Tag 2000s and 2010s style

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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
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Rule 34 – 00s 1080p 1440×1080 1boy 1boy1girl 1girls 2000s 2000s and 2010s style 2004 2d 2d (artwork) 2d animation 3girls animated anime big breasts bisexual (female) black hair blue eyes blue eyes female blue hair blue hair female blush breasts brown hair brown hair female building caught cheating caught in 4k caught in the act cellphone clothed male coercion cowgirl position creampie cum cum inside cum overflow cum trail day daytime dirty talk doggy style elf (company) english dub english voice english voice acting female femsub flashback ghost giving in to pleasure grabbing penis groping penis hd hentai hi res highres hosome eyes indoors itou kisaku kashiwagi ayano kimisaki hiromi kimisaki hiromi (kisaku) kisaku kisaku spirit lipstick long hair female long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute male mp4 nipples no bra office orange hair female over 480p phone phone ringing pink dress pink pineapple possession red lips red lipstick seduction seductive body seductive look sex shiraishi momoko (kisaku) shocked shocked expression short hair shy male sound straight supernatural sweat sweaty table tagme tears tears of pleasure ugly man uncensored upset vaginal penetration vaginal sex video voice acted what did he say yellow eyes yellow eyes female yellow towel | 9598745
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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
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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
7 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
11 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
7 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
4 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
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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
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 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
9 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
6 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
5 views
Rule 34 – 1boy 1girls 2000 2000s 2000s and 2010s style 2d 2d (artwork) 2d animation ahe gao ail soft akiyama miku animated animation barefoot blow blush breast breasts defloration deflowered deflowering female female focus hairbun hairbuns hentai hetero sex hi res high resolution highres intercourse kyouhaku longer than 30 seconds longer than one minute lowres male nude nude female nutech digital perky nipples petite petite body petite breasts petite female pink hair pink hair female pink pineapple pubic hair purple eyes purple eyes female rape retro school sex small breasts straight straight straight sex tagme teacher vaginal blood vaginal penetration vaginal rape vaginal sex video virgin virginal blood virginity loss young young female young woman | 10956275
5 views
Rule 34 – 00s 1080p 1440×1080 1boy 1boy1girl 1girl1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2004 2d 2d (artwork) 2d animation 2girls big ass black hair male blush bondage harness boobs 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 audio 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/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 tagme taking a nap thighhighs thinking about sex tied hair tits uncensored vaginal penetration vaginal sex veiny penis video voice acted watching watching sex wavy hair younger male | 10955620
4 views
Rule 34 – 00s 1080p 1440×1080 1boy 1boy1girl 1girl1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2004 2d 2d (artwork) 2d animation 2girls bondage harness bouncing breasts brown hair brown hair female city consensual cowgirl position cum cum on face dubbed version earrings english audio english dialogue english dub english voice english voice acting erection erection through clothing erection under clothes facial fellatio female masturbation female pubic hair fingering pussy food grey eyes huge breasts jewelry karen (vinus file) large penis lipstick long video longer than 30 seconds longer than 3 minutes longer than 5 minutes longer than one minute male pubic hair mature female meganekko mp4 night not a virgin nutech digital older female over 480p pubes pubic hair pussy juice red lips red lipstick red rope rooftops rope harness sex shin ban megami tantei vinus file sound spying stomach noises straddle straight tagme thighhighs thinking about sex uncensored vaginal penetration vaginal sex veiny penis video video voice acted watching watching sex wavy hair younger male | 10955620
3 views
Rule 34 – 00s 1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2003 2d 2d (artwork) 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 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 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 | 10946668
7 views
Rule 34 – 00s 2000s 2000s (style) 2000s and 2010s style 2003 2d 2d (artwork) 2d animation 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 creampie crying crying female cum cum in pussy cum inside dark shell death defloration drool 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 nakadashi no bra nutech digital old man older impregnating younger older male older man and teenage girl ovum panicking panting peeing petite female pistol 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 until they like it unwanted creampie unwanted impregnation vaginal juices vaginal penetration veteran video virgin virginal blood voice acted war crime | 10946668
5 views
Rule 34 – 00s 1boy 2000s 2000s (style) 2000s and 2010s style 2d 2girls 720p all fours animated armbinder assertive female audible ejaculation bad girl black lips black lipstick blindfold bondage breasts brown hair brown hair female ceiling light chains chikami yukari (kurohime: shikkoku no yakata) clothed clothed female collar cum cum drip cum dripping from ass cum on ass cum on back cumshot cunnilingus dirty talk discovery (company) doggy style dominatrix drool dungeon english audio english dub english voice english voice acting female femdom femsub forced bondage forced cunnilingus forced partners hi res high resolution highres indoors kurohime: shikkoku no yakata kurohime (spd) licking ass licking nipples lipstick long hair long hair female longer than 2 minutes longer than 30 seconds longer than one minute male male/female male and female subs malesub maya (kurohime: shikkoku no yakata) mouth gag mp4 multiple subs multiple subs one dom mutual rape naked nipples nude nude female nude male over 480p pubes pubic hair saliva sex sex slave shorter than 3 minutes shorter than five minutes shorter than four minutes slave sound straight submissive submissive female tongue tongue in anus uncensored vaginal penetration vaginal sex video voice acted | 10920687
6 views
Rule 34 – 1boy 1boy1girl 1girl1boy 1girls 2000s 2000s (style) 2000s and 2010s style 2002 2d 2d (artwork) 2d animation 540p 960×540 abs angry animated animation apartment audible ejaculation begging big breasts blackmail blue eyes blue eyes female bondage breasts convulsing convulsions creampie cum cum in pussy cum inside defloration deflowering delivery delivery man dildo dirty talk dubbed version electric shock electricity electro electrodes electrostimulation english audio english dub english voice english voice acting erect nipples erect penis faceslap 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 shock shocked shocking short hair silver hair silver hair female sound spasm spasming spasms straight strap-on sucking penis sweat sweaty body table tagme tied down twitching uncensored until they like it vaginal creampie vaginal penetration vaginal sex veiny penis video virgin virginity loss voice acted wires | 10856933
5 views
Rule 34 – 1080p 1boy1girl 1girl1boy 2000s and 2010s style 2010s 2020s 2d 2d (artwork) 3girls :>= alternate version available artist name ass back view beach big ass big breasts blonde female blonde hair blue lips blue lipstick butt crack cum cum on ass cum on body dat ass deepthroat ero-enzo erza scarlet faceless male fairy tail fat man fellatio female female focus hi res high resolution highres hyper ass hyper breasts indoors kiss mark laxus dreyar lipstick lipstick mark lipstick on penis lipstick on stomach long red hair lucy heartfilia mirajane strauss mp4 no sound nude male oral outdoors nudity over 480p red hair red hair female red lips red lipstick rtenzo silver hair silver hair female silver lips silver lipstick slideshow squatting sucking sucking penis tagme tattoo tattoo on arm tattoo on ass thick ass thick thighs unseen male face veiny penis video wide hips writing on ass writing on wall | 10813145
9 views