Yes

"Well, but wouldn't that be kind of gay? You know I love pussy, right?" Gary still has doubts, but you sense you're close to getting him to jerk you.

"Me too! But you know, the motion is the same, it just feels way better if it's not you, right?"

"Ok man, but... how do we start this?" You knew you would convince him. He may be smart, but you know his every weakness. This time you just relied on his horniness...

You position yourself next to Gary on his bed, and just reach over and grab his cock. It's a little shorter, but at least as thick as yours. You feel Gary's hand on your dick now, too, and slowly start stroking his. He follows your lead, and shortly after, the two of you are moaning in pleasure while you're jacking off eachother. Since you already showed so much self-assurance, you think of testing out your limits.