Flattering Best Friends Mom

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.

"Wait," Ben wrote, "Do you have a second?"

Tammy replied that she did and Ben boldly apologized for the semen leaving. With the adrenaline rushing through his veins, he anxiously waited for her reply. She accepted the apology and added "I was a bit freaked out about the overstepping of boundaries on your part, but it was very flattering which trumps all else." Ben was stunned. This conservative mother had just expressed that she was flattered that a handsome, tall, 18 year old left his dick's juices in her large pair of white cotton panties. Tammy repeated to him that everything was OK and that she used her discretion and didn't tell Ben's mother.

As Tammy said good night once again, Ben ended the conversation with, "I owe you."

A few days later, Ben made plans to spend time at Matt's and play a little XBOX. What he didn't know was that Matt wasn't the one operating Matt's cell phone. Ben drove over to the Bomes house and was greeted at the door by Tammy. He hugged her like normal, but her reaction wasn't the same. She reached her hand to Ben's jeans and grabbed his cock. "I wanted to see if I was working with a good one," she said. Ben, stunned, was told, "Come upstairs. Matt isn't home."

He followed Tammy upstairs, watching her chubby ass sway back and forth, nervous with a massive hard-on. Next thing he knew he was watching his best friend's mom remove the top she had on, unveiling her 34C breasts. She motioned for him to approach her on the bed. "You told me you owed me one. Now, what I would like is for you to bring your handsome face down to my pussy and lick me and fuck me until I cum," demanded the 47 year old. Ben was too stunned to say anything and obeyed.

His friend's mom unveiled what had to be the finest brown bush any woman could have. He glided his tongue up and down her slit, as she moaned and ran her hand through his thick, brown hair. "Pl...play with my boobs," she requested in ecstasy. As Ben worked his magic on her, she grabbed for his cock and began stroking it up and down as her head tilted back. "Let me taste you baby," Tammy repeated until the man she watched grow up inserted his manhood in between her fine lips.

As soon as Ben began quivering, Tammy removed his cock and motioned with her eyes for Ben to begin fucking her. Slowly, he entered her as she screamed in delight. "Work and the kids makes this never happen with Greg, but it could never be as good as this is." Ben couldn't believe what was happening, as he jammed his hard cock in and out of, basically, his second mother. Finally, she shrieked, signaling to Ben that it was time to unload the same cum that sat in her underwear. They came together, concluding an unrivaled sexual experience for the two.

They went back to playing their iPhone games, not discussing this day until...

The Bomes and Wilks went to visit a college together.