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When I was a promiscuous young man (read: straight college boy), I had lots of casual sex. I particularly loved anal sex. And I very particularly loved rough, unlubricated anal sex with women who enjoyed same. I swore thatI 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 anal sex, but we just can't make it happen. Toys, fingering, eating ass, fucking—it all hurts her. She is a ballerina and, therefore, small with a tight frame. Is there a best plan of action here? 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 and ineptly employed, can hurt. Fingers, with bony knuckles and sharp nails, can hurt. Fucking, which involves fucking, can hurt. But eating ass never hurt anyone. 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: 1. Your tongue is four feet long and it irritates her esophagus when you rim her. 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. 3. She doesn't like anal and never will, but she's telling you what you want to hear.

But let's take her at her word: She wants it. So what can you do to make it happen? First, forget those women you met at college who liked their anal rough and unlubricated. (Where the fuck did you go to college? The University of North Carolina at Bloody Stool?) Most people—sober people, male and female people—require tons of foreplay and gallons of lube before buttfucking. The foreplay can include rimming, fingers, vibrators, and the sensuous application of lube—lots of lube. Then, once everyone is nice and relaxed, you slowly penetrate your partner, giving his or her anal sphincter additional time to relax.

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

My boyfriend and I have a problem with anal sex. We're gay, I'm a top. 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. I'm a loving guy and I can deal with it—but what is causing it? 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, written consent, of course—but cease all movement. He should breathe deeply, riding out his orgasm, and allowing his sphincter, which tensed up as he came, to relax. Once his orgasm subsides and his ass calms down, you should be able to start fucking again—very slowly, just like you would at the start.

I think my 13-year-old brother is gay.

I came home from school this past Christmas. One night I turned on my MacBook to check e-mail and there were pages of gay porn displayed on my screen. Hoping it was some freakish virus, I downloaded HistoryHound and the results showed similar entries every time I came home for a holiday.

Only one person might have gone down to the basement to use 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, and it would be done. But the deeper I looked, the more disturbed I became. On the sites he accessed, I found violent porn with themes of rape and domination.

This kid has a good heart and shows a lot of love to everyone he knows, but how do I talk to him about this without him feeling ashamed? How do I address the violent porn? And finally, what should I do as his brother?

Concerned Older Brother In Kansas

Sounds like your brother is gay and kinky, COBIK, and he needs to be told that he can ethically indulge his more extreme fantasies with consenting adults—when he's an adult. So tell him. A few other things to tell him: Eventually he'll want to come out to the whole family, but in the meantime he needs to be more cautious about his computer usage. Adult gay men that seek him out online are not his "gay brothers," but sexual predators. And he won't get to date much in high school—but reassure him that he'll make out like a bandit once at college.

Finally, COBIK, gay teens get into trouble because they're isolated—they have no one to confide in about their romantic problems. Be his older, wiser, supportive sibling, COBIK, 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 significant difference is the likelihood of any given husband hearing these 11 magic words: "Honey, it's been way too long since we had a three-way."

Some readers had issues with my advice for Unlucky In Cuckoldry and Slaveboy's Husband Has Hesitations. Their letters—and my responses—are at www.thestranger.com/savage/slaveboy.

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