Going Out Crossdressed For The First Time (Again)

Dreaming of going out crossdressed for the first time

A few weeks ago I shared my experience going out crossdressed for the first time. There are few things that get the adrenaline pumping, the voice quavering and the nerves tingling in quite the same way. I also shared the story about Vicki’s first time out in public outside of transgender meets. Today, Vicki shares her perspective on the outing that day.

If you’ve had a crossdressing success – perhaps it’s your first time out in public, or the first time attending a transgender event I’d love to hear about it. Take a moment to share the story of your first time crossdressed in public.

Vicki’s First Time Crossdressed in Public

Crossdresser Heaven - Find Your Tribe

This is my follow-up to Vanessa’s post about my first time out in a real public place cross-dressed. It was a mix of apprehension, followed by some moments of self consciousness, but overwhelmingly colored by a sense of accomplishment and joy. Vanessa remarks that her observation of the look on my face was far exceeded by what I was feeling inside. The biggest lesson I learned though was get a sensible pair of heels if one is going to go mall walking. What I hate to admit is that after all the feelings of apprehension and fear, once I was there, I wanted it to keep on going, but my vanity for 5” heels forced us back to the car and finally to home.

I suppose that I may not even have made it this far if it were not for my girlfriend who I have mentioned before is so supportive of and handy to my expression of my femme side. Without her makeup and fashion sense it is hard to believe I would have ever been presentable enough to do it on my own, but more importantly her moral encouragement is truly what has finally gotten me out the door and into the world. The morning of the intended venture I must have talked myself out of it a hundred times, and came very close to letting Vanessa know that I had once more chickened out. My lame excuse had ultimately come down to getting past the neighbors. What the response was, so what,. She told me to remember that my ultimate goal is to present a positive and teaching presence to a world that looks at us strangely. If I can’t get off the block because I’m afraid of what people think then I’m only lying to myself about my motives. Plus, she said, nobody is going to be looking out the window in all likelihood anyway.

So the last excuse was gone and all there was to do was get to it. Madeup, tastefully, and I’ve let my hair grow a little so a short upswept do. We decided that a pair of jeans, a nice blouse with my lacy things under, and a pair of my more comfortable boots would do. I met Vanessa at her car and off we went. Lunch at a nice Chinese restaurant and to be honest once I was inside I felt more and more comfortable. We ordered, aye, and chatted, and for the most part were left to ourselves and as far as I could tell, were not being stared at. As my girlfriend has told me in past attempts to go out, they don’t know me from Adam or Eve anyway. We paid our bills, we had to ask for separate checks and then off to the ladies. I boldly went and used the ladies and then off to the mall.

When Vanessa suggested the mall, it seemed as natural as anything to say yes. I think just being out was giving me little shots of confidence. This of course would be more public, it was the Saturday after Thanksgiving after all, But we parked at Northgate, walked up to the doors, passing many people on the way. I was a little self conscious, but I also felt very ecstatic about what we were doing. By the way, Vanessa carries herself with an air of confidence and an attitude of I belong here too that is easy to feed off and say what the heck. Well, we strolled up one side and down the other, if people were staring I tried not to notice, we browsed at a couple of kiosks, window shopped a couple of stores, went into Macy’s and browsed a couple of departments. Back out and into a bath goods store. We spent some time in there and eventually I allowed myself to detach from Vanessa’s side and allow her to do her own browsing and I did my own. As I was looking at a neat little massage tool, one of the female clerks came up to me and did a very good job of customer service. Alas, I was short of cash in my gf’s little LV purse, but I felt another surge of excitement that I was actually doing this. Vanessa was paying for something back at the check stand and I made my way back to meet up with her once more. We made some small talk with the checker and then we are off and back out on the mall. I was feeling very proud, but my feet at this point were killing me. As much as I wished to continue on, my gosh, I felt like I wished the day would go on forever, but my feet were killing me and we had a long way back to the car.

Well, to bring this to a close, I am hooked. I have not been out in public again yet, but the fears that kept me from even getting out the door are past. I am looking forward to my next venture with Vanessa, with my girlfriend, or just by myself. Not everyone can do it, trust me, I stayed inside for a lot of years, but if you feel strongly about it, then by all means do so. One of my problems has always been that I like to dress as femininely as possible, but as Vanessa and my girlfriend have pointed out, look at the women that are out shopping, sure a nice skirt and heels will work, but not that black latex mini and the platform sandals. Choose something feminine but subtle, by all means go with a friend if you are so fortunate to have someone like Vanessa about. (God bless you V) But most of all, act like you belong. I admit, Seattle is a pretty open minded city so I am lucky there too, but if you act as if you were strolling in male mode, which means YOU aren’t thinking about what you are wearing, you’ve done half the battle. Good luck and good dressing to all you wonderful gals, we are a special community.

Are you looking for confidence stepping out? With this crossdressing guide you’ll present your best crossdressed foot forward every time!

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  1. Morgan Staar 2 months ago

    My first venture out the front door was to the mall too..My friend Mark kept bugging me to get out of the house and experience the real world..lol..I was really dressed to stay under the radar. Simple make-up, jeans, waist length leather jacket ( a prize find in the school’s lost and found), and short leather boots (courtesy of mom’s closet)..We took the bus, walked the mall, grabbed some food at the food court and came home. Heart pounding the whole time
    I had mixed feelings about no one noticing me. Did I pass? Or was I so plain that no cared. hmmmm

  2. Nikki Jackson 9 months ago

    I have only been cross dressing in private. As of late I have been increasing my dress up 2-3 times a week. I got a nice nu bra which gives me cleavage and some fishnet stockings. Targets clearance rack had a beautiful pink lacy bra and I bought one of their 3 pack panties. I dress and feel amazing until I have to go back to reality so I don’t get caught by my wife. I am unsure about how to share this part of me with her but I know it is an eventuality that scares the heck out of me. Your stories of going out inspire courage in me as I hope to some day have the courage to go out on the town.

  3. SusieQue 2 years ago

    I enjoyed the outing stories, so I thought that I would provide one of my own. But first, I am 65 and have been cross dressing for as long as I can remember. I wear support pantyhose or thigh hi stockings nearly every day. In the summer, i wear shorts most of the time, so my shaved, nylon covered legs are on display for all to see in the small Arkansas town that I live in. I have not had any problems (other than sweat). On one very hot august day, I was whiping away sweat as I walked in to Kroger, I met a lady dressed in a very nice skirted suit who said (don’t you just hate pantyhose in this heat)! I laughed and said something about being a slave to fashion, she smiled and suggested that pantyhose are a lot cooler under a skirt plus you can wear stockings instead of pantyhose without the tops showing, and that I should try it. I told her thanks for the suggestion and said that I didn’t think out town was ready for a guy running around in a skirt or dress, at that she said, “you just might be surprised so try it” the only negative response that I have received it that guys tend to keep their distance, even long time friends. Ladies are a lot more understanding, and accepting because they know what we go through to look presentable. Oh yes, since my heart attack in 2007, I have gained almost 75 lbs so nothing about me is even remotely feminine. I have gone from a 16 dress size to a 24. My suggestion is to get out and enjoy!!

  4. Lady Donna 2 years ago

    Just wanted to let you know that reading about your experience’s has raised my confidence level to a new high. Ive been a closeted gal for a very long time and the desire to be out and about as Donna is something I think about every time I dress, which I do every morning for several hours, I do pass very well and have gone out some without any problems but was just to a casino when I was out of town.


  5. Cathy38c 7 years ago

    My cross-dressing in public started out very low key. 1st I was wearing panties, and was a big customer of Victoria’s Secret, I gradually worked my way up to trying on and wearing bras. The Sales Associates were all  very friendly and helpful, bending over backwards to suggest different styles and combinations.  I slowly built my confidence to wear a bra under my straight street cloths. I moved up to wearing women’s stretch denim blue jeans from Lane Bryant. This is the shop I now frequent most. No one seems to notice that I am wearing women’s bra, panties, and blue jeans as my normal street wear.  I’m now adding women’s tops, and shirts to my collection. I have not gone public with a skirt or dress as of yet, but I’m building up to it.

    • Vanessa Law 7 years ago

      A great way to build up confidence hon – that’s good advice for others who are still fearful of going out.

    • Brittany Asher 2 years ago

      At 6 ft. 4 ” and 205 I stand out in the crowd no matter how I am dressed. I have gotten the courage up a couple of times to go out in a dress and heels. I learned about heels the same way you did. % in” heel no matter how tall you are take lots of practice getting used to them. I love my heels but am very self destructive in them. As much as I live the really frilly dresses it is hard to wear them out in public as your girl friend said , look around , it just is not common so you will really stand out. So I have some nice skirts and blouses now and the best I could find in shoes is a pair of 3 in” heels which are a lot better than the 5″ but still when you are already towering over people you really stand out. add that to I am not very shall we say pretty even with make up. I am very scared I guess is the best way to put it to go out much. I really wish I could get past it because I would so love to go everywhere as a female. I love the clothes and the feeling I get getting dressed up. I am just not passable I don’t think. Wish I had someone like V to get me past it. You are very lucky Girl.

  6. Vermont Wyrick 9 years ago

    Just wanted to let you all know that I went out as Vermont today. I went to a beauty and wig shop and got great help in getting a new wig and the lady helping me did not care about me being a cd in fact she said keep it up. I also went to carson parrie scott and got help with makeup there. The lady there said you have to live the way you want and I bought the product from her after she put makeup on me (eyeshadow, masscara, foundation, and lipstick.) and I left there feeling even better and far more comfortable. Like you all said you need to like who you are and not worry about what others might say for it is how you feel. I plan to go out again as Vermont, but this time with maybe a skirt on instead of women’s bluejeans hope to have fun.

  7. Patti 9 years ago

    If you are not use to wearing high heels, wear shoes that are under 2-inches, otherwise by the time you walk into the mall and back out the door, your feet will feel like they are on fire.

    It is very exhilarating to get out and do what you are comfortable with. As a first step, it is always the hardest one, but you have actually made the goal that you’ve set out to do.

    For a few years I lived as a woman, went to work as a woman and went out as a woman. The first time I ever went out, I was full of anxiety and highly nervous. Some friends and I went to a TG Club in San Antonio, TX where they had drag shows. It made me feel much more at ease. After that, I started going out other places too… Straight clubs, bars, shopping (both clothing and grocery), and many other places. Each time you go out, you build your confidence in yourself.

    There is one thing to be wary of though, and all of us need to be alert and aware of what is happening around us, those are the people who get angry and violent. Granted, we are still “male”. It does give us a bit of an upperhand to situations. Confidence in these types of situations helps.

    You need to also prepare yourself for those who wish to make butts of themselves and point you out. Handle it in a polite way, and even sometimes others will step in, but never count on it. BE ON YOUR TOES.

    I have been followed, poked in appropriately at places, breasts grabbed, fondled without my consent and other things. Fortunately, I am confident and used my head in each situation. I’ve had bartenders escort people out of the place, happen to find a police officer once when I was being followed.

    I’m not telling you this to scare people, I am telling you this as you need to be VERY aware so you keep yourself safe.

    Never drink to the point you are drunk, never wear heels that are too high that you will hurt yourself and always, always go with people you know.

    Confidence is one thing, protecting yourself is the utmost priority when you go out.

    Sorry if I got of track, I’ve just heard too many horror stories that I have become very cautious and I honestly do not want to see anyone get hurt or worse yet, get killed because of who they are and the lack of understanding by some.

    • Brittany Asher 2 years ago

      Very true and very sound advice. I live an a very small community and going out there in red neck country is suicide. There is a nice place in Alburquerque Nm. called sidewinders. But getting there from where I was at I had to do most of the trip as a male. there are some very nice people there but there are the other kind too.
      I am very tall so it makes me really self conscious which only makes it harder to enjoy myself. Then add I cannot find any 2″ or smaller heel in a size 15 , I get up to 6′ 7″ dressed up as a female. That really gets a lot of attention. My long blonde wig, 3″ heels and a dress or skirt and blouse I stand out.

  8. Ragina 9 years ago

    Hi Raquel, I’m Ragina.
    I loved your comment about folks going from” redneck homophobes” to understanding friends and supporters. If more folks would be just a little bit more open about things, then all of us would be a lot better off allover the world, not just in transgenderland. I found this to be so true when I spent a years tour of duty in Iraq. The local nationals that I interacted with, be they contractors or the barber who cut my hair, those of us who treated the locals with respect and were genuinly interested in making a relationship with them had a better time than those who didn’t respect them. If those people we incountered as we are out and about dressed would be able to see us as people, everyone would be better off in the long run. So I say, be out, be visable be proud and be beautiful ladies, we are people too!!!!

  9. Vicki 9 years ago

    Thanks for all the input girls, and the encouragement. Racquel Lynn, I really appreciate the thoughts on just being yourself and not worrying about or looking to see what kind of reactions you are getting. I really tried to do that on our outing. Of course it helped that I wasn’t wearing my contacts that day, (Vanessa drove) so it made it hard to really focus too far off. So, as I continue to keep going out, I keep in mind exactly what you say, focus as if I were just on a normal walk in the mall or where ever, don’t try and overhear if anyone is commenting. In all likelihood they’ll wait until you are out of earshot, and be ready to engage someone without a lot of histrionics or shyness. I’m there for me of course, but I also represent a large community just like me. When I was in high school and played football and baseball the coaches would say to do nothing that would bring shame on your school. My kids were told to “represent”. So that is what I try and do now. Represent. I’m playing for a really good team and I want the spectators to see a good representation

  10. Racquel Lynn 9 years ago

    Being relaxed and confident is as important in passing (if not more important) that what you wear and having your hair and make-up right. When you go out and wonder what everyone is thinking and looking around to see who is noticing you and may be staring, you draw more attention to yourself and people will look closer.
    When you just relax and be yourself and not care who’s looking, if they figured you out, or what they may be saying, and just go about your business as you normally would, then you are not only much more passable, but even if they do figure it out, you are usually much more accepted and other people think about it less when you have the confidence to be yourself. And when people know and respectfully ask you questions, don’t get nervous, but give a respectful question an honest and respectful answer. I have found that many people who may normally be against what we do will often reconsider and become supportive as long as you are honest and respectful and simply talk with them and answer their questions. I have met some strangers that seemed like real redneck homophobes that would never accept crossdressing as “normal”, but have approached me and asked me questions and when I am straight up, open and honest, the questions slowly go from the feeling of “why would you do this/this is wrong” and starts going to a feeling of “I’m starting to understand a little and want to know more” and they walk away being a new friend and very supportive.

    • Racquel Lynn 9 years ago

      It sounds like you had a great time out Vicky. Maybeone day I will be able to visit Seattle and Vanessa, You and I can all go shopping and hit the town!
      Congradulations!!! Hope you get out again soon and often!

      If you’re ever in Louisville, KY. we’ll go hang out here!

  11. Ragina 9 years ago

    Hi Vicki, WOW, it sounds like the two of you had a grand time. I would have loved to have been with you and enjoy the day. Alas, Georgia is a long way from Seattle, so I’l enjoy the trip through your eyes. I hope to be able to go out soon myself. There are still a few things that I need to do before then, so I’d better get to them. I’ll keep you all posted as I venture out.
    Best to all, Ragina

  12. Leslee 9 years ago

    I learned very early not to wear such high heels, even tho are very femme. I normally wear flats when I go places and rarely more than a 2′ heel. Look around as there are some cute flats to fit anyone. Being tall I also wear them so I fit in better. I tend to wear stylish cloths with blending colors and style. I think my style sence is better than my wife. I had a great girl friend who helped me with the style cordinations. That is a must. Now I have both the courage and looks to do things in public.

    • Ragina 9 years ago

      Hi Leslee. I agree with you. 4 inch heels are sooooo sexy to wear, but really impractacle for anywhere but home. I have a pair of 2inch Hushpuppies that look great with just about anything, but are still very comfortable for a long while. Ragina

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