Naked Houseboy , his BBW Boss Ch. 21

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Şub 13, 2022 // By:analsex // No Comment

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Part 21 of an ongoing story…

Friday was a difficult day for me. Last night, Thursday, was the night that I had slept in Carrie’s bed. But Friday morning, she had acted as if nothing had happened and then she’d gone to work. So I was left home alone, wondering if it had all been a mistake. Would we simply never talk about it?

I had spent the day trying to lose myself in my work and trying to distract myself with porn. But I could never really get it off my mind. Would she say anything when she got home? What would that evening be like?

I have to admit that, in the end, I was disappointed. Carrie was pleasant when she came home from work. She was never not pleasant. But she still made no mention of last night’s events. I was coming to the realization that I’d have to let it go. It seemed clear to me that she viewed it as a lapse in judgment. Nothing to be ashamed of, nothing to make things awkward between us. But also, something to be forgotten and never to be repeated. I might need a couple of days, but I’d get over it.

After dinner, Carrie said that she was pretty burned out from work and just wanted to go to bed early. In and of itself, that wasn’t unusual. But, on this occasion, I found it rather frustrating. See, I’d hoped we might spend some time together that evening. Because even if we weren’t going to talk about it, at least if we spent some time together, maybe we could start getting back to normal.

And so, Carrie disappeared off to her room and I to mine. To take my mind off things and to kill some time, I decided to watch a movie. But when the movie was over, I was still wide awake. Which meant it was time to jerk off. Now, normally jerking off before bed clears my head and puts me right to sleep. But that night, I couldn’t get anywhere close to sleep. And so, after a few hours of tossing and turning, I decided to go down to the kitchen and pour myself a glass of scotch. It was 2:30 in the morning.

As I drew near the kitchen, I noticed that the light was on. That was unusual. But maybe I’d forgotten to turn it off. I never imagined that when I entered the kitchen, I would see Carrie there. Yet there she was, sitting at the kitchen table with a bottle of wine before her and a glass in her hand. I noticed that the bottle was already half-empty.

“Fancy meeting you here,” I smiled.

“Couldn’t sleep,” she said softly, avoiding eye contact.

“Yeah, me either. I was gonna have a glass of scotch,” I said, opening the cupboard. “Mind if I join you?”

“Sure,” she said, looking into her glass.

With a bottle of scotch in one hand and a rocks glass in the other, I sat down across from Carrie. I poured myself two fingers. For what seemed like forever, neither of us said anything. Finally, she looked at me.

“I think we should talk about last night.” She was nearly whispering. Part of me was overjoyed that we would finally be having this conversation. But part of me was nervous too, because she didn’t exactly look happy.

“So…” I wasn’t sure what to say.

“Look,” she took over. “I want to say some things. Please don’t interrupt, OK? Just let me talk.” There was a softness to her words, a vulnerability. I nodded. She took a a deep breath before beginning. “I feel very strongly that for our professional relationship to work, it’s important that we respect certain boundaries. And it’s not that I don’t feel close to you or like you or anything like that. In fact, I feel very close to you. And I consider you to be my friend. Maybe my best friend. But I’m also your boss. And you’re my employee. And I think it’s important that we don’t lose sight of that.”

“I understand.”

“From kadıköy escort day one, I’ve worried that if we got too close, it would run the risk of undermining that professional relationship. And if things went south, I wouldn’t just be out the best houseboy I could ever hope for, but I’d also be out a dear friend. That’s not something I ever wanted to risk.”

“I totally get it.” I was trying my best to sound understanding and supportive. But I was also growing increasingly nervous about where this was going.

“But now I have a dilemma.” And for the first time that night, she looked me in the eye. “You see, last night was the best I’ve slept in years. It was the most peaceful, the most restful sleep I can remember having. And I wanted to lie to myself. I wanted to believe it was because we drank a lot. I wanted to believe it was because we had a lovely night dancing and watching a movie. I hoped that if I just ignored it, we could move on and pretend it never happened.” She took a sip of wine and refilled her glass.

“But the truth is,” she went on, “I know that the reason I slept so well was because you were there with me. And more to the point, I know that the reason I can’t sleep now is because you’re not there with me. So this is my dilemma. I can either invite you back to my room again and destroy that boundary at the risk of all of this. Or I can tell you that it can never happen again. And never again sleep as well as I did last night. I honestly don’t know what to do.” She looked at me with hope in her eyes. Hope that I might somehow solve this problem for her.

“Carrie, I don’t know what to say.” Which, at least, had the virtue of being true.

“Just be honest with me. Tell me what last night was for you.” And as she looked at me, tears were welling in her eyes. “If you tell me that last night was nothing special for you and that you could sleep just as well in your own bed, then OK. I’ll get over this. If anything, that will make this easier for me.”

“Oh, Carrie,” I sighed, taking a sip of scotch. “Believe me when I tell you, the last thing I want to do is risk what we have here.”

“I know,” she whispered, turning her eyes down towards her glass.

“But the truth is,” I said softly, “I slept like a baby last night. I honestly can’t remember the last time I slept so well. And I think that’s why I can’t sleep tonight. Like, after last night, how could I possibly sleep alone in my bed? I mean, I was tossing and turning for like two hours before I came down here.” I frowned, knowing that my answer could only complicate things. I looked at Carrie. “I’m sorry, C.”

“Don’t be,” she said, reaching her hand across the table.

“So what do we do now?” I asked, taking hold of her hand.

“We go to bed. Together.” As she rose to her feet, she pulled me up along with her.

“But Car,” I protested weakly. “If we do this, there’s no going back. I mean, that particular boundary is gone forever.”

“There are still other boundaries,” she smiled. With that, my hand in hers, she led me upstairs to her room.

When we entered her bedroom, we stood for a moment looking at the bed.

“Now what?” I asked

“Now we go to sleep,” she smiled. And so she walked around to the far side of the bed and climbed in under the covers. “You coming?” she looked up at me? I nodded. A moment later, we were both under the covers. Just as the night before, she lay on her side, stretching her arm across my chest.

“Are you OK?” she whispered.

“Why do you ask?”

“Your heart is racing. I can feel it.”

My heart was indeed racing. There maltepe escort was no way I could fall asleep like this. Not yet, anyway.

“I think I know what the problem is,” she smiled softly in the darkness. And she pulled back the blanket to reveal my raging hard on. “You always jerk off before you go to sleep, don’t you?” The question was rhetorical.

“Maybe I should got to my room and take care of this. Then we can go to sleep,” I suggested.

“Why would you go to your room?”

“What? To jerk off. So we…so I…can fall asleep?”

“I know,” she said softly. “But why would you go to your room? Why not just do it here?”

“What, in your bed?” I couldn’t believe what she was suggesting. It was one thing to sleep in Carrie’s bed. But to masturbate there? It seemed wrong somehow.

“Oh, come on,” she smiled, patting my chest. “Did you suddenly become a prude? And anyway, is there anywhere in this house that you haven’t jerked off?”

“Well, yeah, your bed,” I protested. “I mean, this is where you sleep.”

“Yes,” she nodded. “That’s what beds are for. But they’re for other things too. Or hadn’t you heard?” I liked her when she was sassy.

“Your sure you don’t mind?” I needed to be sure.

“Honestly, at this point, I’d be more offended if you left. I’d be asking myself, what’s wrong with my bed? You don’t want to offend me, do you?”

“Never,” I acceded.

“Well then. Get to it!”

She was encouraging me to masturbate in her bed. With her there. And yet, she didn’t move. She stayed just as she was, on her side with her arm stretched across my chest, her head on my shoulder. I suddenly felt all warm inside as `I reached down and began to stroke my cock. And as I did so, I could feel my body relax.

“There. Isn’t that better?”

“Mmhmm.” Word were beyond me at that point. I turned my head so that we were face to face, our noses millimeters apart. I looked into her eyes, and she into mine, as I jerked myself off. It was a beautiful moment. And I wanted it to last forever. But there was no way I could make this last even two minutes. Before I knew it, I was pumping furiously, hot cum shooting from the tip of my dick and splattering across my belly. I exhaled deeply.

“Well done,” she smiled and patted my chest again. “Now we can go to sleep?”

“Now we can…oh, shit.”

“What’s wrong?”

“Have you got any tissues?” I asked.

“In the bathroom,” she whispered.

“Would you mind grabbing me some? I’d go myself, but I don’t want to drip on your carpet.”

“Don’t worry about it,” she smiled.

“But – “

“Didn’t you once tell me,” she said, cutting me off, “that you often don’t clean yourself off before you go to sleep?”

“Well, yeah,” I admitted. “But that’s in my bed. With my sheets.”

“I really don’t feel like getting up,” she sighed. “And anyway, you do the laundry around here, so I’m not worried about it.”

“Still though,” I protested. “I’d feel bad.”

“I’ll tell you what…” she trailed off. She didn’t actually tell me anything. Instead, she slid her hand down from my chest to my belly and began massaging the cum into my skin, as if it were nothing more than moisturizer. I was too surprised to say anything. Not that I would have tried to stop her. It felt good. And it was intensely intimate. So I let her do it and just enjoyed the moment.

When she finished, I expected that she would once more drape her arm across my chest in the same way that we had fallen asleep the night before. But she didn’t. She simply left her hand on my belly.

“I want to touch it,” she whispered.

“Huh?” escort bayan This caught me totally off guard.

“Your penis,” she said softly. “Can I touch it?”

“You touch it every day for inspection,” I said coolly. “You don’t need my permission.”

“But this isn’t an inspection,” she smiled.

“I’m done with it,” I smiled back. “Do as you like.”

So she slid her hand further down and took hold of my now soft penis. Gently, softly, she began to pull on it, massage it, feel it.

“I like the way it feels when it’s like this,” she cooed. “You work that poor thing so hard, I feel like it needs some gentle affection.” I had the feeling her words were more for herself than for me. But there was no denying that I loved the way she was handling my spent, limp dick.

Now, I know this is going to sound strange, but there was nothing ‘sexual’ about what she was doing. I had just cum and it would be several minutes before I had even the slightest chance of getting hard again. And so, in those few minutes, my penis was not a sexual organ, but rather just another tired, overworked part of my body. It would have been no different than if she had given me a shoulder rub after a long day of work.

“And these,” she said, taking hold of my balls with a gentle grip, ” shouldn’t be neglected either. You work them pretty hard too,” she added with a giggle.

It was bliss, believe me when I tell you. I closed my eyes, enjoying the softness of her touch on my exhausted balls.

“Are you falling asleep?” she asked.

“Not yet,” I whispered, my eyes still closed. “But soon, I think.”

“OK,” she answered in her own whisper. Then she removed her hand from me and pulled the blanket back up over us, draping her arm across me once more. I was already beginning to doze off when she spoke again.

“Jack, I want to tell you something. I hope it’s not gonna sound weird.”

“What is it?”

“It means a lot to me to be able to touch you like I just was.”

“It was really nice for me too…”

“Shh, let me say what I want to say. I know how much masturbation means to you. I know that if it was physically possible, you’d be jerking off every minute of every day. I know that, if you could, you’d never take your hand off your dick. So the fact that you let me touch your penis, that you let me hold your balls, even for just a few minutes, it’s like…it’s like a privilege. There’s something that’s so important to you and yet you let me have it for a little while. That’s really special to me. Thank you. And I hope that’s not weird.”

“It’s not weird at all, Car,” I said, my eyes still closed. “It made me feel really special, the way you were touching me. It made me feel really close to you. I like that.”

“Really?” she purred.

“Really. And I’ll tell you something else,” I said, opening my eyes and turning to face her. “I don’t every want you to ask for permission again. From now on, anytime after I jerk off, if you feel like you want to touch me like that, you just do it, OK? Don’t ask.”

“You mean it? Or are you just saying that because your in a moment?”

“I mean it.” And I bumped my nose against hers to seal the deal.

“Like, even now?”

“Even now,” I smiled. And she reached and under the covers and wrapped her hand around my soft dick and balls.

“Do you think you could fall asleep like this?” she whispered.

“I could definitely fall asleep like this,” I said, closing my eyes.

“Just promise me one thing,” she said.

“Of course.”

“If you wake up…you know, with an urge. And I’m still sleeping. Do what you have to do, OK? Here. And don’t worry about waking me up. Promise?” She was smiling softly in the darkness.

“I promise.”

“Good night, Jack.”

“Good night, Carrie.”

And so I feel asleep in Carrie’s bed, with Carrie lying on her side next to me, the palm of her hand resting against my penis, her fingers wrapped around my balls…

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