I’m in my 30s, and I’ve had a fair bit of sexual experience. Not much surprises or shocks me, sad to say, but this time I’m stumped. Here’s what happened: I was at a club with someone I’d met a few weeks prior, and we were getting pretty steamy. We were off in a corner, … Read More »

With the assistance of a wickedly unsqueamish lover, I have managed to excrete from my obliging body almost all of the fluids I can produce, i.e., bloodsweatspitcumpiss. But, alas, we lack one precious secretion: breast milk. As I am unwilling to undergo the nine-month infestation that traditionally prompts the production of breast milk, I implore … Read More »

Your response to New York City Girl was INSENSITIVE. There is no longer any question that you are a MAN! I was raped (with a dildo) by a female lover. I was hurt and angry, but I gave in and forgave her. Needless to say, the abuse continued throughout our time together. While NYCG wasn’t … Read More »

I’ll be blunt. I dig being smacked in bed. My boyfriend is willing to do this, but seems to think twice a month is enough. When he does smack me, he only does it until I’m horny enough to let him proceed with the after-hitting festivities. He’s just not hitting me long enough or hard … Read More »

I thought maybe an outsider could give me some insight into my heartache. I dated this guy–call him Ron–for seven months. We were deeply in love, but broke up. Almost a year later we tried to be friends. We hung out a couple of times but he kissed me, and there was a lot of … Read More »

After watching a few episodes of Mind of the Married Man on HBO, I thought I would go out and try to get a massage with a “happy ending.” I looked through the Yellow Pages and classified ads and found a massage “spa” in a neighboring town. Heart full of hope, I went to the … Read More »

I am a 25-year-old, bisexual female grad student in NYC. This summer I had sex with a man for the first time. It was casual sex, but we were together for a few days. I was spending the summer in California, and met him there; he now lives in Philadelphia. Today I called him up … Read More »

How come your masturbation horror story contest was only open to men? Women masturbate, and I’m sure we have horror stories! I’m a woman and I masturbate. Fortunately, I don’t have a horror story to share. I just wanted to bitch. You’re Extremely Sexist I never said the masturbation horror story contest was closed to … Read More »

Remember that reader who suggested you take submissions for the most embarrassing masturbation story? You promised your readers a contest, with prizes awarded to the author of the best (or worst) masturbation horror story. Did the events of September 11 preempt your masturbation horror-story contest? If so, I feel cheated. Wanna Laugh at the Freaks … Read More »

Some months back, I was involved in a serious auto accident. In the trauma unit at the hospital, a Foley catheter was inserted into my urethra to aid in waste removal, as I was laid up and could not use a washroom. Every so often, when a nurse came to check on me, she’d adjust … Read More »

My friend, let’s call him John, writes a sex column for our college newspaper. Much of his inspiration comes from his now-ex-boyfriend. My friend only uses the ex’s first name, and reveals no details that are too intimately embarrassing (except for once, but that’s not really pertinent). Anyway, the ex is now threatening to sue. … Read More »

Like you, I was horrified by the events of September 11. The Red Cross has advised people to avoid repeated viewings of the event, talk about our feelings, and return to our normal routines to reduce stress. Well, sex feels good and lowers stress. But the stress of current events leaves my partner feeling rather … Read More »

I share the pain and anger you feel in the wake of the heinous attacks of September 11. However, I’m writing to administer a gentle knock for your subsequent column. I’m not upset about your take on God. But while you may have sat down to write on September 12 in an emotionally shattered state, … Read More »

Imagine this hypothetical scenario: Guy meets Girl. Guy cooks dinner for Girl on second date, and make-out session erupts on living room couch. Guy takes Girl kayaking on third date, and make-out session breaks out after romantic picnic. Guy and Girl meet for a drink as she prepares to leave for a week-long vacation. Girl … Read More »

I’m 20, gay, and I just moved to the big city. I’m good-looking, I guess, because really hot guys are always hitting on me. I don’t actually like anal sex much, but I’m trying to learn. And that’s the problem: Most guys I sleep with don’t want to use condoms. How do I handle this? … Read More »

I have a recurring fantasy about having a threesome with my husband and his brother. I’m not interested in other men, and I’m not interested in my in-law without my spouse’s involvement. So how do I bring this up? Or will the aftermath of even asking be too weird to live with? Obsessed with My … Read More »

You recently called a person who wants to wait to have sex “some sort of saving-yourself-for-something-or-other sociopath.” Come on, Dan. Do you really think saving yourself for the right person is stupid? I’m a 25-year-old hetero male who made the choice to wait until I got married. Sound stupid? I don’t think so. Do you … Read More »

I have a BIG problem. The woman I love is 26 and I’m 28. We’ve been together for about four years, and in that time she’s gotten really fat. I tried to approach her about her weight in a gentle way (women and weight is a bad chat to have), and she cried and said … Read More »

This girl I’m seeing is a stripper and an escort. I’m fine with the stripping, but the idea of her alone in hotel rooms with old horny men bothers me. I’m fairly naive about the escort scene, and lately this woman who used to be a stripper has been filling my head with all sorts … Read More »

My husband and I recently let our best man borrow our New York apartment while we went away for the weekend. On Monday morning, my husband turned on our computer. Turns out our friend had been surfing hardcore porn sites all weekend. Our home page had been changed. Many of the links that he left … Read More »

I recently started dating a girl who has a strange fetish. The first time we slept together, she wanted to wear a Catholic schoolgirl outfit. The schoolgirl fantasy turned me on, although I thought it was a bit odd to go that far our first time together. Now she’s taking things even further, going places … Read More »

Your advice to MSL, the gay guy who wanted to suck off his straight roommate, was logical, but I must, as a heterosexual male, object. If MSL wants to freak his roommate out, then, by all means, he should follow your advice and “jokingly” offer to suck him off. But you forgot to take the … Read More »

The votes are in, they’ve been counted, recounted, and… actually, I’m going to resist making the stock Florida/hanging-chad/Republican-coup jokes. After all, this is serious business: What term, from this day forward, will be the commonly accepted slang for a woman fucking a man in the ass with a strap-on dildo? Three candidates stood in this … Read More »

You’ve often come to the aid of many a sick, demented fetishist, which has inspired me, a 23-year-old overweight, brown-skinned dude who has never gotten laid, or for that matter even achieved the least intimacy with a lady, sexy or otherwise, to beg your help in locating some kindly lady who might be willing, so … Read More »

A couple of weeks ago I convinced my girlfriend to dress up in her old school uniform for sex. We started going out long after high school ended, so I never got a chance to do the deed with her in uniform. I get the feeling she didn’t enjoy herself as much as I did … Read More »

If some straight guy went around bashing gays in print in the way you’ve been bashing poo-eaters, we’d all assume he was a closet case. So how about it, Dan: What’s your real motivation, huh? Expressing personal preference is one thing, but publishing letters just so you can point out how disgusted you are is … Read More »

At the end of last week’s column, you asked what we should call it when a woman fucks a man in the ass with a strap-on dildo. We should call it “a woman fucking a man in the ass with a strap-on dildo.” Does every sexual practice need a cute term? I’m sick of not … Read More »

For crying out loud! What the fuck is wrong with people?! What the fuck is going on when someone wants noxious gas sprayed in their face for sexual pleasure? For the love of god, what the fuck is going on when a man wants to consume feces? I know you get the weird stuff all … Read More »

Your column used to be filled with disgusting letters from sickos. Now it’s real people with real problems. Bring back the perverts! Disappointed in You Two weeks ago I promised to get back to the freak show, and last week I thoughtlessly filled my column with real people experiencing real problems. Sorry about that, DIY, … Read More »

I’m a 30-year-old straight male. I am successful and reasonably good-looking. Anyway, here’s the deal: There is a woman about my age whom I find mentally stimulating, but only moderately physically attractive. I’ve found through experience that single, independent women who’ve made it to their 30s alone are the type of women I respect and … Read More »

After reading all the responses to your “why is being a dyke so easily shrugged off” query, I have to say, who cares? There’s no way this question can ever be answered to everyone’s satisfaction, so why bother? I don’t read your column for abstract conversations about sexual identity. No, I read your column for … Read More »

In a recent column you mentioned that three lesbian friends had run off with men. “One… is married to a man,” you wrote, “one is living with a man, and the third is a man.” You observed that none of your gay male friends had run off with women, and asked, “What is it about … Read More »

I am a 30-year-old male, married to a woman for five years. Our sex life is average, with sessions typically including a little oral and mutual fondling, followed by missionary-position intercourse. My wife has requested a spanking from time to time, which I have reluctantly given her. Recently on our shared credit card bill I … Read More »

This question concerns both sex and etiquette: How much privacy can one reasonably expect while engaging in consensual sex in a sex club? While visiting one of those open-to-the-public establishments that cater to men who want to get off with other men, I saw an uptight but openly gay prig who is a member of … Read More »

I need your help. On Saturday, February 17, I went out dancing with some friends from work. We ended up at Electra (in Cincinnati), where I wound up dancing with this really attractive Asian woman. We danced all night and built up a really magical rapport. Her ride was pressuring her to leave, so in … Read More »

I’m a 21-year-old college guy. I used to be chubby, and then, about a year ago, I hit the gym. Then I started having my sister dress me, because I have no fashion sense. When the weight came off and muscles came on, women really started to notice me. Suddenly women couldn’t keep their hands … Read More »

When I am soft, my cock is tiny. Yet when I am hard, it is long and thick. I have asked girlfriends about this and none has ever seen such a change. In your vast experience with male organs, what can you tell me about growth? Wee-Willie Winkie/Pink Giant Putting aside my vast experience with … Read More »

We are a male/female bisexual couple facing an ethical dilemma. We’ve been together 10 years. He’s a gorgeous, well-built man with a strong sex drive. I’m a beautiful woman with a normal sex drive. I have also been HIV-positive for 12 years. He’s negative. We would really like to explore his bisexuality together and have … Read More »

Thank you for printing a column on cunnilingus. Your straight female readers appreciate it! And while I understand your distaste at having to read so many e-mails about the practice, I feel compelled to respond. After printing lots of contradictory advice from women about cunnilingus, you told straight men simply to ask the women they’re … Read More »

My boyfriend of one year phoned me to tell me he almost cheated on me. An old girlfriend invited him back to her house. The only reason he didn’t, he said, was because he had too much homework (we are both university students), NOT because he loved me too much to do such a thing. … Read More »

A couple of months ago you invited women to send in cunnilingus tips for straight guys. Didn’t any women send in tips? Straight Guy Anxious for Pointers I got 500 letters from straight women with advice for men on the whole pussy-eating subject. Why haven’t these letters appeared in this column? Well, I have a … Read More »

I tried to ask this question of Van, the porn star who sells his dirty underwear via his website, www.vanhotman.com. I wrote to him via his website and asked him to call me, but I never heard back. Perhaps you could have him contact me? You see, I’m a 40-year-old gay man living in Manhattan … Read More »

I have been seeing a guy for about four months who recently moved to my city from out-of-state. A contributing factor in his move (although not a major factor) was that he wanted to get on with his life following the breakup of a long-term relationship. He keeps saying that he does not want a … Read More »