Naked Houseboy , his BBW Boss Ch. 08

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Babes

*Part 8 of an ongoing story…

After checking out of the hotel where I’d been staying for the last two months, I arrived at Carrie’s house at 5:00, as agreed. Carrie’s house. “My new home,” I reflected as I trundled up the driveway with my two suitcases in tow. I didn’t have to ring the bell this time. She was already waiting for me at the front door.

“Welcome home,” she said with a smile, waving me inside.

“It’s good to be home,” I grinned.

“Here, let me help you with that,” she said, taking one of my suitcases. “I’ll show you to your room.”

I followed her upstairs. My room was on the left. Her room was across the hall on the right. One door down was my bathroom. She had her own off the bedroom. She set the suitcase down on the floor of my room and I followed suit.

“I’ll leave you be. I’m sure you want some time to unpack and set things up the way you like them. I took the liberty of putting fresh sheets, blankets and pillows on your bed. But if they’re not to your liking, we can go shopping tomorrow.”

“I’m sure they’re fine, thanks,” I said politely.

“Oh, they are fine. But this is your home now. And I want you to feel at home. So I’d be more than happy to take you shopping. I’d feel better knowing you were sleeping on sheets you chose rather than what I happened to have laying around.”

“That’s very kind, thank you.” I couldn’t help but smile.

“Great. OK, so I’m going to head downstairs. But listen, I was thinking. Maybe tonight we can just order a pizza. And if you’re not too tired, after that we can maybe have a glass of wine?”

“That sounds great,” I said, unbuttoning my shirt. “What time were you thinking?”

“Seven?” My shirt was off now.

“Perfect,” I agreed, beginning to unzip my pants.

“What do you like on your pizza?” Now my pants were off.

“Oh, just plain, thanks.” I slipped my boxers off.

“No kidding? I always get plain.” She was smiling, but not at my being naked. It was as if she hadn’t even noticed that I’d completely undressed in front of her. No, she was just smiling because with both liked plain pizza. I loved how easy this was, and I was getting the feeling that she was of a similar mind.

“Great then,” I nodded, placing my hands on my hips. “So, I’ll see you at seven.”

“See you at seven,” she echoed before departing.

Once she’d gone, I looked around the room. There was a bed and a nightstand. A desk and a chair. And a bookshelf. Nothing decorative, nothing to indicate that anybody actually used this room. Except for two things. On the night stand was a scrap of paper with the WiFi password. And beside it, a box of tissues. I had to laugh at that. After this morning’s experience, she’d clearly gone out of her way to add this little touch. And I was most appreciative.

“Unpacking can wait,” I thought. “I need a nap.” With that, I closed the door, set my alarm for two hours and threw myself into my new bed. Which was very comfortable, not for nothing. I was out before I could count three sheep.

Next thing I knew, my alarm was going off. Groggily, I rubbed my eyes. “Two hours already?” I shuffled downstairs, still half-asleep.

“Good morning,” called Carrie from the bottom of the stairs. “Sleep well?”

“Very and also not enough,” I smiled weakly. “Is the pizza here yet?”

“Just arrived,” she confirmed, waving me into the kitchen.

After a lovely meal, we decided to move into the living room. Carrie grabbed a bottle of white from the fridge. “Grab two glasses from the cabinet above and to the left of the sink, would you?”

I opened the cabinet to find an array of glassware. Champagne flutes, large glasses for red, smaller ones for white, even whiskey tumblers. “Was there whiskey?” I wondered to myself. Taking two white-wine glasses, I followed her into the living room.

She sat down on a large sofa while gesturing towards a comfortable looking recliner, which sat at a right angle to the sofa. There was a small lamp-stand between them, where I placed the wine glasses.

“So you know the difference between glasses for red and white. Off to a good start,” she winked. With that, she poured us each a glass. “Cheers.”

“Cheers.” We clinked. And then said nothing. For almost two minutes.

“So…” she offered.

“So…” I agreed.

“Any problems checking out?” she queried.

“Nope,” I sipped. “Nope. No problems.”

“That’s good,” she sipped. “That’s definitely good.”

“Definitely good,” I echoed, taking another sip.

“So um…”

“Yes?”

“I mean…”

“You have questions,” I suggested.

“I do,” she nodded, taking another sip. Those furtive eyes again, avoiding my own.

“Ask away.” I also took another sip.

“I bahis firmaları know. But this is just…”

“A little awkward?” I offered.

“I mean, just a little.”

“Hence the wine,” I smiled.

“Hence the wine,” she repeated. She inhaled deeply before speaking again. “Like, I have so many questions. But I don’t want to make things more awkward. And I definitely don’t want to say the wrong thing and offend you. Which is weird, because at work, I’ll say anything to anybody. I don’t give a fuck. But this is so no that, and I’m scared I’ll ruin things on your first night and oh my god I’m rambling.” She stopped short.

“It’s totally fine!” She was making me laugh. Well, her and the wine. “You’re not ruining anything. And you won’t,” I added seriously. “I promise.”

“How can you promise when you don’t even know what I’m going to ask?”

“Look, can I make a ground rule?” I leaned forward a little.

“Let’s hear it.”

“You can ask me literally anything at literally any time. And I promise – cross my heart – I won’t be offended or get mad. The worst I’ll ever say is, ‘That’s personal’ or ‘I’d rather not answer that.’ OK?”

“But how can you – “

“Because I know how I’m feeling right now. And I can only imagine how you must be feeling. This is new for both of us. We’re both trying to keep an open mind here, right? So I promise to take any question you ask me with that attitude. Deal?”

“Deal!” And with that she stretched her glass to me and clinked again.

“So?”

“So,” she steadied herself. “This masturbation thing – it’s OK if we talk about this? If ask you about it?”

“Is it OK if we talk about my favorite subject in the world?” I asked with pretended ponderousness. “I think so.” And I threw her a wink.

“So this masturbation thing,” she continued. “How long have you been…I mean, were you always…have you always loved it? The way you talked about it at the interview, I mean.”

“For as long as I can remember, absolutely.” I tried to make my answer earnest, honest, confident. To show, without saying, that I was truly comfortable talking about this.

“And when you said that the ‘no sex’ thing wouldn’t be a problem. You meant, because you’d rather masturbate?”

“Well,” I paused. I mean, she was right. But it still felt weird to say it. Like, that’s not what you’re ‘supposed to’ say. Who in their right mind prefers jerking off to sex? Or, at least, that’s the message we’re constantly bombarded with. Form television, movies, music, even our friends. And yet, it was true for me. And wasn’t the point of all this that I was finally in a place where I could admit that?

“See,” she interrupted my thoughts. “I knew I would make things awkward with my questions.”

“No, not at all!” I insisted. “I was just trying to find the best words for my answer.” She didn’t look convinced. “Look, your question was: Would I rather jerk off than have sex. That’s your question, right?” She nodded, avoiding my eyes. “Well, the answer is…usually.”

“Usually?” She looked up at me.

“Look,” I sighed. “When I’m with somebody that I truly care about, somebody that I really have feelings for, then I’m all in on the sex and jerking off can…pardon the pun…go fuck itself. But it’s so rare that I find myself with a person like that. I guess I kinda need to be in love,” I shrugged.

“And if you’re not in love?”

“Then sex just kinda feels like work, to be honest with you.” Now it was me who was having trouble meeting her eyes. This was something that I knew was true about myself, but it was not something that I particularly loved about myself. “The thing is, I’ve always had a hard time separating the physical from the emotional. Like I need to be emotionally invested for it be fun.”

“That’s,” she said finding my eyes, “actually kind of beautiful.” And as soon as she had found my eyes, she looked away again. “I wish just one of the guys who have ever fucked me could have said that.”

“Oh, Carrie, I…”

“No, it’s OK.” She downed what was left of her glass. “That’s my baggage. And we’re talking about you now. I want to know more.”

“OK,” I nodded. “Anyway, to answer your question, barring some dream girl that I’m head over heels for, yeah, I’d much rather jerk off than fuck.”

“Well that answers the first question,” she smiled, returning to herself.

“You mean there’re more?” I smiled, finishing my own glass.

“Oh, for sure,” she grinned mischievously. “But first, another glass?”

“Please.” She refilled our goblets.

“So you’ve explained why masturbation over sex. Good. But what I’m really curious about it is, why do you love it so much? Why do you want to be doing it as much as possible?”

“I suppose if I said, ‘It makes me feel kaçak iddaa good,’ that wouldn’t be enough of an answer, huh?”

“Not if we’re gonna get through that over there,” she answered, nodding at the half-empty (half-full?) bottle of wine.

“Right,” I shrugged. “So obviously it feels good physically. But more than that, it brings me to a place of no worries, no stress. I feel relaxed when I’m masturbating, comfortable. Not just with my own body, but with myself; with the world, even. It brings me to another reality, one that I often think is better than this one. Oh, fuck.”

“What is it?” she asked, showing some concern.

“Nothing. It’s just, I’ve never verbalized that before. And hearing myself say it, it sounds like a drug. Fuck.”

“Yeah, maybe,” she acquiesced. “But also, I mean, I think people would describe yoga the exact same way.” And she laughed. “But I say that having never done a bit of yoga in my life, so what the hell do I know?” She sipped some more wine.

“I’ll take it,” I smiled. “No, but really, that’s basically it. I love the way it makes me feel. And the longer I go for, the better I feel. The more often I do it, the better I feel. I don’t know if it’s some kind of chasing-the-dragon or what. But if it is, well, masturbation is my dragon.”

“Hmm,” she screwed up her face in thought.

“What?”

“Well, just, I mean…if that’s how you feel, why aren’t you doing it right now?”

“Is that a serious question?”

“Oh, fuck. I’m sorry. I didn’t mean…see!? This is what I mean. I’ll ruin everything with all my stupid questions.”

“What? Who’s ruining anything?” I was incredulous.

“But you said – “

“I asked if it was a serious question, yeah,” I repeated, as if it were obvious. “This is our first evening together. We’re still getting to know each other. I haven’t even slept one night in this house. Why am I not jerking off right now? You think I don’t want to be? But come on, how rude would that be? You think you’re worried about making things awkward with an ill-considered question? I’m fucking terrified that I’ll start touching myself without even realizing it. At which point you would obviously be wondering, ‘What kind of sleazy perv did I just hire?’ That’s what I meant by, ‘Is that a serious question?'” I stared hard at her. She stared hard back at me.

And then we both burst out laughing.

“You thought…” she said, holding her sides.

“And you thought…” I said, shaking my head.

“Look,” she rolled her eyes, laughter subsiding. “It’s clear we’re both kind of walking on egg-shells here. And it’s just as clear that neither of us wants the other to be walking on egg shells. So how do we get past this?”

“It’s a good question,” I agreed.

“And one that you can think about while I go change into my pajamas. Maybe that will help.” She didn’t wait for an answer, she just popped up off the sofa and went up to her room. While I awaited her return, I poured myself another glass of wine. Mere moments later, she descended the staircase. At which point, my eyes nearly popped out of my head.

Her ‘pajamas’ were nothing more than a very long and very baggy white T-shirt. It was at once clear that she was not wearing a bra. Through the shirt, I could see her mammoth breasts, hanging down nearly to her waist, swaying gently from side to side as she hopped lightly from step to step. Nothing was left to the imagination.

Well, not nothing. It wasn’t possible to tell if she was wearing panties. A small detail.

And then she was seated on the couch again, just as she had been before.

“You call that ‘pajamas’?” I asked, trying not to be too obvious.

“Well, it’s how I sleep,” she shrugged. “And if you define ‘pajamas’ as what you wear to sleep, then yes.”

“Can’t argue with that,” I yielded.

“So look,” she said. Her tone indicated that she was picking up where we’d left off. But I was so distracted by her ‘sleep-wear’ that I’d plum forgotten where we’d left off. “If you’re not in the mood, I get that. Just, the way you talk about masturbation, I guess I just assumed you’d be doing it now. You can, you know.” And she finished her second glass of wine.

“Well like I said, I didn’t want to be rude.”

“Dude, seriously?” She picked up her glass again, only to find it empty. She reached for the bottle. That too was empty. “We need another bottle. In the fridge.” It was a command. And she was clearly getting a little tipsy.

“Right. Back in a jiff.” Moments later, I returned with the new bottle, from which I refreshed our glasses. “You were saying?”

“I was saying?”

“I don’t know. All you said was, ‘Dude, seriously?'”

“Oh, right!” she exclaimed, taking another sip. “Dude, seriously? Do you think I kaçak bahis would hire a naked houseboy? No, fuck that. Do you think I would hire YOU? After everything you told me about your great undying love for all things masturbation, do you think I would hire you if seeing you do it would put me off? Be real.”

“Well, I…”

“You’re very sweet, is what you are.” She smiled pleasantly. She might have been tipsy, but she wasn’t drunk. And her words were honest. “Thank you. Seriously. Thank you for making every effort to be respectful. Honestly, you’re probably right. If you had started going at it with no consideration of how it might make feel, maybe I would have thought you were rude and inconsiderate. But I’m telling you now,” she said taking another sip, “it’s OK. If you want to, you should.”

“Thank you, Carrie. Really.” I paused. “Because I really want to.”

“Then go for it,” she smiled.

So I put my wine glass on the table and reached down to my still soft penis with my right hand. Slowly, I started massaging it. Not much was happening yet, but it felt good.

“So like, how many times today?” She eyed me curiously.

“Well, let’s see. Once when I woke up. Another after I called you. Once here, after the interview – “

“Yeah, I remember that one,” she chuckled.

“And then again back at the hotel. So four. I think.” I was starting to get hard. Not rock hard, but enough that I could tug properly.

“You think?”

“Well, I jerked off after we got off the phone. Then I took a nap. I guess I don’t remember if I jerked again before I came over for the interview.”

“I see. So, either four or five.”

“Well, five or six, counting this now.”

“Hmph.” She sounded…what, I don’t know. Unconvinced?

“I’m sorry.” She avoided my eyes. “I don’t want to keep you from it. If you’d rather go up to your room…”

“What are you talking about?”

“No, I just thought we could use the evening to get to know each other. But if you want to masturbate, that’s totally fine. You should go do that. We’ll have plenty of time talk and get to know each other. Don’t let me keep you.”

“Seriously, Carrie, what are you talking about? We are getting to know each other. Why would I want to leave now?”

“Because…” she couldn’t finish her thought. But I followed her eyes. She was looking at my not very hard cock.

“Oh, my god, Carrie. You think because I’m not rock-hard right now I’d rather be somewhere else?”

“Well…wouldn’t you?”

“Oh, Carrie,” I smiled. “You wanted us to get to know each other. So let’s get to know each other. I’m going to tell you something about me now, OK?”

“Tell me.”

“Jerking off, for me, it’s not about being hard. And it’s definitely not about cumming.”

“It’s not?” She looked lost. “Then what’s it about?”

“Jerking off is about jerking off. It’s about the act itself. I don’t care if I’m hard or not. I’m just happy be playing with myself, to be in that headspace, to have that physical feeling. Look at me.” She looked me in the eye. “No, look at me,” I nodded downward.

Her eyes fell to my crotch.

“Look at me. I’ve jerked off four, maybe five times today. We’re already on our second bottle of wine. I’m pretty limp-dicked at the moment. And I don’t care. Because I’m jerking off, and it feels good.”

“So you like this?”

“Carrie, I love it. And the fact that I get to share this with you? I mean, come on. Look, you asked me before about masturbation versus sex. Well, here’s another reason. What good would I be to a woman right now? But I can’t disappoint myself.”

“Wow.”

“Yeah, look, I guess it’s kinda sad, but…”

“No, it’s not sad. I like how at peace with yourself you are about all this. I wish I could…but, you don’t want to go upstairs?”

“Not in the least. There’s nowhere else I’d rather be, nothing else I’d rather be doing. And no one else I’d rather be with.” She squinted at me.

“You don’t believe me?”

“I believe you. I was just thinking. You said, ‘it’s definitely not about cumming.’ What did you mean?”

“Oh, just, when I cum, it’s game over. This thing that I love, this thing I’ve been enjoying, it’s over. No orgasm can match how good it feels to be three hours deep in a jerk session. I just meant, I don’t jerk off to cum. I jerk off to jerk off. If that makes any sense.”

“I think I understand.” Maybe she did, maybe she didn’t. But there wasn’t much left to say on the matter. So we sat in silence for a while. Me absent-mindedly pulling on my let’s-be-honest mostly limp dick in complete contentment, her eyeing me curiously over her glass of wine.

After a few minutes, I managed to take my hand off my cock and wrap it around my glass of wine instead. The spell was momentarily broken. I spoke.

“Hey, you know, so far you’ve been doing all the asking. But I have some questions for you too.” I took a sip. “I mean, if that’s OK?”

“Ask away,” she smiled obligingly…

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