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Cuckold comfort

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, […]

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Nothing but the truth?

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 […]

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A bit of brevity

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 […]

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Quick sick hits

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 […]

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Elder care

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 […]

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A most violent year

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 […]

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Long time coming

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 […]

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Toy stories

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 […]

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Vore vore vore

Q I’m a straight 18-year-old girl in my first sexual relationship. Things are a little awkward, and I could chalk it up to inexperience, but here’s what I feel conflicted about: I have a vore fetish. It was a fascination for me as a young child and became a sexual thing around the time I […]

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The porn hub

Q My fiancee is extremely bothered by me looking at porn. It revolves around insecurities that have gotten so bad that even other girls bother her. (We can hardly go to a beach anymore.) I don’t have any weird relationship with porn—no addiction, no violent stuff, and I look pretty infrequently. She acknowledges that it’s […]

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Tips for a good letter

Q I have been wearing bras and panties with stockings for so long now, it’s become a part of me. I was wondering if you have heard of this before. —Sent From Samsung Mobile A That is something I’ve heard of before. A quick programming note: Some weeks, half the questions I get are longer […]

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Short short man

Q I’m a short guy and I need advice. I don’t want a small paragraph’s worth of advice, like you gave Below Their League a few years ago. I need advice beyond “Women like men taller than them, get over it!” I get it. I’m short (five foot two), and most women are taller than […]

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