I am a 28 year old bi guy and live in the San Francisco bay area. I am 6 feet, three inches tall, weigh 180 lbs, brown hair and eyes and I keep in good shape by riding my bike a lot. I have my pilots license and am lucky to work for a company that lets me fly around the state for business whenever the need arises.
I had to fly down to a small town along the California coast for business one day this last December. It was beautiful and clear in the morning when I took off. The flight takes about an hour and a half and there's not much to do once you get up to cruise altitude and on course. I had finished my cup of coffee and was enjoying the view somewhere over Watsonville at 5,500 feet when I started to get a hard on. I though "why not?" Not exactly the mile high club, but what better way to pass the time by myself? I hadn't seen my girlfriend for a couple of days and I hadn't jerked off since I'd last been with her. I unbuttoned my jeans and pulled them down around my ankles. I still had my feet free so I could operate the rudder pedals if I had too. The air was clear and completely calm.
I was wearing loose fitting white Calvin Klein boxer briefs. My dick was really hard and tenting them by the time I got my pants down. My briefs were loose and soft, and I was able to close my hand around my penis covered by them. For several minutes, I enjoyed just stoking my shaft in my underwear this way. The one thing I couldn't do except for a moment or two was use my left hand to touch my balls. I had to keep my left hand on the yoke to keep the plane from entering a gradual turn to the left.
I kept slowly stroking my cock through my underwear until a wet spot appeared where my precum leaked out of my slit and into my shorts. Once it started flowing, it kept coming. Pretty soon, there was a wet spot the size of a quarter right on the tip of my penis. The wet fabric rubbed the tip ever time I stroked down, and I could see the shape of the head of my cock clearly through the fabric. I wanted more friction, so I spread apart the fly on my briefs and poked my hardon out through it.
Keeping my eyes on the instruments prevented me from closing them and indulging in a visual fantasy, but had the benefit of focusing the rest of my attention on the incredible feeling of stroking my cock. Other than watching direction and altitude, I became almost totally lost in the pure pleasure of my penis. Now that it was out of my shorts, I could stare into its eye and just marvel at the feeling of pleasure that happened as my just stared at my wet hand slipped over its swollen head. I could feel my balls tingling and tightening inside of my underwear. I wanted to rub them, but had only one hand. I stopped stroking for a minute and opened the fly on my briefs and pulled my balls out of the fly as well. Then, I was able to pull the bottom of the fly opening against the base of my balls. I squeezed some more clear precum out of my cock and got it wet again. Then I grabbed part of my underwear with my fingers and closed my hand around my shaft. The effect was great. Each time I stroked up my shaft, my underwear pulled against my balls. Stroking down, my balls would relax and rub on the fabric.
I was getting close to coming and I could feel the warmth filling up my hard cock from the base torwards the head. I kept stroking my shaft but only let my hand barely rub the bottom of the crown of the head of my penis. I felt my orgasm building higher and higher and my cock felt so warm and tight. The head of my cock turned purple and the hole in the end opened in anticipation of cum. I pointed my cock up so I was looking right into my cum hole. I didn't want to get my cum all over the plane. One more tight push down to the base of my penis and it went into convulsions, squirting a stream of white cum out its tip, and up onto my chest. I kept pumping it and it squirted more times until my chest and hand were wet with my semen. When it finally stopped squirting, I held my cock for a moment and just enjoyed the heat in my face and the warmth of cum all over my genitals.
I grabbed some tissues and cleaned up as best I could. Then I tucked my dick back inside my underwear and pulled up my pants. My underwear was still wet from jacking off inside of it, and from the semen that had run down my shaft and soaked in around the fly. It was hard getting my shirt tucked in again while sitting down, but I got it done and then settled down to enjoy the rest of the trip. The whole plane smelled like cum. Needless to say, I had a happy landing.