I have jacked off many times while someone has watched but the hottest time was several years ago. I went with several friends on a golf getaway. We had finished the day with a lot of drinking. I had the room to myself as my room mate had gone with a couple others to go to a bar. I was really horny so I stripped down and was playing with myself. I got the idea to go out on the balcony and play in the warm night air.
The room was on the second floor and overlooked the parking lot. It was about midnight and no one was around the lot so I stood at the rail and jacked. As I stood there I heard quiet voices and looked to my right. About 50 feet away were 2 women. They looked like they could be mother and daughter. Mom about 50ish, daughter about 20ish. They were looking right at me.
I was just about to bolt back inside but didn't move. I looked right at them and continued to jack. They moved a little closer and talked quietly to each other. I was so hot by this time that my cum erupted from my cock like a fountain. It just missed the hood of the car parked right below.
When I was finished cumming I saw the 2 ladies smile. Mom waved and they turned and went inside. Though I have tried I have never been able to have a repeat of that night.