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Good Times At Cheddar High: Part One

High school boy long for his first sexual experience
Part One

The following story reads just short of a small book, a tale in four parts. It had to be that way because growing up is a long slow process, sometimes joyous, sometimes painful but always eventful. An abridged version of a young man coming of age would be a betrayal to the drama and excitement of youthful fantasies and indiscretions. After many false starts and several near misses, Richard reaches a spectacular happy ending with an unexpected conclusion. So you are invited to follow Richard Walton as he traverses the hills and valleys on his path to manhood.

In the beginning: Richard finds a girlfriend, gains a reputation and receives a mysterious note.

My name is Richard Walton. I grew up in a southern Wisconsin town large enough to have its own high school but nothing close to the size of Madison or Milwaukee . We were the kind of town where everyone knew each other and most folks didn't bother to lock their doors. Like most mid-sized towns in America , we had a few who were called the 'rich people' and others that were just getting by. Most of us were somewhere in the middle and of course, that included my family.

Growing up in a Midwestern town is like growing up in many places but like lots of kids my age, there are challenges especially for late bloomers like me. When my classmates were firmly entrenched in the dating scene and dealing with the opposite sex, I was on the outside looking in. Several defects slowed my interaction with girls, such as being short on confidence, a bountiful supply of shyness, and deceptively low self-esteem. However, I had one physical trait to make up for all of that, but more on that later.

I was not a loaner. I had lots of friends; it's just at fifteen, none were female. Things would change in a big way but it took time and patience. Eventually, raging testosterone levels and a typical teenager's libido conspired to overwhelm all obstacles. This is to say, it was a long journey before my fantasies caught up with reality entailing many events along the way.

I didn't get interested in girls until late in junior high school. Before that it was only about sports, mostly baseball, football, and basketball. My friends and I didn't abandon our interest in sports when girl awareness became a pandemic among us. Girls just added one more sport to the list. Some of the guys took up this new vocation with great dedication, more for some than for others. The laggards like me had no idea about women although it was already clear that girls were something more than targets to be teased.

I met Becky as a freshman in high school. She was in my science class and we soon hung out together. 'Girlfriend' at fifteen means mostly phone calls. A date was usually at McDonald's or at the local movie theater. Oh yes, we occasionally did homework together as an excuse to see each other and occasionally we met at the library but books and studying were not a primary interest.

Every Friday night after basketball games, there was a dance at the high school gym but no one danced. It was just a place to hook up, not in sexual sense, but more of a social event. Of course, a few of the guys would brag the next day about how they got a little tit but that seemed to be ridiculous. To begin with, there wasn't much there to touch and most of us weren't brave enough to try anything more than holding hands. I was by far the most innocent, naive , and timid of them all.

Basketball was my game and by the time I was a junior in high school, I made the varsity as a reserve point guard. We were known as the Trojans as in "Trounce 'em Trojans." It wasn't points on the scoreboard that brought me recognition but it was elsewhere that I scored.

The team shower room is a great measure of men and boys. I suppose that's why males shower openly together while women tend to shower more privately. Anyway, my teammates were clearly envious of my "hose" for that is what it was affectionately called. Those who have been around athletes know that good-natured ribbing is a mainstay of the culture and believe me, I got plenty of sports 'culture'. The thing was, in a relatively modest size town, there are no secrets that last more than few hours.

So, the news of my "hose" was out and had even circulated among the girls at school. I had a reputation by then that wasn't easy to live down. Yet, what seems to be a disaster often turns into good fortune but fortunate comes in small doses.

Becky and I were still friends in our junior year. Like me, she had changed physically and now had a woman's body. It wasn't the sexiest body in town but nice and comfortable. Some of the girls showed off their new equipment wearing tight fitting clothes but not Becky. She dressed conservatively but always with a sophisticated style. Her father ran the local drugstore so her family was closer to the wealthy side of town and she could afford buying nice clothes.

We ran around with a group made up of our basketball team and our girlfriends. Most dates during our junior and senior year meant going to Stan's house to watch videos. Stan's real name is Stanley but the girls called him 'Johnny' because of his resemblance to Johnny Depp. Stan had a special way with the girls and living in an upscale neighborhood with a hot car didn't hurt. Stan's folks were the wealthiest people in town. They had an indoor swimming pool and the most fantastic entertainment center imaginable. Sometimes there were fifteen to twenty kids laying around watching movies on their large screen, no huge, wall to wall TV.

By that stage in high school, our hormones were raging but mostly in check for fear of making fools of ourselves because of limited experience. Other than Nolan, our center, no one openly said they had sex with a girl and he only fucked a girl at the community college because she thought he was older. The rest of us got off watching porno movies and fantasizing in our bedrooms. One thing was for sure, when I ejaculated, there was enough semen to populate a city the size of Milwaukee !

As the minutes ticked away toward graduation, things began to change in our group. Virgins became an endangered specie at Cheddar High School but Becky and I were like monks and nuns resigned to celibacy. My plan was to reform and leave the monastery, but it wasn't as easy as it seemed.

On Thursday before the game with our biggest rival, I opened my math book and noticed a folded piece of paper with my name on it, "Hose." I opened it and it read, "Go Trojans" but what was really weird was a little icon drawing of a penis. It wasn't signed and I wondered who was playing a joke on me.

The next week we were playing our cross town rival and another sheet of paper appeared but this time in my science book. It said, "Get it on, Trojans" and the drawing was larger and more detailed but it was definitely a stiff cock. Now I was getting hyper. This was both exciting and scary. Who was doing this and why? I just couldn't just go around the school asking, "Who is the cock artist?"

We had a bye the next week and no drawing appeared but at the beginning of March, the playoffs started. Our first game was Wednesday night with the Red Demons that were known for upsets but we were by far a prohibitive favorite.

I had almost forgotten the messages from earlier until my English book contained a new note on Wednesday morning. This time the message was, "Trojans! Give me ecstasy." The drawing was more like a detailed painting because it was a massive cock showing veins and a nice cap on the end with a hint of a pee hole at the tip. It might have been my imagination but there seemed to be a little moisture oozing from the orifice in a shape like the letters bj. Was someone trying to encourage me or upset me? "BJ" could mean only mean one thing. I needed to find the artist and get to the bottom of this mystery.

Our basketball season ended abruptly as we unexpectedly lost to the Demons in overtime although I had my best game. Our starting point guard had fouled out early giving me a chance to score some points. After the game we took the bus back to school where I met Becky.

Our group met at Stan's but no one was in the mood for a video. I took Becky home early but not before we enjoyed a little romance in the car. We had moved onto having a more physical relationship. Becky liked being touched and I enjoyed giving her the attention she craved.

This night she even removed her bra and let see her nicely protruding tits. Her breasts were firm and her nipples were still at the puffy stage. Seeing them under the dim light of a March night drove me wild. It surprised me when she began to softly moan as I kissed her nipples.

When I began sucking on them, she let out a little yelp that startled me. I finally got up the nerve to take her hand and move it over to my hard cock but that was as far as she was willing to go. I couldn't hold back as streams of cum filled my pants. Becky could feel the wet spot on my jeans but said nothing. We kissed goodnight and said how sorry she was about the game.

That's when she said, "I'll find a way to make it up to you."

The basketball season was over by the time I turned eighteen in April and everyone was looking forward to graduation. The guys gave the Hose a birthday/bachelor party on a Friday night at Stan's. We used the pool, watched some porn flicks and drank a few beers from the stash located in the garage frig. Stan was already eighteen and bought a couple of cases of Old Style for the occasion.

I'm not a drinker so two beers were all I could handle. We had a good time and decided since the party was in honor of the Hose, we should be skinny dipping. That's what we did until one AM and by that time we were either tired, drunk or both. Driving home, I thought about Becky's surprise. She said Saturday night was bowling night for her parents and to come over around seven. It was kind of hard sleeping while fantasizing about her intentions. Hopefully, she was going to let me fuck her and pop that delectable cherry. It was something I had imagined doing all senior year.

Saturday night we had unusual weather. The temperature had dipped down to 28 degrees and it was snowing. When I rang Becky's doorbell, I was shivering. Was it from anticipation or the cold? Becky opened the door flashing her dazzling smile punctuated by a pair of killer dimples.

She was dressed nicely with a lavender button-down blouse and jeans. She wore no shoes but had little pink bows on either side of her head holding two tiny blond pigtails. She looked so Barbie doll cute and smelled delicious!

"I have a surprise for you birthday boy," she said smiling.

"Oh, what is it?" I replied in my manliest voice.

"I'll show you after you take off your clothes, wait, I meant coat. There's something here to help us celebrate!"

"Have your parents left for the bowling alley?" I asked in a hushed voice.

"Yep, they left a half hour ago. Okay, your surprise is in the frig. Take a look."

Sure enough, a chilled bottle of French Champagne with two identical flute shaped glasses painted with "Happy Birthday, Hose! stood in the refrigerator."

"Where did you get these glasses?" I blurted out.

"Oh, they came from the Party Store in town. Do you like 'em?"

"I LOVE 'em!!! Do ya want a glass now?"

"Sure, let's do it."

I'm no sommelier but I had tasted champagne during New Years Eve parties and I knew how to open champagne bottles. It was a good thing that it wasn't Chardonnay where I had to use a corkscrew. That would have been a sure way to illustrate my inexperience.

The cork made a loud pop startling Becky and she made a little hop at the sound making both of her jugs jiggle. The scene got me thinking of last night's porn flick where a lady's boobs jiggled while giving a guy a well lubricated hand job. Cum slowly cascaded down his dick just like the tasty bubbly oozing over the neck of the Champagne bottle. It was so sexy and suggestive; I had to bite my tongue to keep me from laughing.

A little champagne goes a long way with me. After the second glass, I was feeling really good and Becky seemed to have a little buzz as well.

She said, "Let's take our drinks upstairs. I want to show you my latest painting."

Becky planned to be an art major in college and I had seen several of her pieces shown at the art gallery in town. She was really talented! I didn't know that her easel and art supplies were in a corner of her bedroom and that is where we were headed. Again, my imagination got the best of me and I swore Becky was showing a little more cleavage than usual.

Once in the room, she closed the door and simply said in a calm voice, "I want to paint you."

That's when it dawned on me! ... "It was YOU!" I croaked.

"What was me?" she asked looking guilty.

"The notes in my books."

"Didn't you know? Maybe you didn't see my initials hidden in the painting before tournament."

"I saw it but I thought it meant something else."

"Like what?" she asked

"Never mind. I just didn't think that BJ stood for Becky Johansson. I should have guessed it was you."

"That's okay. My art did the job because you were great in that last game. I got hot just thinking about you out there wearing those flimsy shorts."

"Thanks, I think," was the best I could say.

"So are you going to show me or not?" Becky asked rather forcefully.

" Show you what?" I asked.

"I'm going to paint you like Michelangelo's David, but on canvas instead. My parents are only away for a couple of hours so we better get going!" sounding too much like my mom.

Modeling: Richard finds a new vocation

Okay, I have to admit here that I had no idea who Becky's friend Michael Anglo was or his buddy, David. Becky explained. She said that Michelangelo was a 16th Century Italian who carved a famous statue of David, the boy who killed Goliath. She showed me a picture and David turned out to be a totally naked stone statue. They say, "A picture is worth a thousand words." It must be true because I was starting to catch on.

So I became a male model, a nervous model. It's one thing to strip naked in the locker room but it is something else in your girlfriend's bedroom. I took off my shirt then the jeans and finally and a little reluctantly, my boxer shorts. There I was standing in front of Becky naked like David, and like the statue, my hose was lifeless.

Becky took a look at her model and gave me a quick assessment.

"Everyone says you are so big but you don't look that big," she said clearly disappointed. "I want to see it big. Can you make it bigger?" Becky asked.

"Well, I need some encouragement," I answered a little embarrassed. "How about you taking off your clothes too?"

She hadn't counted on her participation other than doing the painting.

She was confused for a second, then said, "Alright, but only my top."

Becky Johansson removed her lavender blouse. When she took off her bra, her tits flopped as they were set free from captivity. What a sight to behold! I swear her twins had grown since seeing them in my car and they looked more mature. Her nipples were a pink and upturned.

She threw her bra on the dresser and said slightly irritated, "Okay are you satisfied now?"

My response was between my legs as the hose started to twitch and it didn't take long to nearly be at full strength.

I really didn't need more 'encouragement' but said, "Hey Beck ... if you want it really big, you have to come here and touch it. Hurry, before your parents get back."

Again she hesitated but she walked over and gave the hose not much more than a quick touch, like a fist pump.

"Beck, don't be so afraid. It doesn't bite. Hold it."

After a frown, Becky worked up the nerve to put her hand around my growing cock. It took no time for my erection to stretch to the desired length.

"Jeez Dick, it's kinda hard and it is big, really big like they said!" she said as if surprised.

"Touch it a few more times and I'll be ready!" I pleaded.

She did, but this time her hand caressed my organ as though it was a new and precious gift.

Basically, an artist makes sketches before doing a finished painting. In this case, it was easier for her to take some digital shots and she would do the artwork later. So during the next half hour, she clicked dozens of pictures with me posing in different position

She seemed to be particularly pleased when I stood sideways with my hose standing straight out from my thighs. Sometimes she zoomed into my erection to get close-ups. Of course she had to hug the hose from time to time to keep it stiff.

"Dick, I think this is going to be wonderful. I'm going to do you with that big thingy sticking out, okay?

"Fine. I wonder why Michelangelo didn't think of that," I said.

When we heard her parent's car coming up the driveway, we quickly dressed. She slipped the camera into her desk and we went down to the kitchen to say, "Hi" to Mr. and Mrs. Johansson. They, of course, wanted to know about the champagne but were okay with it when hearing about my birthday. Becky would be eighteen in May so it was no big deal.

As I left, Becky asked, "So what do you think of my birthday surprise?"

"Delicious!" I replied.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.

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