Originally posted to Deviantart on March 19, 2016.
It was a stupid idea, and needlessly risky. However, Josie was a little short on the cash she needed for a new sundress that she really liked. If she completed her friends little dare, she would have the money and some change to spare.
The challenge? Get her friend some drinks from the rest stop vending machine. With nothing but a towel.
“You can’t be serious… what if someone sees?” Josie protested.
“Hey, if you don’t want the fifty dollars, that’s fine. You don’t have to do it,” replied her friend Becky. “It’d be a shame if you chickened out though, it’s easy money.”
Josie bit her lip. In truth, it really wasn’t that bad. The two were on a road trip together, and at a rest stop. It seemed like they were the only ones there. If she could be brave enough to do this, she could have that money.
The black haired girl took a deep breath, and stepped out of the privacy stall of the rest stops restroom. Her clothes were in a bag, and there was only a towel on her body. Josie would be quick. She could do this.
“Oooh, you’re going to do it, huh?” Becky giggled. “Alright then,” she took out some money. “Come back with four drinks, and you’ll get the fifty dollars.”
Josie blushed, but took the money in her hand, and tried to force a smirk onto her face. “I’ll be right back.”
She took slow, careful steps towards the exit of the restroom. Those vending machines faced the road, but if she didn’t look at the road it would be easy.
“Hey Josie,” Becky said with a giggle. “How about… double or nothing, and do it without the towel?”
Josie froze, and slowly turned to Becky. “W-what? I can’t do this completely naked!”
Becky slowly revealed a one hundred dollar bill. “I saw a hat that goes really well with that dress you want at the mall. It ain’t cheap either.” She waved it as if to taunt Josie.
Josie appeared to have a lot of internal conflict going on. Doing this with a towel was one thing, but completely naked was another. However, she reminded herself, that they had barely seen any other cars during their road trip that day. If she braved being naked, she would have extra money to brag about.
The black haired girl gave into monetary motivation, and slowly unwrapped the towel from her body. Her breasts were no longer restrained by the fabric, and gave a brief bounce as she took the towel off.
Her shapely rear also came into view, which earned a surprised look from Becky. Becky seemed to like what she saw, and nodded approvingly.
“Keep that handy,” Josie pointed to the hundred dollar bill, trying to look sly. She held the vending machine money in her hand, and slowly pushed the restroom door open, and stepped outside.
Almost immediately, Josie’s false confidence disappeared. Her tightly held her chest, and put a hand between her legs, frantically looking left and right. She mentally screamed at herself, wondering why she thought this was a good idea.
Wanting to get the dare over with as quickly as possible, Josie took careful walked around the rest stop towards its other side where the vending machines where. Her heart was thumping away as she thought of how she was absolutely naked. It wasn’t like she was at the beach, or had taken a shower, this was a roadside rest stop!
Josie started a quick jog as her face had a bright shade of red. Each step she took away from the restroom, her brain nagged at her more for doing this dare. But with the vending machine around the corner, she wasn’t going to give up.
The naked girl finally reached the vending machines, and gave another frantic look around to make sure nobody was near. Then she inserted the bill into the vending machine. Wanting to move quickly, Josie quickly pressed the buttons for a can of pop, but was greeted with the message, “Insufficient funds.”
“What the…” Josie looked, and saw the machine had spat the dollar back out. She took it, flattened it frantically against the machine, and tried it again. However, the machine still refused to take the dollar.
Josie took the dollar and tried to fatten it once again, as she started to wonder if Becky had purposefully chosen a faded, crumpled dollar to prolong her exposure. If a car passed by, they would see Josie’s naked backside.
The third time was the charm as the machine finally accept the money, and Josie was finally able to select a simple can of pop. Once the can tumbled down, it also spat out a pile of quarters. Josie still needed three more drinks.
Her heart was racing as she picked up the cold can and the coins, and held the can between her arm and her chest, as she counted coins. Josie gasped in surprise when the can made contact with her skin. If the drink wasn’t froze, it wasn’t far off.
Soon, Josie had reason to panic, as she heard the sound of a car approaching! Josie looked, and saw a car parking at the rest stop, prompting her to hide behind one of the vending machines. A passing car wouldn’t see her, unless the driver was looking directly at the rest stop. However, her view of the car was also blocked.
She held herself firmly against the wall, trying to steady her breathing. If they saw her…
A car door opened and shut, and there were footsteps getting closer. Josie braced herself, expecting to be found, but instead heard the sound of the bathroom door squeaking, and then shutting.
Josie sighed with relief, knowing she didn’t have much time. She started inserting the coins into the vending machine again, and selected another can of pop. With a second cold beverage pinned between her arm and her left breast, Josie shivered, feeling goosebumps go up her skin.
“Get it together… that money’s yours.” Josie said, attempting to motivate herself. Her shaking hand inserted a few more coins, and this time got a bottle of water. With her left arm now supporting three cold drinks against her breast, she noticed a reaction she had to it. Her left nipple was now hardening in response to the cold.
Wanting to end this as quickly as she could, Josie started popping coins into the vending machine. Just one more bottle of water, and she could run back to the ladies room. Josie’s nervous, unsteady hand hit the buttons, and a bottle of water tumbled down. She retrieved it, and tried to hold all the drinks in a balanced way.
Four drinks were simply too many for one arm to hold, so Josie needed both arms to hold them against her chest. Unfortunately, this meant she had no free hand to cover herself between the legs. Josie had no choice but to go forward like this.
The cold drinks quickly had a similar effect on her other breast. Feeling the cold against her skin soon made both of her nipples stand up.
Before Josie could reach the ladies room, she heard a honk. The black haired girl turned her head, and saw Becky waiting at their car.
“Over here! Hurry up!” Becky waved with a grin.
Josie looked at the car, out in a more open area of the parking lot, then back to the rest stop. She then started running towards the passenger seat of the car.
Becky reached over and opened the door for her, letting Josie climb in.
“Becky, why did you leave the bathroom? You were supposed to wait for me!” Josie said, setting the drinks in the cup holders.
“We had a visitor, a girl visitor as a matter of fact. I figured you didn’t want to be seen.” Becky said. “First thing’s first, a bet’s a bet. Here you go,” she said, handing Josie the one hundred dollar bill.
Josie took the money with a small smile, and ducked low to keep the view of her naked body blocked. “Heh… it was scary, but at least it was worth it.” She then looked at Becky. “Where are my clothes?”
“They’re in the trunk,” Becky said, as she nonchalantly opened a can of pop. “Don’t worry, I folded them nice and neat.” She then sipped her drink.
“W-what? But I still have to get dressed! We can’t keep going while I’m naked!” Josie protested.
“Sure we can! Watch,” Becky said, as she put the key in the ignition and turned it. The engine purred to life, and Becky reached for the gear shifter. “See? It works!”