"What are you thinking, Whisper?" Tangle asked as Whisper hopped off the bed. She went over to the closet and looked inside. Much to Tails' surprise, there were a few outfits hanging on the rack. He gave it a minute of thought, however, and it all made sense. No doubt the company had a few spare costumes and outfits, and it was sensible to just store all that in the perfectly serviceable storage space on-site.

"Pretty sure we have... ah, here's one!" Whisper pulled out a dress from the rack. It was a schoolgirl uniform, except the shirt was more like a crop top.

"Here, try this on." she said, tossing it to Tails.

"What? But this is a girl's outfit!" Tails protested. The ensemble also came with a pair of white thigh high socks.

"Come on, just try it on." Whisper said. "Don't worry; all the clothes are cleaned before they're put back up on the rack."

"No, I'm with Whisper on this. Try it on; you might look very cute in it." Tangle said.

"But I-"

"Oh come on, what's to be embarrassed about?" Tangle asked. "Whisper and I are in porn, we're seeing each other naked right now, and I've seen you go balls deep inside a camgirl's bladder."

"Just put the damn outfit on; I don't suggest this for just any man." Whisper said.

"Alright, fine, if you insist." Tails said. He first slipped on the stockings, which were long enough that they came up to his upper thighs. In a way they almost felt like tights. He didn't understand why, but they also felt strangely comfortable to wear. And... appropriate?

Next went on the skirt and then the shirt. The skirt was short enough that his dick almost peaked out from underneath the hem. The shirt tied together at the bottom, and after he did so, Tails could tell that it was meant for someone with a sizable chest to fill out. He wondered what it would feel like to have breasts to fill out the shirt.

"Huh, not bad, actually." Whisper said, taking a step back to get a good look at him. "Yours are surprisingly narrow. Not as much as a girl's, of course, but, like... that's pretty good for a boy."

"With a bit of makeup, you could easily pass as a girl." Tangle added. "That being said, our makeup artist isn't in today, so-"

"Hey hey! That's a little much!" Tails protested. "I mean, even this is already too much!"

"You should learn to lighten up." Whisper said. Much to his and Tangle's surprise, she pressed him up against the wall. "You're fine enough with letting an audience watch you fuck, and this is the line you won't cross?"

Her hand moved down between his legs and she grabbed at his dick. It was still wet from Tangle's pussy juices and his own sperm. It was still swollen with blood from the erection and had yet to be redirected. Of course, once she grabbed him, he started to get hard again. Even if he was still a young boy at the very beginning of adolescence and possibly puberty, to bounce back so quickly was pretty impressive. The men and transwomen in porn had to usually take the blue pill or some sort of injection to stay hard even after cumming.

Whisper considered her next actions. She was very hard on her stance as a lesbian, Tails passed very well in the schoolgirl outfit, and it stirred something within her. Something she didn't normally feel when looking at a guy. And if he was going to be in the room interrupting their private time together, she might as well have a little bit of fun with him. What the hell, couldn't hurt, right?

"Count your lucky stars today, kid." Whisper said, moving back over to the bed and presenting her rear to him. "You get the very rare priviledge of being allowed to fuck me."

"H-huh?!" Tails exclaimed.

"You heard me! I don't let just any man fuck me."

"Or any man, period." Tangle said. "You should hurry up and stick it in her, Tails, before she changes her mind."

Tails stepped forward and, holding his dick in his hand, pushed it into Whisper's pussy. She wasn't tight, at least at first; the instant his dick poked past her labia, she tensed up, and her muscles gripped him like a vice.

"Shit, I kind of forgot how this feels." she muttered.

"Never thought I'd see the day." Tangle said. "I should get a camera."

"Don't, Tangle." Whisper said. "Just in case I start to have regrets later."

Once Tails bottomed out inside of her, he felt her labia clench the base of his dick. Her interior was strangely welcoming despite her hostility towards him. Her vaginal muscles seemed intent on keeping him inside.

"Guh! Please, go slow at first." Whisper said after Tails began a thrusting motion. "It's been a while."

Tails had to restrain himself a surprising amount to not go completely feral on top of Whisper. However, he still pressed her top half down onto the mattress, where she kept herself up by her elbows. He reached around with both hands and cupped her breasts in his hands. They were larger than Tangle's, and a little bit softer but not by much. It was a lot of fun feeling up breasts. He wondered what Cream's breasts felt like.

He wondered what his own would feel like if he somehow grew a set.

Tangle left the room briefly; neither of them noticed until she returned a few minutes later, holding something in her hand.

"What do you have there, Tangle?" Whisper asked, tilting her head to the side.

"You make quite the sexy bitch, Tails." Tangle said. "I just can't resist; I want to have a go at that cute little ass of yours!"

Tails heard ass and his ears perked up, but he didn't stop thrusting into Whisper. He looked over at Tangle to see her holding a strangely shaped dildo. The base of it had a weird curve, almost like a hook.

"Hope you don't mind if I rejoin." she said, pushing the hook end into her pussy. Some more of Tails' spunk leaked out of her and coated the toy. She trembled as it fit over her labia as snugly as a glove.

"Heh, lucky for you, I've been training my ass for the past week!" Tails said. "Go ahead and give it all you got!"

"Oh, bad move to say to a girl." Tangle said. She applied some lube to the dildo and positioned herself behind Tails. She probed at his asshole with two fingers to spread some of the lube around his tight sphincter muscle. His twin tails poked out from under the hem of the skirt and prevented it from laying flat against his butt. He was surprisingly soft and malleable down there; his butthole didn't provide much resistance to getting probed. He must have been practicing every night since the stream to remain that loose; otherwise he would have tightened back up by now.

There was a lot of evidence to suggest this young boy was a slut in the making, and Tangle was all too eager to shove him down that rabbit hole.

"Open wide, baby!" Tangle said as she pressed up against Tails from behind. She prodded the dildo against his ass cheeks. "Mommy's coming in, whether you're ready or not!"

"Heh, you're not old enough to be a mo-HUH-HUAAAAHH!" Tails' bemusement turned to shock as he felt the tip of the dildo probe against his asshole. He had been training his butt for the past week to take in dicks, but until now it was under his own control and authority. To have it pushed in outside of his control was very different. On top of that, the fake dick was a bit larger than what he was practicing with, and even though it was an easy insertion, all things considered, it still stretched his butthole out a lot further than he was accustomed to at this point.

The most amazing part of all of it, though, was how good it felt, and how it seemed to make his dick even harder. There was some part of him, between his butt and his dick, that suddenly glowed in his mind's eye like a beacon. The dildo rubbed against it briefly, which was indescribably intense, almost like a mini-orgasm in and of itself.

"Oohh, fuck, it really does feel like it's a part of me." Tangle gasped as her hips bumped up against Tails' butt. "I can feel your asshole clenching down around the dick as I push it into you."

"It's... it's bigger than I am used to." Tails said between heavy breaths.

"Just wait. When I'm done with you, you'll be so loose, you'll be able to take even larger dicks!"

"Ggh! Shit! He just got bigger inside me!" Whisper hissed. Hearing that "threat" did indeed make his dick throb powerfully. Whisper's legs trembled, and she tensed up. With him now sandwiched between both girls, he could no longer thrust into Whisper.

Not that that was much of an obstacle. Tangle pulled out of Tails, then slammed her hips right back in. This forced Tails' hips forward into Whisper, the head of his dick slamming into her cervix. Tangle pulled out again, and Tails slid back with her.

"Heh heh! I'm fucking you with a boy toy, Whisper!" Tangle said as she picked up the pace. Her vagina tingled from the part of the feeldoe inside her pushing against her G-spot every time she pulled out. It constantly felt like it was threatening to pop out of her, but the tightness of her insides plus the size of the bulb made that almost impossible.

"Oh geez, this is... wow, this is amazing!" Whisper panted. Tails continued to squeeze her breasts. She seemed to be getting more used to it as they went on, as she was no longer tensing up at his touch. She angled her hips in a weird manner, and she lifted one leg up and leaned back into Tails.

"Come on, come on. Almost there" she said, adjusting her position again. "Keep thrusting right there! It's going to - I'm gonna - OHHH!"

Her vaginal muscles suddenly contracted, attempting to milk Tails of his sperm. It was very nearly enough to make him cum again, but it was difficult to tell when his prostate was being stimulated and making him feel like he was constantly cumming. Whisper pulled out of his grip and climbed up on the bed. She rolled around, spreading her legs wide open, and then slid back down underneath him.

"Alright, let's try it in this position, stud muffin!" she growled in a husky voice. She grabbed Tails by his arms and pulled him closer so he was on top of her. Tangle slammed the full length back into Tails, and he in turn was pushed forward and buried himself up to the hilt inside Whisper. She tensed up around him; her body was still having micro contractions from her orgasm, but when his dick brushed past her G-spot, she clamped up again around him.

Tangle pushed Tails all the way down on top of Whisper so their chests pressed together. Their snouts collided, and Tangle kept Tails' head down so he couldn't pull away.

"Here! Give your girlfriend a kiss!" Tangle said. She put one foot up on the bed to get a better angle thrusting into Tails' ass.

"Hey, that's going a little too far! I'm still a lesbi-mmphh!" Whisper was silenced by Tails giving her a full on kiss on the lips. He was fully inside of her, grinding his dick into her most sensitive areas. Every time Tangle thrust into him, he was pushed deeper into Whisper. Tangle had her hands on his lower back, keeping him pinned down. Whisper struggled to break free at first, but every time Tails was pushed forward, his dick grinding into her G-spot, her resistance softened. When her second orgasm hit, she became fully compliant. Their hands found each other, and Tails held them in his like a lover, just as he did with Tangle. Maybe there was something to her claims about his romantic personality.

"Fuck it, just cum inside me!" she said, breaking away from the kiss with Tails. "Do whatever you want. Just keep making me cum! Keep... fuck, keep grinding it into my sweet spot!"

Tails wasn't sure if that was directed at him or Tangle. Not like he could have even done anything about it, and he really wanted to. Making girls cum started to become an obsession for him. It wasn't enough to just have sex with them; Tails wanted them to writhe in absolute bliss under his treatment.

"Gh! Shuh-shit!" Whisper hissed as her vaginal muscles contracted around Tails again. Tangle's assault on his prostate kept making his dick twitch violently, brushing against her G-spot over and over again. It had been so long since she had a dick inside her, real or otherwise; she forgot what it was like, and how pleasant it could actually be. If only she could find a transwoman to fuck. Then she'd have everything she'd ever need between her and Tangle.

Tails' prostate burned more brightly in his mind's eye. Even as he was still recovering through his refractory period, his vision glazed over as he was suddenly wracked by a powerful anal orgasm. His dick was throbbing violently within Whisper's folds. Even as he blew another huge wad into her, his dick was somehow on the verge of climaxing, too. The ceaseless stimulation to his prostate made the rest of his body numb, but the pleasure in his dick only continued to intensify.

Tangle picked up the pace, thrusting with greater intensity as she neared her orgasm. She found pegging this young boy strangely invigorating and empowering, especially as it forced him to cum in her own partner and girlfriend. From her perspective, Tails wasn't a person. He was just an object; an extension of the Feeldoe she wore, and she was using him to fuck her girlfriend.

This realization sparked something within her, and she doubled over him as she was wracked with a powerful orgasm. The endorphins were so strong that her vision narrowed, the corners turning into dancing lights amid darkness. The burst of energy she had displayed vanished suddenly, and she fell over on top of Tails like a puppet whose strings had just been cut.

Whisper pushed Tails and Tangle off of her and rolled away. She could feel the gooey sperm oozing out of her pussy. It was disgusting, and yet at the same time, something about it was exciting. She didn't normally like men or the idea of getting fucked by one, much less having one cum inside her, but she figured she could make an exception just this once.

She moved Tangle's leg and grabbed at the Feeldoe. She pulled it out of her and inserted it into herself.

"I hope you're not spent yet, because now I want a turn!" Whisper growled.

They continued for several more sessions, at which point they were finally spent. Tails gathered his belongings and stumbled out the door, and Whisper and Tangle were cuddling together in their afterglow. Tails' seed oozed out of them in a prodigious volume. It was a hell of a lot more than he ever imagined he could make in a week, much less a few hours. His butt was also pleasantly sore, and after Tangle was done railing him (and after Whisper had a turn), there was a slight limp to his walk.

He was still wearing the schoolgirl outfit, which was starting to slack off of his body in the aftermath of the rough play. He considered leaving it in the room, but he liked how it felt to wear. He stopped in the middle of the hallway to readjust it to appear slightly more appropriate, then made his way back downstairs.

His foot didn't even touch the bottom stair when he heard an argument coming from a room two doors down in a hallway just off the foyer. He looked over; the door was open, and there were two voices.

"That's bullshit!" a male voice said. "I'm old enough for porn! I've been alive longer than your entire family line!"

"I understand that, but documentation aside, you are... well, you look like a child." a female voice said. "Overland law dictates that all actresses must not only be at least eighteen years old, but also have legal documentation and absolutely must look of age as well."

"How the fuck do you even be the judge of that?!"

"I don't get to decide what the laws are. If I did, we wouldn't even be having this conversation. If you want my advice off the record? There are some streaming sites you might be able to make content on, but you'll either be doing it alone or with some very open-minded partners. Partners who aren't the face of a business."

A young boy, or at least, what looked like a young boy of about eight years old, stormed out of the room. He was a little red chihuahua with a large white tuft of fur around his neck. He was also completely naked, but despite his seeming age, he was sporting a pretty large dick. It dangled almost halfway down to his legs, and more to the point, the entire length was wet and oozing cum out of the tip. His fur looked slightly dishevelled. Another person, a woman, a teal-quilled hedgehog with purple tips, stumbled up to and leaned against the door frame. She was also naked, with an enormous volume of cum dripping out of her. She was a much larger mess than the chihuahua; her quills were askew in every direction, and her makeup was running down her face.

"Well I hope you find something." she called after him. "I'll see you and your big fucking dick later."

"Such... hypocrites." the boy complained to Tails after the woman went back into the office. "They'll fuck a child in private - or at least someone who looks like one - but they're scared shitless of the age of consent laws."

"Well I mean, yeah. It's the law, and people get squidgy about minors and sex and porn." Tails said. "Even people who can pass as kids in the right kind of light."

"It's not even Mobian law!" he protested. "It's Overlander law! And when was the last time you saw an Overlander?!"

Overlanders, or humans, as they once called themselves, were precursors to all the Mobian and Echidna civilizations on Mobius. They decimated their own population multiple times over the centuries, between the gene bombs, the war with the Mobians, and then the war with Robotnik, and finally a mass exodus into space. Robotnik himself was an Overlander - the last of his kind on the planet, and nobody missed him when he was finally defeated.

That being said, there was a brief period of time in history when both parties co-exised peacefully, and the Overlanders instated laws regarding when someone was legally allowed to have sex. Eventually those laws were believed to be based on psychology or physiology when they were, in fact, not. Tails understood this, but the general population didn't, and they were conditioned to be mortified at the prospect of minors having sex.

"It sucks, but what can you do?" Tails asked, shrugging his shoulders.

"Change the fucking laws!"

"Easier said than done. Is it really true what you said, though? Are you really, like... ancient?"

"Yeah! I've been around for... eons, I think." the boy said. "I just look like this! I... don't remember exactly when I was born. The years start to get a bit blurry, especially when they change the calendars and civilizations collapse."

"What made you want to do porn?" Tails asked.

"Because it's fun! Sex is like the most universally fun thing anyone has ever made! Movies, art, music; that all disappears with society, eventually. Sex, though? That's a forever thing. Man, you could not imagine some of the orgies I've been to! Several hundred of us, men, women, even children, all having sex in the woods, for weeks on end! That's how the Carathians would court each other for relationships. You'd end up with a lot of really interesting family dynamics because of it."

"You seem pretty cool." Tails said, offering a hand to the boy. "The name's Tails. What's yours?"

"Chip." They shook hands. "I'm always on the hunt for sex. If you're interested, we can keep in touch. I'll let you know when I find something good."

"It's a deal. And you can swing by my place if you ever just wanna have fun." Tails said the words before he even knew they left his mouth. He realized he was not making eye contact with Chip, but was rather staring at his cock the entire time. It was quite the beautiful dick. The foreskin was pulled back, revealing the rosy red head. The meatus was slightly agape, and he was still dripping cum. It was a good thing the bottom floor was mostly tile, but the rugs were going to need washing if he walked over them.

Tails left the mansion continuing to think about that dick, and how it felt to get fucked in the ass by Tangle and Whisper. He thought about sucking it, licking that gaping meatus with his tongue and lapping up all of his cum as it gouted all over his face in huge, thick ropes.

The thought was enough to make him erect again, and since he wasn't wearing any underwear, it made his erection pop right up, lifting the skirt with it. He didn't feel embarrassed, though; he passed by another pedestrian who noticed the heat he was packing and did a double take. Tails winked at him and turned around to flip the skirt and flash his butt. He trotted away like a feral fawn down the street and around the corner. It didn't occur to him until a few minutes later that he was acting like such a cocktease.

Much like Cream, actually.

It also didn't occur to him that he left Vanilla back at the Mega-32 mansion until she sent him a message asking where he went. He wheeled back around and returned to the mansion. As exhilarating as it was to be out dressed like this, it was still a very long walk back to his home.