Naked Houseboy & his BBW Boss Ch. 16

Part 16 of an ongoing story...

Carrie's phone was ringing. It was Vicky, one of her best friends from college. "Wanna have some fun?" Carrie had asked when she saw who was calling. "Follow my lead." She answered the phone, putting the call on speaker. As she did so, she put one finger over her lips indicating that I should be silent.

"Hello?" she said.

"Hey girl," came the voice from over the phone. There was a little gravel to Vicky's voice, but it was very sexy. "How you doing?"

"I'm good, I'm good..."

"Yeah, I'll bet you're good, you and your naked houseboy over there!" Vicky wasted no time.

"First of all, the 'naked houseboy' has a name. And second of all, are you trying to imply something?" Carrie was sounding indignant, but then she winked at me to let me know this was part of the game.

"Me?" asked Vicky plaintively. "What on earth could I be trying to imply? I'm just saying, I'm sure you're...well taken care of...you know...by Jack."

"For the millionth time, Vix, we're not fucking."

"So you say, so you say. But you're happy with his, uh, work?"

"Very happy," answered Carrie with a roll of her eyes.

"Still though, even if you're not fucking - which I'm still not convinced of, by the way - it must be nice to have that naked body to look at all the time."

"I'll give you that," said Carrie. And she looked me up and down with a big smile. "He's very nice to look at."

"Come on, don't be coy. Tell me about his dick." As Vicky said this, Carrie shrugged apologetically.

"I don't know Vicky, it's a penis, what do you want me to say?"

"How big is it? Is he circumcised? All the usual things!"

"Why don't you ask him yourself?" answered Carrie with a wicked grin. Then, turning to me, she put a fist in front of her crotch and started pumping it in the universal jerk-off symbol. With her other hand, she pointed at me, telling me this is what I should be doing. I didn't need to be asked twice. I immediately started playing with myself.

"Ask him myself?" replied Vicky. "What do you...wait. Is he there right now? Am I on speaker?" Carrie nodded at me.

"Heeeyyy Vicky," I cut in.

"You bitch!" she chided Carrie. "Hello, Jack. Nice to finally meet you. How are you?"

"I'm fine, thanks. 6 and yes."

"I'm sorry?" Vicky sounded confused.

"You were asking about my dick. Six inches and yes I'm circumcised. Is there anything else you'd like to know?"

"No, uh...actually, that's...that's fine, thanks." Carrie was working hard to hold back her giggling. It was clear that we had caught Vicky and she was looking to change the subject. Carrie was not about to let her off the hook. "So, um, what are you guys up to," asked Vicky.

"Well," replied Carrie, "I'm having a glass of wine and Jack here, well, how can I put this? Jack is masturbating." Silence from the other end. "You still there?"

"I'm here. Sorry, it sounded like you said Jack - "

"Is masturbating, that's right." Carrie was only to happy to finish her friend's sentence.

"Ok, good one, Car, you got me."

"I'm not kidding," Carrie answered coldly. But Vicky wasn't having it.

"Bullshit. Jack?"

"Yeah, Vix?"

"For real now, what are you doing?" She asked in a way that sounded like she thought I could get her out of this mess.

"Carrie told you. I'm masturbating. Jerking off. Having a wank. Choking the - "

"OK, I get it. Well you guys obviously just want to fuck with me, so I should probably go..."

"No, don't go!" Carrie and I called out together. Then Carrie came over to me and whispered in my ear: "Give her the hard sell." To be honest, I wasn't totally sure what she meant. So I just did what came first to my mind. I started speeding up my stroke and then I spoke, ladening my voice with heavy breathing and little moans.

"Vicky...please don't...don't go yet...it's so hot to finally hear your...oh god, your voice...fuck...we really want...I really want you to...to - fuck! - to stay..."

"Ha ha ha, very funny you guys. Masturbating, my ass. Jack, that was a little over the top if you ask me." Carrie and I looked at each other, trying not to laugh. "Car, I'll talk to you later, OK?

"Later, Vix!" And then she hung up. As soon as the call was ended, we both burst out laughing. "Jack, you fucking nailed that! I could fucking hug you right now." And then she looked at me, still masturbating. "Obviously I'm not going to. Not now, anyway."

"Fair," I replied. "That's fair."

"Anyway, she had it coming. First of all," Carrie started to explain, "she's convinced we're fucking and she always brings it up and there's nothing I can say to convince her we're not. And second, she's always asking about you, about your body, about your dick."

"She is?" That was news to me. Hot news, too.

"Oh sure. Her and all the other girls. But I don't tell them anything other than that you're doing a great job and I'm very happy. I want to respect your privacy."

"Thanks," I said almost as an afterthought. "But what do you mean 'all the other girls' exactly?" That was clearly the more important issue here.

"Oh, just Vicky and my other three friends from college. You know, my little circle. They're the only ones who even know about you."

"And they ask about me?"

"All the damn time. Honestly, it's kind of annoying at this point."

"Well maybe I should meet them and then they wouldn't need to pester you any more."

"Wait, are you being serious right now?"

"Why not? I've heard you talk all about them, I'd be curious to meet them. And they're obviously curious to meet me. So what's the problem?"

"There's no problem," protested Carrie. "I just didn't want to put you in any kind of position where you felt forced or uncomfortable. And I could imagine it might be overwhelming to meet a group of women if they know you're a naked houseboy."

"Is there something wrong with being a naked houseboy?" I tried to sound hurt, but I wasn't.

"Stop that, you know what I mean. But if you're serious about this..."

"I am," I assured her. "Look, we can even make a fancy dinner party out of it."

"Ooh, a fancy dinner party!" echoed Carrie. "I like that idea. We can all get dressed up. What would you wear?"

"Why would I wear anything?" I queried.

"Oh, well, I just assumed. I mean, you've never met them. Maybe it would be weird for you to be naked in front of a group of women you've never met."

"But part of the point of this is, they want to meet your naked houseboy, right? Won't they be disappointed if the show up and said houseboy isn't actually naked?"

"Maybe. But I'm less worried about disappointing them and more worried about how you would feel."

"That's really sweet of you, honestly. But do you know what my least favorite part of this job is? I'm not complaining," I added hurriedly. "I'm just asking. Any idea, what my least favorite thing is with this job?"

"I guess have no idea," she answered slowly.

"Going shopping," I answered my own question. "Because it's the only time I have to get dressed. At this point, when I'm wearing clothes, I feel like a different person. Some past version of myself that was never as happy as I've become since I started working for you. So the truth is, I'd actually feel more uncomfortable if I did have to get dressed for this party. I'd feel like I was pretending to be something I'm not."

"Well, when you put it that way. And come to think of it," she added slowly, "I do remember how natural it was when you took your clothes off at our interview. Alright, naked houseboy it is."

"Good, then we're agreed. I mean, I can trust them, right?" The questions had only just occurred to me in that moment.

"Of course! You can trust them every bit as much as you trust me. They're my best friends in the world. I vouch for them." She paused. "You know, I was just thinking..."

"What?"

"I mean, because you really can trust them as much as you trust me..."

"What is it, Carrie?"

"Well, I was just remembering something you told me once. You always say one of the best things about living with me is how you're free to be yourself, how you can express yourself without fear of judgement. But one time you told me that it made you a little sad that I was the only person you could talk about these things with. How you wished you could be free to talk about your love of masturbating, but that's just not the world we live in..."

"I did say that," I nodded.

"Well, I'm just thinking. Since you can trust them the way you trust me, this could be an opportunity to share yourself with more than just me. You could tell them who you really are. I mean, if you're comfortable with doing that..."

"Oh, wow." I was not expecting this. Sure, walking around naked in front of her friends sounded like fun, serving them drinks and whatever. But opening up about my passion? That had never occurred to me. But the more I thought about it, the more exciting the idea became. There was only one thing.

"Carrie? I don't want to weird them out. I mean, what if they think I'm some kind of creepy perv or something?"

"Oh, don't worry about that. First of all, they're very open minded. Shit, I mean, you heard Vicky on the phone. If anything, I'm worried that you're gonna be the one thinking she's a perv." She laughed in a way that hinted at some truth behind the jest. "But beyond that, I'll be right there with you. I promise I won't let them think you're a creep or a perv. I got your back."

"Alright, well, if it happens, then that would kind of be a dream come true, I'm not gonna lie. But let's play it by ear, OK?"

"Sure, however you want," she smiled warmly, putting me at ease. And now that I was feeling more comfortable again, my mind started working. The ideas started coming.

"You know, C, if they're going to get the 'naked' experience, we should make sure they also get the 'houseboy' experience."

"What do you mean, Jack?"

"Well, I don't want to be a guest at this party. I want to be a working houseboy. I want to be on everybody's beck and call. I want them to take full advantage of being at a party where they can be waited on hand and foot. Let's make it an unforgettable experience."

"Be careful what you wish for, buddy boy." The way she was looking at me almost gave me a chill. It was like she was saying, 'You don't know my friends. You can trust them. But you might get more than you bargained for.' I could feel my dick growing harder in my hand. "Maybe we should make some ground rules," she added.

"Hey, great idea! Actually, why don't we write the ground rules into the invitation?" I suggested.

"What do you mean?" she asked.

"Follow me." And I walked out of the kitchen and across the hall into the computer room. "Open up an email," I directed. Carrie sat down in the computer and did as I asked while I stood beside her, still playing with myself. "Do you take dictation?" I joked.

"I have a secretary for that," she answered coldly but with a wink. "Alright, what do you want to say?"

"OK, subject line: 'You're Invited.'" She started typing. "Title in the body of the email: 'Meet the Naked Houseboy.' Good, now the text." I spoke the words as they came into my mind and Carrie dutifully typed them out.

>>Dear Friends,

I have decided that it's finally time for you to meet Jack, my naked houseboy. And for Jack to meet you all, my best friends in the world. Therefore, we would like to invite you to a fancy dinner party on...<<

"When do we want to do this?" I interrupted myself.

"A week from Friday?" suggested Carrie. I nodded.

>>...on Friday the 18th, 8pm. Everything will be provided. You need not bring anything except yourselves and an open mind.<<

"An open mind, I like that," interjected Carrie. I smiled and continued.

>>Now, as I suspect none of you have ever attended a party with a naked houseboy before, I thought it would best if we offered some guidelines and suggestions on how to act, so as to best avoid any awkward situations or social discomfort.

It may be that your first instinct will be to stare. You are more than welcome to do so. In fact, it's encouraged. We don't want anybody to spend the whole evening feeling like they have to avert their eyes. After all, what's the point of a naked houseboy if you can't look?

For most of a us, a naked houseboy is a novelty. We assume you will have questions. We know each other long enough, I'm confident you won't be shy about asking me questions. But as this is the first time you'll be meeting Jack, perhaps you will be shy about asking him questions. Don't be. You are free to ask him about literally anything, from the banal to the deeply personal. He may decline to answer a particular question, but you should never feel awkward about asking.<<

"So far so good?" I checked.

"Oh yeah, this is great!" Carrie nodded enthusiastically.

"OK, this next bit...maybe it's going to surprise you. For now, just type what I say. If you don't love it, we can always take it out." She looked up at me suspiciously, but nodded all the same. I went on.

>>That should cover things as far as actually meeting Jack. But this is more than just a meet-and-greet. This is a party. And as such, we want you to have the full houseboy experience. Therefore, we ask you to remember that Jack is not only Carrie's friend, but very much her employee. He works for her, and this evening, he will work for you too. Anything you need, you have simply to ask, and he will provide it for you. Our home is your home. Do not feel shy about asking Jack for even the smallest convenience.

With that in mind, we want to maximize the naked houseboy experience as much as possible. In this case, that means making this a hands-on experience. For example, Jack is happy to provide foot rubs and shoulder rubs upon request. Again, these are examples. If there is something you want, don't hesitate to ask.

But when we say 'hands-on,' we mean it. Just as you are welcome to stare, you are also welcome to touch. At any time, you may touch any part of Jack's body in any way that you wish. We only ask you to respect his wishes, so that if he asks you to stop, you must stop.<< I paused and looked down at Carrie while still slowly pulling on my cock. She looked up at me.

"Jeezus, Jack!"

"No good?"

"I didn't say that! Just...are you sure?"

"I'm sure," I nodded. "I mean, if we're gonna do this, we go all in. Don't you think?" Carrie's look of surprise changed into a wicked grin as she shook her head.

"Boy, they're gonna love you" she said more to herself than to me. And then louder, "Anything else?"

"That's all I got," I shrugged. "Anything you want to add?" She thought for a moment before shaking her head.

"Let's wrap it up," she said. And then she composed the last part herself, narrating as she typed.

>>So much for suggestions and guidelines. We very much hope you will all be able to attend. And know that Jack is looking forward to meeting you as much as you are looking forward to meeting him.

- Love, C & J.<<

"You sure about this?" she asked when she'd finished typing, looking up at me with soft eyes.

"I am," I answered confidently.

"Then...sent!" It was official.

But then something else occurred to me.

"Carrie?" I asked, as I slowly sat down on the sofa which was against the near wall, still playing with myself.

"What's up?"

"I want to suggest something, and I'm not sure how you're gonna feel about it. I mean, it's something we've never really discussed before."

"What is it? Are you OK?" She seemed concerned. The tone of my voice made it sound more serious than it was. At least, more serious than I thought it was. I took a deep breath.

"I think for the party...I think you should put me in chastity."

"What? In chastity? Why on earth..." She couldn't bring herself to finish the question.

"Well, because I'm going to be working. And I want to make the best impression possible, for both of us. I want them to see that you have the best naked houseboy in the world. But if my dick is free, it's going to be too distracting. Especially if I'm surrounded by five beautiful women." Five beautiful women. She heard me including her in that number and she blushed. I'm not sure I'd ever told her she was beautiful before, and I was annoyed with myself. If this really was the first time I told her, what a shitty way to do it, to let it just slip out absent-mindedly as part of a group compliment. Hoping to gloss over it, I hurried on.

"Plus, I'm so used to being able to touch myself whenever I want, I'm concerned that I'll do it at the party and not even realize that I'm doing it."

"Yeah, but they won't mind..."

"It's not that they'll mind. But maybe I'll be slow to bring somebody a drink or whatever. Because I'm distracted. I just think it will be for the best."

"You really think so?" She sounded disappointed.

"I do." I tried to sound serious. Her eyes drifted downwards. She was watching me as I stroked my cock, slowly but steadily. There was almost a sad look in her eye, as if she were imaging a polar bear behind bars at a zoo. But the look lasted only a moment, for then her eyes grew wide and she started grinning that evil grin of hers.

"Alright, I'll agree to put you in chastity. On one condition."

"Oh, and what's that?"

"You have to let me arrange a special surprise. You know, for the party." That fucking grin.

"Well, I do like surprises..."

"Good, then it's settled." She leaned back in her chair. And then, just as quickly, she popped forward again. "Hey, you wanna see a picture of me and the girls? You know, just so you have some idea about who's coming?"

"Yeah, sure!" Now that was a fine idea.

So she picked up an iPad that was on the computer table and came over and sat next to me on the couch. In a sign of how close we'd become, of how comfortable we were with one another, she sat down so close to me that our hips and elbows were touching and the fact that I was jerking off didn't even register. She simply started swiping through her photos. Finally, she settled on one and balanced the iPad on her right knee and my left.

"It's not the most recent picture," she apologized. The picture was of five women who appeared to be in their early to mid-thirties. They were standing shoulder to shoulder, wearing big smiles and dressed for a night on the town. I had never seen a picture of younger Carrie before. She was absolutely stunning. She was a little slimmer then, but still a big, full-figured woman. Even then she was a conservative dresser, by far the most understated of the group. But there was no hiding those massive tits. And her face was gorgeous. But after my 'beautiful' slip before, I didn't say anything now. She placed her index finger over the girl on the far left of the shot.

"That's Samantha." An absolutely adorable redhead, a head shorter than the rest and quite petite. "She's a total sweetheart. You're gonna love her."

"And that's Allison," she said, moving her finger over one. She was showing me a brunette with glasses and sharp features. She was wearing a pencil skirt and had 'sexy librarian' written all over her. "We always joke that she's the smart one."

"What's she do?" I asked.

"Banking something. Honestly, every time she talks about her job, we all kinda fall asleep. She's great though. Lotta fun. Great dancer, can really hold her liquor. Just don't ask her about work," she added with a laugh.

"And this one," she said moving her finger again.

"Lemme guess. Vicky?" I was looking at a girl with jet black hair and a sarcastic smile. She was a head taller than the rest with legs like you wouldn't believe. She stood with the confidence of woman who knows exactly how hot she is.

"How'd you know?"

"She kinda looks like she sounds. Does that make sense?"

"Completely," nodded Carrie. "Now, this is Kara," she said as she moved her finger over to the last girl of the group, who was standing shoulder to shoulder with Carrie herself. And the two could have been sisters. Same height, same build, even their faces were similar. There were only two differences. Where Carrie was blonde, Kara was a brunette. And where Carrie was dressed conservatively, Kara was absolutely flaunting what she had. And oh god did she ever have it.