Her Best Friend's Son

"You should stay here tonight," Julie told her best friend's son.

It was snowing steadily, but it wasn't really that bad. He could make the thirty miles back. But that wasn't the point. She put on a face, something between hopeful and pouty, and looked at Ryan imploringly. He paused, thinking. Then she saw him look at her. She bit her lip. He agreed. That was all there was to it. Julie knew that he had no ulterior motives, no expectations.

But she did.

Julie hadn't planned this. It had all just fallen into place. Visiting Kristin. Then her car wouldn't start, it seemed the starter was out. Her friend had had to get ready for her evening shift, but she had suggested Ryan. He was a senior in high school, had just turned eighteen years old a few weeks earlier. Julie had made note of the birthday, though it was mostly just idle fantasies that flitted through her head. But opportunity began to present itself. The snow came down harder. And why not? Her husband Dan had been gone for a week and wasn't due back for another. He had just called that morning from St. Louis, where he'd picked up a load bound for Seattle. It was perfect.

And she was ready. At thirty-eight years old, Julie knew she was a total MILF. Five-seven and one-hundred-twenty pounds, c-cups, short dark hair, pretty. She wore the usual, jeans and a top that revealed a little but not too much, just her preference was for attire that was a little too tight. Anyway, Dan loved it. But then, he didn't know about Stephen, their neighbor at the first house they had owned. Or Royce, who she had met on that girl's weekend in Atlanta. Or Mr. Erickson, who did their taxes. And he wouldn't know about Ryan.

Yes, Ryan. Julie had known him for years. A cute boy. Then a handsome young man. It was the birthday that had got her really thinking. Fantasizing. He played football, linebacker, tall with square shoulders. And so handsome. A lovely smile. Confidence underpinned with that innocent uncertainty that is part of a life of limited experiences. And Julie wanted to be one to expand Ryan's experiences.

He had a girlfriend. Brittany. Kristin had showed her a picture of the two of them. The girl was very attractive, which surely said something about Ryan. She was shorter than Julie, with long golden blonde hair. Smaller boobs. The contrast was good, Julie thought.

She went to the refrigerator and grabbed two of Dan's beers, opened them, and went to the living room and sat down on the sofa. She offered one to Ryan, setting it on the coffee table and patting the cushion next to her. He sat down and took a drink, trying too hard to look casual. She smiled and took a drink herself.

"So," she said, "tell me about Brittany. She's cute."

Ryan fumbled for what to say, then found some vague platitudes about his girlfriend.

"Your mom thinks you're fucking her. Is that true?"

Julie looked at the young man with a bit of an amused smirk. He again struggled for what to say, and she could see that a denial of some sort was in the offing. She preemptively arched her eyebrows.

"Yes," he said finally.

For a moment she just pondered her best friend's son.

"How many times?"

"What?"

"The number of times you've fucked her. Tell me."

Julie knew perfectly well that Ryan would know. The young man would have been counting. He just looked at her, an expression of denial on his face that faded to admission.

"Nineteen. Nineteen times."

"I see," Julie said. "What positions?"

"What?" he asked, clearly flustered.

Julie peered at him pointedly, then said slowly, "In what positions are you and your girlfriend engaging in intercourse?"

"Uh," he began, stammering, "Missionary. And..."

"And doggy, no doubt. I mean, your mom showed me a picture of her. I'll bet she has a nice ass."

He nodded, clearly embarrassed. She leaned toward him.

"Does she give you blowjobs?"

He went red, and gave a nod along with a barely audible 'yes'. This was all quite awkward for him, she could see. At the same time, there was also palpable excitement. No doubt from having such a discussion with an older and attractive woman.

"I'll bet she's tight."

He looked away. Mortified now.

"Oh, wait," she said, "do you even have any frame of reference?"

He looked at her.

"How many pussies have you had the pleasure of entering, young man?"

Ryan's mouth literally fell open.

"Just... Brittany's."

Julie smiled.

"You know, there's more to sexual pleasure than merely physical attributes. There's experience. Sensuality. A certain... je ne sais quoi, you might say."

He nodded, but Julie saw that he didn't really understand what she was saying.

"If you could fuck anyone else, who would that be?" she asked him.

He hesitated. She gave him a look that let him know she had to answer.

"Melissa Sanderson. She'll be prom queen. She's... everything."

"I see. Who else?"

"Chloe. I don't know her last name, she's a junior at the U. We work together at Donatello's."

That was the pizza place where Ryan delivered pies. The woman must be a server.

"Older woman," Julie observed. Ryan grinned.

"But she's, what, twenty-one? Not that old, Ryan. I mean, I didn't even make your list?"

He looked like a deer caught in the headlights and shook his head too earnestly. Julie looked at him with an intentionally conspicuous look of wounded pride on her face. But she was grinning. Still, this didn't erase his look of uncertainty.

"Not once? You've never stroked that young cock of yours while imagining me?"

He didn't say anything. Just stared. Julie kicked off one shoe and then another. Then she undid the top button of her blouse and slid over next to Ryan. She put down her drink and ran a hand across his jeans-covered thigh.

"Because I've touched myself, closed my eyes, and imagined you, young man. Does that surprise you?"

He said nothing again. But he didn't have to.

"Oh, I know I'm not as tight as Brittany. And I'm sure my tits aren't as perky. But they're still nice tits. Do you want to see them?"

She didn't wait for any answer and removed her top. Ryan stared at her bra-covered breasts until she had removed that as well.

"And I'll bet I'm a much better cocksucker," she said smoothly, looking at him. "Do you want me to suck your cock, Ryan?"

"Yes," he whispered, uncertain wonder in his eyes.

Then Julie leaned over and kissed him, sleekly snaking her arm down to feel him through his pants, to feel his young hardness. She knelt on the floor, guiding him to stand so she could unzip him. As she did this, she looked up at him with a sly smile. Running her hand over his underwear to feel him one last time that way, she then liberated his cock from its restraints. An involuntary moan, ever so slight, escaped him. Julie tongue-flicked the head of his cock, then took in in her mouth. Ryan looked incredulous. Slowly, she engulfed it.

Attentive to his body, she sucked him. Taking all of his cock, watching his reactions. The look on his face ran through a variety of expressions. Wonder. Ecstasy. Uncertainty. Then he was clearly becoming lost in the moment. She smiled, though she imagined with amusement that the cock in her mouth probably masked this. As Ryan relaxed, so too did his body. Julie wanted to keep sucking him, wanted the payoff. But she wanted something more. She let his cock slide from her mouth and took it in her hand. Stroking slowly, she looked Ryan in the eyes.

"Am I a better cocksucker than your girlfriend?"

"God, yes!" he blurted out.

Wait until I finish what I started, she thought. Then she stood and kissed him again.

"Let's go to the bedroom."

When they were there, standing next to her marital bed, she watched as Ryan removed the rest of his clothes. He did so hurriedly. No grace. He certainly was eighteen years old. It wasn't about refinement but his raw energy. She loved that. When he was done, she slid out of her pants and kicked them aside, put her hands on her hips, and watched him take her all in. Standing there in nothing but her black panties, she watched. Then she slipped off the panties. Her bush was dark and thick. She saw the young man's dick, relaxed somewhat since her oral attentions had ceased, twitch in reaction. Brittany would be shaved, she supposed. Well, she was a woman and not a girl, and so she looked the part. Julie did not lack in confidence.

After kissing Ryan once more, she put her mouth next to his ear.

"You're going to eat my pussy. And if you can make me cum, I'm going to let you fuck my pussy."

Then she pulled back to see his response. A hurried nod, as if he was worried that the offer might be withdrawn. Julie laid back on the bed and parted her legs to give Ryan access to her. Then she closed her eyes and sighed softly as he began his attentions.

What the young man lacked in technique, he made up for in enthusiasm. Brittany would be inexperienced as well, and perhaps communication was not what it might have been between the two. Maybe the girl was not orgasmic, which would have been problematic as Ryan attempted to understand the vagaries of the female body and how to push its buttons. But Julie found him eager and attentive.

He explored, licking and sucking and, adorably, kissing her pussy. At first his attention was on her lips. But she then began guiding him to do the things that she liked. Little flicks of his tongue into her. Soft caresses, fingers run through her bush. And she gave him directions to her clit, describing just how she'd like him to attend to it. If his mouth was getting sore, he did not complain, and soon she felt her arousal progressing to another level entirely, and she was on orgasm's door.

With that, Julie reached down and took Ryan's head firmly in her hands. He appeared to understand, and he followed her lead.

"Just like that," she whispered breathlessly. "There... right there... don't stop..."

Then, everything froze. She hung on a balance, and Ryan continued to softly suck her clit, just as she'd positioned him to do. Slowly, her body clenched, quivered, and then her release came, accompanied by her loud cries of his name. This was always how Julie orgasmed, and she loved the discovery of the way the appellation 'Ryan', that name new to her, sounded in that way that she could never fake. Over and over she called it out as the waves of pleasure washed through her, as her body grooved to the ecstasy. All the while, Ryan did as she needed, partly following her lead and in part, she could tell, instinctively. He was good, she thought to herself. Very good.

Patiently, he did not let up until she indicated that he do so, well after she was finished. Julie watched as he rose from between her legs. His lips glistened with her wetness, and she smiled at the sight. She leaned over and took a cigarette from the nightstand drawer. Though no longer a smoker, she occasionally had one when her sexual satisfaction hit a certain high. Perhaps once or twice a year this normally occurred, and there was no doubt today that Ryan's mouth had taken her to such heights. She silently offered him one with a querying look, and he slid up next to her and they smoked.

"I bet you want to fuck me now," she said musingly. Of course, he hadn't even cum yet. He looked very ready to go.

She took a long, cigarette-finishing drag and put it out. Then she reached for his and put it away as well. Julie spread her legs again.

"Well? I'd say that a deal's a deal because I promised this as a reward if you got me off, but honestly, Sweetie? This isn't anything less than what I want. Fuck me."

Ryan moved into position, his erection bobbing. He was hesitant.

"A problem, Dear?"

He looked uncertain.

"Do you-, I mean, should I-"

She knew perfectly well that he thought she might want him to wear a condom.

"What? Oh, don't you want to cum in me?"

"Oh, yes!" he said, way too hurriedly, and she could not suppress a smile.

"Good," Julie replied smoothly, "because I need to feel your bare dick in me, and I need you to put every drop you've got in this married pussy."

She gave him a very certain expectant look, and when he got over his momentary astonishment, he moved forward and positioned himself and entered her. She watched the expression on his face as he did so and could see how heavenly she felt to him. This would not be a long session, that she knew. He was young, beyond primed for this to happen, and she was his first older woman as well as his first married lover. Even as she was thinking these things, he acknowledged as much.

"Oh, God, you feel so good," he said to her as he slowed down his pace.

"Fuck me, Ryan," she said with a piercing look, "fuck me hard."

His pace did not increase.

"I'm not sure I-"

"You've done your part and earned this. Anyway, what I really want is to feel your hard dick pounding into me."

She reached up and took his chin in her hand.

"Fuck me!" Julie told him firmly.

And Ryan proceeded to fuck her properly. He kept making eye contact, trying to look serious and sexy and intense, but the married woman could see with amusement that his mask kept slipping to reveal his disbelieving joy. She could not help but smile. He was good. Not so much his skill. It wasn't refined but simple. And she knew that he was lost in new experiences. Her age. The sinful delight of being with someone's wife, and his mother's best friend at that. She watched as the expression came over his face. Surprise, he was going to cum even sooner than he had thought. Ecstasy as it approached. Yet disappointment, for she could see that he did not want it to be over too soon, for either of them. This would make him a wonderful lover one day, she thought. He already was a good one. But she did not want him to have any doubts about what was transpiring.

"Yes, Ryan! Fuck me! Cum in me! Fuck me and cum in me!"

The young man fucked her harder.

"Yes, fuck me harder! Fill this married pussy!"

With only a couple more thrusts, that's what he began to do. There in her marital bed, Julie was getting her pussy pumped full of eighteen-year-old spunk. The loss of control on his face was complete as his eyes closed and let the bliss overwhelm him. She would not orgasm again, not now, but that was all right. Mentally, she was beyond aroused, and enjoyed every last thrust, every last pumping of cum deep into her, and Ryan's final spending of energy when he collapsed, still within her.

She put his arms around him and they kissed, their bodies together. Slowly, he softened inside of her and slipped out. An embarrassed look came across his face, but her own look balanced between pleased and understanding, and then he laughed.

In the morning Julie woke first and showered. As the warm water fell over her, she thought of the night before. It would linger fondly in her memory, but she knew that it was an experience that Ryan would absolutely never forget. She would forever be his first older woman, his first married woman, his first affair. When she had been twenty, she had been seduced by a fortysomething man, the sexy and talented husband of a coworker. It never failed to arouse her when she recalled it. So she understood.

When she was done, Julie toweled off and went back to the bedroom. Ryan stirred, then looked at her. She stood before him, giving him a full view, which he took in with eyes openly hungry in an almost innocent way. When he went into the bathroom, she simply waited by the door, listening to him shower. In time, the water stopped, and a few minutes later the door opened. She was pleased to see that Ryan had followed her lead. He was fully nude, his dick erect. Julie looked at it conspicuously, and then saw the pleased expression on his face that resulted. She went over and kissed him and took him in her hand. He shuddered at her touch. That thrilled her but she played it cool. Contemplating him for a moment, she knelt, never breaking her gaze as she did. For a second time, she took that lovely young cock in her mouth, but this time was no prelude. Julie sucked him easily, then took all of him so that the head entered her throat momentarily. The visceral reaction to this delighted her. She fellated him smoothly, neither hurrying nor dallying. But the previous evening was hours ago, and the young man was more than ready. She detected in his expression once again, amidst the pleasure and amazement therein, a conflict between the approaching pleasure explosion and a desire to prolong what she knew was a magnificent moment for him. And she might have wanted the same, did she not desire even more that explosion. In her mouth. And so she sucked him to the inevitable conclusion, the trembling and the moaning despite himself, the reaching out for the wall for steadying, the uncertainty in not knowing if he was allowed to cum in her mouth, and the final realization that he was going to be allowed to do just that, which he surely wanted so badly.

Ryan's cum pulsed into Julie's mouth. She knew it was just her imagination, but she thought he tasted so fresh. She sucked and she swallowed, and then she sucked some more because he was still spurting. She swallowed again.

Then she stood.

"How soon will you be ready to fuck me?" she said throatily, her hand finding his slick dick. It responded.

Julie turned and got onto the bed on her hands and knees, facing away from him. Beckoning with a wiggle of her ass, she waited. The bed moved as he got on it behind her. A pause, and she could tell that he was manipulating himself. Then she felt the soft cock, only semi-erect, placed in the cleft of her ass. Slowly, he began to move it back and forth. Julie closed her eyes and smiled. He was confident and inventive. She felt the cock getting gradually harder. The shaft slid over and over across her asshole, and it occurred to her that had he tried to fuck her ass she would have let him. But she knew he would do no such thing. No such assumption would be made. Soon he was ready, ready for her pussy that itself was long wet and ready.

This time, Ryan did not wait for her to either ask or demand. He pushed his cock into her, placing his hands on either of her firm ass cheeks for balance. Then he began to fuck her in earnest. This was what she wanted. Pushing back on him, she subtly and wordlessly urged him to go harder, and he picked up immediately on the cue. Soon Julie could discern that Ryan, having just spent himself so recently, would go now for a long time. Long enough for her to cum, because as much as she loved the oral attention he had given her the night before, there was nothing like cumming with a cock inside of her.

There was something about his approach, and the young cock was hitting her just right each time it plunged into her. Probably accidental, as he just didn't have the experience to be doing it on purpose. But Julie was certainly fine with the result. Anyway, it wasn't the physical act itself that was the overriding source of her pleasure at that moment. It was everything else. The fact that she was cheating on her husband. She always forgot just what an intense thrill it was and was invariably delighted to rediscover it. The fact that the dick inside of her belonged to a man less than half her age, and one that had a hot young girlfriend as well. The fact, of course, the most sublime fact of all, that the man fucking her right then and there was her best friend's son. Lost in that thought, her climax came suddenly. Julie curled up her hands, clenching the bedsheet, and the pleasure ran through her like a beautiful electric current that just throbbed on and on. She was aware of sounds she was making, incoherent noises, for Julie had now lost all self-control and was simply living in the moment. When she finally came out of it, Ryan was still filling her pussy with his fine young cock.