“Ask Kai: Advice for the Apocalypse” is a column by Kai Cheng Thom to help you survive and thrive in a challenging world. Have a question? Email askkai@xtramagazine.com.
Hi Kai!
I’m asexual and a virgin, and I’ve decided I want to have sex for the first time. Despite my curiosity, the thought of having sex with someone else makes me feel kinda squeamish and uncomfortable. I want to make sure that it goes well (or at least okay), but I don’t really know what to do.
I have a lot of issues that make it difficult to communicate with people—I tend to go non-verbal when distressed or excited, and stammer heavily when I’m not, so I’m worried I’ll clam up in the middle of sex. I’m also not that attractive, so finding someone to have sex with me to begin with will be hard, and there are quite a few boundaries I have (that probably seem mundane/silly to others, but are very important to me) that I’m afraid will be crossed because potential partners won’t take me seriously.
At this point, I’m looking to hire a sex worker, but my issues with communication won’t just go away, and even then, I’m worried I just won’t like it. Is there any way to get over my sex aversion or communication issues? If not, do you have any advice for me in general? I’m sure I want to have sex at least once, but not really sure how to go about it.
Sleepy In My Bed
Dear Sleepy,
What a tender question! Having sex for the first time is a big deal for most people, and when we bring in asexuality and non-verbality, I can certainly see why you might feel nervous. I want to acknowledge that it takes courage to explore ourselves sexually, and I’d like to validate and honour that courage, Sleepy. I hope you can too.
When it comes to advice, let’s begin by affirming an essential foundation of pleasurable sex—that is, the right not to have it! You may already know this, Sleepy, and you mention in your letter that you’re sure you’d like to have sex at least once, but I do think it’s worth stating here that no one should have to have sex if they don’t want to. Having sex is not, contrary to popular belief, a developmental or psychological imperative for everyone; it does not make us more or less mature than anyone else; and not everyone needs it to live a rich and happy life. Sex is more important to some people and less important to others for many reasons, and every place along the spectrum of wanting or not wanting sex represents a valid way to be human.
As a somatic sex educator, I say this to everyone who asks me about having sex when they’re sure they would like to try it, but are also feeling some ambivalence or anxiety: It is important to respect your body’s yeses and nos equally, and it is absolutely normal and quite common to feel both a yes and a no to sex simultaneously. In your case, Sleepy, I perceive that ambivalence when you say “I want to have sex for the first time, but the thought of having sex with someone else makes me feel kinda squeamish and uncomfortable.” That squeamish, uncomfortable feeling? It’s your body saying no.
When we have both a yes and no to sex in our bodies concurrently, a typical response is to try and force ourselves past the no. We try to override our body’s resistance by pushing ourselves harder and faster. Sometimes we try to mimic images and ideas that we’ve seen in the mainstream media and pornography about how sex is “supposed” to be.
Most often, this does not work, at least not in the sense of getting us to the pleasurable sex that we so desire. The body, when pushed past the limit of its resistance, tends to respond by resisting harder. This is where, during sex, we often start to feel shut down, repulsed, numbed out or even physical pain.
So what’s an erotic explorer to do instead of forcing ourselves to have sex when we want to try something, but some part of us is saying “no?” I think it begins with giving ourselves permission to stop at any time, a permission that needs to be equally held and understood with our prospective sexual partners. With that baseline established, the body often already starts to relax and open up to new physical sensations.
From there, another often helpful way of doing things is to go slowly and to only engage with activities that feel good, or at least okay. As soon as you start to feel that squeamish feeling, I would suggest that you pause and take a break. What would help that squeamish feeling to feel better? Could the sexual activity be adjusted, or would it better to move on to another one entirely? If you really want to challenge yourself and see if you can push through the squeamish feeling, I’d advise waiting for no more than 10 seconds before taking a break. Sex should not have to be endured, and enduring can have the opposite of the desired effect of dropping into relaxation, and ideally, pleasure.
It can be helpful as well to remember that “having sex” spans a vast range of activities and is defined in an infinite number of ways, depending on whom you ask. It is not necessary, for example, to engage in genital or anal penetration in order to think of yourself as having “had sex.” Many other activities such as digital stimulation (hand jobs), oral sex and others “count” as having sex if you want them to. You get to define what sex is for you, and the more practice we have at taking control of our own sexual experiences and making empowered choices, the better sex tends to become.
When it comes to communication, Sleepy, it seems to me like a big part of the challenge you are facing is feeling overwhelmed and self-conscious. Of course, self-consciousness tends to be an unfortunate self-fulfilling prophecy in that the more anxious we feel about not relating “properly” to others, the more likely it is that our anxiety will get in the way of having the kind of interactions we want to have. Practice in a low-stakes, nurturing environment can be immensely helpful in reducing anxiety and overwhelm when it comes to flirtation, sex and intimacy.
These days, there are lots of great, low-pressure workshops and other educational programs for adults who want to learn more about sexuality and practice setting boundaries and asking for what they want. I particularly recommend courses run or endorsed by the School of Consent.
An advantage of group adult sexuality classes is that there is often less intensity than one-on-one work, and a lot of room to engage with exercises and lessons in a way that works for you. However, one-on-one sexuality coaching can also offer extremely valuable opportunities to practice the intricacies of flirtation and intimate communication.
When it comes to these highly detailed, idiosyncratic skills, I tend to recommend sexuality coaching over sex therapy. Sex coaching tends to get a lot more hands-on than sex therapy, which I recommend more for sexuality issues related to mental health and trauma. One coaching modality that may be particularly helpful in your case, Sleepy, is Somatica, which was designed particularly to strengthen the skills of embodied erotic communication, and develop a sense of inner safety and confidence. Somatic sex education, my own modality, could be really helpful with the pieces around sexual aversion and discomfort.
At the end of the day, I encourage you to follow any path that helps you to feel best in your own body and most confident in yourself. Sex coaching and education make up one way to get there, but so are connecting with friends, doing social activities that bring you pleasure and wearing outfits that make you feel good. You write that you are “not that attractive,” but I believe firmly in the old cliché that confidence is attractive—not the surface-level, cocky confidence peddled by pick-up artists, but rather a deep and clear understanding of your own best qualities, inside and out. If you can’t be smooth and suave, lean into being earnest and authentic. Shyness becomes sexy when you really own it.
Good luck on this adventure, Sleepy! You got this. Give yourself the space to get messy and make mistakes. Honour both your yes and your no. Trust your body. Always remember how brave you are.
Kai Cheng Thom is no longer a registered or practicing mental health professional. The opinions expressed in this column are not intended or implied to be a substitute for professional medical advice, diagnosis or treatment. All content in this column, including, but not limited to, all text, graphics, videos and images, is for general information purposes only. This column, its author, Xtra (including its parent and affiliated companies, as well as their directors, officers, employees, successors and assigns) and any guest authors are not responsible for the accuracy of the information contained in this column or the outcome of following any information provided directly or indirectly from it.
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