Sometimes it simply boils down to patience. About a decade ago I started visiting a southside RMT, nice looking woman, mature (some would say an auntie).
She dressed modestly, slacks and a top, not hint of cleavage. Provided a really good massage, always draped with a towel, a small one but none the less adequate to cover the parts. I asked if I could remove it and got a quick but firm "NO".
Enjoyed her massage so much I became a regular, after some time I noticed that she was working lower on the abdomen, higher on the thighs, but I said nothing as I thought she is simply getting more comfortable with me. Then one day she accidentally brushed the LG, which was lying against one thigh under the towel, was nice but thought nothing of it.
On the next visit, it happened a number of times, and this caused the LG to start to stand at attention, nothing to serious, but it was obvious he was aroused. so while she was oiling her hands up and not looking I slipped the towel to the side a bit so the LG was partially exposed. I assumed she would cover him up right away, but to my surprise she did not. the massage continued, but now she was continuously brushing up against the shaft and it was hard as a rock. The massage continued with her massaging my lower abdomen, lower than she had ever gone before, finger brushing the base of shaft under the towel. So in for a penny, in for a pound, I removed the towel leaving a raging hard on fully exposed, not a word said. She continued, my cock up on my belly, her working my abdomen and her hand going under my cock. I then took her hand and placed it on the shaft, not a word said and she proceeded to provide a very nice ending.
Future visits were without towel, always a nice finish but never a word said about it. On one visit I finally told her it was very nice what she did for me and asked her why it took so many visits. She told me it was not something she ever offered, but I was a "very nice man" and hadn't asked or pressured her and it was obvious to her that I was aroused by her and this made her feel good, she giggled that I was much bigger than the past men in her life, she also asked me never to tell anyone. On future visits I was allowed to undo her bra and play and suck on here breasts. Unfortunately, she eventually moved on.
Now for the patience part, whole process took about 2 years and maybe 40 visits. Never expected anything other than legit massage and was pleasantly surprised