Boys Halfway House: Incident #156 (Pretty Boy Railed Senseless) (Bareback)

We got a new resident this week. He is a pretty boy for sure: blond hair, bright blue eyes, an innocent demeanor, and an appropriately deferential attitude. I'd read his enrollment report and figured out just what kind of guy he was before I even met him. Lots of talent and expectation early on, falls in with some friends who lead him astray, thinks he will never get caught. Then his grades start falling and he barely manages to graduate. He's disappointed his parents and fucked up just enough that they are worried. So they send him to our humble House. Even though he reeks of entitlement he'll probably get a long just fine.