The Life and CFNM Times of Herbert Smith Ch. 01

(Author's Note: The idea for this story was suggested to me by my number one fan, Kevin, a great guy with the most unique imagination. I hope all my readers enjoy this story as much as I have enjoyed writing it!)

Chapter 1

The Smith family had lived in Point Lookout, North Carolina a good long time. Some residents can attest that the family had settled there just after the Revolutionary War. However, the Point Lookout Chamber of Commerce has a record on file of one "Smythe" family "newly arrived from Manchester, England," on February 24th, 1757, passengers on the British frigate Dulcimer, which landed at Point Lookout on the southern coast of North Carolina during an exceptionally heavy winter storm. John Smythe and his wife Abigail, who was five months pregnant at the time, were seeking a chance at a new life. Somewhere far from their squalid and increasingly debilitating existence lied a land of boundless opportunities, where a man might make his fortune. This new land, this New World, too abundant in promise to ignore, beckoned incessantly until both he and his wife could no longer sanction keeping their feet on English soil. And so they left, with only their courage and Abigail's modest dowry in their possession when they finally set foot on the shore of icy Point Lookout.

John's cousin James Smythe and his wife had settled in Point Lookout two years earlier. It was here that John and Abigail lived while their house was being built, only a few miles from his cousin's farmstead. Abigail's dowry was enough to purchase a twenty-acre plot of rich, fertile farmland upon which the house was to be built, and in less than a month the small, four-room cabin became the couple's new home.

John and Abigail worked hard over the years at making their farm a success, using slaves to perform the difficult labor of picking cotton. As a result, by the time the War of Independence broke out, they were one of the preeminent producers of cotton in all of North Carolina, making enough money to hire dozens of slaves to work the fields.

It was no secret to Abigail that her husband had a keen eye for pretty black girls, and she caught him on more than one occasion exposing himself to one or several of them while they picked cotton. She never said anything to him about it because his fascination with the girls never went beyond him masturbating in front of them. She thought it a most peculiar fetish, but a harmless one, and so she remained silent. But for John, the daily romps in the cotton fields were enervating. He loved jerking himself off in front of the giggling girls, who seemed to really enjoy watching his huge prick fire off gigantic volleys of cum high into the air. But the one thing they loved the most was the size of his member—at full mast, an impressive 13 inches in length. Huge penises seemed to be a hereditary trait in the Smythe family.

As the Revolutionary War raged on, John's cousin James decided to quit the rebellion and take sides with the British. James' Tory sentiments did not sit well with John and Abigail, and as a result, the cousins became ostracized, with John finally making it known that he wanted nothing more to do with the Tory sympathizers. In January of 1774 John officially had his surname changed to the more commonplace "Smith," forever disassociating himself from his cousin, and declaring to all that there was no doubt of where his allegiance lied.

The Smith family business became very wealthy and prosperous in the years following the Revolution, and was the major supplier of clothing for Confederate troops during the Civil War. When machines finally replaced slave labor the business prospered even more, ultimately becoming North Carolina's most prestigious producer of cotton goods. This success continued well into the twentieth century until the Great Depression forced a halt to the family's continued good fortune. By that time the company's stocks had dwindled and most of the family properties had to be auctioned off. However, the Smith General Store, which was started as an ancillary and modest enterprise, continued to be successful, and this success allowed the family to build several more stores in and around Point Lookout. During succeeding generations, a multi-mega corporation bought out the company, with the Smith family retaining 51 percent share of the company's holdings. The Smith family—rich, powerful, and with an eye to the future—seemed to have it made.

Herbert Smith, the latest incarnation of the quirky, fetishistic male line, was born on July 4, 1991. His mother, Helen, had died several years earlier in a boating accident, leaving his father Michael heartbroken. At 18, he was the youngest of three brothers, the other two, Frederick and William, being 20 and 22 years old, respectively. Herbert was the complete antithesis of his two older brothers. Gawky and bookish, and the shortest in stature at 5' 7", he had none of his sibling's fascination with cars, sports, and fast living. Although he did share Frederick and William's passion for the opposite sex, he was always awkward around girls, lacking confidence in himself and therefore unable to form any real attachments. It wasn't as though girls didn't find him attractive—they did. In fact, he was the most handsome of all the brothers, but unlike his gregarious and extroverted counterparts, he found his comfort in music and books, eschewing parties and almost all types of social gatherings where he might become the focus of attention.

But beyond the more apparent reasons for Herbert's semi-withdrawal from the world lie another vastly important consideration—one which was as much a part of his psychological makeup as it was a fact of anatomy: Herbert had a 15-inch penis. This abnormality was a daily reminder to the boy that the tube of flesh that hung between his legs would forever preclude him from having a normal sexual life and, even worse, make him the laughingstock of any females unfortunate enough to lay their eyes on it. His mother was the only woman ever to have seen his penis erect. And that was by accident. Helen Smith was a woman of 44 years of age. A tall, slender, brunette beauty, she was a kind and loving woman, but tended to have a stern personality. She warned her son that such a penis would prove problematical in his relationships with girls and that he should never expect any girl to become involved with him without him fully disclosing the truth about his "freak of nature". If there was any overarching reason why Herbert had become dysfunctional around girls, it was his mother's use of the word "freak" that most inculcated his young mind towards sociopathy. His brothers frequently kidded him about his "size," but such frivolity was usually reserved for when the three of them were alone. That they were circumspect about his condition did much to alleviate his anxieties, but his insecurities could not be assuaged. He knew his penis would always be a problem, and it would be so for the rest of his life. His mother may have died, but the legacy she left her son was not a healthy one.

Herbert's father was a man whose business took him to all parts of the globe. He was the CEO of Smith Industries, a company that had grown from its modest beginnings as a clothing manufacturer to producing a vast array of correlated goods, such as thermal clothing, heat-retardant flight suits, and protective underwater gear capable of withstanding enormous pressures. Michael himself had invented some of these types of apparatus and held over one hundred various patents. After Helen died, he threw himself into his work, taking on more and more assignments that often forced him to spend a great deal of time overseas. However, it was during one of the increasingly rare occasions when he found himself home that he had the good fortune to meet and fall in love with a beautiful woman attorney whose family lived in Raleigh, and had a similarly respected lineage as his own. Her name was Constance Ainsworth and she was a divorced mother of three young girls: Fiona, Lillian, and Amy, who were 21, 19, and 18, respectively. All three girls were blonde, like their mother, and each one just as beautiful. Herbert remembered the first time he had met Constance and her daughters. It was a month before the marriage ceremony and he was overcome with his soon-to-be stepmother's great beauty and charm. She reminded him a lot of Helen—tall, aristocratic, and proud, but without the sternness that prevailed in his mother's behavior. Constance was all fun and spontaneity—something the Smith household desperately needed. So it was with no small sense of gratitude that Herbert and his brothers welcomed their new stepmother and her equally intriguing daughters into their home.

Helen had taught her three sons to be courteous and deferential when it came to women. She demanded obedience and respect from the boys, and they gave it to her unconditionally. It was by sheer force of her personality that she retained such control over them, and it was not always easy to do so, especially once they reached their preteen years. But her perseverance in this respect paid off handsomely: she had raised three civilized young men of whom she could be proud.

Despite those rare occasions when the boys misbehaved, she never had to employ corporal punishment. This was left to Michael, if it was at all deemed necessary, which it rarely was. Helen thought that a system of rewards was far more effective than the strap, and that praise and encouragement were superior forms of conditioning than abusive words or behavior. In this she was proven correct, because each of the boys, and in particular Herbert, was always polite and respectful to everyone, especially any females with whom they may come into contact. Friends, family, and visitors to the home would often remark how well behaved and courteous all three boys were, and this had made Helen very happy indeed.

Immediately following the marriage, Constance and her daughters moved into the Smith estate. During the first few weeks she and the girls slowly became acclimated to their new, and far more luxurious, surroundings. She and her husband had divorced five years earlier, and she had raised the children on her own. The girls themselves were models of perfection; tall, graceful, and beautiful, their similar physiognomies offset by a dissimilarity in temperament that was more a matter of degree than of kind, which is to say that although each of them were possessed of a willful and determined nature, their likes and dislikes varied greatly. In the months to come, Herbert and his brothers were to experience firsthand just how willful and determined these girls really were.

Herbert's indoctrination into the world of CFNM fetishism began in a most unexpected way. One day he had been sitting by the pool in the backyard when Amy came casually waltzing by with a glass of lemonade in her hands. He had never seen the girl in a bikini before and it gave him quite a jolt. Although she had celebrated her eighteenth birthday only a few weeks before, her body retained nothing of the girlish baby fat so common in girls her age. Her high cheekbones, pouting lips, and large, liquid blue eyes, coupled with her tiny waist, long, shimmering blonde hair, and graceful, athletic legs, combined to form an essence of womanly loveliness that served as an immediate aphrodisiac to the insecure young boy. He watched her intently as she placed her glass on the table and then sat down a short distance away from him, thrusting her luscious limbs in front of her to catch the sun's rays. He was absorbed by her lithe, cat-like movements, so emblematic of the trait shared by her mother and sisters. For a while she said nothing, content to simply close her eyes and raise her head up toward the sun.

The simple fact that such a goddess was sitting within arms reach would be enough to drive any man to distraction. But in Herbert's case, her presence enjoined a much more vivid response: he got a huge hard on.

He didn't mean for it to happen, but it seemed his penis had a mind of its own. Slowly he felt the huge monster within his bathing suit start to grow, and the only thing he could do was to throw his towel over his lap to conceal it. Thankfully, Amy's eyes were still closed, but he could not stop staring at her even though he knew that in doing so he would only exacerbate his problem.

She was indeed beautiful. For the nearly two months that Constance and her children had lived in the Smith home, he had observed mother and daughters closely (as he knew his brothers had also done), finding them congenial and kind, although somewhat elusive and even, at times, distant. The girls, especially Fiona and Lillian, seemed to have more in common with Frederick and William and spent more time with them than they did with him. But Amy seemed to genuinely like Herbert and often sought out his company. Herbert thought this was due to them being both the same age, but it was also because Herbert actually listened to what Amy had to say, unlike her older sisters and his brothers who saw her simply as someone who was too young to be taken seriously.

Now, as she sat before him in all her resplendent glory, drinking in the sunlight as if it were some rare form of rejuvenating tonic, he tried to forget that she was his stepsister and imagined himself licking the underside of her dainty little feet, absorbing each pretty toe within his mouth one by one and lavishing his utmost attention upon them. He knew he shouldn't be thinking of her in such a vulgar way, but it was the very idea that he could think such sinful thoughts that made his libidinous imaginings so utterly enthralling. As he sat there contemplating how wonderful it would be to lick and suck those delicious, inviting toes, Amy opened her eyes and caught him staring down at her feet.

"Is there a bug on me?" she asked, drawing both of her legs back.

"No," Herbert replied, annoyed at himself for having been caught staring.

Amy smiled wryly. "Then what were you looking at?"

"Nothing."

Herbert knew Amy was no fool. In fact, she was far more astute and intuitive than either of her sisters. This was one quality she shared in abundance with her mother.

"Nothing…right." Amy took a sip of lemonade and once more extended her legs in front of her. She then reached for a tube of sunscreen and held it toward Herbert. "Well? Would you like to do the honors?"

She had never asked him to do anything for her, let alone touch her body. He felt thrilled at the idea of running his hands over her legs, but he paused nervously, knowing that he couldn't stand up without revealing his erection. The opportunity to actually make physical contact with this beautiful girl was overwhelming, but his sense of shame was more powerful still.

"I'd like to but I can't right now," he said.

She looked him straight in the eyes, the edges of her mouth lowering into a frown. "What do you mean, you can't? Or don't you want to be bothered?"

He felt her gaze cut right into his soul. "No, it's not that. I really can't. That's all."

For a few moments she simply looked at him, pondering his vague expression. Then she burst into laughter. "Oh, now I get it! This has to do with us being a family—it's the stepbrother/stepsister thing, right?"

Herbert jumped at her incorrect conclusion. "It would make me feel uncomfortable."

"You know, we're not related by blood, Herbert. So you really shouldn't feel uncomfortable at all."

"I guess so," he replied, feeling foolish.

"So, come on," she said, holding the tube of cream in front of him once more. "Do your 'sister' a favor."

She said this with such delightful coyness that Herbert couldn't refuse. Thinking quickly, he moved his chair toward her without having to stand up. With only a few moves, he had positioned himself so that he was directly facing her. "Okay, put your legs up."

Amy happily complied, raising one leg, then the other onto Herbert's bony knees. She then thrust the sunscreen into his hand. "Get to work, brother!"

He took the tube from her and drew out a large blob of cream onto his palm. He then rubbed his hands together briskly and began to apply the sunscreen to her right foot. As soon as he made contact with her skin he felt his penis expand to new heights.

"Mmm…"she said, contentedly. "That feels nice."

"You have great skin," he said, feeling the need to compliment her.

Amy watched him rub the lotion over and in between her toes. "You think so? I always thought my skin was kind of dry."

"I don't think so," he said, concentrating on the area just above her ankle.

Amy studied his handsome face and smiled. She loved being appreciated—especially when that appreciation was shown by boys.

Herbert's prick was now at full mast. Heavy with semen from not having ejaculated for over a week, he knew that it wouldn't take much to get him off. If Amy even moved her foot so much as an inch or two toward his erection, he might lose control and cum right there in his bathing suit. He had to focus his mind on other things.

"You know my dad is going away for three months, don't you?" he said.

"I know. Mom told me."

"He'll be in England most of the time, and then he's going to Germany, France, and Italy. I wish I could go with him."

"I'd love to go to Europe," she said, as she watched Herbert apply lotion to her other leg. "I think the Europeans are much more civilized than we are."

Herbert laughed. "I think you make a good point."

As he continued to assiduously concentrate his efforts on the young girl's graceful limbs, the towel, which had previously been his only source of protection from her penetrating gaze, had fallen onto the patio floor. Suddenly he was gripped with fear.

Looking down at the towel and then at Amy, he realized his secret was out. Bad enough that he had an erection at all, but the size of his penis, now unabashedly revealed through the fabric of his tight-fitting bathing suit, made her gasp with disbelief.

"Oh, my God!" she cried. "Please don't tell me that thing is real!"

The abomination he had managed to successfully conceal from all the females in the household for the past two months was now exposed. Herbert hurriedly reached for the towel and placed it in his lap. He felt like his penis had betrayed him. "I'm sorry. I'm so sorry," he repeated over and over again. He held the towel in front of him and removed her legs from his knees. Rising to his feet he apologized profusely to the startled young girl.

Amy's expression changed abruptly from one of incredulity to one of amused curiosity. "It's okay. It's okay," she said, trying to calm him down. "I know all about it. I just didn't really believe…"

"You know about me?" asked Herbert, his voice full of agitation.

"It's kind of like, common knowledge, you know."

He swallowed hard. "Common knowledge! Are you kidding me?"

"I thought you knew."

"I can't believe this! It was Frederick and William, right? They had to go and open their big mouths! God forbid those guys should ever keep a fucking secret!"

"It wasn't them," she said calmly.

"Then who told you? Who was it?"

She paused before answering, hoping the delay might lessen the blow. "My mother told me—and my sisters."

Herbert looked at her in disbelief. "Your mother?"

"Your father told her and she told us."

Herbert's erection had disappeared, deflated, just like his ego. "My old man. I don't believe it. Why would he do that to me?"

"Don't be too hard on him, Herbert. My mother caught you once in your room masturbating. Your door wasn't locked and she thought you were out. She asked your father about you and he told her. She has a way of getting what she wants."