Chronicles of Cole

Stirring awake, my bearings were a little off from waking up in an unfamiliar room. I had never slept in the pool house bedroom despite it being built years before as it was reserved for guests. Bailey was still snuggled up to me except with her back against my left side.

I reached over and grabbed my phone off the side table. Tapping on the screen, I saw that it was 7:33 a.m. meaning I had gotten nearly seven and a half hours of sleep. Not wanting to get up yet, I stared up at the ceiling thinking about last night's wild action that saw Bailey lose her anal virginity to my ex-girlfriend. It all concluded with me fucking Bailey in her ass that saw us reach intense mutual orgasms.

"Umm," came from Bailey as she turned over and slung her arm across my chest. Looking down at her, I saw her smiling up at me.

"Morning, beautiful," I said.

"Good morning. Last night was really fun. Hope you enjoyed the surprise," said Bailey.

"I did have an amazing time, especially once I got to fuck your ass," I replied while reaching down and grabbing one of her ass cheeks.

"Hmm... don't even think about fucking my ass right now. It is pretty sore," she said while rubbing her hand lightly over my chest. "I would love to stay in this position for a while, but I need to take a shower. You do too, because we both smell."

"Together?" I asked.

"Another time. If we did, it wouldn't just be a shower. Plus I really have to get back home," said Bailey before stretching up and giving me a quick kiss on the lips.

She then rolled over and sat up on the edge of the bed. After stretching her arms out, she stood up and headed to the bathroom. I admired her backside as she walked which caused a stirring in my loins.

I scrolled through social media apps while Bailey was in the bathroom. Initially disappointed I wasn't in there fucking her in the shower, I did realize it was better that wasn't happening. I would need my rest for Britney Williams' initiation ceremony tonight with the swingers group.

When I heard the shower turn off, I gave it a couple more minutes before getting out of bed and heading to the bathroom. I opened the door and saw Bailey wrapping a towel around her fantastic body. Her hair was wet and hung down limply.

"The shower is all yours. Don't mind me, I'll finish looking presentable while you are in there," my girlfriend said.

Jumping into the shower, I quickly dumped a good amount of body wash into a washcloth and started scrubbing my chest clean of the dried cum and sweat from last night. About 15 minutes later, I exited the shower all clean for the day. I noticed Bailey had left the bathroom at some point as I reached for a towel to dry myself off.

Once I had dried off, I left the bathroom and found Bailey had placed my clothes from last night in a pile at the end of the bed. I quickly put my clothes on and left the bedroom. That is when I saw my girlfriend sitting on the couch putting on her shoes.

"Those aren't the clothes you wore last night," I said to her.

"Alex stopped by before you picked me up yesterday and I gave her these clothes to bring over. Before you ask, she took my clothes from last night with her when she left. I'm going to pick them up later."

"That was trusting of you," I said slide my socks and shoes on. "She could have just taken your clothes and left you with nothing to wear."

"If she had, there would be hell to pay. Although I'm sure you would have given me some clothes to wear home," she responded.

"What makes you think I wouldn't have driven you back to your house naked?"

"Because..." she started to say while getting up. She stood in front of me and leaned in mere inches from my face before continuing. "If you did that, I would bring a hell storm down on you like you can't imagine. That would be followed by me breaking up with you," she then closed the gap and gave me a quick peck on the lips.

"Good to know for the future," I responded.

After I tied my shoes, I walked hand-in-hand with Bailey through the backyard to the house. It was still kind of cool outside, but I knew it would warm up soon.

Entering through the back door, Bailey started to say, "I checked my work schedule and have to... OH SHIT!"

I turned to where she was looking and was surprised to see my dad standing by the kitchen table. He had a mug in one hand.

"Well, good morning to you two," he said.

"Morning, Dad," I answered.

"Good... good morning, Mr. Webb," Bailey said nervously.

"What are you doing here?" I asked.

"I live here," he sarcastically responded before taking a drink of coffee.

"I mean, why are back here this early?" I questioned him.

"Maria and I were talking last night about how our planned trip had to be canceled. Since we are both off the rest of the week, we looked up and found a great deal for a hotel in Carmel-by-the-Sea. So, I came back early to repack my luggage for the rest of the week before picking Maria up."

"Okay. When will you be back home?" I asked.

"Sometime Sunday evening is the plan. If anything changes, I will let you know. Just don't burn down the house or cause any damage while I'm gone."

"Can do on both parts," I said.

"Hope you have a good weekend there. Cole, I really do need to get home, said Bailey while pulling my hand.

"Yeah... I got to take Bailey home. If I'm not back by the time you leave, I'll see you on Sunday, Dad."

"I won't keep you two. See you all later," he said.

Bailey yanked pretty hard on my right arm as we made our way to the front door. After getting on the road back to her house, she said in a worried tone, "That was so fucking embarrassing. I can't believe your dad caught us coming in from the pool house. He absolutely knows what we were doing last night."

"He doesn't know EXACTLY what we were doing. Plus, he already knows that we have been having sex," I told her.

"Seriously, Cole!?! Why aren't you embarrassed or worried or something about your dad catching us?" She questioned me.

"It was a little embarrassing, but it wasn't like he walked in us mid-action or anything. He probably already knew we were out there since my car was in the driveway and we weren't in my bedroom," I said.

"Well... it is still embarrassing to me," said Bailey.

It was quiet between us for the next few minutes before she spoke again. "What I was going to say about my work schedule before we were interrupted was that I have the early shift tomorrow morning."

"Okay. Will you be coming over any night while my dad is gone?"

"About the weekend... Anna and Olivia are both heading up north for some college visits. They asked me to go along with them, and I said yes. Anna's dad and mine are going to be sharing the driving duties. It also gives us a chance to visit with Claire as they are checking out a college I'm not interested in."

"So, you will be gone all weekend as well?" I asked.

"Unfortunately, I will be. We will be getting back late on Sunday. Think you can survivor by yourself for the weekend?" she asked as I pulled into her driveway.

Putting my RAV4 into park, I responded, "I think I'll survivor. When did this trip come about?"

"Yesterday at the Hamilton's party when we were tanning by the pool. We got to talking and they really pushed me to come on the trip. Kind of making it into a girls' trip except with mine and Anna's dad also coming along."

"Gotch ya. I guess I will see you at some point next week then. Hope you have a great trip," I said before leaning over and giving Bailey a kiss on the lips.

"Thanks. Text me if you get bored and I might send you some fun photos," my girlfriend said with a wink. "I'll see you later. Love you, Cole," she added while opening the passenger side door.

"I'll definitely text you for some photos. Love you too, Bailey." I responded.

Giving me a big smile, Bailey blew me another kiss before closing the car door. I watched as she walked up the sidewalk towards the front door. As she got to the top step, the door swung open and her mom, Jennifer Shaw, stood in the doorway.

The hot, blonde MILF was wearing a slightly oversize white t-shirt, grey leggings and tennis shoes while her hair was pulled back in a ponytail. Her clothing was partially damp from what I assume was sweat having most likely gotten back from a morning run not that long ago.

Jen held the door open for her daughter to enter the house. After Bailey did, Mrs. Shaw looked over at me and gave me a slight wave and a knowing smile before closing the front door.

I drove back home and when I got there my dad had already left. He left a note on the kitchen table asking me to clean up the pool house as soon as possible. That is what I did after grabbing breakfast and relaxing for a while.

Due to the swinger group initiation later in the night, I stayed at home to rest for evenings activities. It was early in the afternoon when my phone pinged with a text message notification. I saw that it was from Britney.

[Britney]: Hope you are ready for tonight because I am. Also, bring your friend Doug or whatever his name is with you tomorrow to help "clean" the pool to completely my end of the deal.

[Cole]: I'm ready for tonight. His name is Rob and I'll make sure to bring him along.

[Britney]: Good. I'm going to rock your world tonight and your friend's tomorrow 😈.

[Cole]: Looking forward to it 😏.

[Britney]: You better be...

The next text from Britney was a selfie of herself that had me hard instantly. She had a seductive look on her face while holding her right arm across her bare chest. The pressure from her arm caused her breasts to push upward and show off a large amount of cleavage.

It was tempting to start jerking off to the photo, but I needed to hold off for tonight. I saved the photo so I could masturbate to it later.

I then texted Rob making up a story about Britney's parents throwing a party yesterday and needing their hot tub cleaned along with their pool tomorrow. Since it was going to be more work, I asked if he wanted to help me out and make some extra cash. He agreed to assist me almost immediately.

Just before 5 p.m. I started to get ready to head to the Hamilton's house. I took another shower to smell nice for Britney. Since I was going to be naked, I decided against bringing any extra clothes with me.

After eating dinner, I left to drive over to the Hamilton's place. I parked where Kate told me in the Jones' driveway. When I pulled in, I suddenly started getting nervous. It wasn't about fucking Britney but more about having sex in front of a group of people.

My hands were sweaty as I rang the doorbell of the Hamilton's house just before 7:30 p.m. I shook my arms out hoping to relieve some of my nervousness. Right after, the front door opened. There in front of me stood Kate Hamilton. She had on a t-shirt and blue athletic shorts while her shoulder-length hair had some extra volume to it.

"Hi, Cole. Come on in. You are right on time. Do you want anything to eat or drink to hold you over until the fun begins?" asked the older blonde woman.

"I'll take some water and something to snack on while I wait. I'm assuming Britney is here?" I asked.

"She did and is currently getting ready," Kate answered while leading me to the kitchen.

I took the opportunity to check out her pert ass as it swayed while I followed her. Memories of grabbing, spanking and fingering it throughout the summer flashed through my head. Part of me wanted to take the blonde MILF right there in the kitchen. However, I knew I needed to save my energy for what would be happening in just a few hours in the house.

Mrs. Hamilton fixed me a glass of water and then grabbed some snack bags of peanuts, gushers and a fruit cup. Handing me the items, she said, "Hope you don't mind these snacks. It is all we have that the kids wouldn't make a big mess of when eating."

"Not a problem. These will helpful until it is show time," I responded.

"Good! Now, follow me to the room. A few of the attendees like to arrive early to hang out for a bit and will be arriving any minute. Plus, I need to finish getting ready," she said with a smile.

I followed Mrs. Hamilton up the stairs and to the room she had shown me yesterday at the Fourth of July party. She had an extra sway with each step she took up the stairs. Tempting me with her ass knowing I couldn't do anything as I carried the glass of water and snacks in my hands.

Kate held the door open for me while partially blocking the entrance. This caused me to have to slide by her. She took the opportunity to grab my penis through my shorts, which stopped me in my tracks.

"I wish I was getting fucked by this big dick tonight," she said while squeezing my cock. "I've been craving it stuffed in my pussy for nearly two weeks. So, you better be prepared to give me a good fucking on Friday when you come over."

"You can't count on that happening," I told her.

Mrs. Hamilton gave me a beaming smile as she gave my penis one last squeeze before letting go. I moved the rest of the way into the room and the door closed behind me. After placing the water and snacks on an end table, I sat down on the right side of the bed. That is when the door opened suddenly.

"Before I get to busy entertaining, be ready to go around 9 p.m. I will come up and get you around that time. Also, here is your mask for tonight," said Kate. She tossed a bundled up red item at me that I caught.

As soon as the mask was in my grasp, the door was quickly closed. Unfurling the wad of fabric, I saw that it was it was a luchador mask made out of a stretchy material. It was mostly red except for thick, silver bands around the eyes and mouth. The eye areas actually had coverings over them that had numerous small holes that I would be able to see out of but prevented others from seeing my eyes.

It was an excruciating long wait in the room. I heard people arrive at the house over the next hour. Sounds drifted upstairs of people talking and laughing, but I couldn't make out anyone in particular. At a quarter 'til nine, I stripped off my clothes and wrapped a white bath towel around my waist that was laying on a dresser. I then pulled the mask over my head. It took a couple of minutes for me to adjust it so that everything was inline.

My initial worry about the eye covering was muted. Turns out they barely hindered my vision.

I sat down on the bed and nervously rubbed my hands together. I was worried someone would be able to recognize me or that I would say something that might give myself away. Right before the clock struck 9 pm, there was a knock on the bedroom door before it opened.

There stood Kate Hamilton wearing a red teddy that fell just below her crotch. She was wearing matching red panties. The teddy material was sheer and didn't hide the fact that she was not wearing a bra. Her nipples were hard on her still perky b-cup breasts. The older woman had her shoulder length dyed blonde hair blown out.

She had hunger in her eyes as she looked me up and down before saying, "Ready for your fun tonight?"

"Yeah, I am," I told her while being able to hide any nervousness I was having from her.

"Good. Follow me. Everybody is ready for you and Britney to put on a show," she answered back.

Kate turned on her heels and started walking down the hallway. I stepped out into the hallway and closed the door before starting after her. Looking at her from behind, I saw to no surprise that she was wearing a thong that accentuated her pert ass cheeks.

Right before we got to the stairs, she suddenly stopped and turned around to face me. The older woman put her right hand on my chest and looked into my eyes before saying, "Just so you know, you might recognize a couple people here. I hope you don't use that to your advantage in any way. This group is a secret among friends that we don't want everybody to know about."

"I understand and will keep my mouth shut," I told her.

A soft smile spread over Kate's face as she said, "I figured you would. Now, after your part is done with Britney, head back up to the room, get dressed and use the backway to exit."

"Will do," I said.

"Good," she responded while sliding her hand down my chest and stomach before stopping right as she reached the towel around my waist. "Now, go put on a show and give that hot, big tit blonde a good fucking."

"I'm planning on doing just that," I told her.

Kate turned back around and started to head down the stairs. At the same time, she grabbed my right hand to lead me down. As we got closer to the landing, I noticed that the lights had been dimmed and there were lit candles spread out around the room.

Multiple eyes were immediately upon us when my feet hit the floor of the living room. Besides Mr. Hamilton sitting by himself at the moment, there were five other couples sitting around on couches or love seats. I didn't get a good look at who they were before Kate spoke.

"Everybody, let me introduce you all to Britney's selected dick for her initiation tonight. He goes by Cock. To remind you all again, no matter how much you beg, only Britney and I know his true identity and will not be telling any of you all. Also, Cock here has promised not to tell anybody about what happens here tonight under the threat of very, VERY bad punishment."

I was thankful that the mask hid my face as Mrs. Hamilton never mentioned any type of punishment if I let the secret out. The quick look she gave with a slightly sexy look hinted that any punishment would be sexual in nature.

"Now," she started to say turning back to her guest. "Who's ready for a hot, live sex show?"

A cheer rose from all of the couples in response. That must have been the queue for Britney to make her appearance. From my left, she came sauntering into the room from down the first-floor hallway. All Britney had on was a black satin robe that fell just past her crotch. It was tied around her waist and open at the top to show off a lot of cleavage.

She walked up and stopped inches from me with a big, excited smile. Wearing four-inch black high heels put her nearly even in height with me. I noticed that she had her blonde hair pulled back into a loose ponytail.

"Ready to blow all of their minds?" Britney quietly asked me. At the same time, she started to rub her hands over my abs and up to my chest.

My mouth had gone dry with anticipation and nervousness. All I could do was nod my head in response.

Somehow Britney's smile got even bigger. She then took a step back and untied the matching satin belt from her robe. Grasping both sides of the robe, Britney quickly took her robe off in one motion to stand in front of all of us in her naked glory.

My mouth dropped open at the amazing sight before me and after all the teasing she had done to me during the summer. Her DD size breasts sat high on her chest with a slight sag and were capped off by quarter size areolas and hard nipples.

Britney's flat stomach led to a bare pussy. There was a slight glint from her excitement. She turned to face our audience and said, "I know Cock here likes what he sees. What about you all?"

"Fuck yeah!"

"Hell yes!"

"Woo!"

In response, Britney shook her big tits for the audience before pinching both of her nipples. While they admired her breasts, I couldn't help but admire her round ass cheeks. They were definitely a good handful for myself.

Britney turned back to me and said, "Your turn, Cock."

She then dropped down to her knees in front of me. Looking up at me, she grabbed ahold of the towel and opened it up. The right side she held up to block the audience's view of my dick.

"Fuck!" Britney let out seeing my mostly hard cock pop up and just barely miss smacking her in the face. Her eyes were wide in amazement. I noticed her lick her lips while letting out a slight moan.