Category: First Time Stories

Naughty Tomboy Neighbor

by MrJack©

Readers; I couldn't get the idea for this 'dirty-old-man' story out of my mind, so I went ahead and wrote it. I suppose this is a tale of forbidden seduction, but after writing it, I'm not sure of who seduced whom. Did the 'old man' seduce his 'innocent' neighbor or did the 'young woman' seduce him? If you have an answer, please let me know. Thank you.


(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."

Although Bill was a decade younger than me, he I had been good friends since he'd bought the farm adjoining mine twenty years ago. Why, just last weekend we'd celebrated my 50th and his 40th birthdays together 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 repentantly said. "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 several years younger than my own 28-year-old married daughter!

At my advanced years in age, I referred to all young females as 'girls'. In truth, this girl Rachel was now a fully-matured young woman who'd just recently turned 18 and was about to graduate from high school. She had plans for college in a few months. The senior student must have driven her truck home from school and then come down to the apple orchard shortly afterward.

By picking and selling truck-loads of apples, Rachel was raising money for college. But, this girl always seemed to end up spending as much time climbing as she did picking. I believe this young lady loved climbing trees more than any other outdoor activity. To put it bluntly, Rachel 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, the tomboy girl 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 good bit 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 and maybe shut you up!"

Not knowing why I did it, I said, "Alright Monkey, I'll take that bet. I don't know how you can verify it, but I'll say it's time to 'put up' or 'shut up' and prove that you don't have a tail!"

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 mature, beautifully-formed female's ass! Rachel's young body had developed nicely from the gangly 'kid' she used to be. She didn't 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, this young woman might make a good 'piece-of-tail' for some lucky 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 teaser. 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 young lady, 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 tree-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 tomboy who was timid around boys. I had known this girl all her life and I knew she was so bashful and 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 young woman'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 young lady reached for the hem of her sundress and started pulling it up. She lifted it above her panties and her abdomen. An unadorned white sports 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 pink nipples looked ripe for sucking. The stirring in my pants was now growing into a stiffening erection.

Goddamn pervert, get your dirty 'old' mind off this young woman's tits! Shaking my head to rid my thoughts from wickedness, I heard a feminine voice say, "Well, Mister, are you going to pay me my dollar, or not?"

Suddenly, my mind decided to take its own turn at stubbornness. I wasn't yet ready to give up on this game of teasing intimacy. "No!" I heard myself say. "I haven't lost the bet yet! Miss Prissy, you boasted of being a 'girl' from head to toe. I've seen your head, I've seen your toes, but girlie I haven't seen 'everything' in between. I'll be keeping my dollar until you prove your boast is true fact!"

An irritated look settled on Rachel's face. She was infuriated by this abrupt turn of events. "Damn you!" she furiously said. "You're not getting the best of me. I'll have that dollar won before I'm through!"

The determined girl gazed at me menacingly. She jerked her dress over her head and threw the yellow article of clothing in my face. I was pushing the dress aside when the bra slapped my face. I watched in stunned disbelief as the unwitting seductress slip her cotton panties down off of her ass and legs. I caught the white garment before it too hit me.

"Now Mr. devil-be-damned," Rachel said in triumphant victory. "Just look at me and tell me I'm not a 'girl' from head to toe! Do you see my pigtailed girl's hair? Do you see my girl's breasts? And, do you see the girl's pussy between my legs? Tell me Mister, is there anything here that doesn't belong on the body of a 'girl'?"

At the moment, I wasn't exactly sure whether my eyes were seeing what they were looking at or not. Yeah, I saw two pigtailed braids. Yeah, I saw those two nice small tits. And yeah, I was seeing the finest feminine pussy I'd ever seen in my life!

I didn't answer Rachel's question. My mind was too mesmerized by the wondrous splendor of the girl's pussy. The swollen mound of feminine flesh puffed out prominently between slim, short legs. Split down the center by an enticing slit, the 'pretty-as-a-picture' pussy was framed by a thin bush of sparkling blond curls! The erotic teen vaginal beauty was a magnificent piece of feminine 'art'! As for a clit, why I could only see a tantalizing tip sneaking a peek out through outer pussy folds!

"Hey you, do I get my dollar?" Rachel inquired. "And while you're at it, you'd better give me my clothes. I can't hang around naked in this tree all day long."

Without taking my eyes off the adolescent nude girl, I pulled another dollar bill from my pocket and handed it to her. Giving in to my better senses, I held out the panties and slowly slipped them up the girl's legs. Reluctantly, I pulled them up over her hips and hid the pussy I had become enthralled with. Rachel held out her arms and I slipped the bra over her head and settled it over her small sweet tits. Finally, I slipped the dress over her head.

"Thank you kind Sir," the girl mockingly said. "And, thanks for the extra dollar. I told you I'd get it, didn't I? Like I said before, I'm smarter than you are! Hey, do you want another apple?"

Just as if nothing unusual had happened, Rachel scampered up the tree and grabbed an apple. "Look out below," she said as she dropped a handful of fruit. "I don't want to be accused of doing any more ball-busting today!"

I began chomping into the apple. Rachel was climbing all over the tree picking and dropping apples into bushel baskets. The cute young tomboy swung around from limb to limb like a monkey playing in a jungle forest. Oh I forgot, I'm not supposed to think of her as a monkey anymore. Well hell, after seeing her naked, I won't be having any problem thinking of her as a 'girl' anymore! The occasional flash of tight white panties were a pleasant reminder of her girlish, womanly gender.

After several more minutes, Rachel climbed back down to the lower branch she'd been sitting on before. This time, she sat with her back turned towards me. Unexpectedly, the girl let go of the limb with both hands and fell straight backwards! Oh god, she's going to fall and break her neck!

Before I could catch her, the girl caught herself with the underside of her legs. She giggled merrily and swung her body back and forth on the limb. It became very obvious that this 'part-monkey', tree-climbing girl was just as comfortable hanging upside down as she was sitting up.

Something else became obvious to my eyes also. When Rachel fell back, her sundress dropped down over her body and the billowing skirt was now dangling down over her upside-down head. White panties and bra sprang into view.

The reasoning behind why people do some of the things they do is sometimes unexplainable. For some reason, my hands reached out and touched the girl's belly. Unreasonably, one hand slipped under the elastic waistband of her panties and grabbed a handful of pussy. And, for some unfathomable reason, Rachel was making no protests or complaints!

My hand was cupping a warm soft mound of teen femininity. I could feel the flesh swell and stiffen as hot blood raced throughout it. My own blood was racing as the erection inside my jeans grew rigid.

I had to see it. I had to see what I was touching. I hoped to hell Rachel wouldn't protest now. Using both hands, I grabbed the waistband of her panties and slipped them up off her hips. It felt a little strange having to pull panties 'up' when trying to see a pussy. Usually, a guy had to pull a female's underwear down to get to the 'good stuff'.

Up, down, whatever the hell, I got the job done! Rachel's bush-framed pussy was exposed in all it feminine glory. My hands took turns playing with the seductive, swollen, split mound. My mind instructed my fingers to spread the cracked pussy lips apart.

And there it was. The hidden clit was revealed. Oh god, what a beautiful sight the erect protrusion was! The girl's quivering daintiness daringly tempted forbidden intimacies.

The way Rachel was hanging in the tree, her pussy was only inches from my face. Unable to resist the daring temptation, my lips moved closer and closed over the clit. My moisturized tongue darted out and wetted the tantalizing feminine jewel. Unbelievably sweet, it was! My clit-hungry lips and tongue licked and sucked greedily. Rachel sighed softly.

Licking and searching, my probing tongue opened the delicate wings of this girl's inner pussy lips and found the entrance to her vaginal cavity. Puberty had visited this body so the pussy hole was drippy wet with feminine moisture. My exploring tongue found an unbroken hymen. Rachel squirmed as I teased and tested the strength of this protective virginal membrane.

I closed the pussy slit and concentrated on kissing this girl's swollen pussy mound. I loved the sweet warmth of the soft crevasse between her throbbing mound and her thighs.

Kissing and licking, I savored the taste of every delectable inch of the petite, yet fully-matured, feminine fruit. A musky pussy smell filled my nostrils. Oh god, there is nothing in this world that inspires manly horniness like the seductive aroma of a musky pussy!

Getting weak in the legs, I dropped to my knees in the grass. On the way down, I kissed a soft smooth belly and tongue-tickled a bellybutton. My face was now near the nice small tits I remembered from earlier.

Pushing the bra off the dangling tits, I transferred my sex hunger from Rachel's pussy to her breasts. These small, nubile mounds were already swollen with desire. The cute pink nipple nubs fit nicely in my mouth. My fondling hands squeezed and played.

As I kissed around and around the undersized breasts, I imagined what these 'girls' might look like if they were bigger. Hell, they would be larger is all; they couldn't be any more beautiful! I decided then and there that small sized tits were now my favorites.

Rachel had pulled her dress all the way off. It was covering her face so much she could hardly breathe. She reached up and pulled the bra off, too. I was wishing she'd take her panties off, but I knew she couldn't do it from the upside-down position she was in.

As if reading my mind, the nimble tomboy proved me wrong. Jerking her slim young body upwards, she sat back up on the limb, removed her panties, and dropped them on the ground. She then fell backwards again with her legs spread wide in open invitation.

Hell, I didn't need an engraved invitation to that pussy-eating party! I stood back up and had another helping of musky, sweet, young pussy. With a clit in my mouth and my tongue in a virginal vaginal hole, I began giving quite a bit of thought to how much I'd like to fuck my tomboy neighbor.

Damn your dirty old mind! You can't do it! You can't let this get out of hand and end up taking away this girl's last vestige of virginal innocence! There was only one answer and I'll tell it to the girl.

Dropping back on my knees, I started to speak, but then stopped. Looking at Rachel's pretty, upside-down face, I unconsciously recalled the Spiderman movie where 'Spidey' had an upside-down kiss with a girl. Did I dare try it myself?

Answering my own question, I cradled Rachel's pigtailed head in my hands and pulled her face towards mine. My mouth was still wet from eating her pussy. My moisturized lips tenderly touched hers.

Rachel's response was to mold her lips against mine and kiss me back. Although this upside-down kissing was awkward, we two soon mastered the basic mechanics and kissed passionately.

"Damnit Rachel, we have to stop this!" I finally managed to say. "Girlie girl, if you were older than you are and if was more of a 'dirty-old-man' than I am then girl I'd fuck you right here and now! But, I can't do it and I won't do it! Listen here Honey, I'm going to make you 'cum' and then I'm running away. Afterwards, I want us both to forget this ever happened!'

Paying no attention to the defiant look on Rachel's rebellious face, I stood back up and wildly attacked the young pussy between her legs. My mouth kissed, my lips sucked, and my flicking tongue licked.

Category: First Time Stories