City of Bears: The Skin Between (Part 8)

“Are…are you sure this is work? I…I don’t, I mean, that felt good and all, but this isn’t like any work I’ve done before,” the Ruff said.

“You’re doing great, don’t stress out about new things, you’re perfect for this.”

“I…I don’t think this…I don’t know about this, I feel weird.”

“It’s alright, you’re doing great.”

“I…feel so hot.”

“That’s normal,” Darren said, and took the Ruff’s hand and pulled him closer, one hand slowly stroking his rubber cock, and seeing the Ruff’s breathing quicken. “Now, how about I show you how to use this new tool of yours? It can be a bit strange to begin with, but I think you’ll be a natural.”

“Do…do I use it on…on nails, or…” The Ruff stammered, “Or like, metal, or…or would you stop that?” he pushed Darren’s hand away, “I…It feels really good, but I can’t think…”

“You don’t need to think for this job–you just need to feel good,” Darren said, and gripped the shaft again, stroking it a bit faster, “If you feel good, and I feel good, then you’re doing good work.” The Ruff didn’t object again, and Darren took the chance to enjoy his body a bit, smelling and tasting his divine pits, feeling the soft fur all over his body, always stroking, getting the Ruff accustomed to pleasure–probably for the first time in it’s occasional existence.

The Ruff pulled away with a shudder after a moment, a flustered look on his face. “This isn’t right, this isn’t the right work, I…I don’t feel right,” he reached up to take the hat off, but Darren lunged forward, dragging his arms back down.

“No, you aren’t done with the job yet,” Darren said, “I’m…I’m the boss right now, you know. I’m the foreman. That means you have to do what I say, and you aren’t done with the work until I say so.”

The Ruff didn’t know what to do, but it…felt good to have a foreman, someone to listen to, someone who could direct him. He nodded. “A-Alright, if you…say so, but it doesn’t feel right.”

“Just trust me, it’ll feel amazing once you get used to it,” Darren said, and went back to slowly stroking the rubber cock, but it was clear that the Ruff wasn’t quite sure what to do with himself. His hands kept moving, first handing on his hips, and then just hanging at his sides, and on occasion he would moan or whimper with a bit of pleasure, but also wince, like something had unexpectedly hurt. Still, Darren didn’t really care–he was getting what he’d wanted, what he’d always fantasized about, and he wasn’t about to stop now. “Alright, now why don’t I show you how to use your new tool?”

The Ruff nodded, and let out the breath it had been holding. It…didn’t like how it felt, when the foreman stroked his tool. It felt…good on one hand, but it made his head hurt in a way that really worried him too, in a way he couldn’t quite explain. “Yeah, I think I like work better than…this. Just show me what you need me to do.”

Darren stripped, and the Ruff just looked at him, confused, and Darren climbed up onto the bed, his ass pointing towards the Ruff. “Alright, do you see the hole back there?”

The Ruff nodded.

“Alright–here’s your job. You’re going to put that tool in the hole, ok? Slow at first, just kind of ease it in there.”

The Ruff felt the nerves return, and he took a step back. “This…still doesn’t seem like work.”

“This is the job–I thought you Ruffs were supposed to be good with tools?”

“I am, but like, normal stuff. Hammers and nails, not…not this, I guess…”

“Well, I think you can do it–why don’t you at least give it a try?”

The Ruff supposed that just trying couldn’t really hurt. He stepped up, put the rubber tool against the hole, and pushed, gently, until the foreman told him to push a bit harder, and the dildo began to slide into his ass. The same pleasure was there, and the deeper the tool went, the better it felt, but the pain would come too–a few flinches at first, but when the dildo was about halfway in, something worse happened. To the Ruff, it was like someone had taken a mental mallet and slammed it against his skull. He cried out and pulled the tool free of the hole, stumbling around, trying to focus again, and Darren flipped over and looked at him, confused. Neither of them noticed the hairline crack that had appeared in back of the RuffHat, running from the back brim, all the way to the crown. “No,” the Ruff said, “No, that…I can’t do that, it hurts!”

“What the fuck are you talking about?” Darren said, and got off the bed, “It feels good, doesn’t it?”

“Yeah, but…but then it hurts, I don’t like this job, can’t I do something easier?”

“Here, let’s try it a different way,” Darren said, walked over, and grabbed hold of the Ruff’s hand, pulling him over to the bed. “Go ahead and lay down here, alright?” The Ruff tried to protest, but Darren just shoved him down onto the bed, climbed up on him, and straddled him, his ass over the rubber cock, and he lowered himself down onto it. “Yeah, that’s it,” Darren said, “We’ll turn you into a fucker one way or another.”

The Ruff didn’t know what to do, and so he just froze, feeling wave after wave of pleasure washing over him as Darren slid down onto the rubber cock, taking the entire thing into his ass, and then sliding back up. The pain was there still, but not as forceful as it had been, but it wasn’t going away. All the Ruff could do was hope Darren’s job would be over quickly. Darren began fucking himself on the tool faster, and the pleasure kept getting stronger. The Ruff…felt like he was coming apart at the seams, like he didn’t know how to even begin processing what it was experiencing. There were other flashes of pain, not as harsh, but strong enough to make him wince. Then, without warning, there was a splitting ache in his mind, and the Ruff came apart.

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