I feel you man, growing up I wasn't bad looking but I just sort of stayed to myself. Growing up folks would sometimes talk about how this or that girl liked me but I never believed them due to not knowing just what the hell they saw in me.It is what it is breh, I mean you gotta get it out of the way at some point. Just fake it till you make it, if the chick isn't impressed then don't take it personally.
And you don't have to "explain" anything. I lost my V-card at at relatively late age too (19 almost 20) and I didn't bother telling the chick it was my first time. Was slightly awkward at first but it worked out. A little alcohol can help ease the nerves...but not too much, trust me.
Then there's the time in college where I was pretty much on the 1 yard line and pussied out because of me not having done it before.
Since then I've had to deal with depression due to not succeeding at college, porn addiction and my own laziness and here I am. I'm just now really starting to win the fight against these things so I'm heading in the right direction I guess. Performance anxiety is gonna be a whenever I do get that far though.
Can't get out of my own head.