Jemmy reckoned that he could rightly be accounted some sort of expert in the field of whippings, having been on the receiving end of so many licks during his service as whipping boy to the notorious Prince Brat, but handing them out was something that he was still getting used to.
He laid down a stripe with his cane, right where the buttocks met the backside of the thighs. It went crooked and crossed one of his earlier welts, as red and angry as this new one was white and shocked. His victim absorbed the blow with a slight shudder, and an exhalation through his nostrils like a balky horse, only audible if you were listening carefully for it, which Jemmy was. Then, loosing tightly-shut jaws, he said peevishly, "How many times have I ordered you not to hold back?"
Jemmy grinned broadly and had to school himself to sound serious. "I give the orders in this chamber, or have you forgotten our agreement?"
There was a longish pause. Prince Horace, as he was now known to most of his subjects, or just Horace, as Jemmy addressed him in most contexts, or just Brat, as Jemmy addressed him in other contexts, had learnt a certain amount of manners along with his letters and arithmetic and history, but he was still very much accustomed to having his own way. "No," he ground out, sullenly.
"Then remind me," Jemmy said. When he did not get an immediate response, he added, "Remind me, Brat, or you can do up your breeches and leave."
"In this room I am not a prince, therefore it is permissible for you to strike me," Horace recited hastily. "Please."
Jemmy rewarded him with another two strokes of the springy flexible cane in quick succession, so fast that he knew, from his own painful experience, that they would feel like they had both landed at once. Horace rocked and, no longer able to keep silent, made a sound that was somewhere between a cry and a moan. This was the part that Jemmy liked best.
When the prince had first suggested that his former whipping boy should turn the tables on him, Jemmy had dismissed the idea with an awkward laugh.
"Trying to get rid of me, are you?" he'd said, lightly. "Well, even if I'm hanged, the king won't raise your allowance." Although Jemmy had stayed on at the castle for many years as Prince Horace's whipping boy only after Horace had solemnly sworn that he wouldn't be earning Jemmy any whippings, he had eventually been promoted to the position of assistant bookkeeper to the king's treasurer.
Horace had jerked on his horse's reins, pulling the poor beast up short. "Of course I'm not trying to get rid of you, idiot," he'd said, as Jemmy wheeled his horse around to get a glimpse of his face.
"Then don't even talk about such things," Jemmy'd hissed, looking left and right as though somebody might be listening behind a tree, which, given his youthful adventures in the king's forests, was not a completely far-fetched notion. "You know it's as much as my life is worth to lay a hand on you."
"But I thought you'd want to pay me back after all the lickings I got you!" Horace had sounded oddly frustrated. "I thought you'd have them all tallied up, like the marks in your ledger." Jemmy shrugged.
"I've gotten over it," he said. He'd seen the prince whipped, once, and he'd proven not to enjoy it very much. "I thought we were friends now."
"We are friends."
"Then drop it."
Prince Horace had fallen silent for a very long moment, and Jemmy had devoutly hoped that that would be the end of it, but the prince tried a different tack instead. "What if I said 'please'?" he said quietly.
"Gaw." Jemmy was startled back into Jemmy-from-the-streets.
Jemmy had been very emphatic from the outset that if the prince wanted him to stop, he was to say so at once, partly because he was afraid for his life if something went wrong, but mostly because Horace really was his friend and he didn't particularly want to hurt him. They had tried out all sorts of things--switches, to start out with, paddles and riding crops and, on one memorable occasion, a cat o' nine tails that Jemmy had fashioned himself--but never once had the prince been the one to give in first.
Once Horace began moaning, all aching and needy-like, Jemmy had a hard time resisting the temptation to throw down the cane and fuck him right then. He took out his sexual frustration in another stroke, really putting his back into it this time.
"Stop rutting up against the desk, Brat," he said as Horace wriggled and cried out. "Do you want me to fuck you?"
"Yes," he moaned, and yelped with surprise when Jemmy caned him again, not quite as hard."
"Yes what, Brat?" Jemmy growled, and felt his prick give a little bob of satisfaction when Prince Horace babbled, "Yes, please, please, oh, yes." He enjoyed the whippings because his prince did, whatever his reason for that might be, but he enjoyed the begging for its own sake.
Jemmy did toss the cane aside now, and probed his handiwork with rough, appraising fingers. The prince's royal buttocks were a mass of welts, hot and throbbing with the beats of his heart. He was breathing in shallow pants and Jemmy could feel the tension of restraint in his muscles as he waited obediently for what came next.
The first time they had done this, Jemmy had been so aroused that he had come messily almost as soon as he had fumbled with his lacings without a clear idea of what he would do with his prick once he wrestled it free. After that, they had fooled around a lot in bed (and in the broom closet, and in the stables, and in the treasury, and any number of private and semi-private places) they had gotten a pretty good idea of what sorts of things they liked and how to go about them, but Horace's favorite thing was a good hard fucking after a good hard whipping, and Jemmy's favorite thing was giving it to him.
His prick was already drooling with anticipation, but he slicked it up hastily with a smear of goose grease before pressing it urgently between the prince's burning cheeks. When Horace imperiously demanded harder, faster, now, he didn't bother to demand a please, just slid in roughly and all at once.
The prince groaned with satisfaction and began to rub up against the writing desk again. Jemmy didn't chastise him, but reached around and let him thrust into his right hand while he kept a firm grip on his hip with the left. He felt the hot sticky splatter of seed and milked every drop of it with insistent fingers before he let himself go, crying out and shaking with pleasure. Finally he collapsed against the fine linen of the prince's dress shirt in preference to landing in a puddle on the floor.
They stayed in that position for a moment, hot and sticky and nice, with no distinction between them.
"You can enter that into the credit side of your ledger," Horace said, with a little forced laugh. He kept to the story that Jemmy was merely settling old with him with every whipping, and Jemmy put this down to the fact that he wasn't very accustomed to people liking him or doing things for him without being ordered, much less doing things that he could barely bring himself to ask for.
"Don't worry," Jemmy assured him, smacking his arse lightly, "you're nowhere near balancing the books."