Chapter 1: Caught by Teacher

Charlie was a handsome, intelligent and fit fourteen-year old boy who lived under very sad, stressful, and demanding circumstances. His mother died when he was six leaving him and his overworked, fifty year old father to patch together an existence as best they could on their own. It was hard on the boy. He had to forsake the playtime activities his friends enjoyed to help his father maintain their home. Charlie learned responsibility, courage, independence, and determination before he learned his multiplication tables. However, leisure was just a small portion of what he had sacrificed. The absence of a mother figure left a yawning gap in Charlie’s life, a fact that did not go unnoticed by his father, who steeled himself to find just the right mother figure for his son.

When Charlie was nine his father met just such a woman and married a very shy but pretty, spinster-librarian of forty-nine named Norma. Norma had waited all of her life for an opportunity to fulfill herself as a wife and a mother. Her lifelong ambition was domesticity and to devote herself to a loving husband and happy children. Sadly, she watched the prime of her life slip by with all opportunity to realize her dreams stifled by her own timidity. At long last, her hope was restored when she was invited to share the lives of Charlie and his father.

Norma was such a kind and sweet lady and she was so good to Charlie and his father. Because she never treated him like a kid but rather as a young friend, Charlie quickly became very doting on her. She would relate to him in detail her long lonely life waiting for a man to love and a family to embrace. Charlie was captivated by her and looked up to her as a tragic heroine that needed the shelter of he and his father. She was their treasure.

At one time Charlie even had a big crush on Norma and cherished her regal feminine grace, heart-shaped face, high cheekbones and large, wise eyes. To Charlie, she was the prettiest, most noble woman in the world and he was proud to be near her. In return, Norma was so grateful to have in her life the love of Charlie and his father and she flourished in the fulfillment she had waited for so long and patiently. They all three enjoyed a peaceful, happy existence. Sadly, it did not last.

When Charlie was 12, his father died tragically. Charlie, of course, was devastated but had to walk the long road to recovery by himself. With the loss of a love in her life, Norma became an empty shell of her former self. Her slightly nervous but energetic and perky nature turned languorous and sullen. Her jet-black hair quickly showed streaks of gray and her light, nimble frame became just a case study in frailty. The first week after the funeral, she clung to Charlie like a life preserver, afraid to lose him too. Charlie, being a good-natured and conscientious boy, did not hold it against her to be so clinging and needy. He understood how she felt and did his best to help her cope and cause her no trouble. Charlie actually loved her a great deal and wanted only for her to be as happy and fulfilled as she had once been. Forced to mature at a very early age, he took it upon himself to take care of her and nurse her wounded spirit. Being truly fond of Charlie, Norma returned his affection ten fold.

Having just entered puberty, his hormones were playing havoc on his emotions as well as other things. He quickly discovered masturbation and he lost himself in it on a nightly basis. Many images and fantasies filled his young mind including a great deal centered around his stepmother, Norma, but the ones that he visited most were of his third period Social Studies teacher, Mrs. Petrova. Mrs. Petrova was a full figured widow in her early fifties who spoke with a distinct East European accent. Her graying dark brown hair piled in neat rolls at the back of her head framed a round, fine-featured face that still bore traces of a slowly relinquished beauty. Charlie had only rudimentary knowledge of female anatomy and even less about sex, but that did not deter his imagination from richly immersing his fantasies of Mrs. Petrova in detail. The more he entertained himself with thoughts of her, the more elaborate the fantasies became.

These fantasies began to extend into his daily life. He would sit at his desk in his Social Studies class never taking his eyes from Mrs. Petrova. He loved every line of her body and paid close attention to whatever bulge or curve that a tight spot in her clothes would reveal. This compounded with his highly detailed imagination never failed to produce an erection. In fact, Charlie had an erection almost the entire time he was in her class and took great pains in trying to conceal it. His worst fear was of being called on in class and having to stand to give the answer. Luckily, his classmates never noticed the tell tale long crease extending up the front of his pants but one day Mrs. Petrova did and just stared at it the entire time he was standing. From that day on, Charlie noticed her shooting glances at his erection every time he stood or walked by her desk. He was so embarrassed but was grateful that she had the discretionary tact not to breach his confidentiality.

Charlie did not know why he was so obsessed with Mrs. Petrova, he had prettier teachers and other thoughts to occupy his attention but for some reason every aspect of her distracted him. His grades were not suffering so he felt no reason to check his lustful thoughts and then one day he went too far and that was when his life began to change drastically.

The class was taking a pop quiz and all the students were silently bent over their desks working on the test. Mrs. Petrova was grading papers, sitting at a table that stood beside her desk at the front of the row of desks where Charlie was seated. He was working so ardently on his test that he had lost his erection and without watching what he was doing, he knocked his eraser off his desk. He immediately dove to the left side of his desk to retrieve it and as he did, he glanced up the row of desks and saw the knee and calf of Mrs. Petrova’s leg under the table. She was wearing that day a white blouse and a plain, woolen skirt that came up to just above her knees.

Charlie was at once thrilled by this small glimpse and sat up pondering the wonders of what was up that skirt. His erection returned. He answered a couple more questions and then faced the nagging curiosity of another foray. He summoned up his courage and then with a surreptitious look around, he pushed his eraser off the right side of his desk. He ducked down after it and then slowly looked up the aisle. There were her legs, her shapely calves rising up to her rounded knees and then between them those softly curved thighs. He focused his gaze and looked as hard as he could between the bulges of flesh, trying to find what lay beyond. As he did, she slightly spread her knees to turn in her chair and when she did Charlie did not see the white triangle of her panties beneath the mesh of pantyhose but rather just a brownish triangle and hose covered flesh above it. A rush of blood pounded through his head as this was the most erotic moment of his life. He was trying to infuse this image on his brain as fuel for his imagination and then all of a sudden her knees slapped closed. Charlie looked up and saw Mrs. Petrova glaring at him over the top of the table.

He sprang back upright and hunched over his test expecting all hell to break loose any second. He harshly reproached himself, how could he do such a thing to his dear Mrs. Petrova? He felt like every eye in the world had seen him and he was now under their contemptuous gaze. He wished he could just shrink out of existence. He tried but he could not finish the test, he sat there loathing himself until the bell rang for the end of the period. Everyone rose to turn in their tests and leave but Charlie lagged behind to postpone the inevitable confrontation as long as possible. As he placed his test on the table Mrs. Petrova looked at him sternly and said, “I would like to see you after school, Charlie,” and nothing more.

Charlie went through the rest of the day in a state of constant worry, watching the clock with fear and dread. He could think about nothing but what would happen when he met Mrs. Petrova. He knew the shame and embarrassment alone would be horrific. The day ended and as his schoolmates happily fled the building, Charlie took his long walk to Mrs. Petrova’s classroom and stood in the hallway. As dreadful as it felt, it was time to face the music. He took a deep breath and walked through the doorway. Mrs. Petrova was at her desk grading papers. She did not look up from her work but she knew he was there. She just said, “Close the door, Charlie, and sit at your desk.”

Charlie did as he was told and sat at his desk feeling the agonizing tenseness in the air. This would definitely be the wrong time to have an erection and he tried as hard as he could to not think of his adored teacher. Finally, Mrs. Petrova set her work aside and rose to her feet. She walked slowly around the desk and then stood in front of the table at the end of Charlie’s row of desks. She folded her arms in front of her and looked gravely at him.

“Charlie, you know that what you did was wrong?” she said, her voice was like a slap of shame in Charlie’s face. He nodded. “Charlie, a woman’s modesty is a sacred thing. How do you think it makes me feel to find you looking up my dress like that?” Charlie hung his head; he did not know what to say. “What would your stepmother say?” she added, knowing Charlie’s guardianship and reverence for Norma. The horror must have shown on Charlie’s face because she calmed him by saying, “Do not worry, I will not bring her into this.” However, she still pressed on her attack with, “How would you feel if your privacy were broken like that?” Charlie was too ashamed to answer. “Perhaps you should find out.” There was an agonizingly long pause before she said, “Charlie, stand up,” she said. He stood up and expected nothing but the humiliation of a paddling and then she spoke very slowly and firmly, “Take down your pants.”

‘She was really going to do it, ‘ he thought to himself, she was really that mad. Reluctantly, he did as he was told, unfastening the belt and the fly, letting them drop to the floor. Then she hit him with an even worse demand, “Your shorts too, Charlie,” she said. He grabbed them and bent down as he thrust them around his ankles. He stood up with his head bowed and waited for her to do something, but she did not. There would be no paddling, she was going to treat him to the same violation he had inflicted on her.

Charlie stood there before her with his pants around his ankles paralyzed with shame. He was more embarrassed and humiliated than he had ever felt in his life but not indignant because he knew she was justified in putting him through this. He had violated the sanctity of her privacy by looking up her skirt. This was fair.

As he stood there in the focus of her gaze, he fell once again to natural impulses he could not control. The thought of this woman he was so obsessed with watching his exposed dick played on his mind. He felt a bond opening up between them, as his exposure became an offering of his devotion to her. A slight draft gently caressing his bare flesh only made things worse. His small, boyish penis began to rise. Charlie tried hard to think about anything but Mrs. Petrova. He tried to think about what his stepmother would feel if she got word of his behavior. He tried to think about his classmates bursting in and witnessing this sight. He tried to think about all the embarrassment that his springing a boner might cause Mrs. Petrova. However, it was no use, the thought of his idolized teacher watching his naked dork was too much for him and his erection grew. It rose in a twitching, jerking motion to its full four-inch length. It stiffened to almost the point of aching. It swelled into an arch with the tip pressed against his belly.

When Mrs. Petrova saw it begin to rise, her eyes opened wide and she gasped. It was more out of dismay that now of all times he should get an erection - when he should be humiliated - than out of disgust. She stared at it a moment and then turned aside as if pondering something, her eyes darted about as if she were busily formulating some plan. She stood gazing out the window contemplatively for quite some time leaving Charlie in a quandary as to what further dread might be in store for him now.

She finally turned, walked to the door and locked it. She spun around on her heal and looked at Charlie with her head cocked to one side and a strangely sardonic smile on her face. “You like me very much, is this true, Charlie?” she asked him flatly.

Charlie got very nervous and antsy but something about the smile on her face gave him reason to believe he could confide his heart to her with no fear of any cruel derision. “Y-yes, ma’am,” he stammered.

“Charlie, I have a need ... I think I can use you for something I have in mind,” she said.

Charlie was very confused; he expected something but definitely something much worse than that. He anxiously waited to see what terms were about to be leveled at him. She casually strolled to face him in front the table. She stood with her hands on her hips and the same smile as she just looked at him, studying him.

“Charlie,” she finally spoke, “there is going to have to be an understanding between us. We are going to share a very special secret and I think I am safe in trusting you to keep this just between us, OK?”

Charlie just nodded his head. She leaned back against the table as she stepped out of her shoes.

“I am going to reveal something to you that you must not discuss with anyone, no matter what. I am sharing this with you because I think your feelings for me will not let you do anything to hurt me, do you understand Charlie?”

“Yes ma’am,” Charlie nodded again; his fear was replaced by curiosity at what she might be inferring. His eyes were fixed now on her feet, drinking in a new aspect of her he had never beheld before. Her hands went to her sides and pressed flat against her skirt then her fingers began pulling the material up to bunch under her palms. Charlie was mesmerized as he watched her hem climb higher and higher up her hose covered thighs, past the point where her pantyhose darkened, all the way up to her hips. He was astounded as to why she would do this or what was about to happen. His excitement mounted as her curvaceous upper legs were revealed to him.

She gathered up her skirt all the way to the hem and then in a quick motion she drew it up to her waist and then dug her fingers underneath to her waistband. Charlie’s arousal rushed to overload and he suddenly felt close to shooting his wad. He could not believe what was taking place before him or how close it brought him to getting off without even touching himself. His eyes were fixed on her upper thighs where her billowed skirt just barely obscured the place he knew the triangular patch of her pussy to be. His eyes darted back and forth between her ample, round hips taking in all the exposed curves she had offered to him.

She hooked her thumbs into the tops of her pantyhose and began to slowly push them down, following the curves of her legs all the way to the floor. Charlie felt disappointment as her skirt fell down behind her hands but also a thrill as he knew her bush was now uncovered below that skirt. Mrs. Petrova pulled the hose from both her feet and then slowly straightened back upright pulling her skirt up with her as she went. Charlie took in the sight of her bare, soft, creamy-white thighs and waited for her to expose the object of his longing. After one last pause, she scooped up the front of her skirt and presented Charlie with the full, unobstructed view of the object of all young males’ wonder - her pussy. She stood there holding up her skirt, still and silent, watching Charlie intently, letting him take it all in and then she raised herself on her toes and sat on the edge of the table, slightly parting her knees, putting herself on display for him.

Upon seeing the first glimpse of her pubic triangle, Charlie actually stopped breathing. To see those light brown curls of femininity framed between soft, round hips and surrounded by smooth, white skin was beyond anything his boyhood imagination could conjure. He was amazed and confused as to why she would just stand there and show him her bush like that, it was contrary to everything he knew about the opposite sex. He followed her lead, lifted his shirttail up out of the way, and held it under his arm. There they both silently stood in front of each other, naked from the waste down, exposing themselves to each other for at least two or three minutes. This moment was the focal point of Charlie’s life and he drank in every aspect of this simple yet tremendous exchange. His libido was overdosed and an orgasm was quickly overtaking him. As it approached, he felt the blood drain from his head. Spasms tore at him and strained every muscle in his body. He felt the familiar surge of joy shoot through his dork like a big feather being pulled out through his loins. His sperm erupted from the tip of his young penis, squirting out in thick jets that gushed onto his belly and ran in a slow drool down the front of his thigh. He lost himself in it; let it go freely, almost pushing it forth proudly like an offering to her.

“Oh, Charlie!” Mrs. Petrova exclaimed as she saw it happen.

Charlie plunged into embarrassment and frantic apologies. “I’m sorry ma’am. I couldn’t help it. I’ll clean it up, I’m real sorry.” He did not know what to do. He bent over to pull up his pants while still holding up his shirttail with the other hand.

“Charlie, Charlie, It is alright. I am not upset. It is just a terrible waste, that is all.” Still holding up her skirt, she stepped forward and placed a hand on his shoulder to reassure him. As she got close to him, he caught a thick, musky scent that he had never encountered before. It was the essence of her sex and it enticed him further. “We must not let that happen again.” She took him by the hand and said, “Come.”

Charlie shuffled behind her as she led him around to the other side of the table and to her desk. She turned and clutching her skirt up tight around her waist, she sat in her chair. She said, “Charlie, come to me. Kneel down in front of me.” Charlie knelt in front of her knees and starred into the mysterious pubic tangle between her thighs. Mrs. Petrova pulled on a lever at the side of her chair and it dropped until her hips were even with his. She spread her knees and drew her chair closer to him, until he was between her thighs.

“Charlie, I am not going to hurt you,” She said in a gentle, low voice, her accent getting thicker. “I am going to do something with you. It will feel very good to you. But you must not speak about this or my special condition.”

Charlie’s head was reeling, could she intend to fuck him? Was he ready for this? Blessed with the almost indefatigable libido of a boy, his erection still stood firmly against his belly. He hoped with all his might that he would perform satisfactorily. He heard a slight slurping noise that he could not quite place, it sounded like it came from between her legs. Mrs. Petrova scooted to the edge of her chair and slowly crossed her calves behind Charlie’s legs and placed her hands on his hips. Charlie was thrilled at the contact, never realizing it was now impossible to pull away from her, as if he would ever want to.

She bent over him so that her head was beside his. “It is time to introduce you to my Charm,” she whispered. Charlie heard more of the wet, gurgling noise and then he saw something move in the center of Mrs. Petrova’s cunt. In the sparse light available between their bodies he could see a finger-like protrusion emerge three inches from where her hole should be. He had never before seen a real pussy up close but he was certain they were not supposed to have anything like that. He pulled away from her to allow light in more than anything else and he met the resistance of her legs and hands.

“It is nothing to be afraid of, Charlie,” she whispered reassuringly, “it is just my special little something extra.” Mrs. Petrova placed her hand before her sex and the tentacle protruding from her pubis reached out and wrapped around two of her fingers. “See? It is part of me. It is going to help us ... be together,” she continued in a sweet voice. She drew her hand along the underside of the strange appendage, stroking it with her fingertips. It greeted and reacted to her touch as naturally and adroitly as one of her own fingers.

She pulled her hand back in presentation and Charlie bent down to examine this wonder. In the dense curls of her pubic hair, he could make out the slit of her pussy. He could see the puffy red inner lips highlighting the groove. Out of the bottom end of the slit, where it curved back toward her butt, where her vagina was, he saw the pinkish gray tentacle glistening and writhing like a large slug. It emerged from her vagina, twisted, and curled against the surface of her mound as if trying to pull itself out of her. It kept working itself out of her until a full ten inches dangled and writhed from her. It was a little more than an inch and a half in diameter at its base and gradually narrowed to a point with a slit at the tip. Charlie just could not stop watching it and the beautiful pussy from which it emerged. Mrs. Petrova just stroked his back and let him examine her. He tentatively extended his hand to touch it, cupping his hand underneath it and slowly lifting. It was wet and slick to the touch. Charlie marveled at how lively it was in his palm, how it curled up and then wound around his thumb; how it caressed the back of his hand in the same way he caressed it. With his other hand, he petted the soft curls of her pussy and gently probed her exposed, pink labia. “Come, Charlie. Let us begin,” she finally said and he straightened himself between her legs as he was before.

‘Begin what, ‘ he wondered. ‘What did she intend to use that thing for?’ With his head bent down, Charlie watched in amazement the spectacle before him. The tip rose and reached for his dick. Secreting its own lubricant from its surface and within, the tentacle licked and slathered a wet, gooey mess all over Charlie’s penis and testicles and slowly smeared it into his skin and sparse hairs. It coiled firmly around his penis three times and he felt himself nearing another climax as the soft slickness and amazing deftness of the organ treated Charlie’s dick like nothing he had ever felt before. After wrapping around him, the tip broke away from the coil and began groping in the air. The end began to open up. At first, it was just a small hole but it stretched wider and fluted outward. When it had opened to about an inch and a half, it uncoiled a couple of turns from around Charlie’s penis and then stretched down toward the dribble of semen on his leg. The mouth-like tip poised over the glob and then pressed onto it. Charlie could actually feel it kind of suck on his skin. Mrs. Petrova sighed and said, “Ahhh. It has been so long.” The tip slurped and smacked against his skin, cleaning off the area. Once finished, the tip rose up toward Charlie’s stomach. It lightly pushed his penis aside and then started to suck up all traces of the spermy mess on his belly. Its touch was light and tickled him as it worked. He watched in amazement at its dexterity and deliberate incentive.