I'm sorry I can't be more specific in my header, I just am unsure how to categorize it since there is a lot on the table as far as subtopics are concerned.
If you are patient enough read this in full, thank you for bearing with me.

My boyfriend and I have been dating long distance for just over a year now. originally he lived in North Carolina, but has migrated to a location slightly closer to myself in Chicago. I personally struggle with the distance, and he has also expressed some concerns of his own, but so far we have managed fairly well. In struggling with my depression i'm often worried it will steer him away, seeing as more of a burden falls on him to reassure and comfort me. I'm composing this post as a way to vent what I feel, because usually I am not graced with such an opportunity, and also to ask for advice. I'm worried about the extent of my feelings...and the repercussions of what I might do if things do not work out.

Upon taking the relationship attachment quiz, I scored a 110 in relationship avoidance, as well as a 85 in relationship anxiety. These results have only confirmed my fears and suspicions. In terms of my personality and sociability, I am very closed off, and find it difficult to meet people, make friends, or essentially open up to anyone. My inability to open up has lead to a lot of difficulties in our already difficult relationship. I often express my concerns to him about being too dependent on him. Every night we skype for a couple hours, but I usually spend the rest of my night crying. I don't expect anyone to sympathize or relate, but considering all the other aspects in my life, he is the only person who sees me as being worth something. After each session I am forced to return to the realization that I am worthless. I get so physically depressed I cut. a lot. I'm left feeling so alone...My thoughts scare me as well as tempt me. I haven't told him how severe things have been for me, but he does know the majority of it. He has noticed that towards the end of each night I begin to shut down. He even asked if it was worse to spend time and miss him so much afterwards than not spending time at all. My nights before and without him I are just as empty. Usually the severity of my depression increases with the hour, getting the most severe at night. I use him to distract me, remind me that I am loved, to talk me down, to keep me from doing things I regret. Regardless of what we try to do, I still get sad...The worst part for me is that he sees it as a personal failure that he can't cheer me up, and takes it even more personally when I cut. It's so difficult for me. I'm balancing precariously between being so sad that I feel like I need to cut, and knowing that by cutting, I've made him feel like a failure, adding on and worsening my sadness. I don't know what to do....

Despite his reassurances that he loves me and plans to marry me, I have severe trust issues. Distance being a significant factor for me. It's hard to believe that despite being hundreds of miles apart one can remain faithful...and there have been slips on his part....

Before meeting me, He was in love with his best friend. They were even at one point living together. I remember crying for days when we first met and he told me how much her loved her. It broke my heart, I was already In love with him by then. He used to make comparisons between me and her, unknowably no doubt, but they cut like knives, and often prompted me to cut afterwards also. Because he would always talk about her, I always compared myself to her, always finding that I fell short. She's beautiful, thin, according to him has a great personality, etc. Whereas I am ugly, could benefit from losing some weight, and struggle with being personable. We've somewhat come to terms with that since then...but I still struggle to not get upset when she appears in the topic of conversation.
In February, I came across an account with his number, where his profile picture was of her, and he was pretending to be her. (I'll go into more detail about why later on.) Needless to say I was upset. It ruined me for a while. To pretend to be her instead of me, his girlfriend crushed me. I didn't understand why he used her instead of me. I never got an explanation...and it's a touchy subject for us both. But I've interpreted it to mean she would attract more attention, seeing as she's much more beautiful.
When drinking with his coworkers (largely female) I'm always slightly paranoid something intimate could happen...He kissed a girl on the cheek once. I forgave him because he was drunk and several people could vouch it as unintentional, but I hate the idea of him drinking now because of it.
Another coworker of his despite knowing he was dating me, and having him physically say that he wasn't interested, sent multiple invitations to her bed....that leaves me in constant fear that he might be tempted. He's a virgin also....Many girls are starting to notice him, and he doesn't realize how attractive he is, and is completely oblivious to all the flirting....it's both a good and bad thing....

Something the both of us are coming to terms with are some of his sexual turn ons....he's intrigued by the idea of becoming 'female.' and gets aroused easily by it. I originally didn't have any issues with it...but I've begun wondering if I'm feminine enough.... I don't dare tell him this. I'm afraid he'll take it to mean I don't enjoy it, and he'll shut down and never bring it up again. I don't want him to hide himself from me, I want him to feel accepted. I do sometimes enjoy it, but lately, when that's all our sexual plights are, it just makes me feel like I'm not enough. I struggle to know what to do with this. How to handle it. I love him. I struggle with the idea of also loving a her. I don't know what to think. Is my body not enough? He says he loves it, but then why does he see it necessary to also become female? he tells me it's the idea of being emasculated and feminized....but does then then mean I am by default more masculine? I don't know what my role is in any of this...I just want him to see me as feminine and beautiful too....