The first time I dropped a load in someone's ass was with this boy I'd had a crush on since high school. We actually met on MySpace, he worked at the local movie theatre and he'd let me into movies for free. His name was Kevin, he has shaggy blonde hair and a sweet smile. Years after high school he came and visited me in my apt in New York, where we had a "stonariffic weekend" basically we were baked the entire time and I acted like a huge tourist and we are great meals. We fucked that weekend on my hardwood floor, but I wrapped it. I remember he got so warm, his body felt like a furnace beneath me. Fast forward about a year, I was dog sitting for my best friends parents at their house in my hometown. He came over, we got insanely fucked up, he laid face down on the bed and I started licking his hole. He moaned like a bitch and I knew that hole was mine. I lubed up and slipped in, it was so right and wet and warm and he immediately started burning up. It's insane how hot this boy gets when a dicks inside him. I pounded his hole while sucking on his neck, and asked, do u care if I cum in u. He didn't say anything so I screamed I'm gonna cum! I buried my dick as deep as it wld go and shot abt six good pumps of cum deep inside his pussy. I can't remember anything else but how good it felt to shoot my load in a raw hole. We both commented how great it was and I licked his hole clean. Later while we made out, he spread his legs and I massaged his filled up cum hole. He knew it was mine.