Male to Male, First time question

To answer your question, doggy because it is the most natural to him. Other positions will likely freak him out and make things difficult. Cowgirl pins him and if he wants to leave during the act, would be unable to
 
Missionary is also not recommended for first time because part of it to him is dominance. You looking at him while he has mounted you can be taken as a challenge and makes him uncomfortable
 
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