Naked Houseboy & his BBW Boss Ch. 33

"Oh, Allie, I can't tell you much I appreciate that!" Indeed, I felt a rush of warmth through my whole body at hearing her words. "But it's not about being embarrassed. It's about wanting to be a good houseboy for this party. About wanting to reflect well on Carrie, so you can see that, whatever else, she did actually hire someone who's good at this job. And if I wasn't caged up right now, I'd be distracted by my overwhelming desire to masturbate. You guys, and my job, wouldn't have my full attention. And that's not how I wanted you guys to meet me."

"Well thank you, Jack," smiled Vicky. And for perhaps the first time that night, it wasn't a wicked or ironic smile, but one of genuine approval. "Both for your answer and for your level of commitment." She paused for a moment, considering her next words. "Look, I always have this problem where, whenever I try to say something honestly, it always comes out sounding sarcastic. But believe me when I say, I think Carrie really hit a home run with you."

"Thanks, Vix." I felt myself blushing at her uncharacteristic display of honesty.

"Actually, I have a question," said Samantha. After letting the others do most of the talking, it was her first question of the evening. "You said that Carrie made it clear that she'd never sleep with whatever houseboy she hired. And you also said that 'one of the reasons' you guys aren't sleeping together is because you'd prefer to masturbate rather than have sex. I dunno, maybe it's just me, but I kinda felt like something was left unsaid there. I mean, are there other reasons besides that that you guys aren't...you know what I mean?"

There was, of course, another reason; a deal-breaking reason. Had Sam picked up on it going back to our first encounter in the hallway, or was this a more innocent question? Whatever the case, I was excited that she'd asked. To this point, I'd declared myself openly for who I really was, explained my passion for masturbation. And it had felt so good to be able to do that and to be accepted by these, my new friends. But until this moment, part of the puzzle was still missing. A piece of me was still hidden. And it was about to come out. I couldn't wait.

"Well," I said slowly, "that's really more a question for Carrie."

All eyes turned to the woman standing beside me, my boss and best friend.

"Yes, Sam," she replied. "There is one other reason that Jack and I aren't fucking, and honestly, never will. The simple fact is, Jack's penis is too small for me."

I watched as all their eyes went wide. Clearly, none of them had expected this answer; not even Sam, judging from the look of shock and even embarrassment on her face.

"Daaaamn, girl," whispered Kara.

"Oh, shit," hissed Vicky.

"Yet you hired him anyway," commented Allison.

"Of course I did," said Carrie. "Vicky already noted how he's a top notch houseboy."

"The houseboy part I get," answered Allison. "It's the naked part that surprises me. I mean, if size is so important to you, why would you hire someone who is 'too small for you?' To use your words."

"It's a good question, Ally. And to be honest with you, when I first settled on the idea of actually hiring a naked houseboy, I wasn't sure what I wanted. I mean, sure, part of me was like, 'Well, if I'm gonna have a naked man around the house, I hope he's fucking hung.' Like, obviously, it would be a lot of fun to have a huge cock around the house to look at every day. Especially knowing that the huge cock in question would be working for me, I'd be the boss of it. I mean, who wouldn't want that?

"But on the other hand, I also knew that I was quite adamant in not wanting to sleep with whoever I hired. For one, it would just complicate things and probably wind up ruining the whole experiment in the end. For another, I was - and am - in a place where I need to be totally independent of men. And I couldn't have that independence if I was fucking my houseboy. So while it would have been fun to have found a houseboy with a big dick, it would have created a level of tension and temptation that I just didn't want to deal with. So I was conflicted."

"Alright, I'm with you so far," nodded Allison. "But then, what was your reaction when Jack came in for the interview and you saw him naked for the first time? Were you disappointed?"

"You know, it's funny," smiled Carrie. "I was worried that I would be. I mean, going into the interview, I kept thinking, 'What if this guy has a small dick? Am I gonna be disappointed?' But then, when I asked him to undress and I saw him naked for the first time..." She trailed off, remembering the moment.

"Yes?" prodded Vicky, impatiently.

"Well, I took one look at his penis and I was like, 'Yeah, no, too small.' But I wasn't disappointed, like, at all. In fact, I was actually relieved. Because I knew that I'd never have to worry about the temptation of wanting to fuck my houseboy. If I wound up hiring this guy, I mean. Like, the world doesn't exist where I could ever get turned on by such a tiny penis, let alone actually agree to allow it inside me. And that was just such a relief."

"I mean...'tiny' feels a bit extreme..." said Sam in a barely audible voice.

"No, you're right, Sam," agreed Carrie. "And it's not, like, objectively tiny. Just, tiny by my standards. I mean, objectively, it's not even what you'd call 'small.' It's average. But anything under eight inches, I'm not even paying attention. And that's like the barely acceptable minimum.

"Anyway, you asked if there was another reason we're not fucking. And the answer is yes, and it's 100% about the size of his penis, and for me, it's an absolute dealbreaker."

During Carrie's discourse regarding my inadequacy, they had all been speaking about me as if I wasn't even there. Only now did they seem to see me again.

"Alright, I have a question for Jack though," said Kara, turning her attention to me. "Doesn't it bother you that Carrie is talking about the size of your penis like this, telling us all this? While you're standing right there? Naked, no less?"

"Oh my god, not at all! I mean, this is a conversation we've had ourselves, so none of this is news to me. Beyond that, the size of my penis actually plays an important part in our relationship. So in that sense, I'm happy to have you guys know about it. Like I said, I want you guys to know me, with nothing to hide."

"Actually, I suppose it works out really well for you," observed Samantha with an incredibly cute smile. "I mean, you each have your own unassailable reasons for not wanting to sleep with each other. Everybody wins."

"Yes! Exactly!" I could barely contain my excitement. Sam not only accepted me, not only considered me her friend already, but she actually seemed to understand me. For a brief moment, our eyes locked until she took a sip of her drink.

"Next question," interjected Allison.

"Keep 'em coming," I smiled.

"Jack," she proceeded in her analytical way, "you said that the size of your penis plays an important role in your relationship with Carrie. I'd love to hear more about that."

"Yeah, me too, actually," added Kara, who by now had grown quite comfortable with the topic.

"I'll second that," agreed Vicky.

"So one thing you all need to understand is, in the time since we've been living together, Carrie has become my best friend. Truly. And that means I only want her to be happy, I want her to have everything in life that she desires and deserves. But obviously, there are some things...well, one thing in particular...that I can't give her.

"Now, she would never ever use the word, right? But I know there must be days when she looks at me and just...I mean she has to feel some disappointment sometimes, right? Not in the sense of having hired the wrong guy or anything like that. But just once in a while to think, 'Oh but wouldn't it be nice if the naked man in my house had a huge dick for me to look at?' It's the one thing I can't give her.

"So it's become a motivating factor for me. Like, despite all the practical reasons that my being too small for her has worked to our advantage, at the end of the day, she's stuck looking at my tiny dick. And that just makes me want to work harder for her, do a better job for her, be a better friend to her.

"And to be clear, that comes entirely from me. Never once has she ever made me feel like I owe her more because I'm...well, less. It's just how I feel. So that's what I mean when I say the size of my penis plays an important role in our relationship. It's an inescapable fact of our existence together. And it drives me."

"But Jack." Kara paused as she tried to formulate her question. "Isn't that exhausting or frustrating or...I dunno what?"

"What do you mean?"

"Well, the way you talk about it, it sounds like...and maybe I'm just not understanding you correctly, but...it sounds like you feel like you constantly have to make up for the size of your penis. That doesn't make you feel bad or inadequate or resentful?"

"First, can I just say I love this question so much?"

"Wait, really? Why?" asked Kara.

"Look, going into tonight, I was just hoping I'd get a chance to open up about my love of masturbation and still be accepted. But the questions you all are asking me, we're going so far beyond that. You're giving me a chance to open up my whole self and I can't tell you how good it feels. Especially since you don't seem to be put off by any of this, this stuff I never dreamed I'd ever be able to talk about with anybody but Carrie."

"Put off?" replied Allison. "Jack, this is far and away the most interesting conversation I've been a part of in literally years.

"And certainly the most unique," added Vicky with a sly grin.

"My question, though," pressed Kara, pulling us back on track.

"So it doesn't make me feel bad in any way whatsoever," I replied. "I mean, yes, I suppose you could describe it as me constantly trying to make up for the size of my penis. But honestly, I love the way that makes me feel. I actually kinda view it as a gift, really."

"Hang on, I think I need to hear that again," interrupted Allison. "You're saying that always feeling like you need to make up for your size is a gift? That you love the way it makes you feel?"

"That's exactly right," I confirmed. "See, at first, I mostly just thought about it in practical terms. Finally I was in a place where my penis was not desired, which meant I could jerk off as much as I wanted without feeling conflicted about it. Already that's a gift. But lately, I've discovered it's so much more than that.

"So like, my whole life, I've always been a person who hated making decisions. I was always the guy who'd say, 'I'm good either way, whatever you prefer.' You know what I mean? And I was never good at taking responsibility. I wasn't good at it and on the rare occasions when I had to do it, I never enjoyed it. I'd always much rather preferred to be given a clear task and then leave me alone and let me do it the best way I know how. I can be creative, I can solve problems. I just don't want to make choices or take responsibility. If that makes any sense?" Their heads nodded affirmatively.

"Then I saw Carrie's job posting. And yeah, obviously I was excited for a job where I'd have to be naked all the time and, hopefully, be able to pursue my passion for jerking off. But more than that, it just seemed like the perfect job for my personality. All the things I hated would be taken off my plate. I'd be given clearly defined tasks and be left alone to complete them.

"And then I met Carrie. This beautiful, confident, powerful, sweet, caring woman. From the moment I met her at the interview, she just oozed authority. And even now, when she's my best friend, she's never not my boss. But I knew immediately that this was where I was supposed to be, that I'd found my place. I just didn't know why, not fully, until very recently, when we had our first conversation about my size.

"That was when I realized. The size of my penis is physical proof that I've found my place, my role. All either of us needs to do is simply look at it, and we know that the person I am in this house and in this relationship is exactly who I'm supposed to be. The guy with the small penis doesn't make decisions or take responsibility. The guy with the small penis does what he's told. Which is always how I wanted it to be for me.

"I mean, I wish I could explain to you what an incredible feeling it is. To stand naked in front of Carrie, to have her look at me and know that I'm too small for her. This feeling of, you're the boss and I'm the houseboy and that's the only way it can be. Because I have a small penis. It's the most free I've ever felt in my life.

"So yeah, as you said, I'm always trying to make up for my size. But it's my size that has me in this role and place that I love, where I feel like I fit and was always meant to be. That's why I never feel frustrated, trying to make up for it. If anything, I feel thankful. Like, 'Thank you for hiring me with my tiny penis and giving me a chance every day to show you what a good houseboy I can be, despite being too small for you.' It really is a gift."

"Can I pose a hypothetical?" asked Samantha. "I mean, I'm just trying to understand."

"Please."

"So originally, Carrie's your boss, she pays you in the way that you both agreed, and as her employee, you follow her instructions. I mean, that's how this all started. But suppose now that Carrie cut off your porn budget. Suppose further that she locked you in that cage so that you could no longer freely masturbate. You would still feel obligated to obey her every word owing to the size of your penis?"

"Absolutely."

"And suppose you were out in public together," she continued. "Obviously you're both dressed in such a situation. Nobody else can see, or has ever seen you naked. Still, you would feel obligated obey her every word, because the both of you would know that your penis is too small for her?"

"Yes! That's exactly how it would be!" The other girls asked questions because they wanted to know the answers. Sam, however, asked questions when she already knew the answers. I just loved the way she seemed to get me. Our eyes locked again, longer this time. There was an undeniable chemistry between us, which honestly confused the hell out of me. The chemistry was there, but I had not the least desire to fuck her. I wasn't even sure I wanted to jerk off to her. I began to think that maybe what I wanted was just for her to sit beside me while I jerked off to Kara's bra-busting cleavage -

"Any other questions?" My thoughts were interrupted by Carrie's last call, as it were. When nobody answered, she continued. "Then this concludes the Q&A portion of the evening. And now, the fun starts. You see, I've planned a little game for us..."