The Playboy Advisor

Q: I love cunnilingus. I can go down on a woman for hours. My favorite sex position is using my tongue to make a woman come while getting myself off. And the woman almost always comes! This means I rarely have penetrative sex, as I am just fine coming without it. A woman I re­cently started dating tells me it’s strange that masturbation gets me off better than her vagina. Should I be worried that I, a straight man, am not that into vaginal sex?—B.K., Colorado Springs, Colorado

A: The first thing to note is that her va­gina is still getting you off. Rest assured that there’s nothing “strange” about pre­ferring masturbation over penetration, because there is no “correct” way to have sex. The goal of sex isn’t penetration; it’s achieving mutual pleasure. You deserve to feel confident and authentic in what­ever helps you do that.

Further, your heterosexuality should not inform anything about your sex life other than the gender of your sexual part­ner (though even that is fluid nowadays). Being straight does not predetermine one’s favored sex positions, nor should it restrict them. Your heterosexuality also isn’t an excuse for anyone to shame you.

Yes, calling someone’s sexual prefer­ences “strange” amounts to a form of shaming, which can quickly turn abusive. Your concern should be about other non­traditional interests your girlfriend might pass judgment on. When we reveal our sex­ual interests to a lover, the response should be one of acceptance—as long as those in­terests are mindful of your partner’s plea­sure and cause no harm to others. Which is why I must ask: Is your partner dissatisfied with receiving only oral sex? Has she asked you to do more than go down on her? Have you refused? If so, it’s your duty to in­corporate more penetration so both your desires are being fulfilled. This doesn’t mean giving up what you like. Introducing a vibrator, for example, leaves one hand free for masturbation while still giving your tongue access to her clitoris.

If she has expressed that oral sex alone satisfies her, you need to tell her how her words make you feel (i.e., inadequate). Our self-worth is an accumulation of how others treat us, but you are responsible for your self-esteem. Human interactions, especially sex, are never neutral. You will always leave a sexual encounter either feeling better about yourself, your body and sex in general—or feeling bad about it all. Choose the former.

Orgasms are hot and fun, but they aren’t guaranteed, nor should they be required. The goal isn’t mutual orgasm but mutual pleasure. By expanding our definition of what we call “sex,” we can create new sexual connections and new kinks.

Q: Why has adultery become so preva­lent? I’ve witnessed three of my friends cheating—separately, though all three did it publicly and in front of me. I’m close with their partners, so their infidelities have complicated our friendships. This has made me quite cynical about dating and relationships. Overall, I don’t know how to handle what I’ve seen. Do I call them out, tell their partners or shut my mouth and toss out my moral compass?—M.F., Overland Park, Kansas

A: Simple answer: Adultery is prevalent because monogamy is hard. According to data collected by the General Social Survey from 2010 to 2016, as many as one in five men have cheated on their spouses. Comparatively, 13 percent of women have cheated on their spouses.

Those figures increase as people get older, however, suggesting that monogamy becomes more difficult with age. Meanwhile, the definition of cheating continues to evolve. According to the 2019 Playboy Sex Survey, 17 percent of fe­male respondents did not consider sex­ual intercourse “a form of cheating.”

The core issue driving people to cheat is not just the tension between desiring commitment and wanting the freedom to explore but also the toxic rules that gov­ern many monogamous relationships. Toxic monogamy is the idea that you have a right to own or control your part­ner. This includes viewing others of the same gender as threats and not respect­ing your partner’s privacy. (How many readers have broken into their lovers’ cell phones?) Such behavior sucks the joy and sustainability out of any relationship.

Cheating is an unacceptable solution for whatever issues your friends may be trying to solve (or run from). It robs a rela­tionship of trust, which is difficult to get back. Most of us could benefit from being honest with our partners about our needs, and that includes a desire to have sex with others while in an exclusive relationship. Deciding to do so without telling a part­ner is nothing short of destructive.

But let’s switch back to you, the inno­cent bystander. I suggest speaking to each of your cheating friends individu­ally so you can better understand their relationships. Not everyone has the same rules, and it’s increasingly common for couples to enter monogamy with differ­ent expectations and dynamics. Some couples are fully open, some allow for casual make-outs and drunk flirting, and the majority are traditional and closed. Might all three of your friends be in open relationships? It’s unlikely—only one in 10 people ages 25 to 34 are—but…perhaps.

While it is not your job to fix anyone’s relationship (or destroy it), you should confront your friends about how they’ve put you in an unfair position. In the end, being a moral friend doesn’t make you the moral police. If they turn on you or respond with anger, you have no reason to stay faithful to them—something they should know a thing or two about.

Q: My husband and I have been married for 14 years. We enjoy a physically intense sex life that includes verbal degradation and sex that leaves us both bruised. We’ve never taken it to the point where either of us feels unsafe; only once have my bruises been large enough that I’ve had to cover them. I recently started bingeing HBO’s Big Little Lies, and on the show, Nicole Kidman and Alexander Skarsgård’s characters engage in similar sexual behavior—though the balance of power in their sex life seems less equitable. The Kidman character’s therapist says she may be addicted to the pain. I never thought such a thing was possible. Is it? Could my husband and I be addicted to pain during sex?—D.B., Santa Monica, California

A: You shouldn’t retroactively pathologize 14 years of a healthy sex life because of a fictitious plotline on a soapy TV show. For one, you cannot be “addicted” to pain. You can seek pain, enjoy it and prefer sex with it, but you cannot be addicted to it.

Our culture likes to dramatize ex­treme interests by deeming them “addictions.” Diverse and subversive sexual acts create anxiety among sex-phobic social puritans. Understand that the purpose of a phrase like sex addiction, which the American Psychiatric Association rejects, is to diagnose someone’s sex life as ab­normal. There’s nothing psychologically wrong with intensely—or even painfully— experiencing your sexuality, as long as it’s safe, consensual and with someone you trust. I work with many patients who strive to heighten their arousal, expand their sex lives and find true compatibility. You and your husband seem to have achieved all that—to which I say congratulations.

Q: I’m a white man who has dated only chunky women of color. No one has ever commented on the similarities between my exes, but today’s climate has made me hyper-aware of body shaming, mi­sogyny and racism. Is it possible I have some underlying, unhealthy attraction to women of a particular race and body type that I’m not fully aware of?—A.P., Detroit, Michigan

A: If I were to read your question a dif­ferent way, it may sound as though you’re covertly asking whether you, a white man, should sleep only with thin white women. The answer to that is an obvious no.

It’s refreshing how aware you are that your sexuality can impact others in ways you may not fully realize. To me, this speaks to your compassion. Having compassion for people who come from different backgrounds is a goal of intersec­tionality. Coined by Kimberlé Crenshaw in 1989 and defined as “the complex, cumu­lative way in which the effects of multiple forms of discrimination (such as racism, sexism and classism) combine, overlap or intersect especially in the experiences of marginalized individuals or groups,” in­tersectionality aims to increase awareness of the power imbalances in all areas of life. That includes our sex lives.

Fetishization is the process of reduc­ing a person to certain physical attributes and ignoring everything else about them. Thus, fetishizing larger women or women of color is indeed a problem. But I don’t believe you exhibit this fetish, as your re­lationships with these women have all gone beyond sex. They’re not sex objects; they’re your partners.

It’s important to be conscious of how you use your privilege and social power, but there’s no politically correct form of sexual desire. Don’t overthink what turns you on, and don’t resist what arouses you because of identity politics. In the U.S., healthy in­terracial relationships have long repre­sented two people pushing back against societal inequality. As long as you treat the women in your life like the gorgeous, intel­ligent, autonomous sexual beings they are, you have nothing to be concerned about.

Q: My sister’s boyfriend recently relo­cated from Chicago, where they were living together, to Boston, where I live, for work. As a straight woman, I find him im­mensely attractive and have had many sex dreams about him throughout their relationship. Now that we live in the same city, he constantly texts me to hang out. I don’t trust myself around him and have gone to great lengths to avoid contact. My sister wants to know why I won’t help her boyfriend settle in. It’s actually causing me a lot of stress. What do I do?—K.H., Boston, Massachusetts

A: Why do you think you wouldn’t be able to control your impulses if the two of you were to spend time together? I suspect you’re harboring some hope of a future in which you two end up together. Sorry, but he isn’t interested in having sex with you. He just wants to spend time with someone he knows in an unfamiliar city.

Your anxiety is par for the course in cases of unrequited love, but don’t lose yourself in a world of what-ifs. Boston is home to many single men you could date. Don’t waste your time obsessing over your sister’s boyfriend, who is unavailable, as if he’s your only option. He isn’t.

In the meantime, make this man—a person your sister loves deeply—feel at home without becoming a home-wrecker. There are many easy ways to make this work. Socialize in public or do group ac­tivities. Don’t spend time alone with each other, and don’t get intoxicated together. Avoiding him isn’t sustainable; should they wed, you’ll be running from him till death do they part.

Q: I’m a virgin, but I want to start hav­ing sex soon. How am I supposed to know which condom is right for me? I’m average length but thick in girth. I’m also uncir­cumcised. I don’t want a condom to ruin the mood when it finally happens.—J.G., Goodyear, Arizona

A: Condom selection, like everything else tied to sex, is trial and error. Determining your condom size is not only important for your (and his/her) pleasure but integral to effective birth control, STI prevention and a healthy sex life. Sizing charts can be found online, but beware: The charts aren’t standard across manufacturers. Condoms are also made from different materials, such as latex, polyisoprene and polyurethane. Some feature studs, rib­bing and prelubricant. Some are colored, others are flavored. All of this is to say finding the right condom goes beyond fit.

Start by investing in a few brands and various styles. Many brands come in packs of one to three and can be pur­chased online. Try one on and wear it while masturbating to kick-start your body into linking protection with arousal. Your first time will be awkward for a lot of unforeseeable reasons, but I can assure you that the person you take to bed will be impressed you came prepared. Oh, and asking your bedfellow to put the condom on you turns a potentially awkward mo­ment into foreplay.

Q: I play in a rugby league, which requires me to wear a cup. My girlfriend loves it. When I come home from a match, she tears off my uniform and asks me to fuck her while wearing my sweaty jockstrap. But pulling the cloth pouch to the side is dis­tracting, and I can’t stay hard. This has left us both frustrated by our spontaneous postgame sex sessions because neither of us finishes. What’s behind my girlfriend’s fetish for my dirty jockstrap, and how can I fulfill her fantasy even when my body isn’t responding?—R.T., Birmingham, U.K.

A: First off, congrats on having an as­sertive, sexually empowered girlfriend. A confident partner who demands sex? You’re luckier than you may realize. Second, your question is a perfect exam­ple of how sex helps us grow and mature, because what you view as problems— an inability to stay hard, an inability to climax—are opportunities to remind you what makes sex so great.

To start, nothing is wrong with your body. Orgasms are hot and fun, but they aren’t guaranteed, nor should they be re­quired for sex between two people to feel complete. Sex is supposed to be fun, and you don’t need to finish to have fun. Ful­fill her fantasy by fucking her while wear­ing the jockstrap. If you go soft, start using your tongue or your fingers, or bring in a toy. Put the jockstrap on her face, switch up positions, ask her to ride you or have her go down on you to bring back your erection.

The goal here isn’t mutual orgasm but mutual pleasure. By expanding our defi­nition of what we call “sex,” we can create new sexual connections and new kinks.

By the way, the science behind fetishes is a theoretical guessing game, as fetishes represent a complex intersection of brain activity, cultural conditioning and personal experience. Don’t sweat about what’s behind a fetish (as long as it’s not the identity-based variety I mentioned earlier). Just enjoy what comes next— even if you don’t.