My first night out dressed! (well, just a walk around the block)

[Victoria Davison]

After countless times dressing up/putting on makeup in the privacy of my own place, I stepped out for the first time fully dressed and in full makeup!

I was in the middle of one of my usual sessions, where I would put on my face and wig, and then try on some combinations of the few outfits I have, and lounge around dressed up.

It was pouring rain out and the TV news was warning about storms coming through. It was pretty bad out. And a little later, just as I was finishing my makeup, the rain suddenly slowed to a drizzle. Either it was inspiration or my femme self pushing me, but I realized that almost no one would be out, it was night, and I could carry an open umbrella to half-cover my face if needed. It was a chance to finally go out, passable or not, no matter!

I hurriedly selected something discreet and muted, and so I went with a grey women's top over a beige dress, with black tights. I also had on a push-up bra with molded cups that really help my man-boobs become more lady-like. And for me, the piece de resistance were some grey suede ankle boots with a heel. I settled my wig and brushed it down a bit, got my phone and keys in a little handbag-like satchel, and did a final mirror check.

I knew it was going to be in the dark with few people around, but I was still concerned about my hairy arms (I don't shave below the neck at all yet, something to think about later). So despite it being summer I put on a light grey long sleeved shirt under the top. The two pictures I attached show with and without that shirt just before I stepped out.

I stepped outside, and it was quiet as I had expected, with only a slight drizzle. I opened my umbrella, keeping it low, and off I went. I had no goal in mind, so I thought I would just take a walk around the block, then decide on anything else from there.

It was funny, being dressed outside felt a lot like being dressed inside (duh!) The biggest issue was the 5-inch heels!
(EDIT: I didn't have a ruler at hand and I eyeballed the shoes, but after checking online with other shoes and comparing, they are probably closer to 4 inches actually)
I had never walked in them more than back in forth in my living room, and now walking down the slightly rough sidewalk was totally different. It seemed if I walked too flat-footed, the heel would scrape and ever so slightly flex the heel area. It felt like I was "doing it wrong", plus I didn't want to ruin my expensive shoes, so I soon found myself walking more as if I were on my tip-toes, and after making contact with the toe area, I would lightly settle back onto the heel part. I stumbled once and made a wild swing with my arms as I caught my balance. In any case, I didn't feel very lady-like as I got used to doing actual walking in heels.

For a while I just tried to visualize how I would look to others, with my awkward walk and rather masculine build. Fortunately, there was no incident or problem. I passed one couple deep in conversation who didn't even look my way. Apart from the rain and, it was still rather hot and humid, and I felt a bit of sweat building up. Once I made a circuit of the block and was approaching my door, I figured with the extra shirt I had put on I was getting too hot, and there was no need to sweat all over my clothes at this point. So I headed back inside, and my first journey outside came to an end.

The one thing I would like to ask others regarding this experience is, is there a certain way to walk in heels that's "best"? I felt like I had to walk toe-then-heel so as not to drag the heel part on the rough sidewalk, but what does that do to my gait? Does it look really strange to a third-person observer?
Also, does anyone have some general walking tips for when in heels? My first concern is to have a natural gait and a "feminine" walk.

Overall, it was a great experience, the most notable thing being how relaxed I felt given it was my first time. I guess months and months of dressing up in private prepared me to be a little more at ease than I thought I would be. I'm really looking forward to the fall, where I can stay out longer without worrying about the heat. For now I'm going to aim for quiet evenings for stepping out, but who knows? :heehee:

[DDee]

You look Great !!! Wish I had a block to walk around but i'm sure if I did it would be late in the night at my age lol

DDee

[Jodie_Lynn]

woo hoo! Go Victoria! Like DDee said, I wish I had a block to walk around.

As for the gait, remember to take smaller steps and to swing your hips a bit. Not too much, else you'll look like your trying too hard.

[Ashley Lyn]

You look great and I guess you worry too much, like me..!
You'd be fine most anywhere, with or without the longer sleeves..
I really don't think there are many people out there looking to see if a girl 'really is'..

[Rachel Morley]

Woo woo! .... awesome, you did it! It takes courage to go out on your first trip beyond the front door. Congratulations. As for walking in high heels I recommend you enter the search string "how to walk in high heels for beginners" into Youtube .... there's literally dozens and dozens of how-to videos out there for you to watch.

Good luck

[Julie Denier]

Congrats on your first steps out ;)

[Kandy Barr]

First let me welcome you to the forum, you look great! As far as walking in heels, practice, practice, then practice some more. lol xxx

[ArleneRaquel]

Hello and you look GREAT. One trip out enfemme will lead to many more. My Best Wishes darlin.

[Michelle (Oz)]

Thanks for sharing Victoria. The first outing is such a thriling experience and the world didn't end. Power to you. It won't be the last! I remember the umbrella trick in my early stages. Gives confidence plus has a use when raining.

I'm a flats girl. I can't wear heels because of arthritis so no advice there. One thing that is important is the 'walk'. If you want to try to blend then stumbling around in high heels isn't the right look so no points off for being practical.

[Sheila11]

Congrats on going out. I still remember the thrill of the first times, 40 years ago. The first thing about going out in 5 inch heels is don't. Save them for your own pleasure in front of the mirror. Move down to 2 1/2 or three, then spend a ton of time wearing them around the house. Before you know it walking in heels will be second nature. 5 inch stilts are sexy but they are best left to the trained professionals.

[Victoria Davison]

Thanks for the praise everyone! Really though, if you notice something "off" please let me know, I'm always striving to improve.

Ashley, I think if you got about an inch closer than my photograph shows my bare arms, you'd get lost in the thickets ;). Probably many people wouldn't notice, but *I* do and I don't know if I could present confidently with my "natural sleeves" out there!

Rachel, I guess I shouldn't be surprised that there are a bunch of Youtube videos out there for reference. There is for anything else after all! Thanks for reminding me Google is my friend ;)

Michelle and Sheila, thanks for the shoe tips. My problem right now is all I have are those 5-inchers! (I dream big!!)
Actually I think I over-estimated the height by eye, and probably they are more around 4 inches, comparing them now to other products online. (I'll edit my original post)
But of course, I'll invest in some flats and some lower heels for sure. I have the usual mens sneakers and sandals, but another pair or two (or three!) of proper shoes never hurts.

I'm already thinking about my next outing and what to wear! I'll keep you up to date if another outing happens.

Thanks again for all the good advice!

[Leah Lynn]

Hi Victoria! Congratulations on making it out the door! When you feel ready, scroll down to Upcoming Events section and find a group to go to. Last weekend we had a girl join our GNO; her first time out. By the end of the evening, she was looking like a pro. Experienced girls in a group will usually help you fit in.

BTW, those tall heels are for S & M! Stand and Model!

Hugs,
Leah

[Jenny CD]

Going out for the first time is intoxicating, isn't it? Believe it or not... the more you go out, you get used to it and it's no big deal. But, I'm really happy and excited for you! Go girl!!!!!!!

[StephanieCD21]

Good for you!
The proper way to walk in heels is plant the heel first then the toe. If you place your foot in front of the other, you will find walking easier. Watch runway models. It also adds a nice sway to your walk.

[alicia45]

You just crossed a major hurtle! Like others have previously stated, it does get easier but it does take practice and sometimes some hard-earned confidence.

[Victoria Davison]

Leah - It took me a couple reads to get your S & M joke. I was like "but I'm not into S & M....OOOohhhhhhhhhhh"
CD jokes, gotta love em!

Stephanie - Thanks for the advice! One of my concerns with the heels is that they seemed to flex a bit if I went heel first. I don't want to break a heel right off the bat! I will try your recommendation, slowly and gently, at home first. It takes a lot of confidence to place all your weight on a tiny little stick like that!

Alicia - I read somewhere that "CrossDressing is ConfiDence".

[heatherdress]

Great Victoria. Congratulations. Sounds like fun. Keep learning and growing.

[AmyGaleRT]

Good going, Victoria! We all have to start somewhere...for me, it was taking the trash out as Amy. :) Hopefully, one day you'll be more used to going out, and not worry about it anymore, just do it! There's a lot of enjoyment out there! :)

- Amy

[Cheryl123]

Congrats Victoria. You look great btw. The old "walking in the rain with a umbrella" trick is a great way to start. But I'm not sure about the 5 inch heels .. because they will draw attention to yourself .. unless that's what you want :)

[Victoria Davison]

Well, I was inspired by both my recent outing and all your kind words and insight. I ordered a lower-heeled sandal that was on sale, and some flats with a very low heel (almost-flats?).

And tonight I went out again sans makeup!...to take the trash out to the curb. I wore a woman's top and some stretch jeans (with the cutest pink flower embroidered on one back pocket), with a bra and the usual on underneath, and just some flip flops. It was a nice minute and a half, the weather was nicer too, no rain. One woman was walking by, but she didn't notice or care, but I also had a slighter feminine silhouette this time.

I just know I'll be going out more and more for some little "walks"!

[Karren H]

Yeah! I have a couple pink umbrellas for the same kind of outings!

[Beverley Sims]

First time out is always fun.
Around the block in diffrent cities can mean a long time away from home.

[linda allen]

Victoria, buy yourself a decent "men's groomer" (an electric clipper with guides to control the length of the cut). You can trim the arm hair (and other hair) using the guides. Trim it a bit, wait a few weeks, and trim it shorter, repeat until you're somewhere between gorilla and shaved.

As for going out for a walk around the block or taking out the trash, if you don't care who notices, that's fine. Me, I play around far from home just to avoid any problems.

As for the "first time out", I just eased into it. Driving a couple times with a stuffed bra but not getting out of the car, then getting out in a deserted parking lot and taking photos. It is a thrill but it leaves me wanting more. I've been out downtown in the daytime dressed but that was over a year ago.

[suchacutie]

High heels have been a fantastic saving grace for me. I used to (notice the past tense) have a lower back that would "go out" once every couple of years that would lay me up for a week. We learned quickly that just standing in heels that were 4 to 5 inches would give the feeling of draining the tension from my back. That led to having heels that I wear every day in the morning before work, and any other time that my back is weak. Wearing them for an hour in the morning has kept me from a back attack for 8 years!

So, why does it work for me? Walking properly in heels is almost like dancing. When we walk as men, our feet go out first. When we walk in heels, it is the upper thighs that lead, creating a swiveling action in the lower back that generates the hip movement that all men enjoy watching! When I first get out of bed I notice that walking in heels requires much shorter steps "in line". After I've been awake long enough to make coffee and shave it's better, but after my morning shower the back is more limber and the walk is clearly that lovely, flowing movement that we all strive for. I also notice that if I try to walk in heels but continue to lead with my feet as a guy would, my ankles and calves tire rapidly.

Take shorter steps, walk more as if you were walking on a tight rope, lead with your upper thighs as if you were dancing, and let your lower back swivel as the leading thighs direct! It really works and feels terrific!

[Victoria Davison]

Linda, thanks for the arm hair advice. It's coarsest near my wrists and fades up the arm, so I'm considering take a trimmer to my lower arms and "fading" the hairline back in baby steps. I did already tweeze my knuckle hairs out! Gorilla is an apt word to describe that!

Suchacutie, I like the way you described how walking in heels feel. I'll have to try walking around my place "leading with my upper thighs", which sounds strange to me looking at it now, but I have a hunch when I have my heels on and walking, it'll make a lot more sense. And it's nice to hear a story of how heels were so therapeutic, sounds like you were made for them!

[BLUE ORCHID]

Hi Victoria, You are out there now there's no turning back now.

[marny]

take a stroll almost every morning with the dogs, boobs on, coat on if it is cold ,no coat if it is warm, stop to chat with neighbours, nobody flinches. Nice! actually walk dogs for two long walks day dressed.

[Victoria Davison]

I would like to thank everyone for their kind words and input. Last night I went on another walk!

I went with a different outfit, stretch jeans and a salmon top, and with 2 big differences: my breasts came in the mail, so I put those on, and new shoes came, too! This time it's a wedge with maybe a 2.5 inch heel. The change from the pin heel of those silly boots was so amazing, I felt much surer on my feet this time. I got some flats, too, along with the wedges, but it didn't feel like a flats night. I'm a heel girl I guess ;) You can see my outfit I went out in, as well as the shoes in another pic.

It was forecast to rain, and I was actually anticipating it to start so I could get out my umbrella and go for it ;)

I got on the makeup and foundation garments and breast forms, and while I watched the weather closely, I spent about an hour going through the possible permutations in my small wardrobe. I was even trying on some of my men's clothes to mix and match.

It was getting late, and I was all dressed up with no umbrella-in-the-rain to hide under :straightface:

Then the VIctoria me said, "screw the rain, go!" And I listened! It was a late night without a soul to be seen. I stepped out and started off on the same "course" I took last time. I was thinking a zillion things about the walking, changing my step as you all generously told me about, as well as many youtube videos I had watched. I worked great! I was taking slightly smaller steps and I felt so feminine to be walking in a very different way.

I was carrying an umbrella just in case it actually did rain, but it was closed and hanging from my hand, Victoria was out there! After a short but satisfying course, I headed back home without any incident. Just as I started undressing and getting ready to wash off the makeup and go to bed, it started raining...

[Tara Power]

Best things in life happen spontaneously I say, and going for a walk in the rain was the kick up the backside you probably needed to get you out there because you've not only done it once, but you done it twice, and in heels so you should be more confident to go out more often. I could only imagine the kind of death trap a normal pavement would be compared to my perfectly flat tiled floor where the only problem is the dips between the tiles and gravity and thats like Level One: Easy Mode in game terms lol

And from this thread, I have learned to walk thigh first so ill put that into practice with my little steps (no, not the sideward/backward grap onto the wall for dear life and balance steps) and heel first which is scary putting faith into a little stick is right!x

[DanielleT]

I couldn't agree more, start slowly and work your way into things. When I first started dressing, I wanted sooo badly to go out in public! My first excursions were things like gassing my car, dropping off dry cleaning at a remote site and so on. As I gained confidence, I started going for walks in public parks and from time to time in shopping malls. What I learned was that if you dress (kind of) modestly, no super short mini skirts or garish makeup, largely, no one will pay any attention to you. Today, I walk about freely as a woman, busy business districts are an ideal place, everyone there is in a hurry and no one will notice you (unless you want them to).

[Lori Kurtz]

Your second walk outfit is 100% better than the first, and it's the breasts that do it. You have fairly broad shoulders, and larger breasts help to compensate for that. You're doing great.

[Victoria Davison]

Your second walk outfit is 100% better than the first, and it's the breasts that do it. You have fairly broad shoulders, and larger breasts help to compensate for that.

Thanks! I did some serious thinking about which forms to buy, since I was doing all over the internet sight-unseen. I knew a D cup would be good for my build, but I was concerned about going TOO big, so I settled on a C-cup size, figuring my man-boobs would build on those. I do need a properly fitting bra for that now. Sigh, does the shopping ever end? (Lol, I don't know if I want the answer to be a "yes" or "no"!)