Naked Houseboy & his BBW Boss Ch. 27

*Part 27 of an ongoing story...

I closed my eyes, exhausted after yet another multi-hour jerk session. I could have fallen asleep then. But I opened my eyes again when I felt Carries fingers around my spent and fading cock. I smiled, loving the fact that she no longer even made a pretense of asking my permission. Whenever I'd finish jerking off, my tired and limp dick was hers to play with. It was becoming our new normal. And I loved our new normal. I closed my eyes again and we lay their for a few minutes in silence as she fondled me absent-mindedly.

"Jack?" she said at last.

"Hmm?"

"I mentioned something earlier, and I feel like you wanted to ask me a question about it, but I kinda shut you down."

"Hmm?" I was still in a state of post-wank euphoria and was not yet thinking clearly.

"You can ask me now," she paused. "If you want."

I turned to look at her. It must have been clear from the look on my face that I didn't know what she was aiming at. She blushed.

"I said..." she trailed off. In a way I can only describe as nervous, she started tugging on my dick, as if she might somehow get me to ejaculate the words she was looking for.

"I said," she tried again, letting go of my penis and sliding her hand up towards my breast, running her fingers through my chest hair. I could see that she was blushing. "I said," she tried for the third time, "that the internet is full of big hard cocks and I know where to look if I really want to see one." She blinked, furtively. "And I feel like you wanted to ask me about that."

"Oh, that!" I said, my eyes widening.

"Yes...that," she whispered, averting her gaze. But in a sign that the most difficult part was now out of the way, she slid her hand back down and once more took up my penis between her thumb and forefinger.

"Right, well," I said, clearing my throat. And I could feel myself blushing. After all, never once had we talked about what kind of porn she looked at. Or even if she looked at porn at all. This was new ground. "Well," I said again. "I guess the obvious question is; Do you, actually? I mean, do you go online and look at big hard cocks?"

With flushed cheeks, she nodded.

"Oh my god, Carrie, this is amazing!" I exclaimed without thinking.

"It is?" she batted her eyelashes.

"Of course it is!" I could hardly contain my excitement.

"Why?" she asked softly.

"Because! This is the first time you're telling me about what kind of porn you watch! Or even that you watch porn at all!"

"Well, I'm not sure I'd call it porn, exactly." There was a timidity in her voice.

"But you just said you look at big hard cocks on the internet. How is that not porn?"

"Well, for me, porn is people doing sexual stuff. But I'm not watching videos of people fucking or masturbating. I'm literally just looking at dick pics."

"An interesting distinction," I replied thoughtfully. "Sure, let's go with that. But OK," I went on. "Do you have any favorites?"

"Favorites?" she repeated.

"Yeah, favorites. Like, guys who you love looking at, that are sort of your go-to's. Know what I mean?"

"Oh" she smiled. "I think so. Like, you have your favorite cam models and porn stars and videos that you always go back to. Like, the stuff that keeps showing up in your browser history month after month?"

"Exactly," I grinned.

"Well, yes and no." She didn't elaborate.

"What do you mean?"

"So, I don't really watch a lot of videos," she explained. "It's more like, I search for pictures. And when I find a picture I like, I add it to my slideshow."

"Whoa, wait a second," I cut in. "You have a slideshow?!"

She nodded, blushing. "I mean, it's nothing crazy."

"What does that mean?"

"Come on, Jack. I've seen your porn library. It's huge. My slideshow is nothing like that. It's just some pictures I've collected over the years that I really like."

"Fair enough." I paused. "Car?"

"Hmm?"

"I wanna see it."

"Come on, Jack, why would you want to see that?"

"Why do you like to look at my browsing history?" I said, answering her question with a question.

"Ah, OK," she nodded slowly.

"No," I insisted. "That wasn't rhetorical. Tell me. Why do you like to look at my browsing history?"

"Seriously?"

"Seriously."

"Well, because it's a window into your most intimate and private self. It's a way for me to know you better, to be closer to you."

"And that's exactly why I want to see your slide show," I said firmly.

"But Jack," she resisted. "You realize it's literally just pictures of cocks."

"So? Like I've never seen a cock before?" I took a breath. "Look, C, I get that it's a very personal thing for you. If you're not comfortable sharing it, just say so. I totally get it."

"No, no," she blushed. "It's not that. I would actually really enjoy sharing it with you. It's just, today is your jerkathon. Maybe it's not the best day to look at dick."

"Hey," I grinned. "I'm between wanks right now. I can't think of a better time."

"You asked for it," she answered with a shrug. Then she rolled over to the keyboard on her nightstand and cued up the slideshow. The first picture came up, and at the bottom of the screen were the numbers "1/3457." Almost 3.500 pictures of nothing but cock. And this was her definition of "nothing crazy"?

Clicking 'play,' she rolled back over to cuddle up against me, her fingers once more finding their way to my resting member. For quite a while, we lay there in silence, watching the pictures flash by. Just as she'd said, all the photos were solo shots. Some were closeups, others were full length. Very rarely, one of the pictures would include a face. But mostly, it was just pictures of all kinds of dicks from all kinds of angles.

After two-hundred or so pics, I started to pick up on some patterns. Although the dicks in her slideshow came in every color, they shared some things in common. Almost all of them were circumcised. The guys were either completely shaven or very closely trimmed. But one thing stood out more than all the rest. Literally. They were all big. Very very big. Not just long, but thick too. I had just discovered that Carrie had a thing for looking at massive cock.

"Wow," I whispered after one particularly enormous specimen flashed across the screen.

"I know, right?" she cooed, giving own my still dormant dick a squeeze.

"You really like 'em huge, don't you?" I asked.

"In that way, we're kinda the same," she laughed.

"Wait, what?"

"Well, I was gonna make a joke about you loving giant strap-ons," she giggled. "But no, seriously. You're the same way with boobs. I mean, you know that, right?"

"Explain, please." I glanced at her momentarily, but the truth was, I couldn't look away from the parade of giant dicks on the screen.

"Well, most guys like big boobs," she stated matter-of-factly. "But what you love are the truly ginormous ones. I'm talking J-cup, K-cup. For you, if a girl rolls up with Double-D's, it's almost like you're disappointed!"

I was about to voice my agreement. She did have a strong point after all. But something about her last sentence caught me off guard. I mean, by any reasonable standard, DD's qualify as big tits. And yet, she had used the word 'disappointed' to describe my reaction to breasts of that size. She wasn't wrong about that either.

I considered my own dick as I watched still more enormous cocks flash across the screen. Six inches. Solid average. Despite the fact that I enjoyed my share of small penis humiliation, I never actually considered myself as being small. I never felt bad about the size of my dick. But Double-D's are well above average, and they're a 'disappointment' to me. Well, forget about 'well above' average. I'm just plain average. So if Carrie looked at cock the way I look at tits, what must she think of me? The only thing worse than learning something unpleasant was not knowing at all. I had no choice but to ask.

"Carrie?" I asked, my voice cracking.

"Hmm?" She barely seemed to hear me, so engrossed was she in her slideshow.

"Now that I know what kind of dicks you like to look at, I have to ask...are you...disappointed in my penis?"

"Jack!" she shot back. "How could you even ask such a thing!?"

"Come on, C, it's OK," I answered, feigning confidence. "I mean, I'd get it. You just got done watching me jerk my limp dick for ninety minutes. And even when I get hard, I'm not half as big as these guys. And now that I know this is what you like to look at...well, I'm just saying, I'd totally understand if you you were disappointed with my penis."

"Wait a second," she said, eyeing me suspiciously. "Are we doing an sph thing here? I mean, it's cool if we are. I just need to know which way I'm supposed to answer you."

"No, Carrie," I answered, using her full name. "We're not doing an sph thing. I'm being serious."

"Then let me answer you seriously." There was a change in the tone of her voice. This was confident, boss Carrie now. "Jack, in all honestly, in no way am I disappointed with your penis."

"Because I would understand if - "

"Jack," she cut me off. "Let me ask you a hypothetical question. If I was a C-cup, would you be 'disappointed' with my boobs?"

"It's not the same thing," I protested. "I walk around naked all day, you don't."

"Oh, give me a break, Jack."

"What?"

"Come on," she said sternly. "I see the way you look at me. The size of my chest is in no way lost on you. So I'm asking you hypothetically, if I was a C-cup, would you be disappointed?"

"Hypothetically," I looked at her. "It wouldn't make an ounce of difference to me. Your body is a part of you and you'll always be beautiful to me because I lo-". I stopped myself short.

"It's OK, Jack," she smiled. "You don't have to say it."

"And anyway," I added, hurrying right along, "you're not my porn."

"Which brings me to my next point," returned Carrie. "In this hypothetical where I'm a C-cup, would that somehow change your porn viewing habits? Would you all of a sudden start jerking off to girls with smaller boobs?"

"Of course not!" Perish the thought. "One thing has absolutely nothing to do with the other."

"Exactly!" Her smile was one of satisfaction at the fact that I'd made her own point for her. "It's the same thing for me. You would not be disappointed if I had smaller boobs, but you'd still masturbate to women with massive tits. Well I'm not the least bit disappointed in your penis, Jack, but that doesn't mean I don't enjoy..." She blushed, unable to finish the sentence.

"So you do?" I nudged her.

"Enjoy looking at large cocks? Of course." Her words were matter of fact.

"I mean, you do...you do enjoy masturbating to them?"

"Jack..." Her face was turning a brighter shade of red. We had never once even hinted at her own masturbation, let alone discussed it. In point of fact, I wasn't even sure if she did.

"Hey, you started the sentence, I'm just trying to finish it."

"Well of course, Jack," she said stiffly, even a little defensively. "Doesn't everybody? I mean, I'm not a prude."

"And this is what you like to watch, when you do?" I was trying hard not to grin.

"Clearly." She was still blushing just a little, but I sensed she was growing more comfortable with the topic.

"I have questions," I said casually.

"I'll bet you do," she answered just as casually. "In fact, I can see the subject has piqued your interest." My dick was starting to stiffen between her fingers. "I'd better give this back to you." Releasing me, she slid her hand up to my chest, while I took hold of myself with my own hand and slowly started massaging my growing erection.

"When do you do it?" I'd always wondered about this. There just didn't seem to be very much time that she was home and alone. I mean, I was always there, in the house. I'd always wondered, if she did it at all, how did she do it without me ever getting wise to it? Well, now I knew she did. But I still didn't know how.

"You really don't know?" she countered.

"I honestly have no clue," I admitted.

"Clueless Jack," she shook her head with a smile. "Until today, you didn't even know I don't where underwear around the house. No wonder you have no idea when I masturbate."

Just hearing the words "I masturbate" from Carrie's lips sent me into a state of complete hardness. I started to stroke, slowly.

"Let me ask you a question," she continued. "You know how some nights, when I come home from work, I tell you that I've had a long day and I just don't have the energy to be social?" So I just go up to my room after dinner?"

"Sure," I nodded. "You like to read or watch TV. That's what you've always told me, at least."

"Well...I do watch TV...in a way..."

"Oh my god, that's your you-time!" It seemed so obvious now, as she was explaining it. But I'd never even considered the possibility before. "But wait. You do it right in the middle of the afternoon?"

"Sure," she smiled.

"When I'm home and awake?" I added, still trying to get my mind around it. How had I never noticed, or even suspected?

"Oh come on, Jack, don't be so surprised. Look, when I tell you I don't have the energy to be social and I go to my room, what's the first thing you do?"

"Well, I go to my room and watch porn, obviously." And it was obvious.

"Exactly. And I know I can count on that," she grinned. "In other words, I know I can count on at least an hour of you being distracted, of you being in your room, of having your attention focused entirely on your own masturbation. So I know there's no fear of you coming to look for me or knocking on my door. I couldn't ask for a better guarantee."

"Incredible," I said softly. And then I remembered something she'd said. "Wait, did you say at least an hour?"

"I did," she laughed. "But that was just a way of saying I know I have plenty of time. I don't normally need more than twenty or thirty minutes, if that."

"I see." It was such a good feeling, jerking off while Carrie shared with me for the very first time even the smallest of tidbits about her own masturbation habits. "And you always watch this slideshow?"

"Pretty much," she nodded. "I mean, sometimes I'll do some internet searches and try to find new pics to add. But yeah, mostly it's just watching this."

I turned my attention once more to the screen. I had to admit, it was a well-curated collection. Not that I consider myself a connoisseur of cock, but after so many years of watching so much porn, I feel like I've developed some sense of what I think a nice penis looks like and what I think a gross one looks like. And somehow, every one that came across the screen was a 'nice one,' by my standards. Could it be that Carrie and I shared a similar taste in penile aesthetics?

"Is this weird for you?" came Carrie's words, interrupting my thoughts.

"Is what weird for me?"

"Jerking off to a slide show of huge dicks." She was grinning.

"Well, I mean, that's not how I would describe it," I said.

"Really? Cos from where I'm laying, you're right now, this very moment, looking at pictures of massive, erect penises and masturbating. How would you describe it?"

"Well, sure, you can make anything sound like anything...with words," I protested weakly. "But I would say, I'm laying in your bed, with you, talking to you for the first time about your own masturbation habits. And I'm not watching 'a' slideshow, I'm watching 'your' slideshow, learning about what you get off to. So no," I said with some finality, "it's not weird for me."

"Good," she smiled. "Then I have another question."

"Go on."

"How long do you think you're going to be?"

"I don't know," I admitted. "I haven't thought about it. Why?"

"Well...I'm afraid I may be having a bit of a pavlovian response to this slide show here..." She was blushing again.

"Ah! Say no more!"

"I mean, I don't want to rush you," she added sheepishly.

"Are you kidding? This is the first time you've ever admitted to me that you're getting in the mood to masturbate. And of course you'll want to be alone for that. I'll try to finish this as quickly as I can," I added, tightening my grip and speeding up my stroke.

"Should I put something else on for you, to help you?"

"No, this is fine," I said softly. And it was surprisingly fine. I was imagining, hoping even, that one day Carrie wouldn't need to be alone. That we could sit and masturbate together. I'd be jerking to big titties and right next to me she'd be working herself to big dicks. I knew it was this thought that was going to make me cum.

But I didn't know if I wanted to tell her. I didn't want to put more pressure on her. It was such a big step for her just to open up the little bit that she had. But if I didn't tell her, she'd probably assume that my orgasm was due to the content of her slideshow alone. Well, why should that bother me? I decided that it didn't.

I went back to picturing the two of us side by side, each at our own computers, masturbating to our own porn. Carrie would look over at my screen and see the enormous breasts I was jerking to, so much like her own. And I'd look over at her screen and see the massive cocks she was fingering herself to, so much bigger than mine. I smiled as I came, the vision was so real in my head. I didn't shoot as far this time and none of my semen landed on Carrie.

She looked at me with expectant eyes.

"I'm going, I'm going," I smiled. "I could use a nap anyway." I slid out of the bed and headed towards my room. "Just, uh, wake me up when you're done, k?"

"You got it, mister. Oh, and Jack? Close the door the door behind you." She winked with a hungry smile on her face.

As I glided towards my room, exhausted, I smiled at the thought of what was about to happen behind Carrie's door...