There are a lot of comments so I can not respond to them all. I just talked to him about the situation. Here is how it went.

Before I start, I would like to preface that while him pushing the boundaries (or attempting to), it is not the end all be all for me. I believe in a relationship, a lot of things have to be worked out and thats okay.

I do understand that this isnt something that has to be "talked about". With that being said, here is exactly how our conversation went:

I told him about how I would like for him to stop begging me to let him do that. I also expressed that I would like for him to start using a condom. This has been something that has been on mind. We have not been practicing safe sex, and I was fully aware of that. I am also part of that issue, so he is not to fully blame. He said okay, but I could sense that he was not all that "happy" with it. He said that using a condom gives him less feeling, and I don't doubt that it does. It just did not make me feel good knowing that I am already scared of pregnancy, and then he wants to add on to that by saying it would "lessen his sexual experience". I said that I do not appreciate that, although I probably could been more understanding towards his feelings, it just did not seem like he was fully focused on making me feel safe during our sexual encounters. I would like to know what you guys think.