If you want the beach, Pattaya would be a good choice. You could go to Phuket, but Pattaya is closer to Bangkok and transport will be less of a hassle.
You might also consider Chiang Mai in the north. No beach but a different atmosphere from both Bangkok and Pattaya.
The
Tarntawan Place Hotel in Bangkok and
Ambiance in Pattaya are good choices for a first-timer.
Tarntawan Place Hotel - Home Page!
Ambiance, premier deluxe gay hotel in Pattaya, Thailand
I suggest you look through the massage and gogo bar threads here (go to the last page of each thread and read back a few pages since the earlier posts will be quite dated).
Also look through Dreaded Ned,
bangkok gay listings - dreaded ned's explore gay thailand
Shameless Mack,
2009 June « Shamelessmack in Thailand and around
and Nicky's
Nicky's Gay Pattaya - Bars, Gogo, Saunas, Massage, Restaurants
You'll need to do a little exploring away from the hotels for massages and gogo bars, but hotel staff can help you. Both hotels are located within the main gay areas.
I would suggest you NOT look for someone claiming to be a
guide. It's not that difficult to explore on your own at first and if you off a boy from one of the bars with whom you feel some chemistry, he can also fill the role of guide if you agree that he'll stay with you for a few days.
Don't commit to any long term arrangement. Just take it a few days at a time since you may want to have freedom to meet other boys too. Do remember that even if the boys enjoy your company and the chance to show you around, it's not a holiday for them, it's how they make a living and these days income is bound to be down. You would be expected to cover all expenses while someone is with you and to provide a reasonable "tip," when you part company.
Have a nice time and report back to us later.
Businesses come and go, but for a general point of reference, relative to the two hotels I suggested here are maps of the main gay areas in Bangkok and Pattaya.
Not sure if the maps are showing when you open the thread. Links to maps of Silom area in Bangkok and all areas in Pattaya are here:
http://www.dreadedned.com/directory/map/1/1/
http://gayaffairspattaya.com/maps/maps.htm