Naked Houseboy & his BBW Boss Ch. 04

*Part 4 of an ongoing series...

"Why don't I start by telling you a little about the job, what it entails, what I expect, that sort of thing?" Her voice had taken on an air of professionalism. This was a job interview after all.

"Please," I agreed. Indeed, I was quite curious to know what she had in mind.

"Your primary responsibilities would be general housekeeping. Cooking, cleaning, laundry, the odd bit of yard work. How is your cooking, by the way?" she added, almost as an afterthought.

"I mean, I'm no professional chef. But I can handle myself In the kitchen. And I quite like to cook, actually."

"Very good, very good," she smiled. "It'll be nice to come home to a home cooked meal."

"And I'd love the opportunity to cook for someone besides just myself for a change." I paused. "Sorry, did you say yard work?"

"Here and there, yes. Nothing major, why?"

"Well, I mean...do you mean you want me to work outside..."

"Naked?!" we said unison.

"Of course not," she laughed. "What would the neighbors think? No, of course, anytime you leave the house, you shall have to dress yourself. Which reminds me. Running errands. I'll need you to go do the shopping, go to the post office, that sort of thing. But you have your own car, so I assume that's no problem?"

"None at all."

"Good, good." She smiled. "Well, look, that's really it, as far as responsibilities go. And that should be more than enough to keep you busy, day to day."

"Yeah, I mean, that's all fine with me. Nothing I can't handle."

"I thought so." Still the smile. "So now let me just tell you a little bit about my expectations. I don't want to give you fixed hours, per se. What I'd rather do, is give you a list of tasks and assignments with deadlines. And you can work out whatever schedule for yourself as seems best to you. I don't much care what time you go to bed or what time you wake up, as long as your work is done on time and to the level of quality that I expect. How does that sound?"

"Sounds great, honestly. I can definitely work that way!" I know I probably sounded a bit over-eager. But better over-eager than disinterested.

"Oh, there is one exception to that, however."

"Go on..."

"I expect dinner to be on the table at 7pm sharp, unless we discuss otherwise."

"That's it?" I asked. I was expecting something more, I dunno, onerous?

"That's it," she confirmed.

"Oh, well," I shrugged, "I mean, yeah, of course. No problem."

"Excellent!" she tilted her head to one side in a very adorable expression of contentment.

"Is that everything, then?" It sounded almost too easy.

"Well, not quite. So, I've told you about the responsibilities and my expectations. Now I'd like to tell you about my hopes."

"Your...hopes?" Responsibilities. Expectations. These were words I expected to hear in a job interview. But hope?

"Yes, hope. Look, if I hire you, I'm going to be your employer and you're going to be my employee. Naturally, that will be the most powerful dynamic affecting our relationship. But..." she trailed off. I could see in her face that she was searching for the best way to express herself.

"I mean," she started again. "We're going to be living together, you and I. The only two people in this house. And don't get me wrong, I fully respect your privacy, your need to have time to yourself. Lord knows I need time to myself too. But, well, what I'm trying to say is..."

Those shy eyes again. She was looking at her hands, folded upon the glass tabletop.

"Just, I hope that we'll spend some time together. Get to know each other. Maybe even become friends. You know, eat together. Maybe watch TV together. Or sometimes just have a glass of wine. What I mean is..." She looked up at me now, with not a little fear in her eyes. "I just don't want us to be strangers to each other in this house. Does that make sense?" Her hands were folded so tightly, her knuckles were white.

"It makes perfect sense!" I gushed. "Honestly, I couldn't have said it better myself. I mean, do you think I wan to move into a strange house, be naked all the time, and feel like a stranger here? I honestly don't care if you see me naked all day, every day. But I would hate it if you looked at me like, 'Ugh, there goes The Help. Let me go to a different room so I don't have to deal with him.' No, everything you said makes perfect sense."

As I said this, I could see her relax. Her hands unwound themselves, pushing her hair back behind her ears. The tension went out of her shoulders. The shyness left her eyes.

"Well then," she sighed pleasantly. "Do you have any questions for me?"

"Yes, I do. Two actually."

"Shoot."

"OK. First, why do you...I mean, how did..." I scratched my ear absentmindedly. The question was harder to formulate than I'd anticipated. "I mean, how come you want..."

"A naked houseboy?" she finished for me.

"Well, yes, actually. Why do you want a naked houseboy?" Emphasis on the 'naked.'

"Look, I'll be honest with you. I'm 48 years old. I've spent my entire career as a woman working her way up the corporate ladder. And not for nothing, I've made it pretty far." The size of the house, the quality of the furnishings testified to that. "And at every step of the way, it's been bullshit. Two-faced people. Self-servers. Or people who have their head so far up their own ass, they've lost all track of what's important. It's all about getting ahead, proving your better than the next guy. At best, people lose track of the human element. Usually, it's worse."

She sighed heavily. Cleary this woman had built a successful career. But it had taken a toll on her.

"And so I guess I just figured," she continued, "that if the person I hired were to be naked all the time, they'd have nowhere to hide. They couldn't be fake. They couldn't be two-faced or full of shit. There's honesty in nakedness. Or that was my idea, anyway. I dunno, I guess that sounds stupid."

"Not at all!" I protested. It made perfect sense to me. After all, I was here because I was tired of pretending to be something I wasn't. And she must have been on to something, because I didn't even notice that -

"Sure. But you had a second question," she broke my train of thought.

"Huh? Oh, yeah." I paused to order my thoughts. "So I know I won't have a fixed schedule, as you said. But, I mean, there will be a distinction between when I'm working and when I'm not, right? I mean, there will be clear times when I'll be able to say that I'm 'off the clock,' as it were?"

"Oh yes, of course!" She almost laughed. "I'm not going to have you on-call 24/7, if that's what you mean."

"OK, and so my 'off' time will be mine to do with as I please?"

"Yes?" She was trying to figure out what I was getting at. Then she started to laugh. "Ah! OK, I think I know where you're going with this."

"You do?"

"I think so," she shook her head, smiling sweetly. "Look, just because we won't be having sex doesn't mean you have to live like a monk. You're free to date. You can even bring girls home if you want, as long as your discreet about it."

"Oh, I...I won't...I won't be doing that," I stammered.

"Oh my god, I'm so sorry!" Her face turned bright red. "I didn't mean to assume. Of course you can bring boys home!" Now I stared to laugh.

"No, no, you don't understand."

"Clearly," she closed her eyes. "Why don't you tell me what you mean, before I say anything else stupid."

"Oh, Carrie, you haven't said anything stupid at all," I said softly. "You...just don't know me. Yet."

"Tell me, then."

"OK." I took a deep breath. "The thing is, I've never told this to anybody before. And I'm afraid that when I do tell you, I'm gonna sink my chances of landing this job. But as you said, there's honesty in nakedness..."

"I'm listening." Her words were a whisper.

"The thing is," I closed my eyes, afraid to look at her.

"It's OK, Jack."

"The thing is...I love to masturbate. A lot. Like, a lot a lot."

"That's it?"

"That's it," I said, my eyes still closed.

"So let me get this straight. You're applying for a job where, if you get it, you will come and live in my house. And your only question is if you can jerk yourself off, in my house, when you're not working? Do I have that right?"

"Fuck," I winced. "I knew this would cost me the job."

"Are you kidding?!" I felt two inches tall. "You think you're the only man who likes to masturbate? You think I would hire a younger man to be a naked houseboy and...and what? Expect that he'd never jerk off?

"Wait, what?" This had taken a turn. Finally, I looked at her. As her eyes met mine, she perceived how nervous I was, how afraid of rejection I'd been. And she flashed me that kind smile. It filled me with warmth, made me feel safe somehow.

"I'm sorry," she whispered. "I didn't mean to react like that. Just, the way you were talking, I was expecting something terrible. No, of course you can do whatever you want with your free time. And if you want to spend your free time masturbating, I would never think of objecting. As long as it doesn't interfere with your work."

"It would never," I swore solemnly.

"I wouldn't have thought so. But, can I ask you something?"

"Please."

"Well, I don't mean to be insensitive, but what's the big deal? I mean, all guys like to jerk off, don't they?"

"Oh, sure," I agreed. "But that's not what I said."

"What did you say, then?"

"I said, I 'love' to masturbate. There's a difference."

"There is?" She seemed genuinely curious.

"Sure there is." I had forgotten my previous anxiety and was speaking comfortably now, leaning back in my chair. "Look, some people love to play tennis, or knit, or play video games, or do yoga, or whatever. It's there favorite thing to do and they do it every chance they get. And they practice it, they get better at it."

"And masturbation is that for you?" She was smiling, in the way that one smiles when one learns something new which they never would have previously imagined.

"Yeah. It's the thing I do every chance I get. The thing I think about doing when I'm not doing it. You could even say that I 'practice,' in a way.

"How interesting." Her chin was in her palms, elbows on the table as she leaned in closer to hear me expound on my favorite subject. Only, I'd said all I'd wanted to say on the subject. At least for now.

"Anyway," I concluded. "That's not something I'd be able to hide if I got the job, even if I wanted to. But also, I wouldn't want to. I've been hiding it forever. Which is why I needed to be up front about it now. Even if it costs me the job. And honestly, even if it does cost me the job, I'm still glad I told you. At least I got to say it once."

For a long moment, there was no answer. She just stared at me with those soft brown eyes, that warm smile, her chin in her palms, her elbows on the table. In that silence, I noticed that it wasn't just her elbows on the table. Her leaning forward like that also brought her massive, bra-supported, sweater-covered breasts onto the table. Had she been wearing something more revealing, no doubt cleavage of epic proportions would have been pushed up and together towards her collarbone, rising like the Himalayas.

I felt my penis twitch. I took a slow, deep breath, trying to control my body. Micky Mantle hit 536 home runs, I told myself, willing the moment to pass. But she just kept looking at me, searching my face. And the way she was looking at me, all I could think of was the way that woman in the video looked at me, leaning forward, her fat, saggy tits resting on her thighs. And now this woman, looking at me, her mountainous breasts on the glass table top.

Oh god, the glass table top! If she so much as glanced downward, she'd see me through the table, see the growing erection I was struggling to control. But she didn't look down. She just kept looking at me. At last she spoke.

"You haven't, you know."

"Huh? I haven't what?" Where had the conversation left off?

"You haven't cost yourself the job."

"I haven't?" My head was spinning.

"No, in fact, you've got the job. That is, if you want it." She leaned back in her chair. And as she did so, an epic battle played out between gravity and the strength of her bra. Her enormous breasts rose off the table slightly slower than the rest of her. But rise they did. The bra had won.

But another battle was lost. I could no longer control my erection.

"Yes, of course I want it! Thank you so much!"

"No, it's me who should be thanking you," she smiled.

"I don't follow."

"Look, I'm sure you'll do a great job, houseboy-wise. But the most important thing for me is the comfort level. I see how comfortable you are being naked around me. And even though it wasn't easy for you to tell me what you just did, nevertheless you did tell me. And that kind of honesty, that's what I'm looking for. You didn't cost yourself the job, telling me about your love of masturbation. If anything, that's what sealed it."

"Go figure," I laughed.

"I'm curious though," she added hesitantly.

"About?"

"How much is 'a lot a lot'?"

"I'm sorry?"

"You said you love to masturbate 'a lot. Like, a lot a lot.'" She parroted my earlier words with air quotes. "I'm curious, how much is 'a lot a lot'?"

"Oh!" I laughed. And straightening myself proudly in my chair, I announced "I would say usually not less than six or seven a day."

"Six or seven," her eyes grew wide, "times...every day?"

"Huh? Oh, no." I shook my head. "Not six or seven 'times.' Six or seven hours!" I couldn't believe how easily I said that. Just a few minutes ago, I was so nervous just to broach the subject. Now I was declaring proudly. And I could feel my hard cock between my legs, adding its vote of confidence.

"Stop it now. Really?" Her voice was all curiosity and fascination. I nodded confidently. "Forgive me, but...doesn't your dick get sore?"

"Well, like I said, I, uh, practice. So no, not really."

"I suppose not," she said with a giggle. Only it wasn't a giggle. It was growing into something more pronounced. Yes, she was really laughing now, although she was doing her best to stifle it, covering her mouth with both hands.

"Is that funny?" I asked with faux-wounded pride. Oh my god, the way her tits were shaking as she laughed. I folded my hands together just to keep from touching myself then and there.

"No, it's not that. it's just..." And she started laughing again. And the way her breasts bounced as she did so, she could laugh at me all day long. "Sorry, sorry," she said gaining control of herself. "It's just...'Forgive me, but 'doesn't your dick get sore?' is not a question I ever thought I'd ask at a job interview."

I had to laugh too. I mean, really.

"So look," she said, turning professional again. "We still need to work out your compensation. But can we agree in principal? Do we have a deal?" At this, she stood up and extended her arm across the table, offering a handshake.

And in that moment, I suddenly remember by hard-on. I blushed, ever so slightly. "Maybe now's not the best time for me to stand up," I said softly.

"Huh?" It took her a moment, but then she looked down, through the glass table top. There was no hiding my erection. I looked up at her. But she was still looking through the table. She regarded my erect penis like she might have regarded a hummingbird fluttering outside the window. Surprising, perhaps even pleasant to look at for a moment. But ultimately nothing particularly novel or interesting.

Then she looked up at me. No different than if I had been wearing a suit and tie. There was no indication that she had just gotten a good, long look at the best hard-on I had to offer.

"Look," she said softly. "Did you really think you'd come live in this house, be naked 24/7, and I'd never see you with an erection? You'll have to get over that sort of prudishness if this is going to work." Her words were firm, but kind.

"I guess you're right," I said, rising to my feet. "I guess that's something I'll have to get used to."

"I usually am," she grinned. "You should get used to that as well."

"Indeed." I stretched my arm out to her and we shook on it. And she kept eye contact the whole time, never once sneaking a look at my naked body, never mind my hard-on. I guess she was right. She'd be seeing plenty of me in the weeks and months to come.

After the handshake, she fell back down into her chair, her tits bouncing slightly as she did so. I tried not to stare. For just a moment, I staid on my feet. I realized that I actually enjoyed standing naked in front of her, my dick at attention. I let it linger just a moment longer before finally sitting back down myself.

"So," she began, "let's talk compensation..."