Naked Houseboy & his BBW Boss Ch. 32

*Part 32 of an ongoing story...

The next morning, we awoke feeling very much refreshed. At first, we followed our usual routines, making no reference to last night's events or conversation. It was only after Carrie had had her coffee and was getting ready to leave for work that things went in a slightly different direction.

I stood naked in the kitchen, facing her, the chastity device on the counter beside me. As she had done the day before, she took the key from around her neck and went to hand it to me, silently indicating that I was to lock myself up again for the day.

"Actually, Carrie," I said, pulling my hand back. "Maybe you should be the one to do it. Just feels like a real power move, you know?"

At this, she grinned wickedly and, with one finger, beckoned me to approach her. Grabbing the chastity device off the counter, I closed the distance between us and placed it in her waiting hand. Carefully, silently, she took hold of my balls and slid the ring around them. Then, with equal attention, she pushed the cage over my dick. Finally, she fit the key to the lock and turned it before hanging it back around her neck. For a moment, we just looked at each other.

"Have a nice day at work," I squeaked.

In response to which, she pulled me into a tight hug. I could feel her enormous breasts pressed against my naked chest, the heft of her belly against my now caged and trapped dick. I could feel her hand sliding down my back until, suddenly, she had taken a firm grip on my ass. My dick was fighting the device, straining against it. And she knew it.

"Have a nice day at work, Jack," she whispered in my ear before at last letting go of me. With that, she started to walk towards the door. When she got about halfway, I called out to her. She turned to look at me.

I knew what I wanted to say. I wanted to say, 'How can you leave me like this?' 'How can you tease me and then leave me here all locked up with no hope of relief?' But I didn't say any of that. I just looked at her. I'm sure she could read it all in my face. Indeed, for a moment, she wore a look of what might have been pity. But her lips quickly turned into a slim smile.

"Yes, Jack? Did you want to say something?"

"Just...I'll see you this evening." It was practically a whimper.

"Yes, you will," she nodded. And then she was gone.

Once she'd left, I was able to get some kind of control over myself and my body. From that point on, it was just a normal day. Well, as normal as a day in chastity can be. I did my assigned work and I did it well. The hours passed pleasantly enough. There was one moment though, where the reality of my present situation caught up with me.

I was putting some laundry away in Carrie's room when I happened to pass in front of her full-length mirror. I stopped and looked at myself, realizing that until that moment, I'd never really seen what I looked like in chastity. At first, it struck me as sort of an odd thing. Had I still been living alone, this was not something I would ever even have considered experimenting with.

In that sense, it was positively weird. For as long as I could remember, all I ever wanted to do was simply jerk off as much as possible. Then I found this, my dream job, and was given the opportunity to do just that. To the point where, just this past weekend, I had masturbated so much that by the end of the jerkathon, I could no longer even get an erection. And I'd been proud of that fact! But now here I was, locked up and unable to wank at all.

Ostensibly, I was doing this chastity thing to prepare for the party. But last night's conversation with Carrie had put it all in an entirely new light. In allowing myself to be locked up - and in the process giving up my freedom to jerk - I was submitting myself to her will, her power. I couldn't find words to describe what I was feeling in that moment, I just knew it felt good. I wondered if she was, even then, playing with the key between her fingers, as I'd often seen her do. I smiled at the thought of her basking in her power over me while I was home alone, helpless to do the one thing I most wanted to do.

----

Carrie arrived home form work at her usual time. As always, I had a glass of wine in hand, waiting for her. As soon as she entered the kitchen, I could tell that whatever strangeness or tension might have existed yesterday had totally passed. Things now felt as easy and natural between us they ever had. The only difference now, was that my being in chastity would necessitate a slight change in our daily routine.

"Well I guess there's no point in doing an inspection," I shrugged. "Obviously I didn't jerk off today."

"Yeah," she frowned. "I was actually thinking about that the whole way home."

"No kidding?" Personally, 'inspection' was always one of my favorite parts of the day. I loved the way she'd crouch down and get her face right up in there, poking around my dick, testing my balls, trying to guess how much I'd masturbated while she was at work. I was surprised, though, that it was on her mind as well.

"Really," she nodded. "It's a shame we'll have to give it up this week. And yet, maybe there's a substitute."

"What kind of substitute."

"Come here," she commanded, pointing to a spot on the floor just in front of her. "And spread your legs just a little bit."

I did as I was told. And when we were standing mere inches from each other, she looked right into my eyes. I was so lost in her gaze that I didn't even see her right hand shoot down between my legs. I only became aware of it when I felt her grip on my balls. My eyes went wide, but she never stopped looking into me. For a moment, we just stood there like that, her hand around my balls, her eyes locked with mine. I opened my mouth to say something, but no words came out.

"Go on, Jack," she smiled. "Speak. If you can."

I just shook my head, my mouth still wide open.

"Then I'll speak. After all, you're kind of a captive audience right now." As if to add effect to her words, she gave my balls a light, momentary squeeze. "Now, I could tell you that what I'm doing here is a different sort of inspection. I could tell you that I'm curious to see how your balls react to a day in chastity. And maybe there's some truth to that. But we both know that's not what this is really about.

"This is about power. You know the expression 'to have someone by the balls'? Of course you do. Well, it seems to me that when you're in chastity and I've got the key, I've kinda got you by the balls. Figuratively, more or less. But as I was driving home, Jack, it occurred to me. Why stop at figuratively? All of a sudden, all I could think about was, what must it feel like to have a man by the balls. Literally."

"And...and how does it feel?" I could barely choke the words out.

"Oh my god, Jack, it's a fucking rush." And then she started to laugh. "Will you listen to me? I'm being so selfish. Is this OK for you? Am I hurting you?"

"This is great for me!" I declared, finally finding my voice. "And you're not hurting me at all." In fact, her grip was extremely light, to the point of being gentle. She may have been exploring this new feeling of power, but she was still being very careful with me. There was nothing about her hold on me that felt threatening or dangerous in any way. If anything, there was something very comforting in it.

"Good," she smiled. "Then you won't mind if I enjoy this a little bit longer."

"Take all the time you want," I offered. "And I would be very happy if we make this a part of our routine for the rest of the week."

"You're only in chastity for two more days, Jack."

"Then you should definitely take your time. In fact, why don't you tell me about your day?" I had learned early on that Carrie didn't love talking about work, especially when she first gets home. So I wasn't in the habit of asking her about her day. But on this occasion, it seemed like a good excuse to remain as we were. And so she did. With a glass of wine in her left hand and my balls in her right, we stood there for over 30 minutes while she told me about her day at work.

"Come on, let's go upstairs," she said when she'd finished. "We can watch a movie or something."

We actually wound up watching two movies, by the end of which, it was time for bed. Which, in fact, was the moment I had been waiting all day for. Finally, Carrie was going to let me out of chastity. I'd be able to jerk off and then we could go to sleep. Apparently, she had other ideas.

"Now Jack," she said coyly. "I COULD let you out now, just like last night. Or, we could try something different."

"What do you mean different?"

"Well, that's the thing. I'm not going to tell you unless you first agree to do it."

"So you're asking me to agree to something that I don't know what it is?"

"Don't you trust me, Jack?"

"Of course, Car. Just..."

"Just what?" Her eyelashes fluttered wickedly.

"Fuck it," I sighed. "Whatever you're thinking, let's do it."

"Oh good! I knew you'd see it my way." Her eyes narrowed. "So here's what's going to happen. Very shortly, I'm going to remove the chastity device from you. At that point, you will have three minutes - exactly three minutes, not a second more - to masturbate. If you can cum, then I expect you'll sleep pretty well. But if you can't cum, then it's going to be a rough night for you. Because if you fail to cum inside of three minutes, Jack, you're going back into chastity. You'll sleep in chastity, you'll wake up in chastity and you'll spend all day tomorrow in chastity. That's what's going to happen. Any questions?"

"Shit, wow. Um, do I at least get to watch some porn?" My mind was scrambling. What the hell had I just agreed to?

"No, of course not," she laughed. "But to show you that I can be kind, here's what I'll do. I'm going to find a picture of Kara on my iPad. Not in a bathing suit, but something where she's at least showing some cleavage. You can jerk off to that."

"Kind is an understatement!" Suddenly, three minutes sounded like plenty of time.

"Are you ready?"

I nodded. Carrie picked up her iPad and began to go through her photos in such a way that I couldn't see the screen. Finally, she selected a picture and handed the tablet to over to me. There was Kara, on vacation somewhere, wearing shorts and an extremely low-cut shirt, cleavage spilling out every which way. I was so engrossed in the picture, I barely noticed as Carrie undid the lock on my chastity device. In another moment, I was free.

"Three minutes," she said, queuing up the timer on her phone. "Starting...now!"

Immediately, I grabbed my dick and started tugging. I don't know if it was the excitement of being able to jerk off to this picture of Kara or the knowledge that I only had three minutes, but I started off at way too fast a pace. And since I wasn't giving my penis a chance to warm up, not much was happening.

"Seriously, Jack?" She sounded annoyed. "You've been locked up all day. How are you not getting hard for this?"

"I just need a minute," I panted, tugging even faster as if that might somehow help.

"You have literally three," she said sternly.

"I know, I know." Suddenly I was gripped by fear. What if I couldn't cum in three minutes? Was she really going to make me stop mid-jerk and put me back in chastity? How the hell would I be able to sleep if that happened? How would I ever get through tomorrow?

"I thought you told me that when you finally get to meet Kara, you want to be able to get hard for her?"

"I do!" I groaned.

"Really? Cause like, this is not a good sign."

"I know, I know."

"It's actually kind of ironic," she said, more to herself than to me. "I mean, you have such a thing for Kara. She's the only woman who, when you so much as hear her name, you automatically start playing with yourself. And yet, it seems like she's the only woman you can't get it up for. Oh my god, Jack, does she make you nervous?"

"I don't...I don't know...I don't...think so?"

"Ninety seconds." And then her demeanor changed. No longer did she sound annoyed. Her voice was filled with warmth and patience. "Jack, you're rushing. And you're panting like a dog. Slow it down. Yes, like that. Long deep breaths. In...out. In...out."

Of course she was right. It's what I should have been doing from the beginning. I felt my muscles relax, the tension leaving my body. I could feel my cock stiffening in my grip.

"Honestly, I always kinda envied her, the way she dresses, you know?" Once again, Carrie was talking to herself, and yet, clearly for my benefit. "I mean, I could never walk around with tits out like that."

God, those tits. I'd only ever seen cleavage like that in porn. But this was a real person. Carrie's friend, who I was going to meet on Friday.

"Oh," she smiled, looking at me. "So you CAN get it up for Kara. That's good to know."

I was rock hard now. Yes, this is how I wanted her to see me when we first met.

"Just in time, too. You've only got...wow, okay. Eleven...ten...nine..."

I was close, I could do this. I started to speed up. Now my cock was ready for it. I could feel myself approaching the brink.

"Eight...seven...six..."

"Fuck, Kara, look how hard I am for you!" I made eye contact with the woman in the picture as I cried the words.

"Five...four..."

"Oh fuuuuck!" The whole day's worth of pent up cum exploded from the tip of my cock, splattering my belly and chest.

"See, Jack? Plenty of time," winked Carrie as she patted cheek.

"Plenty of time, she says," I heaved.

"Yeah, but come on. Tell me that wasn't more fun than just watching some porn before bed."

"I'm learning not to argue with you," I smiled up at her.

"Hmm. I wonder if that's another added benefit of this whole chastity thing." Then she shook her head. "But that's a discussion for another day. Now, I think we should get some sleep."

I closed my eyes and drifted off...

-----

Wednesday and Thursday were not much different and before I knew it, it was Friday, the day of the party. True to her word, Carrie didn't put me into chastity that day. We spent most of the morning and early afternoon prepping, although I did manage to jerk off twice. By four o'clock, everything was ready. However, the girls weren't expected until eight. In other words, just enough time for me to have one more wank, a quick nap and a shower.

At 7:45, Carrie put me back into chastity. We looked at each other. She was dressed in a white blouse with a beige cardigan and a blue skirt. Her beauty was impossible to deny.

"Are you ready?" she asked

"I'm ready. Are you ready?"

"I'm ready," she nodded. "Are you nervous?"

"Maybe just a little," I confessed.

"Hey," she cooed, reaching down and grabbing me by the balls. "You're gonna do great. They're gonna love you. I promise."

Strange to say, perhaps, but feeling her hand wrapped around my balls instantly put me at ease. I felt safe, under her protection. In that moment, I didn't care if her friends ever showed up. I could have spent the whole night like, just standing there, my balls in her gentle grip. I opened my mouth to speak, but before I could say a word, the doorbell rang.

"Now I wonder who that could be." She let go of my balls. "Better go answer the door, houseboy..."