Chronicles of Cole Ch. 05

I was awoken from a deep sleep by the beeping coming from my phone's alarm. After turning it off, I got out of bed and headed to the shower. It had been a rough Memorial Day weekend, and not in the good way.

Friday had started off well as I spent the late morning fucking Kate Hamilton in front of her husband. That sealed an agreement between the three of us in which I would have sex with her after I cleaned their pool.

Everything turned when I got to the public pool after grabbing lunch. As I expected, it was a crowded day, but Rob was able to get two deck chairs at the far end. I passed Bailey in one of the lifeguard chairs walking back there. She gave me a quick smile, but I noticed a slight scowl on her face after she returned her attention back to watching the pool.

Rob quickly pointed out why Bailey was in such a bad mood. Across the way from her was Carter Sullivan, her ex-boyfriend, and the worst person I have ever met, with one of her cheerleader teammates all over him. That cheerleader turned out to be Alexandra "Alex" McCloud, my ex-girlfriend, and a teammate that Bailey had gotten close with recently.

Bailey had told Alex earlier in the week about Carter wanting to go out with her and warned her about him. This new development put Bailey in a bad mood that carried over to our date that night. We had always had sex on date night, but that never came close to happening.

On Saturday, my dad took me to the country club to play a round of golf. Like the last time I played with him, the beverage cart girl on duty was Kate. Both her and my dad flirted with each other when she stopped to take our orders. That was as far as it went due to it being a busy day on the course.

I stayed at home most of Sunday until late in the afternoon. That is when I headed over to the public pool to pick up Bailey due to her not having access to her car. Her mom's vehicle needed emergency work done on it and was stuck in the shop all weekend. Both of her parents needed access to a car that evening, which resulted in me being the good boyfriend turned chauffer home.

After parking in the mostly deserted parking lot, I texted Bailey to let her know that I had arrived. It wasn't long before she was walking out of the clubhouse at a brisk pace. That was odd for her until I saw Alex hustling after her while calling her name.

Stepping out of my RAV4, I heard Bailey yell at Alex, "I told you; I'm not talking to you!"

"Why won't you let me explain what is going on between me and Carter?"

"I don't need your explanation!"

"Cole, can you help me out?" Alex asked me after noticing I had exited my RAV4.

"Let's go, Cole! I am not speaking to this bitch!" harshly exclaimed my girlfriend.

Maybe it was that I also wanted an explanation from Alex about her and Carter. It might have been how rude Bailey was to her teammate and friend. In a rough tone that I only showed with my baseball and football teammates, I said, "Stop Bailey! Let Alex explain what is going on. I want to know why, and I know you do as well."

Both were shocked into silence by my tone. Neither of them had heard me speak that way before as I only did so around my baseball and football teammates.

Bailey was the first to find her words. "Okay... umm... Go on Alex. Explain what is happening between you and... Carter."

"Yeah... so... let me first say that I didn't' do this to hurt either of you. I also thought about it for a while after you told me about what Carter wanted." said Alex. "The reason I have started seeing him is so I can get my fill of dick this summer."

"Seriously?" I quickly asked her.

"Yes. I have needs and figured it would be the easiest way for me to get my fill of cock. Plus, Bailey, you did mention he was a good lay when you two were dating."

"I did but... but... he's a piece of shit!" Bailey exclaimed.

"Yes, he is, and I have already seen that side of him. As I said, I am just using him for his dick. I have no feelings for him regarding a long-term relationship like you two," responded Alex.

Both Bailey and I stood there in silence for a minute as we processed what Alex had told us. It would be Bailey that spoke first.

"I get where you are coming from, but I am still not happy about it. Just be careful around that asshole."

"Don't worry. He thinks he is in control, but it is really me that has the power. I'll break it off with him when I've had my fill of him. What are your thoughts, Cole?"

"It's your life. I'm just not looking forward to him gloating about fucking you to me. But then again, that will be nothing new from him from what he already annoys me with regarding Bailey," I told her.

"So, are we all good now?" Alex asked. The question was directed more towards Bailey than me.

"I guess so, but not sure I will ever be happy about it," said Bailey with a defeated one.

A smile came across Alex's face after Bailey's response. "That works for me," she said before stepping close to her. In a low tone, my ex said, "I won't hold how you treated me over the last couple of days against you. That is unless you want me too,"

Alex surprised both of us by grabbing a handful of Bailey's right breast over her t-shirt. She had a big grin on her face as she gave Bailey's breast a couple of squeezes.

She released her grip and walked away from us. "Think about it and let me know," my ex shouted over her shoulder right before she got to her car. After watching her get in and drive off, I turned my attention back to Bailey.

"Let me apologize for taking that tone with you, but you needed to..."

"Just take me home," Bailey quickly said to cut me off. She then walked over to the passenger side door and got in.

It was an awkward, quiet ride the entire way back to her house. Bailey just stared out the window the entire way lost in her thoughts. I was expecting her to immediately get out of my RAV4 when I came to a stop in her driveway. Instead, she sat there for about 30 seconds until she spoke.

"I want to say that I'm sorry for the way I have been acting the last couple of days. I just didn't take the news of Alex and Carter that well. Even with her explanation of why she is seeing him, I'm still upset about it. Also, you don't have to apologize for your tone in the parking lot. Thank you for driving me home."

"Apology accepted. I get where you are coming from with the news. I wasn't happy about it either, although it affects you a lot more than me. Also, you're welcome for the ride," I said before putting my right hand on her thigh.

Despite giving me a warm smile, Bailey shot done any chance of getting intimate tonight. "Sorry, Cole. I'm not in the mood tonight."

She opened the door and slid out of her seat. "Good night and have a safe drive back home," she said before closing the door. I watched her enter the house before backing out and driving home.

While the thought of jerking off crossed my mind multiple times over the weekend, I had held out hoping to have sex with Bailey. Even with the denial from Bailey on Sunday, I figured I would save up a big load for her later this week. Worst case for me is that it would be her mom that would end up getting my cum on Wednesday.

I hustled out of the house and drove off to the Thomas' house to get there by 9 a.m. Despite it being Memorial Day, Brittany Thomas insisted that I still come by to clean their pool since they had been gone for over a week on vacation. They lived in the same neighborhood as Kate and Steve Hamilton and Brittany Williams' parents. The house was near the top of the hill in the back of the gated community.

Thankfully, there wasn't much traffic on the holiday morning, and I also did not have to check in at the guard gate anymore. That was due to the Hamilton's slipping a swipe card for the gate into the envelope with my tip they gave me on Friday. It was a lot longer drive than I had expected up to the house. I pulled into the Thomas' driveway and parked with two minutes to spare.

Walking up to the front door, I saw a note taped on it. On it was a sentence telling me to follow the path and enter the backyard through the side gate. I followed the instructions, but what I didn't' see was the front door quickly opening and a hand reaching out to quickly take down the note before closing the door just as fast.

Entering the backyard, I noticed the good size pool, hot tube, and waterfall area. It was all capped off by a view of the town from their perch on the hill.

I was taking the view in when I heard a female voice to my right. "Hello, you must be Cole."

Turning to where the voice came from, I saw Gabby Thomas in person for the first time. She was even more beautiful than what I had seen in the photos that she had texted me when we had set up the pool cleaning appointment.

Gabby was wearing a white terry cloth robe that was cinched tight, but I could still make out her large breasts underneath. Her red hair was straight but had just enough volume in it. She was sitting at a table with a cup of coffee in front of her while having a big smile on her youthful face.

"Yes, I am, and you must be Mrs. Thomas," I said.

"You are correct, and please call me Gabby. Calling me Mrs. Thomas makes me sound old," she responded. "Thank you again for coming out today even though it is a holiday."

"I'll do that and it's not problem as I didn't have any plans this morning. So, what do you want me to clean? I don't remember you mentioning anything about the hot tub and waterfall," I said while looking out on the backyard. Taking a closer look, I noticed that the pool was already clean which caused even more confusion.

When I turned back to look at Gabby, I saw a guilty look on her face as she took a sip of her coffee. Before she could answer, the back door opened and out came an older man. He was nearly 60 with salt and pepper hair. The guy was 5-foot, 11-inches tall with a slight gut.

"Hi, Cole. I'm John Thomas. Has Gabby explained everything," he said.

"Umm... no... she hasn't explained anything. I'm confused because I was hired to clean your pool. However, I can tell that it has already been cleaned," I told them.

John gave his wife a look and they seemed to be silently communicating between the two of them. Eventually, Gabby cleared her throat after taking another sip of coffee.

"There is a lot to explain, but I will cut right to the chase. We want to hire you under the premise of cleaning our pool. However, we have a different job we would like you to perform each week. And that would be..."

She took a deep breath to calm her nerves and looked at her husband for reassurance. After he nodded his head, Gabby continued, "We want to hire you to come over and fuck me."

"What... seriously... you want... I don't... what?" I was too stunned to come up with a full thought after the revelation.

"Cole, take a seat and we'll explain everything" she said in a calming tone.

I walked over and took a seat across from Gabby. Her husband joined us and sat on her left side. He seemed nervous about what Gabby was going to reveal regarding their intentions with me.

"To start off, I have to say that I crave sex every day. While I can be satisfied by either pleasuring myself, or John eating me out, or one of my girlfriends getting me off, there are days I just need a good cock to fuck me."

I sat there in silence. Unsure of what to say in this uncharted territory.

"John would love to take care of my cock cravings, but he..."

"I have erectile dysfunction," John quickly interrupted his wife. "My therapist says I need to be able to admit my problem to help my mental state regarding it."

Gabby grabbed his right hand and gave it a loving squeeze. Her eyes focused on him in a loving way before she returned her attention to me.

"Yes, he was ED. Obviously that has caused some issues. He can take Viagra to help him fulfill my needs from time to time, but with the amount of sex I crave it would give him a heart attack to take that much Viagra that often. We don't want that to happen."

"It was easy to take care of her needs when we lived in the Los Angeles area. We knew enough people or could find willing partners to fuck this redheaded beauty. Since we have moved to Clear Falls, however, it is a lot more difficult to find guys that we can trust to keep their mouths shut about sex life," said John.

"Very true. I've had to rely a lot on my toys to fill my cravings. At least our vacation allowed me to get a bunch of cock," Gabby said to her husband.

Seeing that my brain was starting to connect the dots, she quickly did so for me. "I know you are about to figure it out. But to save you the time, yes that short video clip I sent you was with a guy I met at the resort."

"So... I'm guessing you want me to be one of the dicks that fucks you to help you out," I said to her.

"That's correct. You came highly recommended from Jennifer Shaw in the cock department," Gabby said while licking her lips.

"Geez, she just can't keep her mouth shut about me," I said under my breathe.

"Don't you worry. She does know how to keep her mouth shut. She just tells people she truly trusts. Plus, Jen is a VERY good friend," said Gabby.

"Let me guess in how she is a very good friend. Jen and you have had sexual encounters."

"You would be correct. She helps me out from time to time in that area, but she is also one of the few women at the country club that are nice to me. Others think I am a gold digger due to the big age difference between me and John. Those women just don't understand that love knows no age."

This time it was John who reached over and took ahold of Gabby's left hand. They looked into each other's eyes with pure love in them.

"So... umm... back to what we want with you, Cole," Gabby said. "We would like to have you come over ever Monday morning this summer around this time. I would want you to fuck me however I request. Also, John will want to watch when he doesn't have to work.

"We will pay you handsomely for your time if you do accept," added John. "There is one catch. You must decide within the next 10 minutes to do it or not."

"That is not a lot of time to decide. Can I ask some questions before giving you my answer," I asked.

"Of course," said Gabby.

Turning my attention to John. I questioned him, "Would you want to get involved at any point I'm fucking your wife? If so, what would you do?"

"To tell you the truth, if I get an erection then I would want to join in. That would involve me either having Gabby suck me off or fuck her if you aren't."

Nodding my head to his response, I followed with a question for Gabby. "How long would you want me to be here? I do have another pool cleaning appointment on Mondays around 2 p.m."

"I would want you to stay as long as you could. We wouldn't want to make you late for your other appointment."

"Just to clarify, it would just be me, you and occasionally John. You wouldn't invite anyone else over to join?"

Gabby hesitated for a second before responding. "I can't definitively say no. I did have an idea of inviting a girlfriend over to join us. John has never seen me have a threesome with a man and woman before."

I saw John nodding his head in agreement with a smile on his face.

"Can you tell me who is on your list?"

"Hmm... it might be one of my friends from Los Angeles if they come to visit, or it could be someone that lives here. If it was the latter, then I would make sure that they would be able to keep our secret."

"Like Jen?"

"Yes, she would be on the shortlist. There are a couple of others in town I would consider inviting. And before you ask, no, I won't give you a hint even if you accept."

"What would happen if either of us wanted to end the relationship?"

"It would be a mutual parting, and I'd have us all sign an NDA," said John.

"Really?"

"Yes, it would put a financial penalty on us all if we talked about what happened here."

"Would we sign an NDA if I accepted your offer?"

"Not if you accept. We figured you would everybody would want to keep this a secret while it was on going," said John.

"Your time to decide is up. Got any more questions for us," said Gabby.

She had loosened her robe enough to show a hint of cleavage from her large breasts. Her right hand slowly rubbed the exposed skin as she gave me a seductive look.

"Umm... I... how much are you going to be paying me," I was able to get out after being distracted by the sexy redhead.

Gabby reached into a pocket of her robe and pulled out an envelope that she placed on the table. Pushing it towards me, she said, "This much every week in cash. It is non-negotiable."

I took the envelope and looked inside. My eyes went big with all the $20 bills in it. Before I could start counting the money, John chimed in. "To save you the time in counting, it is $1,000 in twenty-dollar bills. Figured it would be more common for you to walk around with twenty-dollar bills instead of fifty- and hundred-dollar bills."

Before I could think of any other questions regarding the offer, Gabby ended those thoughts. "Time is up Cole. What is your decision?"

Looking up from the envelope full of cash, I saw that Gabby had loosened her robe even more. It was now split open down to below her stomach. The sides still covered her nipples but bared a good amount of her porcelain skin breasts with freckles on her upper chest. She started to lightly rub her exposed breasts with her right hand. A teasing smile on her face waiting for my answer. An answer she already knew.

"I think I already know what your answer is going to be, but we want a verbal answer," she said while moving her hand underneath her robe to rub her nipple.

I swallowed hard before managing to get my answer out to them. "Y-y-yes... I accept your offer."

A big smile spread over not only Gabby's face but her husband's as well. Gabby closed her robe before she pushed back her chair and stood up. The 5-foot, 9-inch-tall redhead got up and walked over to me before leaning over and whispering in my ear.

"You made the right choice. We are going to have SO much fun this summer."

Gabby straightened up as I turned my head towards her. She loosened the belt around her waist that loosened the robe. Taking her hands, she slid the robe off her shoulders and let it fall to the ground.

My eyes wide went wide seeing the gorgeous redhead completely nude. Her breasts were E cup size with barely any sag to them. Her medium size areolas were capped off by hard nipples. Looking downward, her tight stomach led to a small tuff of red pubic hair above her bare pussy lips. She had well defined arms and legs from her workout regimen.

"You like what you see?" questioned Gabby.

"Yes," was all I could say while nodding my head and taking her all in.

She ruffled her hair that caused her tits to slightly shake. Turning around, I saw her pert little ass for the first time in person. It was even better than what I had seen in the photos and videos she had texted me.

I watched her walk over to an oversize cushioned chaise lounger. It was easily big enough to accommodate two people. She laid down on her side on it looking at me. Curling her finger, she beckoned me over.

Standing up, my erection was showing prominently in my shorts. Gabby couldn't take her eyes off of my crotch as I walked over to her. When I got to within a few feet, she told me to stop.

"You're overdressed, Cole. Take your clothes off. It's time to see what Jen hyped up to me."

"Knowing Jen, you won't be disappointed in what she told you," I said with a slight smirk.

"Go on, prove her right," responded Gabby.

I quickly took off my t-shirt and threw it over to where I had been sitting. Deciding to have a little fun and tease Gabby, I hooked my thumbs in the waistband of my athletic shorts. I started to slowly lower my shorts down my hip but quickly removed my thumbs from them. Instead, I squatted down and started untying my shoes.