The Old Schoolhouse

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His first time.
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JedJoe50
JedJoe50
12 Followers

It was back in the mid-80s, and I was a skinny 18-year-old socially awkward misfit. It was the last semester of my senior year, and I was looking forward to graduation, summer vacation, and a college future where I imagined myself being cool and having lots of sex.

In my English Lit class that year I sat next to Shannon. She was thin, pale, freckled, dirty blonde, and very funny in a subtle but clever way. She liked the fact that I was smart enough to laugh at her under-her-breath comments, and we became a center of cynicism in the class. Our teacher, Ms. "G", was a difficult person to figure out. She was clearly not old, in her early 30s, but sported an old-lady hairstyle (short perm), was chunky, and dressed frumpily. From that description you would think she was old before her time, but she was also a giggler, and she laughed at or with Shannon and I often. I liked the class.

As that semester marched forward, slowly but inexorably, I settled into a rigid schedule, as my personality type tends to do. I was getting more active in various school activities, getting more hours at my job, keeping up my grades (straight "As" ...got to get that scholarship!) and fantasizing about finally having sex. I know it may sound odd to younger folks today, but back then I don't think it was common for 18-year-old high schoolers to be wandering around having sex all the time. I know I was far from the only virgin in the circles I ran in, and my circle of friends included a few cool people and some athletes, not just nerds like me.

What's odd in hindsight is that even though I was desperate to find someone to experiment with, I was scared of the few girls who I knew were experienced. So, I kept hanging out with girls who were probably as scared of me as I was of them, and my sex life was nothing more than fantasies.

On this weekday in the fall, I had decided to walk through the woods down an almost invisible path to an old, abandoned schoolhouse about a mile from my home, where people dumped their trash. I sometimes found bags full of Playboy and Penthouse magazines down there, and I was hoping to freshen up my current stash.

I rounded the last corner on this path before it opens up into the old school parking lot, and suddenly found myself walking past a parked car. The nose end of the car was up under the trees, while the rear end of the car was exposed to my view off to the left of me. The rear-hatch was completely opened, and inside the back of the car, oblivious to my presence, were two naked people making out.

I instinctively froze, both in fear and fascination. As I overcame my disbelief and became mentally able to turn and run, the man, who was laying on top of the lady, sensed my presence, stopped kissing her, and turned to look at me, growling "What the hell do you want?"

I was two things simultaneously -- scared to death, and horny as hell. "I want to help you take care of her -- mind if I join you?" The horny cynic in me won the battle over how I should respond.

Upon hearing me, the lady lifted her head up to look at me, and I locked eyes with Ms. "G". Other than her face, I could only see her naked feet and calves and a glimpse of her breast exposed when the man had raised himself to look at me. But I could clearly see her face, and it was her. I decided to press my luck: "Come on, y'all, I'm a virgin...wouldn't it be fun to teach me how to please her?"

"Get the hell out of her before I shoot your ass!" the man hollered, and I believed him. I turned and calmly walked back into the woods, abandoning my pursuit of fresh porn magazines as well as my hope to lose my virginity.

I worried for the first 15 seconds or so as I walked away that by turning my back on them, I was giving the man an opportunity to take that shot at me, but I felt it was the best way to show I had no fear, even though I was still scared to death. After that first 15 seconds, I was out of their sight. Now, no longer in fear for my life, I wondered what the hell Ms. G would say to me tomorrow in class. For whatever reason, I felt like I had done something wrong, even though in the big scheme of things I had just stumbled upon them and made a safe escape, nothing more.

The next day I was anxious about what would happen in class, but kept my cool, and behaved normally. In other words, I worked with Shannon to make fun of things and make Ms. G laugh. She did!

Wow, nothing bad was going to happen to me! It's odd that I was worried when I hadn't done anything wrong, but 18-year-old horny young men are not logical, they are emotional. Now that I knew I wasn't in trouble, I continued my normal routine. By the beginning of the next week, I had basically forgotten all about the event at the old schoolhouse. But then we had an odd day in Ms. G's class.

She began the day as she normally did, roll call, collecting homework, etc. But instead of introducing a new book or summarizing the lessons learned from an old one, she announced: "Today we are going to do something different. Part of education is learning about yourself as you learn the subjects you are studying. Today, to help you learn about yourself, we are going to take a personality test. Your answers will be private, and you will score the results yourself, so no one will ever know your answers, your final scores, or your personality ratings unless you choose to share."

Strange, but not completely weird to me. Another of my teachers had given a class the Myers-Briggs inventory, so I had been exposed to this type of stuff before. Ms. G would read the questions, we would write our answers on our own piece of paper, and afterwards she would tell us how many points for various categories our answers were worth.

But she asked one question that was NOT ever a part of any Myers-Briggs inventory I had taken. "If the opportunity occurred, would you engage in kinky sex?"

My heart pounded and my face flushed. Of course, I would, but why is she asking? And what is everyone else thinking? I glanced at Shannon and could see that she had written "Y"! Now I was aroused. I was too afraid to look up at Ms. G, so I just tried to freeze, control my breathing, and will my hard-on to subside.

By the time we got to the end of the questions and had scored our answers, I had calmed down. Now I was thinking -- is Ms. G sending me a message? Did she WANT her man to let me help last week? And how could I ever offer Shannon "the opportunity" for kinky sex? What does Shannon think is kinky sex? So many questions!

I decided to at least test the waters with Ms. G. When class was dismissed, I was walking out of the room with Shannon. As we passed her desk, I went for it. "Thanks for that self-exam Ms. G. I guess I've always known this, but the exam made it clear I prefer a rigid schedule and routine to chaos. That's why I always get my homework done and do well on tests -- it's in my rigid schedule!"

She laughed at me and said something about how having god-given talent didn't hurt either when it came to making good grades. I don't like to talk about this much, but everyone thinks I am very smart and have no trouble doing homework or getting "A"s, so Ms. Gs response was not an unexpected response. But then she super-charged my emotions: "I hope you keep sticking with your schedule and doing well."

I was still walking with Shannon trying to be cool, so my short reply as Shannon and I walked out the door was "of course, you know me, same old routine" and then I was out of her room. Now that I was with Shannon alone, I wanted to know if she would talk about her answer to kinky sex. Being charged up after the exchange with Ms. G, I was finally brave enough to go for it with Shannon.

"Shannon, do you realize how many of those questions were impossible to answer truthfully?"

"What do you mean? Why would you lie to yourself?" Shannon was walking right into my trap!

"Remember the question about "kinky sex"? Well, the word "kinky" means different things to different people, so how can anyone answer that honestly?" I waited to see how Shannon would answer this question.

She replied, "I just figured that was a safe way of saying "oral sex" in front of a class".

So now I knew -- Shannon wanted oral sex! Could I build up the nerve to ask her out? Now I was so hot I almost forgot the bombshell Ms. G had dropped on me -- she wanted me to stick to my routine. But that night, alone in my bed, I thought about oral sex with Shannon, and I thought about my "routine" including walks to the old schoolhouse parking lot. Did Ms. G want me to go to the old schoolhouse tomorrow after school? Why would she want me to go there? Was she going to have that old man kick my ass or was she interested in "teaching" me? There was only one way to find out. My worry over Ms. G thoughts overwhelmed my fantasies about Shannon, so I was too nervous to masturbate and had a hard time going to sleep. But in the end I resolved to go back to that parking lot tomorrow.

The next day, I skipped the "going home" part of my routine and rode my motorcycle straight to the old schoolhouse. Even though I was on my bike I took the path through the woods rather than the main road. I parked a short distance from the end of the path and hid my bike in the bushes off the path. I stayed off the path and worked my way past the spot where the car had been parked a week ago, still hidden in the bushes, anxiously waiting to see if anyone was coming. I was in place almost a half hour earlier than I had arrived here last week because of my motorcycle. Now that I was just waiting, my watch seemed to be moving so much slower than usual. After 20 minutes or so had passed, a car left the main highway and entered the schoolhouse parking lot. Me heart started beating faster and I almost lost my breath.

The car crept slowly towards the parking spot. I felt like my breathing was loud enough for folks on the main highway to hear. As the car passed me, I could see it was Ms. G, and only Ms. G. I couldn't believe it. Thank God that old man wasn't with her -- he was kind of scary to me, tall, hairy, and definitely not amused by me.

I let her start backing into her parking spot before I left the safety of the bushes and started walking towards her car. She saw me and smiled almost as soon as I left the bushes. This was the moment I began to believe that something might actually happen.

She rolled her window down as I approached her car. "Oh my god, I am so glad you are here alone, I thought you might bring that guy with you and have him kick my butt." I said, smiling as I shared my fears. She laughed and said "I can't believe I'm doing this. What am I thinking?" I decided to act experienced and in control and leaned into her window. I kissed her lightly on the lips...such a bold move to make towards someone I had always treated like an authority figure. "I hope you are thinking how much fun it will be to teach me how to please you!"

I straightened back up, and she opened her door and stepped out of her car. This was the first time I ever really sized her up standing next to me. I was 6 feet tall and only weighed about 130 pounds at the time, a true skinny nerd. I was wearing a pair of jeans and a T-shirt I'd gotten at the Jimmy Buffet concert a few weeks before. She was around 5 foot 4 inches, and at least 160 pounds, chunky but curvy. She was wearing the same outfit she'd worn to school that day: a frumpy dress that extended well below her knees and buttoned up the front almost to her neck.

Despite the conservative nature of the dress, it was impossible for me to ignore her figure now that I was really checking her out. She had a large chest, much larger than any of the girls I knew other than the ones that were extremely large. Her skin was pale, and not freckly. She had a beauty mark on one of her cheeks and another on her neck. She had a tummy but that didn't bother me now, because she had a mature feminine figure -- nice wide hips, narrower at the waist, and broad again at her chest. I was enthralled!

I placed my hands on her hips and moved into her embrace. She reached up and pulled my head down to hers, and she kissed me, this time with passion. As she led, I followed. I had made out with girls my own age before, and they all had been the aggressors. I liked it that way. She kissed me, and I allowed her to kiss me however she wanted, just like with the other girls I had kissed. She would gently suck on my lips, sexily lick them, then probe me with her tongue. After making out this way while standing for at least a minute, she opened the back door of her car and said "why don't we get more comfortable."

This was not the same car I had seen last week and did not have a rear-hatch and a fold-down seat to make it easy to lay down next to each other. Instead, we sat in the back seat, and she resumed kissing me. Now that we were in the back seat making out, I started noticing how great she smelled. DAMN, I should have put on cologne...except I still didn't own cologne.

I noticed how turned on I got hearing her breathing mixed with her soft moans. I couldn't help myself and moaned lightly with her, relishing how soft her tongue felt against mine, mesmerized by how soft and creamy her skin felt where I touched her. And her muscle tone was soft as well. I suppose today we would say she was a soft chunky lady, but where I grew up all the girls were basically skin, bones, and hard muscles like I was, so I loved how soft she felt.

Her hands were wandering over my chest, down my stomach, back up under my shirt. I leaned back and helped her get my shirt off.

She made me feel great: "Wow!" she said while rubbing my chest and stomach. My fitness was strictly a function of a lifetime of very active outdoor working and living, being skinny, and playing tennis (my only varsity letter). But when you are skinny the small muscles you have are easy to see, and she seemed genuinely turned on by my taut chest and stomach.

She leaned back towards me, but instead of kissing my lips, she started kissing my neck. I relaxed and enjoyed the attention. She kissed up towards my ear, licking me to the point of goose bumps. I was breathing hard now, eyes closed. She whispered in my ear "god you are so handsome" and exhaled, really making me tingle. I couldn't really do much in the position we were in, even though I really wanted to touch and see her everywhere. She continued pushing me back into the car seat as she kissed back down my neck, to my chest.

It had never occurred to me that my nipples were an erogenous zone, but when she licked and sucked them, I learned that lesson. I sucked in my breath dramatically at the first nibble. I was hard as a rock now, and her hands were rubbing my hardness through my jeans.

She stopped kissing me again, this time so she could concentrate on my jeans. She unbuckled my belt, opened up my jeans, and pulled my cock out from under my underwear. As she ran her hands up and down my shaft, she was looking at me. I was staring back at her, amazed at how different this felt from masturbation.

There was no way I was going to last very long. I almost came just from her exposing my cock to the air. I think she knew what was going through my mind because she reassured me. "Go ahead, cum anytime you want. I know you will be able to get it up again." Then she leaned down and took me in her mouth. Of course, this 18-year-old virgin responded exactly like she knew I would, and I came almost immediately. She slowly sucked my hardness into her mouth while I was cumming and moaned loudly to match my growls as I thrust up with each spurt.

When I relaxed, she sat back up, smiling at me, and leaned back into me, licking my ear. "How did you like that!"

"Oh my god, that was incredible. I can't wait to repay the favor!"

"heee heee heee heee". I loved her giggle. "I was hoping you would say that!"

I started kissing her, exactly like she had kissed me. I kissed her lips, I probed with my tongue, I sucked her tongue when she offered it to me. I kissed and nibbled on her neck, but not too hard (no marks!) before licking and blowing in her ears.

I finally allowed my hands to rub her chest through her dress. When I could tell she was really enjoying my attention, I stopped kissing her so I could concentrate on opening up the top of her dress. My god it had so many buttons. We didn't take the dress off, we just opened it from the top, exposing her bra-covered bosom. I started fighting with the bra, but she showed me the clasp...wow front clasps, another thing I didn't know existed at the time.

With her dress open and bra unclasped, I could finally see her lovely breast. Her nipples were firm, and much larger than I expected, at least a half-inch in length. Her areola were large, probably 2 inches in diameter, matching her cup size. I dove right in, taking her nipples in my mouth, back and forth, just overwhelmed with lust. I sucked them HARD, as if trying to make them longer. She squirmed and inhaled sharply in response and was using her left hand to calm me just a bit by stroking my hair.

My right hand had found its way up under her dress, and she was spreading her legs for me as I pulled her dress up. I stopped sucking her nipples so I could remove her panties. When she lifted up off the seat so I could pull them down, it caused a huge surge of lust to roll through my entire body. For some reason that simple act of cooperation made it clear that she wanted this, and that really turned me on. I was hard again, just like she said!

With her panties off, I leaned in, taking my first close look at a woman. She had a dark, thick bush, which surprised me a bit since her hair color was light brown, almost reddish. I had stared at so many naked pictures, I knew exactly what to do. I spread her with my hands, saw what I knew was her clit, and took it into my mouth, almost like I was sucking her cock. I alternated licking and sucking. I She was moaning loudly now, panting as well. Everything she did let me know what she liked a lot or just a little. When I matched my fingering tempo with my licking tempo, she started humping up in the same tempo. It was like we were working together.

I had two fingers inside her, and was using a technique I had read about in Penthouse to stimulate her g-spot, fingers executing the "come here" motion inside her. At the same time my mouth was really pressuring her clit, whether licking or sucking. Our tempo was getting faster, and faster, and faster...

She EXPLODED up with one massive thrust, while grabbing my head with both her hands. I kept licking and fingering as fast as I could, moaning loudly into her pussy.

"AHHHHHHHHH" It was the sexiest thing I'd ever heard or seen in my life. I had made her cum. As she calmed down, I was getting more and more out of control again, and basically jumped up into the backseat between her legs, trying to finally fuck her.

As she slowed her breathing down, she realized what I was trying to do and helped me -- if she hadn't, I might not have ever found my way. As she adjusted her hips, she guided my cock into her, and then pulled me in close.

Now it was my turn...AHHHHHHHH. This was not a cry from cumming, but of relief. I was finally inside her. She pulled my head to hers, and we started kissing as I just lay on top of her.

Now that I was inside her, I started noticing many things. First was OH MY GOD, how wet and soft and warm and tight she felt. Like we were made to fit. Second was OH MY GOD how intimate it felt to be kissing while inside her. Finally, I realized I could move, and slowly started to thrust.

I broke our kiss and pushed up so I could watch the scene, first looking at her eyes, then down to her chest, and finally down to where I could watch my glistening shaft slide in and out of her. Those were her juices, and she was soaking wet. I was doing good!

JedJoe50
JedJoe50
12 Followers
12