Chronicles of Cole

I woke up with Bailey snuggled up to me with one of her hands draped across my chest. Stretching to grab my phone off my side table, I saw that it was 8:02 a.m. I would have liked to have slept a little long and also stay in this position for a little longer, but I had an urgent need to relieve my bladder.

Slowly, I moved out from under Bailey's arms. That elicited a little groan from her but didn't wake her up. I picked up my athletic shorts that were on the floor and pulled them on before quietly slipping out of my door.

As I exited my room, I smelled breakfast being cooked that was most likely being done by my dad. Right as I was about to grab the door handle to the bathroom, I was startled when it unexpectedly swung open.

Standing there in front of me wrapped in a towel was Olivia. Her blonde hair was wet and slicked backed. When she saw me, a big smile spread across her face.

"Good morning, Cole. How did you and Bailey sleep?"

"I... We slept well. Both of us were pretty tired and were out pretty quickly," I lied to her.

Taking a step towards me so that she was just inches away, she said, "That's not what I heard when I made a stop by the bathroom before going to bed. At least from Bailey due to your mouth and tongue. Hope she returned the favor."

"Umm..."

"That's not nice of her. Want me to help you out?" she offered with a sparkle in her eyes.

"Thanks for the offer, but I'll pass."

"Well... if you change your mind, hit me up. Would love to have you stuffed inside ALL of my holes," Olivia said while at the same time grabbing my dick through my shorts. She gave it a couple of quick squeezes before letting go and walking past me to the guest room. Right as she opened the door, Olivia looked back at me and dropped her towel to give me a view of her slightly tanned bubble butt before walking into the room.

Shaking my head, I entered the bathroom and took care of my business. I then headed downstairs as the smell of breakfast was making me hungry. My dad was cooking eggs, bacon, sausage and had already place a platter of fruit out. I wasn't the first one up as Rob was already sitting at the table eating.

"Morning, Rob," I said entering the dining room.

"Good morning. What time did I pass out last night?" Rob said between bites.

"A little after 10. We all stayed up for about another hour before Daniel, Kyle, Anna, Natalie and Kayla left. Everyone else stayed the night."

"Okay. I didn't miss too much of the action then. Could you give me a ride home later since I rode over with Daniel?"

"Yeah, no problem," I told him as I sat down with my own plate of food.

"Know if anyone else is up?"

"I'm up and ready for the day!" came from an excited Olivia as she bounded into the dining room.

"Good morning. Come grab a plate. There are bacon, eggs, sausage and fruit. Also, some coffee if you want any," said my dad.

"Thank you, Mr. Webb. It all looks and smells delicious," Olivia said with a hint of double meaning. I also noticed her giving my dad a hungry look.

"Hey, Cole. Can you go see if Josh and Markus are up and let them know breakfast is ready?"

"Sure thing," I said after putting my fork down after a bite of eggs.

When I got to the door of the pool house, I hesitated for a second hoping not to walk in on any sexual acts between my teammates and Anna. It was quiet inside when I opened the door. The bedroom door was cracked open, and I looked inside. There was Markus sitting at the end of the bed completely naked. He was rubbing his eyes as it appeared he had just woken up. Knocking twice on the door frame, he looked over and noticed me standing in the doorway.

"Morning, Markus. My dad has made breakfast, and it is ready to eat."

"Thanks," he said yawning. "I'll be in once Josh gets out of the bathroom."

"Cool," I responded. Starting to turn to head back inside, I turned back to him and asked, "Have you seen Anna this morning?"

"No. I didn't see her when I woke up. Although that has only been the past few minutes. She might have gone back inside after both Josh and I fell asleep."

"Okay. Just wondering if she had gone back to the house or not."

"She wasn't here when I woke up. I wish she was because I would have loved to have fucked her one more time," came Josh's voice as he walked out of the bathroom completely nude. Looking at Markus, he said, "Bathroom is all yours."

"Thanks, dude," Markus responded getting up from the bed and walking into the bathroom.

Looking back at me, Josh said, "We'll be right in. Hope there is enough food left for us."

"There will be plenty. My dad made a bunch of food," I told him before leaving the bedroom and heading back to the house.

Back inside, Anna had come down and was sitting at the table having just started to eat. Bailey arrived about 10 minutes later just before Josh and Markus came in themselves. After everyone ate, all of the guests rounded up their things before heading out. Bailey drove Anna and Olivia back to their homes and Josh gave Markus a ride home.

When I pulled into Rob's driveway, I noticed the neighboring house on the right had a sold sign in the yard.

"When did your neighbor's place sell?"

"Oh... That went up on Wednesday. Apparently, the people that bought it are moving in on Thursday. At least that is what my parents said when they talked to the realtor."

"That's a quick turnaround."

"Yeah. The realtor said It's a married couple and the husband got a job in town. They didn't want to rent an apartment while searching for a place or something like that. Thanks for the ride and will see you later."

"No problem, see you later."

I decided to head over to the mall to check out holiday deals at some of the stores. Plus, I needed to get out of the house for a bit. After browsing in a couple of stores, I headed to the food court to grab something to eat. When I was walking by tables on the outskirts of the area, I saw Tanner Ellis eating at one of them.

Tanner is the football team's head equipment manager. Seeing him reminded me that I needed to talk to him about a favor for me hoping to possibly fulfill Gabby Thomas' fantasy request.

"Hey, Tanner. How has your weekend been?" I asked him.

"Hi, Cole," he responded after looking up to see who was speaking to him. "It's been alright. Tomorrow will be better with my family going out to a lake. What about you?"

"It was good. Threw a party yesterday with some of the football guys and cheerleaders. It didn't' get too crazy as my dad ended up staying in town after a change of plans for the weekend."

"Cool, cool."

"Soo... Can I ask you a favor," I said after taking a seat in a chair across from him.

Looking at me skeptically, he asked, "What's the favor?"

"Is there a way I can borrow my full uniform next weekend?"

Tanner had a quizzical look on his face after hearing my request.. He took a sip of soda before responding. "I have had guys ask me to borrow a jersey and maybe a helmet before over the past two years for senior photos, but I will say this is a new one for me." He paused for a few seconds before continuing. "I'm not going to ask what you need it for, but what you're asking is not a favor. It's more of a request and will cost you some money."

"How much are we talking?"

"Depends. When would you pick it up and when would you return it to me before the coaches noticed that it was gone?"

"I would like to get it sometime Friday afternoon, and I could get it back to you Monday evening or Tuesday morning at the latest."

Tanner took another bite of his burger. I could tell he was thinking of a price. After swallowing and taking a sip of soda, he gave me a number. "It's a deal for $500. Plus, if there is any damage to the equipment or uniform then you would have to pay me the cost to replace it. Just so you know, this is a big risk I'm taking doing this and could lose my position if the coaches found out."

"I understand and all of that is reasonable. You got yourself a deal"

"Really? Damn...should have asked for more."

"Too late now. I can give you the money when I pick up the uniform on Friday."

"Cool, cool. Just text me a time when you will be at the school. I'm free all day."

"Can do, and thanks for doing this," I said getting up from the chair.

"Not a problem. See you later, Cole."

"See ya. Have a good rest of your holiday." I told him.

"You too," Tanner responded as I started to walk away while he finished his meal.

Walking over to the pizza place, I couldn't believe that getting the uniform went a whole lot easier than I thought it would. Now I just needed one of the football coaches or a security guard not to be there when I picked up the uniform or dropped it off. After eating, I checked out a couple of more stores but didn't buy anything.

On my way home, I decided to stop by the gym to get a quick workout in. It was nearly empty since it was a Sunday and holiday weekend. I was happy about that as I wouldn't have to wait for any equipment or machines to be available. After changing into some athletic clothing, I decided to make it an arms and shoulders day. I was in the zone when a voice interrupted my concentration.

"Hello, Cole," came the feminine voice from behind my left shoulder.

Turning my head, I saw the familiar face of Anna Fox. The school's 28-year-old cheerleading coach was jerkoff material for every straight male student at the high school Her light brunette hair was pulled back into a ponytail while her brown eyes were sparkling from endorphins. She was wearing a green sports bra that supported c-cup breasts on her fit, thin frame. Her abs had a slight sheen to them from sweat.

Anna wore black spandex shorts that hugged her body tightly. They were short and put her long legs on her 5-foot, 7-inch frame on display. Her calves and thighs muscles were well-defined from her workout regimen.

"Hi, Coach Fox. How are you doing?" I said to her as I took a pause from my dumbbell workout.

"I am doing well. Good to see you getting a workout in during this holiday weekend."

"Thanks. I needed to burn off some energy and was already out after stopping by the mall. Plus, I need some time away from the house for a bit after the party I threw yesterday."

"A party? Hope you didn't get too crazy?"

"Kind of hard to have a party go crazy when my dad was home."

"That's good. Kept you and I'm guessing your teammates and some of my cheerleaders out of trouble."

"You aren't wrong about that."

"Well, the reason I interrupted your workout wasn't just to chit-chat. I need a spotter for some reps with the barbell. The place is pretty empty and nearly everyone else is in the cardio area."

Looking around, I saw that what she said was true. I had been so into my workout that I hadn't noticed how sparse it was over on this side of the gym.

"Sure. I could use a slight break and help you out."

"Thank you very much!"

Coach Fox turned and walked towards the barbell bench she had setup with her weights. I joined her after putting the dumbbells back on the rack. She laid down and settled into position on the bench. Taking the opportunity, I checked out her incredible body and noticed the slight perspiration on her cleavage.

"You ready to spot me?" said Coach Fox that brought my attention back to spotting her.

"Sure am," I responded and positioned myself with my crotch nearly directly over her head.

I watched her go through her reps and assisted slightly at the end of each set to put the bar back into place. Seeing Coach Fox's body as she exerted herself and the movement of her breasts had my blood flowing to my cock to make it partially engorged.

Normally I would have been wearing compression underwear while working out. However, since I had made a last-minute decision to go to the gym, I did not have a clean pair with me. Instead, I had on loose boxers that did very little to help keep my dick down.

When I helped put the bar back on the rack after her final rep, I ended up straddling Coach Fox's head. I caught a glance of her licking her lips while looking up the right leg of the shorts. She was looking directly at my semi-hard cock that was dangling down that leg.

I backed up a step as she sat up on the bench. After taking a drink from her water bottle, Coach Fox said, "Thank you for your help with spotting. That was a great way to conclude my workout. Think I'll hit the sauna before heading out. Think you should join me when you are done."

With that, she stood up and walked towards the back of the gym to the corridor to the sauna. I watched her the entire way, more specifically her ass that shook just right in the black spandex shorts. Coach Fox appeared to put extra emphasis with each step to make her tight ass move just a little bit extra.

Then I saw her reflection in the mirror when she was near the entrance to the corridor. She had a naughty smirk on her face having caught me checking her out. The cheerleading coach then disappeared down the corridor.

I walked over to where I had previously been working out and took a drink from my water bottle. While Coach Fox' offer to join her in the sauna might have been innocent, I was pretty sure it wasn't after catching her reaction to seeing my cock. I knew I shouldn't, but my small brain was winning the battle thanks to the possibly of having a chance with the brunette beauty. My thoughts were interrupted when I heard my phone ding with a text. Checking it, I saw the text was from my dad.

[Dad]: I need you to change the bed sheets and wash the current ones from the bed in the pool house tonight. Also, we've been invited to the Hamilton's house for their annual fourth of July party tomorrow. Probably arrive there just after 11 a.m.

Well, that made the decision easy for me. I finished up my last workout before hitting the shower and changing into clean clothes. As I drifted off to sleep later that night, I had no idea what would be in-store for me on Tuesday.

******************************************

Monday saw my dad and I hang out for a father-son day. He was able to get us a tee time at the country club. It was crowded and we were partially rushed on nearly every hole to keep pace. We ran into Kate, the beverage cart girl, twice during our round. Each time I noticed her and my dad flirting a little with each other.

I ended up shooting an 83 and my dad was 10 strokes better. Afterwards, we had dinner out before returning home to watch a movie. We both went to bed before midnight to be fully rested for the Hamilton's party the next day.

My dad and I arrived at the Hamilton's house at 11:20 a.m. the next day. There was a sign on the door to enter the backyard via the side gate. There were already a little over 20 people there when we walked into the backyard. It was a mix of people ranging from couples with young kids to older couples.

"Welcome Will and Cole. Glad you two could make it despite the last-minute invite," said the sweet voice of Kate Hamilton.

The fit, blonde MILF was wearing a blue and white sundress that had very thin shoulder straps and fell just past her knees. I couldn't tell if she was wearing a bar or not, but if she was then it was strapless.

"Thank you for the invite. How did you know I was going to be in town today?" my dad asked.

"I texted Maria to see how the weekend trip was going. She told me about it being cancelled due to her mom's health issues. Guess it is our gain for you to grace us with your presence today. Now, if you don't mind but I need to borrow Cole for some help inside. You don't mind helping me, do you Cole?"

"No... no problem at all," I responded.

"Well, I'll go say hi and catch up with Steve and some of the other guys. Thanks again for the invite," my dad said before walking over to a group of men hanging out by the grill.

"Follow me, Cole," said Kate.

She then turned and started walking to the back door. I followed a couple of steps behind her. I took advantage and checked out the slight sway in her hips. Immediately, I had thoughts that Kate was leading me inside to have a quickie since we missed out on our usual Friday sex session.

That thought proved to be wrong. Kate led me into the kitchen and opened the walk-in pantry door. There were a bunch of soda and beer cases on the floor.

"Grab a couple cases of soda and take them out onto the deck. The coolers are out there," said Kate.

I grabbed a case in each hand and was about to turn around leave the pantry when I felt Kate press her body up against my back. Feeling her breath on my left ear, she whispered, "This afternoon, we are going to make up for missing out on our usual Friday fun."

Turning my head, I saw her giving me a devilish grin. The older blonde woman then licked my ear and then gave me two quick pats on my butt. Signaling for me to get going on taking the soda out back.

After filling the coolers for Kate, I mingled with some of the other attendees that were boosters of the high school's football and baseball teams. They asked the usual stuff about how the football team was looking. A couple of them wanted some insights about Carter Sullivan and what school he might be committing to.

Thankfully I didn't have to answer too many questions about Carter. A reprieve came when I saw Bailey, her mom and dad enter the backyard. That gave me an excuse to leave the boosters.

"Hey babe," I said approaching Bailey and her parents.

She had a radiant smile seeing me walk towards her. Bailey surprised me when I got within her reach. On her tippy toes, she wrapped her arms around my neck and pulled me in for a kiss. It was a quick but passionate kiss that saw her slip her tongue into my mouth briefly.

"Hey sweetie. Long time no see," were the first words out of Bailey's mouth.

"A little too long if you ask me," I flirted back.

"I think I'll go see how some of the other boosters are doing. Good to see you, Cole," said Tim Shaw.

"Guess I will say hi to our hostess. Enjoy yourselves you two," Jennifer Shaw told us.

I couldn't help but check her out when she walked away. Mrs. Shaw was wearing a yellow sun dress that ended just past her knees. The dress hugged her curves with a hint of cleavage on display that would cause guys risk getting caught for a quick peek.

A lot more skin was being shown by Bailey. She had on an American flag bikini top that pushed her breasts nearly together to show off a good amount of her cleavage. It was more conservative compared to the top she wore to my party on Saturday. She had on a white sarong that was slightly see-through and her matching bikini bottoms were partially viewable.

Bailey and I were the only ones our age at the party. There were younger kids with the oldest among them looking like middle schoolers and maybe a couple of soon to be freshmen in high school. Everybody else was at least in their late 20s or older.

We were standing together on the back porch in the shade waiting for Mr. Hamilton to finish his first round of grilling. That is when Kate approached us.

"How are you two enjoying the party?"

"So far, so good. Although, I am getting hungry if you could tell Steve to hurry up," I responded.

"I'll see what I can do, but I know he will mention something about not being able to rush good food," Kate said back. "How is everything going with you Bailey?"

"Been a busy summer at times working as a lifeguard and trying to cut down my list of colleges," said Bailey.

"Good luck with the college stuff. I know it must be an exciting time for you and your parents. I'm glad I have a few years left before I have to deal with that process. I would chat a bit longer, but I need to be a good host and mingle with some of the other guests. Enjoy the party," said Kate.

"Can you do one thing first?" Bailey asked.

"What is that?"