Fearless Phil

by realoldbill

Copyright© 2015 by realoldbill

Sex Story: A young man develops an amazing ability to please women, many women.

Caution: This Sex Story contains strong sexual content, including mt/ft   Consensual   First   Safe Sex   Oral Sex   Size   School   .

Philip was initiated into the world of women's needs and his own power when he was only fourteen. His young aunt discovered him abusing himself in the shower at the family's beach cottage one afternoon when she returned from sunning herself on the crowded shore. "My god," she said aloud when she saw his upright prong with his fist about it. "Don't waste that."

Quickly she peeled off her one-piece bathing suit and slithered into the curtained stall beside the blushing boy who stood frozen, rigid cock in hand. She gathered him to her ample bosom, kissed him firmly, grasped his young prick and brought its rearing head to her dripping vulva for she had nearly climaxed when she saw her nephew's swollen member which seemed wildly outsized for his slim body and which curved upward in a most amazing way. The fact that she had been fanaticizing a bit while out on the sand with her romance novel probably helped produce her antsy state and dripping sex. Their coupling was frantic and long-lasting.

Phil was an early-maturing adolescent, a virgin who had only discovered the pleasures of masturbation a few weeks before the end of eighth grade and was yet to show any signs of a beard. Now his happy penis, hard as a wooden chair leg, was buried in the folds of his lovely Aunt Joyce's warm body, and he had his arms about her waist and his head between her firm breasts. He humped and thrust, as she seemed to draw him deeper and deeper with her vaginal muscles, his mind completely blank but his hips in violent motion, faster and faster as she bent her knees, and he hunched his slim body into hers, listening to her gasp.

The young woman, married for several years to an inattentive slug, climaxed almost at once and bit her lower lip to keep from crying out as she pushed Phil back against the shower wall and felt his hands slipping down to her buttocks to pull her tightly to his hammering member and sparse pubic hair.

He seemed inexhaustible, unlike her husband who was seldom good for more than six or seven thrusts. Since she was using an oral contraceptive, she had no concerns about enjoying her young nephew who soon experienced his first orgasm in a woman as he spurted three times into his aunt's clinging depths, gasping with joy as he did so. The ejaculation barely slowed him.

Joyce wiggled off the boy's still jutting pole and turned about, putting her hands on the wall and bending at the waist. "Put it back in," she demanded, looking over she shoulder at the astonished young man behind her, his enormous cock in his hand, its head a blunt helmet that dripped sperm.

He did as he was told although it took him three tries before he found the right place and penetrated his young aunt again and then felt the frightening pleasure of slipping his hard member up into her vibrating body with all its wonderful spasms and quivers. He hit her g-spot on the way northward, and she shivered and cried out, scaring him briefly but only briefly. Then he rubbed it a hundred more times before she spasmed.

He tried to count his thrusts but lost track in the wild confusion of the moment, only knowing that it always took him longer to spew out his semen the second time. Joyce, satisfied and all but spent after perhaps a hundred rams of his youthful cock in less than two minutes, wiggled and tried to make him stop, but he held her hips and rutted on, determined to come, accelerating to marching pace of 120 in-and-outs a minute. He soon passed the one thousand mark, grunting and slapping them together.

Finally she turned on both handles of the shower full force and fell slowly to the tiled floor, begging him to cease. Phil followed her down to his knees, still ramming hard and deep and then exploded in her, emptying his balls in pleasure and filling her vagina until it oozed thick white goo. He fell on her arched back, sobbing with release, and then pushed himself free, his cock still long and firm., arching out, seeking more friction.

He helped the young woman up, raked back her hair, rose on his toes and kissed her gently, feeling very grown up, before he left her there under the pouring shower and found a towel, amazed at what had happened. His cock was still stiff but soon eased down and hung loosely between his legs, nearly a half-foot long in its flaccid state.

Back on the beach later that afternoon, Joyce spread the word of Phil's abilities to some of the other guests as well as friends from other cottages. Soon Phil found that he was seldom alone when he frolicked in the surf or swam between the waves, parallel to the beach. One blonde cousin soon attached herself to him, rubbing her small breasts on his arm as they chatted under a beach umbrella, then pulled a t-shirt over her tiny bikini and suggested they go back to the house for a Coke, leaving two other eager young women disappointed

The girl was fifteen, a quite experienced fifteen who had been sucking boys' cocks for a good while and who had given her maidenhead to her older brother the previous Christmas. Since then she had fucked a half-dozen high school boys and believed herself an expert on men, giving advice to many silly maidens on the art of seduction and pleasure. She was on the pill, and she climaxed on her fingers almost every morning while she washed her hair.

Once the cottage door closed behind them, and Jill was sure they were alone in the rented house, she grabbed Phil's hand and hauled him to a bedroom. "Let's do it," she cried happily.

"Do what?" Phil asked as he watched the blonde beauty yanked off her t-shirt and tossed away the top of her miniscule bathing suit.

Her reddish nipples stood out like cherries on her high, round boobs, and she quickly wiggled out of the bottom of her suit and smiled, "What are you waiting for, an engraved invitation?" Her pubic hair had been trimmed down to a tiny knot.

"Oh," said Phil, "Oh, I get it," and he pulled off his wet trunks and hopped up on the bed beside he wriggling girl who lay back, arms and legs wide spread as his outsized prong jumped up, ready for action, despite being cold and wet.

"Eat me first," she said, ignoring his needs. "I just love that."

Phil kissed her open mouth and blinked. "Do what?"

"Lick my pussy, silly, use your tongue. Come on," she said planting her feet and pulling the boy's head down between her wide spread knees, bending his cock double against the mattress.

Phil did his best, not enjoying it much, but following the girl's moaned directions and lapping at her vulva industriously. He discovered her tiny clit with the tip of his tongue and Jill melted, squealing and shivering.

The boy quickly rose and impaled her with his stiff prick before she could fully recover. Her eyes opened widely and her lips parted. "Ohmigawd," she cried and then she fainted and went completely limp under the thrusting boy.

Phil stopped, fully inserted in her tight love box and shook her at the shoulders. Her head lolled from side to side, and she moaned. He rolled over, holding the hundred pounds of girl to him and lay back, rather enjoying the feel of his long prod jumping and squirming deep inside a female vagina whether she knew it or not.

Soon the girl's eyes fluttered open, and she sighed and wiggled. Phil enjoyed that and held her slim butt, thrusting upward into her and holding his cock extended until it jerked and flexed.

"Oh," the girl said, wide-eyed and pushing herself up above the slim boy who was deeper in her vagina that any male had ever been. "Oh, what are you doing?" She tried to squirm away, pushing on his chest.

"Do you want to stop?" he asked, confused.

She nodded and made her pouting lips a thin line as she felt his ram recoil and then extend again, rubbing across a highly sensitive places on the front wall of her pussy and giving her a warm and interesting thrill. "Wait, wait," she sighed when she could speak. "Do that again."

Phil did and Jill squealed and wiggled back up on his body and clamped his slim hips between her knees. She pushed herself upright on his loins. His young cock felt as if it was rearing up to the bottom of her throat, and she began rising and falling on the staff pleasuring her as she sometimes did on her mother's dildo, bringing the boy's hands up to her breasts where her nipples were hard and erect.

This was a new and enjoyable experience for Phil, and he felt as if he could fuck the blonde forever in this position since she was doing almost all the work. But then she trembled and spasmed atop him, clasping his hard member firmly and crying out wordlessly like a trapped animal. She fell on his chest, blubbering, and for a moment he thought she had fainted again, but she kept moaning and writhing as his hard-headed cock surged and jumped within her.

'Stop, stop," she moaned, "haven't you had enough?"

"OK," Phil said, "I'm sorry. Did I hurt you?" He relaxed but his penis did not.

"No, no, it's all right," the girl moaned as she rolled to her back and Phil rolled with her right into the good old missionary position that he had read about so often. He kept his weight on his elbows and just let his body do what it wished.

What it wished was more sex, a lot more sex, and he began humping the spent girl beneath him, humping her hard and deeply despite the fact that she seemed barely conscious of what was happening.

Phil began thinking of his body as though it were an automobile or motorcycle, something with a series of speeds. He geared himself down to low in his mind, like he was going up a steep hill, and gave Jill a long series of slow and gentle rams, holding each one deeply in her for a second or two, enjoying the feel of the hard edge of his glans as it tore at the girl's pussy. He counted in his mind, working on his breathing, and when he had delivered an even hundred thrusts, he shifted gears and moved into second.

Jill screamed and thrashed beneath him as he began thrusting at once a second, banging them together roughly, bruising her mound and thighs. Deeper, deeper, deeper was his goal.

"Stop, stop, please stop," she squealed.

He jumped off of her, yanking out his happy cock with a squishy plop and lay back beside the girl, letting his slim rod flop on his belly.

"My god," sobbed the girl lying beside him. "That was awful." She rolled off the bed, found her bikini and her t-shirt and headed for the bathroom. Phil stroked his blood-hot member and felt at his swollen scrotum. That was interesting, he thought.

Late that evening as he lay nearly asleep out on the screened porch a ghostly figure appeared and sat beside him on the edge of the army cot that was his bed.

"Phil," said a soft female voice, "are you asleep." A small hand stroked his chest and slid down toward his belly.

"Uh," he said, reaching out his arm and slipping his hand along a smooth thigh to a firm butt.

"Will this thing hold both of us, this cot?" she asked.

"I don't know, probably."

"Do you want to try?"

"Sure. But..."

"But what, don't you like girls?'

"Uh huh, sure."

"Well, then?" The girl's seeking hand had moved across his sparse pubic hair and was grasping the root of his young cock. It jumped and quickly filled.

"Do you want to keep your shirt on?"

"It's all I'm wearing."

"I'm naked."

She pulled the big t-shirt over her head and dropped it beside the bed. "So am I."

"Have you done this before?"

"Uh huh," she sniffed, "a few times."

"You want to be on top?"

"OK. I've never done it that way."

Phil tossed back the sheet covering him and grasped his member so it stood upright. A faint bit of light came from a dim streetlight on the next corner, but it was enough for Phil to see the girl's smiling face and his jutting lance. It was oozing out some sort of liquid.

"Jean?" he asked.

"Yeah," she said, swinging a leg over the cot and swallowing as she looked at the skinny rod she was planning to mount.

"But you're going steady, I mean."

"Ah," she sighed as she screwed herself on his pole and wiggled to get all the way down, her hands on the boy's chest and her back arched. It was tearing and surging, merciless.

The cot squeaked and groaned a bit as they began, but soon their gasps and grunts covered up the bed's sounds and their bodies were quickly sweat slick and grinding together. Jean climaxed within minutes, squeezing Phil's striving yard like a gripping hand and then she relaxed. Phil held her at the hips and kept right on ramming upward into her slick vagina, now well into second gear. The girl began making odd sounds in her throat, little whimpers as her vagina liquefied and burned.

"Soon, soon," Phil told her as he changed his grip to her breasts and slipped into high, moving as fast as he could on his back and mounting his passion until he had to bite his lip keep to keep from screaming when he found relief and fired five blasts of his cum into the sobbing girl who was bucking on his young body, feeling nerveless and spent as her overfilled her cunt.

She lowered herself down on him and Phil moved sideways so they lay clamped together, nose-to-nose. His cock, still hard, jumped and quivered in her, needing more.

Jean licked her lips. "Enough?" she asked hopefully.

"OK," said Phil, "but I can do some more if you want."

"Uh uh," she said. "I've had plenty." She kissed him gently and pushed herself away, feeling his long rod slide from her, following by a thick stream of his spend.

Phil pulled up the sheet and put his hand in his groin, feeling his slick member and his hard balls. He exhaled and blinked as the porch door opened and another young woman appeared, wearing just a pajama top.

"Philly," she whispered, "it's May. Have you got room for me?"

"I don't think so," the boy say because he knew his cousin May was a big girl, probably 150 pounds or so, and he didn't think the cot would hold them both. He swung his legs over the side and patted the cot. "Come sit here."

The girl plunked herself down and the youngsters embraced and kissed several times, letting their tongues get acquainted, another new experience for Phil. Then he got to his knees between May's wide-spread legs, grasped her wide buttocks and drew their bodies together, letting his arched up member butt into her slit a time or two before it found her seldom-entered hole and jumped in. There was some resistance, but he popped into her quickly and filled her canal fully. His balls pressed painfully against the side board of the cot so he pulled the girl still closer and began to serve her, keeping his actions in what he thought of as low gear, slow and sure.

May wouldn't have it. "Harder, harder, more, more," she sobbed, feeling this youngster battering her cervix and knowing she was going to climax almost immediately.

Phil gritted his teeth and went into overdrive, ignoring the fact that his balls were being rubbed sore and that the girl's big breasts were boring holes in his chest. May covered her mouth with both hands, leaned back and let her orgasm roll through her like tidal wave, making her see bright lights before her eyes and feel as if her vagina had exploded.

"Oh, oh," she sobbed, hugging Phil and then pushing him away despite the fact that she was well aware that he was long, hard and in need. "Sit up here," she gasped, getting down on her knees.

Phil did as he was told and his cock disappeared into May's mouth. He buried his hands in her curls and relaxed as May gave him her super deluxe blowjob and finished him off by sucking his balls. She vanished indoors and Phil fell back on his cot and was almost instantly asleep.

And so it went that summer with Phil getting laid almost daily and by the time the family's two weeks at the beach was over, he was a most experienced young man with coterie of admiring females. His parents were mystified. His cock was sore.

Phil turned fifteen shortly after school began that fall, entered his sophomore year and began attracting female attention after two of his summer bed-partners spread the word of his equipment and competence. Almost every weekend Phil was out on both Friday and Saturday nights and seldom did he come home without dipping his wick in some young honeypot, or in several cases, more than one.

Browsing the Internet and looking for ways to increase his abilities or his size, Phil came upon a site describing Kegel exercises for men. He had heard something about that name and the things that some girls did to get more pleasure from sex, but he had never heard of men doing cock exercises.

Since he was proud of his developing penis, which he was sure was becoming thicker if not longer, and its abilities as well as pleasantly surprised by his success with girls, almost all of them older than he was, he read the text on the screen carefully and then headed for the bathroom.

As he pissed, seated as instructed, he managed to stop his flow three times for a few seconds each time and thought about what muscle it was that was accomplishing that feat. He put his fingers behind his ball sac and tensed that muscle. He could feel it contract and his cock jumped.

The Internet sex site called it the PC muscle, which he thought was kind of funny, since he found it on his PC. He began following a regimen of PC exercise, doing sets of ten several times each day and then doing five or six sets when he lay down to sleep, his cock jerking happily up and down. He found that he did not have to tense his ass to do the exercises and soon he was doing them longer and somehow deeper and began working on his abdominal muscles as well as those that controlled his cock's thrusting and pumping movements.

Within a month Phil was multi-orgasmic. He could bring himself to the peak of excitement with his hand, feel his jism began to surge, even see the first pearly sign of cum on the tip of his cock and then quickly squeeze down his PC muscle and stop the flow of semen without losing the pleasure of the moment. Then he could bring himself up again with gentle strokes, stop the need to ejaculate once more and repeat the process over and over for nearly half an hour.

The first time he accomplished this feat and let himself come on the third climax, he shot his jism from one side of the shower to the other, hitting the wall almost five feet up. He was amazed. Phil also began doing lifts with his cock, starting with a wet washcloth and increasing until he could lift a five-pound weight six inches. His belly was soon rock hard and his abdominal muscles well defined.

Early in December Phil's already impressive reputation as a woman pleaser got a significant boost when his family and some friends went skiing one weekend. The "children" as the elders called them were relegated to one small room and sleeping bags while their parents had beds and cots. As it turned out, Phil was the only boy after one college freshman said he had a paper to finish and a high school junior had made the basketball team and reneged. So there young Phil was, bedded down in a cozy room with a luscious and horny eighteen-year old, two girls of sixteen, both of whom he had enjoyed at the beach, and a pair of luscious middle school twins, friends of one of the families.

"Now you girls leave Phil alone unless he snores," his mother said as she turned off the light and closed the door at about ten the first evening in the mountains.

"Phil," said the oldest girl after a few quiet minutes, "why don't you come over here."

"Geeze," he said, feeling his cock begin to fill. "You know that door doesn't lock."

"We can be very quiet," she said as he brought himself and his sleeping bag to her side. "Molly told me you were awful good in bed." She unzipped her bag and reached for the boy.

Soon two naked young people were in the girl's bag, and Phil's rigid cock was buried in the high-schooler's tight and quivering quim. She lay back gritting her teeth and squeezing her eyes closed, willing herself to breathe as Phil moved in and out of her in low gear, quietly humming to himself and kissing her lips and tits once in a while. She felt as though she were being split.

The girl came before he shifted gears, pressing her sucking mouth to his chest and spasming over and over as her vagina turned to fire around the driving post in her gut. Phil shivered with delight as she quivered about him, but then was disappointed when she pushed him away and sobbed, "Enough, enough."

"Milly," the boy whispered, holding back his rising need, "where are you?"

A hand reached out and grabbed his arm. He rolled over and found himself between a pair of long legs with a slim-fingered hand about his prod and within ten seconds he was balls-deep in another girl and well into second gear with her tongue in his mouth. "Milly?" he asked, arching up in the dark.

"No," she gasped, "I'm Madison, and my god but you feel good."

They rutted steadily for a few minutes, lost in each other, unaware of the other girls listening to their bodies slapping together. "You about there?" Phil asked her.

"Ah, ah," she gasped nodding.

'Wait 'til you feel this," he said, humping hard and getting ready to display his ability to climax three times in short order. The girl came, mewling and shuddering as Phil reached his first point of ejaculation and clamped down hard with his PC muscle, willing his cock and balls to relax just before they were ready to spurt. He had learned from experience that he had to be quick.

The girl moaned and sobbed as he kept right on thrusting into her sodden quim, once again in low gear, and then she felt him accelerate and come again, but somehow, he did not fill her, just paused briefly, shivering, and then once more trip hammered into her with his huge rod, pounding away fiercely.

"Please, please, " she sobbed feeling her own body about to explode as Phil once more moved his prick into very rapid thrusts, relaxed his muscles and ejaculated, blasting the girl with four thick ropes of spend that squeezed out of her ravaged pussy as Phil continued to piston into her.

"How was that?" he asked her.

"Awful, terrible, I thought you were going to tear me apart."

"Isn't that neat?" Phil made his cock lift and jerk.

"No, no," she sobbed, relaxing. "Can you do it again?"

"I don't know," he said, aware that he had not fully softened despite his mighty ejaculation. "I can try."

"Oh yes, yes," she gasped, wrapping her legs about his warm body.

"Come on," said a voice in Phil's ear. "It's my turn."

"Milly?" asked Phil, as he drove a half-foot of rigid flesh into 16-year-old Madison's lush body

"I'm dying," Milly said. "Hurry, hurry."

'Go on," Madison said with sniff. "Do her, then you can come back to me." She unwrapped her legs, and Phil climbed over to the girl who awaited him with open arms and legs. He was in her at once, finding her more than ready to mate, hot and wet.

"Oh, oh, oh," Milly gasped as she came immediately.

"I found out I can do something really cool," Phil said a few minutes later as they ground together in coital excess.

"I was fingering myself," Milly admitted, "listening to you two. How many time did you do it?"

"Just once, honest, but wait a minute, and I'll show you what I can do."

Phil mentally shifted out of second and began full speed thrusting into Milly's oft-used quim. "OK," he said, trying to control his breathing, "here comes the first one." He held his cock fully extended and felt the semen gushing through his rock-hard balls and clamped down his practiced muscle and stopped the flow, sighing with relief as his prick shuddered.

Then he accelerated again, feeling the girl begin to meet his efforts, rose to a second peak in about three minutes and might have pumped out an ounce of pre-cum before he clamped the muscle down and then flexed his cock, laughing softly with pride.

"Oh god, god, god," Milly moaned as she neared another climax. Phil got back to work, brought her to a gasping orgasm and jolting spasm with her body rigid and then held back for the third time, clamping down extra hard.

"How can you do that?" Milly asked when she could speak and Phil was once more making, long and gentle trusts into her weary body. 'How can you?"

"It's easy," Phil said, accelerating once more, gritting his teeth as he sought his delayed relief and then fired his long cannon into Milly over and over.

She squealed loudly.

Phil scurried away, dragging his bedroll with him and rolled up with his back to the door which popped open, flooding the room with light.

"She kicked me," Milly said.

"Oh," said the woman at the door, looking around. "Well, go to sleep now."

A flashlight flicked to life as soon as the door closed. "Come over here, Phil," said one of the twins sweetly. "We want to see it."

For the next few minutes Phil showed the twins how he could make his cock jump up and then lie down, and he let them put their hands on his shaft, all four of their little hands on his rearing member, stroking and palming the blunt head.

"Oh, it's so soft and smooth," said one soft voice.

"But it's so hard," said the other.

"And hot," said the first.

Phil practiced restraint, flexing his PC muscle and his abs and enjoying himself.


"Phil," said Melissa with a friendly smile as she cornered him near the lockers a month or so later, "will you take me to the dance. Joe and I broke up, and I've got a new dress and everything."

"Sure," the boy said to one the school's hottest juniors who had been a homecoming princess that fall. "But I'm not much of a dancer."

"That's OK. I just want to make him suffer. You don't mind do you?" She edged closer so her high young boobs were right in Phil's face. "We can double date if you want since you don't have a car."

Phil nodded, trying to keep from developing a hard-on right there in the school hall.

So that Saturday evening he walked over to Melissa's upscale home wearing his good suit and well-polished shoes and a silk necktie borrowed from his father's rack. Melissa made him wait and then glided down the steps and held his arm so her mother could take some flash pictures.

Phil was speechless. The girl's dress was low cut and strapless and pretty short, barely clinging to the underside of her round melons in a series of tiny gathers and made decent by a bit of tulle springing above her fine chest like fern leaves. In her heels, she was an inch or so taller than Phil.

"Tommy's coming to pick us up," she said, squeezing his arm to her right boob so that it popped up and displayed her lacy half bra and the top of her areole. Phil wondered what kept the dress up and guessed she used some sort of glue. He helped her into a knitted shawl.

At the dance, Melissa was the belle of the ball and hardly ever paused as she swung about the floor with a series of young and eager men leaving Phil, the only 10th grader he could see, sipping his Coke and wondering why he had come. He had to admit he enjoyed watching the girl dance since her gyrations bared so much of her skin and most of the juniors just ignored him. At about eleven, Melissa pulled him up and dragged him out on the floor for the last dance, a slow one during which she put her head on his shoulder and mashed her firm breasts to his chest.

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