Naked Houseboy & his BBW Boss Ch. 28

*Part 28 of an ongoing story...

I left Carrie alone to "tend to herself" in the company of her big-dick slideshow with the intention of taking a short nap in my own bed. To say I was exhausted would be an understatement. We had officially started the jerkathon at 10:30am. It was now 10:00pm. In that time I had clocked over nine hours of masturbation and cum four times. So naturally, I assumed that when I got into bed I would pass out instantly. But that is not what happened.

You have to remember that we had been watching porn for nearly twelve hours straight with zero interruption. So when I closed my eyes, all I could see was porn. Huge bouncing tits, massive cocks, cum-splattered faces, femdoms with strapons, dildos sliding in and out of wet pussies. I didn't know if I should be delighted or scared. I opened my eyes again to see the four walls of my room. But as soon as I closed them, the porn came back.

And then I remembered Carrie's rule. There must be porn playing at all times during the jerkathon. So I walked over to my computer and put on some cam girls. Now, eyes open or closed, there would be porn. I smiled. Perhaps it was decadent or over the top. But then, the whole point of the jerkathon was to be decadent and over the top.

I then climbed back into bed, intent on catching that nap. But how could I sleep, knowing that at this very moment, Carrie was masturbating in her room? Instinctively, I reached for my dick.

How would she look? Her shirt pulled up just high enough to allow her hand access to her pussy. Her eyes glued to her slideshow. Was she more responsive to clitoral stimulation or to penetration? Was she using a toy? Did she even have toys?

I simply lay there, thinking these thoughts, trying to imagine her as she might be. And all the while, slowly tugging on my dick. Only, I wasn't getting hard. Maybe I shouldn't have been surprised, given how much time I'd already spent masturbating that day. But if I wasn't surprised, I was certainly disappointed. After all, this was the first time that I knew with absolute certainty that Carrie was - at that very moment - masturbating. I should be able to get hard for this.

After a short while, realizing it was a lost cause, I decided to just allow myself to enjoy the sensation of slowly pulling on my limp dick, hoping I'd soon fall asleep from sheer fatigue.

It couldn't have been more than ten or fifteen minutes later when Carrie appeared in my doorway. She looked fresh, glowing even, with a smile of utter contentment on her face.

"That didn't take long," I said, turning my head towards her.

"I thought you were going to nap?" she returned.

"How could I? I mean, knowing what you were doing, there was no way I could fall asleep."

"I kinda figured as much," she answered with a wink. "If I thought you were sleeping, I wouldn't have come by. I'd have let you get your nap in. But something told me you'd be...up." With that last word, she eyed my penis with a wicked little grin. "Guess I was wrong," she added with just a hint of disappointment.

"I'm sorry," I sighed. "I guess I'm just exhausted."

"And you have every reason to be," she smiled softly. "Look, why don't you come back and finish in my room?" she added. "Then we can have a nap together."

"Honestly, C, I think this is kind of a dead end," I replied, giving my tired dick a few exaggerated tugs to illustrate the point. "Probably the best thing for me is just to take a nap now."

"I'm sorry," she shot back, placing her hands on her hips. "Did I hear that correctly? Are you turning down an opportunity to masturbate in my bed?"

"I just think maybe it's not the best idea...just at this moment." I sighed again.

Then Carrie came over and sat down next to me, on the edge of my bed. Taking hold of my right wrist, she removed my hand from my penis. For a moment, she just looked at it, examining it with her eyes. At last, she took my limp member between her thumb and forefinger, applying a very slow and deliberate tugging motion. She looked me in the eye as she spoke.

"OK, Jack. If you can honestly tell me now that you'd rather stay here, alone, and take a nap rather than come back to my room with me and masturbate in my bed...well, then I'll leave you to your nap. But...is that really what you want?"

Oh, for fuck's sake, of course that's not what I really wanted. But there was a difference between what I wanted and what I thought was a good idea. And the fact that I wasn't getting the least bit hard in her hand told me this was a bad idea. Yet the way she was slowly pulling on my inanimate cock, the way she was looking at me, I knew I'd be walking back to her room with her in a matter of seconds.

Which is exactly what happened. Moments later, we were lying her in bed, in our usual positions: me on my back, her curled up beside me, her arm across my chest. My penis, which I was slowly tugging, was still showing no signs of life.

"Any requests, porn-wise?" asked Carrie.

"I dunno," I sighed. "Something softcore, with big tits, I guess." I had almost no energy at that point, and I guess I wanted porn that was low on energy as well. Carrie obliged with something that would have been fit for the Playboy channel. It was exactly what I wanted; not that it did anything to get me hard.

I don't know how long we lay there like that, mindlessly watching softcore porn as I continued to pump my useless dick. Time seemed to slip away. And yet not in that beautiful goon-zone kind of way. It was more like the world had evaporated around me as I become further and further enveloped in a tedious task.

More than once, I fell asleep; or nearly did. I could feel my eyes closing, my hand stopping. It wasn't quite sleep, but rather that gray area on the very edge of it. When this would happen, Carrie would give me a little nudge and whisper something in my ear along the lines of "Hey, don't give up now." It was enough to wake up me, and then I'd be back at it.

At one point, when there were a particularly beautiful pair of breasts on the screen, I felt myself close to cumming, limp as I was. I started tugging faster; tugging became pumping; breathing became panting; I started aggressively thrusting my hips into the air, clenching every muscle in my body. I was so close...so close...god, those tits!...so close...so cl-...and then...nothing. Fucking nothing. I was right there, right on the edge. And I had completely failed to climax.

"Fucking dammit!" I hissed as I collapsed, all the tension going out of my body.

"Hey, hey, it's OK," whispered Carrie, as she wiped the beaded sweat from my brow. "You did your best. I think you've earned that nap now," she added, kissing me on the cheek.

"No, uh-uh," I grunted, still trying to catch my breath. "There's no way I can sleep now if I don't cum."

She smiled, as if this were the answer she was expecting. "That's my Jack. Never give up." And she kissed me on the cheek again.

I won't bore you with the details. But suffice it to say, the same process - and the same failure - repeated itself twice more. We were now well over two hours into this most aggravating jerk-session, and all I had to show for it was a limp dick and sense of extreme frustration.

When, for the fourth time, it seemed as though I was getting close, Carrie decided to intervene.

"Jack, I'm going to help you this time. I want you to close your eyes and just focus on my words, OK? And I want you to keep it slow. Don't speed up until I tell you. Promise."

"Promise," I whispered, closing my eyes.

"We're less than a week away from the party, Jack. On Friday, you're going to meet my girlfriends. And when you meet them, you're going to be entirely naked. Well, except for your little chastity device. We're all gonna have a lot of fun, Jack. I promise you that.

"And I've been thinking about how it's going to be, you meeting my best friends. Personality-wise, I think you're really going to click with Samantha. She's the little redhead, remember. Intellectually, you're gonna love Allison, the one with the sexy-librarian look. You can talk about literature and history and politics with her. Vicki, well, Vick's a lot. But she's gonna challenge you, and you're gonna eat it up, I just know it.

"Oh, but Kara. You remember Kara, don't you? With the massive titties? Of course you do. I'm sure she's gonna wear something low cut. I mean, she just loves to show off the girls, you know? And if you do a good job at the party, Jack, and I mean a really good job, I think they'll probably let you jerk off in front of them before they leave.

"Would you like that, Jack? What kind of question is that, of course you would! And when you do, you'll be able to stare at Kara's cleavage all you want. I mean, she loves the attention. So just think about that. Think about that now. Think about being in front of me and all my friends, jerking yourself off, with Kara's incredible breasts on display, just for you. You can speed up now, honey."

I started to pump my still limp dick with increasing speed.

"Kara's tits," she went on, "are just like the ones you dream about. Fat, heavy, pendulous. I've seen her in a string bikini, you know. String bikinis have no chance against those titties. Her breasts come all the way down to her bellybutton. The deepest most glorious cleavage you've ever seen. Well, you've never seen it. But I have, and I'm telling you. Yes, that's it, faster, Jack. Faster now. You're so close."

Just as before, I began thrusting my hips into the air as I panted for breath, all the while furiously pumping my soft cock.

"I"m sure if she were standing here right now, in that micro bikini, she'd love to see you cum, Jack. She'd be so happy knowing it was the sight of her massive tits that pushed you over the edge. Can you see them? Hanging there in that micro. bikini?"

I was so entranced by the image that Carrie was painting that I couldn't even answer. I just kept flailing away, trying to will myself to orgasm.

"Show her, Jack," hissed Carrie in my ear. And as she did so, she grabbed a fistful of my chest hair, almost forcing me back down into the bed. "Show her what her tits do to you," she said, raising her voice.

I was pumping so hard now that my forearm was burning. I was throwing my whole body into the effort. But with every upward thrust, Carrie forced me back down by her fistful of my chest hair.

"Fucking show her, Jack," she commanded in a still louder voice. "Fucking show her!"

I was so close now. Closer than I'd ever been since we started. So close...and yet, not quite there.

"Do you see those titties, Jack? Look at them! This is what you live for, isn't it? To jerk your little dick to tits like that? It's what you fucking live for. So fucking show her!" She was almost yelling.

I wanted to show her so badly. Carrie was right. Jerking off to tits like Kara's is absolutely what I live for. And yet, just now, somehow, it wasn't getting me to the finish line. Carrie sensed this, and she changed her approach.

"Open your eyes, Jack. Look at me."

I did as I was told. Carrie's face was mere inches from mine. She looked into my eyes as I continued to furiously pump away at my limp dick. I could feel the frustration on my face, the desperation. My cheeks were burning with the shame of not having been able to cum at the though of Kara's wondrous breasts. All this, Carrie read clearly in my face. And in response, her face softened. She lowered her voice back to a whisper. She never broke eye contact with me.

"My poor Jack. My poor Jack, it's OK. Kara's not here. There's no pressure to perform for her. No pressure at all. It's just me, Jack. It's just me - Carrie. You can show me, can't you? You can show me...when you're ready.

"I'm sorry I tried to make this about Kara's tits. I mean, I know the truth. I know the truth is, it's my tits you want to see more than anything. And I'm sorry that I've never let you see them. You've shown me so much, and I've shown you so little. It's not fair to you, Jack. But I'm just not ready. I know you understand. You've been so patient with me, so understanding.

"But I will show you my tits one day, Jack. Look at me," she said, taking hold of my chin with her hand as she looked deep into my eyes. "I promise you, you'll see my tits one day."

That look on her face. Those eyes. Those words. I went off like a firehose, my limp dick spraying droplets of crystal-clear cum in every direction. The look of soft compassion on her face curled into one of wicked satisfaction as warm droplets spattered her cheek and landed in her hair.

Collapsing, panting, drenched in sweat and dripping with cum, I closed my eyes, overwhelmed with a feeling not so much of satisfaction as of relief.

"See, Jack," she smiled. "I knew you could show me."

Then, running her index finger over her cheek so as to collect the cum droplets that had landed there, she put her finger to her lips and applied my seed as if it were lipstick. She leaned in and kissed me with those lips; her cum-covered lips against my own.

"Sleep, Jack. Sleep..."

*****

When I next awoke, it was something like twenty-after-six in the morning. The memories of my last experience had not yet come back to me. For the moment, I only had two sensations. The first was of feeling well-rested and refreshed. The second was of Carrie's hand wrapped around my balls.

I had no memory of her taking hold of me in this way, and so I concluded that she must have done so after I passed out. I smiled. Not only did she no longer feel the need to ask for permission, apparently she now felt comfortable grabbing me by the balls in my sleep.

It was either that, I thought, or she had instinctively reached for my balls in her sleep, the way one might reach for an extra pillow or a stuffed animal to cuddle with. Either way, whether it was a conscious decision or not, I loved the fact that this was where we were in our relationship. Whatever our relationship was.

I turned my head to look at Carrie's sleeping face, her cheeks and hair still flecked with spots of my dried cum. It seemed she'd fallen asleep without even bothering to clean herself off. I'd never seen her naked. Never touched her in any of the ways I dreamed of touching her. And still I knew I loved her.

But my smile quickly faded as the memories came flooding back to me. I was suddenly overcome with feelings of embarrassment and shame. It was bad enough that I couldn't get hard. Bad enough that I failed to cum not once, not twice, but three times. Bad enough that even when she painted me a picture of Kara's enormous tits in a micro bikini, it still wasn't enough to get me off.

No, the worst thing was that which, in the end, did get me off. She had looked me in the eye and promised me that, one day, I would get to see her tits. I mean, I knew - I do know - how self-conscious she is about her body. I know that she's nowhere near ready to be naked in front of me. I know that these things are a real struggle for her.

And yet, she'd said that to me because she believed it was what I needed to cross the finish line. And she was right. But how could I do that to her? How could I put her in that position? Yes, I was embarrassed and ashamed about the other stuff. But I was most ashamed, most embarrassed about this. And so I decided the best thing for me to do - all I wanted to do - was to go off to my room and be alone.

I looked at the clock. There were only four hours left to the jerkathon. It would be a shame, and indeed another failure, to quit now. But how could I face her after all that had just happened? No. I would leave and go to my room and close the door.

But first, I had to get free of her grip. That grip. I looked once more at her peaceful, sleeping face. She wore such a look of contentment. And I too was content, my shame notwithstanding. There was no greater feeling than having her fingers wrapped gently, warmly around my balls. But no. I had to go. As long as she was sleeping, I could handle it. But if she woke, how could I face her?

Slowly, I reached down for her wrist, hoping to pull her hand off of me without waking her. But no sooner had I made contact with her skin did her eyes flutter open.

"Oh, you're awake," she smiled...