Chapter 1
"I lost a bet," said Emma, looking like a mixture of disappointment and apprehension.
The girl had just arrived at her friend Sam's bedroom in a warm afternoon, sitting on the bed. They both lived in the same apartment complex, among many other folks their age.
"What?" Sam asked, perplexed. "What kind of bet? What did you lose?"
"Well..." Emma looked down on the floor and hesitated to continue, "something stupid about which of the guys Karen would kiss."
"Ok, that's stupid. But what did you lose? What do you have to do to pay the bet?" Sam continued to inquire.
"I have to..." Emma was trying to find the words, "go to Chris's party topless."
Sam burst out laughing, "No way! No way at all!"
"Yes, way," Emma said. But I think he just said that so I wouldn't go to the party. I don't think he likes me anyway.
"Oh, no no no. You're going to this party topless or not. The fact he might not like you is an extra reason for you to go," said Sam, decidedly.
"But how am I going to show up at a pool party without my bra?" Emma seemed lost.
"It's simple. You take off your bra."
"Ha."
"Seriously. You need to free yourself up, and I can help you with that," Sam said.
"I don't know. My body is just..." Emma was looking at the floor again.
"Come on. I'll help you out. And you'll show them that you're not ashamed of your body at all. In fact, you'll be proud of it," Sam said excited, getting up from bed.
"Alright. I'll try," Emma made an effort to look positive.
Chapter 2
The next day, Emma and Sam were browsing through Emma's clothes, trying to figure out what's the most revealing piece of wardrobe the girl had. The answer was 'none'.
"You disappoint me, friend. Deeply," said Sam, trying to sound as dramatic as possible.
"Oh, come on. If I had your body, I'd probably have some better clothes," Emma strikes back.
"You know what's worse? I bet you wouldn't," Sam said in a closing tone, "I'll lend you some of mine. Let's go to my apartment."
Sam's words sting, but it was probably true. Emma's never been a very confident person, regardless of her body. It wasn't at all bad. She was slim, her long black hair and pair of glasses gave her what Sam called the "hot teacher look". Maybe it's time to start taking advantage of that.
At Sam's place, Emma tried a few different pieces of clothing. As it was summer and very difficult to stand the heat outside, she tried on a suspicious blue bikini.
"Are you sure about this one?" Emma asked, hesitant.
"Yeah, go ahead. Don't forget the skirt that accompany it, since the bottom is a bit too revealing," Sam said, trying not to laugh.
Sam stripped and put on the blue bikini. It was like nothing she had ever wore before. The top was simply strings holding two small, and I mean small, triangles just enough to cover her tits. Since her boobs were slightly smaller than Sam's, they at least adjusted well, so they probably wouldn't accidentally slip out.
The bottom looked like a common bikini, but the front was cut. Like way cut. If Emma hadn't shaved, her pubes would be completely on view. It was just a bit away from revealing her slit. The side strings that went around her waist were also low enough that the shape of her vulva, and where it connected to her legs were fully visible.
"That's why I told you to wear a skirt," Sam handed the skirt to Emma.
The skirt was short, but nothing compared to the rest of her outfit.
"Ok, what do I do now?" Emma said, still kind of paralyzed by what she was wearing.
Sam wandered off looking at her phone for a bit.
"I'm sorry. It's Jacob, and he's somehow mad that I'm spending time together with you," Sam said, sounding kind of tired.
"Jacob again? You guys broke up like weeks ago. He needs to get over you," Emma said, almost angry.
"I know! I just can't seem to shake him off," Sam said, "anyway, back to the outfit."
"You need to feel comfortable in that. We're going to the apartment complex swimming pool, and then we'll see how you behave. If you wanna be topless at a pool party, this is the first step."
"Alright. I'm ready," said Emma, finding the last bit of courage she had.
Chapter 3
The walk to the pool was already uncomfortable enough for Emma. She had the constant feeling that her tits would slip out at any step she took, or that her bottom would ride down and end up revealing her pussy. At least that was covered by her skirt.
Arriving at the pool, to her relief, not many people were present. A woman sunbathing at one side, two guys taking at the other. Sam made sure they sat directly in front of them, from across the swimming pool.
"Why don't we sit over there in the corner?" Emma asked, with a kind of a desperation in her voice.
"It's perfect here," Sam said, with a smile.
"You're the devil, did you know that?"
Sam looked at Emma and just started laughing.
"Oh, by the way," Sam said, "you're gonna want to adjust that top. Or those guys over there will know your tits are pretty pink."
Emma noticed both guys looking directly at her. She blushed and quickly adjusted her bikini. But there was something thrilling about that exposition.
"I think they like it," Emma said, upon noticing their smiley expressions.
"Who wouldn't?" Sam completed, "that's what I'm trying to show you. You have an amazing body that's been kept hidden for too long. Time to start using it."
"I'll take a walk around the pool and make sure I pass right in front of those two," Emma said as she got up from the lounger, "without my skirt."
Now even Sam was shocked. Emma pulled her skirt down, leaving only a bikini bottom that barely hid her slit, and showed the entire shape of her vulva. At that view, the two guys simply stopped talking and just stared at Emma.
She slowly walked around the pool, her boobs gently but dangerously bouncing up and down against the small triangle that hid them. As she got close to the gentlemen, they didn't know if they looked up or down. Feeling daring, she smiled at them and waved with her left hand, while her right hand was hidden behind her back. Her fingertips grabbed the strings that kept her bikini top in place and without thinking twice, she pulled them in one motion that removed the whole thing.
In a second, her bikini top fell to the ground and her boobs were now completely exposed to these two strangers.
"Oh! I'm sorry," Emma said, pretending to be embarrassed.
"I can help you with that," one of them said, getting up from his chair to pick up the bikini.
"It's alright, I got this," Emma got down, picked her bikini bra and began putting it back up, still with her tits fully on show.
It took more than a few seconds to get everything back in place. Emma was purposely slow, as the feeling of being watched by those two strangers was making her as wet as she ever was.
Once she was done, she smiled and said a quiet "bye", to which they responded similarly. She continued to walk around the pool until she reached Sam again.
"You're learning well," Sam said. Not even I would have thought of the bra drop.
"Well, I have to train for the party, right?"
Chapter 4
A couple of days later, the girls met in Emma's bedroom.
"I have some bad news," Emma started.
"What a coincidence. I have some bad news," Sam said.
"You first," said Emma.
"Uh, ok. Well, it's Jacob," Sam said.
"Oh, your asshole ex-boyfriend. What did he do this time?"
"Yeah, so. He found out about us at the swimming pool and got really mad," Sam looked uncomfortable, "and said that I can't go to Chris's party."
"He can't tell you what to do!" Emma was fuming.
"Jacob said if I show up at this party, he'll share all of the nudes I sent him. I simply can't go, some of them are really private," Emma said, defeated, "but what's your bad news?"
"My bad news is that I lost another bet with Chris," Emma said looking embarrassed, "I know! I can't stop doing it! But this time I thought I was going to win and take back the topless dare. But I only made it worse."
"Worse... how?" Sam asked, afraid she already knew the answer.
"I have to be naked at the party at all times," Emma said without even looking at Sam, "and that's why I need you to be there with me! I can't go to a party naked without any girl support."
"Well, fuck," Sam said.
"We're fucked," Emma said.
"Yes. Yes, we are," Sam finished, defeated.
Chapter 5
Chris's party day has arrived. Acquiesced that her friend Sam wouldn't be there to support her, Emma summoned the courage she could find. She dressed in Sam's blue bikini and skirt, but this time added a tank top, and left the apartment complex. It was a short walk to Chris's house. Although she did get a few looks on the way there, it would be nothing compared to being fully naked.
Upon arriving, she was greeted by Chris himself.