It had been a week since Tails started her training with her new Mommy, Vanilla. During that time, Tails had been endlessly fucked, milked, and teased until she wasn't even sure if she was still alive or in heaven.
They did it everywhere. In the bedroom—obviously—in the living room, the kitchen, the bathroom, even in the backyard. No matter what time, weather, or consent, Vanilla would stick her cock up Tails' boy pussy and use her for hours.
Tails came an ungodly amount of girly cum, despite feeling like she didn't deserve to, but Vanilla insisted she'd enjoy it while it lasted. Honestly, a small part, deep within her memory, was happy to have such freedom. But one day, all of that changed.
It was late morning, and the two had just finished a round of love making and were washing the cum off their fur. Vanilla, as nude as she was gorgeous, looked in the mirror while applying her makeup.
Tails was instructed to stay by her side as she recited a few things. She wore a pair of Cream's panties, which were a little snug even to her tiny crotch, and some pink knee socks.
"We're going out," Vanilla said. "Today, Tails, is your first day of proper conditioning."
"C-Conditioning, Mommy?" Tails repeated nervously.
"Yes, after a week with working you in, I've finally found a routine that will make you into a proper sex doll."
Just thinking about finally making her Mistress Rouge happy made the femboy leak.
"What are we going to do first?" she asked.
"First, I'm going to get dressed." Then Vanilla looked at Tails and smiled. "You . . . can stay just the way you are."
Tails' heart started to race. "Yes, Mommy."
"Then, we're going to go into town and have ourselves a little walk."
"I-In . . . In my panties, Mommy?"
"Well, what else? Or would you prefer going out naked?"
"No, Mommy, I'll . . . thank you for letting me wear panties."
Vanilla giggled. "You're going to let everyone look at you, but don't worry, I won't let any of them touch you. You're safe with me, dear."
Tails simply nodded.
"We're going to a very special place. In a month's time, you'll be making Rouge cum in seconds."
"Th-That's what she deserves," Tails said.
While the foxy femboy stayed in her panties and knee socks, Vanilla dressed in a proper red business suit and knee length skirt. She also put on a pair of heels. The bunny milf was stunning, Tails thought, as the two got into the car and drove to the city.
Once they parked, Vanilla turned to Tails. "Oh, one more thing." She handed her a face mask and a leashed collar. "In case they start taking pictures. We don't want your friends to know you're still around, right?"
"No, Mommy," Tails answered, and put on the mask and collar.
"Good girl. Now, shall we?"
They exited the car. Immediately, the eyes of the masses were on Tails. Regular folk, men, women, even children, sneakily took out their phones to film the poor slave as she was led by Vanilla, who was also wearing a mask as well.
They walked block after block. The stares made Tails' masochistic instincts flare. The sounds of the people mocking her faded behind her beating heart. Blood flowed to her tiny penis, giving her tight pair of panties a little bulge, but she wasn't allowed to hide it.
They walked for a minute or two, until finally making a turn into an alley. There, the pressure of it all finally got Tails to cave in as she fell to her knees. She giggled madly as tears streamed down her face.
"My life . . . really is over, isn't it?" Tails said, still smiling, still crying.
Vanilla warmly returned a smile. "I think so, but it's fine, isn't it? Now, get up. We're not far."
Tails did just that and followed Vanilla down the alley, passing dodgy characters left and right. None made a move on her or Vanilla. Tails guessed it was because Vanilla, like Rouge, owned the place. Otherwise, there was no way someone as beautiful as her would not be pinned to the ground right about now.
As they walked, Vanilla asked, "Do you know why I made you walk half naked in front of all of those people?"
"N-No, Mommy," Tails answered.
"It's because I wanted you to stop being afraid and have more confidence in yourself." Vanilla turned towards Tails. "You are beautiful, Tails. You're just so darn sexy. Everyone there, all the ones taking pictures of you, they wanted to have their way with you. They just held back, was all."
She grabbed Tails' tiny prick through her panties with two fingers and started stroking it. Tails moaned, but stood where she was for Vanilla's convenience.
"The problem, Tails, is that you think you're an object. That you need to have sex." Vanilla shook her head. "That kind of thinking is for disposable sex toys. I'm going to make you last. What you need to do is want to pleasure cock. Not need."
Tails didn't even last a minute, as she came on the spot. Her clear cummies stained her panties. A couple fucking in a corner saw her shameful display and laughed to themselves.
"Once you start wanting, then you're one step closer to understanding your user. You understand?"
"Y-Yes, Mommy," Tails gasped.
"So, what is it that you want to do?"
"I . . . I . . ." Tails searched her heart. Her current desire was quite easy to figure out. "I want to go back on the streets and let the entire city fuck me."
Admitting that let Tails have a mini dry orgasm. Vanilla grinned. "Follow me," she said, and they continued on their trek.
They reached a featureless bricked building. No signs, no directions, just a steel door with a number pad beside it and a camera up top. Vanilla typed in the code and the door opened up. The inside was cold and sterile. Not a speck of dust in sight of the white tiled hallway.
It was here that Tails would finally be broken in. Her new life awaited her.