Naked Houseboy & his BBW Boss Ch. 19

Part 19 of an ongoing story...

The previous day, I had worn the chastity device while Carrie was at work. This day, the plan was for me to put it on when she got home. The idea was for her to get used to seeing me in it and for me to get used to being around her with it on. She had been kind enough to give me the day off.

"Don't worry about doing any work today," she had said. "I suspect it's going to be a long night for you, so it's probably best if you can get as much out of your system as you can." What an angel. "Can I give you some advice?" she added rhetorically. "No marathons, OK? The point isn't to have fun. The point is to empty your balls."

It was good advice and I took it.

"I assume your day was excellent?" she asked when she got home. I nodded. "Let me see." She crouched down into her usual 'inspection' position. "Damn. Your balls look exhausted. Which, I guess given the circumstances is a good thing," she added with a chuckle. Standing back up to her full height, she looked me in the eye. "So how many was that? Five?"

"Six," I corrected proudly.

"Well, well," she smiled. "I hope it was enough."

"I guess we'll see," I answered.

"I guess we will. Are you ready?"

"I'm ready." And with that, I fitted the chastity device over my tired penis. This was now my third time locking myself up and if it didn't exactly feel routine, at least it was starting to feel a touch less strange. She looked down at me. Actually, 'stared' is probably the better word.

"I guess I need to get used to seeing you like this," she said softly.

"That's why we're doing it," I smiled.

Since I hadn't worked that day, I hadn't cooked dinner either. So we decided to order in a pizza. We didn't speak much as we sat at the kitchen table. I could see her eyes constantly drifting downwards in curiosity, but her view was obscured by the tabletop.

"Maybe let's open a bottle of wine," I suggested.

"Good idea," she agreed and started to get up.

"Hey, that's my job," I said, also getting up.

"You're off today, I told you that," she retorted.

"I know. But you need to see me, remember?" She shrugged and sat back down. I could feel her eyes on me as I walked to the cabinet where the wine glasses were kept. A moment later, I was walking back to the table, two glasses in one hand, a bottle in the other.

"Stop," she said abruptly.

"What's up?" I asked.

"I just want to look at you." Her eyes were focused on my caged cock. "It's funny. I see you naked every day. I've seen you masturbate countless times. I figured there were no surprises left. But this feels different somehow. New, somehow." As she spoke, her hand absentmindedly reached for the key around her neck. She held it, her lips curling into an almost imperceptible smile. Maybe she wasn't even aware of it. But I certainly was. Finally, she seemed to come back to herself. "Now, bring the wine," she said with more authority than was usual for her. I didn't hesitate.

"So, what should we do now?" she asked as we were finishing dinner. It was a good question, considering all jerk-related activities were off the table. And then, out of the blue, I had the most random idea.

"Do you slow dance?" I asked.

"Slow dance?" she repeated.

"Sure, you know, like at prom or whatever."

"Actually, my husband hated that shit," she frowned. "He didn't have a romantic bone in his body. But it always looked nice in the movies," she added, her features softening.

"Want me to show you how?"

"Sure, why not," she answered, her enthusiasm growing. We went into the living room where I put on some slow big-band music.

"OK, you stand here," I said, maneuvering her by her shoulders. I took a step back. If she were anybody else, there would have been more than enough room for the Holy Ghost between us. But her enormous bust filled most of the vacuum. "OK, now put your left hand on my hip."

"Like this?"

"Just like that, good," I smiled reassuringly. "Now, give me your right hand." A took her hand in mine and were now in the classic slow-dance pose. "OK, ready?"

"Ready," she nodded.

"Just follow my lead." Slowly, I began to move her around the living room floor, rocking in time with the music. She was getting the hang of things pretty quickly.

"This is nice," she said, looking me in the eye; her eyes seemed to glimmer.

"Isn't it?" We danced in happy silence for a few minutes, just enjoying the music and each other's company. But then she started to laugh.

"What's so funny?"

"I just never pictured myself slow-dancing before. Much less with a naked man," she giggled.

"Well, not totally naked," I suggested.

"Oh right, that." And she titled her head downwards to look at my locked up penis. "It looks different from this angle," she said softly.

"Is that a good thing or a bad thing?"

"Just...different."

"Hey! Careful!" She had just stepped on my foot.

"Sorry! I guess I was distracted."

"It's alright," I smiled.

"Jack?" she said, as the first song transitioned into the next. "I think I'm a little tipsy."

"Me too, C," I answered, giving her hand a squeeze.

"Jack? Do people always stand so far apart when the slow dance?" Her eyes were soft as she looked at me.

"Well," I stammered. "I guess it depends on their relationship."

"And what do people do in a relationship like ours?"

"Do you know anybody with a relationship like ours, Car?" She shook her head innocently. "Then I guess we can make our own rules."

"Good," she whispered, pulling me close to her. As she did so, she moved her hand from my hip to the small of my back and rested her head on my shoulder. I could feel her enormous breasts pressing against me. Having already jerked off six times that day and having just drunk half a bottle of wine, I was pretty sure I could withstand this for a short time. But I didn't want to press my luck. When the second song ended, I let go of her.

"Maybe that's enough for one night," I suggested.

"Maybe," she said forlornly. "But that was nice. Can we do it again sometime?"

"I'd love to. But maybe next time without the cage?"

"Oh god," she gasped. "I didn't even think of that. I didn't hurt you, did I?" She took a step back and took a good look at the apparatus. Once again, her hand reached for the key around her neck.

"No, no, I'm fine. But that was probably the right time to stop," I smiled.

"As long as your OK," she smiled, still fingering the key. "Hey, you wanna watch a movie?"

"Sure. Sounds good to me," I smiled.

"Great, let's watch in my room."

"Wait. Don't you want to watch down here?" I gestured towards the couch.

"Nah," she screwed up her face. "It's more comfortable upstairs."

"Well, if you say so..."

"I say so!" And without waiting for me, she started up the stairs. I followed after her.

Carrie was already standing on the far side of the bed when I entered the room. Her cheeks were red. If I didn't know her better, I'd have thought she was embarrassed.

"Sorry," she said, "this is a little embarrassing."

"What is?" Maybe she was having second thoughts about watching the movie in her room.

"Well, I'm just realizing I never even changed out of my work clothes." That was true. I had noticed it myself. But I hadn't said anything because it was so nice to see her dressed up like that. "And I'd much rather change into my pajamas before we start the movie," she added, pointing to the large, white cotton T-shirt which lay folded on the bed. So that was it.

"No problem," I shrugged. I'll just wait outside." That seemed like a gentlemanly solution to the problem.

"No, don't go," she said, her cheeks brightening. "Just...turn around, OK?"

"As you wish," I smiled, trying to put her at ease. I noticed that as I turned around, she did not. At least not while I could see her. Would she undress facing me? On the one hand, what did it matter if I couldn't see? On the other hand, I kinda loved the idea of this woman taking her clothes off while having her eyes on me.

No sooner was my back to her than I started calculating how many articles of clothing she might be wearing. I tried to picture her in my mind. Blouse, cardigan, knee length skirt. Was that all? And obviously whatever underwear she had on. How good were my ears? Would I be able to hear each piece of clothing as it landed on the floor, or wherever she would put it?

A moment later, I heard the sound of her soft, woolen cardigan as she tossed it onto the rocking chair by the window. One. Next came the continual sound of rustling cotton. If had to guess, this was her pulling her shirt out of her skirt and undoing the buttons. Would I be able to determine the sound of each individual button being undone? Doubtful. But then, it would have driven me crazy if I could. A moment later, the sound of her shirt hitting the rocking chair.

Now came the sound of her feet shuffling back and forth. I guessed this was her trying to slip out of her skirt. I heard her take a deep breath and exhale a moment later. I assumed this was her effort at getting the skirt past her broad hips. Not long after, the sound of another article of clothing falling onto the chair. If I was right, Carrie was now down to her bra and panties. God, what I wouldn't give to turn around now!

The moment I had dreamed of ever since meeting this woman was upon me. Or, at least, some version of it. The unmistakable sound of a bra being unclasped, of it sliding off her shoulders, of it landing on the pile of clothes already on the chair. Her breasts, her enormous, massive, pendulous breasts, were uncovered. And I was in the room with her! And I couldn't turn around! Bitter-sweet torture. I started to sweat. My instinct was to reach for my cock. But that being impossible, locked up as I was, I folded arms. She must have noticed.

"Sorry, I'm almost done!"

To be honest, I thought she was done. What else was left to take off except...oh! The sound of one foot coming off the floor and back down again heavily. Then again a second time. She was taking off her panties? She was taking off her panties!

Now, this had always been a bit of a mystery to me; whether or not she wore panties with her 'pajamas.' The T-shirt she wore as evening-wear was too long to be able to actually see anything when she was standing. And it was loose enough so as not to reveal the outline of anything underneath. Add to that, she was always very discreet in the way she sat, so that it I would have had to stare in the most obvious manner to even have a chance of seeing anything. And even that would have been no guarantee. Her thighs were thick enough that they always touched while sitting anyway. Therefore, try as I might - and believe me, I had tried - I was never able to figure out if she wore panties with her pajamas.

Even now, I was still wondering if she was just changing her underwear, preferring something more comfortable than whatever she had worn to work that day. But now, already I could hear her pulling on that oversized T-shirt. So that was it. The T-shirt and nothing else.

"OK, I'm done," she said at last. "You can turn around now."

I turned to face her. And there she was, looking like she always did. The long, baggy, white T-shirt which came about halfway down her thighs. The rough outline of her enormous breasts, which no T-shirt, no matter how baggy, could fully hide.

And so we stood there, looking at each other from opposite sides of the bed. Her in nothing but a shirt, me in nothing but a chastity device. She looked magnificent. But I didn't say anything.

"You know," she started slowly, cheeks still flush, "I think I'm starting to get used to seeing you in that thing." I raised an eyebrow in response. "Don't get me wrong," she hurried to add. "I prefer you without it. Just...you kinda look good with it, too. Is all I'm saying." She looked away, seemingly embarrassed by the admission, even as she fingered the key hanging around her neck.

"Hey, can I ask you something?" I was trying to change the subject for her sake. But the question that came out of mouth was probably influenced by the wine. It was not something I'd have dared to ask sober. I think.

"OK," she nodded.

"You call this your pajamas," I began. "But it's just a big ol' white T-shirt. Why don't you get a set of actual, comfy PJ's?" She tilted her head to one side as a frown crept across her lips. She closed her eyes and sighed.

"You really want to know?"

"Well, I mean, not if you don't want to tell me. I mean, it's not important. Like, at all." I was backpedaling. We were having such a nice night and now I'd gone and said something which had clearly upset her. That was the last thing I wanted.

"No, no, it's OK," she said, opening her eyes. The frown had disappeared, replaced with a sort of wan, regretful smile...if indeed it was a smile. "I mean, I guess it's better to talk about these things. Like, it's not a good idea to keep things bottled up inside, right?"

"That's what the say," I agreed. "But that doesn't mean we have to talk about it now."

"No, we should. First of all, you asked. And anyway, I may want to bottle it up again when I'm sober. So, you know, now's good."

"OK," I said softly.

She walked over to the full length mirror that stood against the wall opposite the bed. Facing her own reflection, she started to talk. To me or to herself, I wasn't entirely sure.

"So, you know I have body issues, right? Stupid question. Of course you know that. And look, I know what you're going to say. I know the words you would use to describe me. Curvy. Voluptuous. Full-figured. Rubenesque. And I appreciate that. Because I know you mean it. I know that's how you see me. But it's not how I see myself. When I look in the mirror," and she gestured towards the glass before her, "I just see a fat woman. I'm fat, Jack. And I know there's this whole body-positive movement nowadays. I know, rationally, I have nothing to be ashamed of. But I can't get there. Or, at least, I haven't been able to get there yet."

I wanted to say something. Anything to cheer her up. But I knew that, at least in this moment, there was nothing I could say. And I shouldn't try. This was her time to speak, to get this off her chest. To share some of the pain that she was living with every day. All I could do in that moment was be there for her.

"You want to know something?" she continued. "I would honestly love a set of flannel pajamas. I mean, they always look so soft, so comfortable. But I know what I would look like in them. Just a big ball of plaid. I would just hate it. I know I would. That's why I wear these stupid T-shirts, Jack. To be as shapeless as possible. When I look in the mirror now, I just see a soft cloud. No real shape at all, like a cloud. I don't love it, but at least I can live with it." There were tears in her eyes.

"Oh, Carrie..." I was at a total loss for words. The poor woman. Fuck. Nobody should be made to feel that way. Not by anyone else and certainly not by themselves. She was done speaking. But she didn't turn to face me. She just kept staring at herself in the mirror. So I approached her. Walked right up next to her so that we were now standing shoulder to shoulder, both our reflections showing in the mirror. Looking straight ahead into the glass, I spoke to us both.

"I guess it would be stupid of me to say I know how you feel, Car. I can't possibly know how you feel. But I would like to tell you something now that I've never told you before. Never told anybody before, actually."

"What's that, Jack?" Her features relaxed as her pain was overtaken by curiosity.

"I actually hate mirrors, Carrie. I hate seeing myself in mirrors. Especially here, in this house. I avoid them whenever I can."

"But what on earth for?" She was staring straight ahead, making eye contact only with my reflection.

"Look," I said, taking a deep breath. "We talk all the time about how much I love jerking off. You're always telling me how great you think it is that I'm so comfortable with myself. That I'm just me, no pretenses, no bullshit. And like, ninety-nine percent of the time, that's true." I stopped. Did I really want to talk about this?

"Go on, Jack," she whispered. "It's OK." I could see her smile in the mirror. It gave me strength.

"But sometimes, when I see myself in the mirror. When I see myself naked in the mirror...it's like...it's too real, I don't know how else to say it. I see my naked self and I just think, my god, is this what I've done? I've created a life for myself that revolves entirely around masturbation? How sad is that?" I almost choked over the word 'sad.' Now there were tears in my eyes. In the mirror, I could see her opening her mouth, about to say something. I stopped her.

"No, listen. I know what you're going to say. I have a passion and I get after it and how many people can say that. You've said it a hundred times. And I know you mean it. And usually that's how I feel too. But sometimes...in front of the mirror...naked..." I couldn't speak anymore.

"Jack," she said softly. "Will you let me tell you how I see you? No, not how I see you. How I know you. Will you let me tell you that?"

I shrugged. There were no more words for me. Not now, anyway.

"The employee that I've come to know is diligent, hard working and extremely good at his job. A job which, by the way, he always puts first, before any personal passions he may have. That's the employee I know. Now let me tell you about the man I know. The man I know is warm, caring, selfless. He puts the feelings of others before his own. He would do anything to help his friends. And he is my friend. Honestly, probably my best friend in the world. And I don't say that lightly.

"Now," she continued. "So what if this employee, this man, this friend, happens to have a tremendous passion for masturbation? What if this guy, left to his own devices, wants nothing more than to jerk off constantly." She almost giggled at these last words. And I smiled too. It served as an icebreaker of sorts. "Sorry, it's not funny. Seriously. So what? Does that make him a lesser employee? Does it make him a lesser friend or a lesser man? Not to me, it doesn't." She smiled that kind smile of hers; all warmth and sunshine. "So let me ask you a question."

"Shoot."

"If you knew I needed help, right? Would you ever, in a million years...would you ever say, 'Hey, sorry Car, I'm kinda in the middle of a wank here. Can whatever it is wait until I'm done?' Would you ever even dream of saying such a thing?"

"Fuck, no, of course not!"

"Exactly! That's my point. You might look in the mirror and see a chronic wanker, a jerkoff-junkie, a serial masturbator, a gooner, a devoted fist-fucker, an evangelist for self-love, a - "

"Jeez, C, I get the idea!" She burst out laughing at her own string of epithets. She was good, no question about it.

"The point is, maybe that's what you see when you look in the mirror. But when I look at you, all I see is my friend," she closed, pointing at my reflection. I looked at my reflection too. Could I see what she saw? Maybe. Then again, maybe not. But I could try.

Enough about me, I decided. I shifted my attention to Carrie, shifted my gaze from my reflection to hers.

"Would you let me tell you how I see you?"

"Jack," she sighed. "I know how you see me." She met my gaze in the mirror. "But go ahead."

"Alright, Carrie, look. I'm not going to patronize you with words like curvy, or voluptuous or whatever. That's not the point here. What I see is a boss who provides her employee with all the tools he needs to do a good job, who puts a roof over his head and keeps food on the table. I see a woman who is kind, warm, funny - very funny, actually - and most of all, non-judgmental. I see a friend who is encouraging, supportive, always there for me. And yeah, I'll say it. You're my best friend, C. My life would be a much darker place without you in it." There were still tears in her eyes, but she wasn't sad now; just emotional.