Yes, he makes it.

"Hope you're wearing boxers and not briefs…" said Dina, with a grin on her face.

John took a deep breath and fired the rubber band. It flew across the room and hit the courthouse, almost dead in the center. Johns head snaps towards Dina, with a huge grin on his face. Both girls seemed genuinely surprised that he made the shot.

"Holy-" started Dina. "I can't believe you actually did it. I thought we'd be humbling you today for sure."

"A deal's a deal, Dina." Said Hollie, struggling not to laugh. Dina looked at her, and then to John.

"Alright. Hollie, open a stopwatch on your phone… John… Enjoy the show." She led both of them into her office and locked the door. She took a deep breath, and took her shirt off. She was wearing a thin blue bra. John's eyes widened as he got to see her cleavage. After a few seconds, he composed himself. He might have won the chance to see her in her underwear, but this was still his coworker. She smiled at him, and took her belt off.

"Be ready to hit start, Hollie." Said Dina, as she unbuttoned her pants.

"I'm ready. As soon as your pants hit the floor, I'll hit start." Said Hollie. In a comical sense, Hollie seemed to be getting as much of a kick out of this as John. Dina locked eyes with John, and with a sigh, she dropped her pants to reveal matching blue panties.

"Alright, John. Here's your prize, dude. I'm in my underwear." She lifted her arms to the side for a moment, clearly trying to do this with as little shame as possible.

"Nope. Not quite." Chimed in Hollie. "Shoes and socks don't count as underwear."

"Seriously, Hollie?" Asked Dina.

"I would've made John go barefoot, so this is only fair." Said Hollie. Dina stared at her, seemingly a bit mad. "I actually can't hit start until you're in JUST your underwear."

"Fine. Whatever." Said Dina, eager to get this whole ordeal over with. She stripped her socks and shoes off.

"But, while I did say I'd strip to my underwear for five minutes, I never said I'd just stand here on display." Said Dina, walking around the desk, and taking a seat. Everything from her ribs upwards was still visible, and John could see her feet and ankles below the desk, but her waistline was cleanly tucked away behind the safety of her desk. Hollie took the remaining seat, opposite Dina. John shifted his eyes from Dina's chest, to her face for a few moments, while she seemed to check her emails. Hollie checked the watch.

"Halfway done." Said Hollie. John glanced out the window for a moment, trying to walk the line between enjoying his prize and being rude.

"One minute." Said Hollie.

"Thank God…" said Dina. John looked back at her, trying to seal this image into his memory. His sexy brunette coworker, in just her underwear.

"Twenty seconds. " Said Hollie. Dina looked at her, and then to John, as a smile appeared on her face. She stood back up, and walked over to her pile of clothes. She slowly bent over to pick them up, giving John a good look at her rear end. Then, she turned , still bent over to grab her shoes, giving John a view down her bra, at her cleavage. Her breasts were particularly large, but they were gorgeous all the same. She suddenly looked up at John, and shook her body a little, giving John a real look at how her breasts jiggled, which he had imagined many times before.

"AAAnd Time!" Shouted Hollie. Dina smiled, and put her pants back on, one leg at a time. She opted for her socks next, and then her shoes. She held her shirt in one hand, and put her other hand to her right breast, and gave it a little squeeze.

"Hope you enjoyed the view, because this is the only time you'll be seeing me like this." Said Dina, putting her shirt back on. Both John and Hollie were a bit surprised at how explicitly sexual she’s gotten in front of both of you, in your workplace. Dina looked John in the eye once more, than glanced down, and then towards the door. “Though, I guess you gave us a bit of a show, too.” she said, leaving her office. John looked down, and saw that he had started to pitch a tent in his trousers. He had kept his cool enough that he wasn’t at full mass, but it was a noticeable difference. Hollie noticed this, too, and burst out laughing. Hollie, too, trotted out of the office, with glee on her face. John adjusted his package so that it wouldn’t be as noticeable and went back out to the main office area, only to find Dina and Hollie giggling as they both put their jackets on.

“Don’t we still have like, half an hour.” asked John.

“Yeah, but I don’t think we’ll get in trouble for leaving a smidge early just this once. It’s like you said, we’re all down with our assignments for the day, anyways.” said Dina.

“We’ll see you tomorrow!” said Hollie, giggling.