A different public pool

If she's going to do this, she certainly can't do it at her local public pool where everyone knows her. Luckily there was a similarly sized pool not too far away. Maya set up a day and time with Hailey, who was happy to take care of the entry and transportation costs.

Maya was a little shocked when she saw the fancy black car that stopped at her house. And even more so when it was not Hailey that got out but a chauffeur who walked around and opened the door for her. She got in after handing over her bag and found Hailey already sitting in the backseat. "Just how rich are you?"

"Hello to you too." Hailey smiled at her, she was clearly in a good mood. "Are you excited?"

"Mostly feeling like I should have asked for more money in the bet."

"Are you saying my company isn't enough of a reward?"

"I can have your company without embarrassing myself."

"It's going to be fine, but we better get going. Don't want to waste a second of today."

"Great..."

The car took them to the pool and they walked inside. Before going into the changing room, Hailey handed her the swimming trunks. Then Hailey disappeared into the women's changing rooms, while she decided to head to the family stalls instead. Those weren't gender-specific, so no one would question why a "man" was coming out of them.

Quickly she stripped off her shoes and socks. Her shirt and bra took a little longer. It was weird taking it off, knowing she wasn't going to put anything on to replace it. Despite being in a separate stall, she felt oddly naked. Next, she took off her pants, but she hesitated again with her panties. She knew some guys wore underwear under their swim trunks, so maybe she should too. In the end, she decided against it, though. Her panties were quite obviously feminine, so even the waistband sticking out might raise questions.

She pulled up the trunks until they were in place. The weird net underwear, whose purpose she never figured out, sitting against her skin. They fit well enough, especially considering her hips and ass were a different shape than a man's. However, that did mean Hailey had needed to buy trunks slightly too large to cover it up. Maya pulled the string tight and tied it into a knot. Hopefully that would keep it secure.

That was everything. These swim trunks were all she would be wearing at the pool today. Ironically, they covered much more than her normal bikini bottoms, going down to a bit above her knee. Her breasts on the other hand, no matter how small, were more exposed than they had ever been. She could already feel her nipples starting to get hard at the prospect of walking topless in public. That certainly wouldn't make it easier to go unnoticed. But even if she did go unnoticed, everyone in the pool would still have seen her naked tits. The reward was worth it, though.

After building up some courage, she finally opened the door and stepped into the locker room. Which was entirely empty. She quickly put all her stuff in a locker and prepared to step out into the pool area.