awkward best from last month

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1girls :i absurdres adorable adorable_girl ai-generated ai_generated apologizing apology awkward bare_hips bare_legs beautiful bedroom_eyes blonde_hair blue_eyes cartoon covered_nipples covering_crotch covering_nudity covering_pussy covering_vagina cute cute_girl cute_pose disney disney_channel disney_princess disney_xd embarrassed embarrassed_female eyelashes facing_away fake_horns female female_focus flat_chest groin half-closed_eyes heart_cheeks highres hips horn_hairband horns innocent legs legwear leotard lolita_(fashion) lolita_fashion lolita_hairband long_hair looking_at_viewer losforry_custom magical_girl naked nude nude_female pasties petite petite_body petite_female petite_girl plate pretty_girl princess reverse_bunnysuit sexy sexy_body sexy_female sexy_girl simple_background small_breasts small_hips solo standing star_bra star_butterfly star_pasties star_vs_the_forces_of_evil student teen teen_girl teenage teenage_girl teenager thighhighs thin thin_female thin_waist tight_clothing tight_dress white_background wholesome wholesome_nudity younger_female
1girls :i absurdres adorable adorable_girl ai-generated ai_generated apologizing apology awkward bare_hips bare_legs beautiful bedroom_eyes blonde_hair blue_eyes cartoon covered_nipples covering_crotch covering_nudity covering_pussy covering_vagina cute cute_girl cute_pose disney disney_channel disney_princess disney_xd embarrassed embarrassed_female eyelashes facing_away fake_horns female female_focus flat_chest groin half-closed_eyes heart_cheeks highres hips horn_hairband horns innocent legs legwear leotard lolita_(fashion) lolita_fashion lolita_hairband long_hair looking_at_viewer losforry_custom magical_girl naked nude nude_female pasties petite petite_body petite_female petite_girl plate pretty_girl princess reverse_bunnysuit sexy sexy_body sexy_female sexy_girl simple_background small_breasts small_hips solo standing star_bra star_butterfly star_pasties star_vs_the_forces_of_evil student teen teen_girl teenage teenage_girl teenager thighhighs thin thin_female thin_waist tight_clothing tight_dress white_background wholesome wholesome_nudity younger_female
1boy 1boy1girl 1girl1boy anxiety anxious autistic awkward binder_(clothing) boku_no_hero_academia bra chubby chubby_female cuntboy cute cute_expression cute_girl deku doggy_style english_text fat_ass fat_female fatty female funny guyfromliyue(artist) hetero_sex internal_monologue intersex izuku_midoriya midoriya_izuku monologue my_hero_academia nerd nerdy_male ochako_uraraka panties side_view squeezing_butt straight straight_sex strap-on strap-on_sex strapon submissive_female text transgender underwear uraraka_ochako vagina vaginal_penetration vaginal_sex virgin virgin_male wall_of_text worried worried_expression
1boy 1boy1girl 1girl1boy anxiety anxious autistic awkward binder_(clothing) boku_no_hero_academia bra chubby chubby_female cuntboy cute cute_expression cute_girl deku doggy_style english_text fat_ass fat_female fatty female funny guyfromliyue(artist) hetero_sex internal_monologue intersex izuku_midoriya midoriya_izuku monologue my_hero_academia nerd nerdy_male ochako_uraraka panties side_view squeezing_butt straight straight_sex strap-on strap-on_sex strapon submissive_female text transgender underwear uraraka_ochako vagina vaginal_penetration vaginal_sex virgin virgin_male wall_of_text worried worried_expression
1girls 2d ai_generated ass athletic athletic_female awkward bare_shoulders belly big_breasts blonde_female blonde_hair blonde_hair_female cha_hae_in chest curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female female_only fit fit_female focus high_quality legs light-skinned_female light_skin lips lipstick looking_at_viewer makeup mascara medium_breasts midriff naked navel nero100 nervous nipples nude nude_female pale-skinned_female pale_skin panties perky_breasts posing purple_eyes seductive seductive_look shy solo_leveling stable_diffusion thighs thin_thighs thin_waist
1girls 2d ai_generated ass athletic athletic_female awkward bare_shoulders belly big_breasts blonde_female blonde_hair blonde_hair_female cha_hae_in chest curvy curvy_figure cute cute_face detailed eyelashes eyeshadow female female_only fit fit_female focus high_quality legs light-skinned_female light_skin lips lipstick looking_at_viewer makeup mascara medium_breasts midriff naked navel nero100 nervous nipples nude nude_female pale-skinned_female pale_skin panties perky_breasts posing purple_eyes seductive seductive_look shy solo_leveling stable_diffusion thighs thin_thighs thin_waist
2024 3_toes 4_fingers anthro ass awkward bed bedroom blind_eye blush bottomwear breasts canid canid_demon canine chilllum claws clothed clothing clothing_aside collar comic cunnilingus dark_body dark_fur demon dialogue digital_media_(artwork) dominant dominant_male duo english_text eye_scar eyebrow_piercing facial_piercing facial_scar fangs feet female finger_claws fingers fishnet_clothing fishnet_shirt fishnet_topwear food foximoron fur furniture genitals grey_body grey_fur grey_hair hair hand_on_breast hand_on_head hellhound helluva_boss hi_res hindpaw humanoid_hands intraspecies_romance jacket leather leather_clothing leather_jacket leather_topwear leggings legwear licking loona_(helluva_boss) making_love making_out male male/female mammal moan multicolored_body multicolored_fur mythological_canine mythological_creature mythology narrowed_eyes navel nervous nipple_piercing nipples on_bed open_mouth oral panties panties_aside pants partially_clothed paws piercing profanity pushing reassuring red_sclera romantic romantic_ambiance romantic_couple scar sex shirt shy skirt slurping smile spiked_collar spikes spread_legs spreading standing submissive submissive_female tail teeth tender text texting toe_claws toeless_legwear toeless_stockings toes tongue topless_to_partially_bottomless topwear torn_bottomwear torn_clothing torn_legwear torn_pants two_tone_body two_tone_fur underwear underwear_aside undressing url vaginal_penetration vortex_(helluva_boss) white_body white_eyes white_fur wounded
2024 3_toes 4_fingers anthro ass awkward bed bedroom blind_eye blush bottomwear breasts canid canid_demon canine chilllum claws clothed clothing clothing_aside collar comic cunnilingus dark_body dark_fur demon dialogue digital_media_(artwork) dominant dominant_male duo english_text eye_scar eyebrow_piercing facial_piercing facial_scar fangs feet female finger_claws fingers fishnet_clothing fishnet_shirt fishnet_topwear food foximoron fur furniture genitals grey_body grey_fur grey_hair hair hand_on_breast hand_on_head hellhound helluva_boss hi_res hindpaw humanoid_hands intraspecies_romance jacket leather leather_clothing leather_jacket leather_topwear leggings legwear licking loona_(helluva_boss) making_love making_out male male/female mammal moan multicolored_body multicolored_fur mythological_canine mythological_creature mythology narrowed_eyes navel nervous nipple_piercing nipples on_bed open_mouth oral panties panties_aside pants partially_clothed paws piercing profanity pushing reassuring red_sclera romantic romantic_ambiance romantic_couple scar sex shirt shy skirt slurping smile spiked_collar spikes spread_legs spreading standing submissive submissive_female tail teeth tender text texting toe_claws toeless_legwear toeless_stockings toes tongue topless_to_partially_bottomless topwear torn_bottomwear torn_clothing torn_legwear torn_pants two_tone_body two_tone_fur underwear underwear_aside undressing url vaginal_penetration vortex_(helluva_boss) white_body white_eyes white_fur wounded
1:1 2025 2boys 2cuntboys awkward awkward_situation bendu_(danwiki) confused confused_look confusion cuntboy dave_and_bambi_mod digital_drawing_(artwork) digital_media_(artwork) expunged_(rapparep) friday_night_funkin friday_night_funkin_mod goofy_smile gradient_background happy happy_expression happy_male hat hi_res intersex intersex/intersex intersex/male looking_down looking_up mexican mexican_male naked naked_male nizisbizzy no_pubes nude nude_intersex nude_male red_hat shaded shaved_pussy smile smiling smiling_at_another smiling_at_partner toony weird_eyes yellow_hat
1:1 2025 2boys 2cuntboys awkward awkward_situation bendu_(danwiki) confused confused_look confusion cuntboy dave_and_bambi_mod digital_drawing_(artwork) digital_media_(artwork) expunged_(rapparep) friday_night_funkin friday_night_funkin_mod goofy_smile gradient_background happy happy_expression happy_male hat hi_res intersex intersex/intersex intersex/male looking_down looking_up mexican mexican_male naked naked_male nizisbizzy no_pubes nude nude_intersex nude_male red_hat shaded shaved_pussy smile smiling smiling_at_another smiling_at_partner toony weird_eyes yellow_hat
anthro areola ass awkward big_areola big_breasts big_butt big_nipples black_and_white bodily_fluids breasts canid canine clothed clothing digital_drawing_(artwork) digital_media_(artwork) drooling duo dus duskizi dusky_(duskizi) female fish full-length_portrait gaming genitals hi_res huge_breasts huge_butt huge_hips huge_thighs humanoid looking_at_another looking_at_object machine male male/female mammal marine monochrome nintendo nintendo_switch_2 nipples nude nude_female playing_video_game portrait robot saliva shark short_stack sketch switch_dog thick_thighs twosy wide_hips
anthro areola ass awkward big_areola big_breasts big_butt big_nipples black_and_white bodily_fluids breasts canid canine clothed clothing digital_drawing_(artwork) digital_media_(artwork) drooling duo dus duskizi dusky_(duskizi) female fish full-length_portrait gaming genitals hi_res huge_breasts huge_butt huge_hips huge_thighs humanoid looking_at_another looking_at_object machine male male/female mammal marine monochrome nintendo nintendo_switch_2 nipples nude nude_female playing_video_game portrait robot saliva shark short_stack sketch switch_dog thick_thighs twosy wide_hips
absurd_res anthro awkward big_penis clothing erection genitals hi_res hoodie huge_cock leezpunk lizard male male_only masturbation nib-roc pal_(species) palworld penis pocketpair reptile scalie solo topwear under_clothes
absurd_res anthro awkward big_penis clothing erection genitals hi_res hoodie huge_cock leezpunk lizard male male_only masturbation nib-roc pal_(species) palworld penis pocketpair reptile scalie solo topwear under_clothes
4:3 athletic aubrey_lebeau awkward bite_mark deer duo felid feline female female_penetrated from_front_position hi_res kuri_lebeau lying lynx male male/female male_penetrating mammal missionary_position nipple_piercing nipples on_back penetration piercing sabanasmiles sex size_difference slightly_chubby smaller_female tail tail_motion tender
4:3 athletic aubrey_lebeau awkward bite_mark deer duo felid feline female female_penetrated from_front_position hi_res kuri_lebeau lying lynx male male/female male_penetrating mammal missionary_position nipple_piercing nipples on_back penetration piercing sabanasmiles sex size_difference slightly_chubby smaller_female tail tail_motion tender
... 1boy 1girl :3 =_= a-chan_(little_busters!) absurdres arm_at_side awkward bare_arms bare_legs bare_shoulders barefoot bikini blue_eyes blush bow bow_bikini breast_press breasts brown_eyes brown_hair character_print cleavage closed_mouth collarbone commentary_request curvy doruji embarrassed eyes_visible_through_hair face_to_breasts feet fingernails frilled_bikini frills from_above full_body grabbing_another's_ass groping hair_between_eyes hair_over_shoulder halterneck hand_on_another's_ass hand_on_another's_shoulder hetero highres hug kneeling large_breasts legs little_busters! long_hair looking_at_another miiizuno_lbs natsume_kyousuke navel purple_hair simple_background sitting skindentation speech_bubble split_mouth spoken_ellipsis sweat swimsuit toenails toes tsurime very_long_hair wavy_hair white_background white_bikini white_bow yokozuwari
... 1boy 1girl :3 =_= a-chan_(little_busters!) absurdres arm_at_side awkward bare_arms bare_legs bare_shoulders barefoot bikini blue_eyes blush bow bow_bikini breast_press breasts brown_eyes brown_hair character_print cleavage closed_mouth collarbone commentary_request curvy doruji embarrassed eyes_visible_through_hair face_to_breasts feet fingernails frilled_bikini frills from_above full_body grabbing_another's_ass groping hair_between_eyes hair_over_shoulder halterneck hand_on_another's_ass hand_on_another's_shoulder hetero highres hug kneeling large_breasts legs little_busters! long_hair looking_at_another miiizuno_lbs natsume_kyousuke navel purple_hair simple_background sitting skindentation speech_bubble split_mouth spoken_ellipsis sweat swimsuit toenails toes tsurime very_long_hair wavy_hair white_background white_bikini white_bow yokozuwari
1boy awkward bara blush boku_no_hero_academia bunko_(b_unko_3) covering_privates koda_koji looking_at_viewer male_focus muscular muscular_male open_mouth pectorals smile superhero_costume torn_clothes
1boy awkward bara blush boku_no_hero_academia bunko_(b_unko_3) covering_privates koda_koji looking_at_viewer male_focus muscular muscular_male open_mouth pectorals smile superhero_costume torn_clothes
2boys ^_^ armor awkward black_armor closed_eyes deneb ehoumaki food green_armor kamen_rider kamen_rider_den-o_(series) makizushi male_focus momotaros monster monster_boy multiple_boys oni plate red_armor setsubun smile sushi sweat sweatdrop
2boys ^_^ armor awkward black_armor closed_eyes deneb ehoumaki food green_armor kamen_rider kamen_rider_den-o_(series) makizushi male_focus momotaros monster monster_boy multiple_boys oni plate red_armor setsubun smile sushi sweat sweatdrop
4boys armor awkward black_armor black_fur black_shirt blonde_hair blue_eyes blush byleth_(fire_emblem) byleth_(male)_(enlightened)_(fire_emblem) byleth_(male)_(fire_emblem) cape collared_shirt commentary constricted_pupils couple dimitri_alexandre_blaiddyd felix_hugo_fraldarius fire_emblem fire_emblem:_three_houses from_side green_hair green_shirt hair_between_eyes heart highres kiss looking_at_another male_focus medium_hair multiple_boys nintendo purple_hair purple_sweater red_hair shirt short_hair simple_background spiked_hair surprise_kiss surprised sweatdrop sweater sylvain_jose_gautier turtleneck turtleneck_sweater upper_body wa_fe white_background white_fur yaoi
4boys armor awkward black_armor black_fur black_shirt blonde_hair blue_eyes blush byleth_(fire_emblem) byleth_(male)_(enlightened)_(fire_emblem) byleth_(male)_(fire_emblem) cape collared_shirt commentary constricted_pupils couple dimitri_alexandre_blaiddyd felix_hugo_fraldarius fire_emblem fire_emblem:_three_houses from_side green_hair green_shirt hair_between_eyes heart highres kiss looking_at_another male_focus medium_hair multiple_boys nintendo purple_hair purple_sweater red_hair shirt short_hair simple_background spiked_hair surprise_kiss surprised sweatdrop sweater sylvain_jose_gautier turtleneck turtleneck_sweater upper_body wa_fe white_background white_fur yaoi
2girls =_= animal_ears ascot awkward blue_ascot blunt_bangs blunt_tresses bow bowtie brown_hair buttons chrono_genesis_(umamusume) closed_eyes commentary double-breasted ear_ornament earrings epaulettes flying_sweatdrops fukuro_(maruaru00) gloves grey_hair hair_between_eyes headpat height_difference highres horse_ears horse_girl hug jewelry long_bangs long_hair military_uniform multiple_girls naval_uniform perry_steam_(umamusume) puffy_short_sleeves puffy_sleeves purple_bow purple_bowtie purple_shirt sailor_collar sailor_shirt school_uniform shirt short_sleeves sidelocks simple_background single_earring smoke summer_uniform sweatdrop tearing_up tracen_school_uniform umamusume umamusume:_beginning_of_a_new_era white_background white_gloves white_hair white_sailor_collar
2girls =_= animal_ears ascot awkward blue_ascot blunt_bangs blunt_tresses bow bowtie brown_hair buttons chrono_genesis_(umamusume) closed_eyes commentary double-breasted ear_ornament earrings epaulettes flying_sweatdrops fukuro_(maruaru00) gloves grey_hair hair_between_eyes headpat height_difference highres horse_ears horse_girl hug jewelry long_bangs long_hair military_uniform multiple_girls naval_uniform perry_steam_(umamusume) puffy_short_sleeves puffy_sleeves purple_bow purple_bowtie purple_shirt sailor_collar sailor_shirt school_uniform shirt short_sleeves sidelocks simple_background single_earring smoke summer_uniform sweatdrop tearing_up tracen_school_uniform umamusume umamusume:_beginning_of_a_new_era white_background white_gloves white_hair white_sailor_collar