Jenny's Sex Lesson

Middle-age Jeffrey and little neighbor Jenny have always been buddies, but at age 14, Jenny wants to take their relationship in a totally different direction.

Part One

About 30 years ago, I lived on a street where my next-door neighbors were a single mother named Joyce and her daughter named Jenny. Their surname was McKenzie.

I was never told by Joyce what had happened to Jenny’s father; I assumed either Joyce had divorced him or they had never been married in the first place. Whatever the case, there was no male influence in the McKenzie household. Not surprisingly, Jenny sought me out as a father figure just because I was nearby and friendly. It also happened that I was quite fond of this little girl since the first day I had met her when she was six years old—and she quickly became fond of me, too. From Day One she referred to me by my first name. I insisted on it. We’d frequently chat. I’d constantly buy her small gifts. I treated her like she was the daughter that I, Jeffrey Gibson, a confirmed bachelor in his forties, never had.

I discovered early on that Joyce McKenzie wasn’t exactly a demanding parent. Actually, she was far from it. There apparently were no rules for Jenny that I could see as she seemed to do whatever she wanted to do whenever she wanted to do it. I’d hear from Jenny that if there was a movie she wanted to watch on the late show at midnight, she’d stay up and watch it until the wee hours of the morning—even if there was school the following day. Then she’d not get up in a timely manner and miss school entirely that day with no ramifications at all from her mom. Somehow, Jenny was always about a “B” student in school. I figured she could be close to an “A” student with a little more self-discipline, but I felt it was not my place to say anything. Similarly, Jenny was the type of kid who would eat chocolate ripple ice cream for breakfast if she didn’t feel like having something more nutritious, again without Joyce saying a word to her about it being a poor lifestyle choice. Joyce just seemed unable or unwilling to lay down the law with her daughter. I never commented on Joyce’s substandard childrearing skills, but it bugged me a bit as I really cared about Jenny’s overall well-being.

Occasionally, I’d look after Jenny if her mother was out for a night or away for a weekend. I did create rules as her temporary caregiver—which Jenny, on some level, seemed to appreciate. This might be one reason why Jenny was drawn to me, as I represented an adult who established fixed boundaries. I was never paid for my babysitting services, nor did I want to be paid. However, Joyce, who was an excellent baker, would often send me trays full of homemade goodies, which I considered to be sufficient compensation for my time looking after Jenny.

As Jenny grew older, she’d often knock on my door just to see what I was up to. If I was watching something on TV, I’d tell her she was welcome to come in and watch it with me. I can’t recall her ever declining my invitation. It might be a documentary, a sitcom, or a sporting event, but Jenny didn’t seem to care. It was obvious she just wanted to be with me. Whatever was on the boob tube was secondary to my companionship.

At no time in the first eight years that I knew the McKenzies did Jenny and I ever have physical contact. I don’t recall even receiving a single hug from her. This made it all the more startling for me one evening in mid-October when I got a surprise visit from both members of the McKenzie household on a very memorable Saturday—and what happened as a result of it.

I had just finished my dinner and was in the middle of washing the dishes, when I heard a loud knock on my side door. I thought it might be a salesman as I was not expecting anyone. When I opened the door, I first saw Jenny standing there as the sun was setting on the horizon. Thus, I initially assumed she had dropped by for another night of television viewing with me, but then I saw Joyce standing slightly behind Jenny and off to one side. It was highly unusual for Joyce to visit me. Even when she sent me baked goods, she often had Jenny deliver them on her behalf.

I said hello to the two of them, but before I could say anything else, Joyce said, “Jeffrey, we need to have an important talk. May we come in, please?”

“Of course,” I replied. “This sounds very serious. I hope everything is alright with the two of you.”

Joyce assured me it was and then entered my home behind Jenny. We all went to my seldom-used living room and sat on the comfortable chairs there. I waited for Joyce to tell me what the purpose of this important visit was. Joyce got straight down to business.

“You have probably noticed that I have a very liberal attitude toward parenting,” she began—and I nodded my agreement. “This is because I was raised by two parents who were harsh disciplinarians. I didn’t want to raise Jenny that way, so I give her a lot of latitude in her behavior. Perhaps I give her too much. Anyway, we’ve come to an important milestone in Jenny’s life. She’s in the eighth grade now. She’s 14 years old. About two weeks ago, she and her classmates started a detailed unit on human sexuality in health class. This is a first for Jenny—and she’s been bombarding me with all sorts of questions.”

“I suppose that’s just Jenny’s natural curiosity coming to the surface,” I suggested. “I think it’s a positive thing. She wants to know more about what she is studying in school, so she’s come to you for help. I say bravo!”

“Well, it’s a little bit more than that,” Joyce responded. “The curriculum says it is normal for kids around Jenny’s age to experiment sexually. I had an early start. That was true for me when I was 10½, and it’s certainly true for Jenny. She told me tonight that she wants to have sex with a boy she knows.”

I was somewhat shocked by this. Up until this moment I had considered Jenny to be a little girl—not a sexual being. She was underdeveloped for her age, but she liked what she possessed.

Jenny interrupted to proudly announce, “My titties are starting to grow now, Jeffrey! Have you noticed?”

This was not the type of conversation I had ever shared with Jenny before, but I politely and awkwardly agreed that her young body was starting to take on a womanly form—if one looked very hard. Jenny smiled. All the while I was tempted to blush at the content of this discussion!

I believed I was being asked for my input, so I inquired, “Who is this boy you want to have sex with, Jenny? Is he a classmate of yours? This is a big step in your life. I think you are a little bit too young for sex despite what your school curriculum might say.”

Joyce answered for her. “Jenny used the word ‘boy’ rather broadly, Jeffrey. She wants you to be her first sex partner!”

I was never so startled in all my life. I turned toward her and asked, “Is this really true, Jenny?”

Her response was wordless, but it consisted of several enthusiastic nods and a big grin. Holy smokes!

As much as I was intrigued by the possibilities of bedding such a young girl for an evening of carnal delights—I often fantasized about such things—I had never thought of Jenny as being a lover to me. I felt compelled to say, “Jenny, you know I’m way older than you are. I’m 46 years old now, in case you didn’t know that.”

“That’s why I want to do it with you, Jeffrey,” she explained. “You are experienced, so my first time doing sex stuff is bound to be good and fun. The boys at my school probably don’t know what they’re doing. I’d rather have someone like you fuck me. You know I like you very much.” She paused briefly and then added as an amusing afterthought. “Do you have a big penis, Jeffrey?”

I laughed, but Joyce was appalled by Jenny’s curiosity about my anatomy. “Jenny…what a question to ask!” her mother said strongly.

“Jenny, I don’t mind you asking me that,” I replied. “Let’s just say I haven’t gotten any complaints about it.”

“So, this is where my liberal attitude about raising Jenny has gotten me,” Joyce said. “I’ve never been good at saying no to her in the past. I know I became sexually active quite younger than her age with a 13-year-old neighbor boy, so it would be hypocritical of me to say no to Jenny about this. I figure her having sex with you, an adult she adores, would satisfy her curiosity. It would sort of be like a sex lesson for her, so I like Jenny’s idea about you being her first lover. What do you think, Jeffrey?”

Good heavens! What a question to ask me! I didn’t answer right away until I was positive that they were both serious about what they wanted from me. I could tell by their facial expressions and body language that they were indeed certain.

“Well…” I said with a dramatic pause. “How can I say no to such a wonderful offer from a very beautiful girl? If you’re willing, Jenny, I’m your man!”

Jenny’s face lit up and she applauded my words, which made me laugh. Her mother nodded her acquiescence.

“When do you want to do this?” I asked.

Jenny looked at her mother. I could tell this had already been discussed by them.

“As they say,” Joyce said, “there’s no time like the present. How about tonight?”

“I have nothing else planned,” I said. “Yes, Jenny’s sex lesson can be tonight.”

I invited Jenny to stay, but she insisted on going home first to change her clothing from a t-shirt and torn jeans to something a little bit classier. “If you insist,” I said, “but you won’t be wearing it for long.” I smiled and hugged Jenny for the first time in my life. Jenny literally ran to her home to put on a different outfit.

Joyce lingered to wait for her daughter’s return to my home. “Thanks for understanding,” she uttered, as if this was some sort of burden for me. I couldn’t bring myself to say I was already sexually aroused by the mere thought of screwing her eighth-grade daughter.

“By the way,” Joyce added, “Jenny just had a physical exam and there’s no way she can get pregnant yet. Jeffrey, that means you can fuck Jenny without worrying about any potential consequences.” That was certainly a relief.

A few minutes later, Jenny returned to my house wearing a pretty blue dress adorned with white polka dots, and pristine white stockings. She looked like a typical little girl who was a few years younger than Jenny's age. When Jenny came inside, Joyce departed quietly without saying goodbye to either of us.

This was going to be a fun night for me—and hopefully for my youthful bedmate, too.

Part Two

Jenny and I returned to the living room where we had conversed with her mother a few minutes earlier. I happily commented on how lovely she looked. “You know, you look just like an angel sitting there, Jenny. I’ve always thought you were a beautiful little girl, but I’ve never told you so. I didn’t want to risk spoiling our friendship by saying anything about your good looks. But now I can. You are an absolute doll, my dear.”

I was being completely honest. Even when Jenny was six, she was especially cute. She had wavy brown hair that descended to the end of her neck, big brown eyes, and delightfully high cheekbones that gave her a very pretty face. I figured she was about average height for her age, but perhaps slightly smaller. Jenny was right that her breasts were slowly beginning to take shape, but they were really just at the developmental stage.

“Alright, young Miss Jenny McKenzie, you are here tonight for a sex lesson,” I said in a comically stern teacher voice. “My job tonight is to teach you some basic things about intercourse. In doing so, I intend to give you the fucking of your life! Is that understood?”

“Yes, Jeffrey,” she said obediently. “But any fucking you give me will be the fucking of my life. I’ve never fucked with anyone before!”

“Point well taken!” I replied. “I’ll do my best to make this occasion memorable and pleasurable for you. It certainly will be pleasurable for me! Come here, sweetheart. Let’s begin!”

Jenny walked towards the chair where I was sitting. I lifted her onto my lap and began kissing her face beginning at her forehead, down to her cheeks, and then to her neck. I then moved to her lips to give her a very passionate buss. I sensed Jenny was a little nervous and hesitant.

I advised her, “Just do what comes naturally, Jenny. Relax and have fun.”

She smiled and started kissing my forehead and cheeks. Then we touched lips again. Jenny was in no hurry for the kiss to end—and neither was I. “I don’t want to stop, Jeffrey!” she said softly.

“Who says we have to stop?” I replied. “We have all the time in the world. Kissing is great foreplay before sex. It will get us both in the mood for intercourse—like I’m not already!”

As the kissing continued at Jenny’s insistence, I began to fondle her small body. I ran my fingers through her hair, I caressed her forehead and back, and then I began feeling Jenny’s barely-there breasts through her blue dress—which caused her to sigh noticeably.

“Do that some more, Jeffrey,” Jenny said with a slight giggle. “I like it when you touch my boobies.”

“Well, I do too!” I said in response. “I’m going to carry you to my bedroom where we can do this properly, my love.” I lifted her up and romantically kissed her as I carried the eighth-grade cutie to the place where I would ravage her—but I would do it like a gentleman, of course.

“Let’s get you undressed, Jenny, so I can see how beautiful and sexy you are,” I said. Then I proceeded to unzip her dress. Jenny assisted me in pulling it over her head to reveal the small bra I had already noticed she was wearing. I asked her to remove her shoes and pull down her stockings. She did and tossed everything onto the carpeted floor near where her dress was now lying. Jenny was reclining on the king-sized bed in her lovely girlish undies as I took off my shirt, trousers, shoes and socks. I stood in front of her wearing only my briefs which did little to conceal the major erection I had developed at the mere thought of making love to this girl whom I had come to adore over the past eight years. I climbed onto the bed beside her.

“Jenny,” I instructed, “please pull down my underwear and free my dick from being confined!” Jenny did it with a broad smile on her face. My erect phallus sprang up immediately.

“I think that’s a very big penis,” she said. “Am I right, Jeffrey?”

“I’d like to think so—and you’re the cause of it being as hard as it is,” I said. “I’m going to please you with it more than once tonight, I promise you that. Now let me get a good look at your bodily treasures.”

Jenny pulled off her bra which revealed not very much at all in the way of tits. Nevertheless, the fact that she was exposing her virgin breasts to me made it as exciting as if a busty, 20-year-old Playboy centerfold model was showing me her melons. I felt my dick grow even harder. I took the liberty of removing Jenny’s sexy pink panties. She had only the slightest amount of pubic hair, but she had as nice a vagina as I had seen on a girl of any age. I folded the panties neatly and put them on the table beside my clock radio. I told Jenny I might want them as a keepsake from this momentous night.

“I get it,” Jenny declared. “Kind of like a trophy.”

“Well, I’d prefer to think of your pretty panties as more of a memento than a trophy,” I thoughtfully replied, “but there’s a trophy aspect to it, for sure!”

I slid down the bed, so I was close to Jenny’s lower abdomen. I noted, “Here’s where I start to have fun with your body, Jenny. You have a beautiful pussy. I can’t wait to start licking and sucking it. Just lie back and enjoy the sensation, my sweet girl! I guarantee you’ll like it!”
I planted my face directly on Jenny’s youthful snatch. I licked it and kissed it. I sucked on it and fingered it. I lapped up the wetness that Jenny had unleashed. I found her clit and rubbed it sensually. Jenny did more than lie back: she began to squirm and make contented sounds. Turning Jenny on was also turning me on!

“Jeffrey, I’m feeling funny down there!” Jenny said, obviously referring to her vaginal area.

“That’s perfectly normal,” I insisted. “Believe me, something very nice is about to happen to you, sweetheart.”

I had barely got those words out of my mouth when Jenny experienced a terrific orgasm that made a portion of the bed quite moist. When she stopped moaning, Jenny apologized for the mess.

I responded, “Not to worry, my love. That’s a trophy for me that I made you have such a great orgasm!” I eagerly kissed her pussy again and licked her girlish juices. Between slurps I said, “Jenny, I have a hunch the bed will get a little messier before the night is done!”

We embraced and kissed passionately again. “Time for me to fondle your breasts, Jenny.”

“There’s not much to fondle, Jeffrey,” she said somewhat sadly.

“Nonsense! I insisted. “It’s about quality not quantity!”

My mouth surrounded her left breast bud and a sucked away at it until I felt her nipple harden. “Another trophy for me!” I said. “I want a matching set!” I did the same to her tiny right tit until her nipple was prominently stiff. Then I positioned myself to where I could rub my erect penis against her little goodies. I loved it! Jenny didn’t object to this sex act, but she did question what I was doing. “I’m giving my dick a treat. It likes your tits as much as my mouth does.”

After about a minute of fucking the tiniest tits in my sexual experience, I warned Jenny, “Now I’m going to please you with my penis. I’m going to fuck your beautiful pussy until I come inside you—and there’s no doubt I will come inside you, my sexy little angel. Be prepared!”

I got onto my feet, grabbed Jenny by her waist and drew her towards the end of my bed. I spread her legs, which were quite sexy for someone just 14 years old, and placed my hard rod at the opening to her heavenly pussy. “Here we go!” I said as I shoved my dick inside of her. She moaned sexily as I pushed my seven inches steadily into her love canal. I slid it slowly in and out of her, all the while I began blathering, “You have a great, tight pussy, Jenny. You are a terrific fuck! You’re too good to be fucked by some little schoolboy. Your cunt was made for my dick! Jenny, I’m not going to last much longer.”

I knew I was about to come in the virginal cunt of young Jenny McKenzie, age 14, and I had the freedom to ejaculate a massive load without fear of any consequences. It was sexual liberation for me at its fullest—and I let loose with a huge wad of semen. I felt four shots leave my cock and enter the body of sexy little Jenny. “This is the best feeling of my life!” I excitedly told her.

Jenny had been merrily moaning for the last several minutes, unable to form coherent words nor sentences. Now she was in control of herself enough to be able to agree. “Oh, yes! Me too!” she squealed. “Keep doing what you’re doing, please, Jeffrey.”

But a 46-year-old man is not the same physiologically as an 18-year-old, so I had to stop, pull my rod out of Jenny’s cunny, and give my dick a much-needed breather.

“Why did you stop thrusting your penis in my pussy, Jeffrey? It was fabulous. Keep doing it. Don’t stop!”

“This is another sex lesson for you, Jenny.” I explained, “A woman can pretty much have sexual intercourse all night without having to stop. A man cannot. He needs time to recharge his dick. The older he his, the longer he needs to take a rest. That doesn’t mean we can’t enjoy each other’s body while we wait, though. I’m certainly not through enjoying yours, you terrific little sexpot!”

For the next 30 minutes, I instructed little Jenny how to please a man both orally and by just using her hands. I caressed Jenny’s cute little bottom, sucked on her tiny tits for a spell, and exchanged passionate kisses with her. After about an hour of these carnal delights, I alerted Jenny to my erect dick.

“Does this mean you can do more fucking now?” she asked eagerly.

I didn’t answer with words. While I contentedly lied on the bed, I picked Jenny up and set her crotch on my penis and guided her up and down. “Ride it, cowgirl!” I shouted.

“Oh, I like doing this too!” Jenny roared.

Jenny was not alone. I liked it so much I knew I was about to come very soon. I lifted Jenny off my penis and laid her onto the bed. I got on my knees near her face and shot a surprisingly powerful wad of goo onto her lips, nose and forehead. One strand went straight into her wavy brown locks. I groaned with pleasure, but Jenny wasn’t too thrilled by where my latest ejaculation had ended up.

“I liked it way better when you came in my pussy,” she admitted while cleaning herself up with a fistful of tissues. “Why did you have to come on my face, Jeffrey? I don’t think I liked you doing that.”

I apologized immediately. “Oh, I’m really sorry you didn’t like it, Jenny. Some girls like it a lot. All guys like doing it. That’s for sure. It’s sort of a way a man shows off. He’s proving that he can control when and where he shoots his cum. This is a good lesson for you, Jenny dear. Sex should be an enjoyable thing. If there’s something you don’t like, say so. A decent guy ought to respect that and not do it.”

“Okay,” said Jenny. “You made your point, Jeffrey. You proved to me you can hold your cum shot. Please don’t come on my face again; I don’t like it.”

I promptly kissed her and helped her clean my semen from her hair and face.

“It’s a crying shame that you don’t like it,” I said with a laugh. “Jenny, you looked really sexy with my load splattered all over your pretty face!”

I suggested that Jenny get into the shower to cleanse herself before we resumed our sex lesson. While she was doing that, I telephoned Joyce to get something clarified.

“Hi, Joyce,” I said. “This is Jeffrey checking in. I’m not sure if you were expecting Jenny to come home tonight, but I can guarantee she’ll be sharing my bed all night.”

Joyce confirmed she expected Jenny to be my bedmate until the next morning. Being curious, she also wanted an update. “How are you two getting along in the sack?” she asked anxiously.

“Well, let me review what’s happened,” I replied. “So far, it’s two cum shots from me, one in Jenny’s fabulous, tight pussy and one on her pretty face. Jenny has had at least two orgasms—only she knows the exact total for sure. There’s been pussy-licking, dick-sucking and jerking, titty-fucking and sucking. I’d say that is quite a good start for us.”

“What’s next on the agenda for my promiscuous little daughter?” Joyce asked rather enthusiastically.

I told her, “Once I hang up the phone, I’m going to surprise Jenny by getting into the shower with her and have her bend over so I can fuck her roughly from behind. I intend to fire another cum shot all over her precious tiny little titties.”

“Wow!” Joyce marveled. “What a night of glorious sex you two have been enjoying!”

“Yeah,” I agreed. “I’ll have to come up with a few kinkier things to show Jenny for lesson number two next Saturday night.”