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Q I’m an American woman living abroad and have started a relationship with a wonderful man from a Middle Eastern country. We are having a great time exploring what is a foreign country for both of us. The looming issue is sex, of course. He is a moderate Muslim, but he grew up in a […]

Q I consider myself a straight guy—but for the last four years, I’ve been having an affair with “Connie,” a trans girl I met online. It was just casual at first, but over time we developed a deeper personal relationship but kept it hidden. At some point, I figured out she was in love with […]

Q I found this in an online sex ad: “Straight guy with an addiction to massive cocks in my ass.” This “straight guy” went on to mention his girlfriend. Can a person really identify as straight while wanting to be fucked by men? I understand that straight guys can like ass play too, but it’s […]

Q I’m a straight guy in my 30s dating a woman in her mid-20s. We’ve been together for a year, and I’m crazy about her. In love, even. She’s gorgeous, sweet, kind, loving and very sexual. She’s perfect. In her late teens and early 20s, she had a wild sex life. She attended sex parties, […]

Q When I was 15, I had a three-month-long sexual relationship with a 32-year-old woman. She was a friend of the family, and my parents were going through a divorce. I stayed with her for the summer, and she initiated a sexual relationship. Looking back, I can see that she had been grooming me. We […]

Q wife issues. lack of intimacy. cuckold, etc. —need help A While I typically encourage people to keep their questions brief, it is possible to be too brief, NH. But I’ve gotten so many questions from wannabe cuckolds with wife issues over the years that I’m going to hazard a series of guesses and take […]

Q I have been reading your column for years, Dan, and now I’m writing you for the first time to ask for a favour. I met this dude online in December and I felt like we had a good connection. He “dumped” me, though, because he was busy and was going through career shit and […]

Q My father is 65 years old and has been a devoted husband to my mother who has been battling a medical condition for the past 30 years—a condition that prevents her from engaging in sexual activity of any kind. He has not had sex in all this time and is desperately frustrated. He’s not […]

Q My 15-year-old son has been watching sadistic porn—and ONLY sadistic porn—for a couple of years. He also tells us (husband and me) that, though he’s not had sex (which he defines as penetration), he’s had oral sex, handjobs, et cetera, and that he didn’t “flash on” violent images at those times. But he says […]

Q My husband and I are a straight couple in our early 50s, and we’ve been married for more than 30 years. We were raised to wait for sex till we got married—this was back in the early ’80s—and we did. Our wedding night was pretty disappointing since neither of us knew what we were […]

Q I have a dildo that I loooooove, and I was wondering if it’s safe for me to use it in both my ass and my cunt. I would clean it in between uses/orifices, of course, and it has a flared base, so it’s safe for anal play. Can I do this or do I […]