apprentice best from all time

Time frame

Tags

apprentice

1boy1girl 2024 ahoge all_the_way_to_the_base amber_eyes apprentice armor ass bareback bent_over bent_over_desk black_dress blonde_hair blue_eyes books borrowed_character breezebender brown_hair candle candlelight cape cape_aside cock copulating copulation crotchless crotchless_clothes crotchless_clothing crotchless_pantyhose cum_inside_request desk dialogue dialogue_bubble dungeons_and_dragons eyes female_moaning fornicating fornication from_behind from_behind_position gloves half_plate hard_sex holding_hip holding_hips imminent_ejaculation imminent_orgasm internal internal_vaginal internal_view light-skinned_female light-skinned_male long_hair long_hair_female looking_at_another looking_at_partner luccia_(breezebender) luccia_firebrand mage male_moaning mark_(doodlepoodle) markus_neverember medieval medieval_fantasy moaning moaning_girl moaning_in_pleasure moaning_on_cock neverwinter_eye night nylons open_book original original_character pantyhose pantyhose_texture pauldrons penetration penis penis_in_pussy penis_on_ass plate_armor precum precum_drip precum_on_penis purple_dress pussy pussy_penetration raw_sex reading reading_book ripped_clothing ripped_pantyhose self_upload sex sex_from_behind sexual_intercourse side_bangs skindentation speech speech_bubble speech_bubbles spell_book stack_of_books sweat sweatdrop tales_from_the_tables text text_bubble thrusting thrusting_into_pussy tight_clothing tight_pussy tights tome torn_clothes torn_clothing torn_pantyhose two_tone_hair unprotected_sex uterus vaginal_penetration vaginal_sex wizard x-ray
1boy1girl 2024 ahoge all_the_way_to_the_base amber_eyes apprentice armor ass bareback bent_over bent_over_desk black_dress blonde_hair blue_eyes books borrowed_character breezebender brown_hair candle candlelight cape cape_aside cock copulating copulation crotchless crotchless_clothes crotchless_clothing crotchless_pantyhose cum_inside_request desk dialogue dialogue_bubble dungeons_and_dragons eyes female_moaning fornicating fornication from_behind from_behind_position gloves half_plate hard_sex holding_hip holding_hips imminent_ejaculation imminent_orgasm internal internal_vaginal internal_view light-skinned_female light-skinned_male long_hair long_hair_female looking_at_another looking_at_partner luccia_(breezebender) luccia_firebrand mage male_moaning mark_(doodlepoodle) markus_neverember medieval medieval_fantasy moaning moaning_girl moaning_in_pleasure moaning_on_cock neverwinter_eye night nylons open_book original original_character pantyhose pantyhose_texture pauldrons penetration penis penis_in_pussy penis_on_ass plate_armor precum precum_drip precum_on_penis purple_dress pussy pussy_penetration raw_sex reading reading_book ripped_clothing ripped_pantyhose self_upload sex sex_from_behind sexual_intercourse side_bangs skindentation speech speech_bubble speech_bubbles spell_book stack_of_books sweat sweatdrop tales_from_the_tables text text_bubble thrusting thrusting_into_pussy tight_clothing tight_pussy tights tome torn_clothes torn_clothing torn_pantyhose two_tone_hair unprotected_sex uterus vaginal_penetration vaginal_sex wizard x-ray
absurd_res ahe_gao anthro anus apprentice bodily_fluids cum cum_inside double_penetration female gaping gaping_anus gaping_cervix gaping_pussy generation_5_pokemon genital_fluids genitals gigantamax_pokemon gigantamax_urshifu group hi_res hyper_insertion inflation legendary_pokemon looking_pleasured male male/male/female master mienfoo nintendo penetration pokemon pokemon_(species) pussy ridiculous_fit stomach_bulge student teacher teacher_and_student trio v3rg3
absurd_res ahe_gao anthro anus apprentice bodily_fluids cum cum_inside double_penetration female gaping gaping_anus gaping_cervix gaping_pussy generation_5_pokemon genital_fluids genitals gigantamax_pokemon gigantamax_urshifu group hi_res hyper_insertion inflation legendary_pokemon looking_pleasured male male/male/female master mienfoo nintendo penetration pokemon pokemon_(species) pussy ridiculous_fit stomach_bulge student teacher teacher_and_student trio v3rg3
1boy1girl 2024 ahoge amber_eyes apprentice armor ass ass_job belt bent_over bent_over_desk black_dress blonde_hair blue_eyes books borrowed_character breezebender brown_hair buttjob candle candlelight cape cape_aside cock desk dialogue dialogue_bubble dungeons_and_dragons eyes from_behind from_behind_position gloves grinding grinding_through_clothes half_plate holding_hip holding_hips light-skinned_female light-skinned_male long_hair long_hair_female looking_at_another looking_at_partner luccia_(breezebender) luccia_firebrand mage mark_(doodlepoodle) markus_neverember medieval medieval_fantasy neverwinter_eye night nylons open_book original original_character pantyhose pantyhose_texture pauldrons penis penis_on_ass plate_armor precum precum_drip precum_on_penis purple_dress reading reading_book self_upload side_bangs speech speech_bubble speech_bubbles spell_book stack_of_books tales_from_the_tables text text_bubble tight_clothing tights tome two_tone_hair wizard
1boy1girl 2024 ahoge amber_eyes apprentice armor ass ass_job belt bent_over bent_over_desk black_dress blonde_hair blue_eyes books borrowed_character breezebender brown_hair buttjob candle candlelight cape cape_aside cock desk dialogue dialogue_bubble dungeons_and_dragons eyes from_behind from_behind_position gloves grinding grinding_through_clothes half_plate holding_hip holding_hips light-skinned_female light-skinned_male long_hair long_hair_female looking_at_another looking_at_partner luccia_(breezebender) luccia_firebrand mage mark_(doodlepoodle) markus_neverember medieval medieval_fantasy neverwinter_eye night nylons open_book original original_character pantyhose pantyhose_texture pauldrons penis penis_on_ass plate_armor precum precum_drip precum_on_penis purple_dress reading reading_book self_upload side_bangs speech speech_bubble speech_bubbles spell_book stack_of_books tales_from_the_tables text text_bubble tight_clothing tights tome two_tone_hair wizard
apprentice gameplay_mechanics mage mephiscrypie robe skyrim the_elder_scrolls
apprentice gameplay_mechanics mage mephiscrypie robe skyrim the_elder_scrolls
absurd_res aeromercury age_difference amercury anal apprentice bramblepaw bramblestar_(warriors) breath cub domestic_cat duo felid feline felis feral feral_on_feral firestar_(warriors) fur hi_res male male/male male_penetrating mammal mentor moan open_mouth panting penetration sex size_difference warrior warriors warriors_(cats) young younger_male younger_penetrated
absurd_res aeromercury age_difference amercury anal apprentice bramblepaw bramblestar_(warriors) breath cub domestic_cat duo felid feline felis feral feral_on_feral firestar_(warriors) fur hi_res male male/male male_penetrating mammal mentor moan open_mouth panting penetration sex size_difference warrior warriors warriors_(cats) young younger_male younger_penetrated
absurd_res ahe_gao anthro apprentice bodily_fluids cervical_penetration double_penetration female generation_5_pokemon genital_fluids gigantamax_pokemon gigantamax_urshifu group hi_res hyper_insertion large_insertion legendary_pokemon looking_pleasured male male/male/female master mienfoo nintendo penetration pokemon pokemon_(species) ridiculous_fit stomach_bulge student teacher teacher_and_student trio v3rg3 vaginal_fluids vaginal_penetration vaginal_penetration
absurd_res ahe_gao anthro apprentice bodily_fluids cervical_penetration double_penetration female generation_5_pokemon genital_fluids gigantamax_pokemon gigantamax_urshifu group hi_res hyper_insertion large_insertion legendary_pokemon looking_pleasured male male/male/female master mienfoo nintendo penetration pokemon pokemon_(species) ridiculous_fit stomach_bulge student teacher teacher_and_student trio v3rg3 vaginal_fluids vaginal_penetration vaginal_penetration
absurd_res anthro apprentice areola assisted_exposure bite bodily_fluids bondage bound canid canine canis discipline domestic_cat dominant dominant_female dominatrix dripping duo erect_nipples felid feline felis female feral finger_fuck fingering genital_fluids genitals glaria hi_res humiliation magic magic_user mammal master memonius mind_control nipple_piercing nipples pain piercing precum precum_drip puffy_nipples pussy pussy_juice reptile scalie snake tongue tongue_out vaginal_penetration venomous witch wolf
absurd_res anthro apprentice areola assisted_exposure bite bodily_fluids bondage bound canid canine canis discipline domestic_cat dominant dominant_female dominatrix dripping duo erect_nipples felid feline felis female feral finger_fuck fingering genital_fluids genitals glaria hi_res humiliation magic magic_user mammal master memonius mind_control nipple_piercing nipples pain piercing precum precum_drip puffy_nipples pussy pussy_juice reptile scalie snake tongue tongue_out vaginal_penetration venomous witch wolf
1girl 2boys abs absurd_res apprentice artist_request asian_female black_hair blonde_hair blowjob breasts brittney_wong brown_eyes brown_hair caucasian_male cave_girl cavegirl caveman cavewoman closed_eyes completely_naked completely_naked_female completely_naked_male completely_nude_female completely_nude_male disney disney_channel elf elf_ears fellatio feral hairy_balls half-closed_eyes hand_on_another's_shoulder hand_on_shoulder headband hi_res hunter_(the_owl_house) initiation interracial jungle jungle_boy jungle_girl junglegirl large_breasts large_penis long_penis lordofchaos male_focus marco_diaz master mole_under_eye muscles muscular muscular_arms muscular_chest muscular_legs muscular_male naked naked_female naked_male nervous nervous_face nose_piercing nude nude_female nude_male ooga_booga penis prehistoric primal primitive purple_eyes ritual ritual_sex savage savage_land six_pack smiling snu_snu star_vs_the_forces_of_evil stone_age sucking_penis tarzan the_owl_house tooth_necklace training tribal tribal_jewelry uncensored uncensored_penis unga_bunga unga_unga veiny_penis wild
1girl 2boys abs absurd_res apprentice artist_request asian_female black_hair blonde_hair blowjob breasts brittney_wong brown_eyes brown_hair caucasian_male cave_girl cavegirl caveman cavewoman closed_eyes completely_naked completely_naked_female completely_naked_male completely_nude_female completely_nude_male disney disney_channel elf elf_ears fellatio feral hairy_balls half-closed_eyes hand_on_another's_shoulder hand_on_shoulder headband hi_res hunter_(the_owl_house) initiation interracial jungle jungle_boy jungle_girl junglegirl large_breasts large_penis long_penis lordofchaos male_focus marco_diaz master mole_under_eye muscles muscular muscular_arms muscular_chest muscular_legs muscular_male naked naked_female naked_male nervous nervous_face nose_piercing nude nude_female nude_male ooga_booga penis prehistoric primal primitive purple_eyes ritual ritual_sex savage savage_land six_pack smiling snu_snu star_vs_the_forces_of_evil stone_age sucking_penis tarzan the_owl_house tooth_necklace training tribal tribal_jewelry uncensored uncensored_penis unga_bunga unga_unga veiny_penis wild
2girls adapted_costume alternate_costume apprentice areolae arm_under_breasts bangs black_hair blush bodystocking bondage bound breasts bridal_gauntlets cape cleavage cleavage_cutout cosplay covered_navel covered_nipples embarrassed english_text female female_only femdom femsub fire_emblem fire_emblem:_three_houses fire_emblem_awakening holding holding_leash leash leotard limited_palette long_hair looking_at_viewer looking_away lysithea_von_ordelia mage medium_breasts multiple_girls nintendo nipples pelvic_curtain pointing restrained see-through small_breasts student teacher teacher_and_student tethered_angel text tharja_(fire_emblem) tharja_(fire_emblem)_(cosplay) wavy_mouth white_hair yuri
2girls adapted_costume alternate_costume apprentice areolae arm_under_breasts bangs black_hair blush bodystocking bondage bound breasts bridal_gauntlets cape cleavage cleavage_cutout cosplay covered_navel covered_nipples embarrassed english_text female female_only femdom femsub fire_emblem fire_emblem:_three_houses fire_emblem_awakening holding holding_leash leash leotard limited_palette long_hair looking_at_viewer looking_away lysithea_von_ordelia mage medium_breasts multiple_girls nintendo nipples pelvic_curtain pointing restrained see-through small_breasts student teacher teacher_and_student tethered_angel text tharja_(fire_emblem) tharja_(fire_emblem)_(cosplay) wavy_mouth white_hair yuri
2022 absurd_res age_difference anal anal_sex animal_genitalia animal_penis anus apprentice ass ball_size_difference balls bodily_fluids claws clenched_teeth closed_eyes cum cum_from_ass cum_in_ass cum_in_mouth cum_inside cum_on_balls cum_on_face cum_on_penis cum_pool cum_string dirt dirty dirty_feet domestic_cat erection face_fucking felid feline felis fellatio feral feral_on_feral feral_penetrated feral_penetrating feral_penetrating_feral firestar_(warriors) from_behind_position fur gay genital_fluids genitals graystripe_(warriors) group group_sex hi_res irrumatio larger_male lionheart_(warriors) lying male male/male male_penetrated male_penetrating male_penetrating_male mammal mentor messy mounting nude older_male on_back open_mouth oral outside penetration penile penile_penetration penis penis_in_ass plant quadruped saliva sex sheath size_difference smaller_penetrated teeth thathornycat threesome toe_claws tree trio warriors warriors_(cats) young younger_male younger_penetrated
2022 absurd_res age_difference anal anal_sex animal_genitalia animal_penis anus apprentice ass ball_size_difference balls bodily_fluids claws clenched_teeth closed_eyes cum cum_from_ass cum_in_ass cum_in_mouth cum_inside cum_on_balls cum_on_face cum_on_penis cum_pool cum_string dirt dirty dirty_feet domestic_cat erection face_fucking felid feline felis fellatio feral feral_on_feral feral_penetrated feral_penetrating feral_penetrating_feral firestar_(warriors) from_behind_position fur gay genital_fluids genitals graystripe_(warriors) group group_sex hi_res irrumatio larger_male lionheart_(warriors) lying male male/male male_penetrated male_penetrating male_penetrating_male mammal mentor messy mounting nude older_male on_back open_mouth oral outside penetration penile penile_penetration penis penis_in_ass plant quadruped saliva sex sheath size_difference smaller_penetrated teeth thathornycat threesome toe_claws tree trio warriors warriors_(cats) young younger_male younger_penetrated
absurd_res aeromercury age_difference amercury apprentice balls black_body black_fur brown_body brown_fur claws close-up cub domestic_cat duo feet felid feline felis female feral fur genitals glowing glowing_eyes half-erect hi_res hollyleaf_(warriors) hollypaw male male/female mammal markings multicolored_body multicolored_fur orange_eyes paws penile_spines penis size_difference smile smirk solid_color striped_markings stripes tigerclaw tigerstar_(warriors) toes warriors_(cats) young younger_female
absurd_res aeromercury age_difference amercury apprentice balls black_body black_fur brown_body brown_fur claws close-up cub domestic_cat duo feet felid feline felis female feral fur genitals glowing glowing_eyes half-erect hi_res hollyleaf_(warriors) hollypaw male male/female mammal markings multicolored_body multicolored_fur orange_eyes paws penile_spines penis size_difference smile smirk solid_color striped_markings stripes tigerclaw tigerstar_(warriors) toes warriors_(cats) young younger_female
apprentice blush cum cum_on_pussy felid feline felis feral feral_genetalia feral_on_feral incest kitten leafpool_(warriors) lesbian_sex lighting scissoring sobblanket squirrelflight_(warriors) warrior_cats warriors_(cats) watermark yuri
apprentice blush cum cum_on_pussy felid feline felis feral feral_genetalia feral_on_feral incest kitten leafpool_(warriors) lesbian_sex lighting scissoring sobblanket squirrelflight_(warriors) warrior_cats warriors_(cats) watermark yuri
2girls adapted_costume alternate_costume apprentice arm_under_breasts bangs black_hair blush bodystocking bondage bound breasts bridal_gauntlets cape cleavage cleavage_cutout cosplay covered_navel covered_nipples embarrassed english_text female female_only femdom femsub fire_emblem fire_emblem:_three_houses fire_emblem_awakening holding holding_leash leash leotard limited_palette long_hair looking_at_viewer looking_away lysithea_von_ordelia mage medium_breasts multiple_girls nintendo pelvic_curtain pointing restrained small_breasts student teacher teacher_and_student tethered_angel text tharja_(fire_emblem) tharja_(fire_emblem)_(cosplay) wavy_mouth white_hair yuri
2girls adapted_costume alternate_costume apprentice arm_under_breasts bangs black_hair blush bodystocking bondage bound breasts bridal_gauntlets cape cleavage cleavage_cutout cosplay covered_navel covered_nipples embarrassed english_text female female_only femdom femsub fire_emblem fire_emblem:_three_houses fire_emblem_awakening holding holding_leash leash leotard limited_palette long_hair looking_at_viewer looking_away lysithea_von_ordelia mage medium_breasts multiple_girls nintendo pelvic_curtain pointing restrained small_breasts student teacher teacher_and_student tethered_angel text tharja_(fire_emblem) tharja_(fire_emblem)_(cosplay) wavy_mouth white_hair yuri
1girls ai_generated anal_insertion anal_penetration apprentice areolae belly blonde_hair dildo female holding_object hourglass_figure jedi jedi_knight jedi_master jedi_padawan light-skinned_female light_saber light_skin looking_away low_res masturbation medium_hair navel nipples original_character parted_lips patreon_username pubic_hair pussy sith sith_lady slim_waist small_breasts solo solo_female spread_legs squatting star_wars thighs tied_hair wide_hips
1girls ai_generated anal_insertion anal_penetration apprentice areolae belly blonde_hair dildo female holding_object hourglass_figure jedi jedi_knight jedi_master jedi_padawan light-skinned_female light_saber light_skin looking_away low_res masturbation medium_hair navel nipples original_character parted_lips patreon_username pubic_hair pussy sith sith_lady slim_waist small_breasts solo solo_female spread_legs squatting star_wars thighs tied_hair wide_hips
apprentice briarlight_(warriors) comic crying cum felid feline feline_genitalia felis feral_on_feral jayfeather_(warriors) medicine_cat nonconsensual panels rape warrior warriors_(cats) younger_female
apprentice briarlight_(warriors) comic crying cum felid feline feline_genitalia felis feral_on_feral jayfeather_(warriors) medicine_cat nonconsensual panels rape warrior warriors_(cats) younger_female
absurd absurd_res anal animal_genitalia animal_penis anus apprentice balls bodily_fluids bramblestar_(warriors) brown_body brown_fur cum cum_in_ass cum_inside cum_on_ground digital_drawing_(artwork) digital_media_(artwork) domestic_cat ejaculation erection felid feline feline_penis felis feral feralbeans fluffy fluffy_tail fur genital_fluids genitals grass hi_res leaf long_tail looking_at_viewer male mammal nude open_mouth orgasm outside pawpads penile_spines penis plant puffy_anus sand sex smile solo text tongue twig warriors_(cats) water white_body white_fur young
absurd absurd_res anal animal_genitalia animal_penis anus apprentice balls bodily_fluids bramblestar_(warriors) brown_body brown_fur cum cum_in_ass cum_inside cum_on_ground digital_drawing_(artwork) digital_media_(artwork) domestic_cat ejaculation erection felid feline feline_penis felis feral feralbeans fluffy fluffy_tail fur genital_fluids genitals grass hi_res leaf long_tail looking_at_viewer male mammal nude open_mouth orgasm outside pawpads penile_spines penis plant puffy_anus sand sex smile solo text tongue twig warriors_(cats) water white_body white_fur young
2girls apprentice artist_request blue_hair brown_eyes female female_on_top female_only female_with_female green_hair multiple_girls oc orange_eyes scissoring small_breasts tagme the_apprentice the_arcana the_arcana_game tribadism yuri
2girls apprentice artist_request blue_hair brown_eyes female female_on_top female_only female_with_female green_hair multiple_girls oc orange_eyes scissoring small_breasts tagme the_apprentice the_arcana the_arcana_game tribadism yuri
apprentice bite bodily_fluids claws crying digital_drawing_(artwork) digital_media_(artwork) domestic_cat felid feline felis female feral feralbeans finleap_(warriors) forced fur male male/female mammal open_mouth penetration rape sex tears text toe_claws twigbranch_(warriors) warriors_(cats)
apprentice bite bodily_fluids claws crying digital_drawing_(artwork) digital_media_(artwork) domestic_cat felid feline felis female feral feralbeans finleap_(warriors) forced fur male male/female mammal open_mouth penetration rape sex tears text toe_claws twigbranch_(warriors) warriors_(cats)
aggressive angry angry_expression angry_face apprentice armed badge bags_under_eyes big_breasts bloodhoundghostly0 brainwashed brainwashing care_taker crazy curse cursed dangerous dark_blue_outfit dark_blue_skirt daycare_attendant_(pzop) death_wish delightful_mary earrings evil evil_eyes gemusetto_mizu glowing_eyes hair_ribbon heel_shoes holding_object holding_weapon hoop_earrings insane killer long_hair mary_sinorcourt-brimbringers maryanne_brimbringers mature_female medium_breasts misery nail_polish nickelodeon nicktoons outfit pink_bow pink_bowtie pink_eyeshadow pink_lipstick pink_panties poor_unfortunable_soul possessed possession pzop red_hair red_shirt reference_image rockymd serial_killer servant servant_(fate) skirt taser teeth teeth_clenched the_pixiez_oddparents ubisoft uniform uniform_bottom uniform_top villain villainess weapon white_background wife yellow_eyes
aggressive angry angry_expression angry_face apprentice armed badge bags_under_eyes big_breasts bloodhoundghostly0 brainwashed brainwashing care_taker crazy curse cursed dangerous dark_blue_outfit dark_blue_skirt daycare_attendant_(pzop) death_wish delightful_mary earrings evil evil_eyes gemusetto_mizu glowing_eyes hair_ribbon heel_shoes holding_object holding_weapon hoop_earrings insane killer long_hair mary_sinorcourt-brimbringers maryanne_brimbringers mature_female medium_breasts misery nail_polish nickelodeon nicktoons outfit pink_bow pink_bowtie pink_eyeshadow pink_lipstick pink_panties poor_unfortunable_soul possessed possession pzop red_hair red_shirt reference_image rockymd serial_killer servant servant_(fate) skirt taser teeth teeth_clenched the_pixiez_oddparents ubisoft uniform uniform_bottom uniform_top villain villainess weapon white_background wife yellow_eyes