Naked Houseboy & his BBW Boss Ch. 30

*Part 30 of an ongoing story...

Kara and I were still standing in front of the mirror. She was in the process of explaining to me why and how she had decided to help me get off the last time, when I so clearly needed all the help I could get...

"...so I decided I'd try to help you along," she was saying. "And I figured what better way than painting a picture of Kara in a string bikini. I mean, I know what she does to you. And you haven't even met her yet!"

"What does she do to me?" I tried to sound indignant.

"Well for starters, any time I so much as mention her name, you immediately start playing with yourself."

"I do not!"

"Jack, look in the mirror."

Sure enough, without even realizing it, I had started tugging on my dick again. And for no other reason, apparently, than that I'd heard the words 'Kara in a string bikini.'

"You may have a point," I conceded. "I guess she does have an effect on me."

"Yeah, well, maybe the effect has been somewhat overstated. Hashtag penis issues."

We both looked towards the center of the mirror, where it was plain to see that, despite the steady tugging motion I was applying to myself, I was no harder now than I had been earlier.

"Penis issues aside," I deadpanned as I continued to stroke my limp cock, "you were saying?"

"I was saying, I thought by talking to you about Kara in a string bikini, I could help get you over the edge. But when even that didn't work, I figured I owed you something special. After all the frustration of the past 2-plus hours, after allowing me to see you fail so completely, I figured it was time for me to open myself up too. And I was happy to make you that promise, Jack. Especially because it worked."

"Well, I guess all I can say is, thank you, C. For all of it." I paused then, a new thought occurring to me. "Actually, can I ask you one more question?"

"Anything," she smiled.

"What made you give up on the Kara fantasy? I mean, how did you decide it just wasn't gonna work?"

"Oh, come on, Jack. If you want to jerk off to Kara now, just do it. We don't need the whole charade."

"No, I'm serious."

"Serious about wanting to jerk off," she amended.

"Yes," I sighed.

"To Kara."

"Also, yes."

"Just so we're clear," she grinned.

"Yes, we're clear. I want to jerk off thinking about Kara and her massive titties in a string bikini," I declared, continuing to tug on my still non-responsive penis. "Now please tell me why you gave up on that particular line of encouragement."

"Well, I could just tell by looking at you, it was never gonna work," she shrugged.

"What's that supposed to mean?"

"Oh, Jack, if you could only have seen yourself, you'd understand."

"Help me understand, Carrie."

"This was basically you."

Saying these words, she shifted her position so that, still next to me and facing the mirror, she was now standing with her feet shoulder-length apart. Then she moved her right hand just in front of her crotch, pinching her thumb and index finger nearly together. "Because when you can't get it up, you only jerk with these two fingers," she was saying. (I looked down, and sure enough, my limp dick was firmly gripped between my thumb and index finger). "And you were literally like this..."

Without any buildup, she immediately went into convulsions, furiously pumping her limp-dick grip in front of her crotch, thrusting her hips wildly, moaning loudly, gasping for air, panting, cursing, hissing. She was throwing her whole body into it, such that her enormous tits began to sway and bounce uncontrollably. It was one hell of a show.

"Agh! Ungh! Fuck! Fuck everything, fuck!" she was screaming. I was mesmerized. For a few seconds, I couldn't take my eyes off her giant breasts as they fought the constraint of her T-shirt. But soon enough, I was focused on her right hand. It wasn't just the the thumb-and-index-finger grip she was affecting, it was the furious but very short strokes which showed that she too was fighting an uncooperative penis in this reenactment. "Oh, oh god! Almost! Almost! Yes, yes...FUCK! Fucking dammit!"

She brought herself all the way to a carbon copy of my failed orgasm and then...'scene.' The character of me she had been impersonating disappeared and it was just Carrie again.

"That, my friend, was you." She smiled broadly.

"Jeez, that was intense!" It was surreal to see 'myself' like that from the outside.

"Yeah, I mean, I thought it was intense when I watched you go through it. It was fucking intense to just pretend too."

"Is that really what I look like though?" Even then, I wasn't sure how much of that had been put on for effect and how much of that was meant to be real.

"See for yourself," she shrugged.

"Wait, what?"

"Well, you want to jerk off to Kara, right? So I'm gonna talk to you about Kara now. And you just go crazy. I mean, give it everything you've got. Don't hold back. Right here, in front of the mirror. And you can see for yourself how good I was."

I couldn't argue with that logic. And so, just as she had done, I stood with my feet shoulder-length apart. I was already jerking my limp dick between my thumb and index finger, so I just kept that going as Carrie started to speak.

I don't remember much of what she said at first. Something about how the two of them used to order 20-30 bras at a time online and then spend an afternoon trying them on in front of each other. I was hearing some of it, but I was increasingly lost in my own world. A world I was actually watching.

Before long, I was exactly like Carrie had portrayed me. Thrusting my hips violently, panting, sweating, pumping furiously on my useless penis...

"Imagine if she walked into the room right now and saw you like this, Jack. 'What's he so worked up about?' she might ask. 'Oh, I was just telling him about how we used to try on bras together,' I'd tell her. Then she'd take one look at your limp dick and say, 'And he can't even get hard for that? I thought he was supposed to be in love with my tits.' So of course I'd have to tell her, 'He's very much in love with your tits. But he's also got some penis issues.'"

"Oh, fuck, fuck!" I heard myself hissing as I gasped for air. "Oh god!" I could see myself in the mirror, but in my imagination I could also see Kara entering the room, watching me go all out. And I was going all out, trying to put on a show for her.

"Then she'd feel kind of bad, right?" continued Carrie. "Like, 'Oh, I'm so sorry, I didn't realize he had...a condition.' And of course, I'd be like, 'Oh, it's a condition alright. Not a medical one, though. His condition is, he jerks off so much he can't even get it up anymore.' Then she'd look at you, as you try to cajole the least bit of life into your useless dick and she'd say, 'So he did this to himself?'"

"Oh, god, fucking yes, Kara! I did this to myself!"

"Wow," I heard Carrie say in a hushed whisper. Clearly she had not expected me to jump into this fictitious conversation she was crafting. The truth is, I was shocked myself. I was so caught up in the moment, in the story Carrie was painting, I actually believed I was in it.

As for Carrie, she quickly regained her composure and jumped right back into things. "'But why, Jack?' she would say. 'Why would you do this to yourself?'"

"Because I fucking love jerking off so much! Fuck! Agh, Kara, can't you see? All I wanna do is masturbate. I don't want to slow down, I don't wanna take breaks. Dammit, I don't even want to sleep. And I definitely don't wanna cum, because when I cum it's over. I just want to jerk myself stupid, even if it means I can't get hard! Oh, god, fuck!"

I was sweating profusely, throwing my whole body into the effort, pumping like a demon. I really believed, in that moment, that I was talking to Kara. It felt so good to say those things, and not just say them but shout them. Out of the corner of my eye, I saw a strange look on Carrie's face. It was not a look I'd ever seen from her before. Had I just crossed some line? Had I finally humiliated myself in front of her in a way she just couldn't get on board with?

But those doubts were dispelled with her next words as she resumed the scenario. "If you wanna jerk off so much that your dick doesn't even work anymore, that's up to you," she was saying. "I guess I just feel like, at the very least, the sheer enormity of Kara's breasts deserve the simple dignity of an erection, you know? I mean, you've spent your whole life dreaming of tits like hers, jerking off to tits like hers. And now you're in the same room with her, you can't even show your appreciation."

"But I'm trying to show my appreciation," I groaned loudly. "Look at me! Oh god, fuck!"

"And she would look at you, Jack. But do you know what she'd say? She'd say, 'All I see is your appreciation for jerking off. I mean, you'd be doing this whether I was in the room or not.'"

"But I want to show my appreciation, Kara! How can I show my appreciation?" It was more of a whimper, the sound that came out of me, the pathetic, red-faced, sweaty limp-dick apparition in the mirror.

"She'd put her hands on her hips," Carrie was saying. "Then she'd look at you and say, 'Nothing would make me feel more appreciated than to just lean over a little bit and let you look down my blouse...and see you get rock hard just from that. But obviously that's not gonna happen. I mean, I could take my top off. I could take my bra off. Hell, I could wrap my naked tits around your limp, little penis down there and you still wouldn't be able to get it up.'"

"But there must be something I can do...fuck!...to show my...fuck me!...appreciation!" I was pushing myself more and more, as if just by jerking off harder and faster I could show her the appreciation she deserved.

"Be careful what you wish for, Jack," interjected Carrie, once again flashing that unfamiliar look.

"I need to show her," I grunted through clenched teeth.

"Then I guess she'd say," proceeded Carrie, "something like, 'Well, Jack, since you obviously can't get hard for me, I suppose there's only one thing you can really do to show me your appreciation.'"

"Anything! Tell me!" I pleaded.

"'You have to do the one thing you don't want to do,' she'd say. 'You have to cum for me. Sacrifice this jerk off session, end it now and cum for me. Then I'll know you appreciate me and my magnificent tits.'"

"Yes, Kara, I will cum for you..."

I was close. I could feel it building. I thought I was going all out before, but now I was truly giving it everything I had. Almost there. The thought of Kara's cleavage. Carrie, watching all this unfold, even as she was orchestrating it. So close. Teeth clenched. Every muscle contracted, straining. My right forearm on fire, my excuse for a cock ready to explode. And then...nothing. Nothing at all. Fuck! Fuck how did it not happen!?? I was so close!

Exhausted, defeated, I turned to Carrie. She was still wearing that look. But now, finally, I understood it. She didn't need to say anything, but she said it anyway.

"I'm sorry to do that to you, Jack. But this is how you were before. I knew from the beginning that talking about Kara wouldn't be enough then. Just like I knew it wouldn't be enough now. I don't know how I knew, but I knew. And the only way I could prove that to you was to take you all the way through it and let you find out for yourself. I'm sorry, Jack, I know that had to be incredibly frustrating."

"Um, the ending was frustrating, yeah. But the rest of it?" I shook my head. "I mean, I feel like you just helped me discover a truth about myself."

"Wait, seriously?"

"Oh my god, yeah. Come here, Car." Taking my right hand from my cock, I put my arm around Carrie's waist and pulled her up close to me, so that we were once again standing side by side facing the full-length mirror. "It started with something you said."

"What'd I say?"

"Well, you were explaining to Kara that the reason I can't get hard is because I jerk off too much. And then you had her say, 'So he did this to himself?' Remember?"

"Of course I remember," she frowned. "But listen, Jack, don't read into any of that. I was just playing with you, just having fun. We've never done a jerkathon before. This is the by far the most you've ever masturbated in a 24-hour period. Hell, we're not even at 24 hours yet. Your dick has every right to be exhausted. I mean, I guess in that very narrow sense of just the past however many hours, sure, you did this to yourself. But you haven't given yourself a 'condition' or whatever."

"I appreciate that, C, really. And rationally, everything you said makes perfect sense. In fact, I would agree with you entirely. If it weren't for just one thing."

"What's that, Jack?"

"When you said those words...I FELT something. I mean, that's why I practically shouted, 'fuck yes, I did this to myself.' Which I know caught you off guard, by the way."

"Yeah, I definitely wasn't expecting that," she smiled, remembering the moment. "But I assumed that was just you getting into the story. I didn't think there was anything deeper going on. But you're saying there was?"

"Right. Do you remember what I said next?"

"Hmm," she paused. "Wasn't it something like, 'I love masturbating, it's all I wanna do and I never wanna stop'? In other words, your usual spiel?"

"My usual spiel, yeah," I grimaced. "Except I added something new at the end, something I don't think I've ever said before. Remember?"

"OH," her eyes grew wide. "Yeah, I do remember! You said, 'I just wanna jerk myself stupid, even if it means I can't get hard.' Is that what you mean?"

"That's exactly what I mean!" I was so excited that she'd remembered my words so precisely. "And that is exactly what I'm trying to tell you. When I said that, that wasn't me just playing along with the story. That wasn't me just having some fun. That was me discovering a truth about myself.

"In that moment, I realized that I love masturbating so much, realized that I truly want to jerk off so much...even if this is what it does to me." My right arm still around Carrie's waist, I grabbed my penis between my left thumb and index finger and started to stroke again; the complete lack of response illustrating my point. "So when you had her ask me why I would do this to myself, and I got to tell her...god, Carrie, it felt so good to tell her that."

"Can I ask you a serious question, Jack?" Her voice was almost a whisper.

"Always."

"Do you want Kara to see you like this?" She paused, taking a deep breath. "I don't mean like before, with all the theatrics. I don't mean like today, nearing the end of this jerkathon that has clearly taken you to your limits. I mean, do you want Kara to see you like this...like the person you just calmly and rationally described to me, the guy who not only jerks off so much he can no longer even get an erection, but the guy who loves jerking off so much that he actually thinks that's a fair price to pay. Do you want Kara to see you like that?"

"Wow, C, that's a helluva question."

"I'm sorry. I guess I'm just trying to understand the depths of this self-discovery you're sharing with me."

"Hey, I'm trying to understand it to. It's a good question. Let me think about it for a second." And I did think about it. I also continued to jerk off, pulling on my impotent member as I pondered her question. At least, I did so until I was interrupted by the sound of her laughter. "What's so funny?"

"I literally can't tell if you're just playing with yourself while you think or if you've forgotten all about the question and are only jerking off now."

"I was really thinking about!" I shot her a look. "At least until I was rudely interrupted."

"Sorry," she blushed.

"OK, here's what I think."

"Tell me."

"I think this is all very new to me right now. And this thing I'm discovering, I don't know if it's just one part of me, something to explore and have some fun with, or if..."

"If what, Jack?"

"I dunno. If...if maybe this is really who I'm supposed to be."

"And the answer to that question determines whether you'd want Kara to see you like this or not?"

"I wanna say yes. Yeah," I added with slightly more confidence.

"I think I understand," she nodded. "Like, if this is really the person you're supposed to be, then you'd like to face the world that way, as it were. You'd like for her to see the real you."

"Actually?" I looked at her eyes reflecting in the mirror. "The opposite. If this turns out to only be a new kink for me, something that's fun if it happens occasionally, then I'd love to let her in on it. Let's turn the humiliation up to 11 and see what happens. But if it turns out this is really who I'm supposed to be..." I stopped, unsure how to finish my thought.

"It's alright, Jack," smiled Carrie sweetly.

"If this is really me," I continued, nodding downwards towards my zone of play and failure, "I think I'd like for it to just stay between us. At least for a while."

"Of course, Jack. If that's how you feel. In fact, I have to say I'm honored that you would allow me to share in this discovery and exploration with you. But I'm curious about something."

"What's that?"

"You never get tired of expressing your love of masturbation. You'd shout it from the rooftops if you thought you could. Because that's who you are, somebody who just loves masturbating. And part of the reason you're going to meet my friends on Friday is so you can express that to more people than just me, be your real self with more people than just me. People we know are going to accept you for who you are."

"Right? So what's the question."

"The question is, if this new thing we're talking about turns out to be just as much a part of you as your general love of jerking off, why would you not want to be open about it and share it in the same way?"

"Wow, you're really bringing the hard ones today, aren't you?"

"Well, I mean, probably at least one of us should be bringing something hard, no?" She tried to keep a straight face, but I could see the corner of her mouth twitching.

"And that right there is why I want to share this with you and only you," I declared.

"Because I ask you hard questions?"

"No," I shook my head. "Well, yes, that too. You challenge me, it's great. But no, I mean because you're able to joke about it. And not in a mean way, but just in a like, 'how can we not see the humor in this' kinda way. You're the only person I trust to do that."

"Jack." Carrie blushed a little, unsure how to answer. And then she remembered her question. "But you still haven't told me why you wouldn't want to be open about this in the same way."

"I dunno, C. But like, my love of masturbation...that never felt wrong to me. It always felt so right. Socially not so acceptable to brag about at parties, perhaps. And yeah, I often worried that most people wouldn't understand why I'd prefer to jerk off than fuck. But it always felt right to me. Being able to share it with you has been a literal dream come true. And I can't wait to share it with your friends. Because I'm not embarrassed by it or ashamed of it."

"But this new thing?"

"Yeah, this new thing," I nodded. "And look, we're like walking on eggshells just the way we talk about it. 'This new thing.' 'This discovery.' Whatever. Honestly, I'm not even sure if we were joking before, but I think I liked it better when we just called it my penis issues."

"So let's call it your penis issues then. But Jack, are you embarrassed by or ashamed of your penis issues?"

"I'm honestly not sure, C. I mean, when we were in the middle of that scenario with Kara before, I wasn't. But now..."

For a minute or so, neither of us said anything. I think Carrie was just trying to give me space and time to think. But eventually, she seemed to think I needed a nudge.