Be Honest

I ordered something from a crossdressing store in the city and went to pick it up last Sunday. When I go there is probably the only time I go out in daylight and look forward to those few steps to her door. Unfortunately she was very busy that day and apologized and gave me the order but couldn't let me in the store because someone reserved some private time. I was very disappointed because I don't do this very often and I have to build up a lot of confidence to walk those few steps out in daylight.
When I got home I realized she gave me the wrong thing, as much as I was disappointed I was also looking forward to dressing again so I went back on Tuesday. When I got there on Tuesday afternoon for some reason the streets were very quit, I looked around and got out of my car and seen there were a few people around but not like usual. I decided not to rush like I usally do but instead walk slowly and try to take it all in and just take my time, it was amazing the whole outdoor feeling. When I got in the store it was quit in there and she apologized for Sunday but this time she was more relaxed and almost wanted to just talk.
She asked me if I made any other advantages since the last time we talked? I asked her if she could give me a honest opinion, I told her my wife is the only one who sees me dressed but I have a hard time asking her if I could pass as a women or if not pass at least fit in alittle. I took a step back and asked her what she thought and to be honest and I would respect some suggestions and to be honest.
Without a flinch she told me I look beautiful and told me I put everything together well and with those long legs to die for. She told me that with the situation I'm in with only my wife knowing and that we could fight genetics as much as me want but obviously I am a man dressed as a women. But not to get discouraged because in the right environment that would change, her store is in our gay community of the city and she tells me that I could walk these streets and nobody will give me a second look. She told if I wanted to open up more why would I go to a regular coffee shop or club when there are so many in that area that are so exceptiing of crossdressers and that I could literally walk in sit down and have a coffee dressed the way I was and nobody would say a thing. She gave me a few names of some restaurants and coffee shops that I could go out for dinner with my wife, she won't feel intimidated because there's going to be a mixture of everything and they are used to seeing men dressed as women. She told me that maybe I don't totally pass as a women but in the right environment it would make it all possible that I could enjoy expressing myself with less pressure and enjoying a dinner or a coffee with my wife or alone and not have to worry about anything. She did put out the warning that just like a person having an affair there is a chance of getting caught and that could cause some family problems. She always gives me so much confidence, the last time I went for a coffee with her a few doors down from her store and maybe because I was with her I felt comfortable but nobody did give me a second look. Well that coffee shop we went to last time was closed because of the Covid but she asked me why on my way home I don't go to a coffee shop she suggested and go in and order a coffee and sit down and enjoy. Well I laughed but she wasn't laughing and she pulled me over to her mirror and told me to look at myself and see that I'm not a women but a beautiful crossdresser. I don't know why but this feeling of emotion went threw me, i wanted to hug her and she seen the emotion and joked that i better not tear up its going to ruin my make-up. Her final statement was to never believe we are trapped of no hope or give up, we just have to adjust and put ourselves in the right place that we can make it work, even if it's the smallest step. I got my order and this time again I just took my time relaxed walking to the car and when I got to my car she yield out to me the name of the coffee shop and we both laughed.
I know there are a lot more experienced dressers here who do go out in public, what do you think did she give me good advice?

Yes, she did.

That being said she also said there is always the chance, however remote, of being recognized. You have to decide if the reduced risk is worth the reward.

Lastly, what would your wife think or say if you went you as suggested?

Have I been out and about, yes. Have I traveled and stayed enfemme away from home, yes. Was it worth it? Yes!

In the end only you know the answer to "your" question.

Yes she did. There is always a chance someone will say something or you will see someone you know but the experience is worth the risk.

If you see someone you know at a coffee shop in a gay community, what would you think of them being there? Seems to me, they would be there for the same reason you are.

I would say that she gave you the right advice, there is always that chance you take that you might run into someone that you know, but look at it this way
it is your life and not theirs's, so as long as you are happy that's all that counts. She also took the time to stand you in front of a mirror so you could see how you look. Read into that just a little, she was showing you to look at yourself and maybe make some little improvements in the future

A good post - you are lucky to have at least two women in your life who support you and give honest feedback when you ask

"She pulled me over to her mirror and told me to look at myself and see that I'm not a woman but a beautiful cross dresser."

I think that is a good analysis applicable to most cross dressers. As stated we can "fight genetics" as much as we want, but, cannot escape the obvious; man in a dress. She does bring out the fact where we choose to go is of importance. Yes, hanging out in an accepting environment makes a lot of sense, obvious to me. The problem is many cross dressers do not live in a community large enough to have some geographic safe area. Then, there is the prospect of being shunned by family, friends, co-workers, whoever.

I did find it interest you were not able to get into her store because "someone reserved some private time." Kind of obvious to me you're not alone in your community. I think she is offering a valuable service in your community. I remember decades ago there was a woman's wear shop that had a small printed sign near the entrance indicating there were after hours appointments available.

In my opinion she gave you excellent advice. I for one have not worn men's clothes in over a year. I do now identify as transgender but have yet to even be in HRT due to other medical things that may become worse. I have been all over this city and a few other cities and even some small towns. I wont lie and say there is never negativity and laughter. But that is few and far between. I dont specifically go to only gay places either, with the exception of bars. That is only because I dont drink, I go for shows and fund raising events. So yes get out there enjoy yourself. The more you do it the more you will want because you will see the fear is in your mind. Of course always be aware of your surroundings but not over vigilant you don't have fun.

Listen to her but more importantly listen to your heart.

I went out two days ago and when I came back my wife asked me if people notice. I told her most people are wrapped up in their lives and don't care. Plus, they don’t know who I am (I'm 7,500 miles away from my regular home, but I do know a handful of people here).

Here's what I did. Took a train to the city (Melbourne, Australia), then a tram, walked on a pier, had lunch at a restaurant, changed into a bikini, walked along the beach, tram back to city, walked twenty minutes, visited a store (the SA told me to come out and strut on the catwalk), bought a jumpsuit, train home. Lots of people saw me, zero people said anything (well, the people at the store said I looked great and they were happy to see me).

The biggest risk is going in public with your wife, but as she seems to be willing to take the risk, why don't you?

Life is about risk. Every day we drive we risk our lives. Going out dressed in the right place is a very reasonable risk to take, and becomes easy once your overcome the fear.

I honestly think that was great advice. I honestly want to go out en femme as often as possible. My wife isn't okay with it because she might be embarrassed. For me I am passed that point. When I dress it completes me. It is honestly the missing part of my life.

She gave you wonderful advice Maria. If you are still concerned about going to the places she mentioned because they might be too near where you live go back & ask her if she can recommend similar places farther away where you chances of running into someone you know are much less.

I agree with others that her advice was very good. I also particularly agree with Stephanie. If you see someone you know while you're in the area of the gay community, turn the tables if you must and wonder why they are there. It is a 2 way street and you have every right to be in the lane you choose.

It?s amazing how much of an impact a complete stranger will have on us. We just want to feel beautiful and pretty. It?s that easy to be kind in this world.

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Originally Posted by Maria 60

Her final statement was to never believe we are trapped of no hope or give up, we just have to adjust and put ourselves in the right place that we can make it work, even if it's the smallest step.

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If that's not the best advice ever given (not just for going out dressed, but for any situation), I don't know what is. I need to follow it myself!

Maria, you were given great advice. I don't know anything about the area where you live, but where I live in the metro Atlanta area I get out and about as Phoebe just about everywhere without any problems. I know that I don't truly "pass", but it doesn't matter. These days it's not necessary for a crossdresser to pass as someone who was a female at birth. All you need to do is be accepted respectfully as a transgender woman. From what your store owner friend said, it sounds like you do that very well.

Maria, I think the advice was excellent. I realize I am not going to pass, but I try to look the best I can every time I go out.

Really great advice from the store owner. I have been out in public a long time now, and always have gone out with the expectation of being read. With that behind me, I just focus on enjoying the experience. If you go to one of the transfriendly local establishments, you will be able to completely put those doubts out of your mind. I think its a great idea to include your wife in such an adventure, maybe even bring along your SIL and have GNO!

Maria: I think the advice was great. She provided you with affirmation about the person that she see's. Our own limiting beliefs seem to affect that a great deal. At this stage in my life, I am more interested in enjoying anytime that I am able to go out dressed as I like to dress. I have gone out without makeup (don't wear much of that) and I do not own a wig at this time. I have short hair. If that was the only dead give away of my being a man then that would be fine. I think when I get the chance to dress as Jenni I have more confidence than any other time. This helps me to just take the risk. Mine are calculated risks but just the same I push myself. My time to spin on this planet gets shorter and shorter everyday. So the opportunities that I do have I must capture.