"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.