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Quid Pro Quo
Date: 3/15/2024, Categories: Transgender & Crossdressers, Author: byLukesmitty
... tight hole. He takes off his shirt and stands naked. He pours some lube onto his meaty shaft and rubs it up and down, making his cock shiny. "Um....I think it's best if you put on a condom." Samantha says nervously. "Are you clean?" Luke asks. Samantha responds with a head nod. "Great! I'm clean too. Fuck the rubber. I'm going in raw. You have a problem with that?" Luke asks her, roughly spreading her rear cheeks wide open. "No sir." Luke grabs his thick rod, firmly pushing it into Samantha's perineum. He rubs his mushroom along her smooth skin in between her scrotum and anus, then slides himself down to her tight hole. At first Luke thinks about going into Samantha gently. A quick flashback to all the times when "Sam" the team captain humiliated him back in gym class each day, picking him last for all sporting activities convinced him otherwise. Luke pushes his cock against her sphincter and forces his way up her asshole. He feels her body shake as she winces in pain. Samantha begins to yelp, trying to stay silent. She can feel the tears forming in her eyes with Luke standing behind her. He grunts loudly with every inch of his cock sliding up her tight passage. She can't believe how thick his penis is. Throughout the years of her playing with herself, she'd masturbate and play with a small selection of toys. None of her dildos were as thick as Luke's cock. She's never had the courage to train her asshole for large objects. Now her soon to be boss and ...
... former classmate is deep inside of her ass, stretching her out. Samantha takes deep breaths and begins to relax. A wave of nirvana floods her body once her body adjusts to the monster inside of her. When Luke takes long strides pulling himself back and forth, Samantha springs out a deep grunt, desperately trying to conceal the masculinity of her voice. When Luke senses how she enjoys him fucking her, she feels a hand of his grab her neck with aggression. "Looks like someone is enjoying this. Let's see how tough you are bitch!!" Luke says with a hint of anger in his voice. He grabs the back of Samantha's neck with his right hand, clutching onto her firmly. He feels his hand shake as he chokes her aggressively, taking deep strokes in and out of her rear end. Samantha tries to breath while Luke fucks her. With his other hand, he spanks her buttocks. Luke switches from one cheek to another, spanking her with violent force. The loudness of the spanks have an echo. Samantha releases a muffled cry each time he hits her. Luke begins to calm down and focus on the penetration. He spreads Samantha's ripened cheeks, pushing himself deep into her as he can and back. He pulls himself out of her just enough for his tip to stay lodged up her ass and slams his way up inside her rectum, far enough to where his testicles collide with her rear. Luke grunts softly, thinking about how tight this transgender bitch is. He makes a decision to allow for her to take over. "Lean down. I want you ...