I admit this has gotten quite long, so I don't expect everyone to read it. If you want to avoid the back story, you can skip down to the end

I have been cross dressing for about a year. In my teens I secretly experimented with wearing womens clothing. Obviously my sister's and mom's. I was "discovered", and it sort of ended there, though the thoughts about wishing I had been born female did not go away. I don't know when I first had these thoughts, though I had somehow mistakenly thought females had all the advantages. Of course, that may have been partially because I was the older brother, and I may have felt my sisters were favored. I was also incredibly shy, and attracting female attention through my teens was rather difficult.

I remember thinking in my youth that I wished I was female, yet also very clearly having an attraction for females. I had considered a gender change, but realized that's quite a lot of work, and there's no magic pill to make it happen. Eventually I decided to just accept my gender as it'd be far easier to meet a hetero girl whose interested in a hetero guy, than to go through the process (plus reveal to everyone I knew of that part of me), find a woman who is open to being with another woman who was originally a man...

I tend to prefer not to "rock the boat" so to speak, so I default to the status quo when it comes to a decision like this. I'd rather not go through the process of explaining myself to people if I don't have to.

Fast forward a dozen or so years to last year. I was cleaning out some stuff when I came across a garbage bag full of clothes that an ex had left when she moved out a year previous. At first I didn't do anything with this, though I did contact her about it, and she said to just throw them out. I don't know what sparked my interest to look inside that bag, but I did and explored what was inside it. Most were just your typical t-shirts and other stuff, though I did find a couple pairs of jeans (one pair I still regularly wear). My ex was a plus sized girl, so I could put most on, but were either too short (in the torso or arms), and in some cases a little tight in places. There was one pair of nightwear from my ex that did fit perfectly (seems at least 80% of stuff that is labelled 2XL fit me quite well).

I may have first started wearing womens clothings as a bit of a fetish, but it wasn't long before it started to feel natural wearing them. It should be noted that before I started cross dressing, I typically didn't wear clothing around the house. Almost like I was rebelling against my nature. From the moment I'd arrive home after work or from being out of the house, the first thing I'd do is strip out of my male clothing. Unless I have to go out somewhere, I have a tendency to choose to stay at home, rather than be uncomfortable in my male clothing. Fortunately I've lived alone and on my own for the last 3 years, but even then I'd typically wear the minimal necessary for decency. I'd previously sleep nude, as I could never have seemed to fall asleep otherwise, but after I started wearing womens nightwear, I'd have no problems falling asleep. I'd only go nude if it was an incredibly warm night.

One interesting thing I've noticed about myself in the last 10 years is that I almost rarely, if ever buy or replace my mens clothing, unless it's socks, shoes or underwear. Any new mens clothing I may receive are typically in the form of christmas or birthday gifts. One exception was this summer when I didn't have enough clothing to cover a 3 week "vacation", but that shopping trip was by necessity, rather than desire. On the other hand, I have absolutely no problems going on ebay and spending hundreds of $$$ over the last year buying womens clothing. Accumulating more and more each month in a variety of different colors and styles. My appetite for womens clothing is almost bottomless in style and color to mix and match. Yet when I might buy mens shirts, I might only ever buy basic t-shirts of the same color (the only reason to buy the same mens shirt in a different color is so that it doesn't look like I'm wearing the same shirt over and over again....)

When I look back over how my life has progressed, I have contemplated a few aspects in my past. Back in highschool, I was (and to a lesser degree still am) involved in fantasy roleplaying games. Most people in roleplaying typically play characters of their own gender. Although I had my fair share of male characters, I probably created and played just as many female characters. In computer games such as the Sims (or where you can choose your heros gender) I almost invariably create female characters. Partially because they're nice to look at if rendered well, but possibly it's because I want to explore that part of me that I can't easily be in real life.

Several years ago I got involved in online chatting (via yahoo chat rooms). There is typically far more guys on the internet than women, and as such was relatively difficult to find women to chat with. Spending hours bored wandering the chat rooms being fortunate to come across one or maybe two women to chat with was not a great idea of fun. Being rather socially inept with women made it difficult and frustrating. With that said, I was curious what women had to deal with online. Were there as many jerks as I'd heard about, or how do other guys typically interact online with women. At that point I decided to do a social experiment. Go online undercover as a woman and see how women are treated. I created a backstory about my persona, so as to keep my story straight and consistent. In order to avoid any sticky situations with these guys wanting to date me, I decided that my persona was in a relationship, and I was only interested in chatting

Most of the guys that I seemed to "attract" were middle-eastern guys looking for a wife to marry. Eventually I got bored with that, and stopped my general chatting. I was still interested in chatting, but I was looking for something a bit different. I started going into the erotic chat rooms, for a bit of roleplay. If you think it might be hard to find women for general chat, try finding the needle in a haystack of erotic roleplaying

For obvious reasons it is far easier to find guys willing to do erotic roleplay (though for them it's mostly a form of cyber sex). I wasn't too interested in chatting with other guys about sex, and sexual acts, that I decided to be a little more creative. In order to facilitate this, and to try to find those guys who are more interested in erotic storytelling rather than mutual masterbation, I set about creating a website and established a school for erotic roleplaying. I posted transcripts of previous chats, as well as what not to send to some random faceless female on the internet. Some were quite humorous, but likewise pathetic. I tried to give tips to guys to improve the quality of roleplaying and raise the bar by educating them what not to do, and what they could do. I actually spent more time on the website than I actually did in chat, which I somewhat preferred. The "school" enabled me to weed out those guys who didn't meet my standards so I could avoid roleplaying with the undesireables, and have an excuse.

Through all that, I doubt most guys knew that I was not female. Unless of course they chose not to reveal that they knew, but knowing the ratio of guys to girls on the chat, they were probably happy to chat with anyone, as long as they figured their anonymous chat partner was female.

Part of me had wondered in the past if there was something wrong with me. It's one thing to do a social experiment for a week to see how women were treated online, but if I kept on going back day after day and continued to chat with guys online, was I gay, bi or confused? Was the online social experiment simply an excuse I told myself. This paragraph is rhertorical, just merely thoughts I've had.

Adding everything up, and stepping back from my life up to now, I can see that much of it may be just the gender I should have been born as, trying to assert itself. Unfortunately you can't pick the body you are born with.

Well, although I didn't intend to write a book about this aspect of my life, I suppose I needed to say a lot of it.





When I found this place, I had already made a decision that cross dressing wasn't merely a phase or stage in my life. It's probably going to be a part of me for many years, and thus I need to figure out where I want this to go. When I first started, I figured I'd just wear some clothing around the house, but it's become more. When I'm wandering around town and see women, my first thought isn't to look at them as a sex object (like most guys typically do), but to check what they are wearing, and then go through a series of emotions from envy (wishing I had what they were wearing), frustration (that I can't do that in public), anger (as though they are teasing me because as I can't!!!) to acceptance (meh, what else can I do).

Seeing the pictures of some of the ladies on here, some of those things come to the surface, but I also feel hope that I might be able to achieve what some of you have done. At this point I have two options:

1) Chart a course with a goal of SRS and a complete gender change. This unfortunately comes with the task of "coming out" to everyone I know (or at least those I wish to continue to interact with). Looking at my facebook account, I have at least 3 major but distinct "circles" of friends not including my family. To tell anyone in any of those circles is to inevitably have the news circulate throughout. As I'm the sort who doesn't like to rock the boat, and maintain the status quo on this subject, I don't envy this option. If the last two years of my life hadn't happened the way it did, I'd only have my family and high school circle of friends to deal with (of which except for my immediate family I've mostly lost touch with). One of my circles of friends is a youth group I'm involved with, and so I'm not sure what news of this part of me would do. Would I be viewed as weird or different, and be turned away, cutting off valuable experience of a future career.

2) The second option is to keep this as a hidden part of my life. Never truly being free to be the woman I want to be, but otherwise living a "normal" life.

Regardless, I would like to someday in the future to have a family, and be married. Since I'm not into guys, and most women aren't inclined to date cross dressers, I pretty much have to find an open minded lesbian or bi-girl.