I joined the Navy when I was eighteen, and my first duty assignment was aboard a patrol ship. Being that I was new and had no rank, I was forced to live on the ship even when it was docked for the first year and a half, and had no private quarters of my own. I slept in a berthing area with 16 other guys, and had few moments alone on the ship when I could masturbate. I did have a car however where I would make daily trips for a much needed release.
I was extremely horny all the time at that age, and kept a few magazines in my trunk to which I would frequently look at while masturbating. Living in a metro coastal city, my only problem was finding a place to masturbate where I would not attract too much attention. I mostly found places in the back or sides of supermarkets or industrial building that were somewhat secluded, and where I liked the idea of being caught, not knowing who I would be caught by was always a concern. Often my raging penis and the need to release made me impatient with trying to find the perfect place, settling sometimes for parking lots that where mostly empty with a low but existing risk.
After just pulling in from a three month voyage at sea, and not having masturbated in over five days, I was in desperate need to cum, and my penis started leaking pre cum from the very moment I got in my car. It was the middle of the afternoon, and I immediately drove to a parking lot on the side of a grocery store that had a few cars sporadically parked in the open space. I settled for this location and decided to park directly next to a mini van, to give me a little cover on the driver's side. I knew that it wouldn't take long so I figured that the chances of the owner (of the minivan) catching me was fairly slim.
I took out a magazine and an extra pair of boxers to catch the cum, and was furiously rubbing my penis after one last quick glance to make sure the coast was clear. As I was flipping through the pages with my other hand, having the magazine sitting in the passenger seat, my head and my focus was turned completely away from the minivan. After a few minutes I was repositioning the extra pair of boxers, getting it ready for when I was going to soon be cumming, and out of the corner of my eye, I saw movement from the minivan directly next to me. The minivan was parked not more than four feet away from my low sitting car. I instantly froze, not wanting to turn my head. Hearing the noise of grocery bags being placed in the van, I knew that if I haven't been seen already, this fate was inevitable. All of a sudden all the noise stopped and I could just feel eyes staring down on me. I knew I had just been caught with my hand still frozen on my hard cock.
After about 10 seconds of sitting completely still, and not hearing any movement, I slowly I turned my head, and there was a middle age woman looking right at me. Her faced turned from an expression of shock to a wide smile. She was fairly attractive, had brown hair, looked about 35, and had medium build. After the initial reaction of staring, being that she had just caught a man in the car next to her masturbating, she continued to put groceries into the side door of her van, smiling with a grin of seductive satisfaction. She took each bag out of her cart, one by one, looking over at me after she placed each bag in the van and after she reached for another bag from the cart. Her smile never left her face, and a sense of excitement raced through me body from the possibility that she was enjoying, and maybe even excited by this moment.
With the panic of being caught suddenly absolved, I then resumed stroking my cock with her watching me as she slowly put her bags away. My focus now turned towards her, as she then started to put the bags unusually far into the other side of the van, leaning one knee on the floor of the van while exposing her rear up in the air that was fitted in a tight pair of jeans. It was obvious that she was trying to subtley give me motivation to look at her while I continued to stroke. This continued as she put each bag in, and loose items like milk and cases of soda, one at a time, intentionally prolonging her viewing.
After she finished putting the last bag in she left to go put the cart away at its docking station, which was about 35 yards away. As she was gone I knew that she would return probably to look at least once more, so I pulled my pants all the way down to my knees and sped up my pace wanting her to witness my penis as I was spewing cum. I was just about at climax as she was walking back, and sure enough rather than walking the direct route to the drivers side door, she walked past her passenger door, then around the front of her car to the driver's side. Just as she walked past my car and was looking right down on me, I started to cum. Kind of caught between steps she realized that I was about to cum and stopped in her tracks to watch with a look of amazement. I did not cover my penis in the boxers like I normally do when cumming to prevent a mess, instead I let the first shot shoot into the air, pointed a little to the left, shooting one long stream against the window, with some hitting the roof of my car. I then covered my penis with my hand for the subsequent squirts using it as lubrication for my stroking. I came, and I came, and I came, with a huge handful of slippery cum, dripping all over my penis and my lap. It absolutely soaked my pubic region almost as if I had just come out of the shower, with an eruption of cum all over hand, wrist, thigh, while soaking my pubic hair, and dripping down to my sac.
She looked on through the cum splashed window, with her mouth wide open and her eyes glued on my lap, which lasted for what seemed like an hour but was probably more like 40 seconds. I slowed down to long slow strokes, then I started just rubbing the cum like it was soap all over my lap as if I was washing my crotch. Still kind of in between steps from where she had stopped walking to look at me, she stumbled into a walk again, as she went around the hood of the car, to her driver's side door. She got in backed up and cut the wheel so her diver's side window got one last glance at my now disastrous mess of a lap.
Being 18 and still having masturbation being sort of a taboo subject, this was the first woman who had watched me masturbate from start to finish. I like to imagine that she left her groceries in the car when she got home, and ran to her bathroom to masturbate replaying the experience in her head. This moment has always been a lifetime rush for me lasting to this very day.