Chronicles of Cole Ch. 04

A loud piercing beep emanated from my alarm clock. I hated being woken up by an alarm, especially during the summer. The big difference on this Monday was that it was the start of a busy week for me with four new pool cleaning clients and having a fifth the next week. All of them taking me on thanks to my girlfriend's mom, Jennifer Shaw.

My dad woke up earlier than me and made breakfast. As I came into the kitchen, he was getting up to leave to head into the office. It was rare for him to go to work on a Monday, but he had a big meeting to attend.

After eating, I got in my RAV4 and headed over to the Hamilton's. While mine and Bailey's parents lived in high-priced neighborhoods, the Hamilton's house was located in the most expensive development in Clear Falls, California. Living in a gate community, I had to check in at the guard shack before being allowed to proceed.

The houses in the development were all mini mansions with considerable size lots. Arriving at the address that Kate Hamilton had given me, the house was located at the end of a cul-de-sac. Due to the location, their closest neighbors were far enough away to provide a lot of privacy.

I parked in the large driveway and rang the doorbell. Just when I was about to ring the doorbell again, the door swung open. There stood a stunning older woman with dyed blonde hair that was shoulder length. She stood around 5-foot, 3-inches tall, slightly tan, with B cup breasts. She was in great shape and looked about a decade younger than her actual age of 45. She was wearing a blue tank top that matched her eyes and white jean shorts that were more common for people around my age to wear.

"Hi, you must be Cole. I'm Kate Hamilton," she said with a friendly smile while extending her hand.

"Yes, I am. It is nice to meet you Mrs. Hamilton," I responded as I shook her hand and noticing her eyeing me up and down.

"Hope you didn't have any problem finding the house."

"I had no problem at all finding the place. Just wasn't used to having to deal with the guards at the entrance to the neighborhood."

"They didn't give you too much trouble?" she asked.

"No, problem at all with them Mrs. Hamilton," I responded.

"Good. Come in and I'll show you to the pool. By the way, you can call me Kate," the older woman said with a wink.

I followed her through the first floor of the massive house. It had an expansive layout from what I did see and knew from the outside there were more rooms off to each side. I also took the opportunity to check out Kate's pert ass as she led me to the pool. Anyone would have with the bottom of her ass cheeks peeking out from them.

"Wow!" The house was nice, but the pool was really incredible. It had a waterfall on one end and a grotto along the right side. Plus, they had a good-sized guest house in the back left corner.

"Pretty impressive, huh?"

"Yes, it is. This is the nicest pool I have ever seen."

"It is one of the reasons we bought the house, along with the location. It allows us to throw some pretty fun parties without bothering the neighbors," she said.

"I bet. You all have a lot of space back here. So, where are the pool cleaning supplies?"

"Follow me. They are in a shed at the back of the guest house. Plus, I have to unlock it," she said while pulling a key out of her jean short pocket.

As I walked behind her to the shed, I noticed she was putting extra emphasis in her hip movements that drew my attention to her ass. Mrs. Hamilton's words broke me out of my trance on her backside.

"My husband Steve and I added the grotto section a couple of years ago. It was a great decision as it has been an IMMENSELY popular area at our parties," she said. Standing there for a few seconds, I could tell she was reminiscing on some fun times in the grotto from her past parties. Her right hand brushed lightly over her breasts as her hard nipples were visible through her tank top.

"Umm... well... on to the shed," came from Mrs. Hamilton as she regained her focus back to the present.

When we got to the shed, she pulled out the key and unlocked the door. She led me into it and pointed out the pool cleaning supplies in the back corner.

"Sorry they are so far back. I insisted to Steve on making sure they were stored there in case the kids somehow got into the shed and caused mischief. Figured if they did get in, then the most likely place it would happen would be closer to the door," she stated.

"That makes sense," I said as I navigated to the back between pool floats and boxes. "How old are your kids?"

"We got a 10-year-old boy and an eight-year-old girl. We dropped them off at Steve's parent's house yesterday for a two-week stay with them," was her response.

"That is a nice long break visit for them."

"Yes, it is. What's better is that it gives me and Steve a lot of alone time," she said winking at me. "Another added benefit is we don't have to find someone to take the kids for the night when we host our party this weekend."

From what she had mentioned about the parties just a few minutes earlier, I was hoping to figure out a way to possibly get an invite. Unfortunately, that was not going to be the case as Mrs. Hamilton was apparently a mind reader.

"I bet you are hoping to get an invite for it. However, that is not going to happen. Steve and I like to keep our parties 21 and older. We don't want to encourage underage drinking or deal with the fallout if something happens to them. That is a shame you aren't older enough because you would be a big hit at the party from what Jen told me," she said.

At the same time, she brushed her hand lightly down my chest and stomach. She pulled her hand away right before she reached the waist band of my shorts. The look in her eyes and her smile had a naughty intent in them.

"Well, I'll let you get to work. We need the pool in the best shape possible for the party," said Mrs. Hamilton.

I couldn't help but stare at her ass against as she walked back towards the house. For a woman her age, she has a fantastic butt that anyone would want to get their hands on. Mrs. Hamilton looked over her shoulder and caught me staring at her. I caught a smirk on her face before she started slightly strutting to show her backside even more.

Once Mrs. Hamilton was closer to the house, I shook my head to clear my thoughts of her butt and got to work cleaning. It took me a lot longer than normal for me to do the job due to the massive pool's massive size.

The heat and sun didn't help matters either. The local meteorologist was right in that the temperatures would increase this week beginning this morning. The beating sun had me taking off my shirt when I was only halfway through the job.

Topping it off was when Mrs. Hamilton came out in a blue string bikini and laid out on one of their deck chairs. I was getting déjà vu from last week with Jennifer Shaw. I took plenty of glances over at the mature blonde woman. She had an incredibly fit body despite her age and having had two kids.

Eventually, I finished cleaning the pool area and started to head over to work on the grotto. That is when Mrs. Hamilton spoke for the first time since coming out in her bikini.

"Cole don't worry about the grotto. There is someone else we have that comes by to clean that up before out parties."

"Okay. That sounds good. Well, that means I am done cleaning and just need to put the supplies away," I said.

I took the supplies back into the shed and used the time out of the sun to cool off some. I was glad that my next two appointments today were not in this neighborhood and would have smaller pools compared to the one I just cleaned.

Hearing the door close caught me off guard. I turned around and saw Mrs. Hamilton standing there in her bikini with a hand on her hip and a devilish smirk on her face. From my experience over the last five days, I had a feeling where this was headed.

"You did a good job cleaning the pool. Glad I listened to Jen and hired you. Now I want to give you a tip and thought the best way was to show you a little bit of what you are missing out on at our party," she said.

The blonde woman beckoned me over to her which I didn't hesitate to do. When I stopped in front of her, she started running her hands over my sweaty bare chest and abs.

Looking up at me with her sparkling blue eyes, she said, "Jen told me what happened with you two this past Wednesday. Sounds like you two had a fantastic time."

"Umm... I was hoping she would keep that a secret. Do you know how many people she might have told?" I questioned her while feeling my cock start to inflate as Mrs. Hamilton kept feeling up my chest and abs.

"Not for sure but have a feeling it was at least one or two more. We have a couple of close, mutual friends. But don't worry, I know how to keep my mouth shut," she tried to reassure me.

"I... I... I should get going. I have another client today and cleaning your pool took a lot LOOONGER!"

"Oh yes! It is a lot longer than what I normally get," said Mrs. Hamilton as her hand grabbed my cock through my shorts. "Jen wasn't lying either when she said you were hung."

"I... umm... oh fuck!" I let out as she slipped her hand into my waist band and started rubbing me to full hardness.

"Don't worry, I won't keep you around much longer or make you late for your next client. Just want a taste for myself," she said before squatting in front of me. I helped her out by untying the draw string of my shorts before she pulled them down.

The shock of surprise on her face or any woman's face would never get old for me when they saw my cock for the first time. Like the ones before her, Mrs. Hamilton was left speechless at my size.

"Oh... wow... it is incredible... so big... so thick," came out of her mouth in a whisper. She rubbed both of her hands all over my cock. When she grabbed it with both hands, there was a decent enough gap between her finger's tips on both hands due to my thickness.

"It has been a while since one of our regular party attendees has had a cock this amazing at our parties. Probably Donte Jenkins was the last one. His cock is so fucking amazing, and he can really fuck. Wish he hadn't gotten been deployed overseas," she was saying out loud to herself while still jerking me off.

I was surprised to hear her mention Donte Jenkins, who was in the military and recently deployed for a tour of duty. He is also the father of Alonzo Jenkins, who danced with Bailey at the club just two days ago.

Looking up at me with pleading eyes after realizing what she had said was out loud, she asked, "Please don't repeat what I just said to anyone. I don't want to ruin his reputation or end up exposing anyone else. I'll reward you if you don't say a word."

I only need a few seconds to respond as I already knew what I wanted. "I promise to not tell anyone on the condition you invite me to some of your parities and allow me to bring a friend or two."

"Fuck! I'll have to talk to my husband about it before I can agree to that. We'll let you know for sure later this week.

"That works for me," I responded.

"Good! Now it is time for today's tip." Mrs. Hamilton then inhaled as much as my cock into her mouth as she could.

"FUCK YEAH!" I yelled. My head involuntary tilting back and my eyes closed from the sensation of filling the blonde women's mouth. She had stuffed about six inches of my dick into her mouth and throat.

Pulling off my cock with a pop sound, she looked up at me while jerking my now saliva-soaked cock. "If you like that, then you are really going to love when I really get going."

With that, she inhaled my cock again and began bobbing up and down on me. Add in her jerking the part of my dick not in her mouth, I was in a near euphoric state. Mrs. Hamilton continued to work and eventually I felt her lips meet my pelvis.

"God Damn!" I let out. Her eyes were watering a little while looking up at me. Somehow, she made the blowjob even better as I felt her tongue start to tickle a part of my balls. Mrs. Hamilton was just the third woman to ever deepthroat me, but she had taken the top spot for her blowjob skills.

"Aww! Your... cock... is... fucking... amazing!" she said after pulling off my cock but continuing to jerk me. There was still a string of salvia attached from my cock head to her bottom lip.

It wasn't long before her mouth as stretched over my cock again as she continued her blowjob. Her mouth was heavenly as she worked her magic. I had to close my eyes and concentrate on not blowing my load too early.

Pop! Came from below me as she pulled off again. "You are already so close to blowing you load. I can sense it. It is why I left so many men happy back in my day in the club."

Before I could completely process what Mrs. Hamilton had just said about a club, she went back to work on my cock with gusto. "Gawk, gawk, gawk, gawk," was constantly coming from her.

I put my hand on the back of her head and started to thrust into her mouth to help speed up the process. The urge to cum had gotten to me. "Fuck! You are so good! I'm so close to cumming!"

That only motivated the older woman. She started sucking and jerking me faster, which was driving me to the edge.

"Oh fuck! I'm about there, keep going, don't... stop! Fuck... fuck... I'm... I'm... right... there... I AM CUUUMMMIIINNNGGG!"

Mrs. Hamilton quickly pulled off and aimed my cock at her chest. At some point during the blowjob, she had moved the triangles of her bikini top to the side that exposed her breasts that were capped off by hard pink nipples. She jerked hard and fast to get me to unleash shot after shot of cum on her chest and neck.

"So much cum! You absolutely coated me. How long has it been since you came?" she asked. Her hands still slowly moving up and down the top half of my cock to try and squeeze out the last of my cum.

Looking down at her, my cum had covered her chest and neck area. Some droplets had even splattered on her chin. "Last night... last night when... I fucked my girlfriend," I said while breathing heavily.

"Wow! That's such a big load after about 12 hours. I would love to see how much you could produce after a day, or two, or a week," Mrs. Hamilton stated before licking the head of my cock for the last remnants of my load out of me.

As I caught my breathe from the best blowjob I had every gotten, Mrs. Hamilton used my dick to scoop up my cum off her chest before sucking it clean. She continued this for a couple of minutes before letting me go. Her actions kept me semi-hard. Had I not had another client today, I'm pretty sure I would have ended fucking her wherever she wanted to around her house.

"Well, I hope you liked your tip," Mrs. Hamilton said saw she got off her knees and put her bikini top triangles back into place. "Follow me and I'll pay you for cleaning the pool."

I pulled up my shorts and noticed she was already out the door. I quickly made my way out of the shed and was greeted with the site of her small but perfectly round ass completely exposed to me by her thong bikini bottoms. That didn't help my cock as it got even harder as I had to readjust it before following her to the back patio.

Mrs. Hamilton hand me an envelope of cash before telling me, "Thanks for cleaning the pool. I will talk to my husband about your condition for keeping quiet about our parties and let you know ASAP."

I thanked her and followed her into the house to the foyer. The whole time I couldn't take my eyes off her ass split in two by her blue thong bottoms.

"Would have loved for you to stay to enjoy that big, thick cock of yours more, but I don't want you to lose any jobs due to little, old me. I'll be looking forward to next week when you are back over here,"

"I hope you remember that it will be next Friday when you're on my schedule next. Got another client that is taking over this Monday spot," I told her.

"That's right," she said with some disappointment in her voice. Then she surprised me by grabbed my cock through my shorts. "Guess I need one more feel to hold me over until then."

After a couple of squeezes, Mrs. Hamilton released her grip on me. That had caused my dick to become partially engorged.

"Well, guess I should show you out," she said walking to the front door. "It was a real pleasure, Cole."

"Thanks, Mrs. Hamilton. I hope you were satisfied with my service," I responded.

"Oh, I was satisfied with your SERVICE. By the way, call me Kate from now on. That is unless you want to do some roleplaying," she said while giving me a flirty look.

"That's good to know Mrs. Hamilton... I mean Kate. I look forward to seeing you next week," I said while walking out the door. I got into my RAV4, and she was still standing in the doorway. When she saw that I was looking at her, Kate untied her bikini top and took it off leaving her topless. She also had a big smile on her face as she gave me a flirty wave before turning around and closing the door.

Shaking my head while thinking about what I had experienced this morning, I put my RAV4 into reverse and backed out of the driveway. I was stopped at a light having left the neighborhood when my brain started to finally comprehend what type of parties Kate Hamilton and her husband hosted.

People using the grotto area of the pool, knowing about Donte Jenkins' dick size and how he fucks, mentioning how big of a hit I would be at said events from what Jennifer Shaw had told her. It added up to being swinger parties.

I remembered all the times that Bailey had mentioned that her parents would be going over to the Hamilton's place for parties. That included the first time me and her had fucked on Christmas Eve when the Hamilton's were hosting a Christmas party. There were also a couple of their parties that I knew my dad had gone to with whomever he was seeing at the time.

My thoughts were broken by a car horn from behind me due to the traffic light changing to green. I hit the gas pedal and drove off to my next pool cleaning client. Thankfully, my other appointment just wanted me to clean their pool and never showed a hint about trying to get into my shorts.

That night I got an email with the summer football workout and individual skill schedule that begins next week. My position's individual skill slate was on Wednesdays, and we are required to show up twice between Monday through Thursday for strength and condition. The good news was that they had open slots from 8 am to 8 pm. The bad news was that with my pool cleaning appointments, the only time I could go in for the strength and conditioning practices were evenings outside of Wednesdays.

I texted Bailey to let her know about the schedule.

(Cole): I got my practice and workout schedule. I'm locked into Wednesday evenings for the individual skill portion. Have to go in twice more for strength & conditioning. Those must be in the evenings, as well.

(Bailey): Thanks for letting me know. I got my schedule, too. Practice on Tuesdays & Thursdays in the evenings and have to choose one more day for the gym.

(Cole): Damn, the only day and time we could work out together would be on Mondays. I was hoping to do the gym work on Tuesdays & Thursdays.

(Bailey): Haha... great minds think alike. I was hoping to do Wednesdays for my time in the gym.

(Cole): So, Mondays then for the workouts? That way we can have Wednesday available for a date night.

(Bailey): Yes. Although Wednesdays will be an odd day for us. Fucking in the morning and going out in the evenings. Think it should be reversed 😉.

(Cole): LOL... I prefer to think of it as starting and ending the day with sex 😈.

(Bailey): You got a dirty mind Cole Webb.

(Cole): 😈😈😈

(Bailey): What am I going to do with you? Since I've been slacking on working out, want to go to CF Gym with me tomorrow?