Mark Gets Milked

This story has a bent towards what I tend to think of as gentle femdom type themes, in this case involving an older woman and younger man. If that's not for you I completely understand.

All characters are clearly over 18.

Feedback is always appreciated.

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Mark heard the bedroom door open before he could cover himself. He'd woken up with a huge morning erection, like always, but he wasn't always staying at his best friend's house. He and Jacob met during freshman orientation at college and they'd been close ever since. Now, a year later, he was at Jacob's house for the entire summer break while his parents were in Europe.

But not only had he woken up with an erection, he realized with a sudden horror that he'd had a wet dream too, which hadn't happened in years, and to make it worse there was still a wet spot on the sheet beside him.

"Mark?" The door was open, and standing in it was Jacob's mom, Jessica.

Jessica was hot. Not just "for a woman in her 40s" hot, but the type of hot that made men stare and women jealous. Long black hair. Crystalline blue eyes. Full lips. Big boobs that she liked to show off in low cut tops and that he couldn't help but steal glances at. Fantastically curvy hips and bottom. Today she was wearing a t-shirt and tennis skirt that showed the tops of her tanned thighs. Sometimes he couldn't believe she had a nineteen-year old son.

"I was just going to tell you that Jacob had to go over to his dad's for a while," said Jessica. "He didn't want to wake you up. I'm going out to practice my game soon, and I didn't want you to worry if no one was here."

Jessica leaned down to tighten her sneaker laces leaving her breasts dangling right in front of him and it was all he could do not to groan out loud..

"Okay. Thanks," he mumbled.

"What?" Jessica finished tying her laces and started over toward the bed. "I couldn't hear you."

"Oh! Nothing. Nothing. I just said thanks!" He tried not to let her hear the panic in his voice and hoped she would go away, but she didn't. In a few short steps, she was there.

"Oh, dear," she said. "My sheets. Did you spill something?"

Mark could feel his face turning scarlet. "Um. Yes," he said. "I ummmm..." He searched for words, but now Jessica was standing over him. He was staring directly up at her breasts and he knew his hard on was completely visible. He couldn't think straight enough to come up with an excuse.

"Oh!"

He could see the dawning realization in Jessica's eyes, and he wanted to die.

Jessica laughed.

"You look uncomfortable, Mark," she said.

"Please go away," he said, as he rolled over and buried his face in his pillow

"Well, I would," she said, stretching the words out just a little too long, as she perched on the edge of the bed. "But it seems like you could use a little help. Would you like some help, Mark? I've noticed that you're a very excitable boy."

"I am?" He couldn't tell whether that was excitement in his voice or terror.

She slid her hand under him and placed her palm directly on top of his cock and he moaned. He couldn't help it, he could feel himself throbbing.

She laughed. "You are. Every time I see you, I can see a bulge in your pants. And now this," she said, withdrawing her hand and touching the wet spot on the sheets next to him with the tip of her finger.

"I can explain," he said, although he certainly could not.

"Can you?" Her face turned serious. "I think the explanation is obvious, Mark. And I think the remedy is too. You could benefit from a good milking," she said, with a soft smile on her face.

"A what?" Could he be any more embarrassed? He could barely focus on what she was saying.

"Milking," she said, again. "Would you like me to show you?"

He could feel himself nodding as she pushed against his hip to roll him to his back and placed her hand back on his cock. He tried to breathe deeply, but her hand felt amazing settling on top of his boxers. He couldn't help himself as he thrust up against her.

"See," she said, putting her other hand on his thigh to keep him pressed down on the bed. "That's what I mean. You're too excitable, Mark. I don't even know how you get any work done at school. Do you have an A average?"

"B," he admitted.

She tut-tutted. "That's what I'm saying. I suppose you don't have a girlfriend to help keep you nice and empty."

"No," he gulped. Was he really having this conversation with his friend's mother? And what did she mean by empty?

"That's a shame," she said. "And you're so handsome too. You'll find a girl soon to help you manage all of this. But in the meantime," she said, pointing again at the wet spot, "This really isn't acceptable in my house. So, why don't you lean back and let me manage it."

He couldn't believe this was happening. "But what about Jacob," he managed to say, as she encouraged him to lift his hips so she could slide his boxer shorts off.

"It's okay. He won't be back for at least a few hours. We have plenty of time."

Now he was totally naked in front of his friend's gorgeous mother. He tried to cover himself with his hand, but she quickly moved it away.

"None of that," she said, guiding his hands underneath him. "In fact, why don't you put your hands under your back. I'm not sure you can control yourself."

With one hand on his thigh and one hand on his cock, Jessica slowly began to stroke him up and down. Her hands were as beautiful as the rest of her. Soft. Long elegant fingers with red, manicured fingernails. Mark couldn't stop staring at them.

"You see, Mark," she said. "Young men like you have too much testosterone. And you're too easily excited. You can't focus on the things you need to focus on. You also can't keep your hands off yourselves, and that leads to bad habits. What you need is to be put on a regular milking schedule. No touching yourself in between milkings. You just let me take care of your erections."

"But," he protested. No touching himself? He was still confused, but her hand felt so good and she was such a fantasy of his that he couldn't really sound convincing with his objections.

"Look," she said. "I don't even need any lube, you're producing so much pre-cum. Do you see how badly you need this?"

His cock was still engorged. In fact, it felt harder than when he'd woken up. Ever since he'd gotten here and seen Jessica, lounging by the pool in her bathing suit or preparing breakfast in the kitchen as her pajama shorts clung to her ass, he'd felt like he was in a permanent state of arousal. He nodded, embarrassed but realizing that what she said was true. He did need this.

"But can't I touch you?" he whined. He wanted so much to have one of those big breasts in his mouth. To slide his lips over it and suck at her nipple.

"Ssshhh," she said. "You just lie there like a good boy, and let me take care of you. It will be over soon."

Her hand moved on him, pumping up and down, rotating around his bulbous head and treating him to sensations he'd never felt in his life. She looked at him seriously while he bit his lip to try to stop his moaning. The girls he'd been with had never been this good at giving hand jobs. It was like she knew exactly the right places to put her hand and exactly the right movements to make to bring him to the edge. He couldn't stop himself, even if he'd wanted to.

Much sooner than he'd expected he heard himself groaning, "I'm going to cum. I'm going to cum."

"That's a good boy," she said, soothingly. "Get it all out for me now. Come on."

Something about the words spurred him on. Yes, he would be a good boy. He would be good for her. He felt the cum building up in him, ready to spurt out, and then he realized too late that she'd taken her hand away. He couldn't stop himself, though. He felt himself thrusting into the empty air, cum spurting out of him without all of the delicious pleasure.

He whimpered. "What did you do?" He felt drained but still profoundly horny and his cock was still achingly hard.

"I know. I know," she said, stroking his cock softly with her hand. "That was difficult. Wasn't it?"

"Why did you do that?" he asked. "I'm still...I'm still...."

"You're still hard and aroused," she finished for him. "It's part of the process of getting you all emptied out. I know it's frustrating, but you're doing such a good job for me. You should be proud of yourself."

And strangely, he did feel proud of himself, glad that he'd pleased her. He wanted more, more of her, more of what she was doing to him.

She slowly started stroking him again, using his cum as lube, and he could feel his breathing getting heavier. How was it possible that he was getting more horny? But, still, now he was nervous about what she was going to do.

"It's okay, baby," said Jessica. "Don't hold back on me. Here," she said, pausing to take off her t-shirt and pull down her bra. "I think this will help," she said, and she leaned down and guided one breast to his mouth so he could suckle on her nipple. With the other hand, she resumed her ministrations of his cock.

He felt taken care of. Calm. As those sensations swept over him, his orgasm appeared almost out of nowhere, and he whimpered into her breast. But she seemed to know it was coming, and she again took her hand away at the last moment, leaving him to shoot his cum all over himself. He could feel that there was less now. She was right.

This time he didn't protest. He continued to suckle at Jessica's breast while she stroked him very gently, waiting for him to be ready again. Even though he was frustrated, he had to admit there was something pleasurable about it. And he knew Jessica would take care of him.

"That's a good boy," she whispered into his ear. "See. You're getting the hang of it now. Aren't you? It's not so bad, especially when you're distracted."

And then she began again, with measured strokes, letting the pleasure build in him again.

"I've helped a few other boys," she said, as her slippery hands glided softly over his shaft. "It's good you'll be here all summer. You'll see. By the end of the summer, you'll understand why it's so much better this way. And if you don't find a girlfriend by then, school isn't too far. I don't mind helping you until we can train someone else."

"I think I'm going to cum again," he whispered, momentarily removing his mouth from her perfect breast.

"What a good boy for letting me know," she said, happily.

This time when he came, he could feel that there was hardly anything left to come out of him. He felt himself straining to empty what little was left in his balls, pumping at the air. Jessica kept her hand planted firmly around the base of his shaft, to help him get out as much cum as much as possible, even while refusing him the pleasure of a full orgasm.

When he was done, he felt totally empty, but still hard. It was a strange feeling he'd never experienced before.

"You did such a good job for me," said Jessica, removing her hand. She grabbed a tissue off the side table and wiped him off. "Now, let's do one more thing. Okay?"

Before he could even say yes, she'd stood up and pulled off her panties, shoes and socks. Clad only in her short tennis skirt and her pulled down bra, she climbed on the bed, and planted herself over him, sinking herself down onto his still hard but totally drained cock.

"Oh, my god," he said, as he felt her warm, wet pussy envelop him. It felt heavenly, and yet, he knew as soon as he felt her slide up and down on him that he was never going to be able to cum. He could last forever.

"This is the best part," Jessica said, as she fucked him slowly and languorously, her gorgeous breasts swaying right in his face as she rolled her hips. "Now I don't have to worry about you cumming too soon and I can use your pretty cock to cum as many times as I want. You don't mind, do you, Mark? Especially after I've taken such good care of you?"

Mark couldn't speak. But he knew it didn't matter. It was going to be a long, dry summer and he was overjoyed to have Jessica taking care of him and to be giving her pleasure.