Naked Houseboy , his BBW Boss Ch. 25

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*Part 25 of an ongoing story…

Carrie and I lay snuggling in her bed after my second orgasm of the day. The huge breasted bbw woman I had so enjoyed jerking too just moments ago was still on the screen. I still couldn’t take my eyes off her.

“Jack?”

“Hmm?” I regret to say she didn’t exactly have my full attention.

“Do you mind if we turn this off?” She was looking at me, not at the screen.

“Huh? But it was your idea to – “

“I know,” she interrupted. “And let’s definitely put something else on. It’s just, I’d prefer it if we didn’t have to watch this, specifically. Please?”

“Aww hey, sure.” The unusually plaintive tone of her request was enough to break the spell. “Maybe a break is in order anyway,” I aded. Picking up the keyboard again, I switched off the screen.

“Nuh-uh, no breaks,” she shot back playfully, wresting the keyboard from me. She then put back on the lesbian porn she had originally chosen. Only this time, with the sound muted. “Part of the rules with a 24 hour jerkathon, is that there has to be some kind of porn on at all times.”

“Those are the rules, huh?” I asked gamely.

“Are you objecting?” she asked as she set the keyboard back on the nightstand.

“I wouldn’t dream of it,” I smiled.

“Good.” Snuggling back up to me, she slid her hand down between my legs, and in a move that seemed quickly to be becoming a habit, she took my flacid penis between her thumb and forefinger. And I was glad that she didn’t ask for permission. But the warm feeling passed when, moments later, a question popped into my head.

“Carrie?” I tried gently. “You seemed really adamant about getting that particular porn off the screen. Can I ask why?” For what seemed like two full minutes, she said nothing. “Car?”

“Oh, Jack,” she sighed. But then said nothing more.

“Hey,” I brushed my hand against her cheek. “You don’t owe me an explanation. Forget I asked.”

“No, no, I want to tell you,” she answered hesitantly. “I’m just trying to formulate my thoughts is all.” She took a deep breath. “So, first of all, watching that video with you was really informative. Well, I shouldn’t say ‘watching.’ I didn’t watch it. ‘Experiencing’ that video with you…I feel like I learned something about you.”

“And what’s that?”

“So obviously I’ve been all through your browsing history, I know you look at girls like that all the time.” She was certainly beginning her answer in a roundabout way. And once again, she’d said ‘girls like that’ as if it was the least interesting thing in the world. “But the truth is – and I know this is going to sound horribly narcissistic – but, part of me always wondered if you weren’t doing that for me.”

“I’m not sure I follow.”

“I know, sorry,” she closed her eyes. “What I mean is. See, from the very beginning, I’ve been open with you about my body-image issues, how I don’t feel comfortable in my own skin, all that stuff. And I know you want to help me in any way you can. So when I go into your browsing history, and I start finding women who are built like me…”

“Wait, you think I was going out of my way to leave that there for you to find?” I asked, unable to hide my surprise.

“Well, the thought occurred to me, yeah. Like, (switching to her mock-Jack voice) ‘If Carrie sees that I jerk off to women who look like her, maybe it’ll help her feel appreciated and sexy.’ I know, it’s crazy.”

“It’s not totally crazy,” I said, running my hand through her hair. “I mean, it’s a little crazy maybe. But not the idea that there’s nothing I wouldn’t do to help you.”

“Well, right, exactly. But the worst thing,” she went on, “is that because I’m so uncomfortable with my own body, I was convinced there was no way you could actually enjoy masturbating to women who look like me. I mean, there were times – not always, but times – when I even thought you might be loading up your browser history with this stuff, just so I’d see it. But then you’d actually go jerk to something else entirely.”

“Wow, C, I mean…”

“I know, it’s terrible,” she said with a touch of sadness.

“No, it’s not terrible,” I said firmly. “I mean, it’s terrible that you felt that way…but, Car, it couldn’t be farther from the truth!”

“I know that now,” she smiled softly. “That’s what I wanted to say. Having experienced that video with you, I get it. Well, I don’t know if I get ‘it,’ but I think I get you. Hearing the passion with which you described that woman, seeing the look on your face as you devoured her with your eyes…hell, even watching you drift off into your goon-zone. It’s clear to me now that you weren’t doing me any favors. It’s clear to me now that you genuinely find women like her beautiful, sexy. She really is your type.”

“She is 100% my type. The kind of woman I love jerking off to more than any other. The kind of woman I dream of spending hours mindlessly masturbating to in my goon-zone, entranced by her beauty. And that’s why I wanted us to watch that together. Because I wanted to Esenyurt escort bayan share that with you.”

“I know,” she whispered.

“But that’s also the reason I’m asking why you’re so adamant about not watching it.”

“Because, Jack, she looks like me and I hate looking at myself!” She just blurted it out, her eyes moist with tears. At the same time, her fingers were playing with my still limp dick. Of course, ‘playing’ is not the right word. Perhaps ‘manipulating’ is better. But in a mindless sort of way. Indeed, I’m almost certain she wasn’t even aware what she was doing. For want of a better comparison, it was almost like my tired penis was a fidget-spinner or a stress ball for her. Obviously, I didn’t mind.

In fact, I almost had to laugh. Like, instead of saying, ‘If you’re sad, you can cry on my shoulder,’ I could now say, ‘If you’re sad, you can handle my lifeless dick.’ But this amusing thought was quickly dispelled by Carrie’s distress.

“Wait, hang on,” I said, getting back on track. “You hate looking at yourself? Carrie, those are really strong words.”

“Not always,” she sighed. “I mean, I more or less like the way I look when I get dressed up for work, or whatever. But Jack, honestly, I hate looking at my naked body. Seriously, I go out of my way to avoid it.”

“You go out of your way to avoid looking at your naked body?” I asked, struggling to believe such a thing.

“Not just to look at it. Jack,” she groaned, “I go out of my way to avoid being naked, period.” She must have observed my complete lack of comprehension at such an idea, because the next thing she said was, “Sweet Jack, you’re so comfortable being naked, you don’t see how hard it can be for other people.”

“I guess I don’t,” I admitted. “But I want to understand. I want to know what it’s like for you. I mean, if you’re comfortable telling me.”

“Well, I mean basically because of my history,” she began, “I’ve just never liked the sight of my naked body. You know, when I was younger, in school, before puberty, people teased me for being fat. Then, when my boobs started to grow…and grow…and grow…I got teased for that. We’ve already talked about how there were no examples of ‘beautiful’ women who looked like me in pop culture. And then after I got married, well…you know. That bastard never made me feel good about myself.” She took a breath before continuing. “So for as long as I can remember, I just didn’t like seeing myself naked. And somewhere along the line, I guess I just figured the easiest thing to do, was to be naked as little as possible.”

“Jeez, Car.” It honestly broke my heart to hear her speak that way. And yet, I still didn’t full understand. “But I still don’t get how…” I didn’t have it in me to finish the sentence.

“How I go about it?” she said boldly.

“Well…yes.”

“So, apart from the shower, where obviously I have to be naked, I pretty much try to have at least one article of clothing on at all times. I know it sounds crazy, but I basically have it down to a system.” There was a calmness in her voice that indicated she didn’t actually mind speaking about this.

“Dare I ask about this system?”

“OK, maybe ‘system’ is too strong a word,” she answered with a slight laugh. “But sure. So like, when I get out of the shower for example, the first thing I do is wrap myself in a towel. And anything I have to do in front of the mirror – brush my hair or teeth, do my makeup, whatever – I’m always wrapped up in a towel. And like, I might be totally dry at that point. I might not need a towel. But I keep it on, so I don’t have to see myself.” She paused. “This can’t be interesting to you.”

“No, please, Car. Go on. I really want to hear about this.”

“Right,” she sighed. There was still a calmness to her voice, but I was beginning to suspect that talking about this wasn’t as easy as I had first surmised. “Well after the shower, I need to get dressed, right? So I always make sure that all my clothes are laid out in advance. That way, there’s no chance of being half dressed and realizing I have to start looking around for something.”

“Logical,” I interjected.

“I think so. Anyway,” she went on, “all my clothes are laid out in advance. And the first thing I’ll always do, is pull my panties on while I’m still wearing the towel. Obviously that’s not much, but at least that way, when I take the towel off -psychologically at least – I’m not really naked. And then, you know, I basically get dressed as quickly as I can.”

I was trying to process all this when a new thought came to me. Carrie did have, after all, a full length mirror in her room. Hell, she’d made me stand naked in front of it and declare my love of masturbation out loud. How did that fit into this? I eyed the mirror curiously. She must have noticed.

“You’re wondering about the mirror,” she remarked. “I get dressed with my back to it. I never stand in front of it naked. I won’t even stand in front of it in my towel. It’s basically Escort Etiler there to help me adjust my outfits and make sure I look good after I’m already dressed.”

“Ah, I was wondering about that,” I admitted.

“Well, yeah. And also, to make you stand in front of it and say things like (switching to her mock-Jack voice), ‘My name is Jack and I love jerking off more than anything in the whole wide world.'” And as she said that, she gave my still limp penis a few quick tugs between her thumb and forefinger. “Nothing, huh?” she said, noting my lack of arousal. “I guess that gives us more time to talk,” she added with a wink.

“Well, I wouldn’t say ‘nothing,'” I countered.

“Jack,” she shot back under narrowed eyes. “Who are you trying to fool?” Then, still with her thumb and forefinger only, she started tugging again on my lifeless dick. “Nothing’s happening down here,” she said, looking me in the eye.

“OK, OK, you’ve made your point!” In answer to which, she stopped tugging, though without actually letting go of me. “When I said something was happening, all I meant was, I’m totally loving these impressions of me that you’re doing. And every time you do a new one, I love it more. That’s all I meant.”

“Oh,” she blushed.

“Also…?”

“Yes?”

“That was like the worst handjob ever.”

“For you or for me?” she shot back without a moment’s hesitation. And then, seeing that I had no answer, she said, “And anyway, it wasn’t a handjob, you brute.” With that, she removed her hand from my penis and slapped me lightly across the cheek. Having made her point, she rested her arm across my chest.

“Anyway, back to the original discussion,” I suggested. “So, I guess when you want to get undressed, it’s the same in reverse?”

“Right,” she said, somewhat reluctantly. “So when I get home, I’ll lay out my pajama shirt first. Then I’ll get out of my clothes as quickly as I can, down to my bra and panties. Then I’ll throw the big pajama shirt on. Only then will I take my underwear off.”

Wait, what?! ‘Underwear’? What did that mean? To be sure, there was no hiding the fact that Carrie went around bra-less when she was in her pajama shirt. But did she routinely not wear panties as well? This is something I had always wondered about, to be honest. Her shirts were so long (and her thighs so thick, not for nothing), that it I could never really see one way or the other when she would sit down. And her shirts were so baggy, that it was difficult to make out any kind of panty line, if indeed there was one. And if she were to wear a thong, or something similarly minimalist, the evidence would be even more difficult to spot. Was it possible that this mystery was about to be solved? I had to ask.

“Carrie, forgive me, I know it’s hardly the point right now, but when you say ‘underwear’…”

“Bra and panties, Jack,” she answered mechanically. “Don’t you know what underwear is?”

“Of course I know what underwear is,” I stammered. “It’s just…I mean…this whole time…” I don’t know why I was struggling to find the words.

“Spit it out, dear boy,” she countered patiently.

“This whole time,” I tried again. “When you get into your pajamas…I mean, when you’re in your pajamas…you’re not…I mean, you don’t…you don’t wear panties?”

“Of course not,” she said reflexively. “I thought you knew that.” It was clear from her voice that she was in no way trying to tease me. This was the simple truth of it, and she genuinely believed that I already knew it.

“I had no idea,” I answered softly.

“Oh god, Jack, I hate wearing panties! I honestly just find them uncomfortable. Obviously I wear them to work, but as soon as I get home, I can’t wait to get them off. As long as, you know, I’m wearing something else that keeps me covered up.”

“I can’t believe I didn’t know this.” I shook my head in disbelief.

“Yeah, I’m quite surprised as well, if I’m being honest. Although, now that we’re talking about it, I guess, how could you really know? I suppose my pajama shirts keep things pretty well hidden in that department.”

“Clearly they do,” I agreed. “But can I make an observation?”

“Of course.”

“Well, given the extent to which you dislike being naked, I guess I’m surprised that you choose to walk around without underwear.”

“Yeah, well…” she said thoughtfully. “Here’s how I see it. The reason I wear these big, baggy pajama shirts is not only because they cover me up in a pretty shapeless way – I’m guessing you’ve long since figured that out – but also because they’re comfortable. I guess the thing to understand is, just because I don’t like being naked, doesn’t mean I don’t like being comfortable. And I just find underwear very uncomfortable in general. Bras, panties, doesn’t matter. And I guess I don’t really feel ‘more naked’ if I’m not wearing underwear, as long as I’m covered up in some other way. Does that make any sense?”

“Yeah, I suppose it does actually.” I paused. “Well, except Eyüp escort for one thing.” I stopped myself. “Look, I feel like we’re getting into ever more personal territory here. I don’t want to push you or ask you something where it’s not my place, you know?”

“I appreciate that, Jack. I really do,” she said, giving me a little kiss on the cheek. “But don’t worry about that. I’ll tell you if you overstep; I’ll tell you if there’s something I’d rather not discuss. What’s your question?”

“Well, so, the thing about not wearing a bra…” I started timidly. “I mean, it’s pretty revealing…you know…in it’s own way…”

“Oh god, Jack,” she started to laugh. “You know, I’m so used to living with these things, I honestly never stopped to think about how it must look from a man’s perspective.”

“Well now I’m definitely confused,” I admitted.

“I mean, you’ll tell me if I’m wrong here,” she stated, “but I’m assuming, in your normal everyday life, when you’re out and about in the real world, you’re accustomed to seeing – you expect to see, even – women wearing bras, right?”

“Right.”

“And if you happen to see a woman walking around bra-less, especially if she’s well endowed…well, tell me. What’s your reaction?”

“I notice for sure,” I told her. “And yeah, I suppose I find it out of the ordinary. Don’t get be wrong,” I hurried to add. “I don’t judge. I’m not one of those guys who think women owe it to men to wear a bra, or that they’re being somehow inappropriate if they don’t. But yeah…it tends to stand out. To me, anyway.”

“That’s all I meant, Jack,” she smiled. “Whereas to me, I’m stuck with these girls no matter what. And there’s nothing I can do to hide them either, no matter how baggy my shirt is. To me, they’re always just gonna be…’out there.’ High, low, whatever. So given all that, I choose to at least be physically comfortable.”

“Well I guess I never considered it from that angle. Thanks for explaining it to me. And hey,” I smiled. “If it makes you feel any better, I also hate wearing underwear!”

“You’re shitting me!” she laughed.

“I shit you not,” I answered solemnly.

“Good thing you found this job then, eh?”

“A very good thing indeed,” I replied, snuggling up even closer to her. We lay there in silence for a few moments, simply enjoying being together.

“Jack, I want to tell you something,” she whispered after some time.

“What’s that?”

“I want you to know…I genuinely want to be naked with you. One day. I’m…just not read yet.”

“It’s OK, C – “

“No, it’s not,” she cut me off. “I love cuddling with you, just like we are right now. But also, I hate that there’s this layer of cotton between us. I wish it was different, but I’m just not there. Not yet.”

“You’ll get there, C,” I offered. “There’s no rush. You’ll get there when it’s right for you.”

“But what if it’s never right? Will you help me?” she pleaded.

“I’ll help you any way I can, of course. But what can I do?”

“I don’t even know.” There was a catch in her voice. “I guess I just thought…”

“What? Tell me.” I tried to sound as patient and comforting as I could.

“It’s stupid,” she shut her eyes.

“Nothing about this is stupid, C,” I said reassuringly. “You can tell me.”

“I guess I just thought,” she tried again, “you know…when you wanted to break your masturbation records, I helped you, right? Even though in the beginning I wasn’t really sure how I could help you. But in the end, I did. And I just thought maybe…you could help me find a way to feel OK being naked.”

“Ah, now I see,” I smiled. “So, obviously the short answer is yes. I’ll do anything I can. Just let me think for a bit.”

“Why did you put it that way?” she asked.

“What way?

“You said, ‘the short answer is yes.’ Is there a long answer?”

“Well, let’s be honest C,” I said cautiously. “I’m not exactly neutral. It’s not like I don’t have an interest in this.”

“You mean, because you want me to be naked too,” she deduced.

“To say the least,” I nodded.

“To say the least,” she echoed. “Is there more to say?”

There was clearly quite a bit more to say. The question was, did I actually want to say it. Could I say it even if I wanted to? I pondered the issue for what seemed like minutes.

“Jack?” she prodded me in the side. “Did you actually want to say something more?”

“That will depend on how you answer this question,” I said, looking her in the eye. “Carrie, in all seriousness now, do you truly, genuinely want me to help you with being naked?”

“I truly honestly do, Jack,” she answered, meeting my gaze.

When she made that answer, I got out of the bed and walked over to the full-length mirror.

“What’s happening?” she asked.

“Come here,” I motioned with my hand. She approached and stood beside me, both of us reflected in the mirror, her in her giant T-shirt and me, naked.

“If I’m going to help you, Carrie,” I began, speaking to our reflections, “then I need to tell you something. And it’s something that I would not be telling you in literally any other circumstance.”

“What is it you need to tell me, Jack?” she asked. And perhaps in reaction to the seriousness of my tone, she put an arm around my shoulder and pulled me closer to her.

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