Naked Houseboy & his BBW Boss Ch. 12

*Part 12 of an ongoing story...

Sunday had been the first time Carrie had watched any porn with me, despite us having lived together for months by that point. By pure chance, I had been watching a lesbian strap-on orgy when she came into my room. Without me saying a word, she had somehow intuited just how hot I found a woman with a strap-on. Although apparently she knew even more than she had let on that day, as I would soon find out...

It was Wednesday night, and as was so common for us, we were just hanging out with a bottle of wine in the living room. As usual, she was wearing her oversized pajama T-shirt, sitting on the sofa, while I was naked and playing with myself in the easy chair. She didn't waste any time.

"Alright, Jack. I want to talk to you about something. Now, every time I ask you if it's OK if ask you something personal, you tell me not to ask permission, that I can ask you anything. So I'm just gonna get straight to it, OK?"

"Go for it," I smiled, although I had no idea what was coming.

"So I have to say, I was pretty surprised by the video you were watching the other day. I mean, not by the video itself. More your reaction to it. Because I know you, and I know your type of girl. You go for the curvy girls with huge boobs." I wondered if she was aware that she just as easily could have been describing herself. "So when you said your favorite girl in the video was the skinny girl with the small tits, that got my attention. And then when I saw the size of the strap-on she was swinging, I got very curious."

"Go on," I nodded. She still hadn't actually asked a question.

"So I started going through your browsing history." She said it so matter-of-factly. And she had every right to. Remember that during my interview, she had agreed to pay for all my porn on the condition that she would have unfettered access to my browser history.

"I see," I said slowly. I could feel my cheeks getting redder and my dick getting harder at the same time. Of course I knew subconsciously that she could have been checking my browsing history this whole time. But the subject had never come up. Now that she was telling me about it, I was somehow simultaneously embarrassed and turned on. Especially given her lead-in.

"And do you know what I found?" This had to be rhetorical. Of course I knew damn well everything that I'd been watching. And even if I didn't know specifically what she was aiming at, I was beginning to get a general idea where this was going.

"What did you find?" I played along.

"You've been watching quite a lot of strap-on videos. And not just lesbian orgies, either. But orgies where it's a bunch of girls with strap-ons and one guy. And then this other kind of video that I didn't even know existed before, although in hindsight I'm not surprised."

"And what's that?" I could feel my heart racing, waiting on her next words.

"Well, I wouldn't even know what to call them. Except I was so curious, I wound up doing a bit of research. Femdom humiliation videos, I guess they're called. Just one woman, with a strap-on, talking to the viewer. Being bitchy, calling him names, telling him what she's going to do to him. Or telling him what she knows he wants her to do to him."

There was no judgement in her voice. Not even surprise really. As always with her, it was curiosity more than anything. Fascination, even. That she had uncovered something new and deeply personal about me. And yet, there was so much more to learn. She knew what I was watching, but she didn't yet know what I was thinking or feeling. And I could see in her face that this was where she was going.

But even though there was no judgement, she was still putting me on the spot. This was the first time she'd ever asked me something so personal without asking my permission first. Nor did I want her to ask my permission. I loved that she was just going for it. Nevertheless, putting me on the spot was exactly what she was doing. And I was loving every second of it. I wondered if she had noticed the precum that was beginning to ooze from the tip of my cock.

"Ok..." I said softly.

"OK, what?"

"OK, ask your questions," I specified. She looked at me for a moment.

"Jack! I want to know everything! Tell me everything!" She was leaning forward, elbows on her knees, chin in her palms.

"Carrie, I'll tell you anything, you know that. But I don't even know where to start. You gotta give me at least one question here."

"OK, OK," she smiled. "Let's start with..." she paused in thought for a moment. "Right, so you're obviously turned on by a woman with a strap-on. Why? What about it?" I nodded. Yes, now we were getting somewhere.

"You mean apart from I just think it looks hot?" I smiled, knowing this was not any kind of answer. Not in the sense of the answers she was looking for.

"Yes, apart from that," she rolled her eyes in mock frustration.

"Well, I guess..." I actually had to think about my answer. I'd never formulated these feeling in words before. "I mean, when I see a woman with a strap-on, there's this confidence, this power, this authority. It's kind of intoxicating. The way they stand, the way they walk, the way they move. I feel like I'm under their power, under their control."

"And you like that?"

"Well, yeah, I guess I do. I mean, it's very freeing, very liberating in a way."

"How so?" She tilted her head a bit to one side, waiting for my answer.

"I mean, it frees me of any responsibility. I don't have to make any choices or think or worry about anything. I just do what I'm told."

"How interesting," she smiled to herself. "I never thought about it that way. But maybe that kinda matches up with why you're here. I mean, I don't talk to you the way they do and I obviously don't walk around with a strap-on. But, on some level, you don't have to be responsible for decisions here. You can just do what I tell you."

"Exactly!" I'd never put that together myself even, but she was absolutely right. "Being with you - and I've told you this - is the most free I've ever felt. I guess there is some connection between the two."

"Sure, sure. But let's not get off topic here." She seemed to forget this revelation almost as soon as she'd come upon it. "But look, power, authority, control. A woman doesn't need a strap-on to have these things. Does she?"

"No, of course not. And perhaps you've noticed, I watch plenty of femdom and humiliation videos where there's no strap-ons."

"I've noticed," she added nonchalantly. "But then, so what is it about the strap-ons that gets you going so much?"

In that moment, I knew what my answer was going to be. But I was suddenly very embarrassed by it. I wasn't sure I wanted to tell her. No, that's not quite true. I wanted very much to tell her. I wasn't sure I was ready to. And I could feel my cheeks burning, even as my cock was rock hard at the thought of sharing this very intimate kink.

Normally, this is where she would say that I didn't have to tell her if I didn't want to. That we could drop it if I was uncomfortable. But she didn't say that this time. She didn't say anything at all. She just kept looking at me, waiting for an answer. I took a deep breath.

"OK, remember the girl from the video we watched together?"

"Of course."

"Good. I want you to picture her. Now, try to remember as many of the other girls as you can. Especially from the one-on-one humiliation videos. Can you picture any of them?" She closed her eyes.

"Yeah, I think so," she said slowly.

"Do you...notice any kind of pattern?" I prodded. She thought silently for a moment, eyes still closed. And then, suddenly, her eyes opened wide, a look of sheer surprise crossing her face.

"Oh, my," she blinked. "Oh, my."

"What do you notice," I asked softly, almost at a whisper.

"They're all huge! Like, twelve inches huge." I nodded without saying a word. "Wow, Jack. So you don't just like a girl with a strap-on, you like a girl with a massive strap-on. You know I'm gonna ask you 'why' now, right?" I nodded again.

"I like it when their dicks are bigger than mine. The bigger, the better."

"You do?" She was clearly surprised. "But why?"

"I find it very comforting. It puts me in my place. And it's a place I like being."

"And what place is that?"

"So look," I began, backtracking a bit. "We've talked a lot about how I'm not really that interested in sex. How I prefer masturbation. And how coming here, living with you, I've been able to explore that. And truly, this is the happiest I've ever been. I mean, I don't ever have to think about or worry about sex here. I can just be my best jerk-off-loving self."

"I know," she smiled kindly.

"But the truth is," I continued, "there are times where I'm still conflicted about that. Times when I feel like feeling this way is somehow wrong. That I'm 'supposed to' want sex."

"The only thing you're 'supposed to' be, Jack, is yourself."

"I know, I know." I smiled. She really was an incredible woman; an incredible human being. "I'm just telling you how I feel sometimes. And I'm trying to answer your question."

"OK, I'm sorry. Please, go on."

"Yeah, so when I see a girl with a huge strap-on, it takes that pressure away. It's like she's saying, 'As long as I'm here, my dick is king. As long as I'm here, nobody's even gonna think about wanting to fuck your dick. So you can just use it for jerking off. Because that's your place. That's your roll. But you can be good in your roll. And you can serve me. And if you serve me and if you do a good job, I'll take care of you. As long as I'm here, my dick is king and I am your queen. And you will be happy this way.' And, Carrie, I love that feeling.

"Wow, Jack. I had no idea you felt that way." There was only kindness in her eyes.

"Didn't you? I mean, sure, maybe you didn't know in such detail. But this can't be much of a surprise. I mean, you said it yourself. Think about my role here. I work as hard as I can to do a good job here, to make you happy. And I'm not looking for sex out of this relationship. I just want to jerk off. And you give me that. So much of what I just described also describes how things are here, with us."

"I guess that's true," she conceded. "On some level. But I don't wear a strap-on. And I certainly don't talk to you the way the girls in those videos do."

"Nor would I want you to."

"And yet you get off to it."

"I get off to a fantasy. I'm not sure I want all of my fantasies to come true, you know?"

"Hmm, I suppose," she nodded slowly. "But, I have more questions."

"I'm sure you do," I smiled. "So let's get into it."

"Right, right," she nodded, thinking about her next question. "So, when we watched that video together, I noticed...or, I think I noticed..."

"Go on," I nudged.

"I mean, it seemed like you got really excited watching the other girls suck off the skinny girl. Like, I had the feeling that you wished it was you there, on your knees, with her strap-on in your mouth. Am I wrong?"

"You're not wrong," I nodded, cheeks burning.

"Have you ever done that? Sucked a strap-on, I mean."

"Never," I whispered.

"But you'd like to? Or is that another fantasy that you'd prefer didn't come true?"

"To be honest, I'm not sure. I guess it would depend on the girl, on the situation."

"OK, fair enough. We'll come back to that," she added calmly. "But let's stick with the fantasy for now." It wasn't a question.

"Sure," I said softly, slowly pumping my cock.

"So, in this fantasy, what is it that turns you on so much about sucking a woman's strap-on?" The calmness with which she posed the question, it could have come for a sex therapist. But there was a genuine curiosity behind it all. She wasn't asking as a therapist. She was asking as my friend. A friend who, at this point, knew more about me than anybody else in the world.

"The submission," I said unthinkingly. I was deep into my jerk-session now, and I was just letting the words come, without trying to frame them in any way. "And the trust."

"Trust?" This was an answer she clearly hadn't expected.

"Trust, yes. Like, to do this thing," I continued, "there has to be trust. I have to trust the woman that she won't take advantage of me in that situation. And she has to trust me that I'm going to do this thing out of a selfless desire to serve her, even if I get no reward from it."

"When you describe it that way, it sounds very intimate."

"Well, I suppose it is."

"But, and forgive me if I'm overstepping, but, not all of the videos you watch seem to be 'intimate,' if that makes sense. At least, not in the way you just described."

"It sounds like you have something in mind," I suggested.

"Well, for example." She clearly had something in mind. "There was this one video with several women wearing strap-ons. And one guy. And they all take turns making him suck them off. More like a toy, then a cherished..."

"Slave?"

"I was going to say servant. But even friend. Which I think is maybe important to you."

"Maybe," I agreed.

"But so what about that video?"

"Well, to be honest, I sort of super-impose my own fantasy on top of that."

"So, now you know I'm going to ask you to tell me about that fantasy."

"Obviously," I smiled. "Right, so, in my fantasy, I always have a special relationship with one of the girls. We can call her my mistress, for lack of a better term. But even friend will work."

"And let me guess. She's always the one with the biggest strap-on."

"Actually, no."

"Wait, really?" She didn't try to hide her surprise.

"No," I clarified. "It's always the one with the kindest face."

"Ah, I see," she nodded. "The one you can trust the most."

"Exactly."

"OK, so there's the one you have a relationship with. And the others?"

"The others are her friends," I went on. And I began to speed up my stroke as I talked myself deeper into my fantasy. "And she's invited them over to show me off."

"To show you off? Like, what, a new car or something?"

"No, no," I shook my head. "I don't know if there's anything you can compare it to. But the point is, and this is key, she's proud of me. It's about pride, in this case."

"Pride?"

"Yeah, pride. She's always very proud of me, and she wants her friends to see that."

"And what is she proud of?" pressed Carrie.

"How well I follow directions, to start with. But anybody can follow directions, you know? She's also proud of how well I do everything I'm told to do." I paused, trying to think of an example. "OK, like, suppose one of her friends asks for a martini. I don't just make her a martini, I make her the best martini she's ever had. If another friend asks for a foot massage, I don't just do it, it's - "

"The best foot massage she's ever had, yeah." She nodded. "I think I get it. But the strap-ons..."

"I'm coming to that," I answered hurriedly. "So look, it's one thing to make a drink or give a foot rub, right? But to get on your knees and suck a strap-on, that's a whole new level of commitment, of submission. And she wants to show her friends how willingly and how eagerly I will do that, if she so much as asks. And how I'll do it for all of her friends too."

"OK, OK, but why is this the thing?" She was scratching her head in thought now. "I mean, a well made drink, an excellent foot rub. That I can understand. But if the other girls don't have that relationship with you, what do they get from having their strap-ons sucked? I mean, it's rubber. They can't feel that."

"Not in that way," I smiled.

"Then in what way?" she pressed.

"So now we get into why my woman is proud of me, why she wants to show me off." I paused. Carried leaned forward in anticipation. "The care with which I approach the task, the attention I give them, the way I submit myself to them completely and without question..."

"Yes, yes?!" I had her hooked, I knew it. And I was having fun drawing this out, even as I was drawing out my own jerk-session.

"I will make each one of them feel like a goddess. I will make them feel revered, loved, feared, in ways they've never felt before. And when my women sees her friends feeling that way, because of ME, that's when she will be most proud of me."

Silence. For what felt like minutes, Carrie said nothing. She just looked at me. Finally, she spoke.

"So that's your fantasy." I nodded silently. "And yet," she continued, "it doesn't get you off." She added this observation with a raised eyebrow.

"I'm sorry?"

"You don't get off to this fantasy," she repeated. "It doesn't make you cum."

"Why would you say that?" Now it was my turn to be confused.

"Well," she shrugged, "I'm just looking at you." She didn't say anything more than that.

But she was right. My erection had lost some of its stiffness. I was so caught up in describing my fantasy, I hadn't even noticed.

"I guess you're right, Carrie." I shook my head in disbelief. "I guess you're right. It's more about here," I said, taking my left hand from my balls and pointing to my heart, "than here." And I moved my hand back to my balls.

"Which is fine," she smiled. "And very interesting actually. But I'm assuming you do actually cum when you watch these videos?" It was a rhetorical question. "So what does actually get you off in the end?" A good question. I thought for a moment.

"Usually I have to beg them for permission to jerk off."

"And how does that go?"

"Well?" I smiled.

"Stupid," she laughed. "I mean, describe what that's like."

"I know, I know," I grinned. "Well, first I just ask for permission. I say, modestly, that I've done everything that they've asked of me and if they are happy with how I've served them, perhaps they would be kind enough to allow me to jerk off."

"And are they? Do they?"

"Well, first they usually want me to beg. Grovel. Humiliate myself. I have to declare myself a jerk-off addict. I have to tell them how it's the only thing I want for myself in the world, apart from serving them." I could feel myself getting harder again as I spoke the words.

"And that convinces them?"

"Sometimes. But usually it's not enough."

"Then what's enough," asked Carrie, leaning forward again.

"One of the girls, usually the bitchiest one, will say something like, 'Maybe we should let him. But he's only allowed to touch himself if he has a strap-on in his mouth.' And she'll step forward."

"And then?" She was totally engrossed.

"And then I have to get on my knees and take her strap-on in my mouth. But it's different than it was before. Before it was about serving her, making her feel like a queen. Now, it's only about showing my own submission. And she'll fuck my face. Grab me by the hair and force me down on her, Just because she knows she can. Just to show her power. And whereas before, my woman was showing me off as something special, now this woman is showing me off to the other girls as something pathetic, something that will humiliate itself just for the chance to masturbate."

Carrie sat entranced, staring at me. I was rock hard again, and nearing climax. But I noticed that even her cheeks had grown somewhat flushed. And was she sweating?

"So now this girl is fucking my face as the other girls stand around me in a semi-circle, slapping me with their strap-ons, laughing at me. And that's..." I inhaled sharply.

"And that's?" whispered Carrie.

"That's usually when I..." I closed my eyes. I was stroking my rock-hard cock furiously now. "When I..."

I never finished the sentence. Hot cum shot from the tip of my dick, splattering on my chest, my shoulder, my chin even.

"Fuck," I exhaled.

"Fuck, indeed," she repeated, in a whisper. For a long moment, she just looked at me. I closed my eyes, sweating, still trembling from my orgasm. "Jack," she said softly.

"Huh?" She didn't answer. She only patted the seat beside her on the sofa. I tiptoed over and fell into the sofa beside her, pressing my cum-spattered body into her soft frame, only a T-shirt between us. She put her arm around me.