This is gonna be a long one - TL;DR at the bottom but I’d appreciate it if you stuck around for the whole story because this has been bothering me for months.

Background information: I’m (M18) transgender, but my ex (M19) knew me before I came out. I’m going to call him Jeff for this post. We met in middle school and ended up going to the same high school too, but we had an extremely rocky friendship (even longer story so I’m skipping it) until the end of my sophomore year when he convinced me to join a club at our school. We started hanging out a lot during my junior year, and I developed a crush on both him and my now-girlfriend about that October. I had come out to him two weeks previous and he was chill about it, but I knew he was straight so I figured if I asked him out, he’d just reject me and I could move on with my life since that avenue was entirely closed and ask out my current girlfriend instead.

To my surprise, he said yes anyway. The way he said yes should have been my first red flag. He said, “Well, you’re a dude, so I won’t date you, but we can be friends with benefits.” Now, I was stupid and felt validated and was shocked so I said sure and we made out in his car. When he took me home after that, I felt weird, like I wasn’t really myself? It’s hard to describe, but I found myself staring at my reflection in the mirror and feeling off for a while that night. I brushed it off at the time, but it’ll come back up later.

Over the next two weeks, he slowly warmed up to the idea of us dating. These are the next red flags. He asked me if he could call me his girlfriend, which I was so...weirded out that I was left speechless. We also did a lot of semi-public making out and third base which made me sort of uncomfortable but I wanted the relationship (one that I felt I barely could even have in the first place considering the circumstances) to work so I didn’t say anything and just went along with it when he’d ask to make out for an hour in his car or for me to give him a handjob.

Eventually my own anxiety caught up with me and I impulsively broke it off that December. He seemed crushed, as he was finally developing romantic feelings for me, but the addition of romantic pressure to what I recognized was mounting discomfort with physical stuff (particularly because the dynamic of the physical stuff made me feel like “the girl” of the relationship) was too much for me so I nipped it in the bud to save myself.

If only I had listened to my gut and my raging dysphoria.

He ended up dating a girl pretty soon after and I started dating my current girlfriend for the first time (our first relationship was pretty dry because we were both pretty awkward so we broke it off after a few months, but we’re extremely happy and almost at 6 months going strong this time around!). However, after we had both broken up with/been broken up with our SOs, he asked me if I wanted to try a relationship again in June. We had been best friends the whole time we were broken up, so it wasn’t hard for feelings to be rekindled there and I agreed.

This time he upped the ante sexually and every single time we hung out he’d ask for some sort of sexual act, usually a blowjob but sometimes more. He’d also ask me if he could do things to me that made me extremely dysphoric (touching certain parts of my body for extended periods of time and using certain language) and I’d tell him no repeatedly but he’d still ask almost every time we hung out. Our relationship continued into my senior year, which worked because he was in college but living at home. We only saw one another on weekends, time that became unspoken “his time” with me.

I barely hung out with my friends outside of school functions that year because all of my weekends were taken up with Jeff. He didn’t have any friends at college (this probably will come off as biased but everyone I’ve known from high school agrees that he has a weird superiority-inferiority complex that leads him to not give people the time of day if they’re not “smart enough” for him) and his high school friends largely went elsewhere except for two of them.

Most of our time in person and over text was taken up with him talking about his interests and his financial problems with me just having to go along with the conversation and him asking for sexual favors (either sexting, which I was uncomfortable with, or actual sex, which I increasingly turned down out of the crippling anxiety/dysphoria it gave me and actual physical pain it caused me in some circumstances). Because I was in senior year, more and more of my time was taken up with college applications and big projects, so I started saying no to more and more invitations to hang out.

I will admit that that’s not always the only reason I said no, as he was becoming clingy and demanding to the point where just thinking about the weekend made me uncomfortable. I tried my best to communicate my discomfort to him, to the point where I broke down crying on his bed trying to explain my discomfort when he kept asking me for a blowjob when we were watching a movie. After I finished crying, he asked me again and coerced me into putting his dick in my mouth, after which I broke down crying again and asked if he could drive me home. He did, and that was the last time we hung out, as after that I would both deflect for OBVIOUS REASONS! and also because AP exams were approaching and I needed to study.

The night before one of my exams, he texted me asking if I could come over. I said no, I was studying and had an exam the next day, but he then launched into a long message about how I was avoiding him and “he never had this much work in senior year and he had taken much harder classes than I did” (which may be true on some level as he was taking engineering classes, but I was still taking 4 AP classes, a dual enrollment math class, and an intensive film seminar where I had to make my own short film that was due in a few weeks, so the comparison wasn’t fair in my opinion). He threw out a few different arguments all with the intent to keep me from studying for an exam (including but not
limited to making fun of the college I committed to when it’s literally the same college he goes to!) I paid $93 dollars for just so I could give him a blowjob and cuddle him for two hours maximum. I had had enough at that point and told him as such and ended the conversation.

We didn’t talk much from there and two weeks later he broke up with me, citing how distant I was for the previous few months. As he was breaking up with me, he asked if we could “still cuddle sometimes” to which I said yes, mostly because I didn’t want to burn the bridge at that point, didn’t want him to be upset with me (as he had fallen into a depression in the past over ended relationships), and was riding the relief high of no longer being trapped in the relationship.

For clarity, I didn’t break up with him myself because I was too scared of disappointing him or at worst sending him spiraling into depression. He was still my best friend, and I cared about him, but I know my choice to sour our romantic relationship without talking to him properly was a very very bad one. I apologized to him for it the day we broke up and he seemed to understand and forgave me.

We broke up a week before prom, so I ended up going with a group of friends (he didn’t even want to go to prom so this was the plan anyway). It was a great night that I still remember well, except for what happened afterwards. My best friend who we’ll call Nina planned on having a get-together afterwards. We usually had holiday parties or afterparties at her house so this was normal, with the only difference being the very small number of people coming to her house this time around (only like 7, two of whom left before the sleepover portion and one of whom being her boyfriend who was on break from college). Jeff asked her a few days before prom if she was having a party, to which she said yes. No other words were exchanged - he didn’t ask what kind of party, how many people, times, and not if he was invited.

At midnight, we hear the doorbell ring. I’m upstairs in the spare bedroom (which is on the third floor, for reference) with my current-girlfriend and her then-best friend while Nina, her boyfriend, and our other friend are in the kitchen downstairs. I don’t hear who it is or know what’s going on until a few minutes later. Jeff and his friend are standing in the doorway of the spare bedroom. Nina is standing behind him looking EXTREMELY uncomfortable as he just stands there, smiling awkwardly and not saying anything.

My CGF asks him what he’s doing here, to which he responds that they were coming back from a metal show and decided to stop by since they were in the area. Keep in mind this is a private party, it was literally the middle of the night, Nina’s parents and sister were sleeping on the second floor, and he had shown up unannounced and with an additional person most of us weren’t really friends with. And he thought this was okay.

He doesn’t leave until every single person there expresses to him that they’re not going to speak with him until he leaves (apparently he had specifically asked Nina where I was so he could come talk to me, which he should have realized was weird because we hadn’t spoken sense the breakup). When asked about it repeatedly after the fact by me and other people, he refuses to see that he did anything weird, wrong, or otherwise.

After that, talking was a bit awkward so I asked him if we could take a bit of a break from our friendship too, as I knew he wasn’t totally over me and I wasn’t totally over my own discomfort being around him (multiplied by that weird encounter after prom).

The longer we didn’t have contact, though, the more I realized that - not to be dramatic - I m