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The weekly sex advice column that started it all

Mind the Gap

Thirty-year-old trans woman here, Dan, and I have a question about what is surely one of your favorite subjects: the “age gap discourse.” About four years ago, I had a sexual experience that I go back and forth on whether to label as sexual assault. When I was 26 years old, I met a 19-year-old … Read More »

Quickies

I’m a cis woman. I had a quasi-relationship with a man last year that only lasted a couple of months. The sex was great, and sexting was always a big part of our connection. Since the breakup, we’ve fluctuated between staying in touch and radio silence, sometimes going months without speaking. During our periods of … Read More »

Figuratively Pissed

I’m worried this may be above your pay grade. LOL. My boyfriend and I have been together for nearly five years. When we first got together, he shared a fetish with me, which has honestly gotten out of hand. I’m not close-minded and I genuinely love pleasing people, and my approach to sex has always … Read More »

Power Tripping

I’m a 26-year-old masculine straight guy who loves exploiting the fantasies so many gay men have about straight men. When a gay guy is into me because I look like his straight-masculine-jock dream, it’s a power trip like no other. It’s always a specific type of bottom gay dude I seek out when I get … Read More »

Hands On

I’m a 35-year-old straight woman living in the Midwest. I was seeing a massage therapist for three years and we became very close friends. I referred my friends to him and helped him grow his business. He eventually disclosed to me that he had developed feelings for me. I went into instant shock and said … Read More »

On the Down Blow

I’m a gay man. After a decade together and five years of marriage, my husband informed me he wasn’t really interested in sex anymore. That was a year ago and we haven’t had sex since. He told me I should leave him, if regular sex was “really that important” to me, but if I chose … Read More »

Counseled Culture

Hello! I am a heterosexual man! My wife came out as a lesbian after thirty years of marriage. We have children together and we love each other. Therefore, we’ve decided not to divorce. We visited some therapists, and they all coerced us to divorce even though we really do not want that. We believe that … Read More »

Quickies

I’m a woman who recently went out on a third date with a man. I invited him back to my place and we started making out, which led to him going down on me. Moments later he took off his pants and to my surprise he had a micro penis. I was shocked and turned … Read More »

Game Over

Is it ever ok to stop being GGG? I’ve been with my husband for 26 years. Shortly after we got together, my husband disclosed a major kink: MFM threesomes. I was young and a virgin and up for anything then, but we didn’t start hooking up with other men until around year six of our … Read More »

Reunion Blues

I fell in love with my second cousin about four years ago at a family reunion. (I hadn’t laid eyes on him since I was a kid!) I was fifteen when we met, he was two years older, and we were in a long-distance relationship for three years. We ended things a year ago, and … Read More »