Naked Houseboy , his BBW Boss Ch. 09

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*Part 9 in an ongoing series…

After answering her questions, after telling her so much about myself, now it was my turn to do the asking. I put down my glass of wine and brought my hand back down to my dick. I still wasn’t very hard, but it felt good nonetheless.

I looked at her for a moment, preparing my queries. The outline of her massive, heavy breasts, showing through her oversized white T-shirt was spectacular. If she leaned back on the sofa, they hung nearly to her waist. But if she leaned forward, even just a little, they came to rest on her thighs. I felt myself getting harder, just looking at her.

And then I blushed, realizing that I was dangerously close to the line between jerking off in front of my boss and actually jerking off to my boss. I looked away, reaching for the wine again. I hoped she hadn’t noticed.

“Well?” she said, as I took a sip.

“Right,” I nodded. “So, during the interview, I asked you why you wanted a naked houseboy. And you explained that you were tired of dealing with all the bullshit and two-timing that comes with working in the corporate world. That, if your houseboy was naked, he couldn’t be fake with you, the way so many of your colleagues are.”

“That’s right,” she confirmed.

“OK, and that makes sense. But, I guess I’m curious, why do you want a live-in houseboy? I mean, surely you could get the same effect if I were to come by for a few hours each day. Why do you want somebody who’s going to live with you? Why do you want somebody that you can have a meaningful personal relationship with?”

“Wow,” she sighed. “You don’t beat around the bush, do you?”

“I’m sorry,” I winced. “You don’t have to answer if it’s too personal. Maybe it’s none of my business.”

“Don’t be,” she smiled. “And of course it’s your business. It directly affects you, after all.” And she took a sip of wine as she looked up at the ceiling. She exhaled sharply. “Fair is fair,” she said, almost to herself.

“I’m sorry?”

“Fair is fair,” she repeated, louder this time. “You told me something about yourself that you’d never told anybody before. Now I’m going to tell you something about me that I’ve never told anybody.”

“Carrie,” I said softly. “You don’t have to…”

“No, I want to.” She nodded, affirming her conviction to herself.

“OK, I’m listening.” In an effort to appear as earnest as possible, I placed my hands on my knees. If she was going to tell me something serious, something personal, it didn’t seem right to be touching myself.

“What are you doing?” She looked at me quizzically.

“I’m…listening?”

“Honey, I need you to be real right now. Don’t change yourself, it feels forced.”

“OK,” I shrugged, reaching again for my penis. I was toying with it slowly as she began to speak.

“I got divorced two years ago.”

“I’m sorry.”

“Please don’t interrupt.”

“I’m sorry.”

“And don’t apologize. I hate that.”

“I’m sorry,” I winked. She smiled.

“I got divorced two years ago,” she started again. “And I’m glad I did. It was a terrible marriage. I married my high-school güvenilir bahis sweetheart, actually. My first boyfriend. He was the only guy I’d ever been with. And I guess I just assumed all relationships were that way.” She shook her head.

“I’ll spare you the backstory,” she continued. “But it came down to this. He never let me feel good about myself. Physically, I mean. He was very supportive of my career. Or at least it seemed that way. As time went on, it turned out he was just very supportive of me making enough money to take care of him. But that would have been fine.

“The problem, like I said was, he never made me feel good about myself physically. He never made me feel attractive or desirable. Sex was terrible. It was always about him. It was always in the dark, and it was always over fast. Which was a blessing, in a way, I guess. Like I said, it was always all about him. So the sooner it was over, the sooner I was done with it. But that’s no way to live, you know?” I nodded.

“Look, I know I’m a large woman. I know I’m not everybody’s type. So on some level – and I know now how fucked up this is – but on some level, I could rationalize the whole sex-only-in-the-dark thing. But he never once complimented me. Never said, ‘Hey hon, you look nice today.’ Or, ‘You have pretty eyes’ or ‘I love your smile.’ Just, never a kind word, you know?”

What the fuck was I hearing? First of all, what an asshole. But also, was this asshole blind? This woman had the softest brown eyes, the most wonderful smile. Dude couldn’t notice that in 25-30 years of marriage? And also, just, that’s now how you treat people. Especially people you love.

As I was thinking, reacting to her story, I noticed that she had crossed her arms across her chest; an obvious sign of feeling self-conscious. But what did she have to feel self-conscious about? She was a big lady, sure. But she had it all.

I wasn’t about to interrupt her story with my school-yard analogy. But my feeling has always been this. Everybody loves a Ferrari. Small, slim, agile, fast. An archetype of beauty. Now think of a ’57 Chevy. Not as fast or powerful. Big and curvy. But whose head doesn’t turn when that American classic comes rolling down the street? Point being, beauty comes in all shapes and sizes. But I kept my mouth shut.

“Anyway,” she resumed, arms still crossed. “I decided that at 48 years old, it was time for me to start feeling good about myself, time to start feeling good in my own skin. And I guess I thought, maybe if I lived with someone who didn’t mind being around me with the lights on. If I could live with somebody who actually enjoyed being around me as a person, well, maybe that would help. Does that make sense?” she added after a pause.

“Well, it explains why you’d want a roommate,” I conceded. “I guess I’m still not sure why you’d want a naked roommate though.”

“Sure. So, it wasn’t just that my husband made me feel like he didn’t want to see me naked. He didn’t like to be naked himself around me. And I hated that. He wouldn’t get dressed or undressed in front of me. He never slept naked with me, even after türkçe bahis sex. And the thing is, I never once got the impression that it was because he wasn’t comfortable being naked, or wasn’t comfortable with his own body.

“I always felt like he was thinking, ‘Why would I want to be naked around you?’ And that made feel terrible, you know? So I guess I just thought, if I could find a roommate – houseboy, whatever – who felt OK being naked around me, then I would know I wasn’t the problem.” She wasn’t crying. But she was biting her lip, avoiding my gaze.

But what could I say? What a terrible thing for a person to feel. I reached for my glass of wine. In that moment, any thought of touching myself evaporated. I wanted to give her a hug, to tell her she didn’t have to feel like that anymore. But beside the fact that we were both tipsy, I was naked and she was wearing nothing but an oversized T-shirt. Nothing could be more inappropriate than a hug. With no idea of what else to do, I reached for my wineglass.

“Well I’m here now,” I said finally, after a long silence. “And I’m very happy to be naked around you. Not only that, I would be happy to be around even if I was dressed. I mean, not as happy, obviously,” I added. She cracked a smile. “Seriously,” I went on. “You don’t know how lucky I feel to be here right now.” I took another sip of wine.

“Look,” I said, trying to sound more serious than drunk. “I’ve always enjoyed being naked. And I know I just got here. But already, being naked around you is the best being naked has ever felt.” Another sip.

“You’re drunk,” she observed.

“Doesn’t make it less true,” I countered. “In vino veritas. And anyway, you’re drunk too.”

“In wine there is truth,” she translated. “Not drunk enough to miss your clichéd Latin.” Her lips softened into a slim smile. “But you’re very sweet. And thank you for listening. Now you know my baggage.”

“We all have baggage,” I shrugged.

“I guess, but thanks all the same.” I don’t know why, but at that moment, her eyes flitted down between my legs. It lasted but a moment. But it was long enough for me to realize that I’d stopped playing with myself when the conversation got serious. My right hand was holding the stem of my wine glass, my left arm stretched over the back of my chair. What she had seen, in her momentary glance, was a completely flacid penis.

“You’re right about one thing, at least,” she said with a smirk.

“Only one?” I parried

“I am drunk.”

“I see.”

“Which is why I’m going to say something now.” She hesitated. “Maybe.”

“Well you can’t do that!” I protested. “Now you have to say it.”

“It’s going to sound weird,” she resisted.

“We’re doing weird tonight. Go for it.”

“I don’t want to sound mean.”

“I’m not too worried about it,” I rolled my eyes. “Speak.”

“Just remember, I’m drunk.”

“Yeah, yeah.”

“Fine,” she said, fortifying herself with one last sip of wine. “I like seeing your limp dick.”

“The fuck?” I said, eyes wide.

“Shh,” she whispered. “Lemme finish. It’s cute, first of all. You have a güvenilir bahis siteleri cute dick. But that’s not the point.”

“If there’s a point here, I’m dying to hear it.”

“Ssh,” she repeated. “Dick pics are a dime a dozen. You can’t swing a dead cat on the internet without hitting 27 dick pics. And my husband, the bastard…”

“The bastard,” I echoed.

“He only ever came to me with a hard-on. Which was not very impressive, by the way. Yours is much nicer. I mean, when you have one.” She giggled. Wait, did she just compliment me or insult me? Or both? Whatever, I was drunk too. And her giggle was all kinds of cute.

“But with him, it was always,” and she affected a low, manly voice, “Hey, I’m here to fuck you now. Here’s my dick. Ah, I’m fucking you! Ah…I’m done.” She started laughing, partly at him, but mostly at her own impression of him. “Anyway, when its was over, he always put is boxers back on. Like he was embarrassed of his cock if he wasn’t fucking with it.”

“The bastard,” I said again. Alcohol was robbing me of my conversational skills.

“The bastard, that’s right!” she agreed. “See, you get it.” She smiled softly at me. “Anyway, I like how you let me see you when you’re not hard. I like how you’re not embarrassed. Like, if you’re in a job interview or just hanging out on the couch; if you’re jerking off or…what’s the opposite of jerking off?”

“Not…jerking off?” I offered

“Yes! That. If you’re jerking off or if you’re not jerking off. You’re always just like,” and now she affected a different kind of male voice, not quite as asshole-y as her husbands, “you’re always just like, ‘Well, here’s me, here I am, I’m naked, probably I’m jerking off but maybe not but either way, who cares, here I am, doopty-doo.’ That’s you.”

“Doopty-doo?” I sad under raised eyebrows. “That’s me?”

“Something like that,” she shrugged. “Look, I’m just trying to say that I like how you don’t try to hide anything about yourself and how you don’t seem to be embarrassed about your body at all.”

“Is that what you’re trying to say?” I pressed with strained credulity.

“Yes?”

“Because I think your exact words were, ‘I like seeing your limp dick.'”

“I might have said that,” she grimaced.

“You did say that,” I confirmed.

“But I meant…”

“Oh, you explained what you meant.”

“Then you’re not mad?”

“At you?”

“Yeah, at me.”

“Never,” I said solemnly.

“Oh look,” she said, tilting her head.

“What?”

“You’re back at it,” she said, as she nodded downward. And yeah, without even realizing it, I had started jerking again. And not only that, I was growing harder again. Now that the time of serious and personal conversation had passed, I could focus on the task at hand. Pun intended.

“But I think it’s bedtime for me. I’m gonna head upstairs. You stay as long as you like though. Look,” she pointed at the table where my wine glass was resting. Only then did I realize the box of tissues.

“For me?” I asked. She nodded. “You’re sweet.”

“No, you’re sweet.” She stood up. “Good night, Jack.” She started up the stairs. About halfway up, she stopped and looked down at me. “Jack?”

“Yeah, Carrie?”

“Welcome home.” With that, she disappeared upstairs, leaving me alone in the living room to finish myself off…

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