Don’t be a dickhead
Spend more time on your play away from the puck, guys

Dear Josey,

I’m a curious 14-year-old boy with some questions:

1) At my age, is it worth getting circumcised?

2) "The bigger, the better," right? I have a six-and-a-half-inch penis – is that sufficient or should I look into penis enhancers?

3) How can I prolong ejaculation?

4) How is it that the guys in porn flicks have so much cum? (They can spray it everywhere!)

Dear Dick,

And here I thought boys your age just worried about staining the sheets after a wet dream or getting to "third base"...

I mean, I’m glad that you kids are getting better info about sex these days (especially being someone who contributes toward spreading all this filth), but I’m a little disappointed by such conventional concerns. You do know by now that penis size and amount of ejaculate are not crucial to a good sex life, right? So, no, it’s not necessarily "the bigger, the better." You’re doing more than fine at just over half a foot. I wouldn’t recommend penis enhancers.

As for prolonging ejaculation, please don’t buy into the myth that women need you to last until they’re chafed and raw. However, if you really can’t make it much past the gate, here’s a trick: masturbate before a date where you know you might have sex. This might help you last longer when it’s showtime.

Is it "worth" getting circumcised? Well, plenty of women have no problem with uncircumcised men – some even prefer it. And I’ve always maintained that an uncut penis provides its own built-in lubrication thanks to the extra skin. But I truly think it’s strange that guys who won’t let someone swab ’em (or stick a finger up their bum) to test for diseases are willing to consider having a big flap of skin sliced off their penis. Unless you really have issues with your foreskin, leave it be.

And the men in porn flicks don’t have any more cum than you or the next guy. But thanks to the magic of video, they can make it look like they do. It’s all fantasy (ditto for those "perfect" models in the fashion mags). Can we all just get over it, already?

So stop worrying about all this superficial stuff. You’re better off learning how to become an attentive, affectionate and skilled lover. That’ll get you much further than a 14-inch penis that shoots like a geyser.

Dear Josey,

I am a 19-year-old girl in a fairly new relationship with a 24-year-old. Everything is going great and I feel really close to him on many levels. But I’m nervous about first-time sex with my guy, since he’s more experienced than I am. I did have sex with a long-time boyfriend in the past, but never fully enjoyed it. (In fact, it hurt like crazy when we started out, and then got to the point where it was simply uncomfortable.) I am not scared of sex and feel as though I’m ready to share that with this new guy. I want to be able to have good sex, but I need to get over the initial awkwardness and insecurity. Advice?

Dear Seeking,

Maybe it’s a back-to-school thing, but I seem to be hearing from all the young’uns this month. The truth is, in most cases, sex usually takes a few kicks at the can to become fun for girls (for guys too, really, but they at least get off from intercourse, even early in the game). Many women have told me that the first few times weren’t exactly blissful and, yes, were often even painful. It does get better, trust me.

If you feel close to your new guy, you should be able to talk to him about this. Tell him you’d like to take your relationship to a sexual level, but that you’re nervous and worried that you won’t live up to his expectations. Ask him if he’ll be patient and share some of his experience with you. If he’s a nice guy, he’ll be charmed that you’re being honest – and flattered that you want him to teach you. (And it’s quite erotic to have a partner who can open you up to the joys of sex.)

But don’t be so sure that, at 24, he’s necessarily all that experienced. If our 14-year-old friend above is any indication, are guys really learning anything about what it means to be a good lover? It’s all about communication, honey. Talk to each other.

Dear Josey,

When is the right time to put on the condom? During or after foreplay, and should the female or the male roll it onto the penis? This and any advice that you can give a first-timer would be appreciated.

Dear Ready,

Well, you don’t want to be like the guy I heard about once who put the condom on before he went out on his date...

OK, I’m happy that you’re asking about condom use, but find it a little distressing that you create such a definite line between foreplay and the act. Is nothing I’ve been harping on all these years getting through to you people? Foreplay is part of sex, not a separate thing. End of story.

That aside, bottom line, you have to put the condom on before vaginal or anal penetration. Whether you do that as soon as you’re naked or after hours of glorious kissing, humping, and sucking is up to you. Ditto for who puts it on. If she’s comfy, it can be fun and erotic to involve the gal. If things are a bit awkward, it might be easier for you boys to do it since you own the equipment. And make sure you find a condom that’s right for you. There’s nothing sexier than a guy who has a "brand" he likes. It shows you care.

Other than that, I don’t care if you roll it on while standing on your head. As long as you’re covered up when you enter her (or him), that’s all that matters.