Chapter 1: Foundations

With a final grunt of effort, Jake buried the last inch of his cock into the clenching asshole of the whimpering girl beneath him. It had taken the better part of an hour to work his way into her anal cavity, despite a generous amount of Astroglide easing the way, as every inch he had had to pause to allow Lisha’s body to adjust. Literally every inch; it took a full seven pauses before he was finally embeded. Relieved that he could finally get started- motionless sex wasn’t very stimulating, no matter how tight the hole was- Jake adjusted his knees and began to pull his hips backwards.

“Oh, oh, hold on, stop...” Lisha gasped out, taking her mouth off the pillow she had been biting.

Suppressing a sigh, Jake dutifully paused his retreat. He had barely pulled out half an inch before she stopped him and as pleasant as her insides felt wrapped around his shaft, he was becoming increasingly impatient to get to the good part.

Granted, the entire situation was partially his fault. He had smooth-talked his way into Lisha’s ass without setting up any prepwork; no thumbs slyly popped in during sex, no buttplug training to subty stretch and train her anus to accept his seven inch cock, just a few whispered platitudes and a large dollop of the Astroglide he kept at the bottom of his backpack.

It’s not as if he had expected the going to be easy, of course. In fact, he hadn’t actually expected Lisha to even seriously consider the idea. After all, the small red stain on her cotton-white sheets (tossed onto the floor after the act) from just a few hours ago were a color-coded marker of her sexual inexperience, but in all honesty Jake had grown somewhat tired of Lisha. So he’d decided he may as well go for broke.

Jake had been casually working on Lisha for a few weeks before he finally got to pop her. She was cute enough, but nothing special. A 15-year old Sophomore from the same highschool, Westwood High, she was about as generically attractive as a teenager could be: white, midwestern skin tone, straight brown hair worn down to her shoulders, nice B-sized tits with normal, pink nipples and, somewhat unfortunately, a flat white girl ass. She was also supremely uninteresting. The entirety of Jake’s seduction had been based on his seniority and good lucks, relying on mysterious, silent smiles in her direction and banal conversations in the school hallways, conversations about nothing at all since as far as Jake could tell, Lisha had absolutely no hobbies. No particular likes or dislikes. So average and boring that Jake normally wouldn’t have bothered.

But still. She’d been a virgin. A point was a point. If he managed to somehow smuggle the blood-stained sheets out of the house, he’d get an extra point, since actual bleeders were pretty rare, most girls busting their cherries from gymnastics or biking or a little too much enthusiasm with certain vegetables. And he was, after all, seven- or rather, six and a half- inches into her rectum, so maybe she wasn’t quite as boring as he’d thought. Maybe.

Bringing himself back to the present, he considered the situation with an expereinced eye. Lisha clearly wasn’t going to adjust to his girth in any reasonable amount of time, so he decided to simply take matters into his own hands.

Firmly taking an asscheek in each hand, Jake first thurst forward slightly, embedding the half-inch of dick he’d extracted back inside, earning a distinctly unladylike grunt from Lisha, muffled once again since her face was shoved into her pillow. Then, ignoring Lisha’s mumbled protests, he slowly but steadily pulled out until only the head of his cock remained inside its’ sheath. Lisha let out a heavy groan, picking her head up and starting to turn her face back towards him. It seemed she thought he was just going to give up and pull out.

Silly girl. She’d learn.

Shifting his hips a bit so he could angle straight downwards, Jake thurst the entirety of the dick up the poor teen’s asshole before she could register what was happening. With a squawk Lisha attempted to pull forward and away, but Jake lifted his left hand off her flat ass and onto the back of her head, gently but firmly grasping a fistful of hair.

Then, leaning his body over her back, he forcefully shoved her face into the pillow while he took his pleasure.

It wasn’t the easiest way, obviously. At first Lisha squirmed wildly, trying to lift her head or else at least knock him off his stride. But Jake was not only much larger and stronger than the poor girl, he also had leverage on his side. Keeping her pinned down while he sawed his cock in and out of her ass was a bit troublesome, but it was better than taking all day to get his rocks off.

Finally, after about five minutes of solidly pounding her teenage asshole, Jake thurst forward a final time, letting his grip on Lisha’s head relax as he spewed a load inside of her. Not that there was all that much left to give; he’d already cum three times today, twice in Lisha’s formerly virgin pussy and once earlier in the day, at lunchtime, down the throat of a cheerleader named Amber.