Jack: Dresses, Skirts, and Makeup

Today was an odd one so far. First Jack found a device that allowed him to possess his girlfriend. Then he realized he was stuck as his girlfriend. He was blackmailed and dressed up and now found himself in a clothing store, being dragged around by Steph as she tried to decide what he, or rather Sam, should be wearing today.

"We don't want something too long, really like to see that lingerie stick out," Steph said, looking through a floor length dress. "So this isn't long enough. Really I think that a skirt would do well. However you will need a dress tonight. But that could just be a surprise."

"Tonight? What's happening tonight?" Jack asked, following closely behind.

"Don't worry about it babe," Steph said with a wry smile and a wink. "Anyways, here lets get you dressed up."

The outfit that Steph picked out left very little to the imagination. A tight top that had a deep cut down Jack's front, giving a great view of Sam's wonderful cleavage. It barely covered Sam's tummy as well, so if he moved at all, slight glimpses of skin would show. To compliment it, Steph gave Jack a checkered skirt. The skirt was short, but easily went past the top of the lingerie socks. The outfit was a massive turn on for Jack. Just watching Sam mimic him in the mirror, the skirt swaying this way and that as he craned her neck to see each curve, it was getting him absolutely heated underneath. Sam looked really good dressed girly like this, but this was past that. It was positively slutty.

Next up, shoes. This part was significantly harder. Steph picked out some black heels for Jack to wear. He tried them on, and his first step, he nearly broke an ankle. Steph helped him up, laughing the whole way.

"Wow, you weren't kidding. Here, let me show you," Steph offered.

Jack kicked off the heels, passing them to Steph. She slipped them on and took a step. She talked about the strategy for walking with heels and showed how her hips swayed with each step. She took slow steps, talking the whole way through, like a teacher explaining to a child, which in this case was pretty close Jack guessed.

Next up was Jack's turn again. The heels weren't tall, just a couple inches of a curved wedge really. With it, he was just shy of Steph's height. As she held his hand while he took his first few steps, he felt his heart flutter when Steph put her hand behind Jack's waist. Secretly, he wished she'd go a bit lower. Seemingly reading his mind, Steph's hand roamed down to Jack's ass, giving it a soft squeeze. Jack smiled, feeling his face burn a bit as he lost focus, and once again almost fell. This time, Steph caught him and the two fell in a heap, with Jack landing squarely on top of Steph. He pushed himself up, realizing he was staring down at Steph.

"Your shirt babe," Steph said with a smile.

Looking down, he saw that his tits had fallen out of the slip. Quickly putting them back in, Steph started laughing and Jack couldn't help but appreciate this view.

"Well get off me, we have more practice to do with the heels," Steph said.

It took some time, but after awhile, Jack was walking like a champ. He had to go slow, but he could reasonably go without tripping too much. He felt very accomplished as the two of them walked out of the store. The click from the heels definitely was fun to listen to as he walked and he was very aware of his body was moving as he walked. The sway of his hips coupled with the flowing skirt made each step feel amazing.

Last but not least was makeup. Steph gave him a full makeover, buying all the stuff and applying it in store. She talked the entire time, explaining what each thing was and how it worked. Jack was lost in her words, just enjoying the attention he was getting from her. Just gazing into her eyes as she closely went over each part of Jack's face, was mesmerizing. Sam's pussy was purring the entire time.

"And that's it, how do you like it?" Steph said.

Jack stood Sam up, walking her over to a nearby full length mirror. A black shirt that barely contained his tits that complimented his checkered short skirt. It went over the top of his black thigh highs and heels. All complimented perfectly by his absolutely amazing face. Sam looked hot. He looked hot, he thought to himself.

"I think my little girlfriend is dressed quite nicely, don't you think?" Steph asked.

"I do too," Jack mumbled back.