Silk screening will provide the most durable images. A good silk screened image may out last the shirt, itself.
Yes, it's a lot of work to produce the screens and do the actual printing yourself, but that's why designers tend to hire out the actuall printing to a professional shirt printer. The costs tend to be nearly cancelled out, the greater the volume of shirts ordered.
For smaller runs, of, say one to twenty shirts, the heat transfers may be more economical, and well within the capabilities of a designer's home studio. Just be aware that those buyers who recognize quality will also know a heat transfer from a silk screen and will only be willing to pay a correspondingly lower price per shirt.
Interestingly, people, even conniseurs, are willing to pay the highest prices for custom airbrushed shirts, even though airbrushed designs are about the most fragile and ephemeral of wearable images. But then, they are paying for one of a kind, original artwork and not some mass produced images.
Quality is hard to define.
There is nothing wrong with wearing girl's clothes. Clothes are just pieces of fabric we wrap ourselves in. They are not who we are inside.
If you've heard the word transvestite - that is men who wear women's clothes. Some of those men are gay, some of them are straight, some are bisexual. A transvestite or cross-dresser is not the same as a transsexual. That is someone who feels they were born in the wrong body, and are really the other sex than what their body is. There is nothing wrong with that either, but that doesn't sound like you from what you say.
Search for transvestite support or similar online and find folk to talk to about this. It is not bad in any way, but take care with who you tell. Many people don't understand and will get all weird about it.