Supervisor and Cashier Part IV Confessions
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Supervisor And Cashier Part II: A Night At Ashleigh’s free porn video
- The third week of June, 2017 -
It had nearly been a week since I followed Ashleigh back to her townhouse last Saturday night. I never worked Sundays, and she didn’t work the following Monday, but we had texted back and forth. Most of our conversation was reliving small moments from that night while others were general conversation – including gossip and trash-talking coworkers.
Anyways, on Tuesday, I was the afternoon and evening self-checkout attendant, and Ashleigh was a regular cashier for a few hours that night in the middle of my shift. She clocked in for her shift at 4:00 p.m. and walked down to me to grab a water from the employee cooler that was located by self-checkout.
“Hey there, Jack…” Ashleigh said with a ‘look at how sexy I am’ type of look with the proper walk to go with it.
“Ashleigh, how are you doing on this hot day today,” I said, trying to play it cool.
“Ughh, it’s so hot. I didn’t want to wear a bra today, but I knew if Carla or Rose were working today, they would write me up, so I’m toughing it out,” she said with a bit of frustration.
“Yeah, that would have been a shame to be written up for being comfortable,” I responded with a smirk, leaning against the self-checkout podium, making her feel taller.
“Oh, Jack, shut up, or people will figure out what happened,” she said, glancing around.
I chuckled and just looked at her face as she looked at mine, albeit being a brief stare for each of us.
“So . . . what time do you get off tonight?” I asked her genuinely.
“Eight o’clock and I have bad news for you . . . and me, too, really,” she said, chuckling. “Andy has decided to stay a bit longer. He took some extra days off from work to spend with me.”
Ashleigh was happy and disappointed to have her boyfriend visit her. He had arrived on Sunday evening from Illinois and was only planning to stay through Tuesday but decided to take the rest of the week off.
I shrugged, chuckled, and said, “Oh well . . . I suppose I’ll just have to go home and cry then.”
She hit my shoulder and laughed.
“Stop it. I’m already conflicted so, please don’t make me worry about you went you leave this place. He leaves Friday so…,” her voice trailed off.
“So what?” I responded.
“So, we both get off at ten o’clock on Saturday,” she said with a naughty smile as she cocked her hips. “Why don’t you bring an overnight bag with you and spend the night at my place?”
I was jumping for joy inside, but I somehow played it cool as any man talking to Ashleigh could hope for.
“That sounds like a great idea,” I winked and smiled in response.
She perked right up on her tiptoes and pushed her 34B out at me.
“Awesome!”
Without saying another word, she walked towards that day’s front end supervisor and put her hair up in a ponytail.
We finished Tuesday out and worked together on Thursday as well, exchanging a kiss here and there. Ashleigh never missed an opportunity to say how much she was looking forward to Saturday night, as did I. We both had Wednesday off, and she found someone to take her shift on Friday so she could spend time with Andy before he left to go back home to Illinois. On Saturday, though, she was asked to come in a half-an-hour sooner. So instead of working from 2 to 10 p.m., it was 1:30 p.m. to 9:30 p.m. This meant we wouldn’t get off at the same time. Not a big deal, but I was oddly looking forward to following her home. Probably because I loved looking at her ass.
“Alright, Jack. I’m clocking out. See you next week!” she said cheerfully, but in a tone that sold that we weren’t going to see each other until next week.
Of course, I knew better. I said ‘cya’ and waved goodbye as I worked to help some customers checkout.
As I was walking out to my car, Ashleigh texted me, instructing me to park my car in her driveway tonight. I was a little surprised, but I did as I was told. Ashleigh’s townhouse was owned one of four owned by her father. During the school year, an out of town student going to the local college lived there, and she lived in it during the summer. She told me that she had gotten accustomed to living on her own during her freshman year of school, and it drove her crazy living with her parents the summer between her freshman and sophomore years. Now she was between her sophomore and junior years, and her father said she could live in one of his townhouses if she wanted. Obviously, she said yes.
Having parked my car in the driveway as I was told, I rang her doorbell.
Opening the door, she had changed into a loose grey t-shirt with pink booty shorts. Her long, smooth legs put on display for me, and she had left her blonde hair up in a ponytail.
“Hello Jack,” she said, leaning against the door with her hip out.
“Hello, Ashleigh,” I said with a glowing smile. “You look gorgeous tonight.”
She motioned me inside. I stepped in with my overnight bag draped on my shoulder. Ashleigh closed the door and kissed me on the cheek.
“Here, let me take that to the bedroom,” she said, taking my bag from me. “Please have a seat on the couch.”
She returned a moment later and went straight to the fridge and grabbing a beer and a water bottle.
“Aren’t you only twenty, Miss?” I said with a chuckle.
“Andy is twenty-one, so while he was here, he bought some and just left them here for next time he visits,” she said, handing me the beer as she sipped her water bottle.
“Thank you,” I said, nodding and accepting the beer. “Great minds think alike. This is my favorite.” I winked at her.
“Well, you and Andy both have great tastes,” she motioned her hand down along her body.
We set our drinks down on the table and kissed passionately for the first time in a week.
She broke off the kiss to say, “But let’s not talk any more about Andy. This is you and me time, and it’s going to be great!”
She scooted closer to me, and I wrapped my arms around her. Our lips met once again, and we sat on her couch, kissing for minutes on end. I didn’t try anything fresh as I knew that time would come. She didn’t either. We both just moved our hands across the others back, legs, sides, and face. We were soaking up the way each other felt. The slowly, Ashleigh broke off the kiss.
“I haven’t showered yet, and I can tell you are a bit sweaty yourself,” she chuckled. “Why don’t we hop in and give ourselves a good wash?”
“Good idea. I think I’d love a shower right about now.”
Ashleigh grabbed my hand and led me to her bathroom. It was quite spacious with a walk-in shower and a separate tub.
“My dad remodeled this place when he bought it. Do you like it?” She asked with a smirk.
“I love it, Ash,” I responded with a smile.
“Ooohhh, call me Ash more, Jack,” she said as she lifted her t-shirt over her head, revealing once again to me her beautiful breasts.
I unbuttoned my shirt and lifted it, and my undershirt over my head to find that Ashleigh had already removed and stepped out of her booty shorts. She was completely naked as she started the shower. I purposefully waited to drop my slacks and briefs until Ashleigh turned back around. When she did, I dropped them not fast but not slow either, and my cock was beginning to grow. I wasn’t anticipating shower sex, but that didn’t stop me from acknowledging Ashleigh’s beauty.
“Mmmmmm, I missed seeing that,” Ashleigh said, staring at my rapidly growing cock.
Ashleigh let down her hair before extending her hand to me. I took it, and she guided into the shower under the running water. I wrapped my arms around Ashleigh, pulling her close.
“Ash, you are so beautiful,” I said as I gently kissed her lips.
“Thank you, Jack,” she said. “Now, let's wash our hair.”
I held out my hands, and Ashleigh poured shampoo into them before pouring some into hers. We each washed our own hair. I admired her body with her arms up. The water cascaded down her athletic stature. I was done with my hair first, and I washed out the shampoo. Ashleigh soon followed.
“Okay, now let me wash your body for you, please,” Ashleigh said, grabbing her body wash.
I nodded. How could I even think about denying her at this moment?
“Sorry, girly soap here,” she said, giggling.
I moved back away from the falling water. Ashleigh started rubbing my chest and shoulders. Ashleigh motioned me to spin around, and she washed my arms, then my back, followed by my buttock, and finishing with my legs. She really took her time because it felt like I stood with my back to her for 10 minutes when it actually was only a few.
Ashleigh then guided me to turn back around. She washed my legs once again and worked her way up to my shaft. All Ashleigh did was smile. Washing my abdomen side and thighs, she then moved to my cock and scrotum. She lightly kissed the head of my cock and stroked my cock to clean it and rubbed my scrotum down too. Obviously, this wasn’t the first time a woman had touch either, but the sensation of Ashleigh washing my cock and balls sent shivers through my body. She stood back up and finished washing my chest before guiding me under the showerhead to wash off.
No words were exchanged as I grabbed her body wash for myself and poured some in my hand. Ashleigh positioned herself where I had just stood. I decided to replicate what she did. I started with her neck, shoulder, and top of her breasts. I gently spun her around and started washing her back, making my way to her beautifully rounded ass. I took a chance and kissed each cheek before washing them. She giggled in response. I took my time there, making sure her ass was nice and clean before I washed her legs.
I grabbed her hips and gently spun her around, rewashing her legs as she did mine. I worked back up her legs and washed her thighs. I arrived up at her pussy. She had recently shaved, possibly that morning. I kissed her clit gently, she moaned in response and guided my hands to wash her pussy.
Moving up, I washed her abdomen and up towards her breasts, taking each in my hand as I stood up. I washed her breasts by massaging them. As I rubbed soap across her chest, she looked down, and I followed her. My cock head had just poked her pussy.
She looked back up at me and said, “You are pretty good at this, but let’s finish up here…,” she said as she grabbed my cock and pushed me through the water so she could wash off. After her body had been rinsed of soap, we kissed under the falling water. As we did, she reached around and shut off the water. I broke off the kiss, and we stepped out, each drying off our clean bodies well.
“Follow me, Jack,” Ashleigh said, taking my hand and leading me back to her bed. She let go as she got to the bed's edge. She crawled on, and I followed her. As she laid on her back, I propped myself over her and kissed her lips. Her arms wrapped around my neck, and we held our positions as our tongues danced a slow dance with each other.
Ashleigh eventually reached her hand down and took ahold of my cock once again.
“Mmmmm . . . I need you inside me, Jack,” Ashleigh said between kisses.
I broke the kiss and kissed my way down her body. Starting with her neck, I worked down past each of her breasts, her stomach, belly button, clit, inside of each of her thighs, and on down to her feet. She squirmed the entire way. When I reached her feet, I was at the end of the bed. I grabbed hold of her ankles and pulled her body to the edge of the bed.
“Oh my! Please don’t hurt me,” Ashleigh playfully said.
“I’d never dream of it,” I said, bending over and brushing her cheek. Saying nothing more, I guided my cock to her entrance and began to penetrate. I pulled what little had entered her and rubbed it around her clit.
“Oh Jack, please quit teasing me and shove your big cock in me already,” she playfully exclaimed.
“As you wish…,” I cleverly responded as I slowly penetrated her pussy.
She softly moaned as I slowly entered her depths once again. Ashleigh arched her back, and her head went backward, gripping the bed comforter. Soon, I was completely inside her, and I wiggled my hips to tease her a bit.
“Jack..,” she said with her eyes closed.
I withdrew myself from her and pushed back in faster. She moved her arms down and brought her legs out in a spread eagle position, allowing me to penetrate even deeper. I positioned my hands at her side and thrust into her with only my hips as guidance.
“Mmmmphhh, Mmmmphhh, Mmmmphhh,” was all that could escape Ashleigh’s lips as my cock penetrated to the hilt with each hip through downward.
My neck became weak from the sensation of Ashleigh’s pussy, squeezing my cock. They ran up my spine and to my neck. With my head down, I lowered myself enough to kiss her neck and shoulders. Her then arms wrapped behind me, her nails digging into my shoulder. And yes, she did leave temporary marks.
We were both so turned on that I don’t know how we got through the shower without tearing into one another. That is why I wasn’t surprised when I could sense that Ashleigh was on the break of an orgasm. Her breathing began to become choppy, and small convulsions inside her pussy started and grew in intensity.
“Jack…Jack…Jackkkkkkk” was all she could get out before she came. With force, she pulled me into her, and our chests nearly aligned. I continued slow pumps into her as we kissed through her orgasm.
“Oh, Jack,” Ashleigh said, still catching her breath with my cock still pumping in and out. “I need your cum inside me. Please cum inside me.”
My face didn’t give a sign that I was worried about pregnancy, even though I should have been. But Ashleigh sensed its somehow and said, “Don’t worry, I’m on the pill. Now please,” pausing impressively, “fuck me and cum inside me.”
I withdrew my cock and sat upward on my knees. I quickly grabbed a pillow from behind her and shoved it beneath her ass. Ashleigh knew precisely what I meant to do. She pulled her legs back to her head. I stood up on my knees and reentered her pussy.
I placed my hands on her legs and began to thrust my hips back and forth. As my cock rocked in and out of her pussy, Ashleigh rubbed her clit. Her head was back, and her eyes closed once again. Her blonde was spread all out as I began to reach my own orgasm.
“Harder baby,” Ashleigh said in the most seductive way possible. It was also the first time she had used a pet name with me, which turned me on even more. I didn’t think that was possible.
Moaning and grunting, I was approaching the end. My hips pounded my cock into her as I gripped her legs with my hands.
I began to edge myself and hold my breath, trying to hold back the inevitable.
Softly whispering through my teeth, I said to Ashleigh, “I’m cumming,” right as I thrust inside her one final time before releasing my cum deep inside. I started pumping again after the first few spurts of sailed out of me, before ultimately softly collapsing on top of her as a second orgasm rocketed through her body. She nearly screamed this time as her hand gripped into my back as if trying to keep from falling off a ledge.
After a few moments of the two of us catching our breath, we looked at each other and into each other’s eyes. We held our stare before our lips attached, and we softly kissed for minutes on end. Ashleigh was the first to break the kiss.
“Here, let me scoot back here,” she said. She moved back towards the headboard of her bed. Propping herself up with pillows, she patted her lap, telling me to lay my head down there. I did as I was told with a second thought.
“Jack, I am so glad you don’t have to leave tonight,” she said as her fingers ran through my hair.
“Me too, Ash,” and I brought my hand up to rest on her cheek.
After a few moments of chatting back and forth, Ashleigh glanced down my body and to my cock, which had returned to a hardened state.
Chuckling, she said, “Are you looking for some more fun?”
I glanced down my body. I had felt myself getting hard once again but had tried to ignore it.
“Ummm . . . yeah, maybe,” I replied with a smile and little chuckle.
“Not tonight. You wore me out, but we can have some fun in the morning before you leave,” Ashleigh said with a sincere smile.
“I’d like that,” I said.
We talked for a while more with my head still in her lap before tucking ourselves under her bed covers and going to sleep. We spooned with me as the big spoon, draping my arm below her breasts.
*
I woke the next morning on the opposite side I fell asleep on and tingling below my beltline. There Ashleigh was, giving me a morning wake up blow job.
“There he is…” she said with my cock against her cheek. “Turn on you back and sit back because I’m going to thank you for last night.”
I moved back against the pillows, Ashleigh scooted with me and brushed her hair to the right side.
“Mmmmm, such a great cock to wake up each morning to…” her voice trailing off once again as she planted her tongue on my balls. She then started to slide her tongue up my balls, to the base of my cock and up to my head. Once to top, she dived down, taking most of my cock inside. Ashleigh worked diligently to take the remaining length inside her mouth.
“Mmmmm, Ash,” moaning I said, “You are…” I couldn’t finish my thought. All I could do was moan and stare as she worked to take my entire cock in her mouth while her tongue was planted on the bottom side.
Once she was able to take my entire length inside her, she began to bob up and down. She stroked my shaft and cupped my balls back and forth. Her ass stuck up in the air, all tanned and smooth. My hand rested at the base of her neck but not guiding her up and down. There was no need to force what was happening.
As I stared down at her in pure bliss, her eyes looked up and into mine. She smirked as my cock passed in and out between her lips. Ashleigh twisted her fingers and mouth as she bobbed up and down, occasionally gagging herself. I matched her rhythm slowly, moving my hips up and down, too.
Next, Ashleigh began to make some exaggerated moans as I began to moan more and more for real. Rotating between licking my entire cock, sucking, and teasing my head, she was bringing me closure to cumming – and she knew it.
My breathing became shorter and shallower, and my head collapsed behind me. Ashleigh cupped my balls and began to bob up and down faster and faster.
“Ashleigh . . . I’m cumminggggggg,” I exclaimed.
I blew my load right into her mouth. She continued to bob up and down as she sucked every last drop out she could.
“Mmmmm, Jack, you are a dream,” she said, swallowing and leaning forward for a kiss.
Still catching my breath, I said, “No, you are the dream, Ash. You!”
She purred and kissed down my chest and down to my cock again.
“It’s 10:45 so go grab a shower, and I’ll fix you something to eat. Okay?”
I nodded and got up to wash myself of sweat and cum. After a bit, I exited, got dressed, and went into the kitchen. Ashleigh had made a few things of sausage, eggs, and toast.
“Wow, breakfast of champions here. Thank you,” I said, happy to accept.
She had put a robe on and sat next to me with her plate.
“No, breakfast of great fuckers,” she said, winking.
We ate breakfast together before I ultimately had to leave. We kissed at the door, embracing each other more like boyfriend and girlfriend, rather than merely lovers. Ashleigh kissed me deeply while I pulled her close.
“See you on Tuesday, boss,” she said, winking and slapping my butt on the way out the door.
“Behave yourself, or I’ll write you up.”
I turned and walked out the door, but as I turned back to wave, she flashed her breasts at me and shut the door. I hopped in my car and drove away, recanting one of the best nights, if not the best night, of my life.
- To be continued with Part III -
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