Tiffini’s dilemma

I lead Tiffini back to her bed and climb in to cuddle with her for a while. She’s shaky enough that she leans on me for support. She curls in to me, spooning, and puts my hands on her boobs. To my surprise, she begins crying softly. “Tiffini, what’s wrong?” I ask gently.

“Andrew?” she asks tentatively.

“Yes—I’m here for you,” I tell her. “What’s wrong?”

“That was wonderful—you were wonderful—you made me feel incredible—but now what do I do?” Tiffini asks, her voice thick with tears. “My sister wants to date you—she just hasn’t admitted it to herself—and I couldn’t compete with her even if I wanted to—and I do, I want you so badly, but I couldn’t do that to her—even if I thought you’d rather have a high-school girl than her. But the boys in my school are—”

“Stupid, I know,” I interrupt softly. “But surely not all of them are stupid, are they? Don’t you have any friends who are boys?”

“My best friend, Marc,” she answers. “We’re in a bunch of the same classes, and we study together all the time. He’s sweet and funny, and he’s really smart.” She pauses for a moment to think. “He’s actually pretty cute when he takes his glasses off. But he’s not into girls.”

“Really?” I ask, pretty sure I know where this is going. “Why do you say that?”

“He never talks about girls,” Tiffini says. “I talk about boys some, but he never talks about girls at all.”

“When you talk about boys, does he join in?”

“No, he just gets really quiet until I change the subject,” she replies innocently.

“That doesn’t mean he’s not into girls,” I tell her gently. “It means he’s into you.” Her body stiffens against me. “I could be wrong, but I’m sure I’m not. You’re his best friend, you like him as a person, he likes you as a person—and he probably thinks you’re the sexiest girl on the planet, and he knows you’re way out of his league. I’d bet he’s been head over heels for you for years, and scared to death to say anything because he’s sure it would end your friendship. This way, at least he gets to be close to you, and he doesn’t want to lose that.”

Tiffini turns her head to look at me. Her eyes are wide, and brimming over with tears. “I’ve been hurting him, haven’t I? And I never knew it. What do I do?”

I kiss her softly. “Anything you want, I’m sure,” I say with a grin. “Have him over to study—preferably sometime when Kimberly isn’t here—and jump him. Maybe something time-honored; tell him you’re too warm and take off your shirt. If his eyes don’t bug out, he’d have to be dead. Play coy, ask him if he likes what he sees, then just respond to whatever he does. Ask him if he wants to see more, and take off your bra. Maybe ask him to touch your tits, or kiss them. Maybe comment on the bulge in his pants, especially if it’s big, and ask to see it. Ask if you can touch it, then go down on him. You’re a naturally-gifted little cocksucker; once you’ve gotten your mouth on his dick—or his mouth on your tits, either way—he’ll be yours.”

Tiffini flushes with pleasure, then asks, “Do you think he’ll be as good at eating pussy as you are?”

I consider how to respond for a moment, then tell her frankly, “I’d expect he’ll know every bit as much about it as I did this time last year—which is to say, 100% of nothing.” Her face falls a little. “Everything I know, I’ve learned this school year, most of it because Alyssa taught me. You’ve had your pussy eaten now, so you have some idea what you like. You can teach him to please you, and then the two of you can discover more together. I will say this.”

“Yes?” Tiffini asks hopefully.

“I’m sure as sunrise that if you give him a chance, he will do anything and everything he can to please you, and he’ll give it everything he has to do it as well as he possibly can. He’ll do it because he gets off on it himself, I would expect, and he’ll do it because he wants to make the most of his chance. The more he pleases you, the more likely you are to keep him. If he’s in love with you and eager to please you, everything else will come.”

Tiffini giggles at my unintended pun. Once she calms down, she says quietly, “I’ll do it.” Her voice lifts as she adds firmly, “Marc won’t know what hit him.”