This story is fiction. All characters are 18-years-old or older.
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My name is Lee. My story begins in High School. Although smart and reasonably good-looking, I was immature, both physically and socially. I suffered low self-esteem, as other boys experienced growth spurts around 12 or 13, my hormones did not kick in until around my 18th birthday. As my schoolmates developed relationships, I could not talk to girls with any self-assurance. I was not charismatic - in fact, quite the opposite. In fact, making any new friends at school was not easy. I was the classic loner.
When I was a senior, puberty progressed to the point I learned to masturbate. One day when no one was home, I jerked-off in the family room. I walked through the living room to get to the kitchen for some paper towels to clean up the results. As I passed by the large front window in the living room, a woman was walking by on the sidewalk. Instead of running in to the kitchen I stopped. She glanced over and locked eyes with me but kept moving. My limp cock began to grow quickly, even though I had just shot a load. She kept walking at the same pace and continued to stare at me until she was out of sight. Feelings of fear, embarrassment, and humiliation washed over me. But my boner was like a rock. I went in the kitchen and jerked off again. The second time in less than 5 minutes. I splattered cum on the kitchen floor and then had two places to clean up. Every time I was home alone after that, I would strip and wait by the picture window. When I saw a woman walking by, I would nonchalantly pace around, looking for clothes, clearly visible to the female walking past. I made no eye-contact. It was supposed to look purely "accidental." Even though I turned so my boner wasn't visible, I knew it was dangerous. When the woman has passed, I would go in the kitchen and jerk-off. I worried that neighbors might see and tell my mother. It was even possible the woman might tell the police, or that it would get around the neighborhood that I was a pervert. But I loved doing it, so temptation won out. I shot loads of cum with this activity that year.
In the summer after graduation a friend, Greg, from school asked me to make up a foursome for a walk along the nearby beach. His girlfriend had a friend, Linda, who I was to keep company. I was tongue-tied as usual, but Linda proved to be an expert communicator. I soon found out she had left high school, gotten her GED, and was at Business College learning secretarial work. She lived in the next block, less than 100 yards from me. She was able to get me to relax and we seemed to get on well. I wanted to see her again but struggled to find the courage. At the end of the day Linda said, "I enjoyed myself Lee. Let's meet again tomorrow at that coffee shop around the corner from our neighborhood." I blushed and said I'd love to. For the rest of June, we met two or three times a week and talked. I should say she talked, but I was fascinated. Among other things, she disclosed that she was doing very well in school and planned to become an office administrator. I admired her plan and told her so. Later in the month, she told me she was sexually active. My face turned a bright red when I admitted my virginity.
Early in July, she told me that a friend of hers had seen me naked at the front window and believed that it had not been accidental. I was horrified. I had been exposed as a deviate, and Linda would be appalled, and possibly even spread the fact around, possibly even to my mother. My concern was unwarranted. It soon became obvious that this news had made me more a more interesting person to her. After she had coerced me into admitting that the exhibitionism was staged, she asked for a showing herself. I was trapped. Linda used her persuasion skills, and even though I really was conflicted, I did agree. We set a date and time when no-one else was home. I was in mental anguish awaiting the date, excitedly looking forward to the event, but also worried about all the potential consequences. As the time arrived, I was naked waiting to see if she would show up and wondering if I would even go through with it. There she was! At the corner, across the road, smiling at me. But now I had a new problem - an erection. This had happened to me when flashing previously, but I would turn away and not allow myself to be so exposed and humiliated. So, again I stood with only my naked back on display, hiding my boner from Linda. I then left the room, not looking forward to our next meeting. That happened very quickly, as she came to the door and rang the bell. I pulled on a robe to hide my hardon and opened the door. She knew I must have been hiding an erection. She asked to see it, but I turned bright red and started stuttering. She let me off the hook, and convinced me to try again, facing the window, erect, or not. She went back outside to her viewing place. As I looked across the road at her, my cock stood straight up and hard. As our eyes met, it felt as though my cock would burst through its skin. It was the most wonderful experience I had ever. After she left, with the Full Monty achieved, I shot a gigantic load of cum all over the kitchen floor.
Linda urged multiple repeats during August. She got closer to the window each time and I kept extending my naked time in front of the window. We were having coffee one afternoon and she asked, "What would you do if two people were watching you?"
"I couldn't do that," I said, turning a bright shade of red.
"I want to bring a friend with me."
"Why?"
"I think it's hot. You're hot and I want my friend to see you."
"I'm not hot," I said, unable to make eye contact.
"Lee, you are handsome, have a nice body, and a great looking cock!"
I was more embarrassed than I usually am standing naked in front of the window. I mumbled, "You really think so?"
"Yes, I do, and I want to show you off to my girlfriend. Do it for me."
I cleared my throat. "OK, I will do it for you." I immediately regretted it and thought, 'I will die of shame.'
"I'm not going to tell you beforehand. So, it will be a surprise."
I thought about it constantly. I mean that literally. I would be eating breakfast and think, "Will it be today?" Or sitting in class, feeling anxious and realizing I was worrying it might happen this afternoon. I realized I enjoyed showing myself to Linda... I was comfortable with her seeing me. It was kind of strange, but we had a relationship. We were friends. Adding a stranger ramped up my anxiety because of fear. I didn't know what the new girl would think. Would she tell anyone? Would she laugh at me? Showing my naked butt to a female stranger, while pretending to look for clothes, was vastly different from standing naked and hard in front of a girl from my school. It was dangerous and that caused the fear. But to me it was also very erotic and exciting.
Linda waited several times before she showed up with a friend. I peeked around the curtain and saw her with her friend. She was tall and athletic looking. She was also familiar to me. "Oh my God!" I realized we were in Algebra together last year. I never talked to her. Fear factor went through the roof. I was sweating and my heart rate galloped. Despite the effects of fear, my cock was fiercely pointing at the ceiling. I knew then I was going to walk out there, and I did. I could see both girls clap, as I made my appearance. I stood before them separated by the window. My dick throbbed with my heartbeat, and I felt a rush of pleasure at being seen.
Linda smiled, as her friend talked animatedly to her. She then pointed at her eyes and then her butt. The sign language was clear -- "We want to see your butt."
