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after_sex bald black_body blush bodypillow butt chubby chubby_male cum cum_drip full_body fully_nude garter_straps heart hearts_boxcars homestuck laying_down laying_on_bed laying_on_stomach microsoft_paint ms_paint_adventures problem_sleuth red_socks socks submissive_male sweat sweatdrop sweating sweaty tentabulge tentacle tentacle_penis white_eyes
after_sex bald black_body blush bodypillow butt chubby chubby_male cum cum_drip full_body fully_nude garter_straps heart hearts_boxcars homestuck laying_down laying_on_bed laying_on_stomach microsoft_paint ms_paint_adventures problem_sleuth red_socks socks submissive_male sweat sweatdrop sweating sweaty tentabulge tentacle tentacle_penis white_eyes
1boy angry angry_face bald black_body black_clothing blush boots degradation fishnets flustered gloves homestuck ibispaintx jack_noir leash leash_pull male_only ms_paint_adventures nipples problem_sleuth red_background red_leash spades_slick speech_bubble stripping text
1boy angry angry_face bald black_body black_clothing blush boots degradation fishnets flustered gloves homestuck ibispaintx jack_noir leash leash_pull male_only ms_paint_adventures nipples problem_sleuth red_background red_leash spades_slick speech_bubble stripping text
>.< anal anal_sex animal_humanoid antennae_(anatomy) anthro arthropod arthropod_humanoid ass balls bee bee_humanoid big_butt big_penis black_and_white blush bodily_fluids butt_focus censored_speech censored_text closed_eyes cum cum_in_ass cum_inside cum_while_penetrated cumming_while_penetrating curled_hair dialogue dialogue_box digital_drawing_(artwork) digital_media_(artwork) ejaculation embarrassed erection eyewear fozuna genital_fluids genitals glasses group hair hi_res holding_leg_up holding_object honeybee_professor humanoid humanoid_genitalia humanoid_penis hymenopteran hymenopteran_humanoid insect_humanoid insects male male/male male_penetrated male_penetrating male_penetrating_male monochrome nude open_mouth orgasm penetration penile penis perspective_shot pickle_inspector portal presenting presenting_hindquarters problem_sleuth rear_view sex simultaneous_orgasms size_difference stinger stinger_(anatomy) stinger_tail stuck sweat thick_thighs through_portal trio wide_hips window window_portal wings yelling
>.< anal anal_sex animal_humanoid antennae_(anatomy) anthro arthropod arthropod_humanoid ass balls bee bee_humanoid big_butt big_penis black_and_white blush bodily_fluids butt_focus censored_speech censored_text closed_eyes cum cum_in_ass cum_inside cum_while_penetrated cumming_while_penetrating curled_hair dialogue dialogue_box digital_drawing_(artwork) digital_media_(artwork) ejaculation embarrassed erection eyewear fozuna genital_fluids genitals glasses group hair hi_res holding_leg_up holding_object honeybee_professor humanoid humanoid_genitalia humanoid_penis hymenopteran hymenopteran_humanoid insect_humanoid insects male male/male male_penetrated male_penetrating male_penetrating_male monochrome nude open_mouth orgasm penetration penile penis perspective_shot pickle_inspector portal presenting presenting_hindquarters problem_sleuth rear_view sex simultaneous_orgasms size_difference stinger stinger_(anatomy) stinger_tail stuck sweat thick_thighs through_portal trio wide_hips window window_portal wings yelling
1girls black_hair blue_background blue_eyes book breasts brown_skin chubby dark-skinned_female dark_skin female glasses homestuck jane_crocker large_breasts ms_paint_adventures nipples panties problem_sleuth puni_(artist) red_glasses red_panties short_hair slightly_chubby socks solo thick_thighs thigh_highs wide_hips
1girls black_hair blue_background blue_eyes book breasts brown_skin chubby dark-skinned_female dark_skin female glasses homestuck jane_crocker large_breasts ms_paint_adventures nipples panties problem_sleuth puni_(artist) red_glasses red_panties short_hair slightly_chubby socks solo thick_thighs thigh_highs wide_hips
2girls aroused breasts breasts_out chubby chubby_female fingering hand_on_breast hand_on_crotch hand_on_partner hand_on_pussy hand_on_shoulder holding_breast hysterical_dame lesbian lesbian_sex mouth_open ms_paint_adventures naked naked_female nervous_broad problem_sleuth tagme yuri
2girls aroused breasts breasts_out chubby chubby_female fingering hand_on_breast hand_on_crotch hand_on_partner hand_on_pussy hand_on_shoulder holding_breast hysterical_dame lesbian lesbian_sex mouth_open ms_paint_adventures naked naked_female nervous_broad problem_sleuth tagme yuri
demimonde_semigoddess ms_paint_adventures problem_sleuth tagme
demimonde_semigoddess ms_paint_adventures problem_sleuth tagme
ace_dick demimonde_semigoddess fiesta_ace_dick mindwipe ms_paint_adventures pointy_chin problem_sleuth
ace_dick demimonde_semigoddess fiesta_ace_dick mindwipe ms_paint_adventures pointy_chin problem_sleuth
ace_dick demimonde_semigoddess fiesta_ace_dick mindwipe ms_paint_adventures pointy_chin problem_sleuth
ace_dick demimonde_semigoddess fiesta_ace_dick mindwipe ms_paint_adventures pointy_chin problem_sleuth
2boys anal cuddling gay gay_sex implied_anal ms_paint_adventures naked pickle_inspector problem_sleuth problem_sleuth_(character) shrimpboat smiling tagme
2boys anal cuddling gay gay_sex implied_anal ms_paint_adventures naked pickle_inspector problem_sleuth problem_sleuth_(character) shrimpboat smiling tagme
<3 1boy 2011 fellatio gay gay_sex heart kissing_penis licking licking_penis ms_paint_adventures pickle_inspector problem_sleuth shrimpboat solo solo_focus solo_male submissive submissive_male sucking sucking_penis tagme unseen_character
<3 1boy 2011 fellatio gay gay_sex heart kissing_penis licking licking_penis ms_paint_adventures pickle_inspector problem_sleuth shrimpboat solo solo_focus solo_male submissive submissive_male sucking sucking_penis tagme unseen_character
1boy 2011 ace_dick blush blushing dubious_consent gay lying lying_down lying_on_back lying_on_ground masturbating_other ms_paint_adventures problem_sleuth purple_tentacles restrained tagme tentacle_masturbation tentacle_on_penis tentacle_sex tentacles unknown_artist
1boy 2011 ace_dick blush blushing dubious_consent gay lying lying_down lying_on_back lying_on_ground masturbating_other ms_paint_adventures problem_sleuth purple_tentacles restrained tagme tentacle_masturbation tentacle_on_penis tentacle_sex tentacles unknown_artist
1boy anal artist_request clothing hat horrorterrors labrn lube lube_bottle ms_paint_adventures penis problem_sleuth short_hair solo stripping tentacle tentacle_sex white_background white_hair white_skin
1boy anal artist_request clothing hat horrorterrors labrn lube lube_bottle ms_paint_adventures penis problem_sleuth short_hair solo stripping tentacle tentacle_sex white_background white_hair white_skin
1boy 2011 ace_dick anal anal_sex blush blushing bound_arms bound_by_tentacles dubious_consent epic_face gay gay_sex horrorterrors ms_paint_adventures problem_sleuth rape shrimpboat sweating tagme tentacle_rape tentacle_sex tentacles
1boy 2011 ace_dick anal anal_sex blush blushing bound_arms bound_by_tentacles dubious_consent epic_face gay gay_sex horrorterrors ms_paint_adventures problem_sleuth rape shrimpboat sweating tagme tentacle_rape tentacle_sex tentacles
1boy 1boy1girl 1girls biting_lip chain_leash chain_pull chained chains female_dominating_male femdom leash_pull leashed madame_murel male/female mobster_kingpin problem_sleuth tagme unknown_artist
1boy 1boy1girl 1girls biting_lip chain_leash chain_pull chained chains female_dominating_male femdom leash_pull leashed madame_murel male/female mobster_kingpin problem_sleuth tagme unknown_artist
ace_dick hestooskinny ms_paint_adventures pickle_inspector problem_sleuth problem_sleuth_(character)
ace_dick hestooskinny ms_paint_adventures pickle_inspector problem_sleuth problem_sleuth_(character)
ms_paint_adventures nervous_broad pickle_inspector problem_sleuth tagme
ms_paint_adventures nervous_broad pickle_inspector problem_sleuth tagme
1boy1girl blush blushing bondage bound bound_to_bed dominant_female femdom hands_bound hysterical_dame ms_paint_adventures power_bottom problem_sleuth problem_sleuth_(character) riding shrimpboat submissive_male sweat sweating tagme
1boy1girl blush blushing bondage bound bound_to_bed dominant_female femdom hands_bound hysterical_dame ms_paint_adventures power_bottom problem_sleuth problem_sleuth_(character) riding shrimpboat submissive_male sweat sweating tagme
ace_dick bisexual_male ms_paint_adventures pickle_inspector problem_sleuth tagme threesome
ace_dick bisexual_male ms_paint_adventures pickle_inspector problem_sleuth tagme threesome
ace_dick fiesta_ace_dick male/ambiguous ms_paint_adventures problem_sleuth
ace_dick fiesta_ace_dick male/ambiguous ms_paint_adventures problem_sleuth
2010 2girls 3boys ace_dick bisexual bowler_hat cuddling hysterical_dame ms_paint_adventures nervous_broad pickle_inspector polyamory problem_sleuth problem_sleuth_(character) shrimpboat
2010 2girls 3boys ace_dick bisexual bowler_hat cuddling hysterical_dame ms_paint_adventures nervous_broad pickle_inspector polyamory problem_sleuth problem_sleuth_(character) shrimpboat
2010 2girls blush blushing cuddling fingering fingering_partner holding_breast holding_onto_partner hysterical_dame lesbian ms_paint_adventures multiple_girls nervous_broad problem_sleuth shrimpboat sweat sweatdrop yuri
2010 2girls blush blushing cuddling fingering fingering_partner holding_breast holding_onto_partner hysterical_dame lesbian ms_paint_adventures multiple_girls nervous_broad problem_sleuth shrimpboat sweat sweatdrop yuri
<3 1boy 1girl 1girls black_and_white blush blushing dominant_female female/male female_penetrating female_penetrating_male femdom jacking_off_another male_penetrated ms_paint_adventures nervous_broad pegging pickle_inspector problem_sleuth shrimpboat strap-on strapon submissive_male
<3 1boy 1girl 1girls black_and_white blush blushing dominant_female female/male female_penetrating female_penetrating_male femdom jacking_off_another male_penetrated ms_paint_adventures nervous_broad pegging pickle_inspector problem_sleuth shrimpboat strap-on strapon submissive_male
dapper_swain hysterical_dame ms_paint_adventures problem_sleuth tagme
dapper_swain hysterical_dame ms_paint_adventures problem_sleuth tagme
2010 3boys anal anal_sex blushing cuddling eyes_closed fellatio future_pickle_inspector gay gay_sex holding_onto_partner male_only ms_paint_adventures past_future_pickle_inspector pickle_inspector pleasured problem_sleuth selfcest shrimpboat sucking sucking_penis sweating sweating_profusely time_paradox
2010 3boys anal anal_sex blushing cuddling eyes_closed fellatio future_pickle_inspector gay gay_sex holding_onto_partner male_only ms_paint_adventures past_future_pickle_inspector pickle_inspector pleasured problem_sleuth selfcest shrimpboat sucking sucking_penis sweating sweating_profusely time_paradox
1boy 2010 anal anal_penetration anal_sex angry angry_face annoyed blush blushing bound bound_by_tentacles demonhead_mobster_kingpin dubious_consent gay gay_sex mobster_kingpin ms_paint_adventures nonconsensual problem_sleuth rape shrimpboat tagme tentacle tentacle_on_male tentacle_rape tentacle_sex tentacles trapped
1boy 2010 anal anal_penetration anal_sex angry angry_face annoyed blush blushing bound bound_by_tentacles demonhead_mobster_kingpin dubious_consent gay gay_sex mobster_kingpin ms_paint_adventures nonconsensual problem_sleuth rape shrimpboat tagme tentacle tentacle_on_male tentacle_rape tentacle_sex tentacles trapped
! 1girls 2boys 2boys1girl caressing_face clone future_pickle_inspector ms_paint_adventures nervous_broad pickle_inspector problem_sleuth red_outline scared scared_expression shocked shrimpboat surprised time_paradox
! 1girls 2boys 2boys1girl caressing_face clone future_pickle_inspector ms_paint_adventures nervous_broad pickle_inspector problem_sleuth red_outline scared scared_expression shocked shrimpboat surprised time_paradox
1boy1girl hysterical_dame lying lying_down ms_paint_adventures problem_sleuth problem_sleuth_(character) riding tagme
1boy1girl hysterical_dame lying lying_down ms_paint_adventures problem_sleuth problem_sleuth_(character) riding tagme