I've always been shy but never more painfully so than when I was a teenager.
Growing up I was never comfortable talking to girls. I just didn't have any game or know quite what to say. That didn't mean that I wasn't interested. I'd discovered my dad's magazine collection in jr. high and once I'd been told about masturbation by friends, I could not get enough of it! In the long hot summers in the small southern town I grew up in, the heat kept me indoors much of the day. I'd go to my parents bathroom where the magazines were hidden and beat off 5-6 times a day until my folks came home from work.
But I still longed to know the touch and feel of a girl. In high school as a freshman, I had a French class that had several Seniors in it. I and a few of my friends (all Freshman boys) sat in this class like a bunch of puppies around a short, busty Italian girl who was a Senior and who loved the attention. We were somewhat emboldened because there were no upper class guys in the class, so we had her attention and visa versa. She was quite cute, and short curvy women became an archetype for me. My jack-off sessions centered around thoughts of her. I spent the last months of that school year in agony. By night, just with thoughts of her, I rubbed my prick raw imagining what we would do together. My desire built to a fever pitch and I took to leaving the confines of the house to masturbate outside in the heat of early spring nights. I'd get so entranced and would ache with desire so much that I began coating my body with vaseline and rubbing into my torso with one hand, running my balls and ass as I beat off in the night. When I came, It would allow me to sleep, but I repeated this ritual more than a few times.
The last week of school, I had built up the "courage" to write her a poem that I intended to sneak into her locker before the last day - the last day I knew I would see her ever again. However, my shyness got the better of me, and I could not bring myself to do it, believing that I'd be caught or otherwise found out, even though I'd left me name off of the poem.
Friday came and went. I was crushed beyond belief at my own failure and her absence. My outdoor ritual one night included burning the poem in the backyard of my parents house, while I stood naked under the stars, covered in vaseline but unable to find comfort in pleasuring myself. My first big crush was gone but I remained alive and yearning for contact.
My ritual ceased for a while. After a few weeks, my desire drove me back out into the night. The summer air was thick and the humidity suffocating. Standing under the stars and tall trees of the back yard peering up at the sky was not getting me there like it had before. The idea that my parents and siblings were inside and asleep but that I could be caught was what I realized made it so exciting. I was naked and if any one of them had come to the back door to look out they would have clearly seen me standing there doing my business, with nothing on. A thought began to develop in my mind of how to bring back the edgy excitement of my ritual. The house was only a two short blocks from the main street in town. The house was on a corner and the back corner of the back yard was close to w very well lit but little travelled intersection with a stop sign. The intersection was in line of sight from the main street and the exit from a popular bar's parking lot where people leaving at closing time would pass. The headlights of cars leaving the lot would scan past the well lit intersection when they turned out, as I had noticed on other nights standing in the back yard. My thoughts now drew me to go back inside for a tank top to cover my torso. As I crept back outside, my lower half, smeared with vaseline, was bare and my penis as rock hard as ever. I crept around the fence and hedges from the back yard, to the side street and on to the intersection. The sound of crickets buzzed loudly in me ears as I stood under the bright street light in the intersection, my dick throbbing in the heat. Sweat began to collect on my neck and a planted my feet apart, arched my back and began stroking my cock. I didn't have to wait long before I saw the headlights of a car leaving the lot. My head was thrown back as I stroked by dick, and the light from the car turned my way. The driver paused for a second, and either because he was drunk or checking for traffic, but he did not head my direction, obviously not seeing me. A my breathing quickened as I felt a wave begin to build. As I began feeling the pressure mount, and another car approached the lot exit. As it stopped at the street its lights pointed directly at me. I could feel my heart pound and my hand sped up and gripped my shaft tighter, stroking and making sure my movements would be seen. The couple in the car clearly saw me, and it lunged out into the street, headed right to where I stood. My mind registered this and panic caused my feet to turn and head back the way I had come. As I ran, the car sped up and barrelled towards the spot where I had stood and turned onto the side street. I reached the cover of the hedges as the car turned onto the side street and I remained there as the car slowly rolled past, looking for me. The car made the entire block, but I remained in the cover of the bushes panting with my heart beating in my throat over the close call.
I did not complete the act that night, but simply went back to bed, glad to be safe and anonymous to the strangers I had exposed my body to. I never did go out into the night, especially not into the intersection, again after that to masturbate, fearing being caught. But I can still remember the pain of my first crush and the thrill of exposing myself to the summer night and to two strangers who still must wonder about the young man they saw.