In the hot tub

It was in the evening, almost at closing time, when Maya was chilling in the hot tub with another regular. She was wearing an orange bikini that complemented her tanned skin nicely. Her hair was brown, very short and normally a little messy, but right now it was still drying from her swim earlier. Her ass was nicely shaped and probably her best feature. Her breasts on the other hand, were a little lacking. She barely qualified as an A cup, and that didn't look like much on her tall frame. She had made her peace with it though, it was others who seemed to care more about it.

"So it's this challenge where women only wear men's swimming trunks and pretend to be men to get away with it. I think it started as drawings, but now some people are actually doing it. It's really going viral and you're perfect for it! No one would notice you are a girl with your tiny tits!"

"Even if that were true, I don't think I want to go viral for that."

The girl in front of her, Hailey, was about 19, same as Maya. She was shorter and curvier, though not in a bad way. Her tits were bigger, quite big relative to her size in fact. Her ass wasn't any worse, as she had wide hips and a round butt. Her skin was a little lighter and she had long blond hair. "So we won't film it, just doing it for the love of the game. But what do you mean if it were true? It's definitely true?"

Okay Maya wasn't self-conscious, but even she had her limits. "They're still noticable, I'm not completely flat! Besides, my nipples would be obvious if they got hard."

"It doesn't have to look perfect. People will see someone with short hair, no tits, and male clothes. They're not going to question it any further, no one is analyzing men's nipples at the pool."

"Maybe you have a point, but my tan lines would definitely betray me."

She really thought that would stump Hailey. She worked hard on her tan, but she always did it at the pool, where going topless was not allowed. But Hailey moved right past her objection. "So we'll get you some sessions at a tanning salon first."

"I can't pay for that!"

"That's fine, my treat! I'll get you the swimming trunks too and any other expenses that come up. My family is rich, remember?"

Hailey really had it all figured out. But there was still no way Maya could do it. "Regardless, I'm not going anywhere in public without a top."

"What, are you a chicken? Come on, I dare you!"

"I'm not. Just... what do I even get out of it?"

"How about we turn it into a bet? Let's say that if I'm right and no one notices, you have to come on my next vacation. Two weeks overseas filled with beaches, water parks and whatever else I can think of."

"That doesn't really sound like a punishment."

"Exactly! And if you're right and you do get caught, you can dare me to do something equally embarrassing. You don't even have to decide the dare now. Plus, I'll pay your pool membership for the next 5 years!"

That was actually a really good offer. She might get embarrassed, but she kind of won either way. And she needed that membership, that shit is expensive on a student budget. A two-week overseas vacation, on the other hand, might be a once-in-a-lifetime opportunity for her. The choice was clear. "I can't believe I'm doing this."

A few weeks later everything was ready. Hailey turned out to be pretty committed to the idea. She had paid for multiple sessions at the tanning salon and had bought the swimming trunks. Maya was getting more nervous as her tan lines disappeared, but the reward was too much to pass up. Now there was no backing out.