Why wouldn't you? It always amazes me that there is a small (thankfully very small) percentage of guys who think they shouldn't have to pay or that it's even ok to ask or assume that it's ok to expect freebies...
Generally guys give one of the following three justifications/explanantions/commiserations:
1. "I am hot I don't pay for sex.." So why would I care? There are plenty of 'hot' guys who are both respectful enough to appreciate that they are paying for a service and understand that everyone has to make money and it's a perfectly normal thing to do..
2. "I have no money- can I fix you up next time.." I appreciate that everyone has different financial situations but like any service provider we all have to make money- you don't go to a mechanic or a doctor or a hairdresser and say "look things are tight- have to fix you up next time"
3."I don't like paying I feel like I am disrespecting you by giving you money.." asking a person whose job is that of an escort if it's ok not to pay because it doesn't read well on your moral compass? Now that is disrespectful!
Supply and Demand it's a simple business concept. The number of guys into TS out numbers the available number of TS in the country by tens of thousands to one. Transgendered people are about 1 in 50 000 if not less than this. So while you could spend hours trawling hoping and wishing to get a free 'hook up' from an adult dating website chances are you will spend hours trawling period! AND you might get lucky and most likely she or he will hit you up for cash anyway as is often the case i'm told.
Transexuals would not exist if it weren't for money... Think about it as a token gesture of your appreciation for transexuals, shemales, t-girls or whatever term you prefer. Take into consideration that TS women are THE most margianlised minority group in Australia and 'normal' jobs are not always an option for transexuals. Without money for medical cosmetic and scientific intervention.. transexuals would not look anything like the revered creatures they are today.. well they would still be creatures but by a different meaning mostly!
As Dolly Parton says "It costs a lot of money to look this cheap"..