Naked Houseboy & his BBW Boss Ch. 34

*Part 34 of an ongoing story...

"Then this concludes the Q&A portion of the evening," Carrie was saying. "And now, the fun starts. You see, I've planned a little game for us."

"Game?" I asked. "What game?" For all the talking and planning we'd done regarding the party, never once had Carrie mentioned anything about a game.

"That's my special surprise for you," she winked. "For all of us, really," she added to the group. "Now, if you'll excuse me, I need to get some things from my room. You know, for the game. In the meantime, Jack, why don't you make another round of drinks for the girls?" With that, Carrie disappeared upstairs.

As for me, I went into the kitchen to make the drinks, as I had been instructed. As I was mixing the first martini, I heard soft footsteps coming up behind me.

"Can I help you?" It was Samantha. My heart skipped a beat. Was she simply trying to be helpful or was she, just maybe, looking for an excuse to be alone with me for a few minutes?

"Of course not," I answered pleasantly. "I'm the houseboy and you're the guest. I don't want you to lift a finger."

"Fair enough," she answered, coming to stand beside me at the counter. "But you don't mind if I hang out in here with you while you work, do you?"

"Mind? I'd be delighted!" Perhaps she was just looking for an excuse to spend some time alone with me. I smiled at the thought of it.

"I have to say Jack, I'm really quite impressed," she said, seemingly apropos of nothing.

"With what?"

"With how comfortable you were back there, how open you were. I mean, that was some incredibly personal stuff. If it were me, I would have been embarrassed for sure. In fact, I..."

"What, Sam?" I noticed that she was blushing.

"You know what's funny, Jack? I barely know you. But somehow, I feel like I can talk to you about things I'd never talk about with anybody else. And that's because of you. Something about you just puts me at ease. Like, if you're not embarrassed, why on earth should I be?"

"Thank you, Sam. That means a lot to me. Honestly." And I noticed that now I was blushing.

"Can I be honest with you, Jack?"

"Wouldn't have it any other way," I answered as I stirred the first martini.

"When Carrie said she would never sleep with you because of your size, I was positively mortified. I couldn't believe she would say that about you, especially with you standing right there. I mean, it was downright shocking. But once you started to explain how it made you feel, with zero shame and even actually passionately, any feeling of embarrassment just completely evaporated. To the point where, after a few minutes, the idea of all of us having a conversation about the size of your penis seemed like the most normal thing in the world. Is that weird?"

"I don't know," I answered with a laugh. "I mean, is it any weirder than coming to a party and be waited on by a naked houseboy in chastity?"

"That's exactly what I'm trying to make sense of, Jack. On paper, everything about this night is so fucking weird. And yet, the actual experience...it doesn't feel weird at all. I mean, here you are, totally naked except for that cage and it just feels...I dunno, normal. Okay, so I told you that I would like to consider us friends already. I told you I already feel like I can talk to you about anything. And the thing is, I think that's precisely because you're naked. You just put it all out there with no hint of embarrassment and that just makes me feel incredibly comfortable around you."

"Wow, Sam," I said softly.

"I'm sorry. I've said too much, haven't I." Blushing, she took a step back.

"No, not at all!" I said, turning to face her. "You just caught me by surprise is all. The truth is, in a way that I can't explain, I feel very close to you somehow. I mean, don't get me wrong, the others are lovely, and I feel totally comfortable around them, accepted by them. But with you, I feel something different. Almost like I've known you forever."

"So you feel it too," she said softly as her eyes met mine.

"Can I be honest with you now?" I asked.

"Please, Jack."

"Right when we first met, I knew we'd get along. But the truth is, there was a particular moment when I really felt something...something special..."

"When I grabbed you by the balls." Her words were almost a whisper.

I nodded.

"Oh my god, Jack, that was electric! Honestly, I'd never grabbed a man like that before. And when Vicky was pushing me to do it, I didn't know what the hell to expect. But once I had you..." She paused, looking at me. "It was like the whole world faded out around us and it was just you and me. And it felt so right."

"It felt so fucking right." I looked at her. "Sam, would you like to..."

"Jack, more than anything." I could feel my heart pounding as I watched her hand reach for my -

"Hey! How's it coming with the drinks in there!?" yelled Vicky from the living room.

"Shit," I groaned.

"Back to work, houseboy," winked Sam. But before I could turn back around to the counter, she took a step towards me. Then, grabbing my balls, she leaned in and kissed me lightly on the lips. It only lasted two or three seconds. A few minutes later, she was helping me carry the next round of drinks back to the living room.

"Finally," declared Kara, accepting a martini from me.

"Finally," declared Vicky as she saw Carrie coming down the steps.

We all turned to look. Carrie was carrying in her arms five black boxes. The boxes were roughly 18 inches in length and about four inches in both width and height. All five boxes were seemingly identical and devoid of any marking. I think it's fair to say that none of us had the slightest idea what Carrie had in store for us.

Without saying a word, Carrie laid out all five boxes in a neat row on the coffee table. Our eyes darted back and forth between her mischievous smile and the black packages before us.

"I suppose you're wondering what this is all about," she grinned.

"That would be an understatement," replied Allison.

"Then listen up," said Carrie. "We're going to play a little game. Each of the boxes you see before you contains a dildo and a strap-on harness."

"This is already interesting!" said Kara, leaning forward, much to my delight.

"Sshh!" hissed Vicky.

"Each dildo is a different size," continued Carrie. "Now, what we're going to do is, we're going to draw numbers, one through five. And then each of us will choose a box in the order of our numbers. But you're not allowed to touch the box before you choose it. You just have to guess."

"And then what?!" asked Kara, clearly intrigued.

"Sshh!" hissed Vicky and Allison together.

"Once we've all made our selections, we'll open the boxes and see what we've got. Then we'll put them on."

"Okay, this IS interesting," said Allison in hushed tones.

Vicky shot her a look.

"Well it is!" she protested.

"And then," interrupted Carrie, looking around for dramatic effect. "And then, we're going to have a dick measuring contest. The winner will be determined by who has the biggest dick. And of course the loser will be the one with the smallest."

I looked at Samantha, but she was hanging on Carrie's every word. What she'd said in the kitchen seemed to be true. She was, by now, well past any sense of embarrassment.

"And that's where things get interesting," continued Carrie. "Because the loser will have to suck the winner's dick. For...oh, I dunno...let's say 90 seconds. Which means, the lucky winner gets a blowjob. And the loser gets to show off their technique."

"Well then I hope I fucking lose," declared Kara, which drew the stares of everyone else in the room. "What? I love having a cock in my mouth, you all know that."

"No, that's true," admitted Allison. "You were kind of the blowjob queen in college."

"That's funny," said Vicky. "Normally, it's other people who get on their knees before the queen rather than the other way around."

"Well, presumably nothing is stopping you from sucking one of our strap-ons once the game is over," noted Sam dryly.

"Meh, it wouldn't be the same," shrugged Kara. "Plus, if I lose, me and Jack can start our own Little Dick Club. Right, buddy?"

"Hell yeah, girl!" To emphasize my enthusiasm, I walked over to where Kara was sitting and high-fived her with just enough force that it caused her enormous breasts to jiggle ever so slightly. Of course the truth was, whatever club Kara was in, I desperately wanted to be a member of.

A moment later, Carrie was passing around a small bowl which contained five folded pieces of paper, upon each of which was written a number. When all the girls had drawn their numbers, they began to choose their boxes. They proceeded in quick succession until each woman sat cradling their own selection in their laps.

As for me, I was enraptured. I'd had no idea that Carrie had this game in mind. But it was clear to me that her idea had come from our experiences together, from my porn that we'd watched together. For the time being, I simply assumed that she was bringing some of my favorite porn to life for me in the most exciting way imaginable. But I would soon learn that this was just the beginning.

"So who opens their box first?" asked Vicky.

"We open them in the order that we chose, obviously," replied Carrie.

"Welp, that'd be me," announced Kara. She considered for a moment the box which lay in her lap before finally removing the lid. As yet, none of us could see what the box contained. We could only see what seemed to be a look of ambivalence on her face. She then reached into the box and produced her prize dildo for all of us to see. It was a silicone piece, very true to life except for the color which was a sort of neon blue. It was also quite large. Roughly nine inches in length, if I had to guess.

"I guess I'm not gonna lose this one," she frowned.

"Don't be so sure," said Carrie. "Remember, anything under eight inches, and I don't even notice. Who knows, you might yet have the smallest dick," she added with a wink.

In response, Kara simply shrugged. Then, turning the dildo upside down so that the head was facing the floor, she slid it in between her breasts, simply as a way of conveniently holding it, much the same way that you or I might slide a dollar bill into our pocket.

"I guess I'm next," said Vicky. Opening her own box, she extracted a dildo quite similar to Kara's, the obvious difference being that Vicky's was bright red. As to the size, it may have been slightly longer or slightly shorter than Kara's, but without actually measuring it was impossible to tell.

"Me next," announced Carrie as she unceremoniously flipped the cover off her own box. She held up her dildo for all to see. Pink in color and quite lifelike with respect to detail, it was clearly larger than either Kara's or Vicky's. "Hmm. Not bad," was all she said.

"Big enough for ya?" quipped Vicky.

"I can live with it," shrugged Carrie. That thing was, I swear, no less than twelve inches. That's what she could 'live with.'

"That's me then," said Allison. Taking the cover off her box, she looked at her prize and smiled. "I like purple," she announced as she raised her dildo. It was indeed a deep violet. It was also roughly the same size as Carrie's. Once again, we'd need to measure to know who's was actually bigger.

"I guess that leaves me," sad Sam somewhat sheepishly. Slowly, almost hesitantly, she lifted the cover from her box. Her eyes went wide as she silently mouthed the words 'Oh my god.' Instead of taking out the dildo as the other girls had done, she turned the box upright so that we could see her prize as it lay within.

"Fuuuck," whispered Vicky.

"Oh my..." noted Allison.

"Goddamn," declared Kara.

"I guess we have a winner," smiled Carrie.

Carrie was right, the winner was not in question. Sam's dildo stretched from one end of the box to the other, the full eighteen inches (assuming I'd guessed correctly). Flesh colored and ribbed, it also looked to be roughly three inches in diameter.

"I really hope I fucking lose this thing," moaned Kara, her mouth practically watering.

As for Sam, she seemed to sit up a little straighter, seemed to exude a sense of a pride as she held up her prize before us. I don't know, maybe I was just seeing what I wanted to see, but it was almost as if she wore a look of, 'Yes, this is appropriate. I absolutely deserve to have a cock this big and each and every one of you knows it, too.' Whatever the truth of the matter, I know that I personally felt that she absolutely deserved to have a cock that big.

"And now we put them on," announced Carrie, returning us all to reality. And without further ado, she fit her dildo to its harness and pulled it on. It was a bit tricky managing it with her skirt, but as her skirt was not super tight, she was able to shift it into position without too much trouble. Kara and Sam, who were both wearing jeans, had no difficulty at all getting their strap-ons into place.

Allison, however, was wearing a knee-length pencil skirt. To get her harness into place would require some doing. She looked from person to person, considering her surroundings. At last, she spoke.

"Look, this will just be easier if I take my skirt off," she announced as if she were reading the day's weather report. Then, with one flick of the wrist and one quick swirl of her hips, her skirt was on the floor around her ankles. At least, I think it was on the floor around her ankles. The truth is, my eyes never made it that far. Because as her skirt came down, we all discovered that she was not wearing any underwear. Her incredibly long legs instantly became that much longer, leading to her silky smooth pussy. For a long moment, she simply stood there, naked from the waist down, cradling her strap-on in her hands.

"Going commando, eh?" smirked Kara.

"Hey, if you know, you know," winked Allison. She then stepped out of her skirt and into her harness, pulling it up into position. The view of her pussy - which I'd truly enjoyed - was now replaced by that of her new, quite large, silicone penis.

"Two can play at that game," announced Vicky, as she shimmied out of her own, all-too-short skirt. But where Ally's nether regions were perfectly smooth, Vicky was sporting a full-on, untamed bush. I was surprised to find myself thinking that it was simply glorious, despite that not really being 'my thing.' But something about her attitude, the way she stood with her hips thrust slightly forward...god, I just wanted to get my face up in there! But she too soon robbed me of this exquisite view by pulling her strap-on into place. Even so, her powerful bush was making itself known around every edge her harness.

Foolishly, I allowed myself to think it couldn't get any better than this. I say foolishly, because I had not yet properly cast my eyes on Sam. But when I did? Good god.

There was Samantha, maybe 5'2"...maybe 110 pounds dripping wet. Beautiful under any circumstances, with her red hair, green eyes and button nose. But petite, tiny even. And now, swinging something like an 18" dick between her legs. I was dumbstruck. Carrie might be my best friend, my boss...maybe even my mistress. But this woman, with her enormous cock, she was my queen. My immediate instinct was to kneel before her, and it took all of my willpower to simply stay standing as I was and just stare in awe.

But then a new thought occurred to me. I looked around the room at the other four women, each with her own quite large dildo. And I wondered who would wind up being the smallest. Who would be the loser of this game? Who would end up with the privilege of sucking Samantha's dick. Whoever it was, I was about to be insanely jealous of her. Because I didn't just want Sam's cock in my mouth, I didn't just want to taste it. I wanted to show her how much of it I could take. I wanted to worship her giant silicone penis and demonstrate my devotion. More than anything, I wanted to 'win' the right to do so. In that moment, I was imagining myself losing the dick measuring contest, looking at all five of those women and declaring, 'I very obviously have the smallest penis in the room...therefore I must serve and worship Samantha's enormous penis.'

Lost in thought as I was, I didn't notice that Kara had walked over to Allison until I heard her call out, "Sword fight!" We all turned to look. Kara and Ally had both grabbed their dildos at the base and were engaged in mock battle, silicone against silicone. Each thrust and parry set Kara's enormous breasts bouncing this way and that. It was all I could do not to drool.

Suddenly, I felt a hand on my ass. It was Vicky. I hadn't even noticed her as she came to stand beside me.

"God, those things are huge," she commented.

"I've never seen tits that big in my life," I said softly.

"I meant the dildos, but yeah, those too," she laughed. Then she leaned her head close to mine and whispered in my ear. "How bad do you wish you could be jerking off to this right now?"

"There are no words, VIx."

"Well, you can stroke my cock if you think it'll help," she said, giving my ass a squeeze.

"I would be honored," I said, reaching my hand towards her own large dildo. Carefully, I wrapped my hand around the shaft, its girth such that my fingertips were only barely touching. Slowly, I began to slide my hand up and down its not inconsiderable length. As I watched the 'sword fight' and Kara's bouncing boobs, I began to speed up my pace, almost if I were stroking my own cock.

"Must be quite a change for you," said Vicky. "I mean, after spending your whole life jerking that little thing."

What I loved about her comment - and, god, did I love it - was that there was nothing cruel or belittling in her tone. It was just a simple observation. And that's exactly where I wanted to be with these women, to be able to talk openly and casually, even joke about, the size of my penis. With that one comment, I felt like Vicky too was starting to 'get' me. Then I smiled, remembering Kara's crack about starting a Little Dick Club and realized that she also 'got' me.

"Yes," I agreed. "A very 'big' change."

Carrie, noticing the two of us, came over and stood on the other side of me. "You just can't help yourself, can you?" she winked. "Even chastity can't stop you from masturbating. I should have known."

"I still have a free hand, you know," I countered, eyeing her even larger dildo.

"Oh please," she groaned. "If I'm not gonna sleep with you, what makes you think I'm gonna let you jerk me off?"

"What the hell, Jack?" demanded Vicky somewhat indignantly. "Don't I deserve your full attention?" Then she slapped my ass. Hard. I responded by stroking her strap-on even faster.

It was then that I caught Sam's eye. How long had she been watching me? Something in her look told me she liked what she was seeing. I liked what I was seeing too, the way she stood there, hands on her hips, gigantic dildo hanging between her legs. Once again, the world started to fade out around me until all that was left was me and Sam...and Vicky's cock in my hand.

And that was a most strange sensation indeed. After all, Vicky's dick was significantly larger than my own, both in length and girth. Yet compared with Sam's massive member, it couldn't even pretend to measure up. As I stood there jerking Vicky off, I simply stared at Sam and thought, "No, no, I want THAT one!"

It was like being hit with a lightning bolt. The way I suddenly felt about Vicky's cock must be exactly how Carrie felt whenever she looked at my penis. And the way I was feeling about Sam's, that must be exactly how Carrie felt whenever she watched her slideshow. Suddenly, I understood her in a way I never had before.

"Alright, girls, break it up," ordered Carrie, inserting herself between the two would-be fencers. Ally and Kara both took a step back as Carrie placed a hand on each of their shoulders. And I had to admit, watching Carrie give commands while swinging her big strap-on was nothing short of magnificent. "Jack," she called over her shoulder, "would you bring the measuring tape from the kitchen?"