Toby pulled up along the tree-lined street, parking in front of the stately home. He fixed his short blond hair in the mirror. He thought better of honking his horn and instead walked up to the door and rang the bell. A voluptuous MILF opened the door, ushering him inside. Toby was still slightly stoned from the night before, and something about the woman seemed uncanny. Her very large tits pressed against a tight blouse, making her nipples visible. “Come on in, Toby. Wendy’s still getting ready.” The older woman shook Toby’s hand with a strong grip, smiling warmly at him.

“Milly Manson.”

“Toby Thompson, pleased to meet you, ma’am.”

The older woman seemed pleased to be addressed as “ma’am.”

Mrs. Manson led Toby from the entrance hall to her office. She closed the door behind them and sat at her desk in a plush executive office chair, leaving Toby standing before her. Wendy’s mother was imposing in her demeanor and attitude. She looked to be in her late 40s, with long black hair and large tits. She was sexy as hell.

“Wendy’s told me all about you, Toby. I hear you’re starting at Stanford this fall.”

Toby told her a little about himself, including his summer job at a law firm, his college experience, his fraternity, his studies, and the athletics he was involved in. He and Wendy had known each other a bit in high school but became friends this summer. Then, the conversation took a turn.

“Now, Toby, I was your age once. I know boys your age have only one thing on their minds.”

Toby inhaled, not liking where this was going. Wendy had warned her that her mom was ‘old-fashioned.’

“Sex, of course. Penetration. ‘Getting your dicks wet’ is what guys used to call it.”

Toby felt his face redden, and he suppressed a smile. The older woman shook her finger at the young man as she spoke.

“You’re permitted to date Wendy, but you’re not permitted to engage in any sort of sexual activity with her. Do you understand, son?” she lectured.

“Yes, ma’am,” Toby said, her voice wavering nervously.

“These pants are to stay on, mister.”

She leaned forward in her chair and pinched the fabric of Toby’s trousers, snapping it, making the young man flinch.

‘Understood, ma’am.” Toby nodded, staring straight ahead, hoping to move past this uncomfortable conversation.

“I forbid you from putting your little dick anywhere near my daughter.” Mrs. Manson’s beautiful face appeared twisted with anger at the prospect, like she was picturing Toby with his pants down on top of her little girl, hips pumping.

“I—” Toby started, but Mrs. Manson continued, smiling again.

“Well, there’s only one way to be certain you’ll keep your word.” Toby looked at her with confusion, and the middle-aged woman clarified as she leaned back in her chair. Her feminine voice was clear and booming. “Drop your pants and jerk off.”

She spoke as casually as if he were offering Toby a glass of water. Toby’s face went bright red. The older woman held her gaze. She was not joking.

Toby, it’s nothing I haven’t seen before. I have two sons. Now take out your little babydick and jerk it off. I know you know how, boy.”

Mrs. Manson stared at him firmly, lifting her hand and flicking her wrist back and forth, the universal symbol of spanking the monkey.

“You can lower your pants and underwear and masturbate your little dick right now, or you can turn right around and leave,” she demanded once more, then crossed her arms, leaning back.

The young man took a breath. He could get the hell out of there. Just leave this crazy family. Wendy was cute, but was she worth dealing with a maniac of a mother? But something about Mrs. Manson’s bearing entranced him. Her overbearing confidence, the smugness. As if there was nothing out of the ordinary about this demand, Toby found himself wanting to obey and reveal himself to the domineering woman. He wanted Mrs. Manson to see him naked. He wanted Mrs. Manson to watch him abuse himself.

He felt his hands at his waist. His fingers trembling, they opened his belt and unzipped his fly. It felt like it was someone else’s hands undressing him. He saw Milly nod approvingly as he reluctantly stripped. Closing his eyes, he pulled down his pants to his thighs.

“Undies too, Toby. I want to see the semen come right out of the tip of your tiny dick.”

Keeping his eyes closed, he lowered her underwear to mid-thigh, too. Exposing himself to this woman he had met only moments ago.

He opened his eyes and looked down at the endowment nestled between his thighs. His downy blonde pubic bush was neatly trimmed, and his short, slender pale dick was resting atop his small nuts.

Milly Manson leaned toward the standing young man and grabbed his bare hips, pulling him toward her. Toby gasped at the woman’s strong hands on his slender waist, his feet shuffling to place himself between the woman’s spread legs. He winced as the woman lightly touched his scrotum with her index finger.

“Now, see? Look at those testicles. They’re quite small, but you can tell that they’re plump with your jizz. Aching with your semen. You’re horny all the time, aren’t you, Toby?”

She kept her hands on the young man’s naked hips, looking up at Toby from her seat.

“Yes, ma’am.” Toby stared straight ahead.

“Why, I bet you still have nocturnal emissions. Wet dreams?” Milly interrogated, smiling at Toby.

Grinning at the ridiculous idea of Toby’s little penis getting hard and shooting all by itself as he tossed and turned.

“Sometimes, ma’am,” Toby admitted.

The older woman smirked at him. Toby felt a wave of humiliation roiling in his stomach. It felt like the woman was there in his bedroom, watching him cum helplessly under the sheets. Toby closed his eyes, and against his better judgment, he spoke again.

“Actually, a lot, ma’am. At least twice a week.”

Milly openly laughed at the boy’s ridiculous confession, and Toby felt a new rush of shame pour over him from his head to his groin. She did not understand this strange impulse to divulge his shameful secrets, to embarrass himself before this powerful woman.

“My, that must be quite embarrassing. A lot of stains in your jockeys, or do you sleep bare butt naked?” the woman asked.

Toby’s head was racing. Why was he discussing this with his date’s mother, a woman old enough to be his mom?

“Bare butt naked, ma’am,” he squeaked out, gratuitously echoing Milly’s choice of words.

“Good for you to sleep bare butt naked, given your constant little accidents. Still, it must make quite a mess, regularly waking up to dried semen pasted all over your pubic hair and belly. How do you handle it?” Milly asked as casually as if inquiring about Toby’s studies. Still, a slight smirk betrayed how much she enjoyed verbally degrading the boy.

Yes, ma’am, it’s a mess. I have to go to the bathroom and just ... wash my crotch and everything.”

Toby felt a rush from divulging such embarrassing information to this strange, insistent woman.

“You have to wash the dried semen out of your little blonde bush and your belly, then?”

Milly pointed at the kid’s neatly trimmed pubes and ran his fingers over the golden happy trail running up his taut abdomen.

Toby nodded.

“And you do that bare butt naked too, don’t you, son? Just tiptoe naked to the bathroom, then push your tummy up against the sink and wash your little dickie?” the woman asked with an incredulous grin on her face.

“Yes, ma’am ... I do it naked.”

Toby shuddered, remembering all the mornings when he had to sneak to the shared bathroom on the third floor of his frat house and hump up to one of the sinks to douse his groin and clean the big, dried patches of jizz from his belly. Standing on tiptoes, hoping no one else would come into the bathroom. Aroused by the exposure, by the risk of it. His shameful morning ablutions. Milly sighed as he examined his genitals.