My Day as a Pool Boy

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This is a Summer Lovin’ 2015 Contest entry. It starts slowly so please be patient. All characters are eighteen years or older

“Dylan is grounded for two weeks.”

“Grounded? Isn’t he a bit old to be grounded?”

“Mom found a bag of pot in his room and she went nuts. She wanted to turn it over to the cops to teach him a lesson. Dad came up with the idea of grounding Dylan instead. He can’t go anywhere and none of his friends can come over. He’s got a long list of projects to do around the house.”

I sighed. I had been looking forward to talking with Alex, but my sister Emily was embarrassing me in front of her long-time best friend. I continued brushing our pool and pretended to not hear my sister talking.

Alex was a tall, thin beauty with shoulder-length light brown hair. This was my favorite time of year to talk with her. She was incredibly smart and incredibly driven. Saturday, she would graduate valedictorian from my sister’s school. During the school year, she didn’t give boys the time of day. Once school was over, she flirted like crazy until she found a boyfriend. I enjoyed flirting with her. Because she was so smart, she was great at word play and could keep up a constant stream of innuendo and double entendres.

Alex walked over to me.

“Not the best start to your summer, Dylan?”

“I would consider you being here a good start.”

Alex smiled. “Let me really give you a good start.” She grabbed the bottom of her T-shirt and slowly pulled it up, exposing her long sexy stomach. A little higher and her small red bikini top came into view. She flashed me a smile when I mimicked a wolf whistle. She pulled her shirt off then turned around. The back of the bikini top was two strings. She slowly slid down her shorts, revealing a thong bikini bottom and her small ass. Alex ran regularly to keep in shape. She shook her ass at me as continued sliding her shorts all the way down.

“Down boy, don’t you have some pool brushing to do?”

I had forgotten the pool while watching the show Alex gave me. I glanced at my sister Emily. She was applying sunscreen and giving me a disgusted look. My sister was good looking as well – dark brown hair that tumbled down past her shoulders, dark brown eyes, long dark lashes, a pretty face and a body with many appealing curves. She was wearing a white bikini that I considered on the skimpy side, though it had a lot more material than Alex’s.

“So Dylan’s going to be our pool boy today?” smirked Alex.

“I’m almost done here, then I’ve other chores.” I had already mowed the front and back yards, and pulling weeds was next on the hit parade.

“I’ve always wanted a pool boy,” said Alex as she gave me a sexy pout.

I continued talking with Alex, acting the straight man to her constant flirting. Emily had told me a few summers back that flirting was how Alex blew off steam after the school year and she got upset when a guy took the flirting to mean that it was open season to hit on her. Alex liked being in control of her relationships. Emily was laying out on one of the four chaise lounges and listened with amusement to our banter.

Emily had invited her three best friends to spend the day hanging out around our pool. They were off from school because seniors didn’t have to take finals. They had tomorrow off too, then would do some pre-graduation events on Friday and graduate from high school on Saturday. I had done the same last year.

Emily got a text, checked it, and announced that Dakota was here. She went into the house to let her in.

Alex said to me in a sultry voice, “Be a good pool boy and I’ll make it worth your while.”

I smiled and continued brushing. Worth my while? That sounded hot, but I knew she was just flirting.

Emily’s friend Dakota came out to the pool and Alex left me to join them. My sister happily told Dakota about my being grounded. I smiled to myself because Emily didn’t know the whole story. Mom had indeed freaked out when she found the bag of pot, and she really had almost called the cops to “teach me a lesson.”

Yeah, a couple of years in jail and a criminal record would make a great lesson.

Fortunately, Dad had been there to calm her down. Dad pulled me aside and told me he didn’t consider that I smoked pot a big deal. “I smoked pot at your age.” However, he had been very disappointed by my bringing pot into the house. “Cities can try to seize the house when cops find pot. Pot doesn’t have the owner’s name written on it and you put all of us at risk by bringing it home.” Dad then had told me if I accepted the punishment and did a good job on the projects around the house, that he would pay me for the work.

“Jesus, you were stupid,” Dakota said to me. That was Dakota – she said whatever she thought.

I shrugged. I had been stupid. “Why aren’t you guys laying out at your pool?” Dakota’s parents had money and their house was much nicer than ours. They had given her a Beemer convertible for her sixteenth birthday.

“The bursa evi olan escort pump and some other equipment are out. The parts are on order. The repair company will come out next week to fix it.”

I nodded and went back to work. I brushed some sections twice so I could be around when Dakota stripped down to her bikini. Dakota took off her shirt and shorts to reveal a bright orange bikini. She also had bright orange fingernails and toenails. Impressive color coordination. Dakota had a very toned body as she had played on the school’s volleyball team. Dakota was average height like Emily. She had blond hair cut short and a perfect smile. Sadly, her nose was too big so she wasn’t as good-looking as the other girls. Still, I would leap at the chance of going out with her, but I doubted that I have a chance – she seemed only interested in guys who had cars at least as nice as hers.

I finished cleaning the pool, dove in to cool off and was putting the pool things away when Faith arrived.

“Hi, Faith!” I said with genuine enthusiasm.

Of Emily’s three best friends, I liked Faith the best. All of them were smart and good-looking. However, Faith was very sweet and mature and made me feel good every time I talked with her. Nothing got her excited or angry. The few times I had had big fights with Emily, I had called Faith for advice on how to patch things up. I had never had a chance to date Faith as she had been dating the same guy for the last three years. He was finishing his junior year in college. Faith was a little on the short side without much in the way of curves. Her black hair came down almost to her waist. She had a really cute face that made her look a few years younger than eighteen.

I toweled off and headed into the house as Emily once again told the story of my being grounded. I hadn’t stuck around for the reveal of Faith’s bikini as she wasn’t the type of girl that I felt good about ogling.

As I reached for the door handle, I heard Alex’s voice. “Pool boy! Could you get us some drinks?”

I ignored her and went inside. I got out a pitcher of lemonade and poured myself a glass. I thought about something else Dad had told me. “Emily dated this football player for a while and she hasn’t been the same since. She’s not the happy, bubbly girl she’s always been. Your mom and I have tried to find out what’s wrong, but she always denies that there’s a problem. While you’re home, do what you can to make her happy.” I had only been home a few days from college, but I had noticed the change and it made me sad. I loved Emily. Yes, we fought like every other brother and sister, but for the most part we got along very well.

Drinks? What the hell. Hopefully if I brought out drinks for her friends, it would make Emily happy. I pulled out five plastic cups, filled them with lemonade and took them out the pool.

“Lemonade!” I announced to the delight of the girls. As I gave Faith hers, I checked out her bikini – it was a blue one with a conservative cut.

The girls were sitting or lying on chaise lounges. I was left with a chair. I mainly listened as I drank my glass of lemonade. Whenever I said anything, Alex would twist it into an innuendo, much to the other girls’ delight. Alex’s chaise lounge was next to my chair and beyond her were Emily, Dakota and Faith.

“Have fun! I’m off to pull weeds.”

I pulled weeds in the front yard until I got hot, then I went in the back and dove into the pool. When I got out, Alex called, “Pool boy! More lemonade please.” She held up her cup. “See, I marked the cups so you can keep them straight.”

I snorted. I was tempted to tell Alex to get it herself, but decided to make everyone happy. “Okay, another round.”

I took the cups inside, filled them with lemonade and brought them out.

“Thanks, pool boy,” said Alex while batting her lashes at me. What could she have meant by making it worth my while?

Again, I sat with them as I drank my lemonade. Again, Alex amusingly twisted my words whenever I said anything. I went back to the front yard and pulled more weeds. When I had finished pulling all of them, I dove into the pool again. When I got out, Dakota asked, “Dylan, could you get us something to drink with more kick than lemonade?”

“You mean like beer?”


“No. If I gave you any of my dad’s beer, he’d notice and I’d catch hell.”

“Please, Dylan?” asked Emily. “It would nice to catch a little buzz while we lay out.”

I sighed. Emily seemed to be having a good time and I didn’t want to put a damper on her party. “I have some wine coolers hidden in the garage.” That brought smiles to the girls’ faces. “I was going to pull them out when I saw Megan next, but I can’t see her for two weeks. But! Wine coolers aren’t cheap. You’re going to have to pay me for them.”

“Okay,” said Dakota.

“Megan?” asked Faith.

“My girlfriend from college. I’ll show you a picture in a minute.”

Megan lived 45 minutes from me altıparmak escort and I had planned on having her over today before Mom found my pot. I had placed the wine coolers with some ice in a cooler so they would be cool when Megan got here.

“So no nookie for you for two weeks,” said Alex.

I ignored her and headed out to the garage. I pulled out the cooler from underneath some of my other stuff. I went in the house and got my phone, then went out to the pool. The girls made a circle around my chair so they would be close to the cooler.

“I’ve got eight wine coolers. I’m drinking two, so some of you aren’t going to get a second.”

“I’ll pass,” said Faith, “so there’ll be two for everyone.”

I took a swig of the wine cooler then pulled up a picture of Megan on my phone. “This is Megan,” I said as I handed Faith my phone.

“Are you two serious?” asked Faith.

“No. We aren’t serious at all.”

Faith passed my phone to Dakota.

“Wow. I thought you would be dating someone better looking,” said Dakota.

“Dakota!” said Faith.

No filter with Dakota. “Yeah, I could do better.” Megan was short, a little heavy and didn’t have much in the way of tits. “I began dating her as a rebound after Chelsea dumped me.” Chelsea had been my girlfriend my senior year. She was a year younger than me. We had kept dating my freshman year at college, then she had hooked up with someone at a Halloween party and had dumped me. “But we have fun together.”

“She’s good in bed then?” asked Alex. She was holding my phone now.

“I can’t complain about the quality or quantity of sex.” Sex was what kept the relationship together.

“Would you dump her to go out with one of us?”

“For a date? No.”

“What about for more than a date?”

I didn’t want to go there, so I decided the best answer was to ignore the question. “How about I tell you guys what it’s like at college?”

“Yeah!” they all said. All four were going to go to college, though at different schools.

“It’s really different than high school in lots of ways. The biggest difference is how people treat you. Teachers in high school don’t get paid a lot, so I think most of them teach because they like teenagers and want to see them succeed. Professors, they don’t give a shit about you. They are at the college to do research and every minute they spend on students is a minute wasted. To the other people who work at the college, you are an annoyance. Yet another problem they have to deal with. If you decide to party hardy and get behind on your studies, nobody will care. Just don’t make a mess when you throw up. The only people who give a damn about you are your fellow students. Find some friends at college like the four of you, friends who want you to do your best and will help you out when you need help. It took me a while to learn to steer clear of the partiers except when I wanted to blow off steam.”

I told them stories of college as I drank my wine coolers. Once everyone was done with theirs, I put all the evidence of the wine coolers back into the cooler then put it back into its hiding spot in the garage. Then I went out to the backyard to pull weeds.

I listened to the girls talk as I pulled weeds. They talked about everything – guys, other girls, celebrities, movies, music. From the conversation, Faith was the only one with a boyfriend currently. Alex sounded like she was ready to start looking hard for a guy. Dakota was open to dating, but wasn’t in a hurry. Emily expressed no interest in guys.

Dakota shocked her friends with, “I’m getting a nose job this summer.” They talked about that for quite a bit, discussing all the details. Dakota was going to have the surgery just before she went off to college. As Dakota’s parents had the money and her nose really did detract from her looks, it made sense to me.

Emily was having a good time, so I was happy. The girls went inside for lunch. Faith came out with a sandwich and a glass of lemonade.

“Thanks for getting us the drinks.”

“I was glad to.”

Faith was so sweet. She went back inside the house and eventually the girls came back out to sun some more. I was almost done weeding when Faith dropped a bomb.

“Elijah and I are thinking of getting engaged.”

“No way!” said Dakota. “You’re eighteen! That’s way too young to get engaged.”

“We’ve been dating three years now and we love each other. He’s the guy I want to marry. I don’t see the point of waiting any longer to get engaged.”

An animated conversation followed. Dakota felt strongly that Faith was too young to get engaged. Alex’s opinion was similar to Dakota’s, but not as strong. Emily had her doubts, but was generally supportive of Faith.

Once I finished weeding, I dove into the pool then got everyone another round of lemonade. I chatted for a while and fortunately no one asked me my opinion of Faith’s possible engagement. I didn’t want to hurt her feelings.

When gemlik escort my cup was empty, I headed to my next project – a thorough cleaning of the garage. I was to take everything out, clean the floors and walls, throw out what should be trashed then put everything else back. I wouldn’t be able to finish the project today as I needed Mom and Dad’s input on what to keep and what to trash.

The garage was on the right side of our house. To its right was a gate to the side yard, which led to our backyard. Our fence was nine feet high and neighbors couldn’t see into our backyard. It didn’t take me long to get hot and dusty so I headed for the pool. When I rounded the corner from the side yard, I got a surprise – Alex was sunbathing with her top off. I stopped in my tracks.

Alex waved me on. “Come on! You’ve seen tits before. Only not as big.”

They had moved the chaise lounges and my chair to the other side of the pool to get the afternoon sun and they were all in the same order. I walked to the edge of the pool close to where Alex was sunning. She was smirking at me.

“Emily’s tits are bigger,” I said, then dove in.

I don’t know why I said it. Probably because I felt like taking Alex down a notch. It had just come out.

I surfaced and headed back to the edge where I had dove in. As I was pulling myself out, Alex said, “So you’ve been checking out your sister’s tits?”

I shrugged as I headed towards my towel. “I’ve seen her in bikinis and night shirts often enough to know that she’s bigger than you.”

I gave her a defiant look as I toweled off. She looked super hot with only a tiny bikini bottom on. Did she shave? I didn’t see any crotch hairs.

“Next time you come to the backyard, pool boy, call out before you turn the corner.”


I went back to garage. Was showing me her tits her way of “making it worth my while”? Was she interested in me? Was she just cockteasing me? I didn’t know.

Pick up, carry to the driveway, set down. Pick up, carry to the driveway, set down. Lot of the stuff was covered with dust. There were lots of paint cans. I opened all of them as most of them were dried out. I found two sets of training wheels – I didn’t think Emily or I were going to need them again. I tried to organize things on the driveway so the review process with Mom and Dad would go quickly. I made sure my cooler was buried under stuff. I was ready for another dip.

I made the hike down the side yard towards the pool. I stopped before I turned the corner and called out, “Pool boy!”

I heard some rustling then Alex called out, “Come on!”

Alex was still topless, though she was lying on her stomach this time. I guessed that at least one other girl had been sunning topless but had put her top back on. I dove into the pool and when I got out, it was Dakota who talked to me.

“Would you please go get us some more wine coolers?”

“I can’t drive anywhere. My parents noted the mileage on my car.”

“I could let you drive my car.”

Her Beemer? Damn. “No.”

“How about if all of us showed you our boobs?” suggested Alex.

I cracked up. It was nice of her to volunteer the other girls to show me their tits too. “Still no. For three reasons.” I sat down in my chair and faced Alex. “Number one, you can’t make that offer as Faith isn’t going to show me her tits and as serious as she is with Elijah, I don’t want to see her tits.”

I smirked as I had caught her out. “Number two, having you guys drink wine coolers now is too risky. It’s past two. How much longer are you going to be here?”

“Two hours,” said Alex meekly. I had finally gotten her back on her heels.

“Then you go home to see your parents. What if they smell alcohol on your breath? What if a cop pulls you over for drunk driving? The shit would hit the fan.”

It was probably Dakota’s idea to drink some more wine coolers, but Alex had been the one giving me grief all day so she was the one that I was going to tell no.

“Number three, I screwed up. I agreed to this punishment and I’m not going to cheat on it. I’m not driving anywhere for two weeks, even if you offered to let me drive Dakota’s Beemer with all of you topless. No more wine coolers today and if you want wine coolers tomorrow, you’ll have to get them yourself.”

“It’s not as easy for girls to get booze.”

I didn’t know what to say. I felt like I had done enough. I stood up and said, “I need to get back to the garage.”

* * * *

The next time I called out “Pool boy!” while standing in the side year, I heard words instead of rustling.

“Come on!” called out Alex.

When I turned the corner, everyone but Faith was topless. Dakota was lying down on her stomach on a chaise lounge, so I only saw a little more of her back. Alex and Emily were lying on their backs. I noticed that I had been right – Emily’s tits were a little bigger than Alex’s. I knew it was wrong to check out my sister’s tits, but they were so nice – big and proud with large, brown nipples. Alex’s nipples were smaller and pink. I walked over to Alex and tried to check out Emily’s tits out of the corner of my eye. Alex gave me a knowing smile. Did she know I was secretly checking out my sister’s tits? Or did she think I was checking out her tits and wanted to encourage me?

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