Naked Houseboy & his BBW Boss Ch. 22

Part 22 of an ongoing story...

I woke up in the middle of the night. I didn't know what time it was. In fact, for a moment, I didn't even know where I was. It took me a moment to remember that I was sleeping in Carrie's bed. When I had fallen asleep, Carrie was on her side, facing me; the palm of her hand resting on my spent, limp dick; her fingers wrapped softly around my balls. But in her sleep, she had rolled over to her other side, her back to me.

I woke up in the middle of the night, hard and in need of a wank. Carrie had made me promise that if I woke up with an "urge," I would take care of it there, in her bed. And I wouldn't worry about waking her up.

"Carrie?" I whispered, making sure that she was actually asleep. She didn't stir. Well, a promise is a promise. Slowly, gently, I peeled back my side of the blanket, exposing my erect cock to the cool night air.

Slowly, with as little motion as possible, I began to massage my dick. She had said not to worry about waking her. I took that to mean, if it happened, it happened. But I would at least try to do this without interrupting her sleep. So for a while, I didn't even stroke. I just sort of rubbed my shaft with the palm of my hand.

Strange, I thought. Given how much I jerk off, it was a pretty rare thing for me to do it without porn or without Carrie and with no time pressure. I mean, even when I would have a two hour jerk session during the day, always in the back of my mind I would know that at some point I had to get back to work. Or when I'd go for three or four hours at night, I always knew I had to get up the next day for work.

But now, there was no porn to urge me towards orgasm. There was no Carrie; or, at least, no Carrie to talk to. And I had all the time in the world. So for quite a while - maybe twenty minutes - I just lay there, rubbing myself. And it was wonderful. I just felt so relaxed, so at peace.

But after twenty minutes or so, just rubbing wasn't enough. And so I wrapped my hand around my cock and began to stroke. Slowly, still. For I was still conscious of trying not to shake the bed, of trying not to wake Carrie. But after another ten minutes or so, I could no longer control myself. I started to speed up my pace. And as I did so, the bed started to shake slightly, in time with my rhythm.

It was at that moment that Carrie rolled over to face me, opening her groggy eyes with a soft smile. I froze.

"Hi," she whispered.

"Hi," I croaked dryly.

"Couldn't sleep..." she added softly.

"You or me?" I asked.

"You, I'm guessing." She was smiling.

"Sorry I woke you," I cringed.

"I told you not to worry about it." And she placed her hand on my chest, running her fingers through my chest hair. That was enough to put me back at ease and I resumed stroking. "How long have you been at it?"

"I don't know," I confessed. "Maybe half an hour?"

"That's nice," she cooed.

"Did you only just wake up?" I followed.

"I actually woke up about ten minutes ago. But I didn't want to disturb you. Plus, I was enjoying how you were making the bed rock. To be honest, I wanted to see if I could fall back asleep while you were jerking. You know, like falling asleep in the car."

"I take it you couldn't?"

"Actually, I nearly did. But then you started speeding things up and it was too much. So that's when I rolled over."

"Oh. I'm sorry," I frowned.

"I told you not to be," she hissed, landing a light slap on my chest.

"I know, I know. But wait," I added. "You said you wanted to fall asleep while I was jerking?"

"Yeah, I did. I mean, I know it sounds silly. But in my half-waking haze, the idea of falling asleep while you jerk off next to me in my bed struck me as super romantic. Like, what a great sign of how comfortable we are with each other when I can fall asleep to the rhythm of your masturbation?"

"That's actually really sweet," I answered. "I mean, I really like that idea. On one level."

"Only on one level?"

"Well, I mean, I really like the idea. But I'd be lying if I said I wasn't glad you rolled over. Because now you're here with me."

"Ooh, smooth talker," she answered in a husky tone. And then she sighed.

"What is it?"

"I kinda lied to you just now a little bit."

"You did?"

"Yeah," she frowned. "See, I told you that I couldn't fall asleep once you started going faster. But that wasn't exactly true. I mean, it wasn't totally false either..."

"What do you mean?"

"I mean, when I closed my eyes, all I could see was you. Your face, your body, your hand jerking your cock, your balls. And while you were going slow, it was this peaceful sorta hazy vision, you know? But once you started going faster, it became very vivid, very active, very..."

"Hot?"

"Shut up." And she slapped my chest again. "No, I just sorta realized, why am I gonna try and fall asleep imagining something when I can just turn over and see the real thing?"

"Well I'm glad you did," I proclaimed.

"So am I," she smiled.

At that point, it seemed there was little left to say. So we just lay there in the dark, me jerking off, her with her hand on my chest. It was several minutes before she spoke again.

"What are you thinking about?"

"Are you sure you want to know?"

"Come on, Jack. I never don't want to know what you're thinking about when you masturbate."

"Well, I was thinking about the party..."

"Oh?"

"More specifically, I was wondering about Kara."

"Ah yes, Kara with her enormous tits. Why am I not surprised."

"Hey, you asked."

"True. I did. OK, so what about Kara?"

"I was thinking about what she might wear. Do you think she'll wear something that shows off her boobs?"

"Well, if I know Kara, she's going to wear something super low-cut. I mean, bordering on obscene."

"You think?" Just the thought of it. I started jerking faster.

"Oh yeah. I'm sure the girls will be front and center." She paused. "Well, maybe not center. Maybe a little lower than center, given her age. But certainly front!" She started to laugh. "But yeah. I mean, we invited four guests to the party. But really, it's five. Kara and her plus-one; her cleavage."

"Wouldn't that be plus-two," I panted.

"I remember this one time," Carrie went on, ignoring me. "Me and the girls went to this very fancy restaurant. And we all take our linen napkins and tuck them into our shirt collars. Except for poor Kara, whose neckline basically came down to the table top. She had nowhere to tuck her napkin in!"

"Oh my god," I whispered.

"Hey, you know? Maybe I'll ask her if she still has that dress. I can tell her you requested it special for the party. Or would that embarrass you?"

The thought of Kara showing up with her monstrous tits in a dress with an 'obscenely' plunging neckline...and her knowing that I'd asked to see her - to meet her - that way...

"I mean, I wouldn't want to embarrass you..."

"No, please ask...please tell...please...embarrass me!" As I said these last words, I could see Kara, proudly displaying her cleavage, looking at me, looking at my naked body, at my caged dick, laughing wickedly, knowing that all I wanted in the world was to jerk off to her cleavage...and yet, in chastity!

I exploded so hard that a few drops of cum landed on the back of Carrie's hand as it rested on my chest.

"Wow! Nice shot," she added, turning her hand over, wiping the cum into my chest hair.

"Sorry," I sighed. "I didn't mean to hit you with it."

"Oh, don't be such a prude," grinned Carrie in the darkness. "Just try to keep it out of my hair, OK?"

"Now who's a prude?" I shot back.

"It has nothing to do with being a prude," she said sternly. "It's just a pain in the ass to wash it out, that's all. I mean, you're not going to wash my hair for me too now, are you?"

"Would that mean I get to come into the shower with you?"

"Aaand, we're changing the subject," countered Carrie.

"Oh we are, huh?" I paused for a moment. "And what shall we change it to?"

"Actually, I think it's best if we got some sleep. Tomorrow's going to be a long day, and you're going to need your energy," she added as she massaged the still warm spattering of cum into my chest.

"It is?" I asked. "I am? I don't suppose you're going to tell me what for?"

"Not yet," she answered, nuzzling her head into my shoulder. "I'll explain in the morning. But now, try to get some sleep."

"If you insist," I agreed. "But could I ask you to do something for me?"

"What is it?"

"Well, before, when we fell asleep, you kinda had your hand..."

"...on your balls," she finished for me. "Did you like that?"

"Very much," I whispered. "Very much.

"Like this?" And she slid her hand down between my legs, gently wrapping her fingers around balls. She didn't squeeze, she just sort of cradled them in her fingers.

"Just like that, yes," I whispered.

"Alright, Jack. But tell me why. I want to hear you say why."

"Because," I said, turning to look at her, "when my balls are in your hand like this, it makes me fell warm inside. It makes me feel safe."

"Well," she smiled. "Safe and warm is how I want you to feel. Now," she added, giving my balls a soft and momentary squeeze, "get some sleep. Sweet dreams, Jack."

"Sweet dreams, Carrie."

With my balls safely - and literally - in the palm of Carrie's hand, it wasn't long before I drifted off to slumber, wondering what the next day held in store....