Helen: Sometimes, Dreams Come True

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Sister with brother & pimps for him with Ma's friends.
11.1k words
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caprine
caprine
215 Followers

DISCLAIMERS:

[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. It is a fantasy and as such, the story may or may not conform entirely with reality. But isn't that the whole point of fantasies? With historical exceptions, all other locations, events, and characters are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental.]

I do not practice nor do I condone any of the sexual acts about which I write, other than straight, heterosexual relationships. Other than the fact that most other forms of sexual behavior are illegal, I still don't judge others for their sexual preferences except where such behavior is hurtful/harmful to others, such as pedophilia.

None-the-less, many people have FANTASIES of such taboo laden behavior to achieve sexual gratification or whatever, but have no intentions whatsoever of carrying out such behavior in actual practice. That said, if I have struck a particular fantasy of yours, read and enjoy.

CHARACTERS

Helen Cobbler 20 .............................................. main female character, caretaker for mother
Jacob Cobbler 25 ............................................... older brother of Helen
Sara Cobbler 49 ............................................... mother of Helen & Jacob
Jesse Cope 33 .............................................. good friend of Sara Cobbler, widowed
Jan Colmer 35 .............................................. good friend of Sara Cobbler, divorced
Sue Springer 38 .............................................. good friend of Sara Cobbler, divorced
Carmen Swisher 21 .............................................. best friend of Helen Cobbler

************

The birds were singing, the sun was shining, and the early morning air was crisp and invigorating. And I was sweating like a pig. Yeah, I know, pigs don't sweat, but I do. I was climbing steadily in shadowy pursuit of my older brother. Jacob, Jake to me, was twenty-five and home for a two week visit.

Me? I'm "lil Sis," to my brother. My name's Helen and I just had my twentieth birthday a month ago. I live at home with my widowed mother, Sara, aged forty-nine. I worked during the day as an executive secretary and attended college part time at night.

The sun barely got above the horizon that Saturday morning before Jake was out in a tee, shorts, and sturdy shoes. He likes his morning runs through the light woods behind our property and up the twisting trail of a large hill beyond that.

Why am I furtively following Jake?

Good question. Deserves a good answer.

The short of it is that I've had a crush on brother Jake for over six years now. It all started shortly before my fourteenth birthday when I saw him, not quite nineteen yet, naked as he slowly strolled down the hall from the upstairs bathroom to his room at the other end. He was sporting one, damned, God-awful, big hardon. Looked big, anyway, to my (almost) fourteen year old eyes.

I'd just stepped out into the hall way to head for the same bathroom Jake'd just left. He didn't change his pace, he didn't try to cover up. He just grinned, wolfishly. When he got right next to me, he also spoke--quietly.

"Take a good look, Lil Sis, some day you may get much more than a peek at this rod after you grow up a little more."

He kept on walking and disappeared into his room. I liked the way his butt wiggled!

God, I nearly fainted. I did falter in my step but managed not to fall as I stepped into the bathroom. Checking the seat position first, I dropped like a stone on the pot and peed a good one. My hormones had jumped from high straight to super-high at the sight of that gorgeous and very rigid dick and ass my brother sported.

Christ, seeing a real, live, dick--other than the young ones I baby sat for--had been uppermost in my mind for the past six months. I'd entered puberty a year earlier with my first period and had since developed a fixation on cocks. As I said, my hormones had tripped directly to super high from the get go.

Along with my first period came other bodily changes. My boobs developed fairly quickly. Oh, I'll never have centerfold boobs, but they are a size no boy could resist. My flaming red hair was an attention getter, though I shaved smooth on the pubes. The rest of my body was in pleasing proportion to my five foot ten inch frame.

So, by now you know what I was doing, shadowing my brother on his morning, uphill run. I was perving on him as a voyeur. I was sorely hoping to get a good look at his now mature and maybe even bigger cock. Maybe he'd have to pee somewhere on the trail before we got back. I couldn't help myself. I could only fantasize about anything else happening.

I couldn't follow Jake too closely or he'd spot me. So, when he turned off the main trail, I almost missed the fact. If he'd not caught his Tee on a thorn and left a little piece just after he took the side path, I would've missed him. Naturally, I turned to follow.

It seemed like forever, but in reality, less than half an hour later, I topped a small rise and stopped dead in my tracks. Spread out below me was a small meadow with a sizable, creek fed pond, short, waterfall and all. Out in the middle of the pond was Jake, swimming with lazy strokes. A sudden dive gave a flash of his bare, white ass as he went under.

Oh my God! He's naked. Now I'll maybe get my chance.

I stepped into the underbrush for better concealment and continued to watch Jake play in the water. Then, damn, the urge to pee hit me hard. I dropped my shorts and panties to squat. I quickly found I had to more than just pee. Doing my duty took more time than I had wanted and I had to scrounge for dry leaves to clean up myself. That wasn't fun, either.

By the time I could look back to the pond, Jake his back to me, was already in his Tee and was just stepping into his shorts. I got a good look at--his bare ass, but nothing else. Shit! He sat and had shoes and socks on in a jiffy. He took off on his return run, passing by my hiding place by just feet. I waited ten minutes before I started back.

Jake was at the kitchen table, drinking coffee when I got back.

"God, Lil Sis, you're sweaty and rumpled. Where you been?"

"I went for a jog of my own this morning and I desperately need a shower. See you in a bit. Save some coffee for me."

I dashed upstairs. I laid out clean clothes: shorts and panties, sandals, and a halter top. Brazenly, I omitted laying out a bra. I was going to let my twins bob free and see if that got Jake's attention. Then, into the shower I stepped after peeling off my sweat stained clothes and tossing them into the hamper.

Damn, my nipples are hard. They sure are tingling. Hotter. I need hotter water. God, but that pelting hot water feels almost orgasmic all by its self.

What a fiasco! A little bare ass is all I got for all that walking and sweating. Oh--fingering my nipples really shot of sparks there. Damn. Let's see what adding a little action between my legs does for me. Ok, finger down the slit, ah yes, like that. Here clitty, clitty. Oh God, rub it just like that girl. God, but I wish it were Jake's cock instead of my finger! Now, one finger in the coosy--ah, all the way in. Yesss!

Oh Shit, Oh Shit. Unh.

My orgasm snuck up on me damned quick. God, but I was still horny and psyched up. My knees went rubbery but I was able to remain standing. I soaped and rinsed again before climbing out of the shower to towel off.

Jake was still at the kitchen table when I got back there.

"I heard you coming down the stairs, Lil Sis, so I poured a hot cup of coffee and added one Splenda."

"Oh, Jake, you remembered. Just the way I like it."

"Oh, I remember a lot about you, Lil Sis: how you've grown up, how you've become a gorgeous young woman, lots of things."

Yes, I blushed. And when I blush, I go fire engine red to my boobs.

"Well, Lil Sis, whose not really so little anymore, I've got to be off."

"Where you going today, Jake.'

"Got to take my car in to the garage for routine service and a little other tweaking and checking. See you later."

"Bye, Jake."

I had some errands to run, so shortly, I took off as well, but in my own car. I had to get back in time to fix lunch for the three of us.

Mom entered the kitchen five minutes after I got back. She was stunning, to say the least.

"Jeeze, Mom, you trying to set fire to the neighborhood?"

"What makes you think that, Helen?"

"Well, just look at yourself, Mom."

"What's wrong with me?"

At forty-nine, not much was wrong with her. She could pass for late twenties, well maybe mid thirties, without even blinking.

"For one, that skimpy tube top is way too small, too tight for you. Your boobs put Dolly Parton's to shame."

"And yours don't in their current, braless state?"

"Come on Mom, mine aren't anywhere near that huge. Just a good hand full."

"Humph."

"And those way too tight short shorts. My God, Mom, you've got a cameltoe to end all camel-toes."

"But it sure gets the attention of any male wandering near, doesn't it."

"God, Mother, that's what I mean, you trying to set the neighborhood ablaze?"

"Could be, Helen, could be. I'm looking for a man again."

"WHAT?"

"Oh, don't worry, I not interested in getting married again right off--but damn, I get horny too and need some relief sometimes that only a cock can give. If you don't know what I mean, you will before long."

'Oh, I know what you mean, I lost my virginity quite some time ago, BUT, I don't flaunt myself quite so brazenly."

"Humph."

Jake drove in about then. He found us in the kitchen,

"What's all the yel..."

Jake just stopped mid-sentence and stared open mouthed at Mom who was standing with her butt against the counter, talking to me at the stove. She and I both had flushed faces.

"Isn't she acting slutty, Jake? She says she's advertising for a man."

"Well, she'll damn soon find one, dressed like that. My God she looks hot to trot."

"She looks like a street walker, Bro!"

"Hey, you two, I'm standing right here. You don't have to talk about me as if I were off in Timbuktu or somewhere."

"Sorry, Mom," said Jake, "you just caught me quite off guard with that outfit."

"Be that as it may, let's get some lunch on the table, you two, I'm starved."

Lunch was quickly served. We sat and gossiped as we ate. Some belated blushing still making an appearance from time to time, even on Mom's face.

After lunch, Mom went back to her beloved flower beds, Jake went onto the backyard deck to soak up some rays, and I had some house cleaning to do. The day was unusual. Normally, I have all Saturday afternoon to myself for my house cleaning and I like to do so bare ass naked. Don't ask me why, I just do. Of course, that wouldn't do this time as both Mom and Jake were home.

But, by God, I'm not going to give in entirely. I'm going to at least clean house topless, just so. Ah, freedom.

My top came off as I thought to myself and landed on the kitchen table. I got out the dust cloth and sweeper and went to work. I even hummed a merry little tune as I did so. Some time later, I never heard the back kitchen door slam shut while I ran the vacuum over the living room rug.

"Hey, Lil Sis, what's your top doing on the kitchen table?"

"Yeow!" I shrieked and jumped a good foot. Jake was behind me, so for the moment, all he saw was my bare back.

"You scared hell out of me, Jake, I didn't hear you come into the room."

"Obviously. Do you always vacuum topless?'

Still facing away from him, I answered.

"No, usually I do my house cleaning quite naked. But with you and Mom home, I didn't think that was too good an idea."

I turned around so Jake got a full, front on look at my jiggling jugs. Even so, I couldn't keep the red flush from appearing--forehead to boobs, naturally.

"Jesus, Helen, you've got a gorgeous rack there. Looks good enough to eat, er, ah, at least good enough to lick."

"Jake! Damn. Now get out and let me finish my Saturday cleaning."

"Lil Sis, I swear, between you and our mother, I'm going to have a raging hardon the whole damned time I'm home. You can see the tent in my shorts now."

I got brave and reposted with, "Nothing I haven't seen before, big brother."

With a lewd grin, Jake said, "INTEResting, and just where did you see that?" Without waiting for an answer, he turned to amble up the stairs to his room. Over his shoulder, he got off the last word.

"You still got a beautiful set of tits, Lil Sis."

Shortly, I heard the upstairs shower running. Damn, I wonder if I could catch a glimpse?

My timing was accidentally impeccable. I was reaching for the bathroom doorknob just as the door opened. Jake stood there, surprised, and staring directly at my naked boobs and their erect nipples.

"Oh, Lil Sis, you startled me."

"Yeah, I had to pee really bad."

"You coudda used the main bathroom downstairs, hmmm?"

"Coudda, I guess. just used to coming up here."

God Damn it. Jake had a towel around his waist. No naked cock to see. Shit, foiled again. Jake suddenly got a look as if a light bulb had gone off in his head (or on in his head).

"Not this time, Lil Sis."

Shit, was he suddenly remembering six years ago?

I had stepped back just a bit in surprise when the door had opened and Jake squeezed by me. He again had the last word as he ambled down the hall into his room. Just before he stepped through the door, he pulled the towel free, showing only his bare ass, and spoke.

"Again, Lil Sis, nice rack. Very nice."

The door closed, firmly.

God Damn it, foiled again. No visible bare cock.

I went in and peed. I also used my finger to frig myself to orgasm. Just as I moaned once in climax, I heard Jake's steps as he passed by on his way downstairs.

Did he hear me? Did he figure out what I was doing in here?

I finished up, put myself back together, and went back downstairs to finish the cleaning. Jake was nowhere in sight. The cleaning was quickly finished. I got my top back on just as Mom drove into the yard and parked in front of the garage.

Damn, orgasm or not just a little while ago, I remained as horny as a buck deer in rutting season.

Supper came and went.

"No date tonight, Jake?"

"No, Lil Sis, you're stuck with me here at home tonight."

"Oh, I don't consider that 'stuck,' Jake. I enjoy your company."

"Uh huh."

The three of us played a couple of board games, watched some TV together, and at the end, did our own thing. I got on the computer and e-mailed some girl friends. Jake read a book, and Mom got her embroidery out.

Mom left for bed first, stifling a yawn. Half an hour or so later, I yawned and said goodnight to Jake. He just growled something in response, eyes never leaving his book.

The next afternoon, Sunday, I decided to soak up a few rays myself on our back deck. I put on my string bikini bottoms, which barely covered the bare necessity in front, and left the top off. It covered little more than my nipples anyway. I didn't want any string or patch lines.

Besides, Jake had already admired my naked boobs. To tell the truth, I hoped he'd admire them some more before the afternoon ended.

Our back yard was entirely surrounded with a ten foot high, basket weave fence. We were also far enough away from any neighbors houses and there weren't any two story buildings anywhere near our property. Privacy was assured.

I slathered my legs, arms, torso, and face with sun screen and lay back in the lounger with a heavy sigh. A tall glass of iced tea sat on a little table by my side.

Now this is the way to relax. Too bad I can't take my bottoms off as well.

Jake walked by on his way to the garage workshop.

"Good looking chest decorations there, Lil Sis."

"Is that all you see when you look at me?"

Jake stopped a moment.

"Beautiful face, too."

"Anything else?"

"You're fishing, Lil Sis."

"Damned right I am."

"OK, damn good set of pins as well."

"Awe, Jake, you tell all the girls those things."

"Maybe, but I mean them in your case."

He walked off into the workshop before I could answer him.

Damn that man, brother or no, can be irritating as hell sometimes.

"JAKE!" I yelled loudly.

He stuck his head out the open door of the workshop.

"Yes, my lady?"

"I want to turn over, but I need someone to do my back--with sunscreen."

"Gotta go wash the grease off my hands first, Lil Sis."

Sometime later, Jake came back and stood beside me.

"Jeeze, Jake, I could've fried if the sun hadn't ducked under for a bit there."

"You're goin' to have to turn over, Lil Sis, if you want me to do your back. Too bad, too."

"Why is that too bad, Jake?"

"Because I really like what I'm lookin' at right now."

I rolled over onto my stomach with another full red blush from my forehead to the bottom of my boobs.

Jake started on my neck and shoulders before he did the backs of both arms. My back was next. He massaged the oil in like a professional. My arousal was steadily growing, knowing it was my brother being so sensual made my arousal even worse.

A portion of the side of my naked boobs was visible. When Jake rubbed on the side of the first one, I nearly climaxed. When he did the exposed portion of my other boob, I did climax with a shudder. I also left a wet ass crack dripping onto the lounger.

Jake knew exactly what happened. He had to have known. Before he continued, he squatted lower on his knees and let his bone hard dick ride at the top of my ass crack. He got a second small orgasm out of me and chuckled. Damn him, anyway.

I was very aware, that for all practical purposes, my backside was essentially naked. The narrow waist string and the tiny string coming up my ass crack left everything really bare. Even my pussy was three quarters bare as the tiny patch didn't cover the entire area of my pussy lips and didn't cover any of the back portion of those lips.

As he worked the oil into my ass cheeks, Jake was getting a Goddamned good look at my nearly naked pussy, not to mention all the pussy juice dripping and pooling beneath me and I still hadn't seen a thing of his equipment. True, I did feel his cock on my ass crack, but no visual reinforcement.

"You know, don't you Lil Sis, you're turning me on big time with this job."

"That's the whole point, isn't it?"

Jake didn't respond to that comment. He just went back to work on my body. How he did it, I don't know, but Jake bypassed my pussy to do my inner thighs and legs. I nearly died of frustration.

Damn it, big brother, take what's offered. Cop a feel, for God's sake.

He didn't. When Jake finished, he gave me another of his devilish grins and said, "I've got to get that job done out in the garage before supper time."

With that, he strode away and disappeared once more into the workshop. Shit, shit, shit. I was burning up and it wasn't the sun that was to blame. My backside was just short of reaching the burn stage when I decided to quit and go back into the house, still wildly frustrated and horny. Horny for my big brother.

After supper, we had the same unbelievably quiet evening like we did the evening before. I enjoyed the evening, but I was edgy the whole time. Like ready to crawl out of my skin. Even Jake didn't seem to be quite his composed self. I knew what my problem was--a bad case of unrequited horniness. I didn't know for sure what Jake's problem was, but I certainly hoped I was the cause of it.

I noticed Jake having a problem because I had seen him surreptitiously try to rearrange things between his legs more than once during the evening. At least one of those times, he saw me watching him during one of those rearrangements. He had the grace to blush, that time.

caprine
caprine
215 Followers