When I started college I was lucky to have Michael as a roommate. I didn't know him very well but had seen his cock in high school and hoped to even get to stroke it.
He wasn't very open but I noticed he liked to play cards. I decided to ask him to play strip poker.
He agreed and it was on! We played and then it was the game before the real game. We were in our boxers and I won. He slowly pulled them down.
I asked him 'wanna play again?' He said he had nothing to bet and I told him if I won he would stroke me. I lost that game on purpose. I stroked him until he shot five long ropes. Now we have fun like that all the time. We have many jack-off sessions.