Tag 2000s and 2010s style

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Rule34 – 00s 1boy 2000s 2000s_(style) 2000s_and_2010s_style 2girls 960×540 advertising anal_bleeding anal_virgin angry big_breasts bisexual_female bleeding_from_anus blonde_female blonde_hair_female blood bondage bondage_outfit box breasts candle_wax candles captured_female computer crime cum cum_in_mouth cum_on_face delivery_man dildo dirty_talk dominatrix drinking_pee dubbed_version english_audio english_dub english_voice english_voice_acting evidence evil_female facial female_collaborator female_masturbation female_pervert female_pubic_hair femsub fingering fingering_pussy green_eyes_female groping_own_breasts horny_female horseplay implied_crime latex_armwear latex_bodysuit latex_stockings licking_breasts licking_pussy lip_gloss long_hair_female longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute male_rape_victim mansion moaning_in_pain moaning_in_pleasure multiple_girls nutech_digital object_insertion over_480p painal payback peeing photo planning pubes pubic_hair public_humilation public_indecency punishment pussy_juice rape red_latex red_latex_armwear red_latex_legwear revenge revenge_rape rope rope_bondage rope_tied rough_sex sadism sadistic_girl sex_dungeon sex_slave short_hair shower sitting_pee spread_pussy spying stun_gun tape taser tied_hair tokudachi_ayame uncensored urinating_female urination urine vibrator video videotape wax_on_body wax_on_breasts wealthly_female whip whipping whipping_butt yuka_(living_sex_toy_delivery)
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Rule 34 – 2000s 2000s and 2010s style 2010s 2d 2d (artwork) 2d artwork 90s ai ai art ai generated anime anime style bare arms bare legs bare midriff bare shoulders bare thighs barefoot belly button belly dancer belly dancer outfit bikini bikini top blush blushing at viewer bracelet collar crossover crossover cosplay eyelashes forest forest background ginger ginger hair gold (metal) gold bracelets gold collar gold hair ornament gold jewelry golden bracelets golden collar golden hair ornaments green bikini green bikini top green bra green eyes hair ornament harem girl harem outfit kasumi (pokemon) lake lakeside light-skinned female light skin loincloth looking at viewer metal bra metal bracelet metal collar midriff moon moonlight navel night night sky pokemon pokemon (anime) pokemon anime ponytail red loincloth short hair slave slave bikini slave collar slave leia slave leia (cosplay) slave outfit slavegirl star wars stars thick thighs trees | 12876516
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Rule34 – 00s 2+boys 2000s 2000s_(style) 2000s_and_2010s_style 720p 960×720 ass_grab brown_hair_female brown_hair_male cellphone central_park_media clothed_female clothed_male confident_smile drool dubbed_version elf_ears english_audio english_dub english_voice english_voice_acting female_moaning female_orgasm fingering fingering_another fingering_from_behind garter_belt garter_straps green_dress grey_hair grey_hair_male grope grope_from_behind groping hd hd_(traditional) impressed informative inner_thoughts lavender_hair lip_gloss lipstick long_hair long_hair_female long_purple_hair longer_than_2_minutes longer_than_30_seconds longer_than_one_minute low_twintails moustache multiple_girls old_man over_480p panting policewoman purse shades shorter_than_five_minutes shorter_than_four_minutes sunset train train_interior trying_not_to_cum uncensored undercover_policewoman video wet_pussy white_panties
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Rule34 – 00s 2000s 2000s_(style) 2000s_and_2010s_style 2girls 6boys 720p 960×720 anal_fingering ass_grab assisted_fingering blue_eyes_male blue_hair blue_hair_female bra_down breast_fondle breast_grab brown_hair_male central_park_media clothed_female clothed_male cum cum_on_ass cum_on_clothes cum_on_face day dildo elf_ears elf_male english_audio english_voice english_voice_acting facial female female_moaning fingered_from_behind fingering fingering_pussy grabbed_from_behind grey_hair grey_hair_male grope_from_behind groping ground_vehicle guided_handjob hd hd_(traditional) holding_baby inner_thoughts letting_it_happen long_hair long_hair_female long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute milf mother moustache multiple_boys multiple_girls not_really_rape old_man over_480p panties_down pee_puddle peeing penis pink_panties pink_panties_down public pulling_panties red_eyes red_eyes_female scar scar_on_eye schoolgirl secretly_loves_it sex shades skirt squirt stealth_sex sunset surrounded_by_men sweat tears tears_of_pleasure temptation train train_interior unable_to_resist unaware_sex uncensored urine vibrator vibrator_in_pussy vibrator_on_nipple video voyeurism wet_pussy young_female young_male
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Rule34 – 00s 2000s 2000s_(style) 2000s_and_2010s_style 2boys 720p 960×720 almost_caught ass_grab blue_eyes_male blue_hair blue_hair_female brown_hair_male central_park_media clothed_female clothed_male convincing english_audio english_voice english_voice_acting female female_moaning fingered_from_behind fingering fingering_pussy grabbed_from_behind grope_from_behind groping handshake hd hd_(traditional) implied_crime initiation inner_thoughts letting_it_happen long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute multiple_boys multiple_girls old_man pee_puddle peeing public red_eyes red_eyes_female scar scar_on_eye schoolgirl sex shades shocked shocked_expression shocked_look skirt smoke squirt standing_doggy_style standing_sex stealth_sex sweat tears tears_of_pleasure telepath temptation train unable_to_resist unaware_sex uncensored urine video voyeurism wet_pussy young_female young_male
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Rule34 – 1boy 1girls 2000s_and_2010s_style ahoge aquamarina areolae ass_pillow bed bed_sheet braid breasts chibi chibi_style female large_breasts mob_face nipples penetration pillow sex straight vagina vaginal_penetration
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Rule34 – 00s 2000s 2000s_and_2010s_style 2girls 720p 960×720 arrest attempted_rescue beer big_breasts black_hair black_hair_female breasts brown_hair brown_hair_female computer computer_screen criminal cum cum_in_pussy cum_inside cum_on_body cum_on_breasts dirty_talk doggy_style dubbed_version english_audio english_dub english_voice english_voice_acting female female_moaning female_orgasm flashback gangbang gangrape happy_ending hd implied_crime indoors inner_thoughts inverted_nipples karen_(the_venus_files) kidnapped_female lactating lactating_breasts lactation leggings lipstick long_black_hair long_hair long_hair_female long_video longer_than_10_minutes longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute masturbating_partner mature_female mature_male meganekko necklace night nighttime nipples non-virgin not_a_virgin nutech_digital older_female orgasm orgasm_denial over_480p pubes pubic_hair pussy rape rapist_male red_leggings red_lips red_lipstick rescue resisting_pleasure rio_(the_venus_files) sex sex_slave shin-ban_megami_tantei_vinus_file smug_face squirt squirting stun_gun syringe trap uncensored vaginal_penetration vaginal_sex veiny_penis video wanting_sex watching wavy_hair
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Rule 34 – 00s 2000s 2000s and 2010s style 2004 2d 2d (artwork) 2d animation 2girls arrest attempted rescue beer big breasts black hair black hair female breasts breasts breasts brown hair brown hair female computer computer screen criminal cum cum in pussy cum inside cum on body cum on breasts dirty talk doggy style dubbed version english audio english dub english voice english voice acting female female moaning female orgasm flashback gangbang gangrape happy ending hd hi res high resolution highres implied crime indoors inner thoughts inverted nipples karen (the venus files) kidnapped female lactating lactating breasts lactation leggings lipstick long black hair long hair long hair female long video longer than 10 minutes longer than 2 minutes longer than 30 seconds longer than 3 minutes longer than 4 minutes longer than 5 minutes longer than one minute masturbating partner mature female mature male meganekko mp4 necklace night nighttime nipples non-virgin not a virgin nutech digital older female orgasm orgasm denial over 480p pubes pubic hair pussy rape rapist male red leggings red lips red lipstick rescue resisting pleasure rio (the venus files) sex sex slave shin-ban megami tantei vinus file smug face sound squirt squirting stungun syringe tagme trap uncensored vaginal penetration vaginal sex veiny penis video video voice acted wanting sex watching wavy hair | 12343129
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Rule34 – 00s 1futa1girl 1girl1futa 2000s 2000s_(style) 2000s_and_2010s_style 4girls attempted_escape barefoot big_breasts big_penis blonde blonde_female blonde_hair blonde_hair_female blue_hair blue_hair_female blush boobjob bouncing_breasts breast_grab breasts choker cum cum_on_face decapitation dirty_talk doggy_style dubbed_version english_audio english_dub english_voice english_voice_acting enjoyment extreme_content facial female_moaning female_warrior freya_(ikusa_otome_valkyrie) futanari futanari/female futanari_masturbation futanari_transformation green_eyes green_eyes_female hip_grab indoors kitty_media lip_gloss long_blonde_hair long_blue_hair long_hair_female long_twintails long_video longer_than_2_minutes longer_than_30_seconds longer_than_3_minutes longer_than_4_minutes longer_than_5_minutes longer_than_one_minute losing_resistence male_orc mole mole_under_eye nun over_480p penis_creature red_eyes red_eyes_female red_hair red_hair_female red_twintails sex size_difference standing_doggy_style sweat sword tile_floor tiles trying_to_resist twintails_(hairstyle) uncensored vagina vaginal_sex video wanting_sex watching watching_sex
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Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2001 2d 2d animation 5+girls 6girls akagawa rika anal expulsion angry male animated anime style asakawa kotomi begging to stop big breasts bitch taken for walk black hair female boobjob boobs braided hair braided twintails breasts brown hair brown hair female chains clothed male creampie cum cum in pussy cum inside cum on face defloration deflowering dirty talk distress domination drinking urine drool dubbed version enema english audio english dub english voice english voice acting explicitly stated nonconsent facial forced forced urination helpless female hentai series hi res high resolution highres indoors inner thoughts isaku isaku respect japanese female licking licking pussy licking through clothes listening long hair long hair female long twintails long video longer than 10 minutes longer than 2 minutes longer than 30 seconds longer than 3 minutes longer than 4 minutes longer than 5 minutes longer than one minute microphone mikihara akemi mp4 nipple piercing nipples nonconsensual nutech digital older dom older male over 480p pants down peeing pervert male pink hair female pink pineapple rape rape victim rope bondage rope tied sakaki miyuki saliva serizawa mio socks sound speakers squatting squirt stomach noises straight submissive female tagme takashima kumi tears tears of sadness tits twintails uncensored unwanted creampie unwanted impregnation unwanted sex urinating female urine video videotape virginity loss voice acted voyeurism whip mark on butt whip marks whipping younger female | 11526926
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Rule 34 – 00s 1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2002 720p animated bed bedroom bible black big breasts breasts cum cum in pussy cum on body cum on upper body doggy style english audio english dialogue english text english voice acting fellatio female fingering grabbing another’s breast groping handjob large breasts long hair milky animation label minase taki nipples nude older woman and younger man oral orgasm over 480p pubic hair purple eyes purple eyes female red hair sex sex from behind sound standing standing sex straight subtitled tagme takashiro hiroko teacher teacher and student uncensored underwear vaginal penetration video voice acted wanting more | 11662996
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Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2boys 2d 2d (artwork) 2d animation 6girls 720p 960×720 acquiescent female akagawa rika all fours asakawa kotomi ass licking audible ejaculation beaten up bitch taken for walk black hair female black hair male blowjob boobjob boobs braid braided hair braided twintails breasts brought to obedience brown eyes brown eyes female ceased resistance chains clothed male nude female cock worship cum cum on body cum on face cumshot dominant male domination double penetration dream dubbed version ejaculation elf (company) english audio english dub english voice english voice acting facial fellatio femsub fever dream giving up helpless helpless female hosome eyes indoors inner thoughts isaku isaku respect licking penis long brown hair long hair long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute loser male rapist maledom medium breasts meganekko mikihara akemi moaning moaning girl nipples ntr obedience older dom older male older male younger female older man and teenage girl older penetrating younger one leg raised over 480p paizuri peeing pink eyes female pink hair female pink pineapple pubic hair pussy rape rapist rimjob sakaki miyuki serizawa mio sex sex slave sound submissive female tagme takashima kumi tits torment twin braids twintails ugly man uncensored urinating female urine vaginal penetration video voice acted whimpering whip whip marks whipping butt younger female younger male | 11564190
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Rule 34 – 00s 1boy 1futa 2000s 2000s (style) 2000s and 2010s style 2001 3girls all fours amatsuki jun anal anal fingering anal sex animated ass ass grab assisted sex bad acting bad voice acting bible black big breasts big penis bisexual female blonde female blonde futa blonde hair blue hair blush bouncing breasts breast grab breast press breasts brown hair candle candles closed eyes clothed clothes removed completely nude completely nude female completely nude futanari completely nude male covered in cum creampie cum cum in ass cum in pussy cum on body cum on face cumming while penetrating dfm threesome dickgirl dickgirl/female dickgirl penetrating doggy style double breast grab double creampie double penetration english audio english dialogue english dub english voice english voice acting facial female collaborator female masturbation female moaning ffm threesome finger on nipple fingering fingering partner fucked silly full-package futanari futa only futa sans balls futa with female futanari grabbing another’s breast grabbing own breast green eyes groping group sex kitami reika kurimoto maki large breasts light blue hair lips long hair longer than 3 minutes longer than one minute lowres lying magic circle male male penetrating masturbating masturbation medium breasts milky animation label minase taki missionary position moaning multiple girls nail polish nipples nude on back on floor open mouth panties panties around one leg panties removed penis penis in ass penis in pussy ponytail pubic hair purple eyes purple nails rape reverse cowgirl double penetration reverse cowgirl position saeki kaori sex sex from behind shiraki rika short hair shorter than five minutes shorter than four minutes sidelocks sorcery sound spread legs sweat sweatdrop tagme teamwork threesome twintails uncensored undressing vaginal penetration video voice acted witch witches | 11621259
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Rule 34 – 00s 1boy 2000s 2000s (style) 2000s and 2010s style 2002 5girls 720p 960×720 anal sex anorexic apologizing assertive female begging for more bible black bible black gaiden big breasts black hair female blonde female blonde hair blonde hair female blue eyes blue eyes female book breast grab breasts cowgirl position cum cum in pussy cum inside displeased doggy style english audio english dub english voice english voice acting forced groping groping breasts hairbow hi res high quality high resolution highres hiratani seiichi indoors infatuation kitami reika kozono nami long hair long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute magic milky animation label missionary position mp4 muscular male nipple pinching nipple tweak nipples over 480p ponytail pubic hair purple hair purple hair female rejection request rie morita school school uniform schoolgirl sex skinny male sorcery sound spoon position straight tagme takashiro hiroko thighhighs tits uncensored upset vagina vaginal penetration vaginal sex video virgin male voice acted wanting more witchcraft yellow eyes yellow eyes female yuri | 11606122
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Rule 34 – 00s 1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2002 720p animated bed bedroom bible black breasts cum cum in pussy cum on body cum on upper body doggy style english audio english dialogue english text english voice acting fellatio female fingering grabbing another’s breast groping handjob large breasts long hair milky animation label minase taki nipples nude older woman and younger man oral orgasm over 480p pubic hair purple eyes purple eyes female red hair sex sex from behind sound standing standing sex straight subtitled tagme takashiro hiroko teacher teacher and student uncensored underwear vaginal penetration video voice acted wanting more | 11662996
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Rule 34 – 00s 1boy 2000s 2000s (style) 2000s and 2010s style 2002 6+boys 720p all fours amatsuki jun anal anal creampie anal lube anal penetration anal virgin animated anus ass audible creampie audible ejaculation bed begging to stop bent over bible black black dress blonde hair blue eyes blush bouncing breasts breasts brown hair chains choker cleavage closed eyes clothes lift collar compliment cross cross earrings cum cum in ass cum inside cum leaking cum leaking out of anus dirty talk doggy style dominant female dress dubbed version earrings ejaculation english audio english dialogue english dub evil female forced anal forced partners from behind green eyes green eyes female hanging breasts imari kurumi insults jewelry kitami reika kneeling large breasts lipstick long hair long hair female longer than 30 seconds longer than 3 minutes longer than one minute lowres makeup male moaning milky animation label minase taki moaning multiple girls naughty face nipples nude on floor open mouth over 480p panties penis pillow ponytail pubic hair purple eyes pussy rape saeki kaori sex sex from behind short dress short hair shorter than five minutes shorter than four minutes side ponytail sideboob skirt skirt lift sorceress sound sweat tagme teal eyes thighhighs thighs tongue top-down bottom-up uncensored underwear until they like it video witch | 11629638
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Rule 34 – 00s 1280×720 1boy 2000s 2000s (style) 2000s and 2010s style 2001 2d 2d (artwork) 2d animation 6+girls animated animation asking a question bad acting barefoot bible black big breasts black cloak blonde female blonde hair blonde hair female blue eyes blue eyes female boobs boyfriend-girlfriend brown hair brown hair female candles candlestick captured girl ceased resistance chains chastity belt clothed male collar confession cross earrings defiant at first dirty talk drugs dubbed version embarrassed nude female english audio english dialogue english voice english voice acting erection under pants female pervert femdom folding fondling breasts forced forced to watch giving in grabbing penis through clothes green eyes green eyes male hair ornament hi res high resolution highres imari kurumi implied masturbation indoors kitami reika lipstick long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute magic circle milky animation label minase taki moaning mp4 nail polish night nighttime nipples nonconsensual nude female older female older female younger female over 480p ponytail purple nail polish purple nails resisting resisting drugs restrained restraining secretly horny side ponytail sorceress sound table tagme takashiro hiroko teal eyes tits touching pussy uncensored video villainess virgin watching younger female | 11703108
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Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2003 2boys 2boys1girl 2d 2on1 4girls 960×540 abuse of power acquiescent female anal anal juice anal juice trail anal licking anilingus animated arm grab arms above head ass begging to stop big breasts blonde female blonde hair blonde hair female blue eyes blue eyes female bothered bra breast fondling breast grab breasts clothed clothes removed cum cum in ass cum in pussy cum inside dark-skinned female dark shell death dirty talk double breast grab double penetration english dub english voice acting female female soldier fingering anus fingering pussy forced forced to watch fukushima hiroshi giving in to pleasure group group rape gunshot hands on back headshot hi res high resolution highres indoors indoors sex karma kissing kobeyakawa aki konishi yuuka kuroda leg lift letting it happen licking anus licking breasts light-skinned female light-skinned male light skin listening to sex long hair female long purple hair long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute male male death male soldier married woman military clothing military uniform mp4 naked naked footwear nipple suck nipple tweak nipples nude nude female nutech digital over 480p panties peeing peeing after sex peeing female penetration penis penis in pussy pubic hair purple hair female pussy juice pussy juice trail rape rapist male resisting pleasure reverse forced oral rimming rimming female short hair short hair female smoking sniper sound standing standing double penetration standing on one leg standing sex ukita moe ukita tomoko uncensored until they like it upset upskirt urine vaginal penetration video voice acted watching watching sex whimpering | 11058074
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Rule 34 – 00s 1boy 2000s 2000s (style) 2000s and 2010s style 2002 6+boys 720p all fours amatsuki jun anal anal lube anal penetration anal virgin animated anus ass bed begging to stop bent over bible black black dress blonde hair blue eyes blush bouncing breasts breasts brown hair chains choker cleavage closed eyes clothes lift collar cross cross earrings cum doggy style dominant female dress dubbed version earrings english audio english dialogue english dub forced anal forced partners from behind green eyes green eyes female hanging breasts imari kurumi insults jewelry kitami reika kneeling large breasts lipstick long hair long hair female longer than 30 seconds longer than 3 minutes longer than one minute lowres makeup minase taki moaning multiple boys multiple girls naughty face nipples nude on floor open mouth over 480p panties penis pillow ponytail pubic hair purple eyes pussy rape saeki kaori sex sex from behind short dress short hair shorter than five minutes shorter than four minutes side ponytail sideboob skirt skirt lift sound tagme thighhighs thighs tongue top-down bottom-up uncensored underwear video | 11629638
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Rule 34 – 2000 2000s 2000s and 2010s style 2d 2d (artwork) 2d animation 2girls 3boys age difference ahe gao ail soft akiyama miku animated animation anus balls balls deep barefoot blow blush bouncing breasts breast breasts carrying position completely nude completely nude female cowgirl position crying cum cum drip cum dripping cum dripping out of pussy cum gushing cum in pussy cum inside cum leaking cum leaking out of pussy cum overflow cum puddle deep penetration defloration deflowered deflowering double penetration english subtitles erect nipples female female focus female rape victim forced forced to watch hairbun hairbuns hentai hetero sex hi res high resolution highres hymen torn intercourse japanese dialogue kyouhaku larger male leaking leaking cum longer than 30 seconds longer than one minute loss of virginity male missionary position moaning nipples nude nude female nutech digital older male older man and younger girl older penetrating younger penis penis in pussy perky nipples petite petite body petite breasts petite female pink hair pink hair female pink pineapple pubes pubic hair purple eyes purple eyes female pussy rape raped female restrained retro reverse suspended congress school school girl screaming sex size difference small breasts smaller female stand and carry position straight straight sex subbed version subtitled tagme teacher teen teen girl teenage girl teenager testicles thrusting uncensored vaginal blood vaginal penetration vaginal rape vaginal sex video virgin virginal blood virginity loss young young female young girl | 10956275
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