I'm in a monogamous relationship. can you still get Chlamydia by having anal sex then go back to vaginal sex without washing in between?

I have been with my boyfriend 2 years now, we have had anal sex before. I was not aware of the safety factors of it, and we had anal to vaginal sex...alot. I ended up with a horrible UTI and kidney infection. I also had anal herpes outbreak (never had one before.) This was all over a year ago. Anyway, we are trying to introduce anal play back into our sex life.
I am paranoid (as you can imagine) I need your professional advice, and opinions. Do we need to use a condom for anal since we have been together so long, and already figured out that we have herpes? Also...I am paranoid about the infection thing, obviously I'm not even thinking about anal to vaginal sex, but I am still nervous. Please set my mind at ease.

My boyfriend and I were having sex the other night. He wanted to try anal sex. I've never had anal sex and I wasn't sure about it, but he put his penis into my anus and he only got it a little bit, but couldn't go more than halfway. After a while I told him we would need lubrication. But we didn't have any. Then he stuck his penis back into my vagina. I told him he should have washed off first. It's been four days and I have smelly discharge and it burns a lot. I suppose I have an infection or something from what he did?