Our culture has developed into one with such devotion to MILFs that is almost impossible for a teen not to fall for an older actress, a teacher, or a friend's mom. That's where this story begins. The story is based off of many real events with each participant being at or above the legal age.
Since the 3rd grade, Ben and Matt were inseparable. They shared every hobby, always had a class together, and hung out with each other religiously. Both of them were part of the other's families to the point where their families were nearly inseparable and definitely best friends.
Ben and Matt felt very comfortable discussing sexual topics such as jerking off with each other. Matt had always known that Ben had a thing for older women. At the beginning of his senior year of high school, Ben felt an urge to begin masturbating sometimes to another older women, not a porn star: Matt's mom. Tammy was in her mid-forties, had a pretty face, but was definitely overweight. She was the sweetest woman to Ben. Ben, who was never one for large women, just felt the urge to pull up a picture of her on Facebook and stroke his young cock.
So it began. Ben begin to scheme of ways to flirt with his best friend's mom, who was always around hanging out with his mom or at her own house when Ben was with Matt.
A few weeks after his first masturbating session to Tammy, Ben texted her. She had been helping his mother plan for a big party for Ben's younger brother. He thanked her for her help to his mom, as his dad was not very involved in the party, and included that she looked very pretty that day. She loved the compliments and Ben would occasionally write to her to let her know how he felt. His hugs when he saw her began including a little peck on the cheek, with the urge to try to touch her large butt. With that butt in mind, he snapped a picture of it when with her as he began his collection of pictures to use.
On his next visit to her house, he sprinted upstairs while Matt was in the bathroom and jerked off into her panties: the first physical act of his inclination towards Tammy.
Weeks passed and Tammy and Ben began playing word games against each other on their phones. Conversation sparked from that and Ben used it as an opportunity to flirt with his MILF. Finally, Ben decided to take another step and express that he had a crush on Tammy to her. The likely not sexually active mother of two was flattered. But a few days later, Ben decided to make things more obvious.
When he first left his cum in her large underwear, it was uncertain whether or not she knew it was him. While over her house for a party a night later, he left a massive load in her underwear and returned them to her drawer. Two weeks later, they were texting about their word game when Tammy said she was going to sleep.
