Naked Houseboy & his BBW Boss Ch. 40

*Part 40 of an ongoing story...

"For now, I'm just relieved that it's over," Carrie was saying. "I'm glad we're done."

"Carrie," I said gently, looking up at her from the floor, "we're not done."

"What do you mean we're not done?!" Her words were a mix of worry and excitement.

The reason I was on the floor, after all, was because she'd just squeezed my balls as hard as I could take. Not once, but twice. But by surrendering myself so completely to her, I allayed the jealousy she had been feeling towards me and Sam and our encounters at the party. For her, the 'exercise' had been a success. Mission accomplished. Which explains why she thought we were done. It does not, however, explain the worry and excitement.

She was worried, no doubt, because the first time had been very difficult to her, watching me suffer as she put me through that immense pain. It was hardly a surprise, then, if she was happy to be done with this 'exercise.'

Her excitement, on the other hand, surely stemmed from the second time she had crushed my manhood. She seemed to glory in the power it gave her, to have my balls in the vice-grip of her hand. As worried as she might have been for my well-being, there was no hiding the fact that just the idea of bringing me to my knees again was giving her a rush.

"Carrie," I answered, raising myself on one elbow, "I know it feels like we accomplished our goal here, since you're not jealous anymore. But I know you. All we've done so far is put to bed your feelings about me and Sam's emotional connection. The thing is, there's still the physical connection. And we need to deal with that as well."

"Oh, Jack." There was remorse in her eyes, even as her lips twitched into a fleeting smile. "Are you sure?"

"I'm sure," I smiled through gritted teeth. "Like I said in the beginning, if we don't do this all the way, there's no point. So let's do this all the way."

"Alright, Jack. At least let me help you up." Bending down, she reached a hand to me. For a moment, I regretted that she was still in her party clothes: white blouse, beige cardigan and blue skirt. Because if she had been wearing her usual 'pajamas,' imagine how her enormous breasts would have swung freely down as she bent at the waist... but what was the point? I was in no condition to jerk.

Having helped me up, we were now standing face to face. Which, in light of our current conversation, suddenly felt like an offense on my part. She must have felt it too, which is why she said what she did.

"Jack, honey, you could probably use a minute to regain at least a bit of strength. I'll be right back."

That's all she said. But when she returned, it was in high heels. She now stood a good head taller than me.

"There," she smiled. "That feels better, doesn't it?" I suppose she could have been referring to my aching balls and the extra minute or two of reprieve she'd allowed them. But I'm nearly certain she meant the new height differential.

"Much better," I agreed. While I didn't feel noticeably better physically, I did feel a warm, tingly sensation looking up at her, as if I were in the presence of greatness, not by right but by favor.

"Alright, Jack," she said calmly. "So we're going to do this again?"

"Yes," I nodded. "But this time with a twist."

"What kind of... twist?" There was no more remorse in her eyes. They were sparkling now. She was all-in.

"Okay, Carrie." I took a deep breath. We were really going to do this. "Now you know exactly how hard you can squeeze me before I just can't take any more. Now you know what my breaking point is. So this time, I'm not going to tell you when to stop. I'm going to trust you to know when. No matter how much it hurts, I'm not gonna say a word. I'm in your hands. Or, well, hand."

"Wow," she exhaled, even as she smiled slyly. "Okay, Jack. I think I can do it."

"I'm sure you can," I smiled. "But there's more."

"More?" The look of worry had returned.

"Yes. Carrie, you still trust me, right?"

"Of course, Jack. Now more than ever."

"Good. Start by wrapping your hand - very gently - around my balls. But don't squeeze yet!"

As she did so, I grimaced, momentarily shutting my eyes. I was more tender than I'd realized.

"Are you okay?" she asked hurriedly.

"Yes, I'm fine." I took another deep breath. "Close your eyes, Carrie. Good. Now, I want you to picture me and Sam, just as we were at the party. I want you to see her grabbing me by the balls, exactly like it really was."

Even as I said these words, I could see her jaw clenching, her shoulders stiffening. Which is exactly the effect I was hoping for.

"Good, C. Now, this time, when you start to squeeze, I want you to say - out loud - what that was like for you. As you tighten your grip, I want you to narrate exactly what you were feeling when you saw her grabbing me by the balls, what was going through your mind, what you were thinking. Out loud, remember."

With her eyes closed, her jaw clenched, her shoulders stiff, she nodded silently.

"Now here's where I'm really gonna trust you, Carrie. More than I've ever trusted you with anything. Because as you're narrating your experience, the moment's gonna come when you reach my breaking point. And in that moment, you're going to have a decision to make. You're going to have to decide if I've suffered enough for the jealousy I've made you feel, or... if you need to punish me further."

"Oh my god, Jack." She opened her eyes. "I think it's wonderful - beautiful even - that you trust me not to hurt you. But what you're asking me to do... I mean, if my emotions get the better of me... I'm not sure I trust myself not to hurt you."

"You don't understand, Car." I said reassuringly. "I'm not trusting you NOT to hurt me. I'm trusting you TO hurt me... if that's what you need. I'm willing to take whatever pain is necessary to make sure you never feel jealous about Sam grabbing my balls ever again. That's why I needed you to be certain of my breaking point. So that, when the moment comes, you can go past it knowingly, because you need to."

"Fucking hell, Jack." It was strange to hear those words from a smiling mouth. "The rational part of me would never take you past your breaking point. But shit, what your'e asking me to do... it wont' be my rational self that's squeezing your balls, Jack. Which means, I don't know what's gonna happen. And that scares me. But also," her eyes fluttered, "fuck me is this exciting! Fuck, I mean... no, I'm sorry. I shouldn't have said that. All I want to say, Jack, is... I don't know what's going to happen here. And if I wind up hurting you, I want to apologize now. Before it happens."

"Thank you, Carrie. I appreciate that. Now. Shall we begin?"

"No sense in putting it off," she nodded.

"Okay then. Close your eyes. Aaand... go!"

"I can see it so clearly," she said softly, her grip firming around my balls ever so slightly. "You and Sam. It was obvious that you guys had a spark, right from the beginning. But that didn't bother me at first. Actually, I was happy. Happy that two of my best friends were making a connection. But then she grabbed your balls." Her grip tightened just a touch. "I felt a twinge of something inside, but I brushed it away. We said in the invitation that the girls could handle you however they wanted. And anyway, Vicky had already grabbed your balls. This felt different though. Also, it was only one time. So what?" She relaxed her grip slightly.

"It's funny." She actually laughed. "I watched your connection grow the whole night, all through the party. Not just the way you sucked her strap-on, which, wow. But the way she was always coming to your defense when everybody else was mocking your joke of a penis. And in the moments when she was defending you, I thought that was really sweet. But in other moments, when your tiny dick wasn't the subject anymore, I started to feel like...'Bitch, who are you? He's my houseboy. If anyone is going to defend him, it should be me!'" Her grip began to tighten again.

"Of course, there's really no defending your penis, Jack. Hell, the first time I saw you naked, I wasn't just disappointed, I was fucking offended!" Her grip grew tighter. "And that was back when you could still get it up!" Tighter still. "But then I realized, Sam's not a size queen. And don't you deserve to have a connection with someone who's actually not offended by your pathetic...", she relaxed her grip a touch.

"And that would have been fine," she went on. "Except for the goodbye. Why couldn't she just say some nice words like everybody else? Or give you a hug, even? Why did she have to..." She was squeezing me forcefully now. "It's not just the fact that she grabbed you by the balls," she said, lowering her voice and tightening her fist. "it was her attitude. Like she was saying, 'See? I know Jack better than all of you. Just look how I have him by the balls.' Bitch!" hissed Carrie. "Who the fuck do you think you are? Those are MY balls! You have NO right!"

As her fist began to clench, I shut my eyes against the agony. I was nearly at my breaking point. I was barely hearing her now. I was just focusing on my breathing. And the pain.

"But the worst part was you, Jack! YOU!" With one quick flex of her hand muscles she had brought me to my limit. I opened my eyes wide, oblivious to the tears streaming down my cheeks. My jaw hung open, as useless as my cock.

"How could you do that to me?" Our eyes met. And I could see that she knew. She knew that this is where she'd need to stop if she didn't want to truly hurt me. I could also see that she wasn't done, that she had yet to vent all of her jealousy and hurt. But she didn't say a word. She kept her grip exactly as it was, not yet daring to go further. Her eyes, though, were searching for permission. And I knew that she needed this. Too weak to utter a sound, or even to nod my head, I blinked slowly, my eyelids telling her what my voice could not.

"How could you do that to me, Jack? How could you surrender yourself to another woman? And not just yourself! You surrendered your balls to her. No. Not your balls. MY balls!" That was the moment she broke the barrier. She was now squeezing me harder than she ever had, harder than I thought I could possibly endure. I tried to scream, but all that came out was a pathetic whine.

"Shut up, Jack! I don't want to hear it! It's too late! Isn't it enough that I let you keep your pathetic cock? Isn't it enough that I let you jerk yourself limp? But these - " she squeezed harder - "were always supposed to be MINE."

Very quickly, my knees were turning to jelly. I wasn't sure how much longer I could stay standing.

"Jack, I wanted to cry when I saw the way she had you by the balls. But I didn't deserve to cry. Did I, Jack? Maybe you do, though."

Now, instead of squeezing even tighter, she gave my balls a firm twist. This time I did scream.

"Hard to cry when you're screaming, isn't it." I could feel the tips of her fingernails beginning to dig into my scrotum.

She might have kept talking. I couldn't hear her anymore. There was only pain. I felt my knees slacken. And then I fell forward, into her body, my head landing on her shoulder. In that moment, she let go of my balls and wrapped her arms around the small of my back, bearing me up. As she held me, I began to sob helplessly.

The first moments that followed are a haze, even now. All I can remember is the torturous, throbbing pain in my balls; her powerful arms holding me close; and me, sobbing shamelessly, soaking her shoulder with my tears. The worst part of it all was, even though we'd hugged many times before, this was the tightest she'd ever pressed me against her heavenly bosom. And I couldn't even enjoy that much, such was the pain I was in.

"That's right, Jack," she said softly as she continued to hold me. "Cry. Cry like a little bitch."

In that moment, crying was all I could do. Earlier, when I was stronger, I'd decided that I wouldn't hide my tears from her. Now though, I couldn't have hid them even if I'd wanted to.

"You fucking bitch," she whispered, holding me in that bear-hug. But there was no longer any anger in her voice. The words might have been harsh, but her tone was soft, gentle. "That's what you are now," she said gently. "You know that, right? You're just a fucking bitch. You have a little bitch penis. You cry like a little bitch. And now, my sweet Jack, your bitch balls belong to me."

As I heard those words, crying on her shoulder, I knew that they were true. To this woman, this woman who loved me more than anyone else in my life, my penis was an offense. I was sobbing uncontrollably and I wasn't ashamed. The thought of even trying to deal with this pain 'like a man' never crossed my mind. I just wanted her to hold me and let me go on crying.

And my balls. God, the pain was like nothing I'd ever experienced. Yet there I was, holding on for dear life to the woman who had inflicted that very pain upon me. And I didn't want her to ever let me go.

Through my tears, I began to realize. I wasn't in this terrible agony because of the 'exercise' I'd suggested. I wasn't in this state because Carrie was being somehow cruel to me. I was crying tears of pain because that's what I deserved.

Carrie had given me so much. She'd made so many of my dreams come true. And how had I repaid her? By trusting another woman with my balls. By allowing myself to feel something with that woman's hand between my legs. By making the mistake of thinking my balls were ever mine to give.

From the day Carrie hired me, my balls were no longer my own. I could see that now. Of course they were hers. And she knew it, too. When she began to squeeze me past my breaking point, when she made me scream with pain, it was her way of showing me that she was using HER balls as she pleased.

And when I realized that, I was... grateful. I felt utterly and completely free. Free from having to pretend that I was, in any way, a real man. I never dreamed about sex; only masturbation. My penis was embarrassingly small and perpetually limp. My balls now belonged to the woman on whose shoulder I was crying helplessly. And I'd never felt safer or more secure than I did in that moment.

"You're a fucking bitch," she'd said. And as I hung there, sobbing, all I could think was, 'Oh my god, Carrie. Thank you so much for giving me the opportunity to be the fucking bitch that I know I am!"

I don't know how long I cried. I just remember that she held me for as long as I needed to be held, with all the patience in the world. But when I had no more tears left to give, she began to speak softly in my ear.

"I'm not going to apologize for what I just did to you, Jack. I think you understand now that you deserved it. You also needed it. You needed to be put in your place. I truly believe you're going to emerge from this experience an even better and more devoted houseboy. So I'm not going to apologize. But I am going to thank you. Jack, ever since I hired you, you've been trying to help me find confidence in myself. With what we just did, you've shown me how truly powerful I am. And how truly powerless you are. I hurt you, Jack. And I don't feel the least inclination to apologize for that. What's more, before this is over, you're going to thank me for it. That's real fucking power. Thank you for showing me that I have it."

Still too weak to speak, I nevertheless smiled, my head resting on her shoulder. It was wonderful to hear her speak with this kind of confidence, to listen to her glorying in her power. In accepting the fate that I had deserved, she had been elevated to the place of honor that was rightly hers.

"Jack," she said. "I'm going to let go of you now. And when I do, I expect you're going to fall to the floor. Do you know why?"

"Because that's where I belong," I whispered.

"That's right, honey. That's exactly where you belong."

A moment later, her arms were releasing me and I collapsed to the ground. Laying flat on my back, I looked up at her. She looked down at me. And she was smiling...