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PO’d about P-in-V

QI’m a heterosexual cis woman in a monogamous marriage. My husband and I have always struggled to connect sexually, mostly because he has extreme anxiety that makes doing anything new or different difficult. He’s been in therapy since before I met him, but it doesn’t seem to be helping much. His anxiety has caused him […]

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Hot for student

Q I’m a 40-something gay male professor at a small college. I try hard not to get attracted to students, and usually succeed. But it’s tough to resist when you’re surrounded by hot, smart, horny young guys in a rural area. Over the years, I’ve ended up having sex with several students. None of them […]

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Sissy that talk

Q My boyfriend and I met online to explore our kinks. We’d both been in relationships with kink-shaming people who screwed with our heads. Since we weren’t thinking it was more than a hookup, we put all our baggage on the table early and wound up becoming friends. Eventually we realized we had a real […]

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Quickie thinking

Q My little dick has always held me back. I didn’t date in high school because I couldn’t stand the thought of girls discussing my tiny manhood. That said, I’ve adapted fairly well and become skilled with my tongue and hands. The biggest problem is that my dick is just small enough that the head […]

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Cheaters’ club

Q I am a guy in my 40s and a classic sexual scoundrel. I cheated on my ex-wife and every girlfriend I’ve ever had. I’m currently dating a woman in her 20s. We are both each other’s ideal type. She has as scandalous a past as I do. We met via a hookup app. We […]

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Three-city swing

We brought Savage Love Live to the Music Box Theatre in Chicago, the Barrymore Theatre in Madison, Wisconsin and the Pantages Theatre in Minneapolis over three nights. As is always the case at live shows, the crowd had more questions than I could possibly answer in a single night. In this week’s column I’m going […]

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Bad guys

QI met a guy right around the time my boyfriend dumped me. I met him on a dating site, but he was really only interested in my boobs and me giving him head. I really like having him in my life and he’s very attractive, but he won’t do anything with me other than let […]

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