Remote Work Pt. 04

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His training continues to escalate.
3.8k words
4.1
13.5k
6

Part 4 of the 6 part series

Updated 06/12/2023
Created 01/07/2023
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She grinned at the desperate little ugly man on the floor sucking his jiz off her gloved hands.

"Open the gate and let my friends in, little man," she said in her bubbly tone. "They have limits to test." She gave a little chuckle that made him a little uncomfortable as she walked over to the table to retrieve paper towels to wipe her gloves clean.

Jerry trotted over to the computer and clicked the gate icon so the car could come to the house. His heart pounded when he watched the car on the monitors as it passed through the gate heading up the drive.

"Go greet our guests and show them down, Jerry," she giggled, knowing it was going to be difficult for him as he was completely naked and had never met these people before. He turned and looked at her for a second, frozen in fear. "Yes, just like you are. You'll be naked in front of them all night." He started to slowly move to the stairs reluctantly. She grabbed her crop off the table where she had left it, and started walking towards him. He found a sudden urgency in his step and hastened for the stairs. She stopped and smiled as he disappeared up the stairs.

He saw the car stop in front of the house as he approached the door. As he opened the front door, two people exited the car, a tall thin woman with long blonde hair and a short blonde woman from the driver's side. Jerry just stood looking at them for a moment before the short woman spoke.

"Is that how you greet your superiors, bitch," she said flatly as she closed the car door. "Nice hair, weirdo," she scoffed. She was about his own height, straight blonde hair pulled back in a ponytail. Low cut faded blue jeans hugged her voluptuous hips and legs, ending with her little feet poking out with pink flip-flops and pink toenails to match.

Her shirt was a half top that showed off her ample cleavage and big puffy sleeves with large frills on the cuffs and neckline. A gold cross hung from a delicate gold chain around her neck. Her face was round and friendly, with blue eyes, thick lips, a button nose, and skin that said she was in her early twenties.

Jerry dropped to his knees, assuming that was what she had expected. She grinned her approval, turned and opened the back door of the car where she retrieved a small duffle bag.

The other woman stepped around the car. She was wearing black stiletto heels, stockings with garters that disappeared under a short leather skirt, a leather bra to hold up her large breasts, and a short leather jacket. She was carrying a small box in one hand and that's when Jerry noticed she was a he. The square jaw and adams apple gave her away. She saw the look on his face as she approached him and gave him back a broad grin.

"Aren't your eyes supposed to be on the floor, little fella," she asked as she approached him. Just then he was hit gently in the chest with the bag the driver had gotten out of the back of the car.

"Take us to your leader, worm," said the shorter woman after tossing the bag into him and they both howled with laughter.

Jerry gathered up the bag and headed into the house. "This way, please," he said, still unsure how to address these women. They followed him into the house and down the stairs.

As soon as Jerry made it about two steps into the basement, Sandy's voice rang out, "Present!" Jerry stopped in his tracks and fell to his knees, still holding the duffle bag in front of him.

"HEY!!" All three women yelled simultaneously. Sandy rushed over to greet the women and they all shared embraces and air kisses.

"I brought the glasses," said the taller woman and handed the box to Sandy.

"Thanks, Lisa." Sandy took the box from her and they all walked over to the table with the wine and charcuterie board. "Did you shoot today, Cathy?" Sandy asked the shorter woman.

"Yeah, I've been on a clean out since yesterday. You called me on set, so I didn't even shower after the scene. Lisa and I just grabbed our shit, programmed the GPS, and headed on over," she laughed and looked at Jerry on his knees, staring at the floor. "Your text said I could get as nasty as I want with him, right?"

"Yeah, I wanna see what he'll do for me," Sandy giggled and they both joined her.

"Well, then, let's get this show on the road," Cathy said enthusiastically. "Did you have a place in mind for me," she asked.

"There's a drain in the floor right over there." Sandy gestured to the drain in the bathroom area and walked up to Jerry kneeling on the floor holding the duffle bag.

His mind was a blur. Not sure what they were talking about. Nasty with me how? So nasty you need a drain close by? What the fuck was the plan here? Was she going to make him drink her piss too, and this other woman as well? Was that it? He'd done that, he could do it again. What was the short blonde woman planning to do?

"Cathy does porn, Jerry. She specializes in anal and watersports. She's gonna show you what she likes to do to her slaves. Until she's done with you, she owns you. If you quit on her, you're quitting on me. Do you understand Jerry?" He just knelt there in front of her and nodded his understanding. "Good boy, now take her bag to her." Sandy gestured to Cathy who had moved over to the bathroom area and had disrobed for all but her top, which she was working on. After she removed it she handed it to Lisa, who was holding the rest of her clothes.

"Get over here, bitch," Cathy said as she redid her loose ponytail, her large breasts swaying as she did so. "Put the bag by the sink, turn around and get on your knees," she commanded as she finished with her ponytail and stood looking down at him with her hands on her hips. She now wore nothing but a few rings on her fingers and toes, and a smirk. Jerry came to her and placed the bag where she had gestured and then assumed the position she had directed. He heard her unzip the bag and dig though it for a few seconds before approaching him.

As he waited for Cathy, he watched Lisa and Sandy chatting in hushed voices too quiet for him to hear and drinking wine as they watched Cathy prepare him.

"Open your mouth," she commanded and he opened his mouth. He then saw the metal ring with a leather strap coming from each side pass before his face as Cathy forced the ring into his open mouth and then buckled the straps together behind his head. She then attached the spring clip on his ankle restraints together and then did the same to the wrist restraints. After securing his limbs together, she came around in front of him with a leash and tiny collar. She held it in front of him on one finger, "know what this is?"

He knew. His balls still hurt from the last time he had it on only a half hour ago, if that. He nodded. She giggled as she squatted down in front of him and began gathering his still tender balls together so she could secure them in the device. He groaned in pain as she did so.

"Awww, is it tender," she mockingly pouted at him, and then giggled as she continued to lock the device onto his balls. She stood up and playfully pulled up a few times on the leash, making his balls bounce around as he grimaced. "Nice and tender, huh?" She raised her foot and lightly ran his balls over the top of her foot before giving his balls some gentle taps with the top of her foot. She giggled as he wiggled around in obvious discomfort. "Sandy's already been working on your balls tonight hasn't she," she giggled. He nodded again. "Good, that'll make you easy to control."

She laid the leash over his shoulder as she walked around behind him, before he felt her grab the ponytail sticking off the top of his head and roughly pull him onto his back before dragging him by the hair until his head was close to the drain. Once satisfied with his position, she moved so she had a foot on either side of his head, and then came down hard on his face, grabbed his ponytail in both hands and started rubbing her asshole from his chin to his forehead. Her ass crack felt wet and slick and he thought maybe it was sweat.

"I think my ass is still slick with lube from getting railed in my last scene. Feel how easy I'm gliding on you?" She stopped with her asshole directly over his open mouth. Oh, God, it's not sweat, it's left over lube from her getting fucked in the ass in a porn scene and she was rubbing it all over his face, with his mouth held open by a ring gag. He started to wretch, but managed to keep it to a quick gag, making holding his breath even harder under her.

"Are you gagging already? I haven't even gotten nasty yet," she laughed. "Lick my tender asshole. It took a beating a little while ago. It needs to be loved now."

He was repulsed by the idea of the lube from an earlier buttfucking session still being on her ass to begin with, let alone licking it. He couldn't bring himself to do it. His lungs burned for air but she just sat there waiting, grinding slowly just barely moving on him. After what seemed like an eternity, she suddenly released him and stood up.

"Ok," was all she said as she walked over to her bag and came back with rope, a black stick about two feet long, and a syringe about 1-½" in diameter and 6-7" long. He was relieved to see that there was no needle on the syringe, it just had a hole on the end of a long plastic tip. She dropped the cane and the syringe on the floor next to him.

"Roll over on your side," she said as she kicked him lightly with her foot. He rolled away from her and she knelt down behind him and tied the rope to the link between his wrist restraints. "Bend your knees and bring your feet to your butt." He did as she bid and she tied the rope to the link between his ankle restraints. She picked up the cane and stood back up. "On your back." The cane ripped through the air and landed on the top of his thigh, leaving a stripe of fiery pain in its wake. He yelped from the ring gag and flopped around to quickly get on his back in his new restraints. He could hear the other women in the room laughing at his plight in the background.

"You fucked up when you didn't lick my ass like I told you to do. I was going to go easy but nasty, but now that you've pissed me off, it's gonna be rough and nasty." She straddled him and sat down on his chest facing his feet this time. She grabbed the leash attached to the ball stretcher and pulled it taught, causing him to issue a groan of pain. "Spread your legs." He was able to spread his legs even though his wrist restraints were tied to his ankle restraints by a short piece of rope. He spread his legs as wide as they would go, and then he heard the cane sing its wind cutting song before crashing into the tender skin of his inner thigh. It was a pain unlike anything he had yet experienced. His legs instinctively snapped back together and he writhed in pain under her as a squeal of shock and pain came from him that sounded like somebody else.

"Now that we understand what kind of pain I will bring to you when you disobey me, let's try this again." She scooted herself back positioning her asshole back onto his open mouth. "Open your legs." His body trembled but he spread his legs again and began groaning and begging into her asshole.

"No, no. No noises from you." She tapped on his inner thigh near where her last blow landed. "Start licking," she commanded and pinched his nipple and began twisting it.

His inner thigh burned like fire and now his nipple was in absolute torment. He knew if he didn't perform soon and overcome his repulsion, Sandy would probably leave. She told him he would have to endure this woman's torments until she was done with him. This was the test. FUCK! His mind screamed as his tongue came in contact with her greasy asshole. He began massaging as much as he could with the ring gag in his mouth. The lubricant tasted sweet, almost like grape koolaid, he thought to himself.

"Mmmm, there ya go. Tastes like grapes doesn't it? It's grape flavored lube. It was an ass to mouth scene and I didn't want it to taste like shit." She laughed at her joke as she released his nipple and ground her ass on him as hard as she could and then just sat, balancing all her weight on his face as he lapped at her asshole. She waited until his licking became erratic and he began struggling and trying to turn his head for air before she got up on her knees and let him gasp for air.

"Hey Lisa, can you give me a hand please," Cathy asked.

"Sure babe, whatcha need," she said as she placed her wine on the table and came over to her friend, Sandy right behind her to get a better view of the show.

"Take the syringe and fill it with air, then stick it up my ass and fill me up." She reached down and pulled Jerry's legs together so she could lean on them, and then arched her back to expose her asshole for Lisa. Lisa did as Cathy had asked and then Cathy resumed her seat on Jerry's face. She wiggled around until her asshole was sealed against his mouth again.

"Let's play a game, bitch. You shove your tongue up my ass and try to stop me from farting," she laughed and farted into his mouth before he could even try to stop her. The foul air seemed to almost have a taste. He didn't believe the fumes would be so strong after only a minute in her ass. "Try again, I have more," she laughed. He tried to shove his tongue in her ass but she was already farting again, hard and long this time, billowing his cheeks out until the air started to force its way through the seal between her ass and his mouth, making a loud farting noise. They all laughed loudly and Cathy leaned back up to expose her ass for Lisa. "Give me another shot, babe," she said to Lisa as she looked back over her shoulder.

"Please, no more, please," Jerry begged, but with the ring gag it was so distorted it was barely intelligible.

Lise injected another syringe full of air into Cathy's ass. "I love the begging," she grinned sadistically as she descended upon his face. Grabbing his ponytail, she sat down hard on his face and ground on him a bit before forcing his nose into her asshole. He knew what she was about to do and he started to fight, but his struggles were weak and he was tied. She started laughing as he began to struggle. He felt her asshole push against him and flower out on his nose as the gasses began expelling. Some went into his nose and some just bubbled out from between her ass and his face. Again, they all howled with laughter.

He was laying there, nose up Cathy's putrid ass as she continued to grind on him after farting up his nose and on his face. The gasses burned his nose as they went into him. He wanted to puke, but he choked it back. She dug her heels into the sides of his head, pinching him between them so he couldn't turn his head without a serious fight, then she moved her pussy over his open mouth, stopped wiggling on him and became very still. He was hoping she was going to get up and let him breathe again, but just as the thought crossed his mind, the first dribbles of urine hit his tongue. The dibble quickly turned into a steady stream.

"Drink or drown, bitch," Cathy laughed as her piss began gushing into his mouth. He was in hell, lungs burning for air, nose full of farts, and this evil woman pissing down his throat, and laughing about it. Her flow was outrunning him and he choked. Urine sprayed out onto his chest from between her legs and she quickly jumped up and released him to roll onto his side, choking and coughing on her urine as he gasped desperately for fresh air. He heard Sandy and Lisa give a loud "Ohhh," simultaneously as the incident occured.

"You didn't let me finish," Cathy said as she squatted back down and finished relieving herself on the side of his head as he lay coughing and trying to regain his breath. "I'll give you a couple minutes to regain your composure before we move on." She walked over to the sink and began running water.

Move on? Move on to what? Was that not the end, farts and piss drinking wasn't the end? Jesus, how far did she expect me to go? That's when he saw Cathy bend over and Lisa injected a syringe of warm water into her ass. Cathy stood back up and walked over to him where she removed his ring gag before again straddling his torso and sitting down on his chest facing his feet.

"Now we get nasty, my little worm," she giggled. "I'm gonna give you a chance to redeem yourself, you little piece of shit. If you can suck the enema out of my ass, I'll let this be the end of my games." She scooted back and hovered her ass over his face so that he had to reach his head up to get his mouth near her asshole.

What the fuck!?! Holy shit. No fucking way he could do this. He knew he would be puking everywhere if he tried. That's when Sandy stepped into his view.

"Better get busy Jerry, or you'll never feel my touch again. In fact, you'll never even lay eyes on me, or so much as hear my voice." She then disappeared from his view as he heard her heels clicking across the floor.

"Get busy, bitch," Cathy goaded with a huge grin on her face.

Fuck, fuck, fuck was running through his head. He didn't want this, but Sandy, oh man, he felt his dick twitch. He'd do it for her, he could do it. He steeled himself and raised his mouth to her asshole. He wanted to gag, but choked the urge back and sucked. The enema water poured into his mouth. It tasted like bitter grapes and he just sat there for a moment looking up at her back as she sat there. He watched as she looked over her shoulder down at him and smiled. "Swallow it you fucking worm," she giggled.

NO! Rang through his thoughts as he laid there with a mouthful of enema water. Even as repulsed as he was, he swallowed, and it came right back up. He turned his head and vomited what seemed like a gallon of urine with a small amount of food in it.

"Nice try, shit lips. Do it again, and try to keep it down this time." She pulled on the leash attached to his balls and wiggled her ass in his face. "The longer you wait, the worse it gets." She pulled harder on his balls. He wasn't sure if she meant the enema water in her ass would get worse or the pain in his balls would get worse, but he decided he didn't want to find out. He sealed his mouth on her asshole and just sucked and swallowed as fast as he could until a long fart issued from her and she giggled as she sighed.

"Good job sewer bitch. One more and we'll be done," she said over her shoulder as she raised up on her knees and bent over to expose her ass. "Fill me back up, Lisa."

"No, please. You said if I did it, you'd stop," he begged desperately as Lisa walked over to them with a syringe full of water.

"You didn't do a whole one. You puked up some of it. You do all of this one, and I'll let Sandy have you back," she gave a little hum as Lisa injected the water into her ass again.

He was struggling to keep it down, and now he'd have to take another cup or so more to satisfy her. His stomach was turning as her ass came back down to hover over his face again, a little drip of water running down her ass cheek from her asshole. He closed his eyes and went after it again to hurry and get it over with. His lips locked onto her asshole and he began sucking and drinking as fast as possible.

"Whoa, get it worm," Cathy chuckled as Jerry attacked her asshole. She pushed him down to the floor and settled her weight onto his face as the last of the enema was expelled from her along with another fart. She ground her asshole down on his mouth. "Lick, bitch," she demanded and Jerry complied without hesitation, feeling utter broken at this point and slathering her asshole with licks. How could he go lower than sucking an enema out of someone's asshole and drinking it. He deserved to be called worm, or whatever else they deemed to title him.

"That's a good, bitch," she grinned as she complimented him while he licked her asshole and she ground down on him. "I'm done with him Sandy," she said as she stood up and walked over to the open shower a few feet away. She turned on the water and adjusted the temp so she could rinse her lower half off. The water ran across the floor and started to rinse the vomit, urine, and enema down the drain.

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