Approximately 20% of the population carry some type of STD so if you aren't very selective and you like to fuck odds are you are going to get something. The most likely candidate is Herpes, it's a gift that keeps on giving. I don't like condoms either but I belong to a group that is large enough to provide some variety and we limit out activity to spouses and members of the group. We all get checked a couple of times a year. I get more hassle free pussy than I should be entitled to and NO drama or surprises
It should be noted that not all STIs (herpes, for example) can be prevented with the use of a condom. HIV is very rare, but if you suspect there may be an issue, that is cause for concern, regardless of whether you are using one. It may be worth the talk of testing to be sure.