My[18F] boyfriend[19M] doesn’t listen to me when I say no and I don’t know how to talk to him about it

First of all, I barely use Reddit and don’t really know what I’m doing so please extend me some grace. I don’t really have anyone in my life to talk to about this so I figured I would try here.

For some background, my boyfriend[19M] and I[18F] have been together for a little less than a year(but I’ve know him since middle school) and it’s both of our first real relationships. I typically am the kind of person to just tell my friends to break up, especially because we’re so young, but I think maybe in this case I’m not communicating properly and it’s worth asking for advice and trying before resorting to that. 

Okay, so earlier in our relationship I had to have a talk with him because I felt like he didn’t listen to me, especially about the physical aspect of our relationship(we’ve never actually gone all the way, idk if that matters). I would tell him to back off or say I didn’t want to do something and he would do it anyway or keep pushing until I just gave in, not only with physical things but that’s what upset me the most. He also would do it with things like asking me to hang out with him when I was busy, so I’d let him know that I can’t and he’d ask like five more times, “ just to make sure,” until I felt bad and would rearrange my schedule for him. During this time I fell into a depressive episode(which I’m prone to) partially due to this and it only added onto how upset I was. After we had this conversation he was super sorry and didn’t want to do anything else to upset me so he backed off on asking me anything, really. But maybe a month after this he kind of just went back to his old ways with less physical stuff, but still ignoring my no’s in regular conversations. 

I’ve been trying to tell myself that it’s not a big deal because honestly the stuff he asks for is pretty inconsequential, but every time he does it I’m reminded of all of the things previously in our relationship and how empty and sad I felt. It makes me really uncomfortable around him and I find myself saying no to things that I’d actually be fine with, just because I want him to listen to me sometimes. Now, if any of my friends were telling me this, at this point I would tell them to reconsider the relationship, but I have a couple reasons that I think this is maybe more of a miscommunication than mal intent. 

• First of all, I’m normally a very assertive person. I have no problem telling people no and coming across as a little rude if it’s important, and this is well known about me. Yet, when it comes to him I can barely form the words to tell him to stop so most of the time I say things like, “I’d rather not,” “not right now,” laughing it off, or just going silent. In the conversation that we had he even said that it would help him if I just said no clearly, but I actually can’t make myself do it when it’s him and I don’t know why.
• Second, he doesn’t often get other people’s cues for when he’s doing too much. He’ll sometimes go overboard and won’t realize until later that people were trying to get him to behave differently.
• Third, I feel like I say no too much and therefore he is desensitized to it, especially because I end up caving most of the time anyway. If I let him do more stuff without protest than he might start listening to the important ones more.

Overall I would like advice on how to talk to him this second time and what behaviors I should try to change to make this work. So sorry if this was too rambling or I left out anything major, I’ve never talked to anyone about this before so I realized I had more to say than I thought.

tl;dr

My boyfriend doesn’t often listen when I tell him to stop, no matter the circumstance, and will push me until I give in. I don’t think it’s entirely his fault because I could be more assertive in what I say. How do I speak to him about this and get him to understand me better?