Because I Was a Gentleman

Fourteen-year-old Kenny's gentlemanly traits impede classmate Cassy's plans to have sex with him. She arranges a romp in a storage room to get what she desires.

Part One

My name is Kenny Ingram. I suppose the first official date I ever had with a girl was when I was 12 years old. Her name was Cassandra (Cassy) Mathewson. One Saturday in early June of 1976, our elementary school was hosting an enormous indoor and outdoor “Fun Fair” to raise money for some project. I suggested to Cassy, a cute brunette classmate whose developing charms had recently caught my attention, that we attend together. “I’ll pay for everything,” was enough of an enticement for her to go to the event with me as a pair.

I didn’t appreciate it at the time, but my school was luxurious. Relatively new and located at the end of a dead-end street that was surrounded by undeveloped land, it had vast expanses of open space surrounding it. We had ample acreage for a softball diamond, a soccer field, plus enough room to have two portable classrooms in years when enrollment was high. The Fun Fair took advantage of it. There were dozens of attractions that altruistic parents and teachers had set up for the general amusement for kids of all ages, including adults. The event was well publicized and the late spring weather conveniently cooperated. It attracted an enormous crowd for the six hours it ran, even drawing a considerable number of out-of-towners. I happily paid for everything—both food and games—to make Cassy a happy girl. Isn’t that what a gentleman is supposed to do on a date?

Luckily my father had financed this outing, so it didn’t cost me a dime. When he heard from my mother that I had a asked a female classmate to accompany me to the Fun Fair, he took me aside and jokingly said, “Son, I’m disappointed in you! I started noticing the pretty girls in my class when I was in the fourth grade. Is there something wrong with you, Kenny? Why are you two years behind me?”

He handed me a $20 bill—a significant amount of cash for a 12-year-old to have as pocket money in the mid-1970s. I learned that was true when I tried to pay for Cassy and me to play a game of chance that cost just a nickel apiece. The dour teacher who was running the game, Mrs. Mullavey, had to dig into her own wallet to make change for me.

I gently chastised her by noting, “When my Uncle Nathan opens his hardware store for business, he always has plenty of cash in the till. If someone walks in with a $100 bill and makes a small purchase, he can make change for it without any trouble.” I could tell by the sour expression on her face that Mrs. Mullavey didn’t like being upbraided by a pupil 40 years younger than she was. To gently needle her, I added with a smirk, “Uncle Nathan says it’s part of being prepared—and that’s always important. That’s why he's been successful in business.” Subtly insulting someone was a personality trait I had picked up from Dad, who had no peer in that verbal skill.

A good time was had by all, especially by Cassy and me as we spent nearly all of my father’s $20 over the next three hours. Cassy became more and more affectionate with me as time dragged on. At first, Cassy took my hand. A little bit later, my date hooked her arm around mine as we walked from one fair attraction to another. When we were watching a pair of silent Laurel & Hardy comedies in the school’s gym—at a cost of a dime apiece—Cassy pushed her chair as close to mine as possible. Then she romantically rested her head against my shoulder for the entire 45 minutes of the screening. I had zero experience to compare it to, but I figured my first date was proceeding splendidly.

After gorging ourselves on hot dogs, hamburgers and ice-cold lemonade, I walked Cassy to her home. It was about five blocks from where I lived. We chatted amiably about what the best activities had been at the Fun Fair, the school year, and other trivialities. We each possessed a bagful of various prizes that we had won. Having bought a lucky ticket in a raffle, Cassy had won a $10 gift certificate from a local bookstore—which I thought was a fantastic prize. I was an avid reader.

When we got about a dozen houses away from Cassy’s home, I told her, “This is about the time when you have to make a big decision.”

“What do you mean, Kenny?” she asked with a curious expression on her pretty face.

I mustered enough confidence to say, “I want to be a gentleman about this, Cassy, I really do, but I need to know if you’ll let me kiss you—and where and for how long.”

“Well, that’s actually an easy decision to make,” my wonderful date told me with a brilliant, toothy smile. “You can kiss me on the lips, of course, Kenny. I’d like that. For how long is entirely up to you. But let’s do it here, where we are out of view of my parents and my snoopy little sister, Doreen.” Seconds later I thoroughly enjoyed the first romantic kiss of my life. I estimated it lasted for close to 20 seconds. Throughout it, I could taste the fried onions that Cassy had liberally put on her hot dogs. That didn’t bother me in the slightest.

As Cassy began to enter her house, she turned around briefly and sincerely said, “Thanks for the very fun day at the fair, Kenny. You really are a gentleman. You’ll be rewarded for it someday. Count on it.”

Part Two

When I entered Chandler Heights Middle School a few months later school, I experienced a sudden growth spurt that placed me in the top three in height for the entire school. I was also a better-than-average athlete, doing quite well on the school’s volleyball and softball teams. I was also an excellent student. I figured I was at least an average-looking teenage boy, too, perhaps considered a nine out of ten on those very rare days when my hair was under control. I guess all those attributes combined to make me somewhat desirable to the girls in the school. One of my male classmates, Bobby Nelson, told me one day that his twin sister Bonnie considered me to be “a hunk.” I was puzzled; it was a term that was new to me so I asked Bobby what it meant. “Girls find you very attractive, Kenny, you fool! Didn’t you know that?” Actually, I didn’t! Bobby had been the accidental bearer of very flattering news.

Cassy and I were not exactly a couple throughout middle school, but we did do a few things together but only on occasion. I was typical of my peers. No male I knew who was my age had a steady girlfriend in those days. If there was a school dance or something similar, most of us guys just showed up for it unaccompanied—as did the girls.

When I was well into the eighth grade, during one of those monthly school dances I spent most of the time socializing with Cassy Mathewson, my old fair date from yesteryear. We had both recently turned 14. I couldn’t help but notice Cassy’s obvious good looks, especially in the pretty pale blue party dress she was wearing so well. Cassy was a cutie as a 12-year-old at the Fun Fair in 1976. Now she was an undeniably beautiful girl in June of 1978.

When we weren’t dancing, we were pleasantly chatting. A hugely popular Top 40 song at the time was “Two Out of Three Ain’t Bad” by Meatloaf. The deejay played it. It was an obvious slow-dance tune. Amusingly, we read each other’s mind, embraced each other, and sort of danced to it. (It was mostly a hugging and groping session that we thinly disguised as a dance. Amazingly, it was Cassy who was doing all the groping!) About two-thirds of the way through the song, Cassy stood on her toes for a moment and whispered sweetly in my ear, “Kenny, I’m sure you are enjoying me putting my hands everywhere on your body. I know you strive to be a gentleman, but you can do the same to me. I’m allowing it! Honestly, I don’t mind. In fact, I want you to do it!”

I just smiled and said nothing, but I did slowly lift my hands from Cassy’s waist and, making sure no one else in the school gym could see me, I subtly fondled her burgeoning breasts. Yippee! This was a first. I liked how they felt soft yet firm in my hands. With Cassy’s hands still exploring me in equally interesting places, it wasn’t long before I had the stiffest erection in my life. Thank heavens the song stopped about 30 seconds later. If it had lasted much longer than that I would have had a socially awkward and messy problem to deal with below my beltline. “Two Out of Three Ain’t Bad” was the final song of that night’s dance.

“Thank you for being a gentleman, as usual, Kenny,” Cassy told me with a satisfied grin as we went our separate ways.

Cassy definitely had a different definition of the word “gentleman” than I or Merriam-Webster did. I held my tongue, but I really wanted to say to her as an apt reply, “Thanks for being a little bit slutty, Cassy! I really enjoyed feeling your lovely tits. It was a marvelous experience.”

Part Three

The dance had been on a Friday night. By the time school resumed on Monday morning, I sensed a different vibe throughout the whole building. It was palpable. Girls whom I had barely known were smiling and waving at me, greeting me with hellos as if we were longtime, intimate friends. I slowly came to the conclusion that Cassy had spent most of the weekend on the telephone with her gal pals, telling them what sexual things she had done to me—and vice versa—during the playing of “Two Out of Three Ain’t Bad.” Of course, each of those girls had relayed the details to her circle of friends, thus the scuttlebutt had spread exponentially. I quaintly and naively thought girls would not discuss such personal things openly. I suppose my old-fashioned upbringing had not kept pace with the sexual liberation of the 1970s. I knew my theory was valid when a seventh-grade girl named Patty St. John—whom I had never heard of before that day—slipped an X-rated note into my locker offering me all sorts of “sexual favors better than you got from Cassy Mathewson”—if I took her on a date. Wow!

During our lunch period, Cassy cornered me when I was briefly alone to innocently ask me how my day was going. Without a bit of hesitation, I handed her Patty St. John’s note and said, “This has been the highlight so far.” Cassy was only slightly taken aback.

Cassy merely shrugged her shoulders and said, “I don’t even know who this Patty girl is, but I guess she heard about it somehow. I told a couple of friends about our last dance on Friday night. They’re so jealous!”

“Well, I told no one about what we did during that so-called dance,” I insisted. “Don’t get me wrong, Cassy. I loved every second of it, but my strait-laced parents would have a fit if they knew I was feeling up a girl during a school dance. They think these dances are adequately chaperoned by the teachers here.”

Cassy never replied to my moral concerns. She just forged ahead with her own agenda. With a smile she asked me, “Kenny, towards the end of that last dance, how close were you to ejaculating? Be honest with me.”

What a question to be asked by a 14-year-old girl! Still, I gave Cassy the accurate answer she desired. “If you really want to know, I was no more than about half a minute away from creaming my underpants!”

To my surprise, Cassy replied, “Same with me. If you had put one of your hands on a certain lower part of my anatomy and gave me a few caresses, I would have saturated my panties in a matter of seconds!” She seemed quite excited to tell me that.

While I paused our steamy conversation to mentally picture that sexy business actually happening, Cassy said, “What a shame for both of us that we had to stop just then, huh? Hey, perhaps we can pick up where we left off. Meet me right after school today at this very spot.”

I quickly said, “That sounds great to me!”

Cassy smiled. Just before walking away, she said, “Kenny, as tempting as it might be, please don’t accept that slutty seventh-grade girl’s offer until I’ve bagged you first. Not only are you a gentleman, but you’re a real hunk, too.”

According to my dining companions, I spent the last few minutes of the lunch period staring at nothing in particular with a goofy look on my face. I didn’t dare tell them why I was in such a great mood.

Part Five

As quickly as I could, I raced to the spot in the vacated lunchroom as soon as class was dismissed for the day. Cassy arrived within a minute of my beating her there. She quickly kissed me. It was something we didn’t do all that often, but I certainly wished that we would.

Cassy asked me a strange question: “Have you ever noticed how this lunchroom is used when it’s not being used for lunch?”

“Not really,” I replied. “I just assumed it wasn’t used for anything but lunch.”

“That’s mostly right, Kenny,” she confirmed. “The janitor tends to this room immediately once lunch period is over—and then he and everyone else forgets about it until the next day. It is seldom used by anyone at any other time except for lunch.”

I had no idea where Cassy was going with this conversation, but I didn’t stop her monologue.

“Have you ever noticed that red door near the exit?” Cassy inquired.

I said, “Yes, I have noticed it, but I have no idea what is behind it, though.”

Cassy did. She said, “There’s a big supply room located behind that door. It holds all the cleaning supplies for the lunchroom, extra tables, garbage bags, and so forth. It’s really quite huge. I bet hardly anyone knows about it.”

“Is there a point to this, Cassy?” I asked slightly impatiently, waiting for her to get to the general idea.

“Yes, it’s a very private place. Out of curiosity a few months ago, I walked in here at about this time of day. I turned the knob on that door. It wasn’t locked because it has no lock. I took a minute or two to look around. Yes, it’s loaded with all sorts of stuff, but there is plenty of space for two people to do intimate things without being seen.”

Now the light came on! Cassy had found a spot in this middle school that was an excellent place for an amorous couple to enjoy a quick, private fuck.

“What are we waiting for, Cassy? Let’s start!” I excitedly stated. “You can give me a tour—and whatever else you want to give me!”

Cassy was right; the door had no lock. The light switch was easily located and turned on. An illuminated room confirmed Cassy’s earlier description. She had failed to mention there were several chairs that had to be decades old. They had padded seats. I figure one of them would at least make for a semi-comfortable screwing locale.

We walked about five feet into the room. Cassy positioned a chair for one of us to sit on. It was a bit dusty from years of non-use. Cassy began unbuttoning her top. I stopped her—but just for a moment. “Shouldn’t we kiss and hug first to be romantic about this?” I asked.

“Always the gentleman, aren’t you, Kenny?” she replied with a slight giggle. “Okay, if you insist!”

“Yeah, I do insist,” I said. “I don’t want you to think I’m some sort of 14-year-old sex maniac.”

Cassy and I enjoyed the longest buss since we first tried kissing after the Fun Fair back in the sixth grade. That was now two years ago. Her kissing technique had improved since then as she also used her hands to please me as well as her soft lips.

“You really do like groping my penis, don’t you, Cassy?” I asked her rhetorically. “It’s not a criticism. Not at all. I just find it fascinating what you like best about me.”

“What I like best about you is you, Kenny! Let’s get that straight,” Cassy clarified. “You are a really sweet guy. There’s nothing about you to dislike—except maybe you aren’t aggressive enough.”

“Mr. Connolly, the softball coach, says the same thing to me about fielding ground balls from my position at second base,” I said trying to suppress a laugh. “Somehow I don’t think we’re talking about the same thing, though.”

“Not even close, Kenny,” Cassy grumbled. “I hope you are just kidding me.”

I told her I was.

“Kenny, I want you to give me the best fucking I’ve ever had, so be aggressive in your lovemaking, please.”

“The best you’ve ever had?” I questioned Cassy. “You’ve done this before? This will be a new and terrific experience for me. How many times have you—at age 14—had sexual intercourse?”

Cassy then started to speak in sentence fragments. “Three times. Same guy. Last August. He was 16…a counselor at a church summer camp. I was an assistant. A volunteer there. Something to put on my résumé.”

I was startled by this revelation. I thought Cassy was as virginal as I was.

She continued with her abridged story of youthful debauchery. “When the supervisor found out, Mark—that was the boy’s name—was given the option of resigning without accepting pay or having the police get involved because I was a minor. Guess which option he chose.”

“Jeez, I didn’t mean to pry into your personal past, Cassie. I apologize for doing that,” I said sincerely.

“You just can’t stop being a gentleman, Kenny, even as I’m on the brink of taking my clothes off!” Cassy pointed out with a laugh. “Hey, I was as guilty as Mark was. Sure, he tried to take advantage of me. He wooed me and talked me into having sex. If I hadn’t enjoyed it, do you think I would have fucked him twice more? Anyway, Kenny, you are a gentleman by nature. Kindly put that aside for the next few minutes and see if you can fuck me better than Mark did.”

Without further chitchat, Cassy removed her blouse and skirt, leaving just her knee socks, panties and bra on. I was standing only about three feet away with just my briefs on but with an obvious erection aiming at her.

“You seem ready to begin!” Cassy joked. “Let me see your equipment, Kenny. Drop your drawers!”

I did—and Cassy continued her playful groping of my manhood. For the first time, though, there was no clothing between her hand and my stiff dick. While she was occupied, I figured I should be too, so I undid her bra clasp. (That I instinctively knew how to do that task pleasantly surprised me!) I finally got to see what had gotten me so aroused on Friday night.

They were quite the appealing set of teenage tits. Somewhat pointy, they jiggled with Cassy’s slightest movement. They just begged to be fondled and sucked.

“May I touch your breasts, Cassy?” I asked—apparently too politely.

“For heaven’s sake, Kenny, stop being polite, stop talking to me altogether, and do what comes naturally—just like I’m doing with your rod.” At that point Cassy began to suck on it while kneeling in front of me. That was an amazing, sensual thrill! While Cassy was busy pleasing me orally, I gently placed my hands on her tits and started to gently rub them with the sweaty palms of my hands.

“Be rougher with me, Kenny,” Cassy demanded. “I’m not here for romance.”

I took Cassy’s advice to heart, pulled my dick out of her warm mouth—which somewhat surprised her. I then picked her up and set her cute bottom on the dusty old chair. I slowly pulled her panties off to prepare her for the inevitable fuck. I kneeled in front of her momentarily to lick her nipples. I found it to be awkward, so I said, “Cassy, I’ll sit on the chair. You’ll sit on my lap. That will make it easier for me to enjoy your luscious tits. I was right. It was great fun too. By the time I had finished sucking, licking and caressing her breasts, Cassy’s prominent nipples were hard enough to poke me in the eye. In fact, one did. We both found the incident to be amusing.

“Now you sit on the chair again and spread your vagina for me,” I instructed Cassy. “I’ve always wanted to lick a pretty girl’s pussy. You’re the lucky girl today.”

Cassy had a bit of hair guarding her treasure, but that did not faze me in my quest to find out what a girl’s honey pot tasted like. I placed my face in the appropriate place and began licking Cassie’s vagina as if it were an ice cream cone.

“Oh, I like this, Kenny. Mark never licked my vagina. He told me it would be gross.”

“The damn fool missed out on something special,” I replied and began to lick her with greater gusto. Without an invitation, I stuck the middle finger of my right hand inside Cassy’s twat and began to slide it in and out. This obviously pleased her, so I did it faster and faster. I was rewarded with a sexy squirt and a very wet right hand.

“I just have to fuck that sexy pussy of yours right now, Cassy!” I stated.

“Don’t tell me! Just do it!” she reminded me. “No one is stopping you.”

At first, I entered Cassy while she was seated on the chair with her legs spread widely. It was a truly memorable feeling to slide my rock-hard penis into a nubile female for the first time ever—and this girl was quite a looker! I gave Cassy about 30 solid thrusts before I suggested that it might be more efficient if she rode me while I was seated on the old chair. Cassy willingly complied. She mounted me and took my dick completely inside her. I was surprised she was physically capable of doing that! She bounced on my fully erect penis in a way that demonstrated that she and Mark had done the same thing last summer.

Eventually I reached my breaking point. “I’m going to come soon, Cassie!”

“Let me help you, Kenny,” she offered. Cassy dismounted me, got into a kneeling position and masturbated me to a huge ejaculation. My powerful cum shot reached a height as high as my nose and ended up in all directions. Some of my jism ended up falling into Cassy’s curly tresses. Some ended up on her bare shoulders. Most of it came down on me, however. I thought it was the sexiest thing in the world, because to me, now a former virgin, it had been just that.

“I’m certainly glad there’s an open package of paper towels about ten feet away from us on that shelf. I just made a heck of a mess,” I stated as I pointed to where the towels were stored.

“Correction, Kenny: We just made a big mess together. My pussy juice needs to be cleaned up, too. By the way, Kenny, it was way more fun fucking you than Mark.”

That remark pleased me and my male ego, of course, but I saw we had left plenty of incriminating evidence in this supply room. “Well, Cassie,” I began, “I think we ought to clean ourselves and this place before we are discovered. Let’s each get a roll of towels and get busy!”

“No, you just sit there and relax, Kenny,” Cassie said. Then she gave me a quick kiss on the lips. “I’ll do the cleanup alone. It won’t take long. Besides, it’s your reward for being a gentleman.”