If you read the previous story in this chain, “Supervisor and Cashier Part III: A Shoulder To Cry On,” then you may have predicted what was coming next with Ashleigh and me. Then again, you maybe didn’t.

I had gone over to Ashleigh’s house following my shift last Thursday, allowed her to cry on my shoulder over her boyfriend being an ass, spent the night, and then in the morning, she had rewarded my kindness with a blow job. The next two shifts we had together were that Friday and Saturday. I was a supervisor both days, and Ashleigh was very distant. She didn’t ignore me, but her usual playfulness was absent. She continued to smile at me, which made me feel a little better, and also do her job professionally – which she always did.

On Saturday, Ashleigh was the final cashier to leave, which meant I would clock out before her. I covered the register for her last break, and when she returned, she explained she was thinking a few things over and would talking with Andy the next day. I commented that I hoped Andy cleared his mind and realized he had made some poor decisions with her. Before I clocked out, she said she would see me on Monday here because we both had the same shift. We smiled, and I said I looked forward to seeing her then, and I left.

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Monday arrived, and Ashleigh and I walked in together – it was strictly a coincidence. As we walked in, she said, “Are you able to come by my place tonight?”

“I am. Is everything okay,” I questioned.

“Kinda sorta … I just need to talk with you,” Ashleigh said with her classic million-dollar smile. “I have some things to share.”

“Alright, then. I’ll follow you home after work,” I replied with a smile.

We laughed, and she said she was jealous I was going to be on self-checkout for my entire shift before clocking in.

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Our shifts went by without any significant issues at the store – at least none more than usual. I followed Ashleigh back to her townhouse, and she offered me a glass of water. I accepted as I was parched. She brought my water over as she sat beside me on the couch. As I have mentioned before, Ashleigh knew she was beautiful and knew how to flaunt herself. She wore very tight slacks that day and sat cross-legged and slumped to the side, giving me a great view of her ass and legs. Whether that was intentional or just instinctual, I don’t know. We each took a large gulp of water before she broke the ice.

“You are probably wondering why I was so distant with you last Friday and Saturday,” she said.

“A little bit, but at the risk of getting hit, I figured you needed some time to think following last Thursday night and Friday morning,” I replied.

“You would be right, smartypants,” Ashleigh chuckled and gently kicked my arm. “I did need some time to think. I told Andy the same,” she said as if it was no big deal. My eyes nearly popped out as I thought she had told him or worse, he’d figured Ashleigh and me out.

Ashleigh realized this and said, “Oh, don’t worry. Andy doesn’t know about us.” There was a difference in her tone of voice than what I would have expected. I didn’t pry, however, for why that was.

She continued, “But I needed time to think about what Andy is to me and his and my future. Then, of course, you and me and what we’re doing.” Pausing once again, she confessed something that I didn’t expect to hear from her. “And I needed to think about something else Andy had shared with me last Thursday that I didn’t share with you because … well … I didn’t know how.”

Instantly I sensed that she had spent a lot of time thinking – A LOT – in the past few days. Then she dropped the bombshell of a confession from Andy. To make a long story short, back in early June, Andy had gone a cruise with his family. He and his brother were sharing a room, and that allowed him to have an easier time with “extracurricular activities.” Andy had met this girl, who was in her late twenties, about six-foot, brunette, who was curvier with large, fake DD breasts. And as you can guess, they had sex several times on that cruise. Ashleigh said he had confessed every detail about the woman and their activities in a second call on Thursday before she called me. The first call had been the fight over him visiting, but then he called to confess that he had cheated on her. That is what had sent her over the top with her crying while on the phone with me.

I was shocked, and it hit home with me. Ashleigh was obviously cheating on Andy with me. All at once, that didn’t make me feel the greatest, especially since Ashleigh had just said he didn’t know about me. She leaned over for a hug, and I welcomed it. She didn’t cry like last Thursday, but the few tears that escaped were of guilt mixed with relief.

“I’m sorry I didn’t tell you before, Jack,” Ashleigh said as she backed out of the hug.

“It’s okay. That couldn’t have been easy.”

I had no idea what to say. The realities were hitting me at the same time, so Ashleigh continued with her explanation.

“Andy text me Friday morning after you left. I told him that I’d call him on Sunday because I needed time to think. I was so pissed off at him from the whole situation that I nearly…” she stopped mid-sentence. Ashleigh took another drink of her water and regrouped. “That I nearly had sex with you that morning just to get revenge at him. But I realized that I’d be having sex with you for the wrong reasons … more wrong reasons.”

Ashleigh exhaled and continued, “I wanted your cock to fuck me and not you. I wanted to get … I don’t know what you’d call it … ‘size revenge?’ You know, since you have a bigger penis than Andy.” Her chin dropped to her chest at the guilt of the admission she had just made.

“But I realized that wouldn’t be fair to either one of you. It wouldn’t be fair to you because I’d simply be using you, and it wouldn’t be fair to Andy because he really and truly does satisfy me and make me cum, just like you do. That’s on top of I haven’t been faithful to him, either.”

I’d seen pictures of Andy, and he was only smaller than me in one respect. He looked like a typical six-foot-two high school jock that all the high school girls would gossip about with their friends. But I say, so what if he had a five and a half inch cock? That’s average and just like any man should he knew how to use it properly. Otherwise, I knew Ashleigh well enough to know she wouldn’t say that he satisfied her, and a woman on a cruise wouldn’t come back to him multiple times – especially the latter. I understood Ashleigh’s dilemma. She was in love with a handsome guy – despite his character faults – and who satisfied her in bed. He had cheated on her with a woman who was her complete opposite of her. All the while, she had cheated on him with me.

“I know Andy and I were both in the wrong,” Ashleigh said. “When I called Andy on Sunday, he immediately apologized to me for getting so mad and protective about his decision not to come to meet and visit my family sooner. He actually will be driving over here in the morning to meet my parents over a late lunch and Fourth of July fireworks. He also apologized again and again for cheating on me on the cruise.”

Ashleigh took another drink of her water, and so did I. She also scooted backward a bit to put a little bit of distance between us. Ashleigh also explained, calmly, that she had suspected that he had cheated before with a few different girls but didn’t call him out on any of it. At this moment, she believed the timing to be wrong to bring her previous suspicions up, but even more, she knew she had not been faithful either.

“Andy has also agreed to move his golf outing with his friends and will be visiting again during my family’s barbeque. So, this will be his, what, sixth trip over here but the first where the main reason for the visit isn’t so we can just fuck,” she concluded for the moment.

I have to give the guy credit; Andy had some sort of an epiphany. What triggered it, I have no clue. But he realized that he had something really special with Ashleigh and was doing his best to save it.

“I really don’t know what to say,” I said as I started to speak and was happy to find some words quickly. “I’m sorry Andy cheated on you, and you’ve suspected it for some time. I am, however, happy to hear he seems to have wised up and maybe even matured, realizing he hasn’t been completely fair to you and your family.”

I paused a bit, and Ashleigh allowed me to gather a few more words together.

“I know you like Andy, and you’ve mentioned before, maybe even love him. Maybe this is him realizing he loves you and wants to be with you for the long term.”

Ashleigh smiled and nodded. She looked up at me and said, “I might be crazy, but I hope you are right.” She moved around a bit and resettled on the couch before saying, “How do you feel about all this? Are you … mad or … I don’t know … What are you thinking? Please be honest!”

“I suppose there is the obvious question about why you decided to take me to your bed,” I asked.

“There isn’t a good reason,” Ashleigh began. “I guess … I know Andy was no stranger to sex when we met. A girl can tell both in bed and how she sees her boyfriend talk with his friends. I could tell early on he’d had sex with multiple girls in high school and a few in college before he met me. And there are the suspicions I had but didn’t have solid proof of him cheating.” She paused before continuing, “I had only had sex once before Andy on my senior prom night – cliché I know,” she chuckled. It was the first time she had laughed since I arrived.

“I think I liked how you looked at me and treated me, and deep down, that is what I wanted Andy to do all this time. Maybe I wanted to have a few additional experiences of my own,” she shrugged her shoulders, and a guilty expression swept across her face. “I think I had gotten pretty good at making Andy happy and changing things up from time to time. Maybe I thought I could learn something else with another guy. I don’t know. That’s not and wasn’t a good reason to cheat on him.”

“Why won’t you tell him about you cheating on him?” I asked.

“If you heard Andy on the phone, you’d have sworn he was on his knees admitting what he did wrong and how bad he felt,” Ashleigh explained in a serious tone, looking up at me. “It was like he was begging for his life. Plus, it sort of affirmed my suspicion that he had cheated before the cruise. I think it all came down on him at once. Andy made it sound like the four or five times he met with this woman on the cruise was a metaphor for multiple women. I couldn’t tell him about us because I think it would literally would have broken his heart at that moment.”

Ashleigh gazed over at a sweatshirt that was hanging on a rack that was from Andy’s high school. After a few seconds, she looked back over at me and said, “Is that love?”

I shrugged, “I wouldn’t really know. I haven’t been in love before, but it sounds like it. Plus love is different from person to person.”

What I didn’t and couldn’t say, is that I did like Ashleigh enough to want to pursue a relationship if given the opportunity. But she had to make that decision. Despite all the chaos, I knew Andy made her happy, and I wasn’t going to confess my desire to be with her in a more substantial capacity at this time. That would have simply made the waters murkier.

After a moment of awkward silence, Ashleigh spoke, asking, “Don’t you want to know where this leaves you?”

I nodded and said, “Of course.”

Ashleigh moved around on the couch once again, now sitting on her knees and took my hand in hers.

“I know you know that I’ve enjoyed our times together – at work and here,” she smiled. “You are at the level of maturity I want Andy at … and maybe that’s why I’ve invited you into my bed. Because you are what I want Andy to be today.” Ashleigh paused an thought about her next words. “But is it okay for me to say I’ll know more after this visit with Andy?”

I nodded and said, “I think that’s fair. You two need to have a face to face conversation.”

“Thank you,” she said with a big smile, followed by a kiss on my cheek.

Soon after that, we decided to call it a night, and I would leave to go home. She had traded shifts with others for Tuesday and Wednesday so she could spend more time with Andy. I wouldn’t see her for four days, Friday, July 7. We both had the same shift that day, and we agreed we would talk then. We hugged, and Ashleigh gave me another kiss on the cheek before I left.

As I walked to my car, Ashleigh pleaded from her doorway, “Jack, no matter what happens, I want to stay friends with you!”

I turned around, and even though I didn’t believe the words that came out of my mouth, she and I both needed to hear me say, “I want to stay friends, too, no matter what.” I smiled and entered my car, never losing the smile.

Ashleigh smiled back as she stood in the doorway. I backed out of her driveway and waved. She waved back and remained in the door until I turned the corner. I did not guess what Friday would bring. No matter what, I simply wanted Ashleigh to be happy.

To be continued with Part V