Toby & the MILF
By smallbutmighty.

“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 was 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 her. 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 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 strangle 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.
“You see, son, your body betrays you. To a grown woman like me, your little babydick doesn’t look like much. You look more like a toddler than a man, in my opinion. But your body, those little testes, desperately want to pass on their useless DNA. That little dickie wants nothing more than to knock up my daughter. Left unchecked, the little man-clit could actually do it. But we’re not going to let that happen, are we, son?”
Toby nodded, confused by the older woman’s outlandish talk.
“And all this talk seems to have woken up your little dicklette.” Now she tapped Toby’s half-hard dick, bobbing out horizontally from his crotch.
The young man winced at her touch. He had never been hard in front of an older woman before, not naked and up close like this.
“Time to masturbate, Toby,” Milly commanded calmly.
Toby inhaled and brought his hand to his dick as he had done so many times before. Was he really going to jerk off in front of this MILF?
“It’s time. Show me how you play with yourself. That’s all you should be doing at this stage in your life. Not screwing around with girls, just playing with yourself. Just jerking off in the corner.”
The college student let the older woman’s humiliating words wash over him and began to pump his wrist, pulling on his hardening dick.
“Very good, Toby.”
He began to stroke his dick with two fingers steadily.
In the afternoon silence, the only sound was the young man’s flesh pumping. The unmistakable sound of a man masturbating is known to all. His quiet, panting breath. He felt Mrs. Manson’s eyes over him, calm and intent.
“I imagine you have to wash your little dickie and tummy every morning after your wet dreams caused you to shoot all over your belly, Toby. So ridiculous for a grown man to still be staining the sheets, to have to sneak off to the bathroom to clean up his jizz… and you do it bare butt naked, don’t you?”
Toby nodded.
“You’d like it, wouldn’t you, if one of your frat brothers walked in and saw your naked rear end, saw you washing yourself like that. You’d like for them to catch you like that, wouldn’t you, son?”
Again, the young man nodded in agreement, his eyes closed.
And if they asked what you were doing, you’d tell them the truth, wouldn’t you? That you’re cleaning the dried jizz from yourself after having a wet dream, just like a boy just starting puberty.”
“Yes, ma’am, I’d tell them that I had a wet dream,” Toby chirped, his face flushed from exertion.
“Stand over that wastebasket. When you get close, I want you to get on your knees so that you empty your dick right into it,” Milly commanded.
Toby shifted over and knelt so that his hard-on was pointed into the mouth of the wastebasket.
“My, my, my… Already at orgasm, huh? You must be very horny, son. And not much stamina at all,” Milly guffawed. “That’s it… Jerk it out.”
Toby looked at his little pink dick in his hand. All four inches at their absolute hardest. He couldn’t believe he was jacking off in this woman’s direction.
“Right into the trash where it belongs,” Milly said laughingly.
Toby began pumping his hips, panting, unable to resist giving into his shameless self-pleasure despite being closely inspected by this authoritative older woman.
“Ohhh,” Toby gave a muffled cry, keeping his orgasm quiet.
His butt humped a few more times as he shot him thick, white load right into the empty wastebasket. Mrs. Manson watched intently as the kneeling young man’s pelvis rocked as if electrocuted, ejaculating the sizable deposit into the trash. When the last shot was discharged, she handed Toby a tissue for the jizz on his fingers.
“Good boy. Now, take a breath and start again. I want those baby balls completely drained,” Milly commanded.
Toby made to stand, but Milly’s hand fell heavily on his shoulder.
“Stay on your knees. When you cum, I want you to ejaculate right into the wastebasket again. Dump it out again straight into the trash.”
Toby put his hand on his dick and began to pleasure himself once more. He opened his eyes to find Mrs. Manson staring at him, monitoring his most private act. From his new spot on the floor, Toby found that the older woman loomed over him. He squirmed under the woman’s gaze, looking at the floor self-consciously.
“Look at me, young man. Look me in the eyes while I watch you jerk off.”
Toby obeyed, meeting Mrs. Manson’s gaze. He looked into the woman’s eyes, which were a deep green. Locking eyes while jerking off felt supremely uncomfortable and overwhelmingly intimate. He felt strangely connected to this woman but deeply humiliated to have his shameful jerk-off act so closely supervised.
“Nothing to hide from me, son. I’m going to see it all. Nothing to be ashamed of,” Milly droned. “That’s it, that’s it. Rub it out. Rub it all out,” she coaxed the boy, who began to jerk himself furiously.
“That’s it, boy. I know you have a few more orgasms in you. A few more loads to dispose of. We need to make sure you’re completely sterile.” Milly leaned back in her chair, satisfied as her captive whacked off dutifully. “Do you enjoy jerking yourself off, Toby?”
The ridiculousness of the question stood in stark contrast to Milly’s deep, feminine voice.
He nodded, blushing. “Yes, ma’am.”
“I bet you do it all the time,” Milly said, smirking at the masturbating young man.
“Yes, ma’am,” Toby grunted.
“How often?
“At least once a day, usually more,” he said, and his face reddened at the admission.
“Horny boy. You’re quite the frequent masturbator. I bet you’ve done it in places you shouldn’t have,” Milly said, grinning at the boy.
‘Yes, ma’am.” His face reddened to a darker shade.
“Tell me where,” Milly calmly demanded.
“All kinds of places. My car, in the woods, on the beach. Once, in the school library.”
Milly pounced on this. “Tell me all about when you jerked off in the library, Toby. In the restroom?”
“No, no, right there in one of the big reading rooms. It was during finals, late at night. There was another guy, but his back was to me, and he had headphones on. I… I put porn on my laptop and did it right at the desk I was sitting at.”
Toby’s face radiated with heat at the shame of admitting this. Milly guffawed in disbelief.
“You just whipped it out of your pants and jerked it?” The older woman continued laughing and interrogating.
“No, ma’am, I pulled my pants and underwear down to my ankles,” Toby said, and his face reddened as he divulged this perverted detail.
“All the way to your ankles? You sat down on your bare butt and jerked your little babydick off?” Milly demanded, a tinge of disbelieving amusement in her voice.
Toby remembered the kinky thrill of exposing himself there, the feel of the cold wood on his naked buttocks. The shock of his white thighs under his desk.
“Yes, ma’am.”
Mrs. Manson laughed at this admission and said, “That must have been quite a sight. Your pants and underwear down to your ankles, you sitting down on your bare-naked butt playing with your tiny dick.”
She laughed again at Toby, the irredeemable ridiculousness of his lust. The woman’s open ridicule made Toby’s dick achingly hard.
“Did you like the feel of the chair on your bare naked butt?”
Toby nodded at the ridiculous question. “It felt…sexy and dirty, I guess, ma’am,” he confessed.
“It made you feel dirty to be bare butt naked there, didn’t it? I bet you would have liked to have stripped completely bare butt naked and jerked off. That would have given you a thrill, wouldn’t it?” the older woman taunted him.
“Yes, it would have, ma’am. Being bare butt naked in public like that, it would have been a thrill…” Toby gratuitously confessed.
“Maybe next time you should just go completely bare butt naked then. Make yourself fully exposed.”
Mrs. Manson let Toby think of that as he masturbated, then continued. Perhaps you should consider getting completely undressed in the library or somewhere else in public. Even your shoes and socks. Then, pack your clothes away and find a quiet corner to masturbate. Your naked, pale body is completely on display. Looking down at your hard little babydick poking out ridiculously and your bare feet on the library floor. Just a bare butt masturbator. How would you like that, Toby?”
At her prompting, Toby moaned affirmatively.
“Where did you cum?” Milly demanded.
“On the floor, ma’am. I just shot right between my legs, on the underside of the desk, onto the floor. I wanted to feel…” he trailed off, panting, working his meager erection in his hand.
“Exposed and perverted,” Mrs. Manson answered for him.
“Yes, ma’am.”
“And that’s just what you were. A naked, exposed, perverted boy. A butt-naked masturbator. Sitting on your bare butt and jacking your little dick off in public,” Mrs. Manson accused Toby calmly.
That’s what he was. Not an upstanding young man. Not a popular and well-liked student-athlete. But a butt-naked public masturbator and shameless deviant. The woman saw Toby for exactly what he was.
“If campus security had caught you, maybe they would have taken your picture of you naked with your little dick in your hand and made a sign of it. ‘Warning: Bare Butt Naked Pervert Public Masturbator.’ And put them up all over campus. Would you have liked that, Toby? Toby Thompson: Bare Butt Naked Public Jack Off,” Milly said, her hands framing the imaginary sign.
Toby closed his eyes, and he could see it.
“Spill your jizz, now, Toby.”
And as if she had said the magic word, the young man ejaculated directly into the waste basket. This load was smaller than the first, but he still shot out several ropes of thick jizz. Toby was panting from the exertion.
After a moment, Milly spoke, “What are you waiting for, son? We’re not done. Get your fingers on your little dick.”
“I don’t think… I don’t think I can get it up again, ma’am.” Toby was still breathing heavily, his face flushed.
“Nonsense. Lift your shirt, and show me your manboobs.”
Toby’s face reddened anew at being described that way, with his mostly hairless chest. He complied, revealing his torso to the leering woman. Milly reached over, grabbed the neck of the shirt, and lifted it over his head, hooking it back behind his neck so that he was still wearing the white polo shirt on his arms. Still, his midsection, bust, and neck were completely exposed.
“Now I bet if you play with these nice red nipples you have, it’ll help your little babydick become erect again.” Toby looked down at his bare chest, and Milly barked impatiently. “Play with them! Play with them just like a woman’s breasts. That’ll get that little dick hard again.”
Toby adjusted his position on the floor, spreading his knees wider and stretching his hips, then brought his hands to his chest and found his nipples. This was a fundamental part of his jerk-off ritual. In the library, he had lifted his shirt and fiddled with his tits too. He always played with his nipples when he jerked off, and Mrs. Manson seemed to know. Toby squeezed, tugged, and diddled them, and a wave of shameful pleasure emanated from his nipples to his whole body.
“That’s it. Try gently with just your fingertips. Ah, very nice. Press those little buttons. Attaboy. Play with them. Play with those little rosebuds. Just like a woman’s breasts,” she coaxed Toby on to abuse himself.
“Rub your hand over your belly, too. That’s an erogenous zone, too. Good boy.”
Toby felt himself up lewdly at the woman’s direction.
“That’s it. Rub yourself all over, from your belly to your manboobs, son. Fondle yourself. That’s it. Play with your manboobs, young man.” As the young man molested himself, his dick awoke once more, bobbing up with thickness.
“Oooooh, look who’s back. Your little clit loves when your nipples are played with, Toby.”
The woman spoke in a sing-song voice, leaning forward in her chair, pointing at the college student’s small boner. Sure enough, his dick was obediently swelling as he bothered his chest.
“Not all guys like having their manboobs played with. I think it’s too feminine for many men. But it seems like you just can’t get enough. Keep at it with one hand, then jerk off with your other. Take your little dick in your hand now. Atta boy.”
Toby began jerking off again, one hand keeping pace on his tits, and he exhaled in a high, wavering voice.
“It’s OK. You can moan if it feels good. Wendy’s is very high maintenance. She won’t be downstairs for at least another half hour.”
Toby moaned, wailing sensually in a voice he didn’t recognize.
“That’s it, let it out. You sound just like Mr. Manson when I play with his manboobs,” Milly chuckled as Toby felt his nuts retract closer to him.
He was close.
“Oh my, I think it’s time for you to cum again. Not much sexual stamina at all. Right into the wastebasket—that’s where your jizz belongs.”
His body was wracked for a third time with his orgasm.
“That’s it. Empty those little boy balls.”
Toby held himself up by his left hand, positioned over the wastebasket in a three-point stance as he cranked out his third load.
The woman coaxed him on as Toby pumped away. Finally, he grunted, shuddering over the wastebasket and spilling his third load. Toby stayed like that, letting his dick empty its mess into the trash, and his cockhead touched the top of the bag as his erection deflated. Finally, he got back up into a kneeling position, breathing heavily, his face crimson.
“Get going, Toby. You’re not done. I know there’s still jizz in those little balls,” Mrs. Manson jabbed the young man’s chest.
Toby gasped. Please, ma’am, I’m unable to. I’m spent.”
“Sorry, kiddo. I have to be sure. Stand up now.”
Milly grabbed the young man’s shoulders when he stood and gently positioned his yielding body on her desk so that his chest was down on the surface and his legs. His pants and underwear were crumpled at his ankles. Milly pulled them and his shoes off him, leaving the young man completely naked except for his socks. Toby relaxed, laying his cheek on the cool, polished wood.
“There’s one way to be sure that a boy’s balls are empty,” Toby heard Mrs. Manson say as she retrieved something from her desk. “Have you ever stuck anything up your backside, young man?”
Toby nodded, eyes closed. She heard the woman chuckle above him.
“Mmmm. As I expected. It’s nothing to be ashamed of, young man. Many men your age are ‘anally curious.’ I am happy to help you explore this part of your sexuality.”
She heard the snap of latex above him.
“You have a very tight little asshole, but it will give into my hand, I’m sure of it.”
Toby just whimpered as the woman inserted a gloved, lubricated finger between his ass cheeks. He grunted as Milly forced her index finger inside him.
“Play with your nipples as I penetrate you, Toby,” she instructed, tapping his shoulder with her free hand, prompting the boy to reach underneath his chest and attack his tits once more.
As he pulled at his pink protrusions, he unconsciously pushed out his hips, lifting his bottom off the table and spreading his legs wider, giving Milly even more access to his most private of regions.
Milly sighed contentedly, admiring Toby’s nicely spread nether regions and shapely cheeks. There was a dainty patch of light hair between his asshole and his scrotum, but she noticed that the young man kept his testicles shaven. His asshole welcomed Milly’s second finger. It seemed as though the boy had abandoned all modesty, reservation, or thought of any kind. The horny young man had yielded himself entirely to Milly’s will. With her free hand, he patted Toby’s left butt cheek affectionately.
“Pull your little dick, Toby. Pull your little dick as I play with your prostrate.”
Toby groaned as Milly sped up the pace on him, fingering, jamming in a third finger, and tapping insistently on the boy’s g-spot. The boy mewled like a kitten and pushed back into Milly’s fingers, opening himself up further to the welcome invasion.
“You know, Toby. Looking down at you spread wide open like this, now that I know all about your dirty little habits, I really think this is best for you. With your clothes on, you seem like such an upstanding young man, but really you’re just a perverted, butt-naked masturbator. You shouldn’t be trying to have sex with women. You should just be jerking off in the corner,” Milly pondered absently, as if she wasn’t knuckle-deep in the young man.
“You’re just not built for real sex, son. Nocturnal emissions still plague you, and you regularly wake up with your little dick sticking to your sheets. You jerk off at least three times a day, regularly in public. Why, you sat on your bare butt in the library and jerked off in front of another guy. You need to fondle your manboobs like a woman when you pull that little pecker.
“And you like having things shoved up your backside. You enjoy being fingerbanged! A boy with habits like that shouldn’t be trying to sleep with women. You’re not ready for it. Isn’t this more appropriate for you? Just jerking off in the corner like a sexually frustrated teenager? Like a horny little boy? A sexless beta virgin?”
The molested young man gave a throaty gurgle in response, his voice drunk with pleasure.
“Answer me,” Milly demanded, her voice darkening. Her free hand landed roughly on Toby’s left buttock like a thunderclap.
“Yes, ma’am.” Toby squeaked.
“Just jerking off. That’s best for you. Just jerking off with your pants at your ankles, hiding in the corner. Pulling on your little dick while your little asshole gets diddled.”
Toby pumped his hips back eagerly.
“You like that, son? Diddle, diddle, diddle,” Milly sang in a mocking, high-pitched voice while drilling the young man’s asshole with her digits.
Toby cried out, his voice just as high-pitched, and the woman laughed at him with wanton abandon.
“Tell me that you’ll only jerk off from now on,” Milly ordered.
“I—” Toby trailed off, his voice breaking as the woman continued to fingerbang him ruthlessly.
“Tell me, Toby. Promise me…”
“I’ll only jerk off from now on… I’ll only jerk off! I promise I’ll only jerk off!” Toby pledged as he bucked his hips, pushing his bottom into Milly’s hand.
“That’s it. Your hungry little bottom really seems to enjoy my fingers,” Milly crowed lustily, playing the boy’s ass like a musical instrument.
Toby moaned again, and Milly chuckled.
“My, listen to that. Good boy, to give yourself to me so freely. So shamelessly.”
The woman laughed again at the college student’s lust, laid just as bare as his spread legs.
“Moan louder, boy. Moan for me, just like a whore.”
She again smacked Toby’s cheeks, prompting him to let out a long and high moan like a woman. Soon Toby’s body was again wracked by orgasm, humping into the hardwood of his tormentor’s desk. Milly retracted her finger and lifted the boy’s hips to see what the lad’s little dick had yielded for him this time. She beamed to see that what came out was a meager amount of clear liquid without a trace of white.
“Excellent. Your jizz is now harmless and completely useless,” Milly announced.
Toby felt strangely proud, having pleased Mrs. Manson in this way. He was proud to have sterilized himself for the MILF. Milly whipped off the glove and tossed it into the wastebasket. She then helped the bewildered young man to his feet, supporting his shoulders.
“Good boy,” she said and rubbed his back, comforting him.
Then Mrs. Manson clasped her hand around the back of Toby’s neck, forcing his head downward. A large amount of his jizz lay at the top of the waste basket.
“Look at it. Look at all of your semen in there. That’s where your seed belongs, Toby. Safely disposed of. Wasted.”
Toby felt like a dog being punished for having an accident, forced to look at his mess.
“That’s where your essence as a man belongs, Toby,” she whispered into his ear as the student looked at the gleaming puddle of his wasted jizz.
“Where does your semen belong, Toby?” Milly asked firmly.
“It belongs in the trash, ma’am,” he meekly answered, exhausted.
She then frog-marched Toby to a mirror opposite her desk. Standing behind Toby’s naked body, she clasped one hand firmly over Toby’s shoulder and gestured at his groin with the other.
“Now, look. Look at your little dick. Shriveled up and all tuckered out. It looks even tinier, somehow. I’ve heard that chronic masturbation can permanently shrink a boy’s dick. Perhaps that’s why yours is so small, Toby. Nonetheless, this little dick is completely sterile, at least for now.”
She patted the kid’s shoulder.
Toby looked at himself in the mirror. His dick looked defeated. Instead of its usual alabaster, it was an angry, rosy pink and much thinner and shorter.
“It looks smaller, doesn’t it, Toby?” Milly was looking the young man right in the eyes through the mirror.
“Yes, ma’am, it does look smaller,” he whispered, barely.
“Do you actually think you could fuck anyone with a dick that small, boy?”
“No, ma’am,” he agreed.
Keeping her right hand planted on the small of Toby’s back, Milly leaned down and took it in her fingers, holding the dainty thing between her thumb and pointer finger.
“This little dick couldn’t get anyone pregnant, even if it tried.”
She waggled it around in her fingers, making Toby look at how small and silly his little dick really was. The young man’s whole body felt flush at this last humiliation. Milly had forced him to make himself sexually harmless, impotent, even if temporarily. Stolen from him any possibility of getting lucky tonight.
“It’s only when this little dick has been made sterile and those little balls are empty that you are permitted to spend time with my daughter,” the older woman pronounced.
“Yes, ma’am. I understand.”
Milly then surprised Toby by shaking his hand and slapping him on the back. “Get dressed. Pull yourself together. I now permit you to go on a date with Wendy.”
The woman sat down at her desk and watched Toby dress. The young man slowly clothed himself and stepped out of the woman’s office in a daze.
The date was fun. When Toby dropped Wendy off at 11:30, they shared a chaste kiss before she hopped out of his car. If she had pushed up against him, put her hips to his hips, she would have felt only softness. They dated all summer long, and Milly made sure that the young man never even got to second base with her daughter by making him empty his balls before every date while she supervised.
The End.
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