Dress to Impress

"EEEEEP!!!" Riley squealed out, only just managing to maintain his girly princess voice as Isabelle tore off the final strip of wax from his body.

It had been another few weeks of Riley going through his feminine routines. Skin and haircare, exercise, vocal training, and his favorite, meditation. Everything was progressing better than Isabelle could have possibly dreamed before starting her plan. His freshly waxed skin was soft and supple, his flowing hair was shiny and smooth, his voice was pretty and sweet, and his ass was so perfectly sculpted most women would kill for it. With the convincingly realistic breast forms added on top Riley appeared to be a bombshell with an hourglass figure. His naturally wide hips added to the illusion and his fairly feminine facial features, which he had once hated, made it so he didn't even need makeup to pass as a fully fledged woman.

If she didn't know who Riley was, she would never guess that he was a man. Which meant it was finally time for her plan to move on to the next stage. It was time for the new and improved Riley to meet the outside world.

"Hey Riley," Isabelle addressed her soon-to-be bimbo as he lathered up his hairless legs with body lotion, "I was thinking that tomorrow we should go visit the public gym. You could really use the equipment they have there. Plus I think it's time you debut your new look to all the ladies."

Riley gave a sly grin as he cupped his fake boobs, "It's about time, I was starting to wonder if I'd ever get to reap the benefits of all this work! The ladies won't be able to resist my girls!"

"Well..." Isabelle stifled a giggle as Riley proudly presented his tits, "there is one little problem we need to take care of first. Ever since you got your girls you haven't really been able to fit into your old clothes, have you?"

Riley nodded, thinking back to all the shirts he had to stretch over his impressive chest the past few weeks. The sizing was so off that not a single shirt was able to cover his midriff after being pushed up and out by his girls. His bottom half wasn't fairing any better either. The only pants that fit him anymore were an old pair of sweats that could barely contain his bountiful ass. New clothes were definitely a must.

"You're totally right!" Riley agreed in his meticulously practiced sing-song voice, "With all the muscle I've been packing on I guess it's about time to restock my wardrobe. I'll throw on some rags and head to the store-"

"Now slow down a bit there, missy," Isabelle couldn't help but smirk a little at her own words, "You weren't planning on buying more of the same clothes as you were wearing before, were you? Riley, your choice of clothing was another reason that I broke up with you. Your fashion sense is just terrible! Rather than letting you repeat your mistakes, I'm going to help you pick out some clothes to properly show off the new you."

Riley was a little hurt by Isabelle's blatant insulting of his style, but the feeling passed quickly. She only wants to help and she knows what's best, so he wouldn't question her judgement, "Oh, alright. Did you have a certain store in mind then?"

"There's no need," She took a seat next to him, "Tell me Riley, who is the most fashionable and stylish person you know?"

He thought for a moment. He was never really into fashion and therefore never really noticed whether the people around him were very fashionable. Looking over at Isabelle he could see that she was just as beautiful as she had ever been while they were dating. Surely she knew a lot about fashion right? "I guess that'd be you Isa...?"

"There's no guessing, it is me! So what would be the easiest way for you to become as fashionable and stylish as possible when I'm here to help you?" Isabelle led Riley's train of thought along as per usual.

After another short pause Riley was stumped, "Uhh... I don't know, tell me."

"Oh don't be stupid, girl!" Isabelle gave him a light tap on the head, "Obviously the easiest way would be to have you start dressing like me! If you just wear my clothes then you'll be on the fast track to being a true fashionista!"

While Riley might have normally objected to such an idea even in his highly manipulable state, Isabelle had taken steps to prepare for this moment weeks ago.

Clothing is not gendered. It is a mere coincidence that you might see more girls wearing skirts that guys. When wearing feminine clothing you will not question the fact that other men around you are not wearing bras or dresses themselves.

This subliminal message that Isabelle had planted so long ago was now coming to fruition. Riley no longer saw an issue with wearing women's clothing. In fact, he no longer saw it as clothing meant for women. The only divide that currently existed in Riley's mind was stylish or lame clothing, which Isabelle was carefully manipulating to include short skirts and skimpy tops as stylish, and pants and loose shirts as lame.

"Oooooo that makes a lot of sense!" Riley clapped his hands together to confirm his understanding.

"I'm glad you're catching on so quickly," Isabelle smiled with genuine glee, "Let's go ahead and get you an outfit ready for tomorrow then!"

Moving to the bedroom Isabelle spent very little time gathering the clothes she had in mind for Riley. In truth, she wasn't sharing anything with Riley. She had actually already bought him half a closet worth of feminine and revealing new clothes, on his own card of course. She would "lend" him a boatload of sexy and girly outfits without any intention of asking him to give them back. Eventually they would go on proper shopping sprees, and when that time comes Riley will have all but forgotten that they were never his clothes to begin with.

Isabelle set the bundle of clothes out on the bed to let Riley have a good look at them. Even in his brainwashed state, he was somewhat confused by a specific part of the outfit, "Uh, is that a sports bra? Is that really necessary?"

"Of course it is Riley," Isabelle was quick to dismiss his concerns, "Even if we ignore how good it'd look on you we still need to talk about the elephant in the room. You're girls are too big to leave on their own! Any man with a chest as muscular as yours would need a little bit of support. Here, just try it on and I'm sure you'll see what I mean."

Obediently, Riley followed Isabelle's instruction and pulled the sports bra over his fake chest. The difference was immediately noticeable. His heavy girls where no longer weighing down on his shoulders, in fact they were now more proudly on display than ever before even if they were a bit compressed, "Oh my god, you were so right! This feels great! I don't know why I was so worried about wearing a bra before, I don't think I could ever go back."

"I told you so," Isabelle giggled as she watched Riley inspect his bra encased boobies in the mirror, "Now try on the bottoms as well. I want to see how they fit."

Riley dutifully wiggled into the thong, which Isabelle assured him was necessary to prevent pantie lines, and the booty shorts she had provided him. Giving a little twirl to show off the full outfit he asked her, "How do I look?"

"Well..." Isabelle started as her face scrunched up into a bit of a scowl, "You do look great, trust me on that, but we do seem to have one glaring problem..."