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Chapter 367
by
sexybjgal69
How does Nathan lose his virginity?
Jan. Week 3: Thursday-Nathan fucks Leah doggy style (Suspicion: +5, Silence: +25)
She swept her hair over her shoulder and took a steadying breath.
"Do you know how to put this on?" she asked, her voice flat and businesslike, gesturing to the condom Nathan still held aloft like a nervous altar boy with the communion host. He nodded once, then shook his head, then shrugged, his Adam’s apple bobbing in his throat like he had swallowed a live fish.
"I—I’ve practiced. With a banana. For Health Class," he said, his voice tripping and almost falling. He looked at her as if expecting ridicule, and for a moment, Leah nearly laughed. But what came out was a soft sigh instead.
"I’ll help," she said, halfway surprised by her own tenderness. She took the condom from his trembling hand and rolled it between her fingers. "This isn’t a banana, just so you know."
Nathan’s cheeks burned.
"I know," he mumbled. "It’s a lot bigger than a banana."
"Let’s not get ahead of ourselves," Leah deadpanned, biting back a smile at his earnestness. It was almost endearing. She slid her hands over his waistband, hesitating a split second before undoing his jeans. He shuddered as she brushed against him, his breath hitching as she deftly maneuvered his pants and boxers to the floor. He was, predictably, achingly stiff, and his nervousness made him seem even larger somehow, as if his body was trying to compensate for his lack of bravado.
She paused, absorbing the strange power dynamic—not teacher and student now, but some other, more fucked-up hierarchy where she was both instructor and subject of desire, a curriculum of sin. Her fingers were cool and sure as she tore the wrapper, pinched the tip, and fitted the condom over his length with a slow, deliberate motion. Nathan whimpered at the sensation, and the sound sent a jolt right through her. She met his eyes.
"Are you okay?"
"Yeah, just—I—yes..Yes, I am." He nodded, but his words came out in a rush.
She almost asked what he meant, but decided not to. The less conversation, the better. She stepped out of her heels—practical, not too sexy, but still a part of her professional armor—and hiked her skirt up past her thighs. Her panties were modest, not the lacy kind she wore for Jonathan, but she peeled them down anyway, dropping them to the linoleum floor beside Nathan’s pile of clothes. She leaned over her desk, sweeping a stack of ungraded essays to the floor with a deliberate gesture. Nathan stood behind her, his hands hovering uncertainly at her hips.
"Like this?" he asked. She almost laughed again, but kept her composure.
"Exactly like that," she answered, guiding him with one hand, positioning him at her entrance, where the condom’s chemical slickness met her own warmth. The first moment of penetration was always a little awkward, but Nathan’s inexperience made it almost comical. He pushed too hard, then not at all, his entire body trembling as she coaxed him inside.
It was, she realized, surprisingly intimate—more than she’d expected. He was wholly focused on her, every nerve ending firing, and when he finally slid in, he made a noise like he’d been holding his breath since birth. She arched her back, feeling him fill her, and for a second, all her guilt and shame was replaced by the simple, primal pleasure of it.
He didn’t last long. She knew he wouldn’t. The first time was always ridiculous, a frantic, almost **** thing.

Nathan’s face went slack, his jaw dropping as he gasped and panted, his hands digging into her hips. She could feel him lose control, his body jerking as he came, and she almost pitied him for how quickly it was over.
But then he just stood there, buried in her, breathing hard and looking at her like he’d just witnessed a miracle.
"Sorry…that was so fast…" he said blushing.
She shook her head, touched in spite of herself.
"It’s okay Nate, it was your first time. it is always quick.” She reached her hand around behind her and ensured the condom was still on then slowly wiggled her ass and his cock out of her so there wasn’t a mess or slipping condom. She turned and stroked his hair and felt a weird tenderness for the boy. He smiled gratefully before finally fumbling for his pants.
"Thank you," he whispered. She almost said, For what? But the look in his eyes stopped her. He really meant it. She couldn’t decide if that made things better or worse.
They straightened their clothes, and Nathan slipped out of the door with a furtive glance back, as if he’d wake up at any second and find himself in another, less fucked up reality.
Leah slumped into her desk chair, skirt still wrinkled, and stared at the clock. She could hardly wait for the day to end.
What's next?
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Attaining Tenure
One Female Teacher Does Everything She Can to Get Tenure
Miss Leah Williams is on her final year to get tenure teaching at her beloved high school. She has a wonderful future--a loving fiancé a stable career at a good school. However--all that could change with this school year when a secret threatens to reveal itself...
Updated on Jun 7, 2026
by sexybjgal69
Created on Jun 1, 2022
by sexybjgal69
With every decision at the end of a chapter your game state can change. Here are your current variables.
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