Learning

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.