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Welcome to Playboy Undercover—where our anonymous columnists give you a peek of what’s really going on, well, under the covers. From the curious to the downright kinky, our guides are pulling back the curtains on desire. Wanna invite us undercover? So long as it’s between two (or more!) consenting adults, we’re game. Send your story to [email protected].
It is worth starting with three facts, which is that I am a straight woman, I am a chronic people pleaser, and I hate sex.
Broadly speaking, I think I’ve just always hated my body, not necessarily for its aesthetics, but because I dislike the business of having a body. Except for feeding it, I find all other body-related tasks pretty annoying. Things like having to put my body to sleep (does anyone like drooling against their will?). Having to take it to an orthopedist because its left thumb is sore. Having to drive an hour to get its hair trimmed. Having to lie to fitness instructors that my body is extremely injured so they don’t make it run more than 3 MPH. But no doubt the worst part of having a body is living in a scary society that has normalized bodies touching in a romantic and/or sexual context.
Unsurprisingly, my first experience with sex was a negative one. It involved my high school boyfriend, with whom I planned to lose my virginity the night before leaving for college. He took me to his bedroom (i.e. the garage where he had set down a sheet for us on the concrete floor and turned on all the fluorescent lights. It was an unsettling scene, but instead of saying anything, I immediately took off all my clothes and laid down like a corpse. In the end, he was flaccid, and I was cold (physically, not emotionally), so things did not go well.
Since then, sex has been a series of mild disappointments. There are a variety of tactics I compulsively deploy to keep men from touching me or wanting to touch me again. Whether it’s claiming I have a condition where my period lasts for months, asking about their mothers as they orgasm, or simply farting, I will do almost anything to get out of, or prematurely end, sex. I have literally run away in the middle of intercourse – or more like the beginning because I don’t remember being more than two or three thrusts into the process – with the guy chasing after me asking if it was because I had “finished”. These antics may not paint the picture of a woman who likes to please, but given how irritating I find sex, I think it’s pretty generous and merciful that I put out at all.
But the hardest part of sex, beyond the constant threat of UTIs, is navigating my own pleasure in relation to someone else’s. I’ve only been able to orgasm externally while masturbating, and I’ve been pretty content with this DIY approach. Because physical contact with males has ranged from slightly painful to mediocre at best, I’ve found little motivation to pursue it.
People have asked if I’m asexual, and my honest answer is that I don’t think so, but I’m too busy to confirm. Who has the hours, weeks, years needed to investigate the difference between asexual, graysexual, sex-averse, sex-indifferent and all the other ways one can self-define sexuality these days. Life is short, and there are so many other things I’d rather Google, like spider paws (cute!) and inverted pendulums (cool!).
I was very content to continue my body-unaware, sex-avoidant life, until I approached my 35th birthday, and the internet started plying me with evidence I was old and dying. After months of a targeted attack by the algorithmic gods where I was fed ads suggesting I needed a “mini” facelift, blood “oil change,” and trip to Korea to scan my entire body for disease, I had no choice but to reckon with my mortality. It hit me that my body was a limited resource, and like a discount code about to expire, I should probably start using it for stuff (ideally the kind of stuff that helps my body live longer and less painfully).
That’s how I ended up on the phone with the infamous O-Man, an orgasm expert and miracle bodyworker a friend had paid to give her over an hour of therapeutic ecstasy (ie. nonstop orgasms). Apparently the O-Man was a physical trainer living in LA who had discovered a precise, physiological formula for the female orgasm and has now devoted his life to teaching women how to orgasm more easily. According to my friend, if the goal was to find ways to enjoy being in my body, what better way than to have more orgasms, which many people claim is an enjoyable sensation? Also, knowing my aversion to sex, she thought O-Man could help me cultivate a willingness to sleep with my current boyfriend (a color blind Minnesotan named Bryan), whom I proudly hadn’t touched in ages.
I promptly reassured her everything was great with Bryan because he loved me so much he found our minimal sex life to be “totally fine for now.”
“Just contact O-Man through his website. He’ll create a bespoke program for you based on what your body needs and work with you on the quote,” she encouraged. “I think you’d learn a lot. Plus, orgasms actually shut down the prefrontal cortex, which reduces anxiety and fear and boosts your body’s recovery systems,” she read from an article neither of us had the scientific literacy to understand.
“I like having fear and anxiety. They’re useful emotions that help me make informed, cautious decisions,” I retorted.
After calling me a loser, she left me to my existential spiral.
With Bryan’s blessing (“If this is something you’re curious about, I think you should go for it”), I contacted O-Man, who I’ll just call Hamilton, because I signed an NDA not to reveal his identity, and that was also the name of my beloved childhood hamster. Three weeks later (Hamilton’s earliest availability), I had my introductory phone call.
He first asked me where I felt tight (a genuine musculoskeletal question, not a suggestive one), and I responded, “I have no idea what you’re talking about.”
He tried to reframe and asked, “How does your body feel right now?” which seemed like an escalation of an already hostile trick question.
“Uh…my body is normally one feeling. Unless there is some kind of extreme pain,” I replied.
After grilling me with more onboarding questions, Hamilton concluded, in kinder terms than I’m about to paraphrase, that I basically had such a profound lack of body awareness it would be almost impossible for him to help me remotely (an option he offers clients who are more in touch with themselves or located far away, even though people fly in from all over the world to see him), and it’d be much better if I saw him in person.
“I’m going to make you feel completely different in your body and make you orgasm every way you can, and in the one percent chance that doesn’t happen during our session, I’ll give you the resources and additional help to make that happen on your own.”
His methodology, built on discoveries about muscle imbalance by Czech neurologist and physiotherapist Vladimir Janda, focuses on postural therapy and muscle quality. He claims that his methods have led to orgasms as a fortuitous, but often essential, byproduct for over 600 female clients. Fun fact: Masters and Johnson only studied 382 women.
Hamilton told me that his system works 97% of the time. The 3% that has failed, which haunts him to this day, were all women he saw six years ago at the beginning of his practice, when he was still refining his technique. Nowadays, in the unlikely event someone can’t climax during a session with him, they’re always able to after they do his homework, he says. Even, he thought, someone like me.
Still highly suspicious of any man interested in touching me (even if I was paying him to), I asked him to share anonymous testimonials from happy clients.
From “rolling orgasms” after an inability to have even one to a woman who “felt as if something ruptured inside” her, the reviews were pretty convincing. “Beyond the impressive awakening to pleasure is the way my body and mind continue to feel after our sessions- lighter, more limber, totally pain free with a completely relaxed central nervous system — leaving me feeling calm and centered,” one woman wrote.
For someone whose favorite version of sex is the dissociated kind (a sort of best-worst-case-scenario, if you will), it was intriguing to hear that my mind could be off thinking about things like ecological collapse or my cat’s upcoming dental appointment and I could still experience a barrage of orgasms as long as my body was aligned and the right muscles were relaxed. It sounded so…chill? His signature service was basically a starfish-pillow-princess’s wet dream. Plus, I appreciated that his approach was less “you need my penis” and more “allow me to guide your body towards healing and pleasure.” So I wrote him back and scheduled my appointment.
With the threat of sex on the horizon, my body attempted its classic defense of menstruating immediately, like a startled cephalopod squirting ink to escape. Normally my period would be the perfect out, but because I had already paid for the session and was super motivated to not waste money in this economy, I told Hamilton I needed 3 to 5 days to bleed before I was ready, to which he emailed back, “Ok.”
When I stood outside Hamilton’s North Hollywood apartment complex two weeks later, it was the first time in my life I was meeting a total stranger for sex stuff. The symptoms I usually experience prior to physical contact with males — difficulty breathing, peripheral vision loss, super sweaty armpits — were present, but not nearly as bad. Maybe it was because I knew Hamilton was a specialist with the equivalent of a 5 Star Yelp rating in sex, which I can’t say of any other man I’ve been with. I reminded myself I didn’t have to worry about interacting with his genitals, so there was really nothing to fear (he actually doesn’t allow it — he warns if you try to grab him or to convert the situation into sex, which a few unruly women have attempted, he will kick you out). As I waited for him to meet me, I kept repeating the mantra, “You won’t see his penis,” in an effort to self-soothe, but it only kinda worked.
Eventually a pleasant looking man in a T-shirt and sweatpants appeared at the door and let me inside. I respected that Hamilton didn’t try to do anything crazy, like shake my hand or make too much eye contact. His demeanor was rather professional, if a bit clinical and remote. I was completely silent as I followed him down the hallway to his apartment.
Out of nowhere, he announced, “Your outfit’s really cool.” Note: I too was wearing a T-shirt and sweatpants. He then noticed my furry Crocs and remarked, “Shoes like those are better for your posture because they don’t constrict your feet. A lot of women come here wearing heels, and it’s bad for their alignment.” It was the first time a man had lavished so much praise on my dumpy appearance.
Things were going great for about 30 seconds until we walked into his apartment, and I discovered it was, first and foremost, a visually overwhelming gym. I didn’t realize I’d be expected to orgasm in a literal metal cage surrounded by weights, bars and ropes. He did warn me beforehand his apartment was a gym, but I thought he meant he just had a few dumbbells lying around. He made no attempt at ambiance beyond playing FKA Twigs, who I admittedly love. Before I could get too upset by the visual reminder of exercise (something I hate more than sex), Hamilton gave my body a quick once-over and said, “I can tell you’re a writer.”
“Hah! But I already told you I was a writer,” I replied, confident I had just beat him at whatever mind game this was.
“Yes, but I can also tell from your elevated shoulder and forward head posture and the way your hands drop more forward. You just have a lot of arm and neck tension, which affects your tonic muscles, which affects your pelvic floor, which affects your orgasms.” he said.
As I waited for him to meet me, I kept repeating the mantra, “You won’t see his penis,” in an effort to self-soothe, but it only kinda worked.
In order for a stiff, sedentary writer like myself to orgasm a lot in our two hour session, Hamilton apparently had to release tension in my joints and skeletal muscles ASAP. He directed me to stand on a vibrating platform, close my eyes, hold onto a support rail and relax my body. After about a minute, he asked, “What do you notice happening?”
“I am vibrating,” I responded proudly.
“No… I mean, what’s happening to your body. Can you feel what’s changing?”
“Beyond the vibrations?”
“Yes.”
“Then no,” I replied.
This little dance continued for about 15 minutes. Him guiding me expertly around the gym. Massaging me with a Theragun. Administering some kind of physical therapy to supposedly “lengthen my muscles,” then asking if I noticed anything, and me responding, always, “No.”
After completing the physio part of the program, Hamilton told me to disrobe so he could start making me orgasm “as much as possible.”
I was horrified. Now?! So soon??? Naturally the first thing I had to ask was, “Can I at least keep my socks on?”
“You can keep on whatever you want, but it’ll probably be easier for me to make you orgasm if I can at least access your vagina,” he replied.
Touché, sir.
So I took off all my clothes, save for my bright red socks, and laid down on his couch, which I appreciated was wrapped in a fresh cover. Once again, I was cold.
Hamilton came back holding what looked like a black karaoke mic. “Have you ever used an external vibrator?”
I quickly replied, “No. Is that okay?”
He nodded. Unfazed by dealing with a total n00b, he proceeded to adjust my position on the couch, telling me to close my eyes, stretch my arms and extend my legs in a way that looked awkward, but was undeniably correct because within a few seconds of him touching me with that vibrator thingy, I had three back to back orgasms unlike anything I’d ever experienced on my own. I felt waves of chills along my inner thighs, the parts of my body he said were the most tense. It was the first time I’ve actually seen stars during sex (a phenomenon Hamilton explained was just increased blood flow and hormones flooding my brain — not a stroke), which was all deeply upsetting because it meant I was no longer a part of the demographic of women-who-men-haven’t-made-orgasm I so strongly identified with before.
Despite feeling shell-shocked, I followed Hamilton to the bedroom for the second half of the procedure, where he claimed he would make me orgasm even more. First, he had me lay down on a vibrating bed. Then, he put my feet on a platform that was also vibrating. Afterwards, he whipped out what looked like a dildo attached to a vibrating Theragun, expertly applied lube, and slowly pushed it inside me. I immediately told him it was too deep and felt exactly like my gynecologist scraping my cervix for a pap smear. He quickly adjusted, and then things felt shockingly good. Within minutes, I had my first ever G-spot orgasm, quickly followed by my first ever “blended orgasm” (a phrase I strongly dislike). It was insane.
I immediately asked, “Does everything around me need to be vibrating in order for me to orgasm?”
He kindly responded, “No. It’s not the vibrations. It’s really the way your body is positioned that allows certain muscles to completely relax. An orgasm is a trainable, physical response, and it’s one of the most complete activations of your autonomic nervous system.”
What was miraculous was that for the next hour, he continued to use the same two sex devices on me while I laid in his vibrating bed. He would periodically ask me to adjust my body in ways I would never think to do, with surprising movements that weren’t inherently pleasurable or sexy, like turning my head or stretching my left toes or holding open my jaw, but they somehow always led to an orgasm that completely blindsided me. Hamilton would know when I was going to climax well before I did. He was like the Nostradamus of female orgasms (a reference I hope turns many people on). I was directed to close my eyes, so I had no idea what he was doing down there, but it was obviously working.
At a certain point, he asked the offensive question, “How many orgasms did you have just now?” — which I found impossible to answer. I had never had this large a number and this large a variety of orgasms, so I really had no idea how to count them. I was either having one super long orgasm or a nonstop sequence of shorter orgasms. I honestly started to find the relentless orgasms annoying because they made it nearly impossible to interview him.
“STOP!” I shouted. I had had enough of all this pleasure. I told Hamilton I needed a break because my body felt like it was going to explode. He obliged, of course.
During our recess, I tried to probe into his history, hoping to uncover celebrity gossip or other salacious material. “Who are your other clients? Anyone fun?”
“There’s a big range. I get conservative women. Divorcees. Celebrities. Couples. I just think everybody deserves a chance to feel as good as they can, in a functional body, and to not feel broken. Some of my favorite clients are women with serious injuries or chronic illnesses like MS who didn’t think their bodies were capable, or trans women who get to orgasm for the first time after gender reassignment surgery. I’ve helped women in their late 40s work on their bodies, and it improved their fertility. That’s the work I’m really proud of.”
His saintly response was not the scandalous tea I wanted, so I told him to just go back to making me orgasm. And he did.
After 1.5 hours of orgasms, Hamilton turned off the music, and my sex therapy was finally over.
I had never had this large a number and this large a variety of orgasms, so I really had no idea how to count them.
He then told me, “What you just experienced was the bare minimum your body is capable of. If you continue practicing these techniques, stabilizing and strengthening the muscles in your deep core, your orgasms will consistently be better and more intense” — which was very alarming to hear, because my body could barely handle the orgasms it had just experienced. No one was asking for them to be “more intense.”
“Weird question but as a professional, you can fully divorce your own sexual… reaction… for lack of a better word, from these experiences, even if you’re doing more involved stuff to your clients?” I asked in the fetal position after noticing the very polite absence of his boner.
“Someone asking me for help is not about my enjoyment. I think being earnest about anything where you can feel especially vulnerable is a terrifying proposition. Asking a man on the internet to make you cum a lot has to be one of the most vulnerable positions someone can be in, and I have an obligation toward anyone with enough actual bravery to do that to be fully present and make sure they have nothing to worry about,” he said, worrying me that he might be more empyrean than man.
As I sat on the couch with my legs in a giant foot and calf massager, Hamilton explained all the post-treatment materials he was sending me home with so I could align myself and/or orgasm on my own. I told him there was no chance I could understand it all without his guidance, which is when he proudly revealed he’s been developing a series of apps that will use muscle diagnostics to help people release tension, allowing anyone to access his movement system for their fitness, recovery, or sex goals. He’s patenting his discoveries and will likely branch out into smart devices in the near future, some of them sex-focused, he said.
My body left Hamilton’s place feeling pretty shocked by what just went down. It felt buzzy and shaky and very overwhelmed by all the new sensations. I was astonished when my body willingly hugged Hamilton goodbye, something it almost never does after a sexual encounter. Per our agreement, I promised I would text him when I got home and would follow up the morning after so he could make sure everything was okay. Apparently some women crash their cars after seeing him because they’re so blissed out. Orgasms: good for health, bad for driving.
As I drove at a cautious 50 MPH on the 101, I had the revelation that every woman should pay for sex at least once in her life. Or rather, every woman should go see Hamilton, because calling what he does sex is maybe reductive to the scope of his craft. My experience with him was more like the ultimate full body massage that gave me a complete physical and mental reset. What he really provides, above all else, is a luxury wellness experience, and it was worth every dollar.
When I got home, Bryan was waiting up to make sure I’d survived the perilous journey. Despite feeling like I was high on drugs and had maybe been kicked — ever so slightly — in the vagina, I cheerily recounted every detail of my encounter with Hamilton. Bryan hugged and kissed me and said he was very proud. He even called me “fearless.”
“Should we buy some vibrators?” he asked.
“Probably,” I said.
We did buy the vibrator (Hamilton recommends the Lovense Domi 2 or ones by FemmeFunn after testing all of them) but, so far the only thing I’ve been able to give myself is a headache, not an orgasm. It’s my fault though. I haven’t really been sticking to O-Man’s program Changes I will admit to are that I kinda like having sex with my boyfriend now, certainly more than I did before Sex feels newer (even after 6 years) and like something maybe worthy of time and exploration, even if the results are imperfect. I like to think I’m a little more aligned, a little more relaxed, a little more in my body. I’m not sure if I really am, but at least there’s the genuine possibility of it being true.
Some might consider O-Man’s work to be taboo, but maybe some taboos are a gift? If a serious anti-sexxer like me could appreciate going to him, then anyone can. There’s something satisfying, and obviously liberating, about subverting society’s moral bounds only to realize you’re better off (and better aligned) for it.
I think back to the stars I saw during the first insane orgasms with O-Man, when I started to realize the limits of my body might be endless. Maybe the stars were my body’s attempt to create the sublime, that experience of being briefly overwhelmed by something larger than the self can contain. The body, at its limit, must create its own phenomena. But it does not go dark at the edge. It illuminates.