I Can't Sit On Your Lap! Ch. 01

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."

She didn't seem to mind my hand on her shoulder.

"Would you like to go out with me this weekend?"

Jenny hesitated for a moment, her brain registering what I had just said.

"Sure Jeff, I would be glad to. Just as friends though, and we will see where it goes from there. This weekend won't work though. I have to go out of town with my family. I'm free next weekend though. You get busy thinking of a good place to go for a date."

I smiled at her. I fought hard to contain my joy. I tired to make it look like she hadn't just fulfilled my most desirable wish. I just got to work, focusing on my tasks. Towards the end of the period, Mr. Lockwood emerged from his office. Jenny's eyes darted toward the door, and she began walking to his office before he even uttered a word. This was just like last Friday. What was going on with her on Fridays? When Jenny emerged, she acted normal enough. The only thing unusual about her was her reddened face and a small wet spot on her right cheek, where a tear had probably fallen.

"Hey Jenny, are you OK?"

Jenny just wrapped her arms around me in a tight embrace.

"Yes, I'm OK. You're really nice."

The bell rang, and Jenny broke the embrace.

"Bye Jeff, see you Monday. Wait... here's my number. You can call me when you figure out something for our date later."

Jenny grabbed a pen off the secretary's desk. She then grabbed my hand and wrote her number on my palm. Fortunately, it was not the hand I would be masturbating with very soon, so I didn't need to worry about smearing the ink.

"Hey, I should give you my number too."

I took the pen from her and grabbed one of her soft hands in mine. I took my time writing my number down. I gave her hand a slight squeeze before letting go. I walked happily out of the office, and to the bathroom. I called her on Sunday. I was really nervous, so I just asked her if she would like to go to the movies on Saturday. She said that would be great. I hung up the phone and masturbated again. I just had to have sex with her soon, or I would go insane.

Monday was pleasant. We smiled at each other often. I was ecstatic. The girl of my dreams might actually like me. The days passed too slowly for me. Friday changed everything. As was the case the past two weeks, Mr. Lockwood opened his door, and Jenny went into his office. I was dying to know what had been so upsetting for Jenny these past few weeks. I never liked Mr. Lockwood, and I certainly didn't want him bullying the girl I was in love with. Nobody was allowed into his office without prior permission from him or his secretary. The secretary had stepped out for a family emergency, so I decided to sneak down the hall to the door of his office. He wanted to listen in on what was being said in there.

I quietly walked to the door and pressed his ears against the door. I was frustrated by the apparent soundproofing of the room. I figured that this was done so that Mr. Lockwood wouldn't distract his secretary while he was screaming at a troublemaking student who was sent to his office. I listened carefully. All I could hear was a faint tapping sound. Once, I heard a very quiet "ow" sound. I just had to know what was going on. I needed an excuse to open the door. I finally found an excuse when the phone rang on the secretary's desk. I rushed to pick it up.

"This is Hardwood Academy. Mrs. Wilson isn't in right now. This is Jeff speaking."

Mrs. Wilson's voice was panicked.

"Jeff, go tell Mr. Lockwood that the school superintendent wants to talk to him immediately about something urgent!"

I finally had my chance. I ran down the hall and opened Mr. Lockwood's door. What I saw was a shock. Jenny lifted her head to look at me with her tear stained face. She was bent over Mr. Lockwoods's desk. Behind her stood Mr. Lockwood with a large wooden paddle in his hands. I was caught between panic and fury. I knew I shouldn't be here, but I also knew that this older man had no right to abuse this 18 year-old girl like that. Corporal punishment was discontinued six years ago, and after seeing that monstrous-looking paddle, I can certainly see why. I watched as Mr. Lockwood raised the paddle up and then swung it in a forceful arc to connect with Jenny's butt. Jenny's body seemed to jump a little with the force of the body. Out of her mouth came a howl of pain.

"Ow! Mr. Lockwood. You should stop now. Jeff is here."

Mr. Lockwood turned his head in astonishment to face me. He was speechless.

"Jeff... What are you doing here? This isn't what it looks like!"

"Uh... Mrs. Wilson says that the superintendent wants to speak with you immediately. It's urgent."

Mr. Lockwood dropped the paddle on the floor and walked past me without a word. I noticed that Jenny's skirt had been flipped up. I couldn't really tell from where I was standing, but I thought I saw skin where I should have seen some sort of underwear. Was he really paddling her on her bare butt? I was horrified at the thought of her being exposed to him like that. I was also a little jealous of not being able to see her goods for myself. I then snapped back into reality when I realized what this must be like for Jenny. She was obviously in pain, and he must have intimidated her or blackmailed her somehow into accepting these paddlings.

"Jenny! Are you OK. What did he do to you?"

"Jeff, let's talk about this. Just give me a second."

Jenny slid off the desk and disappeared behind it for a second before standing up with her panties up and her skirt down. She wiped her eyes with her hands. She hugged me tightly. This embrace was more intense than any of the previous ones we had shared.

"Oh Jeff! I'm really not sure how to explain this. Just so you know, Mr. Lockwood is not abusing me. I am letting him paddle me of my own free will because I want it."

"But why would you want that done to you?"

"That's what is so hard to explain. I don't really know. When I was growing up, my dad took discipline seriously. He was definitely not abusive to me either, but if I did something really bad, he would spank me with his belt. I used to really hate it because it hurt. I saw that he hated to spank me, and I realized he did it because he loved me. When my parents got divorced, I lived with my mother, who wasn't willing to spank me. I guess I just had that need for it. I don't expect you to understand, but please don't think I'm some sort of freak. I really like you Jeff, and I don't want this to give you a bad impression of me."

"It's OK Jenny. How did you come to this arrangement with Mr. Lockwood?"

"I was in his office once during the summer to discuss registration issues. I saw his paddle in there, and it led to him talking about the good old days of corporal punishment, and how it used to keep kids in line. I can certainly see why. He was only allowed to give students three swats over their clothes, but he said that was usually effective enough. Of course, he doesn't have those limitations with me. I told him about how I missed the spankings my dad used to give me. He suggested that if spankings made me feel that sort of fatherly concern, then getting regular spankings might help my self-esteem. He offered to give me a mild demonstration of the paddle right then. It hurt, but I knew I needed it. He offered to spank me regularly. We decided that five days a week was too much, so we do it every Friday."

"But Jenny, why that paddle? It looks very painful."

Jenny chuckled.

"Oh, it certainly is painful, but I try not to let that bother me too much. Mr. Lockwood said that I should just get mild hand spankings, but he told me that it would be inappropriate to touch a young woman's butt with his hands, even for a spanking."

"Yeah, but it's a big transition to go from a hand to that paddle. Couldn't he have used a ruler or even a belt?"

"He could have, but I asked for the paddle. It's just something about the esthetics of it. It's not like a ruler or a belt that are designed for other things, but can be used for spanking. This paddle was designed for the sole purpose of being used for corporal punishment. It sort of makes it more formal, and I like that. It really hurts, but the pain keeps me engaged. My mind likes to wonder, and I have trouble keeping focused. Other spanking tools might hurt, but nothing quite gets my attention like the paddle. It just seems to keep my mind engaged in the spanking."

"OK, as long as he isn't being too cruel with the paddle. Why do you think he agreed to do this?"

"I guess he is just frustrated that he can't paddle some of the brats and troublemakers at this school. I heard him mention that he once had to suspend a bully who beat up a freshman. He told me that if he had been allowed to punish this bully the way he saw fit, there would never be a repeat incident. I guess I sort of allow him to at least paddle one student."

"That makes sense. I noticed something though. I know your skirt was up, but did he make you pull your underwear down and paddle you bare?"

Jenny's face blushed with embarrassment.

"Yes, I dropped my panties, and I took the paddling bare. At first, Mr. Lockwood gave me the choice between taking it over my skirt or over my panties. He told me that he always had to paddle students over their clothes, even if it lessened the effectiveness of the punishment. The first time was over my skirt, but next time I told him that I wanted it over panties. I certainly noticed a difference, but it still wasn't enough. I don't know why this is, but it just doesn't really feel like a real spanking unless it's bare. That's the way my dad punished me. When I asked Mr. Lockwood if he would be willing to paddle me bare, he was reluctant at first, but I told him I was eighteen and I gave my consent, so he agreed. It just feels different over bare skin. It's like a proper spanking has to be on bare skin or it doesn't count. Do you know what I mean?"

"Yeah, I think so. It's just a little weird, but I sort of understand. So, I guess you are going to continue to do this every Friday?"

"Jeff, please don't feel bad about it. I like you, and I am looking forward to our date tomorrow. If this is going to ruin anything, then I won't do it anymore. Mr. Lockwood will be fine if I don't want to get paddled anymore."

"You are right. I am uncomfortable with you exposing yourself to Mr. Lockwood like that, and submitting to him in that position. I guess I can live with it though. Maybe if things go well tomorrow, and you trust me enough to expose yourself in that way to me, then I would be willing to spank you if you want."

"Oh thank you so much, Jeff! I will definitely think long and hard about your offer. I promise that if I let you spank me, then I won't let anyone except you spank me from now on. Would you really want to do that for me?"

"Of course I would. If it would help you, and give me an opportunity to get at your butt, I am definitely not going to refuse."

Jenny shot him a glance of mock suspicion, and then hugged him tightly. She lifted her head and kissed him on the lips.

"I will see you tomorrow night."

Jenny walked out of the office slowly, clutching her sore butt in her hands.