<!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/app.barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/app.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","37"),htlbid.setTargeting("Verity_keywords",["ass | barstool sports","anastasia ashley","beanies","hats","flag","hoodies","long time","big game | new football t-shirts","more shop","favorite ass shot","gear","one","love"]),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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I had to post this one. One of my favorite ass shots from Anastasia in a long time. In a long time. Kind of made me fell in love with her ass all over again.</p><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/asahs.jpg"><img class="alignnone size-full wp-image-229696" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="asahs" width="458" height="490" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/asshd.jpg"><img class="alignnone size-large wp-image-229697" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="asshd" width="325" height="608" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/aashsd-480x566.jpg"><img class="alignnone size-large wp-image-229698" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="aashsd-480x566" width="480" height="566" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/adfad.jpg"><img class="alignnone size-large wp-image-229699" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="adfad" width="371" height="587" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a></p><p> </p></body></html>

<p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/adadad.jpg"><img class="alignnone size-full wp-image-229695" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="adadad" width="361" height="304" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="eager" style="aspect-ratio:1.7244444444444444"></a></p><p> </p><p>And the Anastasia Ashley. I had to post this one. One of my favorite ass shots from Anastasia in a long time. In a long time. Kind of made me fell in love with her ass all over again.</p><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/asahs.jpg"><img class="alignnone size-full wp-image-229696" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="asahs" width="458" height="490" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2015/02/asshd.jpg"><img class="alignnone size-large wp-image-229697" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="asshd" width="325" height="608" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a><a 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