SUCKING DICK???

Gianna • I'm here because my life is a mess and I need to track my period and ask questions I never learned in sex ed
so, lately i've been really wanting to suck a dick for the first time. i'm 17, and never have. recently i've been hanging with a guy who im pretty into and trust and i've been seriously considering it with him. i'm comfortable around him and we have a lot in common. but i have 3 issues;
first of all, i have braces and i'm not sure if that could, you know, effect it in some way. 
second of all, he has a pretty big dick. i need tips with how to deal with this
and third, and most important, is im worried with how i will feel about it after. Ladies, how was the first time you gave a guy head? did you regret it after?