Not being able to fight back I tried to relax as much as possible as she probed all around my sphincter, pushing her finger in a little bit at a time, using my precum to lube it up. Getting extremely close she stopped stroking and fingering and said she would be right back.When she comes back she has a look on her face I will never forget. She puts a pillow case over my head and reaches between my open legs and rubs a very cold liquid on my asshole. Massaging it in my mind races with what she will do. She spends the next few minutes probing my ass, using one then two fingers to spread me open. It hurts a bit but that is forgotten with continued cock strokes.I feel something hard at my opening and realize that her shopping trip included a butt plug. My only hope is that it isn't too big for my first time. She pushes it in slowly until it is all the way in. My breathing is erratic and my cock is the hardest I've felt in a long time. She finally says that I can cum but her way. Sitting. “You know, I hate you sometimes, Dave. Bet you could be in her pants in three seconds if you wanted.”Dave shrugged, put on an exaggerated expression of confidence, and said, “What can I say?”“Asshole,” Will chuckled.Then Carl asked, “Do you know who that is?”Dave and Will both shook their heads.“That’s Amy Farber’s daughter, Caitlin,” Carl explained.In an instant, the nagging sense of recognition that had struck Dave the moment she walked over to the table made sense.“Oh, shit,” Will said. “Amy Farber. You banged her and her mom.”It was the incident that had forever cemented Dave’s reputation as the biggest player in town, all those years ago. He had dated Amy for a couple of months, and they’d gotten into an argument over something he couldn’t remember, resulting in her breaking up with him. That night, he’d happened upon her hot mom exiting a bar, and one thing had led to another.Amy had shown up at his place to apologize just as her mother was leaving with an unmistakable,.
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