The Prince’s Boy: Chapter 50

Welcome to The Prince’s Boy by Cecilia Tan, a tale of a prince and his whipping boy ensnared in a plot of dark erotic magic. Warning: explores themes of dubious consent and situations of sexual jeopardy. NSFW.

A new chapter appears every Wednesday. This week is Chapter Fifty: Jorin

50: Jorin


I awoke sore and stiff, my eyes still closed but my awareness of my skin, of my bruises, spreading through my body. Curiously enough, all Sergetten had done last night was beat me with a leather strap until I literally could not take another blow, and was on the verge of begging him for mercy even though I knew I would receive none. Just as I was ready to let the words spill forth, he stopped.

I did not know if the bond spell allowed him to see my thoughts or if it was mere luck.

He did not fuck me nor make me spill, and he had let me go back to sleep immediately.

But now I was awake, and I took stock of my aches. No, it hadn’t been as brutal as Seroi or the king’s last beating of me. And yet it had reduced me somehow.

“I know you’re awake.”

I rolled over carefully—hissing as welts were scraped by the rough blanket—until I could see him. He was seated on a stool at the table, his legs crossed, a sechal twig in his fingers which he chewed fastidiously. I wondered how long he had been sitting there, watching me.

I wondered if I should crawl from the bed to kneel at his feet.

He continued to regard me, but he did not seem to be expecting me to do anything. He stared at me, but seemed deep in thought, nibbling at the bark on the twig and sighing from time to time.

At last, he spoke. He uncrossed his legs and set the twig aside. “Do you wish to know what I did with the milk I forced from you?”

I pushed myself upright enough to get on my knees on the bed before answering, “Yes, Sir.”

He stood, one eyebrow lifted in surprise. “I beat back the blight,” he said crisply. “All of it. In one sweep.”

I bowed my head. “That is good, Sir.”

“I don’t just mean in one orchard. I mean in this entire region.” He stepped to the edge of the bed.

I didn’t know what to say to that, so I said nothing.

“I want you to understand why I am making the decision I am,” he went on, and reached toward me with his open hand.

I flinched away from him and he closed his eyes as if I were testing his patience. I forced myself to hold still and was rewarded by a gentle touch to my hair.

“Your milk is very potent,” he said.

I could not keep silent. “And does that justify milking me in the most painful way possible?”

To my surprise, I did not earn a slap for that, nor even his ire. In fact, he agreed with me. “No,” he said. “It does not. That is why I have decided to return the control of your release to you, at least, in some measure.”

I looked up at him, caught off guard and uncomprehending. “Sir?”

“The evil Night mages of old drew great power from the helplessness of others,” he said. “You have given yourself freely to me, and yet…” He shook his head. “I do not know that I can explain the nuance. Your milk was all the more potent for having been torn from you with pain, and yet, regardless of what good I might do with such power, it is not…” He shook his head. It wasn’t often one saw Sergetten search for words and I wondered if that was because he thought me too stupid to understand the larger ones. “Suffice to say that I will only utilize the spell to force your milk from you should in either the direst of circumstances or if you earn the severest of punishments.”

My head spun. “But… but I thought you said one of the lessons I must learn is that you can hurt me merely because you wish to.”

“I believe you know that perfectly well, now.”

“Um, yes,” I agreed. But that hadn’t been my point.

But now I was not sure what my point had been.

“What I mean when I say you now control your release in some measure is that I will no longer hold you in check with the bond magic, nor will I force you to spill when not aroused.” His fingers brushed a bit of overlong hair from my eyes. “This is not completely a blessing for you, as I will still expect you to be obedient to me. In other words, you will still need my permission to spill, but you will not be magically prevented from doing so. Your own willpower will be the only thing that holds you back until I grant permission.”

I nodded, but could not help but ask, “And what will the punishment be for spilling without permission?”

His fingers slid into my hair and he took a firm but not painful grip. “That will depend on the circumstance and on how disappointed I am. But your worst punishment will no doubt be knowing that whatever magical use I might have put your milk to is utterly wasted if you spill too soon.”

“Oh.” He was perhaps right. After all, a spanking or beating was something I knew how to shrug off. Guilt over ruined crops and the hunger of people? That I would not be so quick to ignore. “I shall do my best then.”

He let out a huff of breath, Sergetten’s idea of a laugh. Keeping one hand tight in my hair, he reached for my cock with the other, or so I thought. Instead he merely drew a line down my stomach with one finger. “Can you make your cock rise without my assistance?”

“You mean…” My hand twitched but I dared not reach for it. I knew too well the kind of traps Sergetten always laid in his lessons. “Untouched?”

He nodded and let go my hair, stepping back. “Stay on your knees. Hands behind your back.”

I posed as he asked and then looked down at my prick. It was half-hard already, which made me wonder truly who was its master, me or Sergetten. Make it rise? I drew a deep breath, trying to think of something arousing.

But thoughts of Kenet quickly slipped from erotic ones to worry over where he might be and what peril he might be in.

I looked up at the sound of something heavy hitting the table. Sergetten had brought out an hourglass and set it running. “If your rod is not stiff by the time the sands wear down, you know that I shall punish you for disobeying me.”

“Yes, Sir,” I said.

“Perhaps I should make you choose what your punishment should be,” he said, taking his seat on the stool again. “What would you deem fair?”

“I thought you said… well, that it would depend on how disappointed you are.” I tried to imagine a hand stroking me, but that made me think of Seroi’s invisible touch, and if anything my milksacks shriveled a bit. “Well… Given that you claim to expect almost nothing of me, as I am stupid and worthless, you cannot truly be very disappointed, can you? So the punishment should be mild.”

Again that huff of a laugh. Apparently his fuse was slow to light today. “You are avoiding making an answer,” he said. “And that, too, is a punishable offense.” He leaned a piece of slate against the wall on the table and made a tally mark upon it. “So now I shall owe you, in any case. Perhaps it will help your answer if I outline for you some choices.”

“Please,” I said.

“There are many methods of punishment. Deprivation is one. It comes in many forms, such as the withholding of food or water, or even attention or affection. Similar but not quite the same is endurance, for example if I were to force you to sleep bound in an uncomfortable position, or to maintain a certain posture.” He took up the sechal twig and stripped off a bit of bark, chewing it slowly as he talked. “Neither of those would require any effort on my part, unlike corporal punishment, with which you are already intimately familiar—striking, flogging, whipping, and so on. Another form that requires me to give some effort is, of course, sexual punishment, which could include anything from requiring you to perform sexual acts you would find distasteful, to fucking you with painful objects. Let us assume for now that those are the four main styles of punishment you should choose between, given that you are a novice at this.”

I wondered what the other styles that weren’t for novices were, then vowed I would never find out, because I would figure out how to please him before then… or would be bonded to Kenet by then. “Well, Sir, I would think deprivation wouldn’t be the best, since maintaining my health is necessary for our—your—goals,” I began.

He gave an approving nod. “Go on.”

“And…” I hesitated for a moment, but his eyes darkened and I hastened on. “And if I had to guess, Sir, I would say that you derive more satisfaction yourself from the latter two, even though they require some effort on your part.”

His grin was crooked. “Just so. Which leaves us with the familiar and the unfamiliar. You have had a rather strong first taste of sexual pain in the past few days. Would you choose it over being beaten?” he leaned forward slightly, hanging on my answer.

I found my eyes on my cock, which appeared to have gone to sleep. “In my estimation, the sexual element adds a level of severity.”

He cocked his head. “Are you sure? For some slaves, the arousal and possibility of release makes it milder than the plain beating-for-beating’s-sake.”

I could only shake my head. “Perhaps it’s merely my upbringing as a whipping boy,” I said. “Beat me across the thighs with a switch, very well. But shove something into me first, and then switch me? Worse.”

“Noted.” He stood. “You still have not chosen.”

“The punishment should match the crime,” I said. “Switch me, then, for failing to answer quickly enough. And should my cock not respond? Then…? Then something more… intimate.”

He pointed to the hourglass. I had not even noticed that the grains had long since run down. I bowed my head, waiting.

Sergetten tossed a pair of boots onto the bed next to me. “Put those on, and go cut your switches, then. For I have none handy, here. If you happen across any villagers in the woods, worry not. They are accustomed to bare-arsed boys haunting these grounds. They know not to lay a hand on you.”

I returned a short while later, my legs scratched from the underbrush, with a handful of green switches. He was waiting in the same small room where I had been sleeping, though it looked to me as if he had done something with the jars and there was a slight smell of something burnt.

Sergetten directed me to bend over and grip the edge of the bed, leaving my back in a long, flat plane and my arse pointed toward him. The beating was not what I would have called severe, though the cutting blows left me with a few bloody welts.

But then came the “more intimate” portion. “Turn around,” he said. “Sit on the edge of the bed. Spread your legs.”

He looped a thin cord around the head of my cock, pulling it up to a stretched length, flaccid as it was, and then putting the other end of the cord in my teeth.

He stepped back and flexed the switch in his hand. “Close your eyes,” he said. “And do not move.”

I heard the switch cut the air half a moment before it struck me on the right milksack, and I let out a strangled cry through my clenched teeth. Another blow, the same as the first, but on the other side. Then four or five in quick succession, leaving me gasping around the cord. Fresh sweat broke out all over me.

But my ballocks were not the only thing to receive his attention. No. He proceeded to stripe my cock itself, all the way from the root to the head, with the thinnest of the switches, until I could not hold the cord any longer because I could not help but scream freely. But even that did not stop it, because, traitorous thing, it had stiffened and grown while being striped and now it stood up proudly to take its punishment.

When he stopped, I fell back limp on the bed, thinking it was over.

I was wrong. His hand closed around my sore but still straining prick. The bed creaked as he sat on the edge and milked me by tugging my loose foreskin up and down in his fist.

I thrashed in his grip, painful and pleasurable at the same time, my wits entirely scattered, and animal noises coming from my throat.

“I have not given you permission to spill,” he warned, but he slowed his hand not at all.

I was near to exploding. “Sir…” I begged. “Sir, I cannot hold it back.”

“But you must,” he said. “I command that you do.”

“But… but…” But there was no holding back. I screamed not in pain, but in helpless ecstasy, as milk shot in spurts up my stomach, one drop even hitting me in the cheek. I must have come with such force that I blacked out for a moment, for when I opened my eyes, he was already standing by the table, shaking his head at me. He then tossed a small jar and a flat wooden spoon to me. “Scrape up what you can, into that jar. I shall return for it later, and to collect on your next.”

Next? Oh. He put another tally mark on the slate. For my coming without his permission.

I resisted the urge to fling the jar against the door after it closed behind him. Could I have actually held back without magical help? Or had this been just a different way to force me?

I had no answers, and a head full of questions. Like, where did humiliation fit in the scheme of punishment types?

* * *

Impatient to find out the fate of Kenet and Jorin? Book one (chapters 1-56) is now on sale for only 99 cents in ebook from all your favorite retailers or direct from Circlet Press!

About the author: Cecilia Tan is the award-winning author of many erotic books and stories and the founder of Circlet Press.


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