"> TOP SEX QUESTIONS ANSWERED BY DR. JESS. | The Chic Confidential

TOP SEX QUESTIONS ANSWERED BY DR. JESS.

sex questions by dr. jess

Hii guys!! Ohmigod, VERY VERY excited about this blog post. We are answering all your burning sex questions! And by we, I actually mean Dr. Jess.

We’re really getting into it in this post. Everything from oral sex, how to go from boring to amazing sex, intimacy, stamina, and MORE.

Jess O’Reilly (@SexWithDrJess) is a sex and relationship expert with a background in education. Her research and passion involves teacher training in sexual health and she volunteers in schools and universities to help bring better sex & relationship education to students across Ontario. Jess is also a television personality, author, podcast host (@SexWithDrJess Podcast) and international speaker who has facilitated hundreds of corporate workshops and retreats in 35 countries from Lebanon to Costa Rica. 

Let’s jump right into this post, shall we?

1. Introduce yourself to The Chic Confidential readers – Tell us about your background and how you got into talking about sex & relationships.

I’m an accidental sexologist. I was a high school teacher in Toronto and saw the costs of a system and curriculum that didn’t address students’ needs with regard  to comprehensive, relevant and inclusive sex and relationship education. My students came to me every day with questions about relationships, abuse, assault, unplanned pregnancies, STIs and more. I  decided to go back to school and look  for ways to support teachers in delivering effective sex and relationship ed.. 

When I graduated, I wanted to work with the school boards, but they weren’t interested, so I started writing and speaking. I landed a few book deals and hosted a reality  show for Playboytv in LA which launched the Sex With Dr. Jess brand. Now, I spend more of time my time travelling to speak to entrepreneurs and their partners with a focus on happier relationships from the boardroom to the bedroom. I’m also always happy to volunteer in public schools, so parents and teachers can feel free to reach out!

2. Okay, let’s get into some juicy questions! How do you go from boring sex, to amazing sex? Give us some tips!

Consider your Core Erotic Feeling & Your Elevated  Erotic Feelings. This text below is from my  latest book (co-authored by Marla Renee Stewart), The Ultimate Guide to Seduction and Foreplay:

One of the most effective ways to better understand, seduce and entice your partner(s) involves understanding and tapping into their Core Erotic Feeling. And if you want to teach your partner(s) how to seduce you, you will want to understand your own core erotic feeling too.

Your core erotic feeling is the feeling you require in order to get in the mood for sex. 

Self- Inquiry: Core Erotic Feeling

Unfortunately we do not have a sure-fire gimmick or quiz to identify your core erotic feeling (CEF) with precision, but we encourage you to answer these questions to begin contemplating what your CEF might be:

  • Do you need to feel relaxed in order to have sex?
  • Do you need to feel loved? 
  • Do you need to feel honored? 
  • Do you need to feel happy and joyful?
  • Perhaps you need to feel safe, powerful, playful or stress-free?
  • Do you find that you are in the mood when you feel sexy and desired?
  • Do you experience sexual desire when you feel comfortable or when you experience a degree of challenge?
  • Do you want sex when you are tired or when you are full of energy?
  • Does sex seem most appealing when you feel vulnerable? Or does it appeal to you most when you feel powerful? 
  • How do you want to feel before you have sex?
  • What puts you in the mood for sex?
  • How do you want to feel during sex?
  • How do you tend to feel after sex?
  • How do you want to feel after sex?

Think of a recent fantasy. How did you feel? How did others relate to you in the fantasy? How did you relate to them?

Think back to a really hot and memorable sexual experience. What did it entail? What made it so hot? How did you feel during the lead-up to this encounter? How did you feel during and after this experience? 

As you explore the feelings associated with past sexual experiences and fantasies, you will likely be able to identify emotional themes. You will probably observe that there is a specific feeling (or two) that you tend to associate with peak erotic experiences. Try to narrow them down to identify the feeling that is indispensable to sex for you — the feeling without which, sex simply isn’t going to happen. 

After considering these questions, how do you most naturally fill in the blank:

In order to (possibly) have sex, I need to feel ________________.

Your Elevated Erotic Feeling (EEF) is the feeling that takes sex to the next level. It makes it more intense in a specific way — this could be related to physical pleasure, psychological thrill, emotional fulfilment, intimate connection, spiritual experience or any other benefit you personally derive from sex.


For example, perhaps you need to feel deeply loved in order to consider having sex — this is your CEF. And perhaps you are in a relationship in which this is your norm. You almost always feel deeply loved so you do not have to specifically work to evoke your CEF in order to have sex.

You may find that sex becomes possible once you feel deeply loved, but sex becomes more alluring and pleasurably overwhelming when you also experience a sense of challenge. When your partner makes you feel loved, but also makes you work for it, your excitement heightens. When they tease you and suggest that they’ll withhold sex, your desire skyrockets. When they threaten to withhold their touch, your body responds with both ache and arousal.


This is your EEF in action and it makes both the possibility and the experience of sex more exciting. In this example, it is the experience of feeling challenged, but your EEF could be entirely different. 
You do not have to master your CEF to identify or experience sexual desire, arousal and pleasure in response to your EEF, but they often go hand-in-hand. 

Upon consideration of your EEF, you might be concerned that some of the emotions that turn you on and make sex intensely gratifying are subversive or make you feel uncomfortable. They may not align with your personal and/or political values. For example, you might thrive in independence in real life, but have a strong desire to be submissive when it comes to sex. You might have built a mutually respectful relationship, but be turned on by consensual degradation. This is perfectly normal.


Your sexual desires and the feelings you associate with pleasure need not reflect your real-life ideals. The person you want to be on Saturday mornings at your child’s soccer game may be different from the person you want to be on Saturday night behind closed doors. You have the right to play multiple roles and sex can provide the sense of escape required for you to do so. 

3. Is the G-Spot really a thing? Tell us more about this.

The G-Spot is not a specific spot, but an area that is accessible through the upper wall of the vagina toward the stomach wall. This shallow zone just beyond the vaginal entrance is not a distinct anatomical entity, but a series of many sensitive nerve pathways, tissues and organs that can be felt through the upper wall of the vagina.

It often feels different than the rest of the vaginal canal and is described as more ridge-like and textured; some folks say that it feels similar to the roof of your mouth, but softer. 

If you reach in to try to locate the G-spot right now, you may not feel anything remarkable, as you are not aroused. As you stimulate the area and blood flows to the genital region, the tissue begins to swell and researchers believe that its sensitivity is connected to corollary stimulation of the vaginal prostate (previously referred to as Skene’s glands), urethral sponge and inner clitoris. 

Much more here:  https://www.sexwithdrjess.com/2017/05/your-guide-to-g-spots-squirting/

4. How do men gain more stamina while having sex?

If they want to last longer, mindfulness practices can help. Oftentimes, this involves tuning into the feelings in your body. You can begin with practices outside the bedroom and then work them into your sex play. I offer an online  course on lasting longer in bed: https://www.happiercouples.com/store/yu7R2zGx

Here are some options to get started with mindfulness:

Breathing: Wave breathing: visualize yourself lying on a beach; with each inhale allow the waves to roll over your body and with each exhale allow the waves to retreat and roll back out to the ocean.

Cloud breathing: visualize yourself inside a warm fluffy cloud; with each inhale, allow the cloud to tighten over your body providing warmth and comfort and with each exhale allow the cloud to expand into the blue sky.

Deep, relaxed breathing can heighten your reaction and encourage your body and mind to experience the pleasure of massage with a genuine degree of presence.

Whether you are giving or receiving, your breath impacts your interpretation of sensations and helps to put your mind into a state conducive to experiencing pleasure. Intrusive thoughts can also often be dismissed through conscious breathing involving a focus on our inhalations and exhalations. 

Breathing is elemental to activating the relaxation response, which is a positive physical state of deep rest considered the opposite of our stress-induced flight or fight response. Harvard physician Herbert Benson’s research suggests that this response gives rise to a sense of calm, pleasure, refreshment, and overall well-being as your blood pressure, heart rate and stress hormones decrease. As your mind is cleared of clutter and your levels of anxiety and stress plummet, your body becomes primed to respond to physical and sexual stimuli.

To help prepare your body for relaxed, conscious breathing and encourage a state of physical tranquility, lie in a comfortable position with one hand on your stomach. Breathe in through your nose allowing your hand to rise as your belly fills up with air. Exhale through your mouth allowing your natural sounds to emanate effortlessly. After a few minutes, perform a mental scan of your body beginning at your toes and working your way up to your scalp to intentionally relax each muscle as much as possible.

You may want to try the tense-and-release method of progressive relaxation or simply visualize each body part falling into a heavy state of serenity. If you find that the massage becomes arousing, embrace the pleasure, but stay focused on your breathing maintaining a steady rhythm and profound depth.  

If your anxiety is related to intrusive thoughts, visualize putting your intrusive thoughts in a box and shelving it away. You can get to it later. If your mind wanders back to it, don’t fret (go easy on yourself!). Simply remind yourself that you can take care of it tomorrow, as it’s shelved away for the time being so that you can enjoy your time with yourself and/or your partner. 

It’s important to note that it’s often easier to develop a skill (like mindfulness for presence) outside of the bedroom first; once you’ve practiced it and it becomes easier, you’ll find that it translates in the bedroom as well. So you may not visualize waves as you breath during sex, but as you become more comfortable being present and in your body, you’ll likely find that feeling in the moment comes more easily during sexual activity — and your anxiety may dissipate. 

Visualisations: This is a stressful time. The constant change, disruption and uncertainty is likely to lead to heightened stress levels and more intense feelings of worry. Daily visualisations can help to reduce stress. The shower visualisation for example can be used before you get into bed: rather than simply rushing to cleanse yourself, take a few moments to feel the water against your skin — notice its temperature, texture, movement and pressure. As the water rinses over you, visualise all of your worries and intrusive thoughts washing down the drain. 

If distracting thoughts pop into your mind in bed, remind yourself that you’ve washed them away for the day and allow your thoughts to come back to the present. 

Touch activities to lay the groundwork for mindful sex:

Hand Caress: The purpose of this activity to build presence and connection between partners so that you both cultivate the skills of giving and receiving.

Find a comfortable position. Relax or close your eyes. Sit back as your partner strokes and caresses your hand and arm for 5-10 minutes. Focus only on your own pleasure as you receive their touch. Tune into the movements, textures, temperature and sensations in your body. If your mind wanders, don’t worry; simply bring it back to the present and hone in on the physical sensations of their touch. 

Facial Caress: Same as above, but with the face and neck.

5. Do you think women have a lower sex drive than men?

Research does suggest that women have fewer sexual thoughts than men, but it varies greatly from person to person. 

It’s also important to remember that the desire for sex doesn’t always arise spontaneously. Many folks (of all genders) need to cultivate desire by getting aroused first. This is referred to as responsive desire.

Most of us assume that we should wait  for the desire for sex to arise on it’s own.  But then we find ourselves waiting  and waiting. 

The reality is that if you don’t find yourself in the mood for sex, but you want to get in the mood for sex, you can simply do something to get yourself aroused first.  And then desire will likely follow. 

For example, you might get aroused by…

Play with erotic material — stories, videos, art, webcam models and porn all offer great shortcuts to arousal (which can produce sexual desire) for many people. 

Fantasize. Think about things you’ve done and all the sexy things you’d like to do. How do you want to be looked at, spoken to, touched and played with? And what do you want to do with a partner? Anything is fair game.

Use toys. Sometimes some vibration, suction or flicking is just what your body needs to get all riled up — and your mind is more likely to follow.  Research reveals that vibrator use is positively correlated with desire, lubrication, orgasm, lower levels of pain and overall sexual satisfaction. 

…and then the desire for sex follows.

6. How to get to a point of total relaxation to enjoy anal sex?

This is a big question with a long answer.

The short answer: Get aroused. Have an orgasm. Use a toy. Tell your partner to go down on you.  When you’re aroused, a cascade of chemicals floods your body.

As arousal builds, the pituitary gland is activated and increased levels of dopamine, endorphins and oxytocin can have a palliative effect on the body; this chemical release may explain why sensations or touch that might feel uncomfortable during the very early stages of arousal can feel overwhelmingly pleasurable as sexual excitement builds.

7. Some major tips on oral sex?

Use more lube and your hands! (Kim here – I’m linking my favourite Coconut Oil Lube here 😉 )


For blow jobs, try the Claudia and the Cheater:

Claudia – use two hands and wrap them right around the shaft. Use at least twice as much lube and twice as much pressure as you normally do. This is the hand job to end all blow jobs. It’s that good. And you can use The Claudia as an extension of your mouth as well.  


Cheater — use  your  fingers to squeeze your lips tighter around the shaft as you suck. Your jaw and lips will get a break, as your fingers do all the work (but your mouth is still  in contact with the penis).

For cunnlingus (using your mouth to stimulate a woman’s genitals), try the tongue tube: roll your tongue into a tube and slide it over the head of the clitoris or into the vagina.

And try the Sucker: open your mouth wide around the full vulva. Suck as your twirl your tongue around the perimeter of your lips.

I have some great video courses to up your oral game and  teach your partner to do the same! https://www.happiercouples.com/

8. How does one get comfortable “talking dirty” in bed?

If you find dirty talk challenging or embarrassing, remember that you do not have to conform to any specific standard of dirty. And dirty talk can be a bit of a misnomer,  because sexy talk doesn’t have to be raunchy — it can be romantic, demanding, teasing, playful or fantasy-based.

For example, in porn, there tends to be an emphasis on screwing harder, faster, stronger, putting things in holes, getting rough, talking about size and declaring a specific type of pleasure (e.g. I’m coming!).

These approaches work for some people, but if they do not work for you, you can still embrace talking dirty in your own style and language. 

9. How can a married couple who has been together forever, spice up their sex life?

Try one new thing every month and take turns planning. It might be a sex toy, an erotic book, a new position or a new location. You might experiment with sexting, watching porn or using an app-enabled sex toy while you’re out at a party.

Hot sex doesn’t happen on its own, you have to prioritize it.

10. How important is intimacy in a relationship?

Intimacy makes for more meaningful relationships. And intimacy can come in many forms including spiritual, sexual, physical, affectional, emotional and relational connections.


I often assign couples an “intimacy interview”  in which you ask deeply personal questions ranging from “What makes you feel most loved?” to “When do you feel most self-assured?” and “What is your greatest fear?”

Talking about vulnerable emotions can deepen intimacy. https://www.sexwithdrjess.com/2017/11/the-formula-for-intimacy/

11. What is ONE takeaway you want couples to know right now? (piece of advice maybe?)

Invest in your relationship. Formally discuss your relational values. Here are a  few prompts to get started:

􏰀 Why do you want to be in this relationship?
􏰀 What do you want to get out of this relationship?
􏰀 What do you want your partner to get out of this relationship?
􏰀 What does a fulfilling relationship mean to you?
􏰀 What do you consider to be the most important practical components of a relationship?
􏰀 What do you consider to be the most important emotional components of a relationship?
􏰀 What do you consider to be the most important sexual components of a relationship?

11. Where can people find you? Drop your social handles.

https://www.instagram.com/sexwithdrjess/

The Sex With Dr Jess podcast – on all podcast platforms


This was BEYOND valuable! Thank you so much Dr. Jess for sharing your knowledge with us. Can’t wait to try the Claudia in bed 😉

I hope you guys enjoyed that! If you want more info on anything else, feel free to reach out to Dr. Jess on her social media channels.

Xx, kim

+ If you guys enjoyed this post, check out Sexy Gifts for Your Significant Other.

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