<!DOCTYPE html><html lang="en"><head><meta charset="utf-8"><meta name="viewport" content="width=device-width,initial-scale=1,maximum-scale=1,user-scalable=no,shrink-to-fit=no"><title>Guess That Ass</title><link rel="stylesheet" type="text/css" href="https://htlbid.com/v3/barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/barstoolsports.com/htlbid.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push((function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("authorId","40"),htlbid.setTargeting("Verity_keywords",["ass | barstool sports","beanies","hats","flag","hoodies","more shop","big game | new football t-shirts","ana cheri","gear","holiday mood","little sexy santa ass","weather","job"]),htlbid.setTargeting("Verity_IABv1",["IAB17","IAB17-12"]),htlbid.setTargeting("Verity_IABv2",["484","483"]),htlbid.setTargeting("Verity_IABv3",["484","483"]),htlbid.setTargeting("Verity_positive","0.33"),htlbid.setTargeting("Verity_neutral","0.67"),htlbid.setTargeting("Verity_GGT5_conf","VERY_HIGH"),htlbid.setTargeting("Verity_GGT5_risk","HIGH"),htlbid.setTargeting("Verity_GGT4_conf","VERY_HIGH"),htlbid.setTargeting("Verity_GGT4_risk","HIGH"),htlbid.setTargeting("is_testing","no"),htlbid.layout()}))</script><script>var googletag = googletag || {};
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        pbjs.setConfig({ pageUrl: https://www.barstoolsports.com/blog/438668/guess-that-ass-501 });</script><script src="https://d9rde3y35j061.cloudfront.net/script.js"></script><script src="https://htlbid.com/v3/barstoolsports.com/htlbid.js" async></script><script src="https://iframely.barstoolsports.com/embed.js" async></script><style>.union__content{font-family:-apple-system,HelveticaNeue,Roboto,sans-serif;font-weight:400;font-size:18px;color:#5a5b5d;word-wrap:break-word;box-sizing:border-box;padding:0 5px 32px 5px}.union__content p{padding:0;margin:16px 0 0 0}.union__content img{display:block;width:100%!important;height:auto;margin:16px 0 0 0}.union__content video{display:block!important;width:100%!important;height:auto;margin:16px 0 0 0}.union__content .articleAd{text-align:center;margin:16px 0 0 0;background-color:#f5f5f5}.union__content .htlad__container{display:inline-block}.union__content p a{color:#377dc4}.union__content .oembed__wrapper{margin:16px 0 0 0}.union__content blockquote:not(.twitter-video){display:block;margin:16px 0 0 0;padding:4px 12px;border-left:4px solid #77889a;font-style:italic;background:#f0f4f8;text-align:left;border-radius:0 6px 6px 0}.union__content blockquote:not(.twitter-video) p{font-style:italic}.union__content blockquote,q{quotes:none}.union__content iframe{max-width:100%}.union__content .bs-image-hidden{display:none}.union__content div.hq-image{width:fit-content;margin:0 auto}.union__content span.image-attribution,.union__content span.image-attribution a{color:#757575;font-size:12px;font-style:italic;letter-spacing:.1px;line-height:14px;text-decoration:none;padding:0;margin:0}.union__content .bs-videoPlayer .bs-videoPlayer__container,.union__content video-js,.wp-video{width:100%!important;height:0!important;position:relative;padding-bottom:56.25%;overflow:hidden;margin:16px 0 0 0}.wp-video video{width:100%!important;height:100%!important}.hq-image video{width:100%!important;height:100%!important}.union__content .bs-videoPlayer__container>iframe{position:absolute;top:0;left:0;width:100%;height:100%;border:none}@media (prefers-color-scheme:dark){.union__content,body,html{background:#1c1c1c;color:#f1f1f1}.union__content blockquote:not(.twitter-video){border-left:4px solid #367dc4;background:#272c35}}</style><script>window.addEventListener("applicationDidBecomeActive",(()=>{document.querySelectorAll(".hq-image video[autoplay]").forEach((e=>e.play()))}))</script></head><body class="union__content"><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.35-PM.png"><img class="alignnone size-full wp-image-438670" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.35-PM.png" alt="Screen Shot 2015-12-16 at 12.20.35 PM" width="601" height="537" sizes="(max-width: 1080px) 100vw, 776px" loading="eager"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.22-PM.png"><img class="alignnone size-large wp-image-438671" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.22-PM.png" alt="Screen Shot 2015-12-16 at 12.20.22 PM" width="430" height="529" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a></p><p> </p><p> </p><p> </p><p>Ana Cheri. Nothing like a little sexy Santa ass to get you in the holiday mood if the weather doesn’t feel like doing its job.</p><p> </p><p> </p><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.18-PM.png"><img class="alignnone size-full wp-image-438673" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.18-PM.png" alt="Screen Shot 2015-12-16 at 12.23.18 PM" width="481" height="355" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.09-PM.png"><img class="alignnone size-large wp-image-438674" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.09-PM.png" alt="Screen Shot 2015-12-16 at 12.23.09 PM" width="403" height="530" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.00-PM.png"><img class="alignnone size-large wp-image-438676" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.00-PM.png" alt="Screen Shot 2015-12-16 at 12.23.00 PM" width="479" height="525" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.52-PM.png"><img class="alignnone size-large wp-image-438677" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.52-PM.png" alt="Screen Shot 2015-12-16 at 12.22.52 PM" width="518" height="525" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.43-PM.png"><img class="alignnone size-large wp-image-438678" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.43-PM.png" alt="Screen Shot 2015-12-16 at 12.22.43 PM" width="413" height="521" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.36-PM.png"><img class="alignnone size-large wp-image-438680" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.36-PM.png" alt="Screen Shot 2015-12-16 at 12.22.36 PM" width="422" height="526" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.25-PM.png"><img class="alignnone size-large wp-image-438681" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.25-PM.png" alt="Screen Shot 2015-12-16 at 12.22.25 PM" width="409" height="520" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a></p></body></html>

<p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.35-PM.png"><img class="alignnone size-full wp-image-438670" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.35-PM.png" alt="Screen Shot 2015-12-16 at 12.20.35 PM" width="601" height="537" sizes="(max-width: 1080px) 100vw, 776px" loading="eager"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.22-PM.png"><img class="alignnone size-large wp-image-438671" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.20.22-PM.png" alt="Screen Shot 2015-12-16 at 12.20.22 PM" width="430" height="529" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a></p><p> </p><p> </p><p> </p><p>Ana Cheri. Nothing like a little sexy Santa ass to get you in the holiday mood if the weather doesn’t feel like doing its job.</p><p> </p><p> </p><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.18-PM.png"><img class="alignnone size-full wp-image-438673" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.18-PM.png" alt="Screen Shot 2015-12-16 at 12.23.18 PM" width="481" height="355" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.09-PM.png"><img class="alignnone size-large wp-image-438674" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.09-PM.png" alt="Screen Shot 2015-12-16 at 12.23.09 PM" width="403" height="530" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.00-PM.png"><img class="alignnone size-large wp-image-438676" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.23.00-PM.png" alt="Screen Shot 2015-12-16 at 12.23.00 PM" width="479" height="525" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.52-PM.png"><img class="alignnone size-large wp-image-438677" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.52-PM.png" alt="Screen Shot 2015-12-16 at 12.22.52 PM" width="518" height="525" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.43-PM.png"><img class="alignnone size-large wp-image-438678" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.43-PM.png" alt="Screen Shot 2015-12-16 at 12.22.43 PM" width="413" height="521" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.36-PM.png"><img class="alignnone size-large wp-image-438680" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.36-PM.png" alt="Screen Shot 2015-12-16 at 12.22.36 PM" width="422" height="526" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.25-PM.png"><img class="alignnone size-large wp-image-438681" src="https://cdn.barstoolsports.com/wp-content/uploads/2015/12/16/Screen-Shot-2015-12-16-at-12.22.25-PM.png" alt="Screen Shot 2015-12-16 at 12.22.25 PM" width="409" height="520" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a></p>

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