I (m21 at the time) went to my family friends for a get together. We’ve been friends since we were kids and I’ve never thought of his mom (f42) in any sexual way until I saw her in a slim bikini.. it squeezed her chest and ass so tight I thought it would rip. I would estimate a DD for her size, slim figure with a cute face and lips that would make me have to adjust myself every bit and then. I always fantasized about her giving me head.. And after that moment, I began to deviate.
I’m not so bad myself. I’m 6’3”, 175lbs, athletic build, and an 8 inches hung. (Dm for pics)
I went over for a family friend gathering and decided to wear some swim trunks that gripped me a little bit once they got wet. I went in the pool to relax and thought of her. I waited until I was bulging and showing off a chub before she came out and offered me water. “Oh thank you Jane! But I can manage, I was just getting out.” As I stepped out, my heart started thumping. She looked, her eyebrows raised, and her mouth opened as she stared at my shaft stretching down my thigh, compressed by the trunks, but you can clearly see me. She then came out of her trance and suggested I dry off in her restroom since there was somebody in the guest restroom.
I followed her with my towel over my shoulder to keep me still in view. And she let me into the restroom. I thanked her and extended my arm for a hug. She came close and hugged me back saying “you’re welcome, big guy” and glanced back down at my dick print before exiting the room.
My first story ever confessing. All is a true story. Lmk if you want more of our history. This was only the beginning