Brian's Milking Lessons

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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.

Jessica laughed.

“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

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Written by The Gentle Domme
Cargado February 15, 2021
Notes Brian learns how to control all those of difficult urges he's been having from his friend's mom.

"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."
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