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Chapter 143 by bobbobbobthethir
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Late night seminar grind with Charmaine
You find yourself in Charmaine’s room a couple hours after dinner, the two of you talking through each other’s papers for the seminar assignment due the next day.
The dark-skinned girl has somehow managed to snag for herself a comfy single. It’s one of the largest rooms that you’ve seen in East Hall—usually, the good rooms all go to the upperclassmen like Emma or Dominic, and you wonder how this one slipped through the cracks. You’re not complaining, though, as you rock back in her arm chair, leafing through her printed copy of her paper while she peruses yours on your laptop.
“You know, this is a surprisingly genuine take on the subject,” you say, as you finish reading Charmaine’s paper.
“I would think so,” she scoffs. “It’s not like I wanted to come off as sarcastic.”
“No, I meant that in a good way,” you say. “I thought the paper came off as authentic. Real. Like you really expressed how you feel about the matter.”
Charmaine tosses her black hair over her shoulder, and gives you an interested glance.
“What do you think I was trying to say?”
“That as the world has gotten more progressive in modern times, it’s been easier than ever for people to actualize their love, to consummate that deep feeling through that beautiful thing we call sex,” you say, liberally stealing lines from her essay. “You come across as a very big fan of love.”
Charmaine turns her face aside, pretending to stare hard at your laptop, but it’s impossible to miss the semi-mortified expression that crosses her face in that moment.
“There’s nothing wrong with that,” you say, bringing a friendly smile to ease her. “I wrote about how sex and love go together well, too.”
“Yes, but still…”
“Would you like to be in love?” you ask her.
“What?” Charmaine laughs, a nervous titter that she abruptly cuts short. “Yes, I mean, yes, why not, with the right person?”
“I know how you can find him,” you say, meeting her eye firmly.
Charmaine shoots you a very skeptical look, pushing your laptop aside.
“How could that work?” she asks.
“The answer’s in your paper, actually,” you say, plopping it down on her desk, complete with your scribbled comments in pen. “See? You wrote it right here: Sex and love are like opposing walls in a hollow cave: they echo the feelings that comes from within, amplifying it in a virtuous cycle to create something greater than was originally there.”
“I… I suppose I did,” she says. “But that sentence needs work. You even wrote so, over here!”
“But the idea behind the sentence, regardless of its construction—that’s something you believe in,” you say.
Charmaine nods her head, and then gulps.
“So does this mean…”
“I think there’s really only one conclusion,”’ you say. “You’ve got to have sex, and that’s how you make love.”
Charmaine regards you in silence, her eyes blinking quickly, her beautiful features looking torn between two callings.
“I haven’t done it with any of the guys here,” she says quietly.
“So I’ve heard,” you nod. “All the guys think it’s because you’re playing hard to get.”
“Am I not?” she asks, looking at you with interest.
“I think you’re still trying to figure things out for yourself,” you say. “You’re not sure if you want to put out for a guy yet.”
Charmaine pauses, and then nods awkwardly.
“I’ve never done it before,” she says quietly. “But you can’t tell anyone!”
“The secret’s safe with me,” you say solemnly. And then: “But, if you’d like, you can get your feet wet with me. It doesn’t have to be the full thing. Have you ever seen a cock before?”
“Only on the internet,” she says, her breath picking up. All of a sudden, it’s like her eyes are glued to your crotch, staying fixated on that spot in a pure fascination that you find endearing.
“Here,” you say, slowly pulling your pants down, and then your boxers to follow.
Your cock springs out, dangling before Charmaine. Though it’s still partially limp and floppy, you can see her eyes widen, her hand instinctively reaching out for it.
“You can touch it,” you smile, taking her hand into yours and guiding it towards your shaft.
“It’s… weirdly warm,” she says, resting her hand on the shaft, looking up at you apprehensively. “And smooth, too. Should I… stroke it?”
“That would feel good,” you nod, and you let out a little groan of pleasure as she slowly begins to jerk you off, the feel of Charmaine’s hand on your cock soon bringing you to full mast.
“So do I just keep doing this?” she asks, as she quickly gets the hang of that iconic back-and-forth gesture.
“Guys tend to like it faster,” you say, and she responds in kind, beginning to move her hand at a faster pace, your cock delighting with each pump of her hand. “And tighter. You can almost squeeze it and it will… there we go...” You grunt aloud as Charmaine gets the idea, her hand clamping down like a vise around your cock. “But… needs lubrication, or else the friction burns like a bitch.”
“So what do I do?” Charmaine asks, quickly loosening her grip.
“A blowjob is one way to do it,” you say, but she quickly shakes her head, for no, that would be going too far for her today. “But your saliva can work, too. Or just good old fashioned lube, if you have any lying around…”
Charmaine goes for the spitting option, getting a good glob of it onto her hand, and as she recommences her handjob, far better lubricated now, you smile. Who’d have thought you’d get her doing this dirty stuff so easily?
“That’s it,” you groan, as she finds a cadence that brings you dangerously close to cumming. “God, I’m close…”
“What do I do?” Charmaine panics, abruptly letting go of your cock.
“Where do you want me to cum?” you ask her.
“Uh… on my face?” comes her answer, and that’s how you know she’s seen this stuff on (and only on) the internet before.
You bring her hand back to your cock, and she begins to stroke you off with a fervor once more; though the momentary lapse in attention stopped the imminent orgasm, you’re back at the edge within seconds.
“Your face, here,” you manage to grunt, and Charmaine dutifully lowers herself to stare up at your cock, her eyes widening slightly in shock as spurts of thick white cum erupt from your cock, painting her face in goopy strands of your semen.
“Aiee!” Charmaine yelps as the cum hits her face, her instinctive flinch back completely understandable given the circumstances.
“You did ask for it,” you chuckle, as she blinks a couple times, making sure that none of the stuff got into her eye.
“I need… I need to clean myself up,” she says, suddenly looking awfully embarrassed at herself once more.
“Nothing that a couple tissues and a good rinse won’t solve,” you say.
You pull your boxers back up and zip your pants, and then look at Charmaine, who’s taken a dab of your cum and licked it off her fingers. She makes a face, and you chuckle.
“So, what do you think? Did sex lead to love?” you ask.
“Jury’s still out,” Charmaine smiles. “But that means the trial’s not over yet.”
Charmaine +25
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The Freshman 15
A young man gets to college late. Can he still screw the Freshman 15?
A young man gets to college late. Can he still screw the Freshman 15?
Updated on Aug 22, 2025
by bobbobbobthethir
Created on Sep 16, 2018
by bobbobbobthethir
With every decision at the end of a chapter your game state can change. Here are your current variables.
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