(#3) Caitlyn and Gwen: Senior Prom

Prom Night

Caitlyn dropped him off at his house after they finished bowling. She made sure to rub his thighs the whole way home, gently touching his panties under the skirt as they kissed in the car before he got out. That had made him excited for the night and he had to carefully hold his skirt down as he made his way inside. He embarrassingly explained why he was wearing a skirt to his mom. His mom thought it was nice of Caitlyn to lend him her skirt. Jared excused himself to take a shower.

While showering he began his Prom preparations. He shaved everything below his neck, up till now he had only shaved his armpits and the waist down. He decided that he should shave his arms for tonight. He stepped out of the shower and gently patted himself dry. He slid some sheer blue panties up his legs, once again enjoying the feel of them sliding over his shaved legs. He put his new strapless bra on, it was a dark blue close, but not quite, the same shade as his panties. He placed the forms in the bra and made sure they laid correctly. He brushed his hair, attempting to style it like Rapunzel at the end of Tangled. He then put his makeup on. He finished with his favorite part, sliding the lipstick across his lips.

He stepped back and looked at his reflection. He thought he looked beautiful. He loved the way his eyes looked tonight, they were slightly smokey and sparkled with some light glitter. His lips and cheeks only had some light touches, mostly leaning into a pink tone. His lips shone from the slight amount of gloss he used on top of the lipstick. He decided that he preferred his B cup breasts as the Cs felt too large, but he'll wear them tonight so his dress could be the best one there.

He slid some soft pants up his legs in case someone was in the hall on his way to his bedroom. He didn't really care if his parents saw him in a bra, but felt the panties would be too much, at least for his dad.

"Mom!" Jared called down the hall, "Can you give me hand?"

Jared couldn't get the zipper up on his own and was stuck. Caitlyn was due to pick him up in about five minutes.

His mom walked in and laughed. "Did you get stuck?"

"No, I just needed some moral support," Jared said sardonically.

His mom giggled again, "Hold still."

Jared felt the bodice tighten around his chest as his mom zipped him into the dress. Once the clasp was closed he felt her arms wrap him in a hug. "You look amazing."

"Thanks, mom," Jared returned the hug.

His mom stepped back and sniffed slightly.

"Are you crying?"

"No," she was obviously getting choked up. "I never thought I'd be here, doing this. All I can say is I'm glad I get the opportunity to see you so beautiful. Stay there."

While his mom was gone he heard the doorbell ring and knew Caitlyn was there. He heard his dad laugh as mom stepped back in. "Your date is here!"

"I heard."

"Your dad asked if you had one of these and I couldn't find one so he went and bought you this." She handed him a small box that was wrapped with a ribbon.

"What is it?" Jared took the box and shook it.

"Open it."

Jared undid the ribbon and took the lid off the box. Inside was a small black clutch that had small pieces of glitter sewed on it so it sparkles like his dress. Jared stared at it flabbergasted because he had forgotten to get a bag for the night. Go dad!

"Do you like it?" His mom prompted.

"I do!" Jared said, pulling it out of the box and attaching the strap that would let it be a crossbody bag. "I did forget one of these." He snapped it open and put his phone, ID, and debit card inside.