Yes. Yes, any contact between the penis and the female introitus (area around the vaginal opening) or vagina carries some risk of pregnancy. The odds of fertilization of the female egg by the male sperm is based on the specific circumstances of this contact. While the fluid which accumulates early in male arousal ("pre-cum" as you term it) has fewer sperm in it, fertilization is quite possible.
Yes - possibly. Most studies have shown low levels of sperm or no sperm in pre-ejaculate with sperm not being motile (however, don't know how promptly samples were examined). One small study published in 2011 showed that there are some individuals with a high motile sperm count in pre-ejaculate. See: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3564677/