Sorry for the long read, but this is important to me and I need to explain it. So I am a guy, but for a long time now I've been questioning both my gender and my sexuality. I honestly feel trapped somewhere in between both genders and it gets confusing. So to start my story I have to go back to my childhood. Around the age of seven I realized I liked girlish stuff just as much as boyish stuff. I tried on my mom's makeup once for 'fun' and got caught by my dad who was angry at me for doing it and threatened me with having to wear it to school if he caught me again. Needless to say I didn't do it again. Now I know a lot of boy's can be curious about their mom's makeup, but I don't know how many of them actually put it on, and out of those how many get yelled at. I'm sure me getting yelled at had a lot to do with the idea that my dad "wasn't going to raise a sissy" or something like that, but of course he wasn't going to say that. Then around this same time I was at a relative's house and while exploring I found a girl's dress hanging up in a room. I immediately knew that I wanted to wear it, and I also knew that I had to be secretive about doing it to prevent any more retribution from an angry parent. So I took the dress and snuck into a bathroom to try it on. I put it on, but I wasn't in it long before I got nervous about getting caught and put it back. This was sort of the beginning of a history of me cross-dressing in secret. Around the age of twelve my parents got divorced and as my dad was now gone I was free to crossdress without worrying too much about getting caught. I would have to borrow my mom's clothes, but I would dress up for hours. Then once I got a car and a job I could afford my own clothes and I started amassing a collection of outfits. I would spend hours in the middle of the night in my room playing dress up. I always sort of questioned my gender and my sexuality based on my desire to dress up from an early age, but I also shrugged it off and thought it must just be a thing for me that I like to dress up. I mostly liked girls and found the idea of anything sexual about men to be disgusting so it didn't make sense that I was anything other than a straight man. Of course adding to this confusion was the fact that I found myself wanting to have sex with men while dressed up. For a long time I hid my crossdressing and no one that I know of ever found out, or if they did they never mentioned it. I would spend time dressed up talking to other crossdressers online and I started talking to guys who liked crossdressers and I started having feelings like I wanted to have sex with some of these people. At one point in my crossdressing "career" a man who I knew was a crossdresser came into a store where I worked and he came up to me and pointed out to me that I would make a good crossdresser. It was such an odd moment because I wanted to confess that I did it, but at the same time I didn't want to be ridiculed by anyone else at work for associating with a known crossdresser. To this day I regret not just telling him and I think about how much fun it would have been to know someone like me. I also regret it from a sexual standpoint as I'm sure he was hitting on me and we would have probably had sex if we had become friends. This pattern of dressing up has continued up until the last few years where I have found myself fantasizing about having sex with men more and more frequently. I have these very elaborate fantasies about meeting men at the gym and having sex, among others fantasies, yet when out in the real world if a guy hits on me I find it creepy, and when I look at guys I think it would be 'weird' to have sex with them. So I am really confused as to whether I am into men or not. I wonder if I am repressing my feeling towards them in public, and then in my mind I am letting it out, or if I actually am just not into them. I wonder if I spent time with another guy in private where no one would see if my behavior would change or if I would still feel weird. I also wonder if I did feel weird would that be a confirmation of my sexuality or just a confirmation of my nervousness. So in between crossdressing and feeling confused about my gender and being confused about my sexuality I decided last year to actually experiment with a guy and see where it took me. I met a guy online. I presented myself as a crossdresser and we hooked up. Nothing much happened beyond me giving him a hand job, and afterwards I did feel a little guilty for being involved in a hook up, which is not something I would normally do, but beyond that I enjoyed it and wanted to do it again and take it a little further. Since the hook up I feel like my fantasizing about men has intensified but I still feel conflicted like I am just going through a phase I will get over, or that I have convinced myself that I like men when I actually don't. So what does everyone think about my situation in regards to this confusing mess of gender and sexuality issues?
First, your sexuality, a somewhat easier and calm issue to talk about. This better be good advice, I'm a bit young though... Have you ever felt emotionally attached to any guy that you saw. Wanted to be sweet, cook dinner for him, just general romantic fluff? I think you need to decide who you are sexually. Look at yourself in say ten years. Could you see yourself being in a sexual and romantic relationship with a guy or the same with a woman? When you take out the other fluff with it...that's pretty much what it all numbs down to. Gender is hard to give good advice on because it's something you just feel deep inside. It isn't something that can be necessarily determined by the way you dress, but if you wanted to take this at face value and the clothes that you wear, you would seem like a woman. If you feel like you don't really belong to any group of gender, then don't belong. Hope I somewhat helped...sort of
Well, how can I feel emotionally attached to any man when I am confused? That is the issue. I had my ability to experiment with gender crushed by my dad at an early age, and so I knew that I would be in trouble if I became emotionally attached to a guy. I can say there were a few guys in my teenage years I liked in a sense, but I knew there was no point in acting on it because of the level of control I was under.
I think you should keep a journal, and describe your feelings and your desires as they come up. If you desire to hook up with a man, write why or why you think you do, and what happened immediately before the desire appeared. The same with your crossdressing. It will give you great insight into who you are if you do this.
Okay. Thanks for the advice. Have you done this before? Kept a journal? What kinds of thoughts did you find yourself having?
Oh, okay. You don't have to tell if you don't want to. I was just wondering because I need something to help guide my examination rather than just thinking in a vacuum.
