The Classic Pool Boy Story

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The Classic Pool Boy Story

*All characters in this story are over the age of 18.*

This story does have a slow build up. But I think it’s integral to the story.

*********************************

My name is John. I know it’s a classic and boring name. But what happened the summer between my senior year of high school and freshman year of college was anything other than boring. Though the story is your classic mature woman meets pool boy story.

The previous summer I worked for a pool cleaning and management company. And even though it was simple chemicals, the idea of taking care of a pool really got my gears going. It made me want to pursue a career in chemical engineering. I buckled down hard in my senior year and was eventually accepted to the local state university on a partial scholarship.

My folks were proud of me. Being an only child meant that every aspect of my life was scrutinized. But when I got accepted to college, my parents saw the hard work and dedication and allowed me to rest a little easier during my final summer before my freshman year.

I planned on working a summer job with the same pool company, but the owner (unknown to anyone else) committed several years of tax evasion. The business was shut down and the owner thrown in prison.

“Just great,” I thought. Here I was hoping to make a little extra money this summer. It was too late to start looking for part-time jobs that I would end up leaving two months later.

That was until my dad, a very successful financial analyst, informed me that one of his clients was looking for some help this summer.

“Hey sport,” my dad began as we sat down for dinner that night. “I was talking with one of my clients today. She asked if I knew anyone who knew how to take care of pools because her regular pool cleaner is having surgery and will be out for the rest of the summer. I mentioned to her you may be interested. Her name is JoAnna Summers. If you want the job, it’s yours.”

“Did she say how often?” I asked.

“She didn’t. I told her I’d let you handle that. Here’s her address. Stop by tomorrow and either tell her yes or no.” He slid over a piece of paper with the address. I recognized the neighborhood. This lady was loaded.

“I’ll stop by tomorrow morning.”

My dad slapped me on the back. “Her husband was an early client of mine. She’s been widowed now for the last two years, unfortunately. But you’ll be doing your old man a solid if you help her out.”

The rest of dinner was very nonchalant. Mom and Dad called it an early night. I went to my room and hopped on my laptop. I punched in the address on Google Maps and was greeted to pictures of a beautiful mansion. The pool looked huge from the picture. This was too good an opportunity to pass up.

I shut the laptop and went to bed.

*****

The next morning I woke up to the smell of waffles being cooked by my mom. I met my folks downstairs for breakfast. Dad and I both ate, and I did the dishes as Mom sat down to eat. Dad left for work, and Mom went to her volunteer roll at the local mission.

I finished the dishes and showered. I threw on my swim trunks and a polo shirt. I combed my hair to look as presentable to Ms. Summer as possible. I hopped in my car and made the 10-minute drive out to the rich side of town.

The pictures on Google did this house no justice. It was a beautiful white brick mansion with black accents. There were two lots that separated the house on either side. The house backed up to a golf course. As I stated, this lady was loaded.

I walked up to the door and knocked. A minute later, a woman opened it. Before me stood Ms. JoAnna Summer. I was immediately stunned by her beauty. She had straight shoulder-length blonde hair with shimmering green eyes and a picture-perfect smile. She was wearing a sundress that flattered her figure very well. Not bad-looking for a woman in her mid-40s.

“You must be John?” she asked.

“Yes, ma’am. And I take it you’re Ms. Summer?”

She held out her hand to shake.

“Good to meet you, John. And please call me JoAnna or Ms. JoAnna. Ms. Summer makes me feel old.”

“Yes, ma’am. Understood.” I chuckled a little at her comment. “My dad tells me you need some help with your pool for the next few months?”

“Yes, my regular cleaner tore his ACL cleaning some gutters at his house and will be out of work for a while. Come inside and get out of this heat. I’ll show you the pool.”

I followed her inside and was immediately taken aback by how huge this house was. The foyer looked like it had white marble everywhere. There was a fountain in the middle of the room accompanied by staircases on either side.

“This house is beautiful.”

“Why, thank you. My husband was an architect and designed every detail of it.”

“I understand he died a few years back. I’m sorry for your loss.”

“Well, aren’t you sweet?” she began saying. “Yes, I miss him terribly. Cancer is such an awful disease. But he was a good man that made sure I was well taken care of before he passed.”

We continued escort bostancı walking through the house. I took in every detail I could. Every corner had some unique design that made you look twice.

“The pool is right this way.”

We walked through two giant glass doors and opened up to a stamped concrete patio. The backyard was just as magnificent as the rest of the house. A covered grilling area, fire pit, and small patch of finely manicured lawn surrounded a huge curved pool.

“Wow,” I audibly said.

JoAnna giggled at my comment. “Yes, it’s all my husband’s doing. I entertain regularly, and this space is wonderful for those summer nights.” We continued walking. “And here is the pool.”

The water was crystal clear with very little debris. Whoever was taking care of it knew exactly what they were doing.

“Like I said, I entertain pretty often, so I’d like the pool cleaned at least three times a week. I’d like the water chemistry to be checked at least twice a week, though. Do whatever you have to do to keep it this clear. All of the chemicals, as well as the pump, are behind that fence there. And if you need to buy anything, just go to the store and bring me a receipt.”

“I can certainly do that. Does Monday, Wednesday, and Friday work?” I asked.

“That will be perfect. Here is a key for the gate. Just let yourself in. There are cold drinks in the mini-fridge by the grill. Please help yourself. I don’t want you getting overheated. And please, help yourself to a swim when you’re finished. I’ll try and give you a notice in advance if I have people coming over or plans change for the week. I’ll give you $200 a day in cash. Do we have a deal?”

She stuck out her hand. “Yes, ma’am, it’s a deal.”

We shook hands, and it was deal made.

“I will let you get started then. Let me know if you need anything.” I watched as she walked away. Her hips swayed as she walked into the house.

“Wow,” I thought to myself, “this is going to be a fun summer.”

I snapped myself out of my daydream and got to work. I scooped up the debris in the pool. I checked the water and the filters. Both were fine but would probably need work on Friday.

It took me about 30 minutes to get everything done. By then, I was sweating from head to toe. I kicked my flip-flops off and pulled my shirt off. It felt a little weird being in just my swimsuit in what was essentially a stranger’s house. But I was told I could use the pool. And the water looked very inviting on such a hot day. I made my way to the steps and walked into the cool water. I began to swim laps.

After about 20 laps or so, I made my way back to the steps and caught my breath. I took in the scenery around me. A stunning house, with an extravagant backyard with complete silence, all owned by a beautiful woman. This is definitely the life.

I walked out of the water and noticed my shirt folded up next to a towel on the chaise lounge. Two one-hundred-dollar bills were pinned to the collar of my polo with a note. I dried off and picked the note up. It read, “John, thank you for agreeing to help with the pool. Here’s your first day’s pay. I went to the city to meet some friends. Please lock the gate on your way out. You can leave the towel by the back door. Thanks again and see you Friday. – JoAnna”.

I dressed and left the towel by the back door. Closing and locking the gate on my way out, I got in my car and went home.

*****

Friday.

The days in between were uneventful. I went to the gym, tanned in the backyard, and did the few chores to help Mom out. I met up with a few friends, and they teased me about my new gig. “It’s a story right out of a porno,” they jokingly said. I didn’t think anything of it.

I went to JoAnna’s at around 10:00 Friday morning. I let myself in through the side gate. Figuring I might as well continue to tan, I took my shirt off and lathered myself with sunscreen before I got to work.

I cleaned some leaves out of the pool and checked the water. I added the necessary chemicals. After ensuring everything was put up, I walked over to the pool and kicked my flip-flops off.

“Good morning, John,” I heard from behind me. I turned around to see JoAnna walking towards me with two glasses and a pitcher of lemonade on a tray.

“Good morning, Ms. JoAnna. How’s it going today?”

“Another day in paradise. And I don’t mean that sarcastically.” She gestured to the magnificent backyard after putting the tray on the nearby table. “Would you like some lemonade? Freshly squeezed”.

“Yes, ma’am. That would be great.”

She poured two glasses. As she poured, I took notice of what she was wearing. She had on a big black sun hat, her sunglasses, and a swimsuit cover-up. The small breeze caught the fabric and moved it against her, revealing the pear-shaped body underneath.

“How’s the pool looking?”

“Nice and clean. I put some more chlorine in it. I would give it about 30 minutes or so before getting in to let everything settle.”

“Wonderful. Gives me a few minutes escort bayan istanbul to work on my own tan.” She said as she inched her sunglasses down her nose and looked me up and down.

She set her glass down and untied the sash holding her swimsuit cover. She took the cover off and placed it on the chaise lounger. I was awe struck. For a woman in her mid 40’s she didn’t look a day over 30. Her medium sized round breasts were supported by a red string bikini. Her stomach was flat. Her hips were wide and were more accentuated by the red swimsuit bottoms she wore. The bottoms covered her mound and sat low on her hips. The back was a slightly cheeky cut. There was not a wrinkle on this woman. I tried not to stare for fear of getting hard in front of her.

She sat on the chaise lounge and began rubbing sunscreen on herself. Taking time to cover herself entirely.

“Would you mind getting my back?” She said and snapped me out of my gaze.

I rubbed the sunscreen into her back and we made small talk.

“Care to join me? I see you’re pretty tan as it is. Might as well maintain it.”

“Uh sure, if you don’t mind”

I laid on the chaise lounge next to her. For the next few minutes we talked about my going to school and what I was majoring in. She filled me in on how her husband made his fortune. At the end of thirty minutes or so I got up and did my laps in the pool. JoAnna watched me from her chair the entire time.

When I was finished she offered me a towel. I finished my lemonade and told her I needed to get going. She gave me my $200.

“Have a good weekend and I’ll see you Monday”. I said as I left.

Throughout the entire ten minute drive I could not get JoAnn’s body off my mind. I hadn’t been all the way with a woman yet in my eighteen years of life. I’d gone down on my prom date and received a blowjob from her, but that’s about as far as it got. Now I was having sexual thought about this older woman. Thinking about all the things I would do to her if given the chance.

I got home, said hello to my mother, and raced up to my room. I quickly stripped off my clothes and jacked off on my bed thinking about JoAnna. I came within a few minutes and just let my orgasm overtake me. Between the sun, the laps in the pool, and the wonderful masturbation session I just hand; it took no time before I fell asleep.

And that was my routine for the next three weeks. Go to “work”, spend time in the pool or tanning with JoAnna, and come home and masturbate. “Not a bad way to spend the summer” I thought.

**********

Monday, week Four

The start of week four was when things began to get interesting. I arrived at JoAnna’s at around 9:30.

I went through the side gate as normal. We had a storm blow in over the weekend so there were quite a few leaves and other debris in the pool. I began making my way over to fence where the equipment was when I heard JoAnna’s voice from behind me.

“Good morning John” I turned around to see her walking my way. Both hands were behind her back. She had her sun hat, sunglasses, and cover up on as had become normal.

“Hey Ms. JoAnna. Have a good weekend?”

“It was lovely until that storm came in Saturday night. My guests and I had to move the party indoors. How was your weekend?”

“It was fine. Hung out with some friends and had dinner with my folks last night. Pretty mundane.”

“At least your with your family, that’s what counts.” She said.

There was a slight lull in the conversation before I said “Guess I’ll go get started. Lord knows I’ve got my work cut out for me today.” I began to walk away.

“John, I uh have something to ask you. A proposition of sorts.”

“Uh yea, what can I do for you?” I asked

“Well, it’s been great getting to know you these past couple of weeks. I’ve enjoyed our time by the pool. I was wondering if you would do something for me.” She said.

“I guess it depends on what it is.” I responded

“You’ll think I’m out of my mind but I’d like you to wear something for me when you work on the pool.”

“Wear something.”

She got this big grin on her face “I’d like you to wear this.” She brought her hands out from behind her back and presented me with a pair of blue swim briefs (or speedo, if you will).

I took the speedo from her and held it up. They were dark blue and looked extremely tight. “You want me to wear this?” I asked. My heart now pounding in my chest.

“Yes. I hope you understand where I’m coming from when I say this. I’ve been lonely for a long time now. And as a single woman in her forties my life is lacking in excitement. You’ve got a great body and I’d like some eye candy. Even if it’s just for an hour or two.”

“Uhh, I don’t know about this.” I said.

“I’ll even make it worth your while. If you wear these when you’re working on the pool; I’ll pay you an extra $150 on top of what you’re already making.” JoAnna said with a big smile on her face.

I thought it over in my head. $350 a day for an hour’s worth of work? I’d be crazy not to. But I’d never worn a escort beykoz speedo before. The thoughts of self consciousness flooded my mind. But the money won out.

“An extra $150?” I asked. JoAnna just shook her head, still smiling. “I guess I can do that.” I finally said.

“Fantastic. You can get changed behind the fence there.”

I turned and headed with slumped shoulders to the fenced area. Not slumped because I was sad. Slumped because I was still wrestling with the decision I made. I made it behind the fence and pulled my shirt off. I kicked off my flip flops and held my hands on the elastic of my modest swim trunks. With a quick breath I pushed my hands down and sent my trunks to my feet. I stepped out of them and grabbed the speedo. I held them up in front of me. “I must be nuts” I whispered to myself before stepping my feet into the leg holes and bringing the fabric up over my crotch.

I felt so exposed in that moment. I took a few deep breaths and looked down. They were flattering. My legs looked good in them. My bulge conformed to the tight fabric. I made some adjustments so that everything was tucked in place. I picked up my discarded clothes. With one more deep breath I stepped out from behind the fence and into view of JoAnna.

I approached her and she had a huge smile on her face. I got within five feet of her before she finally said “Well, seems I still have an eye for sizing men. They look great on you.”

I blushed as she said this. “Thanks”, I stumbled.

“Looks like your legs could use some sun.” She joked. I looked down and saw the farmers tan from where my old swim trunks hung. She was right about that. My thighs were pale.

“Guess I’ll get started.” I turned to walk back to the fence to get the net and supplies.

“John” I turned to look at her. “Your clothes”. She held out her hands. I handed her my clothes. The smile never leaving her face.

“I’ll fold these up for you and get you a towel” She turned with my clothes in her hand and walked back towards the house. “Don’t forget your sunscreen” she said. She turned and winked at me before going into the house

I watched her go into the house before snapping out of my trance and heading to the fence to get the supplies.

I grabbed the net and began my work. It took me about thirty minutes to get all the leaves out of the pool. I began to get more comfortable with the speedo as I worked. The sun felt great on my exposed skin. JoAnna must’ve come out while I had my back turned. I faced her direction and saw her laying in the sun in her bikini watching me. I immediately felt exposed again. My cock began stirring in my swimsuit.

I went and put the net away. Next was testing the water. I went back and forth to the fenced area to grab the appropriate chemicals before adding them to the pool. After another fifteen minutes I was finally finished

I walked over to JoAnna by the chaise lounge. I grabbed the towel she brought and dabbed the sweat off of me.

“John, would you be a dear and put sunscreen on my backside please”. She handed me the bottle and flipped on her back.

Her bikini this time was smaller on the bottom than the ones she had been wearing. It wasn’t quite a thong but almost all of her butt cheeks were hanging out.

I squirted the cream on her back and began rubbing it in. I finished up and was going to sit back on my lounger when she said “my legs too John. Can’t have those burning.”

Now I was really nervous. Did I just hear her right? She wants me to rub sunscreen on her legs. My autopilot took over. I grabbed the sunscreen and squirted it in my hands. I began rubbing her left leg up and down. She opened her legs wider. I ran them on the inside of her leg. She let out a soft moan as I finished up. I did the same to her right leg.

“Mmm. That feels nice” she said as I finished up. I removed my hands and went and laid down on my stomach. My erection straining into the fabric of my barely there swimsuit.

“Thank you John.” JoAnna said.

“No problem”.

We laid there and talked for an hour. I turned onto my back once my erection subsided. I kept stealing glances at her gorgeous body. The sweat accentuated her skin and she laid there and tanned.

After another half hour or so she announce she was heading to lunch with some friends. She got up and came over to my lounger and stood over me. She handed me $350 cash.

“Thanks for indulging this woman’s fantasy. Those look good on you.” She said as she stole a glance down to my crotch. “See you Wednesday. In your appropriate uniform”.

Joanna grabbed her towel and walked back towards the house.

I’m was glad when she turned away. My erection started to come back in full force. I needed to get home fast. I pulled my swim trunks back over my speedo and put my shirt on. I dropped the towel by the door and headed to my car.

I made the ten minute drive home in record time. Basically running to my room. I peeled my clothes off and furiously masturbated. Images of JoAnna flashed through my mind. The memory of her smooth flesh like a drug running through my veins. My orgasm was as quick as it had ever been. I exploded all over my stomach. The shot so powerful it even landed on my chest and neck. I laid there for a while just relishing the blissful feeling in my body. I cleaned myself off and immediately fell asleep.

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