Naked Houseboy & his BBW Boss Ch. 38

*Chapter 38 of an ongoing story...

"Come on, Jack." Kara grabbed my hand and led me into the kitchen. Having just pointed out that both Sam and Carrie had gotten their own one-on-one time with me, she had asked if she could also talk to me in private.

"Is there something particular you wanted to talk about, Kara?" I asked when we were alone.

"I'm not really sure, to be honest. Wait, hang on. You've still got some cum on your chin." She reached her finger to my face and, after wiping away the offending drop, sucked her finger clean. "Sorry. That was distracting me."

"I must look like a mess," I blushed.

"You for sure do," she laughed. "But it suits you somehow."

Then she stopped talking. And I didn't know what to say. Heck, i still didn't even know why she'd asked to see me in the kitchen. But when I realized she wasn't going to speak, I decided to say something.

"Kara? Are we...are we good?"

"Oh, Jack, you silly person. Of course we're good. You're my little buddy!"

"Well that's a relief. But then why..."

"I'm not sure I can explain it, but I'lll try." She took a deep breath. "Jack, I feel like you and me shared more than a few very personal and deeply intimate experiences tonight. Some of them were so horribly embarrassing. Some of them were beyond exhilarating. But all of them happened in front of the whole group. And I guess I just feel like I wanted for us to have a few minutes alone, just you and me. Even if I'm not really sure what we should be saying or doing right now."

"I'm really glad you said that, actually."

"You are?"

"I am," I smiled. "I guess it's my turn to try and explain. See, I'm really happy about the way tonight went. I mean, I loved the shit out of this party and I wouldn't change a thing about it. All the intimate moments between you and me, I'm glad they happened in front of the group, if only because it allowed the girls to see who I really am.

"But Kara, you're different from the rest of them, at least in my eyes. You're the one I fantasize about. Your'e the one who is not only the hottest woman I've ever seen, but the hottest woman I could ever imagine. In my head, I've been alone with you many times. And now, I'm over the fucking moon that we get to have a few minutes together, just you and me."

"Aw, Jack," she blushed. "It feels really good to hear that. In fact...I mean, I don't know what it is about you. Like, despite what you have going on down there - or more accurately, NOT going on - you have a way of making me feel very special."

"You ARE special, Kara."

"Sweet talker," she smiled. "Can I ask you a personal question? Or maybe it's a technical one."

"Ask me literally anything."

"Okay, so like after you finish. How much time do you need before you're ready to, you know, go again?"

"There's no one answer," I explained. "It really depends on a whole bunch of factors. Sometimes I might need two hours or more. Other times, I'm ready to go again after ten minutes or so. Why?"

"Well, I guess what I'm really asking is, could you be ready to go again now?"

"What, like right now?" Was she serious?

"Yes, right now, Jack."

"Geez, Kara. I mean, maybe? Like, I could try. I'm just not sure what would happen."

"Not sure what would happen?" she repeated. "Jack, if you're talking about an erection, I don't expect - "

"Oh, there's no way I'm getting hard," I interrupted.

"Yeah, I didn't think so!" she laughed.

"I just meant I don't know if I'd be able to cum. Like, it might end the same way it did when I was 'failing' for Allie earlier."

"Would that be so bad?"

"Not exactly ideal but...wait. Kara, what's your real question here?"

"Well, it's not so much a question as an idea. I was just thinking that maybe you and me could have one more intimate experience before I have to go. This time without the others. Just Jack and Kara."

"Kara, if you're saying what I think you're saying..." My eyes lit up like a Christmas Tree.

"I'm not gonna show you my tits, Jack," she answered, pulling the plug. "Not tonight, anyway. No, what I was gonna say was, you could stare at me the way you were too polite to in front of the girls and, you know, do what you're best at. And I could stare at you while you do it. And then, however it ends, it ends. If you can finish, then I finally get to see what a limp dick looks like when it cums. And if you can't, we'll share a deeply intimate moment of personal and sexual failure on your part. But it will be a moment we share together, just you and me. And Jack, I can promise you this. If you can't cum, I won't think any less of you. Not one bit."

"That actually sounds...fucking amazing. Yes, please!" I stopped. Something was bothering me. No, not bothering. Just, something was on my mind, and I couldn't quite make sense of it. "Kara, can I ask you something first?"

"Of course, Jack."

"Before, when I went soft while I was looking at you. You seemed so wounded. Yet now, you're actually encouraging me to jerk my limp dick to you. Don't get me wrong, I'm glad that's where you're at. Just, that's quite the turnaround. What happened?"

"The short answer is, your confession cleared it all up for me. The long answer is...slightly more complicated."

"I'd love to hear the long answer, Kara."

"Would you? Because the long answer would mean me saying things to you that might sound unkind, even though I only mean them with kindness."

"That's fine! Whatever happened to bring you to this point, I'm dying to hear it."

"Alright, Jack. So, from the minute I met you, I knew I liked you. But it was weird for me. Because I really like men, you know? And normally, if I meet a man and I like him, I'm already thinking about sucking his dick. The thing is, the way you were standing there, naked except for your caged cock, you didn't really feel like a man to me. So I liked you, but I was confused.

"Fast forward to the dildo measuring contest. Finally, Carrie let you out of chastity. I thought maybe then, being free, I might get some actual 'man' energy from you. But I didn't. They way you stood in the circle with the rest of us, presenting your penis for measurement, all I could think was that you just felt like 'one of the girls.' Not in the sense that you were giving off some kind of feminine energy. You weren't. It was just that you seemed to fit so well with the group, you seemed to be really one of us. In a way that - oh, Jack, forgive the term - but in a way that a 'real man' never could.

"I feel bad about that choice of words," she continued. "But it's true, Jack. You don't feel like a 'real man' to me; only you have to know I mean that as a compliment! I'm tempted to say it's a size thing. Or that size at least has something to do with it. But the truth is, your honestly not that small. I mean, okay maybe Sam was being a little generous when she said 'average.' Check that, not 'maybe.' Definitely 'average' is generous. But you're not tiny is the point.

"And I can see you're smiling now, Jack. And that's my point, actually. It's not about how small you are in reality. It's that you enjoy being naked while clothed women make fun of your penis to your face. That's just not 'real man' vibes."

Here she paused, looking at me. More than looking, examining.

"This is turning you on, isn't it?" she asked.

"What is?"

"Me saying that your penis isn't even average. Saying you don't exude 'real man' vibes. You like hearing that."

"I, uh..." I gulped, blushing.

"It's okay, Jack," she smiled. "You don't have to say anything. I can see it. Not that your dick is any indication. But I can see it in your face. You're loving this, and it's turning you on."

"Kara, I..." She had me at a loss for words. She was putting me on the spot. The thing is, even though I could feel my cheeks burning, I was loving every second of it. There was something about being called out by Kara that was incredibly exciting. I mean, it was excruciatingly embarrassing. And yet, I loved feeling embarrassed in front of her. It made me feel, well, naked. And god was that exciting!

"Come on, little buddy," she grinned. "You think I don't know what makes you tick, at least a little bit, by now? I'm trying to turn you on. And clearly I'm succeeding. The only question is, what are you going to do about it?"

"God, Kara, it's like your personality is as hot as your body!" Okay, so it wasn't exactly poetry. But at least it was true. In answer to her question, I grabbed my dick between my thumb and forefinger and began to tug, slowly.

"See? Isn't that better? Now," she continued, you mentioned that I looked 'wounded' when you went soft looking at my boobs. And yeah, that didn't feel great. But as you were making your confession to me, I began to realize something. I'm not remotely interested in you sexually. But I'm very interested in your sexuality. Maybe it's weird but, even though I don't want to have sex with you, I want us to do sex things together...okay, that doesn't make sense.

"Let me give you an example. After you 'lost' the contest, when I was watching you work Sam's massive strap-on, all I could imagine was you and me, on our knees, side by side, sucking huge strap-ons together."

Oh my god, had she really imagined such a thing? Hearing her words put the image into my own imagination. I closed my eyes. I really could see the two of us, side by side on our knees, sucking massive starp-ons! Holy shit, how much fun would that be! As I pictured it, I started tugging faster.

"Like, I could so see you being the sexy, slutty, partner-in-crime, best girlfriend I never had. Except you're a dude. Except, not exactly?"

Oh my god, yes, Kara! Let me be your sexy, slutty, partner-in-crime best girlfriend! I could feel my breathing getting heavier as I tugged faster. I opened my eyes again and considered myself blessed to be staring at her tits.

"All I know right now is, I love the way you look at me. Without saying a single word, I can see how hot I am to you. And that's one helluva feeling. So I just want you to look at me like that now. Stare all you want, at whatever you want."

Oh, I was staring, alright. God, those tits!

"And i'm gonna stare back at you. Because like I said, Jack, your sexuality fascinates me. I mean, I can see how much you'r enjoying this. Just like I can see that the idea of you getting hard at this point is basically the punchline to a joke."

"This is no joke, Kara." My words were barely audible through my panting.

"I'm sorry, Jack. I didn't hear that." She placed her hands on my cheeks and looked at me. "Stop what you're doing for just a second. Yes, good. Now, look at me. No, up here, little buddy. Hi," she smiled. "Now, what did you want to say."

"I said," catching my breath, "this is no joke. Kara, my penis might be a joke. But my love for masturbation...and my love for your breasts...that's no joke."

"Wait, Jack. Are you saying you love my breasts as much as you love masturbating?"

"I...," I blushed. "I love them the same. What I mean is...Kara, masturbating in a world where your breasts didn't exist...what would be the point?"

"Aww, Jack," she grinned. "You really are sweet when you want to be. But if that's how you feel, then show me." Saying this, she bent slightly at the waist and pushed her shoulders together, really making her cleavage pop.

Mouth agape, face red, I was tugging furiously. My eyes were fixed on her magnificent cleavage, my forearm burning from the effort.

"That's it, Jack," she encouraged. "You're almost there, aren't you?"

I nodded, unable to speak.

"Then maybe this will help." She bounced on her heels, causing her overflowing cleavage to jiggle wondrously.

It did help. My god, what a sight! I was so close!

"Yes, Jack, you're nearly there. In fact, I bet you can finish in three...two..."

I couldn't last until 'one.' The pressure was too much, the hotness overwhelming. I began thrusting my hips into the air as I tugged with demon strength. I was right on the edge. Yes! Here it...

And then...nothing. Fucking nothing! Fuck!

"Oh, Jack," sighed Kara. She straightened herself and pulled up the neckline of her shirt. "I guess it's my fault. It was probably too much to ask."

"I'm sorry, Kara," I said, still red in the face. "I know you were looking forward to seeing a limp dick cum."

"Don't be sorry, Jack," she smiled reassuringly. "I mean, I was looking forward to it. But honestly, I'm glad it ended this way."

"Wait, seriously?"

"Yes, seriously. Jack, can you keep a secret?"

"Damn, I dunno, Kara. I mean, I tell Carrie everything. That's kinda at the core of our relationship." It wasn't easy to say those words. They were true, of course. And I meant them. But also, Kara - KARA! - wanted to share a secret with me?!

"No, you're right. I'm sorry, Jack." She frowned. "It was wrong of me to even put you in that position."

"Hang on," I said, thinking it over more carefully. "Does this secret have anything to do with me? Or with Carrie? Even remotely?"

"Not in the least," she said. "No, it's strictly about me. It's just very personal is all. None of the other girls know."

"None of the other girls know," I repeated. "But you would tell me?"

"Of course, Jack! After everything you've shared tonight? Let me put it this way. Apart from the five women in this house tonight, how would you feel if somebody learned about your penis issues?"

"Fucking mortified," I admitted.

"Well that's kinda how I feel," she explained. "Only, I'm not even at your level of confidence. I would be mortified even if it was just the girls who knew. Because I know that they all have their own personal shit that they don't share with the group. But Jack, you don't hide anything. That's why I feel like I can trust you with this."

"I see." My cheeks would have blushed with pride if they weren't already still red from the effort I'd just put myself through. "Alright, Kara. If it really has nothing to do with me or Carrie, I can keep your secret."

"Thank you, Jack." She let out a deep breath as her shoulders relaxed. "Jack, do you know why I love sucking dick so much?"

"Wow," I whispered. That was one hell of a question. "Honestly, if you had asked me before tonight, I'm not sure I'd have had a clue. But after getting up close and personal with Sam's strap-on, I'm beginning to have some ideas."

"I mean besides the obvious," she grinned.

Okay, so the physical sensation, the power dynamic and the sheer fun of it were apparently 'obvious.'

"No, there's another reason," she continued. "Jack, when I have sex with man, it's very rare that I have an orgasm. I'm not saying it never happens, just that it's very much the exception. And at some point, I got tired of faking it."

"Wait, you faked your orgasms?"

"I used to," she admitted. "And I can see from the look on your face that you're confused. The reason I did it was because that was usually the easiest and fastest way to bring the proceedings to a close. Because once I realized I wasn't going to cum, the fun kinda went out of it. But if I faked it, the guy could feel like he did a good job and then I could send him home happy."

"That sounds...not great," I frowned.

"It was very not great," she nodded. "Which is why I got tired of it. But I also had no interest in explaining to guys that it wasn't anything they were doing or not doing, that it was just about me. For one thing, guys can be really fragile about that sort of thing. For another, I wasn't really interested in putting myself out there like that."

"Kara, I totally get it. Believe me."

"I do," she smiled, eyeing flaccid penis. "That's why I'm telling you and nobody else. Anyway, I discovered that sucking dick was my way out of that mess. If I could go down on a guy and make him cum, then nine times out of ten, he'd be done for the night. That would be enough for him. And I wouldn't have to deal with the whole not cumming from intercourse thing."

"I'm so sorry, Kara. I feel like nobody should have to suffer like that."

"Who said anything about suffering?" she winked. "Don't forget, I absolutely love sucking dick for all the 'obvious' reasons. I mean, they didn't call me 'the blowjob queen' in college for nothing. Plus, at the risk of touting my own horn, I'm pretty fucking good at it. No, it's more like, this thing that I already loved became the thing that got me out of some rather unpleasant situations. And for that, I love it even more."

"I can understand that," I nodded. "But still. I feel like everybody deserves to have a good orgasm when they're with somebody. Maybe not every single time, but in general."

"Oh, I totally agree, Jack. And sometimes I would get lucky. And I'm not talking about the extremely rare guy who could make me cum from fucking. I mean, sometimes I'd get lucky with a really selfless, giving guy. Who, after I went down on him, would want to 'return the favor.' And that pretty much always does the trick. I mean, assuming the guy knows what he's doing."

Then she started to laugh.

"What's so funny?" I asked. "Do most guys not know what they're doing?"

"Oh, no," she chuckled. "Most guy are actually alright in that department. No, it's just funny. I'm only now realizing that its almost always the guys with the little dicks who are most selfless and giving. And after what you did to Vicky tonight," she laughed again, "I shouldn't have been surprised!"

"I guess we feel like we have something to make up for."

"Do you really feel that way, Jack?" She wasn't laughing anymore.

I blushed but didn't answer.

"Because you shouldn't, you know. Not with me, anyway. I wouldn't change a single thing about you. Not your size, not your inability to maintain - or even get - an erection. I think you're perfect just the way you are."

Her words made me feel ten feet tall. Although, honestly, I'm glad I wasn't. Being ten feet tall would just have made my dick look even smaller.

"Anyway," she resumed, "that's why I'm glad your little endeavor ended the way it did. It's not because I wanted you to fail or suffer. Just...it was nice to know that I'm not the only one who has trouble cumming sometimes. And I'm sorry. I know that's selfish of me."

"Don't be sorry!" I encouraged. "If me not being able to cum helped you feel a little bit better, it was totally worth it!"

"That is so on-brand," she giggled.

"What is?"

"You! Once again, the guy with the little dick is selfless and giving."

She was still giggling and, honestly, I had to laugh right along with her. To say nothing of the fact that I found this all incredibly hot, the two of us laughing together about the size of my penis. What's more, when Kara laughed, her tits jiggled ever so slightly. That sound combined with that sight would have been enough to get me hard; if I was capable of getting hard, which I clearly wasn't. And maybe because of that, I reacted to this hotness the only way I could, without even realizing it.

"You just can't help yourself, can you?"

"What?" Her question confused me.

For an answer, she simply nodded downwards. Following her line of sight, I discovered that my 'little guy' was getting a two-finger workout. I hadn't even realized I was doing it. It was a purely instinctive reaction.

"Oh," I blushed. "I guess I can't. Sorry."

"Don't be! And don't stop, either," she encouraged. "I'm loving this. Honestly, I feel like I'm getting to see more of the 'real' Jack in these few minutes than in all the rest of the party put together."

"How do you figure?"

"Let me ask you a question," she countered. "When you're having a non-sexual conversation with Carrie and then something randomly, um...stimulates you. What happens? What do you do?"

"Literally this," I answered almost automatically.

"Okay," she said, tilting her head. "I'm just trying to picture this. So you'll be chatting with Carrie about nothing in particular. And then maybe she laughs in such a way that makes her boobies bounce a little bit. And as soon as that happens, without even thinking about it, you just start tugging your perpetually limp dick?"