It was hot the summer I graduated from high school. I was about to enter my own wonder years, when I would go to college, become comfortable with the opposite sex, stumble onto my first nude beach, and generally grow into my own skin. But all of that was still to come. All I knew then, was that I was hot, bored, and perpetually horny.
My job at the restaurant epitomized all of these sensations. After a night of washing dishes, I could literally wring the sweat and steam out of my shirt. And the waitress. After a night of watching the waitresses prance around in their too-tight polyester uniforms, I would literally be bouncing off the walls. Most of the wait staff was girls from my high school, or college girls who had come home for the summer. When we closed in the evening, they would strip down into shorts and t-shirts, and flirt with themselves and the rest of us while cleaning up. I was in love with about half of them, and far too shy and awkward to flirt back with any potency. I was "friends" with all of them, which, as any adolescent male knows, can be a terrible hell.
I sometimes went home and jerked off in the shower, but this was a poor outlet for my nervous energy. I took to driving around town, listening to the classic rock station. One night I happened to drive by a friend's house. I knew they were out of town, and I found myself drawn to their backyard pool. I parked my car down the street a little, hopped the fence to their backyard. Everything was dark and quiet, so I stripped down and dove in. It was amazing: the initial rush of water over my naked body, the way it cooled and stimulated me at the same time, the taboo of public nudity. It felt better than masturbating. I probably only stayed in the water 15 minutes that first time, but I was hooked, and so began my summer of pool hopping.
This was a small town, and my targets were fairly limited. On the other hand, it was a small town, and security measures were almost non-existent, so I was able to swim with relative impunity. I soon developed a couple of favorites, which I chose based on the quality of the pool, its seclusion, and the ease of parking. (Having a good place to park was pretty important, because my biggest vulnerability was having some cop come along and check out my car. I had all the contingencies worked out--washing dishes gave me a lot of time to plan.) My absolute favorite place was a pool at the home of one of my high school friends. Her family was well off, and had a large, old pool in their backyard. The pool was nice, but the yard was perfect. It was carefully cultivated to look overgrown, with a lot of ivy and old growth trees. At night, with the moonlight whispering through the leaves, I could float in the water and imagine the trees encroaching on the pool and house, like some gothic horror movie. It was hard to get to, as the yard itself emptied into a wooded area, so I had to park down the street and walk (carefully) around the house. But when I had the time, this was usually where I headed.
The house and pool were owned by the family of my friend Amy, although "friends" may be a little too strong to describe our relationship. She had been our class' prom queen, and was the most popular girl in school. She was so far above me that I had never even bothered to fantasize about her, but we were friendly. Amy played trumpet in the band, and we sat beside each other for four years. She was also very intelligent. She hid this fact from most of the school, but I had been in enough advanced classes with her to know better, and we would occasionally talk about books we were reading.
I would like to say that I often thought of Amy as I floated in her pool, but the truth is I didn't, other than to vaguely keep an eye out in case she or her older sister came home late and surprised me. This never happened, however. In fact, I rarely saw any activity in the house at all, other than an occasional light in an upper floor window. The darkened house itself took on an air of mystery, especially when bathed in the tree-filtered light of the moon. The more I went, the more confident I became. I would strip down as soon as I was out of view from the street, hiding my clothes under a clump of bushes. The perfect hiding place, I thought, because I could head straight for them if I had to make a quick retreat.
I almost got to thinking of it was my yard, and my pool, and I even got so that I wouldn't bother checking to see if anyone was around. I would just stroll into the yard, jump in the pool, whatever. It was a recipe for disaster, and sure enough, I climbed out of the pool one hot, sticky night and was squeezing the water out of my hair when I heard a movement in the shadows behind me, and a quiet voice said, "Hello there."
I froze. My hands were in my hair, and I stood still, exposed in the moonlight. My first instinct was to turn and run for my clothes, but the voice was between me and them, and there was something soft and non-threatening about it. So I turned around slowly to see who was there. As I watched, a figure moved out from under a tree. It was Amy, and I had no idea how long she had been there. I was so stunned that I could only stand stupidly, naked and dripping. She regarded me for a moment, with a thoughtful look on her face.
"I've been watching you for some time, you know," she said.
There was a pause. I couldn't think of anything to say, so she continued, "Not just tonight, for a couple of weeks. You're pretty dedicated."
"Yeah," I said lamely, "I like your pool."
"So I've noticed." She watched me as I nervously tried to brush the water off my arms. "Why do you do it?"
"What? Swim in your pool?"
"Well, I'm mostly interested in why you do it naked."
I was glad she couldn't see me blush in the darkness. "I don't know," I said lamely, "it's just fun. A release I guess."
Amy didn't say anything for a second. Finally, she took a deep breath, and said, "I want to try."
"What???"
"I want to try." Her words became easier now. "I've wanted to go skinny dipping for as long as I can remember, and you're the first person I've known who does it. I want you to take me."
I didn't say anything, trying to absorb this.
"I have some friends down the street who are gone on vacation. We can go there tomorrow night. Perfectly safe."
I had a feeling that "perfectly safe" included her being safe from me. I hesitated again, and pushed my hair back while I thought.
"You have to do it," she said, "I'll never do it by myself. And I haven't turned you in. You owe me."
No arguing with that, so I shrugged. "Ok," I said, "I get off work at 11 tomorrow. Meet you right here."
Amy smiled, took one last look at me, and turned to go back to her house.
After work the next night, I drove over to her house. We had decided to start with a pool that belonged to a family friend. Amy was pretty sure that they were out of town, and their house was in a secluded section of the same neighborhood, so it was a safe first bet. I parked in my usual spot and hoofed it over to Amy's yard. My hormones were surging at full throttle, and I had long since decided that I wasn't going to miss a single moment of being naked in front of her. So as soon as I was out of sight of the street, I stripped down, hid my clothes, and jumped into the pool. The water was warm, I remember, and I immediately felt the sweat and grime from the day wash away. I also felt that familiar tingling in my groin area, so I got out and settled into the shadows to wait for Amy.
I didn't have long to wait. Within minutes I heard light footsteps as she walked towards the pool, and I stepped forward to greet her, my heart pounding with anticipation. She was wearing shorts and a dark button down blouse, and she seemed surprised to see me already naked.
"Oh," she said, "I. . ., uh, I don't know. . .uh. . .shouldn't we wait. . . ." Her voice trailed off.
I shrugged and tried to look nonchalant. "Well," I said, "it's not as much fun unless you're naked."