Everyone in this story is above the age of 18.
This is a 100% true story. The only thing changed are the names to protect the identities of both parties involved.
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It all started out innocently enough. The first time that I met one of my mom's best friends was on vacation. We had rented out a beach house on Lake Michigan and her friend, Katherine, was coming up to meet us to spend the day at the beach and stay overnight. I was 18 at the time and just about to start my first year of college. I had no idea who this Katherine lady was and really wasn't that interested in meeting her, after all I had a girlfriend at the time.
I woke up early to get to the beach to go for a run before everyone else was up. I had a scholarship to play baseball for a local college and staying in shape was priority number 1 for that summer. I took my time admiring the sun rising over the lake and the sounds of the birds and waves hitting the rocks. By the time I had gotten back, everyone was up and eating breakfast.
My mom yelled for me to shower and get ready to go to the beach as Katherine would be there shortly and she wanted everyone to go together (AKA she wanted me to help carry stuff). I let the warm water run over me and relax the sore muscles after a long run. By the time I had dried off, thrown on some stuff to wear down to the beach, and run upstairs, I only had time to grab a bagel off the counter before we were out the door. However, there was a new car in the driveway this time. I thought, "That has to be Katherine and her kids." Sure enough, she was out there chatting with my mom while her kids ran wildly around the yard. From where I was standing, I couldn't tell much about her. I knew she was relatively short, very tan, and very skinny. Nothing impressive, yet. She was wearing big sunglasses, a long cover up, and a pair of flip flops that showed off some well-manicured toes. I walked down the stairs to introduce myself.
"Hi Katherine, it's nice to meet you. I'm Austin, obviously, the oldest child of my mother," I said with a chuckle. She held out a hand and politely said, "It's very nice to meet you as well. I've heard so many great stories about you with baseball and how well you do in school, and please just call me Kat."
"Well it's nice to know that my ma has a few good things to say about me!" I said as we all had a good laugh together. "Well let's all get headed down to the beach, can you grab the chairs for us Austin?" my mom asked before we all grabbed our stuff and started to walk to the beach. I grabbed the chairs, as well as my sunglasses, and walked behind the rest of the group.
We made it down to the beach in a few minutes, and even though it was barely 9am, you could tell it was going to be a hot day. I set up the chairs, peeled off my shirt and jogged down to the water before anyone had time to suggest another activity. I waded out a few feet and made sure it was deep enough before jumping in and submerging myself totally under the cool water. The water felt great as I popped back up into the harsh sunlight and I swam around for a little bit. After a few minutes of swimming through the waves, I decided it was time to head back in and lay back and relax. I walked back up the beach, dodging the Frisbees being thrown by the younger kids.
As I approached my chair, my jaw nearly hit the hot sand beneath my feet. Sitting there talking to my mom was this woman with just the most incredible body I had ever seen. She was petite, with a very small stomach and thin legs, but her breasts looked giant compared to the rest of her body. It took me a second to realize that this was Kat sitting next to my mom. Kat was the same age as my mom, 48, but her body reminded me of a 20-year-old, not someone approaching 50.
I composed myself quickly and sat down, quickly throwing a towel over my quickly hardening cock. I was able to maintain some small talk, and was able to catch a few nice glimpses of her large breasts under my sunglasses. Now I know women can tell when a man is looking anywhere but their eyes, but frankly, I did not care.
The rest of the day was relatively uneventful. We kept up the small talk in our small group and around 3 we decided it was time to head back for the day. Being out in the sun like that can really wear you out. As we walked back, I wanted to see if her ass was as amazing as her tits. As we walked, I watched as her ass bounced up and down with each step. Lucky for me I was able to hold the chairs in front of me. As soon as we got back, I excused myself to the basement shower and quickly rubbed one out before redressing and heading back upstairs. Despite my hopes, Kat and her children had decided that they were going to head back home instead of staying the night. I figured that would be the last that I would see of her.
About 2 months into my first semester of college, I received a text from my mom. She asked me if I would be able to help Kat out and tutor her kids in math and social studies. She said that she would pay me for my time, but I saw it as a good opportunity for two things. One, I would be able to see Kat again and two, I would be able to gain some experience working with younger children, as I was an elementary education major. I replied to my mom to just give Kat my number and I'd be glad to help her out.
A few nights later, as I lay in bed after a long day of practice and work outs, I received another text. This time it was from a number that I did not know. "Hey Austin, it's Kat. I talked to your mom about possibly helping me by tutoring my boys a little bit this year. I know you're probably very busy, but if you have some time that would be great!"
I quickly replied saying it would be no problem and I could come by the next day after practice. Since it was a Saturday, practice was over before noon and I had the rest of the day to myself. I showered in the locker room after practice and punched in the address to her house. It was a quick 10-minute drive and despite there being no prior hinting at her wanting to sleep with me, I was nervous as could be.
I pulled into her driveway and recognized her car from the beach. I quickly walked up to the front door and rang the doorbell. She greeted me at the front door in a loose fitting t-shirt and basketball shorts, not exactly the sexiest thing ever. I entered her house and followed her down to the basement where she had some stuff that she wanted me to look over. Interestingly enough, there were no kids in the house. As if reading my mind Kat said, "The boys are at their dad's house for the weekend. I just wanted to give you a chance to take a look at the material to be sure that you could help them out."