Chapter 1: The First Time
I was 18 years young in the summer of 1988. I lived in an average Midwestern town with my father. I had just finished my junior year of high school and was enjoying the freedom that summer brings to a young single male.
My father owned a small but lucrative business in town. I worked there part time growing up and usually spent the summers working at the shop and hanging out with friends. The house I grew up in, and living in at the time of this story, was home in every sense of the word. It was only my dad and I living there which afforded me many liberties as a young adult. Needless to say I was quite independent and adventurous.
My dad was at home every night during the weekdays. I saw him during the day at the shop but not much in the evenings or weekends as I was busy with friends and being a teenager β a kinky one at that. I lived in the basement where, years earlier, my dad built a larger living area comprised of a bedroom, bathroom, and recreation area complete with a fully stocked bar and fireplace. I moved into the downstairs bedroom as a young teen. My dad hosted parties a few times during the year in the recreation area but pretty much kept to himself on the main floor of the house. I kept to myself downstairs in the basement, only venturing upstairs to grab a bite to eat in the kitchen when I was hungry.
I soon realized there were a few unintended benefits to having my own space in the basement. Being a young man I had a rather wild imagination and a libido that was insatiable. I could satisfy my horny urges without worry of getting caught or embarrassed by my dad. Secondly, the house was built on a hill and I could come and go without having to walk upstairs. I had my own private entrance into the house and my living space. I was, for the most part, responsible for myself and enjoying the freedom at 18.
The driveway, where I parked my car, was just outside the door. My dad parked his car under the wooden deck behind the house as well; however, he preferred to walk up the stairs outside and enter through the living room.
It wasn't long after moving into the basement when I began to experiment with my own nakedness. I soon realized how much I enjoyed being nude. I would drive home after school and basketball practice and take a shower. Since I was nearly always alone downstairs I simply didn't bother to put on any clothes afterwards. At first I was nervous about getting caught or being seen but the adrenaline rush I felt kept me doing it more and more. It soon became a daily routine for me to study at my desk, watch TV, or finish my chores without a stitch of clothing on. It was liberating and arousing and made it extremely easy to pleasure myself and masturbate whenever I felt like it (which was quite often).
I enjoyed looking at myself and rubbing my naked body with my hands. I would touch myself from my shoulders down to my ankles enjoying the fact that I was free of my clothes. I soon began to play little games that pushed my kinky desire to be naked and explore past the relative safety of the basement. I would leave the door open or the blinds in the windows up while I streaked around inside in the nude. At night, under the cover of darkness, I would walk outside completely naked and masturbate on the driveway or while hidden in the bushes and trees that lined the house.
As I got older I also ventured out further from my home. I would leave my clothes inside my house and, wearing only a pair of running shoes, sneak around the neighborhood. The adrenaline rush from being outside completely nude and vulnerable was intoxicating. I stayed mostly hidden in the shadows or next to parked cars on the street. I fantasized about being seen by a stranger or a neighbor in my nakedness as I stroked my hard cock in the night air. Sometimes I would push my kinky desires to the edge by jogging naked down the middle of the street or walking directly under a streetlight and exposing my nudity to anyone who might be in the area.
I had gotten so bold as to climb certain trees around the neighborhood and jerk off in the middle of the night while the occasional car drove by. The leaves in the trees concealed my naked body while I watched the cars' headlights slowly drive by. I even made my way onto the high school football field that was a block away from my house. I ran around the track and sat in the bleachers while I stroked my hard cock. There had been a few close calls where I thought somebody had seen me but nobody seemed to know of my nocturnal outings.
So this story begins as I found myself on summer break from high school. I didn't have a steady girlfriend. The summer was going along as most summers did in the Midwest. The warm nights allowed me to fulfill my kinky hobby of being naked outside. This particular summer found me pushing myself to try even kinkier scenarios outside in public.
It must have been the fact that I was 18 and horny every second of the day because I found myself constantly in an aroused state of mind. My dad had the largest stash of Playboy magazines that I had ever seen and I did my best to jerk off to as many centerfold models as possible over the years. I would masturbate in the morning when I woke up and at night before going to bed. Heck, if I had a free moment alone in the basement my dick would get hard instantly.
It was a Saturday evening and I had just got home from a friend's house. I had drank a few beers and wasn't ready to call it a night just yet. I parked my car in the driveway and made my way into the basement. I needed to do some laundry so I decided to take off what I was wearing and add it to the clothes already in the washer. I kicked off my shoes and sat my naked body on the couch to watch some TV.
I flipped the channel to Cinemax hoping there would be some skin flick on. I was in luck. My dick began to stiffen as I watched the movie. It showed a naked chick playing with herself in the woods while some guy spied on her hidden in the distance. I started to stroke my hard cock as I watched in excitement. It wasn't long before I was on the verge of an orgasm. I shot a load of cum onto my stomach and chest and enjoyed the sensation of the release from ejaculating.
I finished watching the skin flick and decided to go to bed. I wiped myself off and walked to my bedroom and laid down between the cool cotton sheets of my bed. They felt good against my naked skin.
I laid in bed, tossing and turning, unable to fall asleep. My mind kept replaying over and over again the scene of the two people naked and masturbating in the woods. I was rock hard lying in bed thinking about this. I kicked off my covers and grabbed my hard cock. I masturbated as I imagined myself being out in the deep woods completely naked.
Suddenly I opened my eyes and sat up. What was I thinking? Why couldn't I just get in my car and drive to the woods right now? I stood up and turned on the light switch. I put on a pair of shorts and a t-shirt. I pulled on some shoes and grabbed my car keys. I walked to the back door and quietly opened it in order to not wake my dad upstairs. My eyes adjusted to the darkness as I walked outside and closed the door behind me.
My erection pushed against my shorts as I made my way in the darkness towards my car. I was wide awake and hornier than ever. I wanted to remove all of my clothes and run around naked somewhere in the woods until morning. I had a desire to stroke my hard cock in the great outdoors and roll around under the trees and stars. I was about to push my kinky nighttime naked activities beyond the neighborhood and into the unknown woods a few miles away.
I opened my car door and put it in neutral. I slowly pushed my car down the driveway and onto the street so I wouldn't wake my dad. I then jumped inside and let my car coast down the street until I was far enough away to start the engine and drive away. I put the car in second gear and began to drive towards the woods on the other side of the neighborhood. There was a section of forest and an open field a few miles away from where I lived. It was a remote area on a dirt road with no streetlights nearby. A small creek divided the woods from a private golf course on the opposite side.
I parked my car on the side of the road about ΒΌ of a mile from the trailhead. I intentionally parked far enough away in case someone noticed my car and stopped to investigate. This way they wouldn't see where I was or, more importantly, what I was doing. I turned off the engine and sat for a moment looking around to see if anyone was in the area. Since my shorts didn't have any pockets I decided to hide my car keys under the driver seat out of sight. The clock on the radio displayed 2:15 AM.
I was nervous and excited as I opened my car door and got out. I quietly closed the door and looked around, waiting for my eyes to adjust in the pitch black darkness. The moon and stars were clearly visible in the cloudless night sky. I watched and listened for any sign of other people or activity. Not seeing anybody, I began walking toward the trailhead that led into the woods.
The warm summer night air was quiet as I walked down the dirt road. I soon found the trailhead that led into an open field and the woods beyond. Crickets and the occasional gust of wind through the leaves in the trees were the only sounds to be heard. I gently grabbed my hard cock in my shorts as I walked through the grassy field trying to find a good spot to remove my clothes and get naked. The excitement was building as I anticipated what I was about to do for the very first time.
I had walked for about five minutes through the open field and into the woods when I decided to stop under a large willow tree. I stood in the quiet darkness and listened. It was dead silent. The grass around me was about three feet tall. I could see the edge of the tree line about 100 feet in front of me which ran parallel to a small creek. On the opposite side of the creek was a private golf course.
This looked like a good spot. I removed my shorts and t-shirt and placed them by the base of the tree. I took off my shoes and placed them next to my clothes as well. I stood naked and fully erect in the tall grass while I began to touch my body from head to toe. The feeling of being completely nude and alone in the forest under the summer night sky felt invigorating. This new experience felt erotic in a whole new way.