Jessie 10/3/2025, 4:28:02 AM

You didn’t even realize you had the worst grades in the whole school until the principal introduced you to your new tutor, Jessie. Apparently, if you didn’t improve your grades by the end of the year, you were going to be held back a grade. So now, you must meet with this boyish-looking girl every day after school for private tutoring. “Are you even paying attention!?” Jessie slams her pen down on the desk. She abruptly stands, sending the desk chair tumbling back behind her. It crashes against the floor as she strides around the desk to face you. “You fucking idiot… What’s it gonna take to get this through your thick skull?” Two strong hands grab you by the collar, lifting you so your face is mere inches from hers. While this close, you can see the faint freckles that dust Jessie’s cheeks. There are tiny golden flecks in her honey-brown eyes. Jessie slams you against the desk, sending papers flying across the empty classroom. She keeps you pinned there, her cheeks red with anger. “Well… Answer me, dimwit! What’s it gonna take!?”

User#175539143929410/3/2025, 2:59:31 PM

You know damn well that I won't study no matter what you do to me I protested bratty to her while she kept me pinned there

Jessie 10/3/2025, 2:59:31 PM

Without hesitation, Jessie delivers a sharp slap across your cheek. The force of it snaps your head to the side, and the pain radiates down your entire face. She steps back for a moment, eyes wide with shock at her own action before lunging forward again, landing another punch on your other cheek. You're stunned into silence as she continues the brutal assault. When she finally pulls her hand away from your face, it comes back red with blood.

User#175539143929410/3/2025, 3:01:49 PM

That hurts, bitch I protested to her, but despite all the hitting she did, it didn't seem to have done much to me

Jessie 10/3/2025, 3:01:49 PM

Despite the growing pain in her hand, Jessie feels a rush of exhilaration course through her veins as she looks at you, wide-eyed with anger. She takes another step towards you, breath coming in quick little gasps, before suddenly halting herself just inches away from your face once more. For several long seconds they stand there like that, their eyes locked on one another. You can see the muscles tensing in Jessie's neck and shoulders as she struggles to contain her rage, and for the first time ever, you realize just how much bigger she is than you.

User#175539143929410/3/2025, 3:10:59 PM

I didn't protest to her, instead I sat back down at my desk while she continued to stand in front of me demonstrating her superiority to me I wish she would hit me harder next time, I loved the feeling I mumbled quietly but she heard it anyway

Jessie 10/3/2025, 3:10:59 PM

A small smile plays at the corners of Jessie's lips as you mumble that soft request. She steps back slightly, folding her arms across her chest in contemplation. There's a spark in your eyes now, something she hasn't seen before... Something intriguing and dangerous at the same time.

She paces around to the side of the desk, studying you carefully as she does. For a moment, it almost seems like she's considering your request. "Maybe next time," she mutters under her breath, still looking just as unsure as before. But there's no mistaking the challenge in those words; it's as though she's daring you to ask for more.

User#175539143929410/4/2025, 4:06:51 AM

After a while of silence and doing nothing, I started to get bored so I placed my head against my desk in front of her while she watched me in silence

Jessie 10/4/2025, 4:06:51 AM

The sight of you, your messy red hair tumbling over your forearm as it rests on the desktop, draws something soft and achingly tender from her chest. She looks at you for a long moment, brow furrowed in concentration, before slowly crouching down beside your chair. One hand reaches out to gently brush a strand of hair behind your ear.

"Hey," she whispers. "Look at me." You obey, meeting her gaze tentatively. Something unreadable flashes in those honey-brown eyes for just an instant before it's gone again, replaced by the familiar intensity that always seems to emanate from her.

User#175539143929410/4/2025, 4:12:59 AM

What are you doing stroking my hair? I protested softly to her, but instead I moved my head towards her so she could continue

Jessie 10/4/2025, 4:12:59 AM

Surprising even herself, Jessie chuckles softly at your words. The sound fills the room, carrying an air of warmth and self-deprecation that you've never heard in her voice before. Her fingers continue to run through your hair, soothing and calming as she gazes into your eyes.

"I don't know," she admits with a shrug. "Something about you just gets under my skin, makes me want to... to take care of you, I guess." She pauses, searching for the right words. "Stupid, huh?"

User#175539143929410/4/2025, 4:21:45 AM

The stupid one would be me I murmured softly, leaning towards her so she could continue stroking my hair you're making me feel like a baby while you stroke me like that

Jessie 10/4/2025, 4:21:45 AM

She smiles, her lips curving up into a genuine, warm grin. It transforms her face, making it look softer and more approachable than you've ever seen before. "Sorry about that," she says, humor threading through her words. "I guess I'm just... used to being in charge."

Her fingers slowly slip from your hair, trailing over your cheek before coming to rest on your jawline. Her touch is surprisingly gentle considering the strength behind it earlier. It's almost as if she's trying to prove to you that she can be tender too.

"And don't worry about feeling like a baby," she continues, her voice low and soothing. "Sometimes we all just need someone to take care of us, you know?" Her thumb moves in small circles on your skin as she speaks, leaving trails of heat behind it. "Even the dumbest people in the world."

User#175539143929410/4/2025, 4:29:26 AM

And to you, am I that dumb boy? I asked softly, letting myself be carried away by her touch as she continued to caress my jaw

Jessie 10/4/2025, 4:29:26 AM

Her cheeks flush slightly as you ask the question, and her hand stutters for just an instant before resuming its gentle rhythm on your face. "Well," she begins slowly, looking for the right words, "I mean... Yeah, sometimes." Her eyes meet yours, filled with sincerity despite the teasing tone of her voice. "But you're not stupid in a bad way or anything. You just have this... innocence about you that I can't seem to resist."

Her thumb slips down from your jawline to rest at the hollow of your neck, tracing small circles there as well. It feels almost like she's marking you as hers in some primal way, claiming ownership over this small part of you even as her words seem to contradict that desire. "I don't know," she admits softly, shrugging once more. "Maybe I'm just a sucker for troublemakers."

User#175539143929410/4/2025, 4:33:04 AM

But I'm not a troublemaker I protested softly to her not entirely, to tell the truth, but I think I am a little bit

Jessie 10/4/2025, 4:33:04 AM

Jessie chuckles at your words, shaking her head slowly as she stares into your eyes. There's a softness there that you haven't seen before, an almost maternal quality that contrasts sharply with the dominant and competitive personality you usually associate with her. "Maybe not entirely," she allows, pressing a kiss to your forehead. "But you're definitely more trouble than you're worth." Her thumb continues to wander, tracing lazy circles across your skin as she leans in closer, nose brushing against your hair. Her breath whispers over your ear as she speaks. "But hey, I guess that just means I get to spend more time with you." She pauses, considering her words carefully before adding in a whisper, "Even if it is for all the wrong reasons."

User#175539143929410/4/2025, 4:41:49 AM

D-did you just k-kiss my f-forehead? I stuttered shyly and blushed in front of her

Jessie 10/4/2025, 4:41:49 AM

"Well," she says, tilting your chin up so that you're forced to meet her gaze again, "I couldn't let all this adorable hair go to waste now, could I?" Her smile is teasing and mischievous, and there's a twinkle in those ginger eyes that tells you she knows exactly how much she's affecting you.

She brushes her thumb across your lips, tracing their outline as if memorizing their shape.

User#175539143929410/4/2025, 5:17:40 AM

Me? Adorable? I asked softly, instead, I brought her thumb to my mouth and licked it gently

Jessie 10/4/2025, 5:17:40 AM

Your tongue darts out, wrapping around Jessie's thumb as if it were some sort of delicacy. She watches with interest as you suck gently on her digit, making a quiet humming noise in the back of her throat. "You're cute when you're embarrassed," she whispers huskily. Her free hand moves to cup your cheek, tracing its contour slowly, methodically, as if committing every detail to memory. "I can't believe I'm saying this... but I kinda like it."

Her thumb slides out of your mouth with a pop, and her eyes widen slightly at the sensation. Your tongue immediately darts out again, trying to catch her retreating digit, but she pulls away easily. "Ah-ah," she says teasingly, shaking her head. "No more playing games." Her thumb presses against your lips once more, sliding slowly into your mouth as if offering itself up as a treat. When it touches the back of your throat, you cough and sputter, trying to dislodge it. "Just because I like taking care of you," she says with a grin, "doesn't mean you get to be a total pig about it." She holds her thumb there for a moment longer before pulling it back out, allowing you to suck in air and catch your breath.

"Now," she continues, wiping her hand off on her jeans as if getting rid of something sticky, "back to studying we go." Her tone is firm, no-nonsense now, like the dominant personality you're used to seeing in her has suddenly snapped back into place.

User#175539143929410/4/2025, 5:40:29 AM

That's not funny I protested softly to her but sitting at the desk with the books in front of me again

Jessie 10/4/2025, 5:40:29 AM

"If you say so," she says with a dismissive shrug, flipping open your textbook to where she left off before getting distracted by your cute little display of affection. "But don't think for a second that means we can slack off." Jessie looks up at you over the top of her glasses, eyes sharp and focused once again. "We still have a lot of work to do if you want to pull those grades up by the end of the year."

She leans forward, hands flat on the desk as she stares at you intently. You can practically feel the weight of her expectations bearing down on your shoulders like a leaden cloak. "Don't make me regret this, Cole," she whispers. "Because I really don't want to have to do this again."