The Life and CFNM Times of Herbert Smith Ch. 02

"Oh," she said almost breathless. "That was very satisfying indeed!"

Herbert didn't think so. "For you, maybe," he replied as he stood up and rubbed his butt cheeks. "You really know how to hurt a guy."

"Well, that's what you get for not being honest with me. Now you know better."

She told Herbert to resume his seat while she got her personal effects together.

"We're going downstairs," she said, still clutching the yardstick in her left hand while in her right hand she held her pocketbook and coat. "There's a little room in the basement that no one ever uses and I made a copy of the key. Let's go!"

Without a word, Herbert did as he was told. His heart was beating wildly at the thought of participating in whatever sexual games his beautiful teacher had in mind. He followed her down a flight of stairs to the lower level of the building. By this time everyone had gone home and only the janitor was left on duty. He was performing his usual routine of sleeping half the evening away while watching television in the guidance teacher's room. Iris was no fool. She could not afford to be.

"I'm dying to measure that penis of yours," she said to him as she put the key in the lock. "That's why I took the yardstick!"

She laughed quietly to herself as they passed into the room. It was a small affair, about 20' x 12' and furnished with only a few chairs and a small circular table. In one corner stood a bunch of cardboard boxes containing textbooks. There was a musty smell to the room but it was not offensive. Overhead was a single light bulb, but the light from the small window behind them offered plenty of illumination.

"What are we going to do?" Herbert asked her, as she put her hands on his belt.

"First, I'd like to measure your dick," she said, rubbing her right hand all over his still erect penis. "Then I'm going to give you a handjob."

Herbert felt his heart skip a beat. His English teacher, this incomparably beautiful woman who only minutes earlier was to him the paragon of womanly virtue, was now acting with the same willful lusts of his stepmother and stepsisters. He could scarcely believe that her demure bearing really harbored the soul of a sexual provocateur. Yet here she was, standing before him now fully clothed, gingerly removing the belt that held his pants up and laughing to herself all the while. It was happening so fast that he really had no time to decide whether what he was doing was immoral or not. But once she had pulled down his underwear and his huge dick was exposed, he really didn't care.

"Holy Jesus!" Iris cried. "That's the biggest schlong I've ever seen!"

She gently slapped his turgid penis back and forth, amusing herself with the way it bobbed from side to side under her touch.

"My mother, my real mother, told me that I would never get a woman to have sex with me because of my dick," Herbert admitted. "But my stepsister, Amy, she helped me to get over that."

"Really? How did she do that?"

Again, Iris forced his prick to rollick from side to side by gently hitting it with her hand, enjoying the tactile sensation of running her fingers along the taught flesh.

"By letting me jack off in front of her."

Iris laughed. "She sounds like a very intelligent and mature woman."

"Well, actually, she's only 18 years old."

"As I said, an intelligent and mature woman. So, she appreciates your cock, does she?"

As she said this, the lovely woman examined his scrotum and found his balls to be heavy with sperm.

"I guess so."

"What about other girls your age? Have you ever gone out with any of them? You know, like on a date?"

"I dated a couple of girls, but most of them are afraid of my cock so they stay away."

"Interesting," Iris said. "You'd think most girls your age would be mature enough to accept you as you are."

"Not when you're carrying around this monstrosity," he replied, fingering his dick. "You see how some of them treat me in school."

She ran her long and delicate fingers over the length of his prick. "Yes, I know. But I happen to like your monstrosity. Now take off all of your clothes and let me measure you."

Herbert did as he was instructed, anxious to please the young woman.

She watched him intently as he disrobed, appreciating the tanned, muscular young body, his cock jutting out before him like a huge kielbasa sausage just begging to be manhandled.

He now stood before her completely nude and unashamed. If it had not been for Amy's acceptance of him, he doubted that he would ever have gone this far, and certainly not with his own teacher! He let her hands roam all over his body, the thrill of her touch exciting him in ways he could not describe. It was one thing to fantasize about such a beautiful woman while she was engaged in her usual duties as a teacher; it was quite another to accept the overwhelming physical reality of her immediate presence—he naked, and at her mercy, she in total control.

"Okay," she said, reaching for the yardstick. "Let's see how big you are."

"I think you'll be surprised," he said, anticipating her reaction.

"Oh, don't tell me. You've already measured yourself, haven't you?"

"Sorry."

She looked suddenly disappointed. "Well, don't say a word. I want to find out for myself."

She deftly maneuvered the yardstick under his penis so that one end touched the base of the shaft where it met the scrotum. Her face was only inches away from his imposing tool.

"Okay, let's see what we have here," she said as she lifted the tip of his penis to place the yardstick directly underneath the head.

Herbert hoped she wouldn't fondle his cock any more than she had to, otherwise he felt that he might orgasm then and there.

She let out a loud whistle. "I don't think there is anything like this in the Guinness Book of World Records! It's goddamn huge!"

Herbert chuckled to himself. "Are you satisfied?"

"Fifteen fucking inches! Fifteen!"

"I warned you."

"And the balls! They're enormous too! God, what a package!"

Iris removed the ruler and took a seat next to him. She was in complete awe over the towering megalith that bobbed proudly in front of her face. It astounded her that, unlike most well-endowed men she had known over the years, Herbert's erect penis defiantly refused to succumb to the effects of gravity, stubbornly maintaining a consistent 45-degree angle to the floor. She noticed that his penis was uniform in shape and skin color, angling straight out without that odd curve that she found disagreeable in some men's penises and totally exempt from any blemishes or other various anomalies. She had never seen a cock so lovely. "Why don't you sit down for a moment and tell me about your new family while I play with your prick."

"Okay," Herbert said as he reached for a chair. He positioned it so that he was directly facing her, giving her immediate and unhampered access to his genitals. "How's this?"

"Fine," she replied. "Now go ahead and start talking. I want to know all about this CFNM household of yours."

As her hands glided gently up and down his shaft, Herbert found it difficult to not concentrate upon the first-class handjob he was receiving. But Iris kept him under total control by periodically and abruptly ceasing stimulation of his penis, thereby forcing him to gather his thoughts. By utilizing this stop and go method, she was not only helping to prepare him for a monstrous orgasm, she was able to learn much about his family life and, especially, the woman who was in control. "Tell me about your stepmother," she inquired, giving him a half a dozen rapid tugs. "Is she nice or is she a bitch?"

"Nice," he replied, taking in several deep breaths. "But she can also be very demanding at times."

"Really? How so?"

He watched as her left hand cupped his nut sack while her right hand consistently beat him off. For a few moments he lost his train of thought, so engrossed was he in observing her.

"I'm going to stop if you don't answer me," Iris warned him.

"Oh, uh…well she insists that we, me and my two brothers I mean, walk around the house naked."

She laughed loudly. "Oh, that's just lovely! Even when company is there too?"

"Sometimes. But only if it's all women."

"I love it!" she exclaimed. "And do you and your brothers enjoy walking around nude?"

"At first it was kind of weird but we got used to it."

"And how long has this been going on?"

"For about six months now. Ever since my dad left for Europe."

"And your father approves of this?"

Herbert laughed. "Are you kidding? My father is like her obedient servant. He does anything he can to please her."

Iris began to stroke him harder, curious to see how long he would hold out. "Her obedient servant, huh? So, in effect, she is the mistress of the household?"

"Yup. She's the boss."

She noticed that Herbert's prick was now producing quite an amount of pre-cum and that his huge balls had become very taught. It was only a matter of minutes now, maybe less.

"Tell me about the CFNM stuff. Do you have parties?"

"We've had a few. In fact, Constance, that's my stepmother's name, is having a really big Halloween party in a few months with lots of strippers. It's going to be insane."

The thought of attending a CFNM party was something Iris had dreamed of for a long time. And now that the opportunity had presented itself to her quite unexpectedly, she was not going to let it escape.

"I've never been to a CFNM party myself," she said, as her fist flew up and down his pole with increasing speed. "I would really like to go to one."

"I…I can have you meet my stepmother if you want," Herbert replied, feeling the cum rise up in his shaft. "I'm sure she would love it if you came."

"I'll bet she would," Iris said, sensing his prick was ready to erupt. "What are your parties like? Tell me about it."

There was no stopping now. She was anxious to watch him cream all over her hands but she wanted his ejaculation to coincide with some libidinous thought, some really vulgar memory that would serve to coax out the boiling sperm within. "So?" she asked again. "Do you masturbate for your stepmother, for your stepsisters… for all the women?"

"Yes!" he blurted out. "Me and my brothers jerk off all the time in front of them. Last weekend all three of us shot our cum into a punch bowl."

Iris giggled at the thought of the three boys filling the bowl with sperm while an audience of women watched the whole spectacle with amusement.

"I hope you got it all in the bowl," she quipped, as she felt his penis twitch.

"Most of it," he rasped, as he threw his head back in ecstasy. "Some of it…landed in her hair."

"Whose hair?" she asked as she squeezed his balls hard with one hand while her other hand pulled on him savagely.

"Mrs. Waterson!" he screamed.

Iris almost stopped stroking his cock at the mention of the woman's name. "Alice Waterson? Our principal?"

"Yes!"

This realization came as a shock to Iris, but seeing that Herbert was now on the verge of orgasm, she tightened her grip on his penis and stroked him for all she was worth. Within seconds he was rocking his body back and forth, fucking her fist as hard as he could. "I want to see you shoot a geyser, Herbert! Give it to me!"

The hot, milky seed erupted joyously from his tortured shaft, spurting high up into the air over Iris's head and splashing into the cardboard boxes beyond. She laughed as the next several volleys also flew completely over her head, leaving not a trace of sperm on her body. However, the next several eruptions did not travel as far, finding their mark on her breasts and neck, with one creamy salvo even finding its way into the luxurious folds of her lustrous red mane. His orgasm was a long one, lasting well over a full minute, the ropes of semen furiously being spit out every time she administered an upward pull on his shaft, culminating at last in what she could only describe as a string of multiple ejaculations, which turned the lower part of her body into a vast puddle of sperm. She sat there looking down upon the reservoir of cum, amazed at the sight.

"My God!" she cried. "What an unbelievable fucking load!"

Herbert was barely able to catch his breath and had to sit down. His prick was still dripping copious amount of sperm. "I think…I think it's because…you're so beautiful," he said breathing hard. "Beautiful women always make me cum like that."

Iris didn't know what to say at first. She was still wondering how she was going to clean up the mess on her skirt. "I'm going to have to take this off," she told him. "Jesus! I've never seen a guy cum so much! It's really incredible!"

Herbert sat there breathing fast, trying to regain his composure. He felt bad that he had ruined his teacher's dress, but there was nothing he could do. "I'm…really sorry," he said, apologizing profusely. "I got so carried away…I should have warned you that I cum like a horse."

Carefully removing her skirt, she then put on her coat and sat down again. "I like that you cum like a horse," she admitted frankly. "I've always been fascinated when guys cum like that. I find it very sexy."

"But I should have warned you."

"It's okay, Herbert. I really don't mind. But what I want to know is…what's the deal with Mrs. Waterson? Were you just putting me on or did she really come to your party?"

Herbert snickered. "Oh, she came all right, and in more ways than one."

"Really? Our uptight, holier-than-thou, rightwing, conservative Mrs. Waterson? Our beloved school principal? She's into CFNM? I don't believe it!"

"Well, it's true. My stepmother had to ask her to leave early because she got so drunk that she was blowing all the strippers."

"No! No way!"

"She's the biggest slut in town. Trust me."

Iris shook her head numbly. She had always believed, mistakenly, that she was an oddity in her community—the person whose interest in the CFNM fetish was relegated to her alone. But now that illusion had been shattered, and suddenly she felt a terrible weight lifted from her shoulders.

"I always thought I was the weird one," she confessed. "But if Mrs. Waterson is into CFNM, then there must be others." She stared at Herbert. "Right? Herbert?"

Herbert suddenly felt himself once more at the mercy of those penetrating eyes. "I don't like to rat out on people," he said sheepishly. "I'm not supposed to be telling you this stuff."

"Why? Because Constance forbade you?"

"Yeah, kind of."

"Well, okay. Then can you tell me if there is anyone that I might know personally who goes to your stepmother's parties?"

Herbert hesitated to answer, and for a moment he turned his head away so that he wouldn't have to look into those compelling eyes.

"Please, Herbert," she resumed. "Just be honest with me."

"I'm not sure you're going to like it," he said, his eyes downcast.

"Tell me, please," she insisted.

He took a deep breath and exhaled. This was not going to be easy. "Okay. Okay. There is one woman…" His voice trailed off.

"Yes," she demanded. "Who?"

He took another breath and held it in. This time he spit the words out. "Your mother."

Iris thought she had misheard him. "What?"

"Your mother," he repeated.

Herbert watched his teacher's face register first surprise and then shock. She sat next to him in silent repose as if she were trying to conjure up an image of her mother being engaged in such an obscene activity as he implied.

"My mother? My mother?"

Herbert shook his head in affirmation. He didn't want to tell her, hoping that somewhere along the way she would have learned the truth on her own. But it was too late. "I'm sorry," he said, gently. "You asked me to be honest."

It took a while for Iris to assimilate this shocking information. Her own mother, a CFNM aficionado! She could hardly believe it.

"Wow," she said, suddenly somber. "My mother, a CFNM lover. Well, they say the apple doesn't fall far from the tree!"

"She never does anything nasty like some of the other women," Herbert assured her. "She just likes to watch, that's all."

Iris laughed. "Well, that's a relief! I never would have guessed that my mom is a voyeur. Not that I have any right whatsoever to judge her!"

"Nobody likes to be judged."

"You're right, Herbert. Nobody likes to be judged. But you know what's funny? All this time I've been thinking that I'm the only person in town who has this fetish for CFNM. And now I find that the universe is a lot bigger than what I thought it was. Me, you, Mrs. Waterson…my mother! God, what a revelation! It's scary to know that I've been living with my head in the sand all this time. Now I don't feel so bad. I don't feel bad at all, in fact. Thank you for being honest with me."

"No problem," he replied. "I hope you don't think less of your mom because of this. She really just likes to watch the strippers and have a few drinks. That's all."

"It's okay," Iris replied. "My mother is a grown woman who can make her own decisions. I'm just surprised by it all. She's so…so shy."

"Not really," he said with a wan smile.

Iris looked so unbelievably lovely at that moment, so much so that he could not stop himself from reaching out and touching her breast. His prick was once more beginning to rise. "Can I make love to you?" he asked her in all earnestness.

She gently removed his hand from her breast. "I think you're confusing love with sex, Herbert. And, no, you can't have sex with me. A simple handjob is one thing, but intercourse is something else. I won't have sex with a guy I don't love. Do you understand?"

"I suppose so," he replied looking downcast. "But you do like me, don't you?"

"Of course I do," she replied, kissing him on the cheek. "You are a very handsome young man and I find you very sexy, but I don't love you. I'm sorry."

Herbert had taken a big risk in making his demand, but he had to try. Maybe she would change her mind at some time in the future. There was always hope.

"Are you still horny?" she asked, seeing that he was sporting another boner.

"I guess so," he replied with a smirk.

Iris thought he looked so cute when he tried to pretend that he was in control of his cock when in reality he was not. "I'll do you again," she offered. "But this time don't get any of it on me, okay?" She looked around the room and eyed an old washbasin sitting on a pile of old magazines. "If you don't mind shooting your load into that…"

Herbert picked up the basin and handed it to her. "I like teachers," he said to her. "They always make you do it twice."

The handjob lasted all of two minutes before he sent another obscenely huge deposit of sperm into the basin. Iris caught all of it this time, marveling at the successive volleys of cum that seemed to go on forever. When he was finished ejaculating she put the basin down and wiped the remaining sperm off his cock with a tissue.

"I'll say one thing for you…you are one hell of a sperm maker!"

Herbert smiled at her and started to get dressed.

Suddenly there was a knock on the door and the sound of laughter coming from the hall. The teacher and her student looked at each other with dismay, but remained quiet, unsure of what to do.

"It's okay, Herbert," came a familiar feminine voice. "It's just me and Cecilia. Let us in."

"That's my sister, Amy!" Herbert exclaimed. "It's okay. Don't worry."

"But how did she know we were here?" Iris asked. "I made sure no one was following us."

"I don't know."

"Oh, God," she sighed heavily. "I'm going to lose my job over this."

"No, no, you wont," Herbert said, reassuringly. "Amy's cool. She won't tell anyone."

"I hope not. Otherwise I'm fucked."

As soon as Herbert opened the door, Amy and her girlfriend quickly ran in, as though they were trying to escape from something.