Naked Houseboy & his BBW Boss Ch. 31

*Part 31 of an ongoing story...

The jerkathon was over. The goal had been to see how much I was capable of masturbating in a 24-hour period. In this, our first attempt at such a test of endurance, I'd managed right around 13.5 hours, cumming a total of six times. Which I thought was a solid effort. Now to be fair, there were some significant stretches in there where I wasn't hard. But after discussing it - and we did discuss it - Carrie and I both agreed that if I was jerking my dick, it counted. This discussion, however, would come later.

In the immediate aftermath of things, we simply passed out. We'd been up for most of the past 24 hours with only one short nap the whole time. When we next woke up, it was nearly 9pm. In other words, we'd slept over ten hours straight. Feeling refreshed, we did a sort of debrief, checking in with Carrie's notes to total up my times and the like. We also agreed that it had been a ton of fun and that we absolutely had to plan more jerkathons in the future. Then the conversation turned towards the coming week.

"I think we need to talk a little bit about the party on Friday," began Carrie, "and how you want to prepare for it."

"Are we talking about chastity now?" I didn't see any sense in being coy about it.

"Well, yeah, that's the idea. But I mean, first things first. Are you sure you even want to go through with it? Being in chastity when you meet my friends, I mean. Working the whole party in chastity."

"It's not so much that I want to, C. It's more that I feel like I absolutely need to."

"Need is such a strong word," she noted. "Why do you put it that way?"

"So like, in general," I began, "I'm so used to being able to touch myself whenever I want. If you don't lock me up, I'm liable to reach for my dick without even thinking about it. And that's all things being equal. But earlier, towards the end of the jerkathon, you pointed out the effect that even just mentioning Kara's name has on me."

"Oh yeah," she smiled. "Every time you hear...her...name, you just start playing with yourself."

"Right, so imagine what it would be like if she's in the room!" I followed. "Every time I look in her general direction I might start going at it."

"Yeah, but Jack, let me ask you. So what?"

"What do you mean 'so what?"

"I mean, so what?" she repeated. "When you meet them, you're going to tell them all about your relationship with masturbation, right? So what's the big deal if you behave in front of them the way you normally behave. Are you embarrassed or worried they won't accept you?"

"Oh, not at all," I laughed. "If we were all just hanging out as friends, I'd have no problem with any of it. And who knows, if we all hit it off on Friday and we get together again in the future, I'd be very happy to do my compulsive jerk off thing in front of them. But that's not what Friday is about. Friday is their chance not just to meet me, the person. It's also their chance to meet your houseboy.

"And when they meet your houseboy, I want them to meet a guy who's attentive and dedicated. Someone's who's focused on serving you and serving them, without getting distracted by his own self-indulgences. And the only way I can trust myself to do that is if I'm locked up. Does that make sense?"

"Jack," she cooed. "It makes perfect sense. And honestly, I personally love the idea. I just wanted to make sure you were doing it for the right reasons. And now I can see that you are. But if you're really going to do this, I have thoughts."

"What kind of thoughts?" I liked the sound of it already.

"Well, we've already done a bit of practice with it. I just think," she bit her lip, "it's not nearly enough. I mean, the point is for you to not be distracted. Well, okay, the chastity device should free you from wank-related distractions. But the device itself could be a distraction. I think it's not enough for you just be comfortable in it. I think you have to actually be used to it."

"What are you proposing?"

"Starting tomorrow, before I go to work, I think we should lock you up. But this time, instead of letting you out when I get home, I think you should stay locked up for the rest of the day until bedtime. Then, just before bed, I'll free you. You can have a quick wank and then we'll go to sleep. Next morning, before I leave, we'll lock you up all over again."

"And you want to do this all week?" It sounded daunting to say the least.

"I was thinking Monday through Thursday, actually. Friday," she continued, "I'm gonna take off work and we can both prep for the party. But also on Friday, I think you should get a couple of rounds in before the girls show up. I think it's probably a good idea if you relieve some pressure in advance, you know what I'm saying?"

"I know exactly what you're saying. I agree about Friday, at least."

"And what about the rest of it?"

"Yeah," I said with a deep breath. "I can't say it sounds like a fun week for me. But I also can't argue with your logic. I just hope a week is enough time for me to get used to the damned thing."

"If anyone can do it, Jack, it's you."

We would soon find out...

----------

My original expectation was that the week would grow more difficult as it went on. In fact, Monday was the worst day. As we'd discussed, I put the device on just before Carrie left for work. And honestly, the workday itself wasn't so bad. Since I'd basically taken the whole weekend off on account of the jerkathon, there was plenty to do around the house.

What made Monday so difficult was spending the whole evening with Carrie while being locked up. And even that wouldn't have been so bad if I'd felt like she was her normal self. But she didn't seem to be her normal self. She barely said a word to me. While we were watching TV, I often caught her glancing at my caged cock when she thought I wasn't looking. I also noticed that she spent a good deal of time toying with the key around her neck, caressing it with her fingers. Once or twice I asked her if everything was alright. She assured me everything was fine, she was just distracted.

Well, alright, maybe she was just having a night. It happens. I just wished, then, that I could go off to my own room and masturbate. I figured that's what I needed, just as she probably needed to be alone. But of course I couldn't. That's what made Monday so difficult.

Finally, at around 11 o'clock, Carrie declared that she was ready for bed. She then, rather unceremoniously, handed me the key from around her neck. Her eyes were riveted as I turned the key in the lock and freed myself from the device. Only when it was finally off did the usual smile return to her face. Neither of us said a word as I began to stroke my dick.

Apparently one day in chastity was enough to cure me of yesterday's penis issues, as I got hard in a hurry. I made no pretense and stared boldly at Carrie's chest as I stroked. God it felt good to be able to stare at her tits and not pretend I wasn't. It also felt good just to have her standing there, silently watching me as I jerked off to her.

I knew I was close. I also knew that I was about to make a mess all over the floor if I didn't think of something. Almost instinctively, I cupped my left hand just in front of my cock. When the moment came, I tried to catch as much of my load as I could. It wasn't long before I was standing in front of Carrie, my dick in my right hand and a pool of cum in my left.

She looked at me with a face that said, 'Now what are you going to do with that?' But she spoke no words. Obligingly, I raised my left hand to my mouth and licked up every last drop of the thick, white liquid. She nodded approvingly. But then she fixed her eyes to a spot on the floor where a few extra drops of cum had landed. I looked at the spot. I looked at her. She nodded again.

In that moment, I wondered if this was the price I had to pay for so brazenly jerking off to her. In any case, it was clear what was expected of me. I got down on my hands and knees and, very carefully, lapped up each drop of cum which I'd failed to catch. When I'd finally swallowed the last of my mess, I looked up at her from the ground, still on my hands and knees. Only when she nodded again did I finally stand back up.

Then she nodded towards the bed. We both climbed in as she flicked off the lights. I expected her to cuddle up against me as she so often did, but this time she just lay beside me, on her back. The silence that followed was borderline uncomfortable and I was glad when she finally broke it.

"Jack," she said, almost in a whisper. "I have a confession to make."

"What is it, Car?" Finally.

"I'm discovering that I really like having you in chastity."

"That's...good?" I paused. Since I was going to be in chastity for most of the week, I figured it was probably a net positive if she enjoyed the experience. I didn't see why it needed to be a confession.

"You don't understand, Jack," she resumed. "I really like HAVING you in chastity. It's not about how you look wearing it. It's not about how you act when you're caged, or how much extra work you do around the house. It's about knowing you're locked up and that I have the key around my neck. It's about knowing you've surrendered the most precious thing in your world and that only I can give it back to you.

"When you're in chastity and I have the key, I feel a kind of power I've never felt before in my life. It's intoxicating, Jack. I love it. But also, it kinda scares me and makes me feel guilty. Like I'm taking advantage of you so I can go on some kind of deranged power trip or feed my ego or whatever. Am I making sense?"

"You're actually making a lot of sense," I replied flatly. "And honestly, given the way your ex-husband treated you, the way you've had to fight for your career...I can only begin to guess how good it must feel to be able to experience that kind of power. I mean, maybe this is another one where I can't exactly 'feel it with you.' But I can certainly appreciate it."

"So you're saying," she said, her voice still a near whisper, "it doesn't bother you? Like, if I told you that while you were home, struggling through your day, unable to jerk off, I was sitting at my desk, playing with the key and just feeling like an absolute queen...that wouldn't bother you?"

"Honestly, C? I much prefer that to the notion that you might be sitting at work worrying about me or feeling guilty. If a side effect of this chastity practice is that gives you a chance to feel powerful, then how can I not love that? In fact, just knowing this is going to make the rest of the week so much easier for me now."

"Really?" She sounded surprised.

"Of course! Now I know I'm not just training myself but doing something to help you feel good. That's gonna make things a thousand times easier."

"Wow, Jack. I was really worried you'd be upset with me. That maybe you'd think I was enjoying the difficulties being in chastity puts you through." Now she turned on to her side and snuggled up against me. "I never should have doubted you. Although..."

"Although what?" I asked.

"Although," she repeated, "I wonder if I should press my luck. Think you can handle another confession?"

"Bring it on."

"So these thoughts about power were on my mind the whole day," she said with more confidence now. "All I could think about was this new kind of power I seemed to have over you. And when you were jerking off before, I got the idea to...well, test you."

"Test me?"

"Or test me. Or maybe both of us. But to do a test, is the point." She paused and thought for a moment. "It would be a test to see if I could get you to do what I wanted using only eye contact and body language. I don't know if that's a test of my power or your obedience or..."

"Aren't they sorta two sides of the same coin?" I suggested.

"I guess they are," she conceded. "Anyway, that was my idea. And it was amazing. I'd think a command in my head, and just the way I'd look at you, you knew exactly what I wanted. Not only that, you did it without flinching or wasting a single second. God, the rush of power I felt, Jack! Watching you get down on all fours to lick up your cum without me saying so much as a word, just from you reading my body language? Fuck, a girl could get used to that sort of thing."

"Then we should find ways to do more of that," I smiled. "I mean, I can hear the excitement in your voice as your talking about it. I want that for you, C. If there's things I can do to help you feel that way, I want to do them. I have no problem getting down on all fours for you if it's gonna give you that power rush."

"Oh, I know," she grinned. "And I'm pretty sure I know why, too. Which actually brings me to my next point."

"And that would be?"

"When I saw you get down on the floor like that, I realized that I was actually really happy about the size of your penis. Because all I could think while I was watching you was, 'I'm pretty sure no guy with a big dick would be doing this right now.' Like, I could just sense that whatever power I already had over you, it was that much more because you know you're too small for me. Which made me feel even more powerful."

"Well this is fucking weird," I muttered.

"Shit, is it?" groaned Carrie. "I guess I thought...I mean, yesterday you were saying you want us to be able to talk openly about the size of your penis."

"Oh, I do want that. No, I love this, are you kidding?" In fact, I loved it so much, I could no longer delay the inevitable and began to slowly pull on my stiffening cock. Though Carrie hardly seemed to notice. "No, what's weird is, I sensed it to."

"What do you mean?"

"So this weekend, we watched some of your slideshow together, right? It was the first time I ever saw what your face looks like when you're looking at dicks that actually turn you on. So then, when I was jerking off before, I looked at your face. And it was very much not the face you had when we were watching your slideshow.

"And I knew, right? Whatever you might have been feeling while you were watching me, it was not a feeling of sexual pleasure or arousal. And I knew it was because of the size of my penis. Suddenly I felt smaller and weaker. But when I looked at you, you looked bigger and more powerful. It was hypnotizing in a way. I thought maybe that feeling would wear off after I came, but it didn't. If anything, it only got stronger."

"Jack," interrupted Carrie. "I think you should be careful about what you say here. The kind of things you're talking about - that we're talking about - these are the kinds of things that could affect the dynamic of our relationship."

"Well," I said carefully, "if the things we're saying are true, then maybe we should be affecting the dynamic of our relationship."

"Maybe, Jack. But also, maybe if we're going to do something like that, you should be talking with a clear head. Maybe we shouldn't have this discussion while you're jerking off." It was the first time she'd given any indication that she was even aware I was masturbating.

"I appreciate that, Carrie. But I want to talk about this now. I feel comfortable talking about it now."

"Alright, Jack. Go on."

"After I came, I saw the way you were looking at me, at my penis. And in that moment, it felt very small in my hand. But then you looked at me, my face, with the warmest smile. And it put this feeling into me where all I wanted was to make you happy. I remember thinking, 'Carrie deserves a bigger dick than this and I can't give her that. So what can I give her?'

"Then I looked at your face again and realized I knew exactly what you were thinking, what you wanted. It was like I could hear your voice in my head, telling me what to do. And when I realized you wanted me to get down on the floor and lick up my cum, I just remember feeling like, well, given the size of my penis, it's literally the least I can do.

"And then...oh, fuck, Carrie, I think you're gonna get your wish." I felt my orgasm approaching like an oncoming freight train. I didn't try to get out of the way. In a matter of moments, it ran me right the fuck over, leaving a mess of cum all over my belly as the feeling vanished into the night.

"What wish is that?" asked Carrie after waiting a few seconds for me to catch my breath.

"That I can have this conversation with a clear head and not while I'm jerking off," I answered calmly.

"Oh, right," she smiled. "Speaking of which, is there anything you'd like to take back or revisit now?"

"Not one word," I grinned. "If anything, I'd like to continue."

"Please do."

"So after I licked up my cum, but while I was still on the floor. I was expecting to be hit with this feeling of humiliation, right? Like, what had I just done? But when I looked up at you and saw the way you were looking at me? Carrie, you were majestic in that moment. The things you'd just made me do, without uttering a single word, I was in awe of you.

"And far from feeling humiliated, I felt like I was exactly where I should be. On my hands and knees, the taste of my own cum in my mouth, just because it pleased you. In fact, honestly, I felt grateful to you. Grateful that you would give me, with my small penis, the opportunity to do this little thing for you.

"You realize what we're saying though, don't you?" Her voice was a mix of concern and excitement.

"What are we saying?"

"We're saying that I love having power over you and that you love being under my control. We're also saying that the size of your penis is something that makes you less powerful and me more powerful. I mean, that is what we're saying, isn't it?"

"It does sound that way," I agreed.

"But, Jack, here's the thing. I never wanted like a domme/sub relationship. Yet isn't that kind of what we're describing?"

"I'm not sure. Maybe it is. But allow me to point something out. You're my literal boss. So already, I have to do whatever you tell me. In addition to that, the terms of my employment require me to be naked at all times; whereas, I've never once seen you naked. I suspect that to some people, this already sounds like a domme/sub relationship. So why not allow ourselves the chance to explore that a little further? I'm open to it if you are."

"That's not an unfair point, Jack," she said thoughtfully. "Fuck it, why not be open to it? This being your week of chastity, it seems like as good a time as any to test some boundaries."

"I can't fucking wait," I grinned.

"Well you'll have to wait until tomorrow, at least," she whispered. "Because we both need to get some sleep." With that, she slid her hand down between my legs and gently took hold of my balls.

"You know I love to fall asleep like this," I said softly as I closed my eyes.

"This isn't about you, honey," she whispered. "This is about me, exercising my power." With those words, she gave my balls a momentary squeeze before we both drifted off to sleep...