Constrained crossdressing is a fact of life we all deal with but as we express ourselves today there are less of them to juggle. Crossdressing itself is more accepted by the public today so things that were considered impossible are now commonplace. Seeing a man dressed as a woman today is for the most part dismissed immediately as no big deal and not worthy of additional thought. Part of it is probably that many of us are looking at our phones anyway and only moderately aware of our surroundings.
Many of the constrained crossdressing we do is of our own making and is not a bad thing for the most part. Secrecy is probably the number one concern for us because once the secret is out you cannot undo it. We all know the downside of being discovered which may vary for some of us but secrecy is still a big priority for us. An older crossdresser friend from Texas used a phrase I always liked about letting our secret out. She said to me once “Have you ever tried getting toothpaste back into the tube” it makes the point very clear.

I am not sure where exactly it ranks for everyone on the constrained crossdressing list but Passing is number two for me. For many it is more of an outright barrier because once in place it never gets reevaluated as time goes on. Even though as I said in the first paragraph people don’t care if you are a guy in a dress. If you don’t bother them and just mind your own business they will will ignore you like the scenery around them. I read posts from constrained crossdressers that they are working on going out for the first time once they perfect their makeup so they can pass. It takes a lot more than perfect makeup to pass and to be honest most crossdressers don’t regardless of how good they look. There is always some little thing that usually a genetic woman picks up on with her intuition. My definition of passing is being able to fool everyone all the time thereby achieving a perfect score of 100%. Not likely!
ADDRESSING CONSTRAINED CROSSDRESSSING
If you are able to eliminate the passing goal of constrained crossdressing the results can be very rewarding once you are liberated. Every year at DIVA Las Vegas, Keystone, and now the Lake Erie Gala crossdressers are moving beyond passing and making their first foray out into the world. The structured events allow them to start slow dipping their toe in the water while enjoying the security of a structured event. Many have big sister programs available for those struggling with their constrained crossdressing to take the big step that so many of us took at one time also.
The passing element of constrained crossdressing is a difficult one to eliminate right away and to be honest it takes a while coming in stages. The 1st timer at one of the crossdressing events gains confidence at the structured event from others she knows don’t pass and are enjoying themselves anyway. Meeting and talking with others who share her struggles gives her further confidence in the semi public environment. She will most likely correspond with her new friends throughout the year and look forward to returning next year.
The second year she will see the people from the 1st year and meet some new ones along the way. The next step is to go out in public to a mainstream restaurant with a group of less constrained crossdressers. She is dead set against it until the group persuades her with first hand accounts from people she trusts that it is not a big deal and their is nothing to worry about. She agrees to go but reserves her right to worry because she does not pass and even though the others don’t either it does not matter to her. She now knows that she likes and respects all of them but it wasn’t until just now that found out for sure that they are all CRAZY!! She wears her lower heels in case she has to run back to the hotel.

The final step is when they walk into the restaurant and the Maître D’ greats them with a hello ladies. Then after navigating the crowded dining room with her knees shaking and having her chair pulled out by a waiter she exhales. Next a woman walking back from the restroom tells her that she was admiring her dress is the perfect color for her. Adding to this the food and service are very good and the other patrons are not glaring them with pitchforks.
Game over! She’s hooked and the passing requirement of her constrained crossdressing rule book is eliminated forever. With that behind her more adventures await with her new friends.
Yes, the scenario above is a bit glossy and some constrained crossdressers will never do any of it because they just can’t make it work. That’s OK what works for one may not for the other but at least they can make an informed decision on their own.




Nice article Miss Micki… As always, how far (and where) we go as crossdressers is purely a personal decision. Have fun…. Staci…
Thanks Staci
Micki
It’s always fun to get out the door , most don’t realize it until they take the fist step , I still remember it and that was over 40 years ago
Susie
Hi Susie,
That is very true I think that first time is etched forever in our minds.
The first time may have been terrifying,, but fulfilling at the same time, NOW it is natural step on the way to do some grocery shopping or having a glass of wine or your favorite cocktail nd chatting with the waitress or the barkeep and receiving a compliment on your nails. All wonderful delites.