Naked Houseboy & his BBW Boss Ch. 01

*Part One of a Series...

I've been in this town two months now. No Friends. No relations. No job. Nothing but a hotel room, two suitcases and a laptop. What do you do? Well, I don't know about other people, but I masturbate. So what if the first thing I did after checking in this afternoon was to jerk off? And then nap. And then jerk off again. And then eat dinner. And then jerk off again. So what? I want to jerk it now and that's what I'm gonna do.

I flip the laptop open, porn still on the screen from my last session. I lean back, naked, in the bed. My right hand is lazily pulling on my not-yet-hard cock. Again. I look at the clock. 11pm. "Eight hours," I think. "I woke up at three. And in eight hours, all I've done is eat, sleep and jerk. And now I'm jerking again." I smiled.

This is why I was here, after all. I'd just gotten out of a bad relationship. I'd just cashed out of a business that I'd lost my passion for. I needed to go somewhere where I didn't know anybody; somewhere where nobody knew me. But most of all, I needed to masturbate. As much as fucking possible.

So there I was. Jerking off for the fourth time in eight hours. Pulling on my still-limp dick. And loving every second of it.

Now, I understand that to some people, that might sound sad or pathetic or just plain uninteresting. But believe me when I tell you, there was no place else I'd rather have been, nothing else I'd rather have been doing, than jerking off alone in that hotel room that night.

And that's when I found the job-posting. I don't know what made me look at job-postings that night. It's not really a wank-related activity, is it? And I had plenty of money saved, so it wasn't like I was stressed about that either. I guess it was as simple as this: One hour and 45 minutes into that jerk-session, I needed a distraction. And wow, was I ever distracted! Because there on the page, among all the mundane listings, I saw this:

"WANTED: NAKED HOUSEBOY"

I clicked the link. I didn't know what to expect, but I was damn curious. I was sitting up now, leaning into the laptop to get closer to the text. It read:

"SWBBW, 48, seeks full-time naked houseboy, 25-35. Tasks to include daily household chores as well as limited personal assistant-type functions. Perks include free room & board, plus generous monthly stipend. To be clear, you will be expected to be nude 24/7, even when not "working." Absolutely NO SEX!! If interested, please contact..."

There was no photograph, which I guess was to be expected. But there was a phone number. I read the ad a second time. And then a third. I was pulling fast and furious on my dick now, panting as I imagined the possibilities.

Surely this was too good to be true. She seemed very adamant about the 'no sex' thing. Maybe she was just a nudist who wanted some nudist help around the house? No, that didn't seem right. I was starting to imagine myself as a little toy for some cougar. It could be hot, I thought, to be objectified like that. So what if I didn't get to actually fuck her? Fucking wasn't really what I was after. As long as I could get a jerk in before lights-out, I'd be fine with it.

I desperately wanted to call this woman, even though I knew the reality of it could never live up to my imagination. But it was now after 1am. The phone call would have to wait until the next day.

"Alright," I thought. "Let my fantasy come crashing down tomorrow. Tonight, I'm running with it." And I already knew just how I would 'run with it.' So, smiling in the glow of the computer monitor, one hand on my cock, I pulled up my favorite bbw site. Then I started my search. I wanted a middle-aged woman, with the biggest, fattest, lowest hanging natural tits I could find. And when I found her, I just let the video play, as I leaned back and imagined that this would be my boss.

In the video, this big voluptuous woman sat down naked on a chair. Then she leaned in to the camera. As she did so, her massive tits came to rest on her thighs. I could almost believe she was staring at me, watching her naked houseboy jerk off right in front of her. But I was lost in her endless cleavage. All I wanted to do was tell her how much I loved her giant saggy tits, how I loved watching them sway past her belly-button, how they were the only thing in the world I wanted to jerk to, and how that really meant something coming from me, because I jerk like a -

I exploded. I came so hard that I had cum dripping down my left shoulder and collarbone. But I didn't let go of my dick, even as I could feel it losing its hardness. I didn't clean myself off or close down the porn either. In fact, the video still had something like 20 minutes left to it. In my post-wank euphoria, I decided that this was how I wanted to fall asleep: hand on my dick, covered in my own cum, and watched over by my fantasy bbw boss.

But first, with my free hand, I punched the real bbw boss' phone number into my cell, so that it would be ready to go, first thing in the morning. Then I turned my head to face the monitor once more. And as I drifted off to sleep under the watchful eyes of my fantasy bbw boss, I had one thought in my mind: god, I fucking love jerking off...