Q Okay, you have to help me out here. Maybe freaked-out missives about anal sex are passé now, but still, I’d rather hear it from you than trawl the Internet with some unsavory search words. So, my boyfriend and I have started having anal sex. He’s slow and gentle and it doesn’t hurt me. We haven’t been using lube, but we haven’t seemed to need to, maybe having to do with him being uncircumcised. The pace we’ve been doing it seems to work just fine for him, and it’s actually felt like a nice, loving, intimate thing. He initiates it very slowly, and eventually I relax and it doesn’t hurt in the least bit and there’s no bleeding or obvious damage at the time. However…it seems that it doesn’t have a negative effect until sometimes as much as 12 hours later, when there will be a lot, and I mean a lot, of blood. Often not until the second time that I go to the bathroom after the act. This scares the crap out of me (no pun intended). I don’t mean to gross anyone out here, but what the hell is going on? Should I be concerned, or is this normal? Why the delayed profuse bleeding? I’m just of the mind that love means never having to say, “Honey, I’m bleeding out of the ass.” This man rocks my world otherwise and I want to please him. Help!

A My whole colorectal area seized up just thinking about you doing anal without lube. Are you out of your mind? That offhanded “eventually I relax” comment makes me think you want to please him so much that you’ve convinced yourself that you’re not in pain during the act itself. But even if his uncircumcised dick does somehow magically make entering your anus a breeze, without lube, all that friction back there is bound to create tears in the tissue of the rectum. This can happen even with lube, resulting in a little back-door blood, but a lot of blood means you’re really chewing yourself up. Just for that, I’m going to insist you have your doctor give your ass a once-over to make sure you haven’t done some serious damage, and then I’m going to demand that, from now on, you lube yourself so much that you run the risk of dropping a jellyfish-like poo.

Q I’m a 28-year-old gay guy and the guy I’m seeing has one serious erogenous zone: his taint. More than his dick, his ass, his balls or nips, he loves having his taint played with. I’m cool with that, except for the fact that there are really only a couple of things you can do with it: lick and fondle. Do you have any taint-handling tips for me?

A As someone who’s actually had to endure having a hypodermic needle injected into his taint (don’t ask—it had something to do with an injury up really high on my hamstring), I can totally relate to the desire to have it treated with the utmost care and nurturing. The best thing I can suggest is combining your taint licking and fondling with simultaneous cock rubbing and/or anus fingering. When you think about it, all of sex pretty much comes down to licking and fondling, so the magic comes from learning to mix things up in surprising and mind-blowing ways.

Good news (for me, at least)! There’s been a backlash against the lactation backlash. Although I’m still getting reamed out by women who were angry that I encouraged nursing mothers to restrict their lactation-device cleaning to the workplace restroom, turns out there are more than a few new moms who actually agree with me. Check this baby out:

Q I just have to say, screw those women who gave you a hard time about the lactation letter. I am so sick of women complaining about how hard it is having a baby! And I am a woman who had a baby! Boo hoo. You have to go back to work! Be glad you have a job to go back to and quit your bitching! Fact is, washing your breast pump in the kitchen is disgusting and it makes people uncomfortable. I am in awe that women would actually want to use the kitchen sink over a private restroom. And the whole “restrooms are full of germs” thing is ridiculous.… Maybe the issue to discuss is not a lactation room at the office, but getting the restroom cleaned once in a while! The kitchen sink has just as many germs as a restroom, and all you need to be sanitary is hot, soapy water, which you can get in the restroom. Whew…I feel better!

A I probably wouldn’t have gone quite that far—my heart actually goes out to working mothers, especially during the first weeks back after having a child. But I honestly didn’t feel like my advice warranted the kind of “you’re such a schmuck” vitriol that it received. I gave in to the ad hominems because I felt as if my guy take on things must have been way off the mark, so it’s good to know that my testicles aren’t fully clouding my vision. Anyhoo, the Great Lactation Battle of 2008 is now officially over.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com. Check out “Sex on the Street” with Jamie Bufalino at timeoutnewyork.tv.

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