I am planning to book a nice hotel in downtown Boston.  I'm not going to roll the dice with Priceline or Hotwire, because I want some specific elements to the room.  I have a few ladies in mind to book a multi-hour outcall on a Sunday night...in mid-December.  Is that too early to make arrangements?

I personally like planning ahead while others prefer to book the week of.  💋

At least that will increase your chances to see who you would like to visit with vs. waiting to the week or day of and maybe missing them due to availability etc. I have had trysts booked as far as 4 1/2months ahead, it was kind of nice, every month that got closer, I would send my gent a candid shot of myself to keep the anticipation alive. Best of luck

I like being able to plan ahead that way.  Especially for outcalls

Especially with the holidays, it can be tough for some of us to take time out for ourselves. So if you see some time where you know you'll be available, seize the opportunity immediately! I myself already have a pretty coherent schedule going for December... as well as January, February, and March. What can I say, I'm a planner It's nice to have something to look forward to!