Naked Houseboy & his BBW Boss Ch. 23

*Part 23 of an ongoing story...

"Good morning," I heard Carrie say as I opened my eyes. She was already awake, sitting up in bed next to me, reading a book. It was around 10:30am.

"Good morning," I yawned.

"I was wondering how long you were going to sleep," she said closing her book and laying it on the night stand. "We have a long day ahead of us."

"We do?" I suddenly remembered her comment from last night. "So you're finally going to tell me what this is about?"

"So I was thinking," she started, sliding back down under the covers to cuddle. "You're going to be spending a fair bit of time in chastity next week, right? To practice for the party?"

"That's my plan, yeah," I nodded.

"Which means you won't be able to masturbate as much as you normally do. I mean, it's going to be a tough week for you, in that regard."

"Well, yeah," I agreed. "But I'm hoping it will be worth it for the party."

"Oh, I'm sure it will be," smiled Carrie. "But that won't make the coming week any easier for you. So I was thinking we should go all-out today."

"All-out? What do you mean?" This sounded interesting.

"I mean, a 24 hour jerkathon," she grinned. "I'm thinking, we don't leave this bed for the next 24 hours. And in that time, let's see how much and how long you can jerk."

"Are you serious?" I couldn't believe what I was hearing. We'd never done anything like that together before.

"Of course I'm serious," she replied. "I mean, we've done plenty of endurance stuff together, seeing how long you can last for one session. But we've never tried it over a whole day. I'm curious what you're capable of."

"So am I!" I paused for a moment. "OK, I'm gonna say my goal is twelve hours."

"Meaning, you want to be actively masturbating for 12 of the next 24 hours?"

"Exactly," I confirmed.

"Excellent. It's good to have goals." Then, turning over, she pulled open the drawer of her nightstand and produced a small notebook and a pencil. "I'll keep time."

"Good idea," I agreed. "So, can I start?"

"Whenever you're ready."

I pulled back the covers and slowly started to massage my dick.

"Ten-thirty-seven," she said, scribbling the time into the book. "OK, buddy, you've got until 10:37 tomorrow morning." Then she put the notebook on the nightstand and turned back towards me. She took up her now familiar position of being on her side, her head on my shoulder, her arm stretched across my chest. For several minutes, we just lay there peacefully as I slowly stroked my dick.

"So," said Carrie after a while. "I'm curious about something."

"What's that?"

"Well, I was thinking about your job interview, when we first met," she began. "You seemed so calm. Weren't you nervous? I mean, I feel like if I was in your place, I would have been super nervous."

"Oh, what an interesting question," I smiled. "You know, it's funny that you ask that. There were two points where I was actually incredibly nervous. But apart from that, I wasn't nervous at all. Like, not even a little."

"Ah, so you were nervous! Twice, even! Will you tell me about it?"

"I'd be happy to," I agreed. "So, the first time I was nervous was when I pulled up in front of your house. Like, once I parked the car, it suddenly became very real. Up to that point, it had just been kind of a fantasy, you know? But when I was parked and I could see your house, it was like, damn, I'm really doing this. I mean, my heart was ready to jump out of my chest. And as I walked up to your front door, it only got more intense. To the point that, even as I was raising my hand to lift the doorbell, I was telling myself it still wasn't too late to turn around, you know?"

"Oh, I totally get that. I mean, if I was you, I'm not sure I could have gone through with it," admitted Carrie.

"Yeah, I really had to will myself to ring that bell. Like, you've come this far, you can't give up now."

"But you did ring the bell," nudged Carrie.

"I did. And as I could hear your footsteps, I thought my heart was going to burst, that's how nervous I was."

"But you looked so calm when I opened the door."

"Well, yeah. I mean, the moment I saw your face - literally that very moment - all my nervousness vanished."

"Why do you suppose that is?" she asked.

"I don't have to suppose," I told her. "I know why."

"Well? Why then?"

"Carrie, I don't know if you know this about yourself, but you have the most amazing smile. And I don't mean it's a pretty smile or a beautiful smile. I mean, it is. But that's not the point. It's more like...I dunno how to express this. There is like this peaceful serenity to your smile. And it just put me totally at ease. Instantly."

"Aww, Jack," she cooed.

"And look, that's not to say I knew that I'd get the job or that we'd get along or anything like that. I just knew, somehow, that you were a kind person and that I had nothing to be nervous about."

"Just from my smile?"

"Just from your smile."

"I'm glad you told me that, Jack. It's a really nice feeling, knowing that."

"It's just the truth, C." I paused. "Also the truth, I love masturbating."

"I know, Jack.

"I know you know. It's still nice to be able to say it out loud, that's all."

"Then say it again," she said encouragingly.

"I love to masturbate!"

"Never gets old," she winked. "But OK, you said there were two times you felt nervous. What was the other one? Was it when I asked you to take your clothes off?"

"Actually, not in the least."

"Really?" she raised an eyebrow. "I, a complete stranger, asked you to get naked and you weren't even the tiniest bit nervous."

"Nope."

"Care to explain that?" she prodded.

"Do you remember what I wore to the interview?" I countered.

"Actually, yeah," she smiled. "You wore a green polo shirt and khakis. Why?"

"Because that's so not me, Carr. I'm very a much a jeans-&-T-shirt kinda guy. But I wanted to look 'presentable.' I wanted to look professional but also not too serious."

"Well, you looked very handsome, Jack. I mean, not that I'm trying to see you dressed anytime soon. But if I had to see you dressed, you'd look very nice wearing that again."

"Thanks, C. But honestly," I went on, "I hate dressing like that. It feels fake, like I'm doing it for other people, not for myself, if that makes any sense."

"Makes total sense," she nodded. "I do it all the time for work."

"Right, and what's the first thing you always do when you get home from work?"

"Umm, inspect your penis? Check your balls? Guess how much you've jerked off that day?" She was laughing as she said it.

"After that," I squinted.

"Oh, well, I guess I go upstairs and change into my pajama shirt."

"Exactly. So now you maybe have some idea of how I was feeling, dressed as I was. The point being, when you asked me to take my clothes off, far from making me nervous, it was actually a relief. And that kinda goes back to your smile again, believe it or not."

"How?"

"Well, like I said, I'd dressed the way I did because I wanted to make a good first impression."

"Which you did," she interjected.

"Right, thanks," I said, taking the compliment. "But once I saw your smile, I knew you didn't actually really care how I dressed. I mean, be honest. If I'd shown up in jeans and a T-shirt, do you think you would have turned me away, or had a worse impression of me?"

"Honestly? Not really," she admitted. "It was never going to be about how you dressed."

"Right, and I could see that in your face, in your smile. And once I saw that," I continued, "I felt foolish for having dressed the way I did. Like, why am I pretending to be something I'm not? The sooner I can get out of these clothes, the better. I was praying you'd ask me to undress. So no," I concluded, "when you finally did, I wasn't the least bit nervous."

"I guess that actually makes sense," said Carrie after a thoughtful pause. "I mean, that's pretty on-brand, actually. But so, when was the second time you felt nervous, then?"

"When you started telling me about how I'd be free to date and be free to bring dates home," I said slowly. "When you started saying that, I began to feel super nervous actually."

"But why?" asked Carrie. "I was just trying to make you feel comfortable."

"Oh, I know that," I said soothingly. "But that was the moment when I realized I'd have to tell you."

"Tell me what?" she pressed.

"About my relationship with masturbation," I exhaled.

"But why did that make you nervous? Just a moment ago, you were telling me - again - how much you love it."

"But at the time, I had no way of knowing how you'd react, right? Like, in my head, the worst case scenario is playing out. I'm about to say something like, 'Well, you don't have to worry about me bringing dates home because I won't be going on dates. Truth is, I'd much rather stay home and jerk off. Speaking of which, by the way, it's my most favorite thing in the world, so you should know that I jerk off as much as I possibly can, and I feel great about it.' Know what I mean?"

"Yeah, but uh, Jack," she said. "That's basically what you did actually say."

"That's my point," I nodded. "I knew, in my head, that I was about to say that. But I didn't know how you'd react. Like, what if you said, 'Oh wow, what kind of loser would rather masturbate than have sex?' Or, 'Well, sure, all guys jerk off, but this is excessive and kinda creepy.' Or maybe you'd just stare at my dick and think, 'Is that what the penis of a chronic masturbator looks like? All he does with that thing is jerk off? How big does it even get? Maybe the reason he's here is because he can't find anybody that actually wants to fuck that thing - "

"Slow down, Jack," she interrupted.

"Sorry, I know you would never actually - "

"No, I mean, slow down," she repeated, this time grabbing hold of my right wrist. "You were turning this into one of your humiliation fantasies and you were speeding up. We're barely an hour into this. You don't want to cum yet."

"Oh!" I blushed. "Sorry."

"Don't be! You know I love hearing what's going on inside your head. We just need to exercise some discretion here." She removed her hand from my wrist and held up her open palm. "Give me your hand." Taking my hand from my dick, I placed my palm against her.s She laced her fingers into mine and held my hand. "Count to ten with me. One, two..." On the count of ten, she let go of my hand. "OK, I think you're ready. But take it easy, OK?"

Taking a deep breath, I returned my hand to my waiting cock and began to stroke again, slowly.

"So," she said, resuming the conversation. "You were nervous about how I'd react when you told me about your love affair with masturbation."

"Yes, very," I confessed. "OK, I was getting carried away before. But I did genuinely worry that by telling you, I'd blow up my chances for the job. Like, maybe you just woulda said, 'Well, thanks for your honesty and to each his own, but that's not really what I'm looking for in a houseboy.' But once I saw you were OK with it, then it passed. And honestly, I've never felt nervous in this house since that day."

"Well thanks for sharing that with me Jack, I've been curious about it for a long time."

"No problem, C. It was nice to share it, actually. But what about you?" I continued. Were you nervous at all? If you were, it certainly didn't show."

"Funnily enough," she began, "I also was very nervous at two specific moments, but otherwise not at all."

"I'd love to hear about it," I said, enjoying the feeling of masturbating beside Carrie in her own bed.

"Nah, I'd rather not," she grinned.

"Alright, fine," I conceded. "But if this conversation is over, I may as well hurry up and finish." At which point I started to stroke faster.

"Oh, don't be such a baby. I was just fucking with you."

"I know, but it was a good excuse to speed up for a bit."

"So slow down and I'll tell you all about it."

I did as I was told, obviously.

"So, just like you, I was crazy nervous leading up to the interview," she began. "That whole morning, I was pacing around the house. I mean, I couldn't sit still. I just kept thinking, 'What am I doing? What kind of creeps are gonna turn out for this add I posted.' In fact, it's a good thing you didn't give me a cell phone number or I might have called you up and cancelled."

"Seriously?" I had no idea she'd been that nervous.

"Oh yeah," she nodded. "I'm not saying I definitely would have. But the thought crossed my mind more than once. And then when I saw your car pull up, I thought I was gonna lose it. I mean, I honestly considered hiding in my room and just pretending not to be home."

"That bad, huh?"

"That bad, yeah." She paused.

"So what made you decide to go through with it?" I pressed.

"Well, I started going over all the reasons I had posted the add in the first place. That I was lonely, and my job wasn't giving me much time to meet people. That even if I did have time to meet people, I had no desire to go on dates. That I wasn't looking for a sexual relationship. That having a naked houseboy who was comfortable in his own skin might help me feel more comfortable myself. I told myself all these things over and over. And then you rang the bell."

"So you were nervous when you opened the door?" I asked. "I had no idea. You seemed so calm, so professional."

"Yeah, I was so nervous," she conceded. "Right up until I saw you. And then I wasn't nervous anymore. I mean, one look at you, and I just knew."

"One look at me and you just knew," I repeated. "That you were going to hire me?"

"Ha!" she laughed. "No, hardly. Just, one look at you, and I knew you were a decent guy. I knew I had nothing to be nervous about. That said, I had no idea if you'd be right for the job. I still didn't know if we'd hit it off, or - even if we did - how comfortable you'd be being naked around me."

"I see," I said softly, pulling on my dick with renewed vigor. "Well, clearly I'm very comfortable being naked around you."

"Take it easy, pal," she said, touching my wrist. "But I'll tell you this," she went on. "Welcoming you into my house, it felt right. Like, somehow, it felt as though you'd been here all along."

"I'll admit, I did kinda feel at home here, right from the moment I walked through the door. But," I went on, "you were nervous before I arrived. What was the second time? Was it when you asked me to undress?"

"Actually, no," she replied. "I mean, I thought I would be. The whole time leading up to the interview, I just kept thinking how awkward it was going to be to ask a complete stranger to get naked in front of me, in my own home. And then, when he does, to conduct a freakin' job interview that way. But when the moment came, I actually thought, 'Well, it doesn't even make sense to talk to him when he's dressed. Either this will be awkward, in which case he's not the right guy. Or it will be fine, in which case, we go on.' So I wasn't really nervous. Just curious to see what would happen."

"But was it actually awkward for you at all?" I asked. "I mean, clearly it wasn't for me. But I guess I never thought about if it was for you."

"I was very ready for it be," replied Carrie. "But the way you neatly folded each piece of clothing as you took it off, and then that little spin you did at the end, that was enough to kill any awkwardness. And then I could see how comfortable you were being naked, and I just knew that part of things would be fine."

"Well, I'm glad my little stunt paid off," I said with a laugh.

"But it was more than just that," she said. "Look, I know you said you weren't nervous after you saw my face."

"Your smile," I corrected.

"My smile, fine. But the truth is, Jack," she went on, "you must have been at least a little bit, even if it was just the regular job interview jitters."

"Why do you say that?" This was news to me.

"Well, you were kinda fidgety," answered Carrie. "Your hands were constantly going in and out of your pockets. You were shifting your weight from one foot to the other. Even your posture seemed self-conscious. And again, perfectly normal job interview jitters kind of stuff. I'm just saying I noticed, is all."

"Wow, C, I guess I didn't even notice myself," I concluded.

"Oh, you did. You've said as much," she added. "You just don't realize it."

"Explain, please."

"Well, you yourself said being naked just felt right. That once you were naked, you didn't have to pretend anymore, you could just be yourself. And maybe you don't realize how true that really was. Because once you got your clothes off, you stood a little straighter, a little more confidently. You didn't seem like you didn't know what to do with your hands."

"Well that's because I knew what I wanted to do with my hands, and I knew I couldn't!"

"Come on, Jack, I'm being serious!"

"So am I!" I protested. "I knew it didn't matter what I did with my hands as long as I didn't touch myself. But I take your point. And yeah, I guess you're right. I guess there were still some nerves before I got undressed. But anyway, the question was, when did you get nervous the second time?"

"When I knew I'd have to confirm the whole no-sex thing with you," she answered matter-of-factly.

"Even though it was clearly stated in the add?" I clarified. "Even though you had already asked me about it on the phone? Why?"

"Because I know how guys can be," she sighed. "And I was half expecting an applicant to say anything to get in the door, and then try and turn it into a negotiation. Like, 'What if we get really close?' Or, 'What if I do a really good job for you?' Or, 'Never doesn't really mean never does it?' That kind of thing. And even though you didn't seem like that kind of guy, I still couldn't be sure until I asked, you know?"

"Actually, I'm not sure," I confessed. "I mean, yeah, I see what you mean. But if I was that kind of guy, then that would be all the information you'd need to know I wasn't right for the job. Why be nervous about that?"

"Because," she sighed. "By that point, I already knew I wanted to hire you. We were getting along well. I liked you personally, from the little bit I knew you. And you were so comfortable being naked. It was almost too good to be true. I already knew I wanted it to work out, Jack. So I was nervous that maybe it really was too good to be true. That you'd be just like every other guy. That's why I was nervous."

"Aww, Carr - "

"Shh, don't say anything," she cut me off. "But that's the other time I was nervous. But once you told me you weren't interested in sex with me, I knew everything was gonna work out. And then, later, when you told me about your love affair with masturbation, I was even happier."

"Wait," I stopped her. "You were actively happy about that from the beginning?"

"Of course!" she smiled. "Assuming what you were saying was true, it meant you wouldn't be going out to bars, getting drunk, coming home with god knows who. Plus, I figured if you could tell me that at our very first meeting, then there probably wouldn't be many secrets between us. So yeah," she concluded. "Once we cleared up the whole no-sex thing, I was never nervous again."

That being the end of the story, we fell into a short silence, Carrie snuggled against me as I lay there slowly jerking off.

"You know what's kinda funny?" I said after a while.

"What's that?" she asked softly.

"Considering you were hiring a naked houseboy, I feel like you spent a lot of that interview trying NOT to look at my body."

"You mean the way you spent most of the interview trying 'not' to look at my tits?" she countered.

"I, uh, Carrie, I mean...I wasn't..."

"Oh, come on, Jack. You really think I didn't notice?"

"I was trying to be discreet," I frowned.

"And you were," she laughed. "You were the perfect gentleman. But even the perfect gentleman's eyes wander from time to time. And all I'm saying is, I noticed. It's nothing to feel bad about. But, anyway, you were saying I spent most of the interview trying not to look at your body. And you think that's funny?"