As much as we love a good spicy sex positions article or sharing advice on relationships and intimacy, there are just some questions about sex that remain unbelievably awkward to both ask and answer. After all, sex is a private, unfortunately still taboo topic, and there are parts of the sexual experience that often go undiscussed, whether among friends, in the media, or even in movies and television shows. At the end of the day, we’re all left with a few burning questions about our sex lives that, if answered, just might make our time in the bedroom that much steamier.

For those of us who have brought up intimate questions at the OB-GYN only to realize that our poor gynecologist really does not have the expertise to answer whether or not we should purchase a cock ring, there are sex therapists like Dr. Jenni Skyler, co-director of The Intimacy Institute. To get to the bottom of some of the most taboo questions about sex and intimacy, I asked her for her expertise—and boy, did she deliver. Read on for seven of the questions about sex that you’re too afraid to ask, answered.

Meet the expert
Jenni Skyler
Dr. Skyler is a certified sex therapist, sexologist, and licensed marriage and family therapist. In addition to co-directing The Intimacy Institute, she is the resident expert at Adam & Eve .

I have never had an orgasm. Is this normal, and do you have any tips?

Remember that episode of Sex and the City when Samantha declares to her horrified friends that she has “lost her orgasm”? Unlike the 25 minutes of Samantha’s dramatic search for her misplaced orgasm, in reality, never experiencing “the big O” is a fairly mundane experience for many people, according to Dr. Skyler.

For those who want to go on a far less theatrical journey to orgasming than Samantha’s escapades, Dr. Skyler recommends practicing pleasure, preferably solo. “My main tip is to practice the art of surrendering to sensation and pleasure, ideally when alone to really allow the body to feel safe to do this,” Dr. Skyler said. “Also, notice when your brain goes to the tape recording that replays ‘when will my orgasm arrive,’ and see if you can distract from that to let the body lead.” Focusing less on the alleged destination of orgasming and more on the physical sensations in the body itself will allow you to experience sex or masturbation as a pleasurable experience, regardless of whether or not you end up finishing.

What is a healthy frequency of masturbation?

Masturbation is one of those things that is easy to feel insecure about, mainly because it’s rarely the first thing that comes to mind to chat about over coffee or drinks with friends. Whether you love masturbating and fear that you may be doing it too frequently or have residual shame around fantasizing about sex and never masturbate, it’s unlikely that these are concerns you’ve ever brought up in casual conversation.

Dr. Skyler reassuringly notes that the frequency of masturbation is far less important than how you think about and approach masturbation, emphasizing how crucial it is for your relationship with masturbation to be healthy and grounded. “If you do it constantly to distract from life or escape, that is something to look at,” she said. “If you rarely or never do it because it creates guilt, shame, or embarrassment, this is also something to look at.” If you’re feeling insecure about your frequency of masturbation, it’s likely that that feeling is coming from a strained relationship with self-pleasure, which would be something to look into through journaling or seeing a sex therapist.

What should I do if sex with my partner starts to feel dull or repetitive?

Having a burning question about sex with another person is always a challenge, specifically for that reason—there’s another person involved. If you don’t quite feel comfortable bringing it up with your partner yet, and it’s not something you want to share with friends, experts like Dr. Skyler are a fantastic resource.

Dr. Skyler runs The Intimacy Institute with her husband, Daniel Lebowitz, so she’s no stranger to questions regarding the ebb and flow of libido in a relationship. She recommends gathering your thoughts and concerns before having a conversation with your partner about what might be feeling dull or routine. “Often couples don’t talk about sex, what they want, and what drives their desires. They default to a transactional routine. Talking and changing some things can really serve a couple,” Dr. Skyler said.

Source: Pexels | @cottonbro

How can I communicate with my partner if sex feels too short (or too long)?

This is another one that is challenging to bring up with a partner, especially since the length of sex is such a stigmatized subject. Unlike concerns about dullness, repetition, or a sex slump, Dr. Skyler specifically suggests bringing this conversation up outside of the bedroom. “I recommend talking at a safe time, not during sex,” she said. “Invite the conversation over a dog walk or dinner and ask about making some changes that can create more enjoyment.” Opening up the discussion about the length of sex in a safe environment can eliminate immediate pressure to switch things up and allows your partner time to process your needs, as well as their own.

Why does it hurt when I have sex? How can I start to enjoy the experience?

Sex is something we glorify so much in our culture as an almost entirely pleasurable experience (*cough cough* Bridgerton season 1), so when you experience the exact opposite most of the time during sex, it can be hard to know where to turn. Likely, the reason for painful sex will vary from person to person, as there are a host of reasons, physiological or mental, why one might feel pain during intercourse. However, that doesn’t mean there are no concrete first steps anyone can take toward eliminating physical discomfort during sex.

According to Dr. Skyler, many women experience pain during sex. “The body is brilliant and guards from the possibility of pain or perpetrators. Even though the current partner may be safe, the vagina does not necessarily discern this, and continues to guard and block, creating pain,” Dr. Skyler said. For those who have experienced sexual trauma, or even for those who have feelings of shame surrounding sex, the body will respond according to often subconscious emotions. As Dr. Skyler said, “This psycho-somatic feedback loop requires somatic intervention with pelvic floor physical therapy and psychological intervention with sex therapy.” That said, seeking help for painful sex is something that ought to be totally de-stigmatized since it is such a common experience.

Is it unhealthy to schedule sex or intimate time with my partner?

Listen—I’m a busy girl. My calendar time is sacred, and if my man isn’t one to accept a Google Cal invite for date night, that’s not my man! That said, I have felt insecure in relationships about planning ahead for sex before, fearful of eliminating the romance and spontaneity in my sex life.

Luckily for type-A time-blocking addicts like myself, Dr. Skyler is a huge proponent of scheduling sex. “For the high-desire partner, scheduling sex ensures sexual contact will happen on a particular day. For the lower desire partner, it ensures a break from sexual contact without wondering if it’s always on the table,” Dr. Skyler said. “It also allows for the couple to plan how they want to approach sex, setting up the right ambiance and relaxation prior to the date.” G-Cal invite? Check. Lighting and ambiance set up before we even leave for dinner? Check. Guaranteed extra flirtation over dessert? Check.

Which sex positions stimulate the clitoris, and which are more likely to stimulate the G-spot?

If you’ve ever orgasmed and been unsure of exactly…why you orgasmed, this one is for you. The female-bodied orgasm is, unfortunately, shrouded in mystery for most people, and if you’re seeking a specific type of pleasure, it helps to know what to communicate to your partner. At the same time, though, the question of which sex position works best for you is obviously going to vary from person to person.

“Every body is different. Every penis is different. There is no one size fits all for this question, as each couple fits together in their own unique puzzle configuration,” Dr. Skyler said. “That said, many find that doggy style accesses the g-spot more easily, while a woman on top (especially with a vibrating cock ring on her partner) can really stimulate the clitoris.” Next time you’re hoping to achieve a more intense orgasm, get creative with position—you might just find your new favorite.


Leave a Reply

Your email address will not be published. Required fields are marked *