My partner is 31 years older than I am. I know the math: He’ll be 60 when I’m 29. But that isn’t the problem. The issue is he’s been a lifelong bachelor and never been monogamous. He’s fucked hundreds of women and is close friends with a lot of his former fuck buddies. Because of … Read More »

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 strict … Read More »

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 me. … Read More »

I’m a straight male kinkster who used to do live performances as a rope bondage top, but I recently jumped out of the kink community. I just think I’ll have better luck finding a long-term relationship with a girl from the vanilla world. So long as she’s GGG, I can live with it. As much … Read More »

I think my husband is addicted to porn. I find porn in his browser history almost every single day. He says I’m the only one he wants, but I find that hard to believe knowing he watches nonstop porn before fucking me. He also parties every time he goes on a business trip. Needless to … Read More »

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 not … Read More »

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, had … Read More »

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 used … Read More »

wife issues. lack of intimacy. cuckold, etc. need help 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 a shot … Read More »

I have been reading your column for years, Dan, and now I’m writing you for the first time to ask for a favor. 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 lived … Read More »