Chapter 6: Ruby and the Overseer’s Whip

The overseer’s whip fascinates me. I can tell that it’s the sort that stings rather than damages the victim’s flesh. Which makes sense I suppose. The overseer’s task is to keep order among the slaves in his charge without devaluing their price on the auction block.

Yesterday I heard the pirate captain suggest that if we play our cards right, we could find ourselves living in pampered luxury in some sheik’s harem. I can’t imagine anything worse. Belonging to just one man is the last thing I want. While I was working at the Dead Parrot I was surrounded by men, many of whom didn’t hesitate to take liberties with my body. And Groat, the innkeeper, liked to give his serving wenches an intimate examination every now and then. Nor did he spare his belt when I accidentally spilt or broke something. And that was fairly often, since I find it very difficult to concentrate on serving the inn’s patrons their ale while some man’s hand is busy inside my skirt. My arse cheeks nearly always had a rosy pink sheen.

On board the Red Hawk I was put on display in a very lewd fashion. I’m not complaining since that was partly by my own choice. The lust in the sailors eyes only made me long for one of them to go a step further. However the bosun was quick to use his short knotted rope to make any admiring sailor get back to his work. The bosun would have been justified in using his knotted rope on me instead. After all, I was the one who distracted the sailor in the first place.

The captain didn’t hesitate to use me though. By the time we arrived in Puskin, I was becoming accustomed to being sodomised by the captain. My arse still hurts, but it’s the sort of pain that is worth enduring for the pleasure I gained in exchange. And pain is something I’m used to ... even crave for at times. Applied correctly, pain and pleasure can be two sides of the same coin.

It may seem strange that I enjoy being punished, particularly by a man wielding a belt. However, to me it is a symbol of affection. Groat frequently used his belt on me whenever I deserved punishment, but never too excess. To me a few red marks on my arse are a sign that someone cares about me enough to keep me in line. Like many orphan girls growing up in the squalor of the back streets, I lacked self-discipline. Many of those orphans ultimately suffered as a consequence. The lucky ones ended up as beasts of burden in some man’s kitchen or laundry. The unlucky ones ended up married. This isn’t a gentle or kind world, particularly for a woman, and it isn’t about to change any time soon.

Perhaps I should add that I don’t enjoy pain for the sake of it. Nor do I ever want my body to be torn into a bloody pulp. Groat always showed restraint when administering a punishment. His goal was always to correct my errors rather than to torture me. For that I gratefully thank him, since I know there exist those who get their pleasure from the latter. Naomi said the Vizier of Puskin is just such a man.

I reflect on my own predicament. My neck is chained to a post in the viewing room of some slave dealer’s compound. Naomi and Emerald are similarly chained to the posts either side of me. They are doing their best to entice the steady trickle of prospective buyers into wanting to buy them. Within a matter of days I will be sold into slavery, probably for the rest of my life. How do I feel about that? I can’t prevent Captain Jack from selling me, so I am ambivalent about what is happening here. As Emerald said to him yesterday, no woman in our homeland is ever free in the real sense of the word. Every woman is the property of some man, who can do with her as he wishes. Slavery is only a technical difference from my previous status in life.

The overseer wants me to copy Naomi’s and Emerald’s actions and brazenly display my body to his clients. In reality all I want is to feel the taste of the overseer’s whip. In that respect he is more than happy to oblige, even if he doesn’t initially realise why I’m being so disobedient to his orders. Unfortunately for me, the overseer is no fool and before long he guesses my secret game. He goes to talk with the owner of this establishment and a short while later my neck chain is unfastened and I’m escorted into a different room.

The room I’m taken to is much smaller than the viewing room I’ve just left, although it is clearly used for the same purpose. I’m made to stand on the raised platform. A leg iron bolted to the platform by a short chain is locked onto my left ankle.

“Hands on your head, slave,” orders the overseer.

I do as I am told since I can guess what is about to follow, and the prospect of such intimate attention excites me. The overseer is experienced enough to detect my arousal.

“How many strokes of this can you take before moving your hands or crying out, slave?” asks the overseer while brandishing his light whip through the air. A whip that is a stinger rather than a welt maker.

“Twenty on my bottom and back, or about ten on my tits, master,” I reply, making a reasonable guess based on my past experiences.

“What about this one?” he asks, fetching a much heavier whip from a rack on the wall.

“I’ve never experienced a whip that heavy, master.”

“Then guess how many you might be able to take before moving or crying out,” demands the overseer.

“Umm ... Perhaps ten on my bottom and back. I don’t think I’ll be able to take any on my tits without moving or crying out,” I reply. “Master,” I add, belatedly complying with one of the instructions we were given when we arrived.

“We shall test the heavier whip later. For now let’s see if your first boast is true,” says the overseer reverting to his light whip.

I don’t get any warning before the first stroke of his whip lands on my bottom. I feel incredibly proud that I hold my position and only let out a barely audible hiss. The whip lands with a light sting. I know it will leave a faint red line that will quickly fade. I’m ready for the second stroke, so I easily hold my position. The overseer seems determined to make me lose control, but so far I’ve defeated his best attempts.

Only when we get to the eighteenth stroke do I start to worry about losing my control. My bottom feels as though it is on fire and my insides are like a volcano ready to erupt. My tendency to have an orgasm when I’m treated in this way is partly why I desire such attention in the first place. I try not to let the overseer guess what is going on inside the hidden depths of my body. It’s a forlorn hope. The man is far too experienced in his trade not to notice what is happening.