I haven’t updated in a good while, though I think that may be that the previous updates had let me settle some elements of my “hobby” with myself more comfortably. I’m genuinely coming closer to grips with my crossdressing habit. It feels less and less like a shameful secret and more and just a very personal and periodic fantasy. With this, I’ve begun to make shallow but definite efforts to actually sharing myself dressed in my feminine outfit with other people in a real space. Oh my…
It’s actually been a little while since I’ve dressed… hard for me to part with facial hair 😛
There are lots of things I’m considering in this. Being the crossdresser I am, I’m remarkable a control-freak about how to engage this kind of encounter. Here’s a list of things I’m thinking about… excuse me while I publicly ask myself these things… I appreciate your replies and input as well:
Do I show my crossdressing to people I already know, or to new people?
This one I feel more or less sure about. If the purpose of my meeting is for crossdressing, I’m much more prone to engage with “new” people, in a crossdressing club or circle or sorts (actually, the country I live in is quite friendly to crossdressers in this regard).
But I also consider the idea of, say, going out en-femme for Halloween as an option — or to a costume party, or concert, or other “themed” event. This would make the event much more immediately accessible and also give me the comfort of passing off dressing as a one-time thing or “just for fun” (which, honestly, it most likely only is).
Do I share myself with other crossdressers, or around non-crossdressing people ?
This one I also feel more sure about. Other crossdressers seem much more approachable than even trans-friendly guys or women. General transgendered folk also seem like a safe bet (assuming “transgender” is different from “crossdressing”), though there is a kind of intensified sensation I would feel around someone “openly” transgendered (i.e. they live their normal life as the opposite sex) – as there is this vague sense of “Oh, well he/she can walk outside freely – I have to change… perhaps he/she looks *down* on my secrecy…”.
For first-time encounters, at least, probably other crossdressers would be more comfortable – but what if said person has done it hundreds of times before?
(God, I sound worse than a virgin 16 year-old)
Where do I actually do this… in my own home? In some shared-but-private space?
I live in a country where there are many small privately-owned spaces available for patrons and customers to engage in the kind of behavior I wish to. There are even dedicated “crossdressing bars” to get started at – you can go inside, get dressed up, have a few drinks, even some “play” rooms. This seems like the right kind of place to start, but what if even that feels like a lot to go forward with. Sharing my living room with one other person, just chatting and watching a film or taking pictures together seems like a perfectly fine idea to me, ah.. but…
Do I go one-to-one, or with a group?
As tall and frightening as I am without heels, I’m not really afraid of what can happen in a one-on-one encounter. I’m more concerned about how quickly things can get out of hand. See below…
What do I actually do in this kind of situation?
Crossdressing is still largely a ‘sexual’ activity for me, so I feel like I need to ask “will doing this around another person I’m attracted to lead to sexual activity?” or “Will I be able to control myself… and will doing that make other people uncomfortable, or end badly for myself and/or someone else?” – ugh, and that by itself is a big enough question. I’m actually quite conservative about engaging in sexual activity – well, not in the activity itself, but in the partner(s) I do it with (I’m a terribly emotional sucker).
Writing these ideas out helps me more or less “feel” what I want, and I think that is a good thing. I’d like to get the opportunity to try at least, but I want the decision to go forward to be a free choice. Obviously there are risks involved in doing this, but I feel like sharing it with someone could help me greatly and finally give a sense of “completion” in the emotional and psychological mindfuck experience of crossdressing. Furthermore, having more confidence in this aspect myself makes me more accepting of the risk of it becoming public knowledge.
Will these things continue to be an issue for me? Or will I lose interest?
I’d welcome any and all thoughts on the issue D: