Brian's Milking Lessons
- 2 months ago
- 11 min read
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Brian 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 freshman year at the college dining hall, 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. Jesus, it had been years since that had happened. There was still a wet spot on the sheet beside him.
He tried to pull the covers up, but they were stuck.
“Brian?” The door was open, and standing in it was Jacob’s mom, Jessica.
Jessica was hot. There was no other way to put it. Long black hair. Big boobs he couldn’t help but look at. Jessica liked low cut tops. Sometimes he couldn’t believe she had a nineteen-year old son. Today she was wearing t-shirt and tennis skirt that showed the tops of her tanned thighs.
Was he actually getting harder or was that his imagination? Oh, god. He tugged again on the bedsheets, but to no avail, and he cursed himself for just wearing boxers to bed.
“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 in a bit, and I didn’t want you to worry if no one was here.” Jessica leaned down to tighten her sneaker laces and Brian had a direct line of sight between her breasts. He tried not to groan outright.
“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?”
Brian 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.
He could see the dawning realization in Jessica’s eyes, and he wanted to die. He gave the sheets one more powerful tug, and the bottom one finally came unstuck. Unfortunately, settling on top of his giant boner, it just made his cock look like a ghost.
“You look uncomfortable, Brian,” she said.
“Please go away,” he said.
“Well, I will,” she said, sitting on the edge of the bed and plucking the sheet off him, but it seems like you could use a little help. Would you like some help, Brian? I’ve noticed,” she said, staring down at his erection straining under his boxer shorts, “that you’re a very excitable boy.”
“I am?” He couldn’t tell whether that was excitement in his voice or terror.
She placed her palm directly on top of his cock, and he moaned. He couldn’t help it. He moaned out loud. “Oh, god,” he said. 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, 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, Brian. And I think the remedy is too. You could benefit from some milkings,” she said, with a soft smile on her face.
“Some what?” Could he be any more embarrassed? He could barely focus on what she was saying.
“Milkings,” she said, again. “Would you like me to show you?”
He could feel himself nodding, if only because she was putting 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. He felt himself 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, Brian. I don’t even know how you get any work done at school. Do you have an A average?”
“A B,” he admitted.
She tut-tutted. “That’s what I’m saying. I suppose you don’t have a girlfriend to help to keep you nice and empty.”
“No,” he admitted. Was he really having this conversation with his friend’s mother? Maybe he was still dreaming. If so, did he want to wake up or not?
“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. Red, manicured fingers. Brian couldn’t stop staring at them.
“You see, Brian,” 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 control your erections.”
“But,” he protested. No touching himself? But her hand felt so ooo good sliding up and down his shaft.
“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 her pajama shorts riding up her ass as she prepared breakfast in the morning, 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 asked. 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 this. It will be over soon.”
Her hand worked efficiently, pumping up and down. She looked at him seriously while he bit his lips. He couldn’t stop 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, exactly the right movement 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 come. I’m going to come.”
“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 come 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, come spurting out of him without all of the delicious pleasure.
He whimpered. “What did you do?” He felt emptied but still frustrated, horny. His cock was still 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 come 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 gingerly take off her t-shirt and pull down her bra, showing off her amazing breasts. They were so big and full. “I think this will help,” she said, and she leaned down and put one breast in his mouth. With the other hand, she resumed her ministrations to his cock.
He let his lips settle over her nipple and began to suck at it gently. She guided it into his mouth so he could keep it there with his hands still underneath his back. He felt taken care of. Calm. His next orgasm appeared almost out of nowhere, as 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 come 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 and build in him again.
“I’ve helped a few other boys,” she said, as her slippery hands glided softly over his shaft. “Not Jacob, of course, although he’s had some lessons from a friend of mine, and it’s benefited him so much. He’s a straight A student. My friend even showed his girlfriend how to do it, and that’s why he’s such a good boyfriend. Once she realized the advantages, she was very thankful. 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 come 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 fully come as much as possible, giving him something to anchor him, 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 come. He could last forever.
“This is the best part,” Jessica said, as she fucked him slowly and langorously, her gorgeous breasts right in his face. “Now I can fuck you for as long as I want and use your pretty cock to come as many times as I want. You don’t mind? Do you, Brian? After I’ve been so nice to you. I think you can see why Jacob’s girlfriend appreciated his lessons so much.”
Brian couldn’t speak. But he knew it didn’t matter. It was going to be a long, dry summer.