My New Boss Pt. 20

"Yes Auntie," Suky responded, as if it were perfectly normal for them to be discussing my orgasm schedule. "He is on a very tight program. I should warn you girls, that given the additional stimulation of an audience, he will probably ejaculate very prematurely."

"Nothing new," Rim said dispassionately, to a round of laughs.

"I could numb him, if you want me to prolong the show," Suky suggested.

All the girls giggled and delighted in that idea, although I was dreading the prospect of it.

"Then it is decided," Suky said with a flourish, "go numb yourself, baby. I will come and check on you in a few minutes."

I was embarrassed and humiliated by the turn of events, but my cock was rock-hard and I wanted the opportunity to come. I left the living room and entered the bathroom to coat my cock with the numbing gel. As I was applying it, Suky appeared at the door holding her wine glass, with a huge grin on her face. She was having fun now that she was drunk, her inhibitions reduced, along with any thoughts of going easy on me. I wished that she had allowed me a glass of wine, to take the edge off. She watched me intently, to make sure that I had applied enough gel.

"If you want to come tonight you will have to work for it," she taunted. "Use the cock-ring, but no condom. We want to see how much you can come for us."

Once I maneuvered the cock-ring over my nuts, I felt the familiar tightness. The gel was taking effect too, and my cock felt very warm.

"Come back into the living room when you are ready," she instructed, before abruptly leaving the bathroom.

I was so nervous that I was shaking, and all of my senses were heightened. I wanted to get out of this nightmare, but I knew that I had to pass her latest test. I walked over to the sink and splashed some cold water on my face. As I dried myself I looked in the mirror. I looked absolutely ridiculous. I was naked except for my pink boxers, my hard cock trying to poke its way out of the confines of the silk. I had a large wet spot of pre-cum at the front of them, that would be impossible to hide. I was rooted to the spot unable to move, until Suky finally called out from the living room.

"Don't keep us waiting cabana boy. It's showtime!"

Suky had dictated the pace of our relationship since day one, and had tested me constantly along the way. I felt that tonight was just another test I had to pass, no different than the fashion show, or the ride home from the airport, or being numbed by her to ensure that I could perform for long enough to pleasure her. Just another test.

As I slowly shuffled my way into the living room, I focused on one thing. This was a test. Nothing more. Unless I decided to leave right now, I was going to be put through the ringer, for the amusement of her friends. In the morning,Suky would be looking to punish or reward me, based on tonight's performance. I was going to make her very proud of me, do her bidding, follow her script, play my part, and earn my reward.

My head was down as I entered the living room, almost as if I was trying to block out this surreal scene. Suky had placed my pink, silk, heart-shaped service pillow in the center of the room, and all eyes were on me as I looked at her for further instructions. She took her time, delighting in my public submission to her, and eager to allow all of the girls to take in the fact that I was in desperate need of release!

For reasons unknown to me, she had decided to dominate me in front of most of the massage parlor staff. Even though I was very nervous, my arousal was motivating me and I wanted to come so bad. I knew that in the moment immediately after my release, all of my tension and anxiety would disappear, even if just for a few seconds.

I stood there for what seemed like an eternity, as Suky reveled in her control of me and made me wait by my pillow. My erect cock was straining against the silk of my boxers, and my wet spot had grown.

"Lay down on your front with your crotch on the silk pillow," she instructed me, as the girls watched intently.

I knew not to question her, and I got into her desired position. As soon as I laid on my front, the silk pillow conspired with my silky boxers to make me unload my nuts. I thrust into the pillow a couple of times, before Suky spoke.

"I didn't give you permission to hump your pillow yet," she said, barely suppressing her laughter.

Suky took another large sip of her wine, and as the alcohol emboldened her, she issued her next command.

"Ok, go for it," she said cheerfully. "Fuck your pillow until you orgasm."

Oh fuck! This was bittersweet. It would be so humiliating to dry-hump that silk pillow, but I needed the release, and I would have done anything for it. I started off slowly and immediately felt a churning sensation in my nuts, that typically preceded an orgasm. I hadn't applied too much gel to my nuts, and they still had some feeling in them. The silk boxers caressed my balls with every thrust, and because the pillow was also silk there was no friction. It actually felt really pleasurable, and I tried to block out my "audience" as I increased my tempo.

A few moments later, with my focus solely on my orgasm, I was really fucking that silk pillow, thrusting my hips deep into it as I tried to overwhelm the numbing cream and the cock-ring.

"Get up into a push-up position," Suky instructed me, "the girls want to have a better view."

A wave of humiliation washed over me, as I adjusted my position for the sole benefit of my viewers. As soon as I was in her desired position, I began to thrust my hips and fuck my silk pillow.

"Much better," Suky informed me. "Can you girls see how hard he is working to put on a show for you?" she asked, turning her attention to my audience. "You can see his abs flexing under the strain of holding himself up."

Suky was right about one thing, it was much more physically demanding fucking in a push-up position, and I really wanted to come quickly, before I exhausted myself. The girls had apparently got over the initial shock of how submissive I was to Suky, and were starting to egg me on.

"Fuck that pillow, make it your bitch!" Rim shouted.

"Own it, baby," Suky added, encouraging the girls to taunt me.

As the women voiced their approval, Rosebud picked up her phone to take a picture, but fortunately for me, Suky spared me that humiliation.

"We agreed no pictures," she reminded the young girl.

After Rosebud reluctantly put down her phone, Suky offered a compromise.

"I will take a few pictures," she said, to my horror, "and I will text the best ones to you guys later."

This seemed to appease the group, and they got back to cheering me on with their taunting. By the time that I realized that they were all ready for the money shot, I became aware that I was not going to be able to come, due to the numbing gel. This should not have been a surprise to me, as I had never been able to have an orgasm when I was numb. Suky had run me through all kinds of erotic scenarios, and I still had not been able to blow my wad with the gel on me.

The fact that I couldn't come was maddeningly frustrating, and then I realized that Suky had engineered this whole embarrassing scenario. She had combined my release and punishment for the amusement of her girlfriends, knowing full well that there was no way that I would be able to ejaculate in my current state. She had taken great pleasure in watching me fuck my pink pillow, knowing that it would not end pleasurably for me. Suky took a few more photos of my frustrated attempts to come, as I started to slow my thrusts out of exhaustion.

She had promised me that one day she would use the pink pillow to punish me. Did she know back then, that I would be fucking that pillow in front of her girlfriends? As my exhaustion increased, my pace slowed noticeably. I was sweating and breathing heavily now, out of my mind with frustration and desire.

"Are you unable to come for us, baby?" Suky teased, continuing her relentless fucking with me. "We all want to see you blow your load in your silk boxers!"

As embarrassed as I was by her mocking tone, I needed to come. The desire to be permitted an orgasm overwhelmed all of my other emotions, and I heard myself speak up.

"Please, Suky," I begged. "Remove the gel, let me come."

Suky had me right where she wanted me, and was going to demonstrate her control of me to her friends. The alcohol was coursing through her veins, and she felt very dominant tonight.

"What would you give to come right now?" she taunted me.

"Anything," I responded dumbly, forgetting who I was negotiating with. "I would give anything, Suky."

Her friends were silently watching this exchange, and they were amazed at the power dynamic between us. Suky was firmly in control of my sexual pleasure, and I was submitting willingly.

"One month," Suky replied coldly. "One month until your next release, and the four of us get to witness it!"

"Oh shit!" Rim exclaimed. "Imagine how frustrated he will be thirty days from now. That I want to see."

Suky had forced me to make stupid decisions before, but as I agreed to her terms, I knew that this was quite possibly the worst ever. I nodded my head in agreement, and Suky told me to speak up.

"Yes," I said quietly.

"Yes what?" she responded. "Articulate your thoughts, cabana boy."

Now she is just being mean, I thought to myself, taking a deep breath as I realized what I was about to give up.

"If you let me come now, I will wait thirty days until my next release," I said, in a barely audible whisper.

"And?" she admonished me.

"And your friends can watch my next orgasm," I said, in desperation.

Suky had ground me down to nothing in front of her friends, and the fire was burning between her legs.

"Deal," she said, with a victorious smirk on her face.

My first thought when Suky made a deal with me, was that it was too easy. Normally, she would have made me jump through a bunch of hoops, before giving me what I wanted. However, I focused on my imminent release, and couldn't wait to get the gel and cock-ring off, and have my orgasm.

It wasn't under the most ideal circumstances, given that several of her best friends were going to watch, but as infrequently as I got to come, I had learned to cherish every release. In Suky's words "to seize every opportunity!"

I hadn't stopped grinding my hips into the pillow the whole time she was outlining her terms. I was a million miles from an orgasm, but the silk felt fantastic on my nuts as I humped the pillow.

Suky took the floor and made a theatrical announcement.

"Cabana boy is going to conclude his performance with an orgasm," she said, with a huge smile.

The girls clapped and giggled in anticipation, and I waited to be excused so that I could go and wash the numbing gel off. However, Suky apparently had other plans, because she told me to kneel on the pillow with my hands behind my back.

This was humiliating for me, because it showcased my erection and, more embarrassingly, my wet spot. However, I followed her direction, and once I was on my knees, Suky reached over and grabbed a silk tie that she had got from my closet earlier. She secured my hands behind my back, and I started to worry that she had changed her mind. We had made a deal and this was not part of it.

"Suky," I exclaimed in confusion, "how the hell can I remove the gel without my hands? Also, my cock-ring is really tight and is starting to bother me."

"You will be fine, baby. Trust me," she said dispassionately, doing nothing to wipe the worried look from my face.

Suky went to leave the room, and when she reached the doorway she turned to me and issued me another one-word command, "Stay."

After she left the room, I felt much more vulnerable without her presence. I was kneeling on the pillow with my hands bound behind my back, powerless to hide my massive erection, and my ever-growing wet spot. I had no clue where to look, so I just hung my head and stared at the floor, wishing I was somewhere else, anywhere else. Moments later, Suky strode confidently back into the room, with one hand behind her back.

She relished being the center of attention, and slowly pulled her hand from behind her to reveal that she was holding her massager. A raucous cheer went up from the ladies, as they realized her intent.

"She's going to give him a ruined orgasm," Rim said matter of factly to Rosebud, the least experienced member of the group.

My heart sank as I put the pieces together, and recognized that Suky had put me together. I had agreed to thirty days of restriction, in exchange for an orgasm, without clarifying how that orgasm would be achieved. As I knelt on my service pillow, with my hands bound behind my back, I was completely at the mercy of Suky, and she wasn't a particularly benevolent individual.

"Are we ready ladies?" she asked cheerfully. "For your viewing pleasure I will now attempt to get cabana boy to blow his load in his silk boxers. Let's take bets on how long he lasts."

There was quite a lot of excitement surrounding the bets, with each of the young women having an opinion.

"It's been eight days," I heard Rim say, "that pussy has no staying power. I am going for five minutes."

"It looks like he has already blown his wad," Rosebud said, with a giggle, presumably referring to my wet spot.

After the bets were in, Suky slowly approached me from behind. She knelt behind me and raked her manicured nails across my butt-cheeks, encased as they were in expensive Malaysian silk. I jumped at her touch, expelling a little more pre-cum into my boxers.

"Can I change my bet?" Rosebud asked, with a giggle, "I think I vastly overestimated his stamina."

Suky smiled at Rosebud, sidled closer to me, and whispered in my ear.

"Don't blow your load too quickly, baby. Make me proud of you."

Then she put the massager between my ass-cheeks, so that it ran across my asshole, with the tip at the base of my nuts. She had watched me intently as I had applied the numbing cream, and had noticed that I did not apply as much of it to my balls as she normally would have. Suky knew that if she had any chance of getting me off, my most sensitive area would be my nuts.

Once she had the massager in place, Suky announced the exact time, so that they would be in agreement of who won the bet. Then triumphantly, she turned the massager on to its lowest speed, and held it very firmly against the base of my testicles.

"Holy Fuck," I whimpered, the vibrations causing my cock to stiffen involuntarily. "That feels amazing."

I had endured a lot tonight for the amusement of her friends. I had been rock-hard ever since Joy stuck her foot in my crotch, as I was trying to dry it. I was ready to come, but I was dreading the frustration and humiliation of a ruined orgasm. The young women had no idea what was going to happen. They were under the assumption that Suky was going to make me come in my boxers, as part of our kinky ritualized weekly event. They were happy to watch the show, knowing that Suky totally owned me, and was going to torment me sexually.

After a couple of minutes, I could feel my release getting closer, and I started to flex my ass-cheeks, thereby simulating the motions of fucking.

Suky slapped my ass and chastised me.

"Let it unfurl naturally you greedy bitch," she said contemptuously. "Or I will leave you high and dry."

I hung my head in shame, as the girls tittered and whispered among themselves. Suky gave my ass another slap, before she turned the massager to the next speed setting.

I stiffened as the intensity increased, and I let out another moan.

"Don't you fucking even think about it," Suky whispered in my ear. "My bet is eleven minutes and it has only been four."

Jesus, I thought, not only is my orgasm going to be without pleasure, but it also has to be on command?

Suky kept the massager pressed firmly against the base of my nuts, on the second lowest speed. As we passed the five minute mark, Rim spoke.

"Fuck, I am out. I had him down for five minutes. I can't believe he lasted longer than that."

Rim's clinical assessment of my staying power added to my humiliation, as I realized that they were more concerned with the bet, than with my pleasure.

"Eight minutes," Suky announced to the expectant ladies.

"Damn," Rosebud said, "that's me done. I was sure that he would have come by now, considering he had not come for a week."

"Trust me, it is the numbing cream," Rim said coldly. "That two-pump chump would have spurted in his silky boxers by now, if he hadn't been numbed."

This remark elicited a few more giggles from the ladies, and Suky turned the massager up a notch, and leaned forward so that she was nibbling my ear.

"Two minutes," she whispered. "Then I want you to come in your boxers for the amusement of my friends."

"Joy, can you take some pictures?" Suky asked her Auntie, as she handed her cell phone over.

"Smile for the camera, baby," she instructed me.

I had been staring at the floor for the last several minutes, and I reluctantly looked up, and gave a very forced smile. When I raised my head, I noticed that Suky's friends were watching the show intently. Joy was stood in front of me taking pictures, and the other women had scooted forward in their chairs for a better view.

"Make sure you get his face when he loses control," Suky said to her Auntie.

Suky turned the massager up to the next speed, and I felt the familiar churning deep in my groin. Suky began to quietly egg me on.

"Come on baby," she teased, "show us how long you can last. Make me proud of you."

Even though Suky had conditioned me to want to make her proud of me, I didn't feel like I had any control of when I would ejaculate. I thought I was at the mercy of the massager, and as we approached the eleven minute mark, Suky turned the massager to its highest setting.

As soon as the massager was on its maximum speed, I knew I was done. No amount of desire to please Suky, and no amount of effort to time my release to enable Suky to win the bet, was going to override my body's desire to empty my nuts.

After about twenty seconds on maximum speed, I let out a whimper of frustration as I felt my boxers get wet, but there was no discernible feeling of orgasm.

"He is coming," Joy said enthusiastically, as the women all watched intently.

I didn't feel a thing as the massager drained my nuts. I was aware that I had wet my boxers, but there was no pleasure associated with it. The girls couldn't understand why I wasn't writhing with pleasure as I ejaculated into my silk boxers. Suky kept the massager firmly pressed against the base of my balls, and I leaked for several minutes. As the wet spot continued to grow, Sara matter of factly explained the mechanics of a ruined orgasm.

"He is experiencing zero pleasure," she said with a satisfied smile. "I have only ruined his orgasms twice, but it is his least favorite way to come."

Truth was, I would rather have no orgasm than a ruined one. Not only was there no pleasure, but afterwards I felt more sexually frustrated than before my release.

Suky kept the massager there for much longer than necessary, apparently enjoying my discomfort. At one point, my boxers could no longer contain all of my release, and a few drops of cum ran down my leg and onto the pillow. When she was sure she had milked me dry, she turned the massager off, and got up off her knees. She took an exaggerated bow, and the girls clapped their hands in appreciation of the performance.

I was still kneeling on my pillow, with a massive erection that was not going anywhere in the near future. When Suky came around from behind me to admire her handiwork, she noticed the drops of semen on my pillow.