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"Jenny takes in a shy and inexperienced young man."

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Brian stood outside Jenny’s front door for what seemed like ages. He didn’t know what to expect, but hoped that she would be clairvoyant. Would she just know he was there? His eyes bounced around the four corners of the doorway looking for a way in that didn’t need him to press the doorbell. His thick-rimmed glasses started to cloud over as a result of his rising breath in the cold night air.

He questioned why he was there? Wondered what she would look like and whether he was doing the right thing? He wanted to go through with it, mostly because, at seventeen, he didn’t want to be the last virgin in his class.

His lifted his quivering finger and pressed the doorbell. His friends had assured him that the lady of the house would accommodate all his needs. He immediately regretted his action as soon as the lights flickered on in the entrance hall. A shadow grew larger and larger against the ornamental colored glass door. Brian heard the fumbling of keys in the lock and he nearly turned and ran away.  Only he knew what kept him transfixed to the spot.

When the door opened, Brian’s mouth dropped open.

Jenny’s voluptuous figure stood before him in a black see-through dress that did little to hide her ample cleavage, concentrating Brian’s gaze on the one spot that lay directly between her breasts, though his eyes wobbled from one nipple to the other, before settling back to her cleavage.

Jenny studied him with a smirk on her face as he stared at her. She thrust out her hand.

“I’m Jenny and you must be –”

She twisted her head to one side to try and make eye contact with Brian and to make him offer up his name. Even her lovely smile failed to divert his gaze.

Brian stared straight at her breasts.

“Brian, yes –”

Jenny said eventually, completing the sentence on his behalf. Brian looked up and offered his hand to her. He nodded his head in quick succession, in affirmation of his name being mentioned.

Jenny knew all about Brian. She had been sent a letter by one of Brian’s friends that explained all about him and why he would be visiting her. It was his friends that set up the meeting and it was his friends that egged him on; watching him get excited at the imagery that they painted of this voluptuous and sexy woman. A woman that would look after him.

Still, it was strange seeing him in the flesh, thought Jenny. His prominent cheekbones and broad smile immediately labelled him as attractive. His body looked in reasonably good shape, as it should for his age, but his concentration seemed to suffer from tunnel vision.

Jenny relished the thought of encouraging and enticing him to make him offer more of himself to her forty-two-year-old charms. She thought of what that meant and it suddenly dawned on her that she was nearly two and a half times his age.

“Why don’t you come in?”

Jenny pulled his hand a little towards her.

As her words sunk in, Brian moved through the doorway. It was eventually closed to the prying eyes of the nosey neighbors.

“Go right through to the lounge,” Jenny offered; her hand outstretched in the general direction. Brian’s eyes were forced away from her main charms as he led the way down the narrow passageway and into the lounge. He found the sofa and sat on it, quickly accompanied by Jenny.

Brian looked up, this time to peruse the contents of the dimly lit room and to rest his eyes on Jenny’s face. Jenny smiled.

Brian smiled back but with hesitation that was clear to see. She could see trepidation written all over his face but there was something else there as well. Uncertainty, she thought. Jenny noticed a hint of excitement as well. She had witnessed many boys of his age over the years and she knew how they reacted. Although they knew why they were there, it was always difficult to know where they should start.

Her hand reached out and she stroked Brian’s face.

“Don’t be afraid. I’ll be very nice. I promise.”

Brian nodded.

Jenny suddenly stood up and took a few steps backwards. She placed her hands on her hips and wiggled them. Her breasts immediately swung from left to right and back again before she bent over a little in his direction.

“Do you like them? I saw you looking at them as soon as I opened the door.”

Jenny continued swaying her breasts from side to side. Brian nodded once more, his eyes nearly popped from their sockets as he watched them swing slowly. Jenny finally knelt down in front of Brian, her breasts resting on his knees. She reached out and took his hands in hers.

“I want you to feel them for me,” she said smiling and pursing her lips at the same time. She could see the excitement on his face.

Brian’s eyes were once more locked on her breasts as he watched his hands move forward. He was no longer in control of his thoughts or any of his bodily functions and he let out a longing sigh when his hands brushed the thin black fabric covering Jenny’s breasts. He shook his head from side to side when the palms of his hands rested on them.

Jenny had to move Brian’s hands in a circular motion to encourage him. He eventually got the idea and started to move them on his own accord.

“What would you like to do, Brian?”

Brian said nothing. All of his concentration was intensified into one part of Jenny’s body. He was mesmerized by their size, their silkiness and their softness. The palm of his hand brushed over one of her nipples that had grown significantly and which poked through the thin fabric.

Jenny smiled as she studied his face. Every thought he was having, every feeling he experienced, was elegantly displayed on his face, and in Technicolor; his blushes highlighted the naughtiness of what he was being allowed to do and that was to handle a voluptuous pair of breasts, certainly not like those in magazines. His excitement at squeezing and squashing them, his astonishment at finding her nipples growing beneath his hand was slowly blowing his mind and causing stirrings in his body.

Jenny couldn’t stop looking into his very soul. She knew he was shy and she knew why he was there, but she expected some kind of response from him other than astonishment. It was like he couldn’t believe his luck. But then, Jenny thought, most forty-year-old men looked the same way when they were with her.

“Shall we see what you’ve got down here?”

Jenny’s hands reached along Brian’s trousers. She was making her way down his thigh when she realized that his cock had met her advancing fingers half way. Jenny gasped loudly.

“That is a big one, isn’t it?”

A smile crossed Brian’s face as she spoke. He nodded silently. His hands still circling her breasts and his eyes still fixed on her cleavage.

“I think we should take it out, don’t you?”

Brian said nothing.

“Shall we take it out and have a look at it, Brian?”

The mention of his name caused him to look into Jenny’s eyes. He swallowed hard and nodded furiously. Jenny suddenly realized that she had his attention and leant in for a kiss. He was just about to lower his head and continue staring at her breasts but his lips remained in position while her silky red lipstick smudged over his lips. One of Jenny’s hands came to rest on the side of his head and she pushed their lips together, her tongue trying its best to pry inside. Brian shared his first passionate kiss with Jenny, well, with anyone, except the mirror in the bathroom at home.

Jenny pulled back and started to unbuckle Brian’s belt and undo his trousers. She was past the awkward bit, the part where he acknowledged to himself that he wanted to be there, the part where he allowed her to handle his growing cock and his embarrassment of someone else seeing it. He needn’t be embarrassed, she thought. It was gorgeous. The next awkward bit would be to remove his trousers without breaking the spell, but it had to be done.

“Pinch my nipples, Brian; I love it when they get pinched.”

Brian had to look down to locate her nipples before allowing his fingers and thumbs to rest on either side of them.  As Jenny pulled his belt completely from his trousers, Brian pinched hard.

“Oh fuck, that’s lovely. Do it again.”

Jenny had unzipped his trousers by the time he squeezed again and she never even had to ask him to lift his bottom off the sofa to remove his trousers. She pushed them to the floor and looked at the solid stalk within his boxers.

Jenny let her hand trace the length from his balls to the middle of his thigh. Inexperienced he may have been, but in all her twenty-four years in this job, she had seen few cocks the size of Brian’s. When her hand reached the end of it and started on the return path, her attitude changed. Jenny was no longer thinking of herself as teacher but as student as well. Yes, she would teach Brian all he needed to know, but she was also going to teach him how to use that tool he had been hiding between his legs to pleasure her fully.

Her eyes searched Brian’s for some kind of reaction. She wanted him to look at her and see enjoyment in her eyes but all he did was look to where his fingers were pinching her nipples.

“You have such a gorgeous cock. Have you ever taken this out and showed anyone else?”

Brian shook his head.

“What a shame – still, aren’t I the lucky girl.”

Her broad smile and enthusiastic tone conveyed more than just the words. Her lust was becoming unbearable at the thought of taking his huge cock inside her.

Jenny removed Brian’s hands and placed them at his side.

“You can put them back on my breasts in just a moment. I want to feel you first.”

Jenny pulled his boxer shorts down. She pulled his cock from beneath them and let it spring to attention.

“You know you have a wonderful cock, don’t you?”

Brian’s cock was just about level with the top of her neck and he stared at it.

Jenny’s hand immediately wrapped itself around the base to steady it and the other followed suit a little higher up.

“Beautiful,” she remarked.

Jenny then looked into Brian’s eyes as she stroked her upper hand over his length and onto his crown. On her way down, she gathered his skin and pulled it tight.

Brian breathed deeply before letting out a long moan. The more her hands moved, the faster Brian breathed. Jenny watched his eyes, felt his cock throb in her hands. She was the teacher and yet she couldn’t quite believe her luck in stroking such a young cock of this length.

“It feels so strong, so pleasurable, so –”

The rope of pearly white fluid that shot from the end of Brian’s cock caught Jenny unawares, but by the time his jet of spunk arched into the air and started to fall onto her breasts she had recovered and her mouth had soon wrapped itself around the end of Brian’s cock. Jenny started to suck on his knob while her hand thrashed up and down his stalk milking his balls for every last drop.

Jenny swallowed hard but she could not complete her task and had to suck in some much-needed air and let the remnants of Brian’s spunk dribble over her hand and out of the sides of her mouth.

 “That was a little quick. Never mind, we have all night, don’t we?” she encouraged, inwardly amazed at the copious quantities of sperm he produced.

“I really love swallowing spunk. Did you enjoy that?”

Brian smiled, his cock remained stiff and erect in Jenny’s hand and he eventually nodded.

“Do you want to do that again?”

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His hands went straight for her breasts once more and he started to squeeze them as he nodded once more.

Jenny realized that Brian’s cock was not deflating and that it was there to stay. Her wry grin revealed her inner thoughts; she had hoped this would be the case. It often was with guys as young as Brian.

She removed Brian’s hands from her breasts once more and put them back at his sides.

“We can do better than you fondling them,” she told him while peeling her black see-through top over her shoulders and down over her heavy globes.

Brian looked on amazed. His mouth opened involuntarily as he watched her peel the dress downwards. His cock twitched. Jenny thought he was about to come a second time when her dress slipped over the end of her nipples but he managed to contain himself. Jenny pushed the dress down past her waist and to her knees.

She then gathered up her breasts using both hands and while holding then underneath, separated them slightly. She didn’t need any assistance from Brian as his cock was upright and solid as a rock. She leaned into him and placed his cock between her juicy melons, engulfing the whole length of his cock in her tit flesh.

Brian’s cock leaked pre-cum, or was it post-cum; it didn’t really matter, thought Jenny. It was a welcome sight and the extra lubrication between her breasts made it far better for Brian to feel what was going to happen to him.

Jenny looked into his eyes, smiling all the time and expecting him to say how good it felt, but he said nothing. He did grunt once or twice when her breasts were at the top of her motion and his cock head was deep in between her cleavage. On her downward stroke, the head of his cock was three inches clear, mere centimeters from the tip of her tongue. She couldn’t remember anyone from her past being that far out of her ample tit flesh.

“Come for me again, come in between my breasts. Soak my tits.”

Her words caused her pussy to leak. She could feel herself get wetter with every word she uttered. She wanted Brian’s spunk all over her body and then she was going to fuck him.

Jenny moved her breasts faster. She pushed her hands together to increase the friction and bounced her upper body with added excitement that she would get her rewards.

“Come on them, all over them,” she grunted.

Every time Jenny dropped her breasts onto his thigh, she watched Brian’s cock emerge from its torturous confinement, but this time, as soon as the head appeared; white liquid shot from the end hitting her under the chin.

She had him.

Brian’s spunk splashed over her throat and immediately ran down into her cleavage supplying even more lubrication to her substitute cunt.

Brian grunted every time his muscle clenched, every time his ejaculate left his body, every time his cock emerged from Jenny’s breasts. Jenny made a move to lean back a little to allow his spunk to reach her face. She got her reward when one jet of spunk landed on her extended tongue. She quickly sucked it into her mouth and swallowed before opening it again on the next downward stroke.  There was no loss as all the spunk she missed found its way between her ample cleavage.

Eventually, Brian stopped producing and Jenny stopped fucking him. His eyes were glued to the squidgy mess between Jenny’s breasts when she pulled away from his body. She lifted his face to look at her and smiled at him.

“I need to teach you something – do you want to learn how to pleasure a woman?”

Brian nodded eagerly.

She was pleased that his cock fell towards his body and Jenny realized that if his cock stayed hard after two orgasms she would have a whole lot of trouble on her hands. Her pleasure would at least give him time to recover. She stood up and allowed her black dress to fall to the ground, her nakedness displayed for Brian to see. She noticed him watch her shaven mound.

“Nice, isn’t it?” she said stroking a finger along its length.

Brian’s cock twitched and Jenny immediately saw it move. She closed her eyes in despair but it was a momentary muscle spasm at seeing her perfectly shaved pussy. Still, she didn’t think it would stay flaccid for long, not with what she had in mind.

“I’m going to let you pleasure me now; is that something you want to do?”

Brian nodded profusely.

Jenny once more offered her hand and Brian took it. She pulled him off the sofa before taking his place on it. She motioned for him to kneel between her legs and Brian was ever the dutiful student. His semi-flaccid cock hung from his slim frame as he knelt before his teacher.

Jenny opened her legs wide. Instructions followed and Brian remained attentive. He was told where to lick, where to stick his tongue and what the little pink bud was for at the top of her pussy, the one under the little hood that would come out to play when he had licked her. She had warned him about her juices.

Brian seemed to smile more than being put off by the whole lesson and he soon nestled himself between her thighs. Her smooth sex helped a lot and it wasn’t long before Brian’s tongue was slipping between Jenny’s lips and Jenny was closing her eyes in response. He even took some initiative and started stroking her thighs with his hands.

Her head tilted from side to side as she let him get used to her succulent body. She sighed, heavily, on more than one occasion and her hand rested on his head; her fingers stroked through his jet black hair as she grimaced with her near release.

“That’s it, Brian. I’m gonna cum.”

Jenny kept telling him over and over that she was about to climax and eventually she did. It wasn’t the blinding surge that she thought her orgasm was going to be. It turned out to be more on the tender and loving side of orgasmic release.

“Don’t stop; keep doing it. I want you to give me another one, only this time, do what I told you to do at the end.”

Jenny leaned back in the sofa and Brian once more descended between her thighs and licked her sweet pussy. Her juices flowed onto his tongue and he lapped at them. His tongue alternated between licking her lips and pressing hard into her pink opening. Somehow he had learnt the alphabet. Jenny was unsure where that had come from because she hadn’t told him about that. Brian moved his hand to adjust his growing cock that had started to prod the underside of the sofa.

Jenny’s orgasm encroached upon her, slowly at first but then it started to knock on her orgasmic door.  Not everyone did as they were told, she thought, but then, not everyone was Brian.

Her body flexed to his tune and before she knew it, pressure surges were causing her stomach to clench, her nipples tingled, her pussy was turning inside out and her mind was on fire. Explosions of red and purple light burst from her closed eyes. She was nearly there, nearly –

“Now, do it now, Brian,” she commanded.

Brian lifted his tongue to just under her hood and clamped her clitoris between his lips. He sucked as hard as he could.

Jenny lifted her body off the sofa, suspended in mid-air by her arms and small of her back. Her breathing had stopped but her heart was racing. Brian managed to keep up with her rapid change of position and kept the pressure where it was needed.

Jenny’s verbal outburst peppered the room with sounds that Brian had only heard used as abuse in classes. Jenny’s body convulsed, her legs shook from the sheer energy and her pussy gushed into Brian’s face so hard that he pulled away to avoid drowning in an orgasmic tidal wave.

As soon as her juices subsided, Brian started to lick once more, sucking and swallowing all that Jenny could offer. He wanted to please her as much as she had pleased him earlier and that was exactly what he succeeded in doing.

By the time Jenny had come down from her orgasm, Brian was standing with a huge erection pointing upwards to the ceiling.

“Come here, sit down,” Jenny instructed as she jumped off the sofa to exchange places.

Brian sat on the sofa, his cock vertical and almost comical. He hardly had time to settle himself before Jenny had straddled him and was feeding his cock into her pussy.

“I’m going to fuck you so hard and I want you to fuck me back.”

She sank down on Brian’s cock and stopped with just a few inches still left outside. The palm of her hand came upon his chest as she rested for a few moments.

“Wait a moment, just a minute,” she said as she took a deep breath.

Jenny pushed down a little further and more of his cock disappeared inside. A few more minutes and Brian found himself balls deep in her cunt. Jenny rested on his cock for a few moments before she raised off it a little. Jenny pushed back down and before long she found a rhythm that suited his size.

“This feels so good.”

Brian soon found his head clamped between Jenny’s breasts. Partly because that’s where he wanted his head to be and partly to do with the position and motion that was required in order to take his cock all the way inside her. It was double pleasure for Jenny and triple pleasure for Brian, especially with both sides of his head being massaged and pounded by her soft fleshy mounds.

Brian grunted, his climax overtaking him as he released another load of semen, this time into Jenny’s waiting cunt.

The tempo increased rapidly and Jenny found herself concentrating hard with every backward motion of her bottom. Although he had climaxed, Brian played it safe and stayed relatively still, letting Jenny do all the work. His hands came up on her breasts and played with her nipples.

When one nipple found the insides of his mouth, Jenny came. Her eyes rolled back into her head and her moans and groans once more invaded Brian’s senses. Jenny didn’t stop at just the one. She decided to keep going for as long as Brian’s cock remained solid.

Brian’s cock remained stiff for the next five minutes and she exhausted herself on his prize specimen, experiencing several orgasms before his cock deflated. Even then, it never slipped from her.

In post-orgasmic bliss, their mouths connected and the kissing started.

“That was the best fuck I have ever had,” said Jenny.

Brian just smiled, but he knew, as she did, that the evening would have to end and it was with some sadness from both of them that they dressed.

Jenny finally saw Brian to the door.

They kissed once more, just inside the doorway before Jenny opened it. Brian turned to leave and it was with regret that Jenny waved goodbye to him as he stepped from her house and started walking down the path. Regret at having lost a fantastic cock, but realizing that this was just business.

For the second time that evening Jenny was dressed in her black outfit, but this time her cunt was sore and well used, her breasts covered in dried or drying spunk and her appetite for sex – not quite fully sated. In fact, she was far from wanting to stop.

Jenny closed her eyes and in that moment, all she could think of was the length of cock that she was reluctantly saying goodbye to. She had taken it all: between her breasts, in her pussy. She had swallowed its contents with enthusiasm. And yet, all she could think of was having more. She opened her mouth to shout but when she opened her eyes, Brian stood before her.

Jenny stopped herself, dumbfounded; her mouth refused to work.

“Can we do that again, please?” said Brian.

They stared into each other’s eyes for what seemed like ages before Jenny threw her arms around him and practically pulled him inside, slamming the door shut.

Their mouths met and tongues started battling with each other before Jenny pulled away.

“Did you just say something?”  she asked.

Brian nodded.

 

 

Published 
Written by DarkSide
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