By: Oscar
While on holiday in Florida with a friend, I stayed at a three-story motel which had a pool. After a day's site seeing we would go back to the room, shower and change before going out on the town.
One particular day we had walked miles and my friend said he was going to take a nap before we set out for the evening. I was still wide awake and decided to take a dip in the pool while he rested. I slipped on a pair of ordinary shorts without any underwear underneath, threw a towel over my shoulder and headed for the pool.
The pool was situated on one side of the motel and surrounded on the other three sides by shrubs. As I walked up to it I saw that the pool and pool deck were empty. Not a big surprise as we had taken our vacation in the off-season. The motel itself was scarce of people. Slipping my towel over a chair, I dove in. The water temperature was just right, and I bobbed in the water for a few moments and then started to swim.
As I swam about, the water seemed to caress my cock and balls beneath my shorts. I hadn't had the chance or privacy to jerk off in a couple of days and I started to throw a boner.
As my erection increased I started swimming breast stroke, the length of the pool and the resistance of the water against my now tented cock brought me a sense of increased excitement.
I wanted to feel more so I lowered the front of my shorts below my balls and continued to swim breast stroke. I could now feel my hard-on bending against the flow and brushing the tip of my cock.
As I was contemplating my next move, a couple appeared from their room on the first floor balcony and, looking down at me, smiled, then walked off. Had they noticed my predicament? I didn't know, but it had heightened my erection, which was now throbbing and I hadn't even touched it yet.
I moved to the side of the pool nearest the rooms. From this position anyone looking at the pool would only see my top half. I lowered my shorts to my knees, and, bobbing against the side of the tiled pool, I rubbed my engorged cock.
This felt even better, and I got even bolder and slipped my shorts off completely, enabling me to spread my legs further apart so I could thrust at the wall of the pool.
With shorts in hand I started to slide along the side of the pool to stick them around the step ladder, so I could use both hands to grip the edge of the pool. As I did this I kept my groin in contact with the wall and was pleasantly surprised when I suddenly felt a jet of warm water from the outlet.
Remaining positioned in front of the outlet, the water pummeled against my hard cock just below the underside of my cockhead. This felt great and I squirmed in front of it for a few minutes. The pleasure was now increasing and I felt my nuts starting to tighten.
Backing away slightly, I held my cock by the base with one hand, and moved my other hand down to the outlet opening. It was just the right size. I then did something crazy and daring: I guided my cock into it. The outlet hole was slightly bigger than my now throbbing cock and the sensation of the surging water pushing on and around it caused my dick to vibrate against the sides. It felt amazing!
I started thrusting into the hole, my hands firmly gripping the side of the pool and my legs spread wide to gain optimum entry. It only took about six or seven more thrusts and suddenly I was shuddering and spurting, my face contorted with pleasure. I jerked uncontrollably for a few seconds before regaining my composure and then slipped my dick out. Realizing what I had just done, I very quickly got myself back into my shorts and made my way to the ladder.
As I got out the pool I made a hasty retreat to my room. That was the only time I got to jerk off during my stay, but it has to be the best and most memorable jerk off I've ever experienced!
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