Tries a dating app.

When Jake was a senior, he was just a little bit crushed that he had never really been on a date or even kissed a girl. He decided that he should go on to this dating app, that was made for just highschool seniors. He spent a full night making a profile on the app and did everything he could to try to make himself seem more desirable. He didn't lie or anything like that, he just made sure to mention things he thought girls were looking for. It just wasn't really working out for him at all.

After a month, he matched with this stunningly beautiful girl, Molly who was from the other side of the city. She was a sexy brunette, with long legs, an ass to die for and the nicest set of tits that he had ever seen. She was so nice to him and they talked for a few weeks, talking more times a day, as the weeks went by. She was into all of the same things that he was, so he thought they were building a real connection. Jake was excited and he was dying to meet her in person.

He was constantly daydreaming about her and she was the only person he was really thinking about. Every night he was jerking off while thinking about her and imagining her pleasuring him sexually. Jake was head over heels in love with her and she could clearly tell. A few weeks in, she started to send him sexy pictures and he sent her a few nudes back. She couldn't believe just how tiny his two inch boner was or the fact that he sent her nudes with his face in them.

Unfortunately Molly was the cousin or Kelly, who was most popular and beautiful girl in Jake's school. She thought Jake was a total loser and a creep and of course she told her cousin that. When Kelly saw the pictures of Jake nude, she lost it laughing, seeing how he was even more pathetic then she had previously thought. Molly was only talking to Jake because he cousin found his profile and thought it would be funny. The more Molly talked with him, the more the two cousins thought they could set Jake up for some humiliation.