Naked Houseboy & his BBW Boss Ch. 15

Naked Houseboy & his BBW Boss Ch. 15


Part 15 of an ongoing story...


In the last post, I described what Carrie and I called "The Inspection." Each day when she came home from work, she would ask me how my day was. I would tell her it was anywhere from OK to fantastic. Then she would ask about my masturbation while she was at work. And I would give her a detailed rundown in terms of how many times, how long each session lasted, how much total time and if there was porn or phone sex involved. Then she would crouch down for a close up look at my equipment. Sometimes she would poke and prod a little, sometimes she would just look. But what she was really doing was collecting data. This went on every day for about six weeks. Then one day she came home and she didn't ask me how my day was. At least, not right away.


As always, when I heard her car pull into the driveway, I went into the kitchen to pour her a glass of wine. A few moments later, she was standing in the doorway of kitchen. When she saw me standing there with her drink, a wide grin spread across her face. She walked up to me, happily accepting the glass.


"Hi, you!" she said with a twinkle in her eye.


"Hello. Somebody's in a good mood," I said, stating the obvious.


"That would be me," she smiled, taking a sip of wine. "How about you and me play a little game?"


"A game?" I repeated. "Sure, why not. What do you have in mind?"


"A guessing game."


"Like Clue, or what?"


"No, stupid," she grinned. "A different kind of guessing game."


"Go on..."


"OK, so in a minute, I'm gonna ask you how your day was. And you're going to tell me 'good,' 'great,' whatever. But that's it. No details, got it? And then I'm going to do my Inspection. And I'm gonna guess." Her eyes were twinkling. "So. Wanna play?"


"Sure, what not?" I shrugged. "But I don't know how accurate you think you're going to be..."


"You let me worry about that." She took another sip of wine. "So...how was your day?" She was looking right into my eyes. I returned her stare.


"Pretty good," I shrugged. She closed her eyes.


"Pretty good...pretty good...pretty good," she repeated softly. "OK, let's see what we see." With that she crouched down so that she was face to face with my dick. At first, she just moved her head around, trying to see me from as many angles as possible, all the while making little humming noises. Then, she took my soft dick between her index finger and thumb, raising it up to look at the underside of my shaft. When she'd seen enough, she lowered my dick back to its usual position and let go. Finally, every so gently, she cupped her right hand around my balls. For a moment, she simply cradled them. Them she did some light squeezing, applying the slightest pressure with the tips of each of her fingers in succession. Last of all, with her cupped hand, she raised my balls every so gently, almost as if weighing them. With my balls still in her hand, she looked up at me.


"You know, you almost fooled me. But I think I got it."


"Oh, you do, huh? Well, professor, tell me what you've learned."


"So at first, judging by 'pretty good' - your words - and the way your penis looks, I was going to guess that you masturbated four times while I was at work. Your usual quickie just after I leave, and other quickie after your nap. Right?"


"So far, so good." I loved the way she was looking up at me from that crouched position with my balls in her hand. The funny thing was, I wasn't getting hard. It wasn't a turn on like that. But it was sure as hell fun.


"OK, good. Now, your dick is a little red where you normally grip yourself. But it's not bright red, or anything stronger. So I'm guessing that's the result of roughly two hours of jerking. And it must have been two sessions, because if you jerked for two hours straight, your day would have been better than just 'pretty good,' that's for sure."


So far everything she said was spot on. I did jerk for two hours in the afternoon, and it had been two sessions of about an hour each, just like she said. I couldn't believe she was this accurate. But she wasn't perfect. Not yet, anyway.


"So that's it then?" I asked. 


"Well, at first I thought so. But something wasn't adding up. I mean, I can feel it in your balls." And as she said this, she did that thing again where it was like she was weighing them. "See, I can tell that you finished your last wank not long before I came home."


"You can feel that!?" I was astonished. "Yes. Your balls feel a certain way for about half an hour after you cum. Obviously that's something I only learned over the past six weeks. But once I discovered it, it's unmistakable. And here's another thing that will blow your mind."


"Go on..."


"Your balls don't feel the same after a quickie as they do after an hour long jerk session. And that's what threw me for a minute. But I think I've got it now. See, you came within the last half hour, but this is" - and she lightly squeezed my balls for emphasis - "this is not the result of some hour long jerk session. So what's going on? And then it occurred to me. You had a quickie just before I got home. But a quickie after not one but two hour-long wanks? How is that possible? Unless..." With that word, she released my balls and stood back up, looking me in the eye.


"You, my friend," she said, tapping me on the shoulder, "had a phone sex quickie just before I got home. That makes a total of five times you masturbated while I was at work, for a total of two hours and a half, maybe two forty-five," she declared triumphantly. 


My eyes grew wide. I was in shock. I couldn't believe what I was hearing. She was 100% accurate in everything she said. And the way she reasoned it all out, especially the last part about the phone quickie, I was astounded. I was positively in awe of the woman.


"So? How'd I do?" she asked.


"Oh my god, Carrie, I couldn't have described it better myself! You're amazing!" Then, without even thinking, I threw my arms around her and squeezed her into a tight bear hug. In the moment, her arms wrapped around my back and she pulled me in even closer, squeezing me as tightly as I was squeezing her. Even through her work clothes, I could feel every one of her curves against my naked flesh. But I wasn't thinking about that so much as the fact that this was the first time we had ever hugged each other.


And do you know what? It was just a really nice, warm moment. Look, there's no question that the relationship between her and I was, shall we say, unusual. But we cared about each other very much. Only, in that moment, it was more than just caring. In that hug, I felt something new. In some way, somehow, we loved each other. Of course, we were nowhere near saying those words. But the emotion was there, and it was definitely flowing in both directions.


Yet, even as I was thinking this, biology was doing its job. Feeling her body pressed against mine, particularly the fullness of her massive breasts, caused an unavoidable swelling in my dick. And it was only when she too noticed it that she broke the hug and took a half-step back. As she did so, for the briefest of moments, her eyes flitted downward and a look of what I could only call disappointment flickered across her face at the sight of my semi-erect penis. Almost as if to say, 'Why did you have to go and spoil a perfectly nice moment like that?' But the look vanished almost as soon as it had appeared.


"Im sorry," I blushed.


"Oh that? Don't even worry about it. It's perfectly natural," she said with smile and a wave of the hand.


"I just thought...I mean...we were having a nice...actually," I shifted gears. "What I mean is, I'm sorry I just up and hugged you like that. Without asking you first. I mean, we've never hugged before. And we're very hands-off with each other. For a reason, of course. And I think that it's right that we're hands-off - "


"Jack?" she cut me off. "Thank you for hugging me."


"Wait, what?"


"God, Jack, I can't tell you how many times I've felt like...well, I've felt like I just needed a hug. But I've always been terrified to ask you. Like you said, we're hands-off with each other for a very good reason. And also, as your boss, I was always afraid that you would feel pressured into accommodating me, even if it made you uncomfortable. So I knew I could never ask you. But honestly Jack, that hug just now did me a world of good. Thank you. Really." Her cheeks were beaming. 


"I'm so glad to hear you say that, Carrie." I breathed a sigh of relief. "Honestly, it did me a lot of good too. I don't think humans are meant to be deprived of physical contact, even of the platonic sort. And yet that's what we've boxed ourself into, haven't we?"


"I couldn't agree more, Jack," she nodded. "And look, now that this is out of the way, I hope we can have more hugs in the future. Whenever either of us needs it. If that's OK for you?"


"Of course! I would really like that too," I smiled. "I'm just sorry I ruined this one with my..." I didn't finish my sentence, but simply looked down at my dick, which for some reason had apparently decided to graduate from semi- to full hard-on. 


"Oh, Jack," she winced. "I'm the one who's sorry! When I said it was a perfectly natural reaction, I meant that. I never should have made you feel ashamed like that. That was a shitty thing for me to do."


"Oh come on, it was perfectly understandable," I said soothingly. 


"That's sweet of you to say, but you know I'm right. Look, let me fix this. Come here," she said, opening her arms wide. "I want to hug you again. All of you." As she said the word 'all,' her eyes drifted down to my hard cock. 


"Are you sure?"


"Bring it in," she nodded. And so we embraced a second time. Only this time I didn't feel embarrassed or ashamed of my erection. And instead of wrapping her arms around my shoulders as she did the first time, this time she wrapped them around the small of my back, intentionally pulling my hardness against her, pinning it between our two bodies. It wasn't erotic, exactly. It was more her way of saying that she loved every part of me and that I had nothing to be embarrassed about with her, ever. And then she whispered in my ear.


"But if you get precum on my skirt, the dry-cleaning bill is coming out of your pay," she hissed wickedly.


"We wouldn't even have to worry about if you weren't wearing a skirt," I whispered back. That was enough to end the hug. In one motion she unclasped her arms and slapped me playfully on the back of the head.


"Don't press your luck," she said, grinning wickedly. At just that moment her cell phone rang. She pulled it out of her pocket and looked at the screen. "It's Vicky," she said simply. Vicky was one of her best friends from college. I'd heard plenty about her, but we'd never met or spoken. Then Carrie's wicked grin turned into an evil smile. 


"Hey," she said to me, while still looking at the screen of her phone where Vicky's name was prominently displayed.. "Wanna have some fun?"


"Sure," I smiled. "What do you have in mind?"


"Just follow my lead," she winked. And with that, she answered the phone, putting the call on speaker. "Hello?"...

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