AUTHOR'S NOTE: This story owes a great debt to "Six Times a Day" and its author, spacer_x, along with many others.
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Josh Smyth wasn't much to look at, at least according to his own standards. His long, ropy body couldn't fill out a tee shirt like some of the guys he'd gone to school with, and he certainly didn't think he was turning the heads of any girls. Sure, there'd been dates. He'd managed to convince at least one girl to accompany him for each of the high school dances, though they had ended less exuberantly than he'd hoped.
According to all the prom movies he'd seen (and he'd seen nearly all of them, as prom movies were something of a favorite with his mom), the evening would come to a climax with a kiss on the dance floor, possibly followed by some sexy something at a hotel. Instead, three of the dances ended with a chaste kiss on the cheek. The fourth ended with Aimee Pressler puking in the passenger seat of his rusting Honda Civic. She was the hottest of all the girls he's managed to cull, but the best action of the night was getting to see her panties as she fell out of the car and collapsed on the sidewalk in front of her house. It didn't exactly stir the imagination. Pathetically enough, he used that image in his masturbation session later that night, trying to block out the sour smell from the car and the bleary look on Aimee's face and just focus on the pink, satin patch of fabric between her legs.
He did get off, finally, kneeling in front of his desk, cum dripping down onto the cheap throw rug he kept under it. Why couldn't it be Aimee on the receiving end of that cum, he thought. He could almost see her, down on her knees, devilish eyes looking up at him, and a thin smattering of semen covering her nose and sides of her mouth.
It was all porn-fed fantasy, of course. An expert in all things pornographic, Josh could probably make a list of every possible position for fucking, every imaginable place to stick a dick. It was all possible, just not actual.
By the time he graduated high school, his list of sexual accomplishments included a painfully inept hand job from a former neighbor girl, some titty sucking from a girl at camp named Judy, and a handful of make-out sessions. It was actually Judy that he remembered most fondly, because she'd been so eager and giving. Judy was a counselor, not a fellow camper. Though he was just a few days past his eighteenth birthday, he was inexperienced and awkward. Judy was in college, which seemed impossibly sophisticated. She offered her breasts to him almost as a gift, like Rose of Sharon in the Grapes of Wrath. With the notable exception that Josh wasn't a starving migrant worker, but was hungry nonetheless for some tit.
After the camp incident, his porn habits had shifted towards older women. Yes, the humor was not lost on him that Judy couldn't have been more than 23 years old, but somewhere deep inside him, a switch had been flipped. Older women, the very same women that must have been walking around him all his life, suddenly popped out in bold relief. These weren't just old bags past their prime, like some breed of neutered nuns. There had always been girls in his purview. Now there were women.
Women, big beautiful grown women. Women who had had sex not just a few times in the back of a football players car. Women. Women who'd taken men in high school, and college, in marriage beds, and maybe in their offices. There was probably some wife on his block right now getting a fat dick stuffed in her, sweat running fast between her fat, womanly breasts. Oh god! It was just too much for him.
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He stood up and shook himself off. Thinking about all this sex that was (probably) going on around him nearly had him shaking with horniness. He'd been lying in bed trying to read through some excruciating history textbook for his World History Intro class. A month into his classes so far, college was different than he'd expected it to be. Much of the caste system of high school had been dispensed with, and he no longer felt awkward about enjoying the learning process. He could raise his hand and ask questions without someone hiding the taunt dork! in a loud cough.
The social aspects, sadly, were underwhelming. Again, he'd felt that Hollywood led him astray. Commuting to school was quite a ways away from Animal House. Parties? Yes, a few. Beer? Yes. Panty raids, women throwing themselves at you, and three-ways with hot girls and their roommates. No, no, and no.
So far, college had turned out to be a lot high school in this department: a lot of lusting after girls during the day and a lot of jerking off at night. To his credit, he'd been putting it off for two days, but his balls felt fit to burst and waiting had only made him more titillated throughout the day.
He threw the book down on the bed and checked the lock on the door. The last thing he wanted was Mom walking in during a wank session. Then he made his way to the computer and sat down. His cock jerked in his pants and he knew he wasn't going to last long. No sense in making a meal of it, he thought. Sometimes to get himself in the mood he preferred erotic stories to pictures or video. Josh had always been a reader and found that certain kinds of porn benefitted from a healthy narrative. Sure, a huge pair of tits flopping up and down got his motor going, but so did a seduction story... say of a hot older teacher seducing her student after class. A story like that could keep him on the verge of cumming for over an hour.
Not tonight, though, with a pile of homework stacked on the bed. He jumped right into the fray and pulled up one of those huge, free video repositories. "Older," "MILFS," "May/December..." these were the keywords that stoked his flames. He jumped right into a video of a woman with big tits squeezed into a little sweater. After the brief premise of a "friend" of her son's coming over to drop off some homework, she got to work on his cock. Narrative be damned, he thought, this bitch is hot.
Josh dropped his pants to his ankles and grabbed a hold of his dick. The woman on the screen unzipped her sweater and her huge breasts flopped out. They were just what Josh lusted after: big, jiggly, natural boobs that wobbled and rippled when she moved-- none of that rock-hard silicone business. Time seemed to freeze around him as Josh entered that erotic zone. He wasn't close to cumming, but all other concerns seemed to have slipped away. There was only his cock, his hand, and the video, a closed circle of lust.
The video finished and he went to the next, wanting to see more of this woman. Her sandy blonde hair and the shape of her lips were particularly alluring. Oh. He could feel it happening inside. The thing he tried to keep suppressed. He tried to focus on the actress and her marvelous tits and a hard cock passed between them, but it was too late. He knew what he wanted and he was no longer in control of his body. His left hand moved to the keyboard, as if of its own volition, and started typing in a URL.
