Chronicles of Cole

I was hoping to have a date night with Bailey on Friday. However, her mom wanted to do a girl's night with her since Bailey had been gone most of the week for college tours. My dad was out on a date with Maria and would be out of the house for the night giving me free reign of the place.

Free reign for the evening meant ordering a pizza and playing video games. I would have gone out, but all of my friends were out of town on vacation or at a prospect camp on a college campus. Eventually, I got bored and decided to have some special alone time.

Pulling out my phone, I opened up the first photo that Gabby Thomas sent me yesterday of her wearing a tiny green bikini on vacation. Taking off my shorts, I squirted some lotion and started jerking off to her photos.

I focused the most on the photo of her when she was on her hands and knees on the bed looking back at the camera, along with the short video of Gabby in that position. That video clip and photos got me hard, but I decided to pull up the photos and video clip that Jennifer Shaw sent me Wednesday night.

Seeing those naked photos and the video of her fucking her pussy with one of Bailey's big dildos had me leaking precum. Right as I was thinking back to fucking Mrs. Shaw, I heard my phone ding with a text message.

Speak of the devil. The text was from Mrs. Shaw. With her being out with Bailey for their girls' night, I figured either they got their phones mixed up or she was sending me a photo featuring her daughter in it.

Turned out I was wrong on both fronts. Along with a message, Mrs. Shaw also sent me a photo.

(Jen): I had your cock on my brain. Wanted to show what that does to me 😈.

The photo was a selfie of Mrs. Shaw in a bathroom stall. She had her tits spilling out and her dress was bunched up around her waist. Her right hand was between her legs spreading her bare cunt open.

I couldn't help it and started pumping my cock harder and faster when Mrs. Shaw sent me another text.

(Jen): Wish you were here in this bathroom stuffing me with your fat cock in my Cole!

(Jen): By the way, did you enjoy spying on me riding Tim last night?

(Cole): I'm sorry about spying last night. Just got curious as I was about to leave after hearing noises coming from the room.

(Jen): Cole, don't be sorry about watching. It turned me on knowing I was being watched. Back to my question, did you enjoy spying on Tim and me?

(Cole): I have to admit, it was hot to watch.

(Jen): I figured you did 😈. Would have loved it if you pulled your cock out and jerked off to us 🥵.

(Cole): Maybe next time 😉

After sending that message I immediately had regrets. I just got caught up in the moment. Plus, I had no idea if there would be a next time catching Mr. and Mrs. Shaw fucking.

(Jen): You better! You're making me so wet!!!

Mrs. Shaw also sent a video with the message that had me jerking off even harder.

"Look what you are doing to me Cole. Listen to how wet you have made me. My cunt is absolutely soaked," she said while fucking herself with two fingers. I could hearing the sloshing sound coming from her pussy.

"I'm going to make such a mess in here thinking of you Cole. Being such a slut recording this for my daughter's girlfriend. I'm so close to cumming! Oh god, oh god, oh shit," Mrs. Shaw exclaimed. I heard the same sound that she had, that of someone opening the bathroom door.

Not long after I got text from Mrs. Shaw.

(Jen): Damn lady! I was so close to cumming and am so worked up. Maybe I should drop Bailey off and come over to your house to ride you big cock. Would you like that, Cole?

(Cole): While that would be great, not sure if that would be a good idea.

(Jen): That's disappointing ☹️. Is it because you already shot your load?

(Cole): No, I didn't cum.

(Jen): Prove it to me. Send me a picture of your hard cock.

I snapped a picture of my still hard dick and attached it in the text. I hesitated for a moment. Thinking about what if Bailey or someone else came across the photo in her phone. Then I got another text from her.

(Jen): Well Cole, this horny MILF is waiting for proof.

I hit send and added "This proof enough for you," to the waiting mature woman.

(Jen): Ummm... I need all of that in me! Didn't think I could get even wetter 💦.

I was expecting another text from Mrs. Shaw but didn't receive one. But I did get one from someone else.

(Bailey): Disappointed we couldn't get together tonight. So, here are some photos to enjoy 😈

Six photos then came in from my girlfriend. The first was a selfie from her chest up in a bathroom stall. She was wearing a black dress that showed a good amount of cleavage. Her hair was done up and had a naughty little smirk on her face.

The second picture was basically the same as the first with the exception being her dress was no longer visible. She had unleashed her big, tanned breasts that caused me to start jerking off again.

Photo number three was another selfie of her topless. This one showed her pinching her right nipple with her thumb and index finger of her right hand. Bailey's mouth was slightly open as if she was moaning.

The next photo was taken of her crotch. There was no underwear showing, just a clean view of her nearly bare pussy except for her small landing stripe above her clit. I wondered if she had gone commando or just taken off her panties before taking the photo.

Her fifth pictures consisted her of with two fingers jammed up her pussy. This one had me jerk my cock faster imagining that I was fucking her instead of her fingers.

The sixth and final photo caused me to immediately stop jerking off. It was a full body shot of Bailey sitting on the toilet. Her dress was bunched around her waist with her legs still spread. She had two fingers jammed into her pussy and was also pinching her left nipple with her right hand.

Someone else had taken that photo! I immediately had to text Bailey.

(Cole): Those photos were 🔥! But who took the last pic???

(Bailey): Some woman.

(Cole): How did that happen?

(Bailey): I didn't realize she was in the other stall and heard me moan while I was fingering myself. She startled me but came up with the idea for that photo.

(Cole): I got to say, that might be my favorite photo of the bunch since I get to enjoy seeing your entire, sexy body 😈.

(Bailey): Thanks! 🥰

(Cole): What's next for your night out with your mom?

(Bailey): Not sure. We will see where the night takes us. We are heading out. Will talk to you later on. Love you, Cole!

(Cole): Love you, too, Bailey!

I ended up going back through the photos Bailey sent me and eventually came while looking at that final photo. Thinking of fucking her amazing pussy while playing with her big tits.

Later that night, I got a text from Bailey letting me they were back home. She was tired and had another early day with her lifeguard job, I also got a text from her mom.

(Jen): Bailey's heading to bed. I could still come by your house for that cock of yours 🤤

(Cole): That wouldn't be a good idea. Plus, my dad is going to be home soon.

(Jen): Well, that is disappointing. Maybe next time we can have some fun. Guess I will have to settle for one of Bailey's toys again.

Fuck! This woman had it bad for me, or more correctly my nine-inch cock. Even though I didn't know for sure if my dad was about to be home, the lie turned out to be true. My dad got back to the house about 20 minutes later. Had I given in and told Mrs. Shaw to come over, I surely would have been balls deep in her pussy with her screaming in pleasure. That would have been an awkward situation to have my dad walk into and explain to him.

Saturday morning saw my dad take me to the local country club to play a round of golf. I had a good round for myself with a score of 97. My dad, on the other hand, was 23 strokes better. No surprise considering how much he plays compared to myself.

While out on the course, the cart girl did the typical flirting with me to sell beverages and food. It was different when she talked with my dad. She was extra flirtatious with him, touching him on the arm and laughing extra hard at a joke.

It was more than trying to sell him a drink and something to eat. With no wedding ring, he was definitely a target for gold diggers. Seemed like she wanted to be one. She was at least 21 since she was hawking beer, five and a half feet tall, brunette hair that was tied in a ponytail, and had B cup, may a small C cup breasts.

We met up with her again at the 14th hole. I didn't need anything from her this time and took the opportunity to hit the bathroom at that location. As I rounded the corner coming out, I saw the cart girl standing close to my dad. She was whispering something to him, but her right hand was rubbing his upper left arm while her left hand was rubbing his dick through his pants.

Stunned by what I was seeing, I moved back behind the corner and peeked my head out to see where this could be going. She continued rubbing my dad's dick for about 20 more seconds while my dad started to rub her ass over her skirt. Then I saw his head turn to his right. I heard why as another group was approaching us.

The cart girl pulled away and my dad removed his hand from her ass. I took this as my queue to start heading back to the cart, as well.

"Ready to get going," I asked.

"Let's see if they want to play through," he said while trying to hide his erection.

Unfortunately for him, they didn't want to play thru and instead flirted with the cart girl some. Just before we drove the final feet to the tee box, the cart guy came up to my dad

"Don't forget your change, Mr. Webb," she said while holding a couple of bills in her hands.

"That's okay Kate. You can keep it as a tip," he responded.

"Thank you very much! It was very nice to meet you today," she said while extending her right hand for a handshake.

My dad shook her hand and then we were off. I noticed as we got to the tee box that he had a piece of paper in his right hand.

"What do you go there," I asked.

"Looks like I made an impression on her. She gave me her phone number and one of her social media account handles," he said and then showed me the note.

"Good thing you are dating Maria. If not, I bet you would be calling her once we are done," I said.

"Once we are done? I would be calling her as we were driving to where our next tee shots landed," he jokingly responded.

"Geez, Dad! Talk about making it weird in the cart," I said.

"You want weird," he said while getting out of the cart to grab his driver. "How about her being your new stepmom?"

"Seriously!?!" I quickly responded.

We didn't say any more about Kate the cart girl for the rest of the round. After we were done with our round, I put our clubs away in the car and returned the cart before hitting the shower in the locker room while my dad went straight there after we were done.

After drying off, I headed back to the locker area and heard my dad talking with someone.

"So, you met the new cart girl, Will?" the other guy asked.

"I did John. She was... very friendly," my dad answered back.

"Friendly? How was she friendly," John questioned.

"She worked her hand over my cock pretty well out near the 14th tee box. If that other group hadn't shown up and my son wasn't going to get back from the bathroom soon, I would have given her what she was feeling up," my dad said.

"Damn, Will! All the other guys said she would just flirt with them. How did you get so lucky?"

"Not sure but might be because of my good looks compared to a lot of the other guys here."

"Very funny. Surprised she wasn't all over Cole." John said.

"She is definitely looking for an older guy to take care of her. If she wasn't, then Cole would have been the one being felt up on the course," my dad responded. "The crazy thing is she gave me her phone number and her social handle."

"GET THE FUCK OUT OF HERE!" John exclaimed. "You going to call her to get some of that college pussy?"

"I would if I wasn't dating Maria. That would be one tight pussy to fuck all summer," my dad said.

"Well, if you change your mind and want some of that college pussy, there would be plenty of guys to take Maria off your hands to free you up," John said.

"Thanks for the offer, but that's not going to happen," responded my dad.

The conversation then steered over to business talk. That is when I entered the room to get dressed, and pretended I didn't hear any of what they said.

Later that night, I saw the piece of paper with Kate's number and social handle laying on the counter. I took a picture of it to check out her social media accounts.

Up in my room, I looked up her Instagram page. It was the typical photos from a college student. She had a fit body from the bikini photos she posted. As I was about to leave her page, I noticed the link in her bio. Clicking on it sent me to a surprising website: OnlyFans

I definitely wasn't expecting the link to take me to that site. It was slightly tempting to join her page, but didn't want to pay $25 a month for access.

That night over dinner I brought Kate up to my dad.

"So, I saw that slip of paper that Kate gave you today. Decided to checkout her social media accounts, and found her Instagram page," I said.

"You find anything interesting," my dad asked curiously.

"She had normal pictures you would expect from someone like her in college. Although the link in per profile took me to an unexpected site," I said.

"What's so interesting about the site," he questioned.

"She has an OnlyFans page," I responded.

My dad was surprised by that. He eventually asked," Did you join it?"

"No, I'm not paying $25 a month to have access to her page. She was also way more into you than me."

"That was so true. The good thing is that I will only see her at the club if I decide to go golfing. Even then there is no guarantee that I'd run into her based on when I play, and she works. The odds aren't great of me seeing her again," stated my dad.

After dinner, I texted Bailey to see how her night was going. I knew she was going out with a couple of her cheerleading friends. Like her mom, they didn't have a chance to hang out with Bailey this past week and wanted to make up for this evening.

(Bailey): Hey honey! We are about to pull into the restaurant.

(Cole): Where did you all decide to eat?

(Bailey): Old reliable. Olive Garden. Some of the girls are trying to talk us into going to that new 18-year-old and over club that opened recently.

(Cole): Night Sound? I thought it would be a good place to check out together. But if you all have decided to go, have a great time.

(Bailey): Thanks honey! You have any big plans for tonight?

(Cole): Just hanging around the house. Everybody else is still out of town either for sport camps or vacation. Rob gets back late tonight and we are planning on meeting up at the pool tomorrow.

(Bailey): Awesome! I'll see you two there. Got the late morning/early afternoon shift. Need to go, our table is ready. Love you, Cole! 😘

(Cole): Love you, too, Bailey!

Later in the night while I was watching a movie, I got more text from Bailey.

(Bailey): Hey, honey! Thought you would enjoy these! 😘😘

She had included a few photos and videos that were taken at the club. The first was a group shot of everyone. Bailey stood out with her hair made up and the perfect amount of makeup that brought out all her best features. She wore a blue dress that hugged all her curves tightly and left a decent amount of cleavage showing.

All of her friends were dressed to the nines, as well. They were definitely going to be turning heads that night.

There were a couple other group shots and one of Bailey posing in front of a mural on one of the walls.

Playing the first video clip, it showed the group hanging while panning over to show the club. The camera flipped to Bailey's beautiful face.

"Hey Cole! This place is pretty cool! You're definitely taking me back here soon! Enjoy your night," she yelled over the music.

Most of the other videos were of the group dancing and having a good time. The second to last video was my favorite. Whoever had the phone, they concentrated a lot on Bailey and Alexandra McCloud dancing together.

Alexandra, who prefers to go by Alex, at 5-foot, 3-inches is two inches shorter than Bailey. She has blonde hair that is currently shoulder length, brown eyes, nice B cup breasts and a perky ass. I loved grabbing her ass whenever possible when we dated over a year ago. It had been a year since we broke up. Thankfully it wasn't a bad breakup, and we were still friendly when we were around each other.

The blonde duo would dance close to each other and occasionally run hands up the sides of the other. At one point, Alex grabbed both of Bailey's ass cheeks and pulled my girlfriend right into her. Bailey was laughing and then said something to Alex that wasn't audible over the music. I could see Alex respond, which elicited a big smile from Bailey while nodding her head before the video clip ended.

In the final video, it showed some of the other cheerleaders dancing with random guys. The camera eventually panned over to the left. There was Bailey with her back to a guy that I recognized, Alonzo Jenkins. He was three years ahead of me and Bailey and was currently a defensive back for the UNLV football team.

He had his black hands on her hips while grinding his crotch into Bailey's ass. She was grinding back into him while her hands were on top of his. Alonzo, who was about an inch shorter than me, leaned down and said something into Bailey's right ear. She looked back at him and shook her head in the negative.

Alonzo again said something to her. This time Bailey laughed before again shaking her head no. About 10 seconds later, he said something to her for a third time while sliding his left hand off her hip and ono her stomach. This time, Bailey bit her lip while looking at whoever was holding the phone. She turned her head back to him and that is when the video ended.

I was partially stunned by what I had just seen and curious about what Alonzo had said to her each time. Turned out I was a little turned on as I could feel my cock had harden a bit. I thought about texting Bailey but held back not wanting her to think I was jealous or worried due to that last video.

About 45 minutes later I received a Facetime call from Bailey. Her stunning face popped up when I answered.

"Hey babe, how is everything going," I asked. The background I noticed was light blue fabric. Something you wouldn't find in a club.

"It been a great night. I had such a fun time. And not sure if you heard me in one of the videos I sent you, but you are definitely going to be taking me back," she responded.

"Maybe next weekend. I'm pretty sure I will be free unless my dad surprises me in wanting to do something."

"Sounds like a plan to... umm... me," she slightly moaned.

"Bailey? What is going on and where are you," quizzingly I asked.

A naughty look came across her face before she answered. "I'm at a friend's house. We decided to head here after everybody else had to get home before their curfews. I'll be... Oh yes, that's the spot... staying here for the...umm, you are so good at that... night."

I was speechless as I watched my girlfriend being pleasured by an unknown person at an unknown house.

Sensing I couldn't come up with anything to say, Bailey said, "Don't worry Cole. I'm in... Yes, stick another finger in my pussy... good hands. There isn't anything... God yes, suck my clit. OHH! You are so good at that. Fuck, fuck, fuck!"

Finding my voice, in a raised voice I said, "Bailey, who are you with!?!"

"Oh god, oh god, you are so good at that. We are totally doing this a lot more times," exclaimed my girlfriend. Composing herself just enough I heard her ask, "Should I show him who is eating my pussy?"