With all due care and consideration an attractive, blonde, 40-something woman slowly pushes a lubricated, gloved finger into my anus.

“Is that okay?” she asks.

“Um, yeah,” I lie. “I think so.”

“Just concentrate on your breathing,” she says.

This is easier said than done when you feel like you’re going to the bathroom in reverse, but I give it my best shot. Breathe. In. Out. In. Out.

I am a man approaching 40 years of age, which means that having a perfect stranger digitally probe my lower digestive tract is about to become an annual event. For the time being, however, this sort of thing is neither recommended by my physician nor covered by my health insurance. I’m here, in this rather small, humid, and dimly-lit apartment in New York’s Lower East Side because I’m getting a prostate massage. But as the self-styled “Dr. Rylie” delves ever deeper into my rectum, I struggle to remember exactly why.

My journey to this moment began a few weeks earlier when I happened upon a series of high-quality porn clips that

featured very drawn out, technical-looking penis massage. The practitioner’s coconut-oil-slathered handiwork looked otherworldly, and I became intent on experiencing something similar for myself. It turns out that you can’t conduct an internet search for penis massages in New York City without Dr. Rylie’s name coming up a hell of a lot. I emailed Rylie, of “R and R Intimate Remedies,” with links to the clips that had so captured my imagination, and soon received a friendly response.

“AN ATTRACTIVE WOMAN SLOWLY PUSHES A LUBRICATED, GLOVED FINGER INTO MY ANUS.”

She said that while her services did include a penis massage similar to the one depicted in the clips I’d sent, she strongly recommended that I combine the experience with her “sacred spot prostate massage.” Not only would this have health benefits and teach me how to separate orgasm from ejaculation, she said, but it would also result in a much more intense orgasm than is usually achieved by the penis massage alone.

For me, the word “prostate” had always been fraught with negative associations. The term was always either preceded by “enlarged” or followed by “cancer.” But not too long ago, I began to gather that some men — including friends of mine — took full advantage of the “sacred spot” Rylie mentioned to lift their orgasms to an entirely new level. Always looking to squeeze a little more fun out of life, I’d invited several girlfriends to poke around back there when we were getting it on, but I never experienced anything like the intense orgasms that Rylie was promising. In fact, I found a finger in the ass uncomfortable and off-putting. Perhaps that was because my good, giving, and game partners didn’t know exactly what to do, and I didn’t have the firsthand (or finger) experience to guide them. Maybe, I thought, a session with a knowledgeable professional would enable me to level up. With that potential in mind, I told Rylie that I was — ahem — all in.

It’s still light out when I arrive at Rylie’s apartment, which happens to be within walking distance of my own place. She greets me warmly, offers me a glass of water and a seat.

“I really have every kind of guy come to see me for this,” she says, and lists clerics, construction workers, cab drivers, and captains of industry among her patrons. “Young, old, married, single, disabled, able-bodied. I’ve had thousands of clients, plenty of them regulars.”

Rylie says that by seeing them regularly, she’d been able to help scores of clients with sexual problems including impotency, premature ejaculation, performance anxiety, or even a general loss of interest in sex.

“But nothing has to be wrong for this to be beneficial,” she tells me while cueing up some soft music. “Improving your control and improving your orgasm should be reason enough to try it, right?”

I nod in agreement.

“Ready?” she asks, and invites me to strip naked. I do. She offers me a shower but I tell her I’d just taken one before the short walk to her place. “Some guys come straight from work,” she says.

“Say no more,” I reply, and realize that I have never meant that sentiment more wholeheartedly than just now.

I hop onto a bed face down. Straddling my lower body, she rubs my back and butt for around five minutes. I ask her questions about her life and I’m surprised to learn that Rylie is a grandmother. She doesn’t seem much older than I am. Next Rylie asks me to turn over so that I am looking at the ceiling. She takes up a sitting position between my spread thighs. I want to be rocking an award-winning boner, but due to nerves and a little uncertainty, I instead have the turgidity of a jet-puffed marshmallow.

She reaches for some lubricant — a concoction that she devised herself and markets as “Monkey Milk” — and begins, using it to stroke my penis, which eventually responds appropriately to the situation. All the while we chitchat. I keep asking questions, Rylie keeps offering candid answers. I learn about her recent heart problems and promise to lend her a book I have about lifestyle changes that are purported to reverse heart disease. All the while she cradles my balls in one hand while stroking my penis until I’m harder than a roll of quarters. Her ministrations are not quite as ornate as those depicted in the video clips I’d sent her, but they are certainly effective.

“Tell me when you get close to orgasm,” she says.

Within a minute or two I get close and tell her. She lets go and waits for my erection to subside slightly before she begins again. We go through about a half dozen of these stop-start cycles. Each time, she challenges me to try to get closer and closer to “the point of no return” before raising the flag, which I dutifully do.

Dr. Rylie then reaches for more Monkey Milk and, while continuing to hold my rock hard penis, slowly pushes the business end of a Louisville Slugger into my ass. At least, that’s what it feels like. In actual fact, she’s barely inserted the very tip of her finger. My penis immediately begins to deflate. The sensation makes me feel like I’m sitting on the toilet. I’m also worried that, despite my best efforts, my rectum might not be entirely empty. I wonder if the good, giving, and game women who have invited me to put things in their butts are beset by similar worries. I feel for them like never before.

“THE ERUPTION THAT SOON FOLLOWS IS A DEPARTURE FROM THE NORMAL ORGASMS I EXPERIENCE.”

“Just relax,” she says, and I do my utmost to obey.

Eventually Rylie manages to insert around an inch and a half of her index finger into my ass and starts rubbing in what feels like a “come hither” motion, the very same motion I use on the anterior wall of the vagina to elicit what are commonly called “G-spot” orgasms and, in some women, the ejaculation of fluid. Interestingly, a woman’s Skene’s Gland — the source of much of that ejaculate — is also referred to as the “female prostate.” Studies have shown that the female ejaculate has a similar composition to the fluid generated in the male prostate gland. In men, this “prostatic fluid” makes about 25-30% of an ejaculation. With this factoid in mind, I ask Rylie if most guys come more with prostate massage.

“Yes,” she says. “Bringing guys close several times and manipulating the prostate tends to increase the quantity.”

Like many guys, I like the idea of producing elephantine quantities of jizz, but unlike the apparently many guys who come to Rylie, I’m finding it difficult to stay hard — let alone come — due to the wiggling obstruction in my lower bowel. I decide to dispense with the chitchat and get my head in the game. Eventually, I manage to get used to Rylie’s finger, stay hard, and re-approach the point of no return.

“I’m going to come,” I say.

“Just continue to breathe,” says Rylie.

The eruption that soon follows is indeed a departure from the normal orgasms I experience. The novelty of the feeling causes a heightened state of awareness about what’s going on in every part of my body. I feel it run up the back on my spine and fizzle on my scalp. It radiates through my limbs and I feel its waves in my extremities. In some aspects, it’s more intense but the full body-ness of it seems to make it less sexual. When I eventually manage to open my eyes, I even notice that the volume of ejaculate is probably a little more than usual. But I wouldn’t say it’s more pleasurable. I think that the uncertainty about what to expect may have impacted my enjoyment. Similarly, I didn’t unreservedly enjoy the first piece of sashimi I put in my mouth. I had to get used to it before it became something I liked, then loved, then craved. I sure wanted it to be awesome though: both for me and for Rylie, who has scores of clients who credit her with saving their sex lives, and their marriages.

As she towels me off, Rylie asks what I thought about the experience. I tell her that I found it intense and novel, though not exactly mind-blowing. The wriggling finger was more distracting than stimulating.

“I could tell that you were holding back because you were thinking about it too much,” she says as I gather my clothes and get dressed. “I think that you’d benefit from a couple more sessions now that you know what to expect.”

There are certainly worse things in life to have to get used to. And if it meant attaining a truly transcendental orgasm, I’d be more than happy to give it one, two, or ten more attempts.