Sympathetic Neighbor Girl

Since puberty struck, Brian hasn't convinced any female classmate to have a romp with him. Now 14, Brian's new best friend's 16-year-old sister is sympathetic.

Part One

In March of 1965, when I was approaching my eleventh birthday I, Brian McPhee, was sitting at our kitchen table. I was occupied with an important task: I was busily compiling a list of about a dozen guests whom I wanted to invite to my upcoming party. With the lone exception of a cousin, they were all neighbors and classmates of mine—and they were all males. My father, out of curiosity, glanced at the names I had written. “Those are all boys,” he accurately noted.

“Of course they are!” I replied with the confident, know-it-all attitude of a bright lad who had lived more than a full decade. “Why would I want to invite a girl—any girl—to attend my birthday party? They’re no fun at all to have around.”

Dad smirked, chuckled, and said, “Brian, if you have inherited any of my genes, I strongly suspect that within a year or two your attitude about this will change significantly.” He made no further comment on the topic and quickly walked out of the kitchen.

A year did go by…and Dad’s prediction was proven right! Oh, was he ever right! Puberty had struck me with great force just before I attained the formative age of 12. All of a sudden, I went from not caring a whit about half my classmates to being practically obsessed by them. Brenda Cheevers, Donna Edwards, Kim Nathan, Sandra McClement…the list went on and on. Suddenly, I wanted to “intimately know” all the girls in my classroom! There were no exceptions. Even the ones who were very plain now captured my attention.

The trouble was I was not the most popular boy in the sixth grade. In fact, I was far from it. I was perhaps average-looking, I attained mostly Bs in school with an occasional A in English, and I did not make much of an impression on anyone, male or female, unless I really tried. I was a nameless, faceless plebeian, always the last kid in the class whose name the teacher got around to memorizing. Nevertheless, over the years I had slowly acquired a group of male school chums whom I’d chat with at recess and perhaps even sit alongside at lunchtime. I’d describe them as acquaintances more than friends, however. I wasn’t especially close with any of them.

The relationship I had with my female classmates was even worse. Here’s one example: When I was nine, just before Christmas, I was out shopping for clothes with my mother. By chance, I happened to spot Evelyn Francis, who was in Mrs. Miller’s fourth-grade class with me that year. She was shopping at the same store with her mother. I mentioned to my mom, as an offhand remark, that the girl 50 feet away from us wearing the red winter coat was a classmate of mine. Mom said the polite thing to do would be to approach her and say hello. I did. To my chagrin, Evelyn did not recognize me or even know my name despite us sitting two rows apart in the same classroom of just 30 pupils for nearly four full months. I merely shrugged my shoulders at her willful ignorance of me and walked away, but deep down it made me quite angry.

By the spring of 1966, when I was fully 12 years old, I felt like a loaded cannon ready to explode. The slightest provocation seemingly got me sexually aroused. A benign catalogue of female fashions would get me hard even if the models were dressed quite conservatively, so you can imagine the effect that girls’ swimsuit ads had on me. A slightly older neighbor boy named Darcy had a father who subscribed to Playboy magazine. For a small price, he let me borrow back issues. I happily paid Darcy a quarter for the chance to eye the photos of the first-rate nude models. I fondly recall that Miss April of 1966, Karla Conway, was an absolute knockout—all 4’11” inches of her. I had that magazine for a week and jerked off at least a dozen times while gawking at her. During my seventh “session” with the lovely Malibu beach girl, my father accidentally walked in on me in my bedroom just after I had launched a wad of semen into a handful of tissues. I just sat on the edge of my bed with a guilty expression on my face. Dad, to his credit, merely said, “Son, don’t let your mother see that magazine or catch you doing that. There would be hell to pay.” Then he noticed Karla’s centerfold and added as an aside, “Wow! She is one shapely gal, isn’t she? Brian, if Playboy had been around when I was 12, I would have spent every waking hour staring at those pictures and pulling on my rod.” Dad truly was a terrific and understanding father.

With Dad seemingly as an ally and my behavior deemed normal by him, I wanted to screw a girl more than ever. I decided to take a direct approach. The next day at school, just before the first bell rang, I sauntered up to Cindy Nelson in the hallway.

I deliberately chose Cindy, who cut her dark hair short, specifically because she was very much like me—average on the beauty scale and easily overlooked. I figured because she fell in the middle of the Bell Curve of female classmates that she would be a good test case for me. I said, “Cindy, you’re obviously a 12-year-old girl and I’m a 12-year-old boy. Nature designed our bodies to complement each other. Are you interested in having sex with me? I think it would be a lot of fun for both of us.”

Cindy glared at me for about five seconds before saying, “Brian, if you’re aiming to get your face slapped, you’re on the right track! Don’t bother me again!”

I didn’t. I figured I should lower my expectations and proposition the least attractive girls in the sixth grade the very same way and hope for the best. I didn’t get the best: A couple of them just laughed at me; I ranked that reaction worse than getting my face slapped. One cussed at me—which was something new to me coming from a girl’s lips. One did slap me and another one spat on me. I could only negatively imagine what the reaction of my prettiest classmates would have been.

I was about to resign myself to a life of celibacy when something caused me to realize I was limiting my options. Directly across the hallway from my sixth-grade classroom was Mr. Denny's fifth-grade classroom. The students from both classes hung their coats and jackets on hooks in that hallway before proceeding inside. I noticed a flat-chested 11-year-old girl, who was quite pretty despite that physical shortcoming, taking off her jacket while she watched me doing the same. She smiled and gave me a cute wave with the fingers fluttering on her right hand. I instinctively smiled and waved back at her. At recess she did the same, so I Initiated contact with her.

“Hi,” I greeted her. “My name is Brian McPhee. I don’t know who you are, but you are very friendly, extremely pretty, and I think I ought to get to know you.” I had made a point of practicing pick-up lines to lure girls to me. This one was my personal favorite because it flowed smoothly off my tongue.

I found out her name was Naomi Webster—“like the dictionary,” she added. She had just turned 11 so I was about 15 months older than she was. She admitted she liked “gawking at the older and handsome boys in the sixth grade.” I told Naomi I was definitely older than she was, but I wasn’t so sure about the handsome part. She assured me that I was, so I took the liberty of kissing her on the cheek. Thus, Naomi Webster became the first girl I ever kissed romantically. She giggled and kissed my cheek in return.

We spent the next two days eating lunch together and chatting during morning and afternoon recesses when the other kids in our respective classes were running around. We did not have much in common except that we were attracted to one another. That was okay with me. I didn’t want to date Naomi; I just wanted to screw her. I was quite honest about it. When Carol and Denise, two sixth-grade girls who had turned me down earlier that same week, surmised what I was up to, they angrily asked if it was my intention to fuck a girl from the fifth grade. I replied, “Absolutely!” I cheerfully added, “I want to shove my dick into her vagina as soon as possible and fire a big load of cum! Then I’ll make the same offer to you two again.”

During afternoon recess of the second day, I came on like gangbusters to Naomi, telling her how beautiful and desirable she was to me, adding as an afterthought that it would be great to have sex with her after the final bell in a secluded part of the schoolyard once classes were dismissed. I was overjoyed when Naomi quickly said yes to my idea!

When the final bell rang, I rushed to the hallway to retrieve my jacket. Naomi came out of her classroom with a grin on her face. I quietly told her, “Naomi, before we have our fuck together, we need to wait about 20 minutes until most everyone has left the school grounds. That way we won’t be disturbed.” She nodded in agreement. We both sported naughty smiles. My anticipation level was high. My penis was rock hard. I noticed that I could distinctly see Naomi’s nipples, even though she only had breast buds.

After about 15 minutes I was too antsy to remain still. I led Naomi by the hand to an area of the school so obscure that most of the students seldom saw it. It was a grassy area set between the teachers’ parking lot and the new annex of classrooms that had been added to the school four years earlier, basically doubling its size. The spot where I took Naomi with the intention of fucking her was a nook of maybe 40 square feet that could only be seen from a window inside a specific first-grade classroom. Nobody else could possibly see it. Thus, if nobody was in that classroom, we would have total privacy.

When we got there, I looked into the classroom from the window. To my utter delight, it was vacant. “Get undressed, Naomi, and put your clothing into a pile on the soft grass,” I instructed her. “I’ll do the same.” In my enthusiasm, I practically ripped my clothes off my body. I was down to my briefs and ready to drop them, when I saw that Naomi had stopped when she got down to her undergarments, which consisted of sky-blue panties and something akin to an undershirt. (Under no circumstances could it be mistaken for a bra!) She had the unmistakable look of hesitancy on her face. I could tell that she had changed her mind—and would not be persuaded otherwise.

“I’m sorry, Brian. I just can’t do this,” she sadly explained. “I come from a religious family; I attend church every Sunday. The girls in the congregation have all been taught that this would be a sin since we’re not married.”

I and a certain part of my anatomy were hugely disappointed by the unexpected turn of events, of course, but I took it all in stride. I placed my hands on Naomi’s shoulders, kissed both her cheeks and her forehead, and told her it was okay and it didn’t really matter to me. In other words, I lied. Our relationship from that point onward regressed to merely exchanging occasional hellos in the hallway.

Thirty-four years later when I encountered Naomi at our school’s fiftieth anniversary event in the spring of 2000, she confessed that she had been scared off by the impressive size of the bulge in my briefs! What a compliment—albeit a late one. Naomi was now a well-built 45-year-old and twice divorced. She was apparently serious when she quietly asked me if she could make it up to me that very day by going to the same secluded spot where she had come down with cold feet back in 1966. I would have said yes in a heartbeat, but that plan would not have gone over well with my beloved wife of 20 years who had absented herself for a moment to get a cupful of fruit punch.

I remained involuntarily celibate until age 14, not counting my frequent and always enjoyable tug-time with the Playboy centerfolds courtesy of Darcy and his father's magazine subscription. Those sexy girls never once rejected me. (Dianne Chandler, Miss September of 1966, became my favorite model—and for good reason. She’s well worth seeing!)

Given that I had failed to have sexual relationships with girls my same age and with Naomi Webster who was a year younger than I was, who would have figured my loss of virginity would finally occur with an older neighbor girl?

Part Two

In June of 1968 I was 14 years and three months old. Middle school was winding down for me. In September I would join the ranks of high school students. How many of them were sexually inexperienced is anyone’s guess, but I was certainly annoyed that I was!

My new best friend was Clayton Starling, who claimed his father named him after Clayton Moore, the actor who famously played the Lone Ranger for many years. He was new to my school that year, and we hit it off marvelously. Somehow, we both had the courage to confide with each other about anything and everything. One day we both found out the other was a frustrated virgin. Clayton lived in a newly constructed house on a corner lot at the end of my street that was large enough to accommodate an in-ground swimming pool. It had been built not long after an abandoned nineteenth-century home had been demolished. May 1968 was uncharacteristically hot, and June was even warmer. On the second Saturday of the sixth month, Clayton invited me to have lunch with him followed by an afternoon of swimming. I quickly accepted.

The first thing I noticed when I entered the Starlings’ home was Clayton’s older sister, 16-year-old Jeanette, whom I didn’t know existed until that moment. She was sitting in a green bikini at the kitchen table in front of a typewriter, doing a school assignment of some sort. I was curious—not about Jeanette’s homework, of course—but because of Jeanette herself. She was quite fetching! Her spectacular bikini made her twice as attractive to me. Clayton told me that his parents were away for the day and that Jeannette would prepare lunch for the three of us whenever we wanted to eat.

Clayton introduced me as his best friend from school. Jeannette barely acknowledged my existence—until I pointed out that she had misspelled numerous words in the report she was typing. She asked me which words specifically contained mistakes. I found seven separate errors without trying very hard. I was still a B student on average, but I had always been an excellent speller.

“I’m hopeless at spelling,” she said to me. “I’m not much at writing, either. To top things off, I’m a lousy typist. too. If I make too many spelling errors, I’m bound to get a failing grade on this paper. I guess I’ll have to start all over again.” I looked closely at what Jeanette had written. I could tell it had something to do with how society had changed for American women during the Second World War.

“Would you like me to do the typing for you?” I helpfully asked her. “I taught myself how to type when I was 12 because my handwriting was sloppy and my teacher was complaining. If you just dictate what you want to write, I’ll type it. I’m excellent at spelling, so it won’t have any mistakes in it.”

Jeanete gave me an incredulous look. “You’d do that for me, Bradley?” she asked.

“Yes,” I replied, “Clayton was kind enough to invite me to lunch and to have a swim today in your pool, so this is my way of repaying the Starling family for the hospitality. However, there is one condition: You must get my name right. It’s Brian—not Bradley. I’m Brian McPhee. Nice to know you.” Jeanette apologized for accidentally butchering my name. Then we politely shook hands.

Jeanette explained the assignment. I instructed her to tell me everything she knew about the thesis of her paper and what she had learned from her research. I listened for five minutes and began typing. Within 20 minutes I had created a passable, 1200-word, high school history essay for her.

“That’s amazing!” she exclaimed when I pulled the sixth and final sheet out of the typewriter and told her she could staple her top-notch essay together. “How can I possibly thank you, Brian? You’ve saved me hours of work and done a far better job on it than I could ever hope to do.” She instinctively gave me a hug. I could now attest that having a well-built 16-year-old girl in a tiny bikini unexpectedly give you a hug is always a great pleasure in life when you are a perpetually horny 14-year-old male.

“Well, that’s a start, I suppose!” I quipped. Jeanette laughed at my subtle sexual inference.

Clayton then displayed the greatest act of friendship I had ever experienced in my short life. He made the following suggestion to his comely sister:

“I think Brian has the right idea. Why don’t you thank my buddy by giving him a good fuck? That was a great favor he just did for you. He’s a virgin. That’s right, he’s never had a fuck before—and I think he deserves one from you!” Clayton paused for a moment, then he continued, “Don’t pretend you’re an innocent virgin, Jeanette. I know you’ve screwed half the football team at your high school. Besides, Brian has a pretty big dick for you to enjoy. I’ve seen him naked in the gym changeroom at school. I envy him.”

I could have fallen off my chair after hearing that statement. Honestly, I’m not sure how I remained seated. The next thing I knew was that Jeanette was staring at me—specifically at my tennis shorts where a huge erection was steadily forming. Nothing had changed since I was 12 years old. I was still an easily aroused, healthy, young male. Jeanette’s bikini, her surprise hug, and the latest steamy topic of conversation had combined to set me off.

Amazingly, Jeanette needed no other persuasion to take me to her bed beyond her brother’s lewd suggestion. She cheerfully replied to her sibling, “Well, Brian certainly seems like a nice guy for someone who’s an eighth-grader, he did do me a huge favor, and I get the impression from what’s growing in his shorts that he has a lot to offer me. Furthermore, I’m sympathetic to Brian’s plight.” Then she faced me, smiled warmly, and announced, “Okay, Brian! Let’s go up to my bedroom right now and do it. I’ll make lunch later. I think you’ll really like fucking me.”

I was sure of it!

Part Three

Of course, I had no idea where Jeanette’s bedroom was situated, so I just followed her up the staircase as closely as I could so I wouldn’t get lost somewhere along the way. It was located at the end of a long hallway. She had a fairly large bed with four pillows on it. If you paid me a million dollars, I couldn’t recall anything else about the room. I was focused totally on Jeanette, the bed, and my stiffening dick. At that moment, nothing else in the entire world mattered to me.

Jeanette climbed upon her bed, still clad in her swimsuit, and then froze for a moment. For the slightest instant I was afraid that Jeanette was going to “do a Naomi” on me and change her mind at the last second. She did not. Jeanette had suddenly remembered to douse herself with some sexy perfume before she began. She rushed to her vanity, squirted a flowery scent on several parts of her anatomy that I might find interesting, and then took off her bikini top and dropped it onto the white carpet that covered her bedroom floor.

Jeanette was undeniably a well-proportioned girl! Her appealing breasts were beautiful items—almost as attractive as those I’d seen on the torsos of all my favorite Playboy models over the years. I rushed to disrobe so I could begin exploring her in every possible way. Oddly, Jeanette kept her bikini bottoms on, for a while, anyway. I immediately began fondling her mammary glands with equal amounts of vigor and gentleness. Meanwhile, Jeanette found my erect penis. (She could hardly miss it.) She was giving it sensuous upward strokes all the while telling me to enjoy her tits. This was easily the most fun experience I’d had in all my life! I realized in retrospect that flat-chested Naomi Webster would have been nowhere near as much fun to have as my first real sex partner as shapely Jeanette Starling was.

“Suck on them, if you like, Brian,” she suggested. I didn’t have to be asked twice. Her prominent nipples were at full attention—I’ll take credit for that—so they were ready to be used that way. I rotated between her left and right tit, alternating with licks and sucks. That seemed to amuse Jeanette who giggled at what I was doing. After a few minutes of that activity, Jeanette made a further request. “I like it when a guy licks my pussy. Can you do that for me, Brian? I’d enjoy it a lot.”

At the time, there was quite a bit of a reluctance among males to pleasure females sexually in that way. (I had read numerous letters and a few articles about the controversy, both pro and con, in the Playboy magazines I had borrowed from Darcy.) As a newcomer to carnal activities, I was perfectly willing to give it a try. Frankly, at that moment of high sexual intensity I was willing to give anything a try! (Honestly, if beautiful Jeanette had asked me to pour a kettle of boiling water over my head while chewing on a wad of tin foil to turn her on, I would not have hesitated to do so.) Jeanette finally did remove her bikini bottoms with my assistance, exposing a fairly hairy sex organ. I couldn’t care less about that. I quickly moved my face to her nether regions and began to use my tongue as a sexual device on her vagina. I was rather neutral about it. Cunnilingus neither excited me nor repulsed me--but Jeanette certainly loved being the recipient of it! I could tell because she pressed down on the back of my head so I wouldn’t stop.

Eventually Jeanette said, “You’re doing just great, Brian, but I can’t wait any longer for you to slide your big dick inside me. Honestly, your package is more impressive than what many high school boys possess.”

I figured she was speaking from ample experience, so I thanked her for the compliment. I was ready to mount Jeanette, too. I was extremely worried I’d disappoint her by ejaculating prematurely. I automatically prepared to ride her. Jeanette spread her legs accordingly. A few seconds later I was an experienced man of the world. My days of being a hapless and frustrated virgin were over. I instinctively began to ram my manhood in and out of her. My penis popped out of her pussy four or five times. Jeanette never complained once about my performance, though. She was a true angel of mercy.

Jeanette was just 16, but she was experienced in sexual matters enough to sense when I was at the brink. “You better pull out now, Brian. I don’t want to end up pregnant,” she cautioned me.

Similarly, I didn’t want or need to be a father as a high school freshman, so I quickly, albeit reluctantly, heeded Jeanette’s sound advice. I was going to jerk off to a climax on Jeanette’s tits, but she herself grabbed my shaft and literally took matters into her own hands.

A few seconds and sensual tugs later, it felt like the pressure of a steam kettle had erupted from my phallus. My cum shot flew far and wide with most of it landing on one of the pillows to the left of Jeanette. I couldn’t help but notice a few strands of my semen had fallen into her hair. One little drop of jism had amusingly landed on the tip of her nose. I let out a huge groan of satisfaction and dropped face-first onto the mattress. Jeanette sweetly embraced me and said I had done just quite well for a first-timer. “That is one fine dick you have between your legs, Brian,” she commented. “I thoroughly enjoyed it. Clayton’s suggestion was excellent. We absolutely must do this again sometime—very soon.”

I told Jeanette I was more than willing to service her at a moment’s notice. Before I left the Starling house later that afternoon, I happily gave her my phone number.

Jeanette and I washed up, got dressed, and made our way back to the kitchen where Clayton was sitting at the table, smiling. “It certainly sounded like you two were having a good time together in your birthday suits. Aren’t you glad I suggested it?”

I laughed, shook his hand, and heartily said, “Thanks, buddy! Boy, do I owe you one.” Jeanette hugged and kissed Clayton, a sign of affection that he was not expecting at all from his satisfied sister.

Jeanette made us a huge and excellent brunch of scrambled eggs, bacon, sausages, and home fried potatoes. As we ate it, I tried not to discuss what had happened upstairs, but Jeanette insisted upon it. She declared, “I honestly can’t believe that was your first time, Brian. Imagine all the girls over the years in your class who missed out on something that excellent.”

I replied, “Jeanette, I don’t have to imagine it. I’ve had a complete list of them embedded in my brain since I was 12. If you don’t believe me, here it is: Brenda Cheevers, Donna Edwards, Kim Nathan, Sandra McClement…” I think I named four dozen female classmates with no difficulty at all.