Once again I say, think many girls have the same deluded ideas about jail/prison as they do about womanhood. Speaking with or (god forbid), being arrested and locked-up will quickly disabuse anyone of any fancy notions.
Long story short, if you think LE does not like gays and transgendered persons, much less criminals, corrections aren't that thrilled with them either. Consider also their ranks are filled from the same pool of applicants as LE, so you aren't going to have many enlightened souls. Make their job difficult while you are inside, and they can make yours VERY difficult.
Escorting and what not has become so widespread in the TS community, that many girls assume or even think that LE and the courts have the same sort of generous attitude, and nothing could be farther from the truth.
Time and time again have sat in various NYC courts and watched other low level offenders (smoking a joint on the street, having an opened can of beer or booze on the street, and so forth), get their charges either outright dismissed or six month conditional discharge (where if one is not arrested again in six months, the charges are dismissed and case sealed), where hoes most always get jail time, fines and community service.
Worse, allot of girls enter the system with no legal representation on retainer, or don't even know of an attorney to contact, thus rely on the public defenders office. Knowing nothing about how the system works is a huge disadvantage.
For instance many think just because they are arrested on minor charges, they can plead "not guilty" and will be allowed to go home and await trial. While that is true in theory, the courts can impose bail, which in NYS can be up to 4K for low level crimes. As many girls have found out, just because you have that money stashed under your mattress or in the bank does not mean the court will accept it. Most all states require bail money to be from legitimate sources. So if the DA can prove one has no visable means of support, and that those funds likely have come from prossing, then you are out of luck. Think you can simply say "my uncle gave it to me", think again. Judge will simply ask you to state on the record the source of funds, and probably may verify your story.
Yes, jails and prisons have improved much over the years, but that has brought about it's own backlash, which means the general population has little sympathy for those incarcerated or have been. Reasoning goes this is the USofA, and persons not guilty of a crime do not go to jail/prison, ergo you must have been guilty of SOMETHING and got what you deserved.
The United States has the largest prison population in the Western world. That does not even include various local jails.
Obviously the longer one is incarcerated, the more it can change you, but locking up first time minor offenders with career criminals, in some cases violent criminals does not provide the sort of "rehabilitation" the powers that be think it does.