Savage Love

Dear Dan: I was combing through some old columns/podcasts and came upon a few instances where you counseled women on selling their used underwear online. So I was wondering: Is this particular kink strictly limited to straight guys looking for ladies’ panties? Or is ...

Dear Dan: Last summer, I reconnected with a high-school teacher I hadn’t seen for a year. We first met when I was 15, and I had nothing but respect for him and his intelligence. I also had a crush on him for the next four years. Fast-forward a year. He is sexting me ...

Dear Dan: I’m a gay man in my late 20s, and I can’t get fucked. I have tried to train my ass, but the largest thing I can place inside remains a small butt plug. If I try anything bigger, the pain is unbearable. I’ve always been a very anxious person, and it’s clear ...

Dear Dan: I am a young gay man who has been so freaked out by the idea of catching an STI that I haven’t gotten with anyone for two years. But last night, I hooked up with a cute 21-year-old FTM trans boy, and maybe because it was a person with lady parts, I let ...

Dear Dan: I’ve talked to my girlfriends, my mom and his mom, but I need some unbiased advice. I’m a 28-year-old woman in a relationship for three-and-a-half years with a wonderful man, also 28...

Dear Dan: I’ve got a question I doubt you’ve ever gotten before. It has a bit of everything: sex-work etiquette, long-distance phone interaction, and a het cis chick anxious not to lose her tolerance badge. Here it goes: A few months ago, I started getting hang-up ...

Dear Dan: I am a man who tends to ejaculate prematurely. Not all the time — but at least 50 percent of the time, I’m good for two to three minutes and then I REALLY have to be careful. I’ve learned to manage it and work around it (like, stop if I’m too close and eat ...

Dear Dan: Here’s the Reader’s Digest Condensed Version: I’m a sexually inactive (by my own choice) heterosexual female in my late 40s who up until recently used to be much heavier and in rapidly declining health. Since my type 2 diabetes diagnosis, I have achieved ...

Dear Dan: A big congrats to Caitlyn Jenner on her big reveal and lovely Vanity Fair cover! But I am having a crisis of conscience. On one hand, I support a person’s right to be whoever the heck they want to be. You want to wear women’s clothing and use makeup and ...

My boyfriend of three months, “Marcus,” told me last week that he is a trans man. He’s performed oral sex on me and fingered me, but he never let me reciprocate and told me he didn’t want to have penis-in-vagina sex yet because that was a large commitment. We go to ...

Dear Dan: I am a 30-year-old trans guy, on T since college, happy and comfortable with my sexuality. However, I can’t find any helpful health info on a fetish I’ve developed: I insert needles directly into my clit, maybe an inch and a half in. I’m not talking through...

Dear Dan: Yesterday, I found my 5-year-old son putting things up his butt in the bath. This isn’t the first time — and it’s not just a “Hey! There’s a hole here! Let’s put things in there!” kind of thing. The little dude was rocking quite the stiffy while he did it. ...