Stepping out publicly as a woman is a powerful way to validate your female self.
In fact, I recently published a poll asking “How often do you go out in public as a woman?”
I was happy to see that the majority of my readers (transgender women and crossdressers) go out at least occasionally.
No matter how often you do it, I’m sure you can remember your first time presenting as a woman or crossdressing in public.
Since this is such an important gender-affirming step, I’d love to hear about it!
When was it? Where did you go? And what was your experience?
Please share with us in the comments below!
And if you’ve never been en femme in public, I’m sure you’ll find lots of inspiration in these stories.
As always, thank you for reading and participating!
Love,
Lucille
P.S. If you liked this article, you will love my FREE Unleash Your Inner Woman hypnosis mini session.
I have always thought I had a feminine side to me. But it all started back in 2002, my girlfriend and I was playing some guitar hero and seeing as I was more advanced than her I made a bet with her. If I won she have to clean the house, serve and feed me bed for a whole day in nothing but her underwear. She said and if she won, I said you choose. She said if she won I would have dress as a female (outfit, shoes, make up, hair etc.) and I would have to go out for in public for the day. I said your on, seeing as I knew I had a sucker lol. Well needless to say I lost not only once but 2 out of 3. I asked Ok when do we do this, just wanted to pay off my debt as quickly as possible and seeing as it was close to Halloween she choose that day. One or two days before she took me shopping for an outfit, hair some make up to match my skin tone and heels. She then took me to get a mani and pedi with color. The day of I shaved all the body and facial hair off, she applied the make up and dressed me up (that was an three to four hour process). After all dolling up was done she said now look in the mirror, I was like holy crap is that me? Now, although I thought I looked pretty darn good I was really hesitant on going out in public dressed as a female. She said your bet is not paid off yet, We (I ran nervously) got into her car, she drove us to the marina where they have a small park and walkway path next to the water. She Ok lets take a walk around, I was shaking I was so nervous, I thought about backing out of the deal but I came this far. We got out and walked around next to the water as she took pictures of me, she taught me how to walk in heels, sit on the bench like a female and how I should be moving. There was alot of people there and I felt at anytime someone was going to come and start some trouble. However not one person even really noticed, a few people was jogging towards us and just smiled and said hello. We were out there for about an hour or so, then she said Ok were not done yet. I was like WHAT?!? We got back in the car and she took us to a restaurant, we walked in and she kept reminding me that I had to walk and sit like a female does, the receptionist asked how you two ladies doing this evening. I was wow she saw me as a lady cool, however I was still really nervous. We got seated and seeing as I did not have a female voice she told me she that she would order for us, I was like thank you lord. Lots of people in there the server came and took a double look and smiled, my GF then said doesn’t he look gorgeous, the girl taking our order said wait that’s a MAN, OMG I thought something looked, OMG he is I mean she OMG, she then asked but why if you don’t mind me asking, I then said this is what happens when you think you have a sucker and lose a bet, she says OK I see but you look very much like a woman. I was wow did she really think so. There was two other girls looking my way and one of them came up and asked where do you get your nails done, my GF answered for me, she Ok thanks and went back to table, I think she just wanted a closer look. We finished our drinks and dinner and my GF said Ok I think you paid off your debt now with a BIG ‘ol smile on her face. We got back in the car and drove home. On the way home she said now you know what it’s like and what we go through everyday. She then asked me so how did it feel to do all that. I said it actually felt exciting and exhilarating I never thought that I could pass as a female. We got home I took off the outfit and seeing as we went through all of this four hours of work I left the make up and bra and panties on put on my jammies and went to bed. When I woke up the next morning and looked in the mirror I was still in awe. So sorry for the long story, but since that day I have been dressing as a female, get mani and pedi’s regularly my brows waxed and groomed, I buy and apply my own make up and even shop for my own clothes. I have given my female half her own name, wish I could get an ID card with my female name and picture on it. Would save alot of time and anxiety when asked for an ID. I dress every chance I get and go out every chance I get, and when I can’t dress I ware my female underwear under my male clothes everyday. It’s feels so wonderful when I can get fully made up, I think my next step will be getting an make over by an pro and have some pictures taken. My GF is a total supporter for me she even asks me for make up tips and outfit choices funny huh. With out her I don’t think I would have the courage to do any of this on my own, she is my security and I don’t feel nervous when we are out in public together. However there was one time we were waiting for a table and she had to use the restroom and I waited outside for her, there was a few guys sitting at the bar stairing at me and I thought one them was going to approach me, as he made a move like was. I almost fell apart then she came out and put her arm around me and said I’m so sorry I left you for so long there was a line, she could see I just about lost it. But all went well after that. She’s the greatest.
Thanks reading and I hope this helps anyone out there who is thinking about stepping out and get out of the closet. Your missing a wonderful experience every time you do. Everyday missed is a day lost.
XOXO
Jackie
hi Jackie
you are so lucky to have this woman in your life and to have your desires to dress as a lady.
Being a closet Transvestite I would love for some girlfriends to take me out (and ‘out’), but now it’s just me and I only dare to go to the end of the street at the dark of night.
One day the sun will rise, maybe I shall with it.
Hello Maxine
Thank you for your comment, yes I am quite lucky to have the support of my now wife by my side. It does make things a whole lot easier. However there are times when I too feel nervous stepping out even to this day. But there’s something about me when En-Femme, Jackie is a little more risky and daring and she does venture out on her own quite often, with that said I do have to think about what and where I’m going, what I’m going to do when I get there. Basically I do a lot of prepping before I step out, rather in the day light or in the cover of night. Here are some tips that may help you and others that I do before I begin my venture.
1. Make the plans: Do some research of the places your wanting to venture to. A day or 2 before hand check out the places on the internet or take a drive and see first hand in male mode what the situation is going to be like before the day of the event. Will you have to park far away, will you have to walk far, if there is any trouble is there a easy and safe way out. And don’t forget that at some point you will have to use the restroom so you can also find out if the places your going to will have a gender friendly restroom or one in which you can lock just for you, if none is available and must use the ladies room then use your best judgment or try to hold it until your can return to the safety of your home or room or find another to use. I have used the ladies room and had no issues thus far, I pee wait for it to be safe to leave and get the heck out. No checking my make up in the mirror and I use hand sanitizer which I carry in my purse so I don’t have to stop to wash my hands and run the risk of someone walking in at that point, I can always wash them later I also keep some Clorox wipes and my car.
2. Pick the correct out fit and make up: When I first stared stepping out I wanted to look and feel sexy as all hell, not going to lie I think we all do. Wearing the shortest, tightest dress or skirt, 6″ to 8″ high heels, lots of make up big lashes and so on. Well my dear what happen was I either got hit on a lot or clocked. So I have learned that I did not have to look like a sexy hooker “B” to feel sexy. By wearing the correct outfit and make up for the event in which your going to. If I’m going to do some shopping for clothes, groceries, window shopping etc. then later that evening plan to have some dinner at a restaurant. I would wear a cute pair of jeans and top with a pair of boots or flats and light on the make up for the shopping then return back home or my room and change into a little dress about knee high, 3-5″ heels and add on some dinner make up. And I always carry a pair of flats in my purse just in case. Just remember pretty sexy and not hooker sexy. The more you can blend in with out drawing to much attention the better.
3. Have your transportation ready: I always make sure all the brake, tail, signal, head and parking lights are working properly and all the fluids are topped off. I also make sure the gas tank is full as well. There’s nothing worse than to have a break down and having to call a tow truck in the middle of the evening in a unsafe place. Or getting pulled over by the police for having a tail light out and having to explain the way your dressed and why your looks don’t match your ID. Public transportation is something that I avoid and feel is the most unsafe. Just because there’s no where out and your really trapped until those doors open, I had a bad experience once on a train and I was in male mode, vowed never to do it again. That’s just me.
4. Things to carry in your purse: I always try to carry cash if I’m going to be paying for things, most of the time it’s better than using your ATM or credit card. Having show your ID and having to explain or getting clocked just sucks. Speaking of ID make sure you have that as well. I carry some tissue, lip stick, perfume, some make up for touch ups, eye glass cleaner, hand sanitizer, contact info in case of an emergency in which someone can contact if something should happen to you and some protection. I do mean protection I always have a small pocket knife in my purse just on the in case. I know it may not be the most smartest thing to do but it makes me feel better.
5. All dressed up with no where to go: There are times when I’m all dressed up and have no plans. In those cases I still do the things mentioned above and hop in the car and go for a drive. maybe stop and grab a coffee or something quick eat but I try to stay in areas where I know and feel safe. You don’t want to make a wrong turn down the street and find your self caught in a situation you can’t get out of. Even worse driving into an area that you know very well where friends and family may live as well, you may have a lot of explaining to do. Heck if that happens you could always tell them that you lost a bet, lol.
These are just a few tips I do and I sure hope it helps you and anyone else out there. I know there’s a whole lot more to do and think about this is just a few of what I do.
Just remember to plan ahead, dress appropriate, get your ride in shape, check your purse, keep your head up, walk with a little attitude and let that lady inside come out and be free. And always be safe, when in doubt get the heck out of dodge.
Take care hope this helps you to venture farther down the road instead of just the street.
XOXO
Jackie
My first time was last year. I found a dress maker on the internet that had a studio close to my home and explained my situation and she embraced me coming through for a new dress fitting. Well i got all dolled up (without a wig the first time) and went for measurements. I was really nervous, but the session when very well and i have been back 6 or seven times since. The outfits i have had made are stunning …yay. From the third time onwards i have worn a wig, which i must say made me a lot more confident. lovies Elaine xoxoxox
Congratulations to all you girls who have gone out as a woman, I wish I could have joined you I regret to say I havent had the courage to.
I went out in 2008 and have been out as a woman since and met other women and Tgirls here in Htown. At first, it was a problem, but now it is easy. My voice has changed a lot and made it easier and now I go out without makeup and no one knows about me. I love wearing makeup during the day, but since I don’t have a job, I don’t go out at night. I am trying to find a job and make the money to get my bottom issue taken care of and be the woman that I have yearned to be. If that happens, I will do all and be all woman to all.
I went out in 2008 and have been out as a woman since and met other women and Tgirls here in Htown. At first, it was a problem, but now it is easy. My voice has changed a lot and made it easier and now I go out without makeup and no one knows about me. I love wearing makeup during the day, but since I don’t have a job, I don’t go out at night. I am trying to find a job and make the money to get my bottom issue taken care of and be the woman that I have yearned to be. If that happens, I will do all and be all woman to all.
I went out in 2008 and have been out as a woman since and met other women and Tgirls here in Htown. At first, it was a problem, but now it is easy. My voice has changed a lot and made it easier and now I go out without makeup and no one knows about me. I love wearing makeup during the day, but since I don’t have a job, I don’t go out at night. I am trying to find a job and make the money to get my bottom issue taken care of and be the woman that I have yearned to be. If that happens, I will do all and be all woman to all.
It was a cold February night back in 2004 but still I remember it like it was yesterday I had an appointment with my therapist I was considering going to see her enfemme for several years now and with her encouragement I finally built up the courage to do it. I got fully dressed and made up at home and I can still remember exactly what I wore a pink cashmere turtleneck a black knee length pencil skirt and pair of black Nine West 3inch heels which were and still are one of my favorite pairs of shoes finished off with a pair of black pantyhose I felt complete and ready and loved the feeling of leaving my home and entering my car and driving to my therapist office I still remember crossing the street and feeling the wind blow on my nylon clad legs and hearing the click of my heels as I walked to her office a she was a bit shocked to see me dressed but smiled and was proud of me. Now 10 years later I haven’t looked back my therapist told me she could not recognize me as a man cause it’s been that long she hasn’t seen dressed as a man. All this to say I still feel the same emotions as I get ready to go out wherever I go I just love dressing nice and looking nice
Hi Mirella,
Love your attitude, to feel comfortable in your own clothes (not men’s) is so encouraging for me to go out from my house dressed from tip to toe (That will be a net basque, suspender belt fishnet stockings, silk camisole, and a long lace dress)
Could I get away with it? May so only in the dark!
The first time I went out public as a girl was when a friend of mine to luckys bar (gay bar) in Pittsburgh. I wore my short leather mini skirt and a very low cut blue blouse. I even wore my d cup beast forms and my 3″ heels. I had buy me my drinks and even got a guy to dance with me. Kept calling my by my fem mane of Collen. Told me hot I looked to him, but in my option was not 100 % perfect. yet