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Playboy Advisor: My Girlfriend Wants a Rim Job

Playboy Advisor: My Girlfriend Wants a Rim Job: ILLUSTRATION BY SKIP STERLING

ILLUSTRATION BY SKIP STERLING

My girlfriend wants me to give her a rim job. I’ve heard it can be quite pleasurable for a man too, so I’ve convinced her this is one sexual favor she will have to give me in return. We’re both a bit squeamish, though, since we’re not exactly talking about the cleanest erogenous zone. Can you help put us at ease?— G.M., Nashville, Tennessee
Beyond kissing and spanking, the rim job is one of the few sex acts a straight couple can give to each other in an anatomically balanced fashion, so both of you should take note. Save the ass play for last, as even the cleanest anus can have traces of bacteria you don’t want transferring to each other’s mouths or genitals. Yes, you should both take showers and clean up with a lot of soap. And keep the tongue play shallow; a good rim job is about pleasant pressure, not penetration.

I’m a 28-year-old male who recently ended a five-year relationship. Since the breakup I have been dating as much as I can and, thanks to the Tinder app, have been having more sex than I ever thought possible. Now I’m afraid I’m becoming a sex addict. Maybe I was a sex addict all along and my relationship was hiding that fact without my realizing it. Although my girlfriend and I used to have sex twice a week, I would masturbate to online porn pretty much every day without fail, which seems to be kind of a lot. And now I’m using real women the way I used to use porn—except that these days I have to deal with their wanting to spend the night or have breakfast or hang out. I haven’t felt much more than the thrill of the hookup nor much attraction, and I tend to drop the women afterward. Do you think I’m handling this the right way?— L.D., Brooklyn, New York
We think you’re handling this in a pretty typical way for a horny dude in his 20s who just got out of a long-term relationship. Having as much consensual sex as possible with people who aren’t your five-year partner is a post-breakup ritual worth indulging. If you can handle it honorably and with grace, then by all means enjoy yourself. There’s no way of knowing how long this run will last or remain appealing, so it’s better to have a memory bank full of good stories than regrets about not having acted. The ease with which you can hook up digitally, particularly in a big city such as yours, is a fine thing. In the past, men romanticized the dating prowess they possessed during their high school or college days; in the future, the urban American single people of today will no doubt look back on their 20s and early 30s as the golden era of Eros. You say you’re worried you might have a latent sex addiction. From what you report, your behavior doesn’t sound entirely out of the ordinary. But ask yourself if your family, friendships or work life is suffering as a result of your dating. If any of them are, then assess how much time you spend arranging and carrying out these hookups and see if you can scale back. However, it sounds as though you’re having fun for now, so until it becomes unfun, it’s not likely an addiction.

I’m a 40-year-old woman in a loving and successful marriage with a wonderful man. We count ourselves lucky because we’re both fit, attractive and reasonably happy with our jobs and home life. Our sex life is decent, but my husband complains that I never initiate intimacy, which is true. I don’t have a burning desire for sex, but once I’m aroused I’m ready to go. The way I see it, the ball is really in my husband’s court. The problem is that when he tries to seduce me, he inevitably becomes jokey, saying things like “It’s time to ride the boner machine” and “Are you ready for salivary seduction?” It’s totally obnoxious but actually gets me laughing. It sometimes backfires, though, because I’m ticklish and it takes me 10 minutes to relax and get ready for sex. Why do you think he jokes around like that?— M.T., San Francisco, California
Laughing about your sex life is certainly better than crying. After what we’re guessing is more than a decade of marriage, you’re in a classic situation. It sounds as though your husband is trying to cheer you up and turn your day from the mundane (paying bills, doing dishes, talking about the kids’ college funds) to the playful in the hopes that it will yield to a sexual fantasy worthy of his middle-aged libido. The whole tickle, laugh, seduce ploy is actually pretty common too, albeit more as a juvenile move than the approach of a sophisticated adult. It also sounds as though your husband takes it too far. If you find his hijinks push you further away from the desired mood than a standard appreciative seduction would, ask him to ease off. Suggest he try something actually relaxing that could segue more seamlessly into the erotic—such as a massage, a back rub or even a bath. He shouldn’t expect a lame slapstick routine to suddenly turn you into his horny fantasy.

A friend of mine recently found out he has cancer and has decided against receiving treatment. I’m having a hard time accepting this and feel strongly that he should fight the disease. On the other hand, I don’t believe it is my place to tell anyone facing such a diagnosis how he or she should react. What am I supposed to do?— J.T., Dayton, Ohio
You’re supposed to support your friend fully, no matter what he decides. That said, if you believe he’s been misinformed or under-informed about his chances of survival, you could offer to be his advocate and help him research the science that supports his decision. But you need to be sensitive to his boundaries and prepared to back off when and if he tells you to. As hard as it is to sit by and watch someone get sick and suffer without fighting back, it’s not up to you to decide what’s best for him.

I recently received a bottle of Vieux Carré Absinthe Supérieure as a gift. I’ve never had absinthe before, but I know it was banned in the States for many years. How do I drink it? Some websites recommend using a perforated spoon to “louche” the drink, but is there an alternative method? Also, many sites caution against drinking “low-quality” absinthe. How do I know what’s good and what’s bad?— G.G., San Antonio, Texas
Drink it any way you like; just don’t drink too much of it: It’s among the most powerful spirits on the planet, with an alcohol-by-volume measure of up to 75 percent (that translates to 150 proof). And we hope you like licorice, which is the dominant flavor of absinthe. Although its reputation for having hallucinogenic properties has contributed to its mystique, absinthe is actually a higher-alcohol version of pastis. You owe it to yourself to at least try drinking it the traditional way, which involves, as you correctly label it, “louching” the drink. This entails pouring a little water into the absinthe through a specially designed slotted spoon. The point of this is to slightly dilute the absinthe, which makes it burn less on the palate and also allows the aromatics and volatile compounds to be released into the air, making for a more complex and nuanced drinking experience. Sometimes people pour the water through a sugar cube on the spoon to make the drink more palatable. By far the most popular way to imbibe absinthe today is in a sazerac, a bitter, powerful, aromatic cocktail legendary in New Orleans and worth checking out. Cocktail snobs may quibble with the following proportions, but the resulting drink will by no means suck; it’s a way of incorporating absinthe’s assertive flavor into a lower-proof cocktail that will appeal to anyone who likes a sweet and strong beverage: Crush a sugar cube in the bottom of a rocks glass, add one and a half ounces of rye, a tablespoon of absinthe and two dashes each of Peychaud’s and Angostura bitters. Fill the glass with ice, give it a good stir to combine, and garnish with lemon peel.

I just finished a summer-wedding marathon, and it has left me with a lot of questions: Must your pocket square always match your tie? What’s a respectable per-person monetary gift? (My date said it depends on how close you are to the bride or groom; a wedding planner told me my gift should cover the cost of my plate; another said $50 a person is fine.) At an open bar, is it better to tip large early or funnel singles all night long? (I felt weird leaving a $20 tip for the first drink, thinking it would cover the night, only to have a new bartender take over and make me look like a cheapskate.) In 2015, does the à la mode black dress shoe have a square toe or a fine rounded point?— T.S., Reno, Nevada
First, a pocket square doesn’t always need to match your tie in color or pattern, but it’s a safe way of adding some swagger to your suit. It should at least relate to something else in your outfit: the color of your socks or shirt or some detail or color in your tie. That said, a black, dark gray or blue suit would do well with a pop of contrasting color, but that’s more for the experts. On the gifts question: A nice round $100 is a respectable amount for a cash wedding gift. We always err on the high side, though, so if you can afford more, then go up to double that. That way you’ll probably cover the cost of your dinner and drinks and help pay for the honeymoon. Any more than $200 would be ostentatious. On the tipping front: It’s best not to blow your wad at the get-go. Start with $10 on the front end, then dole out singles and doubles for the rest of the evening. With shoes: Go somewhere smack-dab between a square and a rounded toe. Those shapes swing back and forth with trends, but time has shown that a modestly rounded toe, neither too square nor too pointy, is always in fashion.

I’m currently dating someone who has a famous sibling and is minutely famous in her own right. If you were to google my girlfriend, you would find plenty of pictures and videos of her on television and walking red carpets. I’ve been strategic about not mentioning her fame or her famous brother, possibly to the point of seeming above it all. I don’t want her to think I’m the kind of person—a star-fucker, if you will—who would date her only because of who she is. But this aloofness can continue only for so long, especially if I want things to get serious. Any advice on a subtle way of saying “Hey, I know about you, and I don’t care”?— M.B., Oak Park, Illinois
Not mentioning your girlfriend’s fame or her more famous brother is an over-correction in the extreme. Acting artificially uninterested makes it appear as though what they do for a living is a big deal and so important that they deserve special treatment from “civilians.” This is actually worse than being a star-fucker—you’ve almost made yourself into a star-server, and a mute one at that. Think of it this way: Assume that actors are a rightly and typically insecure bunch who have hitched their fortunes to the fleeting judgment of others in a culture obsessed with beauty and youth. As such, hanging out with you may be a relief for them, which actually gives you a bit more power in the relationship. But that doesn’t mean you can’t acknowledge the world they work in. When the earliest opportunity presents itself, we suggest you bring up something about her career aspirations or how she feels about the whole red-carpet thing. Does she like it? The more serious you get, the sooner you’ll be talking about work. And whether or not fame is part of that work is just a by-product of how the two of you should be relating as human beings.

I’ve been doing yoga for a few months and was hoping my newly gained flexibility would aid with something I think many men would like to achieve: auto-fellatio. I recently tried to suck my own dick and got within four inches of my goal. Any tip on how to bridge the gap between mouth and genitals?— B.C., Santa Fe, New Mexico
“Tip” is right, because if you actually succeed that’s all you’re going to reach. Maybe you’ll be able to lick it with your tongue, but what’s the point? The fantasy we’ve heard about is being able to get a full-blown hummer on demand. Sure, you could spend 70 percent of your fitness routine on getting the flexibility of a contortionist, but the physics, biomechanics and everything else will need to align in a statistically rare way to yield the holy grail. There are better things to spend your time focusing on—like getting someone else to give you a blow job.

Over the years of working together, a female colleague and I have become close; in fact, she’s one of my better friends. She’s a great person, and I’ve also become friends with her husband—so much so that my wife and I often have dinner with them, and the four of us occasionally go to the beach together. I was recently at a convention in Las Vegas with her and several other co-workers. I saw my female colleague making out with a guy at the bar after a work dinner and then go up to what I assume was their room. Should I say something to her or her husband? It’s burning me up, and I don’t know what to do about it.— G.P., Cleveland, Ohio
It’s not your job. You have no idea what’s going on in your colleague’s relationship with her husband. You also have no idea if this was indeed a random guy or whether they have an open relationship. If the “guy” was a professional associate and you had reason to think her relationship with him was influencing business deals, then you’d have a right to say something. But as it is, you’re colleagues first and friends second. And as a friend, you need to stay out of her private affairs. If she comes to you for advice, then that’s another thing.

How do I dial down the intensity of a relationship I’ve fully dived into without upsetting the girl? Here’s the pattern I’ve identified and from which I’d like to break free: I tend to become infatuated with a beautiful and distant woman; I then succeed at sweeping her off her feet and revealing the tender woman within. The problem is, once I’ve set the bar that high, I need to keep topping it. The whole process is exhausting, and it ends with me burning out and my girlfriend being disappointed.— W.M., Beaconsfield, U.K.
You do like a challenge. Beautiful and distant is a thrilling combination when it comes to the chase. Unfortunately, if you keep upping the ante and play the grandiosity-entertainment card too hard, you’ll never know who either of you is in the day-to-day. Don’t pressure yourself to keep up the pace; maybe you’ll find that she would rather downshift after such a splashy start. And if you’re honestly looking for a relationship that will last beyond the courtship phase, we suggest you change not only how you handle these relationships but whom you partner with in the first place. Distance, either emotional or geographic, tends not to be a great predictor of success in relationships.


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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