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!"
For some reason, her saying that turned me on even more. She began to massage my shoulders, chest, abdomen, skipping my over my dick to my upper thighs. I remember my penis involuntarily twitching when she did this.
"Haha, you no worry." she assured me, playfully gazing at my twitching, rock hard penis. "I going to make him feel real good soon."
She wasn't lying. Just a few seconds later, she poured a generous portion of warm oil on the underside of my dick, applied more to her hands and began to stroke away.
Pleasure shot through my body like a lightning bolt. For the first time in my life, a woman's soft, warm hand was running up and down my shaft. She placed one hand around the base of my penis and stroked me with the other.