6. Damian

Damian prowled from left to right and back again. His cock was throbbing, hard and straining up against his briefs. The feeling of having Jake at his mercy was dialling into so many of Damian's dom desires.

And knowing that the boy couldn't escape was making Damian love each and every second with increasing relish too.

The things I could make him do to himself.

The things I could make him do to me.

Fuck. Keep your mind on the task at hand…

‘This isn't a roleplay,' Damian said, deciding that he had just about enough of Jake's obvious attempt at gaming the situation. ‘You may think that you can flutter your eyelashes at me or smile like a cute club dancer or some cam boy and I'll somehow forget exactly what the deal is. You're a thief. And if there's one thing I detest more than a thief, it's a thief who is trying to steal from me.'

Damian could see that his words were making an impression on Jake. Perhaps it was the fact that Jake was in his apartment, but Damian felt like the reality of the situation was dawning on the sassy little brat – and not before time either.

‘But-'

‘No buts,' Damian said. ‘You can plead your innocence or come up with your bullshit excuses all you want. I caught you red-handed. And there must be a price to be paid.'

‘I.. I…'

‘Silence. Speak when you're spoken to,' Damian barked, losing patience with what seemed like was going to be another attempt by Jake to find some wriggle room. ‘We're not at a BDSM club or on some kind of kink app. This is real-fucking-life. I am going to punish you for as long as I think you need to be punished. Better yet, I'm going to train you. Do you understand?'

Damian watched as Jake nodded. It wasn't the perfect response, but it would do for now. The boy had stolen from a mafia man and was lucky to be alive, but Damian recognized that there was some potential inside Jake. The way that Jake hadn't totally broken down and lost all of his spirit was an intriguing and compelling challenge as far as Damian was concerned.

But before the real training could begin, Damian knew that there were some business details between him and Jake that would have to be made clear and agreed upon. Namely, a safeword had to be agreed.

‘It has to be a single word. A word you will never forget,' Damian said, noticing that the reality of the situation was beginning to hit home with Jake. ‘Take your time if you need to. It's important we get the details clear and correct from the start.'

Damian watched as Jake nervously twiddled his fingers together. The boy was showing the first sign of genuine nervousness. All of Jake's cocky and bratty behavior seemed to have gone and now the real boy was on display.

As far as Damian was concerned, this was a good sign. But there was still the matter of an agreed safeword…

‘Perhaps I should fetch you a dictionary?'

‘No, I think I have it,' Jake said, his voice trembling a little bit. ‘I want my safeword to be cosmic.'

‘Cosmic?' Damian said, arching an eyebrow.

‘Yeah, that's it,' Jake said, trying to fight his nerves and come over as a little bit more in control.

‘Fair enough,' Damian said, intentionally keeping his voice cold and emotionless despite the fact he couldn't help but feel his heart skip a beat at just how sweet and innocent the boy in front of him actually was. ‘Well, with that agreed, let's not waste a single second.'

Damian felt his cock tingle and then harden.

With his mind overflowing with excitement and a rush of pure adrenalin, Damian pulled Jake up by his hand and led him over to the grand dining table over in the corner of the apartment's kitchen area.

Flanked by two ceiling-high windows overlooking the dramatic backdrop of the city, Damian firmly positioned Jake, bending him over the table and placing his hands flat on the table's smooth surface.

‘You will thank me after each spank,' Damian said, his voice clear and in command. ‘You will say thank you sir after each and every spank. You will do this without fail. Am I being clear?'

‘Y-y-yes,' Jake said, his voice full of nerves.

‘I'm going to pull your bottoms down now to expose your bare ass,' Damian continued, his hands over the edge of Jake's chef's pants. ‘Your cheeks will feel six spanks each. They will be hard spanks. I am not going to hold back. And I expect you will take the punishment to the absolute best of your ability.'

‘Y-y-yes, D-D-D-D-D-Damian, sir.'

As Damian pulled Jake's pants down, his eyes widened at the sight of Jake's soft, perfectly pale little cheeks. Damian hadn't seen an ass this ripe for punishment in a long, long time.

But Damian knew he didn't have time to savor it. A punishment was due, and that had to be the sole focus of the occasion. This wasn't about admiring or fondling a peachy bottom, this was about teaching a wayward thief a lesson – the first of many lessons too.

‘Spread your legs,' Damian said, watching with intent as Jake shifted his stance, opening his legs a touch wider as ordered. ‘Good. Now arch your back, just a touch. I want the best possible presentation.'

With Jake's ass cheeks now fully on display and offering up the sweetest, most tempting target, Damian knew it was time to proceed.

Remember. This is a punishment, not playtime.

But don't get carried away.

This is just the first of many…

Damian took a second to compose himself and drew his hand back high above his head. Without further ado, he brought it down and landed a crack shot right on the sweet spot of Jake's left cheek.

‘Awwwwwww! Awwwwwww!' Jake cried out, immediately forgetting the instructions that Damian had given before the spanking.

‘Boy! Have you forgotten your lines already?' Damian said. ‘Fear not, we'll start again.'

"Aww-, I mean thank you D-D-D-Damian, sir,' Jake said, his voice quivering.

‘Better. Now, let's start from the top. Six of the best,' Damian said, a look of sheer devilish delight on his face as he saw Jake's cheek begin to glow in an almost neon red.

THWACK!

THWACK!

THWACK!

THWACK!

THWACK!

With each spank being just as hard and accurate as the one before it, Damian was pleasantly surprised with how well Jake was coping. Many a cocky spanking club hook-up would have totally folded after the first spank landed, but Jake was hanging in there very well indeed.

‘Thank you, Damian, sir,' Jake said, his voice still quivering but his legs now beginning to knock together, the severity of each spank beginning to take its toll.

Damian rattled through the remaining spanks, each one delivered with unerring accuracy. And as each one landed, Damian was delighted to hear Jake give a word-perfect rendition of his thanks.

‘And now for the final one…'

THWACK!

‘Awwwwwwww! Awwwwwww! Awwwwww! Thank you, Damian, sir!' Jake said, the pain finally becoming too much for him to bear as Jake hopped up from the table and began to jump around, clutching onto his cheeks.

‘Stop that this instant!' Damian bellowed, his powerful voice echoing around the high-ceilinged apartment. ‘I don't expect my boy to behave in such a dramatic fashion. Stand still or I'll begin the entire punishment again from the very top!'

A tearful Jake managed to get himself under control and stood before Damian with his head bowed. Damian could see that this boy was now in need of some aftercare. It was one thing to deliver a hard dose of discipline, but as far as Damian was concerned it didn't mean much if the Dom didn't look after his boy at the end of it…

‘Well done, now let's get those cheeks looked after,' Damian said, gently lifting Jake over his shoulder and walking through the kitchen area and down the corridor toward the bathroom.

Damian could feel that Jake's body was tense and still reeling from the aftermath of what was a very tough first spanking. Damian suspected that Jake must have been disciplined before, but there was every chance that he had never taken such an intense series of spanks.

As Damian carefully placed Jake down onto the heated bathroom floor, he gave Jake a gentle ruffle on his hair. The bath wouldn't take long to fill up with warm water, but Damian saw this as a great chance to check that everything was okay with his young man…

‘You must tell me if you have any issues with how that went down,' Damian said. ‘I know you didn't use your safeword, but as the person dishing out your punishment it's very important to me that you are feeling okay afterward. Do you understand?'

Jake nodded and there was even a hint of a smile on his face.

‘It did hurt. Like, a lot,' Jake said, his eyes still a little bit red. ‘But I was okay. And I'm okay now too.'

‘That's good to hear,' Damian replied. ‘Now let's get that sore butt of yours in the bath and I'll show you exactly how good my cooling salts are for stingy asses.'

As Jake gingerly climbed into the bath, Damian couldn't help but notice just how smooth and slender Jake's naked body was. In the heat of the spanking, Damian hadn't allowed himself any time to drink in just how unbelievably cute Jake was.

Seeing Jake naked, and with his exposed cock on show too, it made Damian conscious that he would have to work extra hard to keep this situation limited to punishment only.

On a purely biological level, every fiber of Damian's being wanted to ravish this cute boy. But that would be irresponsible. Damian knew that he could never get into any kind of serious sexual entanglement with a thief. It just wasn't the mafia way.

‘How does that feel?' Damian said, gently whipping the water around with his hand so that it created some bubbles to help cover Jake's modesty. ‘You'll be feeling much better before you know it.'

‘It feels good,' Jake said, his pupils dilating and a flash of his sweet smile telling Damian that while the punishment may have been a hard one, there was plenty of room for him to spank even harder next time.

And there absolutely was going to be a next time.

The only question was… when?

* * *

With a triple-layered cozy cover over him, Jake looked extra-cute. The fact that he was also fast asleep probably helped too. As far as Damian was concerned, there was nothing cuter than the sight of a properly disciplined boy sleeping off a spanking.

But that didn't mean that Damian didn't still have his reservations…

He's got potential.

But… I can't shake the feeling that he'll be hard work.

And that's not what I need in my life.

Still, Damian's doubts weren't going to stop him enjoying what had been a very productive spanking and lovely bath to follow up. With Jake asleep, it also gave Damian some time to himself. As always, there was plenty of work to be done.

Being a hitman wasn't simply a case of showing up at a location and unloading a caseload of bullets into some unsuspecting bad guy. Far from it, in fact. The amount of planning and preparation that went into every hit was truly epic. Well, it certainly was when it came to Damian.

While most of the hitmen that Damian had risen through the ranks with had either been killed or put into retirement by serious injury, Damian was still going strong. And a big part of this was down to his total commitment to ensuring that every detail and all angles of a hit were covered.

In actual fact, Damian found the research and preparation phase of a hit to be the most satisfying. Damian liked to be in control. He craved nothing more than knowing each and every eventuality and possible way that a hit could play out.

Perhaps this deep-rooted desire for control was part of what made him a Dom. But now wasn't the time for self-reflection, Damian had to put his energy into working out several escape routes from one of the meanest and most notorious underground clubs in the whole city. And that would take a whole ton of concentration.

But as Damian sat at the dining table with his laptop and various blueprints spread out in front of him, he found that his mind kept wandering back to Jake.

‘Fuck. Just focus, man,' Damian muttered, unable to keep Jake out of his head for more than five seconds at a time.

The truth was, Damian was imagining what it would feel like to put a collar on a naked Jake. Puppy play was something that had long been of interest to Damian, and he knew from the second he saw Jake stealing from the restaurant that he wanted to place a collar around the mischievous little brat's neck.

But not just any collar.

Damian had been given a collar by Gianluca, his former mentor. Gianluca had even told Damian to keep it for his one true special boy. Damian had to almost slap himself to get his mind focused. There was surely no way that Jake could be his true love, that simply wasn't on the cards. So any thought of putting his treasured collar on Jake would just have to be shelved.

As he wrestled with his feelings for Jake, Damian felt relieved to see a message coming through from Nico. But that relief soon turned into something else when he read the message…

Damian, you need to hear this. It's not good. That piece of shit Connor Reed has been taking hits out on all of the city's hitmen. Not for any reason other than some kind of fucked up power play. I know you're one tough, street-smart sonofabitch, but I wanted to warn you. Stay safe, brother. ROCCO.

Damian grimaced. This wasn't good news at all. Connor Reed had long been garnering a reputation as an underhand operator. If he was setting about having the city's hitmen taken out, then there must be a reason for it.

Either way, Damian knew that he would have to step up his own personal security. Damian would have to come up with a plan, some kind of pre-emptive counterstrike perhaps…

I could take out some of Connor's men…

Fire a few lethal warning shots his way…

Maybe even…

With his mind a mix of thoughts, ideas and emotions, Damian cast a glance over toward Jake.

‘Still sleeping, huh?' Damian whispered. ‘Life as a sub must be nice. Not a care in the world. I wish I could say the same.'

With that, Damian poured himself a large glass of vintage whiskey. Connor Reed was a problem that in all likelihood wasn't going to go away any time soon.

But Damian Sorrento feared no man.

And as Gianluca once told Damian over a late-night bowl of home cooked tagliatelle… Sometimes the best form of defense is brutal, blood-soaked offence.