Chapter Twenty-Four
A Suitable Punishment
“That’s fine,” I said, taking a deep breath. “Now, push your trousers down. You’ve been such a naughty boy, Oscar.”
I watched a shudder go through him as he closed his eyes. Then he crept his fingers to the fastenings of his pants. He pierced me with an incendiary gaze as he undid them, and lowered them to his thighs, revealing the perfect, pale globes of his ass.
I whistled. “Why, that’s lovely.”
Oscar blinked, his chest rising and falling with his breaths.
I stepped forward and tapped one pale cheek with the folded leather end of the riding crop.
Oscar started. Then his lips twitched as he settled in for what was coming.
“Be still,” I said.
“Yes, sir.”
He clutched the coverlet in his fists as he waited.
“Hmm. Let me get a feel for this thing before I start.”
I wanted to make sure I could estimate the force of each blow, and I’d rarely even used a crop on a horse, so I turned away from Oscar and swept it through the air a few times.
It made a lovely whooshing sound, and I was sure ’twould deal a nasty blow if I used enough force.
But I only wanted to tease him with a little sting.
I didn’t want to leave a bruise or a cut.
When I turned back, Oscar was about humping the bed, he was so horny for that thing. I almost laughed, but ’twould have given the wrong impression. I didn’t think he was silly at all. But the way he melted at the thought of a little discipline and pain from an ass whooping was amusing as hell.
“All right now. Settle down. I reckon this is gonna hurt. Remember your safeword, now.”
“Yes, Jimmy, I will.”
“Also, you can tell me to stop, and I will. I don’t plan to have you beggin’ for mercy until I’ve got my cock buried inside you.”
“Oh fuck. Je-sus.”
“Uh-huh. I reckon he won’t be able to help you right now.”
Oscar nodded frantically, and I went for it. I brought the crop down quick, so the tip snapped against the skin of his ass with a very satisfying thwack .
Oscar made a noise—something between a grunt and a groan—as he thrust against the bed.
“Don’t you even think about spillin’, boy. We just fucking started.”
“I won’t. I won’t,” he panted, sliding his cheek against the bedspread, his mouth open and his eyes wide.
“All right. Now I want you to count.”
Silence. Then he pushed out a breath.
“What?”
“I want you to count each strike, after it hits you. That was a freebie. So start at one.”
“Oh my— Okay.”
“Okay?”
“Yes, sir, I mean.”
Not sure where I’d got the counting idea, but it seemed right. I wanted Oscar to be mentally engaged in what was happening. Seemed like making him count would add to his debasement. And if I knew Oscar—and I did —debasement combined with a bit of pain was what he lived for.
Fortunately for him, I didn’t mind providing it.
The next strike landed across both buttocks, and he squealed like an animal. If the sound hadn’t become a low, throaty moan, I might have worried ’twas too much.
“One,” Oscar said, gulping a breath and giving a soft grunt of pleasure.
“You all right?” I asked.
“Oh yeah. G-good.”
I did chuckle then. He enjoyed this sort of thing so much, and I couldn’t deny him anything he wanted, no matter how strange it might be.
’Twas his ‘wanting’ as he’d called it—something a person enjoyed that might not make sense to anyone but the person wanting it.
I understood that because there were things I enjoyed, too, like having my boy bent o’er the bed like this, trousers around his ankles, ass in the air for me. I liked it an awful lot.
I gave him eight swats with the crop, ’till there were pink stripes laid out across him in a lovely pattern.
“Eight!” he yelled out after the last one and gave such a godawful groan I imagined I’d either killed him or he’d spent too early.
“Oh fuck, you okay?” I said, dropping the implement and flopping down beside him.
“Yes. Oh God. Jimmy, I’m…fine? I’m in such a good, floaty place right now.”
“You are? Really?”
“Really.”
“What do you want? You want more of the crop or somethin’ else?”
He lay there breathing harshly, considering what I’d asked.
“Somethin’ else,” he said finally.
“Okay.”
He turned his head to regard me, those soft brown eyes full of need. “I want you to spread me with that bar and fuck me. Please, Jimmy.”
Those words from his sweet mouth about did me in.
“Fine,” I panted. “All right. You wanna wait for your ass to calm down?”
He shook his head. “No. I wanna feel it and remember it while you’re tuppin’ me.”
“All right then.”
Part of me was glad, because I sure did want to do that. I only hoped he didn’t regret it once we got going, though I supposed we could make adjustments if needed.
“Take your trousers down all the way then and fold them. Put them on that chair along with your other stuff. And don’t you touch your little nubby. I don’t care how desperate it feels. That nubby’s mine, and I aim to take care of it when the time comes.”
“Yes, sir.”
I went and got the bar, while Oscar did as he’d been told. When he was naked, I had him get up onto the bed.
“Sit on your swatted ass and give me your ankles.”
He shot me a saucy grin as he obeyed, flinching as the skin of his ass made contact.
“Oh, that smarts,” he hissed.
“Good. Bad boys get whooped by their daddies.”
“Fuck,” he murmured, as I buckled one of the leather cuffs around his ankle.
I glanced at his cock. ’Twas bobbing there against his belly, wet at the tip and down the front, too, which was par for the course with Oscar when I took him in hand like this. I reckoned it had started leaking the first time the crop had touched him.
“You sure do like this,” I said.
“You sure do know it.”
I smiled. “Oh yes, I do. Now…”
I straightened and lifted the bar, like I’d seen Trick do when Oscar had been fully clothed.
He went down flat on his back and flinched again as his sore ass rubbed on the sheets.
“Goddamn,” he grunted.
I stared at him for a long moment, savoring the control I had o’er him, before I flipped him quick onto his front.
Oscar groaned and reached for the bed covers, as I held the bar and eyed his rosy, cropped ass.
“Oh, my goodness,” I murmured, licking my lips. My cock pushed against the front of my trousers at the debauched sight of him.
The way the bar kept him spread, I could see between the rosy cheeks of his ass, to that soft pink place I wanted so bad. I saw it contract and release as Oscar imagined what was about to happen.
“God, Jimmy. I’m trapped. You got me.”
“I sure do. Now, what on earth am I gonna do with you?”