College

Andrew and Zach are two Senior roommates in College, They'd met Freshman year and been close ever since, over the years they'd spent way to much time competing with each other.

they'd had too many drinking competitions to count, they competed over grades, both pretty good students, they competed physically too. Just about anything that they could, they'd compete at.

One night, on a rare night of no competing Andrew and Zach were at a bar drinking with a mutual friend of theirs Amanda

Zach had briefly dated Amanda Freshman year, but it didn't last long and it ended amicably.

This particular night, Amanda was talking about what was being discussed in her biology class, about body types and facial structure mostly.

"So that's why Men more often have more squarish faces, while Women have softer rounder ones, you both have pretty soft faces, You'd have been pretty girls" she joked

Andrew joke "Though I'd be much cuter than Zach"

"ha! you wish! we both know I'd be way cuter!" drunkenly argued

"Wanna bet on it?" Andrew retorted

"It's on we'll discuss the details in the morning" Zach continued

"Oh, I can't wait to see this one, I'll help however I can." Amanda

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The next day they all met up to discuss the bet.

"You still in Zach?" asked Andrew

"Like I'd ever back out of a bet" Zach scoffed.

together with Amanda they discussed the terms, and at the end, these were the rules they came up with

Every Day, they would take turns adding one knew feminine thing they both would have to do or wear, The first day, tomorrow and from then on, they would both have to wear girls underwear, Tomorrow Andrew would add a new rule, and the next day Zach would add one, and they'd both have to stick to it until one of them quit

Amanda took them both shopping and helped them select and purchase a few pairs of panties each.

The Next morning both Andrew and Zach woke up, got changed remembering it was panties only for now.

They both went to class like normal, both finding that while panties were tighter, they weren't all that different from wearing briefs.

it wasn't until later that afternoon that they met up again.

Zach spoke up first. "Well that wasn't so bad, whats your addition for tomorrow"

"well i figured since we're wearing panties, might as well start wearing bras as well." Andrew replied

"I figured thats what you'd pick" Zach replied

Amanda chimed in, i figure neither of you want to actually get fitter for a bra, so come back to my place and I'll do the measurements and then we can go shopping."

They both agreed that be a lot less awkward then getting fitted at a store.

The three went back to Andrew and Zach's house and found a tape measure, Amanda measured their chest and looked online for the average cup size for their measurements. Zach being a bit bigger than Andrew had a slightly larger average cup size

An hour later they were back at they're appartment learning to put bras on, it was significantly toughter than taking them off someone else they discovered.

The next day was the same routine, Andrew and Zach woke up got changed, remembering to wear a bra, just hoping they wouldnt show through their shirt too much. They went on with their days.

That afternoon they met up again, it was Zach's turn to add something