Chapter 2
Within a week he had the PO box ready. The “gifts” from his secret admirer were delivered to it soon after. Everything came in a moderately sized box. Not very large or heavy, but he could tell it was packed full.
This was a new kind of torture for Joel, now having to drive home with the box before he could open it. Who knows what kind of fucked up shit could be waiting for him in that package? He didn’t need some random passerby catching a glimpse of whatever was inside. The wait was painful, but still a better alternative to giving some weird sketchy guy on the Internet his home address.
Whether or not the wait was worth it would depend on what was in the box.
Joel grabbed a boxcutter and tore into the tape sealing the box the second he walked in the door. Yeah, he knew he probably shouldn’t do that since the box said not to, but did anyone ever pay attention to that?
Plastic. There was a lot of plastic. Bags, bubble wrap, packing peanuts… So much was tightly packed in the box that he couldn’t even see what was in the bags until he opened them. Annoying. While it was nice that the stuff was new and completely untouched by whatever freak of nature sent all this, it sucked to have to individually unwrap each one. Whatever was in there, his admirer made damn sure it would be getting to its destination safely.
This better be good.
Joel pulled out a sealed bag that looked like… clothes? He wasn’t sure, but considering his admirer asked for all of his clothing sizes, that was probably it. Once he ripped the bag open, he took it out to unfold it for a better look. It turned out to be a very short crop top, baby blue in color with a large heart-shaped hole at the chest. It didn’t take a genius to figure out that this would normally be worn by someone with tits, so he found it to be an odd choice. Oddly cute, even to Joel, but it made him worry about the rest of the items. This couldn’t be the only piece of clothing in the box.
It wasn’t. The next bag had a matching blue-and-white pleated miniskirt, the same shade of light blue as the top. They wanted him to wear this? Christ. What had he gotten himself into? He wasn’t sure what was worse: some weirdo asking him to dress up like this, or the fact that he liked the idea. It got even better — or worse — when he discovered the set of striped knee-high stockings and shiny satin panties in the same colors. Did all of this come as a set, or did they have to search for all the matching pieces? Either way, it had to cost a fucking fortune.
There was something else hidden in the packing peanuts, a hard piece of plastic that his hand bumped into a few times while digging around for the clothes. What he found was an almost intimidating dildo with ribbed sides, sporting an unnatural shade of hot pink, along with a new and unopened bottle of lube that looked like it was one of those fancy and expensive brands.
Holy shit, how loaded is this guy?
He dug around the box, emptying the packing peanuts and bubble wrap just to be sure there was nothing else stashed away in that fucking clown car of depravity.
A few hundred-dollar bills were stuffed into the bottom of the box.
Where they managed to get that kind of money he didn’t want to know, and he didn’t plan to ask.
To his relief, the only thing left was a note.
“Message me if anything doesn’t fit or isn’t to your liking. Only the best for my prince <3
Don’t forget to give us your best ‘oh, daddy!’ while you’re at it.
Excited to see you enjoying yourself with these. Xoxo”
An embarrassing request, but for that kind of money he’d do anything short of showing his face on camera.
Joel admired himself in the bathroom mirror. The thought that he might be into crossdressing never crossed his mind, but now he was eager to show off how he looked in his new pretty blue clothes that hugged all of his features just right. He might just find himself wearing them for his own enjoyment, even when he wasn’t about to perform for his loving fans. Speaking of… well, there was work to do.
Finding himself a good spot to set up his camcorder, he fixed the ribbed dildo to the tiled floor with the small suction cup at the base. His admirer didn’t give him any instructions on how he should do this, and normally that would bother him, but this time he had something special in mind.
From the viewers' perspective, the prep would be skipped; they’d already seen him force himself open with a dildo for his first video, so why not let them skip to the main event this time? Though maybe someone would get off to watching him finger himself… he made a mental note of that for later. Somewhere along the way, he got over not wanting to use his fingers; sometimes that was just what he was in the mood for. Even now as he fingered himself open and lubed up his hole, he was tempted to skip everything and get himself off then and there, but that would only ruin the fun he had in store for his precious fans.
He wouldn’t want to let them down. So he stopped once he was good and ready, drenched the dildo in lube, and turned the camera on with his clean hand.
What his viewers got in the opening shot was Joel on his knees, his legs straddled over either side of the toy. He ran his hands up his body, back down his sides, then down the silky and smooth stockings on his legs. When he brought his hands back up, they moved to ghost over the front of his skirt. He pulled teasingly at the edge of it, allowing the tiniest glimpse of the panties underneath. Just knowing there were going to be people watching him touch himself had him hard and aching. His back arched as his hand settled on his covered dick, groping himself through the soft fabric. The need for more was unbearable; he wanted to tease the audience for a while, but he was just as impatient.
Joel reached underneath his skirt to pull the crotch band of the panties out of the way so he could seat himself down on the toy. It was bigger than what he was used to and much different in shape, but he took it without much of a struggle. The feeling of the ridged edges rubbing along his insides sent shudders up his spine and tore a husky groan from his throat. One long drag of it against the walls of his ass and he was already hooked and craving more.
He leaned his body backward, searching for just the right angle. One hand reached out behind him to keep himself balanced. “Ngh… D… Daddy,” he whimpered, bunching up the front of his skirt in his other hand and lifting it enough to finally give the audience a clear view of the bulge hiding under his panties. A noticeable wet spot was slowly growing with each and every movement Joel made. “I’m already wet for it… oh, God…”
His chest started to heave with rapid and excited breaths as he started to bounce his hips up and down, repeatedly impaling himself on the rubbery length and practically squealing with delight from the size and shape of it. Joel bit his lip to try to stifle some of the noises, but it was all too much; the viewers were going to hear every whimper and whine whether he wanted them to or not.
That didn’t matter. He wanted them to hear it anyway.
If only they could see his face, too. If only they could see how “hard” he was “trying” to suppress those pathetic sounds. They’d never get to see that. All they’d see and hear was how much of a slut he was for even a fake cock. One that he wished were real, pretending it belonged to his “Daddy” who bought him all these sweet gifts. Wouldn’t it be nice to repay him properly? Even if he was essentially getting paid to make this video.
More precum streamed out of him, soaking the confines of his dick and threatening to drip out of the fabric and onto his legs and the floor. “Look… Look how good it feels, Daddy…”
He couldn’t take much more of those ridged edges grinding against his prostate. Each slam of his hips made him shiver and sent him hurtling faster toward his climax, but he let it happen knowing that the people watching from the other side of the screen would be waiting to see him soil those once-clean panties. Should he feel bad? Guilty? They were brand new, but he was wrecking them on their first use.
“Haah, fuck… Daddy, I’m sorry, I’m so sorry, I’m gonna— ngh… Gonna ruin the new panties you bought me, I’m sorry, oh fuck— ”
The words tumbled out of his mouth like water from a faucet. Joel didn’t have any control over them anymore. He just hoped he wouldn’t say anything that would embarrass him enough to have to edit it out (or worse, redo the video). If that were even possible at this point.
“So close, I’m so close, gonna cum…!”
Joel came with a strangled cry, slamming himself down until his ass hit the base of the toy and grinding the ridges hard against his prostate. The wet spot at the crotch of his panties was at its limit and couldn’t hold anymore, and the sudden rush of fluids forced its way out from behind the fabric, dripping down his legs and staining the blue stripes of the stockings. Joel breathed out a sigh of relief when the rush of adrenaline finally blew over and slid off the dildo. His tired body slumped to the floor behind it and the puddle of cum, lube, and sweat pooled around its base.
“Hope you were watching, Daddy. ”
It didn’t take very long this time for a few comments to pop up. Generally, they’d come in later; it seemed to take a few hours for new videos to attract viewers, but a few people who must have been stalking his account were on that video like flies to honey.
>489446012: I knew he couldn’t be straight hehe listen to him moan for daddy
>273810021: can I suck on those panties
>590001273: wish I were daddy :(
>002182033: omfg someone bought those clothes for him… where can I find someone like that? That’s my dream life right there I’m SO jealous
Good. People should be jealous of him. Why wouldn’t they be? Getting paid to masturbate and not even having to show his face was the best thing that’s ever happened to him. Not to mention…
>ph0tofan4tical: Looking good, baby. Don’t feel bad about those panties, I’d say you put them to good use. I’d love to take a good long whiff of them.
There they were, back again. Seeing that username on the screen was enough to make Joel squeeze his legs together from the rush of blood that shot down into his legs and groin. Nobody else’s praise mattered more than theirs.
>hauntedrestless: I wouldn’t mind. Want me to send them back to you?
>ph0tofan4tical: You’re so funny and cute. Money well spent.
>002182033: It was you?! Holy shit what a legend
>hauntedrestless: Well if you’re ever in the mood again for something special, you know where to find me :)
>ph0tofan4tical: How sweet. Can’t wait to see what you do next in the meantime.
What he does next? Joel hadn’t thought about that. What was he supposed to do next without his admirer’s endless wisdom? He started scrolling through some adult shop websites for some ideas. There were so many options. Too many. If only he didn’t have to choose on his own…
Or maybe he didn’t have to choose on his own. What was the harm in just asking?
>hauntedrestless: Would you be willing to do me another favor? <3
>ph0tofan4tical: Let me guess. Something caught your fancy?
>hauntedrestless: I guess you could say that :) But I would like to run it by you first to see if you’d be interested.
>ph0tofan4tical: Whatever my little prince wants, he can have :) As long as you let me see you use them…
>hauntedrestless: I plan on it <3 <3
>ph0tofan4tical: Then show me what’s got your cute little pecker hard, and I’ll let you live out your dreams.
Joel whined and rubbed his thighs together. Being doted on by some faceless stranger was driving him wild.
He sent him the links to his items of choice and pulled his pants down to take care of his painful erection.
Joel had his camera ready to go the moment the new toys were delivered.
That drive home from the post office sucked. He was pawing at his growing boner at every red light and stop sign. He hoped nobody saw him…
He needed a very particular spot for what he planned to do — somewhere right next to a wall that still had adequate lighting. A corner of his bedroom suited his needs.
It was a lot to ask for (kind of expensive) sex toys, but he knew his “Daddy” would be pleased to see him enjoying them. He dressed back up in his frilly new clothes and got to work setting everything up. Everything was still in its packaging and needed to be opened and cleaned.
The first was yet another dildo that was really damn big, even when compared to the others he had. But this one wouldn’t be going in his ass, at least not today. He fixed it to the wall, at a height where his head would be. And where he planned for his head to be was just out of view, though the audience would still be able to see him from the neck down in the position he was going to be in. It took a few tries, going back and forth between his chosen spot and behind the camera to make sure the tripod was at the correct height. But after enough tries, he got it right where he wanted it.
The second toy was a tiny vibrator that would be strapped to his dick. For this video he would be doing without the panties, leaving his dick and the vibrator on full display. He strapped the vibrator to himself and set the remote down within reach. The final toy was another dildo, smaller than the one on the wall, but realistic in appearance and hollow in the center. The idea was that it would be filled with fake cum, which could be forced out by squeezing the balls.
An elaborate setup. If he was being honest, he didn’t originally intend to try out all the toys at once. But he had such a good idea for a video, so how could he resist? Even if it meant fewer videos, quality over quantity, right?
With the camera on, Joel took his place sitting down in the corner and spread out his legs. He balled up the front of his skirt in his fist and lifted it up so he could so off everything underneath to the audience. He reached down for the vibrator’s remote to press a button for one of the lower settings, gasping when it loudly whirred to life. The need to close his legs and rub his thighs together was overwhelming, but he needed to keep them open for his dear fans. Why would he want to ruin their view?
Joel let his body lean weakly into the corner. One of his sprawled legs raised and bent at the knee to spread himself open wider, and for a better view of his hole. The audience wouldn’t know what for until Joel reached for something offscreen and brought the realistic dildo into view. The lubed-up toy was pushed, inch by inch, into his exposed hole. Joel let out a soft hiss from behind clenched teeth as it sunk deeper and deeper until only the balls could be seen pressed flush against his skin. A light squeeze of his hand forced a few drops of its fluids into him. It made his own cock twitch in response, wanting nothing but to be filled with the fake dick’s cum so he could imagine his Daddy giving it to him.
It was a treat he would have to wait for. That was okay. He could pretend he was begging Daddy to hurry up and let him have it.
Joel’s heart was pounding. He was salivating. This was all he needed in life.
“It’s so fucking big, Daddy… So much bigger than me,” he mewled and started to thrust the toy in rough, jerky motions. The sounds that came out of his mouth were supposed to be words, but they weren’t any words he, or anyone else, knew; he babbled a garbled mess of sounds that thought they were words.
Then came the hard part — the dildo on the wall. Joel normally did things on the first take, but this part had to be practiced, and on his smaller dildo first. He took the massive length into his mouth, bobbing his head back and forth for the first few inches. Most of what was happening was out of view, but there was enough motion that the viewers could easily piece together what was going on up there, especially when he started making loud sounds with his mouth as he sucked. Muffled grunts added to the effect. There was no way that anyone wouldn’t be able to tell what he was doing, even before he got to the “best” part. Occasionally he’d stop bobbing just to take it a little deeper, only to gag and cough around it. All part of the act; at this point, he could handle this just fine. Joel moaned loudly around it, tears pricking at the corners of his eyes from what was going on down below.
Now was time for the “best” part. Suddenly he took the entire length to the hilt until it was deep in his throat. What the viewers got to see was the toy bulging out against his throat, growing and receding with each bob of his head. Joel slowed his motions to accentuate the mass moving in his throat all while speeding up the motion of his hand to fuck himself faster. Fevered and high-pitched grunts forced their way out even with the object in the way, along with whimpering and sniffling and crying that anyone could interpret as him begging for more.
Or asking for it to stop, if they were into that. Joel wasn’t one to judge. Whatever gets their rocks off, if it meant getting more views and fans doting on him, loving him, jerking off to him…
His left hand moved away from his skirt for only a moment to press a button on the vibrator’s remote, and suddenly those grunts turned into frenzied screams while he leaked precum all over himself. It warned his audience that his end was approaching fast, his chest heaving faster and faster until he came hard with tears streaming down his face and hips bucking up with each string of cum that dirtied his skirt. Mid-orgasm he remembered to squeeze hard on the balls of the dildo in his ass while shoving it in deep, filling him up with all the fake cum inside.
When he was finally good and spent, he removed the toys stuffing each of his holes, and shut off the vibrator. But Joel wasn’t done having fun with his fans; the camera still had a view of his hole, and he took advantage of the “cum” that would be leaking out of it. His fingers pressed into the plush skin at either side of his hole and gently stretched it open, letting the milky white liquid drip out onto the floor.
Joel leaned back into the corner, his entire body going slack, idly rubbing himself through his skirt. “Thanks for… mmph… watching. Tune in next time, and let me know if you enjoyed it in the comments…”
His breath was raspy and hoarse, sore from taking such a large toy into his throat. Almost on their own, his hips were slowly lifting to meet the touch of his hand.
“Might take me a bit to get this uploaded, I think I need to go another round.”
