Re: How do you know when you are ready?

do you or have you masterbated with a dildo or any other phallic object? do you enjoy the sensation? if you have not gone even that far it might not be your time yet, try getting a butt plug or a dildo and masterbate to some ts porn and see if you get totally turned on.

I'm generally ready when I have $250 to spare.

Realistically, the butt plug idea is a good one.  Don't start with the biggest one you can find.  Thats true of the ts too.  Let her know its your first time and avoid anyone who advertises as 'thick'.

You may want to try a few TS dates first before being topped. It is an exciting fantasy, but in real life, it can hurt. I had several TS dates before I even considered being topped. Even then, the first few were a pain. The provider is key. She has to be into it, not shagged out from working all day, and being horny helps. They still can be a lot of fun without it. At least it will give you a chance to not be so nervous with the whole thing. Read reviews and do your best to pick a TS ASP that provides (or at least has provided in the past) what you are looking to experience. Then, hit the atm and show up on time, but not early, as that never goes over very well. Then, and here is the secret, be prepared for the date to not go exactly as planned. Reviews help, but don't be surprised if you have a date or two where what you were expecting and what you get are two different things. Finally, speak up. She is not a mind reader. Don't be shy about asking for what you want.
Welcome to the hobby.