Naked At The Pool Party

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.

"I don't think you're allowed to wear this many clothes. Remember our agreement?" Chris said, with a malicious smile on his face.

"You really can't wait to see me naked, can you? Anyway, just give me a minute to at least get used to the environment," Emma said, trying to sound funny but still nervous.

"Fair enough. Please, come in," Chris showed her the way.

His house was indeed impressive, and it was clear his parents had a lot of money. On the back, his swimming pool was breathtaking and the lounge area was equally stunning.

In total, Emma counted nine guys. There was Nick, who she was an acquaintance to. Jacob, Sam's asshole ex-boyfriend. Also Michael, who lives nearby. The rest she had never seen before.

Chris introduced her to everybody individually, and they all seemed to smile in a way that shown they knew a secret she didn't. That was slightly uncomfortable until it clicked: Chris probably already told them about her stripping.

Emma took a longer look at Jacob and where he was sitting, talking to his friends, "funny how he seems excited at the idea of seeing me naked, but his ex-girlfriend, my friend Sam, can't come to the party," Emma thought, annoyed.

Everybody was friendly enough, which made her much more comfortable for what was to come.

A few guys were in the pool, and she thought it was her opportunity to make her stripping seem natural. She stopped at a sun lounge near the water and took her tank top off. She immediately realized she needed to adjust her bikini bra, as her tits were almost fully out. Quickly tidying all up, she took a glance at the water.

As expected, all faces were turned to her. When she took the skirt off, she heard some muffled exclamations and comments. Not surprising, as her bikini bottom was just enough to cover her pussy slit, nothing more. Again, she had carefully shaved, or else her pubes would be visible, too.

She went for a swim and made small talk with the guys at the pool. They mentioned Chris won a bet against her and wanted to know more about it. Emma told them the story and how she ended up like this. She received some polite compliments and left the swimming pool.

"It's time, I think," Emma thought to herself.

Taking a deep breath, she pulled the bikini bra strip and let it loose. Her boobs now fully in view of all nine guys. They weren't large boobs like Sam's, but were just right. She put her bra on the lounger and sat back for a while. From the corner of her eye, she saw Chris with his phone in hand. He wasn't even pointing it at her, but she said "I wouldn't mind some pictures."

Chris got up and sat down near her, taking a picture of her face and boobs.

"What about the second part of our bet?" He asked, looking down at her almost exposed pussy.

Emma became suddenly quite nervous.

"Uh...", she was trying to find a way to do this "I'll go to the dressing room if you don't mind."

"Not at all," Chris said.

Emma waited a couple of minutes until Jacob and his friends left the table they were sitting at. Given the opportunity, she got up, went near the now empty table looking for her target and quickly picked it up. Then, she casually walked back to the pool and let it fall down to the bottom.

"Alright. Now to the dressing room," Emma thought.

It was a small dressing room, but still impressive to have one in your own house. It had a few lockers, benches and showers. Emma stripped down from her bikini bottom, which made little difference on how exposed she felt. Looking at the nearby mirror, the only difference now was that her innie pussy slit was visible, as well as her ass.

Chapter 6

"I told you not to show up here!"

It was Jacob's voice.

Emma left the dressing room immediately as she was pretty sure what was going on, and her friend needed help.

Sam had showed up at the party in a sexy orange bikini, just not as revealing as the blue one she had lent Emma. Jacob was mad jealous to see her. Interestingly, everybody was turned at them, and nobody seemed to notice Emma was fully naked.

"I'll expose your photos, you dumb bitch. You're fucked," Jacob said, as Chris tried to calm him down.

Emma made eye contact with Sam. A simple signal told her everything she should know.

"Do it then. Pick up your phone," Sam said.

Emma went back into the dressing room and spied from the door. Jacob looked for his phone at the table where he and his friends were sitting. It wasn't there. He looked down on the floor, around the pool, until he saw it.

At the deep end of the pool, lied Jacob's phone. Forever inoperable.

He was so mad Emma thought he would explode. He just left his broken phone at the pool and left the party without saying a word to anyone.

"Sorry about such a dramatic entrance," Sam said, smiling.

"God, that guy was an asshole," Chris said, as the others agreed, "and welcome, Sam. Beer is over there."

Chapter 7

Emma finally thought it was the right time to come out of the dressing room.

As all looks turned to her, she awkwardly turned around to show she was fully naked, and to give them a view of her ass.

Again, a wave of exclamations came from the guys.

Sam got close to her, and whispered on her ears, "thanks for throwing his phone on the water. He deserved it."

"No problem, sis."

"I feel weird being the only clothed girl in here," Sam said, smiling.

"The dressing room is right there," Emma pointed to the direction.

As Sam went into the dressing room, Emma again laid down at one of the loungers, making sure it was close to where the guys were.

"Never thought you'd be this hot," Chris confessed, "actually, I never thought you'd pay the bet."

"I never thought I would either," Emma replied, "but here I am", she said as she spread her legs a little.

She grabbed Chris's strong hands and pulled it to her thighs. He began caressing her, going up and down. Down near her knees, all the way up, almost touching her pussy. Then he sat down on the lounger on top of her, so he could grab both her thighs.

Noticing all the action, another guy Emma didn't know went behind her and began feeling up her tits. The feeling was amazing, having this complete stranger feeling her up. She extended her arm back to grab his dick, which was already as hard as a rock. She managed to pull it out of his trunks and began masturbating it. She hadn't even seen the guy's face, but she was stroking his cock. He bent down to kiss her, and they did so passionately for what felt like minutes.

Then she was suddenly awake from the kiss by somebody feeling up her pussy. Chris helped her spread her legs as wide as she could and began touching her pussy. His fingers slid from her clit all the way down her entrance, then teased her by pushing in only slightly. She was as wet as one could be.

One by one, all the eight guys approached her. Some felt her boobs, some her face and neck. Four or five disputed some room to touch her pussy. Emma was making involuntary motions with her hips, and feeling as horny as she had ever felt. The attention from so many guys at once was exhilarating.

"Not fair with her!" she heard Sam's voice, "and not fair with me neither. I feel lonely over here."

Turning to look at her friend, Emma saw a completely naked Sam, lying down on a lounger. Her body was indeed beautiful, in ways her couldn't be. Her boobs were large but perfectly shaped, her hips wide, her thighs thick. Her red hair only made her even hotter.

"We'll split. Four for me, four for her. What do you guys think?" Sam said.

"Fair," said Chris, and they split. Chris and three other guys stayed with Emma. The other four went over to Sam.

Already wet from all the flashing, Emma pulled her knees back near her shoulders, "who wants to go first?" Even she was surprised at how forward she was being.

Chris didn't think for a second and positioned himself right between her legs. Her shaved innie pussy was dripping bright, and his thick, long cock slid in with ease. Emma looked down to see just how large it was, and how deep it went. She couldn't believe her pussy was that deep. She was absolutely sure it wouldn't fit all the way to the end, but it did.

Then he slowly pulled it out, then in again, making her moan. Distracted, she didn't notice another cock entering her mouth. She made sure to treat it well, sucking it as good as she could.

"Ok, that's two. There's two more," she thought.

Another guy pulled her right hand and directed it to his cock. She began stroking it as he moaned. The tip and head were already soaking wet with precum, and he came very quickly. Cum flew onto her tits, and some on her hair.

Without warning, Chris came in and out of her pussy, making an sticky mess. He was quickly replaced by the fourth guy, another one Emma didn't know, who pushed his cock in, eased by all the cum left over by Chris.

Emma then felt the cock in her mouth begin pulsating, and she knew what was coming. It quickly filled her mouth and dripped down her chin onto her boobs. As she pulled his cock from her mouth, another shot hit her face. She swallowed what she could.

Down at her pussy, this last guy pushed his cock as deep as he could and finished inside her.

Emma took a deep breath and looked around. All four guys looked satisfied. Looking down at her own body, there was cum on her face, mouth, chin, boobs and her pussy area had more cum than pussy. Not to mention the inside.

As she got up from the lounger, cum spilled from her pussy to the floor and down her inner thighs. Sam was just finishing as well.

"How about we switch places?" Sam asked her friend Emma.

"What? Do you mean going again?" Emma asked, perplexed.

"Yeah, but with different cocks, silly," Sam smiled.

Sam walked to the lounger Emma was lying at, and Emma saw no choice as to move to Sam's previous lounger and have sex with these four strangers.

She walked slowly and was about to lay down, when one of them instructed.

"Wait. Let me lay down here first. You go on top."

This guy laid down on the lounger and pulled Emma on top of him, facing him.

"Like this?" Emma asked as she directed his already hard cock to her soaking pussy.

She bounced up and down on his cock. Again, she didn't think she could take this girth, but she guessed her pussy was already so wet that it was making it easy.

She started looking for the other three guys, as they probably wanted blowjobs, but couldn't find any in front of her.

Then, she felt a wet stiffness being pressed right against her asshole.

"Oh, no. I'm not used to..." Emma tried protesting but it was too late.

The cock had slid in easily, and now she was being double penetrated. One in the pussy, one in the ass.

"I had never..." she couldn't complete her sentences.

The cock in her ass was pulled out just to be replaced with a new one. They'd go on to fuck her for a while, then allow the next one in line. After a few minutes of this, they started to cum, one after another. Some went deep in her ass and left their spunk in there, some came on her ass and let it drip down.