Rachel, My Naughty Little Tomboy Neighbor

JackassTales…Tale #30…Readers; Okay here I go again presenting a story with a teen girl in a sexual relationship with an older man. Please, if this subject bothers or offends you, find something else to read. This site is full of stories to suit anyone’s preference. If you decide to read this story; thank you.

Rachel, My Naughty Little Tomboy Neighbor

(Part one) The Orchard

I heard giggling but there wasn’t anyone in sight. Supposing I had imagined the sound, I ignored it and went back to eating my apple. I was sitting on the ground with my back comfortably resting against a huge apple tree. It was my neighbor’s orchard I had invaded to ‘steal’ some of their succulent fruit.

Of course now, I wasn’t really stealing. I’d been given explicit permission to pick some apples from the bountiful orchard. My friend Bill had said, “Jack, pick all you can eat; we’ve got plenty.”

Bill and I had been neighbors and friends since boyhood. As youngsters we had ripped and run the hills and hollers of our neighboring farms. Now, several decades later, our friendship was as strong as ever. Why, just last weekend we’d celebrated our 35th birthdays at a strip club we occasionally frequented.

I heard the giggly sound again. This time, it was more of a snickering laugh someone was trying to restrain. Before I could locate the source of the puzzling noise, an apple fell from above and landed between my legs. I don’t think Newton’s Law of gravity says anything about the painful effects a falling apple can have when striking a pair of tender testicles. I cried out, “Oh goddamnit, that hurt!”

“Oh Mr. Sharp, I’m sorry,” a voice from above spoke repentantly. “I was just teasing. I didn’t mean to hit you ‘there’.”

Twisting my head to look up, I saw a barefooted, pigtailed form scampering among the tree branches. I spoke a little more sternly than I intended, “Damnit Rachel, you did hit me ‘there’ and it stings like hell!”

“I’m sorry, I’m sorry, I’m sorry,” the girl apologetically said. “Can I do anything to make it stop hurting?”

My mind immediately came up with an answer, but just as quickly tried to dismiss it. I was thinking that ‘yes’ there is something a female can do to relive a man’s testicular discomfort. But, this particular feminine personage was not the one to do it. First of all, she was my friend’s daughter. Secondly, and more importantly, this girl was only 16 years old!

I thought I’d seen the school bus stop a little while ago. Rachel must have scurried over to climb the apple trees shortly afterward. I believe this girl loved climbing trees more than any other activity. To put it bluntly, this girl was a certified, A#1 ‘Tomboy’. She wore scratches and bruises all over her body as badges of tomboyish honor.

Looking more closely at the bedeviling vixen sitting on a branch a foot or so above me, I noticed that today Rachel didn’t look ‘boyish’ at all. Surprisingly, she had on a dress! Sitting as she was, the yellow sundress had hiked up her legs and the hem was now far up on her thighs. The shoeless, sock-less legs were slim and short, yet today they somehow seemed seductively attractive. Why, the girl’s halter-topped dress even displayed a hint of ‘bosomy’ cleavage!

I supposed I ought to stop my unintentional gawking and answer the girl’s question. “Monkey,” I said. “There is not a thing you can do to help me with my ball-busting pain. Next time, Monkey, why don’t you throw a banana at me? They are softer and do less ball-bruising than apples do.”

“Stop calling me ‘Monkey’!” Rachel angrily retorted. “You know I don’t like for you to call me by that name. I’m a ‘girl’ not a monkey!”

While it was true I knew Rachel didn’t like the name, I just couldn’t resist mischievously teasing her with it. “Monkey,” I said. “The way you scamper around in the trees like some wild primate, I wouldn’t be a bit surprised to see a tail sticking out behind you! Hey, Monkey, do you have a tail?”

“I don’t have a damn tail!” Rachel heatedly responded forgetting to watch her language. “I bet you a dollar I don’t and I bet you I can prove it!”

Not knowing why I did it, I said, “Alright Monkey, I’ll take that bet. I don’t know how you can prove it, but I’ll say it’s time to ‘put up’ or ‘shut up’ and prove it!”

I had no idea what Rachel was planning to do, but when she did it, she just about blew my mind. Twisting around on the thick tree branch, the girl turned her back towards me and raised her dress above her waist. “Okay Mister,” she triumphantly said. “Do you see any tail?”

For a fact, I didn’t see a monkey’s tail. Nope, all I saw was a shapely, underwear-covered rear-end. Answering the girl’s question, I said, “You’re right, I don’t see a tail. But, Monkey, for all I know, you might have your tail tucked away under your clothes!”

With her temper inflamed, Rachel reacted instantly. She pulled her dress up higher and then pulled her white cotton panties down several inches. “Now smart-aleck,” she said victoriously. “Do you see a tail? Mister, I believe you owe me a dollar!”

Again, for a fact, I saw no monkey’s tail. What I saw was a beautifully-formed female’s ass! For a girl of 16 years in age, Rachel was developing really well. She didn’t yet have what could be called an ‘hourglass’ figure, but the sight of the nude young ass was causing an undeniable stirring inside my pants. Monkey tail or not, give this girl a little more time and she’d make a good ‘piece-of-tail’ for some guy!

As Rachel pulled up her panties and pulled down her dress, I removed a dollar bill from my jeans. The girl turned back to face me, reached down, snatched the bill away, and tucked it into a sundress pocket.

Not contented to sit back and savor her victory, Rachel pushed her luck. She had ‘bested’ her mischievous neighbor in a teasing game but she wanted to rub salt in the wound. “Mister,” she commanded. “Don’t you dare call me ‘Monkey’ again! Let this be a lesson to you. Sir, I’m smarter than you are!”

Smarter than me, are you? My mind was racing a mile a minute in an effort to formulate a plan to once more get the upper hand over this impish child. Finally, something came to me. “Yes ma’am,” I replied in mock defeat. You’ve proved to me that you’re not a tree-climbing primate. But child, if you’re not a monkey then what are you? I guess you want me to call you a ‘girl’?”

“I most certainly do!” Rachel answered adamantly. “That’s what I am. I’m a girl from the top of my head to the tips of my toes! As a ‘girl’, I’d expect a great deal of respect from an ‘elderly’ gentleman such as yourself!’

This impudent nymph was ‘cruising-for-a-bruising’ and I was just the fella to give it to her. She had taken the bait I’d thrown out and now it was time I sprung my trap. I intended to teach her a lesson and win this teasing game.

“Okay ‘girl’,” I said with a mischievous twinkle in my eye. “You’ve proven to me you’re not a monkey so I’ll accept that fact. But Dearie, am I supposed to just take your word for it that you are indeed a ‘girl’? If you want me to believe this as fact then I guess you’ll just have to ‘prove it’!”

Aha, I had her! She won’t be able to give evidence of ‘girlhood’ without displaying a bit more feminine flesh than a quick flash of naked ass. This was a shy, immature tomboy who was fearful of boys. I had known this child all her life and I knew she was so modest she wouldn’t wear a bathing suit in front of boys. I had this teasing game ‘in the bag’!

Just to taunt and embarrass her into admitting defeat, I said, “I’ll tell you what. I want to win my dollar back, so I’ll bet you a dollar you can’t prove you’re a ‘girl’!”

Sitting there on the outstretched tree limb, Rachel’s face showed conflicting emotions. She was frowning and pouting because her ‘elderly’ neighbor had outsmarted her. Yet, there was also a smirking sneer of rebellion attempting to betray modesty. This girl’s hair was blond, but she sometimes had the temperamental stubbornness of a redhead.

Rachel’s inflamed temper asserted itself now. “Okay, Mister,” her voice angrily wailed. “I’ll take your bet and I’ll take another of your dollars, too!”

Unbelievably, this aggravated girl-child reached for the hem of her sundress and started pulling it up. She lifted it above her panties and her abdomen. A white, lacy bra came into view. The girl lifted the yellow dress higher.

Taking in a deep breath, the girl grabbed the edge of the skimpy bra and pulled the stretchy garment up to her chin. Released from their cloth confinement, a pair of small breasts burst into the open.

With her face blushing with embarrassed awkwardness, Rachel nonetheless spoke triumphantly, “See these, Mister? They’re ‘tits’! Only girls have tits! I have tits therefore this proves I’m a ‘girl’! Smartass, you owe me another dollar!”

I don’t believe I was paying much attention to what my tomboy neighbor was saying. My mind was too busy trying to adjust to the sight before my eyes. Now, I’m a guy who loves tits, but it had been a long-damn time since I’d seen a pair of beautiful young breasts. I was seeing them now! Small and petite, they certainly were, but god they were perfectly proportioned to fit a young lady’s chest! I’d bet they would fit well inside my hands, too. Those perky little nipples looked ripe for sucking. The stirring in my pants was now growing into a stiffening erection.