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When Jim woke up he found that he was still chained to the pole, with the mask and gag still attached to his face. The only difference were two bowls of food and water placed a short distance away, and a cot placed nearby with several ratty blankets laid out haphazardly on top of it.
Jim tried to move, but the chains around his wrists and ankles restricted his movement. He tried to call out for help, but his voice was muffled by the mask and gag. Unexpectedly, a figure approached Jim from behind causing him to jump. It was Garth, dressed in his usual mechanic's uniform. He had a bemused look on his face, and in his hand he held a vibrating plug. Garth kneeled down in front of Jim, his eyes fixated on his restrained form.
"Well, well, well," Garth said, his voice a low growl. "You'd better not be thinking about escaping monkey boy."
He inserted the pre-lubed plug into Jim's ass, turning it on with a low hum. "'In fact you'd better not be thinking anything at all"
After saying that he pressed a button on the control pad next to him causing a strong electric jolt to surges through Jim's body. Jim screamed in pain, and almost involuntarily it came out as an ape-like cry. As Jim writhed and thrashed against the chains, he could feel the vibration of the plug deep inside him, adding to the torment.
"I'm going to lower your chains now, and I want you to take care of yourself and get some rest. Garth said, his voice cold and commanding.
He lowered the chains around Jim's wrists, allowing him to drop his arms to your sides. Jim slumped to the ground, exhausted and sore, deeply feeling the activities from earlier in the day. As he tried to catch his breath, Jim looked up to see another figure approaching him. He was one of the workers from the flophouse, a burly man with tattoos covering his arms. He approached Jim with a smirk on his face, a bottle of whiskey in one hand and a beer in the other.
"Goodnight monkey." Garth said. " And Tim, restrain yourself."
With that, Garth sauntered away from the pole and towards the flophouse, but Jim could have sworn that Garth winked at him before he told Tim to take it easy.
Jim tried to process what just happened, but the vibrating plug was still sending shockwaves through his body, making it difficult to think straight. Jim let out a guttural moan as his cock began to harden from the stimulation. Tim chuckled as he sat down beside Jim on the cot, his warm body radiating against his in the cold evening air.
Tim took a swig from his whiskey bottle and extended an arm out as if to offer Jim a swig. Jim tried to speak to tell him that he didn't want any, but he was interrupted by a sharp cuff to the side of his head that sent him reeling.
"Monkeys don't talk, idiot." Tim bellowed.
He then held the bottle up to Jim's face and tipped it into his open mouth. As Jim felt it burn down his throat and drip down his chest, Tim leaned in and whispers into his ear.
"And monkeys definitely don't say no to actual men."
Tim then grabbed Jim's cock and started to stroke it, his rough fingers sending a shiver down his spine. With the vibrations from the plug intensifying, Jim felt himself getting closer and closer to climax. Unconsciously he started softly hooting to himself.
"Not yet monkey." Tim admonished him. "We can have some fun after your dinner."
Tim quickly stood up and led Jim over to the food and water bowls that had been left a few feet away. Tim made Jim kneel down in front of him and the bowls. Looking down Jim noticed that the food bowl was full of some kind of dry dog food. Tim pulled Jim's chin upwards and made him watch as he chugged the entire bottle of beer he brought with him, the alcohol dripping down his chin. Tim finally looked down at the monkey boy and said
"I don't know how they expected you to eat dry pellets without being able to close your mouth." He laughs. "I can probably help you with that though."
He tousled Jim's hair with one hand while fiddling with his belt buckle using the other. Jim tried to pull away, but Tim was holding him steadily in place with his giant meaty hand. Eventually, Tim managed to unzip his pants letting Jim catch a glimpse of his massive flaccid cock. As he fished it out JIm could see that it was at least 7 inches long, soft, and at least a few inches in diameter. It also flopped forward with the smell of sweat and stale piss.
Without warning Tim started urinating directly into the dry food in the bowl in front of him. The stream was forceful enough that drops from it splashed back onto Jim's naked body.
"There monkey, that should soften your food up for you. Nice and easy to swallow." Tim said as he shook out the last few drops.
Jim couldn't help but feel disgusted by the sight and smell, but he also felt an animalistic need take over his body. Hunger. Tim stepped back and allowed Jim to approach the now wet dog food and almost instantly he pounced on it ravenously.
You shoveled the acrid and wet chunks into his mouth as quickly as possible, pushing them down his throat with his tongue. Some part of him knew he should feel shame but a stronger one just couldn't stop himself. As he finished the bowl, he looked up to see Tim standing over him with his cock still hanging out of his pants.
"You did good, monkey." Tim said with a grin. "Now it's time to thank Tim for his help."
Jim looked up at him and saw his cock twitch as he waited expectantly. Immediately he hooted in response and sat up straight, taking Tim's large cock head into his mouth.
As he started to suck, Tim moaned with pleasure. Tim grabbed Jim's head and pulled it upwards, slowly sinking his face deeper into Tim's hardening cock. The vibrations from the plug intensified, and Jim couldn't help but feel his body respond in kind. Continuing to suck, Tim's cock got harder and harder in Jim's mouth, soon getting too thick to fit through the ring gag that was locked into his mouth.
"Well, fuck. Eh monkey? I guess we'll have to do this a different way." Tim chuckled.
Tim pulled his cock out of Jim's mouth and walked over to the control pad. With a push of some buttons the winch started to retract, pulling Jim backwards towards the pole. Jim felt the metal chains around his wrists tighten as the pulley system did its job. He heard the creaking of the metal and the grinding of the gears as his arms were pulled upwards and eventually his whole body was pulled into a standing position and then hoisted into the air about a foot off the ground.
As Jim hung there, suspended in mid-air, he felt a sense of vulnerability and exposure. The plug inside him is still vibrating and sending waves of pleasure through your body. Jim could see Tim watching him with a mixture of curiosity and lust in his eyes.
"So, what do you think, monkey?" He asked. "Personally I think I want you a little more lively for this next part."
With a few more button presses on the keypad Jim convulsed, bringing his legs up to his chest as a series of e-stimulation began on his body once more. The sensations were overwhelming, and Jim began to hoot and grunt like an ape as his muscles flexed repeatedly.
"I see you're still enjoying your toy," Tim said with a smirk. "But I think it's time for something different." He walked over to the flexing ape and started pulling the vibrating plug out of its hole.
Looking down, Jim saw Tim's fully erect 11" cock looking nearly as thick as a pop can. Before he could mull over that particular implication, the plug popped out of his hole leaving him feeling empty. Silently Jim hoped to himself that he was gaped enough to fit Tim's monster cock inside him.
Tim then stood up off the ground to his full 6'8" height and peeled off his shirt revealing a massive bear-like chest. He lifted the monkey boy's legs and pressed his massive body into him.
"Now, let's see how you like the real thing," Tim said as he lined his cock up with the monkey's hole.
The tip of Tim's massive member touches Jim's entrance, and he could feel it pressing against his stretched and abused hole. Jim smears his cock around the monkey's crack, allowing his precum to coat it before slowly pressing his cock against the sphincter.
Jim could feel the pressure building as Tim tried to push his cock inside, but it was too much. The ape man let out a panicked hoot as the pain hit it, causing tears to stream down its face.
"Easy, easy," Tim said as he pulled back slightly.
Another series of electric shocks hit Jim causing him to clench his hole and flex his biceps. After the e-stim passed Tim pressed again against the monkey's hole, finally breaking through in its more relaxed state.
Jim could feel every inch of the massive bear's throbbing cock as it filled him up, stretching him beyond what he thought was possible. He let out a soft and prolonged moan as gravity slowly pulled him downwards onto Tim's cock. Eventually the pressure stopped just at his prostate as the chains tightened and he couldn't fall any further.
"Perfect, monkey." Tim whispers as he reaches over towards the keypad.
Tim pressed a start button and dropped the pad to the side as the winch began slowly moving once again. The chains slowly lowered Jim downward almost imperceptibly, causing him to take fractions of an inch of Tim's cock deeper into him every second.
The feeling of fullness was overwhelming, and Jim began to pant and grunt like a wild animal, losing grip on reality as endorphins flooded his system, the e-stim still causing him to clench his hole around the massive cock as he continued to descend. Tim held the ape man tightly and it could smell his manly musk and deodorant as he let inch after inch of him slowly slide into his monkey hole.
Delirious, the monkey thought that it must be halfway over, quietly hooting to itself as it got fuller and fuller.
"Good monkey," Tim whispered as he gently kissed the gorilla's neck. "You're about four inches in now."
It huffed and grunted in response, feeling the chains letting it down further and further. As the beast sank further down on Tim's cock, it could feel him restraining himself from thrusting upwards. Instead, he slowly moved his hips back and forth, allowing the monkey boy to adjust to his size. It could feel him grip it tighter every time its hole clenched on his cock from the e-stim. The monkey boy `ooked' with apprehension knowing that it was taking everything Tim had to not wreck its hole.
"Seven inches now, monkey." Tim breathed.
It's unreal how deeply the monkey could feel Tim inside it now, it didn't know anything could feel this full. As it sank further down, it couldn't help but wonder what it would look like when Tim pulled out. The monkey boy could see the muscles in Tim's chest flexing as he held its legs while his sweat dripped down the monkey's skin.
A few inches later, the ape man could feel Tim press against it even harder, and it realized Tim was about to thrust upwards. It braced itself for the pain, but before it could react, Tim thrusted upwards sending shockwaves of pain through its body as his massive cock slammed into its bowels.
The monkey bottomed out, feeling all 11 inches of Tim's girthy cock deep inside its body. It could feel his balls pressed against its ass, and it could hear him moaning in pleasure. Feeling Tim's throbbing cock deep inside its monkey hole, it couldn't help but wonder what would come next.
Tim reached over and stopped the winch before pressing some other buttons on the keypad and pressing enter once again.
"I like edging boy," Tim said. "So enjoy the ride."
The winch started pulling the ape man upward again at a rate of about an inch a second. It could feel Tim's cock sliding out of it, and for a moment, it worried it might pull something out with it. But Tim brought the monkey closer, holding it in place and keeping it steady as his cock slid out of its ass.
After being raised off his cock about five inches, the winch suddenly releases allowing the muscular ape man to quickly slide back down onto Tim's cock. As it descended, it could feel him fill you again. It felt right once his cock was back all the way inside. The e-stim was still shocking the monkey's body, and it felt itself clenching around Tim's massive cock and flexing as it slid down. The ape beast couldn't help but let out a loud hoot as it took him all in again.
A second after falling back down, the winch started to raise the hooting monkey once again. This time, the ascent was slower, giving it time to savor the feeling of Tim's cock leaving its insides. The monkey wanted to beg him not to leave its hole feeling empty like this, but all it could do was grunt, moan, and drool as the e-stim made it clench and flex once again.
As it got closer to the top, it could feel him press against its prostate, and it let out a cry of pain and pleasure.
"Eight inches out," Tim whispers in its ear. "Only eight more to go."
The winch released and the ape slammed back down to the base of Tim's cock. It felt every inch as it sucked him back inside, and it can't help but let out a cry of pleasure.
It continued like this for God knows how long, edging Tim and the ape man by slowly raising it up and slamming it back down on the massive man's cock. The monkey started to become one with this sisyphean task, wondering if it would ever know what it's like to be fully removed from Tim's fat cock.
The monkey's thick ass plunged back down for what felt like the 500th time, this time falling the entire 11 inches as it had nearly been pulled all the way off Tim's dick. As it landed, it could feel the e-stim intensifying, making its hole clench and spasm around Tim's cock. It could feel Tim throbbing inside it as he grunted and held it close. Clearly Tim was getting close to cumming.
As the monkey was fully impaled on him, Tim reached over to the controls and lowered it to the ground, letting it fall onto its neck and back as he stood over it, still fully engaged with its insides. The ape felt Tim's massive weight on top of it, his sweaty body pressing against it. Tim pulled his thick and veiny monster out of the ape and began to fuck its well prepared hole.
The monkey could feel Tim's thick shaft sliding in and out of it, plunging it to the limit. It tried to move, but it couldn't seem to get any leverage with his weight on you. All it could do is lie there and take it, hearing Tim pant and feeling his heavy balls slap against its entrance again and again.
The monkey hooted in rhythm like a good monkey boy should, feeling its own orgasm build as the massive man made it his. The ape felt Tim's grip on its hips tighten as he pounded into it harder and harder, his thrusts becoming erratic and forceful. It could feel its monkey cock getting closer to the edge, and it let out one last hoot before cumming hard, its juices spilling out onto its thighs and mask.
Tim kept going though, getting more and more desperate. The ape could feel his thrusts grow faster and harder, his body shuddering as he approached his own climax. Suddenly, it felt a flood of cum enter its body as Tim let out a bellow like a warcry. He continued fucking the ape man like a freight train as he pumped more and more jizz into its gaping hole.
To the monkey, it doesn't seem like Tim stops cumming for another two or three minutes as the earlier edging seems to have greatly magnified his orgasm. Finally, he collapses on top of the beast, his sweaty body covering it completely. Tim lay there for a few moments, trying to catch his breath before he turned his head to look at you. Jim could see the mix of satisfaction and dominance in his eyes as he smirks at you. "That was fun, monkey."
Tim pulled his shrinking cock out of Jim's ass, leaving him feeling incredibly empty, before pressing it next to your face.
"Now clean me off." Tim ordered.
Jim obeyed, licking Tim's cock clean with his tongue before letting it fall from his mouth. Tim stood up and stretched, his muscles bulging as he did so.
"Now, have a good night, monkey." Tim said, picking Jim up and placing him into the nearby cot.
Tim gave Jim a reassuring pat on the stomach before wandering off back towards the flophouse, shirtless and with his cock still hanging out the front of his jeans. Jim could feel the cum leaking out of him and running down his thighs, pooling on the mattress below. As he lay there, staring at the stars, he wondered what tomorrow might bring.