I’m a 20-year-old straight male, but this isn’t really about me.

I was recently back home for a family event while my younger brother, age 14, was away on a mission trip with his church. My iPad died while I was home and my mother told me to look in the kitchen drawers for a charger. I couldn’t find one there, so she told me to check my brother’s bedside table. I opened the drawer and, with a little digging, found a charger.

I also found a few pictures of gay porn and a couple of pictures of male celebrities with their shirts off that had been clipped from magazines. It isn’t the gay porn I have a problem with, I fully support him coming into his sexuality, whatever it might be, but then I found a few things that were a bit more disturbing: I found a picture of our father in his swim trunks, and another one of a fully naked man with a cutout photo of my father’s face glued over the original model’s face. Needless to say, I was freaked out. I put everything back where I had found ...

Three months ago, I met a woman who I’m really into physically, emotionally, and mentally. She’s someone I could see myself with. Problem is, when we started having sex, she insisted on a condom for birth control. I haven’t worn one in probably eight or nine years. (I’m 33 now.) I would be hard, then put on the condom and start having sex, and go limp because of the feel. This happened many times over the first couple months, leading to frustration on both our parts. She went on the pill a couple weeks ago to deal with the issue, but now I’ve got a mental issue going on and still go limp once we start having sex. As soon as I get inside her, it’s all I think about, and things turn to shit. I feel like it’s not a physical problem, as it hasn’t happened before, so I’m not sure that drugs would even work. I don’t know what to do. It’s at the point of ruining this relationship.
Futile Limp-Ass Cock Is Dreadful

Before I get to your question, FLACID, I wanna pull rank—it’s ...

In response to a wannabe fister who hadn’t told his girlfriend about his kink, you wrote, “At three years, all your kink cards should be lying face-up on the table.” Really? Then my husband and I screwed up. We’ve been married for 19 years, and he told me only five years ago that he wanted to be spanked. Less than two years ago, he mentioned that he had been to a dominatrix before we met. I thought we had talked about everything when it came to sex and fantasies. I was wrong.

While I have your attention: I’m having a problem with the spanking. It just isn’t my thing. I told my husband he could go to a dominatrix if that would satisfy his needs. He agreed to go if I watched the session. I’m not sure I can do that, either. Well, guess what? We can’t even find one in our part of the country. I hate to think we need to plan a special trip outside to visit a dominatrix (“outside” means Lower 48 in Alaska slang). I can’t imagine scheduling something like that when we’re on vacation visiting kids ...

I’m a single 24-year-old gay actor/singer/comedian who’s going to be a doctor in a few years—I have varied interests—and I think being in a porn flick would be really hot. I don’t know what the ramifications of ramming on cam could be with regard to my future career. The field I want to go into is a very specific burgeoning branch of medicine generally unrelated to sex, but still involving patient care, and I want to be on the cutting edge of this type of medicine. I don’t know how much the world of medicine pays attention to this sort of thing when checking up on prospective doctors. Thoughts?
Wants To Film Lusty Orgasmic Lovin’

I don’t know if appearing in porn will make going into medicine more difficult, WTFLOL, but it sure can fuck up a political career.

Sigh.

You know, for a few minutes it looked like Anthony Weiner was going to beat this thing. But the prudes and hypocrites—in Congress and the media—carried the day.

Back to you, WTFLOL: Considering the amount of time and money that you’re going to invest in becoming a doctor ...

I’m a straight man married to a bisexual lady, which is something I would recommend to all other straight men in the world. We’re in our late 20s, have been together for eight years, married four. (I know: too young and too soon, but we’ll see how it turns out.)

My wife has a much higher sex drive than I do, and she’s also into kink, as a domme. My fantasies are vanilla, but I’m GGG.

The problem, as I see it, is that she doesn’t initiate. She’s tied me up and spanked me a handful of times, and it was fine.

Could I have done something wrong? How do you get spanked wrong? When I’ve asked her, she says that it takes a lot of energy to top, which makes sense, but we’ve done plenty of other high-energy activities. Communication is excellent between us. How do we get past this?
Beaten Up Not Nearly Enough

The issue, BUNNE, can be summed up in three little words: “it was fine.” For you, it was fine. Not great, not mind-blowing, not something you love and can’t live without. It was fine ...

I’m a 22-year-old FTM. I will become a legal male this summer. WOOT. Useless hole but still no pole. My friends—all straight—don’t know I’m FTM because I don’t feel it matters. I don’t know any other FTMs, and I really don’t care to. However, I like men. I have never had a boyfriend or been on a date. I go to gay clubs and flirt, get hit on, dance, and make out with other gay men. But when I am up front about being FTM, I never hear from a guy again. My question is, when do I tell a gay man I have been flirting with that I am not a bio male? I don’t want to deceive them, but I at least want a chance for them to get to know me a little bit first.
No Pole, No Go

The first thing Buck Angel—trans activist, public speaker, and porn star—wanted to say, NPNG, was congrats in advance on becoming a legal male. The second thing Buck wanted to say was that hole of yours isn’t useless.

“If he isn’t familiar with my work, maybe ...

My husband and I recently realized that in order for us to remain happily married, we need to fuck other people.

Enter the boyfriend. This 20-year-old hunk has opened the sexual floodgates. He’s gorgeous and athletic and enthusiastic, he gets me off at least twice every time we get together, and tales of our exploits have made things even hotter between my husband and me. Everybody’s happy!

So what’s the problem? Well, after two months of dating and numerous sexual encounters, my new lover has yet to get an erection. I know he’s been able to get it up with previous partners, so I suspect this has something to do with our situation. Maybe there’s a subconscious part of his brain that doesn’t want to bone a married woman? I’ve made it clear to him that there is no pressure and that I am more than satisfied. He insists that he is very attracted to me and that our current activities (lots of oral and hands everywhere) are incredibly satisfying.

Am I missing something, Dan? How can I coax this young man’s erection out of hiding?
Nouveau Mrs. Robinson

Before I get ...

I am a bi woman happily married to a straight man, and we both “participate” in hot sexy times with other women during threesomes. It’s hard to find hot 30ish bi girls where we live, but the encounters we’ve had were for the most part excellent. Everything was great until three weeks ago, when we had a miscarriage. We’d been trying for almost two years, so the recovery is not just physical but emotional for both of us.

We were only recently given the go-ahead to have sex again. We have a well-rounded sex life—kink, BDSM, toys—and both of us have said that, just for right now, we’re not looking for anything more than just us.

I went to the computer this morning to find that my husband had left his e-mail open. His inbox was filled with replies to recent queries sent to girls looking for couples to hook up with. His e-mails to these girls ask what gets them hot and when/where we can all hook up, and they state that his wife is really excited about f-ing her. I’m probably overreacting due to all the extra hormones, but he ...

I suppose you are going to call me an asshole once you have finished reading my letter, but I hope you have some advice for me regardless.

I am a 45-year-old heterosexual male. My last relationship lasted nearly seven years. I am currently single. I am discouraged. One of the reasons for my discouragement: I have to get too far into a relationship before I can determine if it will work out with any particular woman. An awful lot of emotion, time, and effort are required to get that first look into a woman’s panties. And this is where my problem lies. A woman can have the sweetest personality, she can be pretty and hardworking, but if her pussy isn’t bald and her “little man in the boat” doesn’t fit comfortably in my mouth, I am not turned on. I require a shaved pussy and a big clit.

I have asked women with whom I’ve become close to go bald. If the answer is no, there is no need to return. I respect a woman’s control over her own body, of course, but I like a big clit. She may or may not be bald ...

My life is not horrible. I’m an American college student. Compared to most people in the world, I’m pretty well-off. I go to college in Bellingham, Washington—the weed is awesome, the weather is great, and there are lots of hot guys. Score! But! I’m a homo. And I didn’t know how horrible my life was until I got here…

It seems like every gay/queer person who is involved in anything gay/queer on campus has this idea that gay people are SO oppressed that we need to constantly discuss it and feel like victims. Don’t get me wrong: We are a ways away from equality, and I recognize this. But it seems like the constant thread on college campuses for queers—other than talking about Lady Gaga or sucking dick—is complaining about how oppressed queer people are.

How do I respectfully say, “STFU, we’re doing just fine, you white, upper-class American kids” without sounding like an insensitive assdouche?
MG

You know, when I came out to my parents in 1981ishwhateversomething, telling my mom and dad that I was gay didn’t just mean telling them I liked to kissandotherstuff boys. It ...

I was hanging out with a guy who is in a relationship. I told him nothing could happen, and we decided to keep things friendly. A while ago, I made the drunken mistake of climbing into the backseat of a car with him, and things got racy pretty quickly. He asked if I was on birth control; I told him yes, because I was, and he penetrated me and came inside me after one thrust.

The next day, I got all emotional, and he’s since stopped talking to me because I freaked. Here we are a bit later, and I just had a pregnancy scare. Had I been pregnant, I would have had an abortion. If I’d actually been facing an abortion, I would have called and told him. Would that have been the right thing to do?

I wouldn’t have asked for money or support; I would have told him solely because it would have felt wrong not to. I had some feeling, like he should know—because he has a right to know, you know? I can’t imagine I’m the only woman who’s been faced with a “to tell or not to ...

I’m a young heteroflexible guy who has been a “sugar baby” for a handful of wealthy older guys. I love it! I get money, I have fun being with them, and the guys seem to like having me around. The problem is that I just got with a new guy who is really great, except for one thing: He is HIV positive. He says that his doctors predict he won’t have a shortened life span and may not even have any symptoms that would make his life uncomfortable. I like the fact that he told me, and I am open to being with him sexually even though I am HIV negative and want to stay that way.

He is VERY submissive—he wants to be used and abused sexually, physically, and mentally. My question is, what kinds of sex acts are okay to do with this guy? I read on one site that him rimming me is fine, and on another that him giving me a blowjob with a condom is safe, too. But I can’t find a site that specifically explains which sex acts are safe and which ones aren’t when one person is positive ...

My wife and I have been married for a few years and are expecting our first child. I’m really into the idea of being sprayed with my wife’s breast milk. The other night, she was fretting about when her boobs are going to start leaking. This seemed like a good time to bring it up, so I told her about my newly discovered lactation fetish. She freaked out—her comments were along the lines of “Gross!” and “That’s not what that’s for!” This is something I’d really like to explore, but I don’t know how to reapproach the subject.
Man Into Lactation Kink

Not all pregnant women, however thrilled they are about having children, are excited about—much less excited by—the physical changes that come with pregnancy. So you might wanna keep your mouth shut until your wife has some time to get comfortable with her new boobs, MILK, and their new milk-producing superpowers.

Once the kid is out and the milk is in and your wife has fully recovered from the birth experience and you start fucking again… you should probably keep keeping your mouth shut. The wife won’t have forgotten ...

My wife and I click on just about every level—parenting, money, religion, politics, etc.—except for sex. After our last child was born, my advances were increasingly rejected. In an attempt to avoid pressuring her, I stopped initiating. One week passed, nothing. A month passed, nothing. A YEAR passed, nothing. Depression and anger set in. But I was committed to being the “perfect husband,” so I did not pressure her, hoping her libido would return. It didn’t. Our “happy” life continued, and if you were a friend or neighbor, you’d have no idea this was going on. After two years, I finally lost it and confronted her. I expected that an open dialogue would improve the situation, but a month passed, and she never brought it back up.

She’s a stay-at-home parent, so she does most of the shopping, laundry, etc., but I contribute to the housework. We live in a large house, so we also have house cleaners and landscapers. Additionally, our kids are respectful and have been taught to pick up after themselves. The bottom line is that I’ve removed all of the obstacles I can think of.

I realize that I’m ...

I came out as trans-something/genderqueer three years ago. I was born male but live my life predominately as female. I’m 25 now. Coming out involved accepting that it would complicate my ever finding someone. I haven’t dated since.

My problem: Today, a guy my age asked me out while making me a sandwich in a cafe. He told me I was very pretty and asked if he could take me out. I gave him my number. Before I left, he said, “I’d really like a relationship with you.” That sounded like a weirdo red flag. I told him, “We’ll see,” but agreed to the date.

I don’t know the rules and I’m a panicked mess. I know to meet in a public place, in the afternoon, tell people about it—all the safety stuff—but I am afraid that he’s a creep. But no one has ever told me before that I’m pretty. While I’m not ugly, I’m not passable. My questions:

1. Was he way too creepy to go on that date?
2. Was agreeing to a date smart or dumb?
3. Am I acting out of desperation ...