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Introduction:

After arriving back on the island, Libby punishes Riley for failing her task, and rewards me for a successful auction.
After the auction, Libby decided to celebrate my first successful auction by taking a trip to Vegas. We took her plane, and Junko and Sandra tagged along to the casino. Since I had never had the chance to gamble in Vegas before, time got away from me, and we decided to spend the night. While we were in our room, I was treated to a world-class blowjob from Sandra. Then, the two Sluts were let loose on Riley. They were given strict instructions to not let her cum, so for well over an hour, Libby and I pleasured each other to the sight and sounds of Sandra and Junko teasing and denying Riley her orgasm. Eventually, the pair took turns riding Riley's face until they got the orgasm my Toy was so desperate for. Afterward, Libby, Junko, Sandra, and I slept in a content, over-sexed heap on the bed while Riley was forced to sleep on the floor with her hands and ankles cuffed to ensure she didn't play with herself. The next day, we flew back to the island.

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The five of us stepped off the elevator and turned toward my office. Heather saw us from her desk and smiled. "Welcome back, Jason!" she greeted with enthusiasm. "And welcome to you as well, Miss Lawson! It's nice to finally meet you!" She stood up and gave the both of us a respectful slight bow. "I trust everything went well at the auction?" Libby gave Heather a warm smile and responded, "You must be Heather. It's nice to meet the woman that helps keep Jason on track." She turned to me and said, "You've got good taste." Heather blushed and smiled. "Thank you, Miss Lawson. Deputy Kendra and her Toy are in the office already. Shall we join them?" I nodded, and she opened the door and gestured us in.

I stepped into my office and immediately felt like I was at home. Kendra was sitting in my chair, with a bottle of champagne chilling in a bucket on the desk. To her left, occupying the previously-empty space in my office, was a sheet covering Riley's punishment. Standing dutifully to her right side was her Toy, which I could see that she had wasted no time customizing. Her hair had been dyed to fade to dark purple, her bangs had already grown out, and she was wearing a strange body chain that was hooked to nipple and clit piercings and her choker. The choker had a nametag that read "Bara". As I got closer, I saw that a stylized 'K' was tattooed on her inner thigh, sticking out an inch above her simple thigh-high socks. I had to admire Kendra's creativity with the piercings, and it was yet another reminder that I needed to customize Riley.

"Welcome back, Mr. Lead Trainer." Kendra said playfully as the six of us filed into the room. "I kept your seat warm for you. Miss Lawson, always a pleasure." She smiled and gestured to the champagne bucket. "I would've had glasses ready, but I didn't know how many to pour." I looked at Libby and raised an eyebrow. "Four glasses, if you'd be so kind," Libby responded. Heather started to move to do her usual assistant job, but Kendra raised her hand to stop her. "Don't worry about it, Heather. Bara here's got us covered." She reached over and gave the center of her Toy's chain a gentle tug. "Pour Mommy and her friends a drink." The noise Bara made as her chain got yanked was a mixture of a yelp and horny moan. To her credit, she recovered quickly and retrieved glasses from the bar before pouring four glasses and handing them to us.

Libby appraised the Toy's girlish figure as she served us. "So this is the Toy Jason convinced me to let you have, Kendra?" She turned her gaze to Kendra, who was waiting for everyone to get their champagne. "Do you have a thing for little girls, Kendra?" The inquiry, while asked in a tone that was more playful than accusatory, caught Kendra completely off guard. "I... I..." she began to stutter. Libby smiled and giggled, clearly pleased with herself by throwing Kendra off her game. "Don't worry about it. In our line of work, you can't afford to be judgmental. Besides," she gave Kendra a knowing wink, "she's kinda cute." Kendra visibly relaxed, and with herself, Libby, Heather, and me all receiving our glass of champagne, she raised hers and said, "A toast, to our first successful auction of many!"

We clinked our glasses, but before everyone was able to take a drink, I had an idea. "Wait. Why don't we use our Toys as glasses? Heather, you're more than welcome to use Riley with me." "An excellent idea," Libby responded. "Sandra, Junko, strip and lay on the desk." She faced Heather and smiled. "I have two Sluts, so you can use Sandra." Heather smiled and nodded her thanks as Libby's Sluts immediately dropped their maid-like uniforms and laid on my desk. I turned to Riley, who was wearing a cute-but-sexy blue dress that Libby had insisted on buying her in Vegas. "Join them." Her freckled face was already flush, but it turned even more red as she obediently started to disrobe. As she slipped off her panties, Kendra and Heather were treated with the sight of a small antenna betraying the presence of the remote control vibrator currently in her pussy. Libby had placed it in her after our night's stay in Vegas, and had been mercilessly teasing the redhead since. Riley made her way to the desk and joined Libby's Sluts and Bara, who had gotten on while she stripped.

Libby raised her glass for another toast. "If you had told teenage me that I would be licking champagne off the bodies of women I owned, I would've laughed in your face. However, as I stand here, I can honestly say that I wouldn't want to be living any other life. To the insatiable desire for mankind to dominate and fuck!" "Here fucking here!" Kendra responded enthusiastically. Together, the four of us poured our glasses on the Toys and licked them off. I made sure to spend extra time teasing Riley's nipples, causing her to moan and fidget. As I finished, I saw that Libby was watching as Heather and Kendra were kissing Sandra's and Bara's mouths, having poured the lion's share of their drink in them. Shortly after, they finished their drinks, punctuated by a loud suction noise as Heather's lips left Sandra's. "Fuck, that was hot! Thank you, Miss Lawson!"

Libby nodded her acknowledgment before kickstarting what she was here for. "Well, with the celebrating out of the way, it's time for someone to be punished." Riley's breathing quickened a little, as she knew that she was about to experience something she would never have opted into if given the choice. "Heather," Libby continued, pointing to the sheet-covered object, "am I to assume that that's the spitter's steed?" "Yes ma'am. Mr. Jason didn't specify what kind, so I got one that can be switched between plastic, wood, or metal." Libby's face lit up. "An overachiever? Jason certainly chose his assistant well. Let's go with metal." She reached into her purse and pulled out a handheld video camera. "You, Toy," she barked while pointing to Bara. "Do you know how to work one of these?" The tiny girl shook her head, "No, Mistress." Libby handed the camera to Heather. "Please show the Toy how to use this. I would like a reminder of today. Sandra. Junko. Get the horse over by the couches and set Riley up." "Yes, Mistress!" the pair replied in unison.

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As Sandra and Junko marched Riley over to the horse to get her strapped in, and Heather showed Bara how to operate the camera, Libby gestured for Kendra and me to follow her to my bed. Once we got there, she turned to Kendra. "Deputy Kendra," she began in an authoritative tone, "do you appreciate the gift Jason secured for you?" She nodded toward the tiny Japanese Toy. "I really do, ma'am. It's nice to have something that's truly mine." Libby nodded, "And have you properly thanked Jason for sticking his neck out for you?" Kendra looked at me with a wry smile. "Not yet, but it's going to happen as soon as I get the chance."

Libby looked at me, shook her head, then stepped next to me and possessively put her hand on my chest. "Kendra," Libby's tone gained an icy edge, "you do understand that Jason is mine, right?" The sudden shift in questioning and demeanor threw Kendra off. "Why... y... yes, Miss Libby," Kendra responded, searching both of our eyes for any sign as to what was happening. Libby continued, "So you understand that the only reason you get to do anything with him is because I allow you to, right?" Kendra's cheeks turned bright red as she nodded. "Good." Libby moved closer to Kendra and started gently stroking her curly auburn hair. "Did you know that Jason and I haven't actually fucked yet?" Kendra's eyes grew wide as she looked from Libby to me. "Don't get me wrong," Libby continued, "we have done plenty of things together. But I have yet to feel him inside me. Or any dick, for that matter." I looked at her, surprised by the information. Libby saw my look and smiled. "Only fingers, toys, and tongues, love."

Libby moved behind Kendra and smiled at me seductively as she started running her hands all over Kendra's stunned body. "So here's what's going to happen. You're going to thank me for allowing you to play with my man." She gave Kendra's neck a little kiss. "You're going to thank me for allowing you to have a Toy." She gave Kendra's boobs a squeeze. "And you're going to thank Jason for going to bat for you." She gave Kendra's ear a playful nibble as she reached and grabbed the bottom of Kendra's shirt. "Take your clothes off." I watched Libby half-help half-force Kendra out of her clothes. I had seen Libby's dominant side several times, but witnessing Kendra be submissive to any woman was really having an affect on me. I could feel precum already leaking out of my rapidly hardening dick as Kendra's cute red lace panties hit the ground. Libby guided Kendra, whose flush face and closed legs betrayed her own arousal, into a proper presentation stance before she moved back to me. She gave me a deep, lingering kiss before she turned and eyed my Deputy.

"Kendra," Libby began, "you're going to get me ready to receive Jason for the first time. You will eat me out while Jason has his fun with Riley on the horse. After I am properly satisfied, and because you need to know your place, you will watch while Jason takes me for the first time." Kendra swallowed hard. Libby continued, "Since your Toy will be indisposed filming everything, you will please yourself. However..." Libby reached into her purse and pulled something out, keeping it concealed in her closed hand. "You are not allowed to cum until after I leave this island." Kendra gave a pained look, clearly not thrilled about being denied relief. Libby simply smiled and walked back to Kendra. She began to slowly run her fingers down Kendra's naked body while keeping her closed hand behind your back. "If I find out that you have broken this command," her fingers slid between Kendra's legs and spread her soaking pussy, and the hand behind her back revealed a knife as Libby brought it between Kendra's lower lips. "If you break the command," Libby repeated for emphasis, "I will personally turn you into one of those Dolls you're obsessed with. Do you understand?" Kendra whimpered, clearly in uncharted territory as far as power dynamics were concerned. "Yes... Yes, Miss Libby." Libby tutted her tongue, pressing the dull side of her knife against Kendra's bud. "Now, that doesn't seem appropriate for this situation, does it, Kendra? I asked you, 'Do you understand?'" Kendra closed her eyes, overwhelmed by everything that was unfolding. I swear I saw her slowly start to rub against the knife. "Yes, Mistress," she whispered.

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"Wa... One... One hundred." Riley barely murmured as I slapped a riding crop across her inner thigh. For the past hour, the redhead had endured getting whipped while the metal of the horse vibrated and dug into her. In the beginning, she handled the strikes like a champ, but the constant involuntary twitching kept her bouncing on the brutal device. Additionally, the remote in my hand allowed me to constantly change the intensity of the vibrations, as well as the overall temperature of the metal itself, ensuring the Toy never got used to anything that her pussy was experiencing. After the 43rd strike, she lost control and pissed herself. The extra liquid mixing with the fluid that was already leaking from her pussy made it even harder for Riley to find a resting position that didn't wreck her. Like a good girl, Bara caught every strike, moan, and scream. On several occasions, I saw her hand quickly squeeze her little tits and brush against her pussy, betraying that the Toy likely shared some of Kendra's sadistic tendencies.

Heather was lost in her own little world. Libby had given her permission to use her Sluts, and the trio wasted no time ripping each other's clothes off and enjoying themselves. Currently, Heather was sitting in one of the recliners with Junko's face buried between her legs. As Junko furiously serviced Heather with her pierced tongue and herself with her hand, Sandra laid in Heather's lap, making out with my assistant as Heather used one hand to please Sandra's sopping slit and the other to mangle her large tits. On the couch, Libby propped herself up with the throw pillows so she could watch as I played with Riley. At the moment, she had one hand kneading her C-cup while the other firmly gripped Kendra's hair as my Deputy serviced her. Kendra's ass was in the air, and I could see her hand slowly working over her lips, no doubt teasing and edging herself wild.

Libby noticed me watching, and when our eyes met, she wrapped her legs around Kendra's back, locking her in place. "Ok, time to make your Mistress cum one more time like a good girl. Get me nice and wet for Jason." The extra pressure from Libby's legs caused Kendra to moan from surprise, but the glazed look in Libby's eyes told me the move was extremely effective. "Jason, bring your Toy over here. I want to finally make her cum. And you, girl," Libby briefly let go of her boob to point at Bara. "Lick that horse and the floor clean." Bara looked confused as I began to unstrap Riley. "And set the camera on the table so you film yourself doing it." The little Toy nodded reluctantly before responding, "Yes, Mistress." As soon as I got Riley off her mount, Bara got to work, licking every fluid off the horse.

I half-led, half-carried Riley over to the couch. The moment she was within arm's reach, Libby plunged three fingers of her free hand into the Toy's puffy, reddened cunt. Riley could only open her mouth in stunned silence at the aggressive invasion, and, after only 10 seconds, she came. Days'-worth of edging, suffering, and pleasure caused a torrent of squirt to soak Libby's fingers and hand before my Toy collapsed, babbling nonsensically as she skirted the edge of consciousness. "Good girl," Libby said through quickened breath. "My turn." Her cum-covered hand joined her other one holding Kendra down, and she started mercilessly grinding her pussy against Kendra's face. "Kiss me, Jason!" she shouted. Needing no more direction, I dropped down and met her open mouth with mine. The moment our lips touched, Libby's body tensed, then spasmed as a powerful orgasm ran through her.

Libby held the kiss for a full minute as she rode her orgasm through completion and came down from it. Finally, she released Kendra's head and unlocked her legs, and my Deputy sputtered as she slowly raised her head to breathe unimpeded for the first time in almost an hour. Libby leaned forward and gently held Kendra's face. "You did good, and you deserve a reward." As Kendra looked confused, Libby kissed Kendra, seemingly enjoying tasting herself. However, before Kendra could register what was happening and kiss her back, Libby broke contact. Kendra looked a little disappointed, but quickly recovered. "I'm glad I could please you, Mistress."

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I surveyed the scene. Heather, Junko, and Sandra were still on the recliner, lost in a tangled mess of writhing bodies and lust. Bara was shamelessly playing with herself as she ran her tongue all over the various liquids Riley left on the horse and floor. My Toy was on the ground at my feet, fully in a haze now that her torture had finally concluded. Kendra and Libby were still somewhat entangled on the couch, with the former still recovering from what was undoubtedly the longest submissive pussy-eating session of her life. My dick was throbbing. So, I opted to be proactive. I reached down and grabbed Libby. The ebonette squealed from surprise as I effortlessly tossed her over my shoulder and gave her soft, round ass a satisfying slap. "It's my turn now," I said as I began to carry her over to my bed. From behind me, I could feel Libby gesturing for Kendra to follow us.

I threw Libby on my bed and started to take my clothes off. Before I got very far, Libby asked me to stop. "Kendra, get Jason ready for me," she ordered. "Yes, Mistress," Kendra said with a voice that sounded equally sad and excited. Her dark brown eyes never broke contact with mine as she lifted my shirt over my head and undid my pants. As soon as they slid past my dick, it sprang free and slapped Kendra in her face. She made a yelp of surprise, but quickly recovered and began to devour my dick. The sudden warmth and moisture almost brought me to bust instantly. However, after a couple seconds, I was able to calm down, keeping my eyes on the prize. Libby watched the blow job for about a minute before she called for Kendra to stop. Before Libby could give any more instruction, I climbed into my bed and spread her legs apart. With my dick slick with Kendra's saliva and her pussy dripping with need, Libby nodded her consent to take her. "Be careful, baby," she said with surprising vulnerability, "It's my first time."

I didn't care. The ebony-haired woman in my bed belonged to me, and it was finally time to show her. I brought my dick to her pink entrance, and in one smooth motion, took her. She moaned as I entered, and quickly tried to set the pace. I put a firm hand on her hip and shook my head. "No you don't. Right now, the only thing you get to do is cum." Before she could reply, I started. My pubic bone slammed against her clit and my balls slapped against her ass over and over as I fucked her without mercy. After a minute of relentless pounding, she came, barely able to mutter "fuuuuUUUUUuuck" as her body convulsed and her pussy leaked even more fluids.

That wasn't enough for me. Before Libby could process what was happening, I flipped her over on her hands and knees. My left hand grabbed a fistfull of hair and shoved her face into a pillow, while my right reached under and grabbed a tit and squeezed. A muffled noise of confused pleasure came from the pillow as I continued my rough treatment by once again ramming my dick into her waiting pussy. I could tell she was struggling to breathe, but I took no mercy on her. I increased my pace, and while desperately fighting my own orgasm, I said, "You better cum before you pass out!" To emphasize my point, I pushed her face further into the pillow and twisted her boob. Impossibly, her pussy clenched my dick even tighter as the proud heiress was reduced to nothing but a fucktoy. In no time, her body tensed into yet another convulsive orgasm. As I felt it arrive, I yanked her hair, bringing her head out of the pillow. Libby screamed with ecstasy as her body completely gave out and she collapsed onto the bed.

My raging hard-on reminded me that I hadn't had my fill. I laid down on my back, and Libby offered no resistance as I pulled her on top of me, tits in the air. My dick once again found Libby's drenched cunt, and her breath hitched as I rammed myself balls-deep inside. Somehow, my prize found the wherewithal to reach between her legs and furiously rub her button. "Please," she said, straining to have any volume to her voice, "Cum in me." Those were the magic words. I fucked her with reckless abandon, no longer caring about the sensations I was causing her. As I rapidly approached orgasm, Libby suddenly grabbed one of my arms and brought my hand to her throat. I squeezed instinctively, and she choked out a "Yeeeeeesssss," as her legs closed, ushering in another shattering orgasm. Her cunt vibrating on my dick drove me over the edge, and over an hour's-worth of built-up cum shot deep inside her.

Both of our bodies gave out. Neither of us had the strength or motivation to move, so she stayed laying on top of me as we both tried to recover. After a minute or two, I felt a strange sensation between my legs. I opened my eyes to see Kendra slowly pulling my dick out of Libby's pussy. Worldlessly, she took my dick in her mouth and gently sucked it clean. Then, she moved on to Libby, and licked and sucked her clean as well. Libby watched for a while before turning to face me. Her cheeks were red from exertion, and her eyes could barely focus, but there was an unmistakable look of pure bliss on her face. "That was better than I could've possibly imagined." She leaned in and gave me a deep kiss. "You were well worth the wait, baby." I couldn't help but smile. So many men were stuck in sexless relationships, and here I was, fresh off fucking one of the wealthiest women in the world while my second-in-command cleaned us both up. "And you," I leaned up to whisper in her ear, "are mine now, bitch." Libby's usual confident demeanor shifted. She lightly bit her lower lip, lowered her head, looked up at me with just her eyes, and silently nodded her assent.
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