Caleb Fills the Nerd

For a second, Caleb thought he somehow missed and was pushing into her asshole. How could a hole this slippery and built for fucking put up this much of a fight?! But frustration drifted into satisfied assurance as he shoved past the unwilling ring of her entrance, shoved again through a membrane he barely felt himself break, and one last time to slowly push the rest of his length into her.

Gina’s flailing legs and him needing to pin her hands to her face—lest she scream loud enough for help to arrive—did not paint a pretty picture, Caleb knew. But those concerns were quickly outweighed by the gorilla grip his most valuable member was experiencing. He leaned onto her sweaty body, adding ever so slightly to the sensual, vice grip on the head of his cock as he groaned softly and right over her face. He should be saying something, should be making sure this is all still according to plan and that her status hasn’t changed… but he just looked down, locking lustful eyes onto pained ones, and rose only to get better leverage.

Slowly, his explorer withdrew from the path cut through the impenetrable jungle of flesh, trembling as he felt her involuntarily masturbate his trapped dick. He would love to fuck her hard and fast, but it was impossible: with her pussy fighting to squeeze him out with maximum, ridiculous strength at every inch of the way, it was clear he needed to beat this box into submission before he could be off to the races.

So he pulled out, bit by bit, watching her body convulse and the lump on her pelvis shorten until his cock’s head felt that particularly narrow, vicious grip just under the rim. “H-Holy shit.” It was all he could manage while she moaned and cried with hands over her mouth, her flat chest inflating and deflating rapidly as she hyperventilated during his ****.

Her **** of him, he rephrased it in his mind, as he held her down and **** his uncensored, unprotected cock through her blood and lubrication-slick channel… just as she made him do it.

Gina’s hairy mound re-inflated slightly as he re-entered, and she finally collected herself enough to stop most of her screams and to sit up on her elbows. Her hands never left her mouth, even when Caleb let them go; she didn’t want anyone to find her **** this man in the middle of a library, after all. She did her best to sit up and confirm what she already knew: he was inside her, and there was no undoing the harm she had done. The occasional involuntary hug of her thighs was as far as she fought Caleb; she was the one making him do this, after all. As he pushed again to the hilt, again forcing himself into the deepest, least-tense pockets of her vagina, she internalized the only explanation for this horrible, painful loss of her maidenhead and dignity, all with the now palpable, pulsing risk of unprotected sex.

This was punishment. It locked into place in Gina’s mind as her mental trauma transformed to offer a single, perfect explanation. It was the only thing that made sense. This was self-flagellation with the meatiest whip she could find. Where did she grow this need for penile penance? Was it guilt for what she’d done to Caleb until now? Was it her procrastination in getting back to the project sitting idle in the forgotten laptops behind her? Was it for something broader, like her general outlook and approach to life?

Whatever it was, she sobbed knowing she deserved it. She was a **** now, and in her twisted **** mind she made a mockery of her redemption by using Caleb to do it. Worst, she **** him to have intercourse, leaving his unprotected member drooling pre-cum and God-knows-how-much-more into her fertile, **** snatch.

Gina felt she was a monster, irredeemable and ever-consuming, and it was a guilt outweighed only slightly by her sudden awareness of how close to impregnation or venereal diseases she might now be.

Caleb didn’t really pick up on any of these complicated expressions or thoughts as the writhing nerd on his cock sobbed and squinted without her glasses. She was staring and crying at the place of their union, but she smothered herself all the same. She wasn’t stopping him. Given he was inside her hot, incredible depths, the physical therapy appeared to be working perfectly.

“Trust the process,” he groaned with a shuddering voice as he tugged again at her insides, reveling at how much more resistance she gave him as he tried to withdraw. Pulling out of Gina before coming was going to take every ounce of willpower Caleb had, and the thought of coming inside her now occupied his mind. Cool, calm Caleb would have seen the obvious problems there: he was not about to knock up a dubiously-mentally-handicapped, flat-chested chick who was, from his perspective, incredibly rude to him all morning. The only polite thing she seemed to do was let him have his way with her, and even then only because she thought she had enslaved him to do it. Caleb wouldn’t even consider tying his life to all the responsibilities, reputations, and/or police reports knocking this girl up would generate.

But none of that occupied Caleb’s mind right now. He instead considered how incredible it would feel himself swell to ejaculating as his head pushed back in while her pussy resisted and squeezed the whole way. He could swear she thought about the same as she cupped her hissing mouth in one hand and groped the bulge under her stomach with the other, her eyes wide in pain and disbelief. The bulge wouldn’t stay smaller for much longer if he actually dumped his full load into her…

… and it was about at this consideration, with the tip of him rubbing against the farthest portion of her vagina, with his blood flowing hot and his mind freely wandering, that he began to feel that pressure, that gentle, wonderful sensation building somewhere between the base of his spine and the end of his cock. His meat swelled, ready to push against the crushing surroundings enough to permit semen to flow. His balls twitched as he felt her sucking cunt hug the base of his meat. Everything rushed between his heads and...

... well, he knew he should pull out. With his last ounce of sense, the token effort was made... but pulling out was, in his experience, only made possible before because of how little resistance his prior lovers offered. They were happy to let him go, and their excited crotches were pliant, squeezing only slightly in the best circumstances. Lubricated as Gina was, it should have been a simple matter of tugging himself free... save that the wrenching, now-traumatized grip of the dysfunctional vagina wrapped so tightly onto his member that he wondered if semen would escape him at all.

So when Caleb tugged, then tugged harder, he did not escape her. Instead, his pleasure peaked as she resisted his release at the moment of orgasm, freeing him to revel in the animal instinct to seed his fertile victim... and when he pulled one last time, only to be met with that same, incredible resistance, only getting half his cock free as he felt cum rush through him, he didn't give it anymore thought before groaning his delight and surrendering the effort.

Gina, eyes wide and looking over the shoulder of the man collapsing and groaning atop her. She laid helplessly as she felt baby batter fill her, and her mind slowly translated the foreign sensations coming from below. Tight and constricting as she was, the space near her cervix had the right structure to permit a bit of fluid, but she felt how quickly that space became tight with fluid. The little space he freed in her vagina from his failed attempt to pull out—no, no, he just wasn’t permitted to pull out, because she didn’t want him to, she rationalized—was now expanding with jizz that couldn’t escape through the hermetic seal of meats wherever she clenched him. Only Caleb’s slow, resumed withdrawal permitted any relief in the liquid pressure inside her.

When at last he finished pulling out, his sweaty, half-clothed body lifting from her naked one, Caleb knelt at her crotch and tried spreading her lips. The damage was done… and now as he looked at her slightly reddened, irritated hole, he realized that most of the fluid that escaped her was just the combination of lubrication and blood on his dick. There was no sign of his own cum except the last droplet leaking from its head, now finally able to escape; not a single drop left Gina besides as her likely-injured pussy just continued to clench and keep everything inside.

This was a problem for post-nut clarity Caleb. “Push it out,” he shakily commanded, forgetting the narrative here. But to his credit, Gina took that to mean she wanted him to encourage the same… senseless as that was. You didn’t stop pregnancy by dumping the semen out later! So this must mean… she just wants to further humiliate herself.

After all, Gina slowly realized, she must have wanted him to fill her to capacity with spunk. Why else did he only pull out enough to really load her up? It’s… what she wanted.

“But I… I don’t want to have kids…?”

“Neither do I, now hurry up and squat to get it out,” he hissed, frustrated. They’d already made a mess in here, but he’d get all the paper towels in the world if it meant his load would at least finally leak out of her time-locked vault of a—

Knock knock.

Both adults stiffened like children caught stealing. Someone must have heard them. Someone was coming to check on them… someone not deranged like Gina, someone who would knew what **** was and who here had committed it. All Caleb’s delusions of this being anything else were suddenly swept away as reality and consequence stacked too quickly for him to account. He came to a single, angry conclusion.