Naked Houseboy & his BBW Boss Ch. 35

*Chapter 35 of an ongoing story...

"Me first!" Kara had exclaimed as she practically jumped into the middle of the circle. The time had finally come to measure up. Since Kara had drawn the lot to be the first to pick her dildo, she naturally assumed she would also be the first to be measured. Carrie, though, apparently had other ideas.

"I don't think there's any point in following the order of the lots at this point," she said. "I mean, it's pretty clear who the winner is. Why don't we start with Sam and work backwards until we find the loser?"

All eyes turned to me, the obvious loser. I couldn't help myself from grinning.

"Fiiine," sighed Kara with a hint of disappointment as she resumed her place in the circle. Meanwhile, Allison stepped forward, tape measure in hand. She considered Sam's massive strap-on for a moment, presumably thinking about the best way to go about measuring that monstrosity.

"Um, maybe take this end," said Allie as she offered the metal tip of the tape measure to her friend. Sam took hold of it and pulled on the tape until the end was firm against the base of her strap-on harness. As for Allie, she had to bend down to grab the other end of the dildo which, due to its size, was hanging down around Sam's knees. Then, straightening herself back up while also taking a step backwards, she raised the dildo so that it was parallel to the floor, all the while drawing out the tape as she did so.

"I didn't even know they made them this big," whispered Allie, mostly to herself as she inspected the tape measure. Then she looked up to meet Samantha's expectant gaze. "Eighteen inches exactly," she declared.

"Damn," murmured Vicky.

"Fuck me," murmured Kara.

"No, no, no. Fuck ME," declared Carrie.

"Oh, come on," answered Vicky. "That's too big even for you. It's gotta be."

"I'll never know if I don't try," shrugged Carrie.

Sam, though, said nothing. She simply beamed with pride. I dare say, she looked nothing short of regal in that moment. But the moment passed when Sam let go her end of the tape measure. It came flying back to its housing with such force that it nearly jumped out of Allison's hand. In response to which, she dropped her end of the dildo, which went swinging back down between Sam's legs.

It was a genuinely funny moment. And yet, nobody laughed. We were all too busy being astounded by the sheer size of Samantha's cock.

"Um, Carrie, I guess you're next," said Allie, straightening her glasses.

Carrie's dildo was big, no question. But measuring it wasn't a two-person job the way Samantha's had been. As such, Allie stretched the tape across the length of it easily enough. After taking a moment to inspect the result, she looked up at Carrie. "I hope you're not superstitious."

"Why's that?"

"Thirteen," declared Allison.

"Thirteen," repeated Carrie, wrapping both hands around her dildo as if it were the handle of a broadsword. "My new lucky number."

The procedure was repeated, first for Allie herself, who came in at an even twelve inches, and then for Vicky, who measured in at nine. They both seemed satisfied with their results. That left Kara. Once more, Allison performed her measurement.

"Are you sure you want to know?" she asked, looking up at her friend.

"I mean, I guess so," she sighed dejectedly.

"Eight inches," announced Allison in a soft voice as she let go of the dildo.

"Aww, man!" groaned Kara. "I really would have lost!"

"Sorry, girl," I offered with a grimace.

"Ah, it's alright, little buddy," she smiled. "It's just a game."

'Little buddy.' I liked the sound of that.

"Looks like you're up, Jack," said Carrie with a smile.

"Is this really necessary?" I asked. "I mean, I'm clearly the smallest one here."

"You're not embarrassed, are you?" chided Vicky playfully.

I wasn't embarrassed. At least, not embarrassed about being small. If anything, I was worried that I'd be too big. After all, I was already familiar with my own size, having measured myself more than a few times over the years. The truth was, I had really enjoyed the way they had, just moments before, been discussing my penis in 'unflattering terms,' going so far as to declare it 'underwhelming.' But now, when they found out my size, in concrete inches, they might realize that I was perfectly average and only seemed small in comparison with the oversized dildos they were sporting.

But my thoughts were interrupted by Allie, who, without even waiting for my answer, took hold of my dick and began to draw out the tape measure across it's length. While both Vicky and Sam had already grabbed me by the balls that night, this was the first time any of them had actually handled my cock. Allie's manner was so dispassionate as to be borderline clinical. Yet I absolutely loved the fact that she could just take my penis in her hand - and measure it, no less - without thinking it the least bit weird or awkward.

"Six inches, Jack," she said, looking up at me. "But I guess you knew that already." Her words were matter of fact. I shrugged.

"Six," repeated Kara. "That's actually perfectly fine. I guess it just looks smaller next to all of our massive units."

"Perfectly fine for most of us," agreed Vicky. "When it's hard, anyway. But apparently not for the size queen over here."

"I mean, what am I supposed to do with six inches?" shrugged Carrie.

"Jack," interrupted Samantha. "You realize this means I'm literally three times bigger than you."

I stepped into the middle of the circle and faced her. Looking first at her enormous strap-on and then at my own meagre manhood. She had won and I had lost. And I couldn't be happier.

"Looks like you've got your work cut out for you, little buddy," I heard Kara say behind me. And then she slapped my ass.

"Yeah, this oughta be good," decided Vicky.

"Just a sec," said Carrie as she pulled her cell phone from her pocket. "Let me set the timer. Ninety seconds. OK. Whenever you're ready, Jack."

I gulped. The reality of what I was about to do was setting in. I looked at Samantha. She was standing with her hands on her hips, an expectant twinkle in her eye. I approached her. For a moment, we simply looked at each other. All I could see was her green eyes. Suddenly, I felt her hand gripping my balls. She leaned in and whispered in my ear.

"Make this good, Jack. Everybody's watching." Then, letting go of my balls and placing her hands on my chest, she gave me a soft shove.

I stumbled backwards a step. Then, slowly, I went down to my knees. Her 18" strap-on hung down so low, the head was basically even with my sternum. Carefully, I reached out both my hands and took hold of it the way one might grip a telescope. Gently, I raised it to my lips. I could hear the other girls whispering to each other, but I couldn't hear their words. I looked up at Sam. Her hands were back on her hips and she was smiling proudly.

"Ninety seconds, starting...now!" announced Carrie.

I began by kissing her dildo, first the tip of the head, then all around the head, slowly working my way up the first six inches or so of the shaft. Then I opened my mouth and extended my tongue to lick the massive member. I slid my tongue back up the underside of the shaft until I was once more back at the head.

"Ninety seconds, Jack. Not a lot of time for foreplay," called Vicky.

"Yeah, no time to be shy, little buddy!' added Kara.

I paused for a moment, considering the oversized head of this massive dildo. I'd never put a dildo in my mouth before. Much less a strap-on attached to an actual woman. Much less surrounded by four other women, each with their own large cocks. I closed my eyes, opened my mouth and put my head down.

The sensation was an entirely new one. Nothing had ever so completely filled my mouth before. I began to move my head up and down, trying to take as much of it as I could. My eyes were closed, but my ears were working just fine. I could hear the women around me hooting, hollering, catcalling. One voice would encourage me to 'take it, slut!,' while another would encourage Sam to 'get it, girl!'

Remembering Samantha's admonition to 'make this good' and emboldened by the catcalls, I reached up with both hands and started to stroke the foot or so of the shaft that I couldn't get into my mouth. I imagined for a moment how I would jerk myself off if I'd had a twelve inch cock and proceeded to do exactly that to Sam's strap-on, twisting my hands as I ran them faster and faster up and down the length of the beast. The catcalls grew louder and I was only getting more and more into it.

And then...beep beep beep! The timer went off. My ninety seconds were up. I'd done my job. The only thing was, I didn't want to stop. But I did stop. Sort of. I stopped moving. But my hands were still wrapped around the shaft of that massive dildo, the last six inches or so of which were still in my mouth. The girls fell silent, not sure what was going to happen next.

At that moment, I realized that everything I'd been doing so far had really been for me. The experience of sucking a strap-on was so completely new that I'd been almost entirely focused on myself and what I was feeling. And the way the other women were catcalling me made me more focused on putting on a good show for them, such that I hardly had time to think of Sam. But now, finally, I remembered her.

For the first time, I opened my eyes. I looked up at Samantha from my knees, her dildo still in my mouth. With the look on my face, I tried to show her that I wasn't done, that I wanted to keep going. Would she understand? For a moment, she simply stared at me. Then, with the royal dignity of a queen, she nodded ever so slightly, giving me permission to continue.

Without breaking eye-contact, I resumed sucking her dildo. But I was working slower now, showering her massive unit with care and attention. This wasn't about me anymore. This was about her. This was my chance to worship her, the way she deserved to be worshipped.

The others had gone completely silent. But I didn't care. There was only one woman in my universe now, and she was eighteen inches away, at the other end of the enormous dildo in my mouth. She was silent too. But she wore a look that was a mix of satisfaction and righteous expectation. It was as if she was saying, "You're doing a great job, Jack. But never forget that this is exactly how I deserve to be treated and that your place with me is on your knees." It was exhilarating.

The look on her face also told me that I needed to do something to let her know I understood. I needed to do something to show her that I recognized that her satisfaction was paramount and that whether or not I was enjoying this was entirely irrelevant.

Slowly, reverently, I began to push my head down further and further on her strap-on. Deeper and deeper it penetrated into my hungry mouth. Finally, I could feel it hitting the back of my throat. Taking a long, deep breath through my nose, I relaxed every muscle in my body in an attempt to suppress my gag reflex.

To my own surprise, I was somehow able to do this. But I couldn't stop the tears from welling up. My sign to her. I looked up at Sam through watering eyes. And although she smiled down at me, she also tilted her head slightly to one side, as if to ask, "Is that really the best you can do?"

Somehow, I don't know how, I managed to push my head even further down her cock. The effort it took to keep myself from gagging caused my entire body to convulse. And now the tears were streaming down my cheeks, my eyes burning as I gave everything I had to maintain eye-contact with her.

The breaths were coming short and fast through my nostrils now, my cheeks soaked with tears. Looking up at her, I wished only that she could hear my thoughts. I knew she couldn't, but I thought a message to her anyway: "You are my queen and my goddess and I am privileged to worship you. I am honored to humiliate myself in your service."

For a long moment, she simply looked down at me. It was as if she were giving me the time and space to realize that we weren't alone. That four other women were watching me as I struggled not to choke on her strap-on. That I was completely naked with tears rolling down my face in front of five gorgeous ladies.

Then Sam's gaze left my face and darted downward, fixing between my legs. It was her way of reminding me that I was in the position that I was in for a reason. I was not allowed to forget that I easily had the smallest dick in the room. I was not allowed to forget that all five of these women had discussed my penis right in front of me and had determined it to be 'underwhelming.'

Until that moment, I had been incredibly turned on by the totality of the experience. And I'd had the rock-hard erection prove it. But now, suddenly, I felt horribly self-conscious. My face was wet with tears and I didn't know how much longer I could keep myself from gagging. The women around me had been silent for too long, depriving me of their encouragement. Were they not enjoying the show anymore? Knowing that my penis was too small to provide them with any sort of entertainment value, this show was all I had to offer them. If my performance had also become 'underwhelming,' what else did I have?

My cheeks began to burn with embarrassment. And it wasn't just Sam now who was staring at my manhood, but indeed all five of them. I could feel my dick going soft as it suddenly became the center of attention. Nobody said a word, which made things even more difficult to bear.

I looked up at Sam with pleading eyes, but her attention was entirely on my penis, staring stone-faced as I lost my erection. Only when she saw that I was now completely limp did her expression change. A regal, almost haughty, smile spread across her face. Then she took a gentle step backwards, sliding her dildo out of my mouth as she did so.

The result of this was to leave me completely exposed in front of the group. I was no longer putting on a show. Now I was just naked, on my knees, red in the face with tears still rolling down my cheeks, my dick completely limp. But Samantha was still smiling at me. And then, I understood.

It was as though she really had heard my thoughts. As if she were now saying, "You said it was your honor to humiliate yourself in my service. I know you meant those words, but I had to be sure. That is why I have tested you like this. Your humiliation is now complete. And I am satisfied with your service. The question is, do you still feel honored?"

Of course, she didn't actually say a single word. She simply looked down on me with that regal, haughty smile. But somehow, I knew with great certainty that this was exactly what she was thinking.

Did I still feel honored? Unquestionably I did. Greatly honored. I knew now that to worship her, it wasn't enough to simply suck her dildo, to service her strap-on. I had to be willing to make myself shed tears in front of this group of women. I had to endure all of them staring at me as I completely and helplessly lost my erection. Only when I'd gone through all that could I truly be said to have worshipped Samantha. Honored? Not only was I honored, I was grateful for the privilege.

Still on my knees, I now fell forward onto my hands as well. I then crawled across the floor until my head was at Samantha's feet. I decided now to speak the words that until that moment I had only thought.

"Thank you, Samantha," I sad, lowering my face to her toes. "It has been my honor to humiliate myself in your service. I thank you for the privilege." As I dared to kiss her toes, I heard Kara whisper behind me.

"Has he ever done anything like this before?"

"I've never seen anything like it," whispered Carrie in return.

"His butt does look good though, when he's crawling around on the floor like that," snickered Vicky.

"You're not wrong," affirmed Allison.

"You have served me well, Jack," declared Sam. "You may rise."

Humbly, I stood up and faced her, my back to the other four women. For a moment, she simply looked at me with a smile of pure satisfaction. Then, gently, softly, she kissed me on the cheek, no doubt tasting the saltiness of my tear-streaked skin.

"One thing did surprise me though," she said, speaking past me to her friends.

"That homeboy sucks a mean dick?" giggled Kara.

"Actually? Somehow that didn't surprise me at all." She was still talking past me, but I could swear she winked at me. "No, what surprised me is this. Listening to Jack talk, I could really believe that nothing embarrasses him. That nothing fazes him, nothing gets to him. But I guess there are some things a man just can't hide." And as she said this, she cast her eyes once more upon my still flaccid penis. "Jack, please turn around and face the group."

Of course I did as I was told. But what was this about? What was she doing? I felt my heart racing. Was I actually nervous now in front of these women, my apparently new friends? I'd been naked from the moment they met me. I'd shared the intimate details of my love affair with masturbation with them as if it were nothing. Carrie had spilled the beans on my penis issues, and I'd been fine with that too. Hell, I'd just spent the last few minutes on my knees sucking an 18" strap-on. And for the first ninety seconds of it, I'd felt like a rock star. Or at least a porn star.

But this was the second time now that I couldn't get it up. And they were all staring at me. If I was embarrassed the first time it happened, now I was positively mortified. The fact that they were all staring at me in silence only made it worse. I mean, if they were cracking jokes about it, I would have felt better. At least then, I could have persuaded myself we were all just friends having a laugh over the sort of embarrassing thing that could happen to anybody.

Maybe the worst part was, I felt like I was letting Carrie down. Like, I could imagine each of them calling her on the phone the next day, all with the same message. "Some naked houseboy you hired. Can't even stay hard surrounded by a group of five gorgeous women." My head slumped as I stared at the floor, too ashamed to face the women across from me.

Apparently, this was unacceptable to Sam. Grasping my skull with both hands, she raised my head, forcing me to look at my audience. The way they were staring at me, inspecting me, I felt like an animal in a zoo. And not for nothing, the way Sam was holding my head made me feel like she was my trainer. She must have felt it too, because when she began to speak, it was almost like a zookeeper presenting a specimen to an eager audience.

"What we have here," she began, "is a male who, when left alone, his primary urge, his reason for being, is to masturbate. The urge is so strong, in fact, that he will masturbate to the point where it impacts his ability to achieve an erection. And he is not troubled by this in the least. A rare breed, indeed. You will note the penis. Not particularly impressive for his kind, but that is beside the point. You will also notice the surroundings. He is naked, the only male in the company of five attractive females. In most males, this would be more than enough to stimulate an erection. Yet his penis is entirely unresponsive. Even if he tries to stimulate himself. Show them, Jack."

As if I had no free will of my own, I reached for my limp dick and, with almost foreordained futility, began tugging.

"You see?" she continued. "Despite his love of masturbation, he is unable to arouse himself. Which is all the more striking given the subjects stated lust for enormous breasts. For example, such as you yourself possess, madam." This was directed at Kara who instantly blushed. "That's enough, Jack," she added. Removing her hands from my head, she patted me on the ass, the way a trainer might pet a seal who had just performed well for a crowd. In response to which, I stopped tugging and let my hands fall to my sides.