Hollie

The next morning, John entered the office to see Hollie and Dina giggling at Hollie’s desk. He approached casually, hanging his jacket on the back of his chair.

“What are we talking about this morning?” Asked John.

“Oh, y’know… Nothing…” said Hollie, with a smirk.

“Hollie just can’t get over your little reaction to seeing me yesterday.” said Dina. John glanced around the office to make sure there was no one else in earshot.

“What? I thought I handled it pretty maturely, I kept eye contact for most of that time.” said John, worrying he may have gawked a little too much.

“That’s not what we’re talking about.” said Hollie.

“I mean the tent in your pants.” said Dina.

“Oh, no, I wasn’t… I mean, it barely did anything.” said John.

“Please, you blew up like a balloon. I know I’ve got a pretty face, but that’s definitely not what you were thinking about.” said Dina, turning swiftly towards her office.

“I really don’t think I had the reaction you think-” John said, before her office door shut. Hollie took her seat and looked over at John, whose face hadn’t been this red in years.

“Hey, it’s fine, dude. We’re just teasing you. She made it pretty… overt towards the end. We’re not gonna judge you for popping a boner.” said Hollie.

“Yeah, great. Good to know, but I really wasn’t all that…” John said, trying to phrase this carefully, “excited, or anything.”

“Sure, dude.” Hollie said, logging into her desktop. John let it go, knowing that the harder he pushed it, the more embarrassing it would become.

Most of the day passed quickly. Mandy left shortly after lunch, even earlier than the day before, and once again, John and Hollie completed their work with at least forty-five minutes left. They started talking, mostly about work stuff at first. Then, they returned to what they’d both been thinking about all day.

“Y’know, I wasn’t gonna bring up your boner this morning… I think Dina’s mostly just embarrassed about having to strip down, and was trying to shift that on to you. If the story in our minds was about you getting hard, then it would be less about her modesty.” said Hollie.

“That’s… a relief, I guess. Really though, I wasn’t really that hard. Like, maybe halfway, if that.” said John. Hollie raised her eyebrows, clearly not believing him.

“You’re really sticking to that story.” said Hollie.

“It’s the truth.” said John.

“Then how about you prove it.” said Hollie.

“What? How?” asked John.

“How about another bet?” asked Hollie, playfully, yet with a tone of caution.

“Uh, I’m not gonna whip my dick out, if that’s what you have in mind. The underwear bet was taking things pretty far as is…” said John.

“Hear me out. You say you didn’t get hard, even with Dina all stripped down in front of you. We’ve already seen her in her underwear, and I think she’d be happy to shift that embarrassment onto you if given the chance.” said Hollie.

“Okay, but-”

“We’ll get her to strip down again, and then you’ll open your fly up. Maybe drop your pants a few inches. If you’re really not hard, then your undies will cover everything your pants are exposing.” said Hollie.

“How is this a bet? What do I get out of it if I win?” asked John.

“Firstly, you get to prove your point, or lack there of. You’ll have proven that you truly do not think of Dina like that, which would put you in a small group of guys, cause let’s be honest, she’s an objectively attractive woman.” Hollie could see John wasn’t sold, yet. “And… if you win, I’ll strip down to my underwear, too.” John tried to hide the excitement in his eyes. He’d had a crush on Hollie for a while.

“And if I lose?”

“Then you go completely, and I mean totally, naked.” Hollie said, trying to play things cool herself.

“No way! That’s way worse than either of you stripping down to your underwear.” replied John.

“Oh, come on! Think about it, if you really did get a boner, then we’d already be seeing the general size and shape of it, anyways. How much more would we really be learning?” asked Hollie. John thought for a moment, and she did have a point. Plus, the opportunity to see Dina in her underwear again, and potentially also the girl he’d had a crush on for so long, was just too good to turn away from.

“Maybe there’s a way to make this happen, but… it’s too unfair a bet. Especially since, in your theory, I’d now have the idea of not one, but two girls in their underwear in my mind, AND the sensation of having my trousers undone. The odds would be leveled against me.”

“So… what can we do to sweeten the pot?” asked Hollie. John thought for a moment; He wanted to get more out of this deal, but he didn’t want to cross a line by going too far. He didn’t want to lose the opportunity, and much less the personal and professional relationship with Hollie and Dina.

“How about… IF I lose… I do whip my dick out, but nothing more. You’d get the proof you wanted, the embarrassment would definitely be shifted onto me, and you wouldn’t be learning much because you’d already be seeing the shape… But I get to retain some modesty, still. No balls, not butt, no nothing - Except my Johnson…” said John. Hollie’s face had subtly lit up for a second, before falling back to a slight disappointment.

“Well, if that’s the best off you’re going to make…” said Hollie. John was nervous that he’d hedged his bet too much, but then… “I’d make that deal. We have to get Dina to agree again. They marched into Dina’s office. The moment they entered, her face lit up a bit.

“What’s up?” asked Dina. John could see a slight excitement in her eyes, and realized that this may have been planned beforehand.

“Well, John and I were talking, and we want to make another little wager.” Hollie said, locking the door behind her.

“Oh? Is John stripping for us, today?” asked Dina.

“I mean, if he loses. The bet goes like this; You strip down again, which is nothing we haven’t all seen anyways, and John opens the front of his pants enough that we can all see the state of his bulge. If he has the same, or a bigger reaction than yesterday, then he’s gotta show up his big ol’ dick. At least, I’d hope it’s big, cause it’d be even more embarrassing for him if it’s not.” said Hollie, giggling.

“Just his dick? He’s not stripping all the way, like I had to?” asked Dina.

“First of all, you only went town to your underwear. Second of all, you’re the one that made that bet in the first place.” said John.

“Yes, only his dick… Not even his balls.” said Hollie. “It’s all he’s willing to put on the line. On the flip side, if he wins, I’ll strip down to my underwear.”

“For five minutes on each side of the bet?” asked Dina. John hadn’t even thought about the length of time.

“Uh, no. I’d be showing it to you for like, ten seconds.” said John.

“Hold on, now the deals starting to feel lopsided in the other direction.” said Hollie.

“Tell you what, John. Make it a full minute. I’d be gaining something out of you losing, too, not just Hollie… So if you win, I’ll wear a thong tomorrow, to give you yet another peak at my bum - just my bum. That peak would also be for a minute. If you really make it five minutes today without getting an erection, I’ll give you a real reason to get one…” said Dina. John thought for a moment, and accepted the terms.