Hello, everyone! It has been a while since I've posted, so I want to provide you with a brief update (that may lead to a good discussion).
Toward the end of last year (2013) I started posting pictures of myself venturing outside en femme. I continued venturing outside, and it was exciting for a while, but eventually I found myself wanting to do more. I realized that for me, doing things dressed up alone (at my apartment or within walking distance of my apartment) is not nearly as interesting as doing things dressed up while interacting with other people. I was able to solve this problem by becoming active in my local BDSM/kink community.
Now, why BDSM? I had been doing some research on it for a while and discovered pretty quickly that crossdressing is a common part of BDSM activities, and it dawned on me that people who are practitioners of BDSM probably are used to seeing biological males wearing female clothing. I already had an account on FetLife (the kinky version of Facebook) for a year or two but had basically just been a lurker. I found my local community there and started talking to a few people online, and I met up with one of them and he took me on a shopping trip (a lot of the clothes from my previous pictures here were acquired during that trip). It took me several months to get the courage to go to a munch (in the community, informal dinners at restaurants are known as munches, and people don't dress in fetish gear). The first munch I went to was a small gathering of maybe 5-6 people (it was a TNG munch, meaning that it was exclusively for the 18-35 age range). I was very nervous, but everyone was very nice and I felt very comfortable telling them that I am a crossdresser (I was in guy mode, and in the beginning attended most munches as a guy, but now I always go en femme).
Honestly, becoming a part of this group was the best thing for my crossdressing. I regularly attend munches now (en femme) and am currently the leader/main event organizer for the TNG group. One very generous GG friend from the first munch I attended ended up giving me a lot of clothing and makeup she no longer used/needed, and she (and a few others) have been giving me tips about makeup (and I think I can do a pretty decent job now!) I also have been attending play parties. For those who are unfamiliar, play parties are typically private gatherings (usually at someone's house) where people participate in various BDSM activities (bondage, impact play, various types of sensory play, domination/submission scenes, etc). I've discovered through these parties that I really like being a submissive (I had a feeling about it previously, but the parties confirmed it). Like the munches, I only attend play parties en femme (I really have no desire to do any kinky stuff in guy mode). I've also gone out dancing with people from this group (usually at the local gay bar), attended a few shows. I've had a few sexual encounters as well, though I've also simply made some good friends (with whom I do things non-kink related; hanging out, playing card/video games, etc - sometimes en femme, sometimes as a guy).
I've been hit on (often by guys), though I am finding that I don't mind it that much. It's flattering, and I have been slowly experimenting with doing things with guys (though I still find doing things with girls to be more appealing overall).
Of course, I don't want to imply that joining a BDSM group is the solution for everyone, but it may be a possibility. I'm simultaneously a crossdressing fetishist (doing it for sexual pleasure) and a passing-oriented crossdresser (someone interested in going out in the "vanilla" world and interacting with people en femme in completely non-sexual settings). Does anyone have any thoughts/experiences they would like to share?