Sex rags get some weird questions. Even weirder than our Editrix, which is saying something. At least she doesn’t get stupid questions. We’re grateful for this, because if she did, she’d probably make us answer them instead of dealing with them herself in public.

So this guy writes in the Penthouse, right, about how his wife’s vagina is not as tight as it once was and he’s become obsessed with doing her in the ass. We here at Sex and the 405 are distressed by the way that the subject matter was approached, but we’re looking on the bright side: the question provided a perfect platform to discuss anal sex and we find that’s something you can always learn more about.

Here’s an except from Penthouse’s response:

It should never hurt. Pain means something is wrong and is possibly causing harm.

Another key is using lots of good, water-based sex lube made specifically for that purpose (not spit, suntan lotion, or whatever else happens to be handy). However, even with copious lubrication, it still feels bad to stick something up your butt if you don’t really want it there. The muscles of your anal sphincter must be coaxed to relax in order to allow penetration. For that to happen, you have to feel safe, at ease, and completely willing. Don’t try to use booze or drugs as a shortcut, because they’re apt to cloud judgment and obscure pain, increasing the risk of injury. Desensitizing creams or lubes are also strongly discouraged for the same reason.

Before doing it with a partner, it’s a good idea to get comfortable with anal penetration through solo exploration, using fingers or dildos of different sizes. Always proceed slowly, and never force anything through the anus. Whether it’s as slender as a pinky finger or as fat as a soup can, it should slip in effortlessly.

So there you have it. A few good tips on proper anal sexing. Want more? Check out this forum. You’re welcome.

(We were going to call this section “we read the skin rags so you can jack off to the pics” but our Editrix said that’s too long. Alas.)

Image by Redacted. Information via Penthouse.

Some of us are just not looking for a relationship. We have our reasons—and I don’t think there is anything necessarily wrong with it, assuming, of course, that you don’t behave like a total douchebag.

I wrote a piece for Manolith this week that spells out how to go about acquiring and keeping happy lovers.

Here’s a preview:

The object of your attention must be aware that you are not seeking a relationship. This doesn’t necessarily mean sitting the woman down before the first drink and spelling it out for her, but if you’re man enough and do, that’s the best way. Do not assume that your reputation precedes you. By this I don’t mean a bad reputation, I mean a general understanding among members of your social circle that you’re not the relationship kind.

Since I want a partnership where one party looks out for the other as friends do, and there is very little buddy about “fuck buddy,” I avoid that term and put it like this: “I’m not looking for an exclusive relationship. I’m looking for a non-committed, long-term, mutually-beneficial partnership.”

Now, I’m not saying that it’s bad to wish to have a purely physical relationship with someone. If that’s what you want and that’s what she wants, then by all means proceed. However, I should mention that I’ve never met a man who didn’t eventually confess a degree of vexation at the idea that I only kept him around for sex.

It’s human nature. We want to be special. And we should be. Even if our particular brand of special doesn’t involve exclusivity. In any case: The key point here is that the terms of the relationship must be clear to all parties.

If you suspect you need to cloud your intentions because the person you’re pursuing wouldn’t go for you unless you suggested you’d eventually be her man, you: a.) don’t know how to pick your audience, b.) don’t have balls, and c.) should probably stick to getting chicks drunk and taking them home, then never calling them again.

Remember one thing: in today’s world of digital nomads, it’s great folly to burn bridges.

You can read it all here.

Debby Herbernick, the sex professor and author of Because It Feels Good has some pointers for getting it on wet and wild-style:

Wet doesn’t actually mean lubricated.

“As anyone who has spent significant time in a bath tub or shower knows, warm water can dry the skin and turn us all a bit prune-like,” she says. This also applies to the vagina, so make sure that you or your partner are well-lubricated before getting started.

Not all lubricants are created equal.

Water-based lubricant is, duh, soluble in water, so it won’t work. Oil-based lubricants work best in my opinion, but these are unsafe if you’re using a condom (more about this later). The best bet for condoms and showers, then, are silicone lubes. “Silicone based lubricants are slicker, longer lasting and difficult to wash away,” Herbenick notes.

Condoms have not been tested for underwater sex.

Careful here. We don’t know how safe condoms are in water. Will they slip or break more easily? “If you are relying on condoms for the prevention of sexually transmissible infections (STI) or pregnancy, then you should perhaps stick to sex on dry land rather than sex in the shower or bath,” the sex prof says.

Positions in the shower can be challenging.

“Rather than be rigid about how sex in the shower ’should’ be, try expanding your idea of shower play,” Herbenick says. “Why not soap each other’s bodies up, or indulge in some oral sex play, as a means of foreplay? Sex in the shower can be used to enhance excitement and arousal before you transfer to dry sex, or at least the bed, for other types of sex you might wish to engage in.”

Personally, I find sex standing, with penetration happening from behind, most effective. If there are height issues, you can easily adjust at the knees. This requires a little bit of lower body strength, but it’s worth your while if you want the full experience.

The Sexiest MILF on the Planet, Brenda James

On my last diary post, a commenter asked for more on older women, specifically where to find them.

I personally believe potential cougars and MILF partners are everywhere and that it’s more about taking a situation to that level.

So before I get to the question of “where,” let’s list some basic tips:

Older Woman How To

1. Scout’s Motto. Make sure this is what you want – that it is a fantasy you really want played out – and be prepared for an amazing time when it happens. Don’t get soft on her.
2. Game Over. Many older woman are done playing the coy games we do in our twenties.  Be honest about what you want because she will be direct about about her desires.
3. Listen. On that note of directness, listen to her words because she is still a classy woman who will expect you have some brains to read between her obvious lines.
4. Play. She’s not flirting or initiating conversation to waste her or your time.  Flirt back because there’s an endgame that will leave you satisfied.
5. Respect. If she has children, you must understand that she may not want you at her home, or at least when her kids are home. Don’t be pushy, be patient, it’s worth it.
6. Foreplay. It may or may not happen (sometimes, she just wants it… and right now). Go with that flow and give your all if in foreplay mode.
7. Endurance. She’s likely at a sexual peak unlike any before.  It might be a long, but awesome night.  You’re young (that’s part of the attraction) so make sure you’re hard for long enough! Expect to do it multiple times in a night.

Now, on to where to find a frisky kitty woman.  There’s no one answer to this. Here in Los Angeles, cougar dens, as they call them, can be found in suburbia.  Think The Southbay, Agoura Hills/Thousand Oaks, Orange County, Pasadena. That may sound a bit stereotypical but in my experience, the divorced women living here are feeling a bit sheltered so it’s your job to spice up her life.  Still, MILFs are everywhere:

• Online: Whether it be MySpace or Facebook, does she list her self as single and looking? Does she have other younger guys as friends? If on a dating website, does she directly say she likes younger men.  Did she look at your profile? Remember, older women will be more upfront than younger women in most cases. If she’s flirting, follow through because, remember, she’s done with games.
• The grocery store (or any store for this matter), art galleries, coffeeshop: Does she look your way often, make eye contact, did she throw you a smile? And if she asks you a dumb question about where the soy sauce is, the door is definitely open for you to engage.
• At bars, on the casino floor, social situations: Things should be fairly obvious in these situations, but the drinking makes people more flirty  than usual, even if she’s not looking. But hey, in places like that, live it up, be yourself and have fun as that’s what a woman will find attractive.
• On the sidewalk.  In all cases like this, it doesn’t hurt to throw a smile in when you make eye contact. You would be amazed how little people do this and how much such a small gesture can open things up.

Got questions, comments?  Ask, let it be known, etc.  You can also follow me on Twitter at @Arrow405.

Above photo of Brenda James via her website.