Skinny dipping late at night
Whenever I'm back home at my parents house, I always like to sneak around and jerk-off in risky areas. Growing up there, I knew everyone's sleeping habits, and where they hardly venture.
I come from a large family of 5 brothers and sisters, so my house is fairly big, with: 5 bedrooms, 5 bathrooms, a living room, kitchen, laundry room, dinning area, and a large backyard with a pool.
When I was in high school we had a full house, and my masturbation area was limited to the bathroom when I showered, and sometimes my room late at night. After a while of this, I began to get bored of jerking in the same places and began to plan out how I could jerkoff somewhere new without getting caught. The first place I ventured to was the backyard and pool.
I would wait til quite late at night, so that I made sure everyone was either asleep or already in bed and ready to go to sleep. I would quietly leave the hallway where all the rooms where to pass by the dining area and exit to my backyard. The tricky part was exiting to the backyard, because my mother would usually sleep in the living room, which was just by the door I needed to pass. I would exit extra carefully, as to not wakeup her or my dogs. As soon as I was out I would walk to the deep end of the pool, where I was covered by a bush if anyone were to walkout side, and begin to setup camp. I would have a backpack which had in it: a towel, a condom, lube, a few tissues, and my laptop full of porn. Laying the laptop on the ground with the towel right in front of it, I would play my porn playlist, get naked, and slowly lower myself in the pool. At that point id be far from hard due to the cold pool and the adrenalin rush, so I would take some time to swim a bit.
Swimming was the best part. Id swim back and forth underwater as fast as I could for as long as I could, feeling the water rush past my penis and ass. Id also do cartwheels underwater, and spread my legs apart and swim downwards to feel my gouch brake through the water. After a bit of this I was relaxed enough to get turned on, so I began by watching the porn videos from inside the pool with my penis being pushed against the jets. I'd get harder and harder, watching videos of cumshots and facials.
When I was hard enough to want to jerkoff, I would grab the condom from the bag and fill it with some lube and put it on (that way the water didn't washoff the lube when I jerked it). Letting myself float a bit I would jerk myself looking up at the stars and fantasized about being watched by someone in the house. When it would come down to going for the cumshot I wanted to do it outside the pool, so I would get out quickly and takeoff the condom and laydown and jerk off onto my stomach the biggest loads ever. Sometimes I would grab it on tape with the webcam on, but they wouldn't be such good videos because of the lighting. After cumming, id cleanup most of it off my belly with the tissues, and then would dive deep into the pool to washoff any excess, taking a couple of laps before getting out. Finally I'd dry up, get dressed, pack my bag, and sneak quietly back into the house.