"Ready?" Lily said, looking up at you. Her face was flushed pink, her blushing spreading all the way down to her flat, bare chest. You couldn't deny that the sight of your completely nude little sister kneeling in front of you, preparing to pull down your underwear, was having a powerful effect on your teenaged libido. Part of your mind kept warning you that this was deeply perverted and wrong, that you shouldn't be doing this with your own sister. But Lily's expression was so earnest and excited, and despite your outwardly confident mannerisms, you had never actually been with a real live woman before. You know, sexually.
As Lily grasped the waistband of your turquoise boxers, the curse of your persistent virginity loomed large in your mind. You had developed crushes on a number of girls at school, and Lily knew it, but you had never worked up the nerve to confess to most of them. You never told Lily that the few times you'd gone through with it, the results had been...mixed. There was a reason you'd never had a real girlfriend before - at least, not one who was willing to go all the way with you.
"It's...it's okay if you don't want to," you repeated, feeling your apprehension rising, giving you second thoughts yourself.
"I want to," Lily said firmly. She slipped her long, slender fingers underneath the elastic waistband of your boxers and pulled them outward and downward. She looked down inside your underwear and fished her hand around within their snug confines. Her fingertips tickled your lower belly and the top of your groin as they searched for your member, plunging ever deeper. Her touch was clumsy and inexpert, and she accidentally pinched you once or twice as she searched for your manhood, but she finally wrapped her fingers around your aroused shaft.
If you hadn't already been completely erect by now, the touch of your little sister's fingers grasping your penis stimulated you beyond any other sensation you'd ever known. For the very first time, your penis was actually being directly touched by a girl. A real, live, nude girl was actually holding your erect cock in her hand. It felt indescribably exciting, even though the knowledge that it was your own little sister also flooded your fevered mind with shame tinged with forbidden eroticism.
You felt your boxers slide down your legs as Lily peeled them down until they fell limp around your ankles. You were now every bit as wholly nude as your petite, thin, pale little sister who knelt in front of you. She clutched your rigid penis firmly in her fingers, inspecting it closely and wordlessly, her eyes wide.
"It's --" she said finally. "It's so small."
Your heart sank. All of your feelings of confidence and control that you'd exhibited all morning faded away to nothing as your own twelve year-old sister confirmed your sexual inadequacy. "It's not that small," you said.
"It gets bigger when it gets hard, right?" she asked. "That's what I heard other girls say."
"It, um, it already is hard," you said dejectedly. You really didn't want to admit to Lily that, in fact, right now you were harder than you could ever remember being in your entire life. Despite your embarrassment from hearing her judgment of your under-endowment, despite the nagging voice in the back of your head reminding you that you shouldn't be having erotic feelings and experiences with your own little sister, no other girl - be she a girl you crushed on at school or an internet porn model - had ever gotten you as throbbingly, uncontrollably stiff as you were this moment with Lily's slender fingers wrapped around your penis.
"Oh," she said. She didn't let go of it, but continued to hold it this way and that, observing it from all angles. "I mean it's really tiny, Tommy. I've heard other girls talking about them but they always made them sound so big and scary." She lifted it straight up, pressing it against your lower belly. "This isn't big at all. It's really small." She tugged on it a couple of times with her forefinger and thumb. The sensations her rough, amateurish handling sent through your rigid cock felt absolutely delicious, and you realized with rapidly-growing panic that you weren't going to last very long before crossing the point of no return.
"D-don't do that," you warned her, and she stopped, letting go of your penis. Your little dickie bobbed and bounced up and down visibly. You clenched inwardly, trying to prevent a very messy result.
"Did I hurt you?" Lily asked, suddenly concerned for you. "I'm sorry, I didn't mean to."
"No," you admitted reluctantly. "It's not that. It's that...um...if you do that - you know, like to a guy - you might make him..." Your embarrassment was overwhelming you now, making your face so flushed. "Never mind, it's not important."
"Tell me!" Lily whined. "Come on, Tommy, please? I really wanna know." She pouted, giving you her best puppy dog eyes. "It's not like I'm ever gonna get to find out for myself. No boy is gonna want to be with me. Come onnn..."
You sighed. "Do you know what happens when a guy, um...has sex?"
Lily's face seemed to blush anew. She shook her head no.
"When, um, a girl makes him, you know, hard down there," you said, gesturing vaguely at your diminutive member, still at full attention, "she takes it into her, um...her pussy. And the guy, um, pushes it in and out until he, uh, c-cums. Inside her." For all of your teasing and suggestive games, just coming out and explaining the birds and the bees to your little sister was surprisingly difficult for you.
"He 'comes inside her'?" Lily said. "Like how? What does that mean?" You rolled your eyes. How could she be so sheltered?
"Haven't you ever seen porn?" you asked her, exasperated. "Or, you know, played with yourself?"
Lily shifted her weight uncomfortably, resting her hands firmly in her naked lap. She looked away, embarrassed. "Promise you won't tell?"
You laughed, despite your embarrassment. "Lily, do you really think I'm going to tell anyone about all of this?" She looked weirdly awkward, still unable to meet your gaze, so you said, "I promise. You can tell me anything and I won't tell."
She looked up at you again, struggling to hold your gaze without looking away self-consciously. "Sometimes, I touch myself," she said with a guilty expression, as though she were admitting to a terrible crime. "It feels really good, but it isn't just that. Sometimes I think about...things...when I feel myself and, and I get all wet down there, and it feels even better."
"Right," you said. "That's playing with yourself. It's called masturbation. That's when you make yourself feel the feelings you would have when you... you have sex."
"Oh," she said, her eyes getting even wider. "It feels super good," she whispered. "Even though I know I'm not supposed to do it."
"Yeah," you agreed. "But it's okay if you do it, it's nothing to feel bad about." Despite your assurances that masturbation is healthy and normal, you've always felt perverted when you did it, and always worried what the girls from school would think of you if they knew how often you did it, or worse, what fevered tawdry fantasies you imagined about them while doing it. "So, um, when a guy does it, his p-penis shoots out white stuff. It's called cumming. Semen, I mean, it's what it's technically called."
Lily's hands remained firmly between her thighs. You weren't sure, but you began to suspect you noticed subtle movements in her knuckles. Was she playing with herself right in front of you? You felt a surge of sexual desire flood your body, and your erect little dick pulsed in the air.
"I bet it feels really nice," she said wistfully, transfixed by your small erection. "I want to have sex someday."
Your heartbeat was racing. If anyone ever found out about this, your social life would be as good as gone. Your mother would never forgive you. You would be a social pariah. But your twelve year-old little sister was kneeling completely nude in front of you, almost masturbating from sheer horniness, confessing her desire to have sex. Alarm bells were ringing in your brain, telling you how wrong this was, what a pervert you were for even considering the possibility. But your little penis was absolutely erect and nearly dribbling with precum. And now that Lily - who had never before even seen a penis - had confirmed your fears that you had an undersized, inadequate little prick, you worried that you might spend the rest of your life tormented by your virginity if you let this opportunity pass you by.
You swallowed hard. "Lily," you said, your voice hoarse and quiet. "Do you want to have sex with me?"
===
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