The Art of Initiation: A Guide to Your First Anal Experience (A vancouver trans provider Evolving Formula)
Last night was fun. A few visits. Some time spent reviewing content that had been sent my way. But what I really want to write about—what I keep getting asked about—is the prostate massage. The anal initiation. The experience of being a first-time bottom.
I've been saying this for weeks now, but my own self-assessment keeps confirming it: I'm getting better at this. Every session, I find gentler, more intuitive ways to guide someone into this experience. Small adjustments here and there. A little more emphasis on certain things, a little less on others. Sometimes the changes aren't so small. I feel like I've arrived at something close to a perfect formula for introducing someone to anal play.
So for those of you who've never tried it—who are curious but a little scared—let me walk you through it. This is the latest version of the process.
The Lingam Massage
Lingam means penis. A lingam massage is, at its simplest, a penis massage. But the way I was taught—and the way that makes the most sense—is that it's an erotic massage rooted in tantric tradition. It's not just about the most obviously erogenous zone. It's holistic. The whole body is part of the process.
The massage begins by activating and awakening the entire body, releasing tension. If your body is tense, if you're in pain, you won't want to be in your body. You'll retreat into your mind—the past, the future, dissociation. So relaxing the body is step one. Eroticizing it is step two.
I use different types of touch. Earth touch: grounding, kneading, deep pressure. Water touch: light, flowing, as if I'm moving cerebrospinal fluid. Fire touch: more intense, tingly, generating heat and sensation. I play with these qualities depending on what you need.
Every lingam massage is different because every body is different. Some people want deep release—they're willing to endure the discomfort of deep tissue work. Others want something purely sensual, purely pleasurable. Every client arrives with a similar goal but very different needs.
The Ritual
Step one: the shower. As hot as you can take it. That's the first layer of relaxation.
Step two: I'll ask if any part of your body is particularly sore or bothering you. That helps me plan.
Step three: once you're undressed and on the bed, we begin with a small ritual. A few deep breaths. If you like lavender, I'll use a little essential oil—its fragrance helps the nervous system settle. If not, we simply breathe. Three deep, slow breaths. In through the nose, out through the mouth with a big sigh.
There's music playing. Medicine songs, usually. For a long time it was Govinda or Om Ma Ni Padme. This season I'm working with Medicine Buddha. Sometimes it's spiritual jazz—Coltrane, The Comet is Coming, others with that same searching energy.
The body activation phase lasts anywhere from 15 to 30 minutes, depending on how much tension you're carrying and how much focus you want. Up to this point, it could pass for a very good regular massage at a spa. But gradually, I begin introducing other kinds of touch. Brushes here and there. Teasing.
If you're interested in anal play—and if you're reading this, you probably are—I begin teasing your backside. Slowly. Gently. Playfully. Leading you, little by little, to want more. And more. And more.
By the time the full-body portion ends, I'll rest my hand on your rear and listen to the pulsing of your anus. What is it telling me? Is it tense? Receptive? By now, some clients are already moaning. Fully erect. Lifting their pelvis like cats in heat, signaling: I'm ready. Others are quieter. Still. Their breathing or pulse may be faster, but they're more reserved. Shy. Either way, I'm listening.
I learned this technique from a friend: in the first stage of anal stimulation, don't use lube. (I always wear nitrile gloves, by the way—I'm meticulous about hygiene and preventing any cross-contamination.) With a dry fingertip, I press lightly at the entrance and feel how you respond. Does it contract? Do you let out a sound? Do you stay silent, poker-faced?
A personal note, which I've mentioned before but bears repeating: I'm a pleasure Dom. I get off on watching others experience pleasure, especially when that pleasure comes from my actions. If you're moaning, writhing, begging for more—I'm hard. Guaranteed.
If you're silent, rigid, tense, shy—I understand. That's part of the process too. Some people need more stimulation. Some struggle to leave their minds, to release the fear of pain, or the shame around exploring this desire. And that's fine. You're a challenge, but I've gotten very good at helping people like you let go. Be patient. I'll get you there.
I'm genuinely proud of this work. Initiating so many men into the pleasure of their own bodies—helping them explore what's been taboo, what society has shamed—feels beautiful. Necessary.
The Exploration
Once I've assessed your receptivity, I apply lubricant and begin exploring with a finger. How tight are you? Here's something fascinating I've discovered: there are many different kinds of anuses. Some have two distinct layers of contraction—the outer and the inner. Some are more direct. Some are surprisingly open, even if they've never been penetrated before. It's a world.
Every prostate is different too. Some sit lower, some higher. Some are larger, some smaller. Every person reacts differently to stimulation. Some enter a state of glory and ecstasy almost immediately—they could come right then. Others feel discomfort, or a sensation that's intense but not yet pleasurable. Some need simultaneous stimulation of their lingam to start deriving pleasure. Some prefer external prostate massage through the perineum.
Discovering how to maximize pleasure in each new body is a challenge, and it's one I'm becoming more skilled at every session.
Last Night's Initiation
Last night's client reminded me of the friend who first taught me to explore anal pleasure—my first adult relationship with a man, back in 2022. So let's call this new client Canadian Orli, after that friend.
He didn't want an intense massage. He wanted something sensual. So I moved energy across his body, kneaded a little, awakened everything gently. Then I kissed his neck. His ears. Little bites here and there. Stroked his head tenderly. While doing all of that, I used my elbow to release tension in his lower back, then switched hands. It felt skillful and fluid. He was delighted.
And while I did this, I began moving my hips against him—slowly, like a slowed-down dancehall grind. Small thrusts against his rear. His reaction was immediate. That's going into the formula from now on.
We played like that for a while before I moved to my hands. When I put on the glove and tested how deep I could go without lube, I was able to reach quite far. I measure readiness for penetration by how many fingers you can comfortably receive. Two fingers: you're ready. Three: absolutely possible.
I communicated this to him. He'd originally been unsure about bottoming, so I'd recommended he book the lingam massage ($180) and, if I determined he was ready, we could upgrade to full service for an additional $40. I told him yes, his body could take me, and asked if he wanted to proceed—in which case I'd need the payment upfront. Always upfront.
He paid. The bureaucratic interlude resolved. We returned to the action.
I prepared my kit. After much experimentation, I've settled on the perfect combination of toys, lube, and tools.
The Positions
There are two ideal positions for first-time bottoming.
Position One: The SquatYou sit on my dick, in a squat position. You control the rhythm, the depth, the pace. This is excellent because you're in charge, but it requires some leg strength, pelvic floor control, and a certain level of confidence. It can be taxing.
Position Two: The Passive OpeningYou lie face down, one leg straight, the other drawn up toward your chest. This allows easy access to your dick and easy insertion of mine. It's more receptive. More surrendered.
From there, we go as slowly as you need. We find a rhythm that works for your body. And we stay there until something shifts—until the pleasure overtakes the fear, until you forget you were ever nervous.
This is the work. This is the art. And I'm so glad I get to do it.
If you want to book one, you can find my availability for massage and other services here
Fantastic write up. Sounds like fun