Wear them

Reluctantly, Tripp takes the girly underwear. "Fine... I guess I'll have to get used to it at some point if I have to be in this form sometimes... Can you look away though?"

"Oh right, sure," Sam says, and turns away to let Tripp change.

Tripp sighs, eyeing the bundle of white fabric in his hand. It seems so small compared to his normal boxers, and so soft and dainty. He sheds the rest of his clothes and takes a deep breath. Then he steps into the panties and slowly pulls them up until they reach his newly-girlified sex. He releases them with a little snap, and shudders. His girl form came pre-shaved.

Weirdly, the panties are comfortable, at least physically. Mentally, Tripp can feel his masculinity crying out. He feels so tiny and soft and... cute compared to his normal self. His body is all curves and jiggle, with no muscle bulk or sharp lines. The panties only highlight that fact by clinging to his soft skin and gently cupping his pussy and butt.

He tries the bra next, sliding his arms through the straps and reaching back to hook the clasp. It... isn't as easy as he thought it would be. And after a minute, he gets reasonably frustrated.

"What the hell kind of puzzle-box bullshit is this, Sam? How do you put this thing on? My arms don't even bend that way! Who designed this?"

Sam turns around and finds Tripp struggling to latch the hooks of the bra. She bursts out laughing immediately.

"Whoa-ho, watch your language, young lady! It isn't that hard. Don't worry, big tough Sammy will teach you how to wear a bra, wittle Twipp! Or should I say, wittle Dawn!"

She giggles and turns Tripp around, taking the bra.

Tripp blushes but lets his friend dress him.

It's humiliating.

"Watch," she says, and takes the bra strap in hand. First, she pulls it against him normally, with his breasts in the cups, and tests the hooks to see if the first, second, or third row will fit best. Then she turns the bra around and wraps it at his waist so that the hooks are in front where he can reach them. She hooks the third row, spins the bra around, and pulls it up to his chest and lets him slide his arms through the straps.

"Viola!" she says proudly, "You're now wearing a bra! You're such a good girl, Dawn!" she giggles incessantly while she tightens the arm straps.

Tripp groans. "Shut it, Sam! I'm only doing this because you roped us in to being magical girls..."

Sam ignores him and muses to herself, "Hmm, maybe we should try having you wear panties and a bra all the time, just to stay used to it. We could do your hair and makeup, too. You would look so cute, even in your boy form!"

"Sam!!!"

Sam giggles and relents, and finally lets Tripp put on the rest of the outfit.

The sweatpants and T-shirt are surprisingly comfortable. It just feels weird having the panties and bra underneath. He can't stop thinking about the way the panties feel, or how strange and cumbersome it feels to have a bra on under his shirt.

"What do you think?" Sam asks, "Not so bad, right?"

"It's... nicer than I thought it would be..." Tripp admits. "A little snug in the butt and chest though..."

Sam chuckles. "Most girls would love to hear that. You have a great figure. Mmm, wow... You might get hit on if we go out together. I'm a little jealous!"

Tripp groans. It was humiliating, but he did it. He was wearing girl clothes, and it wasn't so bad. Maybe being a magical girl wouldn't be completely awful after all.