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;When I was a promiscuous young man, I had lots of anal sex. I particularly loved rough, unlubricated anal sex with those wonderful women who enjoyed the same. I swore I would never be with a woman who didn't love anal. But I am now dating a woman whom I love intensely and who is open to it, but we just can't make it happen. Toys, fingering, eating ass, fucking — it all hurts her. She wants to do it, but obviously neither of us wants to see her hurt. Please help. This is important to me.

;;Boy Wants Anal Action

;;Toys, if they're too big or ineptly employed, can hurt. Fingers, with their bony knuckles and sharp nails, can hurt. Fucking can hurt. But eating ass never hurt anyone. I mean, tongues and sparkling-clean buttholes go together like rama-lama-lama-ke-ding-a-de-dinga-dong.


;So unless you're wearing a diamond-encrusted grill or you studied eating ass under Jeffrey Dahmer, there are only three plausible explanations for this baffling assertion, listed here in ascending order of plausibility. No. 1: Your tongue is 4 feet long and it irritates her esophagus when you rim her. No. 2: She's got a very serious medical condition — chronic fissures? terminal hemorrhoids? suppurating gunshot wound? — that she hasn't told you about because she doesn't want or need your damn pity. No. 3: She doesn't like anal and never will, but she's telling you what you want to hear.


;But, hey, let's take her at her word: She wants it. What can you do to make it happen? First, forget those women you met at college who liked their anal unlubricated. (Where the fuck did you go to college? Bloody Stool U?) Most people — sober people, male and female people, people who want to live to get fucked another day — require tons of foreplay and gallons of lube before buttfucking. Once everyone is nice and relaxed, you slowly penetrate your partner, giving his or her anal sphincters plenty of time to relax.


;If you've been doing all this and it hasn't worked, well, then dating this woman means going without anal.


;;My boyfriend and I have a problem with anal sex. He says my dick is too thick and that it makes him come too quickly. As soon as he comes he tenses up and we have to stop. Am I doing something wrong?

;;Boy's Irksome Girth

;;If your cock were "too thick," BIG, your boyfriend wouldn't be able to come when it was in his ass. He'd just lie there shrieking, "Get it out of me! Get it out of me!" That you can get it in and fuck him until he comes is proof that you're not too big or too thick. You're just right.


;The issue, it seems, is that your dick quickly pushes your boyfriend over the edge; perhaps, thanks to your girth, your dick slams his prostate in a way no other has. So what can you do? The next time you fuck, stay inside him after he comes — with his prior consent, of course — but cease all movement. He should breathe deeply, riding out his orgasm, and allowing his sphincters, which tensed up as he came, to begin to relax. Once his orgasm subsides and his ass calms down, you should be able to start fucking him again — but very slowly, just like you would at the start.


;;I think my 13-year-old brother is gay. ;I came home from school at Christmas to visit my family. One night I turned on my MacBook and and there was no battery left. I plugged it in. Once it was on I was shocked. There were pages of gay porn displayed on my screen. Hoping it was some freakish virus, I sought out every webpage accessed on my computer. There were similar entries every time I came home for a holiday.


;Only one person might have used my computer: my brother. I didn't say anything to our parents, and I didn't talk to him about it either, because I didn't know what to say. If it were straight porn, I would probably have just told him that he shouldn't be looking at material like that. But on the sites he accessed, I found violent porn with themes of rape and domination.


;How do I talk to him about this without him feeling ashamed? Moreover, how do I address the violent porn? And finally, what should I do as his brother?


;Concerned Older Brother In Kansas

;;Remember what you were like at 13, masturbating furiously and checking out online porn? Your brother is curious about everything that's out there, which could explain the extreme stuff. Or maybe your brother is kinky, in which case, tell him that he can ethically indulge his more extreme fantasies with other consenting adults when he's an adult.


;Eventually he'll want to come out to the whole family, but in the meantime he should be more cautious online. Any adult gay men he meets online are not his "gay brothers," but sexual predators.


;Finally, you ask what you can do as his brother. Gay teenagers often get into trouble because they have no one to confide in, no one to turn to when they have romantic problems. Be his older, wiser, supportive sibling, the person he can turn to for advice.


;;What's the biggest difference between a gay and a straight marriage?

;;Straight Boy Wants To Know

;;The only really significant difference is the likelihood of any given husband hearing these magic words: "Honey, it's been way too long since we had a three-way."

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