Am I out of bounds if I try to have a dialogue with my nephew about masturbation? He's 17 years old and I'm 52. I'm also a balanced bisexual male in a good marriage. I masturbate a lot and enjoy pornography sometimes. My nephew trusts me and brings up the topic constantly.

Some of my previous frank discussions with other nephews have been criticized, especially when a 15-year-old nephew got into my video library. (It happened 15 years ago; today the boy is straight, married, happy and we have a good relationship.) Any advice would be welcome.

Uninformed Nephew Craves Lasting Education

Are your motives pure, UNCLE? Your "previous frank discussions with other nephews" got you into trouble, which either means you're a creepy old fart who gets off on talking about sex with his nephews – and your relatives know it – or that you come across that way when you talk to your nephews about sex. You need to look inside your heart and ask yourself if you want to "have a dialogue" with your nephew about masturbation because he needs a trustworthy, responsible adult to confide in or because it makes your dick hard.

If it's the former, here's how you can avoid coming across like a creepy old bisexual with designs on his nephew: Let him initiate these conversations and refrain from following up answers to his questions with leading questions of your own. Let him begin these conversations, keep your answers simple, absolutely no oversharing (he doesn't need to know about your lube or porn preferences) and let him end the conversations. In short, do nothing that might give your nephew the impression that you beat off about your little chats. If you find that you simply can't be cool, calm, informative, reserved, restrained and respectful, then let your nephew go elsewhere for info.

Every year my family goes on a weeklong vacation to the beach. By family I mean my mom, my brother, my sister-in-law and their kids (10 and 13). When I was married, I came with my wife and our two kids. Two years ago, I came out of the closet and got a divorce.

This year I decided to invite my boyfriend. We have dated on and off since my divorce. But before inviting him, I forgot to mention it to my family. My brother is ultraconservative; I get along well with my sister-in-law, so I approached her with my idea of bringing my significant other to the beach. Her reply was: "David, this has always been a FAMILY VACATION. If your relationship with your boyfriend is stable enough that you consider him 'family,' I can sit my kids down and explain to them why Uncle Dave is bringing his friend and why they are going to be together at the end of the day. But if you don't think your relationship with your boyfriend is that stable, then I don't think it's fair to put our kids through this."

I agree with her to some degree; after all, we all pay for the house and we should all feel comfortable in it. My boyfriend, however, thinks she's full of crap, hiding her prejudice behind her kids. What do you think?

The Gay Uncle

I think straight people say the darndest things sometimes – and I think your boyfriend is right. She's trying to cover her own discomfort with that "I don't think it's fair" crap. Here's what she should have said instead: "We're still getting used to you being gay, and we know we're going to have a conversation about it with our kids sooner or later. If you're serious about this guy, we'll have it now. But if you're not serious about this guy, please spare me from having a conversation I'm not ready to have with my kids."

That would have been more honest – still fucked up, for sure, still full of crap, but honest. At 10 and 13, your nephews know about gay people and they're old enough to know they're related to one. You shouldn't have to be closeted around them, serious boyfriend or no serious boyfriend.

And since when do people have to be "family" before they can come along on a family vacation? If you were dating a woman for two years after your divorce there would be no question about her being made welcome at a family vacation – hell, your family would be anxious to meet her.

So what do you do? Well, you insist. Tell your family that you realize your coming out came as a bit of a shock. But it's been two years and that's plenty of time to absorb the shock. From this point forward you're going to insist on equal treatment. You've been dating this guy for two years – it's time he met your family. If your boyfriend isn't welcome, then your brother and sister-in-law will have to explain to their kids why Uncle Dave isn't coming.

Here it goes: When I was little my uncle raped me. And I'm not talking soft touches in "no-no" spots. He did some pretty nasty stuff. Anyway, I've gotten past that and I'm now with the most loving man I could ever imagine being with. The problem: He likes butt sex. Considering my past, butt sex kinda … freaks me out. He wants it so bad, and part of me wants it too, but when we try it hurts – a LOT – and I get scared. I freak out and he stops, but I know we both want it. Is there any advice you could give me on this?

Running From Her Past

First, you have all my sympathy. I hope your uncle dies/died a horrible, lingering death. Now on to the problem at hand.

The first thing you need to do is expand your definition of butt sex, RFHP. Actual penis-pounding-away-at-butt sex is varsity-level, and you're clearly not ready for that squad. But there are plenty of junior-varsity options for your butt – and for his butt, too – that can help you work your way up. I'm talking gentle, external stroking with lubed-up fingers, lots of licking, vibrators placed on your butthole (that's on or across, not in). If you incorporate these gentler anal pleasures into your regular routine, pretty soon you'll be having mind-blowing orgasms while your boyfriend rims you or holds a vibrator against your ass as he fucks you senseless. In time you'll begin to associate your butt with pleasure, and Uncle Fucker's grip on your ass will loosen. Only then should you go out for the varsity team.

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