My New Boss Pt. 21
After Suky made it clear that Amanda was now in charge, all eyes turned to her, as the young girl took center stage. Despite being only nineteen years of age, Amanda was a sadistic little minx. Shortly after she turned eighteen, she was sexually abused by her father on a regular basis, prior to his eventual incarceration. She was then thrown to the wolves when her mother's new boyfriend picked up where her real Dad left off. The new father figure in her house got drunk and fucked her regularly, when her Mom was at work. By the time she left home she was a man-hater, and had sought refuge in the seedy drug-underworld, which led her to work in a sex shop.
There were no shortage of sex offers for a teenager working in a sex shop, and Amanda did some escorting, before finally realizing that she could make money as a dominatrix. This was the perfect job for her. The money was excellent, she didn't have to have sex with her clients, and she could use pain and discipline as an outlet for her hatred of men.
My first encounter with Amanda had been at the sex shop, when Suky was buying me silky panties to wear. Amanda knew right away, from the way Suky had me on a short leash, that I was going to be an easy man to take control of. She had set her sights on me immediately, suggesting which color panties would look good on me, trying to see how I would respond to her taking control.
Amanda delved a little deeper into my submissive nature on the day that I was forced to go and pick up my cock-cage. Suky must have shared my plight with the young girl, because she was aware that Suky had taken the belt to me. Although, from the way I limped gingerly into the sex shop, it was patently obvious that I had taken a beating.
Now as she stood in my living room, and I realized that I was about to enter her sphere of influence, Amanda had developed into a stone-cold sadist. She was dressed in leather from head to toe, buckles and spikes protruding from different parts of her sinister looking dominatrix outfit, and looking like her sole mission in life was to make my life miserable. I couldn't even look her in the eye, such was my concern for my wellbeing. I could feel my legs shaking as my body trembled in anticipation and fear.
"My boy is yours," Suky offered. "Do with him as you will."
Amanda stepped forward, a look of disdain across her face, as she prepared to take control of me.
"Kneel, boy," she said, using Suky's derisive name for me, despite the fact that I was more than twice her age.
I sank slowly to my knees, the prospect of being taken control of in front of seven women, sufficient to make me almost pass out. As soon as I was kneeling before her, she collared me. She had a really cute Hello Kitty dog collar with a matching leash. The implements of control were the same shade as my boxers, a bright Barbie Pink, the color of choice of teenage girls for their feminine accessories. It contrasted with her all-black ensemble, highlighting the power dynamic between us.
Amanda ran me through a series of humiliating and exhausting poses, tricks and agility exercises, the likes of which I last saw on a television program about competitive obedience at dog shows.
My cock hadn't shown much interest in coming out to play since Suky thoroughly drained my nuts, but under fear of retribution from Amanda, it had positively shriveled up. Amanda had come prepared for every eventuality, and armed with a large bag of sex toys from her place of employment, she selected a vibrating cock-ring as her weapon of choice to get me erect.
The latex stimulator was similar in appearance to the one Suky used on me, although it was bright pink, to match my collar and leash. Amanda had done this before, skillfully maneuvering it over my flaccid cock and under my balls, in a single fluid motion, without having to remove my crotchless panties. One flip of a switch, and my cock started to twitch and dance for her, peeking as it was through the open slit in my underwear.
Amanda took her time to bring me to a complete erection, turning the cock-ring off periodically to demonstrate her complete control of my organ. Finally, once I was fully erect, and had demonstrated the ability to sustain my hard-on, she lined the tip of my cock up with the entrance to my Hello Kitty pocket-pussy. The bright pink sex toy looked pretty pathetic, like it belonged in the lunch box of a teenage girl. In a addition to the whiskers painted on the side, someone had professionally stenciled "Timmy's Puss" down the side of it, which was extremely emasculating.
I could feel the heat emanating from the silk-lined cylinder, one of Amanda's assistants having obviously taken the time to utilize the warming function, that had been described to me. I know it is difficult to imagine being forced to fuck a pocket pussy in front of seven young women, but in my elevated state of arousal, I would have fucked just about anything to get off. It had been eight days since my last proper release, the ruined orgasm having only exacerbated my feelings of lust.
The outer edge of the pocket pussy was slick with lubricant, the pink silk lining shining from the effect of the KY liquid, which had also been heated for comfort. Amanda allowed me to slightly penetrate the lubricated cylinder, but as I pushed forward to enter it, she stopped me.
"Take your time you desperate little bitch," she scolded. "This is as much for our visual enjoyment, as for your sexual pleasure."
With my newly issued instructions embedded in my brain, I started to slowly fuck my new pocket pussy. The silk lining felt amazing, warmed as it was to body temperature, with the internal heating element. The girls had used a very generous helping of lubricant, and as I slid in and out of the sex toy, it felt just like the real thing. I closed my eyes and fantasized about Steph, my balls churning immediately at the mere thought of making love to her.
Strangely enough, my body deviated from its normal physical response to such stimulation, and instead of getting closer to release, I felt detachment, numbness almost. I picked up my pace a little, ignoring Amanda's instructions to prolong my release for their visual amusement. The more I pounded into my pocket pussy, the less arousal I felt, and I realized what had occurred, right as Amanda spoke.
"I think Steph might have used numbing gel instead of KY lubricant," she said in mock surprise, as the girls began to giggle. "Oops!"
I knew there was no way I was going to get off in my current state. I either needed them to remove the gel, or up my level of stimulation. Amanda, apparently was a mind reader, because she came up with such a suggestion.
"Who do you want to simulate fucking?" she asked me, knowing full well who I was fantasizing about when I closed my eyes.
I knew I should have said Suky, but in the heat of the moment, I made eye contact with the young blonde assistant from the sex shop, and upon receiving an agreeable smile, blurted out before thinking it through.
"Steph," I said, with way too much enthusiasm, "I want to get balls-deep in Steph."
The young blonde, who minutes before had hopped off the sofa in her pleated silk mini-skirt, arose from her seated position on my living room floor, inadvertently flashing me her matching pink panties. If I hadn't seen her identification prior to serving her a diet-coke, I wouldn't have thought she was nineteen. She had an angelic face, full of innocence, which was appropriate considering she was a submissive in Amanda's sex shows. Steph approached the sofa, looking at Amanda for direction.
"Simulated missionary," Amanda ordered, "lose your panties."
Steph was obviously used to taking direction from Amanda, because she reached under her short skirt and lowered her panties down to her ankles. She kicked them off and they landed on the sofa to the right of me. Steph climbed onto the sofa in front of me, spread her legs wide apart, and lowered her bare ass onto the leather seat, taking care to position herself about an inch above my Hello Kitty pocket pussy.
The way she was positioned, with her short tennis skirt just covering the entrance to her teenage pussy, made it feel hyper-realistic, like I was inside her tight, young vagina. Once she was satisfied that she was in the right place, Steph placed one of her hands on my ass and pulled me deeper into my pocket pussy. I let out a whimper of pleasure and Steph responded favorably.
"Does that feel good, baby?" she teased, "being inside my tight, young snatch. You are really filling me up."
I let out another moan, and Steph continued her verbal taunting.
"Take your time, baby. There is no rush. We have all night."
She smiled agreeably at me, and to my surprise, leaned in for a kiss. I reciprocated immediately, and as our lips locked I was aware how minty fresh her breath was. She had obviously just used mouthwash, in anticipation of us making out. We kissed for several moments, and my audience disappeared, as the room shrank down to just the two of us.
Steph was a great kisser, and I felt a strong intimate connection with her, as we French kissed and she guided me in and out of my pocket pussy. Occasionally, we would come up for air, and Steph would offer me words of encouragement.
"Oh, yeah, baby, that feels good," she cooed. "You are going to make me come if you keep fucking me like this."
She was so good at perpetuating the illusion of us being coupled, that for a moment I forgot that I was balls-deep in my pocket pussy, and not her teenage snatch. Steph had been dictating the pace ever since she straddled my Hello Kitty sex toy, and she slowly increased the speed and depth of my thrusting.
My first indication that Amanda was back in control, was when I saw her hand reach around me and pick up my pink leash. She gave it a sharp tug and told me to stop thrusting, in a tone that left no room for negotiation. As I stopped fucking my pocket pussy, my world expanded, and the raucous laughter of my audience filled my ears. I went to look over my shoulder to see what Amanda was doing, but she directed me to focus.
"Eyes front," she ordered, "be still."
It was very frustrating to still be inside my pocket pussy, but to be denied permission to fuck it. Amanda knelt behind me, and rested her hand possessively on my ass, before leaning forward and whispering in my ear.
"Steph's beautiful isn't she?" she said quietly. "That perfect mixture of innocence and availability. Would you like to fuck her for real? How much would you pay to get balls-deep in that young goddess?"
I knew she was fucking with me, but I felt the need to make an offer, just in case it was real.
"One thousand dollars," I blurted out, not wishing to offend the young beauty with a lowball offer. "I will pay a thousand dollars if I can have sex with Steph."
"You misunderstood me," Amanda said quietly. "Not only is Steph not a prostitute, but she has no need for your money. We need you to give something much more important to you than money," she said ominously.
The room was hushed now, the girls waiting expectantly to see how much I was prepared to sacrifice, in order to fuck Steph. Suky stepped forward, eager to take the role of negotiator, and to extract as much from me as she could.
"We don't want your money," she reiterated, "we want your time."
"Time?" I repeated in a confused tone.
"Yes, time," Suky said confidently. "How long are you willing to go without another orgasm, in exchange for fucking Steph right now?"
I knew I shouldn't have engaged her. I should have thrown in the towel, forgotten about Steph and focused on busting a nut in my pocket pussy. However, because I am weak, I started to trade my future pleasure, for my current enjoyment, which in retrospect was a disaster waiting to happen. I couldn't hope to win a negotiation with Suky, and the worst thing was, that all of the girls got to witness me beg and cajole Suky to allow me to fuck Steph.
"Seven days?" I offered tentatively, my lack of conviction eliciting an immediate response from Suky.
"Seven days, you disrespectful prick?" she barked at me. "You gave up thirty days for a ruined orgasm and you think a crack at Steph's pussy is only worth seven days?"
Steph was pouting now, giving me a disapproving look, which was just going to spoil my mood. I desperately wanted to fuck her, but I also wanted her smiling at me when I ejaculated inside her teenage pussy.
"Thirty days?" I countered, regretting the words the second they left my mouth.
Even though I am familiar with the "good cop, bad cop," routine, I folded like a pack of cards when Steph leaned into me and joined the negotiations.
"Hey, baby," she teased, "think how good it will feel to bust a nut inside me. Guys always tell me that they can't believe how tight I am. I must be worth more than the ruined orgasm that you traded thirty days chastity for, no?"
Steph kissed me gently on the lips, and I felt the intimate connection between us.
"Forty-five days?" I whispered hoarsely, willing at this point to trade six months, if that is what it took.
"Closer," Steph cooed. "Do you want to put your tip inside me to see how tight I am?" she offered. "I know you like young pussy, but mine is warm, wet and very tight."
We both knew she had me when I dropped my head onto her shoulder, and let out a little whimper of frustration. Steph placed one of her manicured hands on the back of my neck, and raked her nails up across the base of my hairline, causing instant goosebumps on my shoulders. She moved her lips to my earlobe and bit it, before whispering in my ear.
"Give me just a little more, baby," she teased, "and then let's fuck."
Somehow, through a combination of my desire to fuck her and her manipulative negotiation skills, the lovely Steph got me to agree to trade sixty days of chastity for an orgasm right now, inside of her.
Suky, who had been uncharacteristically quiet as Steph manipulated me to this point, recapped my situation for the entire audience.
"Ladies, my boy just agreed to sixty days of no orgasms," she said gleefully. "This will run consecutively to his original thirty days," she reiterated. "He is going to be in a cock-cage for three months!"
The girls chatted excitedly amongst themselves at the prospect of my three months of sexual sobriety, and were already arguing about who had the honors with the application of my cock-cage.
"Guys," Steph pleaded, "let's worry about his chastity later. I want him to fuck me first. He has earned it."
She kissed me again, her minty breath bringing me right back into the moment. She placed one hand on my abdomen, and pushed me slowly backward until I slipped out of the pocket pussy.
"Let's fuck baby," she said sweetly.
Steph looked so angelic as she asked me to fuck her, and her youthful innocence tugged at my conscience. I wanted to make sure that I had her consent, especially as I was twice her age.
"Are you okay with this, Steph," I asked nervously, praying to God that she didn't change her mind.
"I have never wanted anything more, baby," she replied cheerfully, giving me another tender kiss.
Steph grabbed the tip of my cock and lined it up with the entrance of her teenage pussy. Right as I was about to slip between her labia, Amanda's hand appeared out of nowhere, and she wrapped it around Steph's, clenching it into a tight fist. Once she had prevented me from getting inside Steph, Amanda spoke up.
"Safety first," she said with a broad smile. "You need to wear a condom, Timmy."
"I have a very recent STI panel," I said despairingly, "all negative. I get tested twice a month."
Amanda looked across at Suky for confirmation, and to my surprise she nodded affirmation.
"Ever since his indiscretions with Amy, Lisa and Emma, I get him tested regularly," she confirmed. "He is one hundred percent free of any communicable diseases."
My heart soared as Suky stepped up to the plate and supported me in my endeavor to bare-back the beautiful young Steph. Even in my numbed state, I wouldn't last long inside her. The other thing that didn't last long was my new-found euphoria at the prospect of getting balls-deep inside Steph without a condom.
"However," Suky continued, commanding the attention of the room. "Timmy's cock is covered in numbing gel, and while it won't cause Steph any discomfort or pain, why should she have to endure the numbing effects of the gel? Isn't she entitled to release if she feels so inclined? Release, I might add, that will be tempered by the gel, that is completely unnecessary for her."
There was an agreeable murmur around the room, as the ladies processed Suky's words of wisdom.
"Indeed," Amanda concurred, "why should Steph be numbed, because this two-pump chump can't control himself around beautiful women?"
"Then it is decided," Suky said triumphantly, stepping forward holding a condom in her hand.
Even though I wasn't enthused about having to wear a condom to fuck Steph, I recognized the brand and type of condom by the packaging. I had used this Durex extra sensitive condom before, and had enjoyed the fact that it was super thin, and hadn't inhibited my sensitivity too much. I took the condom from Suky, and began to fumble with the packaging, eager to get inside this young blonde.
Amanda was on me in a second, slapping the condom from my hands as I tried to unpackage it.
"I want you to wear this one," she instructed me, handing me an unfamiliar condom, still in its wrapper.
Even though I had never seen this brand of condom before, the words "extra strength" leaped out at me from the packaging, in an ominous warning of reduced sensitivity. My heart sank when I read the words "climax control" and by the time I unwrapped it, I realized that it was way thicker than what I was used to.
"Put it on," Amanda ordered me.
The prophylactic was very heavy and reduced my sensitivity significantly once I had squeezed into it. Combined with the numbing gel, it made my cock feel somewhat detached from my body. Steph didn't seem to care, and she put her hands back on my ass, and pulled me inside her.
She let out a satisfied moan when I entered her, but I could barely feel anything. I knew that she was wet, because there was no friction and I slid into her easily. Once I was balls-deep, I felt her vaginal secretions on my nuts, the one part of me that wasn't numbed. Steph's hands roamed across my ass and lower back, tickling and scratching me in search of a reaction. When she reached under me and gently squeezed my nuts, I leaned into her.
"Fuck, Steph, that feels good," I whispered.
"Your nuts?" she asked, seeking clarification. "Does that feel good when I play with your nuts?"
I nodded excitedly, and Steph focused her attention on the one area of my genitalia that wasn't numbed. She leaned forward and picked up a small plastic bottle from the floor by the sofa. My heart sank as I realized that she was going to apply numbing cream to my nuts too, but she spoke reassuringly.
"Relax baby, it is KY lubricant. This will get you off," she assured me, "despite Suky and Amanda's best efforts to cock-block you, I will help you to come inside me."
She gave me another innocent smile, and after coating her fingertips with the lubricant, began to fondle my testicles, as we kissed. I continued to fuck her as we made out, and once my balls were covered in KY, Steph put the palm of her hand under them and encouraged me to grind my nuts into her hand, to see if that would get me off.
My nuts were very sensitive, and grinding them against her palm felt amazing, I just wasn't sure if it was enough to make me orgasm. Steph was very patient, and continued to tease my ass-cheeks with her other hand, lazily raking her manicured nails across them.
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