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Supervisor and Cashier Part VII: Her Parent's Pool and Bedroom

"Ashleigh invites Jack to a pool party at her parent's house and later, up to her parent's bedroom."

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Author's Notes

"Apologies for the delay on this story. My pace of life, thankfully, has picked back up a little and writing time has been condensed. I still plan to continue writing this series and its spin-offs. I have decided that the 'Supervisor and Cashier' series, will be ten parts. <p> [ADVERT] </p>The main part of this story, Part VII, takes place on a Sunday, during the fourth week of July 2017. I do encourage you to read the first six stories. Either way, enjoy the story below."

A week had passed since Ashleigh, and I had gone to see a Wednesday night showing of “The House,” and we were both working a late Wednesday night shift. Last Saturday, we both worked the late shift that night, and I followed her home to have an in-person demonstration of one of her new bath bombs. Afterward, I was on my knees, scrubbing some soapy water that found its way out of the tub due to Ashleigh and I having extracurricular activities in the water.

But, as I mentioned, it was now Wednesday night. I was the closing self-checkout cashier, and Ashleigh was the final regular cashier. It was slow, and around 10:30 pm, Ashleigh and I were chatting as we cleaned some of the registers.

After a few minutes, Ashleigh said, “Hey, so, my parents are out of town this weekend, and I’m throwing a party at their house since they have a pool and covered patio. Wanna swing by?”

I stopped wiping down the register and teased her. “Just swing by?” I said.

Ashleigh rolled her eyes and said, “Okay, maybe more than just swing by. I want you to come and hang out. I know you don’t work. You never work on Sundays.”

She was right. I always had Sundays off. “Alright,” I began. “Since you asked so nicely, I’ll stop by and hang out.” And I said it with a little sass.

“Thank you, Jack,” she said. “Should be fun. Gonna order pizza, and we have plenty of drinks already. It’s gonna be a fun relaxing Sunday.”

“What time do you want me to show up?” I asked.

“Anytime between noon and one should be good,” she smiled, brushing her hair back.

“That will work. I’m looking forward to it.”

Ashleigh smiled, and we continued to clean the registers. The last 25 minutes of our shift went by fast, despite the lack of customers. Once the night cashier arrived, Ashleigh and I clocked out. In the parking lot, Ashleigh gave me a “follow me home” face, so I did. I think that is self-explanatory, so needless to say, it was a fun night.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

On Sunday, I arrived at Ashleigh’s parent’s house about a quarter ‘til one. I didn’t bother knocking on the door or ringing the doorbell. I simply walked around the side to the gate.

“Jack! You made it,” Ashleigh exclaimed. She ran up to me, as her 34B breasts bounced in her small bikini. She had yet to get more than her legs in the water. Jumping into my arms, Ashleigh kissed my cheek before my lips.

“I just ordered the pizzas. They should be here soon,” Ashleigh said. “Now, let me introduce you to my friends.”

Ashleigh had invited a few of her friends who were accompanied by their boyfriends. The girls were seated on the edge of the pool with their legs in the water. Their boyfriends had already hopped in the pool. One couple was Noel and Braxton, another Pam and Billy, and the third couple way Mikayla and Eli.

“The guys are now useless as they have already dived in the pool,” Ashleigh said. “Now, you can’t get in before the pizzas arrive because you have to help me answer the door.”

Why we waited, I sat in a chair next to the pool with Ashleigh on my lap. The three couples and I chatted. The four girls all went to the same high school with Noel and Braxton and Mikayla and Eli dating since then. Pam had met Billy during the first semester of their freshman year of college. About 25 minutes into our conversation, the doorbell rings. Ashleigh’s parents had the doorbell to ring in the back patio, too – I thought that was fancy ass shit.

Ashleigh stood up and grabbed a coverup on the way inside. When we arrived at the door, I took the pizzas and breadsticks from the delivery guy while she paid. No, the delivery boy didn’t get a show, but he did get a beautiful view of her legs – which he did stare at. As we walked back out, the oven timer went off.

“Fixing something else?” I asked.

“Cookies for dessert,” she smiled.

I carried the pizzas outside, and the three couples were already out of the pool and ready to eat.

“Jack, come back in here and get the cooler!” Ashleigh yelled from back inside. I returned inside to grab the large cooler, which was full of drinks as she carried out a tray of fresh cookies.

Now Ashleigh’s parents had plenty of deck chairs and table space. Her dad was a real estate manager, and he had plenty of real estate at his home. But none of us took advantage of it. The girls all sat in the laps of their guy while we ate the pizza, breadsticks, and cookies. The conversations were tame and didn’t consist of sexual topics. But each girl wiggled their hips from time to time.

Pam and Billy were the athletes of the group. Billy was a baseball player and had a muscular build. I’m confident that Eli and Braxton held the same opinion as me that we may be wished each of us had half his build. Braxton and I were average builds where Eli was a little stockier like a football lineman. Billy’s girlfriend, Pam, was barely five feet tall compared to his nearly six feet. She was skinny and toned as she was a runner at the girl’s university and had jet-black hair with smaller breasts.

Noel was a brunette and was an exact replica of Ashleigh’s body – about 5’7, athletic, but not as athletic as Pam, and 34B breasts. Braxton was about 5’7, too, and again, had an average build. Mikayla was the curviest of the group. Her wide hips, big ass, and 36D breasts (Ashleigh told me) made her stick out compared to her other friends. She was sexy in her own right and had long brunette hair.

Now each girl was wearing a bikini that didn’t hide much. Ashleigh told me this was normal because they each liked to show off and tease each other’s boyfriends. They all were very comfortable around one another as I would learn more later. But after we ate and conversed, Noel spoke up and suggested, “Hey, why don’t we set up the volleyball net and play a round or two?”

“That sounds like fun! Let’s do it!” Ashleigh responded as she and the other girls jumped up.

Us guys stayed seated and watched the girls clumsily, take the net out of the pool storage shack, and then set it up. Of course, there was the view, too.

“Are you four pervs going to just sit there, or are you going to help us?” Mikayla shouted from across the pool. The four of us got up and helped set the net up. Then we all climbed into the pool.

“What are the teams?” Braxton asked.

“Cocks versus pussies?” Pam proclaimed.

“For sure,” Ashleigh nodded. We all agreed and separated to our sides.

“What are we playing for?” Noel asked Ashleigh.

“We’ll play the best of three sets,” Ashleigh began. “The person who scores the winning point in the second win for their team gets to take their partner into the shower room and…” her voice trailed off.

“And what?” implored Noel.

“And they get to decide what happens. Their partner has no say,” Ashleigh proposed slyly.

The guys all agreed, and then the girls did, too. It was a spirited first game with several solid rallies, but the girls won 21-17. The second game was a back-and-forth battle. The girls led 26-25 when a long rally ended with Pam scoring the final and winning point for the girls. After a big group hug, accompanied by joyful cheers, Pam looked over at Billy with ‘come with me’ eyes.

They climbed out and entered the shower room, which was basically a shack. It also had a bench for changing. It was simple yet very nice accommodation that was going to come in handy.

The remaining six of us got out of the pool only briefly to grab more food and drinks. While we grabbed our food, Ashleigh informed me that her friends had two rules for pool parties. The first was, if they want to have any sexual fun with their date, they must do it in front of everybody. That is why it was a treat for the winning point scorer to be able to have fun behind the closed walls of the shower room. The second rule was, if you chose to have sexual fun with your date, you must remain naked for the rest of the party. Apparently, these rules dated back to their years in high school.

I was a little shocked to hear these rules, but they didn’t bother me. Ashleigh made sure it was clear to me that no sharing ever occurred. The closest anyone could call a threesome was one of the girls holding another girl’s hair as a blow job was being performed. Other than that, there was ogling with playful teasing and flirting, but nothing more. They were also fortunate that her parents had tall shrubs intertwining with a steel fence that kept the backyard closed off from peeping eyes.

Then we all heard Pam moan, “Oh William.”

“Oh boy,” said Mikayla

“Yep,” said Ashleigh, and she turned to me. “She only calls Billy, ‘William,’ when he is fucking her in the ass.”

“Come on, everybody. Grab your food and drinks, and let’s hop back in the pool and listen!” Noel was clearly excited to listen to her friend get fucked. We all gathered to the side of the pool and hopped in. The shower room was located about ten feet off the edge, along the long side of the pool. We all sat there for the next few minutes, enjoying our food as Pam moaned and yelped, while Billy grunted as he fucked his girlfriend. Then we heard the pair of them orgasm.

A few moments later, Pam poked her head around the door of the shower room.

“Ashleigh,” she paused as she saw that we all had listened to her and Billy fuck. “You guys didn’t,” Pam asked, knowing the answer. We all nodded like excited school children.

“You guys are terrible … But I would expect nothing less. So, Ashleigh…” Pam’s voice trailed off.

“Yes, Pam,” Ashleigh answered.

“Are we enforcing the rules today?” Pam asked softly.

“Why wouldn’t we?” Ashleigh responded as if she was surprised.

“Well … Jack is new here and…” Pam began, but Ashleigh interrupted her and asked me a serious of questions.

“Jack, do you know what just took place inside the shower room?”

“I do,” I said firmly with a nod.

“Have you ever seen a naked woman before?”

“I have.”

“Have you ever seen a naked man before?”

“I have been in a men’s locker room, yes,” I answered slowly and sheepishly as I had to admit I had seen another man naked before as if that was a surprising answer.

“See Pam. Jack is no stranger to nudity or sex. The rules are the rules.” Ashleigh said, and Noel and Mikayla agreed with her.

“Fine.” Pam sighed. She knew she had lost but also hinted that the rules were never going to be lifted and knew it.

As Pam and Billy walked out, we all whistled, hooted, and hollered at them. Pam wiggled her ass to the six of us before leading Billy to get more food. Each of them followed the rules and stayed nude for the remainder of the party.

Noel and Braxton were the first couple to break away us three couples lined up on the edge of the pool. There was a line of four loungers, and as Pam and Billy sat on a lounger at one end to eat their food, Noel and Braxton claimed the lounger on the other end. Braxton dropped his trunks and laid on his back. Noel stripped off her bikini, got on her knees, and started to suck his cock.

“Like clockwork,” Mikayla said.

“Every time,” Ashleigh said to Mikayla. “She always starts with a blow job for Braxton when she is with us,” Ashleigh clarified to me.

Pam and Billy watched as the four of us in the pool did. I was admiring the openness each couple had with one another, too. But it wasn’t long before Mikayla had admired enough and ushered Eli out of the pool.

“Watch this, Jack,” Mikayla said to me as they climbed out. Ashleigh and I both turned around and followed the couple strip and walk over to a fire pit where Ashleigh’s father had built a circular stone bench. Eli was already hard as he could be when he sat down. Mikayla didn’t hesitate to get on her knees and in one swift motion, was titty-fucking her boyfriend’s cock.

Once Pam and Billy had finished their food, Pam laid Billy down on the lounger, but she climbed on top and sank onto his cock. They made out for the longest time, with Pam moving up and then back down on his cock sporadically. Before anything else happened, Ashleigh led me out of the pool. She grabbed an oversized towel from the pool storage shack and spread it out on the grass. Placing her hands on my shoulder, she kissed me and said, “We aren’t going to do anything here because I have plans for later.” She winked and said, “But take off your trunks and don’t if you get hard … errr … harder.”

We smiled at one another and removed our swimwear. Ashleigh laid down on her side, so I did the same and spooned her. My arm wrapped around under her breasts and my cock hardened more. Ashleigh slipped it between her legs and giggled as she did. It was at this point we both drifted into a nap.

When we awoke, maybe 20 or 30 minutes later, a few things had changed. We awoke from Noel’s cries of joy from Braxton and them fucking in a missionary position in the grass, not 20 feet from us. On the opposite side of the pool, Mikayla was bent over a countertop next to the grill. Eli was plowing her from behind. Pam was still on top of Billy, but now, she was bouncing on him continuously.

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My cock, which had fallen soft during my nap, was growing once more between Ashleigh’s thighs. “Are you enjoying the views?” She asked coyly.

“Don’t pretend that you aren’t,” I said in response because I could feel her pussy was wet. She smirked, looked down at her pussy and my cock, and leaned back to kiss my cheek.

Just then, Braxton released a roar of a grunt and came inside Noel. Once he regained his strength, he moved backward and immediately began to eat out her pussy. Noel had an orgasm soon after. Pam was not quite as she and Billy both came at the same time. Moments later, Eli then burst his load inside Mikayla, who yelled ‘fuck’ at the top of her lungs. The pair then went to the pool where Eli climbed in, Mikayla sat on the edge, and he went to work on eating her pussy.

Noel turned and looked at Ashleigh and me as she said, “Have you two just been laying there this whole time?” She was still catching her breath.

“Yeah, why?” Ashleigh said.

“Don’t you want to have fun with Jack?” Noel asked.

“And what if we want to see him, Ash?” Mikayla added as she moaned from Eli, still licking her pussy.

“Yes, I do, but I want to save that for later when I have him all to myself. You can admire him as is, Mikayla.” Ashleigh lifted her leg, revealing my entire hard on to the others as it rested on her inner thigh next to her pussy.

Pam and Noel took a gander, as did Billy and Braxton. Mikayla, who still hadn’t laid eyes on Ashleigh or me, finally came from Eli’s mouth skills. As rapid as she came, she hopped in the pool and swam over to the side of the poor nearest Ashleigh and me with Eli.

“Are you sure you don’t want to play with Jack?” Pam asked. “I think he is ready,” she said with a giggle.

“I’m sure,” Ashleigh said as she dropped her leg back down. “Maybe next time. I don’t want to spoil Jack during his first pool party,” she grinned and looked up at me. In truth, I didn’t mind not doing anything. I knew that later, Ashleigh and I would have fun. Plus, I’d been running entirely on adrenaline. The entire experience of being nude in front of others like I had been was like nothing I’d ever done before, and I was nervous I’d ‘pop’ too soon in front of the others.

Pam and Billy moved a lounger close to the side of the pool. Except for Mikayla and Eli, who were still in the pool, the rest of us were laying on our sides, spooning with the girls pushing their asses into their man’s crotch as close as they could.

For the next 45 minutes or so, the eight of us exchanged sexual stories and truths. But then the conversation faded to more ordinary topics of discussion about life, school, sports, among other things. Eventually, it came time for the other three couples to leave. Ashleigh and I slipped back on our now dry swimwear, and the others slipped on enough clothes to drive in. I shook each of the guys’ hands and said it was a pleasure to meet them. I did the same for the girls, but they wanted a hug – a tight one.

I followed Ashleigh as she walked the six of them through the house and out the door. As Noel walked through the door, she turned around and said, “I hope to see you at another pool party soon, Jack. Maybe you can come to Illinois next month. The house the four of us are renting this year has a pool!” Pam and Mikayla agreed.

“Maybe so. See you ladies and gents later,” I said and waved.

“Bye!” Ashleigh waved, smiled, and giggled with her friends as the guys waved and rolled their eyes playfully.

Once she closed the door, Ashleigh placed her arms on my shoulder and kissed me. “We need to take a shower. This pool water feels yucky to me, and I’m not going to have fun indoors feeling yucky.” She laughed as she stuck her tongue out in playful disgust.

“I agree,” I said.

“Separate showers, though, and I’ll go first,” she said, and I followed her up the stairs. We went into the master bedroom.

“Why are we in here?” I asked curiously.

“My dad is strongly considering moving my family to Texas for a potential new job. All our family and friends are here. My mom is on board. So, to show my displeasure, we’re going to have sex on their bed,” Ashleigh proclaimed as she stripped out of her bikini.

“Wow, that is a bummer,” I said.

“The good news is that I get to still go to school in Illinois, no matter what. But my summers are questionable, and I’d like to hang out with my friends during the summer, too.”

I walked up to Ashleigh and hugged her as I could tell she was getting upset.

“Thanks, Jack.”

“You’re welcome.”

“Okay, now wait here while I shower,” Ashleigh said as she directed me to her parent’s bed.

Ashleigh was never quick in the shower. I waited and scrolled through videos on YouTube. On the nightstand next to the bed was a picture frame with four pictures of her parents. Her mom was very attractive, like Ashleigh. Her good looks were clearly passed down to her daughter. She looked younger than she was, and her father probably felt like me when I was with Ashleigh – we were outkicking our coverage.

When Ashleigh emerged from the master bathroom, she was wearing a pink bathrobe that just barely covered her butt.

“My mother’s robe. It’s a little big for me,” Ashleigh began as she caught my stare. “You’ve probably noticed the pictures there on the side, especially the one of my mom in her black bikini. You can tell she has more hips and tits than me.” She chuckled and collapsed on the bed onto her stomach. She teased as she was aware that I found her attractive just the way she was.

“Well, I’ll go shower now. Be back soon,” I declared as I ran my hand down her leg. Ashleigh smirked at my touch.

“I left two towels for you since you probably don’t want to wear my dad’s robe. Also, ignore the lube in the shower. Now you know where I get my lust for shower sex,” and she winked.

Ashleigh and I had shower sex a number of times before. I turned around, winked at her as trunks dropped to the floor, and walked towards the shower. Now I was never quick in the shower either and thoroughly enjoyed the warm water washing away the chlorine, sweet, and sunscreen from my body.

I dried myself with one towel and wrapped the second around my waist and head back to Ashleigh. She was still on her stomach, her butt and pussy right in my view as I entered the bedroom. We both knew what was ultimately going to happen, so I removed my towel and flung it onto the bed. Gently, I climbed on top of her, moving her robe up just the little bit needed for my cock to rest between her butt cheeks.

Leaning down close to her face, I whispered, “Whatcha doing?”

“Mmm, texting the girls,” Ashleigh happily responded from my touch.

“Whatcha talking about?” I said after I kissed her neck.

“Well, I did send a pic of the robe I’m wearing,” and then she showed me some of the responses from Pam, Noel, and Mikayla.

“It looks like they are pretty smart girls,” I began. “I think they can predict the future.” Our eyes locked, and we kissed slowly.

As our lips broke free, Ashleigh pleaded, “I need you now. I’ve waited all day for you and me in his bed.” Her right hand slid back and stroked my cock as she raised her butt into the air. Balancing my body with my left arm, my right hand rubbed her hand, which held my hard-on. Smiling, she released her grasp on my, and her hands gripped the edge of the bed. I teased her wet entrance with the head of my shaft.

“Jackkk,” Ashleigh pleaded once more.

Without further hesitation, I sank my length into her warm, wet pussy. Now balanced with both my hands at her sides, I held myself in her depths as I bent down to kiss her. With our lips meeting once more, I slowly began to move my hips. Ashleigh broke the kiss as one thrust caught her attention.

“Ahhh,” she exhaled with her mouth wide open with shock, but it faded to a smirk of lust.

Ashleigh turned facing forward and gripped the edge of the bed more. Every few thrusts I pushed harder into her, causing her to wince. When she summoned the strength once more, she turned her back and looked back at my cock disappearing between her cheeks. I held myself above her and admired her ass jiggle as our skin united.

“Make ‘em jiggle more,” Ashleigh said with a seductive grin before she bit her lip.

Slowly withdrawing my length to the absolute edge, I crashed my hips back into her. Her ass absorbed the contact and jiggled more and more. With every crash into her ass, my hips bounced back out, plunge back into her once again. Ashleigh’s purring turned into winces of joy.

“That’s it, Jack,” she said between breaths. I leaned down and kiss her cheek and then her neck. After about a dozen more thrusts into her depths, Ashleigh pulled herself off my cock. She slid out from under me, leaving me on all fours with my fully hard cock and balls hanging down. I watched her hop off the bed and open the blinds to the two large floor to ceiling windows facing us. When she hopped back into the bed, she laid on her side at the headboard and lifted her right leg into the air. With her smooth pussy on full display to me, she said, “Come over here and fuck me like my mom loves for my dad to do to her.”

I climbed alongside and scotched right up against her. Her right arm cradled my head as our eyes and lips connected. I didn’t wait for a plea this time; my right hand guided my cock into her pussy immediately. Once my shaft was securely inside her warmth, my right hand helped hold her leg in the air. I didn’t begin to move my hips until Ashleigh looked down at her pussy. I was looking at her face as I withdrew and pushed forward for the first time. Her mouth slowly opened as my cock penetrated her depths.

Suddenly, Ashleigh orgasmed and came on my cock. She even squirted just a little when her head it the pillow. Her recovery took a few minutes, but I never stopped fucking her. During this time, her hand found her clit as my cock pierced her pussy. She clamped the walls of her pussy down on my length each time my hips pushed it inside.

Eventually, I lost the strength to continue to prop myself up. My head fell beside hers. Instinctively her right hand left her pussy, and wrapped around the back of my head. Ashleigh held my head close to hers, and my lips danced between her shoulder, neck, and cheek. My right hand released her leg and found her left breast. I squeezed it and massaged it, and she kissed my fingers.

My hips began to thrust my cock harder and harder into her pussy. Ashleigh returned the favor by pushing herself into my thrusts.

“Fuckkk,” Ashleigh exclaimed. I moaned and grunted into her shoulder. With the arm I draped over her body, I pulled her tight against me.

Each of our pants, moans, winces, and grunts grew louder with each thrust. I had held on for as long as I could and was going to burst any second. Suddenly, we both yelled, “I’m cumming!” to the other. Cum flew out of my cock and into her as Ashleigh came around my cock. It was synchronized cumming at its finest.

Neither of us said a word. The room was devoid of sound, aside from our panting. As I panted, I kissed her body anywhere I could. I even grabbed her right breast, pulled it up to meet me halfway to kiss the top of it. Ashleigh would be the first to speak.

“You don’t know how bad I’ve wanted that today.”

“You don’t know how bad I wanted that either.”

“Next time we are going to join my friends in the fun. I just wanted you all to myself today,” Ashleigh explained.

I kissed her shoulder and said, “That’s perfectly alright. I’m not sure how I would have performed out there anyways.”

“I think you would have done fine,” she paused and looked into my eyes. “It takes some getting used to. You should have seen everyone the first time. There were six couples. Two of them we are no longer friends with, but the guys didn’t last long that first time and for a good reason. There are a lot of hot chicks around them.” She winked and giggled.

I chuckled and said, “So you didn’t want me to pop quickly and feel bad?”

“Sorta. The first time Andy joined a party, we didn’t do anything either. But the second time, he knew what to expect and lasted just fine. I imagine it’s a mental guy thing,” and she chuckled.

I smiled and turned to kiss her. As we kissed, I slowly started to withdraw my cock from her pussy.

“Don’t take it out,” Ashleigh exclaimed. “Knowing you, you’ll stay decently hard inside me as we lay here.”

My cock stayed in her as we nestled our bodies together. We began to chat about the day, but soon we were asleep.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Suddenly we were awakened by a text alert from Ashleigh’s phone. She grabbed it from the nightstand, opened it, and gasped.

“What’s wrong,” I asked.

Ashleigh held her phone up. There were three missed phone calls from Andy and a text that read, “I saw your Instagram post that you are off tomorrow. I’m driving over there tomorrow. Be at your place at 3. We need to talk.”

 

To be continued with Part VIII

 

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Written by Jack_01
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