date lined up for this weekend, question

[MascaraSnake]

Maybe two depending on how you look at it. The first is not really a date, we're both bringing along friends to see a movie and I'm not worried at all.

The second one is uncharted territory; a woman much older than me (she's 30, I'm 20). We met at a jam band concert not too far back and we're hanging out this weekend.

Only problem; I'm a virgin. I think this one could go somewhere (there's a lot of game-playing and ball-busting on both sides) and I don't want to kill all of the tension by having to say "oh, by the way, I've never done this before" right before I start.

I'm obviously not going to be able to fake like I'm experienced, so how do I approach it without looking like some sort of wuss?

 

[MascaraSnake]

Thanks much, I'll be sure to.

 

[MotownMack]

Stop worrying about, and just go for it.

No one is expected to be good at something the first time they do it. And odds are, she's had some really bad sex with guys who have done it many times, and still suck.

Don't mention any of this to her, she doesn't need to know. It's not nearly as complicated as you think.

 

[MascaraSnake]

update

Well, the first one flaked...her mom was in town or something. I'm going to set up one more outing with her (and bust on her like mad for being a flake) but if I get ditched again I'm not going to waste my time.

#2 was the one I was asking about anyway...I think that one'll go very well.