Sydney Paige in First Anal with Stepmom. My step-mom, Sydney, walks into my bedroom wearing a bright red dress. She tells me that my father has worked very hard to be able to pay for my college tuition, so I will be going today. I argue with her because I want to be a TikTok star and I dont even want to go to college! Im going to play a game with you. Its the same game that I play with your father when I want him to do something that he doesnt want to do, she tells me. She tells me that she wants to play a game called Just The Tip and she wants me to try and fuck her ass hole with just the tip of my cock. If you fail at this game, youre going to college today! she exclaims. She asks me if I have ever fucked a girls ass before, and I tell her that I havent. Sydney pulls her red dress off, exposing her natural tits to me. Once she is naked, she pulls my cock out from under my shorts and she starts to give me a blowjob. Once my cock is nice and hard, she lies back in the missionary position and I slowly start to fuck her pussy with just the tip of my cock. I start to fuck her tight ass with the tip of my cock next, and I am careful to not put in more than the tip at first. She starts to ride my cock with her ass next, and she is careful to only get the tip inside of her. She switches to her pussy and now she starts to ride my cock completely, ignoring the rules of the game. Sydney switches into the doggystyle position and I start to fuck her pussy and her ass harder now. She flips back into the missionary position so I can stare at her face while I fuck her holes. When I am ready to cum, I explode deep inside of her pussy.