playboy best from all time

Source

Type

Order

Time frame

playboy

14girls 6+girls aladdin anna_(frozen) ariel arms atlantis:_the_lost_empire beauty_and_the_beast belle blue_background brave breast_size_difference breasts casual chel crossover dark-skinned_female dark_skin disney disney_fairies disney_princess dreamworks elsa_(frozen) esmeralda fa_mulan female female_only footwear frozen_(film) gradient_background hands height_difference human kida legs light-skinned_female lineup looking_at_viewer merida minko mulan multiple_girls neckwear nipples nude nude_female nudist open_toe_shoes pale-skinned_female pale_skin peter_pan_(disney) pixar playboy pocahontas pocahontas_(character) princess princess_jasmine pussy rapunzel skin_tone_difference take_your_pick tan-skinned_female tangled the_hunchback_of_notre_dame the_little_mermaid the_princess_and_the_frog the_road_to_el_dorado tiana tinker_bell white_background wristwear

aladdinanna_(frozen)

1boy 1girls 2023 :o after_anal after_sex alternate_version_available anus ass back back_view balls barstool barstool_position big_ass big_penis blue_hair body_markings body_writing chair completely_nude cum cum_drip cum_in_ass cum_inside cyberpunk:_edgerunners cyberpunk_2077 duo erection eyes_rolling_back feet feet_together female fi_zz_ill from_behind from_behind_position gaping gaping_anus genital_fluids genitals green_eyes green_hair grey_background grey_body grey_skin hair heart hearts_around_head hi_res human human_on_humanoid humanoid large_ass large_penis legs_together light-skinned_male light_skin long_hair looking_pleasured male male/female male_human/female_humanoid naked nude nude_female penis penis_grab penis_on_ass playboy pleasure_face ponytail presenting presenting_hindquarters pussy pussy_juice pussy_juice_drip rear_view rebecca_(edgerunners) red_sclera simple_background sitting sitting_on_chair soles standing steam steaming_body steamy_breath stool stool_position straight straight_hair sweat sweatdrop testicles thick_thighs thighs uncensored vagina vaginal_juices vulva wet_pussy

1girls areolae belly belly_button blush breasts dark-skinned_female dark_skin female_only freckles green_eyes looking_away malberrybush malyna nipples pinup playboy ponytail pussy red_hair shirt_lift shorts_down stomach sweat text thighs

1girls azusagawa_sakuta big_breasts bunny_ears cosplay kittew mirror mirror_selfie playboy playboy_bunny pubic_hair purple_hair pussy reverse_bunnysuit sakurajima_mai seishun_buta_yarou_wa_bunny_girl_senpai_no_yume_wo_minai self_shot thick_thighs thighs vagina

azusagawa_sakutabig_breasts

1girls areolae belly belly_button blush breasts dark-skinned_female dark_skin freckles green_eyes implied_sex innuendo looking_away magazine magazine_cover malberrybush malyna nipples no_bra peal_malyna pinup playboy ponytail pun pussy red_hair shirt_lift shorts_down stomach superheroine sweat text thighs tomboy

aladdin aladdin_(1992_disney_film) anna_(frozen) areola areolae ariel ariel_(the_little_mermaid) armpit armpits asymmetrical athletic athletic_female atlantis:_the_lost_empire bare bare_arms bare_breasts bare_chest bare_hips bare_shoulders bare_skin beauty_and_the_beast beauty_and_the_beast_(1991_film) belle belle_(beauty_and_the_beast) big_areola big_breasts big_girl big_woman black_eyes black_hair blonde blue_eyes blush bottomless brave breasts brown_eyes brown_hair brown_skin chel child_bearing_hips collar completely_naked completely_nude curvy curvy_figure cute_face dark-skinned_female dark_skin disney disney_princess earrings elsa_(frozen) embarrassed embarrassed_female esmeralda eyelashes eyeshadow fa_mulan face_markings fairy_wings female female_focus female_only fit fit_female flowing_hair freckles freckles_on_face frozen_(film) genitals ginger green_eyes hair hairless_pussy hand_on_hip hand_on_own_hip high_heels highres hips hourglass_figure huge_breasts human human_only kida large_breasts leaning_on_hand legs light-skinned_female light_skin lingerie lipstick long_hair looking_at_viewer makeup mascara massive_breasts mature medium_breasts merida midriff milf minko mulan mulan_(1998_film) naked naked_female navel necklace nipples no_ass non-web_source nude nude_female older_female olena_minko on_model on_side orange_hair perky peter_pan_(disney) petite petite_body petite_breasts petite_female pink_hair platter playboy playboy_bunny playboy_bunny_logo plump_labia pocahontas pocahontas_(character) posing princess princess_jasmine purple_eyes pussy rapunzel red_hair seductive seductive_look seductive_smile shaved_pussy sisters skinny slim slim_girl slim_waist smile smile_at_viewer smiling smooth_skin solo_female standing stomach straight_hair tagme tan_body tan_skin tangled teenager the_little_mermaid the_little_mermaid_(1989_film) the_princess_and_the_frog the_road_to_el_dorado thick_thighs thighs thin_waist tiana tight_pussy tinker_bell topless topless_female two_tone_hairvagina white_hair wide_hips young young_female young_woman younger_female

aladdinaladdin_(1992_disney_film)

1girls ass barcode big_ass big_butt big_thighs black_text bottom_view brown_background brown_hair butt capcom chun-li dat_ass earrings english_text fat_ass female female_only hairbun hands_on_ass huge_ass huge_butt large_ass lava_(artist) magazine magazine_cover modeling necklace nude nude_female nudity playboy playboy_magazine posing red_text ring spreading_ass spreading_cheeks street_fighter street_fighter_v sweat sweaty sweaty_ass sweaty_thighs text thick_thighs yellow_text

2020s 2021 3girls alternate_breast_size ann_possible april april_(month) big_breasts bikini black_heels black_high_heels bonnie_rockwaller breast_grab bubble_butt cleavage clothing disney disney_channel english_text fake_magazine_cover female female_only footwear full_body g-string gagala high_heels kim_possible kimberly_ann_possible large_breasts looking_at_viewer magazine_cover medium_breasts milf mother_and_daughter no_socks phillipthe2 playboy playtoon posing pumps red_hair red_heels red_high_heels redhead sling_bikini sling_swimsuit slingshot_bikini slingshot_swimsuit standing thong thong_bikini

alternate_breast_sizeann_possible

1:1 2girls 3d alex_(minecraft) ass big_ass big_breasts blue_eyes breasts bunny_ears bunnysuit clothed clothing cuteskyler fat_ass female female_only flower_in_hair green_eyes hand_on_hip huge_ass huge_breasts light-skinned_female light_skin looking_at_viewer looking_back mine-imator minecraft playboy playboy_bunny skyler_quinn stripper thick_thighs wide_hips

alex_(minecraft)ass

$2girls \(genshin address ai_generated animal ass back bare behind black blue brown bunny ear focus from from_below furina_(genshin_impact) genshin_impact hair hat headwear highleg hu_tao_(genshin_impact) huge huge_ass impact\) leotard long multicolored patreon playboy playboy_bunny porkpie rabbit rac3rrr racerai red shoulders tail thighhighs thighs top twintails two-tone$

\(genshinaddress

1girls blonde_female blonde_hair bunny_costume bunny_ear bunny_ears bunny_girl bunny_tail bunnysuit disney disney_channel disney_xd facing_viewer female female_only lying_on_floor mossa on_knees playboy playboy_bunny solo solo_female star star_butterfly star_vs_the_forces_of_evil straight_hair teen teenager white_female

blonde_femaleblonde_hair

alcohol alcohol_bottle alcohol_bottles alcoholic alcoholic_beverage alcoholic_drink blush blush_lines blushing_at_viewer bottle breasts bunny bunny_costume bunny_ear bunny_ears bunny_girl bunny_tail bunnysuit cleavage clothing demon demon_girl demon_horns demon_humanoid demoness female helltaker leggings looking_at_viewer malina_(helltaker) open_mouth playboy playboy_bunny playboy_bunny_costume playboy_bunny_leotard playboy_outfit red_eyes short_hair short_hair_female thick thick_ass thick_hips thick_legs thick_thighs thigh_highs thigh_socks thigh_strap thighhighs thighs usa37107692

alcoholalcohol_bottle

1boy 1girls black_skin bunny_brawler bunny_costume bunnysuit english_text fortnite fortnite:_battle_royale gradient_background halloween halloween_costume luna_(fortnite) mavolier nipple_cover_dress playboy playboy_bunny simple_background speech_bubble tagme uncensored video_games

black_skinbunny_brawler

1girls 2d 2d_(artwork) ass ass_focus big_ass big_butt black_hair bob_cut bottom_heavy bubble_butt bunny_ears bunny_girl bunny_tail bunnysuit butt butt_focus clothed clothed_female clothing female female_only fubuki_(one-punch_man) green_eyes haruhisky high_heels human human_female human_only light-skinned_female light_skin looking_at_viewer looking_back no_sex one-punch_man paag pantyhose playboy realistic_proportions short_hair sideboob simple_background smile smile_at_viewer solo solo_female thick_ass thick_thighs white_background young_woman

2017 5girls :3 animal_humanoid anthro big_breasts blonde_hair blush bowtie breast_grab breasts buckteeth bunnie_rabbot bunny_costume bunnysuit busty cleavage clothed clothing collar cosplay crossover cuffs_(disambiguation) cybernetics cyborg dark_skin detached_collar disney easter english_text eyebrows eyelashes eyeshadow female female_only final_fantasy fur furry group hair hand_on_ass hand_on_breast high_res holidays hourglass_figure huge_breasts humanoid judy_hopps lagomorph large_breasts legwear leotard lola_bunny looking_at_viewer looney_tunes lopunny machine mammal medium_breasts multicolored_fur nintendo open_mouth playboy pokémon_(species) pokemon pokemon_(species) rabbit rabbit_humanoid secretly_saucy sega simple_background size_difference small_breasts smile sonic_(series) square_enix standing tail teeth text thick_thighs tight_clothing tights video_games viera voluptuous warner_brothers white_hair wide_hips wrist_cuffs zootopia

:3animal_humanoid

1boy 1girls ai_generated anime anime_style big_ass big_balls big_breasts big_butt big_penis blonde_hair blonde_hair_female bunny bunny_costume bunny_ear bunny_ears bunny_girl bunny_tail bunnysuit cheating cheating_girlfriend cuck cuckold cuckold_pov cuckolding curvaceous curves curvy curvy_body curvy_female curvy_figure dark-skinned_male english_text female fishnets high_school_student highschool inky_bias kitagawa_marin male mirror mirror_selfie penis playboy playboy_bunny playboy_bunny_leotard qos sex sono_bisque_doll_wa_koi_wo_suru standing standing_sex text thick thick_ass thick_legs thick_penis thick_thighs

ai_generatedanime

2futas 3d alternate_version_available blizzard_entertainment dark-skinned_futanari dark_skin duo egyptian fareeha_amari femshoptop futa_on_futa futa_only futanari hung_bottom hung_futanari illari_(overwatch) illari_quispe_ruiz nyl_pharah overwatch overwatch_2 pharah playboy

alternate_version_availableblizzard_entertainment

3d amanda_de_santa arms_above_head arms_behind_head black_hair black_panties cheating cheating_wife cleavage collarbone erect_nipples expressionless female_focus female_only femsub ga3ddolls grand_theft_auto grand_theft_auto_v hat huge_breasts lingerie navel netorare ntr open_clothes panties playboy raining short_hair solo text thick_thighs thong unamused wet

amanda_de_santaarms_above_head

1girls 3d amanda_de_santa bare_shoulders blue_eyes cheating cheating_wife cleavage collarbone dialogue erect_nipples expressionless female_focus female_only femsub ga3ddolls grand_theft_auto grand_theft_auto_v huge_breasts milf navel netorare ntr parody playboy raining red_lipstick skirt solo text topless unamused wet_breasts wet_clothes

amanda_de_santabare_shoulders

1girls 3d belt breasts dreadlocks female female_only fun_shaundi hand_on_pussy joint playboy saints_row saints_row_2 shaundi smoking solo topless

1futa 3d 3d_(artwork) alternate_version_available blizzard_entertainment casual dark-skinned_futanari dark_skin femshoptop futa_only futanari human illari_(overwatch) intersex magazine_cover overwatch overwatch_2 peruvian playboy

alternate_version_availableblizzard_entertainment

1boy bara brown_hair bunny_ears charluiu crossdressing five_nights_at_freddy's fnaf hip_dips lingerie looking_at_viewer magazine_cover male male_lingerie male_only michael_afton painted_nails playboy playboy_bunny purple_shirt shirt_in_mouth shirt_pull shitpost solo solo_male thighs

1boy 1girls arm_grab arms_behind_back asta_(black_clover) black_clover bunnysuit doggy_style immortalkingart large_breasts leotard muscular_male nipples noelle_silva pantyhose playboy playboy_bunny playboy_bunny_leotard princess purple_eyes rabbit_ears raised_tail royalty sex_from_behind silver_hair twintails

arm_grabarms_behind_back

1girls armpits blank_background blush blush_lines blushing_at_viewer bridget bridget_(guilty_gear) bunny bunny_costume bunny_ear bunny_ears bunny_girl bunnygirl bunnysuit green_eyes guilty_gear heart hearts_around_body hearts_around_head looking_at_viewer plain_background playboy playboy_bunny playboy_bunny_costume playboy_bunny_leotard playboy_outfit playboy_suit rule_63 supacreamss white_background

armpitsblank_background

3d 4girls areolae ariel aurora_(sleeping_beauty) beauty_and_the_beast belle breasts bunny_ears crisisbeat crossover dawn_(princess_quest) detached_collar disney disney_princess elsa_(frozen) eyeshadow female_only fingering frozen_(film) kneeling large_breasts lipstick makeup marina_(princess_quest) masturbation naked nipples nude pinup playboy playboy_bunny pose posing princess princess_quest pussy pussy_juice royalty sleeping_beauty_(1959_film) tan tanline the_little_mermaid winter_(princess_quest)

blue_hair bunny_ears bunny_girl female genjiruu high_heels hip_dips horny neon_(valorant) playboy playboy_bunny playboy_bunny_costume playboy_outfit solo valorant

blue_hairbunny_ears

anthro ass bandai_namco big_ass big_breasts big_butt breasts bunny_ears bunnysuit clothed clothing dialogue digimon digimon_(species) english_text female fishnet fur furry furry_only heart latex legwear looking_back pantyhose playboy pussy rena_(yourdigimongirl) renamon tail text wide_hips yourdigimongirl

1girls ass ass_cleavage big_ass big_breasts bimbo bimbofication bow breast_implants breasts bubble_gum butt_crack cleavage clothed clothing dancing english_text enormous_breasts eyewear feline female food furry graffiti headband hoop_earrings huge_ass huge_breasts hyper hyper_breasts implants long_tail looking_back mammal minx_kitten nike playboy pole pole_dancing ponytail shiny simple_background slit_pupils smutbunny speech_bubble streetwear stripper stripper_pole sweatpants text thick_thighs tied_hair trainers urban wide_hips

assass_cleavage

anthro bow bowtie bunny_ear bunny_ears bunny_girl bunnysuit cat_lingerie catgirl collar degrading demon demon_girl excited feathers fishnet fishnet_legwear helluva_boss horn horns imminent_sex lingerie lipstick maid maid_dress maid_uniform mayberry_(helluva_boss) multiple_females multiple_girls multiple_subs objectification offering offering_to_viewer owl owl_humanoid pink_skin playboy playboy_bunny red_eyes seductive seductive_look seductive_mouth seductive_smile stella_(helluva_boss) succubus three_on_one threesome verosika_mayday_(helluva_boss) white_fur white_hair

2girls 3d big_breasts brecca_(smz-69) busty curvaceous curvy curvy_figure dark_hair female_only hourglass_figure lara_croft lara_croft_(survivor) long_hair magazine magazine_cover naked naked_female narrow_waist nude_female playboy playboy_magazine rude_frog slim_waist smz-69 thigh_gap tomb_raider voluptuous wide_hips

big_breastsbrecca_(smz-69)

1:1 3_toes 4_fingers 4_toes 5_fingers 5_toes a_link_to_the_past absurd_res alien anal anal_beads anal_sex animal_humanoid animatronic anthro archie_comics balls beastars bisexual black_eyes black_sclera blue_balls blue_eyes bonnie_(fnaf) brown_nails bucky_o'hare bucky_o'hare_(series) bunnie_rabbot bunnymund carrot_(one_piece) cherry_blossom claws closed_eyes clothing cream_the_rabbit crossover cybernetics cyborg digimon digimon_(species) disney easter easter_bunny egg eyewear feet female female/female final_fantasy final_fantasy_xiv fingernails fingers five_nights_at_freddy's five_nights_at_freddy's_2 flower foot_fetish furry genitals gloves green_balls green_eyes group group_sex handwear hare haru_(beastars) hi_res holidays humanoid humanoid_feet humanoid_hands jack_savage judy_hopps kissing lagomorph lagomorph_humanoid large_breasts leporid link link_(rabbit_form) lola_bunny looney_tunes lopunny machine male male/male male_lopunny mammal mammal_humanoid masturbation max_(sam_and_max) medium_breasts nail_polish nicecream_man nintendo no893 one_eye_closed one_piece oral_sex orange_nails orgy parsnip_(game) parsnip_bunner pawpads penetration penis peppy_hare petals phone pikachu pink_balls pink_penis plant playboy pokémon_(species) pokemon pokemon_(species) pokemon_dppt pokemon_rgby pokemon_ss pussy rabbit red_eyes red_nails rise_of_the_guardians robot sam_and_max scorbunny sex sex_toy soles sonic_(series) sonic_the_hedgehog_(archie) sonic_the_hedgehog_(comics) spring_(season) square_enix star_fox straight terriermon the_legend_of_zelda toe_claws toenail_polish toenails toes toy_bonnie_(fnaf) train_position tree undertale vaginal_masturbation vaginal_penetration vanilla_the_rabbit video_games viera warner_brothers white_balls white_nails white_penis zootopia

a_link_to_the_pastabsurd_res

1girls ai_generated ass ass_focus ass_grab back back_view bare_back bare_shoulders big_ass big_breasts black_hair breasts bubble_butt bunny_ears bunnysuit cleavage collar curvaceous curvy curvy_female curvy_figure dat_ass elbow_gloves female female_only front_view hourglass_figure huge_ass large_ass large_breasts latex massive_ass nai_diffusion original pale-skinned_female partially_clothed playboy playboy_bunny round_ass short_hair skin_tight slim_waist stable_diffusion thick_thighs thighhighs thighs thunder_thighs tight_clothing viewed_from_below voluptuous voluptuous_female yo_dayo_(ai)

ai_generatedass

2022 arm_stockings ass big_ass big_breasts blush bowtie breasts bunnysuit easter female female_only garter_straps hair hi_res highres horn horns looking_back monster monster_girl my_singing_monsters parlsona playboy ponytail sideboob solo srnava tail thick_thighs video_games werdo werdos_(msm)

arm_stockingsass

1girls 3d bandana belt breasts brown_hair covering dreadlocks female female_only fun_shaundi gun in-game kneeling lip_piercing long_hair looking_at_viewer marijuana medium_breasts nipples nude playboy saints_row saints_row_2 shaundi smile smoking smoking_weed solo tattoo

1girls ai_generated ass ass_cleavage ass_focus ass_grab back back_view bare_back bare_shoulders big_ass big_breasts black_hair breasts bubble_butt bunny_ears bunnysuit butt_crack cleavage collar curvaceous curvy curvy_female curvy_figure dat_ass elbow_gloves female female_only front_view hourglass_figure huge_ass large_ass large_breasts latex massive_ass nai_diffusion original pale-skinned_female partially_clothed playboy playboy_bunny round_ass short_hair skin_tight slim_waist stable_diffusion thick_thighs thighhighs thighs thunder_thighs tight_clothing viewed_from_below voluptuous voluptuous_female yo_dayo_(ai)

ai_generatedass

1boy abs ai_generated anal anus ass bangs blonde_hair blush bow braid bulge bunny clothes clothing cloud cloud_strife cloudy covered crease crop crossdressing easter_egg erection feet femboy final_fantasy final_fantasy_vii grabbing ground hairband indoors insertion jewelry knee knees lace lace-trimmed looking_at_viewer makeup male male_focus male_only muscular nail_polish panties pectorals peek penis pink_fingernails playboy presenting rabbit see-through shoulders sidelocks signature sitting sleeveless solo solo_male spread stomach testicles thigh thighhighs thighs thong toes toned turtleneck twintails underwear wet window xsfmworks

absai_generated

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