Speaking of lingering pain, I’d be lying if I said this whole philosophy of dishing out punishment strategically came together perfectly from day one as a Mistress. The first time I ever hit a man—well, other than my ex-husband—was during my second session, and let’s just say it didn’t go very well.

In fact, saying “it couldn’t have gone any worse” would be a more accurate description of that fateful afternoon.

The problem that day wasn’t the slave we were seeing, nor the Mistress who accompanied me, or even the dark, dank condo we had traveled to for the session.

Nope. The real culprit of that afternoon was the bullwhip that had arrived earlier that week—a very expensive Indiana Jones replica we’d ordered from an online BDSM shop.

You see, Rainy and I had very little in terms of a Mistress’s “tools of the trade.” Most of our gear was still with the original Mistress Jaa. Unfortunately, our working relationship with her had deteriorated to the point where we were no longer on speaking terms.

At the time, Jaa’s British boyfriend, Paul—now her husband—had wedged his foot firmly into the door of the whole jaa4u.com business. Rainy and I were hell-bent on taking it over, but with Paul having Jaa’s ear, there wasn’t much we could do about it just then.

So, Rainy had taken matters into her own hands and started buying toys left, right, and center—dildos, cuffs, restraints, floggers, blindfolds, outfits—pretty much anything you could imagine for the femdom game was arriving daily.

While all those purchases were entirely her idea, I had only ordered one thing: the bullwhip. Even in my fledgling days as a Mistress, I think I instinctively knew that my weapon of choice needed to be formidable. And since having “a blaster at my side” wasn’t exactly an option, I went with Harrison Ford’s other iconic weapon of choice. Makes sense, right? Especially considering how heavily influenced I am by movies.

Now that I think about it, our diversification into two wholly different types of Mistresses began right then and there. Rainy was investing in playful floggers and luxurious leather restraints with furry interiors to make the slave’s wrists and ankles feel comfortably restrained. Meanwhile, all I had bought for my first session as a Mistress was that sublimely painful red-and-black bullwhip—and enough rope to dock a ship, let alone tie a man to a bed.

She bought nipple rings; I bought a castration device.

She wanted to seduce men with her curvy, sultry body. I, on the other hand, wanted to turn men into my personal toilet. Potato, po-tah-to. She was Harvey Two-Face’s pretty little girlfriend Drew Barrymore, while I was the one roasting the pig on the spit in Batman Forever.

Or so it seemed. I had no intention of actually using the whip—just as nowadays I have little to no intention of using the branding iron, the Burdizzo, or the fire oil. They’re meant to be visual deterrents, nothing more.

However, my second session as a Mistress was with a regular client of the original Mistress Jaa, and he turned out to be quite the rare pain slut. I say “rare” because, as I’ve learned over the past decade, the percentage of men who genuinely want to be hit during a session is well below one percent. It was pure coincidence that this kid became the first slave I ever had to hit. Even though it was a dual session with Rainy, she had handed it off to me—inflicting pain wasn’t her thing.

The kid was in his late twenties and worked on a cruise ship in some kind of musical entertainment role. He’d complain endlessly that living on the boat felt like a mental torture chamber. He felt so trapped that when the ship finally docked in Pattaya, he needed a full release—by way of being harshly beaten.

From what I understood, Mistress Jaa’s approach had been relatively straightforward. She’d bend him over her knee and hand-slap his ass for two straight hours. Her technique, though, involved a rather ingenious twist: she’d deliberately strike the exact same spot over and over until the pain in that one small area became utterly intolerable. I have to admit, it’s a brilliantly sadistic method of punishment.

Could it be that the first spark of Mistress Jaa’s imagination for inflicting pain like that came from teaching our Ladyboy Natty how to spank for the first time? I remember her looking back and kindly asking Natty to stop hitting the exact same spot on her ass over and over.

After all, “from the tiny acorn grew the mighty oak,” right? You should know that almost every single technique or mannerism a Mistress uses in a session was born out of pure accident. Dominating another human being isn’t exactly a natural thing, so everything on the path to becoming a head Mistress is something learned, bit by bit.

Anyway, there we were, Rainy and I, on the bus from Bangkok to Pattaya to spend an entire day with this kid. He had nothing better to do on his shore leave than throw a ton of money at us just to be punished in the same ruthless way the original Mistress Jaa had done before.

Only, we had greatly exaggerated our level of experience—sold him a false bill of goods, so to speak—just to secure an all-day session with him. It was a lot of money at the time. You have to understand: just a few weeks earlier, we’d still been working as masseuses. There were days when the shop had no customers, and we’d go home after a ten-hour shift with only eight dollars in our pockets. Back then, getting a big tip felt like winning the lottery. If one of us went home with a thousand-baht bill, it was cause for celebration.

So, turning down what this kid was offering—twelve thousand baht—was out of the question. Honestly, if he’d been asking for surgical castration that day, we’d have probably found a way to make it happen.

As it was, all he wanted was to be bent over a Mistress’s knee and spanked.

Unfortunately for him, I had other ideas about how to approach my first-ever spanking session.

When we arrived at his flea-ridden condo at the end of what seemed like a deserted lane on Naklua Soi 15, well, color me unimpressed. With the money he was spending on the session, I had imagined my biggest problem of the day would be getting past the snobby front desk of a five-star beachfront hotel in the heart of Pattaya City.

Instead, this three-story “mansion” (and I use that term loosely—because in Thailand, “mansion” often means “shithole”) looked like an abandoned building. Yet there he was, right at the foot of the property, ready to greet us by dropping to his knees and kissing both my feet and Rainy’s.

Rainy hadn’t brought anything for the session and fully intended to let me handle the entire day of domination, even though I’d yet to face-slap a man, let alone whip one. The only items in my bag were the bullwhip, an obscene amount of black rope, and a warm bottle of baby oil—which I’ll get to in a moment.

The condo itself was sparsely furnished: a raggedy old sofa, a glass-top kitchen table with metal legs, a few mismatched chairs, and a bed at the back of the room. Not exactly the ideal setting to create a mood, but who needs ambiance when you’ve got enough rope to spend nearly forty minutes securely tying a man bent over and spread-eagled on a kitchen table?

I tied each of his legs to one of the chairs at the table, then ran the ropes to the table legs on either side of his body. His torso was bent forward, leaning against the glass table, with his outstretched hands tied to the far table legs. He was completely immobilized, with no way to escape or avoid his afternoon of impending punishment.

First, though, I needed to reheat the baby oil. It was a trick I’d learned from the boss at the massage shop where I used to work. A man’s manhood is an incredibly sensitive organ and responds very favorably to a warm touch—thus, the necessity of pre-warming the oil. This technique has since become a staple in all my sessions.

With all day and night ahead of us, I was in no rush. My idea for the session—and, thinking back, probably where my “20-game” first originated—was to edge him to the point of insanity. The goal was to get him to beg for release without being coerced. His surrender would serve as the trigger to introduce the punishment portion of the session. As I’ve always said, punishment must have a purpose; it needs a reason, or else it’s a meaningless act.

It took nearly two full hours to finally get him to scream the words I’d been waiting for: “Please, Mistress, I’ll do anything.” While my hand techniques were decent even in those early days, there’s no doubt it was Rainy’s involvement that broke him. She hadn’t done much at first, but when she started seducing him—gently touching him, leaning her body close, and whispering sweetly in his ear—it pushed him over the edge.

I then made him a deal: he was to endure ten lashes with the whip in absolute silence. If he succeeded, I’d consider granting him the release he so desperately craved.

As I reached into my bag and pulled out the whip, a sudden realization hit me: I had absolutely no idea how to use it. Up until that moment, I’d envisioned myself as a free-spirited cowgirl, as comfortable on a horse as with a whip.

Oh, how wrong I was.

The thing I remember most about holding that whip in my hand was how damn heavy it was. Within seconds of swooshing it around, I became acutely aware of how much space I’d need to swing it properly—especially indoors.

But, as luck would have it, the bed was at the back of the room, and with nothing else between it and the table near the front door of the long, rectangular space, I had just enough room to take a few steps back and try some practice swings.

I would’ve been better off swinging an iron broadsword. The level of dexterity needed to flick that whip properly was way beyond me. My first few attempts at the wall were so pathetic that one of the flies buzzing around paused mid-flight, as if to say, “Seriously? That’s the best you’ve got?”

And then it dawned on me—every clumsy attempt behind my tied-up slave only made me seem more incompetent in his eyes. The last thing I needed was for him to lose faith in me and cancel the session; I desperately needed the money at the time.

“Okay, I’m ready. Are you?” I asked, doing my best to inject confidence into my voice.

Rainy, however, didn’t share my enthusiasm. She quietly moved to the far side of the bed behind me, a clear sign she doubted my whip-handling skills. Suddenly, I felt the pressure mount. I have to nail this on the first try, or this session’s going downhill fast, I thought, my stomach twisting in knots.

I knew I needed to flick the whip to get the desired crack, but no matter how hard I tried, I couldn’t recall ever doing anything similar. I wracked my brain for a comparable motion—something, anything—that required a flicking action.

And then it hit me: badminton!

Whenever I played badminton, I loved when someone lofted the shuttlecock high into the air, giving me the perfect opportunity to wind up my swing and snap my wrist with all the fury I could muster. That’s it!

The whip was just an extension of my badminton racket. If I swung it with the same wrist action, I’d surely manage to crack it, just like in all those Indiana Jones movies. Or so I hoped.

So I took an extra step back, tilted my head toward the ceiling, and cocked my right arm with the whip in hand.

From behind me, Rainy asked in Thai, “What the hell are you looking at?”

“Shh, I’m visualizing,” I responded.

Which I was. In my mind’s eye, I could see a feathered, white shuttlecock descending gracefully from somewhere above the ceiling. As it fell into range, my body tensed with anticipation, ready to strike the imaginary target with everything I had.

What followed were three distinct sounds, each improbably louder than the last. I remember them all so vividly, as if time itself slowed down to capture the aftermath of my grand attempt. I must have looked like a baseball player frozen mid-pose after a mammoth home run swing, only my form was a little less heroic.

My arm was fully extended to my right, and the force of my “badminton swing” had spun me around to the left so that I ended up facing the bathroom, now perpendicular to my tied-up slave. Despite this awkward stance, my eyes were glued to him, searching for evidence of whether my whip had connected—and if so, how effectively.

The first sound confirmed it had. The crack of the whip hitting its mark was deafening, slicing through the stillness like a thunderclap.

But the stillness didn’t just shatter; it imploded. The whip had landed squarely in the crack of his ass, and his response—a high-pitched, murderous scream—pierced the room like a siren.

Then came the second sound: the crash of the kitchen table collapsing. The kid, likely acting on pure reflex, tried to leap forward despite his legs being tied wide apart to the table legs. His sudden, violent lurch toppled the two chairs anchoring his feet, sending the table legs on that side buckling.

Finally, the third sound arrived with devastating force. The glass tabletop smashed to the ground, shattering beneath him in a symphony of jagged shards. His body crashed down on top of the wreckage, completing the chaotic scene.

And perhaps the loudest sound of all? His voice as he sucked in a ragged breath and bellowed, “Je—SUS—FUCK—ING—CHRRRR—IST!” Each syllable punctuated like gunfire, reverberating off the walls.

Then I saw it: a thin, pussy-shaped tear in the skin between his cheeks, beginning to ooze blood. A crimson trickle flowed down his leg like a miniature waterfall.

It was then I realized something critical: unless you’re a professional sadist—like, say, one of those prison guards in Singapore trained to administer canings with surgical precision—you’re not supposed to swing a bullwhip with every ounce of strength in your body.

I looked at Rainy who was slack jawed, just staring at the slave face down on the floor still tied to the remnants of the kitchen table, surrounded by shards of broken glass, with a slit right inside the crack of his ass where the whip had landed, and yelling very much like Garry in John Carpenter’s The Thing:

The irony of both men sharing the same name—Garry—only my slave spelled his with just one “R,” hit me like a delayed punchline. Honestly, this is where advanced AI could be my best friend. While others are using it to revolutionize medicine or engineer new frontiers, I’d be using it to comb through a decade of email history to answer the pressing question: Exactly how many slaves named Gary have I tied to furniture?

It’s dozens, no doubt, but none in as absurd a predicament as my Gary now found himself.

Rainy, surveying the aftermath with wide eyes and a slack jaw, simply shrugged her shoulders and mouthed, “I don’t know what to do—fix it,” as though she were delegating a botched manicure.

Fix it? Sure. No problem. Here I was, a rookie with less than a week of experience, staring down the angriest man I’d ever encountered, sprawled out on a shattered glass table with a wound on the rim of his ass that was going to need about twenty stitches—and a hefty bill to repair the damn furniture. You don’t fix that. You ride the chaos.

So I strode forward confidently, cleared my throat, and barked, “ONE!”

“One?” he echoed, utterly baffled. Then, “…the fuck?”

“That’s right—ONE. Say it out loud. Nine more to come.”

He launched into a tirade, ranting about how “you don’t hit someone that hard in a session” and how his job on the cruise ship requires him to sit down at the piano for hours a day. “How the hell am I supposed to do that now?”

“Well, lucky I didn’t hit your fingers then,” I replied, swirling the whip lazily around my body like a coiled snake preparing to strike.

“Whoa, whoa, wait. Wait! Can you just… wait a second? Please?”

Ignoring his pleas, I leveled my gaze and said evenly, “Ass up. I’ll count to three. If I have nothing to aim at, I simply won’t aim.”

And that was it. That was the moment I understood the full scope of what it meant to be a Mistress. When I shouted, “ONE!” I fully expected him to tell me to fuck off, maybe even attempt to untie himself in rage. But no. His mind couldn’t compute rebellion against my authority. He genuinely believed I was going to deliver the next nine lashes as if nothing had happened.

It was an awakening. The realization hit me like a lightning bolt: the power I held in this role wasn’t just physical—it was psychological, almost superhuman. A slave’s mind, once surrendered, offered unlimited obedience. My demeanor alone dictated reality. And so long as I played the part, anything I commanded wouldn’t just go unchallenged—it would be obeyed.