Tag 1999

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Rule 34 – 1990s 1999 1boy 1girls 20th century anilingus areolae arms behind back ass blue background blush bondage breasts clothing color dark-skinned male dark skin duo female genkindo human human only interracial kasumi (pokemon) male nipples open mouth oral oral sex orange eyes orange hair pokemon pussy rape reverse forced oral shirt shirt lift small breasts spread legs straight tears tongue | 150374
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Rule 34 – 1999 1girls breasts closed eyes dark-skinned female dark skin female female only long hair mihoshi kuramitsu monochrome ootake pashio solo tagme tenchi muyo! uncensored | 150010
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Rule 34 – 1990s 1999 20th century boots breast grab breasts faceless male female high heel boots human human only james (pokemon) jessie (pokemon) male meowth nintendo pokemon straight team rocket thigh boots zone | 149951
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Rule 34 – 1990s 1999 1girls 20th century female karin kanzuki rorita rorisuke straight hair street fighter tagme | 149537
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Rule 34 – 1999 2girls aerith gainsborough blush bound together breasts brown hair collar cute erect nipples female female only femsub final fantasy final fantasy vii green eyes huge breasts human large breasts linked collar multiple girls multiple subs nipples pink nipples red eyes see-through straight hair sugitaka aoya tifa lockhart yuri | 149516
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Rule 34 – 1990s 1999 1girls 20th century akira (artist) blue eyes breasts cum curvaceous female green hair horns humanoid large breasts light-skinned female light skin long hair looking at viewer lum nipples oni pointy ears princess pussy solo tagme urusei yatsura | 149234
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Rule 34 – 1990s 1999 1girls 20th century bandeau blue eyes blush bracelet breasts curvaceous dark-skinned female dark skin earrings female fushigi no umi no nadia gainax human jewelry kou (rall2) large breasts loincloth lying nadia la arwall neck ring nipples on back panties princess purple hair shirt lift short hair solo top lift tubetop underwear vest white background white panties | 149165
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Rule 34 – 1990s 1999 20th century 2boys closed eyes cuddle darth maul greyscale horns jedi jedi padawan kneeling male monochrome nude obi-wan kenobi sith sith lord sketch star wars tattoos the phantom menace yaoi zabrak | 148940
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Rule 34 – 1990s 1999 1boy 20th century barefoot blackrose collar cup jedi jedi padawan kneeling male male only nipples nude obi-wan kenobi star wars the phantom menace | 148893
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Rule 34 – 1990s 1999 20th century age difference bed darth maul gay jedi jedi master jedi padawan liam neeson male male/male male only mirsch missionary multiple males obi-wan kenobi qui-gon jinn sith sith lord star wars tattoos the phantom menace voyeur yaoi zabrak | 148892
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Rule 34 – 1990s 1999 1boy 20th century bathing darth maul flaccid male male only penis sith solo star wars the phantom menace towel waterfall wine dragon zabrak | 148889
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Rule 34 – 1990s 1999 20th century 2boys average sized penis bending backwards blackrose closed eyes collar crossed legs erect nipples flaccid flaccid penis head thrown back head tilt jedi jedi master jedi padawan male male only nipples nude obi-wan kenobi penis qui-gon jinn star wars the phantom menace | 148888
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Rule 34 – 1990s 1999 1girls 20th century artist name ass black canary breasts dated dc dc comics dinah lance english text female female only fishnets green arrow (series) human keltic long hair monochrome nipples nude solo thought bubble uncensored | 148242
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Rule 34 – 1990s 1999 1boy 1girls 20th century cain marko covered in cum des manders erect penis female interracial juggernaut male marvel marvel comics monochrome ororo munroe penis sex storm (x-men) straight straight hair tiara x-men | 148240
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Rule 34 – 1999 1girls 3boys all holes anal anal sex arche klein ass ass up bending over breasts christmas christmas headwear christmas outfit clothed sex clothing cum cum on face cumshot dated exposed breasts female foursome gangbang half elf handjob happy happy sex light-skinned male light skin light skinned female long hair male mil (artist) nipples on all fours one eye closed pink hair pussy sex signature small breasts smile straight tales of (series) tales of phantasia teenager tongue tongue out unseen male face vaginal vaginal sex witch | 147747
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Rule 34 – 1990s 1999 1girls 20th century 2d all fours anthro ass babs bunny barefoot bow breasts carrot closed eyes fatalis female female only fur furry furry ass furry breasts furry ears furry tail insertion mammal masturbation nude open mouth pink fur rabbit raised tail side view solo tail tiny toon adventures toony traditional media uncensored white fur | 147647
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Rule 34 – 1990s 1999 20th century animaniacs anthro breasts female female only front view fur furry tail hair mammal minerva mink mink mustelid nipples on one foot pussy solo standing tagme tail yellow fur yellow hair | 147645
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Rule 34 – 1999 a goofy movie anthro anthro only beerman clothing disney female female pubic hair max goof nipples pubic hair roxanne (goof troop) | 147627
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Rule 34 – 1990s 1999 1girls 20th century breasts des manders female gloriana (meggan puceanu) marvel marvel comics nipples solo straight hair x-men | 147570
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Rule 34 – 1990s 1999 20th century bar censor cammy white censored female female only human momoi nanabei solo straight hair street fighter tagme | 146722
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