Twitter Facebook Instagram Google+ Tumblr YouTube E-Mail WhatsApp Sign In Check Close snapchat
Exit Clear
Playboy Advisor Playboy Advisor

Playboy Advisor: November 2015

Playboy Advisor: November 2015: Skip Sterling

Skip Sterling

Am I the only guy who thinks breasts that are clothed are sexier than ones that are bare? There’s nothing hotter than the idea of having sex with a woman who is still wearing her shirt. It’s sort of a fetish for me, and it sometimes makes it difficult to be in public with lots of women. I’ve become quite the connoisseur of breast sizes and shapes, but only if they’re covered up. I love breasts when they’re in sports bras, no bras, sweaters or oxford shirts. Am I weird? —N.R., Las Vegas, Nevada
You’re a little weird for reading a magazine known for publishing photographs of bare-breasted women. While the degree to which you’re attracted to covered breasts isn’t common, most guys have felt some version of what you describe; many fetishes are extreme versions of something we all have inside us.

My boyfriend and I have been together for more than two years, which is amazing considering I have major commitment issues. And for most of those two years we’ve been acting like rabbits in mating season—we literally can’t keep our hands off each other. Surprise, surprise, I’m now pregnant with twins, which is awesome except for how things are going in bed. We still have a strong sexual connection to each other, but the sex is not at all the same. He is way quicker lately, and I can no longer get into some of our favorite positions. We’ve been trying foreplay to make it last, but as soon as we’re getting down to it, it’s over in two minutes. What should we do? —C.H., Cleveland, Ohio
Congratulations on a) the long-term relationship, b) the impending birth of your children and c) the fact that while pregnant with twins you’re still up for having sex. Judging from c) we assume you’re fairly early on in your pregnancy and haven’t gotten too big yet. And when you say “it’s over” in two minutes, we assume you mean he has an orgasm in two minutes and you don’t. And when you say “getting down to it,” we assume you mean having actual old-fashioned penis-in-vagina intercourse. If all that is the case, then you could try to slow down on the foreplay front and really make the most of it. Treat foreplay as play, without the fore. Let the journey be the destination and not a warm-up period, which from the sound of it he at the very least doesn’t need. That said, we understand preferring old-fashioned penis-in-vagina sexual intercourse, or sex classic as it’s been called. Might it be that your boyfriend is coming faster because of the new positions you’re trying? Maybe the angle is stimulating him more than usual while you’re not getting stimulated enough. Depending on the positions you guys are trying, we suggest he add some manual stimulation of your clitoris both before and while penetrating you. It also sounds as though he should be riding the brake a lot harder than he has been. This may sound unfair, but you could make a rule of no blow jobs, hand jobs or any other stimulation of his penis until you’re as close to coming as you can get. And if all that isn’t enough to get you two in sync, don’t fret too much, as this will pass. Plus, you’re in good company. Almost 50 percent of men have orgasms within two minutes of intercourse, so there’s no shame in that.

I’m a recent college graduate and a novice cook. My boss just invited me to a Thanksgiving potluck at his house. His family will be there, as will a few Thanksgiving orphans from work, including my direct manager and a colleague I don’t like very much who sees me as his competition. I’ve been told I’m supposed to bring a “vegetable side.” What should I do to look cool and not appear as though I’m trying too hard? —D.C., Springfield, Illinois
Trying too hard might actually be a good thing in this instance. It’s impossible to over-deliver food, particularly when it comes to Thanksgiving, a holiday that is all about abundance, and especially when you’re trying to impress your boss. What you don’t want to do is try to over-deliver and fall flat on your face. Your best bet is to make something with bacon in it, which will obscure any lack of technique and experience that may be evident in the rest of the dish. This is going to sound weird, but you should make brussels sprouts. They may seem gross at first, but brussels sprouts have actually made a comeback in foodie circles because people finally realized they’re nutty, sweet and delicious when handled correctly. Paired with bacon and glazed with a balsamic-vinegar reduction, they’re transcendent. Here’s a recipe for balsamic glazed brussels sprouts with bacon; it’s kind of a new classic, and everybody digs it. Heat your oven to 400 degrees. On a baking sheet, spread out one and a half pounds of brussels sprouts that have been halved lengthwise and trimmed on the ends. Add a quarter cup of diced bacon and a couple of tablespoons of olive oil, along with some salt and pepper. Mix it all up and spread it out in one layer. Roast the sprouts-bacon mix for about 25 minutes. While it’s cooking, pour a quarter cup of balsamic vinegar into a saucepan and reduce the liquid by half. When the sprouts are done, drizzle them with the balsamic syrup, mix and transfer to a nice bowl. (If you want to be really safe, practice this recipe a few days before the main event to get your confidence up.) And oh yeah, bring a bottle of pinot noir and you’ll look like the star you are.

My girlfriend has genital herpes. Is this curable? If I use a hollow strap-on for intercourse and don’t swap spit with her or lick her vagina, will I catch it? Or should I just keep her as a friend and fuck someone else? —H.C., Detroit, Michigan
Genital herpes is not curable, though it is manageable. The risk of infection rises and falls with the appearance of sores. But having sex only when you don’t see sores isn’t a fail-safe method of preventing the spread of the virus. When there are no sores present, the risk of transmission is extremely low, though once or twice a year an infected person could be shedding virus without any outward signs. If by “hollow strap-on” you mean a condom, then no, you will not be fully protected. Sores can appear both on and in the vicinity of the genitals. Nor will a real strap-on protect you, for the same reason. Additionally, you can get oral herpes from infected genitals. Before you give up on your girl, don’t assume you’ll find safe haven in the world of potential partners. Nearly 20 percent of the adult population has herpes. So if you do decide to ditch her and try fucking someone else, you owe it to the general population to find out if you have any form of the virus: Many people who carry the herpes virus never show symptoms, so don’t be so certain you’re in the clear.

Is the “dry-clean only” label on clothing a joke? I’ve heard you can wash most clothes, even ones marked “dry-clean only,” in cold water using the gentle cycle and then dry them flat or on a hanger. Does the same go for suits? I’m starting a new job that requires me to wear a suit every day and I’m looking for ways to save money. —L.B., Rockport, Maine
We wouldn’t recommend cleaning a suit in a washing machine. While cotton and wool can stand up to gentle washing, the fabric could be a blend of materials that can’t handle water without shrinking considerably or losing their shape. Additionally, the lining might be silk or rayon, neither of which do well in a washing machine. While you can sometimes get away with washing a sweater or shirt, a suit’s construction can be quite complicated and presents far too many opportunities for a machine wash and dry to screw up the lines and drape. Better to be safe than sorry. You don’t want to run the risk of ruining an expensive item in an attempt to save money. That said, dry cleaning can be tough on a suit and wear it out quickly if you take it to the cleaners too many times. Try airing it out and brushing it clean when it needs it. Also, spot-clean spills and dirt as soon as they occur. Once that regimen fails to freshen up your suit, it’s time to take it to the dry cleaner. Many men try to dry-clean their suits only once every six months or less often if they can.

How likely is it that someone could scan your credit-card numbers when the cards are in your wallet and the wallet is in your pocket? Are those woven steel wallets really secure? Can you keep your cards more secure by placing a sheet of tinfoil in the bills section of a trifold wallet? —B.S., Tallahassee, Florida
Only credit cards with radio-frequency identification, or RFID, chips are at risk for having their data scanned remotely. Scanners are cheap and can grab data from up to 25 feet away. Whether or not the hackers can use that data is up for debate. Several years ago some cards were vulnerable to the degree that the cardholders’ names as well as their credit-card numbers could be stolen remotely. Since then companies that issue such cards claim to have encrypted the data, removed personal information and created point-of-sale safeguards that render the data unusable. But since that may not be enough reassurance for some people, metal wallets and sleeves can block such scanning, and yes, so can wrapping the card in foil. Or you could request a non-RFID card from your bank. But don’t think you’re safe from the multibillion-dollar threat that is credit-card fraud: An old-school magnetic-strip card is still susceptible to the much more widespread practice of credit-card skimming.

When I was serving in Afghanistan my wife would talk dirty to me on the phone. The longer I was over there, the dirtier the stories got. After I returned home and went through a hard alcohol phase that lasted much longer than it should have, my wife had a one-night stand. She later told me about it, but instead of being hurt and upset I found it extremely arousing. Now, five or six years later, I’ve been fantasizing about watching her with another guy. How do I bring this up to her, and what do I do if she goes for it? Is this something you’ve heard of before? —J.J., Spokane, Washington
This is one of the top 10 sexual fantasies the Advisor hears about from readers. Many men are aroused by the idea, and we stress “idea.” Safely turning the fantasy into reality is an entirely different matter. Add up the challenges of finding the right guy, making it happen and then dealing with the consequences, and that erotic fantasy can turn into a real-world headache. Another one of our top 10 questions is, How can my wife/girlfriend and I safely arrange a threesome with another woman/man? Again, it’s a very tough thing to pull off if you aren’t connected to a swinging community. The fact that this first came up during a period when you were drinking heavily makes us question whether it’s an area either of you wants to revisit. Presuming things are going well, why mess with a good thing?

My husband and I dabble in making our own sex tapes. Is there a way to profit from our penchant for videography? —D.E., Phoenix, Arizona
Absolutely. It’s called the internet, and there are hundreds of sites that pay for amateur porn they can distribute throughout the web. However, it can be difficult to make significant money without a lot of trial and error and hustle; plus, you’ll have a ton of competition from amateurs around the world. If you’re creating the videos mostly for fun but want to make a little money off them, consider looking into the granddaddy of amateur internet porn, Homegrown Video. It’s a reputable site run by a former Deadhead who got into making porn to finance his world travels following his favorite band. It has been around since the early 1990s and pays anywhere between $200 and several thousand dollars per video. Check out the site’s guidelines and rates at These days a scene with straight sex and a come shot can get you between $250 and $500. Word to the wise: You may want to upgrade from tapes to shooting on an HD digital camera to improve your chances of getting picked up.

Could you please tell me which American brands of tuna in five-ounce cans are entirely processed and canned in the U.S.? I’ve seen internet scares about one brand whose product is canned in China under very unsanitary conditions. I’ve been buying this brand for years and it has nothing on or under the label that clearly tells you where it’s processed. —B.W., Goshen, Connecticut
While it’s slightly more expensive than the better-known brands, the aptly named American Tuna is not only canned domestically, but the tuna is hand-cut after being caught using the sustainable pole-and-line method that reduces by-catch. Additionally, American Tuna catches only younger fish that live closer to the surface of the ocean, which means the mercury levels in its product are far lower than the allowed amounts.

My friends and I are all in our mid-40s and grew up together in a small suburb outside New York. The generation before us grew up experiencing the sexual revolution and free love. Members of today’s younger generation carry devices festooned with countless apps that enable them to meet horny women as easily as ordering a pizza. We, on the other hand, grew up with AIDS and Ed Meese. Getting laid was difficult and required a cosmic combination of luck, circumstance, timing and effort. None of us cheats on our wives, nor do we really wish to (though that seems easy enough too these days). Still, we can’t help feeling a little left out. In the modern history of sex it seems we operated in what would be considered the Dark Ages. In one recent Advisor letter, a guy said that because of Tinder he is “having more sex than I thought humanly possible.” Must be tough. Has the game really gotten that easy? Are we being crybabies, or do we have a right to feel as though we’re stuck with the middle seat between two lottery winners? —B.L., Long Island, New York
Yes, your generation was particularly screwed by timing. And yes, the game has gotten a lot easier thanks to mobile technology. That said, there’s no shortage of data out there that shows today’s generation isn’t any more sexually content than previous ones. It’s that age-old question of quality versus quantity.

My girlfriend and I have a very active and enjoyable sex life, but from time to time I like to wait and hold my ejaculation back so I can make it last longer. She says I shouldn’t do this, that I should just let it go when I’m ready. I don’t see any problem with “waiting” a bit longer—except that once in a while I can’t finish because I held it too much. She claims this isn’t good for me. What’s your take? —P.D., Hogansburg, New York
There’s no compelling science that shows this is bad for you. It could be that she simply wants you to finish up faster and doesn’t have the heart to just come out and say it.

For answers to reasonable questions relating to food and drink, fashion and taste, and sex and dating, write the Playboy Advisor, 9346 Civic Center Drive, Beverly Hills, California 90210, or e-mail The most interesting and pertinent questions will be presented in these pages each month.

More From Playboy Advisor See all Playboy Advisor