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Transgender/Transsexual/Getting all dolled up and hitting the town


What safety precautions should I take?

I'm an 18 year old boy and I am interested in crossdressing and I want to dress up as a female and go out in public but I am concerned that if someone discovers I'm a male they might abuse or even attack me as I am aware that people are brutally killed for these things.

Also can you tell me how I can completely pass a girl?


Sorry about that first post. When I write one of these, I tend to put ideas down and then edit and arrange them before I post. Somehow I hit the review button and send buttons way to early. Not sure how that happened… Here is what I should have sent the first time…

There is a famous quote attributed to Abraham Lincoln. He was an American President BTW... LOL
It states....

"You can fool all the people some of the time, and some of the people all the time, but you cannot fool all the people all the time."  

When I hear other crossdressers talking about passing, it's often with the hope that they are convincing enough to be in public and no one ever figure out they are not female. That is where the fantasy meets the reality. You will never fool everyone, every time. Here is the advice I've given to many CD's venturing out for the first time, and it's also the same advice that was given to me when I first ventured out about passing... DON'T TRY TO PASS!!!...

I know that sounds crazy, but if you go out dressed in fem and expect everyone to just accept you, then it might be unsettling when someone does read you. It will happen; there is simply no way to avoid it. However what do you do when that happens is the key to being out in public as a crossdresser.

Confidence is the key. If you are confident in your appearance and what you are doing than you will not have any trouble.  You often hear drag queens say the last thing they put on is their attitude and that is what you have to do. When you go out, you will have to have a “I don't give a F*^K about what other people think” attitude about you. Most people won’t don’t even notice you. When people are out in public, they are going about their business doing what they do and ignore all those around them. If they do take the time to notice you so what. The people that tend to notice us the most are young teenage girls. Say ages 12 to 16. The reason is they are just learning what it means to be a woman, their bodies are developing, emotions and hormones are playing havoc with them, they are worried about their appearance and what others think. (Sound familiar?) Therefore they tend to pay a bit more attention to other people around them and will likely be the first to read you when you are out.

Pay attention and study how other women dress. Look at how genetic girls your own age present themselves. Women don't walk around in mini skirts and high heels everyday looking like hookers. I've known many CD's that go out the first time doing just that. If you want to be passable, dress to fit in. If your going to mall, dress like the other women at the mall. If your going to a fancy dinner, than wear the appropriate cocktail dress. However if your heading out to the grocery store in a pink mini-skirt, F-me pumps, and a bright red wig in the middle of January, you might be calling some attention to yourself.    

What I have found when I’ve been out in fem is the people who notice us are more curious as to what is going on. When they confront us it is in order to ask a question. That’s the time we get to educate them. Some of the best conversations I've ever had was when I got read and they were curious as to why... I actully spent 3 hours at a late night restaurant once speaking to 2 girls that noticed me in a WalMart buying a bra. (I normally wouldn't go there but it was an emergency.) They agreed to buy me coffee if they could find out a bit more about what I was doing.... Made some great friends that night.

I have had a couple of occasions where someone wanted to say something to me or to the group that was insulting or make a big deal of it. However when the "big girl" in the group drops her voice a bit, they usually back off. It's only the idiots and trouble makers that tend to give us a hard time and when they do it's usually due to their own insecurities.

There is safety in numbers!!!! Find a cross dresser / transgender support group in your area. As I'm in the United States, I haven't had any contact with the support groups where you are, but I know there are several. These groups exist to help other trans people with coming out issues, dressing, being in public, etc. When you go out with a group, you’re less likely to be confronted and someone give you a hard time. The last thing a bully would want would be to be beaten up by a bunch of dudes in dresses… ;)

If you are unable to contact a support group in your area, seek out a female friend or friends who are willing to understand and help you. You will be surprised at the reaction you get from girls vs. guys. I’m willing to bet you might already have a friend who suspects something like this about you. As I said young teenage girls are the first to pick up on things like this.

When you do decide to go out, go to safe places. There are places which are trans friendly. These might include gay bars, restaurants, and various clothing stores, make up counters, etc. The other crossdressers in your area likely know the places which are trans-friendly and can help you as you venture out for the first time. BTW… If you are looking for a place to buy makeup, I cant not recommend MAC Cosmetics enough. Their policy is to cater to both genders equally. I’ve read their employees bible and they are very specific that they cater to both genders. So if your looking for help with makeup, check out a MAC store or counter.

Have fun with it!!!!... Like I said doesn’t worry so much about passing, just go out and be you. If you are worried about what other people are thinking you will never really loosen up and discover who you really are. Speaking of being you, there is no one correct way to be a crossdresser. Everyone has their own personality and your personality will reflect in the way you present yourself. I consider myself a makeup and shoe whore. By that I mean l love good makeup and a great pair of pumps. However I have no problem buying clothing from thrift or second hand stores as long as it looks good when I wear it. However a good friend of mine will wear nothing unless it’s a designer label and has to be less than 2 years old. Another girl I know goes by the name DeDe and that reflects a certain aspect of the way she presents herself. I'll let you guess what that means. So what you do is totally up to you and you alone.

You didn’t say if you were gay or straight or bi, but it doesn’t matter what your orientation is. Most crossdressers are heterosexual and are in traditional relationships with genetic women. (G-girls). Because of this many crossdressers are a bit weary concerning gay bars and the like. As I said there are safety in numbers, find some friends and go out with them. If you uncomfortable with the idea of a gay or alternative lifestyle location, keep in mind gay men are not attracted to females or the female appearance. So they tend to shy away from crossdressers. There are guys known as tranny chassers and you will likely come across them eventually. Some are really nice guys who just enjoy want to enjoy your company, others are looking for a bit more. If you are not interested just let them know. Most are understanding and will leave you alone.

If you would like to chat more, you are more than welcome to send me an email at

Again, I’m sorry about the earlier post that I sent prematurely.   

I hope this helps
Cheryl H.


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Cheryl H


I can answer questions regarding male to female cross dressing and related issues. I will not answer any question dealing with pornography. If you are a minor and are asking adult related questions be prepared for me to either reject the question or tell you to ask an adult. Run on questions and that go on and on with various amounts of unrelated details will likely be rejected. I don't have the attention span to read 14 paragraphs crammed in to one about your high school crush before you get to the point. Fantasy and fetish inspired aka (Too good to be true) situations will likely be rejected. I wasn't born yesterday and I've encountered my share of TG fantasy. I can recognize the themes. Fictionmania exist for a reason. I'm a hetro cross dresser, this means I do not date men! I'm happily married with 2 sons. So don't bother asking me for a date... It's not going to happen and I will reject your question.


I am a life long cross dresser (male to female) and have been presenting in public for the past 10 years. I'm a member of Tri-Ess (Society for the Second Self). I've had the opportunity to get to know 100's of transgender people and have worked though and with those that are new to the transgender community. I have assisted many young and new "girls" when venturing out for the first time and worked with their families to help come to terms with many of the issues related to this life style. I am not a doctor or have any type of degree in this field, but I have cross-dreesed my entire life. Who better to ask a question about transgender issues than a transgender person. I am willing to answer any question I can concerning the Transgender lifestyle however there are some areas I will avoid.

Member of Tri-Ess, and Sigma Epsilon. (Society for the Second Self, Atlanta Chapter.)

No formal "education" but I have 40 years of experience being a cross dresser. Who better to speak with than someone who has been there, done that, and has the t-shirt. I'm willing to lend an open ear "and shoulder" when necessary to who ever has the need.

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