My New Boss Pt. 24

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Amanda and Steph take me to their place for a week.
6.4k words
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Part 24 of the 32 part series

Updated 06/10/2023
Created 11/30/2020
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"Showtime" as my forced sexual performances came to be known, were a regular part of the evening's entertainment, whenever Suky had guests over to my place. She would embarrass and humiliate me over the course of the evening, and then the girls would remind me exactly how many days of my enforced chastity, I had remaining. They never did lock me into the cock-cage, deciding as a group, that while chastity devices were a foolproof way to prevent forbidden release, the psychological torture of having to endure a constant hard-on with no prospect of orgasm, was a much more powerful way to subjugate me.

One night, after I had gone a little over thirty days without release, Steph ended up staying the night. Suky knew that I had a crush on the young girl, and frequently allowed her to take my reins during showtime. Steph would bring me maddeningly close to orgasm, and would occasionally grind me down to the point that I begged her for release.

The massage parlor crew and the sex-shop workers all recognized the chemistry between Steph and I, and it was clear that Steph had developed a soft spot for me. When Steph, Suky and I were alone, the young blonde made an impassioned plea for leniency, and uncharacteristically, Suky relented on my ninety day enforced chastity.

"You know he has a crush on me," Steph began, stating the fucking obvious. "Let me take him for a week, and I will get him so worked up that we can all enjoy taking him past his breaking point, next week. We don't need the full ninety days to crush his resolve."

Suky loved this idea, and in the morning I left with Steph to go and spend a week with her. The girls packed my suitcase, although as I peered into the mostly empty container, I realized I could have left the house with a plastic bag. All that I Ieft with were a few pairs of silky crotchless panties, my toothbrush, my silk boxers and my service pillow. Steph allowed me to grab a bathrobe for modesty, insisting that I took Suky's pink one.

"We can borrow anything else we need from the sex shop," Steph said ominously.

Steph's place was very nice, modern with a minimalist vibe, clean and tidy. She had three bedrooms all with en-suite facilities, and shared it with Amanda and the other sex-shop employee. Steph took control of me as soon as we crossed her threshold, setting the tone for my stay.

"Fuschia," she said, once she showed me to the bedroom that I would be sharing with her.

I surmised, correctly, that Steph wanted me in my new Fuschia panties, and as Steph relaxed on her King Size bed, I changed in front of her, to signal my intent to obey her every command. Once I was naked except for my silky underwear, Steph patted the bed, inviting me to join her.

"I am going to masturbate," she informed me, "and I want you to watch."

Her tone didn't leave much room for negotiation, so I nodded agreeably and sat quietly on the edge of the bed, as she grabbed her vibrator. I watched intently as she turned the vibrator on to its lowest setting and put it directly on her sex. I hadn't seen this side of Steph before, and as she started to bring herself to the boil, we locked eyes and I felt that instant connection that we share, surface. She was just a beautiful, innocent looking girl, and even when she came, she just had an angelic smile on her face.

I watched passively as she brought herself to several more climaxes using the massager. She was a very easy come, and must have enjoyed five or six orgasms before she flopped back on the pillows, and let out a sigh of relief.

"Kneel," she instructed, as I got myself up onto my knees.

Steph turned the massager down to its lowest speed, then carefully placed it on the bed in just the right spot, between my legs. She arose from the bed and stood next to me, placed one hand on my shoulder, and slowly pushed me down until my balls rested on the tip of the massager. She moved me forward just a touch, so that I was exactly where she wanted me.

I was sitting on my heels, and the massager was vibrating into my nuts which felt incredible. Steph was well aware that there would not be enough stimulation to make me orgasm, unless she turned it up to a higher speed. However, in my current state of arousal, she could not trust me to make the right decisions. For this reason, she retrieved the belt of her bathrobe and bound my hands behind my back.

"I am going to take a shower, baby," she informed me. "Stay exactly where you are until I return."

I obediently remained squatting on the bed, as the massager pulsated into my genitals. It was very frustrating because the low speed was enough to make pre-cum leak from my cock-head, but not sufficient to make me orgasm.

Steph purposefully took her time in the shower. She knew that the massager was torture for me, and this thought aroused her immensely. After she was dry, she put on a very cute yellow sundress that flattered her lithe, taut frame. She also slipped on a matching garter belt and picked up a pair of yellow stockings, and then she briefly checked in on me to make sure that I hadn't had an "accident".

Even though I was leaking copious amounts of pre-cum into the front of my Fuschia panties, I hadn't erupted into them yet. Steph patted me appreciatively on the top of my head, telling me I was a good boy. Then she raised one of her slender toned legs on top of the bed, and pulled her stocking on, before securing the top of it into her garter belt straps. She repeated this process with her other leg, before dragging her stockinged foot under my nutsack, which expelled a few drops of pre-cum.

I shivered with pleasure at this stimulation, and she gave me an innocent smile. Steph left the room shortly thereafter, to apply her makeup.

She knew that I thought that she was very angelic looking, and so she accentuated her cheekbones and applied some frosted lip-liner to highlight this. A light spray of my favorite perfume and she was ready to continue messing with me.

When she re-entered the bedroom, she could see how frustrated I was. My cock was rock-hard, and the veins in the shaft were clearly visible. There was pre-cum around the tip, some of which had dripped onto the bed sheets. I was tense and I was grinding my nuts into the massager, trying desperately to achieve release. She seemed glad that she had tied my hands behind my back, cognizant of the fact that I was so horny that I probably would have jerked off while she was in the shower.

It had been over a month since my last release and every day was a challenge. I didn't think that my cock could get any harder than it was, but as soon as I saw her in the yellow sundress, it started to jump around, and a little more pre-cum pooled at the tip. Steph moved closer to me, the scent of her perfume permeating my nostrils and arousing me even more.

She gently touched the very tip of my cock, and noticed that it was warm to the touch. She could feel it throbbing when she gave it a playful squeeze. She delighted in my sexual frustration, and felt her panties getting damp, even though she had just enjoyed several orgasms. She left the massager running, and I continued to grind my nuts into it, in search of release. She smiled at the predicament she had placed me in. She loved to sexually torment me, and she placed one hand on my ass and gave it a playful squeeze, as I continued my thrusting motions.

"Is today the day, baby?" she teased, alluding to my next release. "Have you earned it yet?"

I wanted to tell Steph that it had been thirty-three days since my last release, that as a forty-two year old man, I need to come more frequently than once a month. That I had performed admirably for the girls, each time I had been called upon to do so. That the constant dribble of pre-cum from my cock-head was physical evidence that I was ready to come. However, it was a rhetorical question, so I nodded agreeably.

Steph increased the speed of the massager slightly and started to tease my frenulum, which made me tremble with pleasure almost immediately. She brought me close a few times, expert as she was at edging. The last time she got me to the brink of orgasm, and then abruptly turned off the massager. I exhaled sharply, a combination of exhaustion and frustration. I had been grinding my nuts against that massager forever, trying to bust a nut, and I was very tired. Steph picked up her instrument of torture, turned it on and lightly grazed the underside of my nuts. I let out an audible moan and shuddered.

"Please, Steph," I begged, "let me come, I won't tell anyone."

"Are you ready to come, baby?" Steph asked, her practiced innocence making my nuts ache with desire.

I was still on my knees with my hands tied behind my back, and in this position it was difficult for me to really move too much, without losing my balance. Steph walked over to the bedside table and grabbed my lube. Smiling seductively at me, she poured a generous amount of it onto one of her hands. She walked around behind me and gently nibbled my ear.

Steph leaned into my back, slid one hand under my stomach, and wrapped her lubricated fingers around the tip of my cock, forming a tight fist. My initial instinct was to start fucking her hand, until I achieved orgasm. However, kneeling on the bed with my hands tied behind my back was really having an effect on my balance, and I had to limit my thrusting motion to stop myself from falling forward.

I could only rock slowly forward into her fist, and even though it felt fantastic, it was not going to be enough to get me off. Steph knew this of course, which was the reason she had decided to stand behind me. Had she been more inclined to facilitate my release, she could have easily knelt in front of me and supported my upper body, while I fucked her fist to orgasm. Everything she did was designed to increase my level of frustration and desire, and today was no different. Of course, she wasn't going to tell me that, preferring to pretend that she was trying to help me get off.

Steph was talking dirty to me, as I gingerly rocked forward, gently thrusting my hips to avoid falling forward.

"Fuck it babe! Pound that fist!" she teased.

Steph applied more lube to her fist twice more, before I realized that I wasn't going to be able to come in this position. It was like she had read my mind, because right as I was about to give it up as a lost cause, her other hand started to tickle my nuts. I could feel the stirring in my loins, as I frantically restarted my rocking motions. Steph alternated between teasing my balls, and tickling my asshole, and I could feel my breathing start to quicken.

She was an expert at tease and denial, and she brought me so close to orgasm, that I thought it was a certainty. At the last second, as my nuts started to constrict, she removed her fist from my cock and her finger from my butthole. I let out a frustrated moan, as I realized what she was doing.

My cock danced between my legs as it searched for something to rub against, in the hope that any friction would enable release. My nuts throbbed, the promise of release having been so tantalizing close. I was just about to beg Steph for an orgasm, hoping that our new-found connection, combined with her self-admitted soft spot for me, would inspire her to get me off, hopefully in some spectacular fashion.

The words were formed in my throat, but before I could verbalize them, Amanda's voice broke the silence.

"Did you soften him up for me?" Amanda asked her young subordinate.

"Yes," Steph answered respectfully. "I took him so close, that he was convinced it was his time."

"Look at me, boy," Amanda ordered me.

I rotated very slowly to look at her, trying not to lose my balance in the process. Amanda sat in an upright chair, smoking a cigarette. Her other assistant knelt at her feet holding an ash tray, and Amanda flicked her ash into it periodically. After a couple more drags on the cigarette, Amanda stubbed it out and waved her assistant away.

Amanda looked fearsome, dressed as she was in black leather from head to toe. She no longer resembled the errant teenage rebel, working in a sex shop as a final "fuck-you" to her Daddy, as he served a long term prison sentence. She had morphed into an intimidating dominatrix, and my limited experience of actual forced submission, made me fear her immensely.

Amanda recognized and utilized this fear to her advantage, her control over me affecting her like an aphrodisiac, emboldening her to make me her bitch. She stood up slowly, her lithe frame extending to almost six feet tall in her sky-high black leather stiletto boots. I shuffled nervously in front of her, feeling small in her presence.

Amanda placed her hand under my chin, and raised it up so that my eyes met hers. Whatever horrors she had been through as a kid were reflected in her soulless eyes, as she viewed me with contempt. Amanda reached for an ominous looking black collar, shaking it before me, enjoying the fear in my eyes. The collar had a chrome chain running through the middle of it, which I quickly learned was a choke chain.

After I was collared, Amanda pulled the leash tightly, which immediately cut off my oxygen supply. Concern was quickly replaced with fear as I struggled to breathe. She only interrupted my ability to breathe for a few seconds, but she got my attention. As soon as she released the choke chain, I gasped for breath.

Amanda walked slowly behind me, as I suppressed my desire to swivel my head and follow her movements. Once she was out of my sight, my anxiety increased. Time seemed to slow down as I knelt in silence, trying to control my ragged breathing. I jumped when I felt Amanda's stiletto heel dig into my upper back, the cold steel point seemingly trying to penetrate my skin. As she applied more pressure, I slumped forward until my forehead hit the ground.

"Good boy," she said softly.

Then, as she maintained a constant pressure with her boot heel on my back, she pulled sharply up on the choke collar. It felt the chain constrict my breathing again, although this time it was magnified by the fact that I couldn't lift my body up to facilitate breathing. My head was fully extended upright and Steph's shocked face came into view.

"Amanda, he is suffocating," the frightened young girl exclaimed.

I let out an audible gasp for air before Amanda released the choke chain. Even though I knew she wasn't going to actually suffocate me, it was a terrifying experience to be deprived of oxygen, even if it was only for about ten seconds. Amanda ran me through a series of oxygen deprivation exercises, before she deemed me softened up for her next experiment. Even though I don't condone torture under any circumstances, her physical abuse did make me more compliant.

"Untie his hands," she barked at Steph, the young girl complying immediately.

After my hands were free, Amanda was able to move me through a series of choreographed movements, designed to humiliate me and demonstrate her absolute control of me. I was breathing heavily, sweating and visibly erect by the time she was done.

"Prepare the boy," she barked at her two young friends.

"Do you want us to remove his eyebrows too?" Steph asked innocently. "He has a full-time job."

"He may keep his eyebrows for now," Amanda said magnanimously.

They seemed as scared of Amanda as I was, and I wondered if she had put them through a similarly frightening and dehumanizing session, in order to secure their unwavering compliance. The girls each grabbed an arm of mine, hauled me to my feet, and just before hustling me out of the room, they turned me to face Amanda for just long enough that she could register that I had an erection.

"Don't worry about him," Amanda assured them. "He is obviously enjoying himself."

My first thought as they dragged me out of the room and forced me into the bathroom, was that they had done this before. They were so focused and unified in their efforts to prepare me for Amanda. I was rubbed down with a generous helping of Nair hair

remover, and after six minutes they bundled me into the shower. When I emerged moments later I was completely hairless from the neck down, and felt much less masculine.

The two young women handed me my pink silk boxers and I hurriedly put them on. They escorted me back to Amanda, and forced me to my knees in front of her.

I has always had a healthy respect for Amanda, from the first time I met her. At that point, I was fully clothed, had a three day stubble, and resembled a man. Now, as I knelt before her naked except for my pink silk boxers, and no hair on my body below my neck, I felt like a total fucking pussy.

Amanda lit another cigarette, and as she circled me slowly, she let it hang perilously close to my body. I could feel the heat emanating from the tip of the cigarette, and was very scared that she was going to burn me with it. Luckily for me, this was just part of Amanda's intimidation process, and she never actually touched it against my skin.

Amanda laid out the rules of the house for me, in excruciating detail. I was expected to go to work during the day, as normal, but every night I would be subject to her torment. I spent a week with the three of them, during which I was erect for ninety percent of the time. By the time they returned me to Suky, I was in a heightened state of arousal, my nuts ached almost unbearably, and I was leaking pre-cum continuously.

Suky was concerned enough about my testicle pain, to take me to our local sexual health clinic. We went there every fourteen days to get me tested for STIs anyway, so we just moved my appointment up a couple of days.

Marissa, my nurse, was surprised to see us, having deviated from our two week schedule. However, once I explained my predicament, things fell into place for the young woman.

"I did wonder why you declined the sperm sample the last two times you were here," she informed me, "but now it makes sense, if you were on restriction. How is that working out for you?" she teased.

Marissa wasn't really my type, she was a few pounds overweight, and a little matronly for my liking. However, we had established a flirtatious friendship over the months, especially as I was in there every two weeks, jerking off in a sample cup.

Today, six weeks into my enforced celibacy, I was horny as hell, and Marissa was looking good. If I had attended the medical appointment alone, I might have asked Marissa for a hand, or at least to let me jerk off in front of her. However, as always, Suky accompanied me, and was totally cock-blocking me.

"Tell Marissa what happened, baby," Suky said, relishing my discomfort.

"Well," I began nervously, unsure of where to start. "I haven't had an orgasm in six weeks, and I am feeling pain in my balls."

"Why haven't you had an orgasm in six weeks, baby?" Suky teased. "Marissa needs to know these things."

Because she is a controlling bitch who loves watching me squirm, Suky made me explain how it all started, in excruciating detail. Marissa listened intently, without judgement, but I am sure she noticed my red face and acute embarrassment, as I detailed my nocturnal emission to her.

"It is the silk boxers," I explained, to a round of giggles from Suky and the nurse.

"My boyfriend sleeps in silk boxers," Marissa informed me, "and he has never blown his wad in them."

I knew they were fucking with me now, and Marissa seemed to enjoy my predicament.

"Ok," she said finally, "examination time!"

Marissa examined me and diagnosed "epididymal hypertension" which I later found out to be blue balls. The recommended treatment was an orgasm, and so that night, the girls assembled at my place, to view my medically necessary release.

I was so excited at the prospect of an orgasm, particularly as I knew this one was definitely going to happen, thanks to "Nurse's Orders." I would have preferred a hall-pass, and been offered the opportunity to jerk off in the shower, in privacy, but I was grateful that I was finally going to bust a nut. It had been too long, evidently, and my body was finally pushing back.

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