Remote Work Pt. 03

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The training continues as the game escalates.
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Part 3 of the 6 part series

Updated 06/12/2023
Created 01/07/2023
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The taste of the bottom of her boot reminded him of potting soil. One would probably find the same things in potting soil as found on the bottom of a shoe, he thought. He tried not to gag again like he did on the precum she fed him. That had pissed her off. If she wanted him to totally humiliate himself for her entertainment, he would, and was the smothering supposed to be a punishment? The lack of air had him panicking a few times, but what heaven it was to have her pussy in his face. The thought of her wet pussy on his face and her hand on his cock made him hard again. Even her ass smelled and tasted good. He could spend days under her as she touched his cock. If that was her idea of dominating him, he was down for a lifetime.

She hung the phone up and looked down at the little man licking the bottom of her boot. She gave him a broad grin and chuckled ominously.

"In about an hour or so, some friends of mine are going to show up," She said as she turned her attention back to her phone and started typing on it. "When they get here, I'm going to let them test how far you will go for me." She finished typing and pushed him away with the bottom of her boot on his forehead. He flipped awkwardly onto his back as she stood up from the couch. She moved next to his hips and straddled him. She squatted down and put her pussy on his hard cock, trapping it between her pussy and his pelvis, but with the head of his cock sticking out, untouched, as she started mashing and grinding on it.

"What would you do to fuck me, Jerry," she smiled at him.

"I would do whatever you demanded of me, Goddess," he proclaimed as he looked down at her crotch grinding against him. It was so good that if she kept this up for very long, he'd be coming again.

"Whatever I demand,"she asked. "I have to make demands of you, Jerry." Her voice sounded irritated.

"No, no, no, no, Goddess," he began stammering as she stopped moving on him. "I will do whatever you want, goddess. I'll do whatever it takes to make you happy." She smirked and just stared at him expectantly. "I'll do anything to make you happy, goddess, anything." Her smirk turned to a broad grin. There it is, exactly the words she was waiting to hear. She had met him at three o'clock yesterday, and in less than two hours with I'm in this basement, the desperate little fucker was already prepared to do anything. She was gonna test the shit outta that.

"Anything?" She stared down at him and slid her pussy up and down the front of his cock again. His eyes rolled back from the pleasure.

"Yes, goddess. Whatever your heart desires," he whispered up to the ceiling with closed eyes. She chuckled and stood up, stepped over him and started walking over to the shower in the corner.

"I'm glad you said that, little man. I've been very gentle so far. I know you think I whipped you earlier, but I can assure you, that was light. Disconnect the cuffs on your ankles and come over here," she said as she approached the shower, looking around at everything. It was just the walls in the corner and a shower head for the shower. There was a curved rod for a curtain, but no curtain. The floor was just bare concrete and the drain was more in the middle between the shower, toilet, and sink, than a drain just for the shower.

He sat up and disconnected the spring clip holding the two cuffs together. He realized as he disconnected the cuffs that it was easy to do on the ones on his ankles, but impossible to disconnect the ones on his wrists, as his wrists wouldn't bend far enough to reach the clip. He hopped up off the floor and trotted over to Sandy, his dick bobbing around as he did. He got down on his knees and attempted to assume the position but his hands were tied together in front of him. He didn't know what to do and she was enjoying watching him squirm.

"Anything?" She looked down at him, grinning mischievously.

"Absolutely, Goddess," he proclaimed confidently.

"I have to pee, Jerry," she giggled. "You know what I need you to do before I'll let you drink my golden nectar," she said, hands on her hips as the smirk returned to her face.

Before you LET me drink your pee!?! She wants me to drink piss? No! He thought immediately. It's too much. He just couldn't.

She stepped closer to him, directly in front of him and he looked up at her. The look she gave him scared him. She looked like she was about to kill him as she grabbed his pigtail in her left hand and slapped him harshly with her right. Had she not had a hold of his pigtail, he would have fallen down, but she yanked him back upright.

"Head up, eyes down. You said anything Jerry, prove it. Beg me for it." She laughed.

He knew exactly what she expected at this point. He didn't want to do this, it would be the most disgusting thing he'd ever done, he thought. He wasn't sure he'd even be able to do it without gagging and puking on her.

"Are you done, little man," she teased him. "Is drinking piss your limit? That seems weak," she chuckled at him and released his pigtail. "Then I guess we're done." She started to walk past him and his panic took over. He couldn't let her leave. It can't be that bad, it's just pee. People drink piss all the time, some even like it. He decided he could do it and threw his hands and face to the floor and began begging to drink her piss.

She stopped and turned back to him so that he could scurry over and grovel at her feet. Lavishing kisses on the tops of her boots.

"Please don't leave Goddess, please. I'll do it, I'll do it. I'll do whatever you want," he begged shamelessly as his will continued to break down for her.

"What I want," she asked. "What I want is for you to want it. I want you to want it so bad you'll beg for it. Beg me Jerry," she said sweetly. " Beg for my nectar."

"Please let me drink your nectar, Goddess," he said just loud enough for her to hear.

She could hear the disgust in his voice as he cringed to say the words. She smirked, knowing that he'd go a lot farther than he believed he could to please her. He was so easy to manipulate after a couple orgasms and the smell of her ass and cunt smeared on his face. She would reduce him to the salivating dog she knew he could be.

"Give me your hands." He held his hands up to her and she undid the spring clip binding them together. "Stand up, put your hands behind your back, and turn around." He did as instructed and she reattached the cuffs back together with his arms now behind his back. "Lay on your back with your head near the drain, just in case," she instructed with her usual bubbliness and a smile. He lay on the floor with his head by the drain and she stepped over him with a foot on each side of his head, then squatted down to hover her pussy above his waiting mouth.

"If you fuck this up, the punishment will be severe. You won't be able to sit still and take it like you did earlier," she smiled down to him. "Open up, little man." He opened his mouth as wide as he could. She used her fingers to spread her lips wide and expose her bladder opening so she could try to aim the stream. It dribbled for just a second before shooting a strong stream directly into his mouth, only filling it about half full, and she stopped. The salty and acrid urine sat in his mouth as he looked up at her smiling down at him biting her bottom lip. He wanted to wretch, but managed to control himself. It was much stronger tasting than he had expected and his stomach was turning at the thought of swallowing it.

"Swallow," she bubbled as she smiled down at him and grabbed his nose so he had to swallow the disgusting fluid to breath. He steeled himself to consume the partial mouthful, her smile grew to a large grin as his mouth closed and she laughed out loud as she watched his adams apple bob as he swallowed it and reopened his mouth without command.

"Good job, little man. You didn't cough or gag at all. Little more this time," she giggled and positioned herself again, this time nearly filling his mouth before stopping. She just smiled at him and cocked an eyebrow expectantly. He closed his mouth, swallowed, and reopened it dutifully. It was easier this time. This wasn't that bad, the taste wasn't great, but it wasn't as bad as he had believed, and it wasn't trying to immediately come back up. He could do this, and that meant she'd stay, and if she stayed, fucking her was on the table.

"Well, done. Now let's see how fast you can drink." She grabbed his pigtail and pulled his face up against her pussy, sealing herself tightly against his open mouth and pinching his head tightly with the heels of her feet. His heart started to pound as he thought, don't drown, don't drown, don't drown. He was surprised by the force of the stream as it his the back of his throat and began rapidly filling his mouth. He began swallowing as quickly as he could to try to keep up with her, but was losing the battle. He chugged frantically in fear of displeasing her, and just as he thought his mouth would overflow, her stream began to subside and he started to catch up and overtake her flow until she stopped completely.

She grinned down at him and pushed his head back down to the floor before rocking her hips forward just enough to have her asshole above his mouth. "Thank me," she grinned. He wiped his tongue across her asshole and mumbled an unintelligible thank you into her ass. She gave a deep chuckle and started grinding down on him a little before standing back up.

"I really didn't expect you to do it without gagging, at least a little for your first time, but you were a real trooper, you even kept up with me when I tried to piss into you as hard as I could." She stepped around him so she was standing next to his chest. She placed the toe of her boot on his chest, being sure to put her heel on his nipple. She slowly started to put pressure on his nipple as she calmly talked, her smile growing bigger the more he squirmed. "I thought for sure that would choke you so I would have a reason to whip you again." He was grimacing in pain as she pushed her stiletto into him. "That's ok, I have another pain game we can play to test you while we wait for my friends." She removed her booted foot from him and walked back over to the workbench where her equipment lay, partway across the room, she snapped her fingers and pointed to the floor. He jumped up rubbing his painful nipple and trotted over to the spot she had pointed at, hoping to please her.

She picked up a ball gag and something that looked like nothing but a leash and collar, but the collar was tiny. She walked back over to him with a big grin on her face. She squatted down and grasped his balls, fondling them to make sure she had them both before slipping the tiny coller around the outstretched skin of his scrotum. After she buckled it and released him, his balls were held away from his body by the tiny loop of leather that was too small to allow either ball to go back through. With the leash attached to it, she literally had him by the balls. She stood up, smiled at him, bit her lip as one eyebrow raised and jerked up sharply on the leash, stretching his balls up and forcing him to his feet.

"Up, up, up," she said cheerily as she stretched his scrotum. She let off the pressure and allowed the leash to go limp. She then stuck the ball gag in his mouth and buckled it behind his head. She turned and walked over to the office chair with him in tow. She picked up her riding crop as she passed the pile of her toys on the workbench. It was a high back, overstuffed office chair that could spin all the way around and had wheels on the ends of each of its five legs. Sitting down, she spun herself around to face the middle of the room.

"Over here, little man," she yanked on the leash and brought him hopping quickly in front of her. She dropped the leash on the ground. "Turn around and spread your legs." He did as she said and she unclipped the cuffs on his wrists, freeing his hands, before reaching between his legs and retaking control of the leash.

"Get on your hands and knees, little man." He got down as instructed and she tied the end of the leash around one of the arms of the chair. "Now crawl to the pole in the middle of the room," she laughed, knowing the plight he had ahead of him. "I know you can't beg or talk with the gag, so if you give up, just lay down and quit. As long as you stay on your hands and knees, I'll keep pushing you. If you understand, just start crawling." He began crawling until the leash started to pull tight on his balls. As soon as the leash was taught, she let him have the first stroke. The crop ripped through the air before cracking loudly on his lower back.

"PULL, BITCH," she yelled at him and began a rain of violent blows across his ass and lower back. He lurched forward to get away from the blows only to find his balls aching like they'd been stomped on, but the whip was worse, and he pulled as hard as his balls would let him, and the chair began to roll. He screamed into the gag and tears poured down his cheeks.

"MUSH, MOTHERFUCKER," she howled with laughter as he inched her and the chair across the floor with his balls. She eased up with the frequency and severity of the blows from her whip as the chair started to roll, and stopped completely as the chair approached a slow walking speed after a few feet. Tears streamed down his face as his huffing breath blew snot in and out of his nose.

"Whoa boy," she said in her best cowboy voice as she pulled back on the leash like reins, bringing him to a halt. "Take me to my wine first." She gave him some light taps as he turned and crawled toward the table where her glass sat. Just as before, the moment the leash went tight, she began whipping him violently, the blows rapid and hard. He made noises like an animal as she rained blows on him. It was taking him longer to get the chair moving this time and not as quickly as before, but she stopped whipping anyway.

"Getting tired already. You can have a break at the table." It was only about ten feet, but to him it was a mile of pain. She lifted one of her feet and placed the toe of her boot on his ass cheek so that the stiletto heel of her boot was right on his asshole and pushed very slowly, forcing her heel up his ass about an inch. His moans into the gag turned to screams of fear and renewed discomfort as he pulled harder and the chair sped up a bit. She laughed and pushed her heel a little further and then they were at the table. She pulled her heel out of his ass and stood up from the chair.

He collapsed on the floor and curled into the fetal position. She reached over him and picked up her glass of wine. She looked down at him as she sipped from her glass. She was impressed with his performance, she had seen that game played many times by long time pain sluts who didn't move that far, that fast.

He lay on the floor holding his aching balls, contemplating this whole thing. His back and ass burned so badly from the whip that he thought she must have drawn blood. It's too much. He couldn't do that again. In fact, he wasn't sure he could do any of this at all. Maybe he wasn't up to this after all.

She could see that he was breaking and probably contemplating quitting. Standing next to his head she squatted down and ever so gently laid her hand on his cheek, he flinched away. "Hey, it's ok." She said sweetly and stroked his cheek. "That was really impressive, Jerry. I've seen men bigger than you not even be able to move a mistress in a chair like that, and I've never seen any of them move as fast as you did that first pull." She smiled sweetly and stroked his cheek again. She offered him her hand, he took it and she stood up but stayed bent at the hips holding his hand as he lay on the floor. "Can you walk yet," she giggled.

"Yeah." He started getting up and suddenly realized he had forgotten to call her Goddess. He looked up at her horrified as he sank back to the ground. "I mean yes Goddess. I can walk Goddess." She pulled his hand and shushed him.

"You deserve a break. You can relax and recover. Come on. Let's go sit on the couch." She helped him up and held his hand as they went around the couch. She just needed to give him another taste of pleasure to keep him hooked. She'd have to be nice now and rekindle his desire for her before she could abuse him again and see how far he would go for her.

Did she say he was good at this? He wasn't sure he wanted to be good at that, but she seemed happy about it, and now she was being super nice. Stroking his face and holding his hand, he felt pretty sure she was about to touch more of him, and his now flaccid cock began to twitch again as they walked around the couch.

She sat down and he just stood there looking down at the couch. "I don't think I want to sit down right now Goddess, my ass is on fire from the whip."

She laughed "I bet it is. At least let me get this off of you." She reached up and gently began removing the tiny leather strap around his balls. He tensed up and inhaled sharply, obviously tender to the touch. As she fondled him to remove the device his cock began swelling again. She carefully undid the buckle and it fell away from his scrotum. He half sighed and groaned in relief and his cock became fully erect. She grinned at him.

"Do you want a break or an orgasm? We can keep going if you want to cum. If you want the orgasm, you'll do it licking my ass and gasping for air. Is that what you want," she asked with a sly smile.

What he wanted was to fuck her, to be inside her, but he would definitely take her offer. He dropped to his knees and began begging as he knew she wanted him to. "Please Goddess, sit on my face and touch my dick," he begged, smiling himself this time.

"Lay on your back," she said, gesturing to the open area in front of the couch. He lay down where she had motioned to and she moved over to him, straddled his body and sat on his chest. She reached forward and grasped his hard cock with her right hand. She stroked and fondled it for a moment before looking back at him over her shoulder and releasing his cock.

"That's all you get until you beg like a good little bitch," she laughed down at him.

Please, please Goddess, touch my cock," he begged.

"That's not what I want you to beg for." She giggled and sat motionless, waiting.

He wasn't sure what to beg for to get her to touch him again. She enjoyed hurting him, but mostly only when he begs her to. What did she want him to beg for, her ass? Then it dawned on him, she wanted him to beg to suffer under her for the privilege of the hand job.

"Please smother me with your ass while you touch me Goddess," he begged, feeling confident that's what she wanted.

"Good boy," she chuckled and moved herself back onto his face with her asshole directly over his mouth before wiggling down on him and sealing off his air. "Lick," she commanded. She waited until she felt his tongue slide over her asshole before reaching down and taking his cock in both hands, and stroking it slowly. His cock throbbed in her hands as she thought to herself how far she could push this ugly little man for nothing more than the chance to suck her ass. She smiled broadly and ground her ass down hard on his mouth as the smile turned to a broad grin before releasing his cock and sitting up to giving him a breath. His cock was throbbing and bobbed around as he writhed around gasping for air.

"Control yourself. Focus on your breathing if you can," she snickered. "Deep breath," she teased cheerily as her ass resumed its position on his face. She waited for his tongue to touch her asshole again before she would touch his dick. She wanted to make sure that he was licking her ass when he came. She wrapped her hand around his cock and began slowly stroking it again.

"Stick it in my ass and wiggle it," she demanded. He made his tongue hard and started pushing it into her puckered asshole. She ground down with her full weight to help his tongue go deeper. She stopped stroking his cock and just squeezed it in her hand waiting to feel his tongue wiggle inside her asshole.

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