Women, Would you date a man who has had sex with a transgender woman(shemale)?
Why would past relationships of any sort be anyone's business? This need to spill your guts is a turnoff, as well as the need to hear about every encounter your significant other ever had..I am an old woman now and thankfully well past it but my advice is to be considerate and wonderful to the woman you are with, (or whomever it may be) and don't' waste time and energy about the past...
1) Why don't you tell us why you're asking this question? Needless to say, there are a LOT of guys who have had or are interested in having sex with trans women... otherwise there wouldn't be trans sex workers and trans-themed porn... of which there are a lot of both. A more apt question is "do you feel shame for having had or wanting sex with a trans woman?"
2) The term "shemale" is a porn term... I'm trans and I find it offensive that it's being used on this site. It doesn't mean the same thing as "transgender woman." I understand you're from Brazil (the country which has the highest number of murdered trans women in the world) and the terminology is different. You're probably thinking about the Brazilian term "travesti" which, from my perspective, is also offensive in this context.