The Naughty List #2
And with that, he began. It wasn’t so bad at first, was maybe even as good as Gerry had dreamed of it being. The swats were light and well-dispersed and Santa smelled good and felt good and Gerry had no doubt he deserved to be punished.
But only ten or so strokes in, something shifted. Not just Gerry’s cock, which had been desperately shifting its way through the velveteen cleft between Santa’s thighs this whole time. No, what shifted was the force of Santa’s slaps and the heat in Gerry’s ass.
“Santa,” he complained, throwing an arm back to deflect. “It hurts.”
“Which is exactly what I promised.” Santa didn’t let up at all. If anything, he spanked harder.
“Santa,” Gerry pleaded, tears threatening. “Please.” He squirmed, trying to escape the smacks raining down like hellfire but also to rub his cock harder against Santa’s leg. “Please,” he begged. “Please.”
“Shh.” Santa stopped spanking him. “It’s okay, little boy. Santa’s got you.” His gloved hand rubbed soothing circles on Gerry’s back. “I promised, didn’t I?”
Gerry nodded, mollified. But wait. The only thing Santa had promised was that it was going to hurt.
“No,” he implored. “Noooo.”
“Santa wants you to be good. Can you be good for me, Gerry?”
“I don’t know.” That was the truth. He wanted to be good—to do his work and earn his bonus and not turn every December into a nightmare.
He wanted to keep his job too, and not get fired for looking at porn on his work laptop or jerking off in the bathroom stalls. But he didn’t know if he could do it.
“That’s why Santa’s here, baby. I’m going to turn you good as gold.”
And with that, Santa got back to the spanking.
Gerry didn’t bother to beg anymore—to plead or complain or bargain.
He was bad, but Santa would make him good.
Maybe the fire in his ass would replace the fire in his cock, though right now they were both raging strong.
He humped and squealed and cried and moaned until he was sobbing so hard he almost couldn’t breathe and his cock was so hard he was pretty sure he was going to come right there over Santa’s lap.
Which was when Santa stopped. The bastard.
He sat Gerry up and gave him a warm kiss on the tip of his nose. “What do you have to say?”
“I’m sorry?” He was sorry. Sorry about having been bad and sorry about how fiercely his ass stung and even sorrier that Santa hadn’t gone a little longer so he could have gotten off.
“And?”
“Um.” Gerry thought for a minute. “And I won’t do it again?”
Santa cocked an eyebrow like he didn’t believe it. Gerry didn’t really believe it either.
“How about ‘thank you,’” Santa suggested. “Santa worked up a powerful hard-on taking care of your bad boy bottom. If you want to be good for Santa, you’ll take care of it for him.”
Gerry nodded. He’d felt Santa’s powerful hard-on rubbing against his torso and wouldn’t mind getting his mouth on it. He let Santa lower him to his knees and waited with his mouth open while Santa fished his cock out of his elastic-waisted pants.
Santa was really packing. Gerry slurped him up, his mind as focused on this task as he wished it would be on the job he got paid for.
The fiery rub of his ass against his heels reminded him of how thoroughly he’d been punished, and the deep thrust of Santa’s cock down his throat reminded him that he hadn’t come yet.
He reached for his own cock, which was hanging right there since no one had bothered to pull up his pajama bottoms, but Santa grabbed his hand before he could touch it.
“Oh, no you don’t,” he chastised, which Gerry assumed meant Santa would get him off himself. He worked harder at sucking Santa, eager for his reward. His first reward was a mouthful of come, which he swallowed contentedly. But now for the real reward: an orgasm.
Santa stood up and reassembled his suit into order. He gave Gerry an affectionate head rub, then went to the sack he’d left near Gerry’s front door.
Ooh, toys. Adult ones, hopefully.
Santa rummaged through the sack and came out with something shiny. “We’re going to need some ice for this.”
Some ice for what? To cool off his ass?
Gerry stood up, vaguely concerned as Santa headed for the kitchen.
Santa returned with a handful of ice in his right glove, and before Gerry understood that he should vehemently object to what was about to happen, it had already happened.
Santa had slapped the handful of ice around Gerry’s hot and ready erection.
He shrieked as his cock wilted faster than it ever managed to get hard, shrinking into the smallest, coldest, saddest anti-cock that had ever worn a… cage?
Gerry stared down, disbelieving. Santa had slapped a cage around his dick.
Santa had withered his dick into nothingness and then locked the nothingness up.
Gerry reached for the cage, first touching, then pulling, then yanking hard enough to make himself yowl as the retaining ring tried to separate his balls from his body.
“There you go,” Santa said, as if something had been fixed. “No more pesky erections to distract you from your work.” He patted Gerry on the shoulder, then turned for the door.
“The key.” Gerry tried to follow Santa, stumbled over his pants, which were still around his ankles, yanked his pants up over the offending cage, and managed to get to the door before Santa opened it. “Where’s the key? Give me the key. You can’t leave me like this.”
“Don’t worry, Ger. I’m not abandoning you.
When you’ve earned your bonus, I’ll unlock your dick.
And in the meantime, I’ll be here every night to check in on you and see what kind of punishment you’ve earned.
So be a good boy and go get some work done,” he added cheerfully before departing with a lighthearted whistle and a friendly wave.
Gerry did not, of course, immediately go get some work done.
First he spent a good fifteen minutes holding a screwdriver dangerously close to his ball sack trying to get the cage off, but eventually he gave up.
It was either see what they could do for him at the emergency room or play the hand he’d been dealt, which meant going back to his laptop and using it for something other than watching porn.
The next day at lunch he sat at his usual table in the cafeteria with a hard, foreign weight between his legs, waiting for Hugo. He had something to ask Hugo, something very important.
“Can Human Resources see what we do on our computers?” he demanded, before Hugo even had a chance to sit all the way down.
Hugo shook his head.
Well, that was a relief. A huge relief. He wasn’t about to get fired. But that didn’t explain who Santa was or how he’d known what Gerry had been up to.
“You’re sure?”
“Positive,” Hugo said as he unwrapped a sandwich. He took a healthy bite and chewed it slowly, contemplating Gerry as he did. “That would be a security concern and a violation of several laws. So definitely no, no one can see what you do on your laptop. Except, of course, Audit.”
~~The End~~
If you enjoy seeing a bad boy who’s been spending too much time jerking off get his comeuppance (and his cock in a cage), try His Boy, Alex. Alex really can’t seem to keep his hands off his dick until his boyfriend takes the matter out of his hands
And if you want to deep dive into chastity, take a look at Locked, which fully explores the subject of cock cages with bonus spankings