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

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.

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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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Nikki Jackson
6 years 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… Read more »

Morgan Staar
Morgan Staar
5 years 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… Read more »

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