Tag 2000s (style)

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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
13 views
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 – 1female 1girls 2000s 2000s (style) 2d 2d (artwork) 2d artwork ankle cuffs anklet bare arms bare legs bare midriff bare shoulders bare thighs barefoot belly button belly dancer belly dancer outfit big breasts big breasts blue earrings blue gem blue gemstone bra bracelet captured captured girl captured villainess cleavage clouds cobra tiara collar dancer dancer class dancer girl dancer outfit dancer risky boots earrings female only from behind gem gem on forehead gemstone girl girls only gold (metal) gold anklet gold anklets gold bikini gold bra gold bracelets gold collar gold jewelry gold tiara golden anklets golden bikini golden bikini top golden bra golden bracelets golden collar golden tiara grass harem girl harem jewelry harem outfit heart pasties held up highlights (coloring) lake lakeside loincloth metal collar midriff navel only female only girl open mouth orange tentacles pale-skinned female pale skin palm tree pulling on thong pulling panties purple hair purple heart pasties purple loincloth red eyes risky boots shantae shantae and the pirate’s curse slave slave bikini slave collar slave outfit slavegirl suckers tanline island tentacle tentacle tentacles around arms tentacles around legs tentacles around wrists tentacles everywhere tentacles on female tentacles under clothes text text box text bubble thick thighs tiara trapped unhinged-honey water | 11733837
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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
8 views
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
12 views
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
8 views
Rule 34 – 2000s 2000s (style) 2d 2d (artwork) 2d artwork 5girls advance wars advance wars: dual strike afro arms above head bare arms bare legs bare midriff bare shoulders bare thighs barefoot belly button belly dancer belly dancer outfit black bra black hair black skirt blue bra blue skirt bra brown hair cleavage dancer class dancer girl dancer outfit dancing empty eyes feet female only femsub girls only gray eyes green bra green headband green skirt harem harem girl harem girls harem jewelry harem outfit harem pants headband heart shaped bra heart symbol hypnosis hypnotic eyes hypnotized female intelligent systems jess (advance wars) lash (advance wars) leaning forward light-skinned female light skin long hair micro bikini midriff multiple girls multiple subs navel nintendo only female only girl orange bra orange hair orange skirt overboob rabbit0 red background red hair sami (advance wars) sasha (advance wars) see-through see-through clothing see-through dress see-through shirt see-through veil short hair sideboob slave slave outfit smile sonja (advance wars) tagme tan skin tan skinned female theneko thick thighs twintails underboob veil white skin white skinned female yellow bra yellow highlights yellow skirt | 11408999
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Rule 34 – 1080p 1440×1080 2000s 2000s (style) 2000s and 2010s style 2002 2boys 2d 8girls animated assistance baseball bat beating begging for mercy begging to stop behind closed doors big breasts black heels blue hair female blush blushing at another bondage bondage harness book breasts brought to obedience candle candle wax ceiling light chains crazed look drool earrings english audio english dialogue english dub english voice english voice acting erection erection under clothes evil laugh evil smile feet tied female masturbation female moaning femsub fondling breasts grandfather green eyes hands tied hi res high resolution highres irony kenichi sakaki kurashiki anna lip gloss long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute male maledom milf milky animation label mother and daughter mp4 multiple girls nipple clamps nipples over 480p peeing peeing self pillory pubes pussy spanking red dress red hair ribbon red heels resisting pleasure rope rope harness ryona sadism saliva secretly loves it slave smug face sound spanking spanking ass spectating stepping on head stone floor tears tied hair torture uncensored upset urine video voice acted watching waver wax on breasts wet pussy wooden horse wooden horse (device) yasue kurashiki younger female | 10412597
16 views
Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2003 2boys 2d 2d (artwork) 2men 2on1 4girls 960×540 abuse of power acquiescent female anal juice anal juice trail anal licking begging to stop big breasts blonde female blonde hair blonde hair female blue eyes blue eyes female bothered breast fondling breast grab breasts dark shell death dirty talk double penetration english audio english dub english voice acting female female soldier fingering anus fingering pussy forced forced to watch fukushima hiroshi giving in to pleasure gunshot hands on back headshot hi res high resolution highres indoors indoors sex kobeyakawa aki konishi yuuka kuroda letting it happen licking anus licking breasts light-skinned female 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 soldier married woman military clothing military uniform mp4 nipple tweak nude female nutech digital over 480p peeing peeing after sex peeing female purple hair female pussy juice pussy juice trail rape resisting pleasure short hair short hair female smoking sniper sound standing sex tagme ukita moe ukita tomoko uncensored until they like it upset upskirt urine video voice acted watching watching sex whimpering | 11058074
10 views
Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2d 2girls 3boys abs alcoholic drink animated announcing orgasm bartender beer big breasts black hair female black heels breast grab breasts brown eyes captured heroine cellphone city clothed clothed male criminal cross earrings cum cum inside cum on body cum on face deceit drug dubbed version english dialogue english dub english voice english voice acting enjoying rape facial female female moaning female pubic hair fingering fingering pussy forced forced oral glasses handcuffs hi res high resolution highres implied murder inner thoughts investigation investigator jewelry karen (vinus file) kidnap knife lactating during sex lactating nipples lactation leggings lipstick long hair long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute male meganekko mp4 multiple boys necklace nipples nutech digital overdose penis phone pink panties planning pubes pubic hair public exposure rape rapist red lips red lipstick resisting pleasure rio (vinus file) ripped leggings secretly loves it shin ban megami tantei vinus file sound squirt squirting orgasm straight tricked uncensored upset van veiny penis video voice acted watching watching rape wavy hair | 10990973
11 views
Rule 34 – 00s 1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2003 2d 2d animation 2girls abuse of power adolescent adult and teenager adult male afraid age difference angry animated begging to stop big man blonde female blood breast fondle breasts calling for help crying crying female cum cum in pussy cum in uterus cum inside dark shell death defloration drool ejaculation explicitly stated nonconsent female female death female moaning fertilization fingering pussy forced forced kiss gun helpless female hentai high resolution highres impregnation killing kissing licking licking nipples licking panties longer than 30 seconds longer than 3 minutes longer than one minute male military military clothing military uniform mind break mp4 muscular male no bra nutech digital old man older impregnating younger older male older man and teenage girl ovum panicking panting peeing petite female pistol pussy rape resisting saliva scar sex shirt shirt lift short hair short hair female size difference small breasts soldier sound sperm cell sperm meets ovum tagme tall male tears teenage girl third-party edit traumatize traumatized ukita moe ukita tomoko uncensored until they like it unwanted creampie unwanted impregnation vaginal juices vaginal penetration veteran video virgin virginal blood voice acted war crime x-ray | 10946668
15 views
Rule 34 – 2000 2000s 2000s (style) 2000s and 2010s style 2d 3girls 720p ahe gao ail soft akiyama asuka anal anal rape anal sex anal through clothes animated animation assisted rape assisted sex blow blue hair blue hair female breasts breasts out breasts out of clothes bride defloration deflowered deflowering doggy style doggy style position dominant female double penetration elbow gloves english subtitles female female assisted rape female domination female focus female only femdom femsub fff threesome forced in fabric forced yuri glasses indoors japanese voice acting kyouhaku lesbian rape lesbian sex lipstick long hair longer than 2 minutes longer than 30 seconds longer than one minute lowres miyazaki yumiko mp4 multiple girls nipple licking nutech digital panties penetration penetration through clothes pink pineapple rape red hair red lipstick screencap sex toy short hair sound strap-on strap-on sex teacher threesome uncensored vaginal blood vaginal penetration vaginal rape video virgin virginal blood virginity loss voice acted wedding dress yuri yuuki aya | 10955771
10 views
Rule 34 – 00s 1080p 1440×1080 1boy 1boy1girl 1girls 2000s 2000s (style) 2000s and 2010s style 2004 2d 2girls animated big ass black hair male blush bondage harness bouncing breasts breast fondling breast grab breasts brown hair brown hair female caught masturbating city consensual cowgirl position cum cum on face dat ass dirty talk drool dubbed version earrings english dialogue english dub english voice english voice acting erection erection through clothing erection under clothes facial fellatio female female masturbation female moaning female pubic hair fingering pussy food full moon grey eyes huge breasts hugging inner thoughts jewelry karen (vinus file) lactating lactating nipples large penis lipstick long brown hair long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute male male/female male pubic hair mature female meganekko moon moonlight mp4 night nipples not a virgin nutech digital older female over 480p pinching nipples pink bra pink panties pretending to be unaware pubes pubic hair pussy juice red lips red lipstick red rope rooftops rope harness saliva self fondle sex shin ban megami tantei vinus file shocked male sound spying stomach noises straddle straight taking a nap thighhighs thinking about sex tied hair uncensored vaginal penetration vaginal sex veiny penis video voice acted watching watching sex wavy hair younger male | 10955620
8 views
Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2d 2d (artwork) 2d animation 2girls 3boys abs alcoholic drink animated announcing orgasm bartender beer big breasts black hair female black heels breast grab breasts brown eyes captured heroine cellphone city clothed male criminal cross earrings cum cum inside cum on body cum on face deceit drug dubbed version english audio english dialogue english dub english voice english voice acting enjoying rape facial female female moaning female pubic hair fingering fingering pussy forced forced oral glasses handcuffs hi res high resolution highres implied murder inner thoughts investigation investigator jewelry karen (vinus file) kidnap knife lactating during sex lactating nipples lactation leggings lipstick long hair long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute meganekko multiple males necklace nipples nutech digital overdose phone pink panties planning pubes pubic hair public exposure rape rapist red lips red lipstick resisting pleasure rio (vinus file) ripped leggings secretly loves it shin ban megami tantei vinus file squirt squirting orgasm straight tagme tricked uncensored upset van veiny penis video voice acted watching watching rape wavy hair | 10990973
6 views
Rule 34 – 1boy 1boy1girl 1girls 2000s 2000s (style) 2000s and 2010s style 2002 2d 540p 960×540 abs angry animated animation apartment audible ejaculation begging big breasts blackmail blue eyes blue eyes female bondage breasts convulsing convulsions cum cum in pussy cum inside defloration deflowering delivery delivery man dildo dirty talk dubbed version electric shock electricity electro electrodes electrostimulation english dub english voice english voice acting erect nipples erect penis faceslap female female rapist forced indoors inner thoughts interrogation justified rape karma kay yuzuiri living sex toy delivery longer than 30 seconds longer than 3 minutes longer than 4 minutes longer than 5 minutes longer than one minute male male rape victim milk mp4 muscles muscular muscular female muscular sub nipples nutech digital over 480p penis photos rape red hair female restrained restraint revenge revenge rape reverse rape secretly loves it sex sex toy shock shocked shocking short hair silver hair silver hair female sound spasm spasming spasms straight strap-on sucking penis sweat sweaty body table tied down twitching uncensored until they like it vaginal creampie vaginal penetration vaginal sex veiny penis video virgin virginity loss voice acted wires | 10856933
14 views
Rule 34 – 2000 2000s 2000s (style) 2000s and 2010s style 2d 2d (artwork) 2d animation 3girls 720p ahe gao ail soft akiyama asuka anal anal rape anal sex anal through clothes animated animation assisted rape assisted sex blow blue hair blue hair female breasts breasts out breasts out of clothes bride defloration deflowered deflowering doggy style doggy style position dominant female double penetration elbow gloves female assisted rape female domination female focus female only femdom femsub fff threesome forced in fabric forced yuri glasses hentai indoors kyouhaku lesbian lesbian rape lesbian sex lipstick long hair longer than 2 minutes longer than 30 seconds longer than one minute lowres miyazaki yumiko multiple girls nipple licking nutech digital panties penetration through clothes pink pineapple rape red hair red lipstick screencap short hair sound strap-on strap-on sex tagme teacher threesome uncensored vaginal blood vaginal penetration vaginal rape video virgin virginal blood virginity loss wedding dress yuri yuuki aya | 10955771
13 views
Rule 34 – 00s 1080p 1440×1080 1boy1girl 1girl1boy 2000s 2000s (style) 2000s and 2010s style 2003 3males 5girls aggressive angry male announcing orgasm begging to stop blame blonde hair blonde hair female breast grab breast squeeze broken rape victim brown hair brown hair female building clothed male crazy crazy look creampie crying cum cum on face dark shell dubbed version english audio english dialogue english dub english voice english voice acting faceslap facial female forced forced oral forced sex forced to watch fukushima hiroshi glasses grey eyes hi res high resolution highres holding female indoors ishida rie konishi yuuka leggings letting it happen 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 male soldier meganekko military clothing military uniform missionary position mp4 multiple females night nutech digital peeing piledriver position purple hair purple hair female pussy juice rape restrained female restraining slap sound spanking spanking ass tagme trying to stop rape ukita tomoko uncensored until they like it urine utika moe video virgin voice acted walking away watching watching rape white bra white hair male white leggings white panties | 10963355
10 views
Rule 34 – 2000 2000s 2000s (style) 2000s and 2010s style 2d 2d (artwork) 2d animation 3girls 720p ahe gao ail soft akiyama asuka anal anal rape anal sex animated animation assisted rape blow blue hair blue hair female breast bride defloration deflowered deflowering double penetration female female focus female only fff threesome forced in fabric glasses hentai indoors kyouhaku lesbian sex lipstick longer than 2 minutes longer than 30 seconds longer than one minute lowres miyazaki yumiko multiple girls nutech digital penetration through clothes pink pineapple rape red lips red lipstick school screencap sex strap-on tagme teacher uncensored vaginal blood vaginal penetration vaginal rape video virgin virginal blood virginity loss yuri yuuki aya | 10955771
9 views