Remote Work Pt. 05

Cathy finished rinsing off as Lisa cleaned off the syringe and ring gag before removing the short rope binding Jerry's feet to his hands. She then packed everything back into the bag and retrieved Cathy's clothes from the couch where she had placed them.

"Present," came the bubbly command from Sandy as soon as Lisa had removed the rope from his bindings. Jerry struggled up onto his knees with his hands and feet still bound but not connected to each other, before turning to face her, assuming the position she had demanded of him.

Sandy smiled at how obedient he was, but the look of distress on his face told her how badly he needed a respite. She was impressed with how far he had gone in such a short period, much further and faster than anybody she had ever played with before, but on the other hand, he was the most isolated social outcast she had ever seen. It was easy to see how desperate he was for attention, any attention, and his natural submissiveness begged for her to give him her attention. She had never played with a submissive she found so physically unattractive before, but his almost hyper submissiveness and willingness to endure humiliation and pain for her pleasure made him attractive in a different way. It made her wet to think about the control she could exert over him. The subs she had always played with had hard limits, and they'd walk away easily, refusing to even explore some things, but not this ugly little man. She knew he was so desperate for attention that she could exploit him endlessly, and he would beg for it. Her smile grew into a grin as the thoughts crossed her mind and she walked over to him on his knees.

"Having fun, little man," she asked with a laugh.

He began stammering, searching for something to respond with that he thought she would want to hear.

"Shhhh, it was rhetorical." She moved a few feet in front of him and placed the end of her riding crop under his chin and gently pushed up. "Look at me, Jerry," she said ever so kindly. "You're looking a little rough, so I'm gonna give you a break for a little while." She removed the crop from his chin, walked around behind him, and undid the spring clip holding his wrist restraints together.

"Thank you, Goddess." He just stayed there on his knees, not sure what to do.

"Cathy, would you join me upstairs while Lisa takes care of little man," Sandy asked as she headed to the stairs.

"Sure," Cathy replied and headed to the stairs also, buttoning her jeans as she finished dressing.

The two women disappeared up the stairs and Jerry became very nervous, wondering what Lisa had in store for him.

"I'm sure you have soap and shampoo in an upstairs bath," she asked.

"Yeah, upstairs, in the shower," he replied.

Lisa laughed. "Ok, get the restraints and the ball stretcher off and rinse them in the sink while I go get some things for you to clean up with." She headed up the stairs.

Jerry removed his restraints and went to the sink to rinse them off. His belly was sloshing and he felt ill, but he kept it down for fear of them hearing him hurl.

After a few moments Lisa returned with shampoo, body wash, and towels. She stopped and gave him a somewhat worried look.

"Do you need to purge? You literally look green. If it'll make you feel better you can puke that up."

Why is she being so nice? Yeah, he wanted to puke it up. He didn't need to be told again and immediately spun around and puked into the toilet next to the sink as he dropped to his knees, expelling the contents of his stomach in two strong convulsions followed by a series of dry heaves.

"Drink some water." Lisa helped Jerry up to the sink where he drank from the tap and immediately went back to the toilet to expel the water. "Better," Lisa asked. He nodded. "I know, Cathy can be rough and nasty, that's her thing. If you stay with this, you're going to find out how different each mistress can be." Lisa stood up, went over to the couch and removed all her clothing as Jerry watched her. "Cathy was actually really easy on you because you're Sandy's toy. She usually goes hard with the cane," Lisa said as she turned her back to Jerry, displaying a latticework of purple stripes on her back from the bottom of her shoulder blades to just above her knees. After giving him a second to gaze upon Cathy's work, he turned and came back to Jerry, still sitting on the floor by the toilet.

"Come on, let's get you clean," she said, offering Jerry her hand. Jerry took it and stood up, before Lisa led him to the shower. "Undo the ponytail," she said as she adjusted the water temperature. Jerry complied and then Lisa pulled him into the warm water with her.

"My real name is Leonard, and I've been Cathy's slave for about 3 years now." Lisa explained as she began washing Jerry's hair. Jerry didn't know what to do, so he just stood there and let Lisa, or is it Leonard, wash the piss and enema out of his hair and talk.

"How long have you known Sandy?"

"I met her yesterday for the first time when she called me into her office," Jerry responded.

The hands working shampoo into his hair stopped. "Yesterday? You met her for the first time yesterday? Damn. How long have you been a sub," she asked as she resumed washing his hair.

"I've never done anything like this before. I've never even fantasized about this. I didn't know I could do these things. She just showed up yesterday evening with a friend who threatened to kick my ass, and then she beat me off before leaving," he explained.

"Holy shit. So no experience at all and straight to the deep end," Lisa chuckled. "Was the woman with Sandy a thick, red haired woman," Lisa asked.

"Yeah, Beverly," Jerry responded.

Lisa chuckled, "She's vicious, mean. Likes to hurt people, men especially. Sandy brought her to the club as a sub 5-6 years ago. Arms up." Jerry put his arms up and Lisa began washig him from his hands all the way down his body.

"I'm not gay," Jerry blurted out as Lisa soaped his genitals. Lisa laughed.

"She doesn't want you to be gay. If you were gay, you'd want to suck my dick, and by now, you know she likes making you do things you don't want to do." Lisa stood up and grabbed Jerry's head firmly in her hands and turned his face up to meet her gaze. She was easily a foot taller than he was. "We both know you're sucking cock before the nights out. We both know if you don't, Sandy leaves, and I'm sure you know from the artwork on my back, that if I don't make it hard on you, Cathy will make it hard on me." She released him and washed the soap off herself before stepping away from the shower and grabbing a towel off the sink to dry herself. "Rinse off and come over to the couch." She dug in the duffle bag and retrieved a brush before walking over towards the couch.

Jerry continued to rinse the soap off himself, then turn off the shower and take the other towel to dry himself. His mind was all over the place. Lisa had been so gentle, washing his hair and his body, her touch a welcome respite from the abuses. He also felt a connection to Lisa after seeing the purple stripes all down her back, stirring a sense of sympathy in him. It gave him a sense that Lisa and he were kinda in this together, for him to get what he wants from Sandy, and for Lisa to avoid displeasing her Mistress. He wasn't gay because he didn't want to do it, but if that's what Sandy wanted, he'd do it, he wouldn't like it, but he'd do it.

He approached the couch after drying himself off with the towel and stood in front of Lisa, who was now sitting on the edge of the couch.

"Bend over and hold your head down so I can brush your hair out and give you a new ponytail." Jerry did as she bid.

"I'll do it. I'll suck cock if that's what she wants me to do," Jerry said quietly.

Lisa grinned a huge and mischievous grin that Jerry couldn't see from his position. It worked exactly as Sandy had said it would. He just needed a little kindness, a tender touch, a bonding moment, and then mention Sandy, that's all it took to lead Jerry by the nose. It was all Lisa could do not to laugh out loud, knowing that cathy wouldn't punish her for not fucking Jerry hard, but Jerry thought that was the deal, and Lisa was gonna find out just how hard she could fuck Jerry. He was so desperate for a friend, that he'd confide in anyone who showed even the slightest kindness to him, and then endure the most heinous acts to keep them. Lisa wondered how many others at the club would fuck this ugly little man before Sandy got bored with him, if she ever did.

Lisa finished up Jerry's ponytail, "You're done. Go let your Goddess know you're clean and ready for the next trial." Jerry trotted off to the upstairs where he found the women in the living room chatting. They fell silent when he entered the room. He paused for a moment and then dropped to his knees and assumed the position he had been taught.

"I'm clean and ready for my next trial, Goddess."

Sandy and Cathy both stood up without another word and just walked to the basement stairs. As they descended the stairs, he heard fingers snap, and Sandy say, "Come." Jerry hopped to his feet and followed them down the stairs, almost eager to show her he would do anything for her, even the most degrading and humiliating things if it pleased her, because if she was pleased, she would pleasure him.

"Are we good," Sandy asked Lisa.

"Oh yeah, he's ready," Lisa replied.

"Good. Rig him up and let's have a show." Sandy walked over to where Jerry was standing at the bottom of the stairs. He dropped to his knees as she approached him. She stopped just in front of him and placed her booted foot out expectantly. Jerry bent down and slathered the top of her boot in kisses. She smiled down at him, relishing her control, she didn't even have to give a command, perfect.

"I'm sure you and Lisa had a little talk while she cleaned you up, so I know you know the score. I expect this will be the hardest thing for you to do tonight. Most subs will suck a dildo with no problem, but draw the line at a real cock. Will you suck cock for me, Jerry?"

"Yes Goddess, I'll suck cock for you," he confessed.

"Convince me, little man. You know what I want you to say," she giggled.

He was confused for a moment before it dawned on him what she wanted. "Please let me suck cock for you, Goddess," he begged between kisses.

"Good boy," she said as she turned and walked away from him towards the table with the wine and charcuterie board, where she picked up her glass and went to the computer desk before rolling the desk chair over towards where Lisa was standing by the support pole in the middle of the room. "His mouth is yours, Lisa. Let's see what it can do," Sandy giggled as she took a seat in the chair, making herself comfortable for the upcoming show.

"Come here little fella," Lisa called to Jerry. She was still naked, but holding some rope and restraints in her hand. He had agreed to sucking her cock, why would she need to restrain him. He felt apprehensive but did as he was bid all the same.

"Lay down on your stomach with the pole between your legs, just above your ankles." He laid down in the position she had commanded him to assume. She then tied his ankles together, and then his calves, leaving the pole between his legs and between the two bindings. "Now get up on your hands and knees and push your ass into the pole," Lisa commanded. He did as she demanded and she tied a rope as high on his thighs as she could get it and around the pole, binding him to it in such a way that his legs were completely immobile. "Put your hands behind your back." As Jerry reached behind him as instructed, he realized that without his arms and hands, he could only hold his face off the floor by using his abdominal muscles, so he just bent over and laid his head on the floor as Lisa bound his hands behind his back.

Lisa stood up and went to the duffle bag by the sink and got a bottle of something, then to the couch to retrieve a cushion. When she returned, she roughly lifted Jerry's head off the floor by the ponytail and placed the cushion under him before kneeling down on it. Lisa was holding Jerry's head at crotch level, and for the first time, he really looked at her cock as it bobbed around directly in front of his face. It looked huge, with thick veins running its length, and a bulbous purple head at the end of the long hard shaft jutting from Lisa's shaved crotch.

Lisa popped open the lid to the bottle and squirted a liberal amount of its viscous contents onto her cock before setting the bottle aside. Jerry recognized the smell, it was the grape flavored lube that was on Cathy's ass when they came here. Why did she need lubricant for him to suck her cock?

Lisa grabbed her cock by the base and aimed it at Jerry's mouth. "Open up, little fella. You're gonna learn to swallow cock."

Swallow!? He thought he was just supposed to suck her dick, not swallow it. He usually gagged just brushing his tongue after his teeth. There's no way he was going to be able to take Lisa's cock down his throat. He looked up at her and Lisa looked back down at him with a smirk on her face. Any mercy or sympathy he had seen in her face earlier, was gone completely. It was while searching for some sign of mercy in Lisa's face that he heard the cane rip through the air before striking his left, outer thigh.

"OPEN! YOUR! FUCKING! MOUTH," Cathy yelled through gritted teeth, delivering a stroke of her cane with each word. Jerry hadn't seen her come up from behind him with her cane. He would now have 4 stripes on his upper thigh to match the multitude of stripes on Lisa's back. The intense pain caused his mouth to gape in a silent scream, letting Lisa push her cock into his mouth. Jerry tried to recoil, and that's when he realized he couldn't back up at all because of the way he was tied to the pole, and with his hands tied behind his back, he was completely at Lisa's mercy. Jerry looked back up at Lisa who just grinned down mischievously.

"All the way, little fella," Lisa goaded as she moved forward, pushing her cock deeper in Jerry's month. Lisa released Jerry's ponytail and grabbed his head firmly in both hands before moving forward again and pressing the head of her cock firmly against the back of Jerry's closed throat. Jerry tried to turn away or back up, but with the way he was tied to the pole, and Lisa holding his head, he couldn't move anywhere near enough to disgorge Lisa's swollen member from his mouth. He wiggled and writhed, but Lisa just held him firm and pushed harder. Jerry started to gag but held it back for fear Lisa's cock would go down his throat. The smell and taste of the lubricant just made him remember Cathy's enema game and that made him want to gag even harder.

"ALL! THE! WAY! DOWN," came the demands from Cathy, again delivering each word with a vicious stroke of her cane, this time on his other thigh. Cathy loved the way a slave writhed under her cane. The way they flinched when the instrument struck the skin of her victims. Cathy saw Lisa buck into Jerry and bury her cock balls deep in him as she delivered the lashes to Jerry's leg. She smiled, thinking about learning to deepthroat when she first got into porn. A friend had helped her out, he had one of those dicks that are still slightly soft when it's fully erect, so it's easy to learn to swallow it, the really rock hard ones hurt until you've learned how to really relax. Cathy knew Lisa had the rock hard kinda cock, and that meant Jerry was in absolute hell. Her smile grew to a grin as she walked around beside them to get a better view of Lisa grinding her crotch into Jerry's face with her cock down his throat. "Ready to quit, worm," she teased as she watched the show.

The sudden shock and intensity of the pain from Cathy's cane caused him to lose focus on his fight with the hard cock trying to force its way into his throat, and the instant his throat relaxed even slightly, the well lubricated dick began to slide in. That's when Jerry realized why Lisa had lubricated her dick, she knew she was going to force him to deep throat her.

Lisa saw her opportunity as she felt his throat relax slightly as her cock gained ground and she bucked forward, driving the entire length of her cock down his throat so violently that her crotch made a slapping sound when it hit his face.

Jerry's eyes watered profusely, more from the cock than the cane, but both were responsible for his tears. Lisa's cock was long, thick, and so hard it was like a rock wrapped in soft skin. It felt like it would rip his throat open, and his body started to involuntarily try to vomit. His stomach was empty from the previous experience, so he had nothing to expel, but his body convulsed repeatedly as it attempted to remove the cock from his throat.

"Well done, little man," Sandy cheered him on from her comfortable chair. Jerry could only catch glimpses of her from the corner of his eye, but he could see she had slumped down in the chair to spread her legs wide and she was playing with her clit. She was cheering him on and masturbating. He was pleasing her, and he knew that meant he would be rewarded later.

"AH, AH! FUCK! YEAH," Lisa yelled down at him, thrusting into his face with each word before just grinding her crotch on his face. "I love the way you squeeze my dick when you gag, but you're gonna have to learn to control that or this is gonna be really bad for you," she chuckled and left her cock resting in Jerry's throat for several more seconds, enjoying the sensations as he continued to convulse, before backing up just enough for her cock to leave his throat, but not his mouth. Jerry immediately began gasping for air, blowing snot and grape flavored lubricant out of his nose, choking and coughing on the mixture as strings of it created bridges between Jerry's face and Lisa's crotch.

"Look what a messy fuck hole you are," Cathy laughed. "If you can learn to relax your throat, it won't be so bad for you." She gave a huge grin. "I hope you don't figure it out. I like watching you squirm."

Lisa allowed Jerry to regain control of his breathing for about 15-20 seconds.

"Deep breath little fella, and relax that throat. We're gonna see how long you can hold your breath while I'm fucking you," she smiled down at him and started pushing forward. Jerry inhaled as deep as he could just before Lisa's cock reached the back of his throat. He tried to relax, but failed and gagged instead. With all the lubricant now in his mouth and throat, Lisa had no problem ramming her cock all the way down his throat the moment his throat relaxed from the convulsion of his gagging. "Nice, now relax and stop gagging so we can start fucking," Lisa ordered as she just ground on his face with her cock down his throat.

Jerry gagged a couple more times before gaining some semblance of control of his gag reflex. Sandy was right, this was harder than anything else he had done so far. Lisa's cock hurt, the gag reflex was a huge hurdle, and even though he seemed to be getting it, it was extremely difficult when Lisa started to move her cock back and forth in his throat. She didn't move back far enough for his face to lose contact with her crotch, instead she just rocked her hips back and as she held his forehead firmly against her stomach, barely moving her cock more than an inch either way as she gave him a slow grinding fuck. He involuntarily gagged a couple more times before really gaining control of the reflex.

Lisa buried her cock as deep as she could after he seemed to have control of his gagging, rocking her hips forward and leaning back with her upper body, so she could see Jerry's face. He had bulging, bloodshot eyes, bright red skin, and every bit of it was covered in a mixture of grape lubricant, snot, and saliva. She grinned down at him, enjoying the mess of his face, the pain of his experience, and most of all, the feel of his throat wrapped around her cock. Lisa wondered if he still felt some connection to her, she got that vibe from him earlier. The only vibe she was getting from Jerry now was that he needed to breathe, and she had no intention of allowing that until he looked like he was going to pass out. Staying on her right knee, Lisa lifted her left leg up and placed her foot on the ground next to Jerry, bracing herself and leaving most of her weight on her right knee. This left Jerry's right cheek pressed into her inner left thigh, so Lisa could now grab his ponytail with her left hand and hold the back of his head with her right, in this position, she was free to move her hips further and throw more weight into her thrusts. She steadied herself on her knee and started slam fucking his face as hard and fast as she could, never fully taking her cock out of his throat and keeping the pace until he started to go limp.