---This time the guy asked if he could send Aston a dildo to really put his rear end to the test. Aston knew what he wanted to say even before he had the chance to say it, but laying there on the same bed he’d fingered himself on for the first time, the feline’s digits typed out, “Yes please!” before hitting send.---

It hadn’t been too hard of a choice for Aston to make. The positive reaction from the guy to his pictures and videos was addictive, and with his first round under his belt, Aston was feeling pretty confident that he could handle whatever was thrown at him. Fingers were a long way from some of the things he’d seen people fit online, and even some of the things he’d seen cubs his age take on the site, but Aston was already planning on practicing a bit beforehand.

The toy, and the agreed upon $100 this time, were due to arrive in a week or two, which left the feline plenty of time to get himself ready. First up were a few more fingering pictures and videos, this time for public viewing. He didn’t think his new Sugar Daddy would be upset if he uploaded some new ones, as long as he kept his first one private just for him. So, picking a good day after school, the feline got himself cleaned out and went back at it.

He was expecting to be a bit sore as his slick fingers traced around his hole, with two of them soon pushing through his young pucker. But, given a few days to recover in between sessions, the feline felt pretty good, and got comfortable with the sensation soon enough. He worked up to three fingers pretty quick, and even tested a forth on his paw to spread himself open. The strain was a bit too much for him at that point, and he had to pull back and relax for a moment, giving up the fight for the time being.

Laying sideways on his bed, with his paw and fur thick with lube, he began to look around his room, seeing if he could find anything to use instead. It was hard to find something that was the right size and shape, and that he didn’t mind making a mess of, but his eyes scanned around the room regardless, feeling his curious mind take hold. Three of his fingers slid back inside his hole to keep full and stretched, rubbing up against his prostate and keeping his cock excited as he did. With a few pumps in and out, the boy snapped some more pictures while he let his mind wander.

After a bit of searching, his gaze zoomed in on a hairbrush that was sitting on his desk, noticing that the handle was a good cylindrical shape - not too big or long, and something he could definitely wash off.  Slipping his fingers out of his rear end and sliding off his bed, he walked over to pick it up, giving it a curious rub down the handle. He’d never thought of his brush quite like this before, but the feline’s mind was entering into some new territory. He figured he might as well give it a shot, and as he hopped back onto his bed and lifted a leg up, it wasn’t all too hard to get that handle lined up and pushed in.

It certainly felt different than his fingers as he let out a surprised little squeal at the new sensation. His fingers were soft and flexible, moldable to how much pressure he wanted to give himself. The handle was solid and steady, having no give, but still fitting into his young butt with a good push all the way down to the beginning of the brush head. He was gentle at first with a few curious pushes in and out, taking a few pictures of the process while trying to make sure his phone had a good view. Yet the feline pushed on, picking up the pace of his thrusts, before his hole finally needed a break. He slid the brush out and got a few shots of his slick and open pucker, before laying on his back and starting to fap for a big finish once again.

That experience opened his eyes to a few more interesting things he could use around the house. Anything with a thicker handle was fair game, and for his next session the feline tried out a broom handle, a lacrosse stick he had stashed in the garage, as well as taking an idea from the internet and raiding the vegetable drawer in the fridge to try a carrot. He was met with mixed success, and everything felt a bit odd and weird, but he couldn’t deny it was getting easier each time he pushed something into himself. Those weird feelings faded faster and left him with a craving to fill himself up with whatever he had, almost looking forward to that stretching burn as he knew he was making progress each time it made his tail twitch. Although, his fingers were still his favorite by far, being so easy to manipulate and hit just where he wanted them to. More pictures, more videos, and many more comments flooded in, causing the feline to watch his page like a hawk, never wanting to miss a single naughty comment or thumbs up on something he’d done.

By the time that package showed up, surprising him outside his front door one day after school, the feline knew he was ready. He’d never seen a real dildo before, and the guy promised the feline that it’d be a good one, not some cheap knockoff. He was quite excited as he raced up to his room and used a claw to carefully slice open the box. He first saw the envelope laying on top of some crumpled packing paper with his money inside, but tossed that across his bed to get at the big purple knotted shaft that lay beneath.

It was… huge. That was his first thought as the feline tugged it free of the paper and grabbed a hold of it, yanking the hefty toy up into his grasp. He soon brought his other paw up to caress it as well, with the weight of the toy being much more than he thought it would be. It was also soft and squishy, wiggling in his grasp as he gave it a few shakes, and the feline couldn’t help squeezing and kneading his digits into the soft silicone as he held onto the base. It wasn’t a strictly canine shape, instead being more werewolf in design. It had a human-like head and gradually tapered knot, ending in a small base at the bottom.

The feline thought he was prepared, but that toy was far bigger than anything he’d practiced with. Aston felt intimidated by its size, but at the same time he saw a challenge in front of him. It was a challenge that the feline was all too eager to take. He let go of the toy and watched it flop down onto his bed before he raced off to get ready, both eager and nervous at the same time.

He felt his own cock grow pretty hard at the thought of taking that toy, and by the time he jumped onto his bed, his cock tip ground down against the sheets as he crawled over to reach for that toy once more. He kept the purple and squishy object close as he turned over and laid on his back, positioning the toy on his chest. He reached for his phone and took a few rough pictures to send to his online friend, even comparing it with his own cock to see the giant difference between them. He felt really naughty at what he saw before him, in a way that the feline hadn’t felt since he’d taken those first pictures, and he had to admit that he loved that sensation. He layed back for a moment just to take it all in, before giving a few strokes to his cock, and then reaching over to his nightstand to grab the bottle of lube he’d placed there.

Of course he was going to start with his own fingers. He wasn’t crazy enough to try and sit on that toy right away. He worked up to three in a quick flash, and he gave his hole a few pulls apart to feel that straining and stretching burn once more. It sent another shiver up his spine as he pushed a bit harder this time, knowing that he needed to work extra for the challenge he had in store. But, with a few deep breaths, and a moment to let the sting subside as he pulled his fingers out, he figured he was as ready as he was going to be.

He let some lube splash onto the soft and spongy purple flesh as the feline held it in his paw, watching a few drips land on his bedsheets below, although not caring much in the moment. He held the toy by the knot, using his lube-slicked paw at first, only to feel it jump out of his grasp and flop down onto the bed, adding to the stains on his sheets.  He struggled to pick it up again and position that floppy shaft to line up with his tail opening as he lay on his side, but after a few wiggles and a little patience, Aston soon had that tip grinding up against his taint. Each grind spread the slick lube through his fur and over his warm hole, although it wasn’t doing much to stretch him open quite yet. With one last deep breath, he applied more pressure and began to push that toy against his hole, gritting his teeth as the strain grew at a rapid pace.

It felt like a solid wall was pushing up against him with the way that thick head ground against his pucker. It wasn’t as pointed as his fingers or a few of the handles were. It was girthy and solid, growing really thick really quick around that human-like head. It left Aston struggling for traction as he felt the pressure grow, only for that shaft to slip past his hole and slide against either his balls or tail base each time. The knot made a good pawhold for sure, but even still it slipped out of his grasp another time or two as he tried to grind and push, making the feline yell out with a frustrated grunt after yet another fumble. 

He wasn’t sure it’d even fit at the moment as he felt it flop down onto the bed again, only to roll into the little depression he made and lay against his ass cheek. He took a second to calm himself, taking a few deep breaths, before he decided to get up and clean off his paws. Perhaps that would help. He grabbed a few paper towels and wiped down that knot and base to get rid of the lube there too, before re-applying some to the tip. He wiped off his paw once more, and reached down to that knot, now getting a good solid grip. With that toy firmly in his grasp, he jumped back onto his side and lifted up a leg, aiming that floppy shaft back toward his hole once more, determined to get it inside.

Aston could tell he was getting close as that cock head sat neatly against his pucker. He tried to relax, pushing it in nice and slow now, gradually increasing the pressure, but not quite feeling himself opening up. Then, all of a sudden, his resistance gave out, sending that head and a few inches of shaft racing into his rear, and causing the feline to arch his back and hiss out from the sudden strain.  His paw jerked at first, trying to pull that dildo back with a simple reflex, but as the feline’s mind caught up to what happened, he held himself steady. A few more deep breaths and gentle hisses shot through his lips, but the feline didn’t dare to move, feeling that straining burn tingle all around his hole, and not wanting to make it any worse.

It was big, it was intense, but the feline wasn’t someone who gave up at the first sign of trouble. He was a trooper, and he held that dildo inside of him, not daring to move or twitch until that sting began to die down. It took a little time, and a few careful movements back and forth to help work out a little of the roughest feelings, but before long the feline’s rear end needed a break. He gave a quick yank and pulled that toy out of him with a wet pop and a heavy gasp, feeling his mind spin as his hole still ached quite a bit, but also felt rather empty at the same time. It was a strange sensation to take in at first, with that tingle still dancing all around. He could feel his pucker clenching a bit then loosening back up, almost on its own, as if recovering from the abuse it’d just gotten. He curiously sent his free paw down to investigate with a gentle rub, actually enjoying that dull ache being massaged away with each grind, keeping it up for a good while as soft moans filled the air.

There was a lot of strain, but there was also a lot of release when that toy left him, and neither sensation could work entirely without the other. As Aston caught his breath, he already knew he needed another hit. He settled back down onto the bed and lifted up that heavy dildo yet again. He moved the tip to press at his pucker, and added a little more pressure to grind it against his opening. He could feel that sting building again, but, at the same time, he knew there’d be a joyful release after he endured the strain. That urged him on to push just a bit more, feeling his sore hole open up once again to swallow the first few inches of that shaft.

The pop inside wasn’t quite as sudden as it was before, and Aston knew what to expect this time so he was better prepared, but it still caused his leg to kick and twitch, as well as a strong gasp to shoot out of his open lips. The burn and strain were about the same as that first shove, but with one more pull out and push back in, the strong sensations began to die down a bit, turning into a manageable and consistent ache instead.

In and out that toy popped through his pucker, still causing Aston’s breath to catch in his throat each time it did, but before long he settled into a steady pace. Not only did he practice pulling that cock completely out and pushing it back in, but he began to push a bit deeper as well, feeling that soft material squish and try to bend along with him. It was tough going as Aston felt something in his guts stopping him, like a solid wall each time he tried to get in deeper. He wanted to keep pushing, figuring that he could find a way to take it, but he knew that he’d already pushed himself pretty far today, and he didn’t want to overdo it. He stuck to what was working, sliding the first third of that cock back and forth through his pucker, until his rear end finally had enough. As the strain began to turn to pain once more, he let it slip out for the last time, a relieved gasp filling the room along with his heavy breaths.

That final emptying was quite intense as he dropped the toy onto the bed and flopped onto his back, stroking himself off while his pucker tingled and burned between his cheeks.  He sent down his paw to dig a few fingers into his rear end, and gasped in surprise at just how easy they all fit, even pushing a good bit of his fourth one inside before the strain started to build once again. He kept that strain low, teasing his prostate and stroking his cock, until he came with a few heavy shots onto his chest. It was only in the afterglow, as his body shook and quivered on the sheets, that he realized something. He hadn’t taken any pictures or videos since he’d started…

The next session was going to have to wait as Aston was sore for a day or two after that, feeling his hole reminding him of what he’d done each time he sat or turned wrong. Yet, he had to admit, it was a nice thing to be reminded of. He didn’t so much remember the pain and the strain, but that empty tingle and his heavy release instead, not to mention the naughty realization that he’d fucked himself with a big dildo. Those sensations were certainly worth working for again. Once his body had gotten used to taking that cock, it did feel really good inside of him. Soft, squishy, and molding to his insides better than even his fingers could. It filled him up just right, although it did push him hard. He knew that the next time would be better, and that he’d have something good to show for it. He was determined to make sure of that.

He did send the first few comparison pictures he’d taken to the guy though, just to let him know the toy had arrived and he’d tried it. He told him that he wanted to practice to really make a good video before showing him anything, which wasn’t all too far from the truth. He seemed okay with that, requesting just a few more teasing shots as he waited, with Aston giving him those when he got home from school. He debated trying to go at it again, but with a soft grind of that toy’s tip against his pucker for those teasing shots, he figured it was best to wait one more day. The next day however, he had no excuse. He was still a tiny bit sore, but Aston couldn’t wait forever. Neither could the guy wanting to see what he could do.
 
So, after getting home from school and getting ready, the feline easily worked up to three fingers, then pushed a fourth one in just a bit, before reaching over for that toy once more. He lubed it up like he’d done before, careful to keep that knot dry as he was pretty sure he wasn’t taking that quite yet. He cleaned off his paw and got a good hold of that knot as he laid on his side, lifted up a leg, and began to prod that head against his ass once again.

There was some more strain, and a few more slides across his ass crack as that head resisted going inside, but with a slower and steadier application of pressure this time, the feline felt his hole give way and soon let that tip creep, then slurp into his rear end with another sudden pop. He was ready though, muffling his hiss and groan, and only giving himself a few deep breaths to get used to the strain, before beginning to slide it in and out of his hole, working down as much as he could until he hit that wall of depth yet again.

“Take picture,” Aston said, with a decent bit of strain in his voice, but his phone recognized what he was wanted and made the capture noise, getting a few slightly out of focus and position shots of him pushing that toy inside him. With Aston’s ass begging for a break after a few pushes in and out, he released the toy from his grasp and reached over to check the photos, only to be a little disappointed in them.  He tried to think of a better idea since propping the phone up against his blanket didn’t work so well, and he knew he needed a more solid place to hold it properly, especially for something as intense as this. He figured he could set his phone on the nightstand and angle it toward the bed. But, it would be hard to lay on his side and still get a good shot of his body like that, so he needed a new position.

He figured he could try riding the toy as the feline got everything set up, and then added a little lube to that tip once again, only to use one paw to hold it down against his sheets near the edge of his bed. He wiggled his way up onto his feet and then positioned his rear end over that cock tip, squatting down until that tip tucked back up underneath his tail. He held it there for a moment, testing to see if he could pull his paw away and still keep that cock standing upright. With a little pressure from his tail hole back down against it, dimpling the base into the softness of his bed, he found that he could.  He got himself ready, taking a big breath, and then pushed down, feeling that tip pop through him again with a strong shake running through his body.

Back down he sank onto that slick shaft, feeling it hit just as deep, if not a little deeper in this position. He took a second to let his body adjust once more, before shaking off any strain on his face and trying his best to give the camera a naughty grin, only to squeak out, “Take picture.” He flashed the camera a peace sign with his fingers and heard the capture noise, which made him smile a bit more as another naughty sensation shot through him. He repeated that a few times at different depth levels, sliding up and down the cock with a few careful bounces, and trying to get a good series of shots to make sure at least some came out good.

It was a workout on his legs as the feline felt them shaking a bit, but the more he got into it the faster he could go, feeling that cock tip punching into his guts time and time again. It kind of hurt, but then again it was kind of fun and intense at the same time, making his mind race and his own cock bounce along with each slide up and down. Of course a few more pictures were taken, with even a little video thrown into the mix, and by the end Aston was starting to feel more comfortable than ever.  He sent down one of his paws to grab his balls and lift them out of the way of another shot, only to lift his other paw up to his mouth and give a finger a sexy little lick, before shouting “Take picture.” He was hoping to immortalize the most naughty and teasing scene he could think of, doing his best to look as big of a slut as some of the other guys he’d seen online. He took a few more pictures, trying to maximize the sexiness and teasing as best as he could, but he knew that he couldn’t last much longer, either with his legs, his tail hole, or his cock. So, after the last few pictures snapped off, he wrapped his paw around his cock and stroked nice and hard. He rose up along that dildo until that cock tip ground against his prostate, while his hips gently rocked back and forth against the toy, giving him more and more pressure. It didn’t take long at all for the feline’s orgasm to build up, and with a few heavy gasps, a set of large streaks shot nearly all the way across his room, flying off the bed and onto his floor in a creamy series of jets.

Aston didn’t remember to yell at his camera to take a video, but that was the least of his worries at this point. He fell back and flopped onto the bed, feeling that toy slip out of his clenching pucker with a wet pop, as he shivered and felt his mind melt into mush from the powerful orgasm. Only after a few minutes of catching his breath and feeling his pucker and insides tingle did he finally stir once more, reaching for his phone to look over what he’d collected. There was a lot of good stuff that made his semi-hard cock stir again, but after an orgasm like that it was just a passing set of throbs. The feline was too sore to really go at it again. Still, after cleaning everything up, and editing the best pictures a bit to make them all that much better, he began the process of uploading them to the site, unable to wait to hear his friend’s reaction.

That reaction came quicker than last time, and quicker than the feline was expecting. After he’d eaten dinner with his parents, and just before heading off to bed, the cat gave his phone one final check to see that message and a ton of comments waiting for him. He opened it as fast as his fingers could press into his phone screen, reading over the paragraphs of praise for the kitten and what he was able to do. 

A heavy rush of accomplishment and pride swelled inside of him as the feline read those words multiple times through. Even after he’d turned his lights out, and he was supposed to have gone to bed, he pulled the message back up to go over it again. Those words got his cock hard again, and he gave himself a quick stroke under the sheets, finishing up in a few tissues he had to scurry across his room to get. Still, there was one thing in the message that left him feeling a bit uneasy, and it left him hesitating to respond.

“So, if I flew out there to meet you, would you want to meet up? Maybe hang a little bit? Maybe do even more?”