19 [M] Living a “Mom’s Best Friend” Scenario

Our next door neighbor, we’ll call her Cindy, was about the same age as my mom, I would guess, like mid 40’s. I don’t know if her and my mom had grown up together but they were extremely close friends. They did everything together and were almost always talking to each other on the phone or she would be at our house, or my mom would be at her house. Cindy had a key to our house so she was always coming in and out either to hang out with my mom or just to use our pool. An avid swimmer, she often came by for a quick swim or tanning session. She was very attractive and I always had a bit of a crush on her. She was tall. She had blonde hair with loose, flowy curls and the most beautiful blue eyes that you could just get lost in. Her body was amazing! Curvy in all the right places. She was also one of the only single women her age in our neighborhood. I was always a little shy around her just because I thought she was so hot!

Once in a while, I would overhear her, my mom and their friends gossiping about other people in the neighborhood and once in a while, the conversation would get dirty. These sweet, small town girls when they got talking amongst themselves could make college kids blush. I overheard one particular story of Cindy’s that involved a patient of hers (she was an rn). She mentioned that he had a horse-cock and she was having trouble focusing when she was examining him.

I thought about that story a lot. It turned me on to hear her talk about sex so openly. Especially to hear that she was a size queen as I had a pretty large penis myself. It had become my goal, from that point forward, to show off to her a little bit because even though I had a crush on her, I was practically invisible to her.

Fast forward a couple months to my younger brother’s birthday party. It was a hot summer day so we decided to have a party by the pool. All of the housewives would lay beside the pool and work on their tans. I had been working out and was in pretty good shape by this time so I tried to get her attention a little bit. She didn’t seem to notice me no matter how hard I tried. I even said hi to her and she barely acknowledged me. I was a little annoyed after about a half-hour of trying to get her attention. After a while, I forgot about her and just tried to enjoy the party.

After a couple hours, my friends and I, including my brother decided to go up the road to get ice cream. I excused myself from the group to go change before we left. I quickly ran to my room, got out of my wet swim trunks and started drying off. I heard the sound of a door closing from the bathroom in my room (my room had a bathroom in it) and turn around completely naked. Who else would be there except Cindy looking amazing in her bikini with a stunned look on her face and a stack of beach towels in her hand. My mom must have sent her to my room to grab more beach towels but I wasn’t thinking about that. Her eyes went straight to my penis of course and I suddenly felt very self-conscious and speedily grabbed my towel to cover up.

“Oh my God!” she shouted. “I’m so sorry I didn’t… I’m sorry!” She raced out of the room with a mischievous grin on her face. I don’t know why I was so embarrassed but I was. I took a couple minutes to just sit down and think about how awkward our encounter was.

Since that day, however, she seemed to begin to look at me differently. She acknowledged me when I was in the room, she smiled at me, and even went out of her way to greet me. Once in a while, when she would come over to our house to sunbathe by the pool, she would wear tiny bikinis that just barely covered her ample assets. One such time, while my mom was at work and my younger brother at school, I decided to take the ultimate step in exhibitionism. While she was sunning by the pool, I made sure that we were home alone, removed every stitch of clothing I had on, and walked from our house to the pool house. She got a great view of my entire body as I walked by and she looked very impressed. Maybe even a little turned-on. “Hi Cindy.” I said elegantly before closing myself in the pool house. My heart was racing but it was so worth it. She noticed me now!

I’ll tell the rest of the story if you guys like this one.

Source: reddit.com/r/gonewildstories/comments/p5ngld/19_m_living_a_moms_best_friend_scenario