I had a childhood friend who had a crush on me. We were friends for a while before it started, but when we were teenagers things changed. At first he would do things like grope me and push me down, I'm on the small side and he was a lot bigger and stronger so he would just pin me then grab at my dick and ass, climb on top of me and tell me I was his. I would joke about him being a rapist because of it, but I didn't take it seriously. My home life was bad so I stayed with him a lot and we'd steal his parents' pills or they'd give us alcohol because they were ok with drinking as long as it was in their house. Sometimes I'd end up in his bed and he'd spoon me and play with my hair all night, we didn't kiss or anything, I'd just let him do that. I was bullied pretty badly for not being straight (I'm bi) and for being too androgynous so I felt uncomfortable going really far with a guy in spite of wanting to.
When his mother died I considered letting him fuck me while he did that, but he didn't push it that far.
He eventually started telling me he was in love with me and getting more pushy, and I told him I didn't think it was a good idea because he had such deep feelings and I thought he seemed like he would hurt me in the end. He said it was ok if I saw other people too so I started letting him kiss me and touch me more.
A couple weeks of that and we're drinking together and he starts to get pushy about me giving him a blowjob so I did and he tells me to fuck him. I wasn't really into it, but I did for a bit and he wasn't into it either. He stopped me pushed me on the bed and started sucking me off and then rimming me, and then he fucked me. I didn't really want it just then I wasn't ready and it hurt, but after a while I enjoyed it.
Since it already happened I figured it didn't matter if he kept fucking me so I let him for years.