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Supervisor and Cashier Part V: On a Break

"Jack finds out the outcome of what Ashleigh and her boyfriend, Andy, discussed."

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Author's Notes

"Sorry for the delay in Part V. Life got busy for a bit. This is the fifth story in the Supervisor and Cashier series. It takes place on Friday, July 7, 2017, four days after the previous story, Supervisor and Cashier Part IV: Confessions. It may prove beneficial to read the previous four stories in the series before this one. Enjoy."

Ashleigh had found someone to take her shifts on Tuesday and Wednesday so she and Andy could spend time together, meet her family, and talk. Andy had dumped a lot of information on her the Thursday prior. I could only imagine what she and Andy were talking about or what conclusions they would reach. I also wondered if Ashleigh would tell Andy about me. I had three full days to wonder about that, and luckily, I had plenty to take my mind off it.

On Friday, I arrived to work to find that Ashleigh was clearly waiting on me since she parked right beside my usual parking spot. She had backed into her parking spot, and I pulled in beside her, so our driver sides were beside one another. We rolled down our windows, exchanged hellos, and then she spoke.

“Have you survived the past three days, Jack?”

“Surviving, Ash. Just surviving,” and I said with sarcasm.

Ashleigh chuckled and said, “Seriously, though, how are you doing?”

“I’m doing fine. As well as can be expected at least not knowing what all was discussed between you and Andy. I've been more worried about you than me,” I replied.

She smiled a fake guilty smile, and we laughed. She began to exit her car. I exited mine once she was out, and we started to walk towards the store’s entrance.

“So, what would your answer be if I said I’m not telling you anything until you come over to my place?” Ashleigh raised her eyebrow as she looked up at me.

I chuckled and said, “I guess I’ll just have to go over to your house after this to find out what you're holding on to.”

“Is that a ‘yes, I’m coming over’ or a ‘no I’m not coming over?’”

“That is a ‘yes, I’ll follow you home after our shift,’” I replied with a bit of sass.

Ashleigh nudged my arm with her elbow and chuckled. “Sounds like a good plan then. Behave yourself in there,” she said.

“I’ll do my best,” I laughed back. “You just don’t screw up any more produce weights.”

We both laughed at that. Ashleigh had messed up once pretty bad, but other cashiers weren’t grasping the new system very well. Our shift went pretty well across the board that day. It was a busy Friday like normal, and like usual, I didn’t take my breaks, and my lunch was only the minimum of twenty-three minutes. I just didn’t trust the office to keep the front-end running while I was gone.

Ashleigh and I clocked out a 10:00 p.m. and headed for our cars. With traffic, we arrived at her townhouse at about 10:30 p.m.

“Did you ever repack a go-bag for your car?” Ashleigh knew I had previously mentioned a “go-bag” for when I stayed the night at friends’ houses or a girl’s place.

“I did repack it. Should I bring it in?” I replied. I was a little shocked she had asked, too.

“It can’t hurt anything if you do,” and she waved me inside. I began to wonder what her intentions were if she was telling me to bring my go bag in with me.

But regardless, it was almost a ritual at this point. I took off my shoes, sat my go bag next to the door, and sat her couch as she poured each of us a glass of water. When Ashleigh came over and sat beside me, we didn’t initially jump into what we were ultimately going to talk about. Instead, we discussed a couple of new baggers and how comical they always are. Not in a mean way, but just how some need more guidance than others to start. Then we talked about what we did over the Fourth of July holiday.

We’d been on the couch for about twenty minutes, and Ashleigh said we both needed to freshen up in the shower, but separate.

“We need to talk before we do anything,” she stated with a chuckle. “I’ll go first. You know how to pull up Netflix. Go ahead and watch something while I shower. I might be a while,” she winked at the end.

“Yes, ma’am,” I said slowly. As she walked off, I stared at her ass as long as I could before she shut the door behind her. I passed the time by watching Netflix, specifically House of Cards.

Ashleigh did take her time because it was about thirty minutes before she emerged from her room. Her hair was still damp, but all she had on was a towel – a small one at that. It barely covered her ass, and had the couch been any lower, I would have had a first-class seat to watch her unmentionables walk by.

“Quit staring and go shower, perv,” she said jokingly. “You know your way around in there. Towels are already out for you.”

I took my go-bag into the bathroom with me. I stripped down and hopped in the shower. The sight of seeing Ashleigh in nothing but a towel certainly painted images in my mind, and my cock was responding to those images. Now on top of bringing my go-bag inside, she had walked past me with nothing on but a towel. The signals were clear and unclear at the same time.

Now a shower after a full day at the grocery store always felt fantastic. The water cascaded through my hair and down my body. It was refreshing to wash the frustrations away metaphorically. However, I couldn’t keep Ashleigh off my mind. I maintained a semi-hard cock without really trying. I tried to make it go away mentally but to no avail. Under no circumstances was I going to jerk off in her shower just to make it go away.

I washed my face last and stood under the falling water a final time for about a minute. I felt the water sliding off the end of my semi-hard cock, which felt wonderful and didn't help my efforts to make it go down. My eyes were closed as I shut the water off, opened the sliding door, and reached for the towel. I was drying my face and hair when…

“Thinking about me in there?” Ashleigh said as my face was covered with the towel. I didn’t answer as I moved the towel down to my chest. Leaning in the doorway of the bathroom was Ashleigh, still only covered by her towel. As she started to walk towards me, the towel dropped to the floor, revealing her beautiful, sexy body to me. My heart began to race as I gazed upon her beauty. I loved every inch of her – what man couldn’t – but I especially loved her full, perky, firm 34B breasts. I stared upon them before meeting her eyes just as she reached out with her left hand to cradle my rapidly hardening cock. Ashleigh lifted her right arm around my neck, and we kissed. We both moaned through the kiss like it was the last kiss before a long trip.

“So much for talking first,” I whispered as our foreheads met.

“We can talk later,” Ashleigh began. “All you need to know is that Andy and I are on a break.” She continued to softly stroke the underside of my now fully hard cock. She then commented, “Looks like someone recently trimmed,” with a purr.

“Last night,” I replied and dropped my towel. Then my hand cupped her pussy and felt her mound. “Looks like you shaved.”

“I did … last night,” Ashleigh replied as she brought my lips to hers.

Ashleigh continued to softly stroke my cock as my hands held her by the small of her back. We kissed softly for a few more minutes before both of us needed air.

She let go of my cock and took my hand. “Come on,” she said and led me to her bed. Once by the side, she spun around and dropped to her knees. Ashleigh gently grasped my cock before kissing the tip. As she ended the kiss, she looked up at me, and never broke eye contact as she took my balls into her mouth. Ashleigh knew I wasn’t a huge fan of this, but her gentle touch sent shockwaves through my body. Stroking my length, she released my balls and kissed my tip once again.

“Don’t worry about cumming too soon, we have all night,” Ashleigh said seductively. “Plus, I know your trick,” and she chuckled a bit as her tongue fell out of her mouth. It ran up and down my length as she proudly held me upward. I wanted to look at her, but my head fell backward. Her touch caused sensations that simply couldn’t be tamed.

My face pointed at the ceiling with my eyes closed when Ashleigh welcomed my cock into her mouth. It was slow, but her warmth jerked my head down. What kept me on my feet, I don’t know. But she had me entirely in her mouth in seconds. Her tongue massaged me while she held herself down on me. When she was ready and had my cock good and wet, she began to suck.

“Ohhhh my God, Ashleighhhhhhh,” I moaned as her lips moved up and down my length.

Ashleigh had a decent rhythm going when her hands clutched my buttocks. That made my eyes bulge a little. I would have never expected that from her. The rhythm she had going was interrupted when she pulled me by my butt into her mouth. I instinctively grabbed her head for balance but didn’t hold her mouth down on me.

Slowly Ashleigh allowed my cock to slide out of her mouth. She gradually increased her lips' suction, and at the end, her lips made a ‘pop’ sound. Ashleigh looked up and chuckled as her eyebrows rapidly flashed. Releasing her hands from my buttocks, she took hold of my cock with her left hand. Her lips planted dozens of kisses up and down my length as her right hand played with her breasts.

“Such a beautiful cock…” Ashleigh whispered with a moan, and her tongue massaged the underside of it. Her blue-grey eyes were staring up at me as her lips kissed and sucked my tip. I moaned – it was all I could do to acknowledge how much I was enjoying this moment.

Her left fingers took firm hold of my cock’s base, and her mouth soon consumed my cock once more. Her pace was quicker than before, and her intention was clear – she wanted to make me cum. My hands fell behind me, and my fingers locked together. My hips moved forward a bit, and I repositioned my feet a tad. Ashleigh’s repositioned her knees as well, spreading them a little.

With my eyes locked open, I stared down at her as my heart raced. Ashleigh sensed my cock swelling and sucked even harder – never breaking concentration on my cock.

I gasped for air as I said, “I’m about to…” but I never said ‘cum.’ Ashleigh’s instincts told her I was about to cum, and just before the first spurt of cum shot into her mouth, her hands flung back to my buttocks. She braced herself as she shoved my entire cock inside her mouth as I came over and over into her throat. Luckily, I was able to brace myself with her bed to my left – that orgasm weakened my legs something fierce.

Ashleigh refused to relinquish my cock until the last spurt of cum had landed on her tongue. Even then, she sucked and cleaned my cock with her tongue as it softened.

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“Ashleigh,” I said as I caught my breath, “where did that come from?”

“Well,” she began in her trademark seductive tone, “I wanted to suck your cock. I wanted to taste your cum. And I wanted you to get hard again returning the favor on me before you stick that thing in me. You know your trick.”

I had taken a seat on the edge of her bed. She was still on her knees, so I helped her up. When I did, I pulled her into me, forcing me on my back and kissed her. After a few moments of locking lips, I rolled Ashleigh onto her back, and I fell to the floor, but as I fell, I made sure to kiss down her body from her neck to her stomach. I got on my knees and grabbed the backs of her knees to lift and pull her to the edge of the bed. Now the ‘trick’ Ashleigh was talking about really wasn’t a trick. I enjoy eating and sucking on a woman’s pussy so much that I get hard from it. I’m sure most guys do, but Ashleigh loved calling it a trick.

With Ashleigh on edge, I wrapped my hands around her thighs and slowly moved closer to her pussy. I could see how wet she was – no way that was water from her shower. I extended my tongue out to just have a taste. “Mmmmmm,” I said as the tip of my tongue touched the juices oozing from the heaven between her legs.

My eyes glanced up, and Ashleigh was ‘gone.’ She was biting her lips, and even though her elbows had her propped up, her head had fallen backward. I gently licked around her entrance, which caused a few moans to escape. Wanting to hear her moan more, I blew on her soaked pussy.

“Mmmmmm … Ohhhhh, Jack,” she purred. I responded with a slow, continuous blow on her clit. Her hips squirmed a bit, but my hands kept her grounded.

My tongue was itching to go to work. I inhaled and planted my tongue right over Ashleigh’s pussy. I was tasting her sweet juices again but feeling her flex down there as I did, and that was a surreal feeling. Slowly, my tongue moved up and toward her clit. Ashleigh was very tense and was huffing and puffing. I swirled my tongue around her clit before licking downward and around her folds.

Ashleigh moaned at various levels and stayed relatively still until I planted my lips at the top of her slit and her clit. When I began to suck, her hips lunged upward, and she gave a big puffed, “Ahhh.” It became apparent even with both my hands I wasn’t going to keep her “pinned down,” so my left hand slowly slid up her stomach and to her right breasts and pinched her nipple.

“Jackkkk … Mmmmm … Don’t stop,” Ashleigh exclaimed as her hips bucked. And I didn’t stop.

I moved my lips around periodically but never strayed too long away from her clit. My left hand was all over her breast, and when I rested it briefly for a moment, Ashleigh captured a couple of my finger in her mouth and sucked on them. I glanced upward, pausing briefly, and our eyes met. With our eyes locked, I sucked harder than ever before on her clit. Her head flew back, and she yelled, “Fuckkkkkkk!”

The gyrations of her hips became stronger. I brought my left hand back down in an attempt to stabilize her. My tongue then went back to work up and down her entrance. I moved my right and slightly to allow my fingers to reach her clit. This was driving her right up to the edge past a point of no return.

A few final thrusts from her hips and her orgasm rushed through her body. I kept swirling my fingers around and over her clit, and my tongue darted in and out of her pussy, then I tasted her cum. I worked hard to gather what all I could with my tongue. Her arms gave way, and she lay flat on her back as her hands reached for my hair and held me down. Moaning and breathing hard, she didn’t even try to be quiet for the neighbors.

Moments later, her orgasm subsided, and I cleaned her up before gazing towards to face.

“Oh my god…” Ashleigh huffed out. “That felt great.”

“I could eat you all night long if you’d like,” I said through a sly grin.

Ashleigh shook her head, “No, stand up.”

I released my hold on her legs but not before one last lick of her pussy. “Just as I suspected,” Ashleigh said as I stood before her. My cock was fully hard once again and bouncing from my heartbeat.

Ashleigh turned and backed towards the pillows and headboard. I reached for the comforter and sheets hanging over the side to move them. I helped move them under her body and out of our way. Slowly, I climbed onto the bed and on top of her with my arms propping me up.

We slowly kissed, and her hands wrapped around my neck. I broke the kiss to kiss her next, but without a rush. My cock and her pussy were touching as our lips found each other once more, and her right hand reached down to grab my hard appendage. Our lips remained locked as her hand slowly moved up and down my length.

Ashleigh brought the head of my cock to the entrance of her pussy. When she did, our kissing stopped, and our eyes met. She didn’t need to tell me; I knew what she wanted. With my arms straight and hands flat, I slowly moved my hips forward with her hand guiding my penetration. As I slowly pushed deeper, she let out a quiet “Mffft.” Ashleigh’s hands flew up to my shoulders, where her fingers nails dug into my skin just shy of me being entirely inside her.

Once I reached her depths, I pulled back out and began moving my hips back and forth slowly. Her eyes were watching my cock move in and out of her. Instinctively with each push inward, her pussy applied the right amount of pressure that simply was perfection.

Ashleigh’s knees gently began to squeeze me tighter, and I could feel her muscle slowly drifting her feet together. Whether it was a hint or not, I took it as she wanted me to be close. Dropping to my elbows, my hands ran under her hair and cupped the underside of her head. Her hands gripped my head just enough to bring me down, and our lips touched just as our nipples connected.

Each of us moaned through our lips as Ashleigh’s feet interlocked behind me and held my butt down with her heels. As we kissed, I left myself planted deep within her. She was the first to need air and broke the kiss. Ashleigh gasped, and my head fell to her right shoulder. Slowly, I began to move my cock in and out – just a little bit. Enough for more sensations to race through our bodies.

With her lips pressed into my shoulder, Ashleigh squealed. My hips moved up and down, working my length in and out slowly. Her arms wrapped under my arms and my back. I was kissing her neck and could tell through her breathing she was working up to tell me something.

“Jack … your big cock … cum inside me,” was all she mustered up.

“With pleasure,” I responded, and pecked her cheek.

I wasn’t approaching my end, but I could sense she had an orgasm building up. I switched it up and began to move my entire body across hers. It was a hot July night, and our sweat helped move my body across hers. Ashleigh was wincing with pleasure every time my cock pushed inside her. She was biting her lips and had her eyes squeezed shut as I looked at her face. I could have easily changed my pace to make her cum faster, but I would have, too. Plus, I wanted to make this last as long as possible.

“Oh my … Oh my. Oh my … OhmyOhmyOhmyOhmyGawwwwwwwwd!” she yelled again as she came and squirted. She had never squirted, with me at least, before. It was just a little bit, but still significant enough to grab my attention. She was too busy to notice as she was trembling from the rest of her orgasm. But the convulsions of her pussy did expedite my orgasm.

I reached for her lips with mine, but she was already on it. She plowed her lips to mine, dragging my face down with her hands. Naturally, my pace quickened as I was about to cum. I loved to treat her pussy (and any woman’s pussy) like a delicate porcelain doll, but as my end neared, that was thrown out the window. My withdraws became lengthier and thrusts harder.

“That’s it, baby, ahhhhh,” Ashleigh said as I broke the kiss and panted next to her ear.

I was grinding my teeth and puffing as I thrust into her depths. The walls of her pussy began to bear down on me, and I thrust my hips hard one final time. Cum rushed out of my cock, filling her pussy.

“Ahhhhhhhhhh,” was all I could say.

“Mmmmmmm Jackkkkkkk,” Ashleigh said as she experienced a minor orgasm on top of my convulsing cock flooding her depths.

My cock spasmed as I continued to move my hips around. I was kissing Ashleigh’s shoulder and neck as I caught my breath. Ashleigh nestled her head against mine as her hands roamed my back and sides. Then after a few minutes, we had gathered ourselves enough to speak, I propped myself up enough to look at her from above.

It wasn’t the greatest timing, but I was wondering about Andy and Ashleigh’s break, and she could sense it. Placing her hands on my cheeks, Ashleigh said, “After some serious conversations and truth-telling, Andy and I decided to take a break until we go back to school.”

“Yes, he and I had some fun times on Tuesday and Wednesday, but he admitted he hadn’t always been faithful with me and to be somewhat fair to him, I told him that after he told me about the woman on the cruise, I wasn’t faithful to him. But I didn’t mention your name.”

Ashleigh took a few breaths before continuing.

“I couldn’t tell which one made him feel worse – his cheating or mine. Either way, we had both hurt the other, and it was Andy who decided that we should take a break.”

“How do you feel about that?” I asked.

She took a few seconds, then responded, “I don’t really know. When Andy suggested it, he struggled to get the words out as if he didn’t want to say it. I guess I’ll find out as the weeks go on if I long for him or not.”

With that said, Ashleigh pushed me off her and onto my back. She rolled on top of me and kissed me – which I reciprocated. I was too tired and in too much of a daze to think about anything else.

“In the meantime, I have you,” she said as she reached down to her cum filled and soaked pussy. When she brought her hand back up, she tasted our ‘cocktail.’ “Mmmmmm, yummy,” Ashleigh purred as she reached back down. This time she brought her hand up to my mouth, and I happily accepted her two cum covered fingers in my mouth. I smiled and kissed her.

We both reached for the covers and pulled the sheet out, and wrapped ourselves up. My arms wrapped around Ashleigh and held her gently. It wasn’t long before Ashleigh was asleep on my chest, and it didn’t take me long after to fall asleep myself.

 

To be continued with Part VI

 

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Written by Jack_01
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