Ryan pulled a box out of his shopping bag from the Sex Shop. Jake felt tense wondering what new horror came from that shop.
Ryan opened the box and reached inside, pulling out a dildo. Jake hadn't ever seen one in person before, but he'd seen them online. This one was a little different though. It was shaped like a dick, with balls built in, and a suction cup on the bottom, but it was at most 4 inches long, and very thin, only a little bigger than Ryan's 11-year-old dick.
Ryan dropped it through the cage ceiling, and it fell in Jake's lap.
"What am I supposed to do with this, master?" asked Jake, feeling the firmness of the silicone.
"Put it up your butt." Ryan's face was lit up with his mischievous smile.
Jake acted on his orders, leaning backwards and spreading his legs to open up access to his hole. "What about lube, master?" Jake asked quickly, having no time to complain, and afraid of shoving something in his most private place.
"Why would you need lube?" asked Ryan, puzzled. Stupid kid, Jake thought, has no idea how anything works.
Jake found his hole with the tip of the dildo, and tried to press it inside. "It's to make it slippery so it'll slide in, master." The dildo slid into Jake's butt, gliding inward, and Jake let out an "Oh!"
Ryan was reading the box. "It says here it's 'self-lubricating.' So I guess you don't need it?"
Jake was driving the short dildo further in, until the fake balls were pressing into his crack. It did feel a lot easier than he expected. Ryan moved to crouch in front of the cage, and Jake, legs spread with a dildo in his butt, made eye contact with his little brother's inquisitive eyes.
"It feels weird, master," said Jake. "Can I take it out?"
"Nope, the sales guy said you have to fuck yourself with it," said Ryan, staring at the dildo penetrating his slave. "I guess that means, like, go in and out a bunch? Do it."
Jake obeyed, pulling the dildo out, and sliding it back in, and he found himself moaning as the dildo pressed along a sensitive spot inside his anus.
"You like it, don't you?" asked Ryan.
Jake tried to say No, but he couldn't lie to his master. Did it really feel that good? "Yes, master," Jake said, unable to hold back the embarrassing confession.
"Keep going, I wonder if it'll make you orgasm," said Ryan.
Jake pressed it in and out, over and over, stroking his insides and sending waves of pleasure out from his butt, making his little balls and dick tingle, forcing Jake to moan with each stroke. It felt really damn good!
The pleasure was building and building, until Jake let out a cry as the most powerful orgasm of his life made his body shudder.
Panting, he left the dildo in for a minute, hoping for one more wave of orgasm.
Ryan laughed. "That was awesome! You actually got an orgasm without touching yourself!"
Jake, feeling foolish in front of his younger sibling, pulled the dildo out of his ass. It was covered in white, slimy liquid, which looked and smelled like watery cum. Jake figured that was the self-lubrication of this dildo. He'd been afraid of brown stuff coming out, but it was just that white liquid. He wiped it clean on one of the napkins his mom had given him earlier.
Ryan opened the cage door. "You can go now, but wash the dildo up, I don't want it stinking up the place, then put it back in your cage. And no more clothes at home, I've decided, unless maybe if we have guests over."
Jake wanted to get out of there, so he crawled out of the cage, dildo in one hand, and crawled down to the bathroom to wash it off, praying his parents wouldn't see him with the sex toy. Once it was clean, he crawled back and put it in the cage.
Before he left, Ryan told him, "Come back at bedtime, you have to sleep in the cage from now on."
Jake crawled away, ready to chill and enjoy some videogames for a while, and put the memory of this humiliation out of his mind. As he was gaming though, he felt an emptiness inside him, waiting to be filled by that incredible dildo again. It made his cocklet hard again, but he couldn't do anything about it thanks to his brother's orders not to play with himself. Did that include the dildo?
When Jake was ready for bed, freshly showered, he crawled back into the cage, bringing a blanket and pillow with him, which wasn't easy while crawling. Ryan wasted no time closing the door, effectively locking Jake inside for the night.
In the darkness, when Ryan's slow breathing indicated he was asleep, Jake couldn't help himself; he grabbed the dildo, and started pumping it in and out of sphincter, trying to stifle his gasps and moans to keep Ryan from waking up.
Jake didn't know it, but Ryan was only pretending to sleep, his own dick hard as he heard the dildo squelching in and out of his older brother. Ryan knew what the dildo would do to his brother, having been told by the salesman. Ryan wasn't sure about it, but the salesman had been very insistent that Ryan give it a try.
In the morning, woken up by Ryan's alarm, Jake found the dildo laying next to his pillow. Surprisingly, it was totally clean. Apparently it self-cleaned too, given time. Jake's insides felt a little sore from the penetration. He didn't care though, he wanted to fuck himself with it again. Ryan turned his alarm off though and got up, wearing only his Minecraft undies, and opened the cage door. Jake stashed the dildo under his blanket so Ryan wouldn't see it.
Jake found that he couldn't get dressed until he was at the front door and ready to leave, and was tugging on his socks right as Ryan came over to demand another blowjob. Jake wondered as he sucked his brother's cock, if this was going to be his life now, sucking cock and fucking himself with a dildo.
After another long day at school, Jake was relieved it was Friday and he wouldn't have to show his bare genitals off in the showers for a couple days. Too bad that would leave him with Ryan for the weekend.
He stepped in the front door of the house right behind Ryan, and immediately dropped to the floor and started undressing. His parents were right there on the couch (they got home from work before they got home from school), and Jake had to strip in front of them. They glanced his way but didn't say anything, and Jake quickly balled up his clothes and crawled with them up to his room, dumping them in his hamper.
Jake did his homework for a while, something that let him sit in a chair, and when he was finished, he dropped back to the floor since he had no reason to be in a chair.
Jake considered what else he could do, and realized he wanted to use that dildo again. He thought about sneaking it out of the cage, but Ryan had told him to leave it there. Jake was so hard, he really wanted to feel one of those anal orgasms again. But Jake wasn't about to go back to the cage just to fuck himself with the dildo...right?