First Time For Jack free porn video

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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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Andersonville 13 Three Finger Jack

It was a perfect Saturday morning in Peace River. It was warm, but not too warm, and I was out taking a stroll around the town trying to get a feel for everything here. Connie had offered to go with me but I declined, saying I needed some time alone. I hated to admit it, but I was missing my life back in Andersonville. As I walked past Shady Pine Cemetery, I spotted Ashlee Gang laying some flowers on a grave. She didn't seem upset, rather the look on her face was comforting, as...

2 years ago
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Madison And Jack

Having graduated from college, I started my own business in commercial design and construction utilizing the skills I had learned while working in the construction industry and my studies in architecture and engineering while in college. Seven years along, I was doing very well in business but working long hours. I had been in a few rather serious relationships but eventually, the females I was involved with realized they came second to my career.At age twenty-eight, my mother, who was now...

First Time
3 years ago
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The Chelmsford Stalker

The Chelmsford Stalker By Michele Nylons The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up revealing most of her well-formed thighs atop long legs encased in sheer...

3 years ago
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SurprisesChapter 15 Jack

The cab driver took one look at me and leered, then propositioned me. I thought about slapping him but just ignored him. He simply figured that a young blonde leaving a hotel in the early morning dressed in an evening gown was a call girl. I let him drive me home and gave him the money Jerry had given me for the cab. I wasn’t sure whether I should be angry or pleased, to think that men would pay me money for my company. I was not about to undertake a career change! I got home and found the...

3 years ago
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Miss Jacks

Miss Jacks.I was at the time in the care of my aunt Muriel had been for some time my parents having been killed in a car crash. She was a high powered business woman, never really knew what she did, Now and then she traveled to different parts of the country. Always first class on these occasions she would take me along.I had just turned 18 and still wore my monkseaten grammar school uniform. I liked to wear it because as a senior along with the dark red school blazer with the gold black...

3 years ago
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The Stepford Children

Once upon a time.... All my life I had always feared God. Growing up I thought he personally stared down at from Heaven watching my every move, listening to my every thought. It was this fear that has always kept me on the straight and narrow and given me my morale courage. My only sorrow is that I was unable to pass this fear down to my children and from this, there will be no retribution. I am surely damned as if I had spent a lifetime of murder and greed. With this knowledge I don't...

3 years ago
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A Night Out with Jack

It had always turned me on, the thought of having a man drop a pill in my drink. Falling into his arms, unable to stop him from unbuttoning my dress. Slipping it off my shoulders, removing my bra and panties, and laying me on the bed. Lying there, unable to move as he spread my legs wide, sliding his hard cock deep into my vagina. Kissing my lips, down my neck, running his hot tongue over my hard nipples and sucking my breasts into his mouth as he thrusts into me. Paralyzed from the drugs, but...

BDSM
2 years ago
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Stepford Meat Swap

Introduction: Jessaica and her father take a road trip to the small california town Stepford to try a special kind of exotic meat, Bassed on a fictional town (Stepford) in the game SecondLife. Stepford Meat Swap Story: #47 Copyright 2010 Written: October 02 2010 A story By: KaosAngel Proofed by: KaosAngel Please send any comments about this story to ([email protected]) ********************************************************* ~~!! NOTE !!~~ This story is bassed on a fictional town within the...

2 years ago
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Truck Guy Beach ShowerChapter 4 Aussie Jack

I looked at the shower entrance just in time to see a short guy in a swimsuit coming from the other direction turn into the shower. At a glance the guy looked younger, maybe in his early 20’s. He was short and skinny, I’m guessing about 5 foot 4 and 130 pounds, wiry with a cocky walk, he was wearing a really skimpy swimsuit - maybe a Speedo. Thanks to my “encounter with the hot pink bikini” I was out of position and had no chance to stop him. I thought my “nude beach” fantasy was ending...

2 years ago
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Visiting Jack

[This one's for the 'real' Jack, and that wonderful back alley glory hole wherein many loads of sperm have been given (and taken), and where many more will surely be as well! Thank you Jack!]It came as a complete surprise to me when I discovered that less than a mile away from where I lived (.8 of a mile to be precise) there was a private glory hole located in an ordinary looking residential neighborhood, and so I ventured to send it's operator (who went by the name of 'Jack') an e-mail...

2 years ago
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Sally and Jack

Sally and JackI rushed around the house and made sure things were straight. Sally and Jack had emailed me a couple of weeks earlier and said they were coming to town for a visit and asked if they could stay at my place. We had been friends for years, ever since Jack and I had worked together back in our younger days. Sally, Jack, June, and I had been almost inseparable for many years. Things changed though, when Jack got transferred and they had to move to Florida. My wife, June, had died about...

Straight Sex
1 year ago
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Jack

Jack has always been horny. The problem was that as a normal Teenager he thought of nothing but girls but like most boys he did not have the nerve to say much more than Hi to one. Most of the time he would pick out a girl, decide to approach her then chicken out. This would usually be followed by a quick jerk off in his room. At 17 he met a girl when she moved in next door. Sue was 18 and a good-looking girl for a Goth Chick. She was wearing loose black pants, A floppy black Rob Zombie t-shirt...

First Time
4 years ago
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The Chelmsford Stalker

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up revealing most of her well-formed thighs atop long legs encased in sheer flesh-toned hose. He thought he could make out a subtle seam...

3 years ago
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Falling for Jack

Lorraine was accustomed to do her main shop travelling to the supermarket by the number 25 bus. In her forties, slim and petite she had looked after herself and boasted good health. Much to the envy of friends who said she was the sort of person that, no matter what she eats, never puts on weight, but Lorraine claimed it was exercise too and keeping away from the temptation of smoking and excess drinking. But although her friends envied her they did not know the real Lorraine, and how she...

4 years ago
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Stepford Meat Swap

Story: #47 Copyright ©2010 Written: October 02 2010 A story By: KaosAngel Proofed by: KaosAngel Please send any comments about this story to ([email protected]) ********************************************************* ~~!! NOTE !!~~ This story is bassed on a fictional town within the game Second Life called Stepford, I would like to thank Ariana RoeCastle, Emilie Muggins & Jerrol Jarvinen of Stepford for thier approval of this...

2 years ago
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Remembering Jack

[ With Covid-19 messing up everything you can imagine(!!!), here's a story looking back to pre-Covid-19 days; and not that far back, either! This is for 'Jack', the best glory hole operator I've ever had the pleasure of knowing first-hand! ]It had all the signs of being a hot, and quite humid summer that year (of 2018), but it was so worth venturing out into that sultry afternoon, knowing that Jack was waiting there for me behind the glory hole in his garage!I might have walked over (it was...

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