The Connoisseur Ch. 02

2. Becoming Alice

The captive female I'd bound that night was called Caroline, although in my mind I already called her Alice. For indeed, she was a very vision of a blond and blue-eyed Alice in Wonderland, grown, undressed, and bound, captured in a Looking-Glass Land of iron, wood, and leather. Our client had a fetish for the storybook Alice. An Alice he had requested; an Alice we would deliver. For the moment, I almost wished I'd left her in lingerie. Something white and lacy, perhaps with blue silk ribbons.

But later. For now, it was best that she feel utterly helpless. Nudity enhances her surrender.

I spoke to her, softly but firmly, in my most seductive voice. "I remember all those talks we had. Do you? Online, by phone. The time we met in person for the first time at that little sidewalk coffee shop. And again, later that very same week. The next week, drinks at my club. Dinner. Do you remember them? Those talks? When you told me your fantasies? Your darkest, secret wishes?"

She couldn't answer, of course, so she simply nodded, trembling, and closed her eyes.

"I am about to make them come true. All of them, my pet."

I made a slow circle around her, examining her closely with the appraising eye of a connoisseur. I don't usually prefer blondes, to be honest. But my client had been quite specific. He may be mad as a hatter (please forgive my private little joke) but he had specific tastes and the money to indulge them. More, he would treat her well, as a most treasured possession (a must!). We screen thoroughly, of course, like the world's most exclusive cupid, in a way. The girl was even English! I made a mental note to have my partner up our price when the time came to sell her on. Accents have value.

She was young, 25, although she looked younger. Her breasts were lush and full, too generous for a C, I judged, but much firmer than natural Ds are generally. Her legs were perfection, shapely and muscular without being too thick. My Alice was an athlete. A dancer, perhaps, although with her ample bosom, that was unlikely. Her bottom was magnificent and absolutely made for the whip, two perfect globes round and utterly unblemished. The pink fig of her cunt was open and inviting. The minx was aroused, for all her fear. She had shaved herself bare. I appreciated that. I wondered if she'd done it just for me.

I completed my circuit. She had full lips, and they stretched wide around the red ball of her harness gag. I chose that gag specifically for her, you know. It matched the shade of her lipstick perfectly. A gentleman must pay attention to detail if he is to fully appreciate a woman.

Her eyes. Ah, those wide, helpless, pleading eyes. They were her best feature. Yes, even when compared to her full and bare breasts. I'd left her breasts with their large, pink, rigid nipples free. No binds, no clips. They were too magnificent to hide. For now, at least. She would have to learn to endure clamps and ornaments in time, of course. It was part of the training program, naturally. Let that me later. For now, I wished to enjoy them as they were.

Besides, while I surely meant to take her well in hand that night, and certainly to introduce her to the whip, I also meant to concentrate on her own sensations, the agony of her own pleasure. She would be staying with me, of course. But I wanted at least part of her to think it was her own idea. I wanted her to beg me to allow her to remain as my captive.

Not that she really had anywhere else to go.

She had no family to speak of, a menial job far beneath her, a rat hole of an apartment she was in very serious danger of losing anyway. As I mentioned, I'd done my homework. She would be far, far better off, first with me, and ultimately with a new owner who would cherish and protect her, the prize of his collection of fine possessions. My partner and I operated, you might say, the ultimate and most exclusive matchmaking service the world has ever known. Although our rather significant fees were paid by only one party, the Master, and our contracts were, shall we say, more binding than usual, especially for the captive woman.

Still, there are steps. Any fool can take a woman. A gentleman, though, he earns his slave.

And while only one party pays, both must be happy. That is the real trick. Fortunately, our screening methods are close to perfect.

But again, I digress.

This new Alice was going to stay with me, but I wanted her to want it. I wanted her to beg.

Tenderly, I knelt to kiss her. A gentle rain of caresses with my lips, around the forehead, on her eyelids, on the tip if her nose. Around her lips, stretched around the red of her gag. I kissed away a single tear. She closed her eyes, and I heard a hint of a sigh from behind her gag. Then I nibbled her ear and kissed her throat above her bondage, first gently and then with true hunger. She was moaning behind her gag when I stopped at last, and her breasts were heaving. I reached around and under to caress them once more.

I poured myself another glass of that excellent wine, and took a good sip before I slipped behind her and began kissing the round and white slopes of her bottom. The bottom is an erogenous zone, you know, as sensitive as the breasts, although the nerves are hidden beneath an ample layer of padding. It takes a firm touch to stimulate a woman's bottom properly. I kissed lower, teasing the tops of her thighs, coming always close to the sleek wetness of her slit before dancing teasingly away. She tried to push herself backwards, an amazing feat given how tightly she was bound. I showed no mercy. She was on edge. If I flicked even the tip of my tongue across the nub of her clitoris, I felt sure she would come. But ah, too soon, too soon! Too soon for that by far.

I stopped, and behind her gag, Alice, née Caroline, mewled with frustration.

I moved to the back of the room, to the cabinet where I kept a selection of whips best suited for a first session. Those designed to cause pain, surely, but not to blemish Alice's perfect skin. She tried to turn her head, hoping to discover some clue to my intentions, but of course the stocks prevented that. I heard her moaning in frustration, and thought briefly about removing her gag. But of course that would be all wrong. Best to leave it until I was ready to replace it with a rock hard cock.

Pity, though. Her accent was lovely and her voice was music itself.

I chose a few favorites from my rather sizable collection of instruments designed both to stimulate and torture a captive woman, and made my way back to her, wondering... with which to start? The flogger? Always a fine choice, if obvious. A paddle? The crop? Perhaps, perhaps. A single tail whip? No. Too much for a first session, I think. I found myself caressing that glorious bottom of hers as I considered. And then I decided.

I pulled over a stool, adjusted the height, and sat down next to her. And than I spanked her solidly with the best implement of all, the one my maker had blessed me with upon my birth: my own right hand.

Perfect as poor Alice's bottom was, it was missing something, at least to my expert's eye. A little color. Yes, that's the ticket. That first hard smack made her closer cheek quiver in the most delightful way, and to my delight it began to pinken at once. I wondered if the other cheek would perform as admirably, so I applied a second good spank. It did not disappoint. Truly, my Alice was a girl born to be spanked for a gentleman's pleasure. I caressed her bottom gently after those first two strikes.

Truly, there are few, if indeed any, pleasures in this life that compare to the art of touching a woman's naked flesh. The gentle caress is bliss itself. The cup or the squeeze? Utter joy. But there is something even grander about the feeling of a gentleman's hand settling smartly on a woman's bared body with some force behind it. Especially when she is bound, helpless, and at one's mercy.

The hand should be fully open, curved slightly but firm for optimal sting, sound, and color. The aim must be precise, and always on one cheek or the other, never across both at the same time.

I started slowly, warming her gently and pausing to massage the bottom between blows. That's the best way to make the spanking last, especially when punishing a woman for the first time. I find it best to spank her first with less intensity. If the spanking is too hard, too fast, it ends too quickly. The girl will remember only the pain; it won't have time to burn slowly and inexplicably into her most unexpected and intense pleasure. She won't learn to crave the punishment, and that's a very great wrong indeed. In my not inconsiderable experience, all women have a nerve that leads directly from their bottoms to their cunts, though few of them are spanked soundly or expertly enough to realize it. So a bit of a warm up, so to speak, is in order. You want the girl to submit. Nothing else will do. Besides, too short a spanking robs the gentleman of much of his own pleasure, and that's no good either.

So one must start slowly and build. Only when the bottom has a nice, evenly-spread pink sheen should the gentleman advance to a harsher punishment. Otherwise, one is left with unsightly bruises, the very telltale sign of a rank amateur, rather than a seasoned connoisseur.

Between the spanks and the caresses, it did not take long for Alice's bottom to take on the proper pink glow. And then I began to work her in earnest, slowly deepening the pink to red. Two hard spanks, one to each cheek, and my poor Alice jumped in her bonds and yelped behind her gag.

I spanked her again, and again after that, alternating between the cheeks, taking care to aim and vary my strokes carefully, so that the deepening red glow would be even. A man who doesn't spank with care soon finds that his captive female sports a splotchy bottom, and of course that's no good.

Smack!

Smack!

Smack!

Poor Alice was whimpering frantically behind her gag; her delicious sounds, accompanied by the martial percussion of my cupped hand upon her naked flesh, were a symphony to my ear.

Smack!

Smack!

Smack!

When I judged that her bottom had taken on a nice and brightly red sheen, I intensified my blows again, raining harder spanks, first on one round and bouncing hemisphere, and then the other. The red glow deepened, and Alice struggled mightily in her stock, strap, and chains. I reminded myself again that she was an athlete, but her bonds were strong. She remained helpless and vulnerable to my every whim.

At that moment, my whim was to spank her, and soundly.

Smack!

Smack!

Smack!

Smack!

Smack!

Smack!

I spanked her harder still, and my blows added yet grander percussion to the music she made behind her gag. And then I noticed that her struggles had changed. She was pushing back, raising her bottom in rhythm with my blows, rising to meet the force of my spanks as they fell. So the pain was turning to pleasure at last. I allowed myself a private smile, but I varied the rhythm and intensity of my spanks all the same. No good letting a woman think she has even this freedom. Her fate, pain or pleasure, must remain in the hand, if you'll forgive the pun, of the gentleman.

When the glow on her bottom was bright enough I judged it time to stop. Reluctantly, I gave to her a few last slaps for good measure, and then I stood to admire my handy work.