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axolotl_tail blush bondage bulge bulge_under_clothes christmas drool drooling gift_wrapped one_male pim_(smiling_friends) pim_pimling restrained ribbon ribbon_bondage smiling_friends suggestive tail
axolotl_tail blush bondage bulge bulge_under_clothes christmas drool drooling gift_wrapped one_male pim_(smiling_friends) pim_pimling restrained ribbon ribbon_bondage smiling_friends suggestive tail
>:3 ambiguous_gender anthro ass_focus ass_up big_belly big_thighs bulge catgirl charlie_(smiling_friends) chowder clothed clothed_female_nude_male cute_male face_in_ass furry fursona huge_ass jesse_meow_(sillymeowster) male/ambiguous original_character overweight role_reversal self_insert self_upload selfship shaded sillymeowster smiling_friends tail trophy_wife
>:3 ambiguous_gender anthro ass_focus ass_up big_belly big_thighs bulge catgirl charlie_(smiling_friends) chowder clothed clothed_female_nude_male cute_male face_in_ass furry fursona huge_ass jesse_meow_(sillymeowster) male/ambiguous original_character overweight role_reversal self_insert self_upload selfship shaded sillymeowster smiling_friends tail trophy_wife
comic crossover drunk_or_something_ragatha_(the_amazing_digital_circus) femboy fingering fleshlight flustered gangle_(the_amazing_digital_circus) gay jax_(the_amazing_digital_circus) male male_focus male_only manager_gangle mcdonald's mr._boss portal_fleshlight portal_sex precum ra4s ragatha_(the_amazing_digital_circus) smiling_friends the_amazing_digital_circus throbbing_penis
comic crossover drunk_or_something_ragatha_(the_amazing_digital_circus) femboy fingering fleshlight flustered gangle_(the_amazing_digital_circus) gay jax_(the_amazing_digital_circus) male male_focus male_only manager_gangle mcdonald's mr._boss portal_fleshlight portal_sex precum ra4s ragatha_(the_amazing_digital_circus) smiling_friends the_amazing_digital_circus throbbing_penis
after_sex alan_(smiling_friends) awkward cum cum_drip cum_in_pussy cum_inside cuntboy cuntboy/male dialogue drooling drooling_tongue glep_(smiling_friends) helmet impossible_fit intersex male non-human non-human_only non_human_genitalia penis pussy saliva saliva_drip saliva_string saliva_trail security_guard smiling_friends swat uniform
after_sex alan_(smiling_friends) awkward cum cum_drip cum_in_pussy cum_inside cuntboy cuntboy/male dialogue drooling drooling_tongue glep_(smiling_friends) helmet impossible_fit intersex male non-human non-human_only non_human_genitalia penis pussy saliva saliva_drip saliva_string saliva_trail security_guard smiling_friends swat uniform
begging blue_skin freckled_body freckles imminent_sex male/male penis penis_against_cheek pim_(smiling_friends) pink_skin pov smiling_friends smormu_(smiling_friends) yaoi
begging blue_skin freckled_body freckles imminent_sex male/male penis penis_against_cheek pim_(smiling_friends) pink_skin pov smiling_friends smormu_(smiling_friends) yaoi
2boys adult_swim archive_of_our_own ass_focus big_ass bigger_male blush blush_lines blushing body_hair bulge bulge_through_clothing charlie_(smiling_friends) charpim choker chubby chubby_male clothing comforting comic compliment complimenting_partner critter critter_(smiling_friends) crossdressing cute digital_media_(artwork) embarrassed fanfiction fat fat_male fat_man feminine_male friends friends_to_lovers garter_straps gay grabbing heels holding_face huge_butt huge_thighs lifting_dress lifting_skirt maid maid_apron maid_headdress maid_outfit maid_uniform male male/male male_in_dress male_only male_wife nipple_piercings no_humans non-human overweight partially_clothed pierced_nipples pim_(smiling_friends) pim_pimling praise presenting reassuring romantic romantic_couple self_upload sillymeowster size_difference small_tail smaller_male smiling_friends sock_garters sweating tail tail_wagging technical_yuri thighhighs vote_for_pedro wholesome yaoi
2boys adult_swim archive_of_our_own ass_focus big_ass bigger_male blush blush_lines blushing body_hair bulge bulge_through_clothing charlie_(smiling_friends) charpim choker chubby chubby_male clothing comforting comic compliment complimenting_partner critter critter_(smiling_friends) crossdressing cute digital_media_(artwork) embarrassed fanfiction fat fat_male fat_man feminine_male friends friends_to_lovers garter_straps gay grabbing heels holding_face huge_butt huge_thighs lifting_dress lifting_skirt maid maid_apron maid_headdress maid_outfit maid_uniform male male/male male_in_dress male_only male_wife nipple_piercings no_humans non-human overweight partially_clothed pierced_nipples pim_(smiling_friends) pim_pimling praise presenting reassuring romantic romantic_couple self_upload sillymeowster size_difference small_tail smaller_male smiling_friends sock_garters sweating tail tail_wagging technical_yuri thighhighs vote_for_pedro wholesome yaoi
charlie_(smiling_friends) claiming crown enchanted_forest larger_sub outside outside_sex panting pim_(smiling_friends) smaller_dominant smiling_friends
charlie_(smiling_friends) claiming crown enchanted_forest larger_sub outside outside_sex panting pim_(smiling_friends) smaller_dominant smiling_friends
anthro charlie_(smiling_friends) charlie_dompler charpim dicks_touching frotting hand_holding pim_(smiling_friends) pim_pimling size_difference smiling_friends tentacle tentacle_penis tentadick two_males
anthro charlie_(smiling_friends) charlie_dompler charpim dicks_touching frotting hand_holding pim_(smiling_friends) pim_pimling size_difference smiling_friends tentacle tentacle_penis tentadick two_males
2boys 2d 2d_animation adult_swim animated bottomless charlie_(smiling_friends) charlie_dompler chest_hair comedy cum drooling ejaculation hat horrified horrified_expression humanoid joke lidded_eyes looking_pleasured male male_focus male_moaning male_only masturbation michael_cusack michael_cusack_(voice) moaning moaning_in_pleasure official_art official_audio pim_(smiling_friends) pim_pimling psychicpebbles semen shitpost shocked shocked_expression sketch smiling_friends sound spinarooz tagme topless video voice_acted what
2boys 2d 2d_animation adult_swim animated bottomless charlie_(smiling_friends) charlie_dompler chest_hair comedy cum drooling ejaculation hat horrified horrified_expression humanoid joke lidded_eyes looking_pleasured male male_focus male_moaning male_only masturbation michael_cusack michael_cusack_(voice) moaning moaning_in_pleasure official_art official_audio pim_(smiling_friends) pim_pimling psychicpebbles semen shitpost shocked shocked_expression sketch smiling_friends sound spinarooz tagme topless video voice_acted what
adult_swim anal_penetration drug_usage drugged drugged_sex grim_(smiling_friends) kartooning lsd male_only male_ryona missing_eye nude_male overdose penetration penis_on_face questionable_consent rape smaller_male smiling_friends snorting snorting_cocaine tears tongue_out toony triple_penetration
adult_swim anal_penetration drug_usage drugged drugged_sex grim_(smiling_friends) kartooning lsd male_only male_ryona missing_eye nude_male overdose penetration penis_on_face questionable_consent rape smaller_male smiling_friends snorting snorting_cocaine tears tongue_out toony triple_penetration
alan_(smiling_friends) anal anal_bleeding anal_rape anal_sex bite_mark bite_marks bleeding bleeding_from_anus blood cumming cumming_from_anal_sex cumming_in_ass cumming_inside cumming_together cumming_while_penetrated cumming_while_penetrating drugged drugged_rape drugged_sex gay intoxicated landlord mr.landlord non-human non_human_genitalia nonconsensual questionable rape raped rough_anal rough_sex smiling_friends stockings stockings_only stoned thighhighs weed
alan_(smiling_friends) anal anal_bleeding anal_rape anal_sex bite_mark bite_marks bleeding bleeding_from_anus blood cumming cumming_from_anal_sex cumming_in_ass cumming_inside cumming_together cumming_while_penetrated cumming_while_penetrating drugged drugged_rape drugged_sex gay intoxicated landlord mr.landlord non-human non_human_genitalia nonconsensual questionable rape raped rough_anal rough_sex smiling_friends stockings stockings_only stoned thighhighs weed
about_to_be_raped alan_(smiling_friends) alien_genitalia annoyed_expression anthro ass_up drugged drugged_rape drugged_sex genital_slit grabbing_legs grabbing_thighs hips_up intoxicated laying_down long_penis male mr.landlord non-human non_human_genitalia penis red_eyes smiling_friends stoned weed
about_to_be_raped alan_(smiling_friends) alien_genitalia annoyed_expression anthro ass_up drugged drugged_rape drugged_sex genital_slit grabbing_legs grabbing_thighs hips_up intoxicated laying_down long_penis male mr.landlord non-human non_human_genitalia penis red_eyes smiling_friends stoned weed
alan_(smiling_friends) annoyed annoyed_expression crazy crazy_eyes crazy_smile dirty_talk groping harassment landlord long_fingers male male/male male_only mr.landlord sexual_harassment smiling_friends
alan_(smiling_friends) annoyed annoyed_expression crazy crazy_eyes crazy_smile dirty_talk groping harassment landlord long_fingers male male/male male_only mr.landlord sexual_harassment smiling_friends
adult_swim annoyed black_eyeshadow blushing_male bulge bulge_through_clothing bunny_costume bunny_ears bunny_suit chubby_male disinterested fishnet_legwear fishnets heels latex pim_(smiling_friends) pink_body self_upload shiny_clothes smiling_friends smilingrinn watermark
adult_swim annoyed black_eyeshadow blushing_male bulge bulge_through_clothing bunny_costume bunny_ears bunny_suit chubby_male disinterested fishnet_legwear fishnets heels latex pim_(smiling_friends) pink_body self_upload shiny_clothes smiling_friends smilingrinn watermark
2girls adult_swim barefoot beach blonde_female blonde_hair completely_nude completely_nude_female crab glasses glep_(smiling_friends) kaijukunny laying_on_stomach looking_back marge_simpson_(smiling_friends) redhead relaxing smiling smiling_friends zoey_(smiling_friends)
2girls adult_swim barefoot beach blonde_female blonde_hair completely_nude completely_nude_female crab glasses glep_(smiling_friends) kaijukunny laying_on_stomach looking_back marge_simpson_(smiling_friends) redhead relaxing smiling smiling_friends zoey_(smiling_friends)
alan_(smiling_friends) allan_red bdsm_gear bisexual bondage charlie_(smiling_friends) charlie_dompler chubby_male domination domination/submission dominatrix domme fat_male fat_man female female_version flat_chest flat_chested male non-human rule_63 smiling_friends smoking smoking_cigarette spiral_eyes strap-on taller_female taller_girl threesome tied_up
alan_(smiling_friends) allan_red bdsm_gear bisexual bondage charlie_(smiling_friends) charlie_dompler chubby_male domination domination/submission dominatrix domme fat_male fat_man female female_version flat_chest flat_chested male non-human rule_63 smiling_friends smoking smoking_cigarette spiral_eyes strap-on taller_female taller_girl threesome tied_up
alan_(smiling_friends) allan_red anal anal_sex blush choking crying crying_while_penetrated crying_with_eyes_open male male_only male_ryona necktie necktie_grab necktie_only necktie_pull nonconsensual null nullo rape raped red_body reptile_humanoid smiling_friends tied_hands tied_up
alan_(smiling_friends) allan_red anal anal_sex blush choking crying crying_while_penetrated crying_with_eyes_open male male_only male_ryona necktie necktie_grab necktie_only necktie_pull nonconsensual null nullo rape raped red_body reptile_humanoid smiling_friends tied_hands tied_up
alan_(smiling_friends) alien_genitalia allan_red angry angry_face asshole bald genital_focus hairless male male_focus male_only non-human non-human_only red_body reptile_humanoid showing_ass showing_off slit smiling_friends swearing
alan_(smiling_friends) alien_genitalia allan_red angry angry_face asshole bald genital_focus hairless male male_focus male_only non-human non-human_only red_body reptile_humanoid showing_ass showing_off slit smiling_friends swearing
ass blush gay gay_sex gnarly_(smiling_friends) grim_(smiling_friends) hairy hairy_ass homonculus oldmeatcurtains oral_sex purple_skin smiling_friends sweat yellow_skin
ass blush gay gay_sex gnarly_(smiling_friends) grim_(smiling_friends) hairy hairy_ass homonculus oldmeatcurtains oral_sex purple_skin smiling_friends sweat yellow_skin
1girls chubby genderswap_(mtf) kneeling nude pim_(smiling_friends) pink_body popeexoxo pubic_hair pussy_juice pussy_juice_drip rule_63 self_upload shortstack shy smiling_friends sweatdrop thick_thighs wet_pussy
1girls chubby genderswap_(mtf) kneeling nude pim_(smiling_friends) pink_body popeexoxo pubic_hair pussy_juice pussy_juice_drip rule_63 self_upload shortstack shy smiling_friends sweatdrop thick_thighs wet_pussy
2023 adult adult_swim ass ass_focus big_ass fanart femboy_hooters pim pim_(smiling_friends) pim_pimling revealing revealing_clothes revealing_outfit shorts smiling_friends solo solo_focus suggestive tight_clothing zornycatboy
2023 adult adult_swim ass ass_focus big_ass fanart femboy_hooters pim pim_(smiling_friends) pim_pimling revealing revealing_clothes revealing_outfit shorts smiling_friends solo solo_focus suggestive tight_clothing zornycatboy
2024 adult_swim arms arms_behind_back bara charlie charlie_(smiling_friends) charlie_dompler chubby fanart fat hairy hairy_armpits hairy_balls hairy_chest hairy_male hat lying_on_side man_boobs moobs musk musky orange_background overweight overweight_male pinup smiling_friends solo solo_male steam telstartelstar
2024 adult_swim arms arms_behind_back bara charlie charlie_(smiling_friends) charlie_dompler chubby fanart fat hairy hairy_armpits hairy_balls hairy_chest hairy_male hat lying_on_side man_boobs moobs musk musky orange_background overweight overweight_male pinup smiling_friends solo solo_male steam telstartelstar
alan_(smiling_friends) ambiguous_gender ambiguous_genitalia blue_tie charlie_(smiling_friends) masturbating masturbation pillow_humping pillow_ride red_body self_upload skydoesxxx smiling_friends solo tie
alan_(smiling_friends) ambiguous_gender ambiguous_genitalia blue_tie charlie_(smiling_friends) masturbating masturbation pillow_humping pillow_ride red_body self_upload skydoesxxx smiling_friends solo tie
2_panel_comic 5boys adult_swim alan_(smiling_friends) big_eyes big_nose blush blush_lines bromance charlie_(smiling_friends) charpim coffee comic critter disembodied_head disgust disgusted disgusted_look doodle eyes gay glep_(smiling_friends) heart kissing love love_wins male/male male_only mug nose_between_eyes oscar_(smiling_friends) peyezuri pim_(smiling_friends) romantic self_upload shitpost smiling_friends sukala-ap yaoi
2_panel_comic 5boys adult_swim alan_(smiling_friends) big_eyes big_nose blush blush_lines bromance charlie_(smiling_friends) charpim coffee comic critter disembodied_head disgust disgusted disgusted_look doodle eyes gay glep_(smiling_friends) heart kissing love love_wins male/male male_only mug nose_between_eyes oscar_(smiling_friends) peyezuri pim_(smiling_friends) romantic self_upload shitpost smiling_friends sukala-ap yaoi
ass big_ass big_breasts blue_pants breasts hick_thighs huge_ass huge_breasts milf oe_overxposure pink_body pink_skin smiling_friends tagme thick_thighs thighs unnamed_character yellow_hair
ass big_ass big_breasts blue_pants breasts hick_thighs huge_ass huge_breasts milf oe_overxposure pink_body pink_skin smiling_friends tagme thick_thighs thighs unnamed_character yellow_hair
203y 2boys adult_swim anal anal_sex anus bigger_male biting_lip blush blush_lines caged_cock caged_penis charlie_(smiling_friends) chastity chastity_cage chastity_device chubby chubby_male critter doggy_style fat fat_male fat_man gay gay_domination gay_sex handprint handprint_on_ass hands_on_thighs looking_pleasured male male/male male_moaning male_only maledom malesub moaning naked naked_male penis pillow_grab pillows pim_(smiling_friends) profanity pulling_hair signature size_difference sketch sketchy small_dom_big_sub small_top_big_bottom smaller_male smile smiling_friends spank_mark spanking spanking_ass spread_legs submissive_male sweat sweating yaoi
203y 2boys adult_swim anal anal_sex anus bigger_male biting_lip blush blush_lines caged_cock caged_penis charlie_(smiling_friends) chastity chastity_cage chastity_device chubby chubby_male critter doggy_style fat fat_male fat_man gay gay_domination gay_sex handprint handprint_on_ass hands_on_thighs looking_pleasured male male/male male_moaning male_only maledom malesub moaning naked naked_male penis pillow_grab pillows pim_(smiling_friends) profanity pulling_hair signature size_difference sketch sketchy small_dom_big_sub small_top_big_bottom smaller_male smile smiling_friends spank_mark spanking spanking_ass spread_legs submissive_male sweat sweating yaoi
3boys adult_swim anal_insertion anthro blowjob charlie_(smiling_friends) chubby chubby_male critter dialogue erect_penis gay gay_sex glasses handjob heart male male/male/male male_only multitasking oral oral_sex pants_down penis penis_grasp pim_(smiling_friends) precum remote_control_vibrator saliva_drip saliva_string saliva_trail shrimp shrimp_(smiling_friends) smiling_friends sucking_penis threesome vibrator vibrator_in_ass vibrator_remote watermark wicpers yaoi
3boys adult_swim anal_insertion anthro blowjob charlie_(smiling_friends) chubby chubby_male critter dialogue erect_penis gay gay_sex glasses handjob heart male male/male/male male_only multitasking oral oral_sex pants_down penis penis_grasp pim_(smiling_friends) precum remote_control_vibrator saliva_drip saliva_string saliva_trail shrimp shrimp_(smiling_friends) smiling_friends sucking_penis threesome vibrator vibrator_in_ass vibrator_remote watermark wicpers yaoi
adult_swim anthro artist_signature bulge chubby_male critter glasses laying_on_side male male_only pinup pose posing posing_for_the_viewer red_speedo seductive seductive_look shrimp shrimp_(smiling_friends) signature signed smiling_friends solo_male speedo wicpers
adult_swim anthro artist_signature bulge chubby_male critter glasses laying_on_side male male_only pinup pose posing posing_for_the_viewer red_speedo seductive seductive_look shrimp shrimp_(smiling_friends) signature signed smiling_friends solo_male speedo wicpers
adult_swim alan_(smiling_friends) anal anus blush boxlifeorbust charlie_(smiling_friends) dialogue embarrassed embarrassed_nude_female fisting funny glep_(smiling_friends) humiliation i_feel_fantastic naked nude pim_(smiling_friends) pussy smiling_friends tara_the_android
adult_swim alan_(smiling_friends) anal anus blush boxlifeorbust charlie_(smiling_friends) dialogue embarrassed embarrassed_nude_female fisting funny glep_(smiling_friends) humiliation i_feel_fantastic naked nude pim_(smiling_friends) pussy smiling_friends tara_the_android
1_eye 1cuntboy 4_fingers abs adult_swim ambiguous_gender andromorph andromorph/male bara bara_tiddies bara_tits big_chest big_muscles big_pecs big_pectorals bodybuilder broad_shoulders cartoon_network chest cuntboy eyeball for_a_head gradient half-closed_eyes headgear holding_chest humanoid humanoid_genitalia humanoid_male humanoid_pussy humanoid_vagina hunk intersex intersex/male jester kneeling looking_at_viewer male massive_thighs mentholplug moobs muscles muscular muscular_cuntboy muscular_male muscular_thighs object_head one_arm_behind_back oscar_(smiling_friends) pecs pectorals pim_(smiling_friends) pink_eyes pussy rainbow rainbow_body red_cape robe serious smiling_friends solo squeezing_pecs thick_thighs vagina vaginal_fluids
1_eye 1cuntboy 4_fingers abs adult_swim ambiguous_gender andromorph andromorph/male bara bara_tiddies bara_tits big_chest big_muscles big_pecs big_pectorals bodybuilder broad_shoulders cartoon_network chest cuntboy eyeball for_a_head gradient half-closed_eyes headgear holding_chest humanoid humanoid_genitalia humanoid_male humanoid_pussy humanoid_vagina hunk intersex intersex/male jester kneeling looking_at_viewer male massive_thighs mentholplug moobs muscles muscular muscular_cuntboy muscular_male muscular_thighs object_head one_arm_behind_back oscar_(smiling_friends) pecs pectorals pim_(smiling_friends) pink_eyes pussy rainbow rainbow_body red_cape robe serious smiling_friends solo squeezing_pecs thick_thighs vagina vaginal_fluids
adult_swim blush blushing_profusely boots bulge bulge_through_clothing cowboy_boots cowboy_hat embarrassed flannel flannel_shirt flustered pim_(smiling_friends) pim_pimling pink_body pink_skin prekupre self_upload short_male short_shorts smaller_male smiling_friends smilingrinn sweat sweatdrop sweaty_body watermark
adult_swim blush blushing_profusely boots bulge bulge_through_clothing cowboy_boots cowboy_hat embarrassed flannel flannel_shirt flustered pim_(smiling_friends) pim_pimling pink_body pink_skin prekupre self_upload short_male short_shorts smaller_male smiling_friends smilingrinn sweat sweatdrop sweaty_body watermark
2girls adult_swim alan_(smiling_friends) big_breasts blank_background blue_hat blue_tie breasts dialogue duo duo_female duo_focus featureless_breasts featureless_crotch female female_focus female_only gender_bender genderbent genderswap_(mtf) glep_(smiling_friends) green_body hat larger_female no_background no_genitals no_nipples red_body rubbing_neck rule_63 shortstack size_difference smaller_female smiling_friends tagme thick thick_thighs thighs tie voideyedpanda voluptuous voluptuous_female white_background wizard_hat
2girls adult_swim alan_(smiling_friends) big_breasts blank_background blue_hat blue_tie breasts dialogue duo duo_female duo_focus featureless_breasts featureless_crotch female female_focus female_only gender_bender genderbent genderswap_(mtf) glep_(smiling_friends) green_body hat larger_female no_background no_genitals no_nipples red_body rubbing_neck rule_63 shortstack size_difference smaller_female smiling_friends tagme thick thick_thighs thighs tie voideyedpanda voluptuous voluptuous_female white_background wizard_hat
adult_swim charlie_(smiling_friends) charlie_dompler fantasizing gay ickystickypink masturbating masturbation pim_(smiling_friends) pim_pimling smiling_friends
adult_swim charlie_(smiling_friends) charlie_dompler fantasizing gay ickystickypink masturbating masturbation pim_(smiling_friends) pim_pimling smiling_friends
adult_swim alan_(smiling_friends) allan_red balding blue_tie blush blushing critter freckles freckles_on_body gay gay_sex hairy human humanoid male_only mr._boss nails_painted non-human old old_man pubes robowhoremangle sagging_breasts skinny slim smiling_friends spine tie yaoi
adult_swim alan_(smiling_friends) allan_red balding blue_tie blush blushing critter freckles freckles_on_body gay gay_sex hairy human humanoid male_only mr._boss nails_painted non-human old old_man pubes robowhoremangle sagging_breasts skinny slim smiling_friends spine tie yaoi
adult_swim cartoony charlie_(smiling_friends) charlie_dompler masturbating masturbation oldmeatcurtains pim_(smiling_friends) pim_pimling pleasure_face smiling_friends
adult_swim cartoony charlie_(smiling_friends) charlie_dompler masturbating masturbation oldmeatcurtains pim_(smiling_friends) pim_pimling pleasure_face smiling_friends
adult_swim blowjob blush blush_lines blushing body_hair charlie_(smiling_friends) charlie_dompler fat_man fellatio gay gay_sex hairy hairy_body heart_eyes hearts male/male oral oral_sex pim_(smiling_friends) pim_pimling size_difference smiling_friends smutmutt69 tail tail_wagging yaoi
adult_swim blowjob blush blush_lines blushing body_hair charlie_(smiling_friends) charlie_dompler fat_man fellatio gay gay_sex hairy hairy_body heart_eyes hearts male/male oral oral_sex pim_(smiling_friends) pim_pimling size_difference smiling_friends smutmutt69 tail tail_wagging yaoi