I ask for it every time. Most are reluctant to comply, especially on a first visit. Since most people don't want to be tickled, masseuse's are taught in their schools of massage techniques to avoid tickling, such as firmer pressure, etc. It's tough to break through all that training.
It's best to find a masseuse that you can really connect with. I found one masseuse who is licensed in many techniques, and is all about health and energy. She is older, about mid forties or so. She is a very warm person. We talked quite a bit about massage, health, and family.
At one point she was massaging my upper thighs and I flinched. She quickly moved on and apologized for tickling me. I told her that no apology was necessary and that I actually like being tickled. Her face lit up. She started telling how much her son loves to be tickled. She tickled my feet for a few minutes and then continued with the massage.
The next time I saw her, I requested a 90 minute session as opposed to just an hour. This was in her home studio whereas the first session was at the acupuncture clinic. Her son was there. He was somewhere in his early to mid twenties. I practically knew his entire history because she talked quite a bit about him and it was clear she loves him dearly.
There was a lot more tickling this time. I asked her to tickle my upper body. She tickled my sides and even teased me a little, explaining that the muscle's she was "massaging" were known as the "lats." Then she went back to the standard massage.
A few minutes later, I asked, "Could you show me where those lats are, again?"
She smiled and started tickling my sides again. "They're right here." She tickled me into near hysterics, pushing to the limit my ability to stay in place on the massage table. Then she returned to the standard massage.
A few minutes later, I asked, "I'm sorry, I seem to have forgotten again where those lats are?" She would dig right in again and tickle me until I was seeing stars. I could tell by the sound of her voice that she was really enjoying this silly little game we were playing. As things wound down, I told her I really enjoyed the tickling and tipped her well.
The third time I went to her was just recently. We talked a lot about the tickling and how good it made me feel. She enthusiastically explained that from a health standpoint it's very good as a stress reliever. Plus she believes that human beings don't touch each other enough. She lamented how unfortunate that in our society, nearly any kind of touch is associated with sexual connotations.
During this third session, I "warned" her that if I didn't get tickled at least every 5 minutes, that I was going to ask for it. She was perfectly okay with it, and I didn't have to ask once. Now I've been tickled all my life by people with various levels of skill and enthusiasm. This woman was a born tickler. She's tall and well built. She's neither thin nor fat, but kind of broad and slightly thick all over. She's a masseuse so her arms and hands are very strong.
She tickled my feet with such enthusiasm I couldn't hold them still, and I usually can. I instructed her to tickle just one foot at a time, firmly holding the ankle down with her free hand. I was in such hysterics, I had to clamp my own hand over my mouth to keep from making too much noise. She'd get me to where I was almost falling off the table, then let me up for air. Then she went to work on the other foot.
One of her favorite spots to tickle was the back of the upper thigh, where she told me her son was extremely ticklish. It was a killer, to be sure. While I was still lying on my stomach with my face resting on the padded ring, I reached my left hand behind my head with the elbow bent and touched my right shoulder. She grabbed my wrist and held it there, and then zealously began tickling my left armpit. This was a great position, because I couldn't struggle very much and she was able to take the tickling to deeper levels. We switched arms and she tickled my other armpit just as vigorously.
I was destroyed, but had never felt better in my life. It was like I was floating on air, completely bereft of any stress or tension.
So yes, it's possible to get a masseuse to tickle you. However, if you're a guy and being tickled gets you aroused, bear in mind that you are naked on your back, and under a flimsy bed sheet. These legitimate therapeutic masseuses will likely ask you to leave at the first sign of a tent pole.