I love to get a massage, and yes, these are typical questions. The professional places invite you to “undress to your level of comfort” which means exactly what it says. I (a guy) used to keep my underwear on, until I realized that tension in the glutes contributes to lower back problems. She needed to massage my glutes, and that helped a lot. After several sessions, the MT and I got comfortable with each other, and I went fully nude. The drapes always covered anything not being worked on, so no embarrassment.
Having said that, occasionally, she would drag her fingers down my sides, which I thoroughly enjoyed, but I was never able to push her to keep doing it! Several years before, I did have one younger MT who was open-minded and a free spirit, who agreed to spend the last 5 minutes tickling my pits and feet. Very nice way to end the session. Unfortunately, she moved away and I have never found another one who would indulge me. Maybe someday…….
In your situation, your bra might get in the way of her working on your back. Just ask her up front and communicate openly. The ultimate goal is your health and wellbeing, which will improve when you get to know each other. My suggestion is, if she happens to do something to your feet, sides, hips, etc. that tickles, definitely let her know that it’s ok. Something like, “Oooh I really like that,” or a similar response would break the ice.
BTW, There have been stories posted on the TMF of guys who saw the same MT each month for two years, got to know them really well, and gradually had them introduce tickling into the session. That would be my ideal situation, and who knows, maybe yours?
Good luck, Idolfan05, and let us know how it goes!