My name is Jeff. I am a high school senior. I am in love. Let me tell you about one amazing girl that I have had the pleasure of knowing intimately.
Her name is Jenny. She is a petite brunette with an absolutely gorgeous body. Her preppy outfits and white hair ribbons make her look like an innocent schoolgirl, but she has a body that just can't help but turn heads. She doesn't really put herself out there, so most guys don't even notice her. I do. Some people just don't recognize a good thing when they see it. Not only is she beautiful, but she is also intelligent and kind. She is basically an incredibly hot bookworm. I have a huge crush on her, but she doesn't know it yet.
I lie awake at night thinking about her. I would pull out my cock and stroke it while picturing her in my head. I imagine her wearing her usual khaki skirt around her pale creamy legs. The wind would blow and push her skirt up, revealing a pair of white cotton panties that look so lovely on her. She turns to me and looks at me with her vibrant eyes, and I gaze longingly at her sensuous lips, then my heart begins to race. My cock buzzes with pleasure until it finally erupts into the wastebasket by my bed. I would then drift of to sleep thinking that tomorrow I would build up the courage to ask her out. Tomorrow never seems to come.
Recently, I have noticed that something is amiss with Jenny. I had a free period this semester, but students are not allowed to just do nothing, even if they are 18. I had to fill that period with something, so I volunteered to be an office assistant. It's really a great way to find out all the gossip about what goes on around school. I don't mean the stupid kind of gossip like the barbie girls talk about in the hallway. I'm talking about the stuff that I can tell people about and it actually makes me more popular. I had no idea that Jenny had also chosen to be an office assistant during that same period. Of course, the office can probably do just fine with one assistant, but this is a public (government) school, and in keeping with the standard of inefficiency set by other government functions, an extra person was given useless tasks to do.
I was pleasantly surprised when I was introduced to Jenny by the school secretary. Of course, Jenny and I had talked before, since we were in two classes together, but now I would finally get to spend some time working with my crush. I loved the tasks that allowed me to be physically close to her, such as file sorting. I loved the smell of her perfume. I would steal glances at her when she wasn't looking. She had a cute nose, and her small ears often had a little pink shading on the top that contrasted with her pale skin. Once, when she was sorting files with me, she had been kneeling on the floor, but then she crouched on her feet to be more comfortable. In my mind, I imagined her falling backwards and spreading her knees, showing me what lay beneath her skirt. Oh, I certainly loved file sorting.
On one of these occasions, we were interrupted by Principal Lockwood. I was busy admiring Jenny's lovely scent as she knelt close to me, when we were interrupted by Mr. Lockwood.
"Jenny."
Jenny and I both turned to look at Mr. Lockwood. He simply continued to look at Jenny. I turned to watch as Jenny stood up and walked towards him without a word. Jenny went down the hall and into his office. Mr. Lockwood followed her into his office and shut the door. I continued my work, but at a slower pace. I wondered what he was talking to Jenny about. She seemed to know what he wanted already. He just spoke her name and she came without a word. Does she have some personal crisis going on that she preferred to keep confidential? Does she have any medical issues? What could be going on?
Finally Jenny emerged from his office and walked slowly down the hall towards me. She flashed me a smile, which eased some of my nervousness. I noticed that she carefully crouched down on her feet to help me finish sorting files.
"So what did Mr. Lockwood want, Jenny?"
Jenny didn't hesitate in her response.
"It's sort of a personal thing. Nothing to worry about."
I let it go at that. We finally finished our file sorting. I set the big box down by the secretary's desk. I was told that we were finished for the day, so we could just wait on the couch until the period was over. I usually tried to finish quickly, so I could have this free time. Jenny and I would just sit together on the blue leather couch in the office to wait out the rest of the period. I loved being able to sit right beside her and talk. She was very friendly, and we had some good conversations, but I never got the nerve to ask her out. Today was different, however. I sat down on the couch and moved to one side to give Jenny a place to sit. She just looked at the couch hesitantly. I gestured to her.
"C'mon Jenny. I won't bite. You can sit down."
Jenny smiled weakly and sat down, wincing as she did so.
"Are you OK, Jenny?"
"Yeah Jeff, I'm OK. It's just my knee has been giving me trouble lately. It's OK though."
I didn't push the question any more. I figured that all that crouching must have strained her knee. When the bell rang, I was slow to stand up. I wanted to maximize every second on the couch with her. When I did stand, I turned to see Jenny still seated.
"Jeff, would you please help me up?"
She held out her hand. I eagerly placed my hand over hers, feeling her soft skin and small fingers. I pulled her up. When she got to her feet, she leaned forward and rested one hand on my shoulder.
"Thank, Jeff."
She leaned her body into me more and gave me a hug. I quickly threw my arms around her and hugged her back. I was nervous, so I lightly rubbed her back with my right hand. She pulled away after a few seconds. That hug didn't last long enough. This period was the last period of the day, so I was able to quickly slip into the nearby bathroom and take care of my erection before anyone noticed. I was frustrated. I wished that Jenny could have been the one with her hand around my cock. I decided to ask her out. It was Friday, so I would wait until last period on Monday.
I lost my nerve on Monday, then Tuesday, then Wednesday, then Thursday. Finally next Friday came. I was tired of being scared. I walked right up to Jenny first thing upon arriving in the office. I placed a hand on her shoulder to get her attention.
"Jenny."
"Yes, Jeff."
