(#3) Caitlyn and Gwen: Senior Prom

Dress Shopping

Jared pulled his bra strap back onto his shoulder while Caitlyn snuggled into him on his couch. They were watching Harry Potter with his parents for a family movie night. It had been a week since the bet was finalized and Caitlyn had convinced Jared's parents that he needed to wear a bra till Prom to "get used to it." His mom had agreed that it could take getting used to but seemed hesitant about the idea. His dad thought it was funny and harmless at first, but when Caitlyn had Jared wearing his breast forms, like now, his dad looked uncomfortable about the idea whenever he remembered it was happening.

The movie ended and Jared's parents made their good nights and went upstairs.

"Good night," Jared and Caitlyn called after them as they ascended the staircase.

Caitlyn turned to her boyfriend, "When are you going shopping, Gwen?"

Jared blushed. He didn't really like Caitlyn calling him that around his parents, although he knew they weren't in the room. He was comfortable with her calling him "Princess" however, and his parents thought it was part of the bet. "Allie and I are going tomorrow actually."

"That's great!" Caitlyn said while tracing the outline of his bra. "I can't wait to see you in it."

Jared shuddered as Caitlyn snapped his bra strap. "I'll let you know what color I get so you can get a matching one while out with Brittany tomorrow."

"You better, girl." Caitlyn gave him a quick kiss. "I wish I could get you to wear makeup while your parents are home. Mine don't care, but I think it would kill your dad."

Jared ran his finger over his bare lips, "We wouldn't want that." He thought back to the other day when Caitlyn's mom actually "taught" Jared how to apply makeup with Caitlyn giggling behind them. Her mom also had him in a skirt whenever they hung out there.

Caitlyn pulled Jared off the couch, "Walk me out, Princess."

Jared held her hand as they made the short walk to the door. He kissed her. "Good night, Cait."

"Good night, Gwen. See you soon!" With that Caitlyn bounced out to her car, her dress flowing in a way that flashed her panties to Jared.

Jared smiled and went to bed.

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
The next morning Jared waited out front for Allie to pick him up in her beat up red Durango.

"Get in loser, we're going shopping!" She called as the breaks squealed when coming to a stop.

Jared laughed at the quote and hopped in.

"Nope," Allie pointed with her thumb to the back. "In there, you need to change."

"What do you mean?" Jared asked, he was wearing  his bra and forms, panties, and some tight jeans.

"Girlfriend's orders," she pointed to a pink bag in the middle row.

"Fine," Jared got out and back into the middle of the car.

"Good girl," Allie sounded like she was praising a dog as she reached back to pat his head.

Jared rolled his eyes as the car moved down the street. He rummaged in the bag and pulled out an extremely skimpy outfit consisting of a super short skirt that wouldn't even cover his panties and a top that might cover his bra. "Caitlyn really wants me to wear this?" He held the outfit up in the rear view mirror.

Allie flushed, "No, sorry, that's for Taylor. She likes to pretend I'm her whore. Your bag is in the back."

Jared wanted to ask, but she was clearly uncomfortable with it. He found an identical bag in the back that had a bright yellow sundress, some makeup, a white headband, and a white choker necklace. He smiled, this was definitely more Caitlyn's style.