Naked Houseboy , his BBW Boss Ch. 20

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Party 20 of an ongoing story…

“So what do you want to watch?” Carrie had asked. Since I was still locked in chastity, we had decided that watching a movie would be a good way to pass the time. Knowing that she, like me, had a bit of a nerdy side, I suggested Star Wars.

“One of the originals?” she asked.

“Are there any others?’ I countered.

“Fair point. Episode Four then?”

“Sounds good,” I smiled. After our last conversation, A New Hope seemed appropriate. So we climbed into her bed and started the movie. But honestly, I was so tired by that point that I passed out before the opening scroll was finished. When I woke up a few hours later, the movie was over, the screen black, the room dark. I was surprised to find Carrie fast asleep beside me. Well, that wasn’t what surprised me. What surprised me was that she had fallen asleep on her side with her arm draped across my chest. Although it was dark, I could still make out her features. She seemed so peaceful, I didn’t dare wake her.

And yet, there was no way I could extricate myself from her bed without waking her. A dilemma. I looked again at her serene face. And I wondered if maybe, just maybe, the reason she looked so peaceful was because I was there with her. I realized then that I was feeling pretty peaceful myself. But having just woken up, I wasn’t quite ready to fall back asleep again. I was simultaneously with Carrie and alone with my thoughts.

It was a strange situation I now found myself in, lying in Carrie’s bed, her sleeping next to me, her arm across my chest. When was the last time I had shared a bed with a woman? I couldn’t even remember. But the fact that it had been so long was very much by design. I mean, I had had opportunities. But the truth was, I didn’t like sharing a bed with a woman. Not casually, anyway. Sure, if she was really special. But I didn’t seem to cross paths with special woman very often, Carrie notwithstanding.

That was why I had turned towards masturbation. More to the point, it was why I had turned away from sex. Failing the right woman, I just didn’t like being close or intimate with anybody. Sure, sex could be fun, if you got it over with quickly enough. My problem – if indeed it was a problem – was that the longer it went on, sex I mean, the more I had time to think about the person I was with. And usually, the more I thought about the person I was with, the more I would invariably lose interest. So that by the time it was over, the last thing I wanted to do was spend more time with whatever willing, kindhearted, but ultimately dimwitted woman had seen fit to izmir escort bayan lay down with me. If I was at her place, I’d just leave, claiming an early day at work the next morning. Or if at my place, I’d move to the couch, pretending I couldn’t sleep while offering some excuse about not wanting to disturb her with my tossing and turning.

At some point, I decided it was just easier to jerk off. It was then that I discovered it wasn’t just easier, it was actually better in every way. Masturbation wasn’t something to be rushed, it was a thing to be enjoyed. I soon learned that I could jerk off for hours and love every minute of it. And when it was over, I felt good. There was no unwanted person around to be avoided. It was everything I wanted.

Except. Except it could get lonely sometimes. Here I had found this thing that I loved and I had no one to share it with. And then I met Carrie. This wonderful woman who wanted to know everything about my little world of masturbation, who wanted to share it with me, enjoy it with me. After I moved in with her, I didn’t feel so lonely anymore. Or so I thought.

But now, laying in her bed with her, I realized that I had, in fact, been missing something. I realized that there really was something beautiful about sharing a bed with a woman. IF it was the right woman. And Carrie certainly seemed to be the right woman. But if she was actually the right woman, shouldn’t I want to fuck her? Did I want to fuck her? Or did I just want her to show me her tits and watch me jerk off to them? That was not a conversation I was ready to have with myself.

One thing I knew for certain, I was very happy to be there in her bed at that moment, her sleeping beside me, her arm across me. Until that moment, I hadn’t realized just how much this had been missing from my life. I smiled. And that was the last thing I could remember before falling back to sleep.

The next thing I remember was being woken up by her alarm the next morning. With a groan, Carrie rolled out of bed and went straight into the bathroom. She had completely ignored me. Had she forgotten I was there? Was she so not a morning person that she couldn’t pay me any mind even if she’d wanted to? Or did she wake up sober and thinking it was a bad idea after all, letting me sleep in her bed? While I certainly hoped it was not the latter, I had to admit that it was a real possibility.

In any case, when I heard the shower begin to run I decided it was time for me to head downstairs. Whether last night had been a good idea or not, I still had a job to do. In a few minutes, Carrie would go escort izmir down to the kitchen and she would be expecting her coffee.

I had a few moments to think while I was waiting for the coffee to brew. I decided that I wouldn’t say anything about last night. If Carrie wanted to bring it up, that was on her. But if she didn’t bring it up, I would take it as a sign that we were not going to talk about it.

When she finally did come down to the kitchen, she smiled at me as she always did. She didn’t say anything. But then again, we never really talked in the mornings anyway. Was this the normal silence or was it something more? It was killing me! But I had resolved not to bring it up and so I kept my mouth shut.

After a few sips of coffee, her eyes seemed to open a bit. She seemed more alert. I tried not to make eye contact, but I could feel her looking at me. Finally, I met her gaze.

“So,” she said softly. Pregnant pause. “How did you sleep last night?”

How did I sleep last night?! How the hell was I supposed to answer that? If she was about to tell me that last night was a mistake and I was too enthusiastic in my answer, I’d look like an idiot and make things awkward. But if she felt good about last night and I wasn’t enthusiastic, then I’d still look like an idiot and would probably make her feel like an idiot too.

“Oh, you know, pretty good, I guess,” I mumbled, trying to sound as tired as possible. I looked at my feet. “How about you?”

“Oh, Jack,” she smiled, nudging me in the ribs. “I slept like a baby! I honestly can’t remember the last time I slept so well!” A smile started to creep slowly across my lips. And I would have been very happy if she’d stopped there. But she didn’t stop there. “I don’t know. Maybe it was the wine, or the dancing, or the movie. Or some combination of those things, I don’t know. All I know is, I slept so well.” She was smiling.

But my smile was fading. The wine? The dancing? The movie? Not a word about me sleeping beside her. So that was that, then. We weren’t going to talk about it. Well, I guess I could live with it. I mean, I had never expected that I would ever sleep in her bed anyway. So why not just take it for what it was – a perfectly lovely night – and leave it at that. I could do that, couldn’t I? She handed the mug back to me.

“Well, I’d better get to work. Don’t want to be late,” she added with a smile before turning to leave. She was about halfway to the kitchen door before I called out to her.

“Hey, C!”

“What’s up?” she turned to face me. For a moment, she just stood there, staring izmir escort at my naked body from across the room. I had hoped it would have been obvious. But she seemed not grasp the reason for my calling to her. “What?” she said again. I pointed to the metal cage around my penis. “Oh!” she gasped. “Right, sorry. Sorry!” With that, she pulled the chain from around her neck. For a moment, she held the key in her hand, looking at it, fingering it. It was almost as if she didn’t want to part with it. I coughed. She looked up at me. With a smile, she tossed the key to me, underhand. By the time I caught it, she was already out the door.

“Well,” I thought as I unlocked myself. “One thing’s for sure. At least she’s gotten used to seeing me in this thing.” Leaving the cage on the kitchen counter, I grabbed my dick and started playing with it. I hadn’t been able to masturbate since yesterday afternoon and it felt so good just to touch myself again. I started up the stairs with the intention of going to my room to finish the job. But at the top of the stairs I got another idea. I wanted to see if last night’s conversation had changed my thinking in any way. And so I did something which, before yesterday, I would never have dreamed of doing. Instead of going to my room, I went to Carrie’s.

I had never allowed myself to masturbate in her room before. It just didn’t seem right. But now her room had something that I needed. I walked right up to the full-length mirror and stood in front of it. I watched my reflection as I jerked my hard cock. And I didn’t mind seeing myself. So what if I love to masturbate? Almost as if hypnotized, I watched myself jerk off. This is who I was and it was time to own it. Carrie was right. I had nothing to be ashamed of.

In the mirror, I could almost see Carrie standing there beside me, smiling. I closed my eyes, remembering how she had undressed behind me the night before. I thought about how, just for a moment, she had been naked in the same room with me. I imagined her massive tits hanging low as she bent down to pick her panties up off the floor. Only this time, she was facing me. Bent at the waist, her enormous breasts hanging down to past knees, smiling at me. I could even hear her voice. “I love how much you love jerking off,” she giggled.

That was all I could handle. Jerking furiously, I exploded all over the mirror. When I opened my eyes, I saw my reflection obscured by the load of cum dripping down the glass. “Shit,” I thought. “Better get the windex!”

After I’d finished cleaning the mirror, I went back to my room for my usual morning nap. I wasn’t really horny anymore, but it was so nice to be out of chastity, that I started playing with myself anyway. I didn’t cum. I didn’t even really get hard. I just sort of drifted off to sleep with my dick in my hand on a smile on my face…

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