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after everyone else left or went to bed we stayed out on the couch, fluff talking, as I had no idea about anything on this site. So she asked me to give her a massage, and I did, a leg massgae up to an upper leg and eventually thigh massage. Under her sweatpants, weird I know.
Just from this part, I would think you had a pretty good shot here. Obviously a lot of kino - very good kino at that - so my guess would be if you flirted and got a little more intimate (instead of the fluff talking), you probably could have reached atleast first base.
I know I'm not the best in this area, but from what you wrote I think you had something going. I'm a little gunshy at times myself and I can totally understand your nervousness (since I can get the same way), if I got to this point and there are a couple other IOI's, I probably just got for it, for better or for worse.
As for your question...the next time you two are together, try flirting with her a bit and see how she responds. If she flirts back, ask her out - again, you have nothing to lose. Don't feel so badly about it right now...people learn from past experiences. I've learned from all my rejections on what I should do to improve. In your situation, you know the next time you're massaging a girl's upper thigh, you could probably pull off a move.
Good luck man.