Caboose 1

Nick did a final check in the mirror, before heading out to the party. He was a pretty average looking 20 year old white guy. Just under six feet tall. 170 pounds. He put on a spritz of cologne and headed out. He was going to this frat party, with the same goal as so many other guys in his college: to find a girl.

Nick had been having bad luck with women. He had been told by several girls that he just wasn't their type. They liked the sex, mostly because he had a large dick. Eight inches long, and very thick. But his demeanor was too passive. Nick knew he had to start being more assertive, and it had to start tonight.

When he got to the party, Nick started to drink, and tried to talk to girls. No luck. He was still being too soft, and it was getting him nowhere. He was growing frustrated. He was even more frustrated, because he couldn't even masturbate, for the last week. His little sister, Katie, had a situation with her roommate, and had moved back home. Nick chose to live at home to save money while in college, but Katie had moved out. When she did, Nick and his parents downsized to a smaller apartment. With Katie moving back, the place was suddenly far too small.

Katie was just eleven months younger than Nick. They were the only children, and had grown up very close. But now she was just everywhere. Thin apartment walls and tight living quarters meant that Nick couldn't get any alone time. She was sleeping on the couch, just on the other side of his bedroom wall. There was no privacy anywhere. Thankfully, Katie went to the community college, while Nick attended the local university, so he didn't have his 19 year old sister following him to school. But the lack of privacy had made Nick frustrated, and somewhat desperate to find a girl.

As the party rolled on, it looked more and more like Nick was gonna strike out. So he sat and drank, and sulked. The night was winding down, and he had all but given up hope of finding a girl. He was, instead, thinking of creative ways to be able to jack off, since he needed relief. He was going to resort to masturbating in his car, when a guy came from the upstairs sleeping area and announced that they were "pulling a train on a hottie."

Nick was slightly disgusted by the idea, but was desperate. He went upstairs to investigate. What he found was a line, with over a dozen guys in it. There was no way to know how many had already been through. So Nick got in line. Someone was passing out condoms, saying that it was a firm rule, from the girl. Nick knew this standard condom wouldn't fit him, so he put it in his pocket, and hoped that by the time he got his turn, she wouldn't even notice he wasn't wearing it.

So Nick waited his turn. It was late enough that nobody else was coming, so he was last in line. The plus side is that this freed him up to go get another drink, without losing his place. For 45 minutes, he waited. Some guys took more than a few minutes, but most took only a couple. These were horny college guys, most of them ready to pop before they even got in the door. Finally, Nick's turn came up. His cock was raging hard, as he walked through the door.

The lighting was very dim, but Nick could see a juicy ass, bent over the edge of the bed. She was in doggy style, and never turned to face him. She whispered to ask if he was the last one. He replied with a simple, "uh huh." She asked if he had a condom on. He gave the same response, knowing fully that he was lying. Then she told him that he better last more than a few minutes. She hadn't been able to cum yet, because these guys were done so fast. With that, she pointed her ass in the air.

Nick held his hard cock in his hand, and stepped forward. He lined up his cock with her wet pussy and pushed forward. She was very wet, and had already been fucked over a dozen times. Even with his thick dick, Nick could barely feel anything. He had a different idea, and was just drunk enough to try it. Now was his time to be assertive. He pulled out of her pussy, and lined up with her little ass.

The girl objected, "No no no no. I've never done that." But Nick ignored her. He pushed forward into her asshole. She pulled away, lying flat on the bed. He followed her, still pushing into her ass. He pinned her to the bed, and buried half his dick in her virgin asshole. She cried out, but Nick couldn't stop now. He pushed further into her ass. Once he buried all eight inches, he started pumping her ass.

Nick never expected what happened next. Her cries of pain turned into moans of pleasure. As he pumped her virgin ass, her hand came back to find her clit. She was rubbing it furiously, and enjoying this new mix of pleasure and pain. She could feel her own orgasm building. She had been teased by the previous guys, unable to satisfy her. This would be a big one.

Nick knew he couldn't hold back, for long. His balls were full, and ready to blow. The girl's orgasm was also building, and she was ready for release. Nick finally pushed every inch into her tight ass, and dumped a massive load of cum in her. A week of pent up frustration shot into her virgin ass. As soon as she felt the hot cum in her, she came harder than she ever has. She squirted, soaking the bed, as a massive orgasm shook her entire body.

As her orgasm subsided, the girl had to know who just brutally and completely fucked her virgin ass. Nick pulled his now-softening cock out of her tight ass, and started to get dressed. She rolled over and made eye contact with...her brother. Nick was frozen. Half-dressed, and still drunk. The realization that he just fucked Katie hadn't yet sunk in. Katie realized she was still naked, and with her brother's cum leaking out of her ass. She made an attempt to cover herself. Nick panicked, and scrambled out the bedroom door, carrying half his clothes.

The real issue was that they lived together. Sooner or later, they'd have to see each other again, and acknowledge what had happened. He knew it was wrong, but on the drive home, all Nick could think about was how amazing Katie's ass felt, wrapped around his thick cock. He had to think of a way to make it happen again...