The Classic Pool Boy Story

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 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 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 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.

****

Wednesday Week 4

I arrived at JoAnna's at my normal 9:30 time Wednesday morning. I stripped to my "work attire" and got started cleaning the pool. JoAnna never came outside. I was disappointed. I grabbed one of the towels by the door before I got in the pool and found a note taped to the door with my name on it.

"John, went to France last minute with some girlfriends. I will pay you in full when I get back. See you soon. XOXO - JoAnna. P. S. feel free to use the pool anytime while I'm away. It's lovely at night."

"Must be nice to just get on a plane and leave whenever." I said out loud to myself. I got in the pool and did my laps. I didn't linger too long today. I dried off and got dressed. I went home and instead of getting myself off like normal I went and helped mom get things ready for her retreat this weekend with dad.

****

Friday Week 4

Joanna wasn't home yet when I went over there Friday morning. I did my routine as normal and went back home.

Around 5:00 that night my folks left for their retreat when dad got home from work. I had the house to myself until Sunday night.

I ordered pizza and ate by myself. I was severely bored. Then it hit me. I was welcome to use the pool at JoAnna's. Why not alleviate my boredom with a late night swim.

I went upstairs and get my stuff together. I looked at the speedo in my drawer. "She'd probably be mad if I was using her pool without wearing these" I thought to myself as I chuckled. I slipped the speedo on and threw some shorts on top of it.

After gathering my stuff I headed out. The drive was uneventful and it was dark by the time I arrived to the mansion.

I unlocked the gate and was welcome to the sight of the beautiful backyard landscape all lit up like a VIP oasis. I put my stuff down and grabbed a drink from the mini fridge.

I dropped my shorts and waded into the water. It was cooler than normal. The underwater light changed colors and illuminated the clear water.

I floated around for a few minutes just enjoying the night. When a thought popped in my head. Why the heck did I still have swimwear on? It's not like anyone was home.

I waded over to the steps and looked around. No one was around. I hitched my thumbs into the waistband of my suit and peeled the suit down my legs. I grabbed them and threw it to the side of the pool. I was now completely naked in JoAnna's backyard.

The feeling of the water around my completely bare skin was invigorating. I felt so alive and free in that moment. I swam around. I'd never skinny dipped before. I know now what all the fuss was about from the stories I'd read.

After a few minutes I got out the pool and grabbed my speedo. I walked over to the chaise lounges I'd been sitting in everyday with JoAnna and took a seat. I reclined back and admired the landscape in front of me as the cool night air dried me off

I imagined I was talking to JoAnna. Her in her swimsuit, me naked. Another fantasy she probably had. The thought of a NMCF moment like I had seen on the internet immediately got me going.

My cock was at full mast. I immediately began stroking myself. My movements were slow at first. As the fantasy of being naked in front of JoAnna flooded my mind became faster and faster.

"Ughh, JoAnna." I moaned loudly. My orgasm quickly approached. My cock spasmed and I was immediately covered in my own seed. My breathing slowed as the rush of pleasure overtook me. Here I was in someone's backyard, naked, and I had just masturbated. The endorphins hit me like a freight train.

I laid there for a few more minutes before realizing I'd better not press my luck any further. I walked to the back door and grabbed a towel. I dried myself off the rest of the way and cleaned my seed off my body. I threw the towel down and walked back to where my stuff was. I took in the scenery one last time before I got dressed and made my way home. A long sleep awaited me.

****

Wednesday Week 5

I didn't see JoAnna Monday when I went to her house. She must've still been away. I did my pool duties however to make sure it was as good as possible for when she finally came home.

Wednesday morning I arrived a little after 10:00. I went through the gate, over to the chaise lounges, and stripped to my speedo before rubbing sunscreen on myself and getting to work.

Five minutes after I began cleaning leaves out of the pool I heard JoAnna call me from behind.

"John! How are you today! It's been so long!"

"Hey, Ms. JoAnna! Good morning. How was your trip?"

"Oh it was lovely. My friend and her husband offered me a spot on their plane to their house in Monaco. Just a week of beautiful beaches, good company and even better cuisine."

"Sounds nice". I really had no response so I went back to cleaning the pool.

"Did you do anything fun while I was away? The pool looked great yesterday when I got back!"

"Not really. I spent some time by myself just getting ready for school in the fall."

"Seems to me like you did a bit more than that" she said coyly.

"Ummm, what do you mean?"

"Skinny dipping in my pool. Getting yourself off the chaise lounge. Seems to me like you enjoyed your Friday night here." A smile creeped across her face as she said that.

I turned bright red. My stomach turned itself it knots as I tried to figure out how to respond.

"How? I mean... I'm sorry. I didn't meant to... How do you know that?"

"John, first off breathe. I'm not mad. I was once young too you know." She began saying. "And second, I have security cameras all over the place. You can't live this type of lifestyle without someone trying to take it from you."

I was dumbfounded. I had never even noticed security cameras on the property. Though as I looked around in my panicked state, I noticed at least three around the outside part of the property. One directly looking at the pool and loungers.

"I got an alert of motion around the back property. So I checked my phone as was greeted to the sight of my pool boy naked. Not what I was expecting but it was a nice surprise."

"I don't know what to say Ms. JoAnna. I just was by myself and thought I'd do something I'd never tried before."

"You don't have to say anything John. I skinny dip back here all the time out here at night. Lord knows I did enough of it this past week at the beach. It's ok. In fact, I'm glad you got to experience it."

"So you're really not mad?" I asked.

"I'm not. Don't think anything of it."

There was a long silence between us.

"I'll go get us some drinks. You finish your work and we can go on as we have the last few weeks." She smiled and walked back to the house."

I watched as she walked away. The conversation constantly replaying in my mind as I finished my work.

Joanna walked back outside with our drinks and sat in the lounger.

I finished up and sat down on the chaise lounge next to her. She handed me a glass and we sipped our drinks in silence.

JoAnna turned on her stomach and laid flat down. I knew she would ask me to apply sunscreen to her as I had been doing but what I saw next really took my breath away.

JoAnna had untied the top of her swimsuit and very carefully lifted herself up and dropped the top next to her on the ground. I caught just the littlest sight of side boob before she laid back down flat.

She then moved her hands to the strings on her bottoms. She toyed with the knots before untying them. She lifted her hips up slightly and set the bottoms next to her top on the ground next to her.

She had been facing away from me this whole time. But she turned her head and looked at me. She caught me with my mouth open staring at her. She just smiled at my reaction.

"I just spent a week going to a nude beach with my friends and my tan lines are almost nonexistent. Have to keep it up you know."

She grabbed the bottle of sunscreen and stuck her arm out to hand it to me. "Can you get my back, dear?"

I took a deep breath and took the sunscreen from her. I knelt down next to her naked body and began applying the sunscreen as I had several times beforehand.

Normally I would have to worry about her swimsuit. It gave me a natural stopping point. But now, JoAnna's full, naked backside was on full display. My cock stretched hard against my speedo now. It was almost painful.

I started with her back as normal. Moving all the way down to where her buttocks began and stopped. Then moving down to her legs I lathered each of them up. She opened her legs ever so slightly that I was greeted to just the faintest glimpse of her lips. I dared to not run my hand too far up and inside to avoid making contact with them; though I desperately wanted to.

I finished her legs and was getting ready to return to my seat when JoAnna said "my butt John. Can't have that burning now can we?"

If my erection was a 10 before it was now at an eleven. She wanted me rub sunscreen on her ass. This was not the summer job I thought I was signing up for.

Nervously I squirted two dollops of sunscreen on each cheek and then slowly started to massage the cream into her skin. She moaned quietly as I came close to her crack. Every motion making her skin bounce as it returned to its natural state.

Not wanting to press my luck I sat back down in my lounger.

"Thank you John." She peeked over the top of her sunglasses at my erection poking the front of my swimsuit.

I had to say something. But what? I didn't want to say the wrong thing and ruin my job (and all of its perks), but curiosity was getting the best of me now.

"You said you spent your time in Monaco at a nude beach?"

"Oh yes, it was quite lovely. My friends Tony and Sarah have a house right off the coast line. We spent almost every day there taking in the sun with nothing on. It was quite the thrill."

"Interesting." I responded.

"You should try it some time. Obviously you're not opposed to nudity." She said with a wink.

"Maybe."

"I hope I'm not making you uncomfortable John. I really enjoy our time together."

"You're not making me uncomfortable at all. It's just a lot. I haven't had many opportunities to do thing outside my comfort zone so I'm not sure how to go about it. Or react."

"Take everything at your own pace" she responded. "You're a young man of eighteen. You have plenty of time to breach out of your comfort zone." She ended her sentence by giving me a warm, comforting smile.

We sat and talked about her trip for a few more minutes. I was meeting my mother for lunch so I couldn't stay long. I managed to get a few more glimpses of side boob when she reached for a drink. I could've sworn I saw a nipple one time. But that could've just been my horny imagination.

JoAnna paid me my back pay. She asked me to look away as she covered up. I left and went home to change before going to lunch. My masturbation was quick and powerful. The launch was so powerful from being so horny that a drop of semen hit my bottom lip. I unexpectedly tasted it. "Salty" I thought to myself with a chuckle.

I couldn't concentrate at all during lunch. My mind drifting back to JoAnna's nude body laid on the lounger. The silky and plump mounds of her ass in my palms. What a whirlwind. "Don't screw this up" I thought to myself.

"How's your new job going?" Mom asked me.

"It's a dream" was all I could muster to say.

*****

Wednesday Week 7

The routine with JoAnna continued. Although now she had no problem tanning naked around me. Though she always laid on her stomach, I got to see plenty of her ass and even a few glimpses of her lips as I applied sunscreen.

This particular Wednesday morning I arrived at my regular time. No one was around. It wasn't until I grabbed a towel by the door that I saw another note from JoAnna.

It read "John, going out of town with Tony and Sarah again. Be back next Tuesday. Feel free to enjoy the pool while I'm away. Thanks for all of your hard work the last few weeks. - XOXO JoAnna"

Another chance to use the pool? How great was this! Maybe I'd explore stepping out if my comfort zone like she insisted. I already had my plan for Friday night. It seemed like I almost skipped to my car I was so excited. Friday couldn't come soon enough.

****

Friday Week 7

My anticipation for Friday night grew and grew as the hours slowly passed. I made sure Friday morning that the pool was in perfect condition for my night time escapade.

I left my house that night around 7:30. My folks believed I was going to a friends house.

I arrived just as it was getting dark outside. I grabbed a towel by the door and walked over to the same chaise loungers we always sat in.

I didn't even bother with a swimsuit this time and stripped off my shirt and basketball shorts. I stood naked in the backyard, just letting the cool night air surround my unencumbered body.

I made my way down the steps of the pool. The water engulfed me in a way I was growing familiar with. Pure elation took over my mind.

I swam for a few minutes before sitting on the steps and taking it all in. I had closed my eyes to relax when suddenly I heard a familiar voice from behind me.

"My my isn't this a nice surprise!"

I turned in a panic to see JoAnna standing over me. I immediately rushed into the pool and covered myself with my hands as I faced her.

"Ms. JoAnna. I'm sorry I thought I was alone. But what are you doing here? I thought you were on a trip with your friends?"

"Oh Tony and Sarah's daughter is currently giving birth. We left late last night and just got in a few hours ago. I was taking a nap when I got a notification of movement in my backyard."

The cameras, I had almost completely forgotten about them.

She dipped her toe in the pool to test the water. "Feels lovely."

"Can you turn away so I can put my shorts on? I'm uh. In kind of naked."

"I know John, the pool light gave it away."

Damn, how much could she see? How much had she already seen?

"Don't worry about it. In fact" she untied her swimsuit wrap and threw it on the ground. I was immediately met with a full frontal, naked JoAnna. "It's too nice of night to swim with anything on."

Now I have seen a woman naked in person before. I had seen many a pornstars flesh on my internet sexcapades. But what I saw before me was pure perfection. JoAnna's body was magnificent. Her shoulders with beautiful bone structure from her collarbone sat just above her breasts. The were round, with a bit of sag, and capped off by two perky nipples with dime sized areoles. Her stomach absolutely flat. Between her shapely legs was nestled a perfect mound. Tight lips tucked inside of her crowned by a nicely trimmed blonde bush. I stood in awe.

My face must've been one of pure shock and awe. This beautiful mature woman who I had gotten to know very well over the last seven weeks was now willing standing in front of me naked. And if I thought my erection had been as hard as it had been earlier in the summer; I was mistaken. If there was a scale out of ten, my hard Milo ness was at a 13, easily.

I didn't say a word. My mouth was hung open in disbelief. JoAnna made no mention and slowly made her way into the cool night water.

"Ooh. This feels lovely. Don't you think John?" She said.

I just nodded up and down in affirmation unable to speak.

"I just love the feeling of the water on my bare skin. It makes me feel alive."

She pushed past me and began doing the backstroke. The full sight of her front on display out of the water. She swam to the edge of the pool and then back towards me. As she reached me she stopped and just floated. Her hair flowing easily amongst the ripples she had created.

I didn't know what to do. I didn't know where to look or what to say. I just simply stared at her.

She must've sensed my discomfort because she rolled back onto her feet and looked at me. Her smile was infectious. The sight of her wet hair draped across her shoulders was almost too much. She was perfect.

I backed up and sat down on the steps as I watched her.

"John, are you ok?" She asked.

"I'm fine. Just, really wasn't expecting the night to go like this." I responded.

"And just how did you think this night would go?"

"I uh, I don't know" I said.

She moved closer to me. "Did you think you might come here alone and skinny dip in my pool? Then get hard and masturbate in the chaise lounges that we sit at during the week? Clean your cum off with my towel?"

"I." I stuttered.

She didn't let me finish. She moved right in front of me. I instinctively covered myself beneath the water. JoAnna pushed my legs open and knelt in between them. "John, I hope I'm not forward when I do this."

"Do what?" I asked.

JoAnna grabbed my face with her hands and kissed me. A deep passionate kiss. I melted into her mouth. Our lips began moving in sync with one another. I let my hands free from in front of me and placed them on her back, pulling her closer to me.

She broke the kiss off and stared at me in the eyes. Eyes filled with love and compassion in this very intense moment.

"You're a very good kisser John."

"Thanks. I like the way you kiss as well."

She pulled our bodies as close as they could be. "Are you still a virgin my dear?"

"Wow, uh ok. Yes, I'm still a virgin." I began saying. "I mean I've had one blowjob and done oral on the same girl, but yes. I'm still a virgin". I looked away embarrassed.

"Was it any good?"

"Was what?"

"The blowjob, silly" She quipped.

"I mean, yea. It was nice. But I don't really have anything other than my hand to compare it to." I joked.

She laughed at my statement. She leaned in close to my ear and whispered "sit on the top step". Then before returning in front of me she kissed my neck lightly. I moaned at the feeling of her lips on skin.

As if I was on autopilot I broke from our embrace and sat on the top step of the pool. I don't know if she got a good look at me before I instinctively again covered my exposed member.

"John, you need to move your hands." She said before grabbing them.

"It's just. I'm not big at all. I'm pretty much average." I looked away from her as I said those words.

"John. Look at me" She said before grabbing my face with her hand and forcing me to look at her. "Let me just tell you something. A woman who is attracted to you, won't care at all. If you know how to use it correctly you can make any woman feel intense pleasure. Don't get hung up about it. And if someday a woman makes you feel awful about the size of yourself, then she doesn't deserve you." She said sympathetically.

I was blown away by her statement. And even more embarrassed that I said what I said. I nodded to JoAnna. She grabbed my arms and moved them to the side. She looked at my 5.5 inches with a smile.

"It's perfect John. Now, relax."

She kissed my neck. And then kissed my neck again. Slowly and teasingly she made her way down my neck to my torso. I moaned at every touch of her lips against my skin. Even louder when she teased my nipples with her tongue. She continued her journey down. I laughed a bit as she kissed my stomach. She smiled as she continued planting kisses.

She made her way down to my pubic area. Her chin grazing the tip of my cock as she kissed the inside parts of my thighs. Her teasing was driving me insane. The pre-cum began flowing like a fountain. Finally after much teasing, she looked me in the eye and then engulfed my shaft with her mouth.

"UGHH" was all I could muster. I don't know if I was just that horny. Or if it was because she knew what she was doing. But this blowjob surpassed my prom night one by a long shot.

Her head bobbed up and down along my cock. She moaned as she took me into her mouth. The teasing of her tongue was driving me mad. It started slow. And then it became faster. And then deeper. Sensations I never knew I could feel before were being realized. I wasn't going to last much longer.

"JoAnna. Ugh, that feels so good." I put my hand on top of her head and steadily held her as she continued to pleasure me. "I"m gonna. FUCK! I'm gonna cum, JoAnna".

That was all the encouragement she needed. She bobbed her head faster. With one of her hands she grabbed my balls and squeezed lightly. My hips began to buck. My orgasm hit me like a truck.

"UUUUGGHHHHH! FUCK!" I screamed into the night air as I emptied my seed into her mouth. The pleasure was almost too intense as she licked me like a lollipop and cleaned me up. Without breaking eye contact she tilted her head back and swallowed.

"That was." I began saying through shallow breaths. "That was amazing JoAnna."

She smiled. "I'm glad you enjoyed it. But, the night is still young."

Having recovered she sat next to me and we kissed for a minute or two. JoAnna looked me in the eyes. "Did the girl you went down on have an orgasm, John?"

"I don't know. She was really quiet. So I'm not really sure."

"Well then lets get you some practice." She said softly.

She stepped up out of the pool and extended her hand. I took it and she pulled me up off the step. We walked over to the chaise lounge and she sat down. She opened up her legs so that I could take in every inch of her sex.

"Now, I'm pretty worked up already. But if I wasn't, some foreplay would be needed. Little things like kisses, touching my breasts, or caressing my inner thighs. Every woman is different"

I must have been staring like an idiot again at her body unsure of what to do.

"Now, lay down in front of me and put your head between my legs."

I did as I was instructed and began to kiss her lips.

"No John. Even if I'm all ready to go; you should still tease me a bit." She began instructing. "Kiss the inside of my thighs"

I did as I was told. I lightly began kissing the inside of her thighs. Up and down, left and right. Moving closer to her sex as I could without touching it. She squirmed a bit as the sides of my lips made contact with her labia.

I moved up her leg and kissed her mound. "Tug my hair lightly with your lips" she said. I moved my lips closer to her sex and pulled the neatly trimmed public hair gently with my teeth. She moaned even harder.

"That's good." She said breathing slightly heavier. "Now, gently kiss the top of my pussy."

I did as instructed. Causing her to squirm more. I looked up to see her eyes closed with her hand on her breasts slowly massaging them.

"Ugghhh that's good John. Now take the flat part of your tongue and lick my clit. Short strokes."

If what I was doing before was working then this took the pleasure to a ten. Her breathing intensified. Her moaning got louder. I tasted her juices flowing across my tongue. The sweet tang of her pussy overloading all of my senses.

"Suck on it. Suck on my clit John!"

Sucking on her clit sent her into overdrive. She no longer gave me instructions. She was tweaking her nipples between her fingers. JoAnna swung her legs over my back and pulled my mouth as close as she could to her. Her hips now bucking. I was holding onto her as hard as I could.

"Fuck, fuck, fuck! JOHN!!!!!" She quivered as her orgasm took over her body. For what felt like minutes wave after wave of pleasure took hold. I was trying to breathe from being nearly suffocated by her legs as they held me close.

Finally JoAnna relaxed. Her breathing returned to normal.

"You're a natural John." She said with a smile.

I stood up and walked over to her. I bent down and gave her a kiss. Her tongue swirled around my mouth to taste her juices.

"Mmm. I hope I tasted as good for you as I do for myself" she said with a chuckle.

"You taste great".

"Looks like someone's ready to go again." She reached out with the tip of her finger and bounced my cock up and down. I hadn't even realized I was hard again.

"Come on. We're going to my room." She took my hand and led me to the back door. We toweled each other off. I took my time teasing her body. She opened the door and grabbed my hard cock. She drug me through the kitchen, the living room and then to her bedroom.

Her bedroom was just as elegant as the rest of the house. Vaulted ceilings with recessed lighting. Two hand carved night stands lined each side of a gorgeous four poster bed. The far window was plated glass with two doors that looked out onto the landscape of the backyard.

JoAnna led me to the edge of the bed. She turned and kissed me deeply. After a minute of kissing she sat on the edge of the bed and kissed the tip of my cock. A trail of precum left on her lips as she leaned back. She scooted herself up to the pillows and laid back. She opened up her legs and ran a finger down her moist slit.

She tapped the bed in front of her. I crawled between her legs and planted another kiss on her lips.

"Do you want to do this John? I will understand wholeheartedly if you don't want to have sex."

"I want nothing more than for you to be my first, JoAnna." I replied.

I leaned in again to kiss her mouth. This time the weight of my hips pressed against hers. The tip of my cock rested against the outer lips of her vagina. I began lightly thrusting against her clit. Her moans escaping as we kissed. She reached out and grabbed me. She ran my erection up and down her slit to lubricate us.

"Line yourself up with my opening." She commanded. I did as instructed.

The tip of my cock broke through the outer lips of her vagina and was daring to enter her.

"Here's what I want you to do. Go in an inch or two and come back out. Then wait a second and go deeper. Do that until you bottom yourself out inside me." She instructed.

It was now or never. I began doing as I was instructed. I thrusted the first two inches of myself into her moist opening. She gripped the sheets with her fingers and let out a soft moan. I receded and waited. My second thrust was deeper. A louder moan and even tighter grip on the sheets followed. I pulled out one last time and while looking JoAnna deep in her eyes; I plunged for the final time into her. My entire cock was now buried inside this beautiful woman.

"Oh my God" JoAnna exclaimed! She wrapped her legs around my back and just held me inside of her. She brought her hands up to my head and pulled me down into a passionate kiss. I instinctively began circling my hips. She moved hers in time with mine until it was too much and moans once again escaped her lips.

"You feel perfect John." She said as she smiled and looked me in the eyes. "Now go out until you've almost left me completely and then come back in. Go slowly at first."

I began moving my hips back until my tip was at her entrance. I then slowly plunged back into her. I watched as her eyes rolled into the back of her head. I began thrusting in rhythm. Trying my best to keep time and see how her body responded.

JoAnna began to moan. "Yes John! Just like that!" She closed her eyes in pleasure. Now with no instruction I kept pounding into her slowly. "Fuck you feel good." She smiled.

I'm glad she had given me a blowjob earlier because I don't know if I would have lasted long. I kept my thrusting up.

"Go faster now". She commanded. I began to gradually pick up the pace. The sound of skin slapping against skin began to drive both of us crazy. I opened her legs up as wide as I could with my elbows and grabbed her hips with my hands. I began pulling her back into my thrusts. Her head came off the pillow as her eyes rolled into the back of her head. I was now on autopilot. My thrusts became mechanical and I watched with delight as JoAnna squirmed below me.

"Don't stop John! I'm almost there". I began to tire out but I was determined to make her cum again. I kept going and going

"YES! YES! YES!" she was screaming now. Her body began to shake under me. I kept thrusting. The pleasure in my own cock becoming more intense.

"Thats it John!" I loved hearing her say my name. "I'm right there."

"UGGGHHHHH... FUCK". She began bucking her hips wildly. Her hands were now on my back and her nails began digging into my skin. That was all it took for me.

"I'm cumming Jo".

"Cum inside me darling". I thrusted one more time and shot my load deep into her. My body shook as the most intense orgasm of my life took over. I was breathing heavy from the exertion. JoAnna was relaxed but watched intently as my orgasm overtook. She smiled that beautiful smile at me.

I was exhausted. I began to pull back out of her slowly. My cock so sensitive from being inside her. As I pulled out and I looked down to see my cum spilling out of her. She reached her finger down and scooped it up out of her. She brought the finger to her lips and sucked my seed clean off of her finger.

I rolled off of her and laid down. She turned her body in my direction and rested her head on my chest. She brought her hand down to my stomach and pulled herself as close as she could to me. We laid there for a minute before she looked up at me and kissed me.

"You're incredible darling. Don't let anyone else tell you otherwise." She said kissing me again.

"I guess our daily routine is about to change." We both laughed at my comment.

"The best thing is, the summer is only half way over."

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

JoAnna and I would continue having sex the rest of the summer. Often times now I would clean the pool naked and then she would reward me with a blowjob. We'd tan and swim. I still got paid, but being with her was payment enough.

She taught me a lot that summer. We tried every position we could think of. She mentored me on the best ways to please a woman. We had incredible sex. We had even better conversations.

Summer did eventually end. As did my time having sex with JoAnna. I went to college that fall. And within two weeks of my being there I began dating my now wife, Lindsey. The lessons from JoAnna made me feel like I could make any woman feel treasured. I was honest with Lindsey about that summer. And she never made me feel bad in anyway about it.

The following summer and for a few more after that I continued to clean JoAnna's pool. I continued to wear my "uniform" which Lindsey appreciated the few times she came with me to JoAnna's to swim. The two of them became close.

JoAnna did eventually begin dating someone during the course of my sophomore year of college. His name was Michael. Michael, JoAnna, Lindsey, and myself became close. We went to each other's weddings eventually. They became like and Aunt and Uncle to Lindsey and I's kids.

The time I shared with JoAnna that summer will forever be a core memory for me. Those memories now flooding back to me years later as I read her obituary. I'm glad she's with her first husband again. I'm glad for our time together. Happy forever to have known JoAnna Summers.