Charlie had always been a curious kid growing up. So naturally when he got his very own computer, he was bound to explore. As Charlie turned 18 and was a senior in high school, he finally found something that really excited him. He saw a woman using a strapon on a man, who seemed to love it. Charlie made a vow to himself that he would get fucked by the time he left high school. Little did he know how many times this would occur.
Charlie began playing around with his ass soon after seeing that video. He began with fingers and slowly moved his way up. He also began watching only strapon and shemale porn, where the guy gets hammered in his ass. Speaking of hammers, as Charlie began wanting larger and larger objects to fuck, he found a thick hammer in his garage that seemed to fit the job perfectly. Using crisco, Charlie would lube the handle up, and after fingering his ass, would slowly slide it in, making sure to rub his prostate. He loved the feeling of getting six inches up his ass, but he felt he was missing something. Girth.
Charlie really wanted to get something more like a dick to use while he jacked off. One day though, while he was in his parent's room, he stumbled across a plastic box under their bed. Inside it there were four or five different dildos of varying size, from 6 inches long and 1.5 inches around to a monster 13 inches long and a good 4 inches around. Charlie's mouth watered at his find, and his ass twitched. He grabbed a black one that was about 7.5 inches long and about 2 inches around, and ran back to his room. He lubed the dildo up, sat it on a chair, and lowered himself down on it. He rode the cock for a good half an hour, loving every minute as the realistic cock stretched him and gave him several powerful orgasms. Once he was finally worn out he sat back down on the cock and stayed there for fifteen minutes, savoring the feeling. Charlie knew that he would not be able to go back to the hammer after experiencing this.
After a month of slowly moving up in size Charlie was ready for the massive 13 inch white dildo. He had already been trying to suck the cock while fucking himself with other dildos, but he was now ready to fuck the huge cock. Charlie wanted to try a new position with this one though, one that would make him feel more submissive, so he mounted the dildo on the wall in his bathroom so he could watch himself doggy style fuck it. Also, so he could finally find a partner, Charlie was video taping the event, so he could post it looking for a domme. After starting off with a smaller dildo, Charlie sucked the huge cock and then lubed it up. Slowly, he backed himself up to the phallus until it nudged his waiting hole. He grabbed the cock head and glided it slowly past his outer ring. He grunted as the huge head finally popped into his hole, which left the long, thick, veined shaft to go.
Slowly, Charlie took all the remaining 12 inches until he felt his balls bump the plastic ones. He began to rock forward and backward on the cock, letting it loosen him up. As the pain that he had felt slowly turned into pleasure, Charlie moved all the way to the end of the cock, barely keeping the head in him, then thrust himself all the way back. He began to quicken his pace, as the warm feeling in his ass began to make him rock hard. Soon, he was flying up and down the cock, moaning, calling himself names, and begging to be fucked harder. After ten minutes he blew his load all over the floor without ever having touched his dick, but he kept fucking the cock with reckless abandon. Twenty minutes later he finally decided he'd had enough and pulled off the cock. He turned the camera off, cleaned the bathroom up, and took a shower. Charlie enjoyed fingering his gaping asshole while he uploaded his video onto the internet.
While Charlie was still waiting to hear from a Domme in his area, he continued on with his semi normal life, which included varsity football. He played Tight End and Defensive End, and had made some good friends on the team. One day after practice, Charlie had to run extra laps because he and his friend Jamal had been screwing around while the coach was talking. As Charlie and Jamal changed for the showers alone, Jamal started up a conversation.
