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Story: Where There's a Will

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Will

My people had to pay extra and make a few phone calls to get Davy’s passport processed quickly, but watching him in Paris, Italy, and then the Isle of Capri made me the happiest man on earth.

On the yacht ride to Capri, I gave him everything he’d need to deal with the hotel, and told him he was going to be my assistant and take care of everything for me. “You’ve watched me deal with people at every location. You’re smart. You can handle it.”

If he was going to hold down a job then he could never truly be my assistant or even take on the duties of house manager, but I intended to hand some more responsibilities to him, and to delineate them in our new contract.

It meant he’d have a charge card for my account in his name, and he’d be responsible for letting my people know what I wanted and needed. Some things, he could just call my business guy and say, “Will needs you to do such and such,” or call Kyleigh and tell her where we were going and what I wanted to happen while we were there. Other things, I’d expect him to handle without getting them involved, like ordering food, or telling the cleaning staff they didn’t do a good enough job last time.

One of the bikers had told me Davy needed a keeper, and it’d bothered me a little then, but the more I’ve gotten to know him, the more it’s bugged me. I completely understand what they were saying, but he’s a grown man.

In a relationship, even a Master/slave relationship, you take care of each other.

So, I determined that people were going to see Davy as much my keeper as they saw me as his.

Because the truth is, I pay a whole lot of people to keep my life going — a business manager for my company, a business manager for my private life, a house manager, a producer and director, a travel person — and that doesn’t even consider all the specialty people like the lawn service, the pool guy, and the tiny little lady who cleans my gutters every year. Sure, my house manager deals with them, but I still see them around the house, taking care of stuff I guess most people handle themselves.

And that reminded me that I’d meant to change the way he referred to his former Masters. I’d never heard the first guy’s name, and I wasn’t going to demand he tell me because there were clearly a lot of legal issues there, but I wanted him to begin referring to him by either his first name or a nickname. Bubbles was a little complicated, so I was going to suggest he refer to him as Bee, if Davy didn’t have a better solution.

But I’d let him deal with the hotel before I added more stress onto him.

He surprised me, though, because he dealt with the driver before I had a chance to, and when we got to the hotel, he stepped forward and acted like he was in control, handling the affairs for his rich boss.

As soon as we were alone in our hotel room, I pressed him against the wall and kissed him like I was starving and he was the first sustenance I’d had in days. I guess being in charge had taken hold, because he stripped me out of my shirt before he took his off, and then it was a mad dash for us to disrobe. The great thing about having a naked slave is that you just unzip, bend them over, and fuck them.

So the frantic clearing-of-the-clothes was kind of new, and then I had Davy on his back on the bed while I scrambled for a condom, removed the skinny-necked three-pound plug, andfinallyforced my dick into his oh-so-tight ass that he’d been squeezing closed to hold the heavy plug in for better than six hours.

I pinched his nipples one at a time but it wasn’t enough, so I sat up enough I could get to his balls while I fucked him, and gave a quick warning before I squeezed. “Silent pain, slave.”

I squeezed and held for a slow count of twelve, and his ass spasmed and squeezed oh-so-deliciously around my cock. Tears formed in his eyes but didn’t fall out of the sides until I slowly released his balls.

“Good boy.”

And then I leaned forward, braced, and fucked him fast and hard until I emptied my balls into the condom.

Damn, but I looked forward to the day when we could fluid bond, but that wasn’t going to happen while I was still fucking women, looking for our third.

I rolled so I collapsed beside him, facing up, and he took a few minutes to breathe before he sat up and dealt with the condom on my dick.

“You did exceptionally well with the driver, concierge, and then tipping the bellhops.”

“Thank you, Master. I enjoyed doing it for you.”

“And then taking my shirt off?”

“I’m sorry if I overstepped, Master.”

He got off the bed to put the condom in a trash receptacle in the bathroom, and I told him, “It caught me off guard, but you weren’t wrong about me wanting it off. Just know, if you choose to do it again, it’s kind of a thin ice area. If you get it right it’s fine, but get it wrong and you’ll pay for it.”

He returned while I was talking and stopped beside the bed. When I finished my sentence, he gave a short nod and said, “Permission to get back on the bed, Master?”

“Denied. Get the lube from the sex kit and bring it to me, then you have permission to bend over the bed so I can put the plug back in.” I looked at my smartwatch. “We have reservations in about an hour, and it’s a thirty-minute stroll, but we can take a little longer and enjoy the view on the way. Also, I’m down to fifteen percent on my watch.” I took it off. “Put this one on the charger and hand me the black one with the analog dial.”

Okay, so yeah. I have three smartwatches — one silver and two black or graphite or whatever they’re calling it this year. I have a face with tons of information on the silver and one of the black, but the other black one looks like a diver’s watch with a main dial for the time and then four smaller dials, only they show me things like temperature and steps, rather than diver stuff. At a glance, it doesn’t look like a smartwatch, though.

And I’ve set it so the big dial is always the local time, while one of the small dials shows me the time in Chattanooga. Comes in handy on tour and on vacation.