Naked Houseboy & his BBW Boss Ch. 33

*Part 33 of an ongoing story...

The doorbell had just rung and now I was about to meet the first of Carrie's friends. And not only would I be naked, I would be in chastity on top of it. I was nervous and I was excited.

I made my way to the door that opened onto the garage. Carrie had instructed her friends to use that entrance so that I could be the one to greet them. After all, it wouldn't do to have a naked man opening the front door of the house. I paused when I reached the door and took a deep breath, wondering which of her four friends would be on the other side.

Exhaling, I turned the knob and pulled open the door. Facing me was a petite red headed woman, a full head shorter than me. Her face was striking, with bright green eyes and the cutest button nose. She looked right at my face and smiled broadly.

"You must be Jack! It's so great to finally meet you!" With these words, she threw her arms around my neck and gave me a friendly hug, pretending not to notice - or genuinely not caring - that she was hugging a naked man. I returned her hug, being careful to leave some daylight between our bodies.

"And you must be Samantha," I said, letting go of her.

"You can call me Sam," she smiled.

I still didn't know what to expect from the rest of her friends, but in Sam's case, she radiated the same warmth and kindness that I'd gotten from Carrie on our first meeting. I knew instantly that I could trust her and that I had nothing to be embarrassed about.

Nevertheless, I hesitated for just a moment. As best I could tell, Sam had not taken the opportunity to look me up down, this naked stranger she had just hugged. So I just kinda stood there, waiting for her curiosity to get the better of her. Not that I wanted or needed the attention. It was more just that I expected even a furtive once-over to be anybody's natural reaction to such a situation.

"Well, aren't you going to show me in?" she finally asked.

"Of course, please excuse me. Where are my manners? Right this way, Sam." I offered her my arm, which she happily took.

"Jack, can I ask you a question?" We were walking rather slowly towards the living room and so had at least a few moments to chat.

"Ask me anything."

"Do you always wear that thing?"

So she had noticed! Sneaky.

"Not usually, no," I answered calmly. "But I guess everyone's gonna ask about it, so probably I should just wait til everybody gets here to explain."

"Oh, sure, that makes sense," she nodded. "I was just asking because, I guess...I mean, is it uncomfortable? It looks kinda cold."

"Oh, that," I shrugged. "Well, I guess I don't really have the biggest - "

"Oh my god, Jack!" Her face turned fire engine red. "That's not what I meant at all! I'm so sorry! I just...I mean, the metal...it looks cold...is all I wanted to - "

"Oh god," I groaned, turning bright red myself. We froze in our tracks, her arm still in mine, and just looked at our feet. Then, in the same instant, we looked at each other. And when we saw how embarrassed we both were, we started to laugh. The ice, it seems, was broken.

"You know, Jack," she said looking directly at me. "I'm guessing this is not the last time something embarrassing is going to happen tonight. Probably we should just try to embrace it."

"Or at least roll with it," I added as we resumed our way to the living room. By the time we entered, we were all smiles.

"Looks like you two are already getting along," observed Carrie, her hands on her hips, as she saw coming in. "Not that I'm surprised." And then, to Samantha, "Come here, girl!"

Sam ran right up to her and gave her just the same sort of hug she'd given me moments ago. Which was nice to see honestly, as it showed me that this was really who she was, that she wasn't acting any differently with me than she normally would. I didn't have much time to think about any of this, though, as the doorbell rang anew.

"That's probably Vicky," surmised Sam. "She was right behind me."

I made my way back to the entranceway. This time I felt none of the nerves which had earlier beset me, though the excitement was still fresh. I opened the door to reveal a woman with jet black hair, a full head taller than me, crazy long legs paired with a crazy short skirt and a sarcastic twinkle in her eye. This was definitely Vicky.

And Vicky made no pretense of discretion. Stepping inside, she brazenly looked me up down, even walking around behind me so as to see me from every angle. When she was once again facing me, she spoke.

"So, we meet at last. Jack, the naked houseboy."

"Nice to meet you, Vix," I answered coolly.

"Tell me, Jack. Does everything you guys wrote in the invitation still stand?"

"Certainly. But I suppose you're referring to something in particular?"

"That business about this being a 'hands-on' experience?" She cut right to the chase.

"Naturally," I nodded.

"So then, this is fine?" she asked, running the palms of her hands over my breasts.

"Of course."

"And this?" She pinched both my nipples.

"Yup."

"Or for example...this?" And she slapped my ass.

"Absolutely."

"Tremendous. Then I guess you won't mind if I also do this." This time it wasn't a question. And without waiting for me to even acknowledge it, she reached down and grabbed my balls. This was not, however, Carrie's gentle grip. This was a firm hold, not painful in itself, but enough to let me know that it could have been. Yet the little I knew of Vicky told me that she wouldn't appreciate a cowering pushover or whimpering sub. I knew how I needed to answer her.

"Listen Vix, hands-on means hands-on. So we can stand here all night while you look for excuses to feel me up. But there's a party waiting for us, and at some point, it might look like you're being rude to your hostess and the other guests."

"I like you, Jack," she grinned, letting go of my balls. "I don't know what this is about though," she added, flicking my cage with her middle finger. "But let's go in then, shall we?"

Moments later, we were all back in the living room. When the girls had all exchanged their greetings, Vicky turned to Samantha.

"So how do you like this whole 'hands-on' experience thing?"

"Well, honestly, I haven't partaken yet?" answered Sam, a bit shyly.

"Why on earth not?"

"I mean, I just met him!" protested Sam. "It hardly seems like the time to just start fondling him. And anyway, maybe I'd like to have a drink first."

"That's my job," I cut in. "What can I get you?"

"Martini?"

"Coming right up." As I disappeared off to the kitchen, I could still hear Vicky trying ot sell Sam on the merits of a true hands-on experience.

"Honestly, it's like getting into a pool," Vicky was saying as I returned with the drink. "If you try to go in one step at a time, it's too cold and you'll never enjoy it. You just have to jump right in."

"And that's relevant to this experience how?" asked Sam, accepting the drink from me and throwing me a winking smile as she did so.

"If you're looking for little ways to get used to the idea, you never will. You just have to go for it. I'm saying, grab him by the balls."

"Vicky!" Samantha was blushing, but I could swear there was something of a twinkle in her eye as she took her first sip.

"I"m telling you, girl, just do it and you'll feel much more comfortable with this whole situation. You might even start to enjoy yourself."

Sam turned to look at Carrie for help, but she only offered a don't-look-at-me shrug of the shoulders. Then Sam made eye contact with me. Only then, for the first time, did she look at my body. Her gaze came to rest between my legs as she bit her lip. Again, she looked up at me.

"Listen, Sam. You shouldn't do anything you don't feel comfortable with. All I can tell you is, if you're worried about me, don't be. I was the one who suggested this whole hands-on thing, not Carrie. So I'm totally okay with this, believe me. But you need to do what feels right for you."

"Well," she said softly, taking another sip, "we said we'd embrace the embarrassing things right?"

"Or at least roll with them," I smiled back.

"So let's roll with it," she said, handing her drink to Vicky. With careful, ginger steps she approached me so that she was now standing mere inches away. She looked up at me with her soft green eyes. "Are you sure you're okay with this?"

"One hundred percent."

Slowly, she reached down and took hold of my balls. It was an entirely new experience. She carefully maneuvered her palm and fingers, trying to find just the right for her hand. When she found it, her grip was firm, warm yet not forceful. And as she did all this, she just kept looking into my eyes, smiling. I got the feeling that this wasn't about power for her. She seemed to truly enjoy the way my balls felt in her hand. With the slightest of motions, I could feel the tips of her fingers moving, touching, probing, her eyes watching my face for any reaction to her change in touch.

I was loving every second of it. And it wasn't about power - or the lack thereof - for me either. This woman had me by the balls, was playing with them, wanting to make me feel good. And it felt so good. It felt like -

"All right, you two, break it up. Or get a room. Or get me a drink, at the fucking least." This was Vicky. And her words broke the spell. Sam immediately let go of me. I looked over at Carrie, and she seemed almost embarrassed by the whole situation. We quickly looked in opposite directions.

"Um, what can I get you, Vix?" I asked, taking a step back from Sam.

"Gin and Tonic, please."

"You got it." I heard the doorbell ring again while I was making the drink. By the time I got back to the living room, I saw that Allison and Kara had arrived; apparently they'd driven together.

Allison still had that sexy librarian look, with the glasses and tied up hair. Slim, wearing a knee-length black skirt, she looked pretty straight-laced. As for Kara, wow. She was wearing jeans and a low cut t-shirt that absolutely did not fit her. She was spilling out of it and she knew it. All I could do was hope I wasn't drooling. Introductions were made and I quickly filled their drink orders. Soon, all four of our guests were sitting on the couch looking at me and Carrie.

"So I'm sure you all have a ton of questions," Carrie began.

"Like, what's with the cage?" asked Allison calmly.

"Yeah, are we gonna get to see his dick or what?" added Vicky.

"Plus, are you guys seriously not fucking?" piled on Kara. Only Sam remained silent.

"All good questions," said Carrie, still standing beside me. "Take it away, Jack."

"Yeah, so as Carrie said, all good questions. And let me just say, I'm open to any questions you might have. Nothing is too personal or embarrassing. So whatever's on your mind, I hope you'll ask."

"Oh, count on it," was Vicky's response.

"Excellent," I smiled. "As for the questions you've already asked, do you want the short answers or the long answers?"

"Definitely the long answers," replied Allison calmly.

"Yeah, Jack, I think I speak for all of us when I say I want to hear literally everything," added Kara. Vicky and Allison nodded their heads in agreement while Sam looked on silently with rapt attention.

"So one of the reasons we organized this party," I began, "was just so that we could all meet and get to know each other. But another reason was to give me the opportunity to open up and be my real self with other people. Because my whole life, I've always felt like I've had to hide my true self, to be what other people expected me to be rather than who I know myself to be. In fact, it was only when I met Carrie that, for the first time in my life, I was able to be my true self with another person. And so, when she told me that I could trust you guys the way I trust her, that's when we decided to have this party."

"And what is this true version of yourself that you've felt you always needed to hide?" asked Allison. "Who are you are, Jack?"

"A devoted and passionate masturbator," I declared. I had felt confident, even proud, as I spoke the words. But they were met, at first, with nothing but stillness and maybe a few raised eyebrows.

"Alright, I'll bite," said Vicky, breaking the silence. "What does that mean, exactly, a devoted and passionate masturbator?"

"It means," I began, "that masturbation is my favorite thing in the whole world. For me, it's not something I do just when I'm bored or horny, it's how I want to spend all my free time. With me, it goes far beyond being even a hobby. It's an absolute passion. My goal, each day when I wake up, is to jerk off as much as possible. When I'm masturbating, I never want it to end, I want it to last as long as possible. And when I'm not masturbating, all I think about it is when I can jerk off again. I just love it so much. To the point where, if you give me the choice between masturbating and sex, I'll choose to jerk off ten times out of ten. Which, if you're prepared to believe that, explains why...well, it's one of the reasons, at least, that you can be sure Carrie and I aren't fucking."

"Why wouldn't we believe you?" asked Sam, speaking now for the first time. There was a softness, a kindness, to her words which indicated that she, at least, saw nothing even remotely strange or abnormal in my declaration. It was almost as if she were saying, 'So that's who you are. And it's genuinely nice to meet you.' The others, however, were not quite there yet.

"So let me get this straight," said Vicky. "Suppose Carrie were to tell you that she wanted to sleep with you. Your answer would be, 'No thanks, I'd rather jerk off?'"

"Well, it's kind of a moot point," I answered. "I mean, she made it clear, first in the job posting and then again at the interview, that under no circumstances would she ever sleep with whomever she hired as her houseboy."

"Granted," followed Kara. "But humor us. Hypothetically..."

"Hypothetically," I answered, "Yes. That would absolutely be my answer, with no hesitation." These words, too, were met with silence. For the first time, I was starting to feel self-conscious. "You all must think that's pretty strange," I added meekly.

"Strange? No, not strange at all," answered Allison dispassionately. "Just...different." She paused, thinking it over. "But I'll tell you this. I, for one, find your honesty refreshing, Jack."

"Oh, me too!" exclaimed Kara, picking up on Allison's sentiment with enthusiasm. "I mean, men are normally so full of shit. The objectify us, they try to manipulate us so we'll sleep with them. And then, when you actually get them into bed, most of them are fucking useless anyway.

"Meanwhile, here you are with your whole 'I don't like sex, I just wanna jerk off' thing and...I dunno, I think Ally had the right word. It's refreshing. Like, I just feel like i can trust you, off the bat. Now, don't take this the wrong way, Jack. I mean, you're a good looking guy, and I'm certainly enjoying the show over here. But when I look at you, I'm not thinking, 'There's a guy I'd like to fuck.' I'm thinking, 'There's a guy I could really be friends with.' I hope that's not, like, a hurtful thing to say?"

"Why would that be hurtful?" I asked.

"Well, just, normally guys talk about the 'friend-zone' as a fate worse than death, you know?"

"But that's exactly my point!" I exclaimed. "The whole point of this night - for me, at least - is to meet people who I can be my true self with and who will still want to be friends with me even after knowing everything I just said about myself. The fact that you just said you think you could be friends with me, I mean, nothing could make me happier." That's what I said, and it was most certainly true. But part of me was still thinking, 'Oh, Kara, if you only knew how desperately I wanted to jerk off to your cleavage right now, would you still want to be my friend?'

"In that case," said Allison calmly, "allow me to say that I would also like to be your friend."

"I'll go one further," added Sam. "Jack, even though we've only just met, I'd like to think that we're already friends."

"See? What'd I tell you?" whispered Carrie in my ear, nudging me gently in the ribs.

"Great, it's settled then. We're all friends," declared Vicky impatiently. "But you still haven't explained the cage."

"Right, I nearly forgot," I smiled. "So one of the wonderful things about Carrie is, she hasn't just accepted me for who I am, but she's actively encouraged me in my passion. Right from the very beginning, our arrangement has always been, as long as I get all my work done, I'm free to masturbate just as much as I want."

"Which is no doubt admirable," commented Allison. "But I have to ask. What you described sounds more like permission. Yet the word you used was 'encouraged.' It sounds like there's more to the story."

It was only then that I realized, that while I was perfectly comfortable talking about myself, I wasn't sure how much I had any business speaking for Carrie. I looked at her and though I didn't say a word, she nodded, seeming to understand my question.

"You're right, Ally," I acknowledged. "Permission is just the beginning. For one thing, we agreed at our interview that it didn't really make sense for her to pay me, in a traditional sense. I mean, I get room and board in exchange for my work. And I don't really leave the house since...well, you know. Point being, I don't really need money. So instead of monetary compensation, Carrie gives me a monthly porn budget that I can spend on videos, subscriptions, phone sex, whatever."

"Wait, you pay for his porn?" asked Vicky.

"I'll ask you to direct all questions to Jack at this time," smiled Carrie.

"Well if she payed me the regular way," I answered, "I'd just wind up spending it all on porn anyway. This way, it saves me the trouble of having to open a bank account or taking out credit cards. Plus, since she's paying for everything, we agreed that she should have complete access to all my passwords and browsing history."

"And you're okay with that?" asked Kara. "I mean, I for sure have looked at some stuff that I'd be embarrassed if other people knew about it. Like, I feel like everybody has watched at least some porn that they'd prefer to keep private. Or no?" In response to which, Ally and Vicky nodded silently. Samantha looked at the floor, blushing.

"In the past, I definitely would have have agreed with you," I answered. "But the whole point of this experience for me is to be as open as possible, to no longer have to hide anything about myself. And that includes literally all of my porn. I mean, maybe it's something about being naked all the time, that the idea of hiding anything now feels ridiculous. Or maybe it's because I just trust Carrie so completely, knowing she'll never judge me for anything I watch or get off to. So yeah, I'm totally okay with it."

"That actually makes sense," said Samantha softly. "It must be nice to never feel embarrassed about that stuff."

"I'm sure it's super great," cut in Vicky. "The cage, Jack."

"Right, right," I nodded. "So basically, we've created an environment where I can masturbate whenever I want. Like, in this house, it's perfectly normal for me to just start playing with myself at any given moment. I mean, sometimes I'll start tugging without even realizing what I'm doing." Like, whenever I hear Kara's name, I thought to myself, trying not stare at her cleavage.

"In other words, there's no way I could trust myself to get through this party without touching myself at some point. Which is not what I want."

"Jack, do you really mean to say that, after everything you've told us, you'd be embarrassed to masturbate in front of us?" asked Allison. "Because I promise you, nobody would be offended. Nobody would think you were being creepy or a perv. Now that we know you, we'd know it would just be you being you."