Kaylee Wolfe

Kaylee Wolfe

It's Time to Up Your Masturbation Game

Imagine you’ve been hooking up with someone for a while. They’re not really the touchy-feely type — with this person, it’s all about the sex. They come over, make a beeline for your crotch, and as soon as you've had an orgasm, they're gone. No cuddling. Not even a “same time next week?” They're just out the door.

I'm willing to bet that even in spite of getting to come, a lot of folks out there wouldn't be totally happy with that arrangement. But when you think about it, what I describe here is essentially how a lot of people approach masturbation. If we wouldn't be satisfied with that kind of treatment from a partner, why do so many of us accept it from ourselves?

Masturbation doesn’t just have to be a means to the end of getting off. It can also be an opportunity for connecting with yourself, an avenue for sexual exploration and experimentation, and a practice that supports your overall health and wellbeing.

That last bit isn’t just some woo-woo sex educator shit either. Studies have shown that masturbation can improve sleep quality, reduce stress, and improve body image. And for people who menstruate, there’s pretty much no better cure for cramps. Self-love is self-care, y’all.

As long as you’re enjoying yourself and not engaging in behavior that could be harmful to your overall health, there’s no right or wrong way to masturbate. For those interested in taking their self-pleasure game to the next level, here are a few quick tips:

Seduce yourself. Spend some time treating yourself the way you’d like a partner to treat you. Take a long shower. Cook a favorite meal. Put down fresh sheets. Light a candle. Whatever it takes to boost your mood and chill you out, do it for yourself. Just like you don’t have to wait for someone else to come along and make you come, you don’t have to wait for someone else to make you feel special beforehand, either.

Take your time. Sex with yourself doesn’t need to be a speed run. Ease into it and give yourself space to actually notice and feel what’s going on in your body—not just in your genitals. One way of doing this is to…

Explore your erogenous zones. Put simply, erogenous zones are parts of your body that feel good to touch. While people tend to think of them only in a sexual context, erogenous zones may or may not be associated with arousal; for example, you may like having your back scratched, but that doesn’t necessarily mean it turns you on. It’s not all about your genitals — just like partnered sex, masturbation can be a full-body experience. Regardless of whether a particular erogenous zone turns you on or just feels nice, spending some time discovering and exploring themwill bring more of your body into the experience.

Mix it up. It’s not uncommon for people to fall into a masturbation routine where they do the same thing, in the same way, at around the same time, in the same place every time they try to get off. While there’s certainly nothing wrong with that, there’s also a lot to be said for incorporating some novelty here and there. If you typically masturbate to porn, consider reading some erotica or using your imagination alone instead. If you usually use a toy, try using your hands, or vice-versa. Maybe give a new lube a test run. Use this time with yourself to experiment in whatever way feels good to you.

Whether you’re in a relationship or not, giving yourself time and space to experience pleasure by yourself is a great way to feel good, de-stress, and learn what you like in bed. And what you learn on these solo expeditions is likely to help make partnered sexual experiences even better in the future.

So go on and get down with yourself. It’s good for you.

Have a question for Kaylee? Email her at This email address is being protected from spambots. You need JavaScript enabled to view it. and you may get an answer in a future edition of That’s What She Said.




It's Quick and (Mostly) Painless — Go Get Tested

Howdy, friend. When’s the last time you got tested for STIs?


April is Sexually Transmitted Infection Awareness Month. Although it’s probably a little harder to get into a celebratory spirit about STI screening than it is about Black History Month in February or Women’s History Month in March, there’s no time like the present for having important conversations with yourself, your healthcare provider, and your partner(s) about checking in on the state of your sexual wellness.


Many people assume that if they get an STI, they’ll know it. But some highly common STIs like chlamydia and gonorrhea can be present in the body without any noticeable symptoms.


That doesn’t mean there aren’t potential consequences, however. In addition to potentially passing the infection on to others, individuals with untreated chlamydia or gonorrhea may develop pelvic inflammatory disease (in people with a uterus and fallopian tubes) or epididymitis (in people with a scrotum and testes). Both of these conditions can cause infertility. 


That’s one of many reasons why getting tested regularly is so important. Screening can catch infections that you don’t even know you have, allowing for early treatment and intervention that can keep you and your partner(s) healthy and safe to go on doin’ it like there’s no tomorrow.(Unless the concept of tomorrow is an important part of your sex play, in which case, keep on doing you.)


The stigma around STIs — particularly chronic conditions like herpes — isreal and pervasive, and unfortunately the fear and shame that stigma generates can discourage people from getting tested or seeking treatment when they need it.


But the reality is that more than half of all people will have an STI at some point in their lifetime. Like any other illness that affects our bodies, STIs aren’t a reflection of a person’s character — they’re a normal part of the human experience no more deserving of judgment than asthma or the flu.


Getting tested is confidential and mostly painless. For chlamydia and gonorrhea, it can be as simple as giving a urine sample, though in some cases providers may opt for taking a swab of the cervix or end of the urethra at the tip of the penis. Other infections, such as syphilis, require a blood test. Rapid HIV testing can be done with either a finger stick or cheek swab, while some other conditions, like herpes and genital warts, tend to rely on a visual diagnosis. For people who have cervixes as well as individuals who have unprotected anal sex, Pap testing of those areas for certain strains of HPV are also important; check in with your healthcare provider to find out how frequently you should be screened based on your age and sexual habits.


Even if you’re in a monogamous relationship, all sexually active folks should get tested at least once a year. If you have multiple sexual partners or other risk factors, more frequent testing might make sense. In some cases, the Centers for Disease Control and Prevention recommends getting tested as frequently as every three months. If you’re not sure how often is right for you, you can always ask a healthcare provider.


If you have private insurance, you can get tested through your primary care provider by requesting STI screening at your annual checkups or by visiting Planned Parenthood. If cost is a concern, Planned Parenthood and India Street Health Center both offer sliding scale and reduced-cost screening options. And our friends at Frannie Peabody offer free, low-barrier screening for HIV and hepatitis C year-round, both at their offices and some community events.


Getting tested and treated for STIs doesn’t just keep you healthy — it also protects the health of your partner(s) and, in a very real public health sense, the wider communities to which we all belong. So do your part for yourself and the greater good and make an appointment today. Your junk and your neighbors will thank you for it.

Have a question for Kaylee? Email her at This email address is being protected from spambots. You need JavaScript enabled to view it.and you may get an answer in a future edition of That's What She Said.





Portland Deserves Better Sex

Hi there, Portland. My name is Kaylee and I’d like to help you have better sex.

Before we jump into making that happen over the coming months, you might be wondering who I am and why I’m qualified help you accomplish that goal. Totally fair. Let’s discuss.

I was born in Cleveland, Ohio. Which, in spite of being a decidedly un-sexy place, is the starting point in my sex educator origin story. That’s because, sex-ed in Ohio, as is the case in many other parts of this country, is often questionable at best.

A health teacher at my public middle school told our class that condoms wouldn’t protect against HIV, pushing a marble through a mesh sports jersey to illustrate how the virus could allegedly wiggle its way through microscopic pores in latex (not true). At the all-girls Catholic high school I later attended, the clitoris had been blacked out of the anatomy diagrams in every biology textbook with a magic marker. When I asked why, I was matter-of-factly told that it just “wasn’t relevant.” The list goes on.

Unfortunately, experiences like these are woefully common. When it comes to sex, far too many of us are thrown into the pool without ever having been taught how to tread water, let alone swim. Young people — and the adults that they grow up to be — deserve better.

Around age 16, as I watched friends and peers stumble into awkward, occasionally risky sexual encounters (with few or no adults around to whom they felt comfortable turning for guidance), I decided to do what I could to fill the gap. I did my own research and started talking to friends about sexual health, contraception, safety, and — perhaps most importantly — pleasure, an aspect of sex that it seemed no one except the porn industry was willing to be upfront about. Eight years, scores of presentations and discussions with high school and college students, countless one-on-one chats, and hundreds of questions answered later, I haven’t stopped. And I don’t intend to anytime soon.

If there’s one thing that all of these conversations have taught me, it’s that sex is complicated (and, in my opinion, endlessly fascinating). Sex means a lot of different things to different people, and because it often feels so deeply personal, holding space for different sets of values, experiences, preferences, and identities can be difficult when they conflict with your own. But, as is true for most fundamental aspects of the human experience, the commonalities outweigh the divergences. We all have to eat, everybody poops, and most of us will, at some point in our lives, decide to have sex. We might as well do it well.

All of my work begins with a belief that we all have a right to feel safe and to be heard and respected by our partner(s), no matter what the nature of our relationship may be outside the bedroom (or kitchen, or car backseat, or open field). We also have a responsibility to do whatever we can to ensure that those same rights are a reality for the people we have sex with. Sex should feel good, physically and emotionally, in whatever way we define for ourselves. And to achieve that, we all have to be willing to learn, listen, and communicate.

With this column, I hope to create a space where all of those things can happen. No matter your age, gender, sexuality, or experiences, by sharing stories, asking questions, making room for nuance, and backing it all up with medically-accurate information and community resources, I believe that better sex and healthier relationships are possible in this charming seaside city we call home.

Have a sex question? Write to Kaylee at This email address is being protected from spambots. You need JavaScript enabled to view it.

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