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<!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>Milf Monday with Jenifer Jenkins</title><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!important;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><script>window.htlAdUnitPath="57249056/in-app-iOS/Article-Page_In-Article-Unit",window.htlKeyvalues={authorId:"63571",category:"Chicago",tags:["jenifer-jenkins","milf","NSFW"],brandName:"Barstool Chicago",brandId:61,pagetype:"standard_post"}</script></head><body class="union__content"><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/G3CPhIP?_showcaption=true" href="https://chumley.barstoolsports.com/union/2023/01/02/EFD7B342-9E9E-4529-882F-4DD0AEABF0F6.26bd854f.png?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63571_61_milf-monday-with-jenifer-jenkins&utm_campaign=barstoolsports_referral_blog_63571_61_milf-monday-with-jenifer-jenkins"></a></div></div></div><p>Milf Mondays. I need all your favorite Milf guilty pleasure suggestions in the comments, please. </p><p>Kicked it off <a href="https://www.barstoolsports.com/blog/3450577/milf-mondays-debbie-st.-pierre" rel="noopener noreferrer" target="_blank">week 1 with Debbie St. Pierre.</a></p><div class="articleAd" id="teads" teads-ad></div><p>Then we had <a href="https://www.barstoolsports.com/blog/3451422/milf-monday-with-callie-bundy" rel="noopener noreferrer" target="_blank">Callie Bundy.</a></p><p>Last week was <a href="https://www.barstoolsports.com/blog/3453459/milf-monday-with-jala-sue" rel="noopener noreferrer" target="_blank">Jala Sue</a>. </p><p>This week we've got Jenifer Jenkins.</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/0LFYcA2?_showcaption=true" href="https://www.instagram.com/reel/CkJpjmeNlpV/?igshid=YmMyMTA2M2Y%3D&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63571_61_milf-monday-with-jenifer-jenkins&utm_campaign=barstoolsports_referral_blog_63571_61_milf-monday-with-jenifer-jenkins"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/XNraDcU" href="https://www.instagram.com/p/Cno_f3dK8h1/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63571_61_milf-monday-with-jenifer-jenkins&utm_campaign=barstoolsports_referral_blog_63571_61_milf-monday-with-jenifer-jenkins"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/Hzsr6va" 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<div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/G3CPhIP?_showcaption=true" href="https://chumley.barstoolsports.com/union/2023/01/02/EFD7B342-9E9E-4529-882F-4DD0AEABF0F6.26bd854f.png?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63571_61_milf-monday-with-jenifer-jenkins&utm_campaign=barstoolsports_referral_blog_63571_61_milf-monday-with-jenifer-jenkins"></a></div></div></div><p>Milf Mondays. I need all your favorite Milf guilty pleasure suggestions in the comments, please. </p><p>Kicked it off <a href="https://www.barstoolsports.com/blog/3450577/milf-mondays-debbie-st.-pierre" rel="noopener noreferrer" target="_blank">week 1 with Debbie St. Pierre.</a></p><div id="Article-Ad-Placeholder" data-union-ad></div><p>Then we had <a href="https://www.barstoolsports.com/blog/3451422/milf-monday-with-callie-bundy" rel="noopener noreferrer" target="_blank">Callie Bundy.</a></p><p>Last week was <a href="https://www.barstoolsports.com/blog/3453459/milf-monday-with-jala-sue" rel="noopener noreferrer" target="_blank">Jala Sue</a>. </p><p>This week we've got Jenifer Jenkins.</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/0LFYcA2?_showcaption=true" 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Milf Monday with Jenifer Jenkins