Poolside Pleasures

I had been babysitting around town since I was 13 years old. With so many families in the area, it was an easy way to make extra cash if you had a good reputation...and my reputation was stellar! I was certified in CPR, always brought fun activities with me for the kids, and made sure the house was picked up and dishes done before the parents came home. And, after my first year of college, I had grown in my knowledge and experience of children through my major: Early Childhood Education. For this reason, I had become used to getting calls on my cell from strangers, as my number often got passed from one family to another. Word of mouth was my main source of advertisement.

So when I got the call Saturday looking for a last minute sitter for the night, I wasn't surprised. What had surprised me was that I was actually free. Usually Saturday nights were booked months in advance, but the family that had previously secured this night had come down with a bug and cancelled. I was excited to be able to fill the slot and not miss out on the extra cash.

The mother, Mrs. Smith, and I discussed her 4 year old son Andrew and the event that would have her gone until 1am. It turns out Mrs. Smith was on the board of the locally infamous nonprofit Heartbeats for Hope, which specialized in raising money for NICU families who didn't have the funds to pay their hospital fees. Tonight was their annual fundraising gala, so Mrs. Smith would be wining and dining with the wealthiest benefactors in the area. When I asked if Mr. Smith would be attending with her, she said that he was busy at a conference this weekend for work. We scheduled a time for me to arrive and I wrote down her address as she told it to me over the phone. Just as I was saying goodbye, she interrupted.

"Oh! And we have a lovely swimming pool that you are welcome to use once Andrew falls asleep if you like."

I did a little happy dance as I hung up the phone. Little kids went to bed early, and a night by the pool sounded like the perfect way to spend my Saturday.

When I arrived, Mrs. Smith buzzed me in through the gate and I drove my Volvo up a beautiful stone paved driveway to an enormous and immaculate home. I walked into the house trying to keep my jaw from falling on the floor as I gazed longingly over the beautiful artwork, furniture, and interior design. I came to a side table covered in a fresh bouquet of exotic flowers and a half dozen photos in striking silver frames. Many of them were of Mrs. Smith and Andrew, I assumed, but one at the end caught my eye. It was a photo of a man on the edge of a cliff, in nothing but shorts and hiking boots. His dazzling smile and incredibly sculpted body left me feeling dazed when suddenly a voice startled me back to reality.

"Whatcha doing?" The young little boy behind me said with no shyness whatsoever.

"Hello Andrew! I'm Kay," I said as I turned to face him. I gave him my friendliest smile and pointed toward the pictures. "I was just looking at these beautiful pictures of you and your mom."

"Don't forget my dad!" Andrew yelled as he pointed at the photo I had not just been gawking at.

"Oh, is that your father?" I asked innocently, while trying to steady the tingles traveling down between my legs.

"Yes. He is awesome!" Andrew said proudly.

"I bet he is," I replied warmly.

"Andrew, mommy's heading out. I need you to be good for Ms. Kay, alright? And don't try to argue about bedtime. It is 9pm sharp, ok?" Mrs. Smith spoke sternly but with love to her son as she descended the stair case in a sparkling navy blue gown.

"I will mommy!" Andrew declared with a smile. He kissed her goodbye and she was out the door in mere seconds. Then it was just Andrew and me.

The night passed quickly as we played with puppets, cards, and I even showed him a few magic tricks. He asked me to teach him one so he could show his dad when he got home, and it was adorable watching him try to hide a coin between his fingers. When it was finally time for bed, he looked as though he wanted to argue but remembered the promise he made to his mother. To ease the transition to bed, I promised to read him two bedtime stories, and before the book was closed, he had lulled off to sleep.

I gently closed the door and headed downstairs, picking up toys and dishes as I went. I highly doubted that the Smiths cleaned their own house, but I still believed it said a lot about my work ethic when I cleaned up at the end of the night. Once I looked around and saw that everything was looking neat and proper, I glanced beyond the sliding glass doors out to the pool sparkling against the moonlight outside. It was the perfect night for a swim, a warm 82 degrees. I found a cabinet full of lush beach towels, and carried one outside with me. I kept the glass door ajar, just in case Andrew woke up and called for me. Then I pulled my light sundress up over my head to reveal my teal string bikini. It was nothing special really, but I loved how it hugged my curves and made me feel sexy. Not that anyone was around to see me now, but the sentiment still stood. I slipped my sandals off and dove into one end of the pool, swimming underwater to the other end. I burst through the water and threw my head back as the droplets in my long brown hair flung around me. I wiped the water from my eyes and sighed with contentment. This was the life.

I continued swimming for around an hour, allowing the water to lap at my tan skin and make me feel even more beautiful. The moon glistened on the water as I cut through its reflection with each stroke. Finally, I pulled myself out of the water and rung out my hair. Suddenly from behind me I heard a throat clear.

I jumped and turned to find Mr. Smith standing in the doorway. His suit jacket seemed to have been discarded, and his tie loosened after a long day. His shirt cuffs were undone and rolled up on his forearms. His short, dark, curly hair seemed a little wild, and I immediately wondered if he had been running his hands through it earlier.

"Mr. Smith! I wasn't expecting you. Andrew is asleep for the night and Mrs. Smith said you were out of town..." my voice trailed off as he began to approach me, his hands in his pockets and his eyes on mine. A breeze blew past as he did so, and I quickly sucked in a breath as I felt my nipples harden under my wet bikini. Mr. Smith stopped about a foot away, and knelt down slowly to pick up the beach towel at the foot of the lounge chair I had placed it on. He unfolded it as he walked closer and gently wrapped it around my shoulders.

"I got home early," he said softly as he rubbed his hands along my shoulders to warm me up. Had I been shivering?

My arms fell to my sides as he dried them with the towel. Then he began drying other parts of me, gently rubbing my body down with the fluffiest towel I had ever felt. I tensed as I felt his hands on my thighs, fighting the urge to moan from his touch. His hands traveled back up and began to rub the towel over my breasts. I gasped and in that moment his mouth was on mine, his tongue invading my open mouth as I moaned against him. His hands dropped the towel and began to knead my breasts with only the thin fabric of my bikini between his skin and mine. He pinched my hardened nipples and my body responded instinctively, rubbing against his, wetting his shirt and suit pants. My hands traveled up his shirt and pulled at his tie until it was undone. Meanwhile his hands traveled down to my ass and groped me. I began to unbutton his shirt, then unbuckled his belt. The silence was only disrupted by our moans as we continued to entangle with one another.

Who was I? I wondered in shock. I had never been one to be intimate with a stranger and I would never get involved with a married man. But as his hand traveled around my hip to the front of my bikini and stroked my pussy through the wet fabric, I found myself unzipping his pants and pressing my pussy against his hands in a wordless act to beg for more.

Suddenly he stepped back from me and I struggled to catch my breath as I imagined how swollen and red my lips must be right now. He continue to say nothing, but as he stared into my eyes, he shrugged off his shirt and pulled down his pants and boxer briefs, discarding them along with his dress shoes and socks. His cock was hard and thick and beautiful, and I felt my clit throb in anticipation. Was I really doing this, cheating with a married man while on the job? As he stepped toward me once more, I silently screamed Yes!

His hands lifted up to my hips, grabbed the strings of my bikini, and tugged until the thin fabric simply fell to the ground, leaving my bare pussy tingling from the breeze. He looked down and a slight smirk played on his lips. Then he took my hand and walked me back toward the pool. He slid into the water but motioned for me to sit at the edge in front of him. I did so slowly, and then leaned back onto the concrete as his hand pushed my torso back into a lying position. I stared up at the stars as I felt him spread my legs and lick the slit of my wet pussy like I was a delicacy he was ready to devour.

"Oh yes," I moaned as he buried his face in my pussy and sucked on my clit. My hand reached down and tangled in his curls as I thrust my pussy up toward his mouth. He moaned in response and continued to eat me out as I squirmed beneath him. His hands slid under my thighs and gripped me as he began to thrust his tongue in and out. My moans grew louder and my breath raspier as my eyes began to roll back in my head.

"Oh god...oh god yes...I'm gonna come...I'm gonna come...I'm--" my body convulsed and spasmed with an explosion of pleasure as he lick every last drop from my dripping pussy.

I fought to catch my breath as I laid there, my legs dangling into the water while my body tingled from head to toe. I felt his hands travel up and down my body, stroking my skin in delicious little patterns that left me moaning from aftershocks of the orgasm he gave me.

Then he gripped my hips and pulled me down into the water with him. While keeping his eyes on mine, he lowered his face until his mouth hovered in front of my breasts. Then he captured one in his mouth and sucked my hard nipple through the triangle of fabric still covering my chest. I kept my eyes locked with his as I groaned. He smiled and pulled back just enough to slide the wet fabric to the side and take my bare nipple into his mouth again. I cried out and heard the sound echo in the night air. There wasn't another house for at least a half mile, and the noises my body unwillingly made were only turning me on more and more as this man, someone else's husband, gave me wave after wave of pleasure.

I felt his hand between my thighs and spread my legs for him. He thanked me by positioning his hard cock at my entrance. He didn't have a condom on, and though it was not the smartest decision, I wanted to feel every inch of him fill me with nothing between us.

"Wrap your arms around me," he said in a low gruff tone. I did as he asked and was rewarded as he thrust every inch of his glorious cock into my aching wet pussy.

"Unnnghh," I cried out as he filled me. I clung onto his back and he pressed his entire sculpted body against mine as he filled me to the hilt.

Then he began to fuck me.

Hard and deep and rough, he fucked me over and over again. My nails dug into his back as he groaned. "You're so wet for me. You want this so bad."

"Yes," I begged breathlessly. "Please don't stop. Please...yes...keep...going!"

He picked up his pace and fucked me harder, his pelvis rubbing against my clit as I wrapped my legs around him underwater. His mouth found mine again and his tongue filled me while his cock did. The overwhelming feeling of fullness brought my climax closer and closer.

"Come for me," he grunted as he thrust inside me. "I want to hear you and feel you as you come on my cock."

I arched my back as he stroked my G-spot with each pump. Crying out, I felt my body begin to spasm as I came again, this time squeezing his cock with my clenched pussy as I rode this pleasure over and over.

"God yes," he grunted into my ear. "Your fucking pussy feels so good. So tight and wet."

"Oh yes," I cried breathlessly. "Come in my tight, wet little pussy. Fuck me deep and hard. I need you...yes!"

He thrust harder and deeper, holding my hips with his hands as he ground against my clit. "Fuck yes, I'm gonna come babe..." he thrust faster and harder. "I'm gonna come inside your sweet little pussy...I'm so close.."

"Oh god," I moaned as he continued grind against me. "I'm coming."

"Oh fuck I'm coming too!"

Suddenly I felt his hot cum fill my pussy as I convulsed with a third wave of pleasure against his cock. Our mouths found each other and we made out as we came together, our heartbeats racing and our breathing labored.

"Fuck me," he sighed as he pulled away and slipped out of me. "Who are you?"

I fixed my bikini top as I breathed out, "I'm your babysitter."

"Jesus," he ran his fingers through his hair. "You do one helluva job."

I smiled as we stared at each other. I wanted to tell him I was not this kind of babysitter. I had never done this before with any client. But just as I opened my mouth to defend my honor, he pressed himself against me and kissed me deep and long.

"Please tell me you're free next Saturday," he said when he pulled away.

"If you promise me a tip this big every time, I'll be free whenever you need me," I joked.

He brought my hand into the water to feel his already hard again cock and replied, "this big tip will be yours every single time."