Mom's 20 Questions

Stacey McAllister, a 45-year-old psychologist with a penchant for tight skirts and low-cut blouses, sat cross-legged in her office chair, her ample thighs brushing against each other with every movement. Her son, Jimmy, fidgeted nervously across from her, his eyes darting around the room, avoiding the framed degrees and diplomas that adorned the walls. He squirmed in his seat, the anticipation building in his stomach like a coiled spring about to snap.

“Okay, Jimmy, we’re recording…” she began, as she hit the button on her phone.

“Do we have to do this?” Jimmy said with a defeated sigh, already aware what the answer would be.

“Yes! This is for my research paper,” she reminded him. “And you only have to answer twenty questions. Besides, it’s all anonymous! Nobody will know what a little pervert you are.”

“Mom!” Jimmy shot back, his skin growing redder.

“Kidding! Just kidding. I don’t know if you’re a pervert yet. We haven’t even gotten to that question yet,” said Stacey playfully. “Okay, remember, Jimmy. No lying. I’m an expert on human behavior. I’ll be able to tell, okay. Now, let’s start with something more simple. Question one. Sexual orientation?”

“Um… straight?” Jimmy replied.

“If you say so,” his mom replied with a little chuckle.

“What? You don’t believe I’m straight?” Jimmy replied.

“Well, you’ve always been a bit of a sissy. I mean, my underwear keeps going missing. Question two: have you been stealing them?”

“...yes. But to jerk off while I sniff them! Not to wear them myself,” Jimmy blurted out, immediately regretting it afterwards.

“Ooh, look at that. I was going to ask what you’ve been doing with ‘em, but you managed to save me a whole question there!” Stacey said triumphantly, her round cheeks breaking out into a sly grin. “And I guess we can answer that question about you being a little perv, too.”

Jimmy’s face flushed red.

“Question three: do you imagine having sex with me every day?” Stacey asked.

“....yeah,” Jimmy said. “I mean… it’s hard not to when I have the hottest mom in the world…”

Stacey groaned a little. “Nice save, Jimmy. But I’m not the hottest Mom in the world. I could stand to lose 25 pounds easy. Unless… question four. Do you like women like that? That chubby, mombod look?” she asked, her hands running across her generous curves for emphasis.

“Yes. I mean… I think so?” Jimmy said, squirming more than ever. “I dunno if you’re my perfect type, or my brain kind of created a ‘type’ that I like based on you…”

“What came first, the chicken or the egg…” Stacey mused. “That doesn’t count as a question, by the way. Anyway, question five. Have you ever jerked off while imagining proposing to me, or marrying me, or just me in a wedding dress?”

“Yes, yes, yes. But that should be three questions,” Jimmy protested meekly, trying to salvage even the smallest of silver linings. He wasn’t sure what was left of his privacy to protect, though.

“Fair enough, Jimmy, I can’t argue with that. And that’s all very flattering, by the way. Question nine: do you imagine you’d want a traditional husband wife relationship, or more of a permanent mother son thing?”

“Mother son thing,” Jimmy said quickly.

“Aww… you wanna be my little boy forever?” Stacey asked, ruffling his hair affectionately.

“Yes,” Jimmy said, his cheeks burning, and the outline of an erection starting to form in his pants.

“I wonder what other fantasies could be correlated with that kind of thing… wanting to preserve that childlike innocence,” Stacey said, sitting back down, stroking her chin and crossing her legs. “Question ten: Have you ever thought about becoming a eunuch?”

Jimmy was stunned that his mother had managed to draw the connection so quickly. But she was the best in the business for a reason. He knew, just as she said, that any attempt to lie would be useless.

“...yes,” he said, reluctantly, as though his voice was being pulled out of him.

“Ooh! Now we’re getting to the really juicy stuff!” Stacey cooed excitedly.

“Mom!” Jimmy protested.

“Hey! Any hormones-filled teenager could look at his mother’s fat ass and think it needs a good pounding,” Stacey shot back. “But it takes a really special boy to want to give up his manhood completely for his mom,” she added. “Question eleven: in your fantasies, who performs the operation?”

“...you do,” Jimmy said. “I mean, I know you’re not that kind of doctor, but…”

“No, no. I could totally do it,” Stacey insisted. “It’s not really that complicated of a procedure. Oh, but I guess I should ask about that too! Question twelve: How would you like it done?” she asked, as casually as a waitress might ask about an order of eggs.

“Um… I dunno,” Jimmy replied.

“But there’s so many options! Bilateral Orchiectomy, Burdizzo, banding, stomping, deep stirring, Neutersol injections, Testi-Gone cream…” she said. “Some gotta be sexier than others, right?”

“That should count as another question!” Jimmy shot back.

“It will if you answer,” said Stacey, reaching out and giving him a playful poke in the chest.

“I like them all, I suppose,” Jimmy conceded. “Neutersol and Testi-Gone don’t require painkillers so I guess those could be fun. I’d like to feel it happening without being in total agony.”

“Question fourteen: Have you ever faked a behavior problem, just in the hope that I’d have you castrated as a punishment?” Stacey asked, licking her lip as she chewed on her pen.

Jimmy winced. Even when he thought she’d already gotten everything out of him, she found a way to make it even more embarrassing.

“Yes. The underwear thing? That was the goal at first, to get you mad so you’d get me snipped. That’s what I jerked off about when I played with them,” Jimmy confessed.

“And I thought you were a little sissy! Well, I wasn’t that far off,” said Stacey, grinning playfully. “Jerking off about being a girl isn’t that different than jerking off over getting neutered.”

Jimmy’s face was now beet-red with embarrassment. He didn’t know how much more of this he could take, but the thought of his mother actually carrying out his darkest desires kept him both terrified and unbearably aroused. He could feel his cock straining against his pants, his heart racing in his chest.

“Okay, okay, let’s keep going,” Stacey said, her eyes sparkling with excitement. She leaned in closer, her ample cleavage threatening to spill out of her blouse. “Question fifteen: What do you imagine your life would be like as a eunuch?”

Jimmy’s throat went dry as he tried to swallow. He’d thought about this so many times before, but never had he been asked to articulate it to anyone, let alone his mother. “Well, I’d be...calmer, I guess. Less distracted by, you know, teenage hormones,” he managed to get out, his voice shaky.

“Ah, so you think castration would be a cure for your rebellious phase, huh?” Stacey said, raising an eyebrow. “Interesting. Question sixteen: how do you imagine our relationship would change?”

Jimmy’s eyes darted to her breasts and back up to her face. “I’d be more... obedient. I wouldn’t have those... urges anymore, so I could focus on making you happy. Like a loyal servant or something,” he mumbled.

Stacey’s grin grew wider. “Ah, so you’d be my little love slave, then... No more sneaking around, just my devoted, castrated boy. Question seventeen: is that what you meant by more of mother son thing, rather than a traditional husband wife thing?” she asked, her voice dripping with a mix of humor and intrigue.

“Y-yes, something like that,” Jimmy stuttered, his eyes fixated on his mother’s full lips.

Stacey leaned in even closer, the scent of her floral perfume overwhelming his senses. “Question eighteen: what would you do for me as my love slave, Jimmy?” she whispered, her breath hot against his cheek.

Jimmy’s mind raced with images of serving her breakfast in bed, doing her laundry, and even cleaning the house while naked, with his newfound subservience to her every whim. “Anything you want, Mom,” he murmured, his voice thick with desire. It was strange. He’d never really enjoyed doing chores, but the thought of doing them as a eunuch seemed so tantilizing.

“Mm, I like the sound of that,” Stacey said, her eyes gleaming. She leaned back in her chair, her hand drifting to her skirt. “Question nineteen: Would you like to have an orgasm right now?”

Jimmy’s eyes grew wide with shock, but his body betrayed his arousal. He nodded, unable to form words.

Stacey leaned over the desk, her voluptuous chest pressing against the wood as she reached for his zipper. Jimmy felt his breath catch in his throat as his mother’s hand found its way inside his pants, wrapping around his hard cock. Her touch was firm but gentle, a stark contrast to the humiliation he felt. She began to stroke him with surprising skill, her eyes never leaving his.

Within seconds, he was at the brink, his body trembling uncontrollably. The feeling of his mother’s hand on him was too much, and he erupted in a powerful orgasm, his cum shooting onto the floor between them. He couldn’t help but let out a strangled cry of pleasure, his eyes squeezed shut.

Stacey’s laughter filled the room, a rich, full-bodied sound that made him feel even more pathetic. “My, my, so eager. I guess I hit the jackpot with that question,” she said, her hand still wrapped around his now-softening cock. She gave it a few more strokes before letting go, watching with amusement he dribbled a little cum onto his thighs.

“Last question: how would you feel if I told you that was your last orgasm ever?”

Jimmy's eyes snapped open, meeting hers with a mix of horror and arousal. He stared at her, trying to gauge if she was joking or serious. The thought of never feeling that release again made him start to question everything.

"Mom... You're not serious, right?" He managed to croak out. It was one thing to sit on the bed and fantasize about it, his cock in one hand, his mother’s panties in the other. But to go through with it for real…

Stacey just winked at him as she opened her desk drawer, pulling out a jar with a cheery label that read "Testi-Gone!" in bright letters. "Oh, but I am," she said with a sultry smile. She unscrewed the cap and dipped her fingers into the cream, bringing them out with a little pop.

Jimmy's eyes grew wide with a mix of horror and excitement as he watched his mother rub the cream onto his balls. The cold sensation made him gasp, and as she began to massage it into his skin, the fear grew. Then the sensation grew warmer, far warmer than he expected.

“You can feel it working, can’t you?” she asked, her voice thick with amusement.

Jimmy’s breath caught in his throat as he felt his testicles shrinking, as though they were retreating from the uncomfortable reality of the situation. He nodded, unable to tear his eyes away from his mother’s hand as she continued to rub the cream in slow, deliberate circles.

“It’s working so fast!” she exclaimed, her eyes gleaming with excitement. “You’re going to be such a good boy for me, aren’t you?”

Jimmy nodded, his eyes glazed over with a mix of fear and euphoria as his testicles continued to shrink. He felt a strange sense of relief, as if a heavy burden was being lifted from him.

“You’re doing so well, baby boy,” Stacey cooed, her voice soothing and motherly despite the macabre nature of her actions. She massaged the cream deeper into his skin, her touch becoming more gentle and loving as his balls grew smaller and smaller. He felt his last remaining fears melt away, fading as fast as his doomed testicles.

“Mom... I can’t believe it’s happening. It feels... right,” Jimmy whispered, his voice trembling with a mix of ecstasy and trepidation. He watched in awe as his mother’s skilled hands continued the transformation, turning his manhood into nothingness.

The pain was surprisingly minimal, replaced by a warmth that spread through his groin and a tingling sensation that grew more intense with every passing second. His cock, once so eager, began to wilt as if bidding farewell to its former glory. The sight of his mother’s smiling face, her eyes alight with a mix of motherly affection and sadistic pleasure, only served to enhance the experience.

Jimmy’s mind was a whirlwind of emotions as he felt his balls completely dissolve. All that was left now was the cords, and a floppy, empty sack.

Part of him was terrified, his body rebelling against the loss of his manhood. But the greater part was overwhelmed by a sense of relief and euphoria. This was what he had always wanted, deep down. To be free of the burden of his desires, to serve his mother without the distraction of his own sexual needs.

“All done,” she said, stopping the recording with her phone. “I’m sure Testi-Gone will appreciate this valuable research.”

“You did all this… for them?” Jimmy asked, feeling betrayed.

“Of course,” she said. “They sponsored me. It’s funny. You’re the 89th guy I’ve done the 20 questions with. Each guy is different, but the last 2 questions are always the same.”

“You mean…” Jimmy said, gulping a little. He didn’t like to imagine he was just one of dozens of guys she’d done this with…

“Why do you think I had the jar just sitting there? Every guy, deep down, wants to give up his balls, huh?” said Stacey. “But enough questions for one day. Time for you to get busy cleaning up these cum stains from the carpet, my perfect little eunuch love slave,” she said, bending down and kissing him on the forehead.

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I hope you enjoyed the story! My DMs are open if you want your own story commission, or you just wanna tell me your favorite fantasy or story ideas.