Naked Houseboy & his BBW Boss Ch. 29

*Part 29 of an ongoing story...

"Oh, you're awake," she had said when I tried to remove her hand from me and sneak out of the room. Before, when I was having difficulty getting off, she'd teased me with talk of one day seeing her naked, going so far as to promise me that one day I'd see her tits. And while that had done the trick, I felt guilty and ashamed for allowing that to happen, knowing how she was still so uncomfortable with her own body and nowhere near ready to be naked with me. At that moment, I didn't want to face her. I just wanted to go to my room and be alone. I was hoping I could get out of there while she was still asleep. But now she was looking at me, smiling softly beneath still-waking eyes.

"Listen, Car, I think I just want to be alone. To be honest, I'm feeling a bit embarrassed and ashamed about what happened before."

"You mean about your penis? Don't feel bad, you were tired."

"I mean, that too," I cringed, remembering my complete inability to get hard during the last jerk session. "But I was actually talking about the way you helped me at the end. The way you promised me...well, things. Because I know you're a long way from being ready for that. And I'd hate to think you felt pressured to say anything you wouldn't otherwise say."

"Oh, Jack," she looked at me. "You really are sweet. But you have to know by now, I never feel pressure when I'm with you, I never feel pressured by you. If I say something to you, it's because I want to say it."

"I guess I know that," I conceded. "It's just, you've never said anything like that to me before. I mean, you've said you'd like to get to the point one day where we can be naked together. But that feels very different than promising me I'll see your tits one day. It was just very unexpected and I hope I didn't do anything to push you outside of your comfort zone."

"Well the truth is, Jack, you did do something to push me out of my comfort zone. But in a good way," she added quickly. "Because when I made you that promise, I honestly felt closer to you than I ever have in all our time living together."

"I'm not sure I understand. What did I do?"

"Maybe we should just leave it there, Jack." She paused, looking at me. "Isn't it enough to know you made me feel very close to you, very special?"

"Honestly, C? It's kinda not." I tried to sound gentle in my answer. "When you tell me I did something to push you out of your comfort zone, that you'd never felt closer to me...I mean, I gotta know what that is."

"I suppose that's only fair. It's just, I don't want to say anything that might hurt your feelings."

"I mean, I appreciate that," I answered slowly. "But I don't see how you could. And anyway, our whole thing here is based on honesty. You need to be able to tell me what's on your mind without fear of hurting me. Or else, what are we even doing?"

"No, you're right," she sighed. "Okay, so I'm just gonna tell you everything that's on my mind then. Like, all of it. Alright?"

"I wouldn't have it any other way."

"So let me start by saying, you've been an inspiration to me in all the ways I hoped having a naked houseboy would be. I get to watch you walk around naked all day, every day, completely comfortable in your own body. You don't just masturbate in front of me, you share all your porn with me. And never once have I sensed in you any sense of fear or embarrassment. That's amazing to me. I wish I could be like that. And having your example to follow, well, I guess it gives me something to shoot for. In other words, just by being yourself, you give me confidence and hope. Most of the time."

"Most of the time?" I repeated, filling the lingering pause she'd left.

"Most of the time," she said again. "Because to be perfectly honest, Jack..."

"Go on," I encouraged. "Say what's on your mind. Be perfectly honest."

"To be perfectly honest, Jack, sometimes I really resent you for it." She looked at me, waiting for an interruption I wouldn't make. She took a breath and continued. "Like, there are times when I think, 'This mutherfucker, it's always so damned easy for him.' It's always so easy for you, Jack. And it's never ever easy for me. And so yeah, while most of the time I really admire you for that, there are times when it pisses me off. And sometimes, it's not even that it pisses me off. It just kinda makes it hard for me to feel close to you. No wait, that came out wrong." She stopped cold.

"It's okay, C," I reassured her. "I know you're talking about particular experiences here. It doesn't change the way you really feel about me. So go on, tell me."

"I'll give you an example," she resumed. "Every day before work, when I come down to the kitchen, you're standing there waiting for me with my cup of coffee. Which I love, by the way. But sometimes I'll look at you, standing there naked, so totally comfortable in yourself, and I'll think, 'He just doesn't get it.' I mean, you've listened to me with endless patience talking about how I feel in and about my body. I know you appreciate it. But you can't feel it with me. And sometimes that's really frustrating, and it makes me feel like there's a limit to how close I can feel to you. Am I making any sense?"

"You're making total sense," I answered. "And not only that, trust me when I tell you I know exactly how you feel. At least about that last part, about there being a limit to the closeness between us."

"Oh no," she grimaced. "Am I that obvious? You can actually feel a wall between us from my self-consciousness?"

"No! Not at all!" Shit, that came out very wrong. "What I mean is...damn, now I'm the one who doesn't want to say the wrong thing."

"Nothing you say here can be wrong, Jack."

"Yeah yeah, alright, doctor." I flashed her a brief smile. "No, what I mean is, you've listened to me with endless patience talking about how much I love masturbating, how central it is to who I am. And I know you appreciate that. But I also know that it's not something you can feel with me. So, yeah, there are times where that makes me feel like it's hard to be as close to you as I'd like. And to be clear, that's not how I normally feel, right? Most of the time, I feel wonderfully close to you. Just...sometimes, you know?"

"I do know," she smiled. "And thank you for sharing that with me, Jack. Just knowing we both have that feeling sometimes, well...it makes me feel closer to you." She kissed my cheek for emphasis.

"But speaking of feeling closer," I resumed, "you still haven't told me what I did that made you feel so much closer to me than before."

"Well...it's more like...what you didn't do."

"You mean how I couldn't get hard?" I managed to say the words without wincing, but I'd be lying if I said I didn't feel a twinge of shame and embarrassment in that moment.

"So, yeah...that, what you just said...that's definitely a part of it. But not just that."

"Carrie," I said, using her name in an attempt to sound more serious. "Whatever it is you have to say to me, I want you to just say it, okay? Just speak plainly. Don't pull your punches, don't look for you euphemisms, don't worry about my ego. This only works if you can be straight with me. Promise?"

"I promise," she whispered. "And Jack, you really are something else. You know that, right?"

"Yeah yeah, I'm fantastic. Now will you please tell me what I apparently didn't do to make you feel so close to me?"

"Well, basically, you didn't have an easy time of things. You struggled, you got frustrated. I mean, I'd never seen you like that before."

"But you've seen me lose my hard-on before," I interrupted.

"Oh, plenty of times! But that's not actually what I'm talking about here. Although I will want to return to the subject of your penis, because it definitely plays a...well, not 'big'...but an important role in the story. Sorry," she giggled, "I couldn't help it."

"Don't apologize," I grinned. "You know I love that shit."

"You're right," she shot back wickedly. "Apology withdrawn." Then, turning serious, she continued. "No, what I really meant was like, no matter what, whenever you jerk off, you're basically the happiest, most blissed-out guy on earth. This was literally the first and only time I've ever seen you masturbate, where I thought, 'Wow, he looks like he's not actually enjoying this. He looks like he just wants to cum and get it over with.' I swear, I'd never seen that from you before."

"And that made you feel closer to me?"

"Oh, my god yeah, Jack! I know this will sound corny, but it was almost like a revelation. Like, 'Oh wow, he struggles too.' And that's what I mean, I guess. It wasn't so much your limp dick as it was the look of frustration on your face." She paused, her cheeks flushing. "Oh, I'm sorry, Jack. That's an unkind way to talk about your..."

"Hey, I asked you to speak plainly, didn't I? Whatever is on your mind, I want to hear it exactly as-is, no punches pulled, right? Really."

"Sure," she nodded. "Anyway, watching you sweat, watching your face twist not with ecstasy but with frustration, the way you were throwing your body around, trying to will yourself to get off...I mean, don't get me wrong, it's not like I enjoyed watching you suffer. It's just, knowing that - at least this one time - it wasn't easy for you...I felt less alone. I felt closer to you."

"Well hey," I smiled, "if a little bit of suffering and frustration on my end from time to time helps you feel closer to me, then sign me up for more frustration and suffering."

"You really are the sweetest, Jack," she said, snuggling her nose into my cheek. "Were you serious, though? Did you really mean what you said?"

"Of course! Sign me up for more - "

"No," she interrupted. "I mean, about wanting to hear everything that's on my mind, no punches pulled."

"Oh," I stopped. "Well, yeah, of course I was serious. Of course I meant that."

"Are you sure? Because this is the part that is actually about your penis. And I could imagine that maybe - "

"Nope." This time, I interrupted her. "I want to hear everything. And listen, I really appreciate that you're trying to take my feelings and my ego into account here. But don't. This only works if you can speak freely. So just go for it."

"Alright, Jack. Here's the unedited version. So like you said, I've seen you lose your hard-on plenty of times. Like, when you first moved in, right? We'd sit downstairs, drink wine and chat. And obviously you'd be jerking off the whole time. And invariably, the conversation would take a decidedly non-sexual turn, or maybe it was just that we'd be chatting for a few hours with a lot of wine...but there'd be points where you'd lose it. In the beginning, I thought maybe it was a sign of you not enjoying yourself. But of course you quickly set me straight on that subject. And anyway, we'd always find our way back to something that would get you hard again so you could cum.

"Then, earlier tonight, I watched you go soft as you drifted into your goon-zone. And you taught me all about how you don't need to be hard to enjoy masturbating, how freeing it is for you to not even have to worry about it. But even with that, when you came back to reality, and the porn went in a direction that you liked, you got rock hard again and had no problem getting off.

"But what I saw from you this last time, it was so not that. I mean, it was completely different. You were like..." She stopped. "Jack, you're sure you want to hear this?"

"Kinda more than anything," I admitted.

"Okay. So like, this was not you going soft for a bit in the middle of a forever jerk session. This was you not being able to get it up, at all, from start to finish. But it wasn't just your total inability to get even a little bit hard, it was the way you seemed so frustrated by it. The way you were pumping and tugging and throwing your body into it. And just not having any success. To be honest, Jack, at first, I was actually feeling kind of embarrassed for you."

"Oh god," I groaned, feeling the hot blood rush to my cheeks.

"Wait, let me finish," she said, rubbing her hand against my breast. "I wasn't embarrassed for you that you couldn't get it up. Like I said, I'd seen that plenty of times before. And to be honest, I actually kind of enjoyed watching you slowly tug away on your soft penis while you were in your goon-zone. Because I could see how much you were enjoying it.

"So, no, when I felt embarrassed for you, it wasn't because of your limp dick per se, it was because you were so clearly frustrated by not being able to get it up."

"Alright," I said quietly. "I'll accept the distinction. But let me ask you. You said, 'at first' you felt embarrassed for me. How long were you feeling that way? How long was 'at first'?"

"Wow, let me think for a second. So that whole limp-dick-jerk-session - which I think is how we should refer to it now, by the way - went on for like two hours and fifteen minutes. A lesser man would have quit, not for nothing. Good for you for sticking with it in the face of - "

"How long, C?" I cut in, saving her from having to finish the sentence.

"Well, probably for like an hour or so. But also, not exactly right from the beginning."

"So you're saying you spent a full hour feeling embarrassed for me. And not even from the beginning. So when did that start?"

"Maybe like a half-hour in?" She paused. "You know what's funny, Jack?"

"What's that?"

"Before, I was worried about hurting your feelings and kept asking if you really wanted to hear this. But now, I fucking love that we're having this conversation. I love that I can talk to you like this. About anything. Even your penis issues."

"Penis issues?" I repeated grimly. "Is that what we're calling it now?"

"Fuck," she hissed. "Here I am trying to tell you how good it feels to be able to talk to you about these things, and instead I'm just ruining it."

"You're not ruining it all," I said, doing my best to sound gentle. "It's just that your choice of words caught me off guard is all. If you think it's helpful to group all of this under the heading of 'Jack's Penis Issues,' then let's do it. I'm very comfortable with that."

"You're sure?"

"Absolutely," I reassured her. "In fact, you know what I'd really like to do right now?"

"What's that, Jack?"

"To turn the lights on and move this conversation in front of the mirror. I mean, I feel like the subject is very much my limp dick now. So let's put it front and center where we can both look at it while we talk. Or what do you think?"

"I think I love the way you just totally embrace your penis issues," she giggled. "Anyway, yes, I think that's a wonderful idea."

With that, we climbed out of bed, Carrie flicking the lights on as we came around to face the full-length mirror. There we stood, C in nothing but her long white T-shirt, and me in nothing at all. Wrapping an arm around my waist, she pulled me close to her.

I'd always liked the way we looked together standing in front of that mirror. Even though it basically always looked exactly like this: me naked and her in her pajama shirt. But this time felt different. The subject here was my limp dick, very much on full display. The woman at my side had just spent over two hours watching me try and fail to get an erection and yet somehow seemed proud to be standing next to me. It was a good feeling.

So I stood there, looking at us in the mirror. And in the reflection, I could see that her eyes were unashamedly focused on my flacid penis. Eventually, that's where my eyes ended up too, when I asked her my question again.

"So you said you started to feel embarrassed for me about half an hour in?"

"Oh, right," she nodded. "Yeah. Cause, like, in the very beginning, I could see how tired you were. Like, 'Aww, poor guy is so exhausted, he can't even get it up.' At which point, I kinda felt a little guilty for goading you into it in the first place. Because you'd told me you just wanted to take a nap, right?"

"So what changed?"

"Well, you did, basically," she shrugged. "It was about a half-hour in that you started to go from tired to frustrated. And I'd never seen you frustrated like that before. I don't mean just in a jerk-off context either. I mean, ever. So yeah, I started to feel embarrassed for you. To the point where - and I don't know if you remember - but I actually suggested maybe you should just give up and have your nap. But you were like - "

"There's no way I can fall asleep if I don't cum."

"Right," she nodded. "And it was hard to watch...uh, no pun intended?"

"Bullshit," I shook my head. "Pun very much intended."

"Indeed," she grinned. "Anyway, it was hard to watch...until I had that sort of revelation."

"You mean, when you could see in my face how I was struggling?"

"Yes. Except, that was just the beginning. Just the opening of the door."

"I don't follow," I replied, meeting her eyes in the mirror.

"Well, like I said, seeing the struggle in your face, I suddenly didn't feel so alone. I had that feeling of, 'Wow, even Jack struggles sometimes.' But at that point, even with that realization, I still felt apart from you, in that it seemed to me that our struggles were very different ones. You were struggling with a momentary experience, whereas I struggle continually with how I feel about my body."

"Enter Jack's Penis Issues, stage right," I surmised.

"Exactly," she smiled, so pleased that I was finally beginning to understand. "See, all the times before when I'd seen you go soft, you never seemed to mind. You were never embarrassed. It was always, 'Hey, this is part of the experience and I'm loving every minute of it.' But this time was different.

"This time, I could tell that you were angry with your own body. Or frustrated? Annoyed? Disappointed? I don't know exactly, I guess. But you weren't happy with your body. And that, finally, was something I could feel with you. Finally, I believed that maybe you could not just appreciate what I feel, but actually feel it with me. And when I realized that, that's when I felt closer to you than I ever have before.

"And that's when I stopped feeling embarrassed for you and started feeling guilty," she concluded.

"Wait, what? Guilty? How, even?"

"Think of the timeline, Jack." Uber-rational Carrie was now making an appearance. "Your limp-dick jerk session ran two hours-fifteen. We've only accounted for the first 90 minutes of it. That means I spent almost forty-five minutes watching you futilely pump your then-useless penis without doing anything to try and help you. And the reason was, I was loving every second of it. I mean, really loving it. I'm sorry, Jack. I know that sounds awful. I mean, it is awful."

"But it's not awful at all," I protested. "I mean, I understand why you would say that. But you finally found a place where you felt like I could share your experience. It only makes sense that you'd want that to last as long as possible."

"Yes," she said very slowly. "But..."

"But what?"

"Well, and this is not so nice maybe, but...it's possible I was kind of testing you."

"What do you mean, testing me?"

"So like, I could see how frustrated you were, how unhappy with your body you were, just wishing to get it over with somehow. And I started to wonder if you'd reach a point where maybe you wouldn't want me to see you like that. Like, maybe you'd just beg off and go to your room where you could finish alone, without the pressure of me watching you just fail and fail and fail.

"Except you never did. Beg off, I mean. You did keep failing though. And every time you came so close, only to lose it at the last second...each time that happened, I felt closer and closer to you. Because you allowed me to see you like that, because you allowed me to watch you fail and never tried to hide yourself or your frustration from me. So yeah, there was a part of me that wanted to see how long and how far that could go on. And the longer it went on, the guiltier I started to feel about it."