First Time for Jack - Cover

First Time for Jack

by Varangian

Copyright© 2000 by Varangian

Erotica Sex Story: When Jack's English teacher took him to bed, she failed to teach him the most important fact.

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Consensual   Romantic   First   .

Jack looked at the departing school bus, half way down the wet street, and mumbled "shit" several times. Not only had he missed the bus, but it was raining hard and he was getting soaked. He was about to return to the school when a Ford Taurus pulled up to the curb, the passenger window came down and the woman driver leaned over and called to him.

"Hi, Jack. Get in before you're drenched."

The fifteen year old boy immediately recognized not only the voice but the face of the woman, Miss Simpson, his tenth grade English teacher. Jack got into the car, where he knew there was no threat and where it was dry.

"I'm sorry, Miss Simpson, but I'm leaking all over your seat," he stammered.

"That's all right, Jack. The seat will dry, but we wouldn't want you to catch your death of cold, would we?"

There was something old fashioned about Miss Simpson, Jack noticed not for the first time. She always dressed very primly and her blonde hair was usually piled onto the back of her head in a bun. To Jack the woman was old, but he knew that she was less than thirty. She was very pretty too, Jack noticed, not for the first time, although he had never fantasized about her.

"You missed the bus again," she remarked, stating the fact, as she pulled the car into traffic.

"Yeah. I don't know how I do this so often. I'm sorry."

"You don't have to apologize to me. It's your problem and you are the one who has to bear the consequences.

"You live in my neighborhood," she continued, looking over at Jack with a smile. "I'll drop you at your house."

Alice Simpson was struck by the boy's beauty, not for the first time. His cheeks had a rosiness to them, and it would be some time before they would feel a razor. His face was pretty in repose, but especially when he tried to express himself in class. Then it would come alive in innocent excitement. His brown eyes would grow large and his lips would strain to shape themselves around every sound. Miss Simpson had seen many pretty boys before, but none of them had struck her as Jack did, a boy who had size, heft. He was almost as tall as she and he probably weighed more. She had seen him more than once in his gym attire. His limbs were shapely and hairless, like those of a younger boy, but the size of him suggested to her that he probably had a virginal, almost adult sized apparatus.

"Do you have a best pal, Jack, someone to whom you tell all your secrets?" she inquired nonchalantly.

"If I told secrets, they wouldn't be secrets any more," he replied, almost giggling.

"But don't you have a best friend?" the woman persisted.

Jack hung his head and murmured, "No, I'm not very social." He hastened to add in an effort to acquit himself of any perceived social deficiency, "But I do like a lot of people."

"So you're a loner? You don't have a girlfriend?"

"Yes, no," Jack replied in confusion, quite deflated by such admissions, which his teacher forced from him.

"Are you religious?" she inquired softly.

"Na! My Dad's an atheist, and my Mom's a Unitarian, which is almost the same thing." Jack's response was smug. He was repeating words that he had heard his uncle use the previous week.

"What if you had a girl, a girl who let you touch her?" Miss Simpson began slowly, looking across at the pretty boy, who gazed back at her with an uncomprehending, open face. "Would you tell people about it? About touching her?"

Jack was flustered by the very idea of touching a girl, but he answered with a firm, "No."

Alice Simpson smiled quietly to herself as she braked at a red light. She looked over at the boy and said: "Jack, there's something I have to do at my house. Would you mind stopping by there for a short while, before I drop you off?"

"No," replied the unsuspecting boy, "not at all."


The week before Alice had been informed by her physician, an old family friend, that the tumor on her brain would disable her within two years and that she would probably be dead in three. This doleful news came as a great shock to the young woman, of course, but she already had an inkling of the truth. Her mother had died of the same disease, when Alice was just a little girl. She was indeed very prim and proper, but at age twenty-eight, still a virgin, she resolved not to exit life with hymen intact. She became determined to make love most grandly with a virginal young Adonis -- with Jack Mattingly, her beautiful, fifteen year old pupil.

"Here we are," Alice announced gaily, as she pulled into the driveway of her handsome property. It was a large tract, abundantly timbered, upon which was placed a smallish, elegant cottage. They got out of the car near the back door of the house, and Jack followed his teacher inside, admiring the place, but suspecting nothing.

"You really are wet," Alice remarked as they stood in the middle of the kitchen, her hands on the boy's shoulders, feeling the damp. Jack liked the touch somehow, without understanding what was possible, or even probable.

"Let me get you a robe," Alice suggested, "and then you can put your clothes into the dryer."

Jack nodded slowly, still obtuse. Alice quickly got a robe for the boy from a nearby closet and handed it to him. Jack took it and went into the bathroom to change. He soon emerged with a bundle of damp clothes in his hands, including his underpants, which he had placed at the bottom of the pile. Alice took them and quickly deposited them into the dryer, located in an alcove near the back door.

The robe that clad Jack's naked, young body was a frilly thing that exposed much of his boyish chest and which came to several inches above his knees. Alice marveled at the sight and tried hard not to stare at his exquisite legs, the calves of which had an almost imperceptible, light down. Jack was gloriously blonde.

"Would you like a Coke?" Alice inquired, as she opened the refrigerator, almost trembling in passion and lust.

"Sure," the boy replied with a bright smile.

Alice handed him the cold bottle. She stood deliberately close to him to gage his height, to determine that they could kiss as they fucked. That was important to her. It was something about which she had often fantasized: to have a male body above her lightly, cock deeply penetrating as they kissed desperately and traded spit. Alice had masturbated frequently to such an image behind her eyelids.

"Come, let's sit in the living room," she suggested to the pretty boy, who came along willingly. The young woman actually pulled Jack down with her onto the sofa where they sat close together, their bodies touching. The movement disturbed Jack's robe and most of one thigh, creamy smooth and soft-looking, was revealed almost to his crotch. Alice could not resist placing her hand on it and rubbing it softly up and down, savoring the touch.

"Jack," she almost whispered.

"Yes?" he responded in great confusion.

"Would you tell if a girl touched you?"

Perhaps Jack was a bit slow, but he was no dummy. He suddenly understood what was happening, and it did not take him more than an instant to accept what Miss Simpson was offering him. He relaxed totally and laid his head on the woman's shoulder.

"I won't tell, anything, ever," he sighed

"When do you have to be home?" Alice inquired anxiously.

"Not for two hours," he responded with a naughty grin, and he nestled his face into the woman's neck, licking it. He breathed the scent of her deeply, a mixture of shampoo and musky arousal. He reached over and cupped her right breast, knowing instinctively that it was permitted.

"Have you kissed before, Jack?" she inquired, her voice sounding far away from her, as if she were in a trance.

"Just my mother and an aunt."

Alice had the boy's robe wide open. She fondled his sleek chest and kissed him deeply. Her hand slid lower to an almost man sized cock that was hard, yet soft to the touch. She pumped it a couple of times. Jack's fast breathing informed her that he would come too soon to please her. She resolved to taste her lover, to experience what most prim people consider disgusting.

She sank quickly upon him. Jack's face showed his astonishment as he felt a warm, moist mouth sucking the end of his cock. He did not try to hold back. He let himself go and spewed ecstatically between Miss Simpson's lips.

Alice was overwhelmed by the flood of the boy's seed. She choked and coughed, and as she pulled her head away from the torrent, her face was slimmed. Still, it was what she wanted, most wanted, and she swallowed what was in her mouth.

 
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