I am a 30-year-old straight man and I’ve been with a 28-year-old bisexual woman for a year. Early in our relationship, after much discussion, we established that it would be open. I would have the liberty to see other women and so would she. We just had to be safe and always keep each other … Read More »

I am a 30-year-old straight man and I’ve been with a 28-year-old bisexual woman for a year. Early in our relationship, after much discussion, we established that it would be open. I would have the liberty to see other women and so would she. We just had to be safe and always keep each other … Read More »

I’m a 24-year-old gay male with few resources and no “marketable” skills. I have made a lot of bad choices and now I struggle to make ends meet in a crappy dead-end job, living paycheck to paycheck in an expensive East Coast city. Recently, someone on Grindr offered me $3,000 to have sex with him. … Read More »

I’m a 24-year-old gay male with few resources and no “marketable” skills. I have made a lot of bad choices and now I struggle to make ends meet in a crappy dead-end job, living paycheck to paycheck in an expensive East Coast city. Recently, someone on Grindr offered me $3,000 to have sex with him. … Read More »

I am a cis woman in my mid 20s. I get a pang or a spasm of pain in a place deep in my clit/urethra area. I can’t pinpoint which part exactly. It takes me by surprise every time it happens, so I jerk around and press my crotch for a hot second—which doesn’t help, … Read More »

I’m a gay man who is ready to start cheating on my boyfriend. We’ve had a wonderful 3.5-year-long relationship full of respect, affection, support, and fun. I love everything about our relationship, and our sex life was great… until he moved in eight months into the relationship. At that point, he lost all interest. I’ve … Read More »

I’ve been dating this guy for almost two months. It’s been pretty good, except the sex isn’t really the best. I have this other male friend who has had a crush on me. Long story short: My friend made a move on me the other night. I told him I couldn’t, and he knew why, … Read More »

I’m a 26-year-old single bi woman. Sometimes my roommate/best friend and I have drunken threesomes with men. We’ve had some great one-night stands (less scary with a friend!), but recently we slept with a man I’ve been (drunkenly) sleeping with over a period of months, my “friend with benefits.” I shared my FWB with my … Read More »

My son, who is almost 30 years old, was married four years ago. He just shared with us that for the last three years, he and his wife have been practicing polyamory. They are committed to their relationship but have each had relationships with both men and women. We are trying to get our heads … Read More »

Is it legal for a man to procure the services of a dominatrix? In the kind of session I have in mind, there’s no nudity or sexual activity or contact involved. There’s not even any whipping or flogging or caning or hardcore BDSM stuff. I just want to see what it would be like to … Read More »

I’m confused about my sexuality. For many years, I thought I preferred hetero-romantic asexual relationships. Exposure to select reading material-thanks to my gender-studies classes-has me convinced I’m an asexual t-type (i.e., “top,” but I prefer not to use such connotative terms) female who is attracted to slight and feminine men. I do not want to … Read More »

Please do a public-service announcement about the Ashley Madison hack, and request that NO ONE look up information on ANYONE other than their own spouse. I’m a former AM user. I’ve been married to my wife for 20 years. We met when we were both 20 years old. Seven years ago, I made a selfish … Read More »

I’m a woman in a straight relationship. I woke up this morning, and my BF wasn’t in bed with me. He felt ill in the middle of the night and went to sleep in the spare room—where he found a condom in its wrapper behind the nightstand. Now my BF thinks I’m cheating on him. … Read More »

{{ image: 1 }} I’ve been reading your column for a while, and you always advise kinky people to go seek the same within the kink community. But in my experience, the kink community is very “sex right away, get to know you later”–oriented. So I have two questions. First, as a gay man who’s … Read More »

Does a person who acts loving only when high on weed really love you? My live-in boyfriend of three years acts sweet, loving, and caring when he’s high, but when the weed runs out, he’s mean, angry, hurtful, and horrible to be around. I’ve asked him when he’s stoned to still act like a loving … Read More »

I have always wanted to have a girls-only sex party, but I’m not sure how I feel about actually organizing one. What’s the etiquette if I do organize one myself? Do I need to provide the dildos for people’s harnesses? Or just the condoms and lube? And how do I find people who want to … Read More »

My wife and I have been together for more than 10 years, practicing some kind of nonmonogamy for more than seven. We tried different things—open, dating others, FWBs—but after a bi threesome with another guy a year ago, we knew that was our thing. For a while, everything was great, but roughly a month after … Read More »

I have been happily married for 12 years. I’m deeply in love with my wife—she’s amazing, very sexy and gorgeous. I used to be jealous, but about six years ago, I lost my feelings of jealousy. In their place, I developed a strong desire to share my wife with other men. It’s my only fantasy. … Read More »

I entered into a civil union with another woman in Vermont in 2000. My ex and I were together until 2003, when we decided to go our separate ways. It is now 2015, and my new partner (who happens to be male) and I are expecting a baby and talking about getting married. We live … Read More »

This is going to sound like bragging, but my appearance is intrinsic to my kink. I’m a gay male gymnast. Most of the guys on my college team are annoyed by the kind of objectification we routinely come in for. (We actually don’t want to be auctioned off at yet another sorority fundraiser, thanks.) But … Read More »

I am a male grad student who is technically engaged to a female grad student. She has numerous positive qualities, but she is repulsed by sex. She is very sensitive about her repulsion and becomes distraught when I broach the subject. She says that even the thought of doing anything sexual with me elicits a … Read More »

My boyfriend and I both spent a lot of time masturbating when we were young, and pretty much trained our brains to come only one way. He can only come from masturbating furiously, or sometimes from a marathon of jackhammer sex. A few years before I met him, I toned down the masturbating to retrain … Read More »

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 style your hair? You look … Read More »

I’m a 35-year-old divorced man. I’ve been on plenty of dates since my marriage ended, but I invariably get asked this question on or before date #2: “Why did you get divorced?” This is where everything goes to shit. I’m honest: “We got divorced because I cheated on my wife. A lot.” This usually catches … Read More »

You often mention asexual people. I believe I may be one. I’m a 51-year-old woman. I’ve been separated from my opposite-sex partner for nearly nine years. I’ve been approached by a variety of men, each one interested in becoming “more than friends.” I haunt Craigslist’s “platonic m4w” section, but each time I reach out to … Read More »

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. I’m well aware of how sexual kids … Read More »

My wife is one of those women who need manual stimulation of her clit during sex to climax. Before meeting her, I had several long-term girlfriends, and not one needed to do this in order to climax. Before we got married, I explained that I wanted to explore and push the boundaries, and she promised … Read More »

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 and sending dick pics … Read More »

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 »

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 internet … Read More »

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, etc., and that he didn’t “flash on” violent images at those times. But he says he thinks … Read More »

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 doing. … Read More »

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 need … Read More »

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 hit … Read More »

My fiancée 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 a … Read More »

I have been wearing bras and panties with stockings for so long now, it’s become a part of me, and I was wondering if you have heard of this before. Sent From Samsung Mobile People wearing bras and panties and stockings—that is something I’ve heard of before. A quick programming note: Some weeks, half the … Read More »