(#1) Caitlyn and Gwen: Florally Welcomed

Caitlyn's House

When Caitlyn's Honda parked in her driveway Jared glanced around to see if anyone was nearby.

Caitlyn laughed, "Are you kidding? You just walked through the mall wearing those cute, tight jeans and now you're worried about someone seeing you?"

Jared blushed, "I'm just nervous is all. I don't want anyone to see me like this."

Caitlyn smiled and opened the garage door, "After you, princess." She winked.

Jared shyly smiled as he walked into her home. He knew that she was only teasing and he liked it since it made him feel like they were growing closer together. Caitlyn, on the other hand, was staring at his butt as he walked into her kitchen. She was surprised at how attracted she was to him at the moment, he looked like a girl from behind and she couldn't understand why she liked his new feminine assets.

The kitchen was modest, nothing too fancy. It was clean with no dishes in the sink, a foreign concept to Jared, and was well kept.

Caitlyn walked up to him and gently brushed his hand as she grabbed the bag of his wet clothes. "I'll get the laundry started."

"Thanks," Jared said. He was a little nervous, this was the first time he had ever been in Caitlyn's house alone with her. There was usually always someone else here. He wasn't sure what to do, so he just got himself a cup of water. "It's a good thing you switched your laundry over before we went to the mall."

"Oh, yeah." Caitlyn laughed nervously. He couldn't have put that together, right?

"So, what do you want to do while we wait for the laundry?" Jared asked. He was trying to stand in a casual way, but he normally put his hands in his pockets when he tried that. He couldn't get his hands in them so he just held them in front of him in a very, though he didn't know, feminine way.

"Well," Caitlyn walked up and stood close to him, "we could have some fun." She reached around him and placed a hand on his butt. She could hear her heartbeat and was sure he could hear it too. She wasn't going to squeeze his bottom but she wanted to. It felt nice and full in her hand.

Jared was surprised at how close she was to him. They were close to the same height so he was staring into her eyes. He could feel her hand both just resting on his butt and simultaneously holding him in place. He wasn't sure what to do so he just placed one hand on the small of her back so he wouldn't stand there awkwardly.

"What kind of fun?" He was hoping they might be able to cuddle on her couch while watching a movie or something.

That was not what Caitlyn had in mind. "I've always wondered what you'd look like if I could dress you up as a girl, and since you're halfway there, could we do the top half?"

Jared was taken aback. She wanted to play dress-up? That was a little odd. He was only wearing what he was wearing because of a spilled drink. "I don't know, Cait. I'm only wearing this because I got wet at the mall."

Caitlyn pouted. She knew she could guilt-trip him into anything if she played her cards right. The pout would certainly make him feel bad about saying no. She also decided to get a little flirty. "Please?" She pleaded, "You're already wearing my panties. Surely the rest wouldn't be so bad."

"I don't know..."

"Besides," She slid her hand off his bottom and wound it up to his chest. "Wouldn't you like to know what my bra would feel like?"

Jared got lost in thought for a second. Did he have a chance to see her bra too? She wouldn't want him to wear it, surely. It wouldn't fit. After all, her chest was larger than his. But if he had to wear a shirt to see her bra, he'd do it. "I have always wondered what it looked like."