_hair robert_terwilliger sideshow_bob spread_legs sweat sweating the_simpsons tongue_out yaoi yellow_skin
2boys anal anal_penetration anal_sex angry_sex big_feet big_hair blush bottomless bowtie cartoony cigarette cloud clown clown_makeup cum_in_ass cum_on_face cum_on_hair gay gloves green_hair instant_loss_2koma krusty_the_clown laughing long_feet machojuice male male_only mating_press missionary_position mouth_open necklace one_eye_closed receiving_on_back red_hair red_nose robert_terwilliger sideshow_bob skirt_around_belly smoking the_simpsons thrusting_into_ass untied_tie yaoi yellow_skin
2boys anal anal_penetration anal_sex angry_sex big_feet big_hair blush bottomless bowtie cartoony cigarette cloud clown clown_makeup cum_in_ass cum_on_face cum_on_hair gay gloves green_hair instant_loss_2koma krusty_the_clown laughing long_feet machojuice male male_only mating_press missionary_position mouth_open necklace one_eye_closed receiving_on_back red_hair red_nose robert_terwilliger sideshow_bob skirt_around_belly smoking the_simpsons thrusting_into_ass untied_tie yaoi yellow_skin
artist_signature blush color gay krusty_the_clown machojuice male_only sideshow_bob the_simpsons yaoi
artist_signature blush color gay krusty_the_clown machojuice male_only sideshow_bob the_simpsons yaoi
angry_face bara dominant dominant_male k_jukesnsfw kidde_jukes male_only muscle_tone muscles panting robert_terwilliger sideshow_bob solo_male the_simpsons thick_penis
angry_face bara dominant dominant_male k_jukesnsfw kidde_jukes male_only muscle_tone muscles panting robert_terwilliger sideshow_bob solo_male the_simpsons thick_penis
2boys anal anal_penetration anal_sex big_feet cartoony chubby circumcised circumcision_scar clown clown_makeup cum_in_ass cum_while_penetrated deep_penetration eyes_closed gay gloves green_hair half-closed_eyes holding_head holding_wrist kissing knife krusty_the_clown legs_held_open machojuice male male_only missionary_position multiple_males multiple_penises nude red_hair robert_terwilliger sideshow_bob spread_legs sweat the_simpsons trembling veiny_penis yaoi yellow_skin
2boys anal anal_penetration anal_sex big_feet cartoony chubby circumcised circumcision_scar clown clown_makeup cum_in_ass cum_while_penetrated deep_penetration eyes_closed gay gloves green_hair half-closed_eyes holding_head holding_wrist kissing knife krusty_the_clown legs_held_open machojuice male male_only missionary_position multiple_males multiple_penises nude red_hair robert_terwilliger sideshow_bob spread_legs sweat the_simpsons trembling veiny_penis yaoi yellow_skin
2boys black_pubic_hair blowjob cheek_bulge clothed cock_gobble cock_hungry cum_hungry deepthroat erection_under_clothes faggotrat feet_out_of_frame fellatio gay giving_head going_down_on half-closed_eyes legs_held_open licking_penis looking_to_the_side male male_only mouthful one_eye_closed oral oral_sex penis_in_mouth precum_bubble red_hair robert_terwilliger saliva_drip sex sideshow_bob spread_legs sucking_off sweatdrops the_simpsons tongue_out veiny_penis yaoi yellow_skin
2boys black_pubic_hair blowjob cheek_bulge clothed cock_gobble cock_hungry cum_hungry deepthroat erection_under_clothes faggotrat feet_out_of_frame fellatio gay giving_head going_down_on half-closed_eyes legs_held_open licking_penis looking_to_the_side male male_only mouthful one_eye_closed oral oral_sex penis_in_mouth precum_bubble red_hair robert_terwilliger saliva_drip sex sideshow_bob spread_legs sucking_off sweatdrops the_simpsons tongue_out veiny_penis yaoi yellow_skin
abuse color girl huge_cock maggie_simpson rape sbb sideshow_bob the_simpsons
abuse color girl huge_cock maggie_simpson rape sbb sideshow_bob the_simpsons
1boy blush buttplug buttplug_tail collar cum cum_in_bowl disembodied_hand english_text erection faggotrat finger_in_mouth gay kneeling leash male male_only nude open_mouth penis petplay robert_terwilliger saliva sideshow_bob solo submissive text the_simpsons yaoi
1boy blush buttplug buttplug_tail collar cum cum_in_bowl disembodied_hand english_text erection faggotrat finger_in_mouth gay kneeling leash male male_only nude open_mouth penis petplay robert_terwilliger saliva sideshow_bob solo submissive text the_simpsons yaoi
1boy after_anal after_sex anal blush buttplug buttplug_tail cuffs cum cum_in_ass cum_inside disembodied_penis faggotrat gay half-closed_eyes male male_only overflow penis petplay presenting presenting_hindquarters robert_terwilliger sideshow_bob simple_background solo spread_legs spreading the_simpsons yaoi
1boy after_anal after_sex anal blush buttplug buttplug_tail cuffs cum cum_in_ass cum_inside disembodied_penis faggotrat gay half-closed_eyes male male_only overflow penis petplay presenting presenting_hindquarters robert_terwilliger sideshow_bob simple_background solo spread_legs spreading the_simpsons yaoi
biting_own_lip erection exposed_penis faggotrat flying_sweatdrops horny looking_at_penis male male_only penis precum_bubble red_hair robert_terwilliger sideshow_bob skirt slightly_chubby solo the_simpsons veiny_penis
biting_own_lip erection exposed_penis faggotrat flying_sweatdrops horny looking_at_penis male male_only penis precum_bubble red_hair robert_terwilliger sideshow_bob skirt slightly_chubby solo the_simpsons veiny_penis
2boys age_difference alternate_hair_color anal_fingering anal_penetration arms_tied balls bart_simpson blowjob blowjob_face bondage bottomless boy_rape brown_hair clothing cock_gobble cock_hungry cum_hungry erection fellatio finger_fuck fingering forced_yaoi gay giving_head going_down_on hate_sex human human_only kneeling_oral_position leg_lift leg_on_shoulder legs_held_open lonleyboy101 male_rape_victim mouth_open older_dom_younger_sub older_man_and_younger_boy older_penetrating_younger open_mouth oral penis penis_in_mouth purple_shirt rape red_hair reverse_forced_oral robert_terwilliger shirt_up sideshow_bob socks spiked_hair spread_legs sucking_off the_simpsons tied_to_pole tied_up tongue tongue_out turquoise_background wide_eyed yaoi yellow_hair yellow_skin younger_penetrating_older
2boys age_difference alternate_hair_color anal_fingering anal_penetration arms_tied balls bart_simpson blowjob blowjob_face bondage bottomless boy_rape brown_hair clothing cock_gobble cock_hungry cum_hungry erection fellatio finger_fuck fingering forced_yaoi gay giving_head going_down_on hate_sex human human_only kneeling_oral_position leg_lift leg_on_shoulder legs_held_open lonleyboy101 male_rape_victim mouth_open older_dom_younger_sub older_man_and_younger_boy older_penetrating_younger open_mouth oral penis penis_in_mouth purple_shirt rape red_hair reverse_forced_oral robert_terwilliger shirt_up sideshow_bob socks spiked_hair spread_legs sucking_off the_simpsons tied_to_pole tied_up tongue tongue_out turquoise_background wide_eyed yaoi yellow_hair yellow_skin younger_penetrating_older
20th_century_fox 2boys anal banhaibao blue_hair chubby chubby_male clown cum cum_in_ass digital_media_(artwork) fat_man gay krusty_the_clown overweight overweight_male penis sideshow_bob tagme the_simpsons uncensored yaoi yellow_skin
20th_century_fox 2boys anal banhaibao blue_hair chubby chubby_male clown cum cum_in_ass digital_media_(artwork) fat_man gay krusty_the_clown overweight overweight_male penis sideshow_bob tagme the_simpsons uncensored yaoi yellow_skin
20th_century_fox 2boys anon banhaibao cum cum_on_feet feet footjob gay prison_uniform prisoner red_hair sideshow_bob skinny solo tagme the_simpsons toony yaoi yellow_skin
20th_century_fox 2boys anon banhaibao cum cum_on_feet feet footjob gay prison_uniform prisoner red_hair sideshow_bob skinny solo tagme the_simpsons toony yaoi yellow_skin
belt blowjob choker collar crossdressing gay human justcartoondicks.com nipples oral oral_sex selfie sideshow_bob stockings the_simpsons yellow_body yellow_skin
belt blowjob choker collar crossdressing gay human justcartoondicks.com nipples oral oral_sex selfie sideshow_bob stockings the_simpsons yellow_body yellow_skin
2boys anal cecil_terwilliger dahlshita male_only penis robert_terwilliger sideshow_bob the_simpsons yaoi
2boys anal cecil_terwilliger dahlshita male_only penis robert_terwilliger sideshow_bob the_simpsons yaoi
2010 2boys balls big_feet bone color cum cum_in_mouth cum_on_face curved_cock erect_nipples erection face_fucking fellatio flaccid_penis gay green_hair half-closed_eyes holding_head indoors insertion irrumatio long_feet long_penis male male_only melvin_van_horne mostly_nude multiple_males necklace nude oral oral_rape partially_retracted_foreskin penis penis_size_difference pubic_hair red_hair robert_terwilliger shoes side_view sideshow_bob sideshow_mel testicles the_simpsons thin_penis uncut victor_hodge wide_eyes yaoi yellow_skin
2010 2boys balls big_feet bone color cum cum_in_mouth cum_on_face curved_cock erect_nipples erection face_fucking fellatio flaccid_penis gay green_hair half-closed_eyes holding_head indoors insertion irrumatio long_feet long_penis male male_only melvin_van_horne mostly_nude multiple_males necklace nude oral oral_rape partially_retracted_foreskin penis penis_size_difference pubic_hair red_hair robert_terwilliger shoes side_view sideshow_bob sideshow_mel testicles the_simpsons thin_penis uncut victor_hodge wide_eyes yaoi yellow_skin
2boys brothers cecil_terwilliger color dirty_blonde_hair erect_penis gay half-closed_eyes hand_on_arm hand_on_shoulder human imminent_anal imminent_penetration incest legs_around_waist lying_on_bed male male_only missionary_position multiple_males naughty_face nude on_back red_hair robert_terwilliger side_view sideshow_bob spoken_heart tagme tattoos the_simpsons yaoi yellow_skin zeriara
2boys brothers cecil_terwilliger color dirty_blonde_hair erect_penis gay half-closed_eyes hand_on_arm hand_on_shoulder human imminent_anal imminent_penetration incest legs_around_waist lying_on_bed male male_only missionary_position multiple_males naughty_face nude on_back red_hair robert_terwilliger side_view sideshow_bob spoken_heart tagme tattoos the_simpsons yaoi yellow_skin zeriara
2boys blood brothers cecil_terwilliger clenched_teeth clothes color crying_with_eyes_open cum cum_in_nose dahlshita erection gay head_out_of_frame incest male male_only multiple_boys nasal_penetration pants_down red_hair robert_terwilliger sideshow_bob sweater_vest tears the_simpsons veiny_penis violence what yaoi
2boys blood brothers cecil_terwilliger clenched_teeth clothes color crying_with_eyes_open cum cum_in_nose dahlshita erection gay head_out_of_frame incest male male_only multiple_boys nasal_penetration pants_down red_hair robert_terwilliger sideshow_bob sweater_vest tears the_simpsons veiny_penis violence what yaoi
2boys cecil_terwilliger cum cum_in_ear cum_inside dahlshita ear_fuck ear_penetration male_only robert_terwilliger sideshow_bob the_simpsons what yaoi yellow_skin
2boys cecil_terwilliger cum cum_in_ear cum_inside dahlshita ear_fuck ear_penetration male_only robert_terwilliger sideshow_bob the_simpsons what yaoi yellow_skin
2boys bart_simpson bath bathtub blonde_hair blowjob closed_eyes cock_gobble cock_hungry color cum_hungry erect_nipple erect_nipples eriath fellatio gay gay_blowjob gay_sex giving_head going_down_on head_down_ass_up human imminent_orgasm knob_polishing male male_only mouth_open multiple_males no_visible_genitalia nude older_man_and_younger_boy oral_sex orgasm_face red_hair robert_terwilliger side_view sideshow_bob sucking_off tagme the_simpsons yaoi yellow_skin
2boys bart_simpson bath bathtub blonde_hair blowjob closed_eyes cock_gobble cock_hungry color cum_hungry erect_nipple erect_nipples eriath fellatio gay gay_blowjob gay_sex giving_head going_down_on head_down_ass_up human imminent_orgasm knob_polishing male male_only mouth_open multiple_males no_visible_genitalia nude older_man_and_younger_boy oral_sex orgasm_face red_hair robert_terwilliger side_view sideshow_bob sucking_off tagme the_simpsons yaoi yellow_skin
3boys angry being_watched blonde_hair blood_stain bottomless brothers cecil_terwilliger chabichou chief_wiggum clancy_wiggum cum_stain donut erection graffiti handjob hands_behind_head human incest jail_cell male male_only motion_blur multiple_males naughty_face pants_down red_hair robert_terwilliger sex sideshow_bob stroking_penis tagme the_simpsons voyeur watching
3boys angry being_watched blonde_hair blood_stain bottomless brothers cecil_terwilliger chabichou chief_wiggum clancy_wiggum cum_stain donut erection graffiti handjob hands_behind_head human incest jail_cell male male_only motion_blur multiple_males naughty_face pants_down red_hair robert_terwilliger sex sideshow_bob stroking_penis tagme the_simpsons voyeur watching
2010 2boys armpit_hair artist_signature chubby clothes clown cmnm color erection gay gloves green_hair half-closed_eyes human indoors krusty_the_clown long_feet looking_sick male male_only mirror multiple_males mwaters naked_with_shoes_on necklace nude_male public_restroom red_hair red_nose robert_terwilliger saliva_drip sideshow_bob sink skirt_removed standing tagme the_simpsons unknown_artist washing_another washing_body yaoi yellow_skin
2010 2boys armpit_hair artist_signature chubby clothes clown cmnm color erection gay gloves green_hair half-closed_eyes human indoors krusty_the_clown long_feet looking_sick male male_only mirror multiple_males mwaters naked_with_shoes_on necklace nude_male public_restroom red_hair red_nose robert_terwilliger saliva_drip sideshow_bob sink skirt_removed standing tagme the_simpsons unknown_artist washing_another washing_body yaoi yellow_skin
20th_century_fox 20th_century_studios blood erection knife ladysomnambule lying male male_only open_mouth penis red_hair robert_terwilliger sideshow_bob solo the_simpsons window yellow_skin
20th_century_fox 20th_century_studios blood erection knife ladysomnambule lying male male_only open_mouth penis red_hair robert_terwilliger sideshow_bob solo the_simpsons window yellow_skin
4boys anal anal_penetration anal_sex cock_hungry color dark-skinned_male disembodied_penis dual_handjob erection front_view gay handjob holding_penis human insertion interracial legs_held_open looking_at_penis male male_only mouth_open multiple_males multiple_penises nipples nude penis penis_size_difference pubic_hair red_hair redpearl robert_terwilliger s sex sideshow_bob sitting_on_penis spread_legs sweat tagme the_simpsons veiny_penis yaoi yellow_skin
4boys anal anal_penetration anal_sex cock_hungry color dark-skinned_male disembodied_penis dual_handjob erection front_view gay handjob holding_penis human insertion interracial legs_held_open looking_at_penis male male_only mouth_open multiple_males multiple_penises nipples nude penis penis_size_difference pubic_hair red_hair redpearl robert_terwilliger s sex sideshow_bob sitting_on_penis spread_legs sweat tagme the_simpsons veiny_penis yaoi yellow_skin
2010 3boys anal anal_penetration anal_sex artist_signature beer_can bottomless cartoony closed_eyes clothed_male_nude_male clothes clown cmnm cock_gobble cock_hungry color cum cum_drinking cum_hungry cum_in_ass cum_in_mouth cum_while_penetrated dated facial_hair fellatio fuck_and_suck fucked_from_behind gay giving_head going_down_on green_hair hand_on_leg hand_on_neck hand_on_shoulder handjob_while_penetrated handjob_while_sucking hate_sex holding_head holding_penis human kissing krusty_the_clown long_feet male male_only malesub melvin_van_horne multiple_males nude oral oral_sex orgasm_from_anal orgasm_from_oral penis pillows red_hair robert_terwilliger sex side_view sideshow_bob sideshow_mel sitting spitroast suck_and_fuck sucking_off the_simpsons threesome toony yaoi yellow_skin
2010 3boys anal anal_penetration anal_sex artist_signature beer_can bottomless cartoony closed_eyes clothed_male_nude_male clothes clown cmnm cock_gobble cock_hungry color cum cum_drinking cum_hungry cum_in_ass cum_in_mouth cum_while_penetrated dated facial_hair fellatio fuck_and_suck fucked_from_behind gay giving_head going_down_on green_hair hand_on_leg hand_on_neck hand_on_shoulder handjob_while_penetrated handjob_while_sucking hate_sex holding_head holding_penis human kissing krusty_the_clown long_feet male male_only malesub melvin_van_horne multiple_males nude oral oral_sex orgasm_from_anal orgasm_from_oral penis pillows red_hair robert_terwilliger sex side_view sideshow_bob sideshow_mel sitting spitroast suck_and_fuck sucking_off the_simpsons threesome toony yaoi yellow_skin
2010 2boys against_wall anal anal_penetration anal_sex artist_signature brothers brown_hair cartoony cecil_terwilliger cock_ring color crying_with_eyes_open cuts dated erection from_behind_position half-closed_eyes hand_on_throat human incest injury long_feet male male_only multiple_males mwaters nipple_ring nipple_ring_pull nude penis questionable_consent red_hair robert_terwilliger sex side_view sideshow_bob tears the_simpsons yaoi yellow_skin
2010 2boys against_wall anal anal_penetration anal_sex artist_signature brothers brown_hair cartoony cecil_terwilliger cock_ring color crying_with_eyes_open cuts dated erection from_behind_position half-closed_eyes hand_on_throat human incest injury long_feet male male_only multiple_males mwaters nipple_ring nipple_ring_pull nude penis questionable_consent red_hair robert_terwilliger sex side_view sideshow_bob tears the_simpsons yaoi yellow_skin
2013 2boys bdsm_gear blonde_hair blush bound brothers cecil_terwilliger censored_penis chabichou chains color fingerless_gloves hair harness human incest looking_at_viewer male male_only multiple_males no_visible_genitalia red_hair robert_terwilliger sideshow_bob spiky_hair spreader_bar tagme the_simpsons two_brothers yaoi yellow_skin
2013 2boys bdsm_gear blonde_hair blush bound brothers cecil_terwilliger censored_penis chabichou chains color fingerless_gloves hair harness human incest looking_at_viewer male male_only multiple_males no_visible_genitalia red_hair robert_terwilliger sideshow_bob spiky_hair spreader_bar tagme the_simpsons two_brothers yaoi yellow_skin
cum dahlshita male_only robert_terwilliger sideshow_bob the_simpsons yaoi
cum dahlshita male_only robert_terwilliger sideshow_bob the_simpsons yaoi
2boys butcherjones color erect_nipples erection front_view gag gagged green_hair hands_behind_back human implied_anal implied_penetration implied_rape knees_together_feet_apart male male_only melvin_van_horne multiple_males nipple_piercing nipple_rings nude red_hair robert_terwilliger sideshow_bob sideshow_mel standing tagme taped_mouth taped_penis the_simpsons what yaoi
2boys butcherjones color erect_nipples erection front_view gag gagged green_hair hands_behind_back human implied_anal implied_penetration implied_rape knees_together_feet_apart male male_only melvin_van_horne multiple_males nipple_piercing nipple_rings nude red_hair robert_terwilliger sideshow_bob sideshow_mel standing tagme taped_mouth taped_penis the_simpsons what yaoi
blush bound brothers butcherjones cecil_terwilliger color erection flaccid front_view human imminent_rape male male_only melvin_van_horne multiple_males naughty_face nude penis penis_size_difference robert_terwilliger sideshow_bob sideshow_mel tagme the_simpsons whip wine wine_glass yaoi
blush bound brothers butcherjones cecil_terwilliger color erection flaccid front_view human imminent_rape male male_only melvin_van_horne multiple_males naughty_face nude penis penis_size_difference robert_terwilliger sideshow_bob sideshow_mel tagme the_simpsons whip wine wine_glass yaoi
asphyxiation death facial hanged ligature male_only napiren penis robert_terwilliger rope sideshow_bob the_simpsons unconscious what
asphyxiation death facial hanged ligature male_only napiren penis robert_terwilliger rope sideshow_bob the_simpsons unconscious what
3boys all_fours angry_face bdsm blush bone brown_hair btk butcherjones buttplug_tail cecil_terwilliger circumcised color erect_nipples erection evil_grin flaccid_penis green_hair human incest leash_and_collar male male_only malesub melvin_van_horne multiple_males multiple_penises naked_footwear nude penis red_hair robert_terwilliger sex_slave sideshow_bob sideshow_mel standing the_simpsons whip white_background yaoi
3boys all_fours angry_face bdsm blush bone brown_hair btk butcherjones buttplug_tail cecil_terwilliger circumcised color erect_nipples erection evil_grin flaccid_penis green_hair human incest leash_and_collar male male_only malesub melvin_van_horne multiple_males multiple_penises naked_footwear nude penis red_hair robert_terwilliger sex_slave sideshow_bob sideshow_mel standing the_simpsons whip white_background yaoi