I notice many respondents wanting to meet other crossdressers are in NY. Have you considered
– the Keystone Conference in PA
– all kinds of opportunities in NY City
– forming your own meetup group… you can initiate this on this site; start by seeing if there are any in your area… others have responded as to how to do this
– let me know if you’d be interested in a cruise. About 20 crossdressers and SOs, along with their spouses, cruise together for a week once or twice a year. I anticipate the next cruise will begin end of October. One of the group runs a travel agency, along with her wife. they plan it out so we can dine together and have opportunities to meet casually… dressed or not as each prefer… and there are lots of shore excursion where people are free to team up with others or go solo as they choose. By the end of the week you can make lots of good friends.
Few crossdressers are brave enough to get out and about in their own town. If you are going to travel to meet others anyway, I can’t understand why there is difficulty finding meetup groups or getting makeup or other crossdressing services within traveling distance. One can find help with makeup and selecting feminine attire at malls, I’m sure many women would be happy to meet after hours or at your home or their shop to help if you like. You could start by asking employees at cosmetic counters at places like Macy’s and Sephora’s who do makeovers regularly. Professional services are not hard to find.
In my lifetime crossdressing has moved from being illegal to being fairly widely acknowledged and accepted as within the realm of normal behavior, certainly far more accessible than it once was. No longer is there need to fear arrest, institutionalization, or anything more than curiosity, embarrassment from or criticism by some. And those who are curious are fun to engage with. I have been stopped by police many times in normal traffic situations and even involved in serious wrecks, and gone nearly everywhere one could imagine in public with seldom a word- at least not a negative one- being said about how I am dressed. There is justification in being concerned about spousal acceptance and how we may impact friends or colleagues, that deserves serious consideration. But the general public hardly notices or cares. We need not be prisoners to our own minds.
It is freeing in many regards to let ourselves be “clocked” by wearing nail polish to a doctor or when having a massage, or taking other risks of discovery, as it generally leads to playful, enjoyable, educational conversations and very seldom to negative judgment or criticism. Such risks carry little downside concern unless done too close to where we live.