The first woman who ever jerked me off was an Asian masseuse. I'm not particularly proud to admit it, but I was 18 years old, a bit shy, with no immediate prospects and I needed some relief.
The experience was probably similar to what many in that situation went through. I visited a well-known Asian massage parlor for which it was common knowledge provided extra services. I entered an empty lobby and heard a buzz sound as I opened the door. I stood there awkwardly. Perhaps about twenty seconds later I was greeted by a very attractive Asian girl who I surmised to be year or two older than I was at the time. She walked me to a side room instructed me to take off all of my clothes and promptly left. Returning about a minute later, we talked prices (It was $60 for "one hour") to which I agreed without protest. She proceeded to give me a rubdown. This was the first time I'd been naked in front of a woman so I was a bit nervous, but my masseuse, was surprisingly jovial, chatty and spoke English quite well through a slightly twangy Asian (Korean, I suspect) accent.
After massaging my back, legs, arms and ass for about 10 minutes she asked, "You're here for something else, aren't you?"
"...yes." I replied somewhat coyly.
She reached between my legs and softly scratched my scrotum before asking, "You want me to rub you here, too?"
When I responded in the positive I was told that service would be an additional $60. This too was paid without protest. She told me to turn over and once again left the room before I could comply. I must admit it, it was a bit strange to be lying alone, naked, in a strange place, with an out-of-control erection knowing that in but a short time a woman would touch my penis for the first time and bring me to orgasm.
A minute or two later she returned, and upon noticing my raging hard on smiled and quipped with a grin, "Oh, you already to go!"