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Playboy Advisor: October 2014

Playboy Advisor: October 2014: Skip Sterling

Skip Sterling

An old college girlfriend and I are having a Facebook affair. I’m married and have kids. I love my wife and my happy family, but my ex-girlfriend brings me joy I haven’t felt in a decade. She wants me to leave my wife, and I’m entertaining the idea. I feel it’s a rare opportunity to experience new love all over again in midlife. Am I crazy?L.H., Dallas, Texas
No, you’re normal to want to have your cake and eat it too. But you are crazy if you think the thrill you feel with your ex-girlfriend online can be sustained in the real world. You’re both living a fantasy untested by the day-to-day reality of a relationship. Your kids, however old, will certainly suffer from the loss of their father, which will undoubtedly have an effect on your emotional state. The sane thing to do is to end your digital dalliance and make the most of what sounds like a great life.

I recently worked on a project with a female colleague. It was just the two of us sitting side by side in a conference room. At one point, as she was talking, I was listening and looking at the paperwork in front of us. She obviously thought I was looking down her shirt because she asked in an angry tone, “What are you looking at?” Completely flustered, I stammered something about looking at the papers. The next time we worked together (the two of us alone in a conference room again), she wore a very revealing blouse—so revealing I not only had a complete view of her breasts but could also see her rib cage and down her side to her waistline. As she talked, she would quickly look up to see where my eyes were. Why would a woman be angry when she thought I was looking at her breasts, then show up at our next meeting wearing a blouse so loose it left little to the imagination?A.G., Sarasota, Florida
Chalk up her initial anger to the misunderstanding you say it was and let it go. It sounds as if you work in an office with a liberal dress code and she’s dressing the way she wants. Although she may be baiting you, it’s best to take the fact that she dressed the way she did at your second meeting as proof that she believes your explanation and everything is copacetic. Still, the description you provide of her anatomy underneath her blouse is pretty detailed. If she shows up next time wearing a burka, you might want to work on controlling your gaze.

In an emergency, is it advisable to use the kind of latex glove doctors use in examining rooms as a condom?M.N., Indianapolis, Indiana
Put that glove on your hand and slap yourself in the face. Under no circumstances should you play MacGyver with issues as serious as contraception and STD prevention. Take the effort you’ve put into writing the Advisor and put it into stocking up on a reserve of condoms. Our favorite new condom company is L., which is a sort of Toms of condoms. For every condom it sells, the company provides free access to condoms in areas of Africa with high rates of HIV and AIDS. It also offers its customers one-hour delivery, but only in Los Angeles, San Francisco and Manhattan at this point. So until L. arrives in your fair city, order a couple dozen condoms from its website (thisisl.com) to keep on hand.

What is your opinion of a “family night” that uses marijuana as a way to improve family unity? I’m thinking about inviting my adult children—they are all over the age of 21—and my elderly father to get stoned with me. My hope is that it will stimulate conversation and spark more quality time together than we enjoy now.O.T., Denver, Colorado
There’s no harm in suggesting it. It may seem radical in certain circles, but smoking cannabis in moderation appears to be less dangerous than indulging in brandy and cigars. Even if people in your family pass on the invitation, it will likely stimulate conversation about how you can all spend more quality time together. If this literal potluck doesn’t work out, you can always resort to more traditional methods of family bonding, such as a round of miniature golf or a few hands of poker on a regular basis.

Please help settle a friendly debate. Is it possible for a guy to catch warts from a hand job?R.R., Langley, Virginia
Yes. There’s some confusion about the role hands play in the transmission of human papillomavirus, or HPV. While it’s true that common warts (which can develop on hands) and genital warts are both in the HPV family, common warts cannot infect genitals, and genital warts cannot infect hands. But hands can pass genital HPV from one partner’s genitals to the other’s. Sorry to break it to you, but the handie isn’t quite as handy as we would like it to be.

When my partner and I have sex, she wants to perform oral on me until I finish. I enjoy it, but I just don’t have the desire to reach orgasm during oral sex. I prefer to finish during actual intercourse. Her wet, warm vagina feels much better, and I have stronger orgasms. She is frustrated. Why am I not on the popular blow-job-orgasm train, and why do I prefer to finish at the final station?S.F., Madison, Wisconsin
Don’t be so sure the blow-job-orgasm train is as packed as you think it is. Sure, there’s a possibility your partner hasn’t mastered the finer points of applied friction and rhythm. But you’re clearly not the only man who prefers the physical and psychological satisfaction of achieving orgasm through vaginal sex, as evidenced by the continued survival of the human race. After all, ejaculating in a woman’s vagina is the biological gold standard. Despite our desire for variety in the bedroom, the evolutionary urge to come inside clearly continues to win out.

I got divorced a year ago and have since started to use the dating app Tinder. I have matched with several women—some who include descriptions in their profiles and others who have nothing. When I ask questions to find out more about them, they will often reply with “Hope you’re having a great day” or some other random remark instead of answering my questions or asking me about myself. Could these be men pretending to be women? I don’t want to end up like Manti Te’o in some cat-fishing scenario. How do I know if I’m connecting with real women?K.N., Phoenix, Arizona
The replies you describe sound innocuous and neutral rather than emotionally or sexually manipulative. Tinder’s primary function is to be a dating and hookup app. The point of the 100-mile geographic range is to facilitate the actual physical meeting of users. Of course a man could post a photo of a woman and flirt and sext with you, but it doesn’t sound as though that is what’s happening in your case. If you use Tinder the way it was intended, you will soon enough find out the gender of other users.

My girlfriend and I have been engaged for about a year. I am 34 and she is 25. Over the past 12 months she has lost about 15 pounds and has never looked better. The only problem is she has also lost what I deemed to be the best set of natural breasts I’d ever seen. She still has a gorgeous rack, but she has lost at least a cup size. It bothers her more than it does me, but breast enhancement is not an option. Do you have any advice?M.M., Sudbury, Ontario
Compliment her, flatter her and be demonstrative in your appreciation of her breasts as they are (in private, of course). Presuming you get married and have kids, you’ll both get the bonus of the natural breast enhancement that comes with pregnancy. But that isn’t reason enough to have kids, and it isn’t lasting. If she wants to add volume to her breasts, she can do an array of pectoral exercises, from push-ups to presses to pec decks at the gym. They can lift and push out what she already has. The main thing you can do is continue to be a supportive partner.

My wife and I recently began to discuss potential baby names, and we have arrived at a fork in the road. I was named after my father and would like to name my first son after myself, which would make him a third. My wife opposes this idea, stating it is an archaic practice and would imply favoritism over our other children. However, I feel that passing down a name from generation to generation is an underutilized tradition that demonstrates strong familial bonds. What is your take on this issue?M.O., Fort Collins, Colorado
Personally, the Advisor likes being the one and only Advisor, not Advisor Jr. or Advisor III. But that’s just us. As for you: Ask yourself how much you really want to fight your wife. Forcing her to adopt something she is steadfastly against will only weaken your family bonds.

Could you please provide me with a list of dating sites for married people that are not rip-offs? I’ve tried about 20 and they’ve all turned out to be full of scam artists. I’m honest about being married and what I’m looking for—specifically, a local friend with benefits whom I can hook up with for simple no-strings-attached sex. The websites I’ve gone to are packed with women who try to persuade me to spend money to join other rip-off sites. There are a million sites out there, and I can’t try all of them. I trust you to provide me with a quality online source for local married women who are looking for extramarital action.U.P., Cleveland, Ohio
There are none that we know of. But the preponderance of pseudo hookup sites targeted at men like you proves that the male fantasy of a world full of uncomplicated extramarital arrangements is an undying and profitable one. You could, like some married men, be frank about your desired arrangement on a dating site such as Tinder or OkCupid, and you may luck out. But don’t count on it, as these sites are geared toward single people. There are websites for people involved in open relationships (also known as polyamory). Many polyamorous couples are married and open with each other about their extramarital activities; however they tend not to get involved with cheating spouses.

You recently suggested that an adventurous traveler take Pepto-Bismol as a way to prevent traveler’s stomach (July/August). I would instead suggest gin and tonics to keep stomach issues at bay. I have been to many exotic places and have never gotten sick while on G&Ts. I’ve concluded they were invented by the British raj for medicinal reasons. I have no evidence of this but would be delighted if you proved me right.C.L., Lafayette, Indiana
We cited drinking alcohol as a preventive measure, but we didn’t get as specific as you have. We have similar taste, as the gin and tonic is definitely our preferred medicinal drink while traveling abroad. Gin tends to be higher proof than vodka and other spirits, and we like the bittersweet taste of tonic. A generous squeeze of fresh lime not only completes the delightful balance of contrasting flavors but also raises the acidity of the drink, thus increasing its antibacterial properties. There is a history of the gin and tonic as a medicinal drink. The tonic water used to prevent malaria during British colonial rule in India was loaded with the antimalarial drug quinine (at a much higher dose than in today’s commercially available tonic waters). Officers found that adding a couple of ounces of gin made taking their medicine more fun.

I’m struggling with a problem related to the behavior of my wife of 20 years, and I can’t seem to get over it. I’d left my laptop at work the other day and asked if I could use hers. She obliged. I was shocked to see a sent e-mail she had left open on her screen in which she encouraged one of her girlfriends to “go ahead and fuck” (those were her words) an old acquaintance the friend had met at a get-together while out of town without her husband. The language my wife used was graphic and appalling, and I closed the page after reading it. The recipient of my wife’s advice and her husband have both been friends of ours for almost 10 years, and my wife says nothing but good things about the husband. I’m fairly certain this friend has remained monogamous throughout her marriage, as I believe my wife has. The tone of the e-mail was all about getting laid for the sake of sex and sex alone. We’re all in our late 40s and have what I thought were happy and trusting relationships. I thought I knew my wife better than this and consider what she has done to be totally out of character. I am so disgusted with her that I can barely look at her, let alone trust her anymore. I can’t confront her because I know from experience that she will somehow try to turn this whole thing around and accuse me of checking up on her and make it my fault. I have nobody to talk to about this and welcome your suggestions.C.M., Tampa, Florida
You actually do have someone you can talk to about this: your wife. The fact that this incident is nagging at you means you need to come clean about what you read. Letting it fester will only add toxicity and mistrust to your relationship. It’s possible your wife was joking. The only way to find out is to bring it up with her. If she was serious, then the two of you need to revisit the values you share, particularly your attitudes toward fidelity. But we think you may have an opportunity to make this work out in your favor—and maybe add some spice to your sex life. You describe your wife’s language as graphic and appalling, but we know a lot of married men who would love to hear their wives of 20 years talk that way. By encouraging her friend to get fucked simply for the sake of sex, she may actually have been expressing a desire for the same thing. It’s normal for a long-term relationship to get dull, and maybe you can reconnect with your wife with some straight talk and good old-fashioned fucking for fucking’s sake.

I’ve heard of porn in which the participants urinate into each other’s mouths and then swallow. Is it harmful to swallow someone else’s urine? Could you become ill from it?R.C., Houston, Texas
Yes, if the other person has a bacterial infection. But that doesn’t dissuade people who get off on drinking other people’s urine. What you’re describing is a fetish known as urophagia, which is sometimes but not always used in bondage and discipline as a way of demonstrating dominance or submission. While it’s rare to become sick from the practice, we suggest playing it safe.


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 email advisor@playboy.com. The most interesting and pertinent questions will be presented in these pages each month.


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