Naked Houseboy & his BBW Boss Ch. 17

Part 17 of an ongoing story...

Literally the same day that we had sent the invitation to the party, we received 'yes' RSVP's from all four of the girls. Clearly they were excited about it. And we were too. There was a palpable electricity in the air for the next two weeks leading up to the party. Carrie and I talked a lot about the preparations. We wanted everything to be just right. But there was one subject Carrie never brought up, and I knew she never would. So it was up to me. I went to go find her.

I found Carrie sitting up in bed, reading on her iPad. Her door was open, so I knocked lightly on the frame. She looked up.

"Hey," she smiled.

"Hey," I smiled back. "You gotta sec?"

"Sure, come on in." As I crossed the threshold, it occurred to me that this was a first. Of course I'd been in Carrie's room many times; to clean, to change the sheets, that sort of thing. But I had never been in her room with her. We never talked about it, but it was her private space. Just one of those unwritten rules. I took a step back.

"It's OK. You're welcome in my room." And she flashed me that warm smile. I stepped forward again. I didn't want to beat around the bush.

"Look, I think we should talk about this chastity thing."

"Oh, that," she frowned, putting down the iPad.

"I know you're not crazy about it," I started.

"It just seems so...cruel," she winced.

"Hey, listen, it's not something I'd normally go in for, believe me. But I really think it's for the best, and I've already told you why." I tried to speak in soothing tones.

"I know, I know," she nodded. "But what's to talk about? I already agreed to it."

"Well, the thing is..." I trailed off. She studied my face.

"This isn't easy for you, is it?" she asked. I shook my head. She sighed softly. Then she patted the bed beside. "Come. Sit."

"Are you sure?" This was a lot. My first time being in Carrie's room with her and now she was asking me to sit on her actual bed? With her? She must have noticed my hesitation. "I don't bite," she smiled and patted the bed again. I climbed on and sat down beside her, my back up against the headboard.

"The thing is, I think we should practice with it. Before the party, that is."

"Practice?" she repeated.

"Well, yeah. I mean, the whole point is to keep me from being distracted. But if it's the first time I'm wearing the thing, I'll probably be very distracted. So I think I should try it out a few times before the party.

"I see," said Carrie slowly. "I suppose that's logical. But you said 'we' should practice. Where do I fit in to this?"

"Well, two ways," I scratched my head. "First, as much as I need to get used to wearing it, I think you should get used to seeing it. I mean, if the first time you see it is at the party, that will be distracting for you too probably." I didn't wait for her to answer. "Also, you need to...I mean, I think you have to keep the key."

"Wait, what?" She sounded shocked. "Why?"

"Well, if I have the key, then it's useless right? Like, that defeats the purpose."

"Hmm," she mused. "Yeah, I guess you're right. Well, OK. Hey," she smiled. "We asked the girls to keep an open mind. I guess I should too, huh?" And then she picked up the iPad, turning her attention away from me.

"What are you doing?"

"Well, we need to go shopping, don't we? The sooner we order this thing, the sooner we can start practicing." I tried not to notice that she didn't do a google search, but simply started typing the address of a particular sex shop, which autofilled after the first three letters. Once the page loaded, she typed the word 'chastity' into the search bar. The results came back instantly. She moved the iPad so it was between us. "See anything you like?" There seemed to be two basic choices. Either a cage type or a shell type.

"The cage probably breathes better," I suggested.

"Yeah, but it also looks like it hurts more if you get aroused," she offered clinically.

"I doubt either of them feel very nice if you get aroused," I countered.

"Probably not," she allowed. "Well, all things being equal, I prefer the cage. It offers a less obstructed view.

"Cage it is," I shrugged. We picked out a model that seemed nice and proceeded to the checkout. Now all we had to do was wait...

--

A few days later, a package arrived while Carrie was it work. The shipping label was discreet. There was no indication that it came from a sex shop. But of course I knew what it was. I wasn't going to open it alone though, so I left it on the kitchen table until Carrie got home from work.

When she finally did get home, I was waiting for her in the kitchen as usual, her glass of wine in my hand. She didn't seem to notice the package at first and we proceeded to our by now usual guessing game.

"How was your day?" she asked

"Meh," I shrugged.

"Just meh?" she repeated. "Let's see about that." Then she crouched down into her usual inspection position, face to face with penis. "Well, this is unexpected," she mumbled to herself. She cupped my balls, every so lightly and frowned. Releasing them a moment later, she stood up again and looked at me. "Just once?"

She wasn't asking for confirmation about her guess. It wasn't even a guess. It was an assertion, and a correct one at that. What she meant was, "What the hell happened that you all only jerked off once today." I looked over her shoulder to the box on the kitchen table. She turned to follow my gaze, only then seeing the box herself for the first time.

"Is that...?" she started.

"Yeah..." I finished.

"Should we open it?"

"We kinda have to, don't we?"

"Don't you want a drink first?" she suggested. I nodded. For once she poured me a glass of wine instead of the other way around. Then, together, we approached the box. After staring at it in silence for what felt like minutes, Carrie finally opened the parcel and removed the packing paper. I just stared. But she, every so slowly, picked up the metal-caged chastity device, rotating it in her fingers, looking at it from every angle. I followed with my eyes. At last, unbidden, she handed it over to me. It felt cold. And while I was holding it, Carrie peered into the box. A moment later, she removed a small key which was attached to a metal necklace. In my hand, the chastity cage, in hers the key. For a long time, neither of us said a word. Finally, I summoned my courage.

"Maybe I should try it on?"

"Are you ready?" she asked, still looking at the key. "Or wouldn't you rather get one out of your system first?"

"Jeez, I don't think I could get hard right now if I tried," I said. Something about that thing was giving me the chills, even as I felt a rush of excitement. Carrie looked at me with growing curiosity. First I slipped on the base which, when in position, formed a ring around the base of my shaft and behind my balls in way that pushed them forward somewhat. Then I slid on the cage itself. It was spacious enough that it wasn't uncomfortable, at least in my current limp state. The only thing left to do was lock it. "Carrie?" I whispered.

"Huh?" she muttered, barely audibly, transfixed by my caged cock.

"They key."

"Oh. Right." And she handed it to me without another word, leaving me to secure it myself. Slowly, I inserted the key into the lock and, taking a deep breath, I turned the key. I then handed it back to Carrie, who hung it around her neck where it adorned her magnificent bust.

"How do you feel?" she asked with genuine concern.

"It's not too bad actually." It wasn't, at least so far. "You know what's funny though?"

"What's that?"

"My balls feel really exposed." I nearly chuckled. "What a weird thing to say, considering I'm naked all the time right? But they feel really...I dunno...out there."

"It's because of the ring," she said, taking a closer look. "It's kinda like a pushup bra for your balls." She started to giggle.

"Oh, that's funny, is it?"

"Yeah, a little!" She tried to stifle a laugh. "Hey Jack, you've got great...ball cleavage!" She couldn't contain herself. She started to cackle. She was laughing so hard her whole body started to shake. The key to my cage was bouncing up and down on her heaving bosom. That was the very last thing I needed in my condition.

Finally, the laughter began to subside. "I'm sorry, Jack." And her smile crept into a frown.

"Ah, forget it," I said with a wave of the hand.

"No, I mean, I'm sorry you feel like you have to do this. All joking aside, I don't love seeing you in that thing."

"I know, C." And then she handed me the key.

"Why don't you take it off, huh? We can start practicing for real tomorrow."

"Sure, why not." Taking the key from her, I quickly undid the lock and removed the device. Almost the moment I was free, I started getting hard.

"Well that didn't take long," groaned Carrie, rolling her eyes.

"Seriously," I said, even as I reached my right hand downwards and started massaging my stiffening cock. "And now, if you'll excuse me."

"Since when do you excuse yourself?" she shot back.

"Fine, I'll stay," I said shortly.

"Don't do me any favors," she sniped.

"Well which the hell is it C, do you want me to stay or do you want me to go?"

"Stay. Go. Do what you want." That's what she said, but it was clear she only meant one of those options.

"Women!" I groaned. Yet my irritation was a front. This banter was really turning me on, and Carrie knew it. She placed her hands on her hips and spoke in a stern voice.

"Look. All I'm saying is, I don't much appreciate it when, the moment you get a hard-on, your first instinct is to run away from me so you can go jerk yourself off somewhere else. I mean, if you're too embarrassed or ashamed to masturbate in front of me, maybe I should just put you back in that little cage!"

God, the way she was talking to me! I was rock hard, red in the face and stroking at full speed. And she could read me like a book.

"I mean, what's the point of a naked houseboy if he's only ever going to show me his useless limp dick and then he runs and hides the minute he starts to get a little hard? If I was interested in seeing your flacid penis I would have locked it up a long time ago!"

I didn't know what the hell this was or where the hell it was coming from, but I knew I was loving it. I closed my eyes and let the words wash over me as I stood there jerking off in the kitchen.

"And now you come to me," she continued, "and suggest chastity for yourself? The nerve! What right do you have to deny me the pleasure - if I can even call it pleasure - of looking at your hard cock?" I was going at if full speed now, breathing heavily. "Well? I'm waiting!"

"No right," I heaved.

"That's right! You have no right to deny me the sight of your hard cock. In fact, you have no right to deny me anything I want to see. Which is why you're going to cum in three...two..." I opened my eyes to see her still staring at me, hands on her hips, eyes narrow. "One!"

At her instruction, I exploded all over the kitchen floor, my knees shaking, face red, sweat dripping from my brow. When I'd spent my last drop, her whole body relaxed and she smiled at me.

And then, without any warning or announcement, she simply walked out of the kitchen, right past me, careful not to step in my mess. When she reached the doorway, she called out with out turning around.

"I'm gonna go change. Clean that up, will you?" And then she was gone...