midnight_crew best from all time

Time frame

Tags

midnight crew

2boys 5_toes anus anus_peek ass bald balls big_ass black_skin feet felon-igoe gay homestuck humanoid humanoid_feet jack_noir justmegabenewell looking_at_viewer looking_back male_only midnight_crew ms_paint_adventures naked presenting_hindquarters soles spades_slick
2boys 5_toes anus anus_peek ass bald balls big_ass black_skin feet felon-igoe gay homestuck humanoid humanoid_feet jack_noir justmegabenewell looking_at_viewer looking_back male_only midnight_crew ms_paint_adventures naked presenting_hindquarters soles spades_slick
2019 2d 2d_artwork 4boys aipeco18 alien alien_boy alien_humanoid anal anal_sex big_dom_small_sub bigger_male biting_lip biting_own_lip blush carapacian clubs_deuce cum cumming diamonds_droog dwarf_male fingering fingering_anus fingering_ass full_nelson gay gay_anal gay_sex heart hearts hearts_boxcars height_difference homestuck looking_back midnight_crew ms_paint_adventures partially_clothed screaming_in_pleasure shocked shocked_expression size_difference small_dom_big_sub smaller_male spades_slick submissive_focus submissive_male yaoi
2019 2d 2d_artwork 4boys aipeco18 alien alien_boy alien_humanoid anal anal_sex big_dom_small_sub bigger_male biting_lip biting_own_lip blush carapacian clubs_deuce cum cumming diamonds_droog dwarf_male fingering fingering_anus fingering_ass full_nelson gay gay_anal gay_sex heart hearts hearts_boxcars height_difference homestuck looking_back midnight_crew ms_paint_adventures partially_clothed screaming_in_pleasure shocked shocked_expression size_difference small_dom_big_sub smaller_male spades_slick submissive_focus submissive_male yaoi
2boys anal ass black_skin clothing derp dialogue doc_scratch eye_patch gay hat homestuck midnight_crew ms_paint_adventures robotic_arm scar sharp_teeth spades_slick text white_background white_skin
2boys anal ass black_skin clothing derp dialogue doc_scratch eye_patch gay hat homestuck midnight_crew ms_paint_adventures robotic_arm scar sharp_teeth spades_slick text white_background white_skin
4boys anal ass bald black_skin blush closed_eyes clothing clubs_deuce comic derp diamonds_droog fellatio gay hat hearts_boxcars homestuck midnight_crew ms_paint_adventures naked open_mouth oral penis sleeping spades_slick white_background white_skin
4boys anal ass bald black_skin blush closed_eyes clothing clubs_deuce comic derp diamonds_droog fellatio gay hat hearts_boxcars homestuck midnight_crew ms_paint_adventures naked open_mouth oral penis sleeping spades_slick white_background white_skin
2boys black_skin blood carapace clothing doc_scratch eye_patch gay handjob homestuck midnight_crew ms_paint_adventures penis precum robotic_arm spades_slick white_eyes white_skin
2boys black_skin blood carapace clothing doc_scratch eye_patch gay handjob homestuck midnight_crew ms_paint_adventures penis precum robotic_arm spades_slick white_eyes white_skin
1boy 1girls areolae artist_name balls ballsack big_breasts black_body black_hair carapace carapacian choker clitoris diamonds_droog dominant_female earring earrings erection female female_focus femdom fish gills glasses grin homestuck horns humanoid humanoid_penis interspecies jewelry labia long_hair male male_penetrating male_penetrating_female midnight_crew ms_paint_adventures nauticallyincriminative nipples nude nude_female nude_male open_mouth partial_male penis penis_in_pussy penis_in_vagina reverse_cowgirl_position ring scrotum shaven size_difference smooth_penis straight submissive_male tagme teeth testicles the_condesce thick_thighs tiara troll vagina
1boy 1girls areolae artist_name balls ballsack big_breasts black_body black_hair carapace carapacian choker clitoris diamonds_droog dominant_female earring earrings erection female female_focus femdom fish gills glasses grin homestuck horns humanoid humanoid_penis interspecies jewelry labia long_hair male male_penetrating male_penetrating_female midnight_crew ms_paint_adventures nauticallyincriminative nipples nude nude_female nude_male open_mouth partial_male penis penis_in_pussy penis_in_vagina reverse_cowgirl_position ring scrotum shaven size_difference smooth_penis straight submissive_male tagme teeth testicles the_condesce thick_thighs tiara troll vagina
1boy 2girls black_background black_skin blush breasts breasts_out closed_eyes clothing cunnilingus derp hat headwear homestuck midnight_crew ms_paint_adventures nipples open_mouth peregrine_mendicant snowman_(homestuck) spades_slick straight the_felt threesome white_skin
1boy 2girls black_background black_skin blush breasts breasts_out closed_eyes clothing cunnilingus derp hat headwear homestuck midnight_crew ms_paint_adventures nipples open_mouth peregrine_mendicant snowman_(homestuck) spades_slick straight the_felt threesome white_skin
1boy alien alien_humanoid arms_tied black_skin chair clothing fully_clothed grey_background hat homestuck humanoid jacket midnight_crew ms_paint_adventures penis rope scar solo spades_slick white_eyes
1boy alien alien_humanoid arms_tied black_skin chair clothing fully_clothed grey_background hat homestuck humanoid jacket midnight_crew ms_paint_adventures penis rope scar solo spades_slick white_eyes
1boy ass boxers gay hearts_boxcars homestuck illuminaughty male male_only midnight_crew ms_paint_adventures seductive seductive_pose smiling underwear_down
1boy ass boxers gay hearts_boxcars homestuck illuminaughty male male_only midnight_crew ms_paint_adventures seductive seductive_pose smiling underwear_down
2boys bald black_skin blood carapace clothing doc_scratch eyepatch gay handjob homestuck midnight_crew ms_paint_adventures no_face penis precum robotic_arm spades_slick white_skin
2boys bald black_skin blood carapace clothing doc_scratch eyepatch gay handjob homestuck midnight_crew ms_paint_adventures no_face penis precum robotic_arm spades_slick white_skin
4boys black_skin blush clothing clubs_deuce derp diamonds_droog fellatio gay handjob hat hearts_boxcars homestuck midnight_crew ms_paint_adventures one_eye_closed oral penis precum spades_slick white_eyes
4boys black_skin blush clothing clubs_deuce derp diamonds_droog fellatio gay handjob hat hearts_boxcars homestuck midnight_crew ms_paint_adventures one_eye_closed oral penis precum spades_slick white_eyes
1boy alien_humanoid bald black_skin chair grey_background homestuck humanoid male male_only masturbation midnight_crew ms_paint_adventures open_mouth penis sharp_teeth shirt solo spades_slick
1boy alien_humanoid bald black_skin chair grey_background homestuck humanoid male male_only masturbation midnight_crew ms_paint_adventures open_mouth penis sharp_teeth shirt solo spades_slick
2boys alien alien_humanoid black_skin blush clothing diamonds_droog fellatio gay green_skin hat homestuck humanoid midnight_crew ms_paint_adventures oral penis source_request stitch_(homestuck) the_felt unknown_artist white_background
2boys alien alien_humanoid black_skin blush clothing diamonds_droog fellatio gay green_skin hat homestuck humanoid midnight_crew ms_paint_adventures oral penis source_request stitch_(homestuck) the_felt unknown_artist white_background
1boy black_skin blush carapace clothing cum cum_on_body drooling hat homestuck midnight_crew ms_paint_adventures scar solo spades_slick white_eyes
1boy black_skin blush carapace clothing cum cum_on_body drooling hat homestuck midnight_crew ms_paint_adventures scar solo spades_slick white_eyes
2boys alien alien_humanoid black_skin blood clothing cockzilla comic dismemberment eggs_(homestuck) gay gore green_skin handjob hat hearts_boxcars homestuck humanoid male/male male_only male_ryona midnight_crew ms_paint_adventures penis sharp_teeth the_felt
2boys alien alien_humanoid black_skin blood clothing cockzilla comic dismemberment eggs_(homestuck) gay gore green_skin handjob hat hearts_boxcars homestuck humanoid male/male male_only male_ryona midnight_crew ms_paint_adventures penis sharp_teeth the_felt
2boys alien alien_humanoid artist_request bald black_skin blush boxers diamonds_droog gay green_skin half-dressed half_naked handjob holding_hands homestuck humanoid midnight_crew ms_paint_adventures naked penis scars stitch_(homestuck) tagme_(artist) the_felt white_background white_eyes
2boys alien alien_humanoid artist_request bald black_skin blush boxers diamonds_droog gay green_skin half-dressed half_naked handjob holding_hands homestuck humanoid midnight_crew ms_paint_adventures naked penis scars stitch_(homestuck) tagme_(artist) the_felt white_background white_eyes
1boy 1girls black_skin breasts cigarette cigarette_holder clothing green_background gun homestuck midnight_crew ms_paint_adventures naked nipples open_mouth penetration penis questionable_consent sharp_teeth smoking snowman_(homestuck) spades_slick straight suicide_threat the_felt white_eyes
1boy 1girls black_skin breasts cigarette cigarette_holder clothing green_background gun homestuck midnight_crew ms_paint_adventures naked nipples open_mouth penetration penis questionable_consent sharp_teeth smoking snowman_(homestuck) spades_slick straight suicide_threat the_felt white_eyes
2012 2boys 2d 2d_artwork artist_signature black_body blood blood_splatter business_suit carapace carapacian color diamonds_droog eye_fucking eye_penetration formal_wear gay gay_sex gore guro hat homestuck male male/male male_only midnight_crew ms_paint_adventures penetration penis penis_out rollingthedices skull_fucking spades_slick suit suit_and_tie
2012 2boys 2d 2d_artwork artist_signature black_body blood blood_splatter business_suit carapace carapacian color diamonds_droog eye_fucking eye_penetration formal_wear gay gay_sex gore guro hat homestuck male male/male male_only midnight_crew ms_paint_adventures penetration penis penis_out rollingthedices skull_fucking spades_slick suit suit_and_tie
2boys anal anal_sex bald black_body blush clubs_deuce cum cum_in_ass formal_wear gay gay_sex hat homestuck ibispaintx jack_noir leaking_cum midnight_crew ms_paint_adventures nipples no_text pillow pink_thighhighs quivering sex size_difference spades_slick submissive_male sweat thighhighs white_eyes yaoi
2boys anal anal_sex bald black_body blush clubs_deuce cum cum_in_ass formal_wear gay gay_sex hat homestuck ibispaintx jack_noir leaking_cum midnight_crew ms_paint_adventures nipples no_text pillow pink_thighhighs quivering sex size_difference spades_slick submissive_male sweat thighhighs white_eyes yaoi
3boys alien alien_humanoid angry biscuits_(homestuck) black_skin clock clothing eggs_(homestuck) green_skin grey_background hat hearts_boxcars homestuck humanoid magazine male/male masturbation midnight_crew ms_paint_adventures naked penis the_felt
3boys alien alien_humanoid angry biscuits_(homestuck) black_skin clock clothing eggs_(homestuck) green_skin grey_background hat hearts_boxcars homestuck humanoid magazine male/male masturbation midnight_crew ms_paint_adventures naked penis the_felt
2boys ass black_skin clothing gay green_background hearts_boxcars homestuck imminent_anal male male_only midnight_crew ms_paint_adventures one_eye_closed pants_down penis precum red_eyes short_hair white_eyes white_hair
2boys ass black_skin clothing gay green_background hearts_boxcars homestuck imminent_anal male male_only midnight_crew ms_paint_adventures one_eye_closed pants_down penis precum red_eyes short_hair white_eyes white_hair