1.You can ask mamasan but better to talk to boy and tell him what you expect before you go to massage room.
2. Boys at pool are either working in massage parlor or gogo boys at night. Your choice to take them for massage or pay standard off fee and take to room.
3. I rarely would tip mamasan unless especially helpful in some way. There is no minimum tip stated in massage parlor but I think 1000 baht is almost always acceptable for massage boy or short time upstairs.
4. Boy from Bangkok is a Boy from Xboys. He is very good company and his English is pretty good. My acceptable rate for overnights in Bangkok is 2000 baht so I just figure number of nights x 2000. Of course this boy got a lot of extras including boys for him to have sex with alone. Thats my choice not something he expected.
By the way that overnight tip is for Bangkok. I think you will find 1500 acceptable in Chiang Mai or Pattaya.
5. They can arrange guides or even gay guides at Hotel. My understanding is they will be guides only.
Boys would not make good guides. First the Chiang Mai boys seem to have very limited English skills and have not travelled much.
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