Alex swam laps in the pool, while the four girls watched him intently. Alex was athletic from his time on the swim team, but he was quiet and nerdy. He wore a legged speedo that did little to conceal the bulge of his dick, even when soft.
Rachel and Rose sat reclined on the lounge chairs by the pool, whispering to each other. Rachel was Alex's oldest friend, a full-figured girl with side-cut black hair, and an ample chest, she wore a white T-shirt over a bikini. Rose was a skinny girl with long blond hair wearing a red tank top and swim skirt over a more modest two-piece suit concealing her B cups.
Ruby, Rose's younger sister, floated in the pool on an inflatable duck. It was clear that she and Rose were related. Ruby shared Rose's skinny body and blond hair, but despite Ruby being younger than her sister, she was at least a foot taller. She was the only one of the girls to openly wear a bikini, showing off her toned abs and A-cup breasts.
John chatted with Emmy, sitting on the edge of the pool with their feet in the water. John was Alex's best friend for most of his life and the brother of Rose and Ruby. He was a year younger than Alex, tall and skinny, and good in a crowd, he fit into all the social situations that Alex dreaded. He was wearing swim trunks and (intentionally) showing off his six-pack to the girls. Emmy was a slightly chubby, but muscular girl, with short brunette hair in a bob-cut, she and Alex were on the swim team together.
***
These were Alex's closest friends. The six of them did everything together and while he would only ever admit this to John, he had a crush on every one of the girls. Of course, he was too shy to do anything about it.
In the middle of the summer, Rachel invited everyone over to her house for a pool party and sleepover. Her parents were out of town for the weekend, and they would have the house to themselves.
***
Emmy dove into the pool and swam up to Alex. She wore a tight-fitting one-piece speedo that was snug in all the right places, accentuating her C-cup breasts. Alex tried not to stare.
"Hey Alex, I still haven't forgiven you for beating me in the swim meet last week," Emmy joked.
"You want a rematch so I can beat you again?" Alex replied, laughing.
"Oh, I'm up for a rematch, and this time you're gonna be the loser, my friend," Emmy said.
"Alright, you're on," Alex replied.
Hearing the challenge, the others gathered around. Rachel hopped into the water and swam up to them. Her white T-shirt was now soaked through and transparent over a bikini that barely held her D-cups in place.
"Hold on, why don't we make it more interesting?"
Emmy looked nervous. "What do you mean by interesting?"
Rachel grinned. "A bet. Whoever loses has to do two more laps naked."
Rose gave a knowing smirk, both John and Ruby perked up and listened intently. Emmy looked nervous.
Alex's heart fluttered. The thought excited him; he had always wanted to see Emmy naked. But he was worried about how she would react if he appeared too eager about the idea. He thought about backing out to not risk the friendship. But he couldn't help but imagine Emmy's body without the suit. The idea of touching her made him feel giddy. He thought about what it would feel like to kiss her, to touch her chest, to feel her pussy wrapped around his cock, he was getting hard under the water. He was almost certain that Rachel's eyes flickered towards his crotch and her smile widened slightly.
He looked at Emmy, "We don't have to do that if you don't want to."
Emmy smiled at him. She looked conflicted. She bit her bottom lip and sighed.
"It's fine Alex," she said. "I'm in."
Her response shocked Alex. Excitement rushed through him, followed shortly after by panic, what if he lost? That thought excited him, too.
He swallowed the fear and replied as nonchalantly as he could, "Ok, it's a race."
The girls all cheered, John let out a whoop.
Alex and Emmy got out of the pool to get to their starting positions. Alex tried to hide his growing cock. Emmy seemed too focused on the race to notice, but the other girls stared at him, Rose bit her lip and Rachel had a devilish smile.
John walked with Alex to the starting position and whispered to him, "Dude, you better win, I see your cock all the time, but I've never seen Emmy's tits."
"Believe me, I'll try," Alex responded.
Rachel spoke up, "Ok, one lap, to the edge of the pool and back, and you'll go on my mark."
Alex and Emmy got into the starting position, crouched, ready to dive. The pool wasn't small, but it was nowhere near regulation size. This race would be over quickly, maybe too quickly. Alex was better at distance than sprints.
Rachel got out her phone and queued up a starting whistle. Alex tensed at the edge of the pool, all distractions gone, there was only the water.
Rachel played the whistle, and the two were off. They each dove perfectly, slicing through the water like a knife. Alex pushed himself harder than he had ever pushed himself before. Emmy must have as well because she pulled ahead for a moment and Alex glimpsed her cameltoe. It momentarily distracted him, but he rushed forward with renewed vigor, determined to see her pussy without the swimsuit.
Alex put everything he had into a burst of speed and caught up to Emmy, they hit the far wall at the same time and performed a perfect flip-turn in unison.
Alex's muscles burned as he reached the wall and slapped the side. He was panting hard. Alex looked over at Emmy, who was also panting. She was wearing a big grin. Alex smiled back at her. They both clung to the side of the pool.
"Who won?" Emmy asked.
"I don't know, it was too close for me to tell."
The two looked at the others. They looked as clueless as the racers. John shrugged.
Rachel grinned. "It was a tie!"
"Seriously?" Alex groaned. "So, I guess neither of us has to swim naked then."
