How To Build Up Courage And Confidence?

[Brooklyn Baby]

I'm a 19 year old top and sometimes I get a few people interested but I never go for it. By all means I'm not a virgin and I've been with many different people but they have always been people that I had known, not strangers. But when it's people that I'm going to meet for the first time, for the sole purpose of sex I get a little worried. I don't have the best body, I am hairy and bear-ish and my cock isn't anything more than average so there's always this feeling there that I might get rejected when we are just about to start fucking. So my question is in the title, any advice? 

Edited December 23, 2014 by Brooklyn Baby

[Guest ff-whole]

Before I would go cruising or on unknown dates, I would suggest hitting the reasonably safety of a gay sauna/club... Gain confidence and let loose... Let total strangers fondle and maybe fuck you (if you are a bottom), after that you feel confident to cruise the streets, scene or parties, you will enjoy all a lot more...

After your first anonymous fuck or maybe even gang bang party, your mind is set to become the bottom slut or master top... And that my friend is the ultimate horny feeling for me at least. The being of a cum slut.

Edited December 23, 2014 by ff-whole

[nastybottom]

Just be honest in your description of yourself and provide good pics. If they agree to meet, you should be confident that you won't be rejected.

[TigerMilner]

Practice.  Lots of practice.  Fuck every chance you get.  As you begin to see the signs of how much a top is appreciated by a bottom, your confidence will grow.  Don't get hung up on comparing yourself to others.  Attitude makes any top more attractive, so as your confidence increases it will be reflected in your attitude, which will lead to more fucking.  And lastly, find a hot older bottom and fuck him alot.  You can't help but get better at fucking when doing it with an experienced bottom. 

[Brooklyn Baby]

Update: I've met this 26 yo dude and fucked & came in his ass.