He probably won't see this, but I want to address the following:

Some of the most common things that make me feel bad about myself are; I can't ever have biological kids, my risk of STD infection is statistically astronomically higher than if I was straight, read something about painful perforations due to long term anal sex as well.

1. You wouldn't have been able to have biological kids with a man either way if you had transitioned. You can still foster/adopt and it may be in your best interest in the future to foster LGB youth that get kicked out of their homes so you can prevent them from going through the same internalized homophobia you experienced as well as have insight into what a toxic same-sex relationship looks like from the inside so you can catch things before they get out of hand.

2. Your risk of STD/STI infection was the same as a "straight transwoman." If you want to prevent STIs, use condoms and insist on protection with every sexual encounter, even in relationships. Too often guys think that dating someone for three months and getting tested means they did the right thing when three months is hardly enough time to known if someone has been exclusive with you or not. Prioritize your health and safety in your relationships so you don't become a statistic.

3. According to other statistics (that I've heard of via word of mouth), most same-sex male couples don't engage in anal. Oral and manual sex are fairly common and don't lead to anal perforations/tearing. Again, if you have concerns, prioritize your health and safety.