Dear Josey,

What kind of sexual pleasure does a women get by trying to penetrate her boyfriend with a dildo? What’s in it for her? Is it that penis-envy thing again?

Strapped for Answers

Dear Strapped,

In The Strap-On Book, author A.H. Dion writes: “Let’s face it: whatever your gender, whatever your orientation, penetration is part of what many of us associate with sex. Entering the body of your lover — with penis, finger, hand, tongue or toy — is an act of incredible, inimitable intimacy…. And to most of us, it feels very, very good.”

I have to agree. Though, I also have to admit, the times I’ve strapped on a penis, it did not stir feelings of envy so much as a sense of the power that goes with having a penis. Because, let’s face it, there’s no denying the potency of the phallus. As Dion also writes: “From skyscrapers to supersonic fighter jets, if it’s longer than it’s wide, it holds a pride of place in our culture.”

There’s also something compelling about learning how the other half lives. Wanting to know what it’s like to penetrate someone is a pretty common fantasy among my female friends. Also, switching roles changes the power dynamics of sex with her entering him and him being entered, and that can be pretty darned exciting and intimate. Suddenly, she is the actor in the act of penetrative sex, and he is the vulnerable receiver.

Does it mean she wants a penis and envies men who have one? Maybe occasionally, but trust me, when it comes right down to it, most women I know are perfectly happy to own a vagina.

A couple of tips if you’re looking to strap one on: While it’s tempting to be like boys and want the biggest dick in town, I suggest you start out small and use lots of lube.

If you want more info, Dion’s book includes tips and answers to all your strap-on questions. It also has some hot pieces of erotic fiction describing strap-on scenarios. Or try The Ultimate Guide to Strap-on Sex by Karlyn Lotney, available online at goodforher.com.

Dear Josey,

Is it polite to give head after only a couple of dates? And what suggestions do you have for leading up to it with a new man (things like kissing his inner thighs, licking, etc.)?

Heading in the Right Direction?

Dear Heading,

As long as you say please and thank you and don’t do it in mixed company, I think it’s perfectly acceptable to have oral sex on a second date if all parties involved agree. Now, I’m presuming you won’t go out to dinner and suggest you go down on him for dessert. Mind you, that would certainly be an exciting way to introduce it. Again, I’d suggest this only if you’re eating at home.

As for the lead-up, every guy is different, but I think it’s always a safe bet to ease your way into it, rather than simply diving in like you’re bobbing for apples. Thigh-kissing is good (heck, why not start at his ankles) and moving in slowly is usually a hit as is licking slowly and lightly around his penis. I’m a fan of giving him a small hint at what’s to come and then moving back out to his thighs, chest, maybe even a nice sensuous kiss on the lips. When you’ve got him worked up into a good frenzy, try taking him in your mouth as far as you can, just once or twice, and then moving back to the outer lying regions. There’s also that lovely little underbelly of the penis just below the head that enjoys a nice lick now and again. While most guys get nervous about the idea of teeth having any kind of involvement with their penis, some guys I’ve been with have enjoyed a (very) gentle grazing of teeth. From what I’ve observed, it pretty much all feels good. Mix it up, and don’t limit yourself, look like you’re having fun (even better, have fun) and be sure to offer him lots of positive feedback. You’re sure to be a hit.

Dear Josey,

Is it normal for a guy not to actually ejaculate, but to have a non-semen-producing kind of orgasm? I ask because I experienced this sensation while going at it with my girlfriend: I didn’t actually come but my arms and hands and fingers were on fire and tingling. After, when I tried to get up off the bed, my knees gave out. Is this normal for guys? And is it healthy?

Feeling Sensational

Dear Feeling,

Congratulations, you’ve achieved what tantric-sex practitioners spend years trying to perfect. You’ve achieved orgasm without ejaculation.

Normal, yes. Common, no. Healthy, yes!