A Sheltered Son

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Joey's sister willingly provides his sexual education.
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Joey's sister willingly provides his sexual education

Joey at eighteen was a shy and introverted young man. His father had died when he was very young and since then he has lived in considerable luxury with his lawyer mother. He has an only sister Penny who is twenty seven, was married at eighteen, and recently became divorced. She, and only on the previous evening, has returned to the family home.

On her first morning back and attracted by noise from the pool outside, Penny wandered over to the bedroom window. Dressed only in the panties in which she had slept the woman paused at the full height glazing and stretched lazily before sliding open the door.

"Joey's up bloody early."

Penny muttered to herself as she stepped out onto the balcony to watch her brother down below who was swimming up and down. Her mother and Joey lived in a property with an amazing location being backed directly onto the beach and with a pool between the house and the shingle shore.

She bent forward to lean indolently against the balustrade, looking out to sea and basking in the warmth of the morning sun, her small up-tilted breasts resting on the oiled teak. Her muscular but shapely legs were well apart, feet planted securely on the timber decking, and her bum was elevated enticingly. But then her attention was suddenly caught by Joey leaving the water.

"My god, what's happened to the nerd I grew up with?"

Having left home when Joey was only fourteen, and only meeting him irregularly since, she had not realised quite how much her brother had physically changed. He was no longer the slender effeminate youth she remembered, okay he was still extraordinarily pretty but overlaying that beauty was a supple muscular development, a pronounced six pack and a bulge in his speedo's which immediately turned her mind to thoughts of sex.

During all the problems with her husband Penny had grown to ignore her previous deep need for sex. In fact she couldn't remember when she had last been fucked nor even her last orgasm, so to be instantly turned on like this was very unusual.

"God, I haven't felt this randy in ages."

She was already making slow circles against the parapet with her aching pudenda but returned to her rumpled bed where she began to hump her pillow with increasing force and with a series of stifled shouts of pleasure. Penny climaxed quickly and then lay panting in wonderment.

So this is what she had been missing. Well now she could get on with her own life! No pandering to a loser, free to do what she wanted.

...

Later Joey watched his sister as she busied herself in the poolside kitchen and then appeared with coffee for them both, but he was by now thrown into complete confusion by the sight of her trim body in a skimpy bikini. In fact a solid erection was soon straining at his trunks forcing him to shift position on the lounger to hide the evidence.

But he was brought up short by the directness of her opening comment.

"Mother reckons you might be homosexual. Not that it particularly disturbs her, it was just an idle observation."

Already troubled by discovering that he fancied his sister Joey found himself temporarily speechless so she continued completely unfazed by his silence.

"Apparently you don't have a girl friend and you never watch porn."

But now he recovered enough to make a stuttering reply.

"No...at least I'm sure of that...I know I'm very pretty, in fact at one time blokes at my public school used to come on to me, but I've never felt any attraction to men."

"Perhaps you're just a late developer and you'll come out later?"

"No chance," he spoke dismissively with his cock throbbing as if to prove his hetero credentials, "but why does my sexuality worry everyone so much?"

Now he was suddenly being combative and Penny was forced to backtrack.

"Personally I don't care a monkey's, it's just something mother said."

That night he had a wet dream and woke in the throes of a shattering climax. He was face down and ejaculating heavily into his jockey's when he surfaced. He was not in the least ashamed of having such a dream as they were fairly regular occurrences but was disturbed at the thought of fucking his sister which had generated this enjoyable and intense fantasy.

...

Penny appeared again on the following morning to join him at the pool. But this time it was Joey who opened the conversation.

"What went wrong Pen, I mean with your marriage?"

"In the end I was just too clever for him and he couldn't cope."

"What do you mean you were 'too clever'?"

"Just that."

"Yes but I still don't understand."

"When we had an argument and he couldn't find the words to win he would always resort to violence."

"Wow. Did this happen often?"

"Enough to make me leave."

It wasn't long before they got into a routine so it was no surprise to Joey when his sister would regularly appear to lay down nearby and, perhaps not surprisingly, they had a lot of catching up to do.

"Have you ever had a girl friend?"

"No. At least not regularly."

"Do you want one?"

"Oh yes, of course. But it's difficult because I get so tongue-tied when we're talking and I've no idea how to progress."

"So have you ever kissed a girl?"

"No."

He was back to the monosyllabic answers and so she moved swiftly on to other things.

The next day however Penny, obviously fascinated, continued to investigate her brother's sexuality.

"Do you masturbate Joey?"

There was a silence as he thought honestly about his sexual habits.

"Sometimes, but I prefer to work out in my gym. That seems to take my mind off sex."

They were silent again for a time until he eventually continued.

"But I do have wet dreams."

"Perhaps that's because you don't wank enough."

"Maybe...but I did have one the other night."

"So who or what did you dream about?"

He was silent again until she finally cottoned on.

"Me?" she paused, then made the obvious connection. "You were fucking me?"

There was an appreciable break before he eventually answered.

"Yup. I think you are really hot."

...

"Do you want to kiss me?"

She had asked on the following morning having made a performance of moving her lounger close to his.

"Of course, but we both know that would be very wrong."

"Not if you were only practising."

He took time to think about that but then replied.

"The trouble is I would soon want a lot more."

Shrugging as if totally unconcerned, but thinking 'you and me both', Penny then lay back and in time dozed off only to be woken later by the soft contact of lips upon hers. She opened her eyes to find Joey kneeling beside her recumbent body.

"Umm, that's nice."

She whispered even as her arms snaked out to imprison him.

...

His kisses on a later morning became more adventurous and he had moaned in pleasure when she had opened her mouth to play with his tongue. Later, as his breathing grew less controlled, Penny disengaged but only to speak.

"Do you want to touch my breasts?"

"Yes please."

As before he was on his knees beside her lounger so she took his hand and placed it on her bikini top.

"Now slip your hand inside."

She spoke seductively then having tentatively fumbled his way beneath the tiny patch of material she heard Joey take in a ragged breath as her nipple grew under his palm. His mind raced for a moment but as he slowly came back to earth his erection was pressing against the metal structure of the lounger and without thought he began humping the frame.

But in her growing passion Penny sucked his tongue into her mouth only to feel him exhale and abruptly break all contact.

"What's the matter Joey?"

"I've cum in my trunks."

"Darling, it's only to be expected."

"What do you mean?"

His head was down and his eyes were unable to meet her gaze.

"You've never touched a woman's naked breasts before, so it's not surprising that the excitement got a bit too much for you."

...

The poolside encounters ceased for the weekend because their mother was home, but were resumed on the following Monday when the weather remained hot and sunny.

"Can you feel how my nipples grow in your hands?"

"Why do they do that?"

"It's because you've turned me on."

"Oh."

"Look Joey, it's the same thing that causes your erection...and makes a woman's clitoris swell."

Now it was her turn to feel the pressure because the temptation to take things further was becoming almost too much to resist. But eventually she tore herself away to get on with some necessary business (she still had to earn a living) although Penny masturbated that night as she had done two or three times a day ever since returning home.

...

But by the following morning she had made up her mind and her plans were aided by a sudden rain storm and Joey's immediately voiced complaint.

"What shall we do today?"

"We could watch a film."

She caught the look which flashed across his face and interpreted it correctly.

"I know you don't have anything that would appeal to me but I've just been sent some new French films to review."

The media room was already darkened and Joey was stretched out on the sofa as Penny inserted a DVD. She raised his shoulders to slide in and then parked his head back on her lap.

"Are you comfortable?" she asked.

"Yeah, I'm fine."

He worked the remote control and they were ten minutes into the action before the first contact occurred between the hero and the mother of his private pupil. This highly charged sexual encounter immediately gave Joey an impressive erection which he made no effort to hide so by now Penny's attention was entirely concentrated on her brother's crotch. The pressure of his head in her lap as they watched the couple get it on was also driving her crazy with desire not helped by a growing need to masturbate.

So unsurprisingly it was not long before her hand stole down his chest to eventually stroke the bulge but after only a few minutes of contact Joey's hips rose, then jerked spasmodically, and she felt his penis throb as he spurted powerfully into his boxers.

"Oh god Pen, I've come again."

"It's perfectly okay luv. Stay here and I'll be back in just a sec."

She slid out but returned within minutes with a washcloth and towel.

"Let me clean you up."

After unzipping his fly she eased down the cropped chinos followed by his semen stained underpants. Then, as his rapidly rejuvenating erection grew in her hand, she tenderly wiped him clean and then dropped a kiss on the circumcised helmet.

Neither sibling was now making even a pretence of watching the film but Joey was wide eyed as his big sister shed her outer clothes to reveal the skimpiest of underwear. His cock bobbed as the sight caused his breath to catch before she spoke in a voice husky with need.

"Take off my bra Joey, then my panties."

Seemingly in a trance, he did as requested. First to go was the bra to expose those erect nipples which had already amazed him by their ability to harden in his hand, then a neatly trimmed triangle of black hair appeared not twenty centimetres from his face.

"Do you know how to find my clitoris?"

She asked softly even as she kicked away the cotton knickers and saw his head shake in the negative. So taking two of his trembling fingers Penny used them to part the soft hair covering her private parts and then placed them on the correct spot.

"Can you feel how large it's grown?"

"Yes."

His voice was wondrous as the blood surged into the source of all her pleasure.

"Stroke my clit Joey, it won't bite."

His fingers moved slowly at first then quicker as her hips began to rock.

"Can you feel how wet I am?"

"Oh yes."

"Keep stroking just like that but tease my nipple with your other hand."

He was transported by the power which he now had over this desirable woman, this woman who wouldn't stay around to be hit by her husband and who he suspected was mentally stronger than he would ever be.

Then, when unable to wait any longer, Penny climbed astride her brother and reared above him while still writhing on the hand that cupped her mons. But now, desperate to be filled, she sank down to impale his erection and not a moment too soon because a shattering climax then made her buck and thrash about.

"I came immediately you were in."

Penny's voice conveyed her wonder as the spasms slowly died away and Joey responded.

"Is that unusual?"

"For me yes, my husband never got me off."

But she soon became aware that Joey's erection was still solid inside her vagina so she rolled them both over and put her mouth to his ear.

"Now fuck me Joey."

"But what if you become pregnant?"

He managed to ask despite his over-bearing excitement.

"I'm on the pill."

This was all the reply he got and despite his efforts to last, at least until he got into the swing of this new and fabulous experience, Joey soon tensed up and pumped his second discharge into his sister's slick vagina.

"You're very good." Giggled his sister later, but her desire was mounting again. "Bring me off with your hand Joey."

He did as he was told but as she grew near the orgasm his erection was up and ready once more and she giggled again before taking him in with an appreciative sigh.

"Oh to be so young and virile."

...

Sadly however now came the remorse. Not for Penny but solely in Joey's mind. He had spent a disturbed night full of shame which he confessed as the pair were returning from a trip to the supermarket.

Later they were by the pool where his sister had now begun sun bathing in the nude and in order to express his worries without distraction Joey had pointedly covered Penny with a towel before beginning.

"I told you it was wrong to even kiss," complained the youth, "look what that developed into. But for me to...to...fuck my sister is even worse."

"Well we can't undo what's already happened."

She replied off-handedly clearly not feeling in any need of repentance.

"But I can't come to terms with...doing that to my sister."

At this point she finally realised what a serious matter this had become to Joey and immediately tried to ease his conscience.

"Listen Joey while I tell you a true story," she then sat up and tied on her bikini before continuing, "when I was eighteen I lost my virginity, in fact I couldn't wait to be rid of it, and over the next couple of years I was pretty liberal with my favours. But that all stopped once I met my future husband and I was totally faithful for six years, even when I discovered that he had a mistress back in his office."

"So he not only beat you but he had a bit on the side."

Joey was now totally caught up in her story.

"Yeah, ironic isn't it."

"No wonder you got a divorce."

"And thank goodness I had no kids."

"And that you've got such an amazingly interesting and well paid job."

"Oh that undoubtedly helps a lot but back to my point. You didn't take advantage of a weak woman, in fact I was randy enough to engineer the whole situation, so if it makes you feel any better you can blame me entirely. I was in need of a good fuck and you were in need of some sexual education. So until we each find an alternative source of pleasure then I suggest we just carry on enjoying what we've got."

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  • COMMENTS
3 Comments
engnr62engnr62about 2 years ago

I enjoyed the story but it ended way short would have liked to see her teach him more I feel that you may contnue if you added another chapter

trite_readertrite_readeralmost 10 years ago
Good Story,

Interesting premise, but terrible writing. Really, if you'd only just re-read your story before you posted it you'd see where you fucked up. Even in the first paragraph, which is a cardinal sin for any authors!

The Brit or Aussie colloquialisms were cute, but I can see how the yanks probably wouldn't get them. And the ending was atrocious, it almost felt as though you stopped the story mid sentence.

A little bit of effort could have turned this story into something top notch. I struggled to justify giving the tale three stars. It really was a two start effort...

quietman200quietman200almost 10 years ago
Nice but too short

This was a pretty nice story, but I wish you had carried it farther. It ended kind of abruptly when there was much more that could've been done with it. Your mechanics certainly need some work. You alternated at first between present and past tense, and the way you structure your dialogue needs attention. With those issues fixed, however, it would be more enjoyable still.

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