#1: Maybe….I beat my dick like it owes me money, and I take forever with women, too. Especially with the few whores I have been with, although I think that is very normal. You should definately mix it up some though. Use your other hand, real light pressure, etc.. better yet, find something you can fuck, like a fleshlight or the homemade variety (roll a towel folded lengthwise into thirds around a latex glove, and fold the glove back over the towel, lube, and hammer away!) This way you will get used to cumming from thrusting, and you can work on your stroke, so you are sure to impress the next time you are with a girl. I had built up plenty of “experience” this way before I was finally able to get laid, and I think I was much better off for it.
#2: No way. Unless she JUST got railed by someone much bigger, the pussy only stretches enough to accomodate your dick. You should feel something. After all, tampons stay in, don’t they?