For the first time since his hobby, Tails felt genuine fear. In the past few weeks, Tails had been going out dressed as a woman. He didn't wear anything sexy, he didn't have the courage for that. Just simple, girly clothes. And he'd go out to places he hoped his friends would never venture. He avoided restaurants, bars, and stores his friends frequented, and so far, he had yet to be caught.
At least that's what the greater portion of his brain wanted. But really, he was addicted to the excitement of getting found out; of one day crossing somebody he knew and they recognized him. What they would think of him. Who they would tell . . . and honestly, secretly, in the deepest part of his soul, what they would do to him. Would they hate him? Or . . . would they be aroused and want him to do something to keep their mouths shut?
The very thought made his penis twitch in its chastity. A drop of precum seeped out of the cage's hole.
At the moment, he was walking down the streets that he and his friends rarely ever visited. He wore a sundress and sandals. He also had a floral bow in his ear and a purse in his hand. Everywhere he went, people pleasantly gawked at him, none the wiser that he was a perverted crossdresser. They only saw a cute, innocent girl.
Underneath the sundress, he wore nothing, not a bra, not panties, he was completely free, save for the chastity cage. A single malicious wind could show the world what a naughty fox he was.
Inside of his ass was an egg vibrator, its controller in his purse. It hummed softly near his prostate. The vibrations kept him on edge and very happy.
Tails was running a simple errand, grocery shopping. Just something he needed for his next upload, which he decided to be a nude photo. His first nude photo, sort of, if his viewers didn't mind whip cream and strawberries covering his private parts.
He got to the store, bought what he wanted, and was going to head home, when he was suddenly stopped by two strangers. A leopard man and a wolf man. Save for the three of them, the streets were eerily empty.
"Hey, cutie," the leopard man said, and casually walked beside Tails. "What's a foxy lady like you doing in a place like this?"
The wolf man, who continued to block Tails' path, leaned against the building and said, "Can't leave a girl like you alone out here. Who knows who you might meet at this hour."
"I-I'm fine, thank you," Tails said, and tried to escape, only to have the leopard man grab his arm.
"Don't be shy, cutie," he said. "Come on, we'll show you a shortcut."
"B-But you—" They didn't even know where Tails was going.
"Yeah, here's a good path over here," the wolf man added, and just like that, they both led him into an alley. "Nice and quiet. Nobody's going to find you here."
Tails should've ran and screamed for help. He wasn't sure if it was the fear of being caught in the act, or the fear of getting hurt by the two men that kept him from doing so. Or worst, what he hated to admit, was that he simply didn't want to escape.
These two men, despite their creepy demeanor, were . . . admittedly, handsome and strapping. Muscular and fit, and Tails was willing to bet half of his patents that they would never dream of caging their cocks.
He eyed their crotches for a moment and saw the outlines of their half hard dicks. They were bigger than him, no question, bigger than he could ever hope to be. Tails realized what was happening.
It was the forums.
Some of the ones he's been reading through recently were very hardcore. Their writers were masochistic and horny. Always talking about betas and alphas. About worshiping cocks larger than their own. About hoping to one day be assaulted by a stranger.
Tails shook his head. He secretly shamed those people. He never told them, of course, because he didn't want to kink shame. But real life was different from what we imagined. This situation should've been scary, and it was, but . . . Tails couldn't help but think about the constant stream coming out of his urethra as the two men dragged him deeper into the alley until they were out of view of the streets.
His arousal won over his fear.
The two men—two real men—that towered over him sat him on a dumpster, so now they were eye level. The wolf man grabbed his purse and tossed it to the side while the leopard man started molesting him.
This was the first time someone had touched him like that. The first time such strong hands held him so firmly. The first time someone looked at him so hungrily. He thought about all the people that saw his photos. How many of them would kill to be in such a situation would him.
"Yeah," the leopard man said. "I like my girls quiet and obedient."
"She clearly wants it," the wolf man added, and slipped his hand under Tails' ass and groped. Tails let out a squeak. "She's not even wearing panties. This bitch is just asking for it."
"I . . . I—" The leopard man put his finger on Tail's lips to shush him.
"Let it happen," he commanded, and kissed Tails, forcing his tongue into his mouth. His hands slipped beneath Tails' sundressed and his thumbs rubbed against his nipples.
As for the wolf man, he spread Tail's legs and started rubbing his thigh. Slowly, he moved up, almost touching Tail's chastity cage, and instead rubbed his stomach. His hand continued to fiercely grope Tail's ass. He quickly realized that they were both teasing him, and he was loving it.
The leopard man pulled away, crafting a trail of saliva between their lips. He aimed for the straps of his sundress and pulled it down, revealing Tails' bare, flat chest to the world. The leopard man grinned and went in for it, sucking on his nipple without a care in the world, while the wolf man bit his neck.
Tails couldn't hold it in anymore and let out a loud moan. The wolf man pulled Tails' face towards him and they kissed. Tails was lost in the pleasure, unaware of where they were touching him, until . . .
"Hey, wait a minute." The wolf man pulled away, his hand grasping Tail's crotch. He pulled the sundress up to reveal Tails' smooth balls and shiny penis cage. "You're a guy?"
"What?" the leopard man stopped sucking on Tails' tit and looked down.
Both of them were shocked. Tails managed to come out of the pleasure and realized what had happened. The shock fueled his fear, and that overpowered his arousal. Tails slipped out between the two men and ran out of the alley.
He headed straight home, looking back every so often to see if he was being followed. He wasn't. At least, that's what he thought.
Unbeknownst to him, throughout the entire affair, a fourth pervert was watching the event unfold along the rooftop. She happened to be there by chance, by fate, by luck. She watched the two confused men grumble this and that before leaving, and she descended the building into the alley.
She picked up and searched the purse on the ground. Strawberries. A can of whip cream. A wallet. She opened it up, snuck the dollars into her tan bosom, and looked at the ID picture.
Rouge grinned. "Looks like I found something interesting."