- Chloe Cherry was super excited for prom! Until her stupid stepbrother told her that her date is gonna expect to get some at the end of the night. This was an issue because Chloe was a virgin and she didn't want to give up her pussy! Good thing stepbro was a quick thinker and suggested she just give up her asshole! She was intrigued, but brother would have to show her how. He attempted to penetrate her narrow asshole, but Chloe was too scared of the sensation and they had to postpone their anal endeavor. A couple of days later, stepbrother was bumbling around the house and he stumbled across a big purple anal plug! What was Chloe up to? Turns out she was trying to stretch her little hole to be ready for prom night. Stepbro of course wanted to help out and had no problem helping chloe add a few extra millimeters to her gape skills. Finally just before prom, Chloe showed her brother that she had finally become a full fledged anal acrobat. She wanted him to test her out one last time, and boy was that hole in perfect shape! Penetration was simple and smooth, and Chloe was able to ride that dick with ease. This not only meant that she was ready for prom, but also ready to get her first taste of a freshly churned semen sample.