Yep, I'd like him to be naked for many of the reasons already stated...both of us are vulnerable and open; dislike clothing touching interrupting the connection; allows me to move in the massage much quicker.
I try to be clear that I am looking for a solid, relaxing massage first and foremost (even if I am talking with an escort) and why in particular that day. As the conversation moves on, I ask if it would be okay if we are both naked. I try to keep the naked part separate from the HE as the later is not as important as a good massage and feeling connected. I am hiring because I am looking for the body work to ease the stress and tension I am carrying; take care of that, and we can see where our connection takes us.
I have only had one hire who wasn't comfortable. The rest of the time it has worked better than expected. One guy I used in DC was a former gymnast from Ukraine. He was comfortable with being naked but that was the boundary. He provided an excellent massage that left me feeling very relaxed. Another guy I hired is so unpredictable, it has helped me to sort out his mood before hand. (He has been previously discussed.)
I guess it comes down to ensuring there is good connection to help me move out of head and relax into the massage. Guys who tend to stay clothed might give a great massage but I dont feel the deeper connection that is important for me. I'd also like to think it helps weed out the guys who sees clients more as an ATM.